#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013996.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_2013996
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o255
_journal_page_last  o257
_publ_section_title
;
Cyano--cyano and chloro--cyano interactions in two imidazole derivatives
;
loop_
_publ_author_name
  'Kubicki, Maciej'
_chemical_formula_moiety  'C11 H7 Cl N4 O2'
_chemical_formula_sum  'C11 H7 Cl N4 O2'
_chemical_formula_iupac  'C11 H7 Cl N4 O2'
_chemical_formula_weight  262.66
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P2~1~/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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  12.6819(16)
_cell_length_b  6.8018(11)
_cell_length_c  15.1799(16)
_cell_angle_alpha  90.00
_cell_angle_beta  114.497(11)
_cell_angle_gamma  90.00
_cell_volume  1191.5(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.464
_diffrn_ambient_temperature  293(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 0.46832(11) 0.6630(2) 0.67776(9) 0.0434(3) Uani d . 1 . . N
  C11 0.50749(14) 0.6680(2) 0.78171(11) 0.0412(4) Uani d . 1 . . C
  C12 0.60610(17) 0.5694(3) 0.83926(13) 0.0568(5) Uani d . 1 . . C
  H12 0.6452(19) 0.502(3) 0.8121(15) 0.069(6) Uiso d . 1 . . H
  C13 0.64644(18) 0.5812(3) 0.93858(13) 0.0585(5) Uani d . 1 . . C
  H13 0.717(2) 0.515(3) 0.9801(18) 0.086(7) Uiso d . 1 . . H
  C14 0.58618(15) 0.6907(2) 0.97752(11) 0.0455(4) Uani d . 1 . . C
  Cl14 0.63698(5) 0.71140(8) 1.10216(3) 0.0664(2) Uani d . 1 . . Cl
  C15 0.48501(17) 0.7841(3) 0.91997(13) 0.0553(5) Uani d . 1 . . C
  H15 0.4392(18) 0.857(3) 0.9473(15) 0.074(6) Uiso d . 1 . . H
  C16 0.44623(17) 0.7743(3) 0.82106(13) 0.0518(4) Uani d . 1 . . C
  H16 0.3826(19) 0.841(3) 0.7848(16) 0.070(6) Uiso d . 1 . . H
  C2 0.49558(15) 0.7966(3) 0.62366(12) 0.0498(4) Uani d . 1 . . C
  C21 0.5734(2) 0.9650(3) 0.66616(15) 0.0724(6) Uani d . 1 . . C
  H21A 0.6519 0.9192 0.6975 0.121(6) Uiso calc R 1 . . H
  H21B 0.5521 1.0291 0.7128 0.121(6) Uiso calc R 1 . . H
  H21C 0.5668 1.0563 0.6159 0.121(6) Uiso calc R 1 . . H
  N3 0.44591(13) 0.7517(2) 0.53080(10) 0.0554(4) Uani d . 1 . . N
  C4 0.38577(14) 0.5863(3) 0.52677(12) 0.0488(4) Uani d . 1 . . C
  N4 0.32041(14) 0.4909(3) 0.43596(11) 0.0599(4) Uani d . 1 . . N
  O41 0.32955(13) 0.5505(2) 0.36420(9) 0.0753(4) Uani d . 1 . . O
  O42 0.25971(16) 0.3541(3) 0.43678(11) 0.0949(6) Uani d . 1 . . O
  C5 0.39676(14) 0.5250(2) 0.61538(11) 0.0449(4) Uani d . 1 . . C
  C51 0.35382(16) 0.3609(3) 0.64710(13) 0.0539(5) Uani d . 1 . . C
  N51 0.32224(18) 0.2276(3) 0.67366(13) 0.0802(6) Uani d . 1 . . N
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 0.0430(8) 0.0511(8) 0.0326(7) -0.0039(6) 0.0120(6) 0.0026(6)
  C11 0.0416(9) 0.0457(9) 0.0326(8) -0.0030(7) 0.0116(7) 0.0034(7)
  C12 0.0513(11) 0.0714(13) 0.0456(10) 0.0165(10) 0.0180(9) 0.0046(9)
  C13 0.0538(11) 0.0682(12) 0.0422(10) 0.0157(10) 0.0087(8) 0.0078(9)
  C14 0.0528(10) 0.0429(9) 0.0345(8) -0.0070(8) 0.0119(7) 0.0023(7)
  Cl14 0.0829(4) 0.0685(3) 0.0350(2) -0.0038(3) 0.0118(2) 0.0012(2)
  C15 0.0573(11) 0.0619(11) 0.0428(10) 0.0092(9) 0.0169(9) -0.0037(9)
  C16 0.0482(10) 0.0581(11) 0.0400(9) 0.0118(9) 0.0091(8) 0.0012(8)
  C2 0.0496(10) 0.0570(10) 0.0373(9) -0.0077(8) 0.0125(7) 0.0072(7)
  C21 0.0798(14) 0.0720(13) 0.0528(11) -0.0289(11) 0.0150(10) 0.0049(10)
  N3 0.0544(9) 0.0680(10) 0.0349(8) -0.0095(8) 0.0097(6) 0.0071(7)
  C4 0.0431(9) 0.0605(11) 0.0361(9) -0.0036(8) 0.0097(7) -0.0007(8)
  N4 0.0548(9) 0.0760(11) 0.0392(9) -0.0057(9) 0.0098(7) -0.0029(8)
  O41 0.0754(10) 0.1053(12) 0.0353(7) -0.0050(8) 0.0132(6) -0.0005(7)
  O42 0.1028(12) 0.1071(13) 0.0618(10) -0.0528(11) 0.0211(9) -0.0194(8)
  C5 0.0406(9) 0.0529(10) 0.0384(9) -0.0058(8) 0.0135(7) -0.0012(7)
  C51 0.0537(11) 0.0610(12) 0.0423(9) -0.0105(9) 0.0153(8) -0.0021(9)
  N51 0.0887(14) 0.0836(13) 0.0651(11) -0.0305(11) 0.0285(10) 0.0002(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 C2 . 1.362(2) ?
  N1 C5 . 1.374(2) ?
  N1 C11 . 1.445(2) ?
  C11 C16 . 1.367(3) ?
  C11 C12 . 1.368(2) ?
  C12 C13 . 1.379(3) ?
  C12 H12 . 0.89(2) ?
  C13 C14 . 1.365(3) ?
  C13 H13 . 0.97(3) ?
  C14 C15 . 1.372(3) ?
  C14 Cl14 . 1.7333(17) ?
  C15 C16 . 1.374(3) ?
  C15 H15 . 0.98(2) ?
  C16 H16 . 0.89(2) ?
  C2 N3 . 1.319(2) ?
  C2 C21 . 1.475(3) ?
  C21 H21A . 0.9600 ?
  C21 H21B . 0.9600 ?
  C21 H21C . 0.9600 ?
  N3 C4 . 1.346(2) ?
  C4 C5 . 1.359(2) ?
  C4 N4 . 1.435(2) ?
  N4 O42 . 1.211(2) ?
  N4 O41 . 1.212(2) ?
  C5 C51 . 1.411(3) ?
  C51 N51 . 1.131(2) ?