#------------------------------------------------------------------------------
#$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013995.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_2013995
_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
;
_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
  'Kubicki, Maciej'
_chemical_formula_moiety  'C11 H8 N4 O2'
_chemical_formula_sum  'C11 H8 N4 O2'
_chemical_formula_iupac  'C11 H8 N4 O2'
_chemical_formula_weight  228.21
_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  9.8976(9)
_cell_length_b  9.6168(9)
_cell_length_c  11.6700(10)
_cell_angle_alpha  90.00
_cell_angle_beta  103.313(7)
_cell_angle_gamma  90.00
_cell_volume  1080.94(17)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.402
_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 0.68836(11) 0.07163(12) 0.35541(10) 0.0422(3) Uani d . 1 . . N
  C11 0.72914(14) 0.05299(14) 0.24477(12) 0.0401(3) Uani d . 1 . . C
  C12 0.64864(17) -0.02692(16) 0.15774(13) 0.0498(4) Uani d . 1 . . C
  H12 0.5670(16) -0.0706(15) 0.1701(12) 0.054(4) Uiso d . 1 . . H
  C13 0.68759(18) -0.0407(2) 0.05250(15) 0.0607(5) Uani d . 1 . . C
  H13 0.6374(17) -0.0988(17) -0.0065(15) 0.069(5) Uiso d . 1 . . H
  C14 0.80361(18) 0.02539(19) 0.03470(16) 0.0618(5) Uani d . 1 . . C
  H14 0.8225(16) 0.0164(18) -0.0381(17) 0.080(6) Uiso d . 1 . . H
  C15 0.88281(19) 0.10485(19) 0.12165(15) 0.0588(5) Uani d . 1 . . C
  H15 0.9612(18) 0.1520(16) 0.1141(14) 0.068(5) Uiso d . 1 . . H
  C16 0.84701(16) 0.11851(17) 0.22847(15) 0.0494(4) Uani d . 1 . . C
  H16 0.9023(16) 0.1678(14) 0.2905(14) 0.054(4) Uiso d . 1 . . H
  C2 0.58798(14) 0.15987(15) 0.37605(13) 0.0464(4) Uani d . 1 . . C
  C21 0.50057(17) 0.24700(17) 0.28327(15) 0.0623(5) Uani d . 1 . . C
  H21A 0.4376 0.3009 0.3167 0.146(5) Uiso calc R 1 . . H
  H21B 0.4488 0.1884 0.2221 0.146(5) Uiso calc R 1 . . H
  H21C 0.5587 0.3083 0.2508 0.146(5) Uiso calc R 1 . . H
  N3 0.58068(12) 0.15680(13) 0.48740(11) 0.0504(3) Uani d . 1 . . N
  C4 0.67827(15) 0.06517(16) 0.53828(12) 0.0467(4) Uani d . 1 . . C
  N4 0.70230(15) 0.03338(16) 0.66203(12) 0.0599(4) Uani d . 1 . . N
  O41 0.63201(15) 0.09102(14) 0.72030(11) 0.0862(4) Uani d . 1 . . O
  O42 0.79373(14) -0.05070(16) 0.70153(10) 0.0839(4) Uani d . 1 . . O
  C5 0.74742(14) 0.00858(15) 0.46121(12) 0.0429(4) Uani d . 1 . . C
  C51 0.85333(16) -0.09359(17) 0.47370(12) 0.0485(4) Uani d . 1 . . C
  N51 0.93848(15) -0.17517(16) 0.48416(12) 0.0680(4) 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 0.0431(7) 0.0448(7) 0.0402(7) -0.0005(6) 0.0128(5) -0.0010(6)
  C11 0.0421(8) 0.0412(8) 0.0380(8) 0.0021(6) 0.0115(6) 0.0018(6)
  C12 0.0445(9) 0.0534(10) 0.0511(10) -0.0031(8) 0.0100(7) -0.0046(7)
  C13 0.0588(11) 0.0735(13) 0.0461(10) 0.0050(9) 0.0042(8) -0.0127(9)
  C14 0.0638(12) 0.0829(13) 0.0420(10) 0.0137(10) 0.0188(9) 0.0035(9)
  C15 0.0542(10) 0.0687(12) 0.0597(11) -0.0004(9) 0.0257(9) 0.0107(9)
  C16 0.0470(9) 0.0531(10) 0.0483(9) -0.0032(8) 0.0114(8) -0.0018(8)
  C2 0.0470(9) 0.0434(9) 0.0519(10) -0.0005(7) 0.0179(7) -0.0020(7)
  C21 0.0643(11) 0.0568(10) 0.0669(11) 0.0157(9) 0.0173(9) 0.0089(8)
  N3 0.0499(7) 0.0541(8) 0.0508(8) -0.0019(6) 0.0192(6) -0.0040(6)
  C4 0.0477(9) 0.0550(10) 0.0392(8) -0.0109(7) 0.0140(7) -0.0018(7)
  N4 0.0580(10) 0.0777(11) 0.0462(8) -0.0130(8) 0.0168(7) -0.0014(8)
  O41 0.0985(10) 0.1148(11) 0.0573(8) -0.0010(8) 0.0428(7) -0.0084(8)
  O42 0.0812(9) 0.1163(12) 0.0531(8) 0.0112(9) 0.0132(7) 0.0181(7)
  C5 0.0412(8) 0.0468(9) 0.0409(8) -0.0050(7) 0.0096(6) 0.0002(7)
  C51 0.0479(9) 0.0529(10) 0.0426(9) -0.0036(8) 0.0063(7) 0.0002(7)
  N51 0.0661(9) 0.0689(10) 0.0644(10) 0.0127(8) 0.0056(7) -0.0014(8)
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 . 1.3695(17) ?
  N1 C5 . 1.3790(17) ?
  N1 C11 . 1.4499(17) ?
  C11 C12 . 1.3726(19) ?
  C11 C16 . 1.377(2) ?
  C12 C13 . 1.376(2) ?
  C12 H12 . 0.951(15) ?
  C13 C14 . 1.370(2) ?
  C13 H13 . 0.935(17) ?
  C14 C15 . 1.365(2) ?
  C14 H14 . 0.914(19) ?
  C15 C16 . 1.379(2) ?
  C15 H15 . 0.920(17) ?
  C16 H16 . 0.930(15) ?
  C2 N3 . 1.3183(17) ?
  C2 C21 . 1.480(2) ?
  C21 H21A . 0.9600 ?
  C21 H21B . 0.9600 ?
  C21 H21C . 0.9600 ?
  N3 C4 . 1.3408(18) ?
  C4 C5 . 1.3628(19) ?
  C4 N4 . 1.4413(19) ?
  N4 O41 . 1.2131(16) ?
  N4 O42 . 1.2220(17) ?
  C5 C51 . 1.419(2) ?
  C51 N51 . 1.1372(18) ?