Pirfenidone–flavonoid cocrystals with reduced solubility and dissolution rate
Meng, Lingshan; Li, Duanxiu; Zhu, Yujing; Wang, Jianming; Deng, Zongwu; Zhang, Hailu; CrystEngComm 25 (2023) 5133–5140; doi:10.1039/D3CE00402C

data_7247204
_publ_section_title
;
 Pirfenidone--flavonoid cocrystals with reduced solubility and dissolution
 rate
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5133
_journal_page_last               5140
_journal_paper_doi               10.1039/D3CE00402C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H10 O5, 2(C12 H11 N O)'
_chemical_formula_sum            'C39 H32 N2 O7'
_chemical_formula_weight         640.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2dfmn4
_audit_creation_date             2023-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.594(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9053(6)
_cell_length_b                   8.2831(2)
_cell_length_c                   20.9395(5)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.098
_cell_measurement_theta_min      4.271
_cell_volume                     3242.19(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21466
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         4.271
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.4997.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1275P)^2^+0.0028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5684
_reflns_number_total             6267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00402c2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7247203--7247204.cif.'
_cod_database_code               7247204
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C24(H24), C26(H26), C17(H17), C27(H27), C19(H19),
 C5A(H5A), C3A(H3A), C2A(H2A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C12A(H12A), C5B(H5B), C3B(H3B), C2B(H2B), C12B(H12B), C11B(H11B), C10B(H10B),
 C9B(H9B), C8B(H8B)
3.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC)
;
_shelx_res_checksum              26835
_olex2_submission_special_instructions 'No special instructions were received'