# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_SALIL_SJ_22_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2271385'
loop_
_audit_author_name
_audit_author_address
'Amlan Kumar Pal'
;Indian Institute of Technology Jammu
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-31
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.133
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.4258(5)
_cell_length_b                   16.5006(11)
_cell_length_c                   7.3773(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.406(2)
_cell_angle_gamma                90
_cell_volume                     1088.70(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9745
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.59
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction'
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_description       block
_exptl_crystal_F_000             543.361
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.9309
_diffrn_reflns_Laue_measured_fraction_max 0.8639
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6754
_diffrn_reflns_point_group_measured_fraction_full 0.9309
_diffrn_reflns_point_group_measured_fraction_max 0.8639
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.28
_diffrn_ambient_temperature      103.0
_diffrn_measured_fraction_theta_full 0.9309
_diffrn_measured_fraction_theta_max 0.8639
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2058
_reflns_number_total             2330
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.6796
_refine_diff_density_min         -0.4566
_refine_diff_density_rms         0.1068
_refine_ls_d_res_high            0.7507
_refine_ls_d_res_low             8.9436
_refine_ls_goodness_of_fit_ref   1.0306
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.0306
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1124
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.70368(3) 0.812810(17) 0.51126(4) 0.02956(16) Uani 1.000000 .
N1 N 0.1698(3) 0.67899(13) 0.4763(4) 0.0256(5) Uani 1.000000 .
N2 N 0.0589(3) 0.79664(15) 0.5064(4) 0.0321(6) Uani 1.000000 .
C10 C 0.2060(4) 0.43043(17) 0.3836(4) 0.0340(7) Uani 1.000000 .
H10 H 0.2146(4) 0.37426(17) 0.3609(4) 0.0408(8) Uiso 1.000000 R
C11 C 0.0778(4) 0.47217(17) 0.2843(5) 0.0371(7) Uani 1.000000 .
H11 H -0.0022(4) 0.44432(17) 0.1946(5) 0.0446(8) Uiso 1.000000 R
C12 C 0.0652(4) 0.55433(17) 0.3148(4) 0.0322(6) Uani 1.000000 .
H12 H -0.0226(4) 0.58299(17) 0.2456(4) 0.0386(8) Uiso 1.000000 R
C7 C 0.1814(3) 0.59412(15) 0.4464(4) 0.0239(5) Uani 1.000000 .
C3 C 0.2774(3) 0.73820(17) 0.4954(3) 0.0236(6) Uani 1.000000 .
C4 C 0.2062(3) 0.81172(15) 0.5157(4) 0.0258(7) Uani 1.000000 .
C5 C 0.2859(4) 0.88426(16) 0.5401(4) 0.0297(6) Uani 1.000000 .
H5 H 0.2404(4) 0.93398(16) 0.5560(4) 0.0357(7) Uiso 1.000000 R
C6 C 0.4321(4) 0.88218(16) 0.5408(4) 0.0299(6) Uani 1.000000 .
H6 H 0.4881(4) 0.93104(16) 0.5585(4) 0.0359(7) Uiso 1.000000 R
C8 C 0.3098(3) 0.55257(17) 0.5497(4) 0.0298(6) Uani 1.000000 .
H8 H 0.3886(3) 0.58003(17) 0.6423(4) 0.0358(7) Uiso 1.000000 R
C9 C 0.3215(4) 0.47072(19) 0.5160(4) 0.0348(7) Uani 1.000000 .
H9 H 0.4095(4) 0.44203(19) 0.5843(4) 0.0417(8) Uiso 1.000000 R
C13 C 0.0438(3) 0.71797(18) 0.4823(4) 0.0308(6) Uani 1.000000 .
H13 H -0.0473(3) 0.69046(18) 0.4700(4) 0.0369(7) Uiso 1.000000 R
C2 C 0.4254(3) 0.73552(16) 0.4935(4) 0.0251(6) Uani 1.000000 .
H2 H 0.4721(3) 0.68616(16) 0.4778(4) 0.0301(7) Uiso 1.000000 R
C1 C 0.4996(4) 0.80915(15) 0.5158(4) 0.0265(6) Uani 1.000000 .


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 C1 1.935(3) . ?
N1 C7 1.427(3) . ?
N1 C3 1.383(4) . ?
N1 C13 1.363(4) . ?
N2 C4 1.391(4) . ?
N2 C13 1.312(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C10 C9 1.382(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C7 1.379(4) . ?
C7 C8 1.391(4) . ?
C3 C4 1.417(4) . ?
C3 C2 1.400(4) . ?
C4 C5 1.394(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C1 1.402(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9500 . ?
C13 H13 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.386(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
C3 N1 C7 128.3(3) . . ?
C13 N1 C7 125.3(3) . . ?
C13 N1 C3 106.4(2) . . ?
C13 N2 C4 104.3(3) . . ?
C11 C10 H10 120.12(17) . . ?
C9 C10 H10 120.12(18) . . ?
C9 C10 C11 119.8(3) . . ?
H11 C11 C10 119.78(17) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.78(19) . . ?
H12 C12 C11 120.30(19) . . ?
C7 C12 C11 119.4(3) . . ?
C7 C12 H12 120.30(16) . . ?
C12 C7 N1 119.6(3) . . ?
C8 C7 N1 119.6(3) . . ?
C8 C7 C12 120.8(3) . . ?
C4 C3 N1 105.0(2) . . ?
C2 C3 N1 132.7(3) . . ?
C2 C3 C4 122.3(3) . . ?
C3 C4 N2 109.9(2) . . ?
C5 C4 N2 130.5(3) . . ?
C5 C4 C3 119.6(3) . . ?
H5 C5 C4 120.75(18) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.75(16) . . ?
H6 C6 C5 119.45(16) . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 H6 119.45(18) . . ?
H8 C8 C7 120.43(17) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4(2) . . ?
C8 C9 C10 120.5(3) . . ?
H9 C9 C10 119.76(18) . . ?
H9 C9 C8 119.8(2) . . ?
N2 C13 N1 114.4(3) . . ?
H13 C13 N1 122.80(16) . . ?
H13 C13 N2 122.80(19) . . ?
H2 C2 C3 122.00(16) . . ?
C1 C2 C3 116.0(3) . . ?
C1 C2 H2 122.00(18) . . ?
C6 C1 Br1 118.1(2) . . ?
C2 C1 Br1 119.5(2) . . ?
C2 C1 C6 122.4(3) . . ?

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
Br1 C1 C6 C5 178.2(2) . . . . ?
Br1 C1 C2 C3 -179.0(2) . . . . ?
N1 C7 C12 C11 179.1(3) . . . . ?
N1 C7 C8 C9 -178.3(3) . . . . ?
N1 C3 C4 N2 -0.7(2) . . . . ?
N1 C3 C4 C5 179.4(2) . . . . ?
N1 C3 C2 C1 179.4(3) . . . . ?
N1 C13 N2 C4 0.5(3) . . . . ?
N2 C4 C3 C2 178.0(2) . . . . ?
N2 C4 C5 C6 -178.9(3) . . . . ?
C10 C11 C12 C7 -0.5(4) . . . . ?
C10 C9 C8 C7 -1.1(3) . . . . ?
C11 C12 C7 C8 -0.6(4) . . . . ?
C12 C7 C8 C9 1.4(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C2 C1 C6 0.6(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C5 C6 C1 C2 -1.4(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        6-bromo-1-phenyl-1H-benzo[d]imidazole
_exptl_crystal_colour            colourless
_chemical_melting_point          'Not determined'
_exptl_crystal_recrystallization_method 
'The crystal was grown by the slow evaporation of the titled compound in ethylacetate.'
_chemical_compound_source        'Synthesized in lab'
####################################################################### 
# 
# 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_mo_ps_100_ow_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2271386'
loop_
_audit_author_name
_audit_author_address
'Amlan Kumar Pal'
;Indian Institute of Technology Jammu
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.04.25 svn.r3594 for OlexSys, GUI svn.r5751)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        5-bromo-1-phenyl-1H-benzo[d]imidazole
_chemical_formula_moiety         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_chemical_melting_point          'Not determined'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.718(3)
_cell_length_b                   3.9640(8)
_cell_length_c                   16.793(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.542(7)
_cell_angle_gamma                90
_cell_volume                     1090.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.522
_exptl_absorpt_coefficient_mu    3.740
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_preparation       'Synthesised in laboratory'
_exptl_crystal_recrystallization_method 
'The crystal was obtained by slow evaporation of the title compound in ethylacetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20489
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_min         1.922
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             2708
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.208
_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)+(0.0092P)²+4.4827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1037
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.56060(2) 0.58080(10) 0.09814(2) 0.02560(13) Uani 1 1 d . . . . .
N1 N 0.52163(17) 0.8220(8) 0.40272(18) 0.0210(6) Uani 1 1 d . . . . .
N2 N 0.64091(16) 0.5849(8) 0.46216(16) 0.0183(5) Uani 1 1 d . . . . .
C1 C 0.5872(2) 0.5609(9) 0.2140(2) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.53551(19) 0.7089(9) 0.2586(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.485801 0.813846 0.233348 0.023 Uiso 1 1 calc R . . . .
C3 C 0.56071(19) 0.6952(9) 0.3432(2) 0.0187(6) Uani 1 1 d . . . . .
C4 C 0.57067(19) 0.7487(9) 0.4715(2) 0.0203(7) Uani 1 1 d . . . . .
H4 H 0.558951 0.803396 0.523019 0.024 Uiso 1 1 calc R . . . .
C5 C 0.63523(19) 0.5459(9) 0.37909(19) 0.0172(6) Uani 1 1 d . . . . .
C6 C 0.6856(2) 0.3891(9) 0.3332(2) 0.0191(6) Uani 1 1 d . . . . .
H6 H 0.734711 0.279385 0.358266 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6606(2) 0.4011(9) 0.2495(2) 0.0205(7) Uani 1 1 d . . . . .
H7 H 0.693323 0.300202 0.215924 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7053(2) 0.4752(8) 0.5264(2) 0.0183(6) Uani 1 1 d . . . . .
C9 C 0.7861(2) 0.5158(9) 0.5193(2) 0.0222(7) Uani 1 1 d . . . . .
H9 H 0.799067 0.616977 0.472171 0.027 Uiso 1 1 calc R . . . .
C10 C 0.8476(2) 0.4060(11) 0.5822(2) 0.0286(8) Uani 1 1 d . . . . .
H10 H 0.903061 0.430898 0.577869 0.034 Uiso 1 1 calc R . . . .
C11 C 0.8288(2) 0.2608(10) 0.6509(2) 0.0305(8) Uani 1 1 d . . . . .
H11 H 0.871325 0.187599 0.693784 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7483(3) 0.2222(10) 0.6573(2) 0.0292(8) Uani 1 1 d . . . . .
H12 H 0.735533 0.121664 0.704573 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6859(2) 0.3292(9) 0.5952(2) 0.0220(7) Uani 1 1 d . . . . .
H13 H 0.630459 0.302773 0.599631 0.026 Uiso 1 1 calc R . . . .


_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 C1 1.909(3) . ?
N1 C3 1.393(4) . ?
N1 C4 1.308(5) . ?
N2 C4 1.378(4) . ?
N2 C5 1.388(4) . ?
N2 C8 1.431(4) . ?
C1 C2 1.383(5) . ?
C1 C7 1.403(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(5) . ?
C3 C5 1.402(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(5) . ?
C8 C13 1.387(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(5) . ?
C13 H13 0.9500 . ?

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
C4 N1 C3 104.6(3) . . ?
C4 N2 C5 106.1(3) . . ?
C4 N2 C8 125.9(3) . . ?
C5 N2 C8 127.9(3) . . ?
C2 C1 Br1 119.4(3) . . ?
C2 C1 C7 123.3(3) . . ?
C7 C1 Br1 117.3(2) . . ?
C1 C2 H2 122.0 . . ?
C1 C2 C3 116.1(3) . . ?
C3 C2 H2 122.0 . . ?
N1 C3 C2 128.7(3) . . ?
N1 C3 C5 110.3(3) . . ?
C2 C3 C5 120.9(3) . . ?
N1 C4 N2 113.7(3) . . ?
N1 C4 H4 123.1 . . ?
N2 C4 H4 123.1 . . ?
N2 C5 C3 105.2(3) . . ?
N2 C5 C6 132.6(3) . . ?
C6 C5 C3 122.2(3) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 H6 121.6 . . ?
C1 C7 H7 119.7 . . ?
C6 C7 C1 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 N2 119.8(3) . . ?
C13 C8 N2 119.3(3) . . ?
C13 C8 C9 120.9(3) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 120.4 . . ?
C12 C13 C8 119.2(3) . . ?
C12 C13 H13 120.4 . . ?

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
Br1 C1 C2 C3 -177.6(2) . . . . ?
Br1 C1 C7 C6 177.3(3) . . . . ?
N1 C3 C5 N2 -0.1(4) . . . . ?
N1 C3 C5 C6 177.9(3) . . . . ?
N2 C5 C6 C7 -179.6(4) . . . . ?
N2 C8 C9 C10 -179.6(3) . . . . ?
N2 C8 C13 C12 179.8(3) . . . . ?
C1 C2 C3 N1 179.9(3) . . . . ?
C1 C2 C3 C5 1.5(5) . . . . ?
C2 C1 C7 C6 -1.0(6) . . . . ?
C2 C3 C5 N2 178.6(3) . . . . ?
C2 C3 C5 C6 -3.5(5) . . . . ?
C3 N1 C4 N2 0.9(4) . . . . ?
C3 C5 C6 C7 3.0(5) . . . . ?
C4 N1 C3 C2 -179.0(4) . . . . ?
C4 N1 C3 C5 -0.5(4) . . . . ?
C4 N2 C5 C3 0.6(4) . . . . ?
C4 N2 C5 C6 -177.1(4) . . . . ?
C4 N2 C8 C9 -138.8(4) . . . . ?
C4 N2 C8 C13 41.2(5) . . . . ?
C5 N2 C4 N1 -1.0(4) . . . . ?
C5 N2 C8 C9 42.2(5) . . . . ?
C5 N2 C8 C13 -137.8(4) . . . . ?
C5 C6 C7 C1 -0.8(5) . . . . ?
C7 C1 C2 C3 0.7(5) . . . . ?
C8 N2 C4 N1 179.9(3) . . . . ?
C8 N2 C5 C3 179.7(3) . . . . ?
C8 N2 C5 C6 2.0(6) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 C8 0.1(6) . . . . ?
C13 C8 C9 C10 0.3(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'On a loop fibre'
_olex2_submission_original_sample_id PS_100_ow
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_compound_source        'Synthesized in lab'
####################################################################### 
# 
# 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_mo_PS_103_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2271388'
loop_
_audit_author_name
_audit_author_address
'Amlan Kumar Pal'
;Indian Institute of Technology Jammu
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_systematic        
'6-bromo-3-methyl-1-phenyl-1H-benzo[d]imidazol-3-ium iodide'
_chemical_formula_moiety         'C14 H12 Br N2, I'
_chemical_formula_sum            'C14 H12 Br I N2'
_chemical_formula_weight         415.067
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.811(3)
_cell_length_b                   22.538(7)
_cell_length_c                   7.398(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.91(1)
_cell_angle_gamma                90
_cell_volume                     1405.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6769
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    5.107
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_description       block
_exptl_crystal_F_000             792.0
_exptl_crystal_preparation       'Synthesized in laboratory'
_exptl_crystal_recrystallization_method 
'Crystals were grown by the slow diffusion of the hexanes into the concentrated solution of the titled compound in ethylacetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.9980
_diffrn_reflns_Laue_measured_fraction_max 0.9943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            37947
_diffrn_reflns_point_group_measured_fraction_full 0.9980
_diffrn_reflns_point_group_measured_fraction_max 0.9943
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.42
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                3126
_reflns_number_total             3491
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         1.6455
_refine_diff_density_min         -1.3586
_refine_diff_density_rms         0.1756
_refine_ls_d_res_high            0.7477
_refine_ls_d_res_low             8.4298
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.0451
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+4.9015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1184
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C5(H5), C6(H6), C13(H13), C2(H2), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
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_refinement_flags_posn
I1 I 1.02483(4) 0.401902(15) 0.74900(4) 0.04097(13) Uani 1.000000 .
Br1 Br 0.37264(8) 0.20485(2) 0.27481(7) 0.05027(18) Uani 1.000000 .
N1 N 0.7040(5) 0.40311(17) 0.2488(5) 0.0324(8) Uani 1.000000 .
N2 N 0.9233(5) 0.3578(2) 0.2507(6) 0.0472(11) Uani 1.000000 .
C10 C 0.3962(6) 0.5444(2) 0.2497(7) 0.0394(10) Uani 1.000000 .
H10 H 0.3266(6) 0.5765(2) 0.2513(7) 0.0473(12) Uiso 1.000000 R
C9 C 0.3378(5) 0.4935(2) 0.1460(7) 0.0340(9) Uani 1.000000 .
H9 H 0.2284(5) 0.4907(2) 0.0785(7) 0.0409(11) Uiso 1.000000 R
C8 C 0.4394(5) 0.44710(18) 0.1413(6) 0.0282(8) Uani 1.000000 .
H8 H 0.4021(5) 0.41288(18) 0.0667(6) 0.0339(9) Uiso 1.000000 R
C7 C 0.5973(5) 0.45163(19) 0.2483(6) 0.0287(8) Uani 1.000000 .
C3 C 0.6745(6) 0.3430(2) 0.2620(6) 0.0331(9) Uani 1.000000 .
C4 C 0.8175(6) 0.3146(2) 0.2644(6) 0.0399(11) Uani 1.000000 .
C5 C 0.8306(7) 0.2530(3) 0.2733(7) 0.0484(13) Uani 1.000000 .
H5 H 0.9267(7) 0.2335(3) 0.2750(7) 0.0581(16) Uiso 1.000000 R
C6 C 0.6983(9) 0.2217(2) 0.2794(7) 0.0564(17) Uani 1.000000 .
H6 H 0.7027(9) 0.1796(2) 0.2850(7) 0.068(2) Uiso 1.000000 R
C13 C 0.8555(6) 0.4103(3) 0.2454(7) 0.0403(11) Uani 1.000000 .
H13 H 0.9054(6) 0.4474(3) 0.2401(7) 0.0483(13) Uiso 1.000000 R
C14 C 1.0910(7) 0.3478(4) 0.2630(9) 0.065(2) Uani 1.000000 .
H14a H 1.1495(15) 0.337(3) 0.392(2) 0.097(3) Uiso 1.000000 GR
H14b H 1.0990(8) 0.3160(18) 0.176(6) 0.097(3) Uiso 1.000000 GR
H14c H 1.136(2) 0.3844(8) 0.229(8) 0.097(3) Uiso 1.000000 GR
C2 C 0.5409(6) 0.3120(2) 0.2717(6) 0.0340(9) Uani 1.000000 .
H2 H 0.4458(6) 0.3314(2) 0.2740(6) 0.0408(11) Uiso 1.000000 R
C1 C 0.5557(7) 0.2509(2) 0.2777(7) 0.0409(11) Uani 1.000000 .
C12 C 0.6560(6) 0.5013(2) 0.3534(6) 0.0349(9) Uani 1.000000 .
H12 H 0.7642(6) 0.5031(2) 0.4265(6) 0.0418(11) Uiso 1.000000 R
C11 C 0.5563(6) 0.5485(2) 0.3516(7) 0.0396(10) Uani 1.000000 .
H11 H 0.5963(6) 0.5837(2) 0.4193(7) 0.0476(12) Uiso 1.000000 R


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 C1 1.913(6) . ?
N1 C7 1.441(6) . ?
N1 C3 1.389(6) . ?
N1 C13 1.352(6) . ?
N2 C4 1.371(8) . ?
N2 C13 1.322(7) . ?
N2 C14 1.471(7) . ?
C10 H10 0.9500 . ?
C10 C9 1.392(7) . ?
C10 C11 1.396(8) . ?
C9 H9 0.9500 . ?
C9 C8 1.384(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(6) . ?
C7 C12 1.376(6) . ?
C3 C4 1.409(6) . ?
C3 C2 1.388(7) . ?
C4 C5 1.393(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(10) . ?
C6 H6 0.9500 . ?
C6 C1 1.416(8) . ?
C13 H13 0.9500 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C2 H2 0.9500 . ?
C2 C1 1.382(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.376(7) . ?
C11 H11 0.9500 . ?

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
C3 N1 C7 127.3(4) . . ?
C13 N1 C7 123.7(4) . . ?
C13 N1 C3 108.9(4) . . ?
C13 N2 C4 109.1(4) . . ?
C14 N2 C4 125.4(5) . . ?
C14 N2 C13 125.1(6) . . ?
C9 C10 H10 119.8(3) . . ?
C11 C10 H10 119.8(3) . . ?
C11 C10 C9 120.4(4) . . ?
H9 C9 C10 120.1(3) . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9 120.1(3) . . ?
H8 C8 C9 120.7(3) . . ?
C7 C8 C9 118.6(4) . . ?
C7 C8 H8 120.7(3) . . ?
C8 C7 N1 119.3(4) . . ?
C12 C7 N1 118.6(4) . . ?
C12 C7 C8 122.1(4) . . ?
C4 C3 N1 105.0(4) . . ?
C2 C3 N1 132.3(4) . . ?
C2 C3 C4 122.7(4) . . ?
C3 C4 N2 107.6(4) . . ?
C5 C4 N2 131.4(5) . . ?
C5 C4 C3 121.0(5) . . ?
H5 C5 C4 121.5(4) . . ?
C6 C5 C4 117.0(5) . . ?
C6 C5 H5 121.5(3) . . ?
H6 C6 C5 119.3(3) . . ?
C1 C6 C5 121.3(5) . . ?
C1 C6 H6 119.3(3) . . ?
N2 C13 N1 109.4(5) . . ?
H13 C13 N1 125.3(3) . . ?
H13 C13 N2 125.3(3) . . ?
H14a C14 N2 109.5 . . ?
H14b C14 N2 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 N2 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H2 C2 C3 122.3(3) . . ?
C1 C2 C3 115.4(5) . . ?
C1 C2 H2 122.3(3) . . ?
C6 C1 Br1 119.4(4) . . ?
C2 C1 Br1 118.0(4) . . ?
C2 C1 C6 122.6(5) . . ?
H12 C12 C7 120.4(3) . . ?
C11 C12 C7 119.3(4) . . ?
C11 C12 H12 120.4(3) . . ?
C12 C11 C10 119.8(4) . . ?
H11 C11 C10 120.1(3) . . ?
H11 C11 C12 120.1(3) . . ?

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
Br1 C1 C6 C5 177.1(4) . . . . ?
Br1 C1 C2 C3 -176.1(3) . . . . ?
N1 C7 C8 C9 178.5(4) . . . . ?
N1 C7 C12 C11 178.8(4) . . . . ?
N1 C3 C4 N2 -0.7(4) . . . . ?
N1 C3 C4 C5 -178.8(4) . . . . ?
N1 C3 C2 C1 178.0(5) . . . . ?
N1 C13 N2 C4 -2.1(5) . . . . ?
N1 C13 N2 C14 -175.3(4) . . . . ?
N2 C4 C3 C2 179.3(4) . . . . ?
N2 C4 C5 C6 -177.6(6) . . . . ?
C10 C9 C8 C7 2.8(5) . . . . ?
C10 C11 C12 C7 2.6(5) . . . . ?
C9 C8 C7 C12 -1.9(5) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C3 C2 C1 C6 1.7(5) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C5 C6 C1 C2 -0.6(6) . . . . ?


_olex2_exptl_crystal_mounting_method 'On a loop fibre'
_olex2_submission_original_sample_id PS-103
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_compound_source        'Synthesized in lab'
####################################################################### 
# 
# 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_mo_ps_102_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2271387'
loop_
_audit_author_name
_audit_author_address
'Amlan Kumar Pal'
;Indian Institute of Technology Jammu
India
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_systematic        
'5-bromo-3-methyl-1-phenyl-1H-benzo[d]imidazol-3-ium iodide'
_chemical_formula_moiety         'C14 H12 Br N2, I'
_chemical_formula_sum            'C14 H12 Br I N2'
_chemical_formula_weight         415.073
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.6109(18)
_cell_length_b                   10.0029(16)
_cell_length_c                   14.313(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.058(5)
_cell_angle_gamma                90
_cell_volume                     1452.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.52
_exptl_absorpt_coefficient_mu    4.940
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0985 after correction.
The Ratio of minimum to maximum transmission is 0.7419.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       block
_exptl_crystal_F_000             792.00
_exptl_crystal_preparation       'Synthesized in laboratory'
_exptl_crystal_recrystallization_method 
'Crystals were obtained by slow evaporation of the title compound in acetone'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.9890
_diffrn_reflns_Laue_measured_fraction_max 0.9791
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40011
_diffrn_reflns_point_group_measured_fraction_full 0.9890
_diffrn_reflns_point_group_measured_fraction_max 0.9791
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9890
_diffrn_measured_fraction_theta_max 0.9791
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3236
_reflns_number_total             3563
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.1190
_refine_diff_density_min         -1.7615
_refine_diff_density_rms         0.2212
_refine_ls_d_res_high            0.7481
_refine_ls_d_res_low             10.1441
_refine_ls_goodness_of_fit_ref   1.0228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.0228
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+2.4797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1063
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C11(H11), C10(H10), C6(H6), C5(H5), C8(H8), C9(H9), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
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_refinement_flags_posn
I1 I 0.62385(3) 0.42001(2) 0.707848(16) 0.03562(11) Uani 1.000000 .
Br1 Br -0.04653(4) 0.19707(5) 0.36734(3) 0.04437(13) Uani 1.000000 .
N1 N 0.2725(3) 0.4506(3) 0.7420(2) 0.0288(6) Uani 1.000000 .
N2 N 0.2694(3) 0.5526(3) 0.6072(2) 0.0310(6) Uani 1.000000 .
C1 C 0.0579(4) 0.2721(4) 0.4881(3) 0.0361(8) Uani 1.000000 .
C2 C 0.1242(4) 0.3899(4) 0.4882(3) 0.0342(7) Uani 1.000000 .
H2 H 0.1225(4) 0.4353(4) 0.4295(3) 0.0411(9) Uiso 1.000000 R
C3 C 0.1940(3) 0.4384(3) 0.5797(3) 0.0289(7) Uani 1.000000 .
C4 C 0.1956(3) 0.3711(3) 0.6652(3) 0.0292(6) Uani 1.000000 .
C7 C 0.3056(3) 0.4219(3) 0.8452(3) 0.0283(7) Uani 1.000000 .
C12 C 0.3580(4) 0.2971(4) 0.8779(3) 0.0322(7) Uani 1.000000 .
H12 H 0.3711(4) 0.2319(4) 0.8334(3) 0.0387(8) Uiso 1.000000 R
C11 C 0.3908(4) 0.2703(4) 0.9774(3) 0.0366(8) Uani 1.000000 .
H11 H 0.4265(4) 0.1856(4) 1.0015(3) 0.0439(9) Uiso 1.000000 R
C10 C 0.3719(4) 0.3659(5) 1.0416(3) 0.0399(8) Uani 1.000000 .
H10 H 0.3949(4) 0.3469(5) 1.1096(3) 0.0479(10) Uiso 1.000000 R
C6 C 0.0593(4) 0.2020(4) 0.5739(3) 0.0378(8) Uani 1.000000 .
H6 H 0.0117(4) 0.1206(4) 0.5693(3) 0.0454(10) Uiso 1.000000 R
C5 C 0.1297(4) 0.2509(4) 0.6648(3) 0.0354(7) Uani 1.000000 .
H5 H 0.1328(4) 0.2049(4) 0.7235(3) 0.0425(9) Uiso 1.000000 R
C8 C 0.2856(4) 0.5177(4) 0.9083(3) 0.0368(8) Uani 1.000000 .
H8 H 0.2490(4) 0.6021(4) 0.8843(3) 0.0442(9) Uiso 1.000000 R
C9 C 0.3193(5) 0.4895(4) 1.0072(3) 0.0432(9) Uani 1.000000 .
H9 H 0.3064(5) 0.5549(4) 1.0515(3) 0.0518(11) Uiso 1.000000 R
C13 C 0.3153(4) 0.5561(3) 0.7041(3) 0.0300(7) Uani 1.000000 .
H13 H 0.3706(4) 0.6241(3) 0.7407(3) 0.0360(8) Uiso 1.000000 R
C14 C 0.3009(4) 0.6491(4) 0.5407(3) 0.0404(8) Uani 1.000000 .
H14a H 0.359(3) 0.718(2) 0.5787(3) 0.0606(13) Uiso 1.000000 GR
H14b H 0.345(3) 0.6032(7) 0.4987(18) 0.0606(13) Uiso 1.000000 GR
H14c H 0.2195(5) 0.690(3) 0.5002(18) 0.0606(13) Uiso 1.000000 GR


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 C1 1.912(4) . ?
N1 C4 1.408(4) . ?
N1 C7 1.443(5) . ?
N1 C13 1.326(5) . ?
N2 C3 1.384(5) . ?
N2 C13 1.328(5) . ?
N2 C14 1.462(5) . ?
C1 C2 1.372(6) . ?
C1 C6 1.410(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(5) . ?
C3 C4 1.392(5) . ?
C4 C5 1.390(5) . ?
C7 C12 1.390(5) . ?
C7 C8 1.376(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.381(6) . ?
C10 H10 0.9500 . ?
C10 C9 1.386(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.383(6) . ?
C9 H9 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?

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 C4 126.8(3) . . ?
C13 N1 C4 108.6(3) . . ?
C13 N1 C7 124.6(3) . . ?
C13 N2 C3 108.9(3) . . ?
C14 N2 C3 125.7(3) . . ?
C14 N2 C13 125.3(3) . . ?
C2 C1 Br1 119.9(3) . . ?
C6 C1 Br1 116.6(3) . . ?
C6 C1 C2 123.5(3) . . ?
H2 C2 C1 122.2(2) . . ?
C3 C2 C1 115.6(4) . . ?
C3 C2 H2 122.2(2) . . ?
C2 C3 N2 131.3(4) . . ?
C4 C3 N2 106.9(3) . . ?
C4 C3 C2 121.7(3) . . ?
C3 C4 N1 105.6(3) . . ?
C5 C4 N1 131.9(3) . . ?
C5 C4 C3 122.5(3) . . ?
C12 C7 N1 118.5(3) . . ?
C8 C7 N1 119.7(3) . . ?
C8 C7 C12 121.8(4) . . ?
H12 C12 C7 120.9(2) . . ?
C11 C12 C7 118.3(3) . . ?
C11 C12 H12 120.9(2) . . ?
H11 C11 C12 119.8(2) . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8(2) . . ?
H10 C10 C11 119.9(2) . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9(2) . . ?
H6 C6 C1 119.8(2) . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.8(2) . . ?
C6 C5 C4 116.2(4) . . ?
H5 C5 C4 121.9(2) . . ?
H5 C5 C6 121.9(2) . . ?
H8 C8 C7 120.4(2) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4(2) . . ?
C8 C9 C10 120.2(4) . . ?
H9 C9 C10 119.9(2) . . ?
H9 C9 C8 119.9(2) . . ?
N2 C13 N1 110.0(3) . . ?
H13 C13 N1 125.0(2) . . ?
H13 C13 N2 125.0(2) . . ?
H14a C14 N2 109.5 . . ?
H14b C14 N2 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 N2 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?

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
Br1 C1 C2 C3 178.0(3) . . . . ?
Br1 C1 C6 C5 -178.4(3) . . . . ?
N1 C4 C3 N2 0.6(3) . . . . ?
N1 C4 C3 C2 -178.6(3) . . . . ?
N1 C4 C5 C6 178.3(4) . . . . ?
N1 C7 C12 C11 179.5(3) . . . . ?
N1 C7 C8 C9 -179.2(4) . . . . ?
N1 C13 N2 C3 -0.8(3) . . . . ?
N1 C13 N2 C14 -177.0(3) . . . . ?
N2 C3 C2 C1 -179.2(4) . . . . ?
N2 C3 C4 C5 -179.7(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C7 C12 C11 C10 -0.2(4) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C11 C10 C9 C8 -0.0(4) . . . . ?


_olex2_exptl_crystal_mounting_method 'On a loop fibre'
_olex2_submission_original_sample_id PS-102
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_melting_point          'Not determined'
_chemical_compound_source        'Synthesized in lab'
