# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shenzhen_wss_3b_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2091170'
loop_
_audit_author_name
_audit_author_address
'Sisi Wang'
;Nanjing University
China
;
_audit_update_record             
;
2021-06-21 deposited with the CCDC.	2022-01-17 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            'C22 H21 B3 F6 N8'
_chemical_formula_weight         543.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 '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                   21.593(13)
_cell_length_b                   17.946(12)
_cell_length_c                   15.446(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.98(3)
_cell_angle_gamma                90
_cell_volume                     5510(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    199(2)
_cell_measurement_reflns_used    1816
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      43.11

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             2224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.600
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      199(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20895
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.886
_diffrn_reflns_theta_max         53.184
_diffrn_reflns_theta_full        53.184
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4889
_reflns_number_gt                1972
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 2014/5 (Sheldrick, 2014)'
_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)+(0.0800P)²+0.5000P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00092(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4889
_refine_ls_number_parameters     385
_refine_ls_number_restraints     324
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.008
_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
F1 F 0.38608(13) 0.66976(14) 0.85650(16) 0.1106(8) Uani 1 1 d . U . . .
B1 B 0.4229(3) 0.6556(3) 0.8037(3) 0.0833(13) Uani 1 1 d . U . . .
N1 N 0.39658(15) 0.69596(18) 0.7080(2) 0.0769(9) Uani 1 1 d . U . . .
C1 C 0.39481(19) 0.7725(2) 0.6935(3) 0.0806(11) Uani 1 1 d . U . . .
F2 F 0.49018(11) 0.66846(13) 0.85705(15) 0.1015(8) Uani 1 1 d . U . . .
B2 B 0.3168(3) 0.7641(3) 0.4223(4) 0.0831(13) Uani 1 1 d . U . . .
N2 N 0.34632(15) 0.74856(19) 0.5281(2) 0.0787(9) Uani 1 1 d . U . . .
C2 C 0.36891(19) 0.7990(2) 0.6020(3) 0.0802(11) Uani 1 1 d . U . . .
F3 F 0.26028(11) 0.80821(12) 0.39132(16) 0.0999(8) Uani 1 1 d . U . . .
N3 N 0.38131(14) 0.57542(18) 0.6631(2) 0.0741(8) Uani 1 1 d . U . . .
C3 C 0.3663(2) 0.8753(3) 0.5862(3) 0.0976(13) Uani 1 1 d . U . . .
H3 H 0.348814 0.893860 0.523626 0.117 Uiso 1 1 calc R U . . .
C4 C 0.3889(2) 0.9238(3) 0.6603(4) 0.1054(14) Uani 1 1 d . U . . .
H4 H 0.385922 0.975952 0.649138 0.126 Uiso 1 1 calc R U . . .
F4 F 0.36324(11) 0.79484(12) 0.39053(16) 0.0986(7) Uani 1 1 d . U . . .
N4 N 0.41156(16) 0.57568(19) 0.7624(2) 0.0847(9) Uani 1 1 d . U . . .
N5 N 0.32042(15) 0.63246(17) 0.4663(2) 0.0752(8) Uani 1 1 d . U . . .
C5 C 0.4158(2) 0.8973(3) 0.7507(4) 0.1039(14) Uani 1 1 d . U . . .
H5 H 0.432590 0.931440 0.801585 0.125 Uiso 1 1 calc R U . . .
N6 N 0.30069(15) 0.68234(17) 0.3905(2) 0.0783(9) Uani 1 1 d . U . . .
C6 C 0.4190(2) 0.8221(3) 0.7689(3) 0.0943(12) Uani 1 1 d . U . . .
H6 H 0.437331 0.804174 0.831787 0.113 Uiso 1 1 calc R U . . .
C7 C 0.37459(17) 0.6468(2) 0.6378(3) 0.0706(10) Uani 1 1 d . U . . .
N7 N 0.38833(17) 0.4329(2) 0.6742(3) 0.0913(10) Uani 1 1 d . U . . .
H7A H 0.374323 0.468129 0.631239 0.110 Uiso 0.299(5) 1 calc R U P A 2
C8 C 0.34678(18) 0.6743(2) 0.5428(3) 0.0723(10) Uani 1 1 d . U . . .
N8 N 0.26220(16) 0.5260(2) 0.3366(2) 0.0871(9) Uani 1 1 d . U . . .
H8A H 0.282998 0.528189 0.398175 0.105 Uiso 0.701(5) 1 calc R U P A 1
C9 C 0.4276(2) 0.5127(3) 0.8086(3) 0.0876(12) Uani 1 1 d . U . . .
H9 H 0.447845 0.515854 0.875196 0.105 Uiso 1 1 calc R U . . .
C10 C 0.4181(2) 0.4433(3) 0.7704(3) 0.0846(11) Uani 1 1 d . U . . .
C11 C 0.4333(2) 0.3737(3) 0.8156(3) 0.0893(12) Uani 1 1 d . U . . .
C12 C 0.4114(2) 0.3221(3) 0.7443(4) 0.1061(14) Uani 1 1 d . U . . .
H12 H 0.414004 0.269546 0.752083 0.127 Uiso 1 1 calc R U . . .
C13 C 0.3848(2) 0.3596(3) 0.6586(4) 0.1031(13) Uani 1 1 d . U . . .
C14 C 0.4668(2) 0.3621(3) 0.9191(3) 0.1030(14) Uani 1 1 d . U . . .
H14A H 0.469489 0.308642 0.932880 0.155 Uiso 1 1 calc R U . . .
H14B H 0.440662 0.386852 0.950334 0.155 Uiso 1 1 calc R U . . .
H14C H 0.512215 0.383241 0.942099 0.155 Uiso 1 1 calc R U . . .
C15 C 0.3559(3) 0.3254(3) 0.5618(4) 0.1365(19) Uani 1 1 d . U . . .
H15A H 0.364236 0.271571 0.566625 0.205 Uiso 1 1 calc R U . . .
H15B H 0.377456 0.347732 0.522705 0.205 Uiso 1 1 calc R U . . .
H15C H 0.307387 0.334676 0.533162 0.205 Uiso 1 1 calc R U . . .
C16 C 0.2698(2) 0.6579(3) 0.3042(3) 0.0854(11) Uani 1 1 d . U . . .
H16 H 0.258424 0.694457 0.255970 0.102 Uiso 1 1 calc R U . . .
C17 C 0.2519(2) 0.5852(3) 0.2748(3) 0.0852(11) Uani 1 1 d . U . . .
C18 C 0.2168(2) 0.5586(3) 0.1830(3) 0.1017(13) Uani 1 1 d . U . . .
C19 C 0.1946(3) 0.6043(3) 0.0957(3) 0.1340(19) Uani 1 1 d . U . . .
H19A H 0.161684 0.576139 0.043599 0.201 Uiso 1 1 calc R U . . .
H19B H 0.233528 0.616331 0.080635 0.201 Uiso 1 1 calc R U . . .
H19C H 0.173889 0.650507 0.105236 0.201 Uiso 1 1 calc R U . . .
C20 C 0.2073(3) 0.4840(3) 0.1920(4) 0.1148(16) Uani 1 1 d . U . . .
H20 H 0.185132 0.450913 0.141269 0.138 Uiso 1 1 calc R U . . .
C21 C 0.2345(2) 0.4640(3) 0.2853(4) 0.0991(13) Uani 1 1 d . U . . .
C22 C 0.2340(3) 0.3911(3) 0.3308(4) 0.1253(17) Uani 1 1 d . U . . .
H22A H 0.199945 0.358577 0.286149 0.188 Uiso 1 1 calc R U . . .
H22B H 0.223394 0.398945 0.386264 0.188 Uiso 1 1 calc R U . . .
H22C H 0.278363 0.367622 0.349895 0.188 Uiso 1 1 calc R U . . .
B3 B 0.3684(3) 0.5035(4) 0.6045(5) 0.0786(18) Uani 0.701(5) 1 d D U P A 1
F5 F 0.3016(2) 0.4978(2) 0.5437(3) 0.0914(13) Uani 0.701(5) 1 d D U P A 1
F6 F 0.4081(2) 0.50344(17) 0.5521(3) 0.0933(13) Uani 0.701(5) 1 d D U P A 1
B3A B 0.3057(6) 0.5413(9) 0.4492(11) 0.079(3) Uani 0.299(5) 1 d D U P A 2
F5A F 0.2671(6) 0.5178(6) 0.4975(8) 0.098(3) Uani 0.299(5) 1 d D U P A 2
F6A F 0.3662(5) 0.5037(4) 0.4790(7) 0.094(3) Uani 0.299(5) 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
F1 B1 1.366(5) . ?
B1 F2 1.381(5) . ?
B1 N1 1.541(6) . ?
B1 N4 1.551(6) . ?
N1 C7 1.333(4) . ?
N1 C1 1.390(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.395(5) . ?
B2 F3 1.375(5) . ?
B2 F4 1.392(5) . ?
B2 N2 1.530(6) . ?
B2 N6 1.543(6) . ?
N2 C8 1.351(5) . ?
N2 C2 1.387(5) . ?
C2 C3 1.388(5) . ?
N3 C7 1.331(5) . ?
N3 N4 1.413(4) . ?
N3 B3 1.539(7) . ?
C3 C4 1.368(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9500 . ?
N4 C9 1.308(5) . ?
N5 C8 1.327(4) . ?
N5 N6 1.401(4) . ?
N5 B3A 1.668(16) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
N6 C16 1.311(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.438(5) . ?
N7 C13 1.335(6) . ?
N7 C10 1.382(5) . ?
N7 B3 1.609(7) . ?
N7 H7A 0.8800 . ?
N8 C21 1.362(5) . ?
N8 C17 1.386(5) . ?
N8 B3A 1.646(16) . ?
N8 H8A 0.8800 . ?
C9 C10 1.359(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(6) . ?
C11 C12 1.375(6) . ?
C11 C14 1.489(6) . ?
C12 C13 1.392(6) . ?
C12 H12 0.9500 . ?
C13 C15 1.508(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.386(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(6) . ?
C18 C20 1.371(6) . ?
C18 C19 1.489(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.487(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B3 F5 1.384(7) . ?
B3 F6 1.389(7) . ?
B3A F6A 1.381(12) . ?
B3A F5A 1.382(12) . ?

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
F1 B1 F2 109.6(4) . . ?
F1 B1 N1 113.8(4) . . ?
F2 B1 N1 113.7(4) . . ?
F1 B1 N4 112.5(4) . . ?
F2 B1 N4 111.1(4) . . ?
N1 B1 N4 95.7(3) . . ?
C7 N1 C1 122.9(3) . . ?
C7 N1 B1 110.5(3) . . ?
C1 N1 B1 126.6(3) . . ?
C2 C1 N1 118.6(4) . . ?
C2 C1 C6 120.2(4) . . ?
N1 C1 C6 121.2(4) . . ?
F3 B2 F4 108.2(4) . . ?
F3 B2 N2 114.8(4) . . ?
F4 B2 N2 113.1(4) . . ?
F3 B2 N6 112.2(4) . . ?
F4 B2 N6 111.6(4) . . ?
N2 B2 N6 96.6(3) . . ?
C8 N2 C2 121.9(3) . . ?
C8 N2 B2 109.4(3) . . ?
C2 N2 B2 128.8(4) . . ?
C1 C2 N2 119.2(4) . . ?
C1 C2 C3 119.4(4) . . ?
N2 C2 C3 121.4(4) . . ?
C7 N3 N4 105.5(3) . . ?
C7 N3 B3 131.3(4) . . ?
N4 N3 B3 122.9(4) . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C9 N4 N3 120.0(4) . . ?
C9 N4 B1 127.5(4) . . ?
N3 N4 B1 112.4(3) . . ?
C8 N5 N6 105.5(3) . . ?
C8 N5 B3A 133.2(6) . . ?
N6 N5 B3A 121.2(6) . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C16 N6 N5 120.2(3) . . ?
C16 N6 B2 127.1(4) . . ?
N5 N6 B2 112.6(3) . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N3 C7 N1 115.7(3) . . ?
N3 C7 C8 125.7(4) . . ?
N1 C7 C8 118.6(4) . . ?
C13 N7 C10 107.2(4) . . ?
C13 N7 B3 132.4(4) . . ?
C10 N7 B3 120.3(4) . . ?
C13 N7 H7A 126.4 . . ?
C10 N7 H7A 126.4 . . ?
N5 C8 N2 115.9(3) . . ?
N5 C8 C7 125.3(4) . . ?
N2 C8 C7 118.8(4) . . ?
C21 N8 C17 108.1(4) . . ?
C21 N8 B3A 133.6(7) . . ?
C17 N8 B3A 118.2(6) . . ?
C21 N8 H8A 126.0 . . ?
C17 N8 H8A 126.0 . . ?
N4 C9 C10 126.4(4) . . ?
N4 C9 H9 116.8 . . ?
C10 C9 H9 116.8 . . ?
C9 C10 N7 121.1(4) . . ?
C9 C10 C11 129.3(4) . . ?
N7 C10 C11 109.6(4) . . ?
C12 C11 C10 105.1(4) . . ?
C12 C11 C14 129.6(4) . . ?
C10 C11 C14 125.4(4) . . ?
C11 C12 C13 108.7(5) . . ?
C11 C12 H12 125.6 . . ?
C13 C12 H12 125.6 . . ?
N7 C13 C12 109.4(5) . . ?
N7 C13 C15 123.5(5) . . ?
C12 C13 C15 127.1(5) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C16 C17 127.8(4) . . ?
N6 C16 H16 116.1 . . ?
C17 C16 H16 116.1 . . ?
C16 C17 N8 123.2(4) . . ?
C16 C17 C18 128.4(4) . . ?
N8 C17 C18 108.2(4) . . ?
C20 C18 C17 105.8(4) . . ?
C20 C18 C19 128.5(5) . . ?
C17 C18 C19 125.7(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 110.0(5) . . ?
C18 C20 H20 125.0 . . ?
C21 C20 H20 125.0 . . ?
N8 C21 C20 107.9(5) . . ?
N8 C21 C22 121.9(5) . . ?
C20 C21 C22 130.2(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F5 B3 F6 108.8(5) . . ?
F5 B3 N3 111.2(5) . . ?
F6 B3 N3 109.4(5) . . ?
F5 B3 N7 109.4(5) . . ?
F6 B3 N7 109.0(5) . . ?
N3 B3 N7 109.0(4) . . ?
F6A B3A F5A 111.3(12) . . ?
F6A B3A N8 110.2(10) . . ?
F5A B3A N8 107.7(10) . . ?
F6A B3A N5 109.2(9) . . ?
F5A B3A N5 109.4(10) . . ?
N8 B3A N5 109.0(9) . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_20200522li_shenzhen_4B_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2091171'
loop_
_audit_author_name
_audit_author_address
'Sisi Wang'
;Nanjing University
China
;
_audit_update_record             
;
2021-06-21 deposited with the CCDC.	2022-01-17 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            'C22 H20 B4 F6 N8 O'
_chemical_formula_weight         569.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.3897(2)
_cell_length_b                   21.0157(6)
_cell_length_c                   13.7432(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.3310(10)
_cell_angle_gamma                90
_cell_volume                     2383.85(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      53.79

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18845
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         53.879
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4316
_reflns_number_gt                3793
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.0517P)²+0.8755P] 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         4316
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
B4 B 0.4181(2) 0.52167(9) 0.25390(14) 0.0314(4) Uani 1 1 d . . . . .
B3 B 0.5407(2) 0.60323(9) 0.15858(14) 0.0319(4) Uani 1 1 d . . . . .
B1 B 0.0625(2) 0.59571(9) 0.37180(15) 0.0324(4) Uani 1 1 d . . . . .
B2 B 0.4883(2) 0.78383(9) 0.23832(16) 0.0342(4) Uani 1 1 d . . . . .
C1 C 0.12564(19) 0.71836(8) 0.35007(12) 0.0307(3) Uani 1 1 d . . . . .
C2 C -0.0059(2) 0.73811(9) 0.39107(14) 0.0369(4) Uani 1 1 d . . . . .
H2 H -0.078058 0.707671 0.410269 0.044 Uiso 1 1 calc R U . . .
C3 C -0.0310(2) 0.80217(9) 0.40368(14) 0.0396(4) Uani 1 1 d . . . . .
H3 H -0.120375 0.815815 0.432090 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0736(2) 0.84702(8) 0.37514(14) 0.0388(4) Uani 1 1 d . . . . .
H4 H 0.055323 0.891042 0.384392 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2039(2) 0.82798(8) 0.33347(14) 0.0361(4) Uani 1 1 d . . . . .
H5 H 0.274831 0.858681 0.313705 0.043 Uiso 1 1 calc R U . . .
C6 C 0.23017(18) 0.76335(8) 0.32071(12) 0.0301(3) Uani 1 1 d . . . . .
C7 C 0.28228(18) 0.63294(8) 0.29756(12) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.38351(18) 0.68011(7) 0.26036(12) 0.0283(3) Uani 1 1 d . . . . .
C9 C 0.71022(19) 0.72730(8) 0.15849(12) 0.0328(4) Uani 1 1 d . . . . .
H9 H 0.761409 0.767076 0.152528 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7786(2) 0.67431(8) 0.12528(13) 0.0323(4) Uani 1 1 d . . . . .
C11 C 0.9242(2) 0.66741(9) 0.08638(13) 0.0373(4) Uani 1 1 d . . . . .
C12 C 0.9349(2) 0.60393(9) 0.06529(14) 0.0419(4) Uani 1 1 d . . . . .
H12 H 1.020693 0.584366 0.039623 0.050 Uiso 1 1 calc R U . . .
C13 C 0.7982(2) 0.57257(9) 0.08788(13) 0.0381(4) Uani 1 1 d . . . . .
C14 C 0.7556(3) 0.50439(9) 0.07032(16) 0.0470(5) Uani 1 1 d . . . . .
H14A H 0.653113 0.495446 0.092378 0.071 Uiso 1 1 calc R U . . .
H14B H 0.841481 0.477768 0.107439 0.071 Uiso 1 1 calc R U . . .
H14C H 0.744216 0.494998 -0.000437 0.071 Uiso 1 1 calc R U . . .
C15 C 1.0362(2) 0.71926(9) 0.06889(15) 0.0426(4) Uani 1 1 d . . . . .
H15A H 1.144090 0.701505 0.068461 0.064 Uiso 1 1 calc R U . . .
H15B H 1.042903 0.751012 0.121690 0.064 Uiso 1 1 calc R U . . .
H15C H 0.995488 0.739446 0.004983 0.064 Uiso 1 1 calc R U . . .
C16 C 0.22036(19) 0.48987(8) 0.39882(13) 0.0330(4) Uani 1 1 d . . . . .
H16 H 0.143929 0.473633 0.435788 0.040 Uiso 1 1 calc R U . . .
C17 C 0.35930(19) 0.45501(8) 0.39815(13) 0.0319(4) Uani 1 1 d . . . . .
C18 C 0.4223(2) 0.40266(8) 0.45706(13) 0.0325(4) Uani 1 1 d . . . . .
C19 C 0.3387(2) 0.37010(9) 0.53114(14) 0.0373(4) Uani 1 1 d . . . . .
H19A H 0.397393 0.331050 0.554258 0.056 Uiso 1 1 calc R U . . .
H19B H 0.227485 0.359432 0.500109 0.056 Uiso 1 1 calc R U . . .
H19C H 0.336760 0.398536 0.587419 0.056 Uiso 1 1 calc R U . . .
C20 C 0.5713(2) 0.39084(8) 0.43388(13) 0.0346(4) Uani 1 1 d . . . . .
H20 H 0.644228 0.358540 0.462399 0.041 Uiso 1 1 calc R U . . .
C21 C 0.59919(19) 0.43442(8) 0.36074(13) 0.0321(4) Uani 1 1 d . . . . .
C22 C 0.7436(2) 0.43729(9) 0.31139(14) 0.0376(4) Uani 1 1 d . . . . .
H22A H 0.716729 0.418219 0.245408 0.056 Uiso 1 1 calc R U . . .
H22B H 0.833360 0.413762 0.350950 0.056 Uiso 1 1 calc R U . . .
H22C H 0.775538 0.481771 0.305398 0.056 Uiso 1 1 calc R U . . .
F1 F 0.42190(13) 0.82441(5) 0.16441(9) 0.0508(3) Uani 1 1 d . . . . .
F2 F 0.58526(12) 0.81585(5) 0.31310(9) 0.0489(3) Uani 1 1 d . . . . .
F3 F -0.08725(11) 0.58963(5) 0.31484(8) 0.0408(3) Uani 1 1 d . . . . .
F4 F 0.05173(12) 0.59725(5) 0.47057(8) 0.0404(3) Uani 1 1 d . . . . .
F5 F 0.41634(12) 0.59955(5) 0.07664(7) 0.0406(3) Uani 1 1 d . . . . .
F6 F 0.31215(12) 0.49022(5) 0.17930(8) 0.0399(2) Uani 1 1 d . . . . .
N1 N 0.35883(15) 0.74184(6) 0.27701(10) 0.0297(3) Uani 1 1 d . . . . .
N2 N 0.15811(15) 0.65386(6) 0.33840(10) 0.0303(3) Uani 1 1 d . . . . .
N3 N 0.18591(16) 0.54465(6) 0.35129(11) 0.0327(3) Uani 1 1 d . . . . .
N4 N 0.47120(16) 0.47357(6) 0.33958(10) 0.0310(3) Uani 1 1 d . . . . .
N5 N 0.30345(15) 0.57042(7) 0.30139(10) 0.0309(3) Uani 1 1 d . . . . .
N6 N 0.50659(16) 0.66853(6) 0.21390(10) 0.0309(3) Uani 1 1 d . . . . .
N7 N 0.57733(16) 0.72712(6) 0.19848(11) 0.0328(3) Uani 1 1 d . . . . .
N8 N 0.70488(17) 0.61478(7) 0.12511(10) 0.0327(3) Uani 1 1 d . . . . .
O1 O 0.54781(13) 0.55306(5) 0.22582(9) 0.0333(3) 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
B4 O1 1.385(2) . ?
B4 F6 1.397(2) . ?
B4 N4 1.555(2) . ?
B4 N5 1.621(2) . ?
B3 F5 1.393(2) . ?
B3 O1 1.396(2) . ?
B3 N8 1.548(2) . ?
B3 N6 1.619(2) . ?
B1 F3 1.362(2) . ?
B1 F4 1.377(2) . ?
B1 N3 1.552(2) . ?
B1 N2 1.575(2) . ?
B2 F1 1.366(2) . ?
B2 F2 1.368(2) . ?
B2 N7 1.557(2) . ?
B2 N1 1.565(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
C1 N2 1.398(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.401(2) . ?
C7 N5 1.326(2) . ?
C7 N2 1.3429(19) . ?
C7 C8 1.456(2) . ?
C8 N6 1.330(2) . ?
C8 N1 1.340(2) . ?
C9 N7 1.328(2) . ?
C9 C10 1.368(2) . ?
C9 H9 0.9500 . ?
C10 N8 1.396(2) . ?
C10 C11 1.425(2) . ?
C11 C12 1.372(3) . ?
C11 C15 1.486(2) . ?
C12 C13 1.405(2) . ?
C12 H12 0.9500 . ?
C13 N8 1.343(2) . ?
C13 C14 1.486(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N3 1.330(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9500 . ?
C17 N4 1.397(2) . ?
C17 C18 1.411(2) . ?
C18 C20 1.368(2) . ?
C18 C19 1.501(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.410(2) . ?
C20 H20 0.9500 . ?
C21 N4 1.343(2) . ?
C21 C22 1.492(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N3 N5 1.4067(17) . ?
N6 N7 1.3994(18) . ?

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
O1 B4 F6 116.69(15) . . ?
O1 B4 N4 112.83(14) . . ?
F6 B4 N4 107.83(13) . . ?
O1 B4 N5 111.34(13) . . ?
F6 B4 N5 104.42(13) . . ?
N4 B4 N5 102.47(13) . . ?
F5 B3 O1 115.48(15) . . ?
F5 B3 N8 110.23(14) . . ?
O1 B3 N8 112.34(14) . . ?
F5 B3 N6 104.90(13) . . ?
O1 B3 N6 108.64(14) . . ?
N8 B3 N6 104.37(13) . . ?
F3 B1 F4 110.61(14) . . ?
F3 B1 N3 114.05(15) . . ?
F4 B1 N3 111.05(14) . . ?
F3 B1 N2 111.78(14) . . ?
F4 B1 N2 113.33(15) . . ?
N3 B1 N2 95.29(12) . . ?
F1 B2 F2 111.08(15) . . ?
F1 B2 N7 111.95(15) . . ?
F2 B2 N7 112.52(14) . . ?
F1 B2 N1 112.89(14) . . ?
F2 B2 N1 112.18(15) . . ?
N7 B2 N1 95.39(12) . . ?
C2 C1 C6 120.02(15) . . ?
C2 C1 N2 121.44(15) . . ?
C6 C1 N2 118.54(14) . . ?
C3 C2 C1 119.53(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.54(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.44(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.35(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.12(15) . . ?
C5 C6 N1 121.37(15) . . ?
C1 C6 N1 118.50(14) . . ?
N5 C7 N2 114.60(14) . . ?
N5 C7 C8 127.32(14) . . ?
N2 C7 C8 117.96(14) . . ?
N6 C8 N1 114.59(14) . . ?
N6 C8 C7 126.56(14) . . ?
N1 C8 C7 118.77(14) . . ?
N7 C9 C10 124.69(15) . . ?
N7 C9 H9 117.7 . . ?
C10 C9 H9 117.7 . . ?
C9 C10 N8 121.18(14) . . ?
C9 C10 C11 130.30(16) . . ?
N8 C10 C11 108.51(15) . . ?
C12 C11 C10 105.74(15) . . ?
C12 C11 C15 127.70(16) . . ?
C10 C11 C15 126.52(17) . . ?
C11 C12 C13 108.80(15) . . ?
C11 C12 H12 125.6 . . ?
C13 C12 H12 125.6 . . ?
N8 C13 C12 109.21(16) . . ?
N8 C13 C14 124.00(16) . . ?
C12 C13 C14 126.74(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 124.51(15) . . ?
N3 C16 H16 117.7 . . ?
C17 C16 H16 117.7 . . ?
C16 C17 N4 120.80(15) . . ?
C16 C17 C18 129.83(15) . . ?
N4 C17 C18 109.08(14) . . ?
C20 C18 C17 105.77(14) . . ?
C20 C18 C19 129.28(16) . . ?
C17 C18 C19 124.92(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 108.88(15) . . ?
C18 C20 H20 125.6 . . ?
C21 C20 H20 125.6 . . ?
N4 C21 C20 108.91(14) . . ?
N4 C21 C22 124.05(15) . . ?
C20 C21 C22 127.03(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C6 122.70(13) . . ?
C8 N1 B2 110.48(13) . . ?
C6 N1 B2 126.80(13) . . ?
C7 N2 C1 123.18(13) . . ?
C7 N2 B1 109.99(13) . . ?
C1 N2 B1 126.82(13) . . ?
C16 N3 N5 117.59(13) . . ?
C16 N3 B1 127.08(14) . . ?
N5 N3 B1 111.80(12) . . ?
C21 N4 C17 107.35(14) . . ?
C21 N4 B4 132.18(14) . . ?
C17 N4 B4 119.13(13) . . ?
C7 N5 N3 107.48(12) . . ?
C7 N5 B4 134.07(13) . . ?
N3 N5 B4 118.15(12) . . ?
C8 N6 N7 107.37(13) . . ?
C8 N6 B3 126.73(13) . . ?
N7 N6 B3 124.01(12) . . ?
C9 N7 N6 118.38(14) . . ?
C9 N7 B2 129.36(14) . . ?
N6 N7 B2 112.15(12) . . ?
C13 N8 C10 107.70(14) . . ?
C13 N8 B3 128.32(15) . . ?
C10 N8 B3 123.92(13) . . ?
B4 O1 B3 126.97(14) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2091172'
loop_
_audit_author_name
_audit_author_address
'Sisi Wang'
;Nanjing University
China
;
_audit_update_record             
;
2021-06-21 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_sum            'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_weight         727.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   12.6730(10)
_cell_length_b                   24.2903(19)
_cell_length_c                   8.7967(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.285(5)
_cell_angle_gamma                90
_cell_volume                     2585.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      60.221
_cell_measurement_theta_min      3.166
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    3.099
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9672
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.605
_diffrn_reflns_theta_min         3.166
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993134
_diffrn_source_voltage           69.69
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2301
_reflns_number_total             2873
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+3.9192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C1(H1)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.67897(3) 0.96762(2) 0.78099(4) 0.03723(12) Uani 1 1 d . . . . .
F1 F 0.75030(13) 0.63013(7) 0.61055(19) 0.0359(4) Uani 1 1 d . . . . .
F2 F 0.59304(14) 0.62848(7) 0.67936(18) 0.0354(4) Uani 1 1 d . . . . .
F3 F 0.40658(13) 0.78260(7) 0.4253(2) 0.0420(4) Uani 1 1 d . . . . .
O1 O 0.500000 0.81333(11) 0.250000 0.0420(8) Uani 1 2 d S T P . .
N2 N 0.63835(17) 0.71383(9) 0.5686(2) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.57483(17) 0.63995(8) 0.3992(2) 0.0230(4) Uani 1 1 d . . . . .
N3 N 0.56892(17) 0.73249(8) 0.4221(2) 0.0241(5) Uani 1 1 d . . . . .
N4 N 0.58028(17) 0.82724(9) 0.5367(2) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.5369(2) 0.68810(10) 0.3314(3) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.5400(2) 0.58963(10) 0.3243(3) 0.0239(5) Uani 1 1 d . . . . .
C6 C 0.6603(2) 0.80557(11) 0.6690(3) 0.0242(5) Uani 1 1 d . . . . .
C7 C 0.7057(2) 0.84892(11) 0.7762(3) 0.0259(6) Uani 1 1 d . . . . .
C2 C 0.5812(2) 0.54002(11) 0.3968(3) 0.0297(6) Uani 1 1 d . . . . .
H2 H 0.636816 0.539827 0.496895 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6822(2) 0.75014(11) 0.6815(3) 0.0255(6) Uani 1 1 d . . . . .
H5 H 0.732162 0.736998 0.777809 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6520(2) 0.89527(11) 0.7043(3) 0.0267(6) Uani 1 1 d . . . . .
C11 C 0.4931(2) 0.91901(11) 0.4477(3) 0.0312(6) Uani 1 1 d . . . . .
H11A H 0.533089 0.943895 0.396498 0.047 Uiso 1 1 calc R U . . .
H11B H 0.453442 0.940621 0.507355 0.047 Uiso 1 1 calc R U . . .
H11C H 0.440198 0.897127 0.366259 0.047 Uiso 1 1 calc R U . . .
C1 C 0.5411(2) 0.49129(11) 0.3227(3) 0.0334(6) Uani 1 1 d . . . . .
H1 H 0.569681 0.457338 0.371379 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7915(2) 0.84501(12) 0.9341(3) 0.0315(6) Uani 1 1 d . . . . .
H8A H 0.758763 0.854697 1.018356 0.047 Uiso 1 1 calc R U . . .
H8B H 0.852090 0.870466 0.936983 0.047 Uiso 1 1 calc R U . . .
H8C H 0.820150 0.807303 0.950618 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5731(2) 0.88165(11) 0.5586(3) 0.0252(5) Uani 1 1 d . . . . .
B2 B 0.5087(3) 0.79158(12) 0.3978(4) 0.0266(6) Uani 1 1 d . . . . .
B1 B 0.6453(2) 0.64921(12) 0.5772(3) 0.0249(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
Br1 C9 1.877(3) . ?
F1 B1 1.357(3) . ?
F2 B1 1.361(3) . ?
F3 B2 1.402(4) . ?
O1 B2 1.377(3) . ?
O1 B2 1.377(3) 2_655 ?
N2 N3 1.403(3) . ?
N2 C5 1.320(3) . ?
N2 B1 1.573(4) . ?
N1 C4 1.336(3) . ?
N1 C3 1.397(3) . ?
N1 B1 1.571(3) . ?
N3 C4 1.331(3) . ?
N3 B2 1.610(4) . ?
N4 C6 1.400(3) . ?
N4 C10 1.343(3) . ?
N4 B2 1.551(3) . ?
C4 C4 1.460(5) 2_655 ?
C3 C3 1.396(5) 2_655 ?
C3 C2 1.391(3) . ?
C6 C7 1.417(3) . ?
C6 C5 1.372(4) . ?
C7 C9 1.369(4) . ?
C7 C8 1.491(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.374(4) . ?
C5 H5 0.9500 . ?
C9 C10 1.411(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.488(4) . ?
C1 C1 1.389(6) 2_655 ?
C1 H1 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
B2 O1 B2 134.9(3) 2_655 . ?
N3 N2 B1 112.15(19) . . ?
C5 N2 N3 118.9(2) . . ?
C5 N2 B1 128.7(2) . . ?
C4 N1 C3 122.3(2) . . ?
C4 N1 B1 110.0(2) . . ?
C3 N1 B1 127.0(2) . . ?
N2 N3 B2 123.6(2) . . ?
C4 N3 N2 106.57(19) . . ?
C4 N3 B2 126.5(2) . . ?
C6 N4 B2 123.7(2) . . ?
C10 N4 C6 108.3(2) . . ?
C10 N4 B2 127.9(2) . . ?
N1 C4 C4 118.60(13) . 2_655 ?
N3 C4 N1 115.9(2) . . ?
N3 C4 C4 125.47(14) . 2_655 ?
C3 C3 N1 118.79(13) 2_655 . ?
C2 C3 N1 121.3(2) . . ?
C2 C3 C3 119.93(16) . 2_655 ?
N4 C6 C7 108.9(2) . . ?
C5 C6 N4 121.0(2) . . ?
C5 C6 C7 130.1(2) . . ?
C6 C7 C8 127.8(2) . . ?
C9 C7 C6 104.8(2) . . ?
C9 C7 C8 127.4(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
N2 C5 C6 124.4(2) . . ?
N2 C5 H5 117.8 . . ?
C6 C5 H5 117.8 . . ?
C7 C9 Br1 126.3(2) . . ?
C7 C9 C10 110.3(2) . . ?
C10 C9 Br1 123.4(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C2 C1 C1 120.51(16) . 2_655 ?
C2 C1 H1 119.7 . . ?
C1 C1 H1 119.7 2_655 . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C10 C9 107.5(2) . . ?
N4 C10 C11 124.6(2) . . ?
C9 C10 C11 127.8(2) . . ?
F3 B2 N3 105.3(2) . . ?
F3 B2 N4 107.7(2) . . ?
O1 B2 F3 113.8(2) . . ?
O1 B2 N3 111.6(2) . . ?
O1 B2 N4 113.1(2) . . ?
N4 B2 N3 104.48(19) . . ?
F1 B1 F2 111.7(2) . . ?
F1 B1 N2 112.9(2) . . ?
F1 B1 N1 113.4(2) . . ?
F2 B1 N2 111.7(2) . . ?
F2 B1 N1 111.2(2) . . ?
N1 B1 N2 95.07(19) . . ?

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
Br1 C9 C10 N4 176.34(19) . . . . ?
Br1 C9 C10 C11 -4.9(4) . . . . ?
N2 N3 C4 N1 1.1(3) . . . . ?
N2 N3 C4 C4 179.6(3) . . . 2_655 ?
N2 N3 B2 F3 -90.3(3) . . . . ?
N2 N3 B2 O1 145.7(2) . . . . ?
N2 N3 B2 N4 23.1(3) . . . . ?
N1 C3 C2 C1 176.9(2) . . . . ?
N3 N2 C5 C6 3.4(4) . . . . ?
N3 N2 B1 F1 123.4(2) . . . . ?
N3 N2 B1 F2 -109.8(2) . . . . ?
N3 N2 B1 N1 5.4(3) . . . . ?
N4 C6 C7 C9 -0.5(3) . . . . ?
N4 C6 C7 C8 178.6(2) . . . . ?
N4 C6 C5 N2 5.7(4) . . . . ?
C4 N1 C3 C3 -2.2(4) . . . 2_655 ?
C4 N1 C3 C2 179.6(2) . . . . ?
C4 N1 B1 F1 -122.2(2) . . . . ?
C4 N1 B1 F2 111.0(2) . . . . ?
C4 N1 B1 N2 -4.6(3) . . . . ?
C4 N3 B2 F3 66.2(3) . . . . ?
C4 N3 B2 O1 -57.8(3) . . . . ?
C4 N3 B2 N4 179.6(2) . . . . ?
C3 N1 C4 N3 173.8(2) . . . . ?
C3 N1 C4 C4 -4.9(4) . . . 2_655 ?
C3 N1 B1 F1 67.2(3) . . . . ?
C3 N1 B1 F2 -59.6(3) . . . . ?
C3 N1 B1 N2 -175.2(2) . . . . ?
C3 C3 C2 C1 -1.3(5) 2_655 . . . ?
C3 C2 C1 C1 -0.7(5) . . . 2_655 ?
C6 N4 C10 C9 1.9(3) . . . . ?
C6 N4 C10 C11 -176.8(2) . . . . ?
C6 N4 B2 F3 97.7(3) . . . . ?
C6 N4 B2 O1 -135.5(2) . . . . ?
C6 N4 B2 N3 -13.9(3) . . . . ?
C6 C7 C9 Br1 -176.94(19) . . . . ?
C6 C7 C9 C10 1.7(3) . . . . ?
C7 C6 C5 N2 -176.2(3) . . . . ?
C7 C9 C10 N4 -2.3(3) . . . . ?
C7 C9 C10 C11 176.4(3) . . . . ?
C5 N2 N3 C4 179.9(2) . . . . ?
C5 N2 N3 B2 -19.7(3) . . . . ?
C5 N2 B1 F1 -61.4(4) . . . . ?
C5 N2 B1 F2 65.4(3) . . . . ?
C5 N2 B1 N1 -179.5(2) . . . . ?
C5 C6 C7 C9 -178.7(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C8 C7 C9 Br1 4.0(4) . . . . ?
C8 C7 C9 C10 -177.4(3) . . . . ?
C10 N4 C6 C7 -0.9(3) . . . . ?
C10 N4 C6 C5 177.5(2) . . . . ?
C10 N4 B2 F3 -77.4(3) . . . . ?
C10 N4 B2 O1 49.4(4) . . . . ?
C10 N4 B2 N3 171.0(2) . . . . ?
B2 O1 B2 F3 -90.0(2) 2_655 . . . ?
B2 O1 B2 N3 29.09(15) 2_655 . . . ?
B2 O1 B2 N4 146.6(2) 2_655 . . . ?
B2 N3 C4 N1 -158.7(2) . . . . ?
B2 N3 C4 C4 19.9(5) . . . 2_655 ?
B2 N4 C6 C7 -176.9(2) . . . . ?
B2 N4 C6 C5 1.6(4) . . . . ?
B2 N4 C10 C9 177.6(2) . . . . ?
B2 N4 C10 C11 -1.1(4) . . . . ?
B1 N2 N3 C4 -4.4(3) . . . . ?
B1 N2 N3 B2 156.0(2) . . . . ?
B1 N2 C5 C6 -171.5(3) . . . . ?
B1 N1 C4 N3 2.7(3) . . . . ?
B1 N1 C4 C4 -176.0(3) . . . 2_655 ?
B1 N1 C3 C3 167.3(3) . . . 2_655 ?
B1 N1 C3 C2 -10.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2091174'
loop_
_audit_author_name
_audit_author_address
'Sisi Wang'
;Nanjing University
China
;
_audit_update_record             
;
2021-06-21 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_sum            'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_weight         727.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2437(8)
_cell_length_b                   12.7062(10)
_cell_length_c                   13.7867(10)
_cell_angle_alpha                107.288(2)
_cell_angle_beta                 98.865(3)
_cell_angle_gamma                96.501(3)
_cell_volume                     1505.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6615
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.489
_shelx_estimated_absorpt_T_max   0.770
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0905 before and 0.0697 after correction.
The Ratio of minimum to maximum transmission is 0.7570.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13774
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.915
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5680
_reflns_number_total             6792
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.040
_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)+(0.0407P)²+0.9211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.65775(4) 0.31820(3) -0.11485(2) 0.04239(10) Uani 1 1 d . . . . .
Br2 Br 0.75220(4) -0.10994(3) 0.36791(3) 0.04926(11) Uani 1 1 d . . . . .
F1 F 0.2128(2) 0.15748(13) 0.10722(12) 0.0344(4) Uani 1 1 d . . . . .
F2 F 0.25324(18) 0.12486(13) 0.30378(12) 0.0300(3) Uani 1 1 d . . . . .
F3 F 0.0833(2) 0.57611(15) 0.19965(14) 0.0416(4) Uani 1 1 d . . . . .
F4 F -0.08356(19) 0.43208(17) 0.20075(13) 0.0417(4) Uani 1 1 d . . . . .
F5 F 0.27230(17) 0.37199(13) 0.63786(11) 0.0281(3) Uani 1 1 d . . . . .
F6 F 0.48581(18) 0.49115(13) 0.66475(11) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.4278(2) 0.22313(14) 0.23963(13) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.3983(3) 0.29164(17) 0.08914(15) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.1548(2) 0.39282(19) 0.15600(16) 0.0260(5) Uani 1 1 d . . . . .
N3 N 0.2406(2) 0.34528(18) 0.22019(15) 0.0225(4) Uani 1 1 d . . . . .
N4 N 0.1482(2) 0.47995(18) 0.32742(16) 0.0218(4) Uani 1 1 d . . . . .
N5 N 0.3017(2) 0.45448(17) 0.50297(15) 0.0208(4) Uani 1 1 d . . . . .
N6 N 0.3868(2) 0.30305(17) 0.41594(15) 0.0211(4) Uani 1 1 d . . . . .
N7 N 0.4407(2) 0.31908(17) 0.52040(15) 0.0223(4) Uani 1 1 d . . . . .
N8 N 0.5127(2) 0.13680(17) 0.37034(16) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.6354(3) 0.2103(2) 0.0817(2) 0.0330(6) Uani 1 1 d . . . . .
H1A H 0.628656 0.207337 0.149646 0.049 Uiso 1 1 calc R U . . .
H1B H 0.731731 0.249062 0.083610 0.049 Uiso 1 1 calc R U . . .
H1C H 0.620866 0.135662 0.034159 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5168(3) 0.2717(2) 0.04636(19) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.5084(3) 0.3151(2) -0.0373(2) 0.0301(6) Uani 1 1 d . . . . .
C4 C 0.3819(3) 0.3601(2) -0.04821(19) 0.0295(6) Uani 1 1 d . . . . .
C5 C 0.3269(4) 0.4134(3) -0.1263(2) 0.0400(7) Uani 1 1 d . . . . .
H5A H 0.409852 0.452791 -0.142630 0.060 Uiso 1 1 calc R U . . .
H5B H 0.263953 0.465054 -0.098492 0.060 Uiso 1 1 calc R U . . .
H5C H 0.271580 0.356893 -0.188012 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3134(3) 0.3472(2) 0.03341(19) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.1952(3) 0.3912(2) 0.06739(19) 0.0275(5) Uani 1 1 d . . . . .
H7 H 0.138660 0.422635 0.025051 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2333(3) 0.4000(2) 0.31716(18) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.3089(3) 0.3834(2) 0.41110(17) 0.0194(5) Uani 1 1 d . . . . .
C10 C 0.1400(3) 0.5534(2) 0.42328(19) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.2208(3) 0.5423(2) 0.51321(19) 0.0215(5) Uani 1 1 d . . . . .
C12 C 0.2179(3) 0.6156(2) 0.6099(2) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.272080 0.608185 0.669542 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1336(3) 0.6997(2) 0.6167(2) 0.0335(6) Uani 1 1 d . . . . .
H13 H 0.131452 0.749557 0.681194 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0518(3) 0.7100(2) 0.5274(2) 0.0326(6) Uani 1 1 d . . . . .
H14 H -0.005661 0.766285 0.532990 0.039 Uiso 1 1 calc R U . . .
C15 C 0.0543(3) 0.6388(2) 0.4314(2) 0.0288(6) Uani 1 1 d . . . . .
H15 H -0.000188 0.646910 0.372210 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5315(3) 0.2548(2) 0.54616(19) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.570178 0.269602 0.616162 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5728(3) 0.1670(2) 0.47601(19) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.6670(3) 0.0913(2) 0.4933(2) 0.0284(6) Uani 1 1 d . . . . .
C19 C 0.6582(3) 0.0157(2) 0.3965(2) 0.0317(6) Uani 1 1 d . . . . .
C20 C 0.5625(3) 0.0437(2) 0.3215(2) 0.0281(5) Uani 1 1 d . . . . .
C21 C 0.5122(4) -0.0189(2) 0.2076(2) 0.0343(6) Uani 1 1 d . . . . .
H21A H 0.410157 -0.053606 0.194188 0.051 Uiso 1 1 calc R U . . .
H21B H 0.572420 -0.075252 0.187090 0.051 Uiso 1 1 calc R U . . .
H21C H 0.521853 0.032237 0.168970 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7554(4) 0.0947(3) 0.5950(2) 0.0395(7) Uani 1 1 d . . . . .
H22A H 0.740898 0.158400 0.648780 0.059 Uiso 1 1 calc R U . . .
H22B H 0.858826 0.100143 0.591642 0.059 Uiso 1 1 calc R U . . .
H22C H 0.723225 0.027616 0.609915 0.059 Uiso 1 1 calc R U . . .
B1 B 0.3912(3) 0.1920(2) 0.3234(2) 0.0222(5) Uani 1 1 d . . . . .
B2 B 0.3252(3) 0.2458(2) 0.1663(2) 0.0233(6) Uani 1 1 d . . . . .
B3 B 0.0633(3) 0.4755(3) 0.2178(2) 0.0288(6) Uani 1 1 d . . . . .
B4 B 0.3759(3) 0.4134(2) 0.5922(2) 0.0218(5) 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
Br1 C3 1.876(3) . ?
Br2 C19 1.873(3) . ?
F1 B2 1.391(3) . ?
F2 B1 1.392(3) . ?
F3 B3 1.372(4) . ?
F4 B3 1.363(4) . ?
F5 B4 1.364(3) . ?
F6 B4 1.371(3) . ?
O1 B1 1.402(3) . ?
O1 B2 1.395(3) . ?
N1 C2 1.336(4) . ?
N1 C6 1.403(3) . ?
N1 B2 1.559(3) . ?
N2 N3 1.410(3) . ?
N2 C7 1.327(3) . ?
N2 B3 1.560(4) . ?
N3 C8 1.327(3) . ?
N3 B2 1.614(4) . ?
N4 C8 1.342(3) . ?
N4 C10 1.392(3) . ?
N4 B3 1.574(3) . ?
N5 C9 1.335(3) . ?
N5 C11 1.397(3) . ?
N5 B4 1.568(3) . ?
N6 N7 1.395(3) . ?
N6 C9 1.326(3) . ?
N6 B1 1.607(3) . ?
N7 C16 1.317(3) . ?
N7 B4 1.553(3) . ?
N8 C17 1.396(3) . ?
N8 C20 1.345(3) . ?
N8 B1 1.548(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.518(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.490(4) . ?
C4 C6 1.414(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.366(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.458(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.402(4) . ?
C11 C12 1.387(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 C18 1.416(4) . ?
C18 C19 1.377(4) . ?
C18 C22 1.496(4) . ?
C19 C20 1.410(4) . ?
C20 C21 1.503(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
B2 O1 B1 124.0(2) . . ?
C2 N1 C6 107.7(2) . . ?
C2 N1 B2 133.4(2) . . ?
C6 N1 B2 117.3(2) . . ?
N3 N2 B3 111.75(19) . . ?
C7 N2 N3 117.4(2) . . ?
C7 N2 B3 127.0(2) . . ?
N2 N3 B2 118.23(19) . . ?
C8 N3 N2 107.0(2) . . ?
C8 N3 B2 134.8(2) . . ?
C8 N4 C10 122.7(2) . . ?
C8 N4 B3 110.0(2) . . ?
C10 N4 B3 127.2(2) . . ?
C9 N5 C11 122.8(2) . . ?
C9 N5 B4 109.9(2) . . ?
C11 N5 B4 126.8(2) . . ?
N7 N6 B1 124.09(19) . . ?
C9 N6 N7 107.49(19) . . ?
C9 N6 B1 127.19(19) . . ?
N6 N7 B4 111.72(19) . . ?
C16 N7 N6 119.5(2) . . ?
C16 N7 B4 128.7(2) . . ?
C17 N8 B1 124.2(2) . . ?
C20 N8 C17 108.1(2) . . ?
C20 N8 B1 127.0(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 124.8(2) . . ?
N1 C2 C3 108.0(2) . . ?
C3 C2 C1 127.3(3) . . ?
C2 C3 Br1 124.0(2) . . ?
C4 C3 Br1 125.6(2) . . ?
C4 C3 C2 110.3(3) . . ?
C3 C4 C5 128.8(3) . . ?
C3 C4 C6 104.6(2) . . ?
C6 C4 C5 126.6(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C4 109.4(2) . . ?
C7 C6 N1 121.0(2) . . ?
C7 C6 C4 129.1(2) . . ?
N2 C7 C6 125.2(2) . . ?
N2 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
N3 C8 N4 114.8(2) . . ?
N3 C8 C9 127.1(2) . . ?
N4 C8 C9 118.0(2) . . ?
N5 C9 C8 118.9(2) . . ?
N6 C9 N5 114.7(2) . . ?
N6 C9 C8 126.4(2) . . ?
N4 C10 C11 119.0(2) . . ?
N4 C10 C15 121.5(2) . . ?
C11 C10 C15 119.6(2) . . ?
N5 C11 C10 118.3(2) . . ?
C12 C11 N5 121.2(2) . . ?
C12 C11 C10 120.5(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.4 . . ?
C14 C15 C10 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
N7 C16 H16 117.9 . . ?
N7 C16 C17 124.1(2) . . ?
C17 C16 H16 117.9 . . ?
N8 C17 C18 109.4(2) . . ?
C16 C17 N8 120.7(2) . . ?
C16 C17 C18 129.7(2) . . ?
C17 C18 C22 126.8(3) . . ?
C19 C18 C17 104.5(2) . . ?
C19 C18 C22 128.7(3) . . ?
C18 C19 Br2 125.5(2) . . ?
C18 C19 C20 110.2(2) . . ?
C20 C19 Br2 124.3(2) . . ?
N8 C20 C19 107.7(2) . . ?
N8 C20 C21 123.5(2) . . ?
C19 C20 C21 128.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F2 B1 O1 115.5(2) . . ?
F2 B1 N6 105.8(2) . . ?
F2 B1 N8 109.5(2) . . ?
O1 B1 N6 108.7(2) . . ?
O1 B1 N8 112.2(2) . . ?
N8 B1 N6 104.31(18) . . ?
F1 B2 O1 116.0(2) . . ?
F1 B2 N1 107.01(19) . . ?
F1 B2 N3 105.2(2) . . ?
O1 B2 N1 113.2(2) . . ?
O1 B2 N3 111.4(2) . . ?
N1 B2 N3 102.94(19) . . ?
F3 B3 N2 111.1(2) . . ?
F3 B3 N4 113.4(2) . . ?
F4 B3 F3 111.5(2) . . ?
F4 B3 N2 113.2(3) . . ?
F4 B3 N4 111.8(2) . . ?
N2 B3 N4 94.78(19) . . ?
F5 B4 F6 111.1(2) . . ?
F5 B4 N5 111.4(2) . . ?
F5 B4 N7 112.1(2) . . ?
F6 B4 N5 114.4(2) . . ?
F6 B4 N7 111.7(2) . . ?
N7 B4 N5 95.25(18) . . ?

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
Br1 C3 C4 C5 4.8(4) . . . . ?
Br1 C3 C4 C6 -174.04(19) . . . . ?
Br2 C19 C20 N8 178.3(2) . . . . ?
Br2 C19 C20 C21 2.0(4) . . . . ?
N1 C2 C3 Br1 174.69(18) . . . . ?
N1 C2 C3 C4 -1.4(3) . . . . ?
N1 C6 C7 N2 4.3(4) . . . . ?
N2 N3 C8 N4 1.3(3) . . . . ?
N2 N3 C8 C9 -177.5(2) . . . . ?
N2 N3 B2 F1 -65.6(3) . . . . ?
N2 N3 B2 O1 168.0(2) . . . . ?
N2 N3 B2 N1 46.4(3) . . . . ?
N3 N2 C7 C6 0.0(4) . . . . ?
N3 N2 B3 F3 129.5(2) . . . . ?
N3 N2 B3 F4 -104.0(2) . . . . ?
N3 N2 B3 N4 12.2(3) . . . . ?
N3 C8 C9 N5 172.7(2) . . . . ?
N3 C8 C9 N6 -7.2(4) . . . . ?
N4 C8 C9 N5 -6.1(3) . . . . ?
N4 C8 C9 N6 173.9(2) . . . . ?
N4 C10 C11 N5 -2.6(3) . . . . ?
N4 C10 C11 C12 178.6(2) . . . . ?
N4 C10 C15 C14 -179.0(2) . . . . ?
N5 C11 C12 C13 -178.4(2) . . . . ?
N6 N7 C16 C17 -3.4(4) . . . . ?
N6 N7 B4 F5 106.4(2) . . . . ?
N6 N7 B4 F6 -128.2(2) . . . . ?
N6 N7 B4 N5 -9.3(2) . . . . ?
N7 N6 C9 N5 -0.6(3) . . . . ?
N7 N6 C9 C8 179.4(2) . . . . ?
N7 N6 B1 F2 95.1(3) . . . . ?
N7 N6 B1 O1 -140.2(2) . . . . ?
N7 N6 B1 N8 -20.4(3) . . . . ?
N7 C16 C17 N8 -3.3(4) . . . . ?
N7 C16 C17 C18 -179.1(3) . . . . ?
N8 C17 C18 C19 -1.1(3) . . . . ?
N8 C17 C18 C22 178.7(3) . . . . ?
C1 C2 C3 Br1 -6.8(4) . . . . ?
C1 C2 C3 C4 177.1(2) . . . . ?
C2 N1 C6 C4 1.1(3) . . . . ?
C2 N1 C6 C7 -171.5(2) . . . . ?
C2 N1 B2 F1 -94.7(3) . . . . ?
C2 N1 B2 O1 34.4(4) . . . . ?
C2 N1 B2 N3 154.8(2) . . . . ?
C2 C3 C4 C5 -179.2(3) . . . . ?
C2 C3 C4 C6 2.0(3) . . . . ?
C3 C4 C6 N1 -1.9(3) . . . . ?
C3 C4 C6 C7 169.9(3) . . . . ?
C4 C6 C7 N2 -166.6(3) . . . . ?
C5 C4 C6 N1 179.3(3) . . . . ?
C5 C4 C6 C7 -8.9(5) . . . . ?
C6 N1 C2 C1 -178.4(2) . . . . ?
C6 N1 C2 C3 0.2(3) . . . . ?
C6 N1 B2 F1 69.3(3) . . . . ?
C6 N1 B2 O1 -161.7(2) . . . . ?
C6 N1 B2 N3 -41.3(3) . . . . ?
C7 N2 N3 C8 150.0(2) . . . . ?
C7 N2 N3 B2 -28.4(3) . . . . ?
C7 N2 B3 F3 -27.6(4) . . . . ?
C7 N2 B3 F4 98.9(3) . . . . ?
C7 N2 B3 N4 -144.9(2) . . . . ?
C8 N3 B2 F1 116.6(3) . . . . ?
C8 N3 B2 O1 -9.8(4) . . . . ?
C8 N3 B2 N1 -131.5(3) . . . . ?
C8 N4 C10 C11 -1.6(4) . . . . ?
C8 N4 C10 C15 177.6(2) . . . . ?
C8 N4 B3 F3 -126.7(2) . . . . ?
C8 N4 B3 F4 106.2(3) . . . . ?
C8 N4 B3 N2 -11.2(3) . . . . ?
C9 N5 C11 C10 2.3(3) . . . . ?
C9 N5 C11 C12 -178.9(2) . . . . ?
C9 N5 B4 F5 -107.4(2) . . . . ?
C9 N5 B4 F6 125.4(2) . . . . ?
C9 N5 B4 N7 8.8(2) . . . . ?
C9 N6 N7 C16 -174.9(2) . . . . ?
C9 N6 N7 B4 7.0(3) . . . . ?
C9 N6 B1 F2 -70.6(3) . . . . ?
C9 N6 B1 O1 54.0(3) . . . . ?
C9 N6 B1 N8 173.8(2) . . . . ?
C10 N4 C8 N3 -173.1(2) . . . . ?
C10 N4 C8 C9 5.9(3) . . . . ?
C10 N4 B3 F3 53.6(4) . . . . ?
C10 N4 B3 F4 -73.5(3) . . . . ?
C10 N4 B3 N2 169.1(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 N5 C9 N6 -178.0(2) . . . . ?
C11 N5 C9 C8 2.1(3) . . . . ?
C11 N5 B4 F5 64.2(3) . . . . ?
C11 N5 B4 F6 -63.0(3) . . . . ?
C11 N5 B4 N7 -179.6(2) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C15 C10 C11 N5 178.1(2) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C16 N7 B4 F5 -71.5(3) . . . . ?
C16 N7 B4 F6 53.9(3) . . . . ?
C16 N7 B4 N5 172.8(2) . . . . ?
C16 C17 C18 C19 175.0(3) . . . . ?
C16 C17 C18 C22 -5.1(5) . . . . ?
C17 N8 C20 C19 -1.4(3) . . . . ?
C17 N8 C20 C21 175.2(3) . . . . ?
C17 N8 B1 F2 -99.3(3) . . . . ?
C17 N8 B1 O1 131.0(2) . . . . ?
C17 N8 B1 N6 13.6(3) . . . . ?
C17 C18 C19 Br2 -177.3(2) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 N8 0.7(3) . . . . ?
C18 C19 C20 C21 -175.6(3) . . . . ?
C20 N8 C17 C16 -174.9(3) . . . . ?
C20 N8 C17 C18 1.6(3) . . . . ?
C20 N8 B1 F2 70.3(3) . . . . ?
C20 N8 B1 O1 -59.4(3) . . . . ?
C20 N8 B1 N6 -176.9(2) . . . . ?
C22 C18 C19 Br2 2.9(5) . . . . ?
C22 C18 C19 C20 -179.6(3) . . . . ?
B1 O1 B2 F1 -62.3(3) . . . . ?
B1 O1 B2 N1 173.4(2) . . . . ?
B1 O1 B2 N3 57.9(3) . . . . ?
B1 N6 N7 C16 17.0(3) . . . . ?
B1 N6 N7 B4 -161.1(2) . . . . ?
B1 N6 C9 N5 167.1(2) . . . . ?
B1 N6 C9 C8 -12.9(4) . . . . ?
B1 N8 C17 C16 -3.7(4) . . . . ?
B1 N8 C17 C18 172.9(2) . . . . ?
B1 N8 C20 C19 -172.3(2) . . . . ?
B1 N8 C20 C21 4.2(4) . . . . ?
B2 O1 B1 F2 35.4(3) . . . . ?
B2 O1 B1 N6 -83.3(3) . . . . ?
B2 O1 B1 N8 161.9(2) . . . . ?
B2 N1 C2 C1 -13.3(4) . . . . ?
B2 N1 C2 C3 165.2(2) . . . . ?
B2 N1 C6 C4 -166.8(2) . . . . ?
B2 N1 C6 C7 20.7(3) . . . . ?
B2 N3 C8 N4 179.3(2) . . . . ?
B2 N3 C8 C9 0.5(4) . . . . ?
B3 N2 N3 C8 -9.5(3) . . . . ?
B3 N2 N3 B2 172.1(2) . . . . ?
B3 N2 C7 C6 156.0(3) . . . . ?
B3 N4 C8 N3 7.2(3) . . . . ?
B3 N4 C8 C9 -173.8(2) . . . . ?
B3 N4 C10 C11 178.0(2) . . . . ?
B3 N4 C10 C15 -2.7(4) . . . . ?
B4 N5 C9 N6 -6.0(3) . . . . ?
B4 N5 C9 C8 174.1(2) . . . . ?
B4 N5 C11 C10 -168.3(2) . . . . ?
B4 N5 C11 C12 10.5(4) . . . . ?
B4 N7 C16 C17 174.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
