#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014627.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2014627
_journal_name_full 'Acta Crystallographica, Section C'
_journal_year 2005
_journal_volume 61
_journal_page_first o105
_journal_page_last o109
_publ_section_title
;
Hydrogen bonding in 1:1 proton-transfer compounds of 5-sulfosalicylic acid with
the 4-X-substituted anilines (X = F, Cl or Br)
;
loop_
_publ_author_name
'Graham Smith '
' Urs D. Wermuth '
' Jonathan M. White '
_chemical_name_common '4-bromoanilinium 5-sulfosalicylate monohydrate'
_chemical_formula_moiety 'C6 H7 Br N +, C7 H5 O6 S -, H2 O'
_chemical_formula_sum 'C13 H14 Br N O7 S'
_chemical_formula_iupac 'C6 H7 Br N +, C7 H5 O6 S -, H2 O'
_chemical_formula_weight 408.22
_chemical_melting_point '514.2--515.7'
_symmetry_cell_setting 'orthorhombic'
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall '-P 2ac 2ab '
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
_cell_length_a 12.7810(19)
_cell_length_b 6.9860(10)
_cell_length_c 35.454(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3165.6(8)
_cell_formula_units_Z 8
_cell_measurement_temperature 295(2)
_exptl_crystal_density_diffrn 1.713
_diffrn_ambient_temperature 295(2)
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S5 0.0443(4) 0.0357(4) 0.0211(3) 0.0017(3) -0.0037(3) 0.0004(3)
O2 0.0601(13) 0.0662(15) 0.0293(11) -0.0235(12) -0.0087(10) -0.0016(10)
O51 0.0463(12) 0.0726(15) 0.0367(12) -0.0118(11) -0.0091(9) 0.0033(10)
O52 0.0673(14) 0.0414(11) 0.0337(11) 0.0092(10) -0.0048(9) -0.0115(9)
O53 0.0682(13) 0.0455(11) 0.0228(9) 0.0081(10) -0.0026(8) 0.0069(8)
O71 0.0582(14) 0.0701(15) 0.0228(11) -0.0234(12) 0.0074(9) -0.0008(10)
O72 0.0586(12) 0.0678(13) 0.0206(10) -0.0136(11) 0.0016(9) -0.0035(10)
C1 0.0410(14) 0.0317(13) 0.0230(13) 0.0007(12) 0.0025(11) -0.0005(11)
C2 0.0429(15) 0.0325(14) 0.0266(13) -0.0034(12) -0.0042(11) -0.0030(11)
C3 0.0388(14) 0.0376(15) 0.0345(15) -0.0103(12) 0.0011(11) -0.0004(11)
C4 0.0452(16) 0.0348(14) 0.0271(13) -0.0028(12) 0.0069(11) 0.0029(11)
C5 0.0376(14) 0.0273(12) 0.0236(13) 0.0022(11) -0.0007(10) 0.0014(10)
C6 0.0356(14) 0.0284(13) 0.0279(13) 0.0002(11) 0.0010(10) -0.0012(10)
C7 0.0457(16) 0.0380(16) 0.0265(14) -0.0028(13) 0.0043(12) -0.0056(11)
Br41 0.1346(5) 0.0798(4) 0.0375(3) -0.0063(3) -0.0071(2) 0.0017(2)
N11 0.0547(15) 0.0372(13) 0.0378(14) -0.0001(12) -0.0040(11) -0.0028(10)
C11 0.0467(16) 0.0299(13) 0.0358(15) -0.0036(13) 0.0015(12) 0.0009(12)
C21 0.0500(18) 0.058(2) 0.0453(19) 0.0065(15) 0.0051(14) 0.0051(15)
C31 0.0553(19) 0.062(2) 0.051(2) 0.0043(16) -0.0072(16) 0.0047(16)
C41 0.077(2) 0.0375(16) 0.0371(17) -0.0077(16) -0.0058(16) -0.0025(13)
C51 0.062(2) 0.0412(17) 0.0487(19) -0.0014(15) 0.0146(16) -0.0010(14)
C61 0.0488(17) 0.0385(17) 0.0506(19) 0.0008(13) 0.0021(14) 0.0000(14)
O1W 0.0653(19) 0.119(3) 0.083(2) -0.005(2) -0.0007(15) 0.045(3)
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
_cod_database_code 2014627