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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/88/7218807.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7218807
loop_
_publ_author_name
'Wang, Jian-Rong'
'Ye, Chanjuan'
'Zhu, Bingqing'
'Zhou, Chun'
'Mei, Xuefeng'
_publ_section_title
;
 Pharmaceutical cocrystals of the anti-tuberculosis drug pyrazinamide with
 dicarboxylic and tricarboxylic acids
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              747
_journal_paper_doi               10.1039/C4CE02044H
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C20 H28 N6 O6'
_chemical_formula_weight         448.48
_chemical_name_common            PZA-SEB
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.781(5)
_cell_angle_beta                 83.380(5)
_cell_angle_gamma                86.981(6)
_cell_formula_units_Z            1
_cell_length_a                   5.0909(4)
_cell_length_b                   5.4368(5)
_cell_length_c                   20.3002(17)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      4.50
_cell_volume                     557.29(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8078
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.1320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1560
_reflns_number_total             1951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce02044h2.cif
_cod_data_source_block           C:\Users\JRWang\Desktop\SEB\2013092.CIF
_cod_depositor_comments
'Adding full bibliography for 7218806--7218809.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218807
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 1.2714(3) 0.3122(2) 0.68785(6) 0.0626(4) Uani 1 1 d .
O2 O 1.0871(3) 0.6558(2) 0.73269(6) 0.0676(4) Uani 1 1 d .
O3 O 0.6283(2) 0.1695(2) 0.06529(6) 0.0550(4) Uani 1 1 d .
N1 N 0.1333(2) 0.6435(2) 0.10287(7) 0.0446(4) Uani 1 1 d .
N2 N 0.2392(3) 0.2421(3) 0.02349(7) 0.0501(4) Uani 1 1 d D
H13 H 0.089(3) 0.320(3) 0.0268(10) 0.075 Uiso 1 1 d D
H11 H 0.271(4) 0.123(3) -0.0034(9) 0.075 Uiso 1 1 d D
N3 N 0.4359(3) 0.7043(3) 0.20688(7) 0.0480(4) Uani 1 1 d .
C1 C 1.1087(3) 0.5097(3) 0.68882(8) 0.0453(4) Uani 1 1 d .
C2 C 0.9531(4) 0.5204(3) 0.63079(8) 0.0546(5) Uani 1 1 d .
H6 H 0.8193 0.3990 0.6379 0.065 Uiso 1 1 calc R
H5 H 1.0711 0.4724 0.5917 0.065 Uiso 1 1 calc R
C3 C 0.8178(4) 0.7658(3) 0.61646(8) 0.0508(4) Uani 1 1 d .
H3 H 0.9471 0.8917 0.6126 0.061 Uiso 1 1 calc R
H2 H 0.6850 0.8079 0.6532 0.061 Uiso 1 1 calc R
C4 C 0.6869(4) 0.7632(3) 0.55315(9) 0.0539(5) Uani 1 1 d .
H4 H 0.8185 0.7060 0.5176 0.065 Uiso 1 1 calc R
H7 H 0.5506 0.6439 0.5588 0.065 Uiso 1 1 calc R
C5 C 0.5637(4) 1.0048(3) 0.53172(8) 0.0526(5) Uani 1 1 d .
H8 H 0.6992 1.1248 0.5260 0.063 Uiso 1 1 calc R
H9 H 0.4306 1.0620 0.5669 0.063 Uiso 1 1 calc R
C6 C 0.2307(3) 0.8573(3) 0.19718(8) 0.0482(4) Uani 1 1 d .
H10 H 0.1870 0.9884 0.2257 0.058 Uiso 1 1 calc R
C7 C 0.0814(3) 0.8258(3) 0.14585(9) 0.0484(4) Uani 1 1 d .
H12 H -0.0612 0.9363 0.1410 0.058 Uiso 1 1 calc R
C8 C 0.3419(3) 0.4924(3) 0.11203(7) 0.0375(4) Uani 1 1 d .
C9 C 0.4140(3) 0.2866(3) 0.06443(7) 0.0394(4) Uani 1 1 d .
C10 C 0.4905(3) 0.5219(3) 0.16381(8) 0.0435(4) Uani 1 1 d .
H14 H 0.6328 0.4113 0.1688 0.052 Uiso 1 1 calc R
H1 H 1.358(4) 0.303(4) 0.7230(10) 0.065 Uiso 1 1 d .
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'
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
C1 O1 H1 111.6(13) . .
C7 N1 C8 115.90(13) . .
C9 N2 H13 120.6(14) . .
C9 N2 H11 119.3(14) . .
H13 N2 H11 119.7(19) . .
C6 N3 C10 116.39(14) . .
O2 C1 O1 122.79(15) . .
O2 C1 C2 125.35(15) . .
O1 C1 C2 111.82(14) . .
C1 C2 C3 116.24(14) . .
C1 C2 H6 108.2 . .
C3 C2 H6 108.2 . .
C1 C2 H5 108.2 . .
C3 C2 H5 108.2 . .
H6 C2 H5 107.4 . .
C2 C3 C4 111.98(14) . .
C2 C3 H3 109.2 . .
C4 C3 H3 109.2 . .
C2 C3 H2 109.2 . .
C4 C3 H2 109.2 . .
H3 C3 H2 107.9 . .
C5 C4 C3 116.13(14) . .
C5 C4 H4 108.3 . .
C3 C4 H4 108.3 . .
C5 C4 H7 108.3 . .
C3 C4 H7 108.3 . .
H4 C4 H7 107.4 . .
C4 C5 C5 114.63(18) . 2_676
C4 C5 H8 108.6 . .
C5 C5 H8 108.6 2_676 .
C4 C5 H9 108.6 . .
C5 C5 H9 108.6 2_676 .
H8 C5 H9 107.6 . .
N3 C6 C7 121.52(15) . .
N3 C6 H10 119.2 . .
C7 C6 H10 119.2 . .
N1 C7 C6 122.52(14) . .
N1 C7 H12 118.7 . .
C6 C7 H12 118.7 . .
N1 C8 C10 121.76(14) . .
N1 C8 C9 118.46(13) . .
C10 C8 C9 119.78(13) . .
O3 C9 N2 123.95(14) . .
O3 C9 C8 119.50(13) . .
N2 C9 C8 116.54(13) . .
N3 C10 C8 121.89(14) . .
N3 C10 H14 119.1 . .
C8 C10 H14 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3198(19) .
O1 H1 0.88(2) .
O2 C1 1.1978(19) .
O3 C9 1.2358(17) .
N1 C7 1.330(2) .
N1 C8 1.3355(18) .
N2 C9 1.3201(19) .
N2 H13 0.852(9) .
N2 H11 0.853(9) .
N3 C6 1.331(2) .
N3 C10 1.333(2) .
C1 C2 1.492(2) .
C2 C3 1.508(2) .
C2 H6 0.9700 .
C2 H5 0.9700 .
C3 C4 1.515(2) .
C3 H3 0.9700 .
C3 H2 0.9700 .
C4 C5 1.503(2) .
C4 H4 0.9700 .
C4 H7 0.9700 .
C5 C5 1.510(3) 2_676
C5 H8 0.9700 .
C5 H9 0.9700 .
C6 C7 1.377(2) .
C6 H10 0.9300 .
C7 H12 0.9300 .
C8 C10 1.381(2) .
C8 C9 1.497(2) .
C10 H14 0.9300 .
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_4
O2 C1 C2 C3 18.0(3) .
O1 C1 C2 C3 -164.07(16) .
C1 C2 C3 C4 174.72(16) .
C2 C3 C4 C5 -175.61(16) .
C3 C4 C5 C5 179.7(2) 2_676
C10 N3 C6 C7 0.8(2) .
C8 N1 C7 C6 -0.6(2) .
N3 C6 C7 N1 -0.5(3) .
C7 N1 C8 C10 1.2(2) .
C7 N1 C8 C9 -178.74(14) .
N1 C8 C9 O3 168.47(15) .
C10 C8 C9 O3 -11.5(2) .
N1 C8 C9 N2 -11.6(2) .
C10 C8 C9 N2 168.49(15) .
C6 N3 C10 C8 -0.2(2) .
N1 C8 C10 N3 -0.9(2) .
C9 C8 C10 N3 179.09(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199496
