# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BAz-H
_database_code_depnum_ccdc_archive 'CCDC 2302562'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2023-10-21 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 B F N2 O2'
_chemical_formula_weight         242.01

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.982(4)
_cell_length_b                   21.445(11)
_cell_length_c                   7.808(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.861(7)
_cell_angle_gamma                90
_cell_volume                     1060.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3171
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8477
_diffrn_reflns_av_unetI/netI     0.1199
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2394
_reflns_number_gt                1272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0215P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     182
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_restrained_S_all      0.801
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2206(3) 0.63999(9) 0.5616(3) 0.0231(5) Uani 1 1 d . . . . .
C2 C 0.3413(4) 0.68513(10) 0.5208(3) 0.0279(5) Uani 1 1 d . . . . .
C3 C 0.2406(4) 0.73597(10) 0.4107(3) 0.0331(6) Uani 1 1 d . . . . .
H3 H 0.318118 0.766824 0.379236 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0253(4) 0.74062(11) 0.3480(3) 0.0380(6) Uani 1 1 d . . . . .
H4 H -0.045491 0.775603 0.273685 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0924(4) 0.69550(11) 0.3903(3) 0.0367(6) Uani 1 1 d . . . . .
H5 H -0.240766 0.700441 0.345405 0.044 Uiso 1 1 calc R U . . .
C6 C 0.0038(4) 0.64419(11) 0.4957(3) 0.0304(6) Uani 1 1 d . . . . .
H6 H -0.075373 0.612709 0.522459 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5038(4) 0.50068(10) 0.7590(3) 0.0263(5) Uani 1 1 d . . . . .
C8 C 0.6944(4) 0.51611(10) 0.7492(3) 0.0297(6) Uani 1 1 d . . . . .
C9 C 0.8489(4) 0.47093(11) 0.7886(3) 0.0358(6) Uani 1 1 d . . . . .
H9 H 0.975312 0.480015 0.775614 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8176(4) 0.41265(11) 0.8468(3) 0.0349(6) Uani 1 1 d . . . . .
H10 H 0.925408 0.382048 0.877932 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6309(4) 0.39797(10) 0.8608(3) 0.0353(6) Uani 1 1 d . . . . .
H11 H 0.612623 0.357722 0.902531 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4745(4) 0.44102(10) 0.8149(3) 0.0309(6) Uani 1 1 d . . . . .
H12 H 0.345304 0.430486 0.820838 0.037 Uiso 1 1 calc R U . . .
N1A N 0.3684(4) 0.59464(11) 0.6648(3) 0.0233(6) Uani 0.915(5) 1 d . . P A 1
O1 O 0.5510(2) 0.67383(7) 0.59049(19) 0.0333(4) Uani 1 1 d . . . . .
N2A N 0.3232(4) 0.53900(11) 0.6923(3) 0.0272(7) Uani 0.915(5) 1 d . . P A 1
O2 O 0.7261(3) 0.57363(7) 0.6938(2) 0.0383(4) Uani 1 1 d . . . . .
B1 B 0.5987(4) 0.62142(12) 0.7207(4) 0.0293(6) Uani 1 1 d . . . . .
F1 F 0.67755(19) 0.64144(6) 0.90686(16) 0.0339(4) Uani 1 1 d . . . . .
N1B N 0.240(4) 0.5773(11) 0.631(3) 0.016(5) Uani 0.085(5) 1 d . U P A 2
N2B N 0.456(4) 0.5658(12) 0.715(3) 0.020(5) Uani 0.085(5) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.382(3) . ?
C1 N1A 1.400(3) . ?
C1 C2 1.405(3) . ?
C1 N1B 1.43(2) . ?
C2 O1 1.352(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.369(3) . ?
C7 C12 1.394(3) . ?
C7 C8 1.405(3) . ?
C7 N2A 1.408(3) . ?
C7 N2B 1.44(3) . ?
C8 O2 1.356(3) . ?
C8 C9 1.385(3) . ?
C8 N2B 1.90(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.358(3) . ?
N1A N2A 1.275(4) . ?
N1A B1 1.586(4) . ?
O1 B1 1.457(3) . ?
O2 B1 1.429(3) . ?
B1 F1 1.388(3) . ?
B1 N2B 1.54(2) . ?
N1B N2B 1.39(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 133.4(2) . . ?
C6 C1 C2 122.5(2) . . ?
N1A C1 C2 104.0(2) . . ?
C6 C1 N1B 96.6(10) . . ?
C2 C1 N1B 139.6(10) . . ?
O1 C2 C3 124.9(2) . . ?
O1 C2 C1 115.87(19) . . ?
C3 C2 C1 119.2(2) . . ?
C4 C3 C2 118.2(2) . . ?
C3 C4 C5 122.0(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C1 117.4(2) . . ?
C12 C7 C8 120.0(2) . . ?
C12 C7 N2A 115.2(2) . . ?
C8 C7 N2A 124.3(2) . . ?
C12 C7 N2B 156.1(10) . . ?
C8 C7 N2B 83.5(10) . . ?
O2 C8 C9 119.4(2) . . ?
O2 C8 C7 121.2(2) . . ?
C9 C8 C7 119.4(2) . . ?
O2 C8 N2B 72.2(8) . . ?
C9 C8 N2B 168.3(8) . . ?
C7 C8 N2B 49.1(8) . . ?
C10 C9 C8 119.4(2) . . ?
C9 C10 C11 121.0(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C7 120.0(2) . . ?
N2A N1A C1 124.9(3) . . ?
N2A N1A B1 125.9(3) . . ?
C1 N1A B1 108.9(2) . . ?
C2 O1 B1 108.09(17) . . ?
N1A N2A C7 111.2(3) . . ?
C8 O2 B1 114.22(19) . . ?
F1 B1 O2 112.2(2) . . ?
F1 B1 O1 111.45(19) . . ?
O2 B1 O1 115.1(2) . . ?
F1 B1 N2B 103.7(8) . . ?
O2 B1 N2B 82.8(9) . . ?
O1 B1 N2B 128.4(10) . . ?
F1 B1 N1A 108.06(19) . . ?
O2 B1 N1A 108.75(19) . . ?
O1 B1 N1A 100.33(19) . . ?
N2B N1B C1 105(2) . . ?
N1B N2B C7 112(2) . . ?
N1B N2B B1 116(2) . . ?
C7 N2B B1 131.5(18) . . ?
N1B N2B C8 151.5(19) . . ?
C7 N2B C8 47.4(8) . . ?
B1 N2B C8 85.1(11) . . ?

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 -178.15(17) . . . . ?
N1A C1 C2 O1 -1.3(2) . . . . ?
N1B C1 C2 O1 -14.2(12) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
N1A C1 C2 C3 176.96(18) . . . . ?
N1B C1 C2 C3 164.1(12) . . . . ?
O1 C2 C3 C4 179.13(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
N1A C1 C6 C5 -177.2(2) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1B C1 C6 C5 -171.1(7) . . . . ?
C12 C7 C8 O2 179.45(18) . . . . ?
N2A C7 C8 O2 8.2(3) . . . . ?
N2B C7 C8 O2 -5.7(9) . . . . ?
C12 C7 C8 C9 2.4(3) . . . . ?
N2A C7 C8 C9 -168.9(2) . . . . ?
N2B C7 C8 C9 177.3(9) . . . . ?
C12 C7 C8 N2B -174.9(9) . . . . ?
O2 C8 C9 C10 179.32(18) . . . . ?
C7 C8 C9 C10 -3.6(3) . . . . ?
N2B C8 C9 C10 7(3) . . . . ?
C8 C9 C10 C11 2.1(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C7 -1.9(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
N2A C7 C12 C11 172.41(19) . . . . ?
N2B C7 C12 C11 -167(2) . . . . ?
C6 C1 N1A N2A 13.9(4) . . . . ?
C2 C1 N1A N2A -162.5(2) . . . . ?
C6 C1 N1A B1 -172.4(2) . . . . ?
C2 C1 N1A B1 11.3(2) . . . . ?
C3 C2 O1 B1 171.7(2) . . . . ?
C1 C2 O1 B1 -10.1(2) . . . . ?
C1 N1A N2A C7 165.33(19) . . . . ?
B1 N1A N2A C7 -7.4(3) . . . . ?
C12 C7 N2A N1A 172.54(18) . . . . ?
C8 C7 N2A N1A -15.8(3) . . . . ?
C9 C8 O2 B1 -159.14(19) . . . . ?
C7 C8 O2 B1 23.8(3) . . . . ?
N2B C8 O2 B1 19.3(7) . . . . ?
C8 O2 B1 F1 79.0(2) . . . . ?
C8 O2 B1 O1 -152.15(19) . . . . ?
C8 O2 B1 N2B -23.0(9) . . . . ?
C8 O2 B1 N1A -40.5(2) . . . . ?
C2 O1 B1 F1 -99.0(2) . . . . ?
C2 O1 B1 O2 131.7(2) . . . . ?
C2 O1 B1 N2B 30.6(11) . . . . ?
C2 O1 B1 N1A 15.2(2) . . . . ?
N2A N1A B1 F1 -86.1(3) . . . . ?
C1 N1A B1 F1 100.2(2) . . . . ?
N2A N1A B1 O2 35.9(3) . . . . ?
C1 N1A B1 O2 -137.77(18) . . . . ?
N2A N1A B1 O1 157.1(2) . . . . ?
C1 N1A B1 O1 -16.6(2) . . . . ?
C6 C1 N1B N2B -176.7(13) . . . . ?
C2 C1 N1B N2B 17(2) . . . . ?
C1 N1B N2B C7 -168.3(12) . . . . ?
C1 N1B N2B B1 4(2) . . . . ?
C1 N1B N2B C8 -130(4) . . . . ?
C12 C7 N2B N1B -35(3) . . . . ?
C8 C7 N2B N1B 156.1(16) . . . . ?
C12 C7 N2B B1 154.1(11) . . . . ?
C8 C7 N2B B1 -15.0(17) . . . . ?
C12 C7 N2B C8 169.0(19) . . . . ?
F1 B1 N2B N1B 103.8(16) . . . . ?
O2 B1 N2B N1B -145.1(17) . . . . ?
O1 B1 N2B N1B -29(2) . . . . ?
F1 B1 N2B C7 -85.4(18) . . . . ?
O2 B1 N2B C7 25.8(17) . . . . ?
O1 B1 N2B C7 142.3(14) . . . . ?
F1 B1 N2B C8 -96.4(6) . . . . ?
O2 B1 N2B C8 14.8(5) . . . . ?
O1 B1 N2B C8 131.2(7) . . . . ?
O2 C8 N2B N1B 123(4) . . . . ?
C9 C8 N2B N1B -64(6) . . . . ?
C7 C8 N2B N1B -52(4) . . . . ?
O2 C8 N2B C7 174.9(8) . . . . ?
C9 C8 N2B C7 -12(4) . . . . ?
O2 C8 N2B B1 -16.3(6) . . . . ?
C9 C8 N2B B1 157(3) . . . . ?
C7 C8 N2B B1 168.8(13) . . . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BAz-F
_database_code_depnum_ccdc_archive 'CCDC 2302563'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2023-10-21 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 B F3 N2 O2'
_chemical_formula_weight         278.00

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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'

_cell_length_a                   21.821(14)
_cell_length_b                   6.154(3)
_cell_length_c                   18.764(12)
_cell_angle_alpha                90
_cell_angle_beta                 120.182(8)
_cell_angle_gamma                90
_cell_volume                     2178(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3096
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8391
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2490
_reflns_number_gt                1196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   0.735
_refine_ls_restrained_S_all      0.735
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BAz-Br
_database_code_depnum_ccdc_archive 'CCDC 2339632'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 B Br2 F N2 O2'
_chemical_formula_weight         399.82

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.975(3)
_cell_length_b                   7.306(3)
_cell_length_c                   14.302(6)
_cell_angle_alpha                95.261(3)
_cell_angle_beta                 97.928(6)
_cell_angle_gamma                115.739(7)
_cell_volume                     640.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1939
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    6.337
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5189
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.141
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2802
_reflns_number_gt                2074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2802
_refine_ls_number_parameters     200
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.759
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.093



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BAz-Cl
_database_code_depnum_ccdc_archive 'CCDC 2302564'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2023-10-21 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 B Cl2 F N2 O2'
_chemical_formula_weight         310.90

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.084(4)
_cell_length_b                   7.205(5)
_cell_length_c                   13.827(7)
_cell_angle_alpha                96.26(3)
_cell_angle_beta                 97.76(5)
_cell_angle_gamma                116.43(2)
_cell_volume                     614.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5015
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2696
_reflns_number_gt                1707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2696
_refine_ls_number_parameters     227
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_preparation       Luminescent
