#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:19:51 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298934 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/75/7717509.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_7717509
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 Cl2 F N2 O2'
_chemical_formula_weight         310.90
_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
;
2023-10-21 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                96.26(3)
_cell_angle_beta                 97.76(5)
_cell_angle_gamma                116.43(2)
_cell_formula_units_Z            2
_cell_length_a                   7.084(4)
_cell_length_b                   7.205(5)
_cell_length_c                   13.827(7)
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     614.7(7)
_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 0.978
_diffrn_measured_fraction_theta_max 0.957
_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  0.0481
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5015
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         3.029
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       Plate
_exptl_crystal_F_000             312
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0544
_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)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1707
_reflns_number_total             2696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02458c2.cif
_cod_data_source_block           BAz-Cl
_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_cell_volume        614.7(6)
_cod_database_code               7717509
_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 0.6369(5) 0.5169(5) 0.7974(2) 0.0280(8) Uani 1 1 d . . . . .
C2 C 0.8120(5) 0.5663(5) 0.8740(2) 0.0264(7) Uani 1 1 d D . . . .
C3 C 0.8372(5) 0.6872(5) 0.9649(2) 0.0268(7) Uani 1 1 d . . . . .
H3 H 0.957083 0.726140 1.017313 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6819(5) 0.7483(5) 0.9760(2) 0.0279(7) Uani 1 1 d . . . . .
C5 C 0.5060(5) 0.6984(5) 0.8993(2) 0.0331(8) Uani 1 1 d . . . . .
H5 H 0.402859 0.744829 0.909781 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4836(5) 0.5817(5) 0.8090(2) 0.0349(9) Uani 1 1 d . . . . .
H6 H 0.365921 0.546770 0.756045 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6807(5) 0.2960(5) 0.5641(2) 0.0272(7) Uani 1 1 d . . . . .
C8 C 0.8822(5) 0.3009(4) 0.5925(2) 0.0235(7) Uani 1 1 d D . . . .
C9 C 0.9778(5) 0.2490(4) 0.5200(2) 0.0241(7) Uani 1 1 d . . . . .
H9 H 1.114897 0.254799 0.537550 0.029 Uiso 1 1 calc R U . . .
C10 C 0.8703(5) 0.1893(5) 0.4225(2) 0.0255(7) Uani 1 1 d . . . . .
C11 C 0.6721(5) 0.1833(5) 0.3928(2) 0.0305(8) Uani 1 1 d . . . . .
H11 H 0.602577 0.141903 0.324612 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5790(5) 0.2381(5) 0.4635(2) 0.0315(8) Uani 1 1 d . . . . .
H12 H 0.444474 0.236890 0.444331 0.038 Uiso 1 1 calc R U . . .
N1A N 0.6681(8) 0.3991(8) 0.7173(4) 0.0227(12) Uani 0.848(9) 1 d . . P A 1
N2A N 0.5786(5) 0.3683(5) 0.6265(3) 0.0261(12) Uani 0.848(9) 1 d . . P A 1
N1B N 0.552(3) 0.440(3) 0.6951(13) 0.026(6) Uani 0.152(9) 1 d . . P A 2
N2B N 0.686(5) 0.370(5) 0.683(2) 0.024(8) Uani 0.152(9) 1 d . U P A 2
O1A O 0.9510(9) 0.4890(8) 0.8539(4) 0.0264(12) Uani 0.848(9) 1 d D . P A 1
O2A O 0.9882(9) 0.3715(10) 0.6877(3) 0.0241(12) Uani 0.848(9) 1 d D . P A 1
O1B O 0.956(5) 0.529(4) 0.835(2) 0.021(5) Uani 0.152(9) 1 d D U P A 2
B1 B 0.8512(6) 0.3404(6) 0.7587(2) 0.0238(8) Uani 1 1 d D . . . .
F1A F 0.7560(16) 0.1337(8) 0.7720(6) 0.0305(12) Uani 0.848(9) 1 d D . P A 1
F1B F 0.746(10) 0.162(5) 0.798(3) 0.034(7) Uani 0.152(9) 1 d D . P A 2
Cl1 Cl 0.70472(15) 0.89315(13) 1.08898(6) 0.0417(3) Uani 1 1 d . . . . .
Cl2 Cl 0.98637(14) 0.11732(13) 0.33202(5) 0.0376(3) Uani 1 1 d . . . . .
O2B O 0.985(6) 0.322(6) 0.690(2) 0.023(5) Uani 0.152(9) 1 d D U P A 2
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'
Cl Cl 0.1484 0.1585 '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 122.2(3) . . ?
C6 C1 N1B 92.5(10) . . ?
C2 C1 N1B 144.5(10) . . ?
C6 C1 N1A 134.1(4) . . ?
C2 C1 N1A 103.8(4) . . ?
C6 C1 N2B 133.0(11) . . ?
C2 C1 N2B 104.7(11) . . ?
N1B C1 N2B 40.6(16) . . ?
O1B C2 C3 129.8(13) . . ?
O1A C2 C3 123.5(3) . . ?
O1B C2 C1 108.0(13) . . ?
O1A C2 C1 116.7(3) . . ?
C3 C2 C1 119.9(3) . . ?
C4 C3 C2 117.4(3) . . ?
C3 C4 C5 122.8(3) . . ?
C3 C4 Cl1 118.6(3) . . ?
C5 C4 Cl1 118.6(3) . . ?
C6 C5 C4 119.6(3) . . ?
C5 C6 C1 118.1(3) . . ?
N2A C7 C12 114.1(3) . . ?
N2A C7 C8 125.7(3) . . ?
C12 C7 C8 119.8(3) . . ?
C12 C7 N2B 150.9(13) . . ?
C8 C7 N2B 89.3(13) . . ?
O2A C8 C9 120.2(3) . . ?
C9 C8 O2B 114.0(13) . . ?
O2A C8 C7 120.1(3) . . ?
C9 C8 C7 119.4(3) . . ?
O2B C8 C7 125.8(13) . . ?
C10 C9 C8 118.8(3) . . ?
C9 C10 C11 122.8(3) . . ?
C9 C10 Cl2 118.8(3) . . ?
C11 C10 Cl2 118.4(2) . . ?
C12 C11 C10 118.7(3) . . ?
C11 C12 C7 120.4(3) . . ?
N2A N1A C1 124.2(5) . . ?
N2A N1A B1 126.7(5) . . ?
C1 N1A B1 108.6(4) . . ?
N1A N2A C7 110.4(4) . . ?
N2B N1B C1 94(2) . . ?
N1B N2B B1 132(2) . . ?
N1B N2B C7 113(3) . . ?
B1 N2B C7 114.8(19) . . ?
N1B N2B C1 45.5(13) . . ?
B1 N2B C1 87.0(13) . . ?
C7 N2B C1 157(2) . . ?
C2 O1A B1 107.2(4) . . ?
C8 O2A B1 114.3(4) . . ?
C2 O1B B1 111(2) . . ?
F1A B1 O2A 111.7(4) . . ?
F1B B1 O1B 112(2) . . ?
F1A B1 O1A 111.6(4) . . ?
O2A B1 O1A 115.1(4) . . ?
F1B B1 O2B 115(2) . . ?
O1B B1 O2B 114.8(19) . . ?
F1B B1 N2B 110(3) . . ?
O1B B1 N2B 106.5(16) . . ?
O2B B1 N2B 97.9(15) . . ?
F1A B1 N1A 109.0(6) . . ?
O2A B1 N1A 107.7(3) . . ?
O1A B1 N1A 101.0(3) . . ?
C8 O2B B1 109(2) . . ?
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 1.381(5) . ?
C1 C2 1.399(4) . ?
C1 N1B 1.405(18) . ?
C1 N1A 1.423(5) . ?
C1 N2B 1.97(3) . ?
C2 O1B 1.33(3) . ?
C2 O1A 1.374(6) . ?
C2 C3 1.390(4) . ?
C3 C4 1.374(4) . ?
C4 C5 1.402(5) . ?
C4 Cl1 1.727(3) . ?
C5 C6 1.375(4) . ?
C7 N2A 1.394(5) . ?
C7 C12 1.401(4) . ?
C7 C8 1.412(4) . ?
C7 N2B 1.66(3) . ?
C8 O2A 1.343(6) . ?
C8 C9 1.389(4) . ?
C8 O2B 1.40(3) . ?
C9 C10 1.374(4) . ?
C10 C11 1.388(4) . ?
C10 Cl2 1.739(3) . ?
C11 C12 1.368(4) . ?
N1A N2A 1.276(7) . ?
N1A B1 1.590(7) . ?
N1B N2B 1.28(4) . ?
N2B B1 1.57(4) . ?
O1A B1 1.465(6) . ?
O2A B1 1.438(6) . ?
O1B B1 1.44(3) . ?
B1 F1A 1.381(6) . ?
B1 F1B 1.38(3) . ?
B1 O2B 1.47(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 O1B -165.1(14) . . . . ?
N1B C1 C2 O1B 1.2(19) . . . . ?
N2B C1 C2 O1B 10.8(17) . . . . ?
C6 C1 C2 O1A 178.7(4) . . . . ?
N1A C1 C2 O1A -1.8(4) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
N1B C1 C2 C3 165.4(14) . . . . ?
N1A C1 C2 C3 178.5(3) . . . . ?
N2B C1 C2 C3 175.0(9) . . . . ?
O1B C2 C3 C4 162.1(17) . . . . ?
O1A C2 C3 C4 -177.8(4) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C2 C3 C4 Cl1 178.4(2) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
Cl1 C4 C5 C6 -179.5(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
N1B C1 C6 C5 -172.2(8) . . . . ?
N1A C1 C6 C5 -179.5(4) . . . . ?
N2B C1 C6 C5 -174.8(12) . . . . ?
N2A C7 C8 O2A 3.0(5) . . . . ?
C12 C7 C8 O2A 175.0(4) . . . . ?
N2A C7 C8 C9 -171.6(3) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
N2B C7 C8 C9 179.8(11) . . . . ?
C12 C7 C8 O2B -168.9(19) . . . . ?
N2B C7 C8 O2B 11(2) . . . . ?
O2A C8 C9 C10 -176.2(4) . . . . ?
O2B C8 C9 C10 168.9(17) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C8 C9 C10 Cl2 -178.3(2) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
Cl2 C10 C11 C12 179.5(2) . . . . ?
C10 C11 C12 C7 -0.9(5) . . . . ?
N2A C7 C12 C11 173.8(3) . . . . ?
C8 C7 C12 C11 0.9(5) . . . . ?
N2B C7 C12 C11 -178(2) . . . . ?
C6 C1 N1A N2A 18.0(7) . . . . ?
C2 C1 N1A N2A -161.4(4) . . . . ?
C6 C1 N1A B1 -169.0(3) . . . . ?
C2 C1 N1A B1 11.6(4) . . . . ?
C1 N1A N2A C7 164.8(4) . . . . ?
B1 N1A N2A C7 -6.9(6) . . . . ?
C12 C7 N2A N1A 173.9(3) . . . . ?
C8 C7 N2A N1A -13.7(5) . . . . ?
C6 C1 N1B N2B -177.2(16) . . . . ?
C2 C1 N1B N2B 14(2) . . . . ?
C1 N1B N2B B1 10(3) . . . . ?
C1 N1B N2B C7 -169.5(17) . . . . ?
C12 C7 N2B N1B -18(4) . . . . ?
C8 C7 N2B N1B 163(2) . . . . ?
C12 C7 N2B B1 162.3(9) . . . . ?
C8 C7 N2B B1 -16.8(17) . . . . ?
C12 C7 N2B C1 -37(6) . . . . ?
C8 C7 N2B C1 144(5) . . . . ?
C3 C2 O1A B1 170.1(3) . . . . ?
C1 C2 O1A B1 -9.6(5) . . . . ?
C9 C8 O2A B1 -156.6(4) . . . . ?
C7 C8 O2A B1 28.8(6) . . . . ?
C3 C2 O1B B1 159.0(9) . . . . ?
C1 C2 O1B B1 -39(2) . . . . ?
C8 O2A B1 F1A 77.2(7) . . . . ?
C8 O2A B1 O1A -154.2(5) . . . . ?
C8 O2A B1 N1A -42.5(6) . . . . ?
C2 O1B B1 F1B -66(4) . . . . ?
C2 O1B B1 O2B 162(2) . . . . ?
C2 O1B B1 N2B 54(2) . . . . ?
C2 O1A B1 F1A -100.6(6) . . . . ?
C2 O1A B1 O2A 130.7(5) . . . . ?
C2 O1A B1 N1A 15.0(5) . . . . ?
N1B N2B B1 F1B 78(3) . . . . ?
C7 N2B B1 F1B -102(2) . . . . ?
C1 N2B B1 F1B 85.4(17) . . . . ?
N1B N2B B1 O1B -43(3) . . . . ?
C7 N2B B1 O1B 136.7(19) . . . . ?
C1 N2B B1 O1B -35.8(17) . . . . ?
N1B N2B B1 O2B -162(3) . . . . ?
C7 N2B B1 O2B 18(2) . . . . ?
C1 N2B B1 O2B -154.8(17) . . . . ?
N2A N1A B1 F1A -86.4(6) . . . . ?
C1 N1A B1 F1A 100.8(4) . . . . ?
N2A N1A B1 O2A 35.0(6) . . . . ?
C1 N1A B1 O2A -137.8(4) . . . . ?
N2A N1A B1 O1A 156.0(5) . . . . ?
C1 N1A B1 O1A -16.7(5) . . . . ?
C9 C8 O2B B1 -170.5(14) . . . . ?
C7 C8 O2B B1 -1(3) . . . . ?
F1B B1 O2B C8 106(4) . . . . ?
O1B B1 O2B C8 -123(2) . . . . ?
N2B B1 O2B C8 -10(3) . . . . ?
