 

data_data 

 

_audit_creation_method            SHELXL 

_chemical_name_systematic 

; 

 ? 

; 

_chemical_name_common             ? 

_chemical_formula_moiety          ? 

_chemical_formula_structural      ? 

_chemical_formula_analytical      ? 

_chemical_formula_sum             'C4 H5 N3 O3 : C7 H9 N5' 

_chemical_formula_weight          306.30 

_chemical_melting_point           ? 

_chemical_compound_source         ? 

 

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                    7.334(3) 

_cell_length_b                    8.164(2) 

_cell_length_c                    12.640(5) 

_cell_angle_alpha                 75.12(3) 

_cell_angle_beta                  82.59(3) 

_cell_angle_gamma                 70.78(3) 

_cell_volume                      689.8(4) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     293(2) 

_cell_measurement_reflns_used     ? 

_cell_measurement_theta_min       ? 

_cell_measurement_theta_max       ? 

 

_exptl_crystal_description        needles

_exptl_crystal_colour             colorless

_exptl_crystal_size_max           0.30 

_exptl_crystal_size_mid           0.25 

_exptl_crystal_size_min           0.30

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.475 

_exptl_crystal_density_method     ? 

_exptl_crystal_F_000              320 

_exptl_absorpt_coefficient_mu     0.113 

_exptl_absorpt_correction_type    ? 

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

 

_exptl_special_details 

; 

 ? 

; 

 

_diffrn_ambient_temperature       293(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        ? 

_diffrn_measurement_method        ? 

_diffrn_standards_number          ? 

_diffrn_standards_interval_count  ? 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             2904 

_diffrn_reflns_av_R_equivalents   0.0992 

_diffrn_reflns_av_sigmaI/netI     0.0879 

_diffrn_reflns_limit_h_min        -8 

_diffrn_reflns_limit_h_max        6 

_diffrn_reflns_limit_k_min        -7 

_diffrn_reflns_limit_k_max        9 

_diffrn_reflns_limit_l_min        -10 

_diffrn_reflns_limit_l_max        14 

_diffrn_reflns_theta_min          1.67 

_diffrn_reflns_theta_max          23.27 

_reflns_number_total              1944 

_reflns_number_observed           1355 

_reflns_observed_criterion        >2sigma(I) 

 

_computing_data_collection        ? 

_computing_cell_refinement        ? 

_computing_data_reduction         ? 

_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 

_computing_molecular_graphics     ? 

_computing_publication_material   ? 

 

_refine_special_details 

; 

 Refinement on F² for ALL reflections except for 39 with very negative F² 

 or flagged by the user for potential systematic errors.  Weighted R-factors 

 wR and all goodnesses of fit S are based on F², conventional R-factors R 

 are based on F, with F set to zero for negative F². The observed criterion 

 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0087P)^2^+0.0894P] where P=(Fo^2^+2Fc^2^)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     ? 

_refine_ls_extinction_method      SHELXL 

_refine_ls_extinction_coef        0.0472(103) 

_refine_ls_extinction_expression 

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

_refine_ls_number_reflns          1905 

_refine_ls_number_parameters      256 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1171 

_refine_ls_R_factor_obs           0.0783 

_refine_ls_wR_factor_all          0.1754 

_refine_ls_wR_factor_obs          0.1380 

_refine_ls_goodness_of_fit_all    1.942 

_refine_ls_goodness_of_fit_obs    1.922 

_refine_ls_restrained_S_all       1.975 

_refine_ls_restrained_S_obs       1.922 

_refine_ls_shift/esd_max          0.455 

_refine_ls_shift/esd_mean         0.028 

 

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_thermal_displace_type 

 _atom_site_occupancy 

 _atom_site_calc_flag 

 _atom_site_refinement_flags 

 _atom_site_disorder_group 

O21 O 0.2554(4) 0.5820(5) 0.9559(3) 0.0492(10) Uani 1 d . . 

O23 O 0.7827(4) 0.2371(5) 0.7954(3) 0.0664(12) Uani 1 d . . 

O22 O 0.2082(5) 0.4702(6) 0.6295(3) 0.0654(12) Uani 1 d . . 

N23 N 0.2265(5) 0.5116(6) 0.7968(3) 0.0441(11) Uani 1 d . . 

N22 N 0.4977(5) 0.3454(6) 0.7088(3) 0.0457(11) Uani 1 d . . 

N21 N 0.5186(5) 0.4021(6) 0.8784(4) 0.0488(12) Uani 1 d . . 

C23 C 0.6113(7) 0.3212(7) 0.7945(4) 0.0476(14) Uani 1 d . . 

C22 C 0.3036(6) 0.4451(7) 0.7068(4) 0.0440(13) Uani 1 d . . 

C21 C 0.3279(6) 0.5057(7) 0.8821(4) 0.0443(13) Uani 1 d . . 

C24 C 0.5911(9) 0.2715(11) 0.6143(6) 0.066(2) Uani 1 d . . 

N15 N 0.4347(5) 0.2518(6) 0.3242(3) 0.0461(11) Uani 1 d . . 

N11 N 0.7320(5) 0.0569(6) 0.2591(3) 0.0467(12) Uani 1 d . . 

N14 N 0.1686(5) 0.3043(6) 0.2123(3) 0.0426(11) Uani 1 d . . 

C17 C 0.4748(6) 0.1212(7) 0.1656(4) 0.0409(12) Uani 1 d . . 

N13 N 0.1946(6) 0.1871(7) 0.0604(4) 0.0524(13) Uani 1 d . . 

C16 C 0.5372(6) 0.1506(7) 0.2551(4) 0.0406(13) Uani 1 d . . 

C15 C 0.2776(6) 0.2037(7) 0.1435(4) 0.0372(12) Uani 1 d . . 

C14 C 0.2506(7) 0.3241(8) 0.2961(4) 0.0465(14) Uani 1 d . . 

N12 N 0.6254(5) 0.0085(6) 0.1139(3) 0.0495(12) Uani 1 d . . 

C12 C 0.8627(8) 0.0361(9) 0.3433(4) 0.0491(14) Uani 1 d . . 

C13 C 0.7740(7) -0.0233(8) 0.1733(4) 0.0503(14) Uani 1 d . . 

C11 C 0.8479(11) -0.1081(11) 0.4417(5) 0.069(2) Uani 1 d . . 

H12B H 1.0085(65) 0.0087(63) 0.3120(37) 0.052(13) Uiso 1 d . . 

H11C H 0.8900(82) -0.2267(99) 0.4201(51) 0.094(23) Uiso 1 d . . 

H13 H 0.9080(65) -0.0983(65) 0.1605(37) 0.051(14) Uiso 1 d . . 

H13B H 0.2750(64) 0.1071(68) 0.0140(39) 0.050(14) Uiso 1 d . . 

H12A H 0.8249(58) 0.1492(70) 0.3617(37) 0.044(14) Uiso 1 d . . 

H13A H 0.0673(72) 0.2557(69) 0.0536(37) 0.053(15) Uiso 1 d . . 

H11B H 0.7202(99) -0.0903(94) 0.4789(59) 0.113(28) Uiso 1 d . . 

H11A H 0.9415(71) -0.1336(76) 0.5037(47) 0.073(16) Uiso 1 d . . 

H21 H 0.5966(61) 0.4006(61) 0.9239(38) 0.034(13) Uiso 1 d . . 

H14 H 0.1521(57) 0.3844(58) 0.3441(35) 0.038(12) Uiso 1 d . . 

H23 H 0.0882(74) 0.5728(72) 0.7949(41) 0.062(15) Uiso 1 d . . 

H24C H 0.4906(103) 0.2877(113) 0.5519(69) 0.144(29) Uiso 1 d . . 

H24A H 0.6660(89) 0.1548(96) 0.6261(53) 0.091(23) Uiso 1 d . . 

H24B H 0.6784(116) 0.3219(126) 0.5662(75) 0.157(39) Uiso 1 d . . 

 


 

_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 

O21 C21 1.222(6) . ? 

O23 C23 1.218(5) . ? 

O22 C22 1.210(6) . ? 

N23 C22 1.363(6) . ? 

N23 C21 1.369(6) . ? 

N23 H23 0.97(5) . ? 

N22 C23 1.386(7) . ? 

N22 C22 1.388(5) . ? 

N22 C24 1.465(7) . ? 

N21 C23 1.378(7) . ? 

N21 C21 1.378(6) . ? 

N21 H21 0.86(5) . ? 

C24 H24C 1.10(9) . ? 

C24 H24A 0.91(7) . ? 

C24 H24B 0.95(9) . ? 

N15 C14 1.338(5) . ? 

N15 C16 1.343(6) . ? 

N11 C13 1.359(7) . ? 

N11 C16 1.381(5) . ? 

N11 C12 1.464(6) . ? 

N14 C15 1.350(6) . ? 

N14 C14 1.351(6) . ? 

C17 C16 1.376(7) . ? 

C17 N12 1.395(6) . ? 

C17 C15 1.410(6) . ? 

N13 C15 1.337(6) . ? 

N13 H13B 0.99(5) . ? 

N13 H13A 0.92(5) . ? 

C14 H14 0.97(4) . ? 

N12 C13 1.320(6) . ? 

C12 C11 1.497(8) . ? 

C12 H12B 1.06(4) . ? 

C12 H12A 0.95(5) . ? 

C13 H13 0.99(5) . ? 

C11 H11C 1.01(8) . ? 

C11 H11B 0.98(7) . ? 

C11 H11A 1.04(6) . ? 

 

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 

C22 N23 C21 125.7(4) . . ? 

C22 N23 H23 113.9(31) . . ? 

C21 N23 H23 120.2(31) . . ? 

C23 N22 C22 122.5(4) . . ? 

C23 N22 C24 118.0(4) . . ? 

C22 N22 C24 119.4(4) . . ? 

C23 N21 C21 125.8(5) . . ? 

C23 N21 H21 113.0(29) . . ? 

C21 N21 H21 120.1(30) . . ? 

O23 C23 N21 121.8(5) . . ? 

O23 C23 N22 122.6(5) . . ? 

N21 C23 N22 115.6(4) . . ? 

O22 C22 N23 122.1(4) . . ? 

O22 C22 N22 121.7(5) . . ? 

N23 C22 N22 116.3(4) . . ? 

O21 C21 N23 123.3(4) . . ? 

O21 C21 N21 123.1(4) . . ? 

N23 C21 N21 113.6(5) . . ? 

N22 C24 H24C 114.1(40) . . ? 

N22 C24 H24A 118.9(43) . . ? 

H24C C24 H24A 105.3(63) . . ? 

N22 C24 H24B 120.2(62) . . ? 

H24C C24 H24B 96.7(62) . . ? 

H24A C24 H24B 98.3(61) . . ? 

C14 N15 C16 110.1(4) . . ? 

C13 N11 C16 105.7(4) . . ? 

C13 N11 C12 126.9(4) . . ? 

C16 N11 C12 127.2(4) . . ? 

C15 N14 C14 119.9(4) . . ? 

C16 C17 N12 111.1(4) . . ? 

C16 C17 C15 116.9(4) . . ? 

N12 C17 C15 132.0(4) . . ? 

C15 N13 H13B 117.7(26) . . ? 

C15 N13 H13A 113.9(31) . . ? 

H13B N13 H13A 128.4(40) . . ? 

N15 C16 C17 128.3(4) . . ? 

N15 C16 N11 125.9(4) . . ? 

C17 C16 N11 105.8(4) . . ? 

N13 C15 N14 119.1(4) . . ? 

N13 C15 C17 124.1(5) . . ? 

N14 C15 C17 116.8(4) . . ? 

N15 C14 N14 128.1(5) . . ? 

N15 C14 H14 120.9(25) . . ? 

N14 C14 H14 110.3(25) . . ? 

C13 N12 C17 102.8(4) . . ? 

N11 C12 C11 111.9(5) . . ? 

N11 C12 H12B 111.3(26) . . ? 

C11 C12 H12B 109.3(25) . . ? 

N11 C12 H12A 105.2(27) . . ? 

C11 C12 H12A 111.2(27) . . ? 

H12B C12 H12A 107.8(38) . . ? 

N12 C13 N11 114.6(4) . . ? 

N12 C13 H13 126.1(28) . . ? 

N11 C13 H13 119.3(28) . . ? 

C12 C11 H11C 109.6(35) . . ? 

C12 C11 H11B 115.1(40) . . ? 

H11C C11 H11B 108.9(56) . . ? 

C12 C11 H11A 115.9(30) . . ? 

H11C C11 H11A 101.7(47) . . ? 

H11B C11 H11A 104.7(52) . . ? 

 

_refine_diff_density_max    0.417 

_refine_diff_density_min   -0.354 

_refine_diff_density_rms    0.112 

