#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013211.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_2013211
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o95
_journal_page_last  o97
_publ_section_title
;
4-Iodo-N-(2-nitrophenylsulfanyl)aniline: \p-stacked sheets generated by
a combination of N---H...O and C---H...O hydrogen bonds
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M. S.'
  'Wardell, James L.'
_chemical_formula_moiety  'C12 H9 I N2 O2 S'
_chemical_formula_sum  'C12 H9 I N2 O2 S'
_chemical_formula_iupac  'C12 H9 I N2 O2 S'
_chemical_formula_weight  372.18
_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'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-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  7.4171(2)
_cell_length_b  22.1145(8)
_cell_length_c  15.7093(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2576.73(13)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.919
_diffrn_ambient_temperature  120(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
  C1 0.5139(5) 0.60187(17) 0.0489(2) 0.0212(9) Uani d . 1 . . C
  C2 0.4337(5) 0.57878(18) -0.0242(2) 0.0256(10) Uani d . 1 . . C
  C3 0.5363(6) 0.55240(18) -0.0871(2) 0.0272(10) Uani d . 1 . . C
  C4 0.7206(6) 0.54941(18) -0.0777(2) 0.0266(10) Uani d . 1 . . C
  I4 0.87720(5) 0.505572(13) -0.171435(16) 0.03766(13) Uani d . 1 . . I
  C5 0.8042(6) 0.57209(18) -0.0058(2) 0.0304(10) Uani d . 1 . . C
  C6 0.6996(5) 0.59855(19) 0.0575(3) 0.0287(10) Uani d . 1 . . C
  S1 0.46633(13) 0.64314(5) 0.21155(6) 0.0236(2) Uani d . 1 . . S
  N1 0.4042(4) 0.62927(15) 0.11064(19) 0.0266(8) Uani d . 1 . . N
  C11 0.5423(5) 0.71901(17) 0.2043(2) 0.0202(9) Uani d . 1 . . C
  C12 0.5882(5) 0.75438(18) 0.2755(2) 0.0208(9) Uani d . 1 . . C
  C13 0.6467(5) 0.81364(19) 0.2685(2) 0.0266(10) Uani d . 1 . . C
  C14 0.6623(6) 0.84010(19) 0.1903(2) 0.0326(11) Uani d . 1 . . C
  C15 0.6187(6) 0.8060(2) 0.1191(2) 0.0347(11) Uani d . 1 . . C
  C16 0.5584(5) 0.74744(19) 0.1254(2) 0.0252(10) Uani d . 1 . . C
  N12 0.5739(4) 0.72846(18) 0.3604(2) 0.0279(8) Uani d . 1 . . N
  O121 0.5351(4) 0.67415(14) 0.36581(15) 0.0286(7) Uani d . 1 . . O
  O122 0.6018(5) 0.76111(15) 0.42184(16) 0.0497(9) Uani d . 1 . . O
  H2 0.3066 0.5812 -0.0309 0.031 Uiso calc R 1 . . H
  H3 0.4804 0.5364 -0.1365 0.033 Uiso calc R 1 . . H
  H5 0.9315 0.5696 0.0003 0.036 Uiso calc R 1 . . H
  H6 0.7558 0.6145 0.1070 0.034 Uiso calc R 1 . . H
  H1 0.2947 0.6400 0.0953 0.032 Uiso calc R 1 . . H
  H13 0.6761 0.8360 0.3183 0.032 Uiso calc R 1 . . H
  H14 0.7020 0.8808 0.1849 0.039 Uiso calc R 1 . . H
  H15 0.6309 0.8237 0.0643 0.042 Uiso calc R 1 . . H
  H16 0.5271 0.7259 0.0752 0.030 Uiso calc R 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
  C1 0.025(2) 0.016(2) 0.022(2) -0.0009(17) 0.0006(19) 0.0003(18)
  C2 0.024(2) 0.025(2) 0.028(2) -0.0011(18) -0.0095(19) 0.0030(19)
  C3 0.037(3) 0.026(3) 0.018(2) 0.002(2) -0.003(2) -0.0033(18)
  C4 0.035(3) 0.021(2) 0.024(2) -0.0022(19) 0.007(2) -0.0006(17)
  I4 0.0514(2) 0.0369(2) 0.02474(17) 0.00869(15) 0.01215(14) 0.00135(13)
  C5 0.023(2) 0.031(3) 0.036(2) -0.0057(19) 0.005(2) -0.006(2)
  C6 0.026(2) 0.033(3) 0.027(2) -0.006(2) -0.004(2) -0.010(2)
  S1 0.0239(5) 0.0254(6) 0.0215(5) -0.0023(5) 0.0015(5) 0.0012(5)
  N1 0.0196(18) 0.033(2) 0.0268(18) 0.0024(15) -0.0075(15) -0.0051(16)
  C11 0.016(2) 0.024(2) 0.021(2) 0.0018(17) 0.0036(18) -0.0015(18)
  C12 0.021(2) 0.027(2) 0.0145(19) 0.0025(17) 0.0028(17) 0.0003(18)
  C13 0.027(2) 0.030(3) 0.023(2) 0.0005(19) 0.002(2) -0.0097(19)
  C14 0.042(3) 0.020(2) 0.035(3) -0.003(2) 0.002(2) 0.006(2)
  C15 0.044(3) 0.037(3) 0.023(2) -0.001(2) 0.006(2) 0.005(2)
  C16 0.028(2) 0.030(3) 0.017(2) -0.0004(18) 0.0003(18) 0.0001(18)
  N12 0.023(2) 0.041(3) 0.0194(18) 0.0032(17) 0.0035(16) 0.0009(18)
  O121 0.0252(16) 0.038(2) 0.0228(15) 0.0003(14) 0.0022(13) 0.0101(14)
  O122 0.078(3) 0.056(2) 0.0151(16) -0.0101(18) -0.0001(16) -0.0103(15)
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
  C1 C6 . 1.386(5) no
  C1 C2 . 1.390(5) no
  C2 C3 . 1.376(5) no
  C2 H2 . 0.95 no
  C3 C4 . 1.376(6) no
  C3 H3 . 0.95 no
  C4 C5 . 1.383(5) no
  C4 I4 . 2.111(4) no
  C5 C6 . 1.390(5) no
  C5 H5 . 0.95 no
  C6 H6 . 0.95 no
  C1 N1 . 1.404(5) y
  S1 N1 . 1.679(3) y
  S1 C11 . 1.774(4) y
  C12 N12 . 1.455(5) y
  N12 O121 . 1.238(4) y
  N12 O122 . 1.224(4) y
  N1 H1 . 0.88 no
  C11 C12 . 1.407(5) y
  C12 C13 . 1.385(6) y
  C13 C14 . 1.365(5) y
  C14 C15 . 1.388(5) y
  C15 C16 . 1.374(6) y
  C16 C11 . 1.394(5) y
  C13 H13 . 0.95 no
  C14 H14 . 0.95 no
  C15 H15 . 0.95 no
  C16 H16 . 0.95 no
_cod_database_code 2013211