#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014627.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014627
loop_
_publ_author_name
'Graham Smith '
' Urs D. Wermuth '
' Jonathan M. White '
_publ_section_title
;
 Hydrogen bonding in 1:1 proton-transfer compounds of 5-sulfosalicylic
 acid with 4-X-substituted anilines (X = 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       'φ  and ω 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/[σ²(Fo²)+(0.0657P)²+0.9744P] where P=(Fo²+2Fc²)/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 >2σ(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
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,y,1/2-z
1/2-x,1/2+y,z
x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
S5 0.47157(5) 0.96199(10) 0.696416(18) 0.0337(2) Uani 1.000 S
O2 0.24796(17) 0.7489(3) 0.55712(6) 0.0519(8) Uani 1.000 O
O51 0.57779(17) 1.0167(3) 0.68714(6) 0.0519(8) Uani 1.000 O
O52 0.41149(17) 1.1239(3) 0.70977(5) 0.0475(7) Uani 1.000 O
O53 0.46616(16) 0.7984(3) 0.72161(5) 0.0455(6) Uani 1.000 O
O71 0.53666(17) 1.0287(3) 0.55021(6) 0.0504(8) Uani 1.000 O
O72 0.40158(17) 0.8994(3) 0.51939(5) 0.0490(7) Uani 1.000 O
C1 0.4033(2) 0.8850(4) 0.58601(7) 0.0319(8) Uani 1.000 C
C2 0.3054(2) 0.7953(4) 0.58797(7) 0.0340(8) Uani 1.000 C
C3 0.2631(2) 0.7498(4) 0.62296(8) 0.0370(8) Uani 1.000 C
C4 0.3146(2) 0.7966(4) 0.65550(7) 0.0357(8) Uani 1.000 C
C5 0.4118(2) 0.8882(4) 0.65387(7) 0.0295(8) Uani 1.000 C
C6 0.4561(2) 0.9302(3) 0.61935(7) 0.0306(8) Uani 1.000 C
C7 0.4472(2) 0.9386(4) 0.54897(8) 0.0367(9) Uani 1.000 C
Br41 0.86288(4) 1.03786(7) 0.534233(11) 0.0840(2) Uani 1.000 Br
N11 0.9246(2) 0.9495(3) 0.70380(7) 0.0432(8) Uani 1.000 N
C11 0.9090(2) 0.9728(4) 0.66345(8) 0.0375(8) Uani 1.000 C
C21 0.8155(3) 1.0409(5) 0.64965(9) 0.0511(11) Uani 1.000 C
C31 0.8019(3) 1.0618(5) 0.61127(10) 0.0561(11) Uani 1.000 C
C41 0.8822(3) 1.0138(4) 0.58725(9) 0.0505(10) Uani 1.000 C
C51 0.9759(3) 0.9469(4) 0.60075(10) 0.0506(11) Uani 1.000 C
C61 0.9894(2) 0.9270(4) 0.63919(9) 0.0460(10) Uani 1.000 C
O1W 0.7294(3) 0.8389(8) 0.73346(11) 0.0891(14) Uani 1.000 O
H2 0.283(3) 0.784(6) 0.5384(11) 0.069(13) Uiso 1.000 H
H3 0.1991 0.6868 0.6243 0.0440 Uiso 1.000 H
H4 0.2850 0.7673 0.6788 0.0430 Uiso 1.000 H
H6 0.5214 0.9888 0.6183 0.0370 Uiso 1.000 H
H72 0.555(3) 1.056(4) 0.5292(10) 0.048(10) Uiso 1.000 H
H11A 0.951(3) 1.059(4) 0.7140(10) 0.068(11) Uiso 1.000 H
H11B 0.970(3) 0.856(4) 0.7080(10) 0.066(10) Uiso 1.000 H
H11C 0.864(3) 0.920(4) 0.7150(10) 0.064(11) Uiso 1.000 H
H21 0.7616 1.0727 0.6661 0.0610 Uiso 1.000 H
H31 0.7389 1.1078 0.6017 0.0670 Uiso 1.000 H
H51 1.0297 0.9154 0.5842 0.0610 Uiso 1.000 H
H61 1.0528 0.8828 0.6487 0.0550 Uiso 1.000 H
H1A 0.708(4) 0.779(8) 0.7487(18) 0.11(2) Uiso 1.000 H
H1B 0.684(4) 0.892(7) 0.7201(17) 0.10(2) Uiso 1.000 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O51 S5 O52 111.44(13) no
O51 S5 O53 113.08(12) no
O51 S5 C5 106.76(12) no
O52 S5 O53 112.87(12) no
O52 S5 C5 106.13(12) no
O53 S5 C5 105.95(12) no
C2 O2 H2 106(3) no
C7 O71 H72 110(3) no
H1A O1W H1B 114(6) no
C11 N11 H11B 110(2) no
C11 N11 H11C 110(2) no
H11A N11 H11B 108(3) no
H11A N11 H11C 110(3) no
H11B N11 H11C 109(3) no
C11 N11 H11A 110(2) no
C2 C1 C6 119.4(2) no
C2 C1 C7 119.8(2) no
C6 C1 C7 120.8(2) no
O2 C2 C1 123.4(2) no
O2 C2 C3 117.0(2) no
C1 C2 C3 119.6(2) no
C2 C3 C4 120.7(2) no
C3 C4 C5 120.1(2) no
C4 C5 C6 119.9(2) no
S5 C5 C6 121.2(2) no
S5 C5 C4 118.82(19) no
C1 C6 C5 120.3(2) no
O72 C7 C1 121.4(2) no
O71 C7 O72 123.4(3) no
O71 C7 C1 115.2(2) no
C2 C3 H3 119.73 no
C4 C3 H3 119.55 no
C3 C4 H4 120.01 no
C5 C4 H4 119.87 no
C5 C6 H6 119.81 no
C1 C6 H6 119.92 no
N11 C11 C61 119.1(2) no
N11 C11 C21 120.5(3) no
C21 C11 C61 120.4(3) no
C11 C21 C31 119.8(3) no
C21 C31 C41 119.4(3) no
Br41 C41 C31 119.6(3) no
Br41 C41 C51 119.2(3) no
C31 C41 C51 121.2(3) no
C41 C51 C61 119.2(3) no
C11 C61 C51 120.0(3) no
C11 C21 H21 120.21 no
C31 C21 H21 120.01 no
C41 C31 H31 120.26 no
C21 C31 H31 120.33 no
C41 C51 H51 120.38 no
C61 C51 H51 120.42 no
C11 C61 H61 120.03 no
C51 C61 H61 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br41 C41 . . 1.903(3) no
S5 O51 . . 1.448(2) no
S5 O53 . . 1.452(2) no
S5 C5 . . 1.768(3) no
S5 O52 . . 1.447(2) no
O2 C2 . . 1.357(3) no
O71 C7 . . 1.306(3) no
O72 C7 . . 1.231(3) no
O2 H2 . . 0.84(4) no
O71 H72 . . 0.80(4) no
O1W H1B . . 0.84(5) no
O1W H1A . . 0.74(6) no
N11 C11 . . 1.454(4) no
N11 H11C . . 0.89(4) no
N11 H11A . . 0.91(3) no
N11 H11B . . 0.89(3) no
C1 C6 . . 1.397(4) no
C1 C7 . . 1.476(4) no
C1 C2 . . 1.401(4) no
C2 C3 . . 1.390(4) no
C3 C4 . . 1.368(4) no
C4 C5 . . 1.399(4) no
C5 C6 . . 1.380(4) no
C3 H3 . . 0.9301 no
C4 H4 . . 0.9314 no
C6 H6 . . 0.9303 no
C11 C61 . . 1.378(4) no
C11 C21 . . 1.376(5) no
C21 C31 . . 1.380(5) no
C31 C41 . . 1.375(5) no
C41 C51 . . 1.372(5) no
C51 C61 . . 1.381(5) no
C21 H21 . . 0.9296 no
C31 H31 . . 0.9310 no
C51 H51 . . 0.9303 no
C61 H61 . . 0.9304 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O72 . 0.84(4) 1.84(4) 2.598(3) 149(4) yes
O71 H72 O72 5_676 0.80(4) 1.84(4) 2.639(3) 176(3) yes
O1W H1A O52 4_646 0.74(6) 2.38(6) 3.090(5) 162(5) yes
O1W H1B O51 . 0.84(5) 1.99(5) 2.827(5) 179(6) yes
N11 H11A O53 7_655 0.91(3) 2.00(3) 2.879(3) 162(3) yes
N11 H11B O53 6_556 0.89(3) 2.53(4) 2.897(3) 106(3) yes
N11 H11B O51 7_645 0.89(3) 2.56(3) 3.081(3) 119(3) yes
N11 H11B O52 7_645 0.89(3) 2.22(3) 3.100(3) 172(3) yes
N11 H11C O1W . 0.89(4) 1.93(4) 2.815(5) 173(3) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O51 S5 C5 C4 169.1(2) no
O52 S5 C5 C4 -71.9(2) no
O53 S5 C5 C4 48.3(3) no
O51 S5 C5 C6 -15.0(3) no
O52 S5 C5 C6 103.9(2) no
O53 S5 C5 C6 -135.8(2) no
C6 C1 C2 C3 -1.1(4) no
C7 C1 C2 O2 1.8(4) no
C6 C1 C7 O72 179.9(2) no
C7 C1 C2 C3 -178.3(3) no
C2 C1 C6 C5 -0.5(4) no
C6 C1 C7 O71 0.0(4) no
C6 C1 C2 O2 179.0(2) no
C2 C1 C7 O71 177.2(2) no
C7 C1 C6 C5 176.7(2) no
C2 C1 C7 O72 -3.0(4) no
O2 C2 C3 C4 -178.1(3) no
C1 C2 C3 C4 1.9(4) no
C2 C3 C4 C5 -1.1(4) no
C3 C4 C5 C6 -0.4(4) no
C3 C4 C5 S5 175.5(2) no
C4 C5 C6 C1 1.3(4) no
S5 C5 C6 C1 -174.5(2) no
N11 C11 C61 C51 179.6(3) no
C61 C11 C21 C31 0.6(5) no
N11 C11 C21 C31 -179.9(3) no
C21 C11 C61 C51 -0.9(4) no
C11 C21 C31 C41 0.1(5) no
C21 C31 C41 Br41 178.8(3) no
C21 C31 C41 C51 -0.5(5) no
C31 C41 C51 C61 0.2(4) no
Br41 C41 C51 C61 -179.1(2) no
C41 C51 C61 C11 0.5(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133976
