#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014625.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_2014625
_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-fluoroanilinium 5-sulfosalicylate monohydrate'
_chemical_formula_moiety 'C6 H7 F N +, C7 H5 O6 S -, H2 O'
_chemical_formula_sum 'C13 H14 F N O7 S'
_chemical_formula_iupac 'C6 H7 F N +, C7 H5 O6 S -, H2 O'
_chemical_formula_weight 347.31
_chemical_melting_point '517.0--518.5 (dec.)'
_symmetry_cell_setting 'Monoclinic'
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 6.7978(7)
_cell_length_b 12.5513(12)
_cell_length_c 8.5306(8)
_cell_angle_alpha 90.00
_cell_angle_beta 96.529(2)
_cell_angle_gamma 90.00
_cell_volume 723.12(12)
_cell_formula_units_Z 2
_cell_measurement_temperature 295(2)
_exptl_crystal_density_diffrn 1.595
_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 0.96121(7) 0.21358(4) 0.44485(6) 0.0276(2) Uani 1.000 S
O2 0.8290(3) -0.13345(14) -0.0200(2) 0.0429(6) Uani 1.000 O
O51 1.1305(2) 0.17912(13) 0.55238(18) 0.0382(5) Uani 1.000 O
O52 0.7843(2) 0.22430(15) 0.52530(16) 0.0363(5) Uani 1.000 O
O53 1.0007(3) 0.31023(13) 0.35849(19) 0.0391(6) Uani 1.000 O
O71 0.8246(3) 0.18239(13) -0.1704(2) 0.0417(6) Uani 1.000 O
O72 0.8297(3) 0.01163(13) -0.24153(18) 0.0439(6) Uani 1.000 O
C1 0.8648(3) 0.05471(17) 0.0316(3) 0.0258(7) Uani 1.000 C
C2 0.8526(3) -0.05107(18) 0.0815(3) 0.0301(7) Uani 1.000 C
C3 0.8631(3) -0.07365(19) 0.2431(3) 0.0350(8) Uani 1.000 C
C4 0.8901(3) 0.00675(18) 0.3517(3) 0.0319(7) Uani 1.000 C
C5 0.9116(3) 0.11223(17) 0.3019(3) 0.0269(7) Uani 1.000 C
C6 0.8986(3) 0.13554(18) 0.1444(2) 0.0265(6) Uani 1.000 C
C7 0.8395(3) 0.08030(18) -0.1378(3) 0.0295(7) Uani 1.000 C
F41 0.5887(3) 0.55890(18) -0.3366(2) 0.0669(6) Uani 1.000 F
N11 0.7149(3) 0.48293(18) 0.3078(2) 0.0412(7) Uani 1.000 N
C11 0.6783(3) 0.5042(2) 0.1366(3) 0.0356(7) Uani 1.000 C
C21 0.6660(3) 0.4190(2) 0.0348(3) 0.0423(9) Uani 1.000 C
C31 0.6357(4) 0.4376(2) -0.1264(3) 0.0464(9) Uani 1.000 C
C41 0.6173(4) 0.5401(2) -0.1784(3) 0.0451(9) Uani 1.000 C
C51 0.6278(3) 0.6267(2) -0.0776(3) 0.0442(9) Uani 1.000 C
C61 0.6589(3) 0.6078(2) 0.0832(3) 0.0399(8) Uani 1.000 C
O1W 0.4444(4) 0.3384(2) 0.3885(4) 0.0733(10) Uani 1.000 O
H2 0.821(4) -0.112(3) -0.109(4) 0.053(10) Uiso 1.000 H
H3 0.8516 -0.1436 0.2767 0.0420 Uiso 1.000 H
H4 0.8941 -0.0085 0.4587 0.0380 Uiso 1.000 H
H6 0.9122 0.2057 0.1120 0.0320 Uiso 1.000 H
H71 0.807(5) 0.196(4) -0.262(5) 0.087(13) Uiso 1.000 H
H11A 0.748(4) 0.543(4) 0.359(4) 0.062(10) Uiso 1.000 H
H11B 0.810(4) 0.435(4) 0.327(4) 0.060(9) Uiso 1.000 H
H11C 0.604(4) 0.455(4) 0.340(4) 0.058(10) Uiso 1.000 H
H21 0.6779 0.3497 0.0735 0.0510 Uiso 1.000 H
H31 0.6280 0.3812 -0.1975 0.0560 Uiso 1.000 H
H51 0.6143 0.6958 -0.1167 0.0530 Uiso 1.000 H
H61 0.6665 0.6642 0.1542 0.0480 Uiso 1.000 H
H1A 0.322(6) 0.333(3) 0.381(5) 0.082(13) Uiso 1.000 H
H1B 0.496(5) 0.294(4) 0.445(5) 0.088(14) 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 0.0385(3) 0.0245(3) 0.0195(2) 0.0000(2) 0.0021(2) 0.0008(2)
O2 0.0684(13) 0.0267(9) 0.0322(11) 0.0031(8) -0.0001(9) 0.0056(8)
O51 0.0448(9) 0.0378(10) 0.0300(9) -0.0021(7) -0.0049(7) 0.0054(7)
O52 0.0454(9) 0.0409(9) 0.0231(7) -0.0074(8) 0.0062(6) -0.0004(8)
O53 0.0624(11) 0.0268(9) 0.0290(9) 0.0066(8) 0.0094(8) 0.0013(7)
O71 0.0735(12) 0.0321(10) 0.0200(9) -0.0032(8) 0.0073(8) -0.0013(7)
O72 0.0717(11) 0.0353(10) 0.0245(9) -0.0011(8) 0.0052(8) 0.0055(7)
C1 0.0288(11) 0.0264(12) 0.0223(11) -0.0007(8) 0.0035(8) -0.0009(9)
C2 0.0327(12) 0.0275(12) 0.0294(12) 0.0003(9) 0.0011(10) 0.0032(10)
C3 0.0469(14) 0.0234(12) 0.0337(13) 0.0031(10) 0.0001(11) -0.0058(9)
C4 0.0407(12) 0.0326(13) 0.0220(11) 0.0045(10) 0.0015(9) -0.0054(9)
C5 0.0301(11) 0.0255(12) 0.0249(12) 0.0001(9) 0.0019(9) 0.0005(9)
C6 0.0316(10) 0.0246(11) 0.0236(11) -0.0006(9) 0.0044(9) -0.0010(8)
C7 0.0372(12) 0.0289(13) 0.0227(11) 0.0009(9) 0.0046(9) 0.0028(9)
F41 0.0653(10) 0.0938(14) 0.0408(9) -0.0072(10) 0.0028(8) 0.0101(9)
N11 0.0420(12) 0.0374(12) 0.0438(12) -0.0050(9) 0.0030(9) 0.0035(10)
C11 0.0301(11) 0.0371(14) 0.0388(13) -0.0036(10) 0.0008(10) 0.0038(10)
C21 0.0404(13) 0.0315(14) 0.0537(17) -0.0013(11) 0.0003(12) 0.0012(11)
C31 0.0419(15) 0.0528(17) 0.0436(16) -0.0018(12) 0.0015(12) -0.0105(13)
C41 0.0343(13) 0.0612(18) 0.0388(15) -0.0030(12) 0.0001(11) 0.0064(13)
C51 0.0373(13) 0.0433(16) 0.0513(17) -0.0033(12) 0.0016(11) 0.0112(13)
C61 0.0364(12) 0.0335(14) 0.0495(16) -0.0035(10) 0.0030(11) -0.0019(11)
O1W 0.0461(13) 0.0627(17) 0.111(2) 0.0001(11) 0.0080(13) 0.0397(15)
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
S5 O51 . . 1.4535(15) no
S5 O52 . . 1.4571(15) no
S5 O53 . . 1.4599(17) no
S5 C5 . . 1.768(2) no
F41 C41 . . 1.362(3) no
O2 C2 . . 1.346(3) no
O71 C7 . . 1.313(3) no
O72 C7 . . 1.232(3) no
O2 H2 . . 0.80(3) no
O71 H71 . . 0.80(4) no
O1W H1B . . 0.79(5) no
O1W H1A . . 0.83(4) no
N11 C11 . . 1.478(3) no
N11 H11C . . 0.90(3) no
N11 H11A . . 0.89(5) no
N11 H11B . . 0.88(4) no
C1 C6 . . 1.399(3) no
C1 C7 . . 1.471(4) no
C1 C2 . . 1.400(3) no
C2 C3 . . 1.401(4) no
C3 C4 . . 1.368(3) no
C4 C5 . . 1.403(3) no
C5 C6 . . 1.368(3) no
C3 H3 . . 0.9296 no
C4 H4 . . 0.9300 no
C6 H6 . . 0.9307 no
C11 C61 . . 1.379(4) no
C11 C21 . . 1.374(4) no
C21 C31 . . 1.387(4) no
C31 C41 . . 1.362(4) no
C41 C51 . . 1.383(4) no
C51 C61 . . 1.384(4) no
C21 H21 . . 0.9306 no
C31 H31 . . 0.9298 no
C51 H51 . . 0.9300 no
C61 H61 . . 0.9292 no