# Supplementary Material (ESI) for Chemical Communications

# This journal is © The Royal Society of Chemistry 2003



data_global



_journal_coden_Cambridge      182





loop_

_publ_author_name

'Mike Zaworotko'

'S. Fleischman'

'L. Morales'

'Brian Moulton'

'N. Rodriguez-Hornedo'

'R. Bailey, Walsh'



_publ_contact_author_name     	'Prof Mike Zaworotko'  

_publ_contact_author_address 

;

Department of Chemistry

University of South Florida

SCA400

4202 E. Fowler Avenue

Tampa

FL

33620

UNITED STATES OF AMERICA

;



_publ_contact_author_email       'XTAL@CHUMA1.CAS.USF.EDU'



_publ_requested_journal       'Chemical Communications'





_publ_section_title		

;

Crystal engineering of the composition of

pharmaceutical phases

;



data_sf0219 

_database_code_CSD                  188913



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C36 H44 N2 O4' 

_chemical_formula_weight          568.73 



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                    5.759(3) 

_cell_length_b                    11.683(6) 

_cell_length_c                    24.705(11) 

_cell_angle_alpha                 93.674(11) 

_cell_angle_beta                  90.880(10) 

_cell_angle_gamma                 104.045(7) 

_cell_volume                      1608.3(13) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     473(2) 

_cell_measurement_reflns_used     ? 

_cell_measurement_theta_min       ? 

_cell_measurement_theta_max       ? 



_exptl_crystal_description        needle 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           .05 

_exptl_crystal_size_mid           .05 

_exptl_crystal_size_min           1.0 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.174 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              612 

_exptl_absorpt_coefficient_mu     0.076 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   0.302 

_exptl_absorpt_correction_T_max   1.000

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       473(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'CCD area detector' 

_diffrn_measurement_method        'phi and omega scans' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             5208 

_diffrn_reflns_av_R_equivalents   0.0826 

_diffrn_reflns_av_sigmaI/netI     0.1182 

_diffrn_reflns_limit_h_min        -5 

_diffrn_reflns_limit_h_max        5 

_diffrn_reflns_limit_k_min        -11 

_diffrn_reflns_limit_k_max        11 

_diffrn_reflns_limit_l_min        -24 

_diffrn_reflns_limit_l_max        20 

_diffrn_reflns_theta_min          0.83 

_diffrn_reflns_theta_max          20.85 

_reflns_number_total              3362 

_reflns_number_gt                 1369 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection        'Bruker SMART' 

_computing_cell_refinement        'Bruker SMART' 

_computing_data_reduction         'Bruker SHELXTL' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'Bruker SHELXTL' 

_computing_publication_material   'Bruker SHELXTL' 



_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)+(0.1643P)²+0.0000P] 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          3362 

_refine_ls_number_parameters      399 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1775 

_refine_ls_R_factor_gt            0.0964 

_refine_ls_wR_factor_ref          0.2987 

_refine_ls_wR_factor_gt           0.2510 

_refine_ls_goodness_of_fit_ref    0.904 

_refine_ls_restrained_S_all       0.904 

_refine_ls_shift/su_max           8.885 

_refine_ls_shift/su_mean          0.118 



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 

N1 N 0.3818(11) 0.7253(5) 0.0909(3) 0.0496(18) Uani 1 1 d . . . 

C1 C 0.5521(15) 0.6706(7) 0.1015(3) 0.059(2) Uani 1 1 d . . . 

H1 H 0.6414 0.6928 0.1338 0.071 Uiso 1 1 calc R . . 

C2 C 0.6051(13) 0.5816(7) 0.0671(3) 0.051(2) Uani 1 1 d . . . 

H2 H 0.7277 0.5465 0.0763 0.061 Uiso 1 1 calc R . . 

C3 C 0.4726(13) 0.5464(6) 0.0194(3) 0.042(2) Uani 1 1 d . . . 

C4 C 0.2928(13) 0.6035(7) 0.0087(3) 0.047(2) Uani 1 1 d . . . 

H4 H 0.2008 0.5832 -0.0234 0.056 Uiso 1 1 calc R . . 

C5 C 0.2498(13) 0.6906(7) 0.0455(3) 0.048(2) Uani 1 1 d . . . 

H5 H 0.1250 0.7255 0.0381 0.057 Uiso 1 1 calc R . . 

N11 N 0.3949(12) 0.2362(6) 0.0870(3) 0.0524(19) Uani 1 1 d . . . 

C11 C 0.5631(15) 0.1805(8) 0.0986(3) 0.060(2) Uani 1 1 d . . . 

H11 H 0.6553 0.2049 0.1304 0.072 Uiso 1 1 calc R . . 

C12 C 0.6096(14) 0.0871(7) 0.0655(3) 0.056(2) Uani 1 1 d . . . 

H12 H 0.7306 0.0517 0.0754 0.067 Uiso 1 1 calc R . . 

C13 C 0.4764(13) 0.0481(6) 0.0186(3) 0.040(2) Uani 1 1 d . . . 

C14 C 0.2960(13) 0.1054(7) 0.0060(3) 0.050(2) Uani 1 1 d . . . 

H14 H 0.2022 0.0832 -0.0256 0.060 Uiso 1 1 calc R . . 

C15 C 0.2604(14) 0.1964(7) 0.0420(4) 0.054(2) Uani 1 1 d . . . 

H15 H 0.1359 0.2313 0.0342 0.065 Uiso 1 1 calc R . . 

O21 O 1.3327(10) 0.3971(4) 0.1620(2) 0.0574(16) Uani 1 1 d . . . 

O22 O 1.0119(10) 0.4185(5) 0.1172(2) 0.0679(18) Uani 1 1 d . . . 

C21 C 1.1418(16) 0.4384(7) 0.1571(4) 0.057(2) Uani 1 1 d . . . 

C22 C 1.1020(19) 0.5068(8) 0.2094(4) 0.077(3) Uani 1 1 d . . . 

H22 H 1.261(14) 0.553(8) 0.222(4) 0.092 Uiso 1 1 calc . . . 

C23 C 0.961(2) 0.5921(9) 0.2023(4) 0.114(4) Uani 1 1 d . . . 

H23A H 0.7997 0.5513 0.1913 0.137 Uiso 1 1 calc R . . 

H23B H 1.0294 0.6438 0.1750 0.137 Uiso 1 1 calc R . . 

H23C H 0.9592 0.6377 0.2360 0.137 Uiso 1 1 calc R . . 

C24 C 1.0227(18) 0.4204(8) 0.2520(3) 0.061(3) Uani 1 1 d . . . 

C25 C 0.7874(18) 0.3537(8) 0.2538(3) 0.070(3) Uani 1 1 d . . . 

H25 H 0.6727 0.3649 0.2291 0.085 Uiso 1 1 calc R . . 

C26 C 0.7221(16) 0.2705(8) 0.2921(4) 0.072(3) Uani 1 1 d . . . 

H26 H 0.5625 0.2293 0.2931 0.086 Uiso 1 1 calc R . . 

C27 C 0.8837(18) 0.2471(8) 0.3283(3) 0.063(3) Uani 1 1 d . . . 

C28 C 1.1166(17) 0.3153(8) 0.3263(3) 0.073(3) Uani 1 1 d . . . 

H28 H 1.2316 0.3051 0.3512 0.088 Uiso 1 1 calc R . . 

C29 C 1.1813(15) 0.3975(8) 0.2886(4) 0.069(3) Uani 1 1 d . . . 

H29 H 1.3407 0.4393 0.2880 0.083 Uiso 1 1 calc R . . 

C30 C 0.8115(17) 0.1538(8) 0.3686(3) 0.082(3) Uani 1 1 d . . . 

H30A H 0.6644 0.0992 0.3549 0.098 Uiso 1 1 calc R . . 

H30B H 0.9338 0.1095 0.3694 0.098 Uiso 1 1 calc R . . 

O41 O 1.3164(10) 0.8858(5) 0.1646(2) 0.0657(17) Uani 1 1 d . . . 

O42 O 1.0087(10) 0.9084(5) 0.1153(2) 0.0674(18) Uani 1 1 d . . . 

C41 C 1.1358(17) 0.9315(7) 0.1554(4) 0.058(3) Uani 1 1 d . . . 

C42 C 1.1076(19) 1.0136(8) 0.2032(4) 0.081(3) Uani 1 1 d . . . 

H42 H 1.271(15) 1.058(8) 0.214(4) 0.097 Uiso 1 1 calc . . . 

C43 C 0.982(2) 1.1018(8) 0.1907(4) 0.117(4) Uani 1 1 d . . . 

H43A H 1.0723 1.1540 0.1659 0.140 Uiso 1 1 calc R . . 

H43B H 0.9610 1.1465 0.2235 0.140 Uiso 1 1 calc R . . 

H43C H 0.8276 1.0637 0.1744 0.140 Uiso 1 1 calc R . . 

C44 C 1.0138(19) 0.9451(8) 0.2523(4) 0.066(3) Uani 1 1 d . . . 

C45 C 1.1589(16) 0.9411(8) 0.2956(4) 0.069(3) Uani 1 1 d . . . 

H45 H 1.3204 0.9791 0.2944 0.083 Uiso 1 1 calc R . . 

C46 C 1.0792(18) 0.8838(8) 0.3407(4) 0.079(3) Uani 1 1 d . . . 

H46 H 1.1856 0.8855 0.3696 0.095 Uiso 1 1 calc R . . 

C47 C 0.8420(18) 0.8234(8) 0.3439(4) 0.071(3) Uani 1 1 d . . . 

C48 C 0.6872(17) 0.8217(8) 0.2992(4) 0.082(3) Uani 1 1 d . . . 

H48 H 0.5275 0.7803 0.2994 0.099 Uiso 1 1 calc R . . 

C49 C 0.7763(19) 0.8825(8) 0.2549(4) 0.075(3) Uani 1 1 d . . . 

H49 H 0.6728 0.8817 0.2255 0.090 Uiso 1 1 calc R . . 

C50 C 0.7470(18) 0.7610(9) 0.3940(4) 0.088(3) Uani 1 1 d . . . 

H50A H 0.8579 0.7927 0.4243 0.106 Uiso 1 1 calc R . . 

H50B H 0.5953 0.7791 0.4025 0.106 Uiso 1 1 calc R . . 

C52 C 0.920(3) 0.5927(11) 0.3761(6) 0.217(10) Uani 1 1 d . . . 

H52A H 0.9971 0.6342 0.3463 0.261 Uiso 1 1 calc R . . 

H52B H 0.8766 0.5093 0.3661 0.261 Uiso 1 1 calc R . . 

H52C H 1.0282 0.6081 0.4071 0.261 Uiso 1 1 calc R . . 

C32 C 0.718(4) 0.0886(12) 0.4586(5) 0.300(13) Uani 1 1 d . . . 

H32A H 0.7559 0.0207 0.4403 0.359 Uiso 1 1 calc R . . 

H32B H 0.5511 0.0705 0.4665 0.359 Uiso 1 1 calc R . . 

H32C H 0.8119 0.1092 0.4919 0.359 Uiso 1 1 calc R . . 

C53 C 0.604(2) 0.5760(12) 0.4387(6) 0.198(8) Uani 1 1 d . . . 

H53A H 0.5749 0.4916 0.4332 0.238 Uiso 1 1 calc R . . 

H53B H 0.4556 0.5972 0.4455 0.238 Uiso 1 1 calc R . . 

H53C H 0.7128 0.6036 0.4692 0.238 Uiso 1 1 calc R . . 

C31 C 0.775(3) 0.1916(13) 0.4227(6) 0.144(7) Uani 1 1 d . . . 

H31 H 0.61(2) 0.193(14) 0.416(7) 0.173 Uiso 1 1 calc . . . 

C51 C 0.711(4) 0.6319(14) 0.3889(5) 0.167(9) Uani 1 1 d . . . 

H51 H 0.59(3) 0.602(13) 0.359(6) 0.201 Uiso 1 1 calc . . . 

C33 C 0.822(5) 0.2784(15) 0.4470(7) 0.38(2) Uani 1 1 d . . . 

H33A H 0.9892 0.3150 0.4436 0.451 Uiso 1 1 calc R . . 

H33B H 0.7897 0.2659 0.4845 0.451 Uiso 1 1 calc R . . 

H33C H 0.7281 0.3290 0.4340 0.451 Uiso 1 1 calc R . . 

H21A H 1.3839 0.3450 0.1294 0.08(3) Uiso 1 1 d R . . 

H41A H 1.3456 0.8288 0.1342 0.07(3) Uiso 1 1 d R . . 






_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 

N1 C1 1.326(9) . ? 

N1 C5 1.329(8) . ? 

C1 C2 1.395(10) . ? 

C2 C3 1.379(9) . ? 

C3 C4 1.391(9) . ? 

C3 C3 1.496(14) 2_665 ? 

C4 C5 1.391(10) . ? 

N11 C11 1.328(9) . ? 

N11 C15 1.336(9) . ? 

C11 C12 1.401(10) . ? 

C12 C13 1.369(9) . ? 

C13 C14 1.406(9) . ? 

C13 C13 1.486(14) 2_655 ? 

C14 C15 1.398(10) . ? 

O21 C21 1.311(9) . ? 

O22 C21 1.204(9) . ? 

C21 C22 1.524(12) . ? 

C22 C23 1.449(12) . ? 

C22 C24 1.504(12) . ? 

C24 C29 1.360(10) . ? 

C24 C25 1.393(11) . ? 

C25 C26 1.390(11) . ? 

C26 C27 1.369(10) . ? 

C27 C28 1.387(11) . ? 

C27 C30 1.511(11) . ? 

C28 C29 1.372(11) . ? 

C30 C31 1.414(15) . ? 

O41 C41 1.302(9) . ? 

O42 C41 1.199(9) . ? 

C41 C42 1.509(12) . ? 

C42 C43 1.442(12) . ? 

C42 C44 1.530(12) . ? 

C44 C45 1.357(11) . ? 

C44 C49 1.390(11) . ? 

C45 C46 1.366(11) . ? 

C46 C47 1.383(11) . ? 

C47 C48 1.406(11) . ? 

C47 C50 1.517(11) . ? 

C48 C49 1.379(11) . ? 

C50 C51 1.469(16) . ? 

C52 C51 1.42(2) . ? 

C32 C31 1.517(17) . ? 

C53 C51 1.501(16) . ? 

C31 C33 1.12(2) . ? 



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 N1 C5 117.8(7) . . ? 

N1 C1 C2 123.8(8) . . ? 

C3 C2 C1 118.9(7) . . ? 

C2 C3 C4 117.0(7) . . ? 

C2 C3 C3 120.7(9) . 2_665 ? 

C4 C3 C3 122.3(10) . 2_665 ? 

C3 C4 C5 120.5(7) . . ? 

N1 C5 C4 122.0(7) . . ? 

C11 N11 C15 116.7(7) . . ? 

N11 C11 C12 123.6(8) . . ? 

C13 C12 C11 119.9(7) . . ? 

C12 C13 C14 117.2(7) . . ? 

C12 C13 C13 121.9(9) . 2_655 ? 

C14 C13 C13 120.9(9) . 2_655 ? 

C15 C14 C13 118.8(7) . . ? 

N11 C15 C14 123.7(7) . . ? 

O22 C21 O21 123.2(8) . . ? 

O22 C21 C22 125.9(9) . . ? 

O21 C21 C22 110.8(8) . . ? 

C23 C22 C24 116.5(8) . . ? 

C23 C22 C21 114.4(9) . . ? 

C24 C22 C21 108.6(7) . . ? 

C29 C24 C25 116.4(8) . . ? 

C29 C24 C22 121.5(9) . . ? 

C25 C24 C22 122.0(9) . . ? 

C26 C25 C24 120.7(8) . . ? 

C27 C26 C25 122.5(9) . . ? 

C26 C27 C28 116.0(8) . . ? 

C26 C27 C30 121.9(9) . . ? 

C28 C27 C30 122.1(9) . . ? 

C29 C28 C27 121.5(8) . . ? 

C24 C29 C28 122.9(8) . . ? 

C31 C30 C27 117.9(9) . . ? 

O42 C41 O41 124.4(8) . . ? 

O42 C41 C42 125.8(9) . . ? 

O41 C41 C42 109.8(9) . . ? 

C43 C42 C41 114.6(9) . . ? 

C43 C42 C44 114.0(8) . . ? 

C41 C42 C44 111.5(7) . . ? 

C45 C44 C49 116.2(8) . . ? 

C45 C44 C42 121.7(10) . . ? 

C49 C44 C42 122.0(10) . . ? 

C44 C45 C46 123.1(9) . . ? 

C45 C46 C47 120.7(9) . . ? 

C46 C47 C48 118.0(8) . . ? 

C46 C47 C50 122.0(9) . . ? 

C48 C47 C50 120.1(9) . . ? 

C49 C48 C47 118.9(9) . . ? 

C48 C49 C44 123.0(9) . . ? 

C51 C50 C47 114.8(9) . . ? 

C33 C31 C30 134.7(16) . . ? 

C33 C31 C32 111.7(15) . . ? 

C30 C31 C32 111.4(12) . . ? 

C52 C51 C50 114.6(15) . . ? 

C52 C51 C53 109.6(13) . . ? 

C50 C51 C53 111.6(12) . . ? 



_diffrn_measured_fraction_theta_max    0.991 

_diffrn_reflns_theta_full              20.85 

_diffrn_measured_fraction_theta_full   0.991 

_refine_diff_density_max    0.588 

_refine_diff_density_min   -0.464 

_refine_diff_density_rms    0.134 



data_sf6282 

_database_code_CSD                  188914



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C40 H34 F2 N2 O4' 

_chemical_formula_weight          644.69 



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' 

'F'  'F'   0.0171   0.0103 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            Monoclinic 

_symmetry_space_group_name_H-M    P2(1)/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                    5.860(4) 

_cell_length_b                    47.49(3) 

_cell_length_c                    5.928(4) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  107.382(8) 

_cell_angle_gamma                 90.00 

_cell_volume                      1574.3(19) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     200(2) 

_cell_measurement_reflns_used     ? 

_cell_measurement_theta_min       ? 

_cell_measurement_theta_max       ? 



_exptl_crystal_description        plate 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           0.02 

_exptl_crystal_size_mid           0.5 

_exptl_crystal_size_min           0.5 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.360 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              676 

_exptl_absorpt_coefficient_mu     0.096 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   0.501 

_exptl_absorpt_correction_T_max   1.000 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       200(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'CCD area detector' 

_diffrn_measurement_method        'phi and omega scans' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             4246 

_diffrn_reflns_av_R_equivalents   0.0677 

_diffrn_reflns_av_sigmaI/netI     0.0658 

_diffrn_reflns_limit_h_min        -5 

_diffrn_reflns_limit_h_max        5 

_diffrn_reflns_limit_k_min        -41 

_diffrn_reflns_limit_k_max        46 

_diffrn_reflns_limit_l_min        -6 

_diffrn_reflns_limit_l_max        5 

_diffrn_reflns_theta_min          0.86 

_diffrn_reflns_theta_max          21.69 

_reflns_number_total              1634 

_reflns_number_gt                 1350 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection        'Bruker SMART' 

_computing_cell_refinement        'Bruker SMART' 

_computing_data_reduction         'Bruker SHELXTL' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'Bruker SHELXTL' 

_computing_publication_material   'Bruker SHELXTL' 



_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)+(0.0878P)²+2.9905P] 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          1634 

_refine_ls_number_parameters      226 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1084 

_refine_ls_R_factor_gt            0.0908 

_refine_ls_wR_factor_ref          0.2209 

_refine_ls_wR_factor_gt           0.2065 

_refine_ls_goodness_of_fit_ref    1.230 

_refine_ls_restrained_S_all       1.230 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 



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 

F1 F -0.0709(9) 0.14901(9) 0.3254(9) 0.0391(14) Uani 0.70 1 d P . . 

F1A F 0.670(2) 0.1894(3) 0.527(2) 0.048(3) Uani 0.30 1 d P . . 

O1 O 0.7931(8) 0.08330(8) 0.7197(8) 0.0467(13) Uani 1 1 d . . . 

H1A H 0.8096 0.0687 0.6457 0.070 Uiso 1 1 calc R . . 

O2 O 0.4940(9) 0.05878(10) 0.7809(8) 0.0518(14) Uani 1 1 d . . . 

C1 C 0.6117(13) 0.07983(14) 0.8074(11) 0.0383(18) Uani 1 1 d . . . 

C2 C 0.5780(13) 0.10592(13) 0.9424(12) 0.0449(19) Uani 1 1 d . . . 

H2A H 0.7404 0.1120 1.0412 0.054 Uiso 1 1 calc R . . 

C3 C 0.4325(15) 0.10092(14) 1.1063(12) 0.058(2) Uani 1 1 d . . . 

H3C H 0.4164 0.1186 1.1858 0.069 Uiso 1 1 calc R . . 

H3A H 0.5118 0.0868 1.2245 0.069 Uiso 1 1 calc R . . 

H3B H 0.2736 0.0941 1.0163 0.069 Uiso 1 1 calc R . . 

C4 C 0.4798(13) 0.12922(12) 0.7607(11) 0.0380(18) Uani 1 1 d . . . 

C5 C 0.2405(14) 0.12951(12) 0.6266(12) 0.0431(19) Uani 1 1 d . . . 

H5A H 0.1350 0.1155 0.6527 0.052 Uiso 1 1 calc R . . 

C6 C 0.1539(13) 0.14996(12) 0.4550(11) 0.0352(17) Uani 1 1 d . . . 

C7 C 0.3001(12) 0.17068(12) 0.4076(11) 0.0351(17) Uani 1 1 d . . . 

C8 C 0.5396(13) 0.17002(13) 0.5478(12) 0.0383(18) Uani 1 1 d . . . 

C9 C 0.6268(12) 0.14985(13) 0.7192(12) 0.0403(18) Uani 1 1 d . . . 

H9A H 0.7906 0.1502 0.8098 0.048 Uiso 1 1 calc R . . 

C10 C 0.2121(12) 0.19185(12) 0.2172(11) 0.0362(17) Uani 1 1 d . . . 

C11 C 0.3311(12) 0.19583(12) 0.0495(12) 0.0385(17) Uani 1 1 d . . . 

H11A H 0.4708 0.1852 0.0590 0.046 Uiso 1 1 calc R . . 

C12 C 0.2489(13) 0.21515(13) -0.1315(12) 0.0447(19) Uani 1 1 d . . . 

H12A H 0.3323 0.2176 -0.2451 0.054 Uiso 1 1 calc R . . 

C13 C 0.0457(13) 0.23088(13) -0.1478(12) 0.0440(18) Uani 1 1 d . . . 

H13A H -0.0105 0.2441 -0.2724 0.053 Uiso 1 1 calc R . . 

C14 C -0.0748(13) 0.22729(13) 0.0176(12) 0.0458(19) Uani 1 1 d . . . 

H14A H -0.2136 0.2382 0.0078 0.055 Uiso 1 1 calc R . . 

C15 C 0.0061(12) 0.20797(14) 0.1969(12) 0.0460(19) Uani 1 1 d . . . 

H15A H -0.0791 0.2055 0.3090 0.055 Uiso 1 1 calc R . . 

N1 N 0.8634(10) 0.04572(11) 0.4163(9) 0.0401(15) Uani 1 1 d . . . 

C16 C 0.7492(12) 0.02134(13) 0.3554(11) 0.0400(18) Uani 1 1 d . . . 

H16A H 0.6288 0.0164 0.4256 0.048 Uiso 1 1 calc R . . 

C17 C 0.7972(11) 0.00289(13) 0.1951(11) 0.0345(16) Uani 1 1 d . . . 

H17A H 0.7118 -0.0144 0.1592 0.041 Uiso 1 1 calc R . . 

C18 C 0.9704(11) 0.00951(12) 0.0861(10) 0.0301(16) Uani 1 1 d . . . 

C19 C 1.0868(12) 0.03494(12) 0.1481(12) 0.0405(18) Uani 1 1 d . . . 

H19A H 1.2057 0.0406 0.0782 0.049 Uiso 1 1 calc R . . 

C20 C 1.0301(13) 0.05214(13) 0.3120(12) 0.0435(18) Uani 1 1 d . . . 

H20A H 1.1140 0.0694 0.3526 0.052 Uiso 1 1 calc R . . 






_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 

F1 C6 1.313(8) . ? 

F1A C8 1.225(13) . ? 

O1 C1 1.325(8) . ? 

O2 C1 1.198(7) . ? 

C1 C2 1.520(9) . ? 

C2 C3 1.491(9) . ? 

C2 C4 1.532(9) . ? 

C4 C9 1.375(9) . ? 

C4 C5 1.390(9) . ? 

C5 C6 1.388(9) . ? 

C6 C7 1.388(8) . ? 

C7 C8 1.401(9) . ? 

C7 C10 1.484(9) . ? 

C8 C9 1.379(9) . ? 

C10 C11 1.387(8) . ? 

C10 C15 1.404(9) . ? 

C11 C12 1.384(9) . ? 

C12 C13 1.384(9) . ? 

C13 C14 1.379(9) . ? 

C14 C15 1.377(9) . ? 

N1 C16 1.332(8) . ? 

N1 C20 1.339(8) . ? 

C16 C17 1.382(8) . ? 

C17 C18 1.392(8) . ? 

C18 C19 1.382(8) . ? 

C18 C18 1.480(11) 3_755 ? 

C19 C20 1.383(9) . ? 



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 

O2 C1 O1 123.4(6) . . ? 

O2 C1 C2 126.1(6) . . ? 

O1 C1 C2 110.6(6) . . ? 

C3 C2 C1 113.8(6) . . ? 

C3 C2 C4 113.9(6) . . ? 

C1 C2 C4 107.4(5) . . ? 

C9 C4 C5 118.0(6) . . ? 

C9 C4 C2 121.1(7) . . ? 

C5 C4 C2 120.8(6) . . ? 

C6 C5 C4 120.8(6) . . ? 

F1 C6 C7 118.6(6) . . ? 

F1 C6 C5 119.2(6) . . ? 

C7 C6 C5 122.1(7) . . ? 

C6 C7 C8 115.7(6) . . ? 

C6 C7 C10 122.6(6) . . ? 

C8 C7 C10 121.7(6) . . ? 

F1A C8 C9 119.4(9) . . ? 

F1A C8 C7 117.8(8) . . ? 

C9 C8 C7 122.5(6) . . ? 

C4 C9 C8 120.8(7) . . ? 

C11 C10 C15 117.9(6) . . ? 

C11 C10 C7 120.1(6) . . ? 

C15 C10 C7 122.0(6) . . ? 

C12 C11 C10 120.8(6) . . ? 

C13 C12 C11 120.3(6) . . ? 

C14 C13 C12 119.7(6) . . ? 

C15 C14 C13 120.0(6) . . ? 

C14 C15 C10 121.2(6) . . ? 

C16 N1 C20 116.7(5) . . ? 

N1 C16 C17 123.3(6) . . ? 

C16 C17 C18 120.1(6) . . ? 

C19 C18 C17 116.4(5) . . ? 

C19 C18 C18 121.2(7) . 3_755 ? 

C17 C18 C18 122.4(7) . 3_755 ? 

C18 C19 C20 120.0(6) . . ? 

N1 C20 C19 123.5(6) . . ? 



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 17.8(10) . . . . ? 

O1 C1 C2 C3 -162.1(6) . . . . ? 

O2 C1 C2 C4 -109.2(7) . . . . ? 

O1 C1 C2 C4 70.8(7) . . . . ? 

C3 C2 C4 C9 132.8(7) . . . . ? 

C1 C2 C4 C9 -100.2(7) . . . . ? 

C3 C2 C4 C5 -49.6(8) . . . . ? 

C1 C2 C4 C5 77.4(7) . . . . ? 

C9 C4 C5 C6 0.4(9) . . . . ? 

C2 C4 C5 C6 -177.3(5) . . . . ? 

C4 C5 C6 F1 177.5(5) . . . . ? 

C4 C5 C6 C7 0.7(9) . . . . ? 

F1 C6 C7 C8 -178.2(5) . . . . ? 

C5 C6 C7 C8 -1.4(8) . . . . ? 

F1 C6 C7 C10 0.3(9) . . . . ? 

C5 C6 C7 C10 177.1(5) . . . . ? 

C6 C7 C8 F1A -173.4(8) . . . . ? 

C10 C7 C8 F1A 8.1(10) . . . . ? 

C6 C7 C8 C9 1.1(9) . . . . ? 

C10 C7 C8 C9 -177.4(5) . . . . ? 

C5 C4 C9 C8 -0.7(9) . . . . ? 

C2 C4 C9 C8 177.0(5) . . . . ? 

F1A C8 C9 C4 174.3(8) . . . . ? 

C7 C8 C9 C4 -0.1(9) . . . . ? 

C6 C7 C10 C11 -127.6(7) . . . . ? 

C8 C7 C10 C11 50.9(9) . . . . ? 

C6 C7 C10 C15 51.1(9) . . . . ? 

C8 C7 C10 C15 -130.4(7) . . . . ? 

C15 C10 C11 C12 0.1(10) . . . . ? 

C7 C10 C11 C12 178.9(6) . . . . ? 

C10 C11 C12 C13 0.0(10) . . . . ? 

C11 C12 C13 C14 0.1(10) . . . . ? 

C12 C13 C14 C15 -0.5(10) . . . . ? 

C13 C14 C15 C10 0.7(10) . . . . ? 

C11 C10 C15 C14 -0.5(10) . . . . ? 

C7 C10 C15 C14 -179.2(6) . . . . ? 

C20 N1 C16 C17 0.7(9) . . . . ? 

N1 C16 C17 C18 -0.8(10) . . . . ? 

C16 C17 C18 C19 0.1(9) . . . . ? 

C16 C17 C18 C18 179.8(7) . . . 3_755 ? 

C17 C18 C19 C20 0.5(9) . . . . ? 

C18 C18 C19 C20 -179.1(7) 3_755 . . . ? 

C16 N1 C20 C19 0.0(10) . . . . ? 

C18 C19 C20 N1 -0.6(10) . . . . ? 



_diffrn_measured_fraction_theta_max    0.887 

_diffrn_reflns_theta_full              21.69 

_diffrn_measured_fraction_theta_full   0.887 

_refine_diff_density_max    0.285 

_refine_diff_density_min   -0.304 

_refine_diff_density_rms    0.064 



data_sf8232 

_database_code_CSD                  188915



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C42 H36 F2 N2 O4' 

_chemical_formula_weight          670.73 



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' 

'F'  'F'   0.0171   0.0103 

'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 



_symmetry_cell_setting            Monoclinic 

_symmetry_space_group_name_H-M    P2(1)/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                    5.8697(9) 

_cell_length_b                    47.357(7) 

_cell_length_c                    6.3587(10) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  109.492(3) 

_cell_angle_gamma                 90.00 

_cell_volume                      1666.2(4) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     200(2) 

_cell_measurement_reflns_used     ? 

_cell_measurement_theta_min       ? 

_cell_measurement_theta_max       ? 



_exptl_crystal_description        plate 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           0.03 

_exptl_crystal_size_mid           0.5 

_exptl_crystal_size_min           0.15 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.337 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              704 

_exptl_absorpt_coefficient_mu     0.093 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   0.852 

_exptl_absorpt_correction_T_max   1.000 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       200(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'CCD area detector' 

_diffrn_measurement_method        'phi and omega scans' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             6977 

_diffrn_reflns_av_R_equivalents   0.0383 

_diffrn_reflns_av_sigmaI/netI     0.0497 

_diffrn_reflns_limit_h_min        -6 

_diffrn_reflns_limit_h_max        6 

_diffrn_reflns_limit_k_min        -52 

_diffrn_reflns_limit_k_max        37 

_diffrn_reflns_limit_l_min        -7 

_diffrn_reflns_limit_l_max        6 

_diffrn_reflns_theta_min          1.72 

_diffrn_reflns_theta_max          23.29 

_reflns_number_total              2383 

_reflns_number_gt                 1253 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection        'Bruker SMART' 

_computing_cell_refinement        'Bruker SMART' 

_computing_data_reduction         'Bruker SHELXTL' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'Bruker SHELXTL' 

_computing_publication_material   'Bruker SHELXTL' 



_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)+(0.0473P)²+1.1298P] 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          2383 

_refine_ls_number_parameters      238 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1403 

_refine_ls_R_factor_gt            0.0686 

_refine_ls_wR_factor_ref          0.1709 

_refine_ls_wR_factor_gt           0.1395 

_refine_ls_goodness_of_fit_ref    1.042 

_refine_ls_restrained_S_all       1.042 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 



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 

F1 F 0.6500(5) 0.15354(8) 1.0771(5) 0.0966(15) Uani 0.761(5) 1 d P . . 

F1A F -0.1001(16) 0.1940(3) 0.9052(15) 0.086(4) Uani 0.239(5) 1 d P . . 

O1 O -0.2337(6) 0.09040(8) 0.6789(7) 0.1168(13) Uani 1 1 d . . . 

H1 H -0.2315 0.0776 0.7709 0.175 Uiso 1 1 calc R . . 

O2 O 0.0652(6) 0.06529(9) 0.6235(7) 0.1405(17) Uani 1 1 d . . . 

N1 N -0.2980(9) 0.05495(10) 0.9761(9) 0.1225(18) Uani 1 1 d . . . 

C1 C -0.0539(9) 0.08638(14) 0.5987(10) 0.1093(19) Uani 1 1 d . . . 

C2 C -0.0207(8) 0.11301(13) 0.4759(9) 0.1025(17) Uani 1 1 d . . . 

H2 H -0.1850 0.1194 0.3803 0.123 Uiso 1 1 calc R . . 

C3 C 0.1275(9) 0.10818(14) 0.3236(10) 0.138(2) Uani 1 1 d . . . 

H3A H 0.2837 0.0998 0.4095 0.206 Uiso 1 1 calc R . . 

H3B H 0.1541 0.1263 0.2604 0.206 Uiso 1 1 calc R . . 

H3C H 0.0403 0.0953 0.2027 0.206 Uiso 1 1 calc R . . 

C4 C 0.0842(8) 0.13602(12) 0.6523(8) 0.0886(15) Uani 1 1 d . . . 

C5 C 0.3304(8) 0.13575(11) 0.7814(8) 0.0891(15) Uani 1 1 d . . . 

H5 H 0.4365 0.1224 0.7521 0.107 Uiso 1 1 calc R . . 

C6 C 0.4165(7) 0.15510(12) 0.9508(8) 0.0865(15) Uani 1 1 d . . . 

C7 C 0.2755(7) 0.17535(11) 1.0053(7) 0.0819(14) Uani 1 1 d . . . 

C8 C 0.0314(7) 0.17590(13) 0.8706(7) 0.0866(16) Uani 1 1 d . . . 

C9 C -0.0595(7) 0.15671(12) 0.7003(8) 0.0919(16) Uani 1 1 d . . . 

H9 H -0.2259 0.1576 0.6128 0.110 Uiso 1 1 calc R . . 

C10 C 0.3706(7) 0.19512(11) 1.1955(7) 0.0818(14) Uani 1 1 d . . . 

C11 C 0.2557(7) 0.19738(11) 1.3534(7) 0.0909(16) Uani 1 1 d . . . 

H11 H 0.1152 0.1864 1.3373 0.109 Uiso 1 1 calc R . . 

C12 C 0.3424(8) 0.21527(13) 1.5330(7) 0.1041(18) Uani 1 1 d . . . 

H12 H 0.2625 0.2165 1.6403 0.125 Uiso 1 1 calc R . . 

C13 C 0.5467(8) 0.23158(12) 1.5579(7) 0.1022(18) Uani 1 1 d . . . 

H13 H 0.6062 0.2441 1.6810 0.123 Uiso 1 1 calc R . . 

C14 C 0.6625(7) 0.22941(12) 1.4014(7) 0.0963(17) Uani 1 1 d . . . 

H14 H 0.8027 0.2404 1.4175 0.116 Uiso 1 1 calc R . . 

C15 C 0.5763(7) 0.21150(11) 1.2233(7) 0.0885(16) Uani 1 1 d . . . 

H15 H 0.6577 0.2102 1.1172 0.106 Uiso 1 1 calc R . . 

C16 C -0.4657(10) 0.06189(14) 1.0688(14) 0.136(3) Uani 1 1 d . . . 

H16 H -0.5524 0.0791 1.0260 0.164 Uiso 1 1 calc R . . 

C17 C -0.5159(9) 0.04489(16) 1.2239(13) 0.132(2) Uani 1 1 d . . . 

H17 H -0.6369 0.0502 1.2849 0.158 Uiso 1 1 calc R . . 

C18 C -0.3896(13) 0.02014(15) 1.2896(13) 0.141(3) Uani 1 1 d . . . 

C19 C -0.2154(11) 0.01312(14) 1.2020(13) 0.138(3) Uani 1 1 d . . . 

H19 H -0.1231 -0.0036 1.2471 0.166 Uiso 1 1 calc R . . 

C20 C -0.1761(9) 0.03082(14) 1.0468(12) 0.126(2) Uani 1 1 d . . . 

H20 H -0.0549 0.0257 0.9854 0.151 Uiso 1 1 calc R . . 

C21 C -0.4330(9) -0.0038(2) 1.4611(17) 0.164(4) Uani 1 1 d . . . 

H21 H -0.3549 -0.0217 1.4900 0.197 Uiso 1 1 calc R . . 






_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 

F1 C6 1.340(5) . ? 

F1A C8 1.221(10) . ? 

O1 C1 1.330(6) . ? 

O2 C1 1.199(6) . ? 

N1 C20 1.344(6) . ? 

N1 C16 1.346(8) . ? 

C1 C2 1.529(7) . ? 

C2 C3 1.520(6) . ? 

C2 C4 1.537(6) . ? 

C4 C9 1.392(6) . ? 

C4 C5 1.404(6) . ? 

C5 C6 1.375(6) . ? 

C6 C7 1.384(6) . ? 

C7 C8 1.403(5) . ? 

C7 C10 1.483(6) . ? 

C8 C9 1.377(6) . ? 

C10 C11 1.388(5) . ? 

C10 C15 1.396(6) . ? 

C11 C12 1.376(6) . ? 

C12 C13 1.390(6) . ? 

C13 C14 1.384(5) . ? 

C14 C15 1.369(6) . ? 

C16 C17 1.379(8) . ? 

C17 C18 1.375(8) . ? 

C18 C19 1.359(9) . ? 

C18 C21 1.652(12) . ? 

C19 C20 1.372(8) . ? 

C21 C21 1.121(14) 3_458 ? 



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 

C20 N1 C16 116.5(6) . . ? 

O2 C1 O1 124.8(6) . . ? 

O2 C1 C2 125.9(6) . . ? 

O1 C1 C2 109.3(5) . . ? 

C3 C2 C1 113.5(5) . . ? 

C3 C2 C4 113.3(4) . . ? 

C1 C2 C4 107.5(5) . . ? 

C9 C4 C5 117.3(5) . . ? 

C9 C4 C2 122.3(4) . . ? 

C5 C4 C2 120.3(5) . . ? 

C6 C5 C4 119.3(5) . . ? 

F1 C6 C5 117.9(5) . . ? 

F1 C6 C7 117.8(5) . . ? 

C5 C6 C7 124.3(4) . . ? 

C6 C7 C8 115.7(5) . . ? 

C6 C7 C10 123.2(4) . . ? 

C8 C7 C10 121.0(5) . . ? 

F1A C8 C9 120.1(6) . . ? 

F1A C8 C7 118.8(6) . . ? 

C9 C8 C7 121.1(5) . . ? 

C8 C9 C4 122.2(4) . . ? 

C11 C10 C15 118.3(4) . . ? 

C11 C10 C7 119.8(4) . . ? 

C15 C10 C7 121.9(4) . . ? 

C12 C11 C10 120.9(4) . . ? 

C11 C12 C13 120.2(4) . . ? 

C14 C13 C12 119.3(5) . . ? 

C15 C14 C13 120.4(5) . . ? 

C14 C15 C10 121.0(4) . . ? 

N1 C16 C17 122.2(6) . . ? 

C18 C17 C16 119.5(7) . . ? 

C19 C18 C17 119.1(7) . . ? 

C19 C18 C21 113.9(7) . . ? 

C17 C18 C21 126.9(8) . . ? 

C18 C19 C20 118.4(7) . . ? 

N1 C20 C19 124.2(6) . . ? 

C21 C21 C18 110.7(13) 3_458 . ? 



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 17.7(8) . . . . ? 

O1 C1 C2 C3 -163.6(4) . . . . ? 

O2 C1 C2 C4 -108.4(6) . . . . ? 

O1 C1 C2 C4 70.3(5) . . . . ? 

C3 C2 C4 C9 135.4(5) . . . . ? 

C1 C2 C4 C9 -98.4(5) . . . . ? 

C3 C2 C4 C5 -48.6(7) . . . . ? 

C1 C2 C4 C5 77.7(6) . . . . ? 

C9 C4 C5 C6 1.7(7) . . . . ? 

C2 C4 C5 C6 -174.6(5) . . . . ? 

C4 C5 C6 F1 177.2(4) . . . . ? 

C4 C5 C6 C7 0.0(8) . . . . ? 

F1 C6 C7 C8 -179.1(4) . . . . ? 

C5 C6 C7 C8 -1.8(7) . . . . ? 

F1 C6 C7 C10 -0.1(7) . . . . ? 

C5 C6 C7 C10 177.1(5) . . . . ? 

C6 C7 C8 F1A -177.3(7) . . . . ? 

C10 C7 C8 F1A 3.7(9) . . . . ? 

C6 C7 C8 C9 1.9(7) . . . . ? 

C10 C7 C8 C9 -177.0(4) . . . . ? 

F1A C8 C9 C4 178.9(7) . . . . ? 

C7 C8 C9 C4 -0.3(8) . . . . ? 

C5 C4 C9 C8 -1.5(7) . . . . ? 

C2 C4 C9 C8 174.6(5) . . . . ? 

C6 C7 C10 C11 -127.1(5) . . . . ? 

C8 C7 C10 C11 51.8(7) . . . . ? 

C6 C7 C10 C15 52.1(7) . . . . ? 

C8 C7 C10 C15 -129.1(5) . . . . ? 

C15 C10 C11 C12 -0.1(7) . . . . ? 

C7 C10 C11 C12 179.1(4) . . . . ? 

C10 C11 C12 C13 0.5(8) . . . . ? 

C11 C12 C13 C14 -0.6(8) . . . . ? 

C12 C13 C14 C15 0.3(8) . . . . ? 

C13 C14 C15 C10 0.1(8) . . . . ? 

C11 C10 C15 C14 -0.2(7) . . . . ? 

C7 C10 C15 C14 -179.3(4) . . . . ? 

C20 N1 C16 C17 -1.7(9) . . . . ? 

N1 C16 C17 C18 0.8(9) . . . . ? 

C16 C17 C18 C19 0.8(9) . . . . ? 

C16 C17 C18 C21 -176.3(6) . . . . ? 

C17 C18 C19 C20 -1.4(9) . . . . ? 

C21 C18 C19 C20 176.0(5) . . . . ? 

C16 N1 C20 C19 1.0(9) . . . . ? 

C18 C19 C20 N1 0.5(9) . . . . ? 

C19 C18 C21 C21 175.3(9) . . . 3_458 ? 

C17 C18 C21 C21 -7.5(14) . . . 3_458 ? 



_diffrn_measured_fraction_theta_max    0.994 

_diffrn_reflns_theta_full              23.29 

_diffrn_measured_fraction_theta_full   0.994 

_refine_diff_density_max    0.134 

_refine_diff_density_min   -0.140 

_refine_diff_density_rms    0.032 



data_asbi06 

_database_code_CSD                  188916



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C28 H24 N2 O8' 

_chemical_formula_weight          516.49 



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            Orthorhombic 

_symmetry_space_group_name_H-M    Pbcn 



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

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

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

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

'-x, -y, -z' 

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

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

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



_cell_length_a                    28.831(3) 

_cell_length_b                    11.3861(12) 

_cell_length_c                    8.4144(9) 

_cell_angle_alpha                 90.00 

_cell_angle_beta                  90.00 

_cell_angle_gamma                 90.00 

_cell_volume                      2762.2(5) 

_cell_formula_units_Z             4 

_cell_measurement_temperature     173(2) 

_cell_measurement_reflns_used     ? 

_cell_measurement_theta_min       ? 

_cell_measurement_theta_max       ? 



_exptl_crystal_description        block 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           0.50 

_exptl_crystal_size_mid           0.40 

_exptl_crystal_size_min           0.30 

_exptl_crystal_density_meas       0 

_exptl_crystal_density_diffrn     1.242 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              1080 

_exptl_absorpt_coefficient_mu     0.092 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   0.732 

_exptl_absorpt_correction_T_max   1.000

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       173(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'fine-focus sealed tube' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'CCD area detector' 

_diffrn_measurement_method        'phi and omega scans' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             12431 

_diffrn_reflns_av_R_equivalents   0.0419 

_diffrn_reflns_av_sigmaI/netI     0.0302 

_diffrn_reflns_limit_h_min        -34 

_diffrn_reflns_limit_h_max        27 

_diffrn_reflns_limit_k_min        -9 

_diffrn_reflns_limit_k_max        13 

_diffrn_reflns_limit_l_min        -10 

_diffrn_reflns_limit_l_max        9 

_diffrn_reflns_theta_min          1.41 

_diffrn_reflns_theta_max          25.07 

_reflns_number_total              2433 

_reflns_number_gt                 1899 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection        'Bruker SMART' 

_computing_cell_refinement        'Bruker SMART' 

_computing_data_reduction         'Bruker SAINT' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'Bruker SHELXTL' 

_computing_publication_material   'Bruker SHELXTL' 



_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)+(0.0941P)²+0.0000P] 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          2433 

_refine_ls_number_parameters      202 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0541 

_refine_ls_R_factor_gt            0.0419 

_refine_ls_wR_factor_ref          0.1482 

_refine_ls_wR_factor_gt           0.1358 

_refine_ls_goodness_of_fit_ref    1.106 

_refine_ls_restrained_S_all       1.106 

_refine_ls_shift/su_max           0.000 

_refine_ls_shift/su_mean          0.000 



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 0.59923(5) 0.74188(13) 1.09717(16) 0.0436(4) Uani 1 1 d . . . 

O2 O 0.65266(5) 0.64072(12) 1.23042(16) 0.0413(4) Uani 1 1 d . . . 

H2O H 0.6292 0.6448 1.3164 0.050 Uiso 1 1 d R . . 

O3 O 0.64057(5) 0.87414(11) 0.85327(16) 0.0377(4) Uani 1 1 d . . . 

O4 O 0.67886(6) 0.95346(13) 1.0584(2) 0.0562(5) Uani 1 1 d . . . 

N1 N 0.41083(6) 0.63907(14) 1.03881(18) 0.0367(4) Uani 1 1 d . . . 

C1 C 0.45431(8) 0.6681(2) 1.0757(2) 0.0508(6) Uani 1 1 d . . . 

H1 H 0.4609 0.6892 1.1826 0.061 Uiso 1 1 calc R . . 

C2 C 0.49012(7) 0.6692(2) 0.9680(2) 0.0463(6) Uani 1 1 d . . . 

H2 H 0.5206 0.6894 1.0008 0.056 Uiso 1 1 calc R . . 

C3 C 0.48117(7) 0.64051(16) 0.8109(2) 0.0298(5) Uani 1 1 d . . . 

C4 C 0.43587(7) 0.61308(17) 0.7718(2) 0.0334(5) Uani 1 1 d . . . 

H4 H 0.4280 0.5947 0.6650 0.040 Uiso 1 1 calc R . . 

C5 C 0.40215(7) 0.61243(17) 0.8881(2) 0.0330(5) Uani 1 1 d . . . 

H5 H 0.3713 0.5920 0.8590 0.040 Uiso 1 1 calc R . . 

C11 C 0.63700(7) 0.69576(17) 1.1034(2) 0.0307(4) Uani 1 1 d . . . 

C12 C 0.67046(6) 0.69294(16) 0.9677(2) 0.0292(4) Uani 1 1 d . . . 

C13 C 0.70194(7) 0.60041(16) 0.9533(2) 0.0333(5) Uani 1 1 d . . . 

H13 H 0.7025 0.5407 1.0322 0.040 Uiso 1 1 calc R . . 

C14 C 0.73229(7) 0.59387(18) 0.8270(2) 0.0395(5) Uani 1 1 d . . . 

H14 H 0.7528 0.5290 0.8176 0.047 Uiso 1 1 calc R . . 

C15 C 0.73277(7) 0.68232(18) 0.7138(2) 0.0415(5) Uani 1 1 d . . . 

H15 H 0.7539 0.6788 0.6274 0.050 Uiso 1 1 calc R . . 

C16 C 0.70250(7) 0.77518(17) 0.7268(2) 0.0368(5) Uani 1 1 d . . . 

H16 H 0.7030 0.8363 0.6500 0.044 Uiso 1 1 calc R . . 

C17 C 0.67152(6) 0.77963(16) 0.8512(2) 0.0309(4) Uani 1 1 d . . . 

C18 C 0.64831(8) 0.95910(18) 0.9643(2) 0.0405(5) Uani 1 1 d . . . 

C19 C 0.61422(11) 1.0560(2) 0.9481(3) 0.0688(8) Uani 1 1 d . . . 

H19A H 0.6204 1.1160 1.0288 0.103 Uiso 1 1 calc R . . 

H19B H 0.5828 1.0250 0.9627 0.103 Uiso 1 1 calc R . . 

H19C H 0.6169 1.0909 0.8420 0.103 Uiso 1 1 calc R . . 

C101 C 0.5000 1.0000 1.0000 0.078(3) Uani 0.50 2 d SP . . 

C102 C 0.5000 0.991(3) 0.7500 0.132(9) Uani 0.50 2 d SP . . 

C103 C 0.4914(5) 1.0458(11) 0.866(3) 0.083(5) Uani 0.25 1 d P . . 

C104 C 0.5101(5) 0.9508(15) 0.826(3) 0.098(8) Uani 0.25 1 d P . . 






_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 C11 1.210(2) . ? 

O2 C11 1.318(2) . ? 

O3 C18 1.363(2) . ? 

O3 C17 1.398(2) . ? 

O4 C18 1.186(3) . ? 

N1 C5 1.328(2) . ? 

N1 C1 1.333(3) . ? 

C1 C2 1.374(3) . ? 

C2 C3 1.386(3) . ? 

C3 C4 1.383(3) . ? 

C3 C3 1.493(4) 3_656 ? 

C4 C5 1.380(3) . ? 

C11 C12 1.495(3) . ? 

C12 C17 1.392(3) . ? 

C12 C13 1.396(3) . ? 

C13 C14 1.379(3) . ? 

C14 C15 1.386(3) . ? 

C15 C16 1.375(3) . ? 

C16 C17 1.377(3) . ? 

C18 C19 1.484(3) . ? 

C101 C103 1.27(2) 5_677 ? 

C101 C103 1.27(2) . ? 

C101 C104 1.60(3) 5_677 ? 

C101 C104 1.60(3) . ? 

C102 C104 0.83(2) . ? 

C102 C104 0.83(2) 3_656 ? 

C102 C103 1.185(18) . ? 

C102 C103 1.185(18) 3_656 ? 

C103 C104 1.25(3) . ? 

C103 C104 1.94(2) 3_656 ? 

C103 C103 2.01(4) 3_656 ? 

C104 C104 1.40(5) 3_656 ? 

C104 C103 1.94(2) 3_656 ? 



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 

C18 O3 C17 116.76(15) . . ? 

C5 N1 C1 117.15(17) . . ? 

N1 C1 C2 123.72(19) . . ? 

C1 C2 C3 119.2(2) . . ? 

C4 C3 C2 117.15(17) . . ? 

C4 C3 C3 121.6(2) . 3_656 ? 

C2 C3 C3 121.3(2) . 3_656 ? 

C5 C4 C3 119.87(17) . . ? 

N1 C5 C4 122.93(18) . . ? 

O1 C11 O2 123.33(17) . . ? 

O1 C11 C12 123.83(17) . . ? 

O2 C11 C12 112.83(16) . . ? 

C17 C12 C13 117.37(17) . . ? 

C17 C12 C11 122.49(17) . . ? 

C13 C12 C11 120.14(17) . . ? 

C14 C13 C12 121.36(18) . . ? 

C13 C14 C15 119.80(19) . . ? 

C16 C15 C14 119.81(18) . . ? 

C15 C16 C17 120.05(18) . . ? 

C16 C17 C12 121.59(18) . . ? 

C16 C17 O3 116.86(17) . . ? 

C12 C17 O3 121.54(16) . . ? 

O4 C18 O3 122.73(19) . . ? 

O4 C18 C19 126.4(2) . . ? 

O3 C18 C19 110.9(2) . . ? 

C103 C101 C103 180.000(3) 5_677 . ? 

C103 C101 C104 50.3(8) 5_677 5_677 ? 

C103 C101 C104 129.7(8) . 5_677 ? 

C103 C101 C104 129.7(8) 5_677 . ? 

C103 C101 C104 50.3(8) . . ? 

C104 C101 C104 180.0(8) 5_677 . ? 

C104 C102 C104 114(6) . 3_656 ? 

C104 C102 C103 75(2) . . ? 

C104 C102 C103 147.5(14) 3_656 . ? 

C104 C102 C103 147.5(14) . 3_656 ? 

C104 C102 C103 75(2) 3_656 3_656 ? 

C103 C102 C103 116(3) . 3_656 ? 

C102 C103 C104 39.9(11) . . ? 

C102 C103 C101 118.2(15) . . ? 

C104 C103 C101 78.4(17) . . ? 

C102 C103 C104 13.4(6) . 3_656 ? 

C104 C103 C104 46(2) . 3_656 ? 

C101 C103 C104 120.9(12) . 3_656 ? 

C102 C103 C103 32.1(17) . 3_656 ? 

C104 C103 C103 68.6(17) . 3_656 ? 

C101 C103 C103 144.5(9) . 3_656 ? 

C104 C103 C103 37.0(9) 3_656 3_656 ? 

C102 C104 C103 66(2) . . ? 

C102 C104 C104 33(3) . 3_656 ? 

C103 C104 C104 93.8(18) . 3_656 ? 

C102 C104 C101 117(3) . . ? 

C103 C104 C101 51.2(16) . . ? 

C104 C104 C101 139.5(16) 3_656 . ? 

C102 C104 C103 19.2(9) . 3_656 ? 

C103 C104 C103 74(2) . 3_656 ? 

C104 C104 C103 40.2(12) 3_656 3_656 ? 

C101 C104 C103 124.2(12) . 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 

C5 N1 C1 C2 -1.5(4) . . . . ? 

N1 C1 C2 C3 1.0(4) . . . . ? 

C1 C2 C3 C4 0.5(3) . . . . ? 

C1 C2 C3 C3 179.93(18) . . . 3_656 ? 

C2 C3 C4 C5 -1.5(3) . . . . ? 

C3 C3 C4 C5 179.09(13) 3_656 . . . ? 

C1 N1 C5 C4 0.4(3) . . . . ? 

C3 C4 C5 N1 1.1(3) . . . . ? 

O1 C11 C12 C17 28.2(3) . . . . ? 

O2 C11 C12 C17 -152.93(17) . . . . ? 

O1 C11 C12 C13 -151.17(19) . . . . ? 

O2 C11 C12 C13 27.7(2) . . . . ? 

C17 C12 C13 C14 -1.2(3) . . . . ? 

C11 C12 C13 C14 178.16(17) . . . . ? 

C12 C13 C14 C15 1.9(3) . . . . ? 

C13 C14 C15 C16 -1.0(3) . . . . ? 

C14 C15 C16 C17 -0.6(3) . . . . ? 

C15 C16 C17 C12 1.3(3) . . . . ? 

C15 C16 C17 O3 -177.50(18) . . . . ? 

C13 C12 C17 C16 -0.4(3) . . . . ? 

C11 C12 C17 C16 -179.76(17) . . . . ? 

C13 C12 C17 O3 178.37(16) . . . . ? 

C11 C12 C17 O3 -1.0(3) . . . . ? 

C18 O3 C17 C16 -107.34(19) . . . . ? 

C18 O3 C17 C12 73.9(2) . . . . ? 

C17 O3 C18 O4 -1.9(3) . . . . ? 

C17 O3 C18 C19 177.5(2) . . . . ? 

C104 C102 C103 C104 111(9) 3_656 . . . ? 

C103 C102 C103 C104 -147.0(17) 3_656 . . . ? 

C104 C102 C103 C101 -5.3(19) . . . . ? 

C104 C102 C103 C101 105(8) 3_656 . . . ? 

C103 C102 C103 C101 -152.3(14) 3_656 . . . ? 

C104 C102 C103 C104 -111(9) . . . 3_656 ? 

C103 C102 C103 C104 102(8) 3_656 . . 3_656 ? 

C104 C102 C103 C103 147.0(18) . . . 3_656 ? 

C104 C102 C103 C103 -102(8) 3_656 . . 3_656 ? 

C103 C101 C103 C102 -107(100) 5_677 . . . ? 

C104 C101 C103 C102 -176.5(12) 5_677 . . . ? 

C104 C101 C103 C102 3.5(12) . . . . ? 

C103 C101 C103 C104 -111(100) 5_677 . . . ? 

C104 C101 C103 C104 180.000(13) 5_677 . . . ? 

C103 C101 C103 C104 -92(100) 5_677 . . 3_656 ? 

C104 C101 C103 C104 -161.5(11) 5_677 . . 3_656 ? 

C104 C101 C103 C104 18.5(11) . . . 3_656 ? 

C103 C101 C103 C103 -132(100) 5_677 . . 3_656 ? 

C104 C101 C103 C103 158.3(15) 5_677 . . 3_656 ? 

C104 C101 C103 C103 -21.7(15) . . . 3_656 ? 

C104 C102 C104 C103 -146.6(13) 3_656 . . . ? 

C103 C102 C104 C103 114(8) 3_656 . . . ? 

C103 C102 C104 C104 146.6(13) . . . 3_656 ? 

C103 C102 C104 C104 -99(7) 3_656 . . 3_656 ? 

C104 C102 C104 C101 -142.4(19) 3_656 . . . ? 

C103 C102 C104 C101 4.2(16) . . . . ? 

C103 C102 C104 C101 118(7) 3_656 . . . ? 

C104 C102 C104 C103 99(7) 3_656 . . 3_656 ? 

C103 C102 C104 C103 -114(8) . . . 3_656 ? 

C101 C103 C104 C102 175.2(17) . . . . ? 

C104 C103 C104 C102 17.5(19) 3_656 . . . ? 

C103 C103 C104 C102 -18.1(15) 3_656 . . . ? 

C102 C103 C104 C104 -17.5(19) . . . 3_656 ? 

C101 C103 C104 C104 157.7(16) . . . 3_656 ? 

C103 C103 C104 C104 -35.6(15) 3_656 . . 3_656 ? 

C102 C103 C104 C101 -175.2(17) . . . . ? 

C104 C103 C104 C101 -157.7(15) 3_656 . . . ? 

C103 C103 C104 C101 166.7(11) 3_656 . . . ? 

C102 C103 C104 C103 18.1(15) . . . 3_656 ? 

C101 C103 C104 C103 -166.7(11) . . . 3_656 ? 

C104 C103 C104 C103 35.6(15) 3_656 . . 3_656 ? 

C103 C101 C104 C102 175.1(19) 5_677 . . . ? 

C103 C101 C104 C102 -4.9(19) . . . . ? 

C104 C101 C104 C102 56(100) 5_677 . . . ? 

C103 C101 C104 C103 180.000(17) 5_677 . . . ? 

C104 C101 C104 C103 61(100) 5_677 . . . ? 

C103 C101 C104 C104 144.3(17) 5_677 . . 3_656 ? 

C103 C101 C104 C104 -35.7(17) . . . 3_656 ? 

C104 C101 C104 C104 25(100) 5_677 . . 3_656 ? 

C103 C101 C104 C103 -164.4(12) 5_677 . . 3_656 ? 

C103 C101 C104 C103 15.6(12) . . . 3_656 ? 

C104 C101 C104 C103 76(100) 5_677 . . 3_656 ? 



_diffrn_measured_fraction_theta_max    0.994 

_diffrn_reflns_theta_full              25.07 

_diffrn_measured_fraction_theta_full   0.994 

_refine_diff_density_max    0.261 

_refine_diff_density_min   -0.176 

_refine_diff_density_rms    0.047 





