#------------------------------------------------------------------------------
#$Date: 2020-05-19 03:37:57 +0200 (mar 19 de may de 2020) $
#$Revision: 252159 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/05/7240547.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_7240547
loop_
_publ_author_name
'Bombicz, Petra Alexandra'
'May, Nóra Veronika'
'Fegyverneki, Daniel'
'Saranchimeg, Avirmed'
'Bereczki, Laura'
_publ_section_title
;
 Methods for easy recognition of isostructurality - Lab Jack-like crystal
 structures of halogenated 2-phenylbenzimidazoles
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00410C
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_chemical_name_common            2-(2-Bromophenyl)-1H-benzimidazole
_chemical_name_systematic        2-(2-Bromophenyl)-1H-benzimidazole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.007(3)
_cell_length_b                   9.936(3)
_cell_length_c                   32.745(3)
_cell_measurement_reflns_used    20157
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.355
_cell_measurement_theta_min      4.050
_cell_volume                     2279.8(12)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Raxis-Rapid
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            23169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         5.403
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    4.675
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.255
_exptl_transmission_factor_max   0.9158
_exptl_transmission_factor_min   0.839
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0369P)²+7.5576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             2078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00410c2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_cell_volume        2279.76(16)
_cod_database_code               7240547
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24081(10) 0.68588(6) 0.05134(2) 0.0579(3) Uani 1 1 d . . . . .
N1 N 0.2556(5) 0.3711(4) 0.14657(10) 0.0298(8) Uani 1 1 d . . . . .
N2 N 0.3031(5) 0.5924(4) 0.14425(11) 0.0283(8) Uani 1 1 d . . . . .
C12 C -0.2815(7) 0.4196(6) 0.08616(18) 0.0564(15) Uani 1 1 d . . . . .
H12 H -0.3869 0.3671 0.0927 0.068 Uiso 1 1 calc R U . . .
C8 C 0.0378(6) 0.4965(5) 0.10196(13) 0.0337(10) Uani 1 1 d . . . . .
C7 C 0.2022(6) 0.4862(4) 0.13013(12) 0.0268(9) Uani 1 1 d . . . . .
C6 C 0.4302(6) 0.5427(4) 0.17272(13) 0.0281(9) Uani 1 1 d . . . . .
C2 C 0.5063(6) 0.3236(5) 0.19990(13) 0.0338(10) Uani 1 1 d . . . . .
H2 H 0.4894 0.2308 0.2005 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6363(6) 0.3855(5) 0.22484(13) 0.0356(10) Uani 1 1 d . . . . .
H3 H 0.7066 0.3338 0.2431 0.043 Uiso 1 1 calc R U . . .
C1 C 0.4001(6) 0.4042(4) 0.17351(12) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.0318(7) 0.5763(5) 0.06685(14) 0.0412(11) Uani 1 1 d . . . . .
C4 C 0.6658(6) 0.5238(5) 0.22351(14) 0.0394(11) Uani 1 1 d . . . . .
H4 H 0.7568 0.5618 0.2407 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5643(6) 0.6066(5) 0.19750(13) 0.0360(10) Uani 1 1 d . . . . .
H5 H 0.5841 0.6991 0.1966 0.043 Uiso 1 1 calc R U . . .
C13 C -0.1228(7) 0.4182(5) 0.11068(16) 0.0460(12) Uani 1 1 d . . . . .
H13 H -0.1221 0.3637 0.1338 0.055 Uiso 1 1 calc R U . . .
C11 C -0.2836(8) 0.4992(8) 0.05170(18) 0.0670(19) Uani 1 1 d . . . . .
H11 H -0.3907 0.4998 0.0349 0.080 Uiso 1 1 calc R U . . .
C10 C -0.1283(9) 0.5777(6) 0.04191(16) 0.0575(16) Uani 1 1 d . . . . .
H10 H -0.1308 0.6315 0.0187 0.069 Uiso 1 1 calc R U . . .
H2N H 0.284(5) 0.669(4) 0.1395(11) 0.007(10) Uiso 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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C7 N1 C1 105.2(3) . . ?
C7 N2 C6 106.8(4) . . ?
C7 N2 H2N 127(3) . . ?
C6 N2 H2N 126(3) . . ?
C13 C12 C11 119.6(6) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C13 C8 C9 117.4(4) . . ?
C13 C8 C7 117.5(4) . . ?
C9 C8 C7 125.1(4) . . ?
N1 C7 N2 112.9(4) . . ?
N1 C7 C8 122.4(4) . . ?
N2 C7 C8 124.5(4) . . ?
N2 C6 C1 105.6(4) . . ?
N2 C6 C5 131.7(4) . . ?
C1 C6 C5 122.8(4) . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N1 C1 C6 109.5(4) . . ?
N1 C1 C2 130.5(4) . . ?
C6 C1 C2 119.9(4) . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 Br1 117.5(4) . . ?
C8 C9 Br1 121.6(4) . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 115.8(4) . . ?
C4 C5 H5 122.1 . . ?
C6 C5 H5 122.1 . . ?
C12 C13 C8 121.8(5) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C10 C9 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
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
Br1 C9 1.894(5) . ?
N1 C7 1.318(6) . ?
N1 C1 1.382(5) . ?
N2 C7 1.352(6) . ?
N2 C6 1.381(5) . ?
N2 H2N 0.79(4) . ?
C12 C13 1.371(7) . ?
C12 C11 1.378(9) . ?
C12 H12 0.9300 . ?
C8 C13 1.397(7) . ?
C8 C9 1.397(6) . ?
C8 C7 1.480(6) . ?
C6 C1 1.392(6) . ?
C6 C5 1.395(6) . ?
C2 C3 1.370(6) . ?
C2 C1 1.393(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C9 C10 1.388(7) . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C11 C10 1.377(10) . ?
C11 H11 0.9300 . ?
C10 H10 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
C1 N1 C7 N2 0.5(5) . . . . ?
C1 N1 C7 C8 -174.6(4) . . . . ?
C6 N2 C7 N1 -1.2(5) . . . . ?
C6 N2 C7 C8 173.9(4) . . . . ?
C13 C8 C7 N1 38.7(6) . . . . ?
C9 C8 C7 N1 -139.9(5) . . . . ?
C13 C8 C7 N2 -135.8(5) . . . . ?
C9 C8 C7 N2 45.5(6) . . . . ?
C7 N2 C6 C1 1.2(4) . . . . ?
C7 N2 C6 C5 -178.0(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C7 N1 C1 C6 0.3(5) . . . . ?
C7 N1 C1 C2 178.4(4) . . . . ?
N2 C6 C1 N1 -1.0(5) . . . . ?
C5 C6 C1 N1 178.4(4) . . . . ?
N2 C6 C1 C2 -179.3(4) . . . . ?
C5 C6 C1 C2 0.1(6) . . . . ?
C3 C2 C1 N1 -177.0(4) . . . . ?
C3 C2 C1 C6 0.9(6) . . . . ?
C13 C8 C9 C10 0.3(7) . . . . ?
C7 C8 C9 C10 179.0(5) . . . . ?
C13 C8 C9 Br1 -179.5(4) . . . . ?
C7 C8 C9 Br1 -0.8(6) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
N2 C6 C5 C4 178.6(4) . . . . ?
C1 C6 C5 C4 -0.6(6) . . . . ?
C11 C12 C13 C8 0.5(8) . . . . ?
C9 C8 C13 C12 -0.4(7) . . . . ?
C7 C8 C13 C12 -179.2(4) . . . . ?
C13 C12 C11 C10 -0.4(9) . . . . ?
C12 C11 C10 C9 0.3(9) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
Br1 C9 C10 C11 179.6(4) . . . . ?
