#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013833.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_2013833
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o65
_journal_page_last  o68
_publ_section_title
;
2-Chlorophenyl 3-nitrobenzenesulfonate and 2,4-dichlorophenyl
3-nitrobenzenesulfonate: supramolecular aggregation through
C---H...O, \p--\p and van der Waals interactions
;
loop_
_publ_author_name
  'Nagarajan Vembu'
  'Maruthai Nallu'
  'Semih Durmus'
  'Mathew Pazner'
  'Jered Garrison'
  'Wiley J. Youngs'
_chemical_formula_moiety  'C12 H7 Cl2 N O5 S'
_chemical_formula_sum  'C12 H7 Cl2 N O5 S'
_chemical_formula_iupac  'C12 H7 Cl2 N O5 S'
_chemical_formula_weight  348.15
_chemical_melting_point  '366-367'
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  6.878(5)
_cell_length_b  13.330(10)
_cell_length_c  14.990(11)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1374.3(17)
_cell_formula_units_Z  4
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.683
_diffrn_ambient_temperature  100(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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1 0.37528(8) 0.72585(4) 1.16297(4) 0.03515(14) Uani d . 1 . . Cl
  Cl2 0.70015(8) 0.36113(4) 1.12658(4) 0.03054(13) Uani d . 1 . . Cl
  S1 1.11206(7) 0.46106(4) 0.96706(3) 0.02198(12) Uani d . 1 . . S
  N1 0.4809(3) 0.53990(16) 0.79536(12) 0.0313(4) Uani d . 1 . . N
  O1 0.3376(3) 0.51043(15) 0.75540(11) 0.0438(5) Uani d . 1 . . O
  O2 0.5212(3) 0.62900(13) 0.80680(12) 0.0405(4) Uani d . 1 . . O
  O3 1.1685(2) 0.55771(11) 0.93622(10) 0.0288(3) Uani d . 1 . . O
  O4 1.2483(2) 0.38069(11) 0.97053(11) 0.0312(3) Uani d . 1 . . O
  O5 1.0425(2) 0.47127(10) 1.06854(9) 0.0226(3) Uani d . 1 . . O
  C1 0.8539(3) 0.32184(16) 0.90651(14) 0.0268(4) Uani d . 1 . . C
  C2 0.9000(3) 0.42355(14) 0.91084(12) 0.0215(4) Uani d . 1 . . C
  C3 0.7817(3) 0.49665(14) 0.87385(13) 0.0224(4) Uani d . 1 . . C
  C4 0.6136(3) 0.46416(16) 0.83191(13) 0.0247(4) Uani d . 1 . . C
  C5 0.5673(4) 0.36347(18) 0.82348(14) 0.0299(5) Uani d . 1 . . C
  C6 0.6883(4) 0.29243(16) 0.86107(15) 0.0313(5) Uani d . 1 . . C
  C7 0.8835(3) 0.53413(14) 1.08739(12) 0.0197(4) Uani d . 1 . . C
  C8 0.8992(3) 0.63802(15) 1.08168(14) 0.0241(4) Uani d . 1 . . C
  C9 0.7417(3) 0.69705(15) 1.10415(15) 0.0258(4) Uani d . 1 . . C
  C10 0.5719(3) 0.65118(15) 1.13297(14) 0.0245(4) Uani d . 1 . . C
  C11 0.5549(3) 0.54799(15) 1.13981(13) 0.0236(4) Uani d . 1 . . C
  C12 0.7131(3) 0.48969(13) 1.11678(13) 0.0205(4) Uani d . 1 . . C
  H1 0.935(4) 0.2748(18) 0.9338(16) 0.025(6) Uiso d . 1 . . H
  H3 0.813(4) 0.5681(18) 0.8779(15) 0.029(6) Uiso d . 1 . . H
  H5 0.470(4) 0.3520(19) 0.7947(16) 0.028(7) Uiso d . 1 . . H
  H6 0.656(4) 0.225(2) 0.8561(17) 0.042(8) Uiso d . 1 . . H
  H8 0.999(4) 0.6661(17) 1.0625(15) 0.022(6) Uiso d . 1 . . H
  H9 0.755(4) 0.7601(19) 1.1020(15) 0.026(6) Uiso d . 1 . . H
  H11 0.447(4) 0.526(2) 1.1590(16) 0.031(7) Uiso d . 1 . . 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
  Cl1 0.0228(2) 0.0310(2) 0.0517(3) 0.0073(2) 0.0069(2) -0.0040(2)
  Cl2 0.0280(3) 0.0203(2) 0.0434(3) -0.00461(19) 0.0014(2) 0.0053(2)
  S1 0.0146(2) 0.0221(2) 0.0292(2) 0.00210(18) 0.00254(19) 0.00104(18)
  N1 0.0225(9) 0.0479(11) 0.0235(8) 0.0066(9) 0.0022(7) 0.0036(8)
  O1 0.0269(9) 0.0703(12) 0.0342(9) 0.0097(8) -0.0102(7) -0.0110(8)
  O2 0.0254(8) 0.0397(9) 0.0563(11) 0.0052(7) 0.0003(8) 0.0170(8)
  O3 0.0212(7) 0.0282(7) 0.0370(8) -0.0039(6) 0.0043(6) 0.0035(6)
  O4 0.0205(7) 0.0319(7) 0.0411(9) 0.0096(6) 0.0034(6) 0.0020(7)
  O5 0.0174(7) 0.0238(6) 0.0265(7) 0.0040(6) -0.0013(5) 0.0013(5)
  C1 0.0290(11) 0.0219(9) 0.0294(10) 0.0013(9) 0.0031(9) -0.0013(8)
  C2 0.0187(9) 0.0227(8) 0.0229(9) 0.0005(8) 0.0042(8) -0.0023(7)
  C3 0.0209(10) 0.0232(8) 0.0230(9) 0.0006(8) 0.0045(8) 0.0013(7)
  C4 0.0197(9) 0.0331(10) 0.0214(9) 0.0035(9) 0.0039(8) 0.0010(8)
  C5 0.0252(11) 0.0410(12) 0.0234(10) -0.0080(10) 0.0025(9) -0.0083(9)
  C6 0.0348(12) 0.0252(9) 0.0338(11) -0.0040(9) 0.0039(10) -0.0063(9)
  C7 0.0157(8) 0.0221(8) 0.0213(9) 0.0019(8) -0.0003(7) -0.0023(7)
  C8 0.0165(9) 0.0236(9) 0.0323(11) -0.0053(8) 0.0009(8) 0.0002(8)
  C9 0.0233(10) 0.0182(8) 0.0359(11) -0.0022(8) -0.0004(8) -0.0039(8)
  C10 0.0169(9) 0.0263(9) 0.0303(10) 0.0047(7) 0.0004(8) -0.0042(8)
  C11 0.0167(9) 0.0265(9) 0.0276(10) -0.0035(8) 0.0024(8) -0.0006(8)
  C12 0.0198(9) 0.0188(8) 0.0230(9) -0.0022(7) -0.0024(8) 0.0008(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl1 C10 . 1.739(2) y
  Cl2 C12 . 1.722(2) y
  S1 O3 . 1.4229(17) y
  S1 O4 . 1.4240(16) y
  S1 O5 . 1.6006(18) y
  S1 C2 . 1.757(2) y
  N1 O1 . 1.219(3) y
  N1 O2 . 1.232(3) y
  N1 C4 . 1.467(3) y
  O5 C7 . 1.406(2) y
  C1 C6 . 1.384(3) ?
  C1 C2 . 1.394(3) ?
  C1 H1 . 0.94(3) ?
  C2 C3 . 1.386(3) ?
  C3 C4 . 1.385(3) ?
  C3 H3 . 0.98(2) ?
  C4 C5 . 1.385(3) ?
  C5 C6 . 1.381(4) ?
  C5 H5 . 0.81(3) ?
  C6 H6 . 0.93(3) ?
  C7 C12 . 1.385(3) ?
  C7 C8 . 1.392(3) ?
  C8 C9 . 1.381(3) ?
  C8 H8 . 0.84(3) ?
  C9 C10 . 1.387(3) ?
  C9 H9 . 0.85(2) ?
  C10 C11 . 1.384(3) ?
  C11 C12 . 1.381(3) ?
  C11 H11 . 0.85(3) ?