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_7247203
_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         'C16 H14 O6, C12 H11 N O'
_chemical_formula_sum            'C28 H25 N O7'
_chemical_formula_weight         487.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dzvkt
_audit_creation_date             2023-04-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-21 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0415(10)
_cell_length_b                   6.6425(4)
_cell_length_c                   44.992(3)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      56.809
_cell_measurement_theta_min      2.943
_cell_volume                     4794.2(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            27396
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.559
_diffrn_source_current           2.85
_diffrn_source_power             0.199101
_diffrn_source_voltage           69.86
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1389 before and 0.0819 after correction.
The Ratio of minimum to maximum transmission is 0.6982.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4864
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0670
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+4.2983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.1960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3666
_reflns_number_total             4864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00402c2.cif
_cod_data_source_block           111
_cod_depositor_comments
'Adding full bibliography for 7247203--7247204.cif.'
_cod_database_code               7247203
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C13B \\sim C13A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C13A)=Sof(H13A)=FVAR(1)
4.a Riding coordinates:
 O5(H5), O4(H4), O7(H7)
4.b Ternary CH refined with riding coordinates:
 C13A(H13A), C13B(H13B)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D)
4.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C5(H5A), C24(H24), C3(H3), C27(H27), C23(H23), C8(H8),
 C2(H2), C9(H9), C12(H12), C10(H10), C11(H11)
4.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              89773
_olex2_submission_special_instructions 'No special instructions were received'