Preparation and solid-state characterization of dapsone pharmaceutical cocrystals through the supramolecular synthon strategy
Zhao, Chenyang; Li, Wanya; Li, Zhonghua; Hu, Weiguo; Zhang, Suoqing; Wu, Songgu; CrystEngComm 23 (2021) 6690–6702; doi:10.1039/D1CE00945A

data_7243682
_publ_section_title
;
 Preparation and solid-state characterization of dapsone pharmaceutical
 cocrystals through the supramolecular synthon strategy
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              6690
_journal_page_last               6702
_journal_paper_doi               10.1039/D1CE00945A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '2(C12 H12 N2 O2 S), C9 H13 N3'
_chemical_formula_sum            'C33 H37 N7 O4 S2'
_chemical_formula_weight         659.81
_chemical_name_systematic        'DAP-PYR (2:1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-20 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.67(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7687(12)
_cell_length_b                   7.8235(16)
_cell_length_c                   35.517(7)
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9344
_cell_measurement_theta_min      2.2947
_cell_volume                     1602.3(6)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'rigaku saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            16270
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_min         2.845
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0573P)^2^+0.1873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2925
_reflns_number_total             3813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00945a2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7243681--7243682.cif.'
_cod_database_code               7243682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N2-H2A = N2-H2B
 0.9 with sigma of 0.01
 H1A-H1B = H2A-H2B
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N3 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim N4 \\sim C18 \\sim
C19 \\sim N5 \\sim C20 \\sim C21: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N3) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(N4) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(N5) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Fixed Sof: N3(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) N4(0.5) C19(0.5) H19A(0.5) H19B(0.5) C18(0.5)
 H18A(0.5) H18B(0.5) N5(0.5) H5A(0.5) C21(0.5) H21A(0.5) H21B(0.5) C20(0.5)
 H20A(0.5) H20B(0.5)
5.a Riding coordinates:
 N5(H5A)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C21(H21A,H21B), C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17)
5.d Fitted hexagon refined as free rotating group:
 N3(C13,C14,C15,C16,C17)
;
_shelx_res_checksum              57122
_shelx_hkl_checksum              35265
_olex2_submission_special_instructions 'No special instructions were received'