New insight into improving the solubility of poorly soluble drugs by preventing the formation of their hydrogen-bonds: a case of dapsone salts with camphorsulfonic and 5-sulfosalicylic acid
Wu, Yanhui; Hao, Xiujia; Li, Jianting; Guan, Aiying; Zhou, Zhengzheng; Guo, Fang; CrystEngComm 23 (2021) 6191–6198; doi:10.1039/D1CE00847A

data_7243302
_publ_section_title
;
 New insight into improving the solubility of poorly soluble drugs by
 preventing the formation of their hydrogen-bonds: a case of dapsone salts
 with camphorsulfonic and 5-sulfosalicylic acid
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6191
_journal_page_last               6198
_journal_paper_doi               10.1039/D1CE00847A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '2(C7 H5 O6 S), C12 H14 N2 O2 S'
_chemical_formula_sum            'C26 H24 N2 O14 S3'
_chemical_formula_weight         684.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-06 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.326(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.252(5)
_cell_length_b                   13.2429(16)
_cell_length_c                   11.3983(15)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.338
_cell_measurement_theta_min      3.076
_cell_volume                     5765.4(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23826
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.9037.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       needle
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0268P)^2^+38.7274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5866
_reflns_number_total             6897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00847a2.cif
_cod_data_source_block           DAP-SSA
_cod_depositor_comments
'Adding full bibliography for 7243301--7243302.cif.'
_cod_original_cell_volume        5765.4(12)
_cod_database_code               7243302
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9022(17)
 0.0978(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C3(H3), C2(H2), C14(H14A), C25(H25), C6(H6), C12(H12),
 C8(H8), C5(H5), C11(H11), C24(H24), C15(H15), C9(H9)
3.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
3.c Idealised tetrahedral OH refined as rotating group:
 O8(H8A), O6(H6A), O12(H12A), O14(H14)
;
_shelx_res_checksum              29662
_olex2_submission_special_instructions 'No special instructions were received'