Sulfonate salts of the therapeutic agent dapsone: 4-[(4-aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4-[(4-aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate
Gaytán-Barrientos, Nancy Sarahy; Morales-Morales, David; Herrera-Ruiz, Dea; Reyes-Martínez, Reyna; Rivera-Islas, Jesús; Acta Crystallographica Section C 72 (2016) 280–284; doi:10.1107/S2053229616003284

data_2020432
_publ_section_title
;
 Sulfonate salts of the therapeutic agent dapsone:
 4-[(4-aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and
 4-[(4-aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate
;
_journal_coeditor_code           OV3072
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              280
_journal_page_last               284
_journal_paper_doi               10.1107/S2053229616003284
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H13 N2 O2 S +, C6 H5 O3 S -, H2 O'
_chemical_formula_moiety         'C12 H13 N2 O2 S +, C6 H5 O3 S -, H2 O'
_chemical_formula_sum            'C18 H20 N2 O6 S2'
_chemical_formula_weight         424.48
_chemical_name_systematic
;
4-[(4-Aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.954(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7220(15)
_cell_length_b                   6.1383(6)
_cell_length_c                   19.5185(19)
_cell_measurement_reflns_used    9553
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.60
_cell_volume                     1876.6(3)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
XP (Bruker, 2012) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15097
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.309
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       Prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.383
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0320P)^2^+1.4352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2988
_reflns_number_total             3415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3072sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2020432--2020433.cif.'
_cod_database_code               2020432
_cod_database_fobs_code          2020432
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              48405
_shelx_res_checksum              63429