#------------------------------------------------------------------------------
#$Date: 2023-05-09 01:49:08 +0300 (Tue, 09 May 2023) $
#$Revision: 283602 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/29/7712968.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_7712968
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         '2(C27 H18 B Br F2 N3 O), C H2 Cl2'
_chemical_formula_sum            'C55 H38 B2 Br2 Cl2 F4 N6 O2'
_chemical_formula_weight         1143.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                111.653(3)
_cell_angle_beta                 93.085(2)
_cell_angle_gamma                108.122(2)
_cell_formula_units_Z            1
_cell_length_a                   9.1247(2)
_cell_length_b                   11.5918(3)
_cell_length_c                   13.4085(4)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.0460
_cell_measurement_theta_min      3.0900
_cell_volume                     1229.75(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0481
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.100
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56837
_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    1.544
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.692
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     2776
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0823
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1232P)²+5.4205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2270
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4103
_reflns_number_total             5026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01199b2.cif
_cod_data_source_block           Complex1
_cod_original_cell_volume        1229.75(6)
_cod_database_code               7712968
_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   0.784
_shelx_estimated_absorpt_t_max   0.839
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.2585(4) 0.7937(3) -0.0603(2) 0.0363(4) Uani 0.858(10) 1 d D U P A 1
Br1A Br 0.281(3) 0.778(2) -0.0775(19) 0.060(5) Uani 0.142(10) 1 d D U P A 2
F1 F 1.0802(5) 1.0979(4) 0.7838(3) 0.0539(11) Uani 1 1 d . U . . .
F2 F 1.0969(4) 0.8974(4) 0.7603(3) 0.0405(8) Uani 1 1 d . U . . .
O1 O 1.1776(7) 0.9963(6) 0.6367(4) 0.0393(17) Uani 0.858(10) 1 d D U P A 1
O1A O 1.178(3) 0.964(4) 0.6341(18) 0.038(5) Uani 0.142(10) 1 d D U P A 2
N1 N 0.8988(7) 0.8996(7) 0.6377(5) 0.0340(17) Uani 0.858(10) 1 d D U P A 1
N1A N 0.900(2) 0.918(5) 0.635(2) 0.035(4) Uani 0.142(10) 1 d D U P A 2
N2 N 0.7148(7) 0.7623(9) 0.4918(5) 0.0321(14) Uani 0.858(10) 1 d D U P A 1
N2A N 0.703(3) 0.770(5) 0.500(2) 0.031(4) Uani 0.142(10) 1 d D U P A 2
N3 N 0.3458(11) 0.3882(6) 0.0890(6) 0.052(2) Uani 0.858(10) 1 d D U P A 1
N3A N 0.382(5) 0.392(2) 0.094(2) 0.030(4) Uani 0.142(10) 1 d D U P A 2
C1 C 0.8651(7) 0.8245(14) 0.5322(6) 0.0290(15) Uani 0.858(10) 1 d D U P A 1
C1A C 0.856(2) 0.820(9) 0.537(3) 0.033(4) Uani 0.142(10) 1 d D U P A 2
C2 C 0.6384(8) 0.8037(12) 0.5803(7) 0.0319(16) Uani 0.858(10) 1 d D U P A 1
C2A C 0.638(2) 0.820(8) 0.592(3) 0.033(4) Uani 0.142(10) 1 d D U P A 2
C3 C 0.4828(8) 0.7750(11) 0.5817(6) 0.0339(16) Uani 0.858(10) 1 d D U P A 1
H3 H 0.407360 0.716470 0.519121 0.041 Uiso 0.858(10) 1 calc R U P A 1
C3A C 0.485(3) 0.791(7) 0.606(4) 0.035(5) Uani 0.142(10) 1 d D U P A 2
H3A H 0.403102 0.726130 0.550211 0.041 Uiso 0.142(10) 1 calc R U P A 2
C4 C 0.4410(8) 0.8357(9) 0.6791(7) 0.0326(17) Uani 0.858(10) 1 d D U P A 1
H4 H 0.335224 0.817790 0.682629 0.039 Uiso 0.858(10) 1 calc R U P A 1
C4A C 0.459(4) 0.861(6) 0.708(4) 0.032(5) Uani 0.142(10) 1 d D U P A 2
H4A H 0.357520 0.855177 0.717397 0.039 Uiso 0.142(10) 1 calc R U P A 2
C5 C 0.5547(10) 0.9238(11) 0.7729(6) 0.0360(18) Uani 0.858(10) 1 d D U P A 1
H5 H 0.523545 0.963243 0.838005 0.043 Uiso 0.858(10) 1 calc R U P A 1
C5A C 0.583(4) 0.940(7) 0.797(3) 0.034(5) Uani 0.142(10) 1 d D U P A 2
H5A H 0.562122 0.978345 0.866689 0.041 Uiso 0.142(10) 1 calc R U P A 2
C6 C 0.7134(10) 0.9532(16) 0.7701(6) 0.0400(19) Uani 0.858(10) 1 d D U P A 1
H6 H 0.790047 1.013054 0.831679 0.048 Uiso 0.858(10) 1 calc R U P A 1
C6A C 0.737(4) 0.962(9) 0.783(3) 0.033(5) Uani 0.142(10) 1 d D U P A 2
H6A H 0.820959 1.006099 0.842379 0.039 Uiso 0.142(10) 1 calc R U P A 2
C7 C 0.7528(7) 0.8893(7) 0.6714(6) 0.0312(17) Uani 0.858(10) 1 d D U P A 1
C7A C 0.759(2) 0.915(5) 0.676(2) 0.034(4) Uani 0.142(10) 1 d D U P A 2
C8 C 1.0021(9) 0.8238(10) 0.4723(6) 0.0316(17) Uani 0.858(10) 1 d D U P A 1
C8A C 0.986(3) 0.806(7) 0.472(3) 0.034(4) Uani 0.142(10) 1 d D U P A 2
C9 C 0.9825(10) 0.7451(8) 0.3586(7) 0.041(2) Uani 0.858(10) 1 d D U P A 1
H9 H 0.883390 0.687746 0.317541 0.050 Uiso 0.858(10) 1 calc R U P A 1
C9A C 0.962(4) 0.714(4) 0.362(2) 0.031(4) Uani 0.142(10) 1 d D U P A 2
H9A H 0.863159 0.648964 0.328063 0.038 Uiso 0.142(10) 1 calc R U P A 2
C10 C 1.1155(11) 0.7558(8) 0.3098(6) 0.0359(19) Uani 0.858(10) 1 d D U P A 1
H10 H 1.106553 0.704104 0.236147 0.043 Uiso 0.858(10) 1 calc R U P A 1
C10A C 1.087(5) 0.722(5) 0.306(3) 0.034(5) Uani 0.142(10) 1 d D U P A 2
H10A H 1.072278 0.664886 0.233066 0.041 Uiso 0.142(10) 1 calc R U P A 2
C11 C 1.2581(10) 0.8433(9) 0.3721(7) 0.0349(18) Uani 0.858(10) 1 d D U P A 1
H11 H 1.346364 0.850243 0.339949 0.042 Uiso 0.858(10) 1 calc R U P A 1
C11A C 1.230(5) 0.814(6) 0.360(3) 0.034(5) Uani 0.142(10) 1 d D U P A 2
H11A H 1.314056 0.819937 0.323409 0.041 Uiso 0.142(10) 1 calc R U P A 2
C12 C 1.2752(10) 0.9197(12) 0.4786(7) 0.0384(18) Uani 0.858(10) 1 d D U P A 1
H12 H 1.374353 0.979677 0.517654 0.046 Uiso 0.858(10) 1 calc R U P A 1
C12A C 1.256(5) 0.899(8) 0.466(3) 0.037(5) Uani 0.142(10) 1 d D U P A 2
H12A H 1.356260 0.960381 0.499987 0.044 Uiso 0.142(10) 1 calc R U P A 2
C13 C 1.1518(10) 0.9115(12) 0.5299(6) 0.0344(17) Uani 0.858(10) 1 d D U P A 1
C13A C 1.138(4) 0.896(9) 0.524(2) 0.035(4) Uani 0.142(10) 1 d D U P A 2
C14 C 0.6317(8) 0.6631(7) 0.3825(5) 0.0281(16) Uani 0.858(10) 1 d D U P A 1
C14A C 0.614(4) 0.667(3) 0.394(2) 0.029(4) Uani 0.142(10) 1 d D U P A 2
C15 C 0.570(2) 0.7018(8) 0.3086(9) 0.027(2) Uani 0.858(10) 1 d D U P A 1
H15 H 0.591573 0.791031 0.323442 0.032 Uiso 0.858(10) 1 calc R U P A 1
C15A C 0.582(13) 0.700(4) 0.308(5) 0.029(5) Uani 0.142(10) 1 d D U P A 2
H15A H 0.635851 0.783589 0.309829 0.035 Uiso 0.142(10) 1 calc R U P A 2
C16 C 0.4734(17) 0.6017(6) 0.2110(6) 0.0230(16) Uani 0.858(10) 1 d D U P A 1
C16A C 0.466(12) 0.604(2) 0.219(4) 0.030(4) Uani 0.142(10) 1 d D U P A 2
C17 C 0.3875(6) 0.6023(5) 0.1185(4) 0.0255(10) Uani 1 1 d . U . . .
C18 C 0.3741(6) 0.7017(5) 0.0879(4) 0.0265(11) Uani 1 1 d . U . . .
C19 C 0.2794(7) 0.6632(6) -0.0112(5) 0.0325(12) Uani 1 1 d . U . . .
C20 C 0.2000(14) 0.5330(9) -0.0798(9) 0.048(3) Uani 0.858(10) 1 d D U P A 1
H20 H 0.133312 0.511896 -0.143917 0.058 Uiso 0.858(10) 1 calc R U P A 1
C20A C 0.230(8) 0.523(4) -0.084(5) 0.036(6) Uani 0.142(10) 1 d D U P A 2
H20A H 0.178397 0.497564 -0.155024 0.043 Uiso 0.142(10) 1 calc R U P A 2
C21 C 0.2183(14) 0.4344(9) -0.0547(8) 0.055(3) Uani 0.858(10) 1 d D U P A 1
H21 H 0.171128 0.345969 -0.103575 0.066 Uiso 0.858(10) 1 calc R U P A 1
C21A C 0.252(7) 0.427(4) -0.058(3) 0.034(5) Uani 0.142(10) 1 d D U P A 2
H21A H 0.207161 0.337708 -0.105723 0.041 Uiso 0.142(10) 1 calc R U P A 2
C22 C 0.3094(11) 0.4686(8) 0.0461(7) 0.042(2) Uani 0.858(10) 1 d D U P A 1
C22A C 0.343(7) 0.463(3) 0.043(3) 0.036(4) Uani 0.142(10) 1 d D U P A 2
C23 C 0.3036(9) 0.2414(7) 0.0323(6) 0.0419(18) Uani 0.858(10) 1 d D U P A 1
H23A H 0.300913 0.214928 -0.045532 0.050 Uiso 0.858(10) 1 calc R U P A 1
H23B H 0.379151 0.213081 0.061380 0.050 Uiso 0.858(10) 1 calc R U P A 1
C23A C 0.414(4) 0.267(3) 0.046(3) 0.053(5) Uani 0.142(10) 1 d D U P A 2
H23C H 0.463263 0.264732 -0.016560 0.064 Uiso 0.142(10) 1 calc R U P A 2
H23D H 0.483313 0.261008 0.099441 0.064 Uiso 0.142(10) 1 calc R U P A 2
C24 C 0.1511(11) 0.1845(12) 0.0528(9) 0.066(3) Uani 0.858(10) 1 d D U P A 1
H24A H 0.077651 0.212389 0.022564 0.098 Uiso 0.858(10) 1 calc R U P A 1
H24B H 0.155402 0.213483 0.130213 0.098 Uiso 0.858(10) 1 calc R U P A 1
H24C H 0.118108 0.089328 0.019399 0.098 Uiso 0.858(10) 1 calc R U P A 1
C24A C 0.267(3) 0.159(3) 0.013(2) 0.015(6) Uani 0.142(10) 1 d D U P A 2
H24D H 0.230961 0.127072 -0.064368 0.022 Uiso 0.142(10) 1 calc R U P A 2
H24E H 0.190560 0.189189 0.051166 0.022 Uiso 0.142(10) 1 calc R U P A 2
H24F H 0.279468 0.088895 0.029734 0.022 Uiso 0.142(10) 1 calc R U P A 2
C25 C 0.4467(9) 0.4685(6) 0.1911(6) 0.0338(17) Uani 0.858(10) 1 d D U P A 1
C25A C 0.409(5) 0.471(3) 0.209(2) 0.031(4) Uani 0.142(10) 1 d D U P A 2
C26 C 0.5058(9) 0.4300(6) 0.2668(6) 0.0330(16) Uani 0.858(10) 1 d D U P A 1
H26 H 0.483896 0.340837 0.252450 0.040 Uiso 0.858(10) 1 calc R U P A 1
C26A C 0.452(5) 0.436(3) 0.293(2) 0.030(4) Uani 0.142(10) 1 d D U P A 2
H26A H 0.410105 0.349416 0.287060 0.036 Uiso 0.142(10) 1 calc R U P A 2
C27 C 0.5988(8) 0.5304(7) 0.3646(5) 0.0248(16) Uani 0.858(10) 1 d D U P A 1
H27 H 0.639004 0.509152 0.417972 0.030 Uiso 0.858(10) 1 calc R U P A 1
C27A C 0.561(6) 0.536(4) 0.384(3) 0.031(5) Uani 0.142(10) 1 d D U P A 2
H27A H 0.598500 0.515179 0.439171 0.037 Uiso 0.142(10) 1 calc R U P A 2
B1 B 1.0643(8) 0.9750(6) 0.7105(5) 0.0312(13) Uani 1 1 d D U . . .
Cl2 Cl 1.0351(12) 0.4889(11) 0.4855(8) 0.119(3) Uani 0.5 1 d D U P B -1
Cl3 Cl 0.8283(7) 0.5542(6) 0.6457(6) 0.111(2) Uani 0.5 1 d D U P B -1
C1B C 1.0184(12) 0.5666(13) 0.6240(10) 0.063(4) Uani 0.5 1 d D U P B -1
H1BA H 1.060264 0.527761 0.666222 0.075 Uiso 0.5 1 calc R U P B -1
H1BB H 1.083369 0.659956 0.652067 0.075 Uiso 0.5 1 calc R U P B -1
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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
C13 O1 B1 122.8(5) . . ?
C13A O1A B1 125.0(19) . . ?
C1 N1 C7 105.9(5) . . ?
C1 N1 B1 126.6(6) . . ?
C7 N1 B1 127.4(5) . . ?
C1A N1A C7A 105.3(12) . . ?
C1A N1A B1 126(2) . . ?
C7A N1A B1 123.3(17) . . ?
C1 N2 C2 105.5(5) . . ?
C1 N2 C14 130.9(6) . . ?
C2 N2 C14 123.5(5) . . ?
C1A N2A C2A 105.0(12) . . ?
C1A N2A C14A 129.4(18) . . ?
C2A N2A C14A 124.8(16) . . ?
C22 N3 C25 108.6(5) . . ?
C22 N3 C23 126.3(6) . . ?
C25 N3 C23 124.7(6) . . ?
C22A N3A C25A 106.3(14) . . ?
C22A N3A C23A 128.8(19) . . ?
C25A N3A C23A 124.3(16) . . ?
N2 C1 N1 114.4(6) . . ?
N2 C1 C8 128.4(6) . . ?
N1 C1 C8 117.2(5) . . ?
N2A C1A N1A 114.0(18) . . ?
N2A C1A C8A 128.0(18) . . ?
N1A C1A C8A 116.0(17) . . ?
C3 C2 C7 122.7(6) . . ?
C3 C2 N2 129.7(6) . . ?
C7 C2 N2 107.5(6) . . ?
C3A C2A C7A 121.3(13) . . ?
C3A C2A N2A 131.1(14) . . ?
C7A C2A N2A 107.6(11) . . ?
C2 C3 C4 117.4(6) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C2A C3A C4A 116.8(16) . . ?
C2A C3A H3A 121.6 . . ?
C4A C3A H3A 121.6 . . ?
C3 C4 C5 121.2(6) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C3A C4A C5A 121.3(17) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A H4A 119.3 . . ?
C6 C5 C4 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C6A C5A C4A 120.4(15) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C7 C6 C5 117.0(6) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C5A C6A C7A 115.9(17) . . ?
C5A C6A H6A 122.0 . . ?
C7A C6A H6A 122.0 . . ?
C2 C7 C6 120.9(6) . . ?
C2 C7 N1 106.6(6) . . ?
C6 C7 N1 132.3(6) . . ?
C2A C7A C6A 121(2) . . ?
C2A C7A N1A 106.6(11) . . ?
C6A C7A N1A 129.4(18) . . ?
C13 C8 C9 118.7(6) . . ?
C13 C8 C1 118.1(6) . . ?
C9 C8 C1 123.0(6) . . ?
C13A C8A C9A 118.9(13) . . ?
C13A C8A C1A 116.5(14) . . ?
C9A C8A C1A 124.6(14) . . ?
C10 C9 C8 118.7(6) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C10A C9A C8A 119.4(16) . . ?
C10A C9A H9A 120.3 . . ?
C8A C9A H9A 120.3 . . ?
C11 C10 C9 118.8(6) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C11A C10A C9A 118.5(15) . . ?
C11A C10A H10A 120.7 . . ?
C9A C10A H10A 120.7 . . ?
C12 C11 C10 122.2(7) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C12A C11A C10A 122.3(16) . . ?
C12A C11A H11A 118.9 . . ?
C10A C11A H11A 118.9 . . ?
C11 C12 C13 121.4(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C11A C12A C13A 121.5(16) . . ?
C11A C12A H12A 119.2 . . ?
C13A C12A H12A 119.2 . . ?
C12 C13 O1 117.8(6) . . ?
C12 C13 C8 120.2(6) . . ?
O1 C13 C8 121.9(6) . . ?
C12A C13A O1A 117.7(18) . . ?
C12A C13A C8A 119.2(13) . . ?
O1A C13A C8A 122(2) . . ?
C15 C14 C27 123.1(5) . . ?
C15 C14 N2 119.7(6) . . ?
C27 C14 N2 116.5(5) . . ?
C15A C14A C27A 122.3(13) . . ?
C15A C14A N2A 120.5(15) . . ?
C27A C14A N2A 117.2(15) . . ?
C14 C15 C16 117.5(6) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C14A C15A C16A 118(2) . . ?
C14A C15A H15A 121.2 . . ?
C16A C15A H15A 121.2 . . ?
C15 C16 C25 119.2(6) . . ?
C15 C16 C17 133.5(6) . . ?
C25 C16 C17 107.3(5) . . ?
C15A C16A C25A 119.2(15) . . ?
C15A C16A C17 134(3) . . ?
C25A C16A C17 106.2(19) . . ?
C18 C17 C22 118.9(5) . . ?
C18 C17 C16 134.3(5) . . ?
C22 C17 C16 106.7(5) . . ?
C18 C17 C22A 123.9(11) . . ?
C18 C17 C16A 133.5(10) . . ?
C22A C17 C16A 101.9(17) . . ?
C19 C18 C17 117.8(5) . . ?
C20 C19 C18 123.0(6) . . ?
C18 C19 C20A 116.0(14) . . ?
C18 C19 Br1A 123.2(8) . . ?
C20A C19 Br1A 115.8(17) . . ?
C20 C19 Br1 116.7(5) . . ?
C18 C19 Br1 120.3(4) . . ?
C21 C20 C19 120.3(7) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21A C20A C19 125(3) . . ?
C21A C20A H20A 117.3 . . ?
C19 C20A H20A 117.3 . . ?
C20 C21 C22 118.6(7) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C20A C21A C22A 119(2) . . ?
C20A C21A H21A 120.7 . . ?
C22A C21A H21A 120.7 . . ?
N3 C22 C21 129.4(7) . . ?
N3 C22 C17 109.3(5) . . ?
C21 C22 C17 121.3(7) . . ?
N3A C22A C21A 132(2) . . ?
N3A C22A C17 110.7(15) . . ?
C21A C22A C17 116(2) . . ?
C24 C23 N3 105.5(8) . . ?
C24 C23 H23A 110.6 . . ?
N3 C23 H23A 110.6 . . ?
C24 C23 H23B 110.6 . . ?
N3 C23 H23B 110.6 . . ?
H23A C23 H23B 108.8 . . ?
C24A C23A N3A 108(2) . . ?
C24A C23A H23C 110.2 . . ?
N3A C23A H23C 110.2 . . ?
C24A C23A H23D 110.2 . . ?
N3A C23A H23D 110.2 . . ?
H23C C23A H23D 108.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C26 C25 C16 123.0(5) . . ?
C26 C25 N3 128.8(6) . . ?
C16 C25 N3 108.1(6) . . ?
C26A C25A C16A 121.9(13) . . ?
C26A C25A N3A 125.9(19) . . ?
C16A C25A N3A 104.4(17) . . ?
C27 C26 C25 117.2(5) . . ?
C27 C26 H26 121.4 . . ?
C25 C26 H26 121.4 . . ?
C27A C26A C25A 117.8(14) . . ?
C27A C26A H26A 121.1 . . ?
C25A C26A H26A 121.1 . . ?
C26 C27 C14 119.8(5) . . ?
C26 C27 H27 120.1 . . ?
C14 C27 H27 120.1 . . ?
C26A C27A C14A 119.8(15) . . ?
C26A C27A H27A 120.1 . . ?
C14A C27A H27A 120.1 . . ?
F1 B1 F2 112.4(5) . . ?
F1 B1 O1 105.9(5) . . ?
F2 B1 O1 110.2(6) . . ?
F1 B1 O1A 117.9(17) . . ?
F2 B1 O1A 98(2) . . ?
F1 B1 N1 112.4(6) . . ?
F2 B1 N1 108.9(5) . . ?
O1 B1 N1 106.9(5) . . ?
F1 B1 N1A 106.6(17) . . ?
F2 B1 N1A 117(2) . . ?
O1A B1 N1A 105.2(17) . . ?
Cl3 C1B Cl2 115.4(7) . . ?
Cl3 C1B H1BA 108.4 . . ?
Cl2 C1B H1BA 108.4 . . ?
Cl3 C1B H1BB 108.4 . . ?
Cl2 C1B H1BB 108.4 . . ?
H1BA C1B H1BB 107.5 . . ?
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 C19 1.913(6) . ?
Br1A C19 1.85(2) . ?
F1 B1 1.357(7) . ?
F2 B1 1.389(7) . ?
O1 C13 1.362(8) . ?
O1 B1 1.497(9) . ?
O1A C13A 1.358(18) . ?
O1A B1 1.499(19) . ?
N1 C1 1.317(8) . ?
N1 C7 1.414(9) . ?
N1 B1 1.545(8) . ?
N1A C1A 1.319(19) . ?
N1A C7A 1.423(15) . ?
N1A B1 1.559(18) . ?
N2 C1 1.308(8) . ?
N2 C2 1.415(8) . ?
N2 C14 1.463(7) . ?
N2A C1A 1.316(17) . ?
N2A C2A 1.414(15) . ?
N2A C14A 1.460(14) . ?
N3 C22 1.371(9) . ?
N3 C25 1.407(8) . ?
N3 C23 1.493(10) . ?
N3A C22A 1.365(17) . ?
N3A C25A 1.438(17) . ?
N3A C23A 1.476(19) . ?
C1 C8 1.522(9) . ?
C1A C8A 1.524(15) . ?
C2 C3 1.356(10) . ?
C2 C7 1.375(9) . ?
C2A C3A 1.363(16) . ?
C2A C7A 1.374(17) . ?
C3 C4 1.374(10) . ?
C3 H3 0.9300 . ?
C3A C4A 1.386(19) . ?
C3A H3A 0.9300 . ?
C4 C5 1.398(10) . ?
C4 H4 0.9300 . ?
C4A C5A 1.40(2) . ?
C4A H4A 0.9300 . ?
C5 C6 1.387(11) . ?
C5 H5 0.9300 . ?
C5A C6A 1.382(19) . ?
C5A H5A 0.9300 . ?
C6 C7 1.386(10) . ?
C6 H6 0.9300 . ?
C6A C7A 1.388(19) . ?
C6A H6A 0.9300 . ?
C8 C13 1.393(9) . ?
C8 C9 1.425(10) . ?
C8A C13A 1.400(18) . ?
C8A C9A 1.415(17) . ?
C9 C10 1.404(11) . ?
C9 H9 0.9300 . ?
C9A C10A 1.403(19) . ?
C9A H9A 0.9300 . ?
C10 C11 1.362(11) . ?
C10 H10 0.9300 . ?
C10A C11A 1.357(19) . ?
C10A H10A 0.9300 . ?
C11 C12 1.342(10) . ?
C11 H11 0.9300 . ?
C11A C12A 1.349(18) . ?
C11A H11A 0.9300 . ?
C12 C13 1.347(10) . ?
C12 H12 0.9300 . ?
C12A C13A 1.357(17) . ?
C12A H12A 0.9300 . ?
C14 C15 1.388(9) . ?
C14 C27 1.396(8) . ?
C14A C15A 1.388(18) . ?
C14A C27A 1.396(17) . ?
C15 C16 1.397(8) . ?
C15 H15 0.9300 . ?
C15A C16A 1.394(19) . ?
C15A H15A 0.9300 . ?
C16 C25 1.403(8) . ?
C16 C17 1.435(9) . ?
C16A C25A 1.417(18) . ?
C16A C17 1.48(3) . ?
C17 C18 1.394(7) . ?
C17 C22 1.407(9) . ?
C17 C22A 1.46(3) . ?
C18 C19 1.383(7) . ?
C19 C20 1.369(10) . ?
C19 C20A 1.46(4) . ?
C20 C21 1.357(11) . ?
C20 H20 0.9300 . ?
C20A C21A 1.36(2) . ?
C20A H20A 0.9300 . ?
C21 C22 1.398(10) . ?
C21 H21 0.9300 . ?
C21A C22A 1.39(2) . ?
C21A H21A 0.9300 . ?
C23 C24 1.431(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23A C24A 1.43(2) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 0.9600 . ?
C25 C26 1.395(9) . ?
C25A C26A 1.397(17) . ?
C26 C27 1.391(8) . ?
C26 H26 0.9300 . ?
C26A C27A 1.393(17) . ?
C26A H26A 0.9300 . ?
C27 H27 0.9300 . ?
C27A H27A 0.9300 . ?
Cl2 C1B 1.779(9) . ?
Cl3 C1B 1.745(8) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
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
C2 N2 C1 N1 1.9(18) . . . . ?
C14 N2 C1 N1 -174.3(9) . . . . ?
C2 N2 C1 C8 -176.0(15) . . . . ?
C14 N2 C1 C8 8(2) . . . . ?
C7 N1 C1 N2 -1.9(16) . . . . ?
B1 N1 C1 N2 174.2(11) . . . . ?
C7 N1 C1 C8 176.2(11) . . . . ?
B1 N1 C1 C8 -7.7(19) . . . . ?
C2A N2A C1A N1A -13(11) . . . . ?
C14A N2A C1A N1A 177(5) . . . . ?
C2A N2A C1A C8A -176(10) . . . . ?
C14A N2A C1A C8A 14(15) . . . . ?
C7A N1A C1A N2A 12(10) . . . . ?
B1 N1A C1A N2A 166(7) . . . . ?
C7A N1A C1A C8A 177(7) . . . . ?
B1 N1A C1A C8A -30(11) . . . . ?
C1 N2 C2 C3 175.8(17) . . . . ?
C14 N2 C2 C3 -8(2) . . . . ?
C1 N2 C2 C7 -1.0(16) . . . . ?
C14 N2 C2 C7 175.5(8) . . . . ?
C1A N2A C2A C3A -172(12) . . . . ?
C14A N2A C2A C3A -1(15) . . . . ?
C1A N2A C2A C7A 9(10) . . . . ?
C14A N2A C2A C7A 180(5) . . . . ?
C7 C2 C3 C4 0(2) . . . . ?
N2 C2 C3 C4 -176.2(14) . . . . ?
C7A C2A C3A C4A 0(14) . . . . ?
N2A C2A C3A C4A -179(9) . . . . ?
C2 C3 C4 C5 0.2(19) . . . . ?
C2A C3A C4A C5A -11(13) . . . . ?
C3 C4 C5 C6 0.4(19) . . . . ?
C3A C4A C5A C6A 7(13) . . . . ?
C4 C5 C6 C7 -1(2) . . . . ?
C4A C5A C6A C7A 7(13) . . . . ?
C3 C2 C7 C6 -1(2) . . . . ?
N2 C2 C7 C6 175.9(12) . . . . ?
C3 C2 C7 N1 -177.1(13) . . . . ?
N2 C2 C7 N1 0.0(13) . . . . ?
C5 C6 C7 C2 1.7(19) . . . . ?
C5 C6 C7 N1 176.4(10) . . . . ?
C1 N1 C7 C2 1.1(13) . . . . ?
B1 N1 C7 C2 -174.9(9) . . . . ?
C1 N1 C7 C6 -174.2(15) . . . . ?
B1 N1 C7 C6 9.8(17) . . . . ?
C3A C2A C7A C6A 15(13) . . . . ?
N2A C2A C7A C6A -166(8) . . . . ?
C3A C2A C7A N1A 178(9) . . . . ?
N2A C2A C7A N1A -3(9) . . . . ?
C5A C6A C7A C2A -18(12) . . . . ?
C5A C6A C7A N1A -177(7) . . . . ?
C1A N1A C7A C2A -5(8) . . . . ?
B1 N1A C7A C2A -160(6) . . . . ?
C1A N1A C7A C6A 156(9) . . . . ?
B1 N1A C7A C6A 2(10) . . . . ?
N2 C1 C8 C13 171.7(17) . . . . ?
N1 C1 C8 C13 -6.1(18) . . . . ?
N2 C1 C8 C9 -3(2) . . . . ?
N1 C1 C8 C9 178.8(13) . . . . ?
N2A C1A C8A C13A 164(11) . . . . ?
N1A C1A C8A C13A 1(11) . . . . ?
N2A C1A C8A C9A -13(15) . . . . ?
N1A C1A C8A C9A -175(9) . . . . ?
C13 C8 C9 C10 2.0(16) . . . . ?
C1 C8 C9 C10 177.2(11) . . . . ?
C13A C8A C9A C10A -5(11) . . . . ?
C1A C8A C9A C10A 172(8) . . . . ?
C8 C9 C10 C11 -1.5(14) . . . . ?
C8A C9A C10A C11A 3(10) . . . . ?
C9 C10 C11 C12 -0.2(17) . . . . ?
C9A C10A C11A C12A 0(12) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C10A C11A C12A C13A 0(15) . . . . ?
C11 C12 C13 O1 -177.3(14) . . . . ?
C11 C12 C13 C8 -1(2) . . . . ?
B1 O1 C13 C12 -163.5(11) . . . . ?
B1 O1 C13 C8 20.3(18) . . . . ?
C9 C8 C13 C12 -0.8(19) . . . . ?
C1 C8 C13 C12 -176.2(14) . . . . ?
C9 C8 C13 O1 175.4(12) . . . . ?
C1 C8 C13 O1 0.0(19) . . . . ?
C11A C12A C13A O1A 167(9) . . . . ?
C11A C12A C13A C8A -2(15) . . . . ?
B1 O1A C13A C12A 178(7) . . . . ?
B1 O1A C13A C8A -13(12) . . . . ?
C9A C8A C13A C12A 5(13) . . . . ?
C1A C8A C13A C12A -172(9) . . . . ?
C9A C8A C13A O1A -164(9) . . . . ?
C1A C8A C13A O1A 20(12) . . . . ?
C1 N2 C14 C15 -99.6(17) . . . . ?
C2 N2 C14 C15 84.8(16) . . . . ?
C1 N2 C14 C27 89.8(15) . . . . ?
C2 N2 C14 C27 -85.7(13) . . . . ?
C1A N2A C14A C15A -90(10) . . . . ?
C2A N2A C14A C15A 102(10) . . . . ?
C1A N2A C14A C27A 91(9) . . . . ?
C2A N2A C14A C27A -77(8) . . . . ?
C27 C14 C15 C16 -2(2) . . . . ?
N2 C14 C15 C16 -171.5(11) . . . . ?
C27A C14A C15A C16A 14(13) . . . . ?
N2A C14A C15A C16A -165(8) . . . . ?
C14 C15 C16 C25 -1(2) . . . . ?
C14 C15 C16 C17 178.3(15) . . . . ?
C14A C15A C16A C25A -12(14) . . . . ?
C14A C15A C16A C17 173(10) . . . . ?
C15 C16 C17 C18 4(2) . . . . ?
C25 C16 C17 C18 -175.9(7) . . . . ?
C15 C16 C17 C22 -179.0(16) . . . . ?
C25 C16 C17 C22 0.9(13) . . . . ?
C15A C16A C17 C18 -17(16) . . . . ?
C25A C16A C17 C18 167(2) . . . . ?
C15A C16A C17 C22A 153(12) . . . . ?
C25A C16A C17 C22A -22(7) . . . . ?
C22 C17 C18 C19 2.3(9) . . . . ?
C16 C17 C18 C19 178.8(10) . . . . ?
C22A C17 C18 C19 17(3) . . . . ?
C16A C17 C18 C19 -175(6) . . . . ?
C17 C18 C19 C20 -0.4(11) . . . . ?
C17 C18 C19 C20A -13(4) . . . . ?
C17 C18 C19 Br1A -166.5(11) . . . . ?
C17 C18 C19 Br1 -178.7(4) . . . . ?
C18 C19 C20 C21 -3.4(16) . . . . ?
Br1 C19 C20 C21 175.0(10) . . . . ?
C18 C19 C20A C21A 9(9) . . . . ?
Br1A C19 C20A C21A 165(6) . . . . ?
C19 C20 C21 C22 5.0(19) . . . . ?
C19 C20A C21A C22A -7(11) . . . . ?
C25 N3 C22 C21 177.5(12) . . . . ?
C23 N3 C22 C21 4.7(18) . . . . ?
C25 N3 C22 C17 0.8(11) . . . . ?
C23 N3 C22 C17 -172.0(9) . . . . ?
C20 C21 C22 N3 -179.4(11) . . . . ?
C20 C21 C22 C17 -3.0(17) . . . . ?
C18 C17 C22 N3 176.4(7) . . . . ?
C16 C17 C22 N3 -1.0(12) . . . . ?
C18 C17 C22 C21 -0.6(13) . . . . ?
C16 C17 C22 C21 -178.0(11) . . . . ?
C25A N3A C22A C21A -152(7) . . . . ?
C23A N3A C22A C21A 37(9) . . . . ?
C25A N3A C22A C17 16(5) . . . . ?
C23A N3A C22A C17 -155(4) . . . . ?
C20A C21A C22A N3A 177(6) . . . . ?
C20A C21A C22A C17 9(9) . . . . ?
C18 C17 C22A N3A 175(3) . . . . ?
C16A C17 C22A N3A 4(7) . . . . ?
C18 C17 C22A C21A -15(7) . . . . ?
C16A C17 C22A C21A 174(6) . . . . ?
C22 N3 C23 C24 -87.7(12) . . . . ?
C25 N3 C23 C24 100.6(11) . . . . ?
C22A N3A C23A C24A -87(5) . . . . ?
C25A N3A C23A C24A 103(4) . . . . ?
C15 C16 C25 C26 3.3(19) . . . . ?
C17 C16 C25 C26 -176.5(8) . . . . ?
C15 C16 C25 N3 179.4(13) . . . . ?
C17 C16 C25 N3 -0.4(14) . . . . ?
C22 N3 C25 C26 175.6(9) . . . . ?
C23 N3 C25 C26 -11.4(16) . . . . ?
C22 N3 C25 C16 -0.2(13) . . . . ?
C23 N3 C25 C16 172.7(10) . . . . ?
C15A C16A C25A C26A 7(11) . . . . ?
C17 C16A C25A C26A -177(5) . . . . ?
C15A C16A C25A N3A -144(9) . . . . ?
C17 C16A C25A N3A 33(6) . . . . ?
C22A N3A C25A C26A -179(4) . . . . ?
C23A N3A C25A C26A -7(6) . . . . ?
C22A N3A C25A C16A -30(5) . . . . ?
C23A N3A C25A C16A 142(5) . . . . ?
C16 C25 C26 C27 -1.9(14) . . . . ?
N3 C25 C26 C27 -177.2(10) . . . . ?
C16A C25A C26A C27A -3(7) . . . . ?
N3A C25A C26A C27A 141(5) . . . . ?
C25 C26 C27 C14 -1.2(11) . . . . ?
C15 C14 C27 C26 3.0(15) . . . . ?
N2 C14 C27 C26 173.2(7) . . . . ?
C25A C26A C27A C14A 5(7) . . . . ?
C15A C14A C27A C26A -11(10) . . . . ?
N2A C14A C27A C26A 169(4) . . . . ?
C13 O1 B1 F1 -149.5(10) . . . . ?
C13 O1 B1 F2 88.7(10) . . . . ?
C13 O1 B1 N1 -29.5(12) . . . . ?
C13A O1A B1 F1 -129(6) . . . . ?
C13A O1A B1 F2 110(7) . . . . ?
C13A O1A B1 N1A -11(7) . . . . ?
C1 N1 B1 F1 139.5(11) . . . . ?
C7 N1 B1 F1 -45.2(10) . . . . ?
C1 N1 B1 F2 -95.3(12) . . . . ?
C7 N1 B1 F2 80.0(9) . . . . ?
C1 N1 B1 O1 23.8(13) . . . . ?
C7 N1 B1 O1 -161.0(8) . . . . ?
C1A N1A B1 F1 159(7) . . . . ?
C7A N1A B1 F1 -51(5) . . . . ?
C1A N1A B1 F2 -74(7) . . . . ?
C7A N1A B1 F2 75(5) . . . . ?
C1A N1A B1 O1A 34(8) . . . . ?
C7A N1A B1 O1A -177(5) . . . . ?
