#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:19:51 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298934 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/75/7717507.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_7717507
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 F3 N2 O2'
_chemical_formula_weight         278.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-21 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.182(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.821(14)
_cell_length_b                   6.154(3)
_cell_length_c                   18.764(12)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     2178(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0799
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8391
_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         27.478
_diffrn_reflns_theta_min         3.482
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.735
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.735
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0439
_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)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1196
_reflns_number_total             2490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02458c2.cif
_cod_data_source_block           BAz-F
_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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7717507
_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   0.979
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.34781(12) 0.7340(4) 0.52783(14) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.31580(11) 0.5306(4) 0.50054(15) 0.0389(6) Uani 1 1 d . . . . .
C3 C 0.27489(11) 0.4911(4) 0.41705(14) 0.0366(6) Uani 1 1 d . . . . .
H3 H 0.251382 0.356170 0.396583 0.044 Uiso 1 1 calc R U . . .
C4 C 0.26969(11) 0.6549(4) 0.36513(14) 0.0343(6) Uani 1 1 d . . . . .
C5 C 0.30064(12) 0.8580(4) 0.38988(15) 0.0363(6) Uani 1 1 d . . . . .
H5 H 0.295209 0.965498 0.350765 0.044 Uiso 1 1 calc R U . . .
C6 C 0.33941(12) 0.8982(4) 0.47296(15) 0.0381(6) Uani 1 1 d . . . . .
H6 H 0.360257 1.036842 0.492706 0.046 Uiso 1 1 calc R U . . .
C7 C 0.41712(11) 0.7607(4) 0.74352(14) 0.0330(6) Uani 1 1 d . . . . .
C8 C 0.39945(11) 0.5595(4) 0.76370(14) 0.0354(6) Uani 1 1 d . . . . .
C9 C 0.40945(12) 0.5290(4) 0.84234(15) 0.0377(6) Uani 1 1 d . . . . .
H9 H 0.397486 0.395965 0.858022 0.045 Uiso 1 1 calc R U . . .
C10 C 0.43739(12) 0.7002(4) 0.89616(13) 0.0341(6) Uani 1 1 d . . . . .
C11 C 0.45608(11) 0.8963(4) 0.87785(14) 0.0359(6) Uani 1 1 d . . . . .
H11 H 0.476296 1.007649 0.918233 0.043 Uiso 1 1 calc R U . . .
C12 C 0.44492(11) 0.9275(4) 0.80022(14) 0.0350(6) Uani 1 1 d . . . . .
H12 H 0.456184 1.062909 0.785317 0.042 Uiso 1 1 calc R U . . .
N1A N 0.3803(3) 0.6917(9) 0.6125(5) 0.0233(17) Uani 0.544(15) 1 d . . P A 1
N2A N 0.4005(2) 0.8473(9) 0.6643(5) 0.0241(18) Uani 0.544(15) 1 d . . P A 1
N1B N 0.3838(3) 0.8463(11) 0.6095(7) 0.031(3) Uani 0.456(15) 1 d . . P A 2
N2B N 0.3965(3) 0.6962(12) 0.6618(7) 0.030(2) Uani 0.456(15) 1 d . . P A 2
O1 O 0.32535(8) 0.3816(3) 0.55823(10) 0.0475(5) Uani 1 1 d . . . . .
F1 F 0.23228(7) 0.6154(2) 0.28301(8) 0.0508(4) Uani 1 1 d . . . . .
O2 O 0.37091(8) 0.4018(2) 0.70578(10) 0.0428(5) Uani 1 1 d . . . . .
F2 F 0.44730(8) 0.6733(2) 0.97320(8) 0.0531(4) Uani 1 1 d . . . . .
F3 F 0.44648(6) 0.35925(18) 0.65233(7) 0.0331(3) Uani 1 1 d . . . . .
B1 B 0.38318(13) 0.4412(4) 0.63831(17) 0.0273(6) 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'
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 N1A 141.2(3) . . ?
C6 C1 C2 121.7(2) . . ?
N1A C1 C2 97.1(3) . . ?
C6 C1 N1B 103.2(4) . . ?
C2 C1 N1B 134.2(4) . . ?
O1 C2 C3 122.7(2) . . ?
O1 C2 C1 117.8(2) . . ?
C3 C2 C1 119.5(2) . . ?
C4 C3 C2 117.0(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
F1 C4 C3 117.7(2) . . ?
F1 C4 C5 117.2(2) . . ?
C3 C4 C5 125.1(2) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C12 C7 C8 121.4(2) . . ?
C12 C7 N2B 144.9(4) . . ?
C8 C7 N2B 93.7(3) . . ?
C12 C7 N2A 107.7(3) . . ?
C8 C7 N2A 130.0(3) . . ?
O2 C8 C9 121.2(2) . . ?
O2 C8 C7 119.6(2) . . ?
C9 C8 C7 119.1(2) . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
F2 C10 C9 117.6(2) . . ?
F2 C10 C11 117.7(2) . . ?
C9 C10 C11 124.7(2) . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
N2A N1A C1 120.6(8) . . ?
N2A N1A B1 123.0(9) . . ?
C1 N1A B1 116.1(5) . . ?
N1A N2A C7 108.6(7) . . ?
N2B N1B C1 104.7(9) . . ?
N1B N2B C7 117.2(10) . . ?
N1B N2B B1 123.7(12) . . ?
C7 N2B B1 118.8(6) . . ?
C2 O1 B1 111.33(18) . . ?
C8 O2 B1 111.82(18) . . ?
F3 B1 O2 112.7(2) . . ?
F3 B1 O1 112.2(2) . . ?
O2 B1 O1 114.9(2) . . ?
F3 B1 N1A 107.2(2) . . ?
O2 B1 N1A 115.4(3) . . ?
O1 B1 N1A 92.8(3) . . ?
F3 B1 N2B 106.3(2) . . ?
O2 B1 N2B 90.6(4) . . ?
O1 B1 N2B 118.3(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
C1 C6 1.388(3) . ?
C1 N1A 1.402(9) . ?
C1 C2 1.399(3) . ?
C1 N1B 1.494(12) . ?
C2 O1 1.352(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 F1 1.354(2) . ?
C4 C5 1.385(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.380(3) . ?
C7 C8 1.404(3) . ?
C7 N2B 1.420(12) . ?
C7 N2A 1.443(9) . ?
C8 O2 1.353(2) . ?
C8 C9 1.392(3) . ?
C9 C10 1.372(3) . ?
C9 H9 0.9500 . ?
C10 F2 1.360(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.364(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N1A N2A 1.274(13) . ?
N1A B1 1.608(7) . ?
N1B N2B 1.273(17) . ?
N2B B1 1.616(8) . ?
O1 B1 1.442(3) . ?
O2 B1 1.440(3) . ?
F3 B1 1.366(3) . ?
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 -178.4(2) . . . . ?
N1A C1 C2 O1 0.6(3) . . . . ?
N1B C1 C2 O1 -11.0(4) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
N1A C1 C2 C3 179.1(2) . . . . ?
N1B C1 C2 C3 167.5(3) . . . . ?
O1 C2 C3 C4 -179.8(2) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C2 C3 C4 F1 177.17(18) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
F1 C4 C5 C6 -179.15(18) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
N1A C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
N1B C1 C6 C5 -172.9(2) . . . . ?
C12 C7 C8 O2 178.59(19) . . . . ?
N2B C7 C8 O2 -2.0(3) . . . . ?
N2A C7 C8 O2 10.4(4) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
N2B C7 C8 C9 -179.9(3) . . . . ?
N2A C7 C8 C9 -167.4(3) . . . . ?
O2 C8 C9 C10 -178.69(19) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 F2 179.80(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
F2 C10 C11 C12 -178.50(19) . . . . ?
C9 C10 C11 C12 1.5(4) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
N2B C7 C12 C11 -178.4(4) . . . . ?
N2A C7 C12 C11 171.1(2) . . . . ?
C6 C1 N1A N2A 18.0(6) . . . . ?
C2 C1 N1A N2A -160.7(4) . . . . ?
C6 C1 N1A B1 -167.6(3) . . . . ?
C2 C1 N1A B1 13.7(3) . . . . ?
C1 N1A N2A C7 167.5(3) . . . . ?
B1 N1A N2A C7 -6.6(5) . . . . ?
C12 C7 N2A N1A 174.7(3) . . . . ?
C8 C7 N2A N1A -15.8(5) . . . . ?
C6 C1 N1B N2B -175.9(3) . . . . ?
C2 C1 N1B N2B 15.1(6) . . . . ?
C1 N1B N2B C7 -167.1(4) . . . . ?
C1 N1B N2B B1 6.9(5) . . . . ?
C12 C7 N2B N1B -20.5(7) . . . . ?
C8 C7 N2B N1B 160.4(4) . . . . ?
C12 C7 N2B B1 165.2(3) . . . . ?
C8 C7 N2B B1 -13.8(4) . . . . ?
C3 C2 O1 B1 165.7(2) . . . . ?
C1 C2 O1 B1 -15.9(3) . . . . ?
C9 C8 O2 B1 -163.9(2) . . . . ?
C7 C8 O2 B1 18.3(3) . . . . ?
C8 O2 B1 F3 86.9(2) . . . . ?
C8 O2 B1 O1 -142.88(19) . . . . ?
C8 O2 B1 N1A -36.6(3) . . . . ?
C8 O2 B1 N2B -21.0(3) . . . . ?
C2 O1 B1 F3 -90.1(2) . . . . ?
C2 O1 B1 O2 139.52(19) . . . . ?
C2 O1 B1 N1A 19.8(3) . . . . ?
C2 O1 B1 N2B 34.2(4) . . . . ?
N2A N1A B1 F3 -92.9(4) . . . . ?
C1 N1A B1 F3 92.9(3) . . . . ?
N2A N1A B1 O2 33.5(4) . . . . ?
C1 N1A B1 O2 -140.8(3) . . . . ?
N2A N1A B1 O1 152.9(3) . . . . ?
C1 N1A B1 O1 -21.4(3) . . . . ?
N1B N2B B1 F3 94.8(5) . . . . ?
C7 N2B B1 F3 -91.3(4) . . . . ?
N1B N2B B1 O2 -151.3(4) . . . . ?
C7 N2B B1 O2 22.6(4) . . . . ?
N1B N2B B1 O1 -32.3(6) . . . . ?
C7 N2B B1 O1 141.5(4) . . . . ?
