#------------------------------------------------------------------------------
#$Date: 2023-09-29 02:04:01 +0300 (Fri, 29 Sep 2023) $
#$Revision: 286601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/40/7714072.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_7714072
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         'C13 H9 Br N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_chemical_melting_point          ?
_chemical_name_systematic        5-bromo-1-phenyl-1H-benzo[d]imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.04.25 svn.r3594 for OlexSys, GUI svn.r5751)
;
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.542(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.718(3)
_cell_length_b                   3.9640(8)
_cell_length_c                   16.793(4)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.14
_cell_volume                     1090.4(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      100.0
_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_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_standards_number         0
_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_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_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
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.128
_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_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0429
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01947k2.cif
_cod_data_source_block           mo_ps_100_ow_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_database_code               7714072
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.522
_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)
;
_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'
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'
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 . . . .
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'
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_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_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) . . . . ?
