#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013970.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_2013970
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o341
_journal_page_last  o343
_publ_section_title
;
1-(4-Bromophenyl)-2-methyl-4-nitro-1H-imidazole: bifurcated Br...O(nitro)
halogen bonds
;
loop_
_publ_author_name
  'Kubicki, Maciej'
_chemical_formula_moiety  'C10 H8 Br N3 O2'
_chemical_formula_sum  'C10 H8 Br N3 O2'
_chemical_formula_iupac  'C10 H8 Br N3 O2'
_chemical_formula_weight  282.10
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P21 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+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  4.1443(5)
_cell_length_b  10.4459(8)
_cell_length_c  24.1758(19)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1046.59(17)
_cell_formula_units_Z  4
_cell_measurement_temperature  100.0(10)
_exptl_crystal_density_diffrn  1.790
_diffrn_ambient_temperature  100.0(10)
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 0.8048(9) 0.6622(3) 0.67555(12) 0.0137(7) Uani d . 1 . . N
  C11 0.8719(10) 0.6033(4) 0.62277(13) 0.0124(8) Uani d . 1 . . C
  C12 1.0078(10) 0.4834(4) 0.62080(15) 0.0153(9) Uani d . 1 . . C
  H12 1.0584 0.4398 0.6542 0.018 Uiso calc R 1 . . H
  C13 1.0716(11) 0.4255(4) 0.57008(15) 0.0174(8) Uani d . 1 . . C
  H13 1.1652 0.3426 0.5685 0.021 Uiso calc R 1 . . H
  C14 0.9959(10) 0.4914(4) 0.52152(15) 0.0148(9) Uani d . 1 . . C
  Br14 1.09105(11) 0.41611(4) 0.451856(15) 0.02178(13) Uani d . 1 . . Br
  C15 0.8543(10) 0.6117(4) 0.52344(15) 0.0185(9) Uani d . 1 . . C
  H15 0.7996 0.6547 0.4901 0.022 Uiso calc R 1 . . H
  C16 0.7923(11) 0.6695(4) 0.57435(15) 0.0165(8) Uani d . 1 . . C
  H16 0.6978 0.7522 0.5761 0.020 Uiso calc R 1 . . H
  C2 0.9153(11) 0.7801(4) 0.69409(14) 0.0142(8) Uani d . 1 . . C
  C21 1.1314(11) 0.8655(4) 0.66054(15) 0.0156(8) Uani d . 1 . . C
  H21A 0.9998 0.9192 0.6361 0.020 Uiso calc R 1 . . H
  H21B 1.2777 0.8129 0.6382 0.020 Uiso calc R 1 . . H
  H21C 1.2577 0.9202 0.6854 0.020 Uiso calc R 1 . . H
  N3 0.8066(8) 0.8049(3) 0.74438(12) 0.0137(7) Uani d . 1 . . N
  C4 0.6262(10) 0.7002(4) 0.75764(14) 0.0109(7) Uani d . 1 . . C
  N4 0.4561(9) 0.6931(3) 0.80942(12) 0.0146(7) Uani d . 1 . . N
  O41 0.4836(7) 0.7810(3) 0.84256(11) 0.0205(7) Uani d . 1 . . O
  O42 0.2918(8) 0.5960(3) 0.81753(11) 0.0214(7) Uani d . 1 . . O
  C5 0.6208(11) 0.6093(4) 0.71680(13) 0.0127(8) Uani d . 1 . . C
  H5 0.5147 0.5287 0.7170 0.015 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 0.0142(19) 0.0160(17) 0.0109(13) -0.0005(14) -0.0001(12) -0.0009(12)
  C11 0.014(2) 0.0130(18) 0.0104(14) -0.0002(17) 0.0015(13) -0.0007(13)
  C12 0.018(2) 0.0151(19) 0.0126(16) -0.0032(16) -0.0028(14) 0.0015(14)
  C13 0.018(2) 0.0181(19) 0.0166(16) 0.001(2) 0.0000(16) -0.0049(15)
  C14 0.017(2) 0.0158(19) 0.0119(16) -0.0001(15) 0.0015(13) -0.0063(14)
  Br14 0.0243(2) 0.0289(2) 0.01213(17) 0.0013(2) 0.00213(16) -0.00668(16)
  C15 0.016(2) 0.028(2) 0.0113(16) 0.0005(18) 0.0002(14) 0.0041(15)
  C16 0.015(2) 0.021(2) 0.0139(18) 0.0037(18) 0.0015(15) 0.0020(16)
  C2 0.013(2) 0.0187(19) 0.0107(15) 0.007(2) -0.0018(16) 0.0000(13)
  C21 0.014(2) 0.0153(18) 0.0173(17) 0.0016(18) 0.0034(15) 0.0025(14)
  N3 0.0129(18) 0.0163(17) 0.0119(14) -0.0008(14) -0.0013(12) 0.0009(12)
  C4 0.014(2) 0.0087(17) 0.0102(15) 0.0035(17) -0.0009(14) 0.0006(12)
  N4 0.0156(19) 0.0175(17) 0.0107(14) 0.0021(15) -0.0015(13) 0.0021(12)
  O41 0.0276(19) 0.0197(15) 0.0142(13) -0.0034(13) 0.0022(11) -0.0065(11)
  O42 0.0264(17) 0.0202(15) 0.0175(13) -0.0076(15) 0.0044(11) 0.0003(12)
  C5 0.015(2) 0.0138(18) 0.0096(14) -0.0021(17) -0.0011(14) 0.0019(12)
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 C5 . 1.372(5) y
  N1 C2 . 1.389(5) y
  N1 C11 . 1.443(4) y
  C11 C12 . 1.375(5) ?
  C11 C16 . 1.399(5) ?
  C12 C13 . 1.392(5) ?
  C12 H12 . 0.9500 ?
  C13 C14 . 1.396(5) ?
  C13 H13 . 0.9500 ?
  C14 C15 . 1.388(6) ?
  C14 Br14 . 1.900(4) y
  C15 C16 . 1.395(5) ?
  C15 H15 . 0.9500 ?
  C16 H16 . 0.9500 ?
  C2 N3 . 1.322(5) y
  C2 C21 . 1.502(6) ?
  C21 H21A . 0.9800 ?
  C21 H21B . 0.9800 ?
  C21 H21C . 0.9800 ?
  N3 C4 . 1.363(5) y
  C4 C5 . 1.370(5) ?
  C4 N4 . 1.439(5) y
  N4 O41 . 1.224(4) y
  N4 O42 . 1.237(4) y
  C5 H5 . 0.9500 ?