Hydrogen bonding in 1:1 proton-transfer compounds of 5-sulfosalicylic acid with 4-<i>X</i>-substituted anilines (<i>X</i> = F, Cl or Br)
Graham Smith; Urs D. Wermuth; Jonathan M. White; Acta Crystallographica Section C 61 (2005) o105–o109; doi:10.1107/S0108270104033451

data_2014627
_publ_section_title
;
 Hydrogen bonding in 1:1 proton-transfer compounds of 5-sulfosalicylic
 acid with 4-<i>X</i>-substituted anilines (<i>X</i> = F, Cl or Br)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o105
_journal_page_last               o109
_journal_paper_doi               10.1107/S0108270104033451
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H7 Br N +, C7 H5 O6 S -, H2 O'
_chemical_formula_moiety         'C6 H7 Br N +, C7 H5 O6 S -, H2 O'
_chemical_formula_sum            'C13 H14 Br N O7 S'
_chemical_formula_weight         408.22
_chemical_melting_point          515.0(8)
_chemical_name_common
'4-bromoanilinium 5-sulfosalicylate monohydrate'
_chemical_name_systematic
;
 4-bromoanilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 (Sheldrick, 1997)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7810(19)
_cell_length_b                   6.9860(10)
_cell_length_c                   35.454(5)
_cell_measurement_reflns_used    4362
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.30
_cell_volume                     3165.6(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector diffractometer'
_diffrn_measurement_method       '\f  and \w scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14778
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_T_max  0.436
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.552
_refine_ls_extinction_method     'none '
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.9744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                2203
_reflns_number_total             2788
_reflns_threshold_expression     'I >2\s(I)'
_cod_data_source_file            bm1595.cif
_cod_data_source_block           (III)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '514.2--515.7' was changed to
'515.0(8)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '514.2--515.7' was changed to
'515.0(8)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               2014627