#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/28/2012882.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_2012882
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o487
_journal_page_last  o490
_publ_section_title
;
2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline
exhibit entirely different patterns of supramolecular aggregation
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M, S.'
  'Wardell, Solange M. S. V.'
  'Wardell, James L.'
_chemical_formula_moiety  'C13 H11 I N2 O2'
_chemical_formula_sum  'C13 H11 I N2 O2'
_chemical_formula_weight  354.14
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x-1/2, y-1/2, -z-1/2'
_cell_length_a  11.4056(3)
_cell_length_b  8.7364(3)
_cell_length_c  12.8357(5)
_cell_angle_alpha  90
_cell_angle_beta  109.0049(12)
_cell_angle_gamma  90
_cell_volume  1209.28(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.945
_diffrn_ambient_temperature  150(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
  N1 0.7374(2) 0.7365(2) 0.38064(18) 0.0166(5) Uani d . 1 . . N
  C1 0.6495(2) 0.6280(3) 0.3288(2) 0.0130(5) Uani d . 1 . . C
  C2 0.6207(2) 0.5946(3) 0.2161(2) 0.0136(5) Uani d . 1 . . C
  I2 0.711807(14) 0.712576(17) 0.121937(13) 0.01622(8) Uani d . 1 . . I
  C3 0.5338(2) 0.4850(3) 0.1652(2) 0.0148(5) Uani d . 1 . . C
  C4 0.4712(2) 0.4055(3) 0.2243(2) 0.0169(6) Uani d . 1 . . C
  C5 0.4995(2) 0.4344(3) 0.3356(2) 0.0172(6) Uani d . 1 . . C
  C6 0.5875(2) 0.5435(3) 0.3871(2) 0.0151(5) Uani d . 1 . . C
  C17 0.7430(3) 0.8005(3) 0.4859(2) 0.0178(6) Uani d . 1 . . C
  C11 0.8153(2) 0.7072(3) 0.5856(2) 0.0139(6) Uani d . 1 . . C
  C12 0.8044(2) 0.7450(3) 0.6866(2) 0.0136(5) Uani d . 1 . . C
  C13 0.8743(2) 0.6655(3) 0.7793(2) 0.0145(5) Uani d . 1 . . C
  N13 0.8625(2) 0.7088(2) 0.88553(19) 0.0176(5) Uani d . 1 . . N
  O131 0.79317(16) 0.8139(2) 0.88930(15) 0.0220(5) Uani d . 1 . . O
  O132 0.92388(19) 0.6373(2) 0.96755(15) 0.0317(5) Uani d . 1 . . O
  C14 0.9539(2) 0.5483(3) 0.7750(2) 0.0164(6) Uani d . 1 . . C
  C15 0.9635(2) 0.5119(3) 0.6738(2) 0.0173(6) Uani d . 1 . . C
  C16 0.8947(2) 0.5901(3) 0.5800(2) 0.0165(6) Uani d . 1 . . C
  H1 0.7910 0.7672 0.3489 0.020 Uiso calc R 1 . . H
  H3 0.5166 0.4639 0.0891 0.018 Uiso calc R 1 . . H
  H4 0.4098 0.3321 0.1887 0.020 Uiso calc R 1 . . H
  H5 0.4583 0.3790 0.3772 0.021 Uiso calc R 1 . . H
  H6 0.6061 0.5612 0.4639 0.018 Uiso calc R 1 . . H
  H17A 0.6572 0.8133 0.4872 0.021 Uiso calc R 1 . . H
  H17B 0.7807 0.9036 0.4924 0.021 Uiso calc R 1 . . H
  H2 0.7497 0.8243 0.6923 0.016 Uiso calc R 1 . . H
  H14 1.0004 0.4947 0.8397 0.020 Uiso calc R 1 . . H
  H15 1.0178 0.4323 0.6683 0.021 Uiso calc R 1 . . H
  H16 0.9020 0.5629 0.5107 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
  N1 0.0183(12) 0.0219(11) 0.0107(12) -0.0057(10) 0.0061(9) -0.0019(9)
  C1 0.0140(12) 0.0115(12) 0.0125(13) 0.0036(11) 0.0028(10) 0.0018(10)
  C2 0.0152(12) 0.0131(12) 0.0134(13) 0.0026(10) 0.0059(10) 0.0035(10)
  I2 0.01897(12) 0.01827(12) 0.01286(12) -0.00237(7) 0.00714(8) 0.00039(6)
  C3 0.0163(12) 0.0167(13) 0.0083(13) 0.0022(11) 0.0000(10) -0.0007(10)
  C4 0.0115(12) 0.0161(13) 0.0203(15) 0.0011(11) 0.0011(11) -0.0021(11)
  C5 0.0177(13) 0.0152(12) 0.0214(15) 0.0019(11) 0.0099(11) 0.0033(11)
  C6 0.0165(12) 0.0194(13) 0.0097(13) 0.0039(11) 0.0050(10) 0.0024(11)
  C17 0.0238(14) 0.0162(13) 0.0112(14) -0.0004(11) 0.0027(12) -0.0019(10)
  C11 0.0136(13) 0.0120(13) 0.0146(14) -0.0035(10) 0.0025(11) -0.0006(10)
  C12 0.0130(13) 0.0134(12) 0.0149(14) -0.0033(10) 0.0053(11) -0.0026(11)
  C13 0.0139(13) 0.0176(12) 0.0124(14) -0.0051(11) 0.0048(11) -0.0013(11)
  N13 0.0160(11) 0.0241(12) 0.0127(12) -0.0043(10) 0.0047(10) -0.0013(9)
  O131 0.0207(11) 0.0271(10) 0.0185(11) 0.0041(8) 0.0067(9) -0.0053(8)
  O132 0.0430(12) 0.0397(12) 0.0130(10) 0.0140(11) 0.0100(9) 0.0092(9)
  C14 0.0158(13) 0.0168(13) 0.0146(14) -0.0022(11) 0.0023(11) 0.0028(11)
  C15 0.0162(12) 0.0149(13) 0.0212(15) 0.0015(11) 0.0068(11) -0.0018(11)
  C16 0.0192(13) 0.0185(13) 0.0125(14) -0.0046(11) 0.0060(11) -0.0040(10)
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
  N1 C1 . 1.383(3) no
  N1 C17 . 1.444(3) no
  N1 H1 . 0.8800 no
  C1 C6 . 1.397(3) no
  C1 C2 . 1.406(3) no
  C2 C3 . 1.380(3) no
  C2 I2 . 2.102(2) no
  C3 C4 . 1.384(4) no
  C3 H3 . 0.9500 no
  C4 C5 . 1.382(4) no
  C4 H4 . 0.9500 no
  C5 C6 . 1.386(3) no
  C5 H5 . 0.9500 no
  C6 H6 . 0.9500 no
  C17 C11 . 1.515(3) no
  C17 H17A . 0.9900 no
  C17 H17B . 0.9900 no
  C11 C12 . 1.382(4) no
  C11 C16 . 1.383(3) no
  C12 C13 . 1.385(3) no
  C12 H2 . 0.9500 no
  C13 C14 . 1.382(3) no
  C13 N13 . 1.463(3) no
  N13 O131 . 1.223(3) no
  N13 O132 . 1.228(3) no
  C14 C15 . 1.375(4) no
  C14 H14 . 0.9500 no
  C15 C16 . 1.385(3) no
  C15 H15 . 0.9500 no
  C16 H16 . 0.9500 no
_cod_database_code 2012882