#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:19:51 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298934 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/75/7717508.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_7717508
loop_
_publ_author_name
'Nakamura, Masashi'
'Gon, Masayuki'
'Tanaka, Kazuo'
_publ_section_title
;
 Contribution of radiative rate constants to crystallization-induced
 emission enhancement in boron-fused azobenzene complexes.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1079
_journal_page_last               1086
_journal_paper_doi               10.1039/d4dt02458c
_journal_volume                  54
_journal_year                    2025
_chemical_formula_sum            'C12 H6 B Br2 F N2 O2'
_chemical_formula_weight         399.82
_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
;
2024-03-12 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                95.261(3)
_cell_angle_beta                 97.928(6)
_cell_angle_gamma                115.739(7)
_cell_formula_units_Z            2
_cell_length_a                   6.975(3)
_cell_length_b                   7.306(3)
_cell_length_c                   14.302(6)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     640.8(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5189
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         3.141
_exptl_absorpt_coefficient_mu    6.337
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_description       Plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0334
_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)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2074
_reflns_number_total             2802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02458c2.cif
_cod_data_source_block           BAz-Br
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7717506--7717509.cif.
;
_cod_database_code               7717508
_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.
;
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
C1 C 0.6327(5) 0.5119(5) 0.7951(2) 0.0267(8) Uani 1 1 d . . . . .
C2 C 0.8070(5) 0.5507(5) 0.8682(2) 0.0272(8) Uani 1 1 d . . . . .
C3 C 0.8340(5) 0.6639(5) 0.9562(2) 0.0268(8) Uani 1 1 d . . . . .
H1 H 0.951956 0.692440 1.006762 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6829(5) 0.7333(5) 0.9675(2) 0.0256(8) Uani 1 1 d . . . . .
C5 C 0.5074(5) 0.6948(5) 0.8959(3) 0.0319(9) Uani 1 1 d . . . . .
H2 H 0.406257 0.744735 0.907470 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4813(5) 0.5831(5) 0.8078(3) 0.0323(9) Uani 1 1 d . . . . .
H3 H 0.363440 0.555752 0.757411 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6680(5) 0.3003(5) 0.5691(3) 0.0254(8) Uani 1 1 d . . . . .
C8 C 0.8721(5) 0.3005(5) 0.5941(2) 0.0236(7) Uani 1 1 d . . . . .
C9 C 0.9658(5) 0.2501(5) 0.5229(2) 0.0233(7) Uani 1 1 d . . . . .
H4 H 1.103915 0.252567 0.538173 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8529(5) 0.1959(5) 0.4291(2) 0.0221(7) Uani 1 1 d . . . . .
C11 C 0.6526(5) 0.1950(5) 0.4038(3) 0.0294(8) Uani 1 1 d . . . . .
H5 H 0.579080 0.157249 0.338796 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5641(5) 0.2487(5) 0.4735(3) 0.0298(8) Uani 1 1 d . . . . .
H6 H 0.428717 0.251208 0.456723 0.036 Uiso 1 1 calc R U . . .
N1A N 0.6606(9) 0.3975(8) 0.7176(3) 0.0238(13) Uani 0.844(9) 1 d . . P A 1
N2A N 0.5684(6) 0.3719(5) 0.6309(3) 0.0241(11) Uani 0.844(9) 1 d . . P A 1
N1B N 0.549(3) 0.440(3) 0.6959(14) 0.015(5) Uani 0.156(9) 1 d . U P A 2
N2B N 0.669(5) 0.367(4) 0.6793(19) 0.015(5) Uani 0.156(9) 1 d . . P A 2
O1 O 0.9451(3) 0.4756(4) 0.84480(16) 0.0312(6) Uani 1 1 d . . . . .
O2 O 0.9800(3) 0.3564(3) 0.68596(16) 0.0291(6) Uani 1 1 d . . . . .
B1 B 0.8433(6) 0.3308(6) 0.7551(3) 0.0235(9) Uani 1 1 d . . . . .
F1 F 0.7421(3) 0.1299(3) 0.76947(14) 0.0369(5) Uani 1 1 d . . . . .
Br1 Br 0.71393(6) 0.88550(5) 1.08789(3) 0.03617(13) Uani 1 1 d . . . . .
Br2 Br 0.97212(6) 0.11606(5) 0.33132(2) 0.03285(12) Uani 1 1 d . . . . .
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'
B B 0.0013 0.0007 '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'
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
C6 C1 C2 121.8(3) . . ?
C6 C1 N1A 134.2(4) . . ?
C2 C1 N1A 104.0(4) . . ?
C6 C1 N1B 94.0(9) . . ?
C2 C1 N1B 143.5(9) . . ?
O1 C2 C3 124.5(3) . . ?
O1 C2 C1 115.4(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 117.2(3) . . ?
C3 C4 C5 123.5(3) . . ?
C3 C4 Br1 118.1(3) . . ?
C5 C4 Br1 118.4(3) . . ?
C6 C5 C4 119.3(3) . . ?
C5 C6 C1 118.0(3) . . ?
C12 C7 N2A 114.3(3) . . ?
C12 C7 C8 119.6(3) . . ?
N2A C7 C8 125.6(3) . . ?
C12 C7 N2B 149.2(11) . . ?
C8 C7 N2B 91.3(11) . . ?
O2 C8 C9 119.5(3) . . ?
O2 C8 C7 120.8(3) . . ?
C9 C8 C7 119.6(3) . . ?
C10 C9 C8 118.4(3) . . ?
C9 C10 C11 122.4(3) . . ?
C9 C10 Br2 119.1(3) . . ?
C11 C10 Br2 118.4(2) . . ?
C12 C11 C10 118.9(3) . . ?
C11 C12 C7 121.1(3) . . ?
N2A N1A C1 124.1(5) . . ?
N2A N1A B1 126.5(4) . . ?
C1 N1A B1 109.0(4) . . ?
N1A N2A C7 110.6(5) . . ?
N2B N1B C1 98(2) . . ?
N1B N2B C7 117(3) . . ?
N1B N2B B1 129(2) . . ?
C7 N2B B1 113.7(16) . . ?
C2 O1 B1 108.8(3) . . ?
C8 O2 B1 114.1(3) . . ?
F1 B1 O2 112.2(3) . . ?
F1 B1 O1 112.2(3) . . ?
O2 B1 O1 115.1(3) . . ?
F1 B1 N1A 108.2(3) . . ?
O2 B1 N1A 108.9(3) . . ?
O1 B1 N1A 99.2(3) . . ?
F1 B1 N2B 107.3(10) . . ?
O2 B1 N2B 90.7(9) . . ?
O1 B1 N2B 117.5(9) . . ?
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
C1 C6 1.390(5) . ?
C1 C2 1.396(4) . ?
C1 N1A 1.413(5) . ?
C1 N1B 1.414(19) . ?
C2 O1 1.362(4) . ?
C2 C3 1.382(5) . ?
C3 C4 1.375(4) . ?
C4 C5 1.389(5) . ?
C4 Br1 1.893(3) . ?
C5 C6 1.381(5) . ?
C7 C12 1.389(5) . ?
C7 N2A 1.392(5) . ?
C7 C8 1.418(4) . ?
C7 N2B 1.60(2) . ?
C8 O2 1.349(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.391(4) . ?
C10 Br2 1.892(3) . ?
C11 C12 1.356(5) . ?
N1A N2A 1.273(7) . ?
N1A B1 1.596(7) . ?
N1B N2B 1.21(4) . ?
N2B B1 1.64(3) . ?
O1 B1 1.455(4) . ?
O2 B1 1.436(4) . ?
B1 F1 1.375(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
C6 C1 C2 O1 -178.5(3) . . . . ?
N1A C1 C2 O1 1.0(4) . . . . ?
N1B C1 C2 O1 -11.0(13) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
N1A C1 C2 C3 179.1(3) . . . . ?
N1B C1 C2 C3 167.1(12) . . . . ?
O1 C2 C3 C4 178.2(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 Br1 179.2(2) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
Br1 C4 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
N1A C1 C6 C5 -179.5(4) . . . . ?
N1B C1 C6 C5 -172.7(7) . . . . ?
C12 C7 C8 O2 177.8(3) . . . . ?
N2A C7 C8 O2 6.1(5) . . . . ?
N2B C7 C8 O2 -2.5(10) . . . . ?
C12 C7 C8 C9 0.2(5) . . . . ?
N2A C7 C8 C9 -171.5(3) . . . . ?
N2B C7 C8 C9 179.9(10) . . . . ?
O2 C8 C9 C10 -179.1(3) . . . . ?
C7 C8 C9 C10 -1.5(5) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C8 C9 C10 Br2 -177.6(2) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
Br2 C10 C11 C12 179.0(2) . . . . ?
C10 C11 C12 C7 -1.3(5) . . . . ?
N2A C7 C12 C11 173.8(3) . . . . ?
C8 C7 C12 C11 1.2(5) . . . . ?
N2B C7 C12 C11 -178.1(19) . . . . ?
C6 C1 N1A N2A 16.7(8) . . . . ?
C2 C1 N1A N2A -162.8(5) . . . . ?
C6 C1 N1A B1 -169.7(4) . . . . ?
C2 C1 N1A B1 10.8(4) . . . . ?
C1 N1A N2A C7 164.6(4) . . . . ?
B1 N1A N2A C7 -7.8(7) . . . . ?
C12 C7 N2A N1A 174.0(4) . . . . ?
C8 C7 N2A N1A -14.0(6) . . . . ?
C6 C1 N1B N2B -177.5(15) . . . . ?
C2 C1 N1B N2B 13(2) . . . . ?
C1 N1B N2B C7 -168.8(16) . . . . ?
C1 N1B N2B B1 9(3) . . . . ?
C12 C7 N2B N1B -19(4) . . . . ?
C8 C7 N2B N1B 161(2) . . . . ?
C12 C7 N2B B1 162.4(8) . . . . ?
C8 C7 N2B B1 -17.0(15) . . . . ?
C3 C2 O1 B1 168.4(3) . . . . ?
C1 C2 O1 B1 -13.6(4) . . . . ?
C9 C8 O2 B1 -158.1(3) . . . . ?
C7 C8 O2 B1 24.3(4) . . . . ?
C8 O2 B1 F1 80.3(4) . . . . ?
C8 O2 B1 O1 -149.8(3) . . . . ?
C8 O2 B1 N1A -39.5(4) . . . . ?
C8 O2 B1 N2B -28.7(10) . . . . ?
C2 O1 B1 F1 -96.3(3) . . . . ?
C2 O1 B1 O2 133.8(3) . . . . ?
C2 O1 B1 N1A 17.8(4) . . . . ?
C2 O1 B1 N2B 28.8(11) . . . . ?
N2A N1A B1 F1 -87.2(6) . . . . ?
C1 N1A B1 F1 99.4(4) . . . . ?
N2A N1A B1 O2 35.0(7) . . . . ?
C1 N1A B1 O2 -138.4(3) . . . . ?
N2A N1A B1 O1 155.7(5) . . . . ?
C1 N1A B1 O1 -17.8(4) . . . . ?
N1B N2B B1 F1 96(3) . . . . ?
C7 N2B B1 F1 -85.5(15) . . . . ?
N1B N2B B1 O2 -150(3) . . . . ?
C7 N2B B1 O2 28.0(15) . . . . ?
N1B N2B B1 O1 -31(3) . . . . ?
C7 N2B B1 O1 147.0(11) . . . . ?
