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#$Date: 2016-03-26 17:10:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180379 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/48/7204837.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_7204837
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         'C13 H7 Cl F N2 O2'
_chemical_formula_sum            'C13 H7 Cl F N2 O2'
_chemical_formula_weight         277.66
_chemical_name_systematic
;
2-(2-chloro,6-fluorophenyl)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                 109.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.370(2)
_cell_length_b                   15.787(3)
_cell_length_c                   7.790(1)
_cell_measurement_reflns_used    9048
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.48
_cell_volume                     1200.8(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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9048
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.8742
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0898
_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)+(0.1345P)²+0.8565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2183
_refine_ls_wR_factor_ref         0.2320
_reflns_number_gt                1524
_reflns_number_total             2106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b400299g.txt
_cod_data_source_block           clf(a)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7204837
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
Cl1 Cl 0.19238(16) 0.02777(9) 1.23145(16) 0.0654(5) Uani 1 1 d . . .
F1 F 0.2080(3) -0.02310(18) 0.6013(3) 0.0595(8) Uani 1 1 d . . .
O1 O 0.1184(3) -0.1721(2) 0.7775(4) 0.0550(9) Uani 1 1 d . . .
O2 O 0.4789(4) -0.0223(2) 1.1762(4) 0.0574(9) Uani 1 1 d . . .
N1 N 0.2327(3) -0.1536(2) 0.8981(4) 0.0396(8) Uani 1 1 d . . .
N2 N 0.4045(4) -0.0823(2) 1.0888(4) 0.0415(9) Uani 1 1 d . . .
C1 C 0.2772(4) -0.0748(3) 0.9581(5) 0.0372(9) Uani 1 1 d . . .
C2 C 0.3331(4) -0.2134(3) 0.9939(5) 0.0413(10) Uani 1 1 d . . .
C3 C 0.3321(5) -0.3009(3) 0.9859(7) 0.0558(12) Uani 1 1 d . . .
H3 H 0.2589 -0.3309 0.9068 0.067 Uiso 1 1 calc R . .
C4 C 0.4461(6) -0.3408(3) 1.1021(9) 0.0702(16) Uani 1 1 d . . .
H4 H 0.4507 -0.3996 1.1014 0.084 Uiso 1 1 calc R . .
C5 C 0.5523(6) -0.2962(4) 1.2183(8) 0.0744(17) Uani 1 1 d . . .
H5 H 0.6269 -0.3261 1.2944 0.089 Uiso 1 1 calc R . .
C6 C 0.5550(5) -0.2085(4) 1.2290(7) 0.0607(13) Uani 1 1 d . . .
H6 H 0.6282 -0.1787 1.3084 0.073 Uiso 1 1 calc R . .
C7 C 0.4400(4) -0.1691(3) 1.1118(6) 0.0448(10) Uani 1 1 d . . .
C8 C 0.2029(4) 0.0033(3) 0.8946(5) 0.0381(9) Uani 1 1 d . . .
C9 C 0.1679(5) 0.0274(3) 0.7140(6) 0.0467(11) Uani 1 1 d . . .
C10 C 0.0954(5) 0.0986(3) 0.6424(7) 0.0555(13) Uani 1 1 d . . .
H10 H 0.0726 0.1116 0.5193 0.067 Uiso 1 1 calc R . .
C11 C 0.0575(5) 0.1502(3) 0.7578(8) 0.0634(14) Uani 1 1 d . . .
H11 H 0.0101 0.1999 0.7125 0.076 Uiso 1 1 calc R . .
C12 C 0.0879(5) 0.1305(3) 0.9409(8) 0.0610(14) Uani 1 1 d . . .
H12 H 0.0604 0.1660 1.0174 0.073 Uiso 1 1 calc R . .
C13 C 0.1610(5) 0.0557(3) 1.0082(6) 0.0469(11) 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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 126.1(3) . . ?
O1 N1 C2 124.9(3) . . ?
C1 N1 C2 109.0(3) . . ?
O2 N2 C1 126.5(4) . . ?
O2 N2 C7 124.8(4) . . ?
C1 N2 C7 108.7(3) . . ?
N1 C1 N2 107.9(3) . . ?
N1 C1 C8 125.7(3) . . ?
N2 C1 C8 126.4(3) . . ?
C7 C2 C3 122.2(4) . . ?
C7 C2 N1 107.3(4) . . ?
C3 C2 N1 130.4(4) . . ?
C4 C3 C2 115.8(5) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 123.4(5) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C7 C6 C5 114.5(5) . . ?
C7 C6 H6 122.8 . . ?
C5 C6 H6 122.8 . . ?
C2 C7 C6 122.4(5) . . ?
C2 C7 N2 107.0(4) . . ?
C6 C7 N2 130.5(4) . . ?
C9 C8 C13 117.1(4) . . ?
C9 C8 C1 120.6(4) . . ?
C13 C8 C1 122.4(4) . . ?
F1 C9 C10 118.0(4) . . ?
F1 C9 C8 117.8(4) . . ?
C10 C9 C8 124.2(4) . . ?
C9 C10 C11 117.7(5) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C10 C11 C12 121.8(5) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C12 120.6(4) . . ?
C8 C13 Cl1 120.1(4) . . ?
C12 C13 Cl1 119.2(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
Cl1 C13 1.716(5) . ?
F1 C9 1.351(5) . ?
O1 N1 1.274(4) . ?
O2 N2 1.265(4) . ?
N1 C1 1.354(5) . ?
N1 C2 1.418(5) . ?
N2 C1 1.374(5) . ?
N2 C7 1.416(6) . ?
C1 C8 1.450(6) . ?
C2 C7 1.370(6) . ?
C2 C3 1.382(7) . ?
C3 C4 1.376(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(6) . ?
C6 H6 0.9300 . ?
C8 C9 1.382(6) . ?
C8 C13 1.385(6) . ?
C9 C10 1.364(7) . ?
C10 C11 1.364(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(7) . ?
C12 H12 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 179.5(4) . . . . ?
C2 N1 C1 N2 0.7(4) . . . . ?
O1 N1 C1 C8 -0.6(6) . . . . ?
C2 N1 C1 C8 -179.5(4) . . . . ?
O2 N2 C1 N1 179.8(4) . . . . ?
C7 N2 C1 N1 -0.5(4) . . . . ?
O2 N2 C1 C8 -0.1(7) . . . . ?
C7 N2 C1 C8 179.7(4) . . . . ?
O1 N1 C2 C7 -179.5(4) . . . . ?
C1 N1 C2 C7 -0.6(4) . . . . ?
O1 N1 C2 C3 -1.8(7) . . . . ?
C1 N1 C2 C3 177.0(4) . . . . ?
C7 C2 C3 C4 -0.9(7) . . . . ?
N1 C2 C3 C4 -178.3(5) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C3 C2 C7 C6 1.0(7) . . . . ?
N1 C2 C7 C6 178.9(4) . . . . ?
C3 C2 C7 N2 -177.6(4) . . . . ?
N1 C2 C7 N2 0.3(4) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
C5 C6 C7 N2 177.6(4) . . . . ?
O2 N2 C7 C2 179.8(4) . . . . ?
C1 N2 C7 C2 0.1(5) . . . . ?
O2 N2 C7 C6 1.4(7) . . . . ?
C1 N2 C7 C6 -178.4(5) . . . . ?
N1 C1 C8 C9 -61.1(6) . . . . ?
N2 C1 C8 C9 118.8(5) . . . . ?
N1 C1 C8 C13 117.2(5) . . . . ?
N2 C1 C8 C13 -62.9(6) . . . . ?
C13 C8 C9 F1 -180.0(4) . . . . ?
C1 C8 C9 F1 -1.6(6) . . . . ?
C13 C8 C9 C10 0.0(6) . . . . ?
C1 C8 C9 C10 178.3(4) . . . . ?
F1 C9 C10 C11 -178.7(4) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C9 C10 C11 C12 -1.6(8) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
C9 C8 C13 C12 -0.9(6) . . . . ?
C1 C8 C13 C12 -179.3(4) . . . . ?
C9 C8 C13 Cl1 176.6(3) . . . . ?
C1 C8 C13 Cl1 -1.8(6) . . . . ?
C11 C12 C13 C8 0.6(7) . . . . ?
C11 C12 C13 Cl1 -176.9(4) . . . . ?
