#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:00:13 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301809 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/12/2311245.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_2311245
loop_
_publ_author_name
'Krishnamurthy, M. S.'
'Begum, Noor Shahina'
_publ_section_title
;
 2-[4-(Tri-fluoro-meth-yl)phen-yl]-1H-benzimidazole.
;
_journal_coeditor_code           LH5706
_journal_issue                   'Pt 7'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o760
_journal_paper_doi               10.1107/S1600536814012963
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H9 F3 N2'
_chemical_formula_moiety         'C14 H9 F3 N2'
_chemical_formula_sum            'C14 H9 F3 N2'
_chemical_formula_weight         262.23
_chemical_name_systematic
;
2-[4-(Trifluoromethyl)phenyl]-1H-benzimidazole
;
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                   9.2292(9)
_cell_length_b                   9.8117(10)
_cell_length_c                   25.347(2)
_cell_measurement_reflns_used    1671
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.73
_cell_volume                     2295.3(4)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13079
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0563
_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)+(0.0847P)²+2.1194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                1671
_reflns_number_total             2501
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5706sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2295.2(4)
_cod_database_code               2311245
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
N N1 0.7803(2) 0.34060(19) -0.15282(8) 0.0231(5) Uani d . 1 1
H H1 0.7333 0.2656 -0.1490 0.028 Uiso calc R 1 1
N N2 0.8319(2) 0.56324(19) -0.14790(8) 0.0226(5) Uani d . 1 1
F F1 0.13831(19) 0.43903(16) -0.01444(8) 0.0575(6) Uani d . 1 1
F F2 0.09362(17) 0.6088(2) -0.06475(7) 0.0547(6) Uani d . 1 1
F F3 0.20033(18) 0.63865(18) 0.00860(7) 0.0495(5) Uani d . 1 1
C C1 1.0744(3) 0.5460(3) -0.19449(10) 0.0266(6) Uani d . 1 1
H H1A 1.0979 0.6380 -0.1922 0.032 Uiso calc R 1 1
C C2 1.1659(3) 0.4549(3) -0.21894(10) 0.0282(6) Uani d . 1 1
H H2 1.2515 0.4866 -0.2339 0.034 Uiso calc R 1 1
C C3 1.1332(3) 0.3152(2) -0.22181(9) 0.0271(6) Uani d . 1 1
H H3 1.1975 0.2567 -0.2387 0.033 Uiso calc R 1 1
C C4 1.0077(3) 0.2629(2) -0.20016(9) 0.0251(5) Uani d . 1 1
H H4 0.9867 0.1703 -0.2014 0.030 Uiso calc R 1 1
C C5 0.9137(2) 0.3561(2) -0.17622(9) 0.0221(5) Uani d . 1 1
C C6 0.9454(2) 0.4960(2) -0.17332(9) 0.0225(5) Uani d . 1 1
C C7 0.7369(2) 0.4661(2) -0.13685(9) 0.0220(5) Uani d . 1 1
C C8 0.5975(2) 0.4891(2) -0.11017(9) 0.0229(5) Uani d . 1 1
C C9 0.4787(3) 0.4059(3) -0.12079(10) 0.0303(6) Uani d . 1 1
H H9 0.4874 0.3348 -0.1449 0.036 Uiso calc R 1 1
C C10 0.3482(3) 0.4286(3) -0.09573(11) 0.0316(6) Uani d . 1 1
H H10 0.2691 0.3729 -0.1029 0.038 Uiso calc R 1 1
C C11 0.3353(3) 0.5344(2) -0.05983(10) 0.0261(6) Uani d . 1 1
C C12 0.4518(3) 0.6180(2) -0.04903(9) 0.0274(6) Uani d . 1 1
H H12 0.4422 0.6892 -0.0251 0.033 Uiso calc R 1 1
C C13 0.5836(3) 0.5953(2) -0.07410(9) 0.0252(5) Uani d . 1 1
H H13 0.6625 0.6512 -0.0668 0.030 Uiso calc R 1 1
C C14 0.1920(3) 0.5553(3) -0.03327(10) 0.0292(6) Uani d . 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
C7 N1 C5 107.02(19)
C7 N1 H1 126.5
C5 N1 H1 126.5
C7 N2 C6 104.73(18)
C2 C1 C6 117.9(2)
C2 C1 H1A 121.0
C6 C1 H1A 121.0
C1 C2 C3 121.7(2)
C1 C2 H2 119.2
C3 C2 H2 119.2
C4 C3 C2 121.5(2)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 116.7(2)
C3 C4 H4 121.6
C5 C4 H4 121.6
N1 C5 C4 132.1(2)
N1 C5 C6 105.74(19)
C4 C5 C6 122.2(2)
N2 C6 C1 130.7(2)
N2 C6 C5 109.3(2)
C1 C6 C5 120.0(2)
N2 C7 N1 113.2(2)
N2 C7 C8 124.5(2)
N1 C7 C8 122.3(2)
C13 C8 C9 119.5(2)
C13 C8 C7 119.8(2)
C9 C8 C7 120.7(2)
C10 C9 C8 120.2(2)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 119.9(2)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 120.6(2)
C12 C11 C14 121.2(2)
C10 C11 C14 118.3(2)
C11 C12 C13 119.8(2)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C8 120.0(2)
C12 C13 H13 120.0
C8 C13 H13 120.0
F2 C14 F1 107.5(2)
F2 C14 F3 106.0(2)
F1 C14 F3 105.1(2)
F2 C14 C11 113.0(2)
F1 C14 C11 111.8(2)
F3 C14 C11 112.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.357(3)
N1 C5 1.375(3)
N1 H1 0.8600
N2 C7 1.325(3)
N2 C6 1.395(3)
F1 C14 1.332(3)
F2 C14 1.318(3)
F3 C14 1.342(3)
C1 C2 1.377(3)
C1 C6 1.395(3)
C1 H1A 0.9300
C2 C3 1.405(4)
C2 H2 0.9300
C3 C4 1.380(3)
C3 H3 0.9300
C4 C5 1.399(3)
C4 H4 0.9300
C5 C6 1.406(3)
C7 C8 1.471(3)
C8 C13 1.393(3)
C8 C9 1.393(3)
C9 C10 1.379(4)
C9 H9 0.9300
C10 C11 1.386(3)
C10 H10 0.9300
C11 C12 1.380(3)
C11 C14 1.498(3)
C12 C13 1.391(3)
C12 H12 0.9300
C13 H13 0.9300
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_755 0.86 2.07 2.914(3) 165
C12 H12 F1 7_665 0.93 2.57 3.374(3) 144
C13 H13 F3 3_565 0.93 2.55 3.275(4) 134
C2 H2 Cg 6_656 0.93 2.94 3.700(3) 140
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
C6 C1 C2 C3 -1.3(4)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 1.2(3)
C7 N1 C5 C4 -179.0(2)
C7 N1 C5 C6 -0.3(2)
C3 C4 C5 N1 177.6(2)
C3 C4 C5 C6 -1.0(3)
C7 N2 C6 C1 179.2(2)
C7 N2 C6 C5 -0.6(2)
C2 C1 C6 N2 -178.2(2)
C2 C1 C6 C5 1.5(3)
N1 C5 C6 N2 0.5(2)
C4 C5 C6 N2 179.4(2)
N1 C5 C6 C1 -179.2(2)
C4 C5 C6 C1 -0.3(3)
C6 N2 C7 N1 0.4(3)
C6 N2 C7 C8 -179.4(2)
C5 N1 C7 N2 -0.1(3)
C5 N1 C7 C8 179.7(2)
N2 C7 C8 C13 -29.9(3)
N1 C7 C8 C13 150.3(2)
N2 C7 C8 C9 149.8(2)
N1 C7 C8 C9 -30.0(3)
C13 C8 C9 C10 -0.1(4)
C7 C8 C9 C10 -179.7(2)
C8 C9 C10 C11 0.0(4)
C9 C10 C11 C12 0.3(4)
C9 C10 C11 C14 -179.7(2)
C10 C11 C12 C13 -0.4(4)
C14 C11 C12 C13 179.6(2)
C11 C12 C13 C8 0.3(4)
C9 C8 C13 C12 -0.1(4)
C7 C8 C13 C12 179.6(2)
C12 C11 C14 F2 106.1(3)
C10 C11 C14 F2 -73.9(3)
C12 C11 C14 F1 -132.4(3)
C10 C11 C14 F1 47.6(3)
C12 C11 C14 F3 -14.1(3)
C10 C11 C14 F3 165.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 621761
