#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:10:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180379 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/48/7204841.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_7204841
loop_
_publ_author_name
'Zakrassov, Alexander'
'Shteiman, Vitaly'
'Sheynin, Yana'
'Tumanskii, Boris'
'Botoshansky, Mark'
'Kapon, Moshe'
'Keren, Amit'
'Kaftory, Menahem'
'Vos, Thomas E.'
'Miller, Joel S.'
_publ_section_title
;
 Synthesis, structural, and magnetic characterization of substituted
 benzoimidazole-l-yl N,N?-dioxides
;
_journal_issue                   12
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1827
_journal_paper_doi               10.1039/b400299g
_journal_volume                  14
_journal_year                    2004
_chemical_formula_moiety         'C14 H8 N3 O2'
_chemical_formula_sum            'C14 H8 N3 O2'
_chemical_formula_weight         250.23
_chemical_name_systematic
;
2-(3-cyanophenyl)benzimidazolyl-N,N'-dioxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 118.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.722(1)
_cell_length_b                   7.138(2)
_cell_length_c                   13.316(1)
_cell_measurement_reflns_used    1811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      1.018
_cell_volume                     1149.1(4)
_computing_cell_refinement       'Denzo SMN (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius 2001)'
_computing_data_reduction        'Denzo SMN (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       omega-scans
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3277
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9608
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                1019
_reflns_number_total             1994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b400299g.txt
_cod_data_source_block           metacn
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7204841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.07749(15) 0.4921(3) 0.29051(17) 0.0689(7) Uani 1 1 d . . .
O2 O 0.02499(15) -0.1212(3) 0.41338(17) 0.0670(6) Uani 1 1 d . . .
N1 N -0.07917(17) 0.3147(3) 0.30554(18) 0.0525(6) Uani 1 1 d . . .
N2 N -0.03047(18) 0.0253(3) 0.36198(19) 0.0522(6) Uani 1 1 d . . .
N3 N 0.4703(3) -0.0483(6) 0.6217(3) 0.1117(13) Uani 1 1 d . . .
C1 C 0.0086(2) 0.2050(4) 0.3738(2) 0.0499(7) Uani 1 1 d . . .
C2 C -0.1760(2) 0.2044(4) 0.2514(2) 0.0503(7) Uani 1 1 d . . .
C3 C -0.2828(2) 0.2555(5) 0.1776(2) 0.0642(9) Uani 1 1 d . . .
H3 H -0.3081 0.4041 0.1517 0.077 Uiso 1 1 d R . .
C4 C -0.3584(2) 0.1100(5) 0.1394(3) 0.0708(9) Uani 1 1 d . . .
H4 H -0.4342 0.1335 0.0848 0.085 Uiso 1 1 d R . .
C5 C -0.3287(2) -0.0743(5) 0.1739(2) 0.0686(9) Uani 1 1 d . . .
H5 H -0.3861 -0.1673 0.1474 0.082 Uiso 1 1 d R . .
C6 C -0.2195(2) -0.1229(4) 0.2483(2) 0.0611(8) Uani 1 1 d . . .
H6 H -0.1956 -0.2538 0.2803 0.073 Uiso 1 1 d R . .
C7 C -0.1449(2) 0.0228(4) 0.2857(2) 0.0505(7) Uani 1 1 d . . .
C8 C 0.1209(2) 0.2661(4) 0.4472(2) 0.0517(7) Uani 1 1 d . . .
C9 C 0.2074(2) 0.1365(4) 0.4844(2) 0.0568(8) Uani 1 1 d . . .
H9 H 0.1892 -0.0078 0.4602 0.068 Uiso 1 1 d R . .
C10 C 0.3145(2) 0.1971(5) 0.5579(2) 0.0630(8) Uani 1 1 d . . .
C11 C 0.3361(3) 0.3807(5) 0.5945(3) 0.0717(9) Uani 1 1 d . . .
H11 H 0.4112 0.4155 0.6449 0.086 Uiso 1 1 d R . .
C12 C 0.2510(3) 0.5074(5) 0.5564(3) 0.0700(9) Uani 1 1 d . . .
H12 H 0.2681 0.6342 0.5830 0.084 Uiso 1 1 d R . .
C13 C 0.1433(2) 0.4533(4) 0.4829(2) 0.0608(8) Uani 1 1 d . . .
H13 H 0.0826 0.5400 0.4548 0.073 Uiso 1 1 d R . .
C14 C 0.4028(3) 0.0605(6) 0.5951(3) 0.0772(10) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C1 126.6(2) . . ?
O1 N1 C2 123.5(2) . . ?
C1 N1 C2 109.9(2) . . ?
O2 N2 C1 126.9(2) . . ?
O2 N2 C7 123.4(2) . . ?
C1 N2 C7 109.7(2) . . ?
N1 C1 N2 106.7(2) . . ?
N1 C1 C8 126.9(3) . . ?
N2 C1 C8 126.4(2) . . ?
C3 C2 C7 123.2(3) . . ?
C3 C2 N1 130.1(3) . . ?
C7 C2 N1 106.7(2) . . ?
C2 C3 C4 115.2(3) . . ?
C2 C3 H3 122.9 . . ?
C4 C3 H3 121.9 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 117.4 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 115.8(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 123.6 . . ?
C2 C7 C6 122.2(3) . . ?
C2 C7 N2 107.0(2) . . ?
C6 C7 N2 130.9(3) . . ?
C9 C8 C13 119.8(2) . . ?
C9 C8 C1 119.6(3) . . ?
C13 C8 C1 120.5(3) . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 121.8 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 C14 120.9(3) . . ?
C9 C10 C14 117.7(3) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 122.2 . . ?
C10 C11 H11 118.2 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 122.3 . . ?
C8 C13 H13 118.1 . . ?
N3 C14 C10 178.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.284(3) . ?
O2 N2 1.284(3) . ?
N1 C1 1.362(3) . ?
N1 C2 1.414(3) . ?
N2 C1 1.370(3) . ?
N2 C7 1.411(3) . ?
N3 C14 1.129(4) . ?
C1 C8 1.447(4) . ?
C2 C3 1.372(4) . ?
C2 C7 1.373(4) . ?
C3 C4 1.384(4) . ?
C3 H3 1.1186 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9601 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9600 . ?
C6 C7 1.376(4) . ?
C6 H6 1.0154 . ?
C8 C9 1.398(4) . ?
C8 C13 1.403(4) . ?
C9 C10 1.395(4) . ?
C9 H9 1.0732 . ?
C10 C11 1.380(4) . ?
C10 C14 1.448(5) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9601 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9600 . ?
C13 H13 0.9601 . ?
