# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1990350'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        2-(2-fluorophenyl)-1H-benzimidazole
_chemical_name_common            2-(2-fluorophenyl)-1H-benzimidazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F N2'
_chemical_formula_sum            'C13 H9 F N2'
_chemical_formula_weight         212.22

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'

_cell_length_a                   7.1246(3)
_cell_length_b                   10.0327(4)
_cell_length_c                   29.6291(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2117.86(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13198
_cell_measurement_theta_min      2.985
_cell_measurement_theta_max      68.155

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   0.97240
_exptl_transmission_factor_max   0.99670
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            21923
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1924
_reflns_number_gt                1343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.9272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1924
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0944
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_restrained_S_all      1.261
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.6911(4) 0.1830(3) 0.04991(8) 0.1134(10) Uani 1 1 d . . . . .
N1 N 0.7381(4) -0.1213(3) 0.13844(9) 0.0517(7) Uani 1 1 d . . . . .
N2 N 0.8083(4) 0.0954(3) 0.13483(10) 0.0510(8) Uani 1 1 d . . . . .
C7 C 0.6949(5) -0.0047(3) 0.12045(11) 0.0469(9) Uani 1 1 d . . . . .
C6 C 0.8877(5) -0.0944(3) 0.16683(11) 0.0477(9) Uani 1 1 d . . . . .
C5 C 0.9882(5) -0.1786(4) 0.19502(13) 0.0636(11) Uani 1 1 d . . . . .
H5 H 0.9617 -0.2693 0.1964 0.076 Uiso 1 1 calc R U . . .
C4 C 1.1268(6) -0.1240(4) 0.22063(14) 0.0720(12) Uani 1 1 d . . . . .
H4 H 1.1948 -0.1789 0.2399 0.086 Uiso 1 1 calc R U . . .
C3 C 1.1703(5) 0.0112(4) 0.21896(14) 0.0738(12) Uani 1 1 d . . . . .
H3 H 1.2660 0.0444 0.2371 0.089 Uiso 1 1 calc R U . . .
C2 C 1.0740(5) 0.0963(4) 0.19097(13) 0.0668(11) Uani 1 1 d . . . . .
H2 H 1.1024 0.1867 0.1896 0.080 Uiso 1 1 calc R U . . .
C1 C 0.9322(5) 0.0406(3) 0.16483(11) 0.0490(9) Uani 1 1 d . . . . .
C8 C 0.5337(5) 0.0173(3) 0.09058(12) 0.0523(9) Uani 1 1 d . . . . .
C13 C 0.5330(6) 0.1106(4) 0.05693(14) 0.0722(12) Uani 1 1 d . . . . .
C12 C 0.3848(8) 0.1356(5) 0.02924(17) 0.1017(17) Uani 1 1 d . . . . .
H12 H 0.3921 0.1993 0.0065 0.122 Uiso 1 1 calc R U . . .
C11 C 0.2240(8) 0.0629(5) 0.03629(19) 0.1006(17) Uani 1 1 d . . . . .
H11 H 0.1193 0.0790 0.0184 0.121 Uiso 1 1 calc R U . . .
C10 C 0.2149(6) -0.0321(5) 0.06899(17) 0.0891(14) Uani 1 1 d . . . . .
H10 H 0.1053 -0.0809 0.0731 0.107 Uiso 1 1 calc R U . . .
C9 C 0.3696(6) -0.0558(4) 0.09617(14) 0.0728(12) Uani 1 1 d . . . . .
H9 H 0.3636 -0.1212 0.1184 0.087 Uiso 1 1 calc R U . . .
H2N H 0.802(5) 0.183(4) 0.1286(11) 0.074(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F1 C13 1.356(4) . ?
N1 C7 1.321(4) . ?
N1 C6 1.384(4) . ?
N2 C7 1.357(4) . ?
N2 C1 1.368(4) . ?
N2 H2N 0.90(4) . ?
C7 C8 1.467(4) . ?
C6 C5 1.387(4) . ?
C6 C1 1.392(4) . ?
C5 C4 1.361(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.392(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.374(5) . ?
C3 H3 0.9300 . ?
C2 C1 1.391(4) . ?
C2 H2 0.9300 . ?
C8 C13 1.367(5) . ?
C8 C9 1.390(5) . ?
C13 C12 1.360(6) . ?
C12 C11 1.374(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.361(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(5) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?

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 C6 104.6(3) . . ?
C7 N2 C1 106.9(3) . . ?
C7 N2 H2N 129(2) . . ?
C1 N2 H2N 124(2) . . ?
N1 C7 N2 113.0(3) . . ?
N1 C7 C8 124.0(3) . . ?
N2 C7 C8 122.9(3) . . ?
N1 C6 C5 130.1(3) . . ?
N1 C6 C1 109.8(3) . . ?
C5 C6 C1 120.1(3) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 116.7(4) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
N2 C1 C2 132.0(3) . . ?
N2 C1 C6 105.8(3) . . ?
C2 C1 C6 122.2(3) . . ?
C13 C8 C9 116.4(4) . . ?
C13 C8 C7 123.1(3) . . ?
C9 C8 C7 120.5(3) . . ?
F1 C13 C12 116.9(4) . . ?
F1 C13 C8 118.4(4) . . ?
C12 C13 C8 124.7(4) . . ?
C13 C12 C11 117.2(5) . . ?
C13 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
C10 C11 C12 121.3(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?

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
C6 N1 C7 N2 0.9(4) . . . . ?
C6 N1 C7 C8 -175.0(3) . . . . ?
C1 N2 C7 N1 -1.0(4) . . . . ?
C1 N2 C7 C8 175.0(3) . . . . ?
C7 N1 C6 C5 178.7(3) . . . . ?
C7 N1 C6 C1 -0.4(4) . . . . ?
N1 C6 C5 C4 -177.9(3) . . . . ?
C1 C6 C5 C4 1.1(5) . . . . ?
C6 C5 C4 C3 -0.6(6) . . . . ?
C5 C4 C3 C2 -0.1(6) . . . . ?
C4 C3 C2 C1 0.2(6) . . . . ?
C7 N2 C1 C2 -177.4(4) . . . . ?
C7 N2 C1 C6 0.7(4) . . . . ?
C3 C2 C1 N2 178.2(3) . . . . ?
C3 C2 C1 C6 0.4(5) . . . . ?
N1 C6 C1 N2 -0.2(4) . . . . ?
C5 C6 C1 N2 -179.4(3) . . . . ?
N1 C6 C1 C2 178.2(3) . . . . ?
C5 C6 C1 C2 -1.1(5) . . . . ?
N1 C7 C8 C13 -149.0(4) . . . . ?
N2 C7 C8 C13 35.5(5) . . . . ?
N1 C7 C8 C9 32.5(5) . . . . ?
N2 C7 C8 C9 -143.0(3) . . . . ?
C9 C8 C13 F1 -179.1(3) . . . . ?
C7 C8 C13 F1 2.3(6) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
C7 C8 C13 C12 -178.6(4) . . . . ?
F1 C13 C12 C11 -179.8(4) . . . . ?
C8 C13 C12 C11 1.1(7) . . . . ?
C13 C12 C11 C10 -1.4(7) . . . . ?
C12 C11 C10 C9 0.6(7) . . . . ?
C11 C10 C9 C8 0.5(7) . . . . ?
C13 C8 C9 C10 -0.8(6) . . . . ?
C7 C8 C9 C10 177.8(3) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1990351'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        2-(2-Bromophenyl)-1H-benzimidazole
_chemical_name_common            2-(2-Bromophenyl)-1H-benzimidazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'

_cell_length_a                   7.007(3)
_cell_length_b                   9.936(3)
_cell_length_c                   32.745(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2279.76(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20157
_cell_measurement_theta_min      4.050
_cell_measurement_theta_max      68.355

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   0.839
_exptl_transmission_factor_max   0.9158
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.255
_exptl_absorpt_coefficient_mu    4.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  Raxis-Rapid
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            23169
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         5.403
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2078
_reflns_number_gt                1916
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+7.5576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.089

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1990353'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        2-(3-bromophenyl)-1H-benzo[d]imidazole
_chemical_name_common            meta-bromo-benzimidazole
_chemical_melting_point          ?
_chemical_formula_moiety         C13H9BrN2
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6755(16)
_cell_length_b                   9.6559(18)
_cell_length_c                   9.7645(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.638(9)
_cell_angle_gamma                90
_cell_volume                     1110.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10369
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.671
_shelx_estimated_absorpt_T_min   0.261
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.3300
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
NUMABS; Higashi, 2002
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'NORMAL-focus sealed tube'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_detector       RX
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            28474
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2033
_reflns_number_gt                1444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  
;
MERCURY (Macrae et al., 2006); Platon (Spek,
 2009
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+7.1057P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2033
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.47411(7) 0.23892(11) -0.46597(10) 0.0834(4) Uani 1 1 d . . . . .
N1 N -0.0164(5) 0.3188(6) -0.1353(6) 0.0496(14) Uani 1 1 d . . . . .
N2 N 0.0057(4) 0.2407(6) 0.0889(5) 0.0476(13) Uani 1 1 d . . . . .
H2N H -0.0090 0.1986 0.1574 0.057 Uiso 1 1 d R U . . .
C1 C 0.1022(5) 0.3147(7) 0.1066(7) 0.0486(16) Uani 1 1 d . . . . .
C2 C 0.1987(6) 0.3424(8) 0.2267(8) 0.0571(19) Uani 1 1 d . . . . .
H2 H 0.2075 0.3095 0.3198 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2813(6) 0.4198(8) 0.2049(8) 0.0600(19) Uani 1 1 d . . . . .
H3 H 0.3479 0.4385 0.2845 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2683(6) 0.4715(8) 0.0663(9) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.3259 0.5246 0.0551 0.075 Uiso 1 1 calc R U . . .
C5 C 0.1712(6) 0.4451(8) -0.0546(8) 0.0596(19) Uani 1 1 d . . . . .
H5 H 0.1625 0.4801 -0.1468 0.072 Uiso 1 1 calc R U . . .
C6 C 0.0867(6) 0.3653(7) -0.0356(7) 0.0487(16) Uani 1 1 d . . . . .
C7 C -0.0624(5) 0.2457(7) -0.0557(6) 0.0436(15) Uani 1 1 d . . . . .
C8 C -0.1714(5) 0.1738(7) -0.1162(7) 0.0483(16) Uani 1 1 d . . . . .
C9 C -0.2550(5) 0.2270(7) -0.2427(7) 0.0492(16) Uani 1 1 d . . . . .
H9 H -0.2409 0.3054 -0.2886 0.059 Uiso 1 1 calc R U . . .
C10 C -0.3589(6) 0.1614(8) -0.2987(8) 0.0550(18) Uani 1 1 d . . . . .
C11 C -0.3802(7) 0.0417(9) -0.2366(8) 0.067(2) Uani 1 1 d . . . . .
H11 H -0.4499 -0.0028 -0.2773 0.080 Uiso 1 1 calc R U . . .
C12 C -0.2959(7) -0.0114(9) -0.1127(9) 0.070(2) Uani 1 1 d . . . . .
H12 H -0.3090 -0.0925 -0.0700 0.084 Uiso 1 1 calc R U . . .
C13 C -0.1927(6) 0.0549(8) -0.0520(7) 0.0597(19) Uani 1 1 d . . . . .
H13 H -0.1373 0.0195 0.0326 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C10 1.898(7) . ?
N1 C7 1.332(8) . ?
N1 C6 1.386(8) . ?
N2 C7 1.357(7) . ?
N2 C1 1.371(8) . ?
N2 H2N 0.8600 . ?
C1 C2 1.373(9) . ?
C1 C6 1.416(9) . ?
C2 C3 1.366(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(10) . ?
C5 H5 0.9300 . ?
C7 C8 1.463(9) . ?
C8 C13 1.382(10) . ?
C8 C9 1.395(9) . ?
C9 C10 1.380(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(11) . ?
C11 C12 1.384(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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 C6 105.3(5) . . ?
C7 N2 C1 107.9(5) . . ?
C7 N2 H2N 126.0 . . ?
C1 N2 H2N 126.0 . . ?
N2 C1 C2 133.0(7) . . ?
N2 C1 C6 105.2(5) . . ?
C2 C1 C6 121.9(7) . . ?
C3 C2 C1 117.8(7) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.6(7) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.9(7) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.6(7) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 N1 131.4(6) . . ?
C5 C6 C1 119.2(6) . . ?
N1 C6 C1 109.3(6) . . ?
N1 C7 N2 112.3(6) . . ?
N1 C7 C8 124.5(5) . . ?
N2 C7 C8 123.2(6) . . ?
C13 C8 C9 119.7(6) . . ?
C13 C8 C7 121.6(6) . . ?
C9 C8 C7 118.6(6) . . ?
C10 C9 C8 119.0(7) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 121.6(7) . . ?
C11 C10 Br1 119.8(6) . . ?
C9 C10 Br1 118.6(6) . . ?
C10 C11 C12 118.8(7) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.3(7) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?

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
C7 N2 C1 C2 -179.1(8) . . . . ?
C7 N2 C1 C6 0.7(7) . . . . ?
N2 C1 C2 C3 179.0(7) . . . . ?
C6 C1 C2 C3 -0.8(11) . . . . ?
C1 C2 C3 C4 1.0(12) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C4 C5 C6 -0.3(12) . . . . ?
C4 C5 C6 N1 -177.6(7) . . . . ?
C4 C5 C6 C1 0.6(11) . . . . ?
C7 N1 C6 C5 179.7(7) . . . . ?
C7 N1 C6 C1 1.3(7) . . . . ?
N2 C1 C6 C5 -179.8(6) . . . . ?
C2 C1 C6 C5 0.0(11) . . . . ?
N2 C1 C6 N1 -1.3(8) . . . . ?
C2 C1 C6 N1 178.6(6) . . . . ?
C6 N1 C7 N2 -0.9(8) . . . . ?
C6 N1 C7 C8 -178.6(6) . . . . ?
C1 N2 C7 N1 0.1(8) . . . . ?
C1 N2 C7 C8 177.8(6) . . . . ?
N1 C7 C8 C13 150.1(7) . . . . ?
N2 C7 C8 C13 -27.3(10) . . . . ?
N1 C7 C8 C9 -29.4(10) . . . . ?
N2 C7 C8 C9 153.2(6) . . . . ?
C13 C8 C9 C10 1.9(10) . . . . ?
C7 C8 C9 C10 -178.7(6) . . . . ?
C8 C9 C10 C11 -2.9(11) . . . . ?
C8 C9 C10 Br1 177.4(5) . . . . ?
C9 C10 C11 C12 1.8(12) . . . . ?
Br1 C10 C11 C12 -178.5(6) . . . . ?
C10 C11 C12 C13 0.4(12) . . . . ?
C11 C12 C13 C8 -1.4(12) . . . . ?
C9 C8 C13 C12 0.3(11) . . . . ?
C7 C8 C13 C12 -179.2(7) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.104

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1990352'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        2-(3-Chlorophenyl)-1H-benzimidazole
_chemical_name_common            2-(3-Chlorophenyl)-1H-benzimidazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Cl N2'
_chemical_formula_sum            'C13 H9 Cl N2'
_chemical_formula_weight         228.67

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5894(10)
_cell_length_b                   9.5051(8)
_cell_length_c                   9.7495(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.933(8)
_cell_angle_gamma                90
_cell_volume                     1082.22(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15162
_cell_measurement_theta_min      3.110
_cell_measurement_theta_max      27.515


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   0.985621
_exptl_transmission_factor_max   0.998395
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.133
_exptl_absorpt_coefficient_mu    0.322
_shelx_estimated_absorpt_T_min   0.98560
_shelx_estimated_absorpt_T_max   1.00000
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19656
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.238
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1959
_reflns_number_gt                1509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)'
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.5066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.02935(7) 0.27084(11) 0.04016(10) 0.0789(4) Uani 1 1 d . . . . .
N2 N 0.5032(2) 0.2610(3) 0.5865(2) 0.0398(6) Uani 1 1 d . . . . .
N1 N 0.48007(19) 0.1811(3) 0.3627(2) 0.0403(6) Uani 1 1 d . . . . .
C7 C 0.4343(2) 0.2551(3) 0.4412(3) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.5844(2) 0.1351(3) 0.4639(3) 0.0372(7) Uani 1 1 d . . . . .
C1 C 0.6000(2) 0.1847(3) 0.6045(3) 0.0372(7) Uani 1 1 d . . . . .
C9 C 0.2397(2) 0.2746(3) 0.2533(3) 0.0440(7) Uani 1 1 d . . . . .
H9 H 0.2541 0.1959 0.2064 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3235(2) 0.3266(3) 0.3811(3) 0.0391(7) Uani 1 1 d . . . . .
C2 C 0.6987(2) 0.1589(3) 0.7259(3) 0.0453(7) Uani 1 1 d . . . . .
H2 H 0.7083 0.1930 0.8191 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3012(3) 0.4457(3) 0.4476(3) 0.0510(8) Uani 1 1 d . . . . .
H13 H 0.3568 0.4810 0.5334 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6694(3) 0.0544(3) 0.4432(3) 0.0462(8) Uani 1 1 d . . . . .
H5 H 0.6601 0.0190 0.3505 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7817(3) 0.0809(3) 0.7028(3) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.8495 0.0621 0.7820 0.062 Uiso 1 1 calc R U . . .
C10 C 0.1356(3) 0.3405(4) 0.1971(3) 0.0503(8) Uani 1 1 d . . . . .
C4 C 0.7669(3) 0.0290(3) 0.5633(3) 0.0521(8) Uani 1 1 d . . . . .
H4 H 0.8249 -0.0243 0.5517 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1123(3) 0.4588(4) 0.2613(4) 0.0592(9) Uani 1 1 d . . . . .
H11 H 0.0412 0.5024 0.2213 0.071 Uiso 1 1 calc R U . . .
C12 C 0.1967(3) 0.5118(4) 0.3865(4) 0.0638(10) Uani 1 1 d . . . . .
H12 H 0.1828 0.5932 0.4302 0.077 Uiso 1 1 calc R U . . .
H2N H 0.486(2) 0.288(3) 0.656(3) 0.039(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C10 1.744(3) . ?
N2 C7 1.358(3) . ?
N2 C1 1.373(4) . ?
N2 H2N 0.82(3) . ?
N1 C7 1.320(3) . ?
N1 C6 1.387(3) . ?
C7 C8 1.462(4) . ?
C6 C5 1.390(4) . ?
C6 C1 1.393(3) . ?
C1 C2 1.380(4) . ?
C9 C10 1.368(4) . ?
C9 C8 1.389(4) . ?
C9 H9 0.9300 . ?
C8 C13 1.385(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C13 C12 1.376(4) . ?
C13 H13 0.9300 . ?
C5 C4 1.364(4) . ?
C5 H5 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C10 C11 1.371(5) . ?
C4 H4 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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 N2 C1 107.6(2) . . ?
C7 N2 H2N 127.7(19) . . ?
C1 N2 H2N 123.3(19) . . ?
C7 N1 C6 105.0(2) . . ?
N1 C7 N2 112.3(2) . . ?
N1 C7 C8 124.9(2) . . ?
N2 C7 C8 122.7(2) . . ?
N1 C6 C5 130.3(2) . . ?
N1 C6 C1 110.0(2) . . ?
C5 C6 C1 119.7(3) . . ?
N2 C1 C2 132.5(3) . . ?
N2 C1 C6 105.1(2) . . ?
C2 C1 C6 122.3(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 C7 121.5(3) . . ?
C9 C8 C7 119.1(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 Cl1 118.9(3) . . ?
C11 C10 Cl1 119.2(3) . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?

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
C6 N1 C7 N2 0.7(3) . . . . ?
C6 N1 C7 C8 179.3(3) . . . . ?
C1 N2 C7 N1 -0.6(3) . . . . ?
C1 N2 C7 C8 -179.2(2) . . . . ?
C7 N1 C6 C5 -179.2(3) . . . . ?
C7 N1 C6 C1 -0.5(3) . . . . ?
C7 N2 C1 C2 177.7(3) . . . . ?
C7 N2 C1 C6 0.3(3) . . . . ?
N1 C6 C1 N2 0.2(3) . . . . ?
C5 C6 C1 N2 179.0(3) . . . . ?
N1 C6 C1 C2 -177.6(3) . . . . ?
C5 C6 C1 C2 1.2(4) . . . . ?
C10 C9 C8 C13 -1.4(4) . . . . ?
C10 C9 C8 C7 179.5(2) . . . . ?
N1 C7 C8 C13 -151.9(3) . . . . ?
N2 C7 C8 C13 26.5(4) . . . . ?
N1 C7 C8 C9 27.1(4) . . . . ?
N2 C7 C8 C9 -154.5(3) . . . . ?
N2 C1 C2 C3 -177.5(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
C7 C8 C13 C12 178.8(3) . . . . ?
N1 C6 C5 C4 177.4(3) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C8 C9 C10 Cl1 -177.8(2) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
Cl1 C10 C11 C12 179.2(2) . . . . ?
C8 C13 C12 C11 1.6(5) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036

