#------------------------------------------------------------------------------
#$Date: 2015-05-18 07:34:52 +0300 (Mon, 18 May 2015) $
#$Revision: 136894 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240733.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_2240733
loop_
_publ_author_name
'Krishnamurthy, M. S.'
'Fathima, Nikhath'
'Nagarajaiah, H.'
'Begum, Noor Shahina'
_publ_section_title
;
 2-(3,4-Difluorophenyl)-1H-benzimidazole
;
_journal_coeditor_code           LH5659
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1689
_journal_paper_doi               10.1107/S1600536813028559
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H8 F2 N2'
_chemical_formula_moiety         'C13 H8 F2 N2'
_chemical_formula_sum            'C13 H8 F2 N2'
_chemical_formula_weight         230.21
_chemical_name_systematic
;
2-(3,4-Difluorophenyl)-1H-benzimidazole
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7195(17)
_cell_length_b                   9.9454(19)
_cell_length_c                   23.389(4)
_cell_measurement_reflns_used    2209
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.91
_cell_volume                     2028.3(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 2012) and
CAMERON (Watkin et al., 1996)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD detector'
_diffrn_measurement_method       'ω 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  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13072
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0593
_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)+(0.0725P)²+2.7172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                1558
_reflns_number_total             2209
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5659sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2028.2(7)
_cod_database_code               2240733
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
F F1 0.14852(18) 0.58743(18) 0.48006(8) 0.0366(5) Uani d . 1 1
F F2 0.38138(19) 0.75233(17) 0.50344(7) 0.0341(5) Uani d . 1 1
N N1 0.8188(2) 0.5958(2) 0.36510(9) 0.0174(5) Uani d . 1 1
H H1 0.8081 0.6819 0.3727 0.021 Uiso calc R 1 1
N N2 0.7666(2) 0.3748(2) 0.36264(9) 0.0182(5) Uani d . 1 1
C C1 0.9394(3) 0.5363(2) 0.33662(11) 0.0177(5) Uani d . 1 1
C C2 0.7191(3) 0.4952(2) 0.37920(10) 0.0160(5) Uani d . 1 1
C C3 1.1638(3) 0.4987(3) 0.28151(11) 0.0211(6) Uani d . 1 1
H H3A 1.2526 0.5311 0.2624 0.025 Uiso calc R 1 1
C C4 1.1307(3) 0.3607(3) 0.28051(11) 0.0219(6) Uani d . 1 1
H H4 1.1975 0.3017 0.2605 0.026 Uiso calc R 1 1
C C5 1.0038(3) 0.3082(3) 0.30778(11) 0.0204(6) Uani d . 1 1
H H5 0.9838 0.2143 0.3076 0.025 Uiso calc R 1 1
C C6 0.9064(3) 0.3973(2) 0.33543(11) 0.0175(5) Uani d . 1 1
C C7 1.0692(3) 0.5888(3) 0.30993(11) 0.0212(6) Uani d . 1 1
H H7 1.0918 0.6822 0.3111 0.025 Uiso calc R 1 1
C C8 0.5694(3) 0.5218(2) 0.40631(11) 0.0185(5) Uani d . 1 1
C C9 0.4478(3) 0.4362(3) 0.39494(12) 0.0228(6) Uani d . 1 1
H H9 0.4632 0.3615 0.3703 0.027 Uiso calc R 1 1
C C10 0.3033(3) 0.4573(3) 0.41895(13) 0.0268(6) Uani d . 1 1
H H10 0.2201 0.3988 0.4106 0.032 Uiso calc R 1 1
C C11 0.2849(3) 0.5654(3) 0.45506(12) 0.0233(6) Uani d . 1 1
C C12 0.4062(3) 0.6501(3) 0.46667(12) 0.0216(6) Uani d . 1 1
C C13 0.5477(3) 0.6304(2) 0.44261(11) 0.0188(5) Uani d . 1 1
H H13 0.6298 0.6902 0.4507 0.023 Uiso calc R 1 1
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C1 106.7(2)
C2 N1 H1 126.6
C1 N1 H1 126.6
C2 N2 C6 105.2(2)
N1 C1 C7 132.4(2)
N1 C1 C6 105.9(2)
C7 C1 C6 121.6(2)
N2 C2 N1 113.1(2)
N2 C2 C8 124.4(2)
N1 C2 C8 122.4(2)
C7 C3 C4 121.2(2)
C7 C3 H3A 119.4
C4 C3 H3A 119.4
C5 C4 C3 121.8(2)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 117.7(2)
C4 C5 H5 121.1
C6 C5 H5 121.1
C5 C6 N2 130.2(2)
C5 C6 C1 120.6(2)
N2 C6 C1 109.1(2)
C3 C7 C1 117.1(2)
C3 C7 H7 121.5
C1 C7 H7 121.5
C9 C8 C13 119.5(2)
C9 C8 C2 118.9(2)
C13 C8 C2 121.6(2)
C8 C9 C10 121.4(2)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C9 118.0(2)
C11 C10 H10 121.0
C9 C10 H10 121.0
F1 C11 C10 119.8(2)
F1 C11 C12 119.5(2)
C10 C11 C12 120.6(2)
F2 C12 C13 120.9(2)
F2 C12 C11 117.6(2)
C13 C12 C11 121.4(2)
C12 C13 C8 119.1(2)
C12 C13 H13 120.5
C8 C13 H13 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.344(3)
F2 C12 1.349(3)
N1 C2 1.366(3)
N1 C1 1.378(3)
N1 H1 0.8800
N2 C2 1.326(3)
N2 C6 1.393(3)
C1 C7 1.394(4)
C1 C6 1.412(3)
C2 C8 1.474(4)
C3 C7 1.388(4)
C3 C4 1.403(4)
C3 H3A 0.9500
C4 C5 1.380(4)
C4 H4 0.9500
C5 C6 1.388(4)
C5 H5 0.9500
C7 H7 0.9500
C8 C9 1.386(4)
C8 C13 1.386(4)
C9 C10 1.396(4)
C9 H9 0.9500
C10 C11 1.376(4)
C10 H10 0.9500
C11 C12 1.379(4)
C12 C13 1.371(4)
C13 H13 0.9500
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
N1 H1 N2 7_765 0.88 2.04 2.874(3) 158
C13 H13 F2 3_566 0.95 2.51 3.379(3) 153
C3 H3A Cg 6_656 0.95 2.89 3.529(3) 125
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 C1 C7 176.2(3)
C2 N1 C1 C6 -0.7(3)
C6 N2 C2 N1 -0.5(3)
C6 N2 C2 C8 175.3(2)
C1 N1 C2 N2 0.7(3)
C1 N1 C2 C8 -175.1(2)
C7 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 1.6(4)
C4 C5 C6 N2 175.1(2)
C4 C5 C6 C1 -1.6(4)
C2 N2 C6 C5 -177.0(3)
C2 N2 C6 C1 0.0(3)
N1 C1 C6 C5 177.8(2)
C7 C1 C6 C5 0.5(4)
N1 C1 C6 N2 0.4(3)
C7 C1 C6 N2 -176.8(2)
C4 C3 C7 C1 -0.8(4)
N1 C1 C7 C3 -175.7(3)
C6 C1 C7 C3 0.7(4)
N2 C2 C8 C9 -26.6(4)
N1 C2 C8 C9 148.7(2)
N2 C2 C8 C13 153.6(2)
N1 C2 C8 C13 -31.1(4)
C13 C8 C9 C10 0.5(4)
C2 C8 C9 C10 -179.4(2)
C8 C9 C10 C11 -0.8(4)
C9 C10 C11 F1 -178.5(2)
C9 C10 C11 C12 0.4(4)
F1 C11 C12 F2 0.3(4)
C10 C11 C12 F2 -178.5(2)
F1 C11 C12 C13 179.2(2)
C10 C11 C12 C13 0.4(4)
F2 C12 C13 C8 178.2(2)
C11 C12 C13 C8 -0.7(4)
C9 C8 C13 C12 0.3(4)
C2 C8 C13 C12 -179.9(2)

_cod_database_fobs_code 2240733
