#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/46/2234612.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_2234612
loop_
_publ_author_name
'Liu, Ming-Liang'
_publ_section_title
;
 2-Trifluoromethyl-1H-benzimidazole
;
_journal_coeditor_code           GO2052
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1518
_journal_paper_doi               10.1107/S1600536812017357
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H5 F3 N2'
_chemical_formula_moiety         'C8 H5 F3 N2'
_chemical_formula_sum            'C8 H5 F3 N2'
_chemical_formula_weight         186.14
_chemical_name_systematic
;
2-Trifluoromethyl-1H-benzimidazole
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_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                   11.859(2)
_cell_length_b                   7.2154(14)
_cell_length_c                   19.508(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      0
_cell_volume                     1669.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13301
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0707
_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)+(0.0577P)²+1.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                983
_reflns_number_total             1523
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            go2052.cif
_cod_data_source_block           I
_cod_database_code               2234612
_cod_database_fobs_code          2234612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, 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
C C2 0.2645(4) 0.2500 0.5000 0.0595(12) Uani d S 1 2
C C1 0.14185(18) 0.2500 0.5000 0.101(2) Uani d S 1 2
F F1A 0.09271(18) 0.1770 0.5534 0.157(4) Uani d PR 0.50 1
F F1B 0.09835(18) 0.1655 0.4469 0.191(5) Uani d PR 0.50 1
F F1C 0.10542(18) 0.4210 0.4964 0.213(5) Uani d PR 0.50 1
N N1 0.3246(2) 0.2091(3) 0.55507(11) 0.0576(7) Uani d . 1 1
H H1A 0.3000 0.1795 0.5951 0.069 Uiso calc PR 0.50 1
C C3 0.4353(2) 0.2242(4) 0.53443(14) 0.0495(7) Uani d . 1 1
C C4 0.5347(3) 0.1964(5) 0.5697(2) 0.0760(11) Uani d . 1 1
H H4 0.5350 0.1606 0.6155 0.091 Uiso calc R 1 1
C C5 0.6321(3) 0.2236(6) 0.5345(2) 0.0986(16) Uani d . 1 1
H H5 0.7006 0.2067 0.5568 0.118 Uiso calc R 1 1
F F10A 0.3495(3) 0.4573(4) 0.80332(12) 0.1403(12) Uani d . 1 1
F F10B 0.4734(4) 0.3146(6) 0.7500 0.1557(19) Uani d S 1 2
N N4 0.2610(2) 0.1033(4) 0.69268(12) 0.0641(8) Uani d . 1 1
H H4A 0.2749 0.1364 0.6512 0.077 Uiso calc PR 0.50 1
C C9 0.3662(6) 0.3519(8) 0.7500 0.0806(17) Uani d S 1 2
C C10 0.2953(4) 0.1861(6) 0.7500 0.0605(12) Uani d S 1 2
C C12 0.1984(3) -0.0467(5) 0.71420(15) 0.0623(9) Uani d . 1 1
C C13 0.1394(3) -0.1800(6) 0.6772(2) 0.0855(12) Uani d . 1 1
H H13 0.1382 -0.1800 0.6295 0.103 Uiso calc R 1 1
C C14 0.0830(4) -0.3113(7) 0.7148(2) 0.1073(16) Uani d . 1 1
H H14 0.0434 -0.4036 0.6917 0.129 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'
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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C2 N1 3_556 . 114.7(4)
N1 C2 C1 3_556 . 122.6(2)
N1 C2 C1 . . 122.6(2)
F1A C1 F1B . . 105.6
F1A C1 F1B 3_556 3_556 105.6
F1A C1 F1C 3_556 3_556 106.0
F1B C1 F1C 3_556 3_556 105.4
F1A C1 F1C . . 106.0
F1B C1 F1C . . 105.4
F1A C1 C2 3_556 . 116.522(6)
F1A C1 C2 . . 116.519(5)
F1B C1 C2 . . 113.229(5)
F1B C1 C2 3_556 . 113.230(5)
F1C C1 C2 3_556 . 109.263(5)
F1C C1 C2 . . 109.262(5)
C2 N1 C3 . . 105.0(3)
C2 N1 H1A . . 127.5
C3 N1 H1A . . 127.5
N1 C3 C4 . . 131.0(3)
N1 C3 C3 . 3_556 107.64(15)
C4 C3 C3 . 3_556 121.3(2)
C5 C4 C3 . . 116.9(4)
C5 C4 H4 . . 121.5
C3 C4 H4 . . 121.5
C4 C5 C5 . 3_556 121.8(2)
C4 C5 H5 . . 119.1
C5 C5 H5 3_556 . 119.1
C10 N4 C12 . . 105.1(3)
C10 N4 H4A . . 127.4
C12 N4 H4A . . 127.4
F10B C9 F10A . . 105.6(4)
F10B C9 F10A . 6_557 105.6(4)
F10A C9 F10A . 6_557 105.9(5)
F10B C9 C10 . . 113.1(5)
F10A C9 C10 . . 113.0(3)
F10A C9 C10 6_557 . 113.0(3)
N4 C10 N4 . 6_557 114.3(4)
N4 C10 C9 . . 122.9(2)
N4 C10 C9 6_557 . 122.9(2)
N4 C12 C13 . . 131.0(3)
N4 C12 C12 . 6_557 107.74(16)
C13 C12 C12 . 6_557 121.3(2)
C14 C13 C12 . . 116.4(4)
C14 C13 H13 . . 121.8
C12 C13 H13 . . 121.8
C13 C14 C14 . 6_557 122.3(2)
C13 C14 H14 . . 118.9
C14 C14 H14 6_557 . 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 N1 3_556 1.323(3)
C2 N1 . 1.323(3)
C2 C1 . 1.454(5)
C1 F1A 3_556 1.3052
C1 F1A . 1.3053
C1 F1B . 1.3079
C1 F1B 3_556 1.3079
C1 F1C 3_556 1.3095
C1 F1C . 1.3095
N1 C3 . 1.377(4)
N1 H1A . 0.8600
C3 C4 . 1.380(4)
C3 C3 3_556 1.394(5)
C4 C5 . 1.359(5)
C4 H4 . 0.9300
C5 C5 3_556 1.399(9)
C5 H5 . 0.9300
F10A C9 . 1.303(4)
F10B C9 . 1.300(7)
N4 C10 . 1.331(3)
N4 C12 . 1.378(4)
N4 H4A . 0.8600
C9 F10A 6_557 1.304(4)
C9 C10 . 1.462(7)
C10 N4 6_557 1.331(3)
C12 C13 . 1.392(5)
C12 C12 6_557 1.397(6)
C13 C14 . 1.372(6)
C13 H13 . 0.9300
C14 C14 6_557 1.375(9)
C14 H14 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A N4 0.86 2.03 2.891(3) 173
N4 H4A N1 0.86 2.03 2.891(3) 174
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C2 C1 F1A 3_556 3_556 -11.43(13)
N1 C2 C1 F1A . 3_556 168.57(13)
N1 C2 C1 F1A 3_556 . 168.57(13)
N1 C2 C1 F1A . . -11.43(13)
N1 C2 C1 F1B 3_556 . 45.84(13)
N1 C2 C1 F1B . . -134.16(13)
N1 C2 C1 F1B 3_556 3_556 -134.16(13)
N1 C2 C1 F1B . 3_556 45.84(13)
N1 C2 C1 F1C 3_556 3_556 108.66(13)
N1 C2 C1 F1C . 3_556 -71.34(13)
N1 C2 C1 F1C 3_556 . -71.34(13)
N1 C2 C1 F1C . . 108.66(13)
N1 C2 N1 C3 3_556 . -0.07(14)
C1 C2 N1 C3 . . 179.93(14)
C2 N1 C3 C4 . . -179.4(3)
C2 N1 C3 C3 . 3_556 0.2(3)
N1 C3 C4 C5 . . -179.7(3)
C3 C3 C4 C5 3_556 . 0.7(5)
C3 C4 C5 C5 . 3_556 -0.4(7)
C12 N4 C10 N4 . 6_557 0.2(5)
C12 N4 C10 C9 . . 179.2(5)
F10B C9 C10 N4 . . -89.5(4)
F10A C9 C10 N4 . . 150.6(4)
F10A C9 C10 N4 6_557 . 30.4(8)
F10B C9 C10 N4 . 6_557 89.5(4)
F10A C9 C10 N4 . 6_557 -30.4(8)
F10A C9 C10 N4 6_557 6_557 -150.6(4)
C10 N4 C12 C13 . . 178.1(4)
C10 N4 C12 C12 . 6_557 -0.1(3)
N4 C12 C13 C14 . . -178.8(4)
C12 C12 C13 C14 6_557 . -0.8(4)
C12 C13 C14 C14 . 6_557 0.8(4)
