#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$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/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013995
loop_
_publ_author_name
'Kubicki, Maciej'
_publ_section_title
;
 Cyano--cyano and chloro--cyano interactions in two imidazole
 derivatives
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o255
_journal_page_last               o257
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C11 H8 N4 O2'
_chemical_formula_moiety         'C11 H8 N4 O2'
_chemical_formula_sum            'C11 H8 N4 O2'
_chemical_formula_weight         228.21
_chemical_name_systematic
;
2-methyl-4-nitro-1-phenyl-1H-imidazole-5-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.313(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8976(9)
_cell_length_b                   9.6168(9)
_cell_length_c                   11.6700(10)
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      3
_cell_volume                     1080.94(17)
_computing_cell_refinement       CrysAlisCCD
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlisRed (Oxford Diffraction, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'KUMA KM-4 CCD four-circle diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6917
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         4.70
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                1380
_reflns_number_total             2708
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    gd1304.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P2~1~/n
_cod_database_code               2013995
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'
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_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_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 106.86(11) ?
C2 N1 C11 126.53(12) ?
C5 N1 C11 126.55(11) ?
C12 C11 C16 121.32(14) ?
C12 C11 N1 119.66(12) ?
C16 C11 N1 119.00(13) ?
C11 C12 C13 118.71(16) ?
C11 C12 H12 120.2(9) ?
C13 C12 H12 121.1(9) ?
C14 C13 C12 120.5(2) y
C14 C13 H13 119.1(10) ?
C12 C13 H13 120.3(10) ?
C15 C14 C13 120.4(2) y
C15 C14 H14 122.6(11) ?
C13 C14 H14 117.0(11) ?
C14 C15 C16 120.2(2) y
C14 C15 H15 123.9(11) ?
C16 C15 H15 115.9(11) ?
C11 C16 C15 118.92(16) ?
C11 C16 H16 119.4(9) ?
C15 C16 H16 121.7(9) ?
N3 C2 N1 111.48(13) ?
N3 C2 C21 125.32(13) ?
N1 C2 C21 123.20(13) ?
C2 C21 H21A 109.5 ?
C2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C2 N3 C4 104.70(12) ?
N3 C4 C5 112.97(13) ?
N3 C4 N4 121.26(13) ?
C5 C4 N4 125.77(15) ?
O41 N4 O42 124.15(15) ?
O41 N4 C4 118.76(16) ?
O42 N4 C4 117.09(14) ?
C4 C5 N1 103.98(12) ?
C4 C5 C51 132.83(14) ?
N1 C5 C51 123.17(12) ?
N51 C51 C5 179.70(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12 O41 3_656 0.95(2) 2.59(2) 3.456(2) 151.0(10)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 C11 C12 -78.56(17)
C5 N1 C11 C12 104.58(16)
C2 N1 C11 C16 100.17(17)
C5 N1 C11 C16 -76.69(18)
C16 C11 C12 C13 -0.1(2)
N1 C11 C12 C13 178.59(13)
C11 C12 C13 C14 -0.7(2)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C16 0.4(3)
C12 C11 C16 C15 1.1(2)
N1 C11 C16 C15 -177.63(13)
C14 C15 C16 C11 -1.2(2)
C5 N1 C2 N3 0.29(15)
C11 N1 C2 N3 -177.07(12)
C5 N1 C2 C21 -179.95(13)
C11 N1 C2 C21 2.7(2)
N1 C2 N3 C4 0.09(16)
C21 C2 N3 C4 -179.67(14)
C2 N3 C4 C5 -0.46(16)
C2 N3 C4 N4 179.88(12)
N3 C4 N4 O41 0.2(2)
C5 C4 N4 O41 -179.43(14)
N3 C4 N4 O42 -179.59(14)
C5 C4 N4 O42 0.8(2)
N3 C4 C5 N1 0.63(16)
N4 C4 C5 N1 -179.73(12)
N3 C4 C5 C51 -177.70(14)
N4 C4 C5 C51 1.9(3)
C2 N1 C5 C4 -0.53(14)
C11 N1 C5 C4 176.83(12)
C2 N1 C5 C51 178.01(13)
C11 N1 C5 C51 -4.6(2)