#------------------------------------------------------------------------------
#$Date: 2023-09-29 02:04:01 +0300 (Fri, 29 Sep 2023) $
#$Revision: 286601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/40/7714074.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7714074
loop_
_publ_author_name
'Gupta, Rahat'
'Sahni, Priya'
'Jana, Salil K.'
'Negi, Anshul'
'Pal, Amlan K.'
_publ_section_title
;
 Effect of substitution on deep-blue Ir(III) N-heterocyclic carbene (NHC)
 emitters
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01947K
_journal_year                    2023
_chemical_compound_source        'Synthesized in lab'
_chemical_formula_moiety         'C14 H12 Br N2, I'
_chemical_formula_sum            'C14 H12 Br I N2'
_chemical_formula_weight         415.073
_chemical_melting_point          ?
_chemical_name_systematic
'5-bromo-3-methyl-1-phenyl-1H-benzo[d]imidazol-3-ium iodide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2023-03-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.058(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6109(18)
_cell_length_b                   10.0029(16)
_cell_length_c                   14.313(2)
_cell_measurement_reflns_used    9702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.52
_cell_volume                     1452.3(4)
_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)'
_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
_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
_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
_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_restrained_S_all      1.0228
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0356
_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
_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)
_cod_data_source_file            d3dt01947k2.cif
_cod_data_source_block           mo_ps_102_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'Not determined' was
changed to '?' -- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1452.4(4)
_cod_database_code               7714074
_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)
;
_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'
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
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_
_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'
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_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_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) . . . . ?
