# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1_pl
_database_code_depnum_ccdc_archive 'CCDC 2077719'
loop_
_audit_author_name
_audit_author_address
'chunhua chen'
;nanjing university
China
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 B F2 N O'
_chemical_formula_weight         375.21

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.493(4)
_cell_length_b                   17.513(6)
_cell_length_c                   18.089(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3641(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9538
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      53.75

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.503
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      213(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 liquid CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53808
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         53.874
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6626
_reflns_number_gt                6277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.5619P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6626
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
F4 F 0.05831(15) 0.10312(9) -0.29693(8) 0.0650(4) Uani 1 1 d . . . . .
F3 F -0.13638(15) 0.12615(9) -0.29329(8) 0.0679(5) Uani 1 1 d . . . . .
O2 O -0.05050(14) 0.08471(8) -0.40226(8) 0.0408(3) Uani 1 1 d . . . . .
N2 N -0.01397(15) 0.21615(10) -0.35657(9) 0.0352(4) Uani 1 1 d . . . . .
C38 C 0.19220(17) 0.20225(12) -0.56376(12) 0.0361(5) Uani 1 1 d . . . . .
C30 C -0.04938(17) 0.19142(11) -0.48456(10) 0.0301(4) Uani 1 1 d . . . . .
C29 C -0.02223(17) 0.24000(12) -0.42442(11) 0.0322(4) Uani 1 1 d . . . . .
H29 H -0.009552 0.292089 -0.434034 0.039 Uiso 1 1 calc R U . . .
C35 C -0.06073(17) 0.11250(11) -0.47067(11) 0.0318(4) Uani 1 1 d . . . . .
C31 C -0.04784(17) 0.21929(11) -0.55833(10) 0.0311(4) Uani 1 1 d . . . . .
C43 C 0.18273(18) 0.14945(13) -0.62102(12) 0.0390(5) Uani 1 1 d . . . . .
H43 H 0.183775 0.166392 -0.670323 0.047 Uiso 1 1 calc R U . . .
C28 C 0.0194(2) 0.27180(13) -0.30080(11) 0.0393(5) Uani 1 1 d . . . . .
C36 C 0.01543(19) 0.29196(12) -0.57827(12) 0.0381(5) Uani 1 1 d . . . . .
H36A H -0.009606 0.332679 -0.544677 0.046 Uiso 1 1 calc R U . . .
H36B H -0.006542 0.306984 -0.628552 0.046 Uiso 1 1 calc R U . . .
C41 C 0.16800(18) 0.04576(12) -0.53385(14) 0.0415(5) Uani 1 1 d . . . . .
C42 C 0.17176(18) 0.07211(13) -0.60603(14) 0.0424(5) Uani 1 1 d . . . . .
H42 H 0.166822 0.037147 -0.645329 0.051 Uiso 1 1 calc R U . . .
C32 C -0.08284(18) 0.16941(12) -0.61297(12) 0.0357(5) Uani 1 1 d . . . . .
H32 H -0.099877 0.188077 -0.660479 0.043 Uiso 1 1 calc R U . . .
C39 C 0.21386(17) 0.17365(13) -0.49342(13) 0.0378(5) Uani 1 1 d . . . . .
H39 H 0.237231 0.206997 -0.455511 0.045 Uiso 1 1 calc R U . . .
C34 C -0.06964(17) 0.06032(11) -0.52955(12) 0.0356(5) Uani 1 1 d . . . . .
C33 C -0.09321(18) 0.09117(13) -0.59829(13) 0.0384(5) Uani 1 1 d . . . . .
H33 H -0.117067 0.058434 -0.636584 0.046 Uiso 1 1 calc R U . . .
C40 C 0.20126(17) 0.09601(13) -0.47855(13) 0.0397(5) Uani 1 1 d . . . . .
H40 H 0.215453 0.077550 -0.430596 0.048 Uiso 1 1 calc R U . . .
C27 C 0.1356(2) 0.28873(16) -0.29107(13) 0.0536(6) Uani 1 1 d . . . . .
H27 H 0.192694 0.262109 -0.317918 0.064 Uiso 1 1 calc R U . . .
C37 C 0.1532(2) 0.28430(13) -0.57403(15) 0.0485(6) Uani 1 1 d . . . . .
H37A H 0.187351 0.304566 -0.619624 0.058 Uiso 1 1 calc R U . . .
H37B H 0.182095 0.315101 -0.532702 0.058 Uiso 1 1 calc R U . . .
C45 C -0.0296(2) -0.02138(12) -0.52016(15) 0.0441(5) Uani 1 1 d . . . . .
H45A H -0.058205 -0.051859 -0.561791 0.053 Uiso 1 1 calc R U . . .
H45B H -0.063500 -0.042313 -0.474784 0.053 Uiso 1 1 calc R U . . .
C23 C -0.0650(2) 0.30895(15) -0.26042(13) 0.0522(6) Uani 1 1 d . . . . .
H23 H -0.143858 0.295836 -0.265951 0.063 Uiso 1 1 calc R U . . .
C44 C 0.1065(2) -0.02863(13) -0.51607(18) 0.0575(7) Uani 1 1 d . . . . .
H44A H 0.128779 -0.045133 -0.466271 0.069 Uiso 1 1 calc R U . . .
H44B H 0.132258 -0.067968 -0.550969 0.069 Uiso 1 1 calc R U . . .
C26 C 0.1678(3) 0.34551(18) -0.24123(15) 0.0633(7) Uani 1 1 d . . . . .
H26 H 0.246828 0.357179 -0.234115 0.076 Uiso 1 1 calc R U . . .
C25 C 0.0839(3) 0.38446(15) -0.20247(14) 0.0607(7) Uani 1 1 d . . . . .
H25 H 0.105584 0.423703 -0.169801 0.073 Uiso 1 1 calc R U . . .
C24 C -0.0319(3) 0.36625(17) -0.21127(14) 0.0621(7) Uani 1 1 d . . . . .
H24 H -0.088818 0.392580 -0.184011 0.075 Uiso 1 1 calc R U . . .
B2 B -0.0368(2) 0.12936(16) -0.33592(13) 0.0418(6) Uani 1 1 d . . . . .
F2 F 0.17688(15) 0.13304(9) 0.19451(9) 0.0705(5) Uani 1 1 d . . . . .
F1 F -0.01750(16) 0.13409(9) 0.21568(8) 0.0685(5) Uani 1 1 d . . . . .
O1 O 0.04952(13) 0.17094(8) 0.10143(8) 0.0379(3) Uani 1 1 d . . . . .
N1 N 0.06160(15) 0.03499(10) 0.13875(9) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.0514(2) -0.02650(11) 0.19221(11) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.07668(16) 0.07191(11) 0.01198(10) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.06898(17) 0.01699(11) 0.06934(11) 0.0312(4) Uani 1 1 d . . . . .
H7 H 0.069241 -0.035005 0.056454 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1506(2) -0.06182(13) 0.21842(13) 0.0459(5) Uani 1 1 d . . . . .
H5 H 0.224711 -0.044634 0.203993 0.055 Uiso 1 1 calc R U . . .
C13 C 0.06370(16) 0.14970(11) 0.03072(11) 0.0304(4) Uani 1 1 d . . . . .
C9 C 0.07596(17) 0.04910(11) -0.06350(11) 0.0319(4) Uani 1 1 d . . . . .
C16 C -0.16437(18) 0.03503(12) -0.05693(13) 0.0377(5) Uani 1 1 d . . . . .
C10 C 0.08928(18) 0.10599(12) -0.11531(12) 0.0365(5) Uani 1 1 d . . . . .
H10 H 0.107243 0.093107 -0.164451 0.044 Uiso 1 1 calc R U . . .
C12 C 0.05032(18) 0.20558(11) -0.02421(11) 0.0337(4) Uani 1 1 d . . . . .
C11 C 0.07634(18) 0.18284(12) -0.09561(12) 0.0383(5) Uani 1 1 d . . . . .
H11 H 0.085690 0.220411 -0.132248 0.046 Uiso 1 1 calc R U . . .
C17 C -0.18836(19) 0.05740(13) 0.01511(13) 0.0411(5) Uani 1 1 d . . . . .
H17 H -0.197130 0.020084 0.052046 0.049 Uiso 1 1 calc R U . . .
C19 C -0.18839(19) 0.19024(13) -0.02021(16) 0.0469(6) Uani 1 1 d . . . . .
C010 C -0.17862(19) 0.08998(13) -0.11172(14) 0.0436(5) Uani 1 1 d . . . . .
H010 H -0.179744 0.075209 -0.161671 0.052 Uiso 1 1 calc R U . . .
C15 C -0.1027(2) -0.03954(13) -0.07269(15) 0.0486(6) Uani 1 1 d . . . . .
H15A H -0.137761 -0.063324 -0.116375 0.058 Uiso 1 1 calc R U . . .
H15B H -0.114074 -0.074195 -0.030775 0.058 Uiso 1 1 calc R U . . .
C22 C -0.01194(19) 0.27980(12) -0.00775(14) 0.0413(5) Uani 1 1 d . . . . .
H22A H 0.004989 0.316466 -0.047232 0.050 Uiso 1 1 calc R U . . .
H22B H 0.018243 0.300949 0.038597 0.050 Uiso 1 1 calc R U . . .
C1 C -0.0582(2) -0.05021(14) 0.21440(13) 0.0485(6) Uani 1 1 d . . . . .
H1 H -0.124896 -0.024944 0.196977 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0328(2) -0.02890(12) -0.08656(11) 0.0385(5) Uani 1 1 d . . . . .
H14A H 0.075346 -0.068032 -0.058853 0.046 Uiso 1 1 calc R U . . .
H14B H 0.049209 -0.036455 -0.139208 0.046 Uiso 1 1 calc R U . . .
C18 C -0.19966(18) 0.13443(14) 0.03352(14) 0.0460(6) Uani 1 1 d . . . . .
H18 H -0.215024 0.148504 0.082709 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1389(3) -0.12332(15) 0.26659(14) 0.0564(6) Uani 1 1 d . . . . .
H4 H 0.205641 -0.148174 0.284579 0.068 Uiso 1 1 calc R U . . .
C20 C -0.1912(2) 0.16665(14) -0.09314(15) 0.0481(6) Uani 1 1 d . . . . .
H20 H -0.201836 0.202991 -0.130782 0.058 Uiso 1 1 calc R U . . .
C3 C 0.0300(3) -0.14811(15) 0.28818(13) 0.0573(7) Uani 1 1 d . . . . .
H3 H 0.022876 -0.189962 0.320397 0.069 Uiso 1 1 calc R U . . .
C2 C -0.0687(3) -0.11146(15) 0.26249(14) 0.0567(7) Uani 1 1 d . . . . .
H2 H -0.142734 -0.128067 0.277602 0.068 Uiso 1 1 calc R U . . .
C21 C -0.1476(2) 0.26993(13) -0.0010(2) 0.0651(8) Uani 1 1 d . . . . .
H21A H -0.171274 0.281827 0.049783 0.078 Uiso 1 1 calc R U . . .
H21B H -0.185823 0.306594 -0.033895 0.078 Uiso 1 1 calc R U . . .
B1 B 0.0680(2) 0.12146(14) 0.16432(13) 0.0414(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
F4 B2 1.380(3) . ?
F3 B2 1.381(3) . ?
O2 C35 1.335(2) . ?
O2 B2 1.441(3) . ?
N2 C29 1.300(3) . ?
N2 C28 1.454(3) . ?
N2 B2 1.587(3) . ?
C38 C39 1.390(3) . ?
C38 C43 1.393(3) . ?
C38 C37 1.517(3) . ?
C30 C35 1.411(3) . ?
C30 C29 1.416(3) . ?
C30 C31 1.421(3) . ?
C29 H29 0.9400 . ?
C35 C34 1.407(3) . ?
C31 C32 1.379(3) . ?
C31 C36 1.510(3) . ?
C43 C42 1.387(3) . ?
C43 H43 0.9400 . ?
C28 C23 1.378(3) . ?
C28 C27 1.379(3) . ?
C36 C37 1.591(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C41 C42 1.385(3) . ?
C41 C40 1.386(3) . ?
C41 C44 1.517(3) . ?
C42 H42 0.9400 . ?
C32 C33 1.401(3) . ?
C32 H32 0.9400 . ?
C39 C40 1.394(3) . ?
C39 H39 0.9400 . ?
C34 C33 1.383(3) . ?
C34 C45 1.513(3) . ?
C33 H33 0.9400 . ?
C40 H40 0.9400 . ?
C27 C26 1.392(4) . ?
C27 H27 0.9400 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C45 C44 1.571(3) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C23 C24 1.394(4) . ?
C23 H23 0.9400 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C26 C25 1.373(4) . ?
C26 H26 0.9400 . ?
C25 C24 1.378(4) . ?
C25 H25 0.9400 . ?
C24 H24 0.9400 . ?
F2 B1 1.380(3) . ?
F1 B1 1.370(3) . ?
O1 C13 1.342(2) . ?
O1 B1 1.446(3) . ?
N1 C7 1.297(3) . ?
N1 C6 1.452(3) . ?
N1 B1 1.585(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.385(3) . ?
C8 C13 1.412(3) . ?
C8 C7 1.418(3) . ?
C8 C9 1.423(3) . ?
C7 H7 0.9400 . ?
C5 C4 1.392(3) . ?
C5 H5 0.9400 . ?
C13 C12 1.403(3) . ?
C9 C10 1.376(3) . ?
C9 C14 1.512(3) . ?
C16 C17 1.388(3) . ?
C16 C010 1.391(3) . ?
C16 C15 1.513(3) . ?
C10 C11 1.400(3) . ?
C10 H10 0.9400 . ?
C12 C11 1.384(3) . ?
C12 C22 1.513(3) . ?
C11 H11 0.9400 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9400 . ?
C19 C20 1.383(4) . ?
C19 C18 1.385(4) . ?
C19 C21 1.513(3) . ?
C010 C20 1.392(3) . ?
C010 H010 0.9400 . ?
C15 C14 1.588(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C22 C21 1.573(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C18 H18 0.9400 . ?
C4 C3 1.381(4) . ?
C4 H4 0.9400 . ?
C20 H20 0.9400 . ?
C3 C2 1.383(4) . ?
C3 H3 0.9400 . ?
C2 H2 0.9400 . ?
C21 H21A 0.9800 . ?
C21 H21B 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
C35 O2 B2 125.71(17) . . ?
C29 N2 C28 117.32(18) . . ?
C29 N2 B2 121.20(18) . . ?
C28 N2 B2 121.47(16) . . ?
C39 C38 C43 117.1(2) . . ?
C39 C38 C37 120.4(2) . . ?
C43 C38 C37 121.0(2) . . ?
C35 C30 C29 118.17(17) . . ?
C35 C30 C31 120.33(17) . . ?
C29 C30 C31 120.83(18) . . ?
N2 C29 C30 123.26(19) . . ?
N2 C29 H29 118.4 . . ?
C30 C29 H29 118.4 . . ?
O2 C35 C34 118.11(17) . . ?
O2 C35 C30 120.95(17) . . ?
C34 C35 C30 120.54(18) . . ?
C32 C31 C30 116.87(19) . . ?
C32 C31 C36 120.22(18) . . ?
C30 C31 C36 121.33(18) . . ?
C42 C43 C38 120.7(2) . . ?
C42 C43 H43 119.7 . . ?
C38 C43 H43 119.7 . . ?
C23 C28 C27 120.9(2) . . ?
C23 C28 N2 119.9(2) . . ?
C27 C28 N2 119.2(2) . . ?
C31 C36 C37 113.38(17) . . ?
C31 C36 H36A 108.9 . . ?
C37 C36 H36A 108.9 . . ?
C31 C36 H36B 108.9 . . ?
C37 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C42 C41 C40 117.4(2) . . ?
C42 C41 C44 120.0(2) . . ?
C40 C41 C44 121.4(2) . . ?
C41 C42 C43 120.8(2) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C31 C32 C33 120.6(2) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C38 C39 C40 120.6(2) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C33 C34 C35 116.19(18) . . ?
C33 C34 C45 122.0(2) . . ?
C35 C34 C45 120.5(2) . . ?
C34 C33 C32 122.4(2) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C41 C40 C39 120.6(2) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C38 C37 C36 112.34(18) . . ?
C38 C37 H37A 109.1 . . ?
C36 C37 H37A 109.1 . . ?
C38 C37 H37B 109.1 . . ?
C36 C37 H37B 109.1 . . ?
H37A C37 H37B 107.9 . . ?
C34 C45 C44 112.64(18) . . ?
C34 C45 H45A 109.1 . . ?
C44 C45 H45A 109.1 . . ?
C34 C45 H45B 109.1 . . ?
C44 C45 H45B 109.1 . . ?
H45A C45 H45B 107.8 . . ?
C28 C23 C24 119.1(3) . . ?
C28 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C41 C44 C45 112.60(19) . . ?
C41 C44 H44A 109.1 . . ?
C45 C44 H44A 109.1 . . ?
C41 C44 H44B 109.1 . . ?
C45 C44 H44B 109.1 . . ?
H44A C44 H44B 107.8 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
F4 B2 F3 110.95(19) . . ?
F4 B2 O2 109.4(2) . . ?
F3 B2 O2 110.6(2) . . ?
F4 B2 N2 108.0(2) . . ?
F3 B2 N2 107.9(2) . . ?
O2 B2 N2 109.98(17) . . ?
C13 O1 B1 124.47(16) . . ?
C7 N1 C6 118.01(17) . . ?
C7 N1 B1 120.76(17) . . ?
C6 N1 B1 121.20(16) . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 N1 119.59(19) . . ?
C1 C6 N1 119.27(19) . . ?
C13 C8 C7 118.18(17) . . ?
C13 C8 C9 120.06(17) . . ?
C7 C8 C9 120.77(18) . . ?
N1 C7 C8 123.21(18) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
O1 C13 C12 117.92(17) . . ?
O1 C13 C8 120.61(17) . . ?
C12 C13 C8 120.97(18) . . ?
C10 C9 C8 116.72(19) . . ?
C10 C9 C14 120.17(18) . . ?
C8 C9 C14 121.36(18) . . ?
C17 C16 C010 116.8(2) . . ?
C17 C16 C15 120.9(2) . . ?
C010 C16 C15 121.2(2) . . ?
C9 C10 C11 120.71(19) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C11 C12 C13 115.88(18) . . ?
C11 C12 C22 122.19(19) . . ?
C13 C12 C22 120.77(19) . . ?
C12 C11 C10 122.47(19) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C20 C19 C18 117.2(2) . . ?
C20 C19 C21 120.2(3) . . ?
C18 C19 C21 121.2(3) . . ?
C16 C010 C20 120.5(2) . . ?
C16 C010 H010 119.7 . . ?
C20 C010 H010 119.7 . . ?
C16 C15 C14 112.82(18) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C12 C22 C21 112.93(18) . . ?
C12 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C12 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C9 C14 C15 112.61(17) . . ?
C9 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C9 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C19 C20 C010 121.1(2) . . ?
C19 C20 H20 119.5 . . ?
C010 C20 H20 119.5 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C19 C21 C22 113.0(2) . . ?
C19 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C19 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
F1 B1 F2 111.0(2) . . ?
F1 B1 O1 109.4(2) . . ?
F2 B1 O1 110.9(2) . . ?
F1 B1 N1 108.6(2) . . ?
F2 B1 N1 107.33(19) . . ?
O1 B1 N1 109.65(16) . . ?

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
C28 N2 C29 C30 177.41(19) . . . . ?
B2 N2 C29 C30 -1.3(3) . . . . ?
C35 C30 C29 N2 -4.1(3) . . . . ?
C31 C30 C29 N2 -174.8(2) . . . . ?
B2 O2 C35 C34 177.9(2) . . . . ?
B2 O2 C35 C30 5.2(3) . . . . ?
C29 C30 C35 O2 2.5(3) . . . . ?
C31 C30 C35 O2 173.14(18) . . . . ?
C29 C30 C35 C34 -170.11(18) . . . . ?
C31 C30 C35 C34 0.6(3) . . . . ?
C35 C30 C31 C32 13.7(3) . . . . ?
C29 C30 C31 C32 -175.85(19) . . . . ?
C35 C30 C31 C36 -151.92(19) . . . . ?
C29 C30 C31 C36 18.5(3) . . . . ?
C39 C38 C43 C42 12.7(3) . . . . ?
C37 C38 C43 C42 -153.4(2) . . . . ?
C29 N2 C28 C23 95.1(3) . . . . ?
B2 N2 C28 C23 -86.2(3) . . . . ?
C29 N2 C28 C27 -82.4(3) . . . . ?
B2 N2 C28 C27 96.3(3) . . . . ?
C32 C31 C36 C37 -95.2(2) . . . . ?
C30 C31 C36 C37 70.0(3) . . . . ?
C40 C41 C42 C43 -14.1(3) . . . . ?
C44 C41 C42 C43 153.7(2) . . . . ?
C38 C43 C42 C41 1.1(3) . . . . ?
C30 C31 C32 C33 -14.1(3) . . . . ?
C36 C31 C32 C33 151.7(2) . . . . ?
C43 C38 C39 C40 -13.6(3) . . . . ?
C37 C38 C39 C40 152.7(2) . . . . ?
O2 C35 C34 C33 172.96(18) . . . . ?
C30 C35 C34 C33 -14.2(3) . . . . ?
O2 C35 C34 C45 -19.9(3) . . . . ?
C30 C35 C34 C45 152.9(2) . . . . ?
C35 C34 C33 C32 14.2(3) . . . . ?
C45 C34 C33 C32 -152.8(2) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
C42 C41 C40 C39 13.2(3) . . . . ?
C44 C41 C40 C39 -154.4(2) . . . . ?
C38 C39 C40 C41 0.6(3) . . . . ?
C23 C28 C27 C26 -1.7(4) . . . . ?
N2 C28 C27 C26 175.8(2) . . . . ?
C39 C38 C37 C36 -94.3(3) . . . . ?
C43 C38 C37 C36 71.4(3) . . . . ?
C31 C36 C37 C38 9.9(3) . . . . ?
C33 C34 C45 C44 94.8(3) . . . . ?
C35 C34 C45 C44 -71.6(3) . . . . ?
C27 C28 C23 C24 2.4(4) . . . . ?
N2 C28 C23 C24 -175.1(2) . . . . ?
C42 C41 C44 C45 -73.1(3) . . . . ?
C40 C41 C44 C45 94.2(3) . . . . ?
C34 C45 C44 C41 -8.6(3) . . . . ?
C28 C27 C26 C25 -0.3(4) . . . . ?
C27 C26 C25 C24 1.7(4) . . . . ?
C26 C25 C24 C23 -1.0(4) . . . . ?
C28 C23 C24 C25 -1.0(4) . . . . ?
C35 O2 B2 F4 -128.0(2) . . . . ?
C35 O2 B2 F3 109.5(2) . . . . ?
C35 O2 B2 N2 -9.6(3) . . . . ?
C29 N2 B2 F4 126.8(2) . . . . ?
C28 N2 B2 F4 -51.8(3) . . . . ?
C29 N2 B2 F3 -113.2(2) . . . . ?
C28 N2 B2 F3 68.2(3) . . . . ?
C29 N2 B2 O2 7.6(3) . . . . ?
C28 N2 B2 O2 -171.07(18) . . . . ?
C7 N1 C6 C5 85.3(3) . . . . ?
B1 N1 C6 C5 -92.6(3) . . . . ?
C7 N1 C6 C1 -92.8(2) . . . . ?
B1 N1 C6 C1 89.3(3) . . . . ?
C6 N1 C7 C8 178.56(18) . . . . ?
B1 N1 C7 C8 -3.5(3) . . . . ?
C13 C8 C7 N1 -6.7(3) . . . . ?
C9 C8 C7 N1 -175.33(19) . . . . ?
C1 C6 C5 C4 1.5(3) . . . . ?
N1 C6 C5 C4 -176.6(2) . . . . ?
B1 O1 C13 C12 -175.7(2) . . . . ?
B1 O1 C13 C8 12.3(3) . . . . ?
C7 C8 C13 O1 2.8(3) . . . . ?
C9 C8 C13 O1 171.55(18) . . . . ?
C7 C8 C13 C12 -168.92(18) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C13 C8 C9 C10 14.5(3) . . . . ?
C7 C8 C9 C10 -177.04(18) . . . . ?
C13 C8 C9 C14 -150.40(19) . . . . ?
C7 C8 C9 C14 18.0(3) . . . . ?
C8 C9 C10 C11 -14.6(3) . . . . ?
C14 C9 C10 C11 150.5(2) . . . . ?
O1 C13 C12 C11 174.18(18) . . . . ?
C8 C13 C12 C11 -13.9(3) . . . . ?
O1 C13 C12 C22 -17.9(3) . . . . ?
C8 C13 C12 C22 154.10(19) . . . . ?
C13 C12 C11 C10 14.1(3) . . . . ?
C22 C12 C11 C10 -153.7(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C010 C16 C17 C18 -14.3(3) . . . . ?
C15 C16 C17 C18 153.5(2) . . . . ?
C17 C16 C010 C20 13.5(3) . . . . ?
C15 C16 C010 C20 -154.3(2) . . . . ?
C17 C16 C15 C14 -98.0(3) . . . . ?
C010 C16 C15 C14 69.3(3) . . . . ?
C11 C12 C22 C21 93.5(3) . . . . ?
C13 C12 C22 C21 -73.7(3) . . . . ?
C5 C6 C1 C2 -1.4(3) . . . . ?
N1 C6 C1 C2 176.7(2) . . . . ?
C10 C9 C14 C15 -97.8(2) . . . . ?
C8 C9 C14 C15 66.6(3) . . . . ?
C16 C15 C14 C9 13.6(3) . . . . ?
C20 C19 C18 C17 13.7(3) . . . . ?
C21 C19 C18 C17 -152.7(2) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C18 C19 C20 C010 -14.5(3) . . . . ?
C21 C19 C20 C010 152.0(2) . . . . ?
C16 C010 C20 C19 0.9(4) . . . . ?
C5 C4 C3 C2 -0.5(4) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C20 C19 C21 C22 -74.4(3) . . . . ?
C18 C19 C21 C22 91.6(3) . . . . ?
C12 C22 C21 C19 -6.1(4) . . . . ?
C13 O1 B1 F1 -139.39(19) . . . . ?
C13 O1 B1 F2 97.9(2) . . . . ?
C13 O1 B1 N1 -20.4(3) . . . . ?
C7 N1 B1 F1 135.3(2) . . . . ?
C6 N1 B1 F1 -46.8(3) . . . . ?
C7 N1 B1 F2 -104.6(2) . . . . ?
C6 N1 B1 F2 73.2(3) . . . . ?
C7 N1 B1 O1 15.9(3) . . . . ?
C6 N1 B1 O1 -166.24(18) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.037

