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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/7/21/88/7218806.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_7218806
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            'C26 H30 N12 O8'
_chemical_formula_weight         638.62
_chemical_name_common            ADI
_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                75.126(11)
_cell_angle_beta                 87.661(10)
_cell_angle_gamma                83.717(11)
_cell_formula_units_Z            1
_cell_length_a                   5.2426(8)
_cell_length_b                   11.965(2)
_cell_length_c                   12.256(2)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      4.50
_cell_volume                     738.5(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10677
_diffrn_reflns_theta_full        24.91
_diffrn_reflns_theta_max         24.91
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0398
_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)+(0.0538P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1709
_reflns_number_total             2567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce02044h2.cif
_cod_data_source_block           C:\Users\JRWang\Desktop\ADI\2013109.CIF
_cod_depositor_comments
'Adding full bibliography for 7218806--7218809.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218806
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 0.6086(3) 0.46151(12) 0.66522(11) 0.0531(4) Uani 1 1 d .
H1 H 0.733(4) 0.4238(19) 0.6213(18) 0.080 Uiso 1 1 d .
O2 O 0.8968(3) 0.39007(14) 0.79811(11) 0.0692(5) Uani 1 1 d .
N3' N -0.0117(3) 1.03953(15) 0.82285(14) 0.0472(5) Uani 1 1 d .
H6 H 0.002(4) 1.0370(18) 0.8934(18) 0.071 Uiso 1 1 d .
O4 O 0.1448(2) 0.96181(11) 0.68166(10) 0.0472(4) Uani 1 1 d .
N3 N 0.6905(3) 0.09054(14) 0.54365(14) 0.0415(4) Uani 1 1 d .
H13 H 0.673(4) 0.0904(16) 0.4711(17) 0.062 Uiso 1 1 d .
O6 O 0.5639(2) 0.15534(12) 0.69641(10) 0.0512(4) Uani 1 1 d .
N1' N 0.3370(3) 0.89693(13) 0.96735(12) 0.0407(4) Uani 1 1 d .
C6 C 0.6932(4) 0.44280(16) 0.76896(15) 0.0410(5) Uani 1 1 d .
C7 C 0.5108(3) 0.49492(17) 0.84314(14) 0.0431(5) Uani 1 1 d .
H3 H 0.3491 0.4617 0.8461 0.052 Uiso 1 1 calc R
H2 H 0.4784 0.5777 0.8091 0.052 Uiso 1 1 calc R
C8 C 0.6015(3) 0.47729(17) 0.96262(14) 0.0433(5) Uani 1 1 d .
H4 H 0.7541 0.5169 0.9608 0.052 Uiso 1 1 calc R
H5 H 0.6477 0.3950 0.9951 0.052 Uiso 1 1 calc R
C5' C 0.1524(3) 0.96902(16) 0.78011(15) 0.0363(5) Uani 1 1 d .
C1' C 0.3559(3) 0.89856(15) 0.85796(14) 0.0340(4) Uani 1 1 d .
C4' C 0.5255(4) 0.83470(16) 1.03208(15) 0.0440(5) Uani 1 1 d .
H19 H 0.5201 0.8312 1.1088 0.053 Uiso 1 1 calc R
C3' C 0.7289(4) 0.77514(16) 0.98952(15) 0.0450(5) Uani 1 1 d .
H7 H 0.8570 0.7335 1.0384 0.054 Uiso 1 1 calc R
N2' N 0.7488(3) 0.77504(14) 0.88118(13) 0.0497(4) Uani 1 1 d .
C2' C 0.5586(4) 0.83760(17) 0.81673(15) 0.0455(5) Uani 1 1 d .
H8 H 0.5632 0.8402 0.7402 0.055 Uiso 1 1 calc R
C5 C 0.5343(3) 0.15295(15) 0.59803(14) 0.0362(4) Uani 1 1 d .
C1 C 0.3108(3) 0.22477(14) 0.53469(14) 0.0334(4) Uani 1 1 d .
N1 N 0.2793(3) 0.22436(13) 0.42717(12) 0.0417(4) Uani 1 1 d .
C4 C 0.0776(4) 0.29044(17) 0.37565(15) 0.0472(5) Uani 1 1 d .
H18 H 0.0480 0.2918 0.3010 0.057 Uiso 1 1 calc R
C3 C -0.0898(4) 0.35719(17) 0.42874(16) 0.0444(5) Uani 1 1 d .
H17 H -0.2273 0.4030 0.3887 0.053 Uiso 1 1 calc R
N2 N -0.0600(3) 0.35783(13) 0.53562(12) 0.0420(4) Uani 1 1 d .
C2 C 0.1414(4) 0.29123(16) 0.58834(15) 0.0408(5) Uani 1 1 d .
H16 H 0.1691 0.2893 0.6633 0.049 Uiso 1 1 calc R
H9 H 0.839(4) 0.0450(16) 0.5839(16) 0.064(6) Uiso 1 1 d .
H10 H -0.169(5) 1.0842(19) 0.7740(18) 0.086(7) 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
C6 O1 H1 109.2(13) . .
C5' N3' H6 117.6(15) . .
C5' N3' H10 118.5(12) . .
H6 N3' H10 123(2) . .
C5 N3 H13 124.3(13) . .
C5 N3 H9 117.6(11) . .
H13 N3 H9 118.0(17) . .
C4' N1' C1' 115.99(15) . .
O2 C6 O1 122.43(17) . .
O2 C6 C7 124.69(17) . .
O1 C6 C7 112.88(16) . .
C6 C7 C8 114.77(16) . .
C6 C7 H3 108.6 . .
C8 C7 H3 108.6 . .
C6 C7 H2 108.6 . .
C8 C7 H2 108.6 . .
H3 C7 H2 107.5 . .
C7 C8 C8 112.52(19) . 2_667
C7 C8 H4 109.1 . .
C8 C8 H4 109.1 2_667 .
C7 C8 H5 109.1 . .
C8 C8 H5 109.1 2_667 .
H4 C8 H5 107.8 . .
O4 C5' N3' 123.26(17) . .
O4 C5' C1' 120.71(16) . .
N3' C5' C1' 116.02(16) . .
N1' C1' C2' 121.19(16) . .
N1' C1' C5' 118.63(16) . .
C2' C1' C5' 120.18(15) . .
N1' C4' C3' 122.24(17) . .
N1' C4' H19 118.9 . .
C3' C4' H19 118.9 . .
N2' C3' C4' 122.39(18) . .
N2' C3' H7 118.8 . .
C4' C3' H7 118.8 . .
C3' N2' C2' 115.02(17) . .
N2' C2' C1' 123.15(17) . .
N2' C2' H8 118.4 . .
C1' C2' H8 118.4 . .
O6 C5 N3 123.92(17) . .
O6 C5 C1 118.84(16) . .
N3 C5 C1 117.24(16) . .
N1 C1 C2 121.40(16) . .
N1 C1 C5 119.32(15) . .
C2 C1 C5 119.29(16) . .
C4 N1 C1 116.26(15) . .
N1 C4 C3 122.36(17) . .
N1 C4 H18 118.8 . .
C3 C4 H18 118.8 . .
N2 C3 C4 121.69(17) . .
N2 C3 H17 119.2 . .
C4 C3 H17 119.2 . .
C3 N2 C2 116.42(16) . .
N2 C2 C1 121.87(17) . .
N2 C2 H16 119.1 . .
C1 C2 H16 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.320(2) .
O1 H1 0.98(2) .
O2 C6 1.197(2) .
N3' C5' 1.326(2) .
N3' H6 0.86(2) .
N3' H10 1.05(2) .
O4 C5' 1.2341(19) .
N3 C5 1.323(2) .
N3 H13 0.90(2) .
N3 H9 0.97(2) .
O6 C5 1.2300(19) .
N1' C4' 1.327(2) .
N1' C1' 1.336(2) .
C6 C7 1.490(2) .
C7 C8 1.514(2) .
C7 H3 0.9700 .
C7 H2 0.9700 .
C8 C8 1.522(3) 2_667
C8 H4 0.9700 .
C8 H5 0.9700 .
C5' C1' 1.494(2) .
C1' C2' 1.376(2) .
C4' C3' 1.377(2) .
C4' H19 0.9300 .
C3' N2' 1.328(2) .
C3' H7 0.9300 .
N2' C2' 1.332(2) .
C2' H8 0.9300 .
C5 C1 1.492(2) .
C1 N1 1.336(2) .
C1 C2 1.386(2) .
N1 C4 1.326(2) .
C4 C3 1.378(2) .
C4 H18 0.9300 .
C3 N2 1.328(2) .
C3 H17 0.9300 .
N2 C2 1.332(2) .
C2 H16 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 C6 C7 C8 0.3(3) .
O1 C6 C7 C8 -179.09(16) .
C6 C7 C8 C8 -174.9(2) 2_667
C4' N1' C1' C2' 0.8(3) .
C4' N1' C1' C5' -178.79(15) .
O4 C5' C1' N1' -171.02(16) .
N3' C5' C1' N1' 10.2(2) .
O4 C5' C1' C2' 9.4(3) .
N3' C5' C1' C2' -169.37(17) .
C1' N1' C4' C3' 0.0(3) .
N1' C4' C3' N2' -0.7(3) .
C4' C3' N2' C2' 0.6(3) .
C3' N2' C2' C1' 0.2(3) .
N1' C1' C2' N2' -0.9(3) .
C5' C1' C2' N2' 178.65(17) .
O6 C5 C1 N1 178.84(16) .
N3 C5 C1 N1 -0.8(2) .
O6 C5 C1 C2 -0.6(3) .
N3 C5 C1 C2 179.75(16) .
C2 C1 N1 C4 -0.2(3) .
C5 C1 N1 C4 -179.70(16) .
C1 N1 C4 C3 0.7(3) .
N1 C4 C3 N2 -0.9(3) .
C4 C3 N2 C2 0.5(3) .
C3 N2 C2 C1 0.0(3) .
N1 C1 C2 N2 -0.1(3) .
C5 C1 C2 N2 179.35(16) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199495
