#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012818.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_2012818
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o428
_journal_page_last  o430
_publ_section_title
;
N-(2-Iodobenzylidene)-3-nitroaniline: sheets formed by a combination of
C-H...O hydrogen bonds and two aromatic \p...\p stacking interactions
;
loop_
_publ_author_name
  'Wardell, James L.'
  'Wardell, Solange M. S. V.'
  'Skakle, Janet M. S.'
  'Low, John N.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C13 H9 I N2 O2'
_chemical_formula_sum  'C13 H9 I N2 O2'
_chemical_formula_weight  352.12
_chemical_melting_point  346
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.7405(2)
_cell_length_b  8.3297(2)
_cell_length_c  11.3317(3)
_cell_angle_alpha  82.2570(9)
_cell_angle_beta  71.5605(8)
_cell_angle_gamma  62.7543(10)
_cell_volume  616.17(3)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.898
_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 0.7422(3) 0.0695(3) 0.3077(2) 0.0164(5) Uani d . 1 . . C
  N1 0.7310(3) 0.1564(3) 0.1922(2) 0.0183(4) Uani d . 1 . . N
  C2 0.7499(4) -0.1018(3) 0.3290(2) 0.0165(5) Uani d . 1 . . C
  C3 0.7636(4) -0.1796(3) 0.4437(2) 0.0172(5) Uani d . 1 . . C
  N3 0.7716(3) -0.3600(3) 0.4652(2) 0.0225(5) Uani d . 1 . . N
  O31 0.7780(4) -0.4380(3) 0.3785(2) 0.0371(5) Uani d . 1 . . O
  O32 0.7710(3) -0.4248(3) 0.5691(2) 0.0322(5) Uani d . 1 . . O
  C4 0.7705(4) -0.0952(4) 0.5378(2) 0.0214(5) Uani d . 1 . . C
  C5 0.7635(4) 0.0749(4) 0.5149(3) 0.0235(6) Uani d . 1 . . C
  C6 0.7519(4) 0.1560(4) 0.4008(3) 0.0201(5) Uani d . 1 . . C
  C11 0.5803(4) 0.2370(3) 0.0246(2) 0.0163(5) Uani d . 1 . . C
  C12 0.4086(4) 0.2768(3) -0.0131(2) 0.0153(5) Uani d . 1 . . C
  I12 0.15723(2) 0.23901(2) 0.102073(14) 0.02085(8) Uani d . 1 . . I
  C13 0.3940(4) 0.3507(3) -0.1292(2) 0.0185(5) Uani d . 1 . . C
  C14 0.5492(4) 0.3842(4) -0.2092(3) 0.0201(5) Uani d . 1 . . C
  C15 0.7211(4) 0.3454(3) -0.1738(3) 0.0205(5) Uani d . 1 . . C
  C16 0.7343(4) 0.2734(3) -0.0579(3) 0.0196(5) Uani d . 1 . . C
  C17 0.6006(4) 0.1579(3) 0.1460(2) 0.0168(5) Uani d . 1 . . C
  H2 0.7458 -0.1640 0.2662 0.020 Uiso calc R 1 . . H
  H4 0.7798 -0.1519 0.6156 0.026 Uiso calc R 1 . . H
  H5 0.7666 0.1367 0.5782 0.028 Uiso calc R 1 . . H
  H6 0.7505 0.2715 0.3860 0.024 Uiso calc R 1 . . H
  H13 0.2767 0.3780 -0.1534 0.022 Uiso calc R 1 . . H
  H14 0.5393 0.4339 -0.2887 0.024 Uiso calc R 1 . . H
  H15 0.8285 0.3684 -0.2289 0.025 Uiso calc R 1 . . H
  H16 0.8513 0.2482 -0.0341 0.023 Uiso calc R 1 . . H
  H17 0.5131 0.1058 0.1918 0.020 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 0.0097(10) 0.0194(12) 0.0192(12) -0.0061(9) -0.0044(9) 0.0025(9)
  N1 0.0185(10) 0.0161(11) 0.0204(11) -0.0074(8) -0.0073(9) 0.0038(8)
  C2 0.0144(11) 0.0187(12) 0.0176(12) -0.0071(9) -0.0068(9) 0.0007(10)
  C3 0.0117(11) 0.0199(12) 0.0205(13) -0.0080(9) -0.0045(9) 0.0022(10)
  N3 0.0178(10) 0.0233(12) 0.0257(12) -0.0092(9) -0.0090(9) 0.0093(10)
  O31 0.0610(15) 0.0246(11) 0.0399(13) -0.0245(10) -0.0278(12) 0.0093(10)
  O32 0.0323(11) 0.0358(12) 0.0282(11) -0.0182(9) -0.0104(9) 0.0176(9)
  C4 0.0148(11) 0.0306(14) 0.0165(12) -0.0081(10) -0.0059(10) 0.0031(10)
  C5 0.0180(12) 0.0295(15) 0.0226(14) -0.0077(11) -0.0071(11) -0.0058(11)
  C6 0.0153(12) 0.0203(13) 0.0268(14) -0.0076(10) -0.0079(11) -0.0031(11)
  C11 0.0151(11) 0.0127(12) 0.0196(13) -0.0046(9) -0.0056(10) -0.0007(9)
  C12 0.0138(11) 0.0138(12) 0.0174(12) -0.0053(9) -0.0041(9) -0.0003(9)
  I12 0.01522(11) 0.02461(13) 0.02394(13) -0.01003(8) -0.00601(8) 0.00203(8)
  C13 0.0193(12) 0.0161(12) 0.0208(13) -0.0052(10) -0.0098(10) -0.0015(10)
  C14 0.0233(13) 0.0183(13) 0.0158(12) -0.0067(10) -0.0060(10) 0.0007(10)
  C15 0.0187(12) 0.0202(13) 0.0200(13) -0.0083(10) -0.0028(10) 0.0004(10)
  C16 0.0159(11) 0.0201(13) 0.0227(13) -0.0079(10) -0.0065(10) 0.0025(10)
  C17 0.0153(11) 0.0142(12) 0.0193(12) -0.0056(9) -0.0049(9) 0.0014(9)
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 C2 . 1.392(4) no
  C1 C6 . 1.394(4) no
  C1 N1 . 1.415(3) no
  N1 C17 . 1.270(3) no
  C2 C3 . 1.385(4) no
  C2 H2 . 0.9500 no
  C3 C4 . 1.381(4) no
  C3 N3 . 1.466(3) no
  N3 O31 . 1.224(3) no
  N3 O32 . 1.227(3) no
  C4 C5 . 1.384(4) no
  C4 H4 . 0.9500 no
  C5 C6 . 1.385(4) no
  C5 H5 . 0.9500 no
  C6 H6 . 0.9500 no
  C11 C16 . 1.392(4) no
  C11 C12 . 1.406(3) no
  C11 C17 . 1.467(4) no
  C12 C13 . 1.391(4) no
  C12 I12 . 2.105(2) no
  C13 C14 . 1.376(4) no
  C13 H13 . 0.9500 no
  C14 C15 . 1.394(4) no
  C14 H14 . 0.9500 no
  C15 C16 . 1.382(4) no
  C15 H15 . 0.9500 no
  C16 H16 . 0.9500 no
  C17 H17 . 0.9500 no