# Supplementary Material (ESI) for Chemical Communications

# This journal is © The Royal Society of Chemistry 2003





data_global



_audit_creation_method            'SHELXL-97 plus manual editing'



_journal_coden_Cambridge      182



loop_

_publ_author_name

'Andrew Bond'



_publ_contact_author_name         'Andrew D. Bond'

_publ_contact_author_address

;

Department of Chemistry

University of Cambridge

Lensfield Road

Cambridge

CB2 1EW

UK

;



_publ_contact_author_email        adb29@cam.ac.uk

_publ_contact_author_fax          '(01223) 336362'

_publ_contact_author_phone        '(01223) 336352'



_publ_requested_journal       'Chemical Communications'





_publ_section_title		

;

In situ co-crystallisation as a tool for

low-temperature crystal engineering

;



data_ab0210 

_database_code_CSD                  192849



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / formic acid'

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C H2 O2)' 

_chemical_formula_sum             'C6 H8 N2 O4' 

_chemical_formula_weight          172.14 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            monoclinic

_symmetry_space_group_name_H-M    P21/c 



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, y+1/2, -z+1/2' 

'-x, -y, -z' 

'x, -y-1/2, z-1/2' 



_cell_length_a                    3.6994(1) 

_cell_length_b                    7.0340(3) 

_cell_length_c                    16.1607(9) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  96.068(2) 

_cell_angle_gamma                 90.00 

_cell_volume                      418.17(3) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     3743 

_cell_measurement_theta_min       1.02

_cell_measurement_theta_max       25.35



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.367 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              180 

_exptl_absorpt_coefficient_mu     0.116 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   0.9604 

_exptl_absorpt_correction_T_max   0.9771 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm capillary at ca. 280 K. More than one crystal

present - only reflections associated with the major component included in the

integration - reflected in relatively high R(int). 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             2895 

_diffrn_reflns_av_R_equivalents   0.1556 

_diffrn_reflns_av_sigmaI/netI     0.0862 

_diffrn_reflns_limit_h_min        -4 

_diffrn_reflns_limit_h_max        4 

_diffrn_reflns_limit_k_min        -7 

_diffrn_reflns_limit_k_max        8 

_diffrn_reflns_limit_l_min        -17 

_diffrn_reflns_limit_l_max        19 

_diffrn_reflns_theta_min          3.85 

_diffrn_reflns_theta_max          25.32 

_diffrn_measured_fraction_theta_max    0.981 

_diffrn_reflns_theta_full              25.32 

_diffrn_measured_fraction_theta_full   0.981 

_reflns_number_total              760 

_reflns_number_gt                 661 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.1003P)²+0.0876P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          760 

_refine_ls_number_parameters      59 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0787 

_refine_ls_R_factor_gt            0.0723 

_refine_ls_wR_factor_ref          0.1925 

_refine_ls_wR_factor_gt           0.1839 

_refine_ls_goodness_of_fit_ref    1.107 

_refine_ls_restrained_S_all       1.107 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.334 

_refine_diff_density_min          -0.236 

_refine_diff_density_rms          0.066 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O 0.3994(5) 0.9644(2) 0.38667(10) 0.0559(6) Uani 1 1 d . . . 

H1 H 0.281(11) 0.873(5) 0.414(2) 0.096(11) Uiso 1 1 d . . . 

O2 O 0.1775(5) 0.8171(2) 0.26999(10) 0.0597(6) Uani 1 1 d . . . 

C1 C 0.3318(6) 0.9476(3) 0.30605(14) 0.0510(7) Uani 1 1 d . . . 

H1A H 0.4120 1.0478 0.2730 0.061 Uiso 1 1 calc R . . 

N1A N 0.1374(5) 0.6608(2) 0.46444(11) 0.0455(6) Uani 1 1 d . . . 

C2A C 0.0975(6) 0.6525(3) 0.54571(13) 0.0464(7) Uani 1 1 d . . . 

H2AA H 0.1640 0.7592 0.5800 0.056 Uiso 1 1 calc R . . 

C1A C 0.0379(6) 0.5075(3) 0.41936(13) 0.0469(7) Uani 1 1 d . . . 

H1AA H 0.0610 0.5086 0.3614 0.056 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0709(12) 0.0392(10) 0.0575(11) 0.0018(7) 0.0061(8) -0.0146(7) 

O2 0.0789(13) 0.0437(10) 0.0562(11) -0.0006(7) 0.0060(9) -0.0058(8) 

C1 0.0608(14) 0.0362(11) 0.0569(13) 0.0045(9) 0.0097(11) -0.0025(9) 

N1A 0.0480(11) 0.0369(10) 0.0516(11) 0.0019(7) 0.0049(8) -0.0038(7) 

C2A 0.0505(13) 0.0372(11) 0.0510(12) -0.0080(9) 0.0036(9) -0.0037(8) 

C1A 0.0528(13) 0.0454(12) 0.0426(11) -0.0014(9) 0.0051(10) -0.0026(8) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.306(3) . ? 

O1 H1 0.92(4) . ? 

O2 C1 1.199(3) . ? 

C1 H1A 0.9500 . ? 

N1A C1A 1.331(3) . ? 

N1A C2A 1.338(3) . ? 

C2A C1A 1.377(3) 3_566 ? 

C2A H2AA 0.9500 . ? 

C1A C2A 1.377(3) 3_566 ? 

C1A H1AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 111(2) . . ? 

O2 C1 O1 125.8(2) . . ? 

O2 C1 H1A 117.1 . . ? 

O1 C1 H1A 117.1 . . ? 

C1A N1A C2A 116.64(17) . . ? 

N1A C2A C1A 121.39(18) . 3_566 ? 

N1A C2A H2AA 119.3 . . ? 

C1A C2A H2AA 119.3 3_566 . ? 

N1A C1A C2A 121.96(18) . 3_566 ? 

N1A C1A H1AA 119.0 . . ? 

C2A C1A H1AA 119.0 3_566 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

C1A N1A C2A C1A 0.4(3) . . . 3_566 ? 

C2A N1A C1A C2A -0.4(3) . . . 3_566 ? 



#===END



data_ab0209 

_database_code_CSD                  192850



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / acetic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C2 H4 O2)' 

_chemical_formula_sum             'C8 H12 N2 O4' 

_chemical_formula_weight          200.20 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            triclinic 

_symmetry_space_group_name_H-M    P-1



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    5.4869(2) 

_cell_length_b                    8.1885(2) 

_cell_length_c                    11.9960(4) 

_cell_angle_alpha                 70.076(1) 

_cell_angle_beta                  86.667(1) 

_cell_angle_gamma                 89.925(2) 

_cell_volume                      505.76(3) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     3505 

_cell_measurement_theta_min       1.02

_cell_measurement_theta_max       27.48



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.315 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              212 

_exptl_absorpt_coefficient_mu     0.106 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm capillary at ca. 275 K 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             5274 

_diffrn_reflns_av_R_equivalents   0.0719 

_diffrn_reflns_av_sigmaI/netI     0.0529 

_diffrn_reflns_limit_h_min        -7 

_diffrn_reflns_limit_h_max        7 

_diffrn_reflns_limit_k_min        -10 

_diffrn_reflns_limit_k_max        10 

_diffrn_reflns_limit_l_min        -13 

_diffrn_reflns_limit_l_max        15 

_diffrn_reflns_theta_min          3.72 

_diffrn_reflns_theta_max          27.51 

_diffrn_measured_fraction_theta_max    0.979 

_diffrn_reflns_theta_full              27.51 

_diffrn_measured_fraction_theta_full   0.979 

_reflns_number_total              2287 

_reflns_number_gt                 1904 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0677P)²+0.1511P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2287 

_refine_ls_number_parameters      137 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0635 

_refine_ls_R_factor_gt            0.0518 

_refine_ls_wR_factor_ref          0.1499 

_refine_ls_wR_factor_gt           0.1370 

_refine_ls_goodness_of_fit_ref    1.061 

_refine_ls_restrained_S_all       1.061 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.240 

_refine_diff_density_min          -0.214 

_refine_diff_density_rms          0.046 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O2_1 O -0.1440(2) 0.32153(17) -0.00707(11) 0.0460(3) Uani 1 1 d . . . 

O1_1 O -0.0215(2) 0.20358(16) 0.17682(10) 0.0426(3) Uani 1 1 d . . . 

H1_1 H 0.093(5) 0.149(3) 0.136(2) 0.077(8) Uiso 1 1 d . . . 

C1_1 C -0.1633(3) 0.3057(2) 0.09716(15) 0.0353(3) Uani 1 1 d . . . 

C2_1 C -0.3504(3) 0.3953(2) 0.15031(16) 0.0444(4) Uani 1 1 d . . . 

H2A_1 H -0.4125 0.4950 0.0875 0.067 Uiso 1 1 calc R . . 

H2B_1 H -0.2757 0.4354 0.2089 0.067 Uiso 1 1 calc R . . 

H2C_1 H -0.4854 0.3140 0.1894 0.067 Uiso 1 1 calc R . . 

N1A_1 N 0.3190(2) 0.05536(18) 0.06390(12) 0.0380(3) Uani 1 1 d . . . 

C1A_1 C 0.3234(3) 0.1024(2) -0.05361(16) 0.0392(4) Uani 1 1 d . . . 

H1AA_1 H 0.1993 0.1753 -0.0950 0.047 Uiso 1 1 calc R . . 

C2A_1 C 0.4952(3) -0.0477(2) 0.11734(15) 0.0388(4) Uani 1 1 d . . . 

H2AA_1 H 0.4971 -0.0850 0.2014 0.047 Uiso 1 1 calc R . . 

O2_2 O 0.2155(2) 0.44093(17) -0.39220(12) 0.0484(3) Uani 1 1 d . . . 

O1_2 O -0.0370(2) 0.21128(15) -0.33587(11) 0.0419(3) Uani 1 1 d . . . 

H1_2 H 0.093(4) 0.163(3) -0.370(2) 0.064(6) Uiso 1 1 d . . . 

C1_2 C 0.0194(3) 0.3743(2) -0.34952(13) 0.0314(3) Uani 1 1 d . . . 

C2_2 C -0.1833(3) 0.4641(2) -0.30628(15) 0.0372(4) Uani 1 1 d . . . 

H2D_2 H -0.1449 0.5887 -0.3315 0.056 Uiso 1 1 calc R . . 

H2E_2 H -0.2020 0.4161 -0.2194 0.056 Uiso 1 1 calc R . . 

H2F_2 H -0.3357 0.4461 -0.3396 0.056 Uiso 1 1 calc R . . 

N1A_2 N 0.3211(2) 0.06645(17) -0.44135(12) 0.0353(3) Uani 1 1 d . . . 

C2A_2 C 0.3004(3) -0.0921(2) -0.44764(15) 0.0367(4) Uani 1 1 d . . . 

H2AB_2 H 0.1598 -0.1616 -0.4110 0.044 Uiso 1 1 calc R . . 

C1A_2 C 0.5214(3) 0.1588(2) -0.49370(14) 0.0343(3) Uani 1 1 d . . . 

H1AB_2 H 0.5429 0.2724 -0.4909 0.041 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O2_1 0.0520(7) 0.0544(8) 0.0366(6) -0.0227(6) 0.0011(5) 0.0095(6) 

O1_1 0.0413(6) 0.0514(7) 0.0375(6) -0.0190(5) 0.0030(5) 0.0167(5) 

C1_1 0.0339(7) 0.0366(8) 0.0383(8) -0.0176(6) 0.0036(6) 0.0016(6) 

C2_1 0.0428(9) 0.0526(10) 0.0458(10) -0.0269(8) -0.0030(7) 0.0172(7) 

N1A_1 0.0338(7) 0.0405(7) 0.0434(8) -0.0211(6) 0.0097(5) 0.0011(5) 

C1A_1 0.0354(8) 0.0379(8) 0.0445(9) -0.0143(7) -0.0009(6) 0.0056(6) 

C2A_1 0.0427(8) 0.0420(9) 0.0324(8) -0.0145(7) 0.0049(6) -0.0013(6) 

O2_2 0.0320(6) 0.0568(8) 0.0634(8) -0.0320(7) 0.0114(5) -0.0059(5) 

O1_2 0.0367(6) 0.0396(6) 0.0525(7) -0.0225(5) 0.0141(5) 0.0028(5) 

C1_2 0.0293(7) 0.0405(8) 0.0277(7) -0.0163(6) 0.0004(5) 0.0040(6) 

C2_2 0.0339(8) 0.0411(8) 0.0405(8) -0.0197(7) 0.0027(6) 0.0069(6) 

N1A_2 0.0333(6) 0.0392(7) 0.0360(7) -0.0173(6) 0.0046(5) 0.0060(5) 

C2A_2 0.0317(7) 0.0384(8) 0.0399(8) -0.0143(7) 0.0050(6) 0.0007(6) 

C1A_2 0.0353(7) 0.0333(7) 0.0372(8) -0.0165(6) 0.0005(6) 0.0038(6) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O2_1 C1_1 1.211(2) . ? 

O1_1 C1_1 1.326(2) . ? 

O1_1 H1_1 0.97(3) . ? 

C1_1 C2_1 1.496(2) . ? 

C2_1 H2A_1 0.9800 . ? 

C2_1 H2B_1 0.9800 . ? 

C2_1 H2C_1 0.9800 . ? 

N1A_1 C2A_1 1.327(2) . ? 

N1A_1 C1A_1 1.327(2) . ? 

C1A_1 C2A_1 1.385(2) 2_655 ? 

C1A_1 H1AA_1 0.9500 . ? 

C2A_1 C1A_1 1.385(2) 2_655 ? 

C2A_1 H2AA_1 0.9500 . ? 

O2_2 C1_2 1.2101(18) . ? 

O1_2 C1_2 1.3235(19) . ? 

O1_2 H1_2 0.95(3) . ? 

C1_2 C2_2 1.4952(19) . ? 

C2_2 H2D_2 0.9800 . ? 

C2_2 H2E_2 0.9800 . ? 

C2_2 H2F_2 0.9800 . ? 

N1A_2 C2A_2 1.331(2) . ? 

N1A_2 C1A_2 1.331(2) . ? 

C2A_2 C1A_2 1.389(2) 2_654 ? 

C2A_2 H2AB_2 0.9500 . ? 

C1A_2 C2A_2 1.389(2) 2_654 ? 

C1A_2 H1AB_2 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1_1 O1_1 H1_1 108.3(15) . . ? 

O2_1 C1_1 O1_1 122.94(14) . . ? 

O2_1 C1_1 C2_1 124.15(15) . . ? 

O1_1 C1_1 C2_1 112.90(14) . . ? 

C1_1 C2_1 H2A_1 109.5 . . ? 

C1_1 C2_1 H2B_1 109.5 . . ? 

H2A_1 C2_1 H2B_1 109.5 . . ? 

C1_1 C2_1 H2C_1 109.5 . . ? 

H2A_1 C2_1 H2C_1 109.5 . . ? 

H2B_1 C2_1 H2C_1 109.5 . . ? 

C2A_1 N1A_1 C1A_1 116.79(13) . . ? 

N1A_1 C1A_1 C2A_1 121.54(15) . 2_655 ? 

N1A_1 C1A_1 H1AA_1 119.2 . . ? 

C2A_1 C1A_1 H1AA_1 119.2 2_655 . ? 

N1A_1 C2A_1 C1A_1 121.67(15) . 2_655 ? 

N1A_1 C2A_1 H2AA_1 119.2 . . ? 

C1A_1 C2A_1 H2AA_1 119.2 2_655 . ? 

C1_2 O1_2 H1_2 109.6(14) . . ? 

O2_2 C1_2 O1_2 122.66(14) . . ? 

O2_2 C1_2 C2_2 124.60(15) . . ? 

O1_2 C1_2 C2_2 112.75(13) . . ? 

C1_2 C2_2 H2D_2 109.5 . . ? 

C1_2 C2_2 H2E_2 109.5 . . ? 

H2D_2 C2_2 H2E_2 109.5 . . ? 

C1_2 C2_2 H2F_2 109.5 . . ? 

H2D_2 C2_2 H2F_2 109.5 . . ? 

H2E_2 C2_2 H2F_2 109.5 . . ? 

C2A_2 N1A_2 C1A_2 116.97(13) . . ? 

N1A_2 C2A_2 C1A_2 121.82(14) . 2_654 ? 

N1A_2 C2A_2 H2AB_2 119.1 . . ? 

C1A_2 C2A_2 H2AB_2 119.1 2_654 . ? 

N1A_2 C1A_2 C2A_2 121.21(14) . 2_654 ? 

N1A_2 C1A_2 H1AB_2 119.4 . . ? 

C2A_2 C1A_2 H1AB_2 119.4 2_654 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

C2A_1 N1A_1 C1A_1 C2A_1 -0.6(3) . . . 2_655 ? 

C1A_1 N1A_1 C2A_1 C1A_1 0.6(3) . . . 2_655 ? 

C1A_2 N1A_2 C2A_2 C1A_2 -0.2(3) . . . 2_654 ? 

C2A_2 N1A_2 C1A_2 C2A_2 0.2(2) . . . 2_654 ? 



#===END



data_ab0206 

_database_code_CSD                  192851



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / propanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C3 H6 O2)' 

_chemical_formula_sum             'C10 H16 N2 O4' 

_chemical_formula_weight          228.25 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            monoclinic

_symmetry_space_group_name_H-M    P21/n 



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x+1/2, y+1/2, -z+1/2' 

'-x, -y, -z' 

'x-1/2, -y-1/2, z-1/2' 



_cell_length_a                    4.8735(2) 

_cell_length_b                    5.4384(2) 

_cell_length_c                    23.2428(10) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  93.197(1) 

_cell_angle_gamma                 90.00 

_cell_volume                      615.07(4) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     6268

_cell_measurement_theta_min       1.02

_cell_measurement_theta_max       25.03



_exptl_crystal_description        cylinder

_exptl_crystal_colour             colourless 

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.232 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              244 

_exptl_absorpt_coefficient_mu     0.096 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm glass capillary at ca. 260 K.  

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             1845 

_diffrn_reflns_av_R_equivalents   0.1186 

_diffrn_reflns_av_sigmaI/netI     0.0950 

_diffrn_reflns_limit_h_min        -5 

_diffrn_reflns_limit_h_max        4 

_diffrn_reflns_limit_k_min        -5 

_diffrn_reflns_limit_k_max        6 

_diffrn_reflns_limit_l_min        -26 

_diffrn_reflns_limit_l_max        27 

_diffrn_reflns_theta_min          3.85 

_diffrn_reflns_theta_max          24.89 

_diffrn_measured_fraction_theta_max    0.830 

_diffrn_reflns_theta_full              24.89 

_diffrn_measured_fraction_theta_full   0.830 

_reflns_number_total              891 

_reflns_number_gt                 664 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.1127P)²+0.0802P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      SHELXL 

_refine_ls_extinction_coef        0.49(9) 

_refine_ls_extinction_expression 

'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 

_refine_ls_number_reflns          891 

_refine_ls_number_parameters      79 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1058 

_refine_ls_R_factor_gt            0.0749 

_refine_ls_wR_factor_ref          0.2189 

_refine_ls_wR_factor_gt           0.1880 

_refine_ls_goodness_of_fit_ref    1.245 

_refine_ls_restrained_S_all       1.245 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.409 

_refine_diff_density_min          -0.531 

_refine_diff_density_rms          0.150 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O -0.0472(6) 0.0299(5) 0.35779(10) 0.0555(10) Uani 1 1 d . . . 

H1 H 0.057(14) 0.006(12) 0.395(3) 0.120(19) Uiso 1 1 d . . . 

O2 O -0.1888(6) 0.3590(4) 0.40456(9) 0.0553(10) Uani 1 1 d . . . 

C1 C -0.2008(8) 0.2286(6) 0.36272(13) 0.0425(10) Uani 1 1 d . . . 

C2 C -0.3934(9) 0.2707(7) 0.31092(13) 0.0555(12) Uani 1 1 d . . . 

H2A H -0.2847 0.2777 0.2762 0.067 Uiso 1 1 calc R . . 

H2B H -0.5192 0.1281 0.3065 0.067 Uiso 1 1 calc R . . 

C3 C -0.5613(9) 0.4995(8) 0.31349(15) 0.0601(13) Uani 1 1 d . . . 

H3A H -0.6772 0.4910 0.3465 0.090 Uiso 1 1 calc R . . 

H3B H -0.6777 0.5156 0.2779 0.090 Uiso 1 1 calc R . . 

H3C H -0.4391 0.6423 0.3177 0.090 Uiso 1 1 calc R . . 

N1A N 0.3126(6) -0.0090(5) 0.45274(10) 0.0458(10) Uani 1 1 d . . . 

C2A C 0.5076(8) -0.1786(6) 0.46148(13) 0.0472(11) Uani 1 1 d . . . 

H2AA H 0.5200 -0.3090 0.4346 0.057 Uiso 1 1 calc R . . 

C1A C 0.3083(8) 0.1696(6) 0.49136(13) 0.0479(11) Uani 1 1 d . . . 

H1AA H 0.1740 0.2955 0.4864 0.058 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.062(2) 0.0474(16) 0.0559(15) -0.0087(10) -0.0049(12) 0.0122(12) 

O2 0.059(2) 0.0550(16) 0.0501(14) -0.0109(10) -0.0088(10) 0.0183(13) 

C1 0.042(3) 0.0406(18) 0.0452(17) -0.0003(13) 0.0043(13) -0.0046(16) 

C2 0.063(3) 0.053(2) 0.048(2) -0.0052(14) -0.0098(16) 0.0051(19) 

C3 0.061(3) 0.059(2) 0.058(2) 0.0043(15) -0.0144(18) 0.0068(19) 

N1A 0.045(3) 0.0424(17) 0.0499(16) 0.0002(11) 0.0016(12) 0.0048(13) 

C2A 0.051(3) 0.0384(18) 0.0525(19) -0.0036(13) 0.0047(14) 0.0081(16) 

C1A 0.050(3) 0.0401(19) 0.0542(19) -0.0012(13) 0.0029(15) 0.0084(16) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.323(4) . ? 

O1 H1 0.98(6) . ? 

O2 C1 1.203(4) . ? 

C1 C2 1.502(5) . ? 

C2 C3 1.492(5) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 H3A 0.9800 . ? 

C3 H3B 0.9800 . ? 

C3 H3C 0.9800 . ? 

N1A C1A 1.323(4) . ? 

N1A C2A 1.332(4) . ? 

C2A C1A 1.378(5) 3_656 ? 

C2A H2AA 0.9500 . ? 

C1A C2A 1.378(5) 3_656 ? 

C1A H1AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 107(4) . . ? 

O2 C1 O1 123.3(3) . . ? 

O2 C1 C2 123.9(3) . . ? 

O1 C1 C2 112.7(3) . . ? 

C3 C2 C1 114.5(3) . . ? 

C3 C2 H2A 108.6 . . ? 

C1 C2 H2A 108.6 . . ? 

C3 C2 H2B 108.6 . . ? 

C1 C2 H2B 108.6 . . ? 

H2A C2 H2B 107.6 . . ? 

C2 C3 H3A 109.5 . . ? 

C2 C3 H3B 109.5 . . ? 

H3A C3 H3B 109.5 . . ? 

C2 C3 H3C 109.5 . . ? 

H3A C3 H3C 109.5 . . ? 

H3B C3 H3C 109.5 . . ? 

C1A N1A C2A 116.3(3) . . ? 

N1A C2A C1A 121.6(3) . 3_656 ? 

N1A C2A H2AA 119.2 . . ? 

C1A C2A H2AA 119.2 3_656 . ? 

N1A C1A C2A 122.1(3) . 3_656 ? 

N1A C1A H1AA 118.9 . . ? 

C2A C1A H1AA 118.9 3_656 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 3.6(6) . . . . ? 

O1 C1 C2 C3 -177.3(3) . . . . ? 

C1A N1A C2A C1A 0.8(6) . . . 3_656 ? 

C2A N1A C1A C2A -0.9(6) . . . 3_656 ? 



#===END





data_ab0207 

_database_code_CSD                  192852



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / butanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C4 H8 O2)' 

_chemical_formula_sum             'C12 H20 N2 O4' 

_chemical_formula_weight          256.30 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            monoclinic

_symmetry_space_group_name_H-M    P21/n 



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x+1/2, y+1/2, -z+1/2' 

'-x, -y, -z' 

'x-1/2, -y-1/2, z-1/2' 



_cell_length_a                    9.8544(7) 

_cell_length_b                    5.7127(4) 

_cell_length_c                    13.5338(13) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  109.736(3) 

_cell_angle_gamma                 90.00 

_cell_volume                      717.13(10) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     7873 

_cell_measurement_theta_min       1.00 

_cell_measurement_theta_max       25.03



_exptl_crystal_description        cylinder

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.187 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              276 

_exptl_absorpt_coefficient_mu     0.089 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm glass capillary at ca. 265 K. 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             3855 

_diffrn_reflns_av_R_equivalents   0.0363 

_diffrn_reflns_av_sigmaI/netI     0.0411 

_diffrn_reflns_limit_h_min        -11 

_diffrn_reflns_limit_h_max        11 

_diffrn_reflns_limit_k_min        -6 

_diffrn_reflns_limit_k_max        6 

_diffrn_reflns_limit_l_min        -13 

_diffrn_reflns_limit_l_max        16 

_diffrn_reflns_theta_min          3.91 

_diffrn_reflns_theta_max          25.03 

_diffrn_measured_fraction_theta_max    0.982 

_diffrn_reflns_theta_full              25.03 

_diffrn_measured_fraction_theta_full   0.982 

_reflns_number_total              1245 

_reflns_number_gt                 1023 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0465P)²+0.2173P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          1245 

_refine_ls_number_parameters      87 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0571 

_refine_ls_R_factor_gt            0.0448 

_refine_ls_wR_factor_ref          0.1154 

_refine_ls_wR_factor_gt           0.1058 

_refine_ls_goodness_of_fit_ref    1.044 

_refine_ls_restrained_S_all       1.044 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.165 

_refine_diff_density_min          -0.169 

_refine_diff_density_rms          0.033 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O -0.25942(18) 0.0583(3) 0.00876(9) 0.0704(5) Uani 1 1 d . . . 

H1 H -0.200(3) -0.063(5) 0.007(2) 0.097(8) Uiso 1 1 d . . . 

O2 O -0.31294(15) 0.0311(2) -0.16337(9) 0.0594(4) Uani 1 1 d . . . 

C1 C -0.33206(18) 0.1209(3) -0.08890(12) 0.0439(4) Uani 1 1 d . . . 

C2 C -0.43771(19) 0.3128(3) -0.09522(12) 0.0493(5) Uani 1 1 d . . . 

H2A H -0.3865 0.4439 -0.0502 0.059 Uiso 1 1 calc R . . 

H2B H -0.5113 0.2544 -0.0664 0.059 Uiso 1 1 calc R . . 

C3 C -0.51327(19) 0.4051(3) -0.20463(13) 0.0495(5) Uani 1 1 d . . . 

H3A H -0.5644 0.2747 -0.2503 0.059 Uiso 1 1 calc R . . 

H3B H -0.4405 0.4669 -0.2334 0.059 Uiso 1 1 calc R . . 

C4 C -0.6208(2) 0.5973(3) -0.20682(14) 0.0581(5) Uani 1 1 d . . . 

H4A H -0.6723 0.6432 -0.2797 0.087 Uiso 1 1 calc R . . 

H4B H -0.5695 0.7331 -0.1673 0.087 Uiso 1 1 calc R . . 

H4C H -0.6900 0.5397 -0.1749 0.087 Uiso 1 1 calc R . . 

N1A N -0.08164(15) -0.3083(2) 0.00979(10) 0.0466(4) Uani 1 1 d . . . 

C2A C 0.0126(2) -0.4124(3) 0.09338(12) 0.0485(5) Uani 1 1 d . . . 

H2AA H 0.0243 -0.3536 0.1614 0.058 Uiso 1 1 calc R . . 

C1A C -0.09307(19) -0.3984(3) -0.08378(12) 0.0455(4) Uani 1 1 d . . . 

H1AA H -0.1587 -0.3297 -0.1453 0.055 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0896(11) 0.0855(10) 0.0310(7) 0.0054(6) 0.0137(6) 0.0416(9) 

O2 0.0710(9) 0.0671(8) 0.0333(7) -0.0030(6) 0.0087(6) 0.0215(7) 

C1 0.0483(10) 0.0491(10) 0.0311(8) -0.0002(7) 0.0094(7) 0.0025(7) 

C2 0.0533(10) 0.0537(10) 0.0401(9) -0.0004(7) 0.0148(8) 0.0068(8) 

C3 0.0500(10) 0.0531(10) 0.0429(9) 0.0036(7) 0.0124(8) 0.0064(8) 

C4 0.0591(12) 0.0579(12) 0.0531(11) 0.0056(8) 0.0135(9) 0.0117(9) 

N1A 0.0534(9) 0.0515(9) 0.0317(7) 0.0016(6) 0.0099(6) 0.0074(6) 

C2A 0.0595(11) 0.0540(10) 0.0274(8) -0.0010(7) 0.0086(7) 0.0054(8) 

C1A 0.0496(10) 0.0523(10) 0.0293(8) 0.0041(7) 0.0063(7) 0.0052(7) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.3222(19) . ? 

O1 H1 0.91(3) . ? 

O2 C1 1.2013(19) . ? 

C1 C2 1.494(2) . ? 

C2 C3 1.510(2) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.520(3) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 H4A 0.9800 . ? 

C4 H4B 0.9800 . ? 

C4 H4C 0.9800 . ? 

N1A C1A 1.336(2) . ? 

N1A C2A 1.337(2) . ? 

C2A C1A 1.372(2) 3_545 ? 

C2A H2AA 0.9500 . ? 

C1A C2A 1.372(2) 3_545 ? 

C1A H1AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 108.4(16) . . ? 

O2 C1 O1 122.53(16) . . ? 

O2 C1 C2 124.68(14) . . ? 

O1 C1 C2 112.79(14) . . ? 

C1 C2 C3 114.56(13) . . ? 

C1 C2 H2A 108.6 . . ? 

C3 C2 H2A 108.6 . . ? 

C1 C2 H2B 108.6 . . ? 

C3 C2 H2B 108.6 . . ? 

H2A C2 H2B 107.6 . . ? 

C2 C3 C4 112.41(14) . . ? 

C2 C3 H3A 109.1 . . ? 

C4 C3 H3A 109.1 . . ? 

C2 C3 H3B 109.1 . . ? 

C4 C3 H3B 109.1 . . ? 

H3A C3 H3B 107.9 . . ? 

C3 C4 H4A 109.5 . . ? 

C3 C4 H4B 109.5 . . ? 

H4A C4 H4B 109.5 . . ? 

C3 C4 H4C 109.5 . . ? 

H4A C4 H4C 109.5 . . ? 

H4B C4 H4C 109.5 . . ? 

C1A N1A C2A 116.28(14) . . ? 

N1A C2A C1A 121.93(14) . 3_545 ? 

N1A C2A H2AA 119.0 . . ? 

C1A C2A H2AA 119.0 3_545 . ? 

N1A C1A C2A 121.79(14) . 3_545 ? 

N1A C1A H1AA 119.1 . . ? 

C2A C1A H1AA 119.1 3_545 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 -5.1(3) . . . . ? 

O1 C1 C2 C3 174.66(16) . . . . ? 

C1 C2 C3 C4 179.24(16) . . . . ? 

C1A N1A C2A C1A -0.1(3) . . . 3_545 ? 

C2A N1A C1A C2A 0.1(3) . . . 3_545 ? 



#===END



data_ab0208 

_database_code_CSD                  192853



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / pentanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C5 H10 O2)' 

_chemical_formula_sum             'C14 H24 N2 O4' 

_chemical_formula_weight          284.35 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            monoclinic

_symmetry_space_group_name_H-M    P21/c



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, y+1/2, -z+1/2' 

'-x, -y, -z' 

'x, -y-1/2, z-1/2' 



_cell_length_a                    13.24490(11) 

_cell_length_b                    5.4022(3) 

_cell_length_c                    11.9960(8) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  105.716(3) 

_cell_angle_gamma                 90.00 

_cell_volume                      826.24(7) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     7756 

_cell_measurement_theta_min       1.02

_cell_measurement_theta_max       25.03



_exptl_crystal_description        cylinder

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.143 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              308 

_exptl_absorpt_coefficient_mu     0.084 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm capillary at ca. 268 K. 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0 

_diffrn_reflns_number             4881 

_diffrn_reflns_av_R_equivalents   0.1216 

_diffrn_reflns_av_sigmaI/netI     0.0747 

_diffrn_reflns_limit_h_min        -15 

_diffrn_reflns_limit_h_max        15 

_diffrn_reflns_limit_k_min        -6 

_diffrn_reflns_limit_k_max        6 

_diffrn_reflns_limit_l_min        -13 

_diffrn_reflns_limit_l_max        14 

_diffrn_reflns_theta_min          4.16 

_diffrn_reflns_theta_max          24.71 

_diffrn_measured_fraction_theta_max    0.979 

_diffrn_reflns_theta_full              24.71 

_diffrn_measured_fraction_theta_full   0.979 

_reflns_number_total              1374 

_reflns_number_gt                 1072 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0742P)²+0.6852P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          1374 

_refine_ls_number_parameters      96 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0943 

_refine_ls_R_factor_gt            0.0726 

_refine_ls_wR_factor_ref          0.1962 

_refine_ls_wR_factor_gt           0.1790 

_refine_ls_goodness_of_fit_ref    1.093 

_refine_ls_restrained_S_all       1.093 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.213 

_refine_diff_density_min          -0.228 

_refine_diff_density_rms          0.058 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O2 O 0.35882(17) 0.1553(4) 0.63730(19) 0.0508(7) Uani 1 1 d . . . 

O1 O 0.27470(18) 0.0369(4) 0.45876(18) 0.0520(7) Uani 1 1 d . . . 

H1 H 0.339(3) -0.093(8) 0.477(3) 0.072(11) Uiso 1 1 d . . . 

C1 C 0.2857(2) 0.1765(5) 0.5524(2) 0.0383(7) Uani 1 1 d . . . 

C2 C 0.1978(2) 0.3573(6) 0.5395(3) 0.0434(8) Uani 1 1 d . . . 

H2A H 0.1315 0.2633 0.5262 0.052 Uiso 1 1 calc R . . 

H2B H 0.1934 0.4585 0.4696 0.052 Uiso 1 1 calc R . . 

C3 C 0.2061(2) 0.5307(6) 0.6410(2) 0.0418(7) Uani 1 1 d . . . 

H3A H 0.2175 0.4325 0.7131 0.050 Uiso 1 1 calc R . . 

H3B H 0.2674 0.6409 0.6493 0.050 Uiso 1 1 calc R . . 

C4 C 0.1081(2) 0.6863(6) 0.6251(3) 0.0474(8) Uani 1 1 d . . . 

H4A H 0.0469 0.5751 0.6152 0.057 Uiso 1 1 calc R . . 

H4B H 0.0975 0.7854 0.5534 0.057 Uiso 1 1 calc R . . 

C5 C 0.1127(3) 0.8597(7) 0.7261(3) 0.0583(9) Uani 1 1 d . . . 

H5A H 0.1190 0.7624 0.7966 0.087 Uiso 1 1 calc R . . 

H5B H 0.0486 0.9594 0.7098 0.087 Uiso 1 1 calc R . . 

H5C H 0.1737 0.9691 0.7372 0.087 Uiso 1 1 calc R . . 

N1A N 0.42684(19) -0.3099(5) 0.4842(2) 0.0440(7) Uani 1 1 d . . . 

C2A C 0.4286(2) -0.4696(6) 0.3993(3) 0.0467(8) Uani 1 1 d . . . 

H2AA H 0.3784 -0.4526 0.3263 0.056 Uiso 1 1 calc R . . 

C1A C 0.4986(2) -0.3421(6) 0.5848(3) 0.0448(8) Uani 1 1 d . . . 

H1AA H 0.4997 -0.2329 0.6472 0.054 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O2 0.0519(13) 0.0520(13) 0.0440(12) -0.0013(10) 0.0053(10) 0.0109(10) 

O1 0.0566(14) 0.0528(14) 0.0437(12) -0.0104(10) 0.0087(9) 0.0155(11) 

C1 0.0435(16) 0.0363(15) 0.0359(15) 0.0034(12) 0.0121(12) -0.0011(12) 

C2 0.0498(17) 0.0412(17) 0.0382(16) -0.0010(12) 0.0101(12) 0.0084(13) 

C3 0.0478(16) 0.0386(16) 0.0396(15) -0.0008(12) 0.0130(12) 0.0025(13) 

C4 0.0489(18) 0.0444(18) 0.0498(18) -0.0046(14) 0.0146(14) 0.0039(14) 

C5 0.068(2) 0.051(2) 0.061(2) -0.0108(15) 0.0244(17) 0.0049(16) 

N1A 0.0448(14) 0.0414(14) 0.0480(15) -0.0033(11) 0.0163(11) 0.0055(11) 

C2A 0.0439(17) 0.0508(18) 0.0441(17) -0.0055(14) 0.0099(13) 0.0018(14) 

C1A 0.0496(17) 0.0416(17) 0.0448(17) -0.0103(13) 0.0157(13) -0.0017(14) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O2 C1 1.206(3) . ? 

O1 C1 1.328(4) . ? 

O1 H1 1.08(4) . ? 

C1 C2 1.495(4) . ? 

C2 C3 1.517(4) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.515(4) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.520(4) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 H5A 0.9800 . ? 

C5 H5B 0.9800 . ? 

C5 H5C 0.9800 . ? 

N1A C1A 1.330(4) . ? 

N1A C2A 1.339(4) . ? 

C2A C1A 1.379(4) 3_646 ? 

C2A H2AA 0.9500 . ? 

C1A C2A 1.379(4) 3_646 ? 

C1A H1AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 107(2) . . ? 

O2 C1 O1 122.7(3) . . ? 

O2 C1 C2 125.0(3) . . ? 

O1 C1 C2 112.3(2) . . ? 

C1 C2 C3 115.8(2) . . ? 

C1 C2 H2A 108.3 . . ? 

C3 C2 H2A 108.3 . . ? 

C1 C2 H2B 108.3 . . ? 

C3 C2 H2B 108.3 . . ? 

H2A C2 H2B 107.4 . . ? 

C4 C3 C2 111.6(2) . . ? 

C4 C3 H3A 109.3 . . ? 

C2 C3 H3A 109.3 . . ? 

C4 C3 H3B 109.3 . . ? 

C2 C3 H3B 109.3 . . ? 

H3A C3 H3B 108.0 . . ? 

C3 C4 C5 113.1(3) . . ? 

C3 C4 H4A 109.0 . . ? 

C5 C4 H4A 109.0 . . ? 

C3 C4 H4B 109.0 . . ? 

C5 C4 H4B 109.0 . . ? 

H4A C4 H4B 107.8 . . ? 

C4 C5 H5A 109.5 . . ? 

C4 C5 H5B 109.5 . . ? 

H5A C5 H5B 109.5 . . ? 

C4 C5 H5C 109.5 . . ? 

H5A C5 H5C 109.5 . . ? 

H5B C5 H5C 109.5 . . ? 

C1A N1A C2A 116.8(3) . . ? 

N1A C2A C1A 121.7(3) . 3_646 ? 

N1A C2A H2AA 119.1 . . ? 

C1A C2A H2AA 119.1 3_646 . ? 

N1A C1A C2A 121.5(3) . 3_646 ? 

N1A C1A H1AA 119.3 . . ? 

C2A C1A H1AA 119.3 3_646 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 2.4(5) . . . . ? 

O1 C1 C2 C3 -177.9(3) . . . . ? 

C1 C2 C3 C4 -173.7(3) . . . . ? 

C2 C3 C4 C5 179.1(3) . . . . ? 

C1A N1A C2A C1A -0.2(5) . . . 3_646 ? 

C2A N1A C1A C2A 0.2(5) . . . 3_646 ? 



#===END



data_ab0204b 

_database_code_CSD                  192854



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / hexanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C6 H12 O2)' 

_chemical_formula_sum             'C16 H28 N2 O4' 

_chemical_formula_weight          312.40 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            monoclinic

_symmetry_space_group_name_H-M    C2/c



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, y, -z+1/2' 

'x+1/2, y+1/2, z' 

'-x+1/2, y+1/2, -z+1/2' 

'-x, -y, -z' 

'x, -y, z-1/2' 

'-x+1/2, -y+1/2, -z' 

'x+1/2, -y+1/2, z-1/2' 



_cell_length_a                    27.6365(7) 

_cell_length_b                    5.4294(1) 

_cell_length_c                    12.2322(4) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  94.639(1) 

_cell_angle_gamma                 90.00 

_cell_volume                      1829.42(8) 

_cell_formula_units_Z             4 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     4824

_cell_measurement_theta_min       1.00

_cell_measurement_theta_max       27.48



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.20 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.134 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              680 

_exptl_absorpt_coefficient_mu     0.081 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm capillary at ca. 280 K. 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             8015 

_diffrn_reflns_av_R_equivalents   0.0443 

_diffrn_reflns_av_sigmaI/netI     0.0324 

_diffrn_reflns_limit_h_min        -34 

_diffrn_reflns_limit_h_max        35 

_diffrn_reflns_limit_k_min        -7 

_diffrn_reflns_limit_k_max        6 

_diffrn_reflns_limit_l_min        -15 

_diffrn_reflns_limit_l_max        15 

_diffrn_reflns_theta_min          3.76 

_diffrn_reflns_theta_max          27.51

_diffrn_measured_fraction_theta_max    0.994 

_diffrn_reflns_theta_full              27.51 

_diffrn_measured_fraction_theta_full   0.994 

_reflns_number_total              2092 

_reflns_number_gt                 1690 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0618P)²+0.7753P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2092 

_refine_ls_number_parameters      105 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0607 

_refine_ls_R_factor_gt            0.0475 

_refine_ls_wR_factor_ref          0.1318 

_refine_ls_wR_factor_gt           0.1205 

_refine_ls_goodness_of_fit_ref    1.063 

_refine_ls_restrained_S_all       1.063 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.208 

_refine_diff_density_min          -0.188 

_refine_diff_density_rms          0.035 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O 0.35251(4) 0.2035(2) 0.54544(8) 0.0513(3) Uani 1 1 d . . . 

H1 H 0.3278(8) 0.317(5) 0.5361(18) 0.087(7) Uiso 1 1 d . . . 

O2 O 0.31481(4) 0.1105(2) 0.69393(8) 0.0497(3) Uani 1 1 d . . . 

C1 C 0.34742(5) 0.0762(2) 0.63625(10) 0.0349(3) Uani 1 1 d . . . 

C2 C 0.38699(5) -0.1124(2) 0.65743(11) 0.0390(3) Uani 1 1 d . . . 

H2A H 0.4187 -0.0262 0.6642 0.047 Uiso 1 1 calc R . . 

H2B H 0.3868 -0.2229 0.5930 0.047 Uiso 1 1 calc R . . 

C3 C 0.38305(5) -0.2681(2) 0.75876(11) 0.0380(3) Uani 1 1 d . . . 

H3A H 0.3530 -0.3682 0.7496 0.046 Uiso 1 1 calc R . . 

H3B H 0.3806 -0.1590 0.8229 0.046 Uiso 1 1 calc R . . 

C4 C 0.42648(5) -0.4381(2) 0.78051(11) 0.0403(3) Uani 1 1 d . . . 

H4A H 0.4288 -0.5465 0.7160 0.048 Uiso 1 1 calc R . . 

H4B H 0.4564 -0.3371 0.7887 0.048 Uiso 1 1 calc R . . 

C5 C 0.42420(5) -0.5972(3) 0.88183(12) 0.0476(4) Uani 1 1 d . . . 

H5A H 0.3948 -0.7014 0.8728 0.057 Uiso 1 1 calc R . . 

H5B H 0.4211 -0.4890 0.9460 0.057 Uiso 1 1 calc R . . 

C6 C 0.46827(6) -0.7622(3) 0.90479(15) 0.0577(4) Uani 1 1 d . . . 

H6A H 0.4719 -0.8688 0.8413 0.087 Uiso 1 1 calc R . . 

H6B H 0.4639 -0.8640 0.9694 0.087 Uiso 1 1 calc R . . 

H6C H 0.4974 -0.6602 0.9185 0.087 Uiso 1 1 calc R . . 

N1A N 0.28340(4) 0.5589(2) 0.51130(10) 0.0422(3) Uani 1 1 d . . . 

C1A C 0.25149(5) 0.5979(3) 0.58522(12) 0.0430(3) Uani 1 1 d . . . 

H1AA H 0.2516 0.4925 0.6472 0.052 Uiso 1 1 calc R . . 

C2A C 0.28165(5) 0.7124(3) 0.42590(12) 0.0441(3) Uani 1 1 d . . . 

H2AA H 0.3038 0.6903 0.3713 0.053 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0547(6) 0.0549(6) 0.0462(6) 0.0191(5) 0.0149(5) 0.0170(5) 

O2 0.0503(6) 0.0546(6) 0.0464(6) 0.0101(4) 0.0166(5) 0.0160(5) 

C1 0.0393(7) 0.0334(6) 0.0322(6) 0.0004(5) 0.0036(5) 0.0005(5) 

C2 0.0418(7) 0.0376(7) 0.0384(7) 0.0028(5) 0.0086(5) 0.0070(5) 

C3 0.0385(7) 0.0369(7) 0.0392(7) 0.0042(5) 0.0067(5) 0.0058(5) 

C4 0.0398(7) 0.0375(7) 0.0440(7) 0.0036(5) 0.0067(5) 0.0056(5) 

C5 0.0451(8) 0.0480(8) 0.0502(8) 0.0113(6) 0.0077(6) 0.0105(6) 

C6 0.0522(9) 0.0600(10) 0.0607(10) 0.0155(7) 0.0044(7) 0.0173(7) 

N1A 0.0390(6) 0.0434(6) 0.0439(7) 0.0075(5) 0.0012(5) 0.0050(5) 

C1A 0.0418(7) 0.0455(8) 0.0415(7) 0.0120(6) 0.0027(6) 0.0010(6) 

C2A 0.0391(7) 0.0519(8) 0.0418(7) 0.0079(6) 0.0069(5) 0.0044(6) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.3255(15) . ? 

O1 H1 0.92(2) . ? 

O2 C1 1.2032(15) . ? 

C1 C2 1.5053(17) . ? 

C2 C3 1.5115(18) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.5203(18) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.5161(19) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 C6 1.520(2) . ? 

C5 H5A 0.9900 . ? 

C5 H5B 0.9900 . ? 

C6 H6A 0.9800 . ? 

C6 H6B 0.9800 . ? 

C6 H6C 0.9800 . ? 

N1A C1A 1.3301(18) . ? 

N1A C2A 1.3341(18) . ? 

C1A C2A 1.378(2) 7_566 ? 

C1A H1AA 0.9500 . ? 

C2A C1A 1.378(2) 7_566 ? 

C2A H2AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 108.9(14) . . ? 

O2 C1 O1 123.10(12) . . ? 

O2 C1 C2 124.94(11) . . ? 

O1 C1 C2 111.97(11) . . ? 

C1 C2 C3 114.96(10) . . ? 

C1 C2 H2A 108.5 . . ? 

C3 C2 H2A 108.5 . . ? 

C1 C2 H2B 108.5 . . ? 

C3 C2 H2B 108.5 . . ? 

H2A C2 H2B 107.5 . . ? 

C2 C3 C4 112.01(11) . . ? 

C2 C3 H3A 109.2 . . ? 

C4 C3 H3A 109.2 . . ? 

C2 C3 H3B 109.2 . . ? 

C4 C3 H3B 109.2 . . ? 

H3A C3 H3B 107.9 . . ? 

C5 C4 C3 113.86(11) . . ? 

C5 C4 H4A 108.8 . . ? 

C3 C4 H4A 108.8 . . ? 

C5 C4 H4B 108.8 . . ? 

C3 C4 H4B 108.8 . . ? 

H4A C4 H4B 107.7 . . ? 

C4 C5 C6 113.66(13) . . ? 

C4 C5 H5A 108.8 . . ? 

C6 C5 H5A 108.8 . . ? 

C4 C5 H5B 108.8 . . ? 

C6 C5 H5B 108.8 . . ? 

H5A C5 H5B 107.7 . . ? 

C5 C6 H6A 109.5 . . ? 

C5 C6 H6B 109.5 . . ? 

H6A C6 H6B 109.5 . . ? 

C5 C6 H6C 109.5 . . ? 

H6A C6 H6C 109.5 . . ? 

H6B C6 H6C 109.5 . . ? 

C1A N1A C2A 116.66(12) . . ? 

N1A C1A C2A 121.60(12) . 7_566 ? 

N1A C1A H1AA 119.2 . . ? 

C2A C1A H1AA 119.2 7_566 . ? 

N1A C2A C1A 121.73(13) . 7_566 ? 

N1A C2A H2AA 119.1 . . ? 

C1A C2A H2AA 119.1 7_566 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 1.2(2) . . . . ? 

O1 C1 C2 C3 -178.95(12) . . . . ? 

C1 C2 C3 C4 -174.91(11) . . . . ? 

C2 C3 C4 C5 179.72(12) . . . . ? 

C3 C4 C5 C6 -178.58(13) . . . . ? 

C2A N1A C1A C2A -0.1(2) . . . 7_566 ? 

C1A N1A C2A C1A 0.1(2) . . . 7_566 ? 



#===END



data_ab0205 

_database_code_CSD                  192855



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / heptanoic acid'

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C7 H14 O2)' 

_chemical_formula_sum             'C18 H32 N2 O4' 

_chemical_formula_weight          340.46 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            triclinic 

_symmetry_space_group_name_H-M    P-1



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    5.5106(3) 

_cell_length_b                    6.8970(3) 

_cell_length_c                    13.7860(8) 

_cell_angle_alpha                 76.816(2) 

_cell_angle_beta                  85.697(2) 

_cell_angle_gamma                 76.802(2) 

_cell_volume                      496.53(5) 

_cell_formula_units_Z             1 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     7215 

_cell_measurement_theta_min       1.00

_cell_measurement_theta_max       27.48



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.139 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              186 

_exptl_absorpt_coefficient_mu     0.080 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm glass capillary at ca. 289 K

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             5160 

_diffrn_reflns_av_R_equivalents   0.0383 

_diffrn_reflns_av_sigmaI/netI     0.0381 

_diffrn_reflns_limit_h_min        -7 

_diffrn_reflns_limit_h_max        7 

_diffrn_reflns_limit_k_min        -8 

_diffrn_reflns_limit_k_max        8 

_diffrn_reflns_limit_l_min        -16 

_diffrn_reflns_limit_l_max        17 

_diffrn_reflns_theta_min          3.74 

_diffrn_reflns_theta_max          27.48 

_diffrn_measured_fraction_theta_max    0.974 

_diffrn_reflns_theta_full              27.48 

_diffrn_measured_fraction_theta_full   0.974 

_reflns_number_total              2210 

_reflns_number_gt                 1874 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0451P)²+0.1191P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2210 

_refine_ls_number_parameters      114 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0526 

_refine_ls_R_factor_gt            0.0436 

_refine_ls_wR_factor_ref          0.1192 

_refine_ls_wR_factor_gt           0.1116 

_refine_ls_goodness_of_fit_ref    1.073 

_refine_ls_restrained_S_all       1.073 

_refine_ls_shift/su_max           0.007 

_refine_ls_shift/su_mean          0.003 

_refine_diff_density_max          0.250 

_refine_diff_density_min          -0.187 

_refine_diff_density_rms          0.033 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O 0.39154(18) 0.25371(15) 0.15556(8) 0.0446(3) Uani 1 1 d . . . 

H1 H 0.526(4) 0.202(3) 0.1165(15) 0.076(6) Uiso 1 1 d . . . 

O2 O 0.58217(18) 0.51172(14) 0.13948(8) 0.0457(3) Uani 1 1 d . . . 

C1 C 0.4098(2) 0.43268(17) 0.17126(9) 0.0308(3) Uani 1 1 d . . . 

C2 C 0.1937(2) 0.51946(17) 0.23318(9) 0.0327(3) Uani 1 1 d . . . 

H2A H 0.1920 0.4227 0.2983 0.039 Uiso 1 1 calc R . . 

H2B H 0.0374 0.5290 0.1996 0.039 Uiso 1 1 calc R . . 

C3 C 0.1943(2) 0.72802(17) 0.25198(9) 0.0320(3) Uani 1 1 d . . . 

H3A H 0.2019 0.8256 0.1875 0.038 Uiso 1 1 calc R . . 

H3B H 0.3441 0.7189 0.2896 0.038 Uiso 1 1 calc R . . 

C4 C -0.0386(2) 0.80597(18) 0.31074(9) 0.0339(3) Uani 1 1 d . . . 

H4A H -0.1871 0.8121 0.2730 0.041 Uiso 1 1 calc R . . 

H4B H -0.0448 0.7067 0.3748 0.041 Uiso 1 1 calc R . . 

C5 C -0.0534(2) 1.01495(18) 0.33238(9) 0.0336(3) Uani 1 1 d . . . 

H5A H -0.0619 1.1172 0.2686 0.040 Uiso 1 1 calc R . . 

H5B H 0.1002 1.0127 0.3659 0.040 Uiso 1 1 calc R . . 

C6 C -0.2789(2) 1.07887(19) 0.39795(10) 0.0385(3) Uani 1 1 d . . . 

H6A H -0.2711 0.9749 0.4611 0.046 Uiso 1 1 calc R . . 

H6B H -0.4321 1.0820 0.3639 0.046 Uiso 1 1 calc R . . 

C7 C -0.2973(3) 1.2866(2) 0.42212(11) 0.0471(4) Uani 1 1 d . . . 

H7A H -0.1489 1.2838 0.4579 0.071 Uiso 1 1 calc R . . 

H7B H -0.4464 1.3185 0.4639 0.071 Uiso 1 1 calc R . . 

H7C H -0.3084 1.3911 0.3601 0.071 Uiso 1 1 calc R . . 

N1A N 0.78932(18) 0.08052(15) 0.05172(7) 0.0326(3) Uani 1 1 d . . . 

C1A C 0.9659(2) 0.18487(18) 0.01901(9) 0.0332(3) Uani 1 1 d . . . 

H1AA H 0.9470 0.3174 0.0315 0.040 Uiso 1 1 calc R . . 

C2A C 0.8238(2) -0.10533(18) 0.03273(9) 0.0336(3) Uani 1 1 d . . . 

H2AA H 0.7019 -0.1844 0.0551 0.040 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0379(5) 0.0437(5) 0.0636(6) -0.0319(5) 0.0184(4) -0.0179(4) 

O2 0.0387(5) 0.0396(5) 0.0637(6) -0.0192(4) 0.0179(4) -0.0165(4) 

C1 0.0288(6) 0.0310(6) 0.0340(6) -0.0096(4) 0.0013(4) -0.0074(4) 

C2 0.0288(6) 0.0314(6) 0.0400(6) -0.0124(5) 0.0053(5) -0.0083(5) 

C3 0.0288(6) 0.0306(6) 0.0387(6) -0.0117(5) 0.0024(5) -0.0076(4) 

C4 0.0323(6) 0.0324(6) 0.0394(6) -0.0128(5) 0.0060(5) -0.0093(5) 

C5 0.0334(6) 0.0316(6) 0.0378(6) -0.0114(5) 0.0041(5) -0.0090(5) 

C6 0.0380(7) 0.0355(6) 0.0427(7) -0.0138(5) 0.0087(5) -0.0071(5) 

C7 0.0521(8) 0.0387(7) 0.0513(8) -0.0198(6) 0.0069(6) -0.0044(6) 

N1A 0.0300(5) 0.0337(5) 0.0353(5) -0.0114(4) 0.0022(4) -0.0067(4) 

C1A 0.0350(6) 0.0285(5) 0.0386(6) -0.0115(5) 0.0004(5) -0.0087(5) 

C2A 0.0309(6) 0.0331(6) 0.0391(6) -0.0089(5) 0.0027(5) -0.0121(5) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.3276(14) . ? 

O1 H1 0.94(2) . ? 

O2 C1 1.2068(14) . ? 

C1 C2 1.5035(16) . ? 

C2 C3 1.5194(15) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.5231(16) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.5205(15) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 C6 1.5230(16) . ? 

C5 H5A 0.9900 . ? 

C5 H5B 0.9900 . ? 

C6 C7 1.5231(17) . ? 

C6 H6A 0.9900 . ? 

C6 H6B 0.9900 . ? 

C7 H7A 0.9800 . ? 

C7 H7B 0.9800 . ? 

C7 H7C 0.9800 . ? 

N1A C1A 1.3319(16) . ? 

N1A C2A 1.3350(15) . ? 

C1A C2A 1.3846(17) 2_755 ? 

C1A H1AA 0.9500 . ? 

C2A C1A 1.3846(17) 2_755 ? 

C2A H2AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 110.8(12) . . ? 

O2 C1 O1 122.87(11) . . ? 

O2 C1 C2 125.40(11) . . ? 

O1 C1 C2 111.72(10) . . ? 

C1 C2 C3 115.41(10) . . ? 

C1 C2 H2A 108.4 . . ? 

C3 C2 H2A 108.4 . . ? 

C1 C2 H2B 108.4 . . ? 

C3 C2 H2B 108.4 . . ? 

H2A C2 H2B 107.5 . . ? 

C2 C3 C4 111.04(9) . . ? 

C2 C3 H3A 109.4 . . ? 

C4 C3 H3A 109.4 . . ? 

C2 C3 H3B 109.4 . . ? 

C4 C3 H3B 109.4 . . ? 

H3A C3 H3B 108.0 . . ? 

C5 C4 C3 114.43(10) . . ? 

C5 C4 H4A 108.7 . . ? 

C3 C4 H4A 108.7 . . ? 

C5 C4 H4B 108.7 . . ? 

C3 C4 H4B 108.7 . . ? 

H4A C4 H4B 107.6 . . ? 

C4 C5 C6 112.40(10) . . ? 

C4 C5 H5A 109.1 . . ? 

C6 C5 H5A 109.1 . . ? 

C4 C5 H5B 109.1 . . ? 

C6 C5 H5B 109.1 . . ? 

H5A C5 H5B 107.9 . . ? 

C5 C6 C7 113.71(11) . . ? 

C5 C6 H6A 108.8 . . ? 

C7 C6 H6A 108.8 . . ? 

C5 C6 H6B 108.8 . . ? 

C7 C6 H6B 108.8 . . ? 

H6A C6 H6B 107.7 . . ? 

C6 C7 H7A 109.5 . . ? 

C6 C7 H7B 109.5 . . ? 

H7A C7 H7B 109.5 . . ? 

C6 C7 H7C 109.5 . . ? 

H7A C7 H7C 109.5 . . ? 

H7B C7 H7C 109.5 . . ? 

C1A N1A C2A 117.10(10) . . ? 

N1A C1A C2A 121.78(11) . 2_755 ? 

N1A C1A H1AA 119.1 . . ? 

C2A C1A H1AA 119.1 2_755 . ? 

N1A C2A C1A 121.12(11) . 2_755 ? 

N1A C2A H2AA 119.4 . . ? 

C1A C2A H2AA 119.4 2_755 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 2.61(18) . . . . ? 

O1 C1 C2 C3 -177.97(10) . . . . ? 

C1 C2 C3 C4 177.14(10) . . . . ? 

C2 C3 C4 C5 -179.72(10) . . . . ? 

C3 C4 C5 C6 -175.59(11) . . . . ? 

C4 C5 C6 C7 179.26(11) . . . . ? 

C2A N1A C1A C2A 0.2(2) . . . 2_755 ? 

C1A N1A C2A C1A -0.18(19) . . . 2_755 ? 



#===END





data_ab0211 

_database_code_CSD                  192856



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / octanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C8 H16 O2)' 

_chemical_formula_sum             'C20 H36 N2 O4' 

_chemical_formula_weight          368.51 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            triclinic

_symmetry_space_group_name_H-M    P-1



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    5.4774(2) 

_cell_length_b                    6.9086(3) 

_cell_length_c                    15.2102(8) 

_cell_angle_alpha                 81.541(2) 

_cell_angle_beta                  84.977(2) 

_cell_angle_gamma                 76.158(4) 

_cell_volume                      551.95(4) 

_cell_formula_units_Z             1 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     3081

_cell_measurement_theta_min       1.02

_cell_measurement_theta_max       27.48



_exptl_crystal_description        cylinder

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.109 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              202 

_exptl_absorpt_coefficient_mu     0.076 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm capillary at ca. 291 K 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             4435 

_diffrn_reflns_av_R_equivalents   0.0786 

_diffrn_reflns_av_sigmaI/netI     0.0759 

_diffrn_reflns_limit_h_min        -7 

_diffrn_reflns_limit_h_max        7 

_diffrn_reflns_limit_k_min        -8 

_diffrn_reflns_limit_k_max        8 

_diffrn_reflns_limit_l_min        -17 

_diffrn_reflns_limit_l_max        19 

_diffrn_reflns_theta_min          3.82 

_diffrn_reflns_theta_max          27.60 

_diffrn_measured_fraction_theta_max    0.959 

_diffrn_reflns_theta_full              27.60 

_diffrn_measured_fraction_theta_full   0.959 

_reflns_number_total              2441 

_reflns_number_gt                 1939 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.1151P)²+0.4608P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2441 

_refine_ls_number_parameters      123 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1083 

_refine_ls_R_factor_gt            0.0882 

_refine_ls_wR_factor_ref          0.2571 

_refine_ls_wR_factor_gt           0.2405 

_refine_ls_goodness_of_fit_ref    1.101 

_refine_ls_restrained_S_all       1.101 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.276 

_refine_diff_density_min          -0.259 

_refine_diff_density_rms          0.068 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O -0.0741(4) -0.6337(3) 0.85963(14) 0.0466(6) Uani 1 1 d . . . 

H1 H 0.056(9) -0.707(7) 0.893(3) 0.079(13) Uiso 1 1 d . . . 

O2 O 0.1117(4) -0.3886(3) 0.87532(14) 0.0474(6) Uani 1 1 d . . . 

C1 C -0.0539(4) -0.4442(4) 0.84616(16) 0.0311(5) Uani 1 1 d . . . 

C2 C -0.2558(4) -0.3122(4) 0.79037(16) 0.0330(6) Uani 1 1 d . . . 

H2A H -0.4211 -0.3222 0.8202 0.040 Uiso 1 1 calc R . . 

H2B H -0.2449 -0.3646 0.7326 0.040 Uiso 1 1 calc R . . 

C3 C -0.2476(4) -0.0924(4) 0.77225(17) 0.0333(6) Uani 1 1 d . . . 

H3A H -0.0859 -0.0795 0.7401 0.040 Uiso 1 1 calc R . . 

H3B H -0.2564 -0.0383 0.8295 0.040 Uiso 1 1 calc R . . 

C4 C -0.4638(5) 0.0294(4) 0.71724(18) 0.0366(6) Uani 1 1 d . . . 

H4A H -0.6245 0.0118 0.7488 0.044 Uiso 1 1 calc R . . 

H4B H -0.4519 -0.0242 0.6597 0.044 Uiso 1 1 calc R . . 

C5 C -0.4691(5) 0.2529(4) 0.69890(17) 0.0352(6) Uani 1 1 d . . . 

H5A H -0.4952 0.3091 0.7561 0.042 Uiso 1 1 calc R . . 

H5B H -0.3036 0.2702 0.6716 0.042 Uiso 1 1 calc R . . 

C6 C -0.6731(5) 0.3706(4) 0.63796(17) 0.0362(6) Uani 1 1 d . . . 

H6A H -0.8388 0.3539 0.6654 0.043 Uiso 1 1 calc R . . 

H6B H -0.6476 0.3141 0.5808 0.043 Uiso 1 1 calc R . . 

C7 C -0.6769(5) 0.5939(4) 0.61947(19) 0.0412(6) Uani 1 1 d . . . 

H7A H -0.7088 0.6509 0.6765 0.049 Uiso 1 1 calc R . . 

H7B H -0.5087 0.6098 0.5945 0.049 Uiso 1 1 calc R . . 

C8 C -0.8724(6) 0.7128(5) 0.5560(2) 0.0552(8) Uani 1 1 d . . . 

H8A H -0.8385 0.6613 0.4984 0.083 Uiso 1 1 calc R . . 

H8B H -0.8656 0.8548 0.5480 0.083 Uiso 1 1 calc R . . 

H8C H -1.0401 0.6995 0.5804 0.083 Uiso 1 1 calc R . . 

N1A N 0.3005(4) -0.8826(3) 0.95326(14) 0.0338(5) Uani 1 1 d . . . 

C2A C 0.3317(4) -1.0812(4) 0.97026(17) 0.0347(6) Uani 1 1 d . . . 

H2AA H 0.2141 -1.1433 0.9498 0.042 Uiso 1 1 calc R . . 

C1A C 0.4690(5) -0.8016(4) 0.98313(17) 0.0346(6) Uani 1 1 d . . . 

H1AA H 0.4515 -0.6601 0.9721 0.041 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0419(11) 0.0280(10) 0.0707(14) 0.0103(8) -0.0267(9) -0.0110(8) 

O2 0.0437(11) 0.0327(10) 0.0682(13) -0.0013(8) -0.0263(9) -0.0084(8) 

C1 0.0279(11) 0.0281(12) 0.0362(12) -0.0012(9) -0.0043(9) -0.0050(9) 

C2 0.0305(12) 0.0255(12) 0.0414(13) -0.0002(9) -0.0097(9) -0.0032(9) 

C3 0.0294(12) 0.0262(12) 0.0428(13) -0.0007(9) -0.0080(9) -0.0038(9) 

C4 0.0339(13) 0.0278(12) 0.0468(14) -0.0015(10) -0.0119(10) -0.0033(9) 

C5 0.0331(12) 0.0289(12) 0.0426(13) 0.0008(10) -0.0093(10) -0.0059(9) 

C6 0.0328(12) 0.0316(13) 0.0420(14) 0.0006(10) -0.0101(10) -0.0036(10) 

C7 0.0406(14) 0.0315(14) 0.0473(15) 0.0039(10) -0.0106(11) -0.0027(10) 

C8 0.0526(17) 0.0452(17) 0.0567(18) 0.0104(13) -0.0158(13) 0.0050(13) 

N1A 0.0302(10) 0.0302(11) 0.0396(11) -0.0002(8) -0.0072(8) -0.0051(8) 

C2A 0.0294(12) 0.0340(13) 0.0422(13) -0.0042(10) -0.0063(9) -0.0093(9) 

C1A 0.0331(12) 0.0251(11) 0.0445(14) -0.0011(9) -0.0051(9) -0.0058(9) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.325(3) . ? 

O1 H1 0.92(5) . ? 

O2 C1 1.206(3) . ? 

C1 C2 1.493(3) . ? 

C2 C3 1.513(3) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.517(3) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.522(3) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 C6 1.515(3) . ? 

C5 H5A 0.9900 . ? 

C5 H5B 0.9900 . ? 

C6 C7 1.523(3) . ? 

C6 H6A 0.9900 . ? 

C6 H6B 0.9900 . ? 

C7 C8 1.510(4) . ? 

C7 H7A 0.9900 . ? 

C7 H7B 0.9900 . ? 

C8 H8A 0.9800 . ? 

C8 H8B 0.9800 . ? 

C8 H8C 0.9800 . ? 

N1A C1A 1.330(3) . ? 

N1A C2A 1.330(3) . ? 

C2A C1A 1.376(3) 2_637 ? 

C2A H2AA 0.9500 . ? 

C1A C2A 1.376(3) 2_637 ? 

C1A H1AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 108(3) . . ? 

O2 C1 O1 122.9(2) . . ? 

O2 C1 C2 125.0(2) . . ? 

O1 C1 C2 112.1(2) . . ? 

C1 C2 C3 115.52(19) . . ? 

C1 C2 H2A 108.4 . . ? 

C3 C2 H2A 108.4 . . ? 

C1 C2 H2B 108.4 . . ? 

C3 C2 H2B 108.4 . . ? 

H2A C2 H2B 107.5 . . ? 

C2 C3 C4 111.42(19) . . ? 

C2 C3 H3A 109.3 . . ? 

C4 C3 H3A 109.3 . . ? 

C2 C3 H3B 109.3 . . ? 

C4 C3 H3B 109.3 . . ? 

H3A C3 H3B 108.0 . . ? 

C3 C4 C5 113.8(2) . . ? 

C3 C4 H4A 108.8 . . ? 

C5 C4 H4A 108.8 . . ? 

C3 C4 H4B 108.8 . . ? 

C5 C4 H4B 108.8 . . ? 

H4A C4 H4B 107.7 . . ? 

C6 C5 C4 113.3(2) . . ? 

C6 C5 H5A 108.9 . . ? 

C4 C5 H5A 108.9 . . ? 

C6 C5 H5B 108.9 . . ? 

C4 C5 H5B 108.9 . . ? 

H5A C5 H5B 107.7 . . ? 

C5 C6 C7 113.2(2) . . ? 

C5 C6 H6A 108.9 . . ? 

C7 C6 H6A 108.9 . . ? 

C5 C6 H6B 108.9 . . ? 

C7 C6 H6B 108.9 . . ? 

H6A C6 H6B 107.8 . . ? 

C8 C7 C6 114.0(2) . . ? 

C8 C7 H7A 108.7 . . ? 

C6 C7 H7A 108.7 . . ? 

C8 C7 H7B 108.7 . . ? 

C6 C7 H7B 108.7 . . ? 

H7A C7 H7B 107.6 . . ? 

C7 C8 H8A 109.5 . . ? 

C7 C8 H8B 109.5 . . ? 

H8A C8 H8B 109.5 . . ? 

C7 C8 H8C 109.5 . . ? 

H8A C8 H8C 109.5 . . ? 

H8B C8 H8C 109.5 . . ? 

C1A N1A C2A 117.5(2) . . ? 

N1A C2A C1A 121.3(2) . 2_637 ? 

N1A C2A H2AA 119.3 . . ? 

C1A C2A H2AA 119.3 2_637 . ? 

N1A C1A C2A 121.2(2) . 2_637 ? 

N1A C1A H1AA 119.4 . . ? 

C2A C1A H1AA 119.4 2_637 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 -1.3(4) . . . . ? 

O1 C1 C2 C3 179.6(2) . . . . ? 

C1 C2 C3 C4 -178.5(2) . . . . ? 

C2 C3 C4 C5 178.5(2) . . . . ? 

C3 C4 C5 C6 175.5(2) . . . . ? 

C4 C5 C6 C7 -179.7(2) . . . . ? 

C5 C6 C7 C8 177.8(2) . . . . ? 

C1A N1A C2A C1A -0.1(4) . . . 2_637 ? 

C2A N1A C1A C2A 0.1(4) . . . 2_637 ? 



#===END





data_ab0212 

_database_code_CSD                  192857



_chemical_name_systematic         ?

_chemical_name_common             'pyrazine / nonanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C9 H18 O2)' 

_chemical_formula_sum             'C22 H40 N2 O4' 

_chemical_formula_weight          396.56 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            triclinic

_symmetry_space_group_name_H-M    P-1



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    5.4731(2) 

_cell_length_b                    6.8775(2) 

_cell_length_c                    16.3824(6) 

_cell_angle_alpha                 89.776(1) 

_cell_angle_beta                  82.992(1) 

_cell_angle_gamma                 76.091(1) 

_cell_volume                      593.89(4) 

_cell_formula_units_Z             1 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     5100 

_cell_measurement_theta_min       1.00

_cell_measurement_theta_max       27.48



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.109 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              218 

_exptl_absorpt_coefficient_mu     0.075 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm glass capillary at ca. 300 K 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             6194 

_diffrn_reflns_av_R_equivalents   0.0648 

_diffrn_reflns_av_sigmaI/netI     0.0509 

_diffrn_reflns_limit_h_min        -7 

_diffrn_reflns_limit_h_max        7 

_diffrn_reflns_limit_k_min        -8 

_diffrn_reflns_limit_k_max        8 

_diffrn_reflns_limit_l_min        -19 

_diffrn_reflns_limit_l_max        21 

_diffrn_reflns_theta_min          3.76 

_diffrn_reflns_theta_max          27.60 

_diffrn_measured_fraction_theta_max    0.969 

_diffrn_reflns_theta_full              27.60 

_diffrn_measured_fraction_theta_full   0.969 

_reflns_number_total              2652 

_reflns_number_gt                 2221 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0638P)²+0.1622P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2652 

_refine_ls_number_parameters      132 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0637 

_refine_ls_R_factor_gt            0.0533 

_refine_ls_wR_factor_ref          0.1489 

_refine_ls_wR_factor_gt           0.1391 

_refine_ls_goodness_of_fit_ref    1.052 

_refine_ls_restrained_S_all       1.052 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.251 

_refine_diff_density_min          -0.200 

_refine_diff_density_rms          0.037 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O -0.4479(2) 0.68345(15) 0.13075(7) 0.0466(3) Uani 1 1 d . . . 

H1 H -0.578(5) 0.748(3) 0.1001(14) 0.079(7) Uiso 1 1 d . . . 

O2 O -0.6328(2) 0.43227(15) 0.11629(7) 0.0468(3) Uani 1 1 d . . . 

C1 C -0.4719(2) 0.49741(18) 0.14293(8) 0.0303(3) Uani 1 1 d . . . 

C2 C -0.2778(2) 0.38372(18) 0.19442(8) 0.0319(3) Uani 1 1 d . . . 

H2A H -0.3008 0.4555 0.2481 0.038 Uiso 1 1 calc R . . 

H2B H -0.1068 0.3847 0.1668 0.038 Uiso 1 1 calc R . . 

C3 C -0.2878(2) 0.16738(18) 0.21008(8) 0.0318(3) Uani 1 1 d . . . 

H3A H -0.2634 0.0931 0.1569 0.038 Uiso 1 1 calc R . . 

H3B H -0.4567 0.1640 0.2388 0.038 Uiso 1 1 calc R . . 

C4 C -0.0827(3) 0.06629(19) 0.26222(9) 0.0349(3) Uani 1 1 d . . . 

H4A H -0.1081 0.1428 0.3149 0.042 Uiso 1 1 calc R . . 

H4B H 0.0848 0.0725 0.2332 0.042 Uiso 1 1 calc R . . 

C5 C -0.0788(3) -0.15198(19) 0.28085(9) 0.0345(3) Uani 1 1 d . . . 

H5A H -0.2484 -0.1600 0.3074 0.041 Uiso 1 1 calc R . . 

H5B H -0.0427 -0.2311 0.2285 0.041 Uiso 1 1 calc R . . 

C6 C 0.1191(3) -0.24309(19) 0.33689(9) 0.0351(3) Uani 1 1 d . . . 

H6A H 0.0835 -0.1620 0.3887 0.042 Uiso 1 1 calc R . . 

H6B H 0.2882 -0.2349 0.3099 0.042 Uiso 1 1 calc R . . 

C7 C 0.1280(3) -0.46059(19) 0.35781(8) 0.0345(3) Uani 1 1 d . . . 

H7A H -0.0431 -0.4706 0.3821 0.041 Uiso 1 1 calc R . . 

H7B H 0.1739 -0.5436 0.3065 0.041 Uiso 1 1 calc R . . 

C8 C 0.3170(3) -0.5441(2) 0.41762(10) 0.0423(4) Uani 1 1 d . . . 

H8A H 0.4879 -0.5340 0.3931 0.051 Uiso 1 1 calc R . . 

H8B H 0.2714 -0.4601 0.4687 0.051 Uiso 1 1 calc R . . 

C9 C 0.3282(4) -0.7608(2) 0.43965(11) 0.0535(4) Uani 1 1 d . . . 

H9A H 0.1595 -0.7727 0.4635 0.080 Uiso 1 1 calc R . . 

H9B H 0.4486 -0.8027 0.4797 0.080 Uiso 1 1 calc R . . 

H9C H 0.3837 -0.8465 0.3899 0.080 Uiso 1 1 calc R . . 

N1A N -0.8074(2) 0.89882(16) 0.04332(7) 0.0331(3) Uani 1 1 d . . . 

C1A C -0.9706(3) 0.80678(19) 0.01611(8) 0.0334(3) Uani 1 1 d . . . 

H1AA H -0.9547 0.6687 0.0267 0.040 Uiso 1 1 calc R . . 

C2A C -0.8366(2) 1.09317(19) 0.02735(8) 0.0337(3) Uani 1 1 d . . . 

H2AA H -0.7237 1.1638 0.0460 0.040 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0478(6) 0.0326(5) 0.0685(8) 0.0208(5) -0.0290(5) -0.0170(4) 

O2 0.0479(6) 0.0330(5) 0.0665(7) 0.0084(5) -0.0280(5) -0.0133(4) 

C1 0.0296(6) 0.0258(6) 0.0354(7) 0.0040(5) -0.0050(5) -0.0058(5) 

C2 0.0319(6) 0.0263(6) 0.0383(7) 0.0050(5) -0.0094(5) -0.0063(5) 

C3 0.0308(6) 0.0258(6) 0.0388(7) 0.0044(5) -0.0068(5) -0.0057(5) 

C4 0.0351(7) 0.0266(6) 0.0444(7) 0.0074(5) -0.0124(6) -0.0068(5) 

C5 0.0340(7) 0.0261(6) 0.0443(8) 0.0063(5) -0.0105(5) -0.0064(5) 

C6 0.0365(7) 0.0285(6) 0.0416(7) 0.0072(5) -0.0114(6) -0.0074(5) 

C7 0.0369(7) 0.0280(6) 0.0387(7) 0.0059(5) -0.0083(5) -0.0062(5) 

C8 0.0465(8) 0.0354(7) 0.0440(8) 0.0100(6) -0.0142(6) -0.0041(6) 

C9 0.0667(11) 0.0365(8) 0.0527(9) 0.0142(7) -0.0126(8) -0.0012(7) 

N1A 0.0315(6) 0.0297(6) 0.0376(6) 0.0044(4) -0.0067(4) -0.0056(4) 

C1A 0.0343(7) 0.0243(6) 0.0413(7) 0.0042(5) -0.0050(5) -0.0067(5) 

C2A 0.0324(6) 0.0295(6) 0.0408(7) 0.0007(5) -0.0067(5) -0.0096(5) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.3291(15) . ? 

O1 H1 0.95(3) . ? 

O2 C1 1.2045(16) . ? 

C1 C2 1.5054(17) . ? 

C2 C3 1.5216(16) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.5256(17) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.5263(16) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 C6 1.5233(18) . ? 

C5 H5A 0.9900 . ? 

C5 H5B 0.9900 . ? 

C6 C7 1.5240(17) . ? 

C6 H6A 0.9900 . ? 

C6 H6B 0.9900 . ? 

C7 C8 1.5223(19) . ? 

C7 H7A 0.9900 . ? 

C7 H7B 0.9900 . ? 

C8 C9 1.521(2) . ? 

C8 H8A 0.9900 . ? 

C8 H8B 0.9900 . ? 

C9 H9A 0.9800 . ? 

C9 H9B 0.9800 . ? 

C9 H9C 0.9800 . ? 

N1A C1A 1.3298(18) . ? 

N1A C2A 1.3362(16) . ? 

C1A C2A 1.3873(19) 2_375 ? 

C1A H1AA 0.9500 . ? 

C2A C1A 1.3873(19) 2_375 ? 

C2A H2AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 107.6(14) . . ? 

O2 C1 O1 123.09(12) . . ? 

O2 C1 C2 125.36(11) . . ? 

O1 C1 C2 111.54(11) . . ? 

C1 C2 C3 115.15(10) . . ? 

C1 C2 H2A 108.5 . . ? 

C3 C2 H2A 108.5 . . ? 

C1 C2 H2B 108.5 . . ? 

C3 C2 H2B 108.5 . . ? 

H2A C2 H2B 107.5 . . ? 

C2 C3 C4 110.77(10) . . ? 

C2 C3 H3A 109.5 . . ? 

C4 C3 H3A 109.5 . . ? 

C2 C3 H3B 109.5 . . ? 

C4 C3 H3B 109.5 . . ? 

H3A C3 H3B 108.1 . . ? 

C3 C4 C5 114.29(11) . . ? 

C3 C4 H4A 108.7 . . ? 

C5 C4 H4A 108.7 . . ? 

C3 C4 H4B 108.7 . . ? 

C5 C4 H4B 108.7 . . ? 

H4A C4 H4B 107.6 . . ? 

C6 C5 C4 112.41(11) . . ? 

C6 C5 H5A 109.1 . . ? 

C4 C5 H5A 109.1 . . ? 

C6 C5 H5B 109.1 . . ? 

C4 C5 H5B 109.1 . . ? 

H5A C5 H5B 107.9 . . ? 

C5 C6 C7 114.23(11) . . ? 

C5 C6 H6A 108.7 . . ? 

C7 C6 H6A 108.7 . . ? 

C5 C6 H6B 108.7 . . ? 

C7 C6 H6B 108.7 . . ? 

H6A C6 H6B 107.6 . . ? 

C8 C7 C6 113.07(12) . . ? 

C8 C7 H7A 109.0 . . ? 

C6 C7 H7A 109.0 . . ? 

C8 C7 H7B 109.0 . . ? 

C6 C7 H7B 109.0 . . ? 

H7A C7 H7B 107.8 . . ? 

C9 C8 C7 113.95(13) . . ? 

C9 C8 H8A 108.8 . . ? 

C7 C8 H8A 108.8 . . ? 

C9 C8 H8B 108.8 . . ? 

C7 C8 H8B 108.8 . . ? 

H8A C8 H8B 107.7 . . ? 

C8 C9 H9A 109.5 . . ? 

C8 C9 H9B 109.5 . . ? 

H9A C9 H9B 109.5 . . ? 

C8 C9 H9C 109.5 . . ? 

H9A C9 H9C 109.5 . . ? 

H9B C9 H9C 109.5 . . ? 

C1A N1A C2A 117.26(11) . . ? 

N1A C1A C2A 121.83(12) . 2_375 ? 

N1A C1A H1AA 119.1 . . ? 

C2A C1A H1AA 119.1 2_375 . ? 

N1A C2A C1A 120.91(12) . 2_375 ? 

N1A C2A H2AA 119.5 . . ? 

C1A C2A H2AA 119.5 2_375 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 2.1(2) . . . . ? 

O1 C1 C2 C3 -178.83(11) . . . . ? 

C1 C2 C3 C4 179.65(11) . . . . ? 

C2 C3 C4 C5 -179.91(11) . . . . ? 

C3 C4 C5 C6 -176.83(11) . . . . ? 

C4 C5 C6 C7 179.45(11) . . . . ? 

C5 C6 C7 C8 -176.81(12) . . . . ? 

C6 C7 C8 C9 179.74(12) . . . . ? 

C2A N1A C1A C2A 0.2(2) . . . 2_375 ? 

C1A N1A C2A C1A -0.2(2) . . . 2_375 ? 



#===END





data_ab0213 

_database_code_CSD                  192858



_chemical_name_systematic         ? 

_chemical_name_common             'pyrazine / decanoic acid' 

_chemical_melting_point           ? 

_chemical_formula_moiety          'C4 H4 N2, 2(C10 H20 O2)' 

_chemical_formula_sum             'C24 H44 N2 O4' 

_chemical_formula_weight          424.61 



loop_ 

_atom_type_symbol 

_atom_type_description 

_atom_type_scat_dispersion_real 

_atom_type_scat_dispersion_imag 

_atom_type_scat_source 

'C'  'C'   0.0033   0.0016 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'H'  'H'   0.0000   0.0000 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'N'  'N'   0.0061   0.0033 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

'O'  'O'   0.0106   0.0060 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            triclinic

_symmetry_space_group_name_H-M    P-1



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    5.4573(2) 

_cell_length_b                    6.8970(2) 

_cell_length_c                    18.0387(6) 

_cell_angle_alpha                 80.575(1) 

_cell_angle_beta                  81.940(1) 

_cell_angle_gamma                 75.554(2) 

_cell_volume                      645.10(4) 

_cell_formula_units_Z             1 

_cell_measurement_temperature     180(2) 

_cell_measurement_reflns_used     6520 

_cell_measurement_theta_min       1.00

_cell_measurement_theta_max       25.03



_exptl_crystal_description        cylinder 

_exptl_crystal_colour             colourless

_exptl_crystal_size_length        0.35 

_exptl_crystal_size_rad           0.10 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.093 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              234 

_exptl_absorpt_coefficient_mu     0.073 

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

Crystal grown in situ in 0.2 mm glass capillary at ca. 308 K 

; 



_diffrn_ambient_temperature       180(2) 

_diffrn_radiation_wavelength      0.7107

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Nonius KappaCCD'

_diffrn_measurement_method        'Thin slice ω and φ scans'

_diffrn_standards_number          0

_diffrn_reflns_number             4697 

_diffrn_reflns_av_R_equivalents   0.0417 

_diffrn_reflns_av_sigmaI/netI     0.0414 

_diffrn_reflns_limit_h_min        -6 

_diffrn_reflns_limit_h_max        6 

_diffrn_reflns_limit_k_min        -7 

_diffrn_reflns_limit_k_max        8 

_diffrn_reflns_limit_l_min        -20 

_diffrn_reflns_limit_l_max        21 

_diffrn_reflns_theta_min          3.88 

_diffrn_reflns_theta_max          25.04 

_diffrn_measured_fraction_theta_max    0.978 

_diffrn_reflns_theta_full              25.04 

_diffrn_measured_fraction_theta_full   0.978 

_reflns_number_total              2235 

_reflns_number_gt                 1988 

_reflns_threshold_expression      I>2σ(I) 



_computing_data_collection        'Collect (Nonius, 1998)'

_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor, 1997)' 

_computing_data_reduction

;

HKL Denzo and Scalepack (Otwinowski & Minor, 1997)

;

_computing_structure_solution     'SIR-92 (Altomare et al., 1994)'

_computing_structure_refinement   'SHELXTL v6.12 (Bruker AXS, 2001)' 

_computing_publication_material   'SHELXTL v6.12 (Bruker AXS, 2001)' 



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0573P)²+0.1626P] where P=(Fo²+2Fc²)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2235 

_refine_ls_number_parameters      141 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0528 

_refine_ls_R_factor_gt            0.0470 

_refine_ls_wR_factor_ref          0.1324 

_refine_ls_wR_factor_gt           0.1269 

_refine_ls_goodness_of_fit_ref    1.102 

_refine_ls_restrained_S_all       1.102 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 

_refine_diff_density_max          0.149 

_refine_diff_density_min          -0.180 

_refine_diff_density_rms          0.031 



loop_ 

_atom_site_label 

_atom_site_type_symbol 

_atom_site_fract_x 

_atom_site_fract_y 

_atom_site_fract_z 

_atom_site_U_iso_or_equiv 

_atom_site_adp_type 

_atom_site_occupancy 

_atom_site_symmetry_multiplicity 

_atom_site_calc_flag 

_atom_site_refinement_flags 

_atom_site_disorder_assembly 

_atom_site_disorder_group 

O1 O 0.3530(2) -0.71362(16) 0.61993(7) 0.0466(3) Uani 1 1 d . . . 

H1 H 0.508(5) -0.773(3) 0.5902(13) 0.078(7) Uiso 1 1 d . . . 

O2 O 0.5492(2) -0.46153(16) 0.60666(7) 0.0468(3) Uani 1 1 d . . . 

C1 C 0.3682(3) -0.5322(2) 0.63133(7) 0.0306(3) Uani 1 1 d . . . 

C2 C 0.1379(3) -0.4308(2) 0.67880(8) 0.0321(3) Uani 1 1 d . . . 

H2A H 0.1237 -0.5168 0.7281 0.039 Uiso 1 1 calc R . . 

H2B H -0.0149 -0.4233 0.6537 0.039 Uiso 1 1 calc R . . 

C3 C 0.1366(3) -0.2196(2) 0.69323(8) 0.0322(3) Uani 1 1 d . . . 

H3A H 0.1491 -0.1313 0.6444 0.039 Uiso 1 1 calc R . . 

H3B H 0.2865 -0.2250 0.7194 0.039 Uiso 1 1 calc R . . 

C4 C -0.1049(3) -0.1306(2) 0.74125(8) 0.0351(4) Uani 1 1 d . . . 

H4A H -0.2532 -0.1260 0.7145 0.042 Uiso 1 1 calc R . . 

H4B H -0.1174 -0.2219 0.7894 0.042 Uiso 1 1 calc R . . 

C5 C -0.1200(3) 0.0802(2) 0.75919(8) 0.0363(4) Uani 1 1 d . . . 

H5A H -0.1186 0.1739 0.7114 0.044 Uiso 1 1 calc R . . 

H5B H 0.0328 0.0779 0.7834 0.044 Uiso 1 1 calc R . . 

C6 C -0.3565(3) 0.1604(2) 0.81104(8) 0.0366(4) Uani 1 1 d . . . 

H6A H -0.5092 0.1618 0.7869 0.044 Uiso 1 1 calc R . . 

H6B H -0.3573 0.0669 0.8589 0.044 Uiso 1 1 calc R . . 

C7 C -0.3737(3) 0.3718(2) 0.82895(8) 0.0354(4) Uani 1 1 d . . . 

H7A H -0.3781 0.4657 0.7811 0.042 Uiso 1 1 calc R . . 

H7B H -0.2179 0.3711 0.8514 0.042 Uiso 1 1 calc R . . 

C8 C -0.6044(3) 0.4522(2) 0.88274(8) 0.0378(4) Uani 1 1 d . . . 

H8A H -0.7609 0.4557 0.8601 0.045 Uiso 1 1 calc R . . 

H8B H -0.6018 0.3582 0.9305 0.045 Uiso 1 1 calc R . . 

C9 C -0.6140(3) 0.6622(2) 0.90027(9) 0.0442(4) Uani 1 1 d . . . 

H9A H -0.4587 0.6576 0.9236 0.053 Uiso 1 1 calc R . . 

H9B H -0.6125 0.7551 0.8522 0.053 Uiso 1 1 calc R . . 

C10 C -0.8451(4) 0.7475(3) 0.95259(11) 0.0615(5) Uani 1 1 d . . . 

H10A H -1.0002 0.7571 0.9293 0.092 Uiso 1 1 calc R . . 

H10B H -0.8376 0.8822 0.9615 0.092 Uiso 1 1 calc R . . 

H10C H -0.8468 0.6583 1.0008 0.092 Uiso 1 1 calc R . . 

N1A N 0.7759(2) -0.90937(17) 0.53984(6) 0.0334(3) Uani 1 1 d . . . 

C1A C 0.9588(3) -0.8113(2) 0.51458(8) 0.0336(3) Uani 1 1 d . . . 

H1AA H 0.9351 -0.6761 0.5242 0.040 Uiso 1 1 calc R . . 

C2A C 0.8174(3) -1.0990(2) 0.52531(8) 0.0340(3) Uani 1 1 d . . . 

H2AA H 0.6912 -1.1737 0.5426 0.041 Uiso 1 1 calc R . . 



loop_ 

_atom_site_aniso_label 

_atom_site_aniso_U_11 

_atom_site_aniso_U_22 

_atom_site_aniso_U_33 

_atom_site_aniso_U_23 

_atom_site_aniso_U_13 

_atom_site_aniso_U_12 

O1 0.0362(6) 0.0391(6) 0.0690(8) -0.0283(5) 0.0149(5) -0.0148(5) 

O2 0.0359(6) 0.0362(6) 0.0681(8) -0.0161(5) 0.0141(5) -0.0127(5) 

C1 0.0280(7) 0.0290(7) 0.0353(7) -0.0067(5) -0.0030(5) -0.0062(6) 

C2 0.0284(7) 0.0294(7) 0.0375(7) -0.0077(6) 0.0012(6) -0.0055(6) 

C3 0.0284(7) 0.0292(7) 0.0392(8) -0.0081(6) -0.0012(6) -0.0063(6) 

C4 0.0313(7) 0.0303(8) 0.0432(8) -0.0103(6) 0.0023(6) -0.0064(6) 

C5 0.0317(7) 0.0300(8) 0.0465(8) -0.0108(6) 0.0012(6) -0.0052(6) 

C6 0.0332(8) 0.0306(8) 0.0452(8) -0.0101(6) 0.0024(6) -0.0064(6) 

C7 0.0329(7) 0.0327(8) 0.0405(8) -0.0107(6) 0.0016(6) -0.0071(6) 

C8 0.0342(8) 0.0380(8) 0.0403(8) -0.0116(6) 0.0015(6) -0.0056(6) 

C9 0.0445(9) 0.0393(9) 0.0477(9) -0.0173(7) 0.0005(7) -0.0030(7) 

C10 0.0580(11) 0.0579(11) 0.0615(11) -0.0282(9) 0.0039(9) 0.0072(9) 

N1A 0.0281(6) 0.0325(7) 0.0389(7) -0.0085(5) -0.0009(5) -0.0051(5) 

C1A 0.0338(7) 0.0264(7) 0.0417(8) -0.0087(6) -0.0038(6) -0.0064(6) 

C2A 0.0295(7) 0.0311(7) 0.0418(8) -0.0054(6) -0.0004(6) -0.0092(6) 



_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

O1 C1 1.3254(17) . ? 

O1 H1 0.97(3) . ? 

O2 C1 1.2068(17) . ? 

C1 C2 1.5023(18) . ? 

C2 C3 1.5194(18) . ? 

C2 H2A 0.9900 . ? 

C2 H2B 0.9900 . ? 

C3 C4 1.5211(18) . ? 

C3 H3A 0.9900 . ? 

C3 H3B 0.9900 . ? 

C4 C5 1.5210(19) . ? 

C4 H4A 0.9900 . ? 

C4 H4B 0.9900 . ? 

C5 C6 1.5234(19) . ? 

C5 H5A 0.9900 . ? 

C5 H5B 0.9900 . ? 

C6 C7 1.5224(19) . ? 

C6 H6A 0.9900 . ? 

C6 H6B 0.9900 . ? 

C7 C8 1.5229(19) . ? 

C7 H7A 0.9900 . ? 

C7 H7B 0.9900 . ? 

C8 C9 1.519(2) . ? 

C8 H8A 0.9900 . ? 

C8 H8B 0.9900 . ? 

C9 C10 1.518(2) . ? 

C9 H9A 0.9900 . ? 

C9 H9B 0.9900 . ? 

C10 H10A 0.9800 . ? 

C10 H10B 0.9800 . ? 

C10 H10C 0.9800 . ? 

N1A C1A 1.3303(19) . ? 

N1A C2A 1.3333(18) . ? 

C1A C2A 1.384(2) 2_736 ? 

C1A H1AA 0.9500 . ? 

C2A C1A 1.384(2) 2_736 ? 

C2A H2AA 0.9500 . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

C1 O1 H1 108.2(14) . . ? 

O2 C1 O1 122.83(13) . . ? 

O2 C1 C2 125.32(12) . . ? 

O1 C1 C2 111.85(11) . . ? 

C1 C2 C3 115.41(11) . . ? 

C1 C2 H2A 108.4 . . ? 

C3 C2 H2A 108.4 . . ? 

C1 C2 H2B 108.4 . . ? 

C3 C2 H2B 108.4 . . ? 

H2A C2 H2B 107.5 . . ? 

C2 C3 C4 111.12(11) . . ? 

C2 C3 H3A 109.4 . . ? 

C4 C3 H3A 109.4 . . ? 

C2 C3 H3B 109.4 . . ? 

C4 C3 H3B 109.4 . . ? 

H3A C3 H3B 108.0 . . ? 

C5 C4 C3 114.51(11) . . ? 

C5 C4 H4A 108.6 . . ? 

C3 C4 H4A 108.6 . . ? 

C5 C4 H4B 108.6 . . ? 

C3 C4 H4B 108.6 . . ? 

H4A C4 H4B 107.6 . . ? 

C4 C5 C6 113.29(12) . . ? 

C4 C5 H5A 108.9 . . ? 

C6 C5 H5A 108.9 . . ? 

C4 C5 H5B 108.9 . . ? 

C6 C5 H5B 108.9 . . ? 

H5A C5 H5B 107.7 . . ? 

C7 C6 C5 113.61(12) . . ? 

C7 C6 H6A 108.8 . . ? 

C5 C6 H6A 108.8 . . ? 

C7 C6 H6B 108.8 . . ? 

C5 C6 H6B 108.8 . . ? 

H6A C6 H6B 107.7 . . ? 

C6 C7 C8 114.48(12) . . ? 

C6 C7 H7A 108.6 . . ? 

C8 C7 H7A 108.6 . . ? 

C6 C7 H7B 108.6 . . ? 

C8 C7 H7B 108.6 . . ? 

H7A C7 H7B 107.6 . . ? 

C9 C8 C7 113.15(12) . . ? 

C9 C8 H8A 108.9 . . ? 

C7 C8 H8A 108.9 . . ? 

C9 C8 H8B 108.9 . . ? 

C7 C8 H8B 108.9 . . ? 

H8A C8 H8B 107.8 . . ? 

C10 C9 C8 114.18(14) . . ? 

C10 C9 H9A 108.7 . . ? 

C8 C9 H9A 108.7 . . ? 

C10 C9 H9B 108.7 . . ? 

C8 C9 H9B 108.7 . . ? 

H9A C9 H9B 107.6 . . ? 

C9 C10 H10A 109.5 . . ? 

C9 C10 H10B 109.5 . . ? 

H10A C10 H10B 109.5 . . ? 

C9 C10 H10C 109.5 . . ? 

H10A C10 H10C 109.5 . . ? 

H10B C10 H10C 109.5 . . ? 

C1A N1A C2A 117.14(12) . . ? 

N1A C1A C2A 121.72(13) . 2_736 ? 

N1A C1A H1AA 119.1 . . ? 

C2A C1A H1AA 119.1 2_736 . ? 

N1A C2A C1A 121.14(13) . 2_736 ? 

N1A C2A H2AA 119.4 . . ? 

C1A C2A H2AA 119.4 2_736 . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 C1 C2 C3 2.2(2) . . . . ? 

O1 C1 C2 C3 -178.66(11) . . . . ? 

C1 C2 C3 C4 179.64(11) . . . . ? 

C2 C3 C4 C5 179.28(11) . . . . ? 

C3 C4 C5 C6 -176.68(12) . . . . ? 

C4 C5 C6 C7 -179.70(12) . . . . ? 

C5 C6 C7 C8 -178.14(12) . . . . ? 

C6 C7 C8 C9 179.21(12) . . . . ? 

C7 C8 C9 C10 178.86(13) . . . . ? 

C2A N1A C1A C2A 0.2(2) . . . 2_736 ? 

C1A N1A C2A C1A -0.2(2) . . . 2_736 ? 



#===END

















