Proton-transfer compounds with 4-amino-<i>N</i>-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine): the structures and hydrogen bonding in the salts with 5-nitrosalicylic acid and picric acid
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 69 (2013) 538–543; doi:10.1107/S0108270113009487

data_2018966
_publ_section_title
;
 Proton-transfer compounds with
 4-amino-<i>N</i>-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
 (sulfamethazine): the structures and hydrogen bonding in the salts with
 5-nitrosalicylic acid and picric acid
;
_journal_coeditor_code           KY3031
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              538
_journal_page_last               543
_journal_paper_doi               10.1107/S0108270113009487
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H15 N4 O2 S + , C7 H4 N O5 -'
_chemical_formula_moiety         'C12 H15 N4 O2 S +, C7 H4 N O5 -'
_chemical_formula_sum            'C19 H19 N5 O7 S'
_chemical_formula_weight         461.46
_chemical_melting_point_gt       478
_chemical_melting_point_lt       479
_chemical_name_common            'sulfamethazinium 5-nitrosalicylate'
_chemical_name_systematic
;
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidinium
2-hydroxy-5-nitrobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.094(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.1611(2)
_cell_length_b                   14.0977(2)
_cell_length_c                   22.1219(3)
_cell_measurement_reflns_used    13808
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.71
_cell_measurement_theta_min      3.22
_cell_volume                     4104.52(10)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1993)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini-S Ultra CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30179
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         8057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0571P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                5991
_reflns_number_total             8057
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ky3031.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018966
_cod_database_fobs_code          2018966