#------------------------------------------------------------------------------
#$Date: 2011-06-13 14:58:51 +0300 (Mon, 13 Jun 2011) $
#$Revision: 20768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014626.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_2014626
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
the 4-<i>X</i>-substituted anilines (<i>X</i> = F, Cl or Br)
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o105
_journal_page_last               o109
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H7 Cl N +, C7 H5 O6 S -, 0.5H2 O'
_chemical_formula_moiety         'C6 H7 Cl N +, C7 H5 O6 S -, 0.5H2 O'
_chemical_formula_sum            'C13 H13 Cl N O6.5 S'
_chemical_formula_weight         354.77
_chemical_melting_point          512.5(8)
_chemical_name_common
'4-chloroanilinium 5-sulfosalicylate hemihydrate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.817(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.455(4)
_cell_length_b                   11.849(7)
_cell_length_c                   33.848(19)
_cell_measurement_temperature    295(2)
_cell_volume                     2990(3)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.576
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_cif_authors_sg_Hall '-P 2ybc '
_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 

'_chemical_melting_point' value '511.6--513.30 ' was changed to
'512.5(8)' - the average value was taken and precision was estimated.

Adriana Da\<skevi\<c, 2011-06-13
;
_cod_database_code               2014626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
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
S5A 0.0280(5) 0.0377(4) 0.0237(3) -0.0082(3) -0.0011(3) 0.0045(2)
O2A 0.0708(19) 0.0506(12) 0.0370(10) -0.0274(11) -0.0009(11) -0.0055(9)
O51A 0.0289(15) 0.0557(12) 0.0439(10) -0.0051(9) -0.0120(9) 0.0124(9)
O52A 0.0352(15) 0.0624(13) 0.0295(9) -0.0103(9) 0.0054(9) -0.0022(8)
O53A 0.0586(16) 0.0357(10) 0.0321(9) -0.0151(9) 0.0027(9) 0.0002(7)
O71A 0.0750(19) 0.0499(12) 0.0253(9) -0.0301(11) 0.0006(10) 0.0020(8)
O72A 0.0648(18) 0.0492(12) 0.0283(10) -0.0192(10) -0.0022(9) -0.0015(8)
C1A 0.0316(19) 0.0301(13) 0.0281(12) 0.0009(11) -0.0010(11) 0.0017(10)
C2A 0.034(2) 0.0320(14) 0.0339(13) -0.0019(11) -0.0030(12) -0.0027(10)
C3A 0.041(2) 0.0307(14) 0.0423(15) -0.0122(12) 0.0020(13) 0.0041(11)
C4A 0.032(2) 0.0366(14) 0.0319(13) -0.0037(11) 0.0011(12) 0.0071(10)
C5A 0.0225(18) 0.0293(13) 0.0291(12) 0.0013(10) -0.0041(11) 0.0029(9)
C6A 0.0254(17) 0.0283(12) 0.0289(12) -0.0022(10) -0.0019(11) 0.0026(9)
C7A 0.038(2) 0.0363(15) 0.0308(13) -0.0010(12) 0.0001(12) 0.0004(11)
S5B 0.0295(5) 0.0355(4) 0.0246(3) 0.0018(3) 0.0023(3) 0.0000(2)
O2B 0.0725(19) 0.0539(12) 0.0382(11) -0.0315(11) -0.0026(11) -0.0050(9)
O51B 0.0342(16) 0.0614(13) 0.0537(12) 0.0045(9) 0.0036(10) -0.0263(10)
O52B 0.0739(19) 0.0529(12) 0.0338(10) -0.0054(11) -0.0112(10) 0.0117(9)
O53B 0.0319(14) 0.0533(12) 0.0377(10) -0.0073(8) 0.0031(9) -0.0033(8)
O71B 0.0647(18) 0.0473(12) 0.0278(9) -0.0223(10) -0.0015(9) 0.0056(8)
O72B 0.0674(18) 0.0479(11) 0.0281(9) -0.0184(10) -0.0042(9) -0.0006(8)
C1B 0.0307(19) 0.0304(13) 0.0258(12) 0.0024(11) -0.0011(11) 0.0018(9)
C2B 0.034(2) 0.0340(14) 0.0358(13) -0.0033(11) -0.0009(12) -0.0026(10)
C3B 0.036(2) 0.0332(14) 0.0432(15) -0.0060(11) 0.0064(13) 0.0044(11)
C4B 0.034(2) 0.0359(14) 0.0322(13) 0.0009(11) 0.0070(12) 0.0070(10)
C5B 0.0242(18) 0.0306(13) 0.0270(12) 0.0046(10) 0.0024(10) -0.0002(9)
C6B 0.0261(18) 0.0264(12) 0.0307(12) 0.0021(10) -0.0003(11) 0.0015(9)
C7B 0.035(2) 0.0350(14) 0.0307(13) -0.0015(11) -0.0019(12) 0.0017(10)
Cl4C 0.1095(11) 0.1205(9) 0.0371(4) 0.0268(7) -0.0118(5) -0.0154(5)
N1C 0.0318(17) 0.0413(13) 0.0339(11) 0.0031(10) 0.0012(10) 0.0010(9)
C1C 0.0257(19) 0.0348(14) 0.0317(13) 0.0072(11) 0.0004(11) -0.0023(10)
C2C 0.046(2) 0.0323(14) 0.0424(15) -0.0022(12) 0.0053(14) -0.0051(11)
C3C 0.059(3) 0.0430(16) 0.0406(15) 0.0078(14) 0.0103(15) 0.0042(12)
C4C 0.052(3) 0.060(2) 0.0374(15) 0.0181(16) -0.0035(15) -0.0068(14)
C5C 0.043(2) 0.0545(19) 0.0569(18) 0.0020(15) -0.0053(16) -0.0240(15)
C6C 0.034(2) 0.0382(15) 0.0553(17) -0.0003(12) 0.0047(14) -0.0047(12)
Cl4D 0.1152(11) 0.0857(7) 0.0482(5) -0.0177(6) 0.0197(5) -0.0067(4)
N1D 0.0293(17) 0.0393(13) 0.0455(13) 0.0020(10) -0.0032(11) -0.0063(10)
C1D 0.0273(19) 0.0325(14) 0.0410(14) -0.0026(11) -0.0001(12) -0.0019(10)
C2D 0.041(2) 0.0353(15) 0.0486(16) 0.0033(12) 0.0006(14) 0.0045(12)
C3D 0.054(3) 0.0348(15) 0.0580(18) -0.0023(13) 0.0121(16) -0.0057(13)
C4D 0.050(2) 0.0488(17) 0.0447(16) -0.0138(15) 0.0067(15) -0.0018(13)
C5D 0.042(2) 0.0532(18) 0.0524(18) -0.0048(14) -0.0038(15) 0.0116(14)
C6D 0.036(2) 0.0359(15) 0.0563(18) 0.0047(12) 0.0001(15) 0.0044(12)
O1W 0.068(2) 0.0478(15) 0.0564(14) 0.0117(13) -0.0104(13) -0.0113(11)
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
S5A 0.24091(10) 0.42594(5) 0.048951(16) 0.0298(2) Uani 1.000 S
O2A 0.4975(3) 0.69127(17) 0.18525(5) 0.0528(8) Uani 1.000 O
O51A 0.0899(3) 0.49596(16) 0.03683(5) 0.0430(7) Uani 1.000 O
O52A 0.3818(3) 0.42376(16) 0.01997(5) 0.0423(7) Uani 1.000 O
O53A 0.1838(3) 0.31643(14) 0.06214(5) 0.0421(5) Uiso 1.000 O
O71A 0.1948(3) 0.40020(16) 0.20242(5) 0.0501(8) Uani 1.000 O
O72A 0.3446(3) 0.54215(16) 0.23032(5) 0.0475(8) Uani 1.000 O
C1A 0.3432(4) 0.5254(2) 0.16093(7) 0.0299(9) Uani 1.000 C
C2A 0.4406(4) 0.6245(2) 0.15523(7) 0.0333(9) Uani 1.000 C
C3A 0.4810(4) 0.6585(2) 0.11718(7) 0.0380(10) Uani 1.000 C
C4A 0.4266(4) 0.5961(2) 0.08543(7) 0.0335(9) Uani 1.000 C
C5A 0.3305(4) 0.49675(19) 0.09081(7) 0.0270(8) Uani 1.000 C
C6A 0.2897(4) 0.46204(19) 0.12809(7) 0.0276(8) Uani 1.000 C
C7A 0.2949(4) 0.4901(2) 0.20068(7) 0.0350(9) Uani 1.000 C
S5B 0.28878(10) 0.44097(5) 0.456715(17) 0.0298(2) Uani 1.000 S
O2B -0.0095(3) 0.18868(18) 0.32133(5) 0.0549(8) Uani 1.000 O
O51B 0.1495(3) 0.51788(17) 0.46989(6) 0.0497(8) Uani 1.000 O
O52B 0.3311(3) 0.35715(17) 0.48601(5) 0.0536(8) Uani 1.000 O
O53B 0.4447(3) 0.50017(16) 0.44251(5) 0.0409(7) Uani 1.000 O
O71B 0.2983(3) 0.47718(16) 0.30390(5) 0.0466(8) Uani 1.000 O
O72B 0.1474(3) 0.33540(16) 0.27594(5) 0.0478(8) Uani 1.000 O
C1B 0.1618(4) 0.3473(2) 0.34553(6) 0.0290(9) Uani 1.000 C
C2B 0.0571(4) 0.2513(2) 0.35121(7) 0.0346(9) Uani 1.000 C
C3B 0.0184(4) 0.2173(2) 0.38963(7) 0.0374(10) Uani 1.000 C
C4B 0.0862(4) 0.2743(2) 0.42123(7) 0.0340(9) Uani 1.000 C
C5B 0.1936(4) 0.36865(19) 0.41585(7) 0.0272(8) Uani 1.000 C
C6B 0.2292(4) 0.40597(19) 0.37819(7) 0.0277(8) Uani 1.000 C
C7B 0.2027(4) 0.3858(2) 0.30559(7) 0.0336(9) Uani 1.000 C
Cl4C 0.18989(18) 0.46444(10) 0.73684(2) 0.0892(5) Uani 1.000 Cl
N1C 0.1900(3) 0.41885(18) 0.56285(6) 0.0357(8) Uani 1.000 N
C1C 0.1839(4) 0.4342(2) 0.60556(7) 0.0307(9) Uani 1.000 C
C2C 0.0969(4) 0.3552(2) 0.62791(8) 0.0402(10) Uani 1.000 C
C3C 0.0968(5) 0.3657(2) 0.66835(8) 0.0474(12) Uani 1.000 C
C4C 0.1836(5) 0.4547(3) 0.68580(8) 0.0498(13) Uani 1.000 C
C5C 0.2647(5) 0.5360(3) 0.66353(9) 0.0515(11) Uani 1.000 C
C6C 0.2643(4) 0.5261(2) 0.62290(8) 0.0425(10) Uani 1.000 C
Cl4D 0.35328(17) 0.77313(9) 0.29620(2) 0.0829(5) Uani 1.000 Cl
N1D 0.2463(3) 0.88873(18) 0.46442(6) 0.0381(8) Uani 1.000 N
C1D 0.2694(4) 0.8581(2) 0.42311(7) 0.0336(9) Uani 1.000 C
C2D 0.3588(4) 0.7606(2) 0.41341(8) 0.0416(10) Uani 1.000 C
C3D 0.3836(5) 0.7348(2) 0.37428(9) 0.0488(13) Uani 1.000 C
C4D 0.3188(5) 0.8056(3) 0.34568(8) 0.0478(10) Uani 1.000 C
C5D 0.2277(5) 0.9020(3) 0.35511(9) 0.0492(11) Uani 1.000 C
C6D 0.2043(4) 0.9286(2) 0.39396(8) 0.0427(10) Uani 1.000 C
O1W 0.2885(5) 0.7015(2) 0.51330(7) 0.0575(10) Uani 1.000 O
H2A 0.473(7) 0.662(4) 0.2061(16) 0.079(14) Uiso 1.000 H
H3A 0.5458 0.7245 0.1133 0.0450 Uiso 1.000 H
H4A 0.4539 0.6199 0.0600 0.0400 Uiso 1.000 H
H6A 0.2257 0.3955 0.1316 0.0330 Uiso 1.000 H
H71A 0.178(6) 0.384(4) 0.2260(15) 0.075(15) Uiso 1.000 H
H2B 0.016(7) 0.218(4) 0.3001(16) 0.082(15) Uiso 1.000 H
H3B -0.0548 0.1549 0.3936 0.0450 Uiso 1.000 H
H4B 0.0607 0.2499 0.4467 0.0410 Uiso 1.000 H
H6B 0.2983 0.4704 0.3746 0.0330 Uiso 1.000 H
H71B 0.302(7) 0.499(4) 0.2812(15) 0.070(14) Uiso 1.000 H
H2C 0.0383 0.2949 0.6158 0.0480 Uiso 1.000 H
H3C 0.0380 0.3126 0.6837 0.0570 Uiso 1.000 H
H5C 0.3197 0.5976 0.6757 0.0620 Uiso 1.000 H
H6C 0.3180 0.5811 0.6075 0.0510 Uiso 1.000 H
H11C 0.091(7) 0.447(4) 0.5518(16) 0.053(15) Uiso 1.000 H
H12C 0.196(7) 0.345(4) 0.5573(17) 0.063(15) Uiso 1.000 H
H13C 0.285(6) 0.454(4) 0.5531(16) 0.057(16) Uiso 1.000 H
H2D 0.4020 0.7126 0.4331 0.0500 Uiso 1.000 H
H3D 0.4444 0.6694 0.3673 0.0590 Uiso 1.000 H
H5D 0.1822 0.9489 0.3353 0.0590 Uiso 1.000 H
H6D 0.1443 0.9944 0.4007 0.0510 Uiso 1.000 H
H11D 0.333(6) 0.933(4) 0.4725(16) 0.057(15) Uiso 1.000 H
H12D 0.251(6) 0.827(4) 0.4793(17) 0.061(16) Uiso 1.000 H
H13D 0.140(6) 0.920(4) 0.4676(16) 0.053(15) Uiso 1.000 H
H1W 0.244(7) 0.643(4) 0.4995(13) 0.077(17) Uiso 1.000 H
H2W 0.414(8) 0.685(4) 0.5121(14) 0.120(19) Uiso 1.000 H
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
Cl4C C4C . . 1.731(3) no
Cl4D C4D . . 1.741(3) no
S5A O53A . . 1.439(2) no
S5A C5A . . 1.769(3) no
S5A O51A . . 1.453(2) no
S5A O52A . . 1.448(2) no
S5B O53B . . 1.446(2) no
S5B O51B . . 1.456(2) no
S5B O52B . . 1.435(2) no
S5B C5B . . 1.767(3) no
O2A C2A . . 1.351(3) no
O71A C7A . . 1.302(3) no
O72A C7A . . 1.230(3) no
O2A H2A . . 0.81(5) no
O71A H71A . . 0.83(5) no
O2B C2B . . 1.344(3) no
O71B C7B . . 1.298(3) no
O72B C7B . . 1.234(3) no
O2B H2B . . 0.82(5) no
O71B H71B . . 0.81(5) no
O1W H2W . . 0.96(6) no
O1W H1W . . 0.90(5) no
N1C C1C . . 1.458(3) no
N1C H11C . . 0.89(5) no
N1C H13C . . 0.89(5) no
N1C H12C . . 0.90(5) no
N1D C1D . . 1.457(3) no
N1D H13D . . 0.88(5) no
N1D H11D . . 0.87(5) no
N1D H12D . . 0.89(5) no
C1A C2A . . 1.395(4) no
C1A C6A . . 1.395(4) no
C1A C7A . . 1.459(4) no
C2A C3A . . 1.387(3) no
C3A C4A . . 1.361(4) no
C4A C5A . . 1.391(4) no
C5A C6A . . 1.366(3) no
C3A H3A . . 0.9295 no
C4A H4A . . 0.9310 no
C6A H6A . . 0.9301 no
C1B C6B . . 1.394(3) no
C1B C2B . . 1.394(4) no
C1B C7B . . 1.463(3) no
C2B C3B . . 1.395(3) no
C3B C4B . . 1.357(4) no
C4B C5B . . 1.389(4) no
C5B C6B . . 1.379(3) no
C3B H3B . . 0.9299 no
C4B H4B . . 0.9315 no
C6B H6B . . 0.9299 no
C1C C6C . . 1.371(4) no
C1C C2C . . 1.372(4) no
C2C C3C . . 1.374(4) no
C3C C4C . . 1.367(5) no
C4C C5C . . 1.369(5) no
C5C C6C . . 1.380(4) no
C2C H2C . . 0.9297 no
C3C H3C . . 0.9298 no
C5C H5C . . 0.9305 no
C6C H6C . . 0.9288 no
C1D C6D . . 1.376(4) no
C1D C2D . . 1.376(4) no
C2D C3D . . 1.374(4) no
C3D C4D . . 1.364(4) no
C4D C5D . . 1.369(5) no
C5D C6D . . 1.366(4) no
C2D H2D . . 0.9302 no
C3D H3D . . 0.9300 no
C5D H5D . . 0.9311 no
C6D H6D . . 0.9289 no