#------------------------------------------------------------------------------
#$Date: 2023-05-09 01:49:08 +0300 (Tue, 09 May 2023) $
#$Revision: 283602 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/29/7712973.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_7712973
loop_
_publ_author_name
'Arumugam, Ramar'
'Nayak, Prakash'
'Dey, Bijoy'
'Kannan, Ramkumar'
'Venkatasubbaiah, Krishnan'
'Chandrasekhar, Vadapalli'
_publ_section_title
;
 2-Hydroxyphenyl Benzimidazoles and their Boron Complexes: Synthesis,
 Structure, Aggregation-Induced Emission and Picric acid Sensing
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01199B
_journal_year                    2023
_chemical_formula_moiety         'C25 H17 Br N2 O2'
_chemical_formula_sum            'C25 H17 Br N2 O2'
_chemical_formula_weight         457.31
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-05 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.230(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3752(4)
_cell_length_b                   22.5930(14)
_cell_length_c                   12.2479(7)
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.7320
_cell_measurement_theta_min      2.9380
_cell_volume                     2014.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15044
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.798
_exptl_absorpt_coefficient_mu    2.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       Block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0317P)²+1.1750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3302
_reflns_number_total             4096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01199b2.cif
_cod_data_source_block           Ligand3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7712973
_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_min   0.820
_shelx_estimated_absorpt_t_max   0.869
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'
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
Br Br 1.29462(3) 0.47266(2) 0.72411(2) 0.02272(10) Uani 1 1 d . . . . .
O2 O 0.5938(2) 0.59524(7) 0.52060(13) 0.0187(4) Uani 1 1 d . . . . .
O1 O 0.0000(2) 0.92604(8) 0.58319(15) 0.0248(4) Uani 1 1 d . . . . .
H1 H -0.028102 0.909641 0.637834 0.037 Uiso 1 1 calc R U . . .
N1 N 0.0178(3) 0.84271(9) 0.73368(17) 0.0174(5) Uani 1 1 d . . . . .
N2 N 0.1903(3) 0.76206(9) 0.71745(16) 0.0139(4) Uani 1 1 d . . . . .
C19 C 1.0722(3) 0.51158(11) 0.66365(19) 0.0148(5) Uani 1 1 d . . . . .
C7 C -0.0412(3) 0.79668(11) 0.7958(2) 0.0157(5) Uani 1 1 d . . . . .
C1 C 0.1549(3) 0.82057(11) 0.68872(19) 0.0150(5) Uani 1 1 d . . . . .
C8 C 0.2554(3) 0.85671(11) 0.6191(2) 0.0164(5) Uani 1 1 d . . . . .
C22 C 0.7537(3) 0.56823(11) 0.57522(19) 0.0141(5) Uani 1 1 d . . . . .
C2 C 0.0639(3) 0.74631(11) 0.78583(19) 0.0137(5) Uani 1 1 d . . . . .
C23 C 0.5064(3) 0.63732(10) 0.5753(2) 0.0142(5) Uani 1 1 d . . . . .
C24 C 0.3697(3) 0.66892(10) 0.50809(19) 0.0145(5) Uani 1 1 d . . . . .
H24 H 0.348067 0.662522 0.432106 0.017 Uiso 1 1 calc R U . . .
C25 C 0.2661(3) 0.70996(10) 0.5552(2) 0.0153(5) Uani 1 1 d . . . . .
H25 H 0.173244 0.730779 0.511015 0.018 Uiso 1 1 calc R U . . .
C13 C 0.1696(3) 0.90780(11) 0.5680(2) 0.0198(6) Uani 1 1 d . . . . .
C20 C 1.0750(3) 0.57187(11) 0.6468(2) 0.0188(5) Uani 1 1 d . . . . .
H20 H 1.183589 0.593090 0.665375 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3011(3) 0.72008(10) 0.6691(2) 0.0141(5) Uani 1 1 d . . . . .
C16 C 0.5404(3) 0.64678(11) 0.6881(2) 0.0155(5) Uani 1 1 d . . . . .
H16 H 0.631699 0.625373 0.732474 0.019 Uiso 1 1 calc R U . . .
C18 C 0.9127(3) 0.47944(11) 0.6377(2) 0.0200(6) Uani 1 1 d . . . . .
H18 H 0.913022 0.438814 0.649931 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0381(3) 0.69340(11) 0.8407(2) 0.0169(5) Uani 1 1 d . . . . .
H3 H 0.107973 0.659824 0.833208 0.020 Uiso 1 1 calc R U . . .
C17 C 0.7510(3) 0.50820(11) 0.5930(2) 0.0192(6) Uani 1 1 d . . . . .
H17 H 0.642095 0.487016 0.575304 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4374(3) 0.68850(11) 0.7350(2) 0.0155(5) Uani 1 1 d . . . . .
H15 H 0.460307 0.695161 0.810928 0.019 Uiso 1 1 calc R U . . .
C21 C 0.9138(3) 0.60059(11) 0.6016(2) 0.0208(6) Uani 1 1 d . . . . .
H21 H 0.913626 0.641211 0.589280 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2571(4) 0.94119(11) 0.4961(2) 0.0242(6) Uani 1 1 d . . . . .
H12 H 0.198505 0.973783 0.459832 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1770(3) 0.79680(11) 0.8629(2) 0.0182(6) Uani 1 1 d . . . . .
H6 H -0.247749 0.830249 0.869887 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4352(3) 0.84386(11) 0.6038(2) 0.0210(6) Uani 1 1 d . . . . .
H9 H 0.496800 0.811880 0.640510 0.025 Uiso 1 1 calc R U . . .
C4 C -0.0977(3) 0.69398(12) 0.9067(2) 0.0183(6) Uani 1 1 d . . . . .
H4 H -0.120487 0.659679 0.944197 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5218(4) 0.87840(12) 0.5345(2) 0.0259(6) Uani 1 1 d . . . . .
H10 H 0.641643 0.869783 0.525215 0.031 Uiso 1 1 calc R U . . .
C5 C -0.2018(3) 0.74479(11) 0.9186(2) 0.0194(6) Uani 1 1 d . . . . .
H5 H -0.289790 0.743564 0.965103 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4307(4) 0.92562(12) 0.4792(2) 0.0240(6) Uani 1 1 d . . . . .
H11 H 0.487640 0.947264 0.429645 0.029 Uiso 1 1 calc R U . . .
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'
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'
Br Br -0.2901 2.4595 '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
C23 O2 C22 119.45(18) . . ?
C13 O1 H1 109.5 . . ?
C1 N1 C7 105.7(2) . . ?
C1 N2 C2 106.24(19) . . ?
C1 N2 C14 128.4(2) . . ?
C2 N2 C14 123.8(2) . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 Br 119.85(18) . . ?
C20 C19 Br 118.84(18) . . ?
C2 C7 C6 121.1(2) . . ?
C2 C7 N1 109.5(2) . . ?
C6 C7 N1 129.4(2) . . ?
N1 C1 N2 112.4(2) . . ?
N1 C1 C8 121.5(2) . . ?
N2 C1 C8 126.1(2) . . ?
C9 C8 C13 118.5(2) . . ?
C9 C8 C1 122.8(2) . . ?
C13 C8 C1 118.7(2) . . ?
C17 C22 C21 121.2(2) . . ?
C17 C22 O2 118.3(2) . . ?
C21 C22 O2 120.3(2) . . ?
C7 C2 N2 106.2(2) . . ?
C7 C2 C3 122.3(2) . . ?
N2 C2 C3 131.4(2) . . ?
O2 C23 C16 124.6(2) . . ?
O2 C23 C24 114.6(2) . . ?
C16 C23 C24 120.7(2) . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C14 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C14 C25 H25 120.0 . . ?
O1 C13 C12 116.9(2) . . ?
O1 C13 C8 123.0(2) . . ?
C12 C13 C8 120.1(2) . . ?
C19 C20 C21 119.3(2) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C15 C14 C25 120.0(2) . . ?
C15 C14 N2 120.4(2) . . ?
C25 C14 N2 119.5(2) . . ?
C23 C16 C15 119.6(2) . . ?
C23 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C4 C3 C2 116.1(2) . . ?
C4 C3 H3 122.0 . . ?
C2 C3 H3 122.0 . . ?
C22 C17 C18 119.3(2) . . ?
C22 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C22 C21 C20 119.4(2) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C5 C6 C7 116.9(2) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
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
Br C19 1.903(2) . ?
O2 C23 1.381(3) . ?
O2 C22 1.399(3) . ?
O1 C13 1.358(3) . ?
O1 H1 0.8200 . ?
N1 C1 1.325(3) . ?
N1 C7 1.399(3) . ?
N2 C1 1.382(3) . ?
N2 C2 1.395(3) . ?
N2 C14 1.440(3) . ?
C19 C18 1.375(3) . ?
C19 C20 1.379(3) . ?
C7 C2 1.393(3) . ?
C7 C6 1.393(3) . ?
C1 C8 1.465(3) . ?
C8 C9 1.399(3) . ?
C8 C13 1.414(3) . ?
C22 C17 1.374(4) . ?
C22 C21 1.383(3) . ?
C2 C3 1.399(3) . ?
C23 C16 1.381(3) . ?
C23 C24 1.392(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C14 1.395(3) . ?
C25 H25 0.9300 . ?
C13 C12 1.394(4) . ?
C20 C21 1.389(3) . ?
C20 H20 0.9300 . ?
C14 C15 1.383(3) . ?
C16 C15 1.392(3) . ?
C16 H16 0.9300 . ?
C18 C17 1.391(3) . ?
C18 H18 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C21 H21 0.9300 . ?
C12 C11 1.375(4) . ?
C12 H12 0.9300 . ?
C6 C5 1.386(4) . ?
C6 H6 0.9300 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 C2 -0.5(3) . . . . ?
C1 N1 C7 C6 177.4(2) . . . . ?
C7 N1 C1 N2 0.1(3) . . . . ?
C7 N1 C1 C8 -178.5(2) . . . . ?
C2 N2 C1 N1 0.3(3) . . . . ?
C14 N2 C1 N1 166.6(2) . . . . ?
C2 N2 C1 C8 178.8(2) . . . . ?
C14 N2 C1 C8 -14.9(4) . . . . ?
N1 C1 C8 C9 155.9(2) . . . . ?
N2 C1 C8 C9 -22.6(4) . . . . ?
N1 C1 C8 C13 -22.0(3) . . . . ?
N2 C1 C8 C13 159.5(2) . . . . ?
C23 O2 C22 C17 117.2(2) . . . . ?
C23 O2 C22 C21 -68.3(3) . . . . ?
C6 C7 C2 N2 -177.4(2) . . . . ?
N1 C7 C2 N2 0.6(3) . . . . ?
C6 C7 C2 C3 0.8(4) . . . . ?
N1 C7 C2 C3 178.9(2) . . . . ?
C1 N2 C2 C7 -0.5(2) . . . . ?
C14 N2 C2 C7 -167.6(2) . . . . ?
C1 N2 C2 C3 -178.6(2) . . . . ?
C14 N2 C2 C3 14.3(4) . . . . ?
C22 O2 C23 C16 -14.5(3) . . . . ?
C22 O2 C23 C24 168.8(2) . . . . ?
O2 C23 C24 C25 176.4(2) . . . . ?
C16 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C14 1.0(4) . . . . ?
C9 C8 C13 O1 -175.9(2) . . . . ?
C1 C8 C13 O1 2.1(4) . . . . ?
C9 C8 C13 C12 5.8(4) . . . . ?
C1 C8 C13 C12 -176.2(2) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
Br C19 C20 C21 179.34(19) . . . . ?
C24 C25 C14 C15 -1.0(4) . . . . ?
C24 C25 C14 N2 -178.8(2) . . . . ?
C1 N2 C14 C15 128.2(3) . . . . ?
C2 N2 C14 C15 -67.7(3) . . . . ?
C1 N2 C14 C25 -54.0(3) . . . . ?
C2 N2 C14 C25 110.2(3) . . . . ?
O2 C23 C16 C15 -176.8(2) . . . . ?
C24 C23 C16 C15 -0.3(4) . . . . ?
C20 C19 C18 C17 0.3(4) . . . . ?
Br C19 C18 C17 -179.66(19) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
N2 C2 C3 C4 177.2(2) . . . . ?
C21 C22 C17 C18 -0.4(4) . . . . ?
O2 C22 C17 C18 174.0(2) . . . . ?
C19 C18 C17 C22 0.2(4) . . . . ?
C25 C14 C15 C16 0.3(4) . . . . ?
N2 C14 C15 C16 178.1(2) . . . . ?
C23 C16 C15 C14 0.3(4) . . . . ?
C17 C22 C21 C20 0.1(4) . . . . ?
O2 C22 C21 C20 -174.2(2) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
O1 C13 C12 C11 178.7(2) . . . . ?
C8 C13 C12 C11 -2.9(4) . . . . ?
C2 C7 C6 C5 0.0(3) . . . . ?
N1 C7 C6 C5 -177.6(2) . . . . ?
C13 C8 C9 C10 -4.1(4) . . . . ?
C1 C8 C9 C10 178.0(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C7 C6 C5 C4 -1.1(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C13 C12 C11 C10 -1.8(4) . . . . ?
C9 C10 C11 C12 3.5(4) . . . . ?
