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_2014625
_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 F N +, C7 H5 O6 S -, H2 O'
_chemical_formula_moiety         'C6 H7 F N +, C7 H5 O6 S -, H2 O'
_chemical_formula_sum            'C13 H14 F N O7 S'
_chemical_formula_weight         347.31
_chemical_name_common
'4-fluoroanilinium 5-sulfosalicylate monohydrate'
_chemical_name_systematic
;
4-fluoroanilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
;
_chemical_temperature_decomposition 517.8(8)
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 96.529(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7978(7)
_cell_length_b                   12.5513(12)
_cell_length_c                   8.5306(8)
_cell_measurement_reflns_used    2628
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.90
_cell_volume                     723.12(12)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3741
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details 'Flack (1983), 1029 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     'none '
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2275
_reflns_number_total             2360
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            bm1595.cif
_cod_data_source_block           (I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '517.0--518.5 (dec.)'. The value was changed to '517.8(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' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '517.0--518.5 (dec.)'. The value was changed to '517.8(8)' - the
average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2014625