# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_jnb018cc_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068070'
loop_
_audit_author_name
_audit_author_address
'Christopher Caputo'
;York University
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H8 B F10 N O'
_chemical_formula_sum            'C24 H8 B F10 N O'
_chemical_formula_weight         527.12
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.4685(5)
_cell_length_b                   12.8091(7)
_cell_length_c                   17.3040(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.621(2)
_cell_angle_gamma                90
_cell_volume                     2096.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1517 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8409.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25799
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.407
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                4036
_reflns_number_total             4833
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.041
_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)+(0.0465P)²+1.2513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23)
;
_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
F1 F 0.30176(13) 0.27617(10) 0.56002(6) 0.0463(3) Uani 1 1 d . . . . .
F2 F 1.10457(12) 0.59573(11) 0.37627(9) 0.0606(4) Uani 1 1 d . . . . .
F3 F 0.81238(11) 0.30323(8) 0.34094(7) 0.0413(3) Uani 1 1 d . . . . .
F4 F 0.89132(11) 0.72085(8) 0.32094(7) 0.0400(3) Uani 1 1 d . . . . .
F5 F 0.64149(10) 0.63834(7) 0.27477(6) 0.0325(2) Uani 1 1 d . . . . .
F6 F 0.28515(12) 0.47964(9) 0.51451(6) 0.0426(3) Uani 1 1 d . . . . .
F7 F 0.41389(11) 0.54160(8) 0.38609(6) 0.0350(2) Uani 1 1 d . . . . .
F8 F 0.44385(13) 0.13635(8) 0.47628(6) 0.0426(3) Uani 1 1 d . . . . .
F9 F 0.55991(11) 0.19511(8) 0.34374(6) 0.0356(2) Uani 1 1 d . . . . .
F10 F 1.06379(12) 0.38638(11) 0.38604(9) 0.0583(4) Uani 1 1 d . . . . .
O1 O 0.30578(12) 0.56834(9) 0.14595(7) 0.0332(3) Uani 1 1 d . . . . .
N1 N 0.48996(13) 0.43062(10) 0.21732(7) 0.0219(3) Uani 1 1 d . . . . .
C1 C 0.36414(18) 0.30743(14) 0.49592(9) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.43575(18) 0.23606(13) 0.45305(10) 0.0296(3) Uani 1 1 d . . . . .
C3 C 0.49702(17) 0.26853(13) 0.38602(9) 0.0267(3) Uani 1 1 d . . . . .
C4 C 0.49217(15) 0.37116(12) 0.36067(9) 0.0228(3) Uani 1 1 d . . . . .
B5 B 0.56591(17) 0.41880(13) 0.28776(10) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.34408(16) 0.39991(12) 0.20481(9) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.29286(17) 0.30250(13) 0.22418(10) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.355293 0.251047 0.245717 0.033 Uiso 1 1 calc R U . . .
C8 C 0.15014(18) 0.28027(14) 0.21204(11) 0.0347(4) Uani 1 1 d . . . . .
H8 H 0.114561 0.213834 0.225879 0.042 Uiso 1 1 calc R U . . .
C9 C 0.05967(18) 0.35480(16) 0.17980(12) 0.0393(4) Uani 1 1 d . . . . .
H9 H -0.038257 0.339663 0.172554 0.047 Uiso 1 1 calc R U . . .
C10 C 0.98035(18) 0.55390(16) 0.35246(11) 0.0363(4) Uani 1 1 d . . . . .
C11 C 0.95941(18) 0.44809(15) 0.35773(11) 0.0358(4) Uani 1 1 d . . . . .
C12 C 0.82979(17) 0.40673(13) 0.33409(10) 0.0276(3) Uani 1 1 d . . . . .
C13 C 0.71861(15) 0.46686(12) 0.30413(8) 0.0221(3) Uani 1 1 d . . . . .
C14 C 0.74488(16) 0.57317(12) 0.29991(9) 0.0236(3) Uani 1 1 d . . . . .
C15 C 0.87274(17) 0.61736(13) 0.32379(10) 0.0291(3) Uani 1 1 d . . . . .
C16 C 0.53747(16) 0.48987(12) 0.15269(9) 0.0242(3) Uani 1 1 d . . . . .
C17 C 0.66990(17) 0.47828(14) 0.12285(9) 0.0295(3) Uani 1 1 d . . . . .
H17 H 0.733483 0.426754 0.143183 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7088(2) 0.54302(15) 0.06268(10) 0.0368(4) Uani 1 1 d . . . . .
H18 H 0.799761 0.535985 0.042232 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6160(2) 0.61737(15) 0.03258(10) 0.0404(4) Uani 1 1 d . . . . .
H19 H 0.644587 0.662524 -0.007358 0.049 Uiso 1 1 calc R U . . .
C20 C 0.4814(2) 0.62656(14) 0.06023(10) 0.0370(4) Uani 1 1 d . . . . .
H20 H 0.416794 0.676510 0.038652 0.044 Uiso 1 1 calc R U . . .
C21 C 0.44257(17) 0.56181(13) 0.11983(9) 0.0279(3) Uani 1 1 d . . . . .
C22 C 0.25310(17) 0.47327(13) 0.16992(10) 0.0282(3) Uani 1 1 d . . . . .
C23 C 0.11048(18) 0.45135(15) 0.15796(11) 0.0369(4) Uani 1 1 d . . . . .
H23 H 0.048257 0.501915 0.135047 0.044 Uiso 1 1 calc R U . . .
C24 C 0.35564(17) 0.41017(14) 0.47286(9) 0.0294(3) Uani 1 1 d . . . . .
C25 C 0.42035(16) 0.44009(12) 0.40664(9) 0.0251(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
F1 C1 1.3415(19) . ?
F2 C10 1.3401(19) . ?
F3 C12 1.3418(19) . ?
F4 C15 1.3385(19) . ?
F5 C14 1.3436(17) . ?
F6 C24 1.3419(19) . ?
F7 C25 1.3486(18) . ?
F8 C2 1.3401(19) . ?
F9 C3 1.3469(19) . ?
F10 C11 1.3406(19) . ?
O1 C21 1.394(2) . ?
O1 C22 1.387(2) . ?
N1 B5 1.395(2) . ?
N1 C6 1.4429(18) . ?
N1 C16 1.441(2) . ?
C1 C2 1.375(2) . ?
C1 C24 1.377(3) . ?
C2 C3 1.384(2) . ?
C3 C4 1.386(2) . ?
C4 B5 1.591(2) . ?
C4 C25 1.387(2) . ?
B5 C13 1.585(2) . ?
C6 C7 1.385(2) . ?
C6 C22 1.394(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C23 1.386(3) . ?
C10 C11 1.373(3) . ?
C10 C15 1.378(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.382(2) . ?
C16 C17 1.386(2) . ?
C16 C21 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.394(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(2) . ?

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
C22 O1 C21 113.37(12) . . ?
B5 N1 C6 123.59(13) . . ?
B5 N1 C16 124.67(13) . . ?
C16 N1 C6 110.97(12) . . ?
F1 C1 C2 119.61(16) . . ?
F1 C1 C24 120.19(16) . . ?
C2 C1 C24 120.19(15) . . ?
F8 C2 C1 119.64(15) . . ?
F8 C2 C3 121.14(15) . . ?
C1 C2 C3 119.21(15) . . ?
F9 C3 C2 117.26(14) . . ?
F9 C3 C4 119.96(14) . . ?
C2 C3 C4 122.75(15) . . ?
C3 C4 B5 127.25(14) . . ?
C3 C4 C25 115.61(14) . . ?
C25 C4 B5 117.06(13) . . ?
N1 B5 C4 120.47(13) . . ?
N1 B5 C13 122.92(14) . . ?
C13 B5 C4 115.92(12) . . ?
C7 C6 N1 123.54(14) . . ?
C7 C6 C22 119.72(14) . . ?
C22 C6 N1 116.73(14) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.83(15) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.03(17) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C23 120.64(16) . . ?
C23 C9 H9 119.7 . . ?
F2 C10 C11 120.10(16) . . ?
F2 C10 C15 119.93(17) . . ?
C11 C10 C15 119.96(15) . . ?
F10 C11 C10 119.99(16) . . ?
F10 C11 C12 120.81(17) . . ?
C10 C11 C12 119.19(15) . . ?
F3 C12 C11 117.63(14) . . ?
F3 C12 C13 119.20(14) . . ?
C11 C12 C13 123.17(15) . . ?
C12 C13 B5 121.48(14) . . ?
C12 C13 C14 115.49(14) . . ?
C14 C13 B5 122.44(13) . . ?
F5 C14 C13 119.81(13) . . ?
F5 C14 C15 117.23(14) . . ?
C15 C14 C13 122.90(14) . . ?
F4 C15 C10 120.08(15) . . ?
F4 C15 C14 120.61(15) . . ?
C10 C15 C14 119.28(15) . . ?
C17 C16 N1 123.56(14) . . ?
C17 C16 C21 119.84(15) . . ?
C21 C16 N1 116.60(14) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.29(17) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.42(17) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.48(17) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.04(17) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 O1 120.00(14) . . ?
C20 C21 O1 119.18(15) . . ?
C20 C21 C16 120.81(16) . . ?
O1 C22 C6 119.87(14) . . ?
C23 C22 O1 119.65(15) . . ?
C23 C22 C6 120.47(16) . . ?
C9 C23 H23 120.4 . . ?
C22 C23 C9 119.23(16) . . ?
C22 C23 H23 120.4 . . ?
F6 C24 C1 120.15(15) . . ?
F6 C24 C25 120.87(16) . . ?
C1 C24 C25 118.98(15) . . ?
F7 C25 C4 118.69(14) . . ?
F7 C25 C24 118.08(14) . . ?
C24 C25 C4 123.23(15) . . ?

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
F1 C1 C2 F8 -0.8(2) . . . . ?
F1 C1 C2 C3 178.52(15) . . . . ?
F1 C1 C24 F6 0.1(2) . . . . ?
F1 C1 C24 C25 -179.80(14) . . . . ?
F2 C10 C11 F10 -0.6(3) . . . . ?
F2 C10 C11 C12 178.92(18) . . . . ?
F2 C10 C15 F4 -1.2(3) . . . . ?
F2 C10 C15 C14 -179.59(16) . . . . ?
F3 C12 C13 B5 7.9(2) . . . . ?
F3 C12 C13 C14 179.24(14) . . . . ?
F5 C14 C15 F4 -0.6(2) . . . . ?
F5 C14 C15 C10 177.84(15) . . . . ?
F6 C24 C25 F7 1.7(2) . . . . ?
F6 C24 C25 C4 -178.72(14) . . . . ?
F8 C2 C3 F9 2.6(2) . . . . ?
F8 C2 C3 C4 -179.26(15) . . . . ?
F9 C3 C4 B5 -5.8(2) . . . . ?
F9 C3 C4 C25 177.57(13) . . . . ?
F10 C11 C12 F3 0.4(3) . . . . ?
F10 C11 C12 C13 -179.71(16) . . . . ?
O1 C22 C23 C9 177.88(17) . . . . ?
N1 B5 C13 C12 -129.57(16) . . . . ?
N1 B5 C13 C14 59.7(2) . . . . ?
N1 C6 C7 C8 178.30(15) . . . . ?
N1 C6 C22 O1 2.9(2) . . . . ?
N1 C6 C22 C23 -178.01(15) . . . . ?
N1 C16 C17 C18 -176.72(14) . . . . ?
N1 C16 C21 O1 -4.6(2) . . . . ?
N1 C16 C21 C20 176.36(14) . . . . ?
C1 C2 C3 F9 -176.71(15) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C24 C25 F7 -178.34(14) . . . . ?
C1 C24 C25 C4 1.2(2) . . . . ?
C2 C1 C24 F6 179.67(15) . . . . ?
C2 C1 C24 C25 -0.3(2) . . . . ?
C2 C3 C4 B5 176.11(15) . . . . ?
C2 C3 C4 C25 -0.6(2) . . . . ?
C3 C4 B5 N1 96.78(19) . . . . ?
C3 C4 B5 C13 -92.45(18) . . . . ?
C3 C4 C25 F7 178.76(13) . . . . ?
C3 C4 C25 C24 -0.8(2) . . . . ?
C4 B5 C13 C12 59.91(19) . . . . ?
C4 B5 C13 C14 -110.84(16) . . . . ?
B5 N1 C6 C7 -50.4(2) . . . . ?
B5 N1 C6 C22 130.87(16) . . . . ?
B5 N1 C16 C17 50.1(2) . . . . ?
B5 N1 C16 C21 -129.97(15) . . . . ?
B5 C4 C25 F7 1.8(2) . . . . ?
B5 C4 C25 C24 -177.82(14) . . . . ?
B5 C13 C14 F5 -5.9(2) . . . . ?
B5 C13 C14 C15 171.23(14) . . . . ?
C6 N1 B5 C4 -1.2(2) . . . . ?
C6 N1 B5 C13 -171.26(14) . . . . ?
C6 N1 C16 C17 -139.69(15) . . . . ?
C6 N1 C16 C21 40.25(18) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C6 C22 C23 C9 -1.2(3) . . . . ?
C7 C6 C22 O1 -175.86(15) . . . . ?
C7 C6 C22 C23 3.2(2) . . . . ?
C7 C8 C9 C23 1.2(3) . . . . ?
C8 C9 C23 C22 -1.0(3) . . . . ?
C10 C11 C12 F3 -179.18(17) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C10 C15 F4 177.82(17) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
C11 C12 C13 B5 -172.03(16) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 F5 -177.14(14) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 F4 -177.75(14) . . . . ?
C13 C14 C15 C10 0.7(2) . . . . ?
C15 C10 C11 F10 -179.62(18) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C16 N1 B5 C4 167.87(14) . . . . ?
C16 N1 B5 C13 -2.2(2) . . . . ?
C16 N1 C6 C7 139.27(15) . . . . ?
C16 N1 C6 C22 -39.48(18) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C16 C21 O1 175.31(14) . . . . ?
C17 C16 C21 C20 -3.7(2) . . . . ?
C17 C18 C19 C20 -1.9(3) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C19 C20 C21 O1 -177.79(15) . . . . ?
C19 C20 C21 C16 1.2(2) . . . . ?
C21 O1 C22 C6 33.6(2) . . . . ?
C21 O1 C22 C23 -145.44(16) . . . . ?
C21 C16 C17 C18 3.3(2) . . . . ?
C22 O1 C21 C16 -32.8(2) . . . . ?
C22 O1 C21 C20 146.20(15) . . . . ?
C22 C6 C7 C8 -3.0(2) . . . . ?
C24 C1 C2 F8 179.70(15) . . . . ?
C24 C1 C2 C3 -1.0(3) . . . . ?
C25 C4 B5 N1 -86.61(18) . . . . ?
C25 C4 B5 C13 84.17(17) . . . . ?

_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_jnb064cc_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068077'
loop_
_audit_author_name
_audit_author_address
'Christopher Caputo'
;York University
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H12 B F10 N)'
_chemical_formula_sum            'C50 H24 B2 F20 N2'
_chemical_formula_weight         1054.33
_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'
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'

_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                   11.1178(6)
_cell_length_b                   12.3316(6)
_cell_length_c                   15.8444(8)
_cell_angle_alpha                83.703(2)
_cell_angle_beta                 89.331(2)
_cell_angle_gamma                89.752(2)
_cell_volume                     2159.01(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5593
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0846 after correction.
The Ratio of minimum to maximum transmission is 0.7501.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61564
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.215
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                8189
_reflns_number_total             9880
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         9880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+1.9678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1A), B2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23),
 C31(H31), C32(H32), C33(H33), C38(H38), C42(H42), C43(H43), C44(H44), C45(H45)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.76013(13) 0.05842(11) -0.13001(8) 0.0469(3) Uani 1 1 d . . . . .
F2 F 0.56486(19) 0.73865(11) 0.10731(11) 0.0744(5) Uani 1 1 d . . . . .
F3 F 0.84743(10) 0.46448(9) 0.18428(7) 0.0341(3) Uani 1 1 d . . . . .
F4 F 0.86236(12) 0.25617(11) -0.11656(8) 0.0438(3) Uani 1 1 d . . . . .
F5 F 0.56383(10) 0.07056(9) 0.13077(7) 0.0344(3) Uani 1 1 d . . . . .
F6 F 0.61721(11) -0.03511(10) -0.00351(9) 0.0434(3) Uani 1 1 d . . . . .
F7 F 0.82171(10) 0.35810(9) 0.02194(7) 0.0323(2) Uani 1 1 d . . . . .
F8 F 0.45314(10) 0.37315(10) 0.11004(8) 0.0376(3) Uani 1 1 d . . . . .
F9 F 0.39756(14) 0.58407(13) 0.08196(10) 0.0635(5) Uani 1 1 d . . . . .
F10 F 0.78953(15) 0.67506(10) 0.15932(8) 0.0523(4) Uani 1 1 d . . . . .
F11 F 0.70009(15) 0.66863(13) 0.32324(8) 0.0595(4) Uani 1 1 d . . . . .
F12 F 0.91022(14) 1.23596(9) 0.63871(9) 0.0499(3) Uani 1 1 d . . . . .
F13 F 1.07637(11) 1.09722(10) 0.58145(8) 0.0418(3) Uani 1 1 d . . . . .
F14 F 0.62125(10) 0.85699(9) 0.55908(7) 0.0341(3) Uani 1 1 d . . . . .
F15 F 0.56277(12) 0.80998(11) 0.40275(8) 0.0467(3) Uani 1 1 d . . . . .
F16 F 0.89791(16) 0.57596(12) 0.40076(10) 0.0607(4) Uani 1 1 d . . . . .
F17 F 0.95362(12) 0.61739(10) 0.55762(9) 0.0476(3) Uani 1 1 d . . . . .
F18 F 0.69641(12) 1.15528(9) 0.70371(8) 0.0394(3) Uani 1 1 d . . . . .
F19 F 0.65156(9) 0.94234(8) 0.71580(7) 0.0283(2) Uani 1 1 d . . . . .
F20 F 1.03255(9) 0.88361(9) 0.59223(7) 0.0312(2) Uani 1 1 d . . . . .
N1 N 0.78435(13) 0.24216(11) 0.23395(9) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.72814(12) 0.71998(11) 0.73097(9) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.73688(18) 0.11144(16) -0.06172(12) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.78854(17) 0.21136(16) -0.05495(11) 0.0292(4) Uani 1 1 d . . . . .
C3 C 0.76452(15) 0.26253(14) 0.01661(11) 0.0239(3) Uani 1 1 d . . . . .
C4 C 0.68957(15) 0.22045(13) 0.08236(10) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.75012(15) 0.24723(14) 0.32377(11) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.77857(17) 0.33836(15) 0.36349(12) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.819449 0.398293 0.333251 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7464(2) 0.34055(18) 0.44812(13) 0.0369(5) Uani 1 1 d . . . . .
H7 H 0.765140 0.402393 0.476280 0.044 Uiso 1 1 calc R U . . .
C8 C 0.6873(2) 0.25332(19) 0.49131(13) 0.0392(5) Uani 1 1 d . . . . .
H8 H 0.664003 0.255678 0.548970 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5923(2) 0.63238(16) 0.12145(14) 0.0434(6) Uani 1 1 d . . . . .
C10 C 0.7053(2) 0.60010(15) 0.14778(12) 0.0357(5) Uani 1 1 d . . . . .
C11 C 0.73219(17) 0.49009(14) 0.16170(11) 0.0251(3) Uani 1 1 d . . . . .
C12 C 0.65049(15) 0.40802(13) 0.15294(10) 0.0204(3) Uani 1 1 d . . . . .
C13 C 0.66263(17) 0.06486(15) 0.00170(13) 0.0299(4) Uani 1 1 d . . . . .
C14 C 0.63841(15) 0.12040(14) 0.07116(11) 0.0252(3) Uani 1 1 d . . . . .
C15 C 0.83049(15) 0.13330(13) 0.22012(11) 0.0216(3) Uani 1 1 d . . . . .
C16 C 0.92681(16) 0.12559(15) 0.16505(12) 0.0266(4) Uani 1 1 d . . . . .
H16 H 0.968272 0.189184 0.141400 0.032 Uiso 1 1 calc R U . . .
C17 C 0.96178(18) 0.02328(17) 0.14496(14) 0.0363(4) Uani 1 1 d . . . . .
H17 H 1.027575 0.016236 0.107132 0.044 Uiso 1 1 calc R U . . .
C18 C 0.9004(2) -0.06859(17) 0.18026(15) 0.0389(5) Uani 1 1 d . . . . .
H18 H 0.923021 -0.138487 0.165420 0.047 Uiso 1 1 calc R U . . .
C19 C 0.80646(19) -0.05905(15) 0.23699(13) 0.0338(4) Uani 1 1 d . . . . .
H19 H 0.766171 -0.122808 0.261593 0.041 Uiso 1 1 calc R U . . .
C20 C 0.76999(16) 0.04278(14) 0.25860(12) 0.0262(4) Uani 1 1 d . . . . .
C21 C 0.67106(18) 0.05748(15) 0.32165(12) 0.0305(4) Uani 1 1 d . . . . .
H21A H 0.666885 -0.007704 0.364011 0.037 Uiso 1 1 calc R U . . .
H21B H 0.593097 0.064872 0.291977 0.037 Uiso 1 1 calc R U . . .
C22 C 0.69269(16) 0.15733(15) 0.36625(11) 0.0263(4) Uani 1 1 d . . . . .
C23 C 0.66140(18) 0.16173(18) 0.45101(12) 0.0336(4) Uani 1 1 d . . . . .
H23 H 0.621868 0.101392 0.481756 0.040 Uiso 1 1 calc R U . . .
C24 C 0.53869(17) 0.44590(15) 0.12451(11) 0.0282(4) Uani 1 1 d . . . . .
C25 C 0.5084(2) 0.55485(18) 0.10905(13) 0.0395(5) Uani 1 1 d . . . . .
C26 C 0.7298(2) 0.69116(17) 0.40181(12) 0.0385(5) Uani 1 1 d . . . . .
C27 C 0.8289(2) 0.64429(16) 0.44085(13) 0.0382(5) Uani 1 1 d . . . . .
C28 C 0.85711(19) 0.66783(15) 0.52190(12) 0.0312(4) Uani 1 1 d . . . . .
C29 C 0.78982(16) 0.73970(13) 0.56519(11) 0.0238(3) Uani 1 1 d . . . . .
C30 C 0.67861(15) 0.61513(13) 0.71051(10) 0.0204(3) Uani 1 1 d . . . . .
C31 C 0.56772(15) 0.61324(14) 0.67126(11) 0.0242(3) Uani 1 1 d . . . . .
H31 H 0.522870 0.678528 0.658069 0.029 Uiso 1 1 calc R U . . .
C32 C 0.52382(17) 0.51381(16) 0.65171(13) 0.0326(4) Uani 1 1 d . . . . .
H32 H 0.448763 0.510681 0.624039 0.039 Uiso 1 1 calc R U . . .
C33 C 0.58975(19) 0.41907(16) 0.67265(15) 0.0365(5) Uani 1 1 d . . . . .
H33 H 0.558947 0.351048 0.659950 0.044 Uiso 1 1 calc R U . . .
C34 C 0.88797(19) 1.12829(14) 0.64387(12) 0.0314(4) Uani 1 1 d . . . . .
C35 C 0.97216(17) 1.05832(15) 0.61553(12) 0.0287(4) Uani 1 1 d . . . . .
C36 C 0.94794(15) 0.94807(14) 0.62259(11) 0.0225(3) Uani 1 1 d . . . . .
C37 C 0.84198(14) 0.90185(13) 0.65752(10) 0.0194(3) Uani 1 1 d . . . . .
C38 C 0.70001(18) 0.42283(15) 0.71188(13) 0.0320(4) Uani 1 1 d . . . . .
H38 H 0.744421 0.357411 0.725613 0.038 Uiso 1 1 calc R U . . .
C39 C 0.74638(16) 0.52161(14) 0.73138(11) 0.0240(3) Uani 1 1 d . . . . .
C40 C 0.86375(16) 0.52978(14) 0.77690(12) 0.0268(4) Uani 1 1 d . . . . .
H40A H 0.883736 0.458432 0.808637 0.032 Uiso 1 1 calc R U . . .
H40B H 0.929119 0.549352 0.735114 0.032 Uiso 1 1 calc R U . . .
C41 C 0.85320(15) 0.61548(14) 0.83746(11) 0.0232(3) Uani 1 1 d . . . . .
C42 C 0.90527(16) 0.60337(16) 0.91708(12) 0.0288(4) Uani 1 1 d . . . . .
H42 H 0.954065 0.541312 0.933303 0.035 Uiso 1 1 calc R U . . .
C43 C 0.88707(18) 0.68054(18) 0.97325(12) 0.0336(4) Uani 1 1 d . . . . .
H43 H 0.924579 0.671786 1.027147 0.040 Uiso 1 1 calc R U . . .
C44 C 0.81440(17) 0.77040(17) 0.95111(12) 0.0309(4) Uani 1 1 d . . . . .
H44 H 0.800827 0.822348 0.990276 0.037 Uiso 1 1 calc R U . . .
C45 C 0.76134(16) 0.78469(14) 0.87173(11) 0.0245(3) Uani 1 1 d . . . . .
H45 H 0.711411 0.846135 0.856016 0.029 Uiso 1 1 calc R U . . .
C46 C 0.78263(14) 0.70754(13) 0.81586(10) 0.0204(3) Uani 1 1 d . . . . .
C47 C 0.65988(19) 0.76314(16) 0.44171(12) 0.0323(4) Uani 1 1 d . . . . .
C48 C 0.69210(17) 0.78584(14) 0.52170(11) 0.0261(4) Uani 1 1 d . . . . .
C49 C 0.76013(15) 0.97673(13) 0.68313(11) 0.0217(3) Uani 1 1 d . . . . .
C50 C 0.78091(18) 1.08759(14) 0.67761(12) 0.0276(4) Uani 1 1 d . . . . .
B1 B 0.66831(16) 0.27688(15) 0.16912(12) 0.0195(3) Uani 1 1 d . . . . .
H1A H 0.593508 0.245146 0.197315 0.023 Uiso 1 1 calc R U . . .
B2 B 0.82779(16) 0.77060(14) 0.65798(12) 0.0197(3) Uani 1 1 d . . . . .
H2A H 0.907597 0.736056 0.672252 0.024 Uiso 1 1 calc R U . . .
H1 H 0.843(2) 0.2913(18) 0.2208(14) 0.031(6) Uiso 1 1 d . . . . .
H2 H 0.666(2) 0.7673(18) 0.7304(14) 0.030(6) Uiso 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
F1 C1 1.346(2) . ?
F2 C9 1.339(2) . ?
F3 C11 1.361(2) . ?
F4 C2 1.341(2) . ?
F5 C14 1.348(2) . ?
F6 C13 1.345(2) . ?
F7 C3 1.353(2) . ?
F8 C24 1.349(2) . ?
F9 C25 1.344(3) . ?
F10 C10 1.347(2) . ?
F11 C26 1.350(2) . ?
F12 C34 1.345(2) . ?
F13 C35 1.341(2) . ?
F14 C48 1.356(2) . ?
F15 C47 1.346(2) . ?
F16 C27 1.342(2) . ?
F17 C28 1.338(2) . ?
F18 C50 1.346(2) . ?
F19 C49 1.359(2) . ?
F20 C36 1.347(2) . ?
N1 C5 1.477(2) . ?
N1 C15 1.473(2) . ?
N1 B1 1.683(2) . ?
N1 H1 0.90(2) . ?
N2 C30 1.477(2) . ?
N2 C46 1.474(2) . ?
N2 B2 1.665(2) . ?
N2 H2 0.90(2) . ?
C1 C2 1.377(3) . ?
C1 C13 1.371(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.383(2) . ?
C4 C14 1.391(2) . ?
C4 B1 1.622(2) . ?
C5 C6 1.386(2) . ?
C5 C22 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9500 . ?
C8 C23 1.390(3) . ?
C9 C10 1.372(3) . ?
C9 C25 1.370(4) . ?
C10 C11 1.382(3) . ?
C11 C12 1.382(2) . ?
C12 C24 1.388(2) . ?
C12 B1 1.621(2) . ?
C13 C14 1.382(3) . ?
C15 C16 1.383(3) . ?
C15 C20 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(3) . ?
C20 C21 1.501(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.507(3) . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C26 C27 1.365(3) . ?
C26 C47 1.377(3) . ?
C27 C28 1.387(3) . ?
C28 C29 1.390(3) . ?
C29 C48 1.380(3) . ?
C29 B2 1.620(2) . ?
C30 C31 1.389(2) . ?
C30 C39 1.386(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.389(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C38 1.384(3) . ?
C34 C35 1.375(3) . ?
C34 C50 1.373(3) . ?
C35 C36 1.379(2) . ?
C36 C37 1.393(2) . ?
C37 C49 1.383(2) . ?
C37 B2 1.626(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.392(2) . ?
C39 C40 1.507(2) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.507(2) . ?
C41 C42 1.387(2) . ?
C41 C46 1.391(2) . ?
C42 H42 0.9500 . ?
C42 C43 1.385(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.389(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.387(2) . ?
C47 C48 1.379(3) . ?
C49 C50 1.381(2) . ?
B1 H1A 1.0000 . ?
B2 H2A 1.0000 . ?

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
C5 N1 B1 111.29(12) . . ?
C5 N1 H1 107.6(14) . . ?
C15 N1 C5 111.31(13) . . ?
C15 N1 B1 110.42(12) . . ?
C15 N1 H1 108.7(14) . . ?
B1 N1 H1 107.4(14) . . ?
C30 N2 B2 111.59(12) . . ?
C30 N2 H2 106.8(14) . . ?
C46 N2 C30 110.72(12) . . ?
C46 N2 B2 110.47(12) . . ?
C46 N2 H2 109.4(14) . . ?
B2 N2 H2 107.7(14) . . ?
F1 C1 C2 120.27(19) . . ?
F1 C1 C13 119.68(18) . . ?
C13 C1 C2 120.04(17) . . ?
F4 C2 C1 119.96(17) . . ?
F4 C2 C3 121.27(18) . . ?
C1 C2 C3 118.76(17) . . ?
F7 C3 C2 116.43(16) . . ?
F7 C3 C4 119.53(15) . . ?
C2 C3 C4 124.01(17) . . ?
C3 C4 C14 114.54(16) . . ?
C3 C4 B1 123.88(15) . . ?
C14 C4 B1 121.45(15) . . ?
C6 C5 N1 120.08(16) . . ?
C6 C5 C22 122.22(17) . . ?
C22 C5 N1 117.68(15) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.88(19) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.09(19) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C23 120.31(19) . . ?
C23 C8 H8 119.8 . . ?
F2 C9 C10 120.2(2) . . ?
F2 C9 C25 120.5(2) . . ?
C25 C9 C10 119.29(18) . . ?
F10 C10 C9 120.22(18) . . ?
F10 C10 C11 120.3(2) . . ?
C9 C10 C11 119.47(19) . . ?
F3 C11 C10 116.07(17) . . ?
F3 C11 C12 119.95(15) . . ?
C12 C11 C10 123.98(18) . . ?
C11 C12 C24 113.73(16) . . ?
C11 C12 B1 129.32(15) . . ?
C24 C12 B1 116.94(15) . . ?
F6 C13 C1 119.62(17) . . ?
F6 C13 C14 121.12(18) . . ?
C1 C13 C14 119.24(17) . . ?
F5 C14 C4 120.38(16) . . ?
F5 C14 C13 116.23(16) . . ?
C13 C14 C4 123.35(17) . . ?
C16 C15 N1 118.91(15) . . ?
C16 C15 C20 122.75(16) . . ?
C20 C15 N1 118.20(15) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.79(18) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.79(19) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.34(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.98(19) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 117.29(18) . . ?
C15 C20 C21 119.56(16) . . ?
C19 C20 C21 123.15(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 C22 110.76(15) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C5 C22 C21 120.04(16) . . ?
C5 C22 C23 117.68(18) . . ?
C23 C22 C21 122.22(17) . . ?
C8 C23 C22 120.81(19) . . ?
C8 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
F8 C24 C12 119.08(16) . . ?
F8 C24 C25 116.79(17) . . ?
C25 C24 C12 124.13(19) . . ?
F9 C25 C9 120.61(19) . . ?
F9 C25 C24 120.1(2) . . ?
C9 C25 C24 119.3(2) . . ?
F11 C26 C27 120.4(2) . . ?
F11 C26 C47 119.3(2) . . ?
C27 C26 C47 120.34(17) . . ?
F16 C27 C26 119.92(19) . . ?
F16 C27 C28 120.7(2) . . ?
C26 C27 C28 119.41(19) . . ?
F17 C28 C27 116.62(18) . . ?
F17 C28 C29 120.66(17) . . ?
C27 C28 C29 122.7(2) . . ?
C28 C29 B2 121.99(16) . . ?
C48 C29 C28 115.04(17) . . ?
C48 C29 B2 122.91(15) . . ?
C31 C30 N2 119.66(14) . . ?
C39 C30 N2 117.85(15) . . ?
C39 C30 C31 122.49(15) . . ?
C30 C31 H31 120.7 . . ?
C30 C31 C32 118.55(16) . . ?
C32 C31 H31 120.7 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 119.90(17) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.7 . . ?
C38 C33 C32 120.56(17) . . ?
C38 C33 H33 119.7 . . ?
F12 C34 C35 120.29(18) . . ?
F12 C34 C50 120.12(18) . . ?
C50 C34 C35 119.59(16) . . ?
F13 C35 C34 120.16(16) . . ?
F13 C35 C36 120.64(18) . . ?
C34 C35 C36 119.21(17) . . ?
F20 C36 C35 116.66(16) . . ?
F20 C36 C37 119.53(15) . . ?
C35 C36 C37 123.80(17) . . ?
C36 C37 B2 116.79(14) . . ?
C49 C37 C36 114.12(15) . . ?
C49 C37 B2 128.98(15) . . ?
C33 C38 H38 119.7 . . ?
C33 C38 C39 120.57(17) . . ?
C39 C38 H38 119.7 . . ?
C30 C39 C38 117.91(16) . . ?
C30 C39 C40 119.32(15) . . ?
C38 C39 C40 122.73(16) . . ?
C39 C40 H40A 109.8 . . ?
C39 C40 H40B 109.8 . . ?
H40A C40 H40B 108.2 . . ?
C41 C40 C39 109.53(14) . . ?
C41 C40 H40A 109.8 . . ?
C41 C40 H40B 109.8 . . ?
C42 C41 C40 122.49(16) . . ?
C42 C41 C46 117.91(16) . . ?
C46 C41 C40 119.46(15) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 C41 120.89(17) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 H43 119.9 . . ?
C44 C43 C42 120.22(17) . . ?
C44 C43 H43 119.9 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.10(17) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 120.6 . . ?
C46 C45 C44 118.72(17) . . ?
C46 C45 H45 120.6 . . ?
C41 C46 N2 117.53(14) . . ?
C45 C46 N2 120.33(15) . . ?
C45 C46 C41 122.13(16) . . ?
F15 C47 C26 120.21(17) . . ?
F15 C47 C48 121.31(19) . . ?
C26 C47 C48 118.47(19) . . ?
F14 C48 C29 119.11(15) . . ?
F14 C48 C47 116.88(17) . . ?
C47 C48 C29 124.00(18) . . ?
F19 C49 C37 119.89(14) . . ?
F19 C49 C50 116.16(15) . . ?
C50 C49 C37 123.95(16) . . ?
F18 C50 C34 120.32(16) . . ?
F18 C50 C49 120.37(17) . . ?
C34 C50 C49 119.31(17) . . ?
N1 B1 H1A 107.8 . . ?
C4 B1 N1 108.04(12) . . ?
C4 B1 H1A 107.8 . . ?
C12 B1 N1 111.82(13) . . ?
C12 B1 C4 113.28(13) . . ?
C12 B1 H1A 107.8 . . ?
N2 B2 H2A 108.1 . . ?
C29 B2 N2 110.08(13) . . ?
C29 B2 C37 110.89(13) . . ?
C29 B2 H2A 108.1 . . ?
C37 B2 N2 111.53(13) . . ?
C37 B2 H2A 108.1 . . ?

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
F1 C1 C2 F4 0.0(3) . . . . ?
F1 C1 C2 C3 -178.82(16) . . . . ?
F1 C1 C13 F6 2.4(3) . . . . ?
F1 C1 C13 C14 -179.39(16) . . . . ?
F2 C9 C10 F10 -0.2(3) . . . . ?
F2 C9 C10 C11 -179.70(18) . . . . ?
F2 C9 C25 F9 0.5(3) . . . . ?
F2 C9 C25 C24 -179.65(18) . . . . ?
F3 C11 C12 C24 -176.15(15) . . . . ?
F3 C11 C12 B1 2.4(3) . . . . ?
F4 C2 C3 F7 -1.7(2) . . . . ?
F4 C2 C3 C4 -179.83(15) . . . . ?
F6 C13 C14 F5 -2.4(2) . . . . ?
F6 C13 C14 C4 175.48(16) . . . . ?
F7 C3 C4 C14 -178.20(14) . . . . ?
F7 C3 C4 B1 -2.2(2) . . . . ?
F8 C24 C25 F9 0.8(3) . . . . ?
F8 C24 C25 C9 -179.05(18) . . . . ?
F10 C10 C11 F3 -2.1(2) . . . . ?
F10 C10 C11 C12 178.71(16) . . . . ?
F11 C26 C27 F16 0.5(3) . . . . ?
F11 C26 C27 C28 -179.42(17) . . . . ?
F11 C26 C47 F15 0.3(3) . . . . ?
F11 C26 C47 C48 -179.50(16) . . . . ?
F12 C34 C35 F13 -0.9(3) . . . . ?
F12 C34 C35 C36 179.09(16) . . . . ?
F12 C34 C50 F18 1.7(3) . . . . ?
F12 C34 C50 C49 -179.38(16) . . . . ?
F13 C35 C36 F20 -1.3(2) . . . . ?
F13 C35 C36 C37 179.76(15) . . . . ?
F15 C47 C48 F14 0.2(3) . . . . ?
F15 C47 C48 C29 179.35(16) . . . . ?
F16 C27 C28 F17 -1.4(3) . . . . ?
F16 C27 C28 C29 178.67(17) . . . . ?
F17 C28 C29 C48 -179.60(16) . . . . ?
F17 C28 C29 B2 3.1(3) . . . . ?
F19 C49 C50 F18 0.0(2) . . . . ?
F19 C49 C50 C34 -178.91(16) . . . . ?
F20 C36 C37 C49 -177.38(14) . . . . ?
F20 C36 C37 B2 -0.7(2) . . . . ?
N1 C5 C6 C7 -179.40(16) . . . . ?
N1 C5 C22 C21 2.1(2) . . . . ?
N1 C5 C22 C23 179.46(15) . . . . ?
N1 C15 C16 C17 -173.07(16) . . . . ?
N1 C15 C20 C19 172.78(15) . . . . ?
N1 C15 C20 C21 -8.1(2) . . . . ?
N2 C30 C31 C32 179.19(16) . . . . ?
N2 C30 C39 C38 -179.79(16) . . . . ?
N2 C30 C39 C40 2.6(2) . . . . ?
C1 C2 C3 F7 177.11(15) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C13 C14 F5 179.36(16) . . . . ?
C1 C13 C14 C4 -2.7(3) . . . . ?
C2 C1 C13 F6 -176.80(16) . . . . ?
C2 C1 C13 C14 1.4(3) . . . . ?
C2 C3 C4 C14 -0.1(2) . . . . ?
C2 C3 C4 B1 175.85(16) . . . . ?
C3 C4 C14 F5 179.85(14) . . . . ?
C3 C4 C14 C13 2.0(2) . . . . ?
C3 C4 B1 N1 -80.99(18) . . . . ?
C3 C4 B1 C12 43.5(2) . . . . ?
C5 N1 C15 C16 -141.04(16) . . . . ?
C5 N1 C15 C20 43.3(2) . . . . ?
C5 N1 B1 C4 -155.27(13) . . . . ?
C5 N1 B1 C12 79.42(16) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C22 C23 C8 -0.1(3) . . . . ?
C6 C5 C22 C21 -176.02(17) . . . . ?
C6 C5 C22 C23 1.3(3) . . . . ?
C6 C7 C8 C23 1.2(3) . . . . ?
C7 C8 C23 C22 -1.2(3) . . . . ?
C9 C10 C11 F3 177.36(17) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C10 C9 C25 F9 -178.92(18) . . . . ?
C10 C9 C25 C24 1.0(3) . . . . ?
C10 C11 C12 C24 3.0(3) . . . . ?
C10 C11 C12 B1 -178.41(16) . . . . ?
C11 C12 C24 F8 177.17(15) . . . . ?
C11 C12 C24 C25 -2.3(3) . . . . ?
C11 C12 B1 N1 21.6(2) . . . . ?
C11 C12 B1 C4 -100.8(2) . . . . ?
C12 C24 C25 F9 -179.69(17) . . . . ?
C12 C24 C25 C9 0.4(3) . . . . ?
C13 C1 C2 F4 179.16(16) . . . . ?
C13 C1 C2 C3 0.3(3) . . . . ?
C14 C4 B1 N1 94.71(17) . . . . ?
C14 C4 B1 C12 -140.85(16) . . . . ?
C15 N1 C5 C6 138.27(16) . . . . ?
C15 N1 C5 C22 -39.91(19) . . . . ?
C15 N1 B1 C4 -31.13(17) . . . . ?
C15 N1 B1 C12 -156.45(14) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C15 C20 C21 C22 -29.1(2) . . . . ?
C16 C15 C20 C19 -2.7(3) . . . . ?
C16 C15 C20 C21 176.35(17) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
C18 C19 C20 C15 0.9(3) . . . . ?
C18 C19 C20 C21 -178.17(19) . . . . ?
C19 C20 C21 C22 149.91(18) . . . . ?
C20 C15 C16 C17 2.4(3) . . . . ?
C20 C21 C22 C5 32.3(2) . . . . ?
C20 C21 C22 C23 -144.90(17) . . . . ?
C21 C22 C23 C8 177.20(18) . . . . ?
C22 C5 C6 C7 -1.3(3) . . . . ?
C24 C12 B1 N1 -159.85(14) . . . . ?
C24 C12 B1 C4 77.78(19) . . . . ?
C25 C9 C10 F10 179.16(18) . . . . ?
C25 C9 C10 C11 -0.3(3) . . . . ?
C26 C27 C28 F17 178.42(17) . . . . ?
C26 C27 C28 C29 -1.5(3) . . . . ?
C26 C47 C48 F14 -179.97(16) . . . . ?
C26 C47 C48 C29 -0.8(3) . . . . ?
C27 C26 C47 F15 179.41(17) . . . . ?
C27 C26 C47 C48 -0.4(3) . . . . ?
C27 C28 C29 C48 0.3(3) . . . . ?
C27 C28 C29 B2 -177.01(17) . . . . ?
C28 C29 C48 F14 179.99(15) . . . . ?
C28 C29 C48 C47 0.9(3) . . . . ?
C28 C29 B2 N2 -112.06(17) . . . . ?
C28 C29 B2 C37 124.03(17) . . . . ?
C30 N2 C46 C41 43.02(19) . . . . ?
C30 N2 C46 C45 -135.81(16) . . . . ?
C30 N2 B2 C29 33.61(17) . . . . ?
C30 N2 B2 C37 157.14(13) . . . . ?
C30 C31 C32 C33 1.0(3) . . . . ?
C30 C39 C40 C41 35.2(2) . . . . ?
C31 C30 C39 C38 -0.1(3) . . . . ?
C31 C30 C39 C40 -177.70(17) . . . . ?
C31 C32 C33 C38 -0.9(3) . . . . ?
C32 C33 C38 C39 0.3(3) . . . . ?
C33 C38 C39 C30 0.2(3) . . . . ?
C33 C38 C39 C40 177.71(19) . . . . ?
C34 C35 C36 F20 178.68(16) . . . . ?
C34 C35 C36 C37 -0.3(3) . . . . ?
C35 C34 C50 F18 -178.37(17) . . . . ?
C35 C34 C50 C49 0.5(3) . . . . ?
C35 C36 C37 C49 1.6(2) . . . . ?
C35 C36 C37 B2 178.28(16) . . . . ?
C36 C37 C49 F19 177.93(14) . . . . ?
C36 C37 C49 C50 -1.9(2) . . . . ?
C36 C37 B2 N2 158.35(14) . . . . ?
C36 C37 B2 C29 -78.58(18) . . . . ?
C37 C49 C50 F18 179.81(16) . . . . ?
C37 C49 C50 C34 0.9(3) . . . . ?
C38 C39 C40 C41 -142.31(18) . . . . ?
C39 C30 C31 C32 -0.5(3) . . . . ?
C39 C40 C41 C42 141.48(17) . . . . ?
C39 C40 C41 C46 -34.3(2) . . . . ?
C40 C41 C42 C43 -175.69(17) . . . . ?
C40 C41 C46 N2 -4.3(2) . . . . ?
C40 C41 C46 C45 174.54(16) . . . . ?
C41 C42 C43 C44 1.2(3) . . . . ?
C42 C41 C46 N2 179.71(15) . . . . ?
C42 C41 C46 C45 -1.5(2) . . . . ?
C42 C43 C44 C45 -1.3(3) . . . . ?
C43 C44 C45 C46 0.1(3) . . . . ?
C44 C45 C46 N2 -179.86(15) . . . . ?
C44 C45 C46 C41 1.4(3) . . . . ?
C46 N2 C30 C31 138.05(16) . . . . ?
C46 N2 C30 C39 -42.2(2) . . . . ?
C46 N2 B2 C29 157.25(13) . . . . ?
C46 N2 B2 C37 -79.22(16) . . . . ?
C46 C41 C42 C43 0.2(3) . . . . ?
C47 C26 C27 F16 -178.63(18) . . . . ?
C47 C26 C27 C28 1.5(3) . . . . ?
C48 C29 B2 N2 70.86(19) . . . . ?
C48 C29 B2 C37 -53.0(2) . . . . ?
C49 C37 B2 N2 -25.5(2) . . . . ?
C49 C37 B2 C29 97.6(2) . . . . ?
C50 C34 C35 F13 179.14(16) . . . . ?
C50 C34 C35 C36 -0.8(3) . . . . ?
B1 N1 C5 C6 -98.10(18) . . . . ?
B1 N1 C5 C22 83.73(17) . . . . ?
B1 N1 C15 C16 94.83(17) . . . . ?
B1 N1 C15 C20 -80.85(18) . . . . ?
B1 C4 C14 F5 3.8(2) . . . . ?
B1 C4 C14 C13 -174.06(16) . . . . ?
B1 C12 C24 F8 -1.6(2) . . . . ?
B1 C12 C24 C25 178.91(17) . . . . ?
B2 N2 C30 C31 -98.46(17) . . . . ?
B2 N2 C30 C39 81.25(18) . . . . ?
B2 N2 C46 C41 -81.11(17) . . . . ?
B2 N2 C46 C45 100.05(17) . . . . ?
B2 C29 C48 F14 -2.7(2) . . . . ?
B2 C29 C48 C47 178.14(16) . . . . ?
B2 C37 C49 F19 1.7(3) . . . . ?
B2 C37 C49 C50 -178.10(16) . . . . ?

_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_jnb036cc_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068072'
loop_
_audit_author_name
_audit_author_address
'Christopher Caputo'
;York University
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-17
_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         'C24 H8 B F10 N'
_chemical_formula_sum            'C24 H8 B F10 N'
_chemical_formula_weight         511.12
_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'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.6108(4)
_cell_length_b                   9.4314(7)
_cell_length_c                   27.7355(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.802(2)
_cell_angle_gamma                90
_cell_volume                     1983.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1559 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.8611.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.2
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            22903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                3725
_reflns_number_total             4547
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.293
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+1.4738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16)
;
_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
F1 F 0.4644(2) 1.11090(14) 0.54826(5) 0.0525(4) Uani 1 1 d . . . . .
F2 F 0.42888(19) 0.46857(16) 0.54409(5) 0.0514(4) Uani 1 1 d . . . . .
F3 F 0.2151(3) 0.31996(17) 0.48020(5) 0.0708(5) Uani 1 1 d . . . . .
F4 F -0.1197(3) 0.25935(16) 0.50078(5) 0.0719(5) Uani 1 1 d . . . . .
F5 F -0.24006(18) 0.35192(16) 0.58432(5) 0.0561(4) Uani 1 1 d . . . . .
F6 F -0.02473(15) 0.49648(13) 0.64873(4) 0.0361(3) Uani 1 1 d . . . . .
F7 F 0.13238(18) 1.03244(13) 0.56553(5) 0.0504(4) Uani 1 1 d . . . . .
F8 F 0.07698(15) 0.78424(12) 0.60927(4) 0.0351(3) Uani 1 1 d . . . . .
F9 F 0.68770(15) 0.69277(13) 0.62075(4) 0.0394(3) Uani 1 1 d . . . . .
F10 F 0.74148(17) 0.94173(14) 0.57661(5) 0.0456(3) Uani 1 1 d . . . . .
N1 N 0.40857(19) 0.51609(15) 0.67919(5) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.3986(2) 0.1101(2) 0.74096(7) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.395557 0.020738 0.756692 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3336(2) 0.12306(19) 0.69292(7) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.289357 0.041144 0.676062 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3311(3) 0.25192(19) 0.66873(7) 0.0279(4) Uani 1 1 d . . . . .
H3 H 0.287459 0.259006 0.635707 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3945(2) 0.37008(18) 0.69444(6) 0.0228(4) Uani 1 1 d . . . . .
B5 B 0.3390(3) 0.5746(2) 0.63508(7) 0.0234(4) Uani 1 1 d . . . . .
C6 C 0.3800(2) 0.72882(19) 0.61637(6) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.5475(2) 0.7741(2) 0.60720(6) 0.0271(4) Uani 1 1 d . . . . .
C8 C 0.5785(3) 0.9015(2) 0.58456(7) 0.0313(4) Uani 1 1 d . . . . .
C9 C 0.4371(3) 0.9873(2) 0.57026(7) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.4677(2) 0.2264(2) 0.76590(6) 0.0267(4) Uani 1 1 d . . . . .
H10 H 0.515556 0.217883 0.798516 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4660(2) 0.35659(18) 0.74235(6) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.5325(2) 0.49363(19) 0.75807(6) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.6158(2) 0.5381(2) 0.80215(7) 0.0290(4) Uani 1 1 d . . . . .
H13 H 0.640906 0.472718 0.827868 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6611(3) 0.6791(2) 0.80760(7) 0.0314(4) Uani 1 1 d . . . . .
H14 H 0.720059 0.711359 0.837125 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6208(2) 0.7742(2) 0.77002(7) 0.0284(4) Uani 1 1 d . . . . .
H15 H 0.650876 0.871245 0.774650 0.034 Uiso 1 1 calc R U . . .
C16 C 0.5379(2) 0.73162(19) 0.72595(6) 0.0257(4) Uani 1 1 d . . . . .
H16 H 0.509941 0.797941 0.700692 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4973(2) 0.58900(19) 0.72000(6) 0.0219(3) Uani 1 1 d . . . . .
C18 C 0.2095(3) 0.48623(19) 0.59858(6) 0.0261(4) Uani 1 1 d . . . . .
C19 C 0.2645(3) 0.4404(2) 0.55477(7) 0.0352(5) Uani 1 1 d . . . . .
C20 C 0.1565(4) 0.3636(2) 0.52196(7) 0.0440(6) Uani 1 1 d . . . . .
C21 C -0.0118(4) 0.3333(2) 0.53211(7) 0.0449(6) Uani 1 1 d . . . . .
C22 C -0.0741(3) 0.3796(2) 0.57479(8) 0.0377(5) Uani 1 1 d . . . . .
C23 C 0.0379(3) 0.45468(19) 0.60716(6) 0.0280(4) Uani 1 1 d . . . . .
C24 C 0.2429(2) 0.81973(19) 0.60133(6) 0.0261(4) Uani 1 1 d . . . . .
C25 C 0.2685(3) 0.9478(2) 0.57871(7) 0.0310(4) 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
F1 C9 1.340(2) . ?
F2 C19 1.336(3) . ?
F3 C20 1.340(3) . ?
F4 C21 1.340(2) . ?
F5 C22 1.338(3) . ?
F6 C23 1.343(2) . ?
F7 C25 1.334(2) . ?
F8 C24 1.343(2) . ?
F9 C7 1.342(2) . ?
F10 C8 1.333(2) . ?
N1 C4 1.447(2) . ?
N1 B5 1.405(2) . ?
N1 C17 1.443(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C10 1.378(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 C11 1.399(2) . ?
B5 C6 1.584(3) . ?
B5 C18 1.589(3) . ?
C6 C7 1.388(3) . ?
C6 C24 1.387(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.378(3) . ?
C9 C25 1.375(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 C12 1.442(2) . ?
C12 C13 1.394(2) . ?
C12 C17 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C18 C19 1.387(3) . ?
C18 C23 1.379(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.365(4) . ?
C21 C22 1.382(3) . ?
C22 C23 1.381(3) . ?
C24 C25 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B5 N1 C4 126.62(15) . . ?
B5 N1 C17 127.85(15) . . ?
C17 N1 C4 105.40(13) . . ?
C2 C1 H1 119.9 . . ?
C10 C1 H1 119.9 . . ?
C10 C1 C2 120.15(17) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.08(18) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.69(16) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 N1 130.16(15) . . ?
C3 C4 C11 120.40(16) . . ?
C11 C4 N1 109.37(15) . . ?
N1 B5 C6 125.16(16) . . ?
N1 B5 C18 121.17(16) . . ?
C6 B5 C18 113.66(15) . . ?
C7 C6 B5 123.46(16) . . ?
C24 C6 B5 120.17(17) . . ?
C24 C6 C7 115.71(17) . . ?
F9 C7 C6 119.60(16) . . ?
F9 C7 C8 117.44(17) . . ?
C8 C7 C6 122.96(17) . . ?
F10 C8 C7 121.22(18) . . ?
F10 C8 C9 120.03(18) . . ?
C9 C8 C7 118.75(18) . . ?
F1 C9 C8 119.68(19) . . ?
F1 C9 C25 119.69(19) . . ?
C25 C9 C8 120.63(18) . . ?
C1 C10 H10 120.7 . . ?
C1 C10 C11 118.65(16) . . ?
C11 C10 H10 120.7 . . ?
C4 C11 C12 107.72(15) . . ?
C10 C11 C4 120.94(16) . . ?
C10 C11 C12 131.32(16) . . ?
C13 C12 C11 131.09(17) . . ?
C13 C12 C17 120.93(17) . . ?
C17 C12 C11 107.98(15) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.52(17) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.16(17) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.02(18) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.76(17) . . ?
C17 C16 H16 121.1 . . ?
C12 C17 N1 109.49(15) . . ?
C16 C17 N1 129.84(16) . . ?
C16 C17 C12 120.55(16) . . ?
C19 C18 B5 120.31(18) . . ?
C23 C18 B5 123.32(16) . . ?
C23 C18 C19 116.33(18) . . ?
F2 C19 C18 119.31(19) . . ?
F2 C19 C20 118.37(19) . . ?
C20 C19 C18 122.3(2) . . ?
F3 C20 C19 120.6(2) . . ?
F3 C20 C21 120.0(2) . . ?
C21 C20 C19 119.5(2) . . ?
F4 C21 C20 120.7(2) . . ?
F4 C21 C22 119.0(2) . . ?
C20 C21 C22 120.37(19) . . ?
F5 C22 C21 120.33(19) . . ?
F5 C22 C23 120.9(2) . . ?
C23 C22 C21 118.8(2) . . ?
F6 C23 C18 119.59(16) . . ?
F6 C23 C22 117.69(19) . . ?
C18 C23 C22 122.72(19) . . ?
F8 C24 C6 119.38(16) . . ?
F8 C24 C25 117.54(16) . . ?
C25 C24 C6 123.08(18) . . ?
F7 C25 C9 120.35(18) . . ?
F7 C25 C24 120.78(18) . . ?
C9 C25 C24 118.87(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
F1 C9 C25 F7 -0.6(3) . . . . ?
F1 C9 C25 C24 179.84(17) . . . . ?
F2 C19 C20 F3 -0.8(3) . . . . ?
F2 C19 C20 C21 179.87(18) . . . . ?
F3 C20 C21 F4 0.4(3) . . . . ?
F3 C20 C21 C22 -179.11(19) . . . . ?
F4 C21 C22 F5 -0.6(3) . . . . ?
F4 C21 C22 C23 179.46(17) . . . . ?
F5 C22 C23 F6 1.2(3) . . . . ?
F5 C22 C23 C18 -179.56(17) . . . . ?
F8 C24 C25 F7 0.2(3) . . . . ?
F8 C24 C25 C9 179.74(17) . . . . ?
F9 C7 C8 F10 -0.1(3) . . . . ?
F9 C7 C8 C9 -179.96(17) . . . . ?
F10 C8 C9 F1 0.2(3) . . . . ?
F10 C8 C9 C25 -179.28(18) . . . . ?
N1 C4 C11 C10 179.57(15) . . . . ?
N1 C4 C11 C12 -1.85(19) . . . . ?
N1 B5 C6 C7 61.8(3) . . . . ?
N1 B5 C6 C24 -127.9(2) . . . . ?
N1 B5 C18 C19 -110.6(2) . . . . ?
N1 B5 C18 C23 71.6(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C10 C11 C4 0.5(3) . . . . ?
C1 C10 C11 C12 -177.71(18) . . . . ?
C2 C1 C10 C11 1.8(3) . . . . ?
C2 C3 C4 N1 179.91(17) . . . . ?
C2 C3 C4 C11 3.1(3) . . . . ?
C3 C4 C11 C10 -3.0(3) . . . . ?
C3 C4 C11 C12 175.60(16) . . . . ?
C4 N1 B5 C6 -170.64(16) . . . . ?
C4 N1 B5 C18 8.7(3) . . . . ?
C4 N1 C17 C12 -0.93(18) . . . . ?
C4 N1 C17 C16 -176.88(18) . . . . ?
C4 C11 C12 C13 -179.89(19) . . . . ?
C4 C11 C12 C17 1.2(2) . . . . ?
B5 N1 C4 C3 8.5(3) . . . . ?
B5 N1 C4 C11 -174.37(17) . . . . ?
B5 N1 C17 C12 175.09(17) . . . . ?
B5 N1 C17 C16 -0.9(3) . . . . ?
B5 C6 C7 F9 -9.6(3) . . . . ?
B5 C6 C7 C8 170.70(17) . . . . ?
B5 C6 C24 F8 9.6(2) . . . . ?
B5 C6 C24 C25 -171.13(17) . . . . ?
B5 C18 C19 F2 1.5(3) . . . . ?
B5 C18 C19 C20 -179.94(17) . . . . ?
B5 C18 C23 F6 -1.7(3) . . . . ?
B5 C18 C23 C22 179.03(17) . . . . ?
C6 B5 C18 C19 68.8(2) . . . . ?
C6 B5 C18 C23 -108.99(19) . . . . ?
C6 C7 C8 F10 179.62(17) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 C24 C25 F7 -179.06(17) . . . . ?
C6 C24 C25 C9 0.5(3) . . . . ?
C7 C6 C24 F8 -179.39(15) . . . . ?
C7 C6 C24 C25 -0.1(3) . . . . ?
C7 C8 C9 F1 -179.94(17) . . . . ?
C7 C8 C9 C25 0.6(3) . . . . ?
C8 C9 C25 F7 178.83(18) . . . . ?
C8 C9 C25 C24 -0.7(3) . . . . ?
C10 C1 C2 C3 -1.7(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C10 C11 C12 C17 179.63(18) . . . . ?
C11 C12 C13 C14 -177.97(19) . . . . ?
C11 C12 C17 N1 -0.17(19) . . . . ?
C11 C12 C17 C16 176.23(16) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C12 C17 N1 -179.17(16) . . . . ?
C13 C12 C17 C16 -2.8(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 N1 178.25(17) . . . . ?
C15 C16 C17 C12 2.7(3) . . . . ?
C17 N1 C4 C3 -175.40(19) . . . . ?
C17 N1 C4 C11 1.72(18) . . . . ?
C17 N1 B5 C6 14.1(3) . . . . ?
C17 N1 B5 C18 -166.49(16) . . . . ?
C17 C12 C13 C14 0.8(3) . . . . ?
C18 B5 C6 C7 -117.58(19) . . . . ?
C18 B5 C6 C24 52.7(2) . . . . ?
C18 C19 C20 F3 -179.31(18) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C19 C18 C23 F6 -179.62(16) . . . . ?
C19 C18 C23 C22 1.1(3) . . . . ?
C19 C20 C21 F4 179.72(18) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 F5 178.84(19) . . . . ?
C20 C21 C22 C23 -1.1(3) . . . . ?
C21 C22 C23 F6 -178.92(17) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C23 C18 C19 F2 179.49(16) . . . . ?
C23 C18 C19 C20 -2.0(3) . . . . ?
C24 C6 C7 F9 179.72(16) . . . . ?
C24 C6 C7 C8 0.0(3) . . . . ?

_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_jnb056cc_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068074'
loop_
_audit_author_name
_audit_author_address
'Christopher Caputo'
;York University
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_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         '2(C31 H18 B F10 N3)'
_chemical_formula_sum            'C62 H36 B2 F20 N6'
_chemical_formula_weight         1266.59
_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'
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'

_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                   30.583(10)
_cell_length_b                   14.745(5)
_cell_length_c                   17.429(6)
_cell_angle_alpha                90
_cell_angle_beta                 122.794(12)
_cell_angle_gamma                90
_cell_volume                     6607(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8756
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.6925
_exptl_absorpt_correction_T_min  0.5962
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.1161 after correction.
The Ratio of minimum to maximum transmission is 0.8609.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            89071
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         1.809
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                5036
_reflns_number_total             7582
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+10.7563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1670
_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:
 C1(H1), C2(H2), C6(H6), C7(H7), C10(H10), C11(H11), C19(H19), C20(H20),
 C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
F1 F 0.62407(8) 0.24541(11) 0.66367(13) 0.0649(5) Uani 1 1 d . . . . .
F2 F 0.68856(6) 0.38114(11) 0.74552(11) 0.0506(4) Uani 1 1 d . . . . .
F3 F 0.53225(8) 0.26879(13) 0.50092(13) 0.0718(6) Uani 1 1 d . . . . .
F4 F 0.50515(6) 0.43732(13) 0.42566(11) 0.0605(5) Uani 1 1 d . . . . .
F5 F 0.56683(6) 0.57771(11) 0.51049(10) 0.0472(4) Uani 1 1 d . . . . .
F6 F 0.61692(8) 0.56566(15) 0.91040(12) 0.0737(6) Uani 1 1 d . . . . .
F7 F 0.67088(7) 0.50858(12) 0.84105(11) 0.0569(5) Uani 1 1 d . . . . .
F8 F 0.55055(6) 0.70693(13) 0.83512(11) 0.0571(5) Uani 1 1 d . . . . .
F9 F 0.54212(6) 0.79584(11) 0.68968(11) 0.0516(4) Uani 1 1 d . . . . .
F10 F 0.59452(6) 0.74152(10) 0.61836(10) 0.0444(4) Uani 1 1 d . . . . .
N1 N 0.72697(7) 0.55621(14) 0.75320(13) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.67142(7) 0.64775(13) 0.61535(13) 0.0311(4) Uani 1 1 d . . . . .
N3 N 0.69497(9) 0.83476(15) 0.46088(16) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.84753(12) 0.6666(2) 0.9981(2) 0.0609(9) Uani 1 1 d . . . . .
H1 H 0.876114 0.688836 1.054257 0.073 Uiso 1 1 calc R U . . .
C2 C 0.85564(11) 0.6057(2) 0.9481(2) 0.0532(8) Uani 1 1 d . . . . .
H2 H 0.889912 0.585928 0.968998 0.064 Uiso 1 1 calc R U . . .
C3 C 0.81362(10) 0.57257(18) 0.86655(17) 0.0394(6) Uani 1 1 d . . . . .
C4 C 0.76250(9) 0.59990(17) 0.83580(16) 0.0340(5) Uani 1 1 d . . . . .
B5 B 0.66889(10) 0.57794(19) 0.68363(18) 0.0312(6) Uani 1 1 d . . . . .
C6 C 0.66123(10) 0.62745(17) 0.53124(17) 0.0351(5) Uani 1 1 d . . . . .
H6 H 0.648268 0.568644 0.507505 0.042 Uiso 1 1 calc R U . . .
C7 C 0.66844(10) 0.68609(17) 0.47884(17) 0.0357(5) Uani 1 1 d . . . . .
H7 H 0.660306 0.667566 0.420299 0.043 Uiso 1 1 calc R U . . .
C8 C 0.68786(9) 0.77414(17) 0.51052(17) 0.0339(5) Uani 1 1 d . . . . .
C9 C 0.71489(14) 0.92563(19) 0.4959(2) 0.0575(8) Uani 1 1 d . . . . .
H9A H 0.686853 0.963327 0.490076 0.086 Uiso 1 1 calc R U . . .
H9B H 0.727949 0.952840 0.460739 0.086 Uiso 1 1 calc R U . . .
H9C H 0.743219 0.921668 0.560271 0.086 Uiso 1 1 calc R U . . .
C10 C 0.83143(13) 0.4150(2) 0.7136(2) 0.0577(8) Uani 1 1 d . . . . .
H10 H 0.856464 0.384139 0.707034 0.069 Uiso 1 1 calc R U . . .
C11 C 0.84731(12) 0.4657(2) 0.7906(2) 0.0533(8) Uani 1 1 d . . . . .
H11 H 0.883128 0.469484 0.837639 0.064 Uiso 1 1 calc R U . . .
C12 C 0.81001(10) 0.51178(18) 0.79873(18) 0.0393(6) Uani 1 1 d . . . . .
C13 C 0.63306(9) 0.48808(17) 0.63035(16) 0.0326(5) Uani 1 1 d . . . . .
C14 C 0.58435(10) 0.49552(18) 0.54968(17) 0.0362(5) Uani 1 1 d . . . . .
C15 C 0.55085(10) 0.4237(2) 0.50501(17) 0.0415(6) Uani 1 1 d . . . . .
C16 C 0.56433(11) 0.3397(2) 0.5427(2) 0.0468(7) Uani 1 1 d . . . . .
C17 C 0.61098(12) 0.32760(18) 0.62424(19) 0.0450(6) Uani 1 1 d . . . . .
C18 C 0.64378(10) 0.40041(18) 0.66550(17) 0.0380(6) Uani 1 1 d . . . . .
C19 C 0.69159(9) 0.73174(17) 0.64750(17) 0.0348(5) Uani 1 1 d . . . . .
H19 H 0.700439 0.747532 0.707117 0.042 Uiso 1 1 calc R U . . .
C20 C 0.69975(9) 0.79389(17) 0.59972(17) 0.0348(5) Uani 1 1 d . . . . .
H20 H 0.713621 0.851566 0.626011 0.042 Uiso 1 1 calc R U . . .
C21 C 0.67829(13) 0.8158(2) 0.3665(2) 0.0543(7) Uani 1 1 d . . . . .
H21A H 0.694226 0.759138 0.364030 0.081 Uiso 1 1 calc R U . . .
H21B H 0.689137 0.865635 0.343168 0.081 Uiso 1 1 calc R U . . .
H21C H 0.640333 0.810002 0.328932 0.081 Uiso 1 1 calc R U . . .
C22 C 0.63769(9) 0.62330(16) 0.72769(15) 0.0316(5) Uani 1 1 d . . . . .
C23 C 0.60299(9) 0.69518(17) 0.69209(16) 0.0333(5) Uani 1 1 d . . . . .
C24 C 0.57398(9) 0.72426(17) 0.72689(17) 0.0364(5) Uani 1 1 d . . . . .
C25 C 0.57833(9) 0.6800(2) 0.80009(17) 0.0405(6) Uani 1 1 d . . . . .
C26 C 0.61189(10) 0.6091(2) 0.83786(18) 0.0454(7) Uani 1 1 d . . . . .
C27 C 0.63984(10) 0.58161(18) 0.80111(17) 0.0395(6) Uani 1 1 d . . . . .
C28 C 0.75674(10) 0.50466(16) 0.72996(17) 0.0348(5) Uani 1 1 d . . . . .
C29 C 0.74119(11) 0.45245(17) 0.65221(19) 0.0423(6) Uani 1 1 d . . . . .
H29 H 0.705494 0.447075 0.604948 0.051 Uiso 1 1 calc R U . . .
C30 C 0.77937(13) 0.40873(19) 0.6460(2) 0.0509(7) Uani 1 1 d . . . . .
H30 H 0.769283 0.373287 0.593401 0.061 Uiso 1 1 calc R U . . .
C31 C 0.75471(11) 0.66424(19) 0.88621(18) 0.0430(6) Uani 1 1 d . . . . .
H31 H 0.720760 0.685690 0.865491 0.052 Uiso 1 1 calc R U . . .
C32 C 0.79746(12) 0.6960(2) 0.96686(19) 0.0527(7) Uani 1 1 d . . . . .
H32 H 0.792403 0.739234 1.001807 0.063 Uiso 1 1 calc R U . . .


_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 C17 1.343(3) . ?
F2 C18 1.354(3) . ?
F3 C16 1.346(3) . ?
F4 C15 1.346(3) . ?
F5 C14 1.351(3) . ?
F6 C26 1.350(3) . ?
F7 C27 1.352(3) . ?
F8 C25 1.346(3) . ?
F9 C24 1.341(3) . ?
F10 C23 1.351(3) . ?
N1 C4 1.405(3) . ?
N1 B5 1.548(3) . ?
N1 C28 1.404(3) . ?
N2 B5 1.607(3) . ?
N2 C6 1.357(3) . ?
N2 C19 1.361(3) . ?
N3 C8 1.341(3) . ?
N3 C9 1.461(4) . ?
N3 C21 1.462(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.365(5) . ?
C1 C32 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C3 C4 1.409(4) . ?
C3 C12 1.439(4) . ?
C4 C31 1.398(4) . ?
B5 C13 1.648(4) . ?
B5 C22 1.656(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.360(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.410(3) . ?
C8 C20 1.422(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.374(5) . ?
C10 C30 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(4) . ?
C12 C28 1.410(4) . ?
C13 C14 1.393(3) . ?
C13 C18 1.391(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.359(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.377(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.349(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.386(3) . ?
C22 C27 1.389(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.374(4) . ?
C25 C26 1.360(4) . ?
C26 C27 1.378(4) . ?
C28 C29 1.399(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.384(4) . ?
C32 H32 0.9500 . ?

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
C4 N1 B5 129.1(2) . . ?
C28 N1 C4 106.3(2) . . ?
C28 N1 B5 122.3(2) . . ?
C6 N2 B5 125.7(2) . . ?
C6 N2 C19 115.7(2) . . ?
C19 N2 B5 118.09(19) . . ?
C8 N3 C9 121.2(2) . . ?
C8 N3 C21 121.3(2) . . ?
C21 N3 C9 117.2(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C32 119.9(3) . . ?
C32 C1 H1 120.0 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 C12 132.5(3) . . ?
C4 C3 C12 106.9(2) . . ?
N1 C4 C3 110.0(2) . . ?
C31 C4 N1 130.9(2) . . ?
C31 C4 C3 119.1(2) . . ?
N1 B5 N2 102.57(18) . . ?
N1 B5 C13 113.9(2) . . ?
N1 B5 C22 115.17(19) . . ?
N2 B5 C13 112.45(19) . . ?
N2 B5 C22 110.84(19) . . ?
C13 B5 C22 102.23(18) . . ?
N2 C6 H6 118.0 . . ?
N2 C6 C7 124.0(2) . . ?
C7 C6 H6 118.0 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
N3 C8 C7 122.8(2) . . ?
N3 C8 C20 122.3(2) . . ?
C7 C8 C20 114.9(2) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C30 120.3(3) . . ?
C30 C10 H10 119.8 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C3 133.0(3) . . ?
C11 C12 C28 120.5(3) . . ?
C28 C12 C3 106.5(2) . . ?
C14 C13 B5 121.8(2) . . ?
C18 C13 B5 124.9(2) . . ?
C18 C13 C14 112.7(2) . . ?
F5 C14 C13 119.7(2) . . ?
F5 C14 C15 115.6(2) . . ?
C15 C14 C13 124.7(2) . . ?
F4 C15 C14 120.3(3) . . ?
F4 C15 C16 120.5(2) . . ?
C16 C15 C14 119.2(2) . . ?
F3 C16 C15 120.4(3) . . ?
F3 C16 C17 120.2(3) . . ?
C15 C16 C17 119.4(2) . . ?
F1 C17 C16 120.0(2) . . ?
F1 C17 C18 120.4(3) . . ?
C16 C17 C18 119.6(3) . . ?
F2 C18 C13 121.0(2) . . ?
F2 C18 C17 114.8(2) . . ?
C17 C18 C13 124.3(2) . . ?
N2 C19 H19 118.0 . . ?
C20 C19 N2 123.9(2) . . ?
C20 C19 H19 118.0 . . ?
C8 C20 H20 119.6 . . ?
C19 C20 C8 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 B5 126.5(2) . . ?
C23 C22 C27 113.2(2) . . ?
C27 C22 B5 119.8(2) . . ?
F10 C23 C22 121.2(2) . . ?
F10 C23 C24 114.9(2) . . ?
C24 C23 C22 123.8(2) . . ?
F9 C24 C23 120.1(2) . . ?
F9 C24 C25 120.1(2) . . ?
C25 C24 C23 119.8(2) . . ?
F8 C25 C24 120.9(2) . . ?
F8 C25 C26 120.2(2) . . ?
C26 C25 C24 118.9(2) . . ?
F6 C26 C25 119.4(2) . . ?
F6 C26 C27 120.8(3) . . ?
C25 C26 C27 119.8(2) . . ?
F7 C27 C22 119.8(2) . . ?
F7 C27 C26 115.7(2) . . ?
C26 C27 C22 124.5(2) . . ?
N1 C28 C12 110.2(2) . . ?
C29 C28 N1 130.1(2) . . ?
C29 C28 C12 119.6(2) . . ?
C28 C29 H29 120.9 . . ?
C30 C29 C28 118.2(3) . . ?
C30 C29 H29 120.9 . . ?
C10 C30 C29 122.2(3) . . ?
C10 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C4 C31 H31 120.7 . . ?
C32 C31 C4 118.7(3) . . ?
C32 C31 H31 120.7 . . ?
C1 C32 H32 119.1 . . ?
C31 C32 C1 121.8(3) . . ?
C31 C32 H32 119.1 . . ?

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
F1 C17 C18 F2 0.5(4) . . . . ?
F1 C17 C18 C13 -179.0(2) . . . . ?
F3 C16 C17 F1 -1.8(4) . . . . ?
F3 C16 C17 C18 178.9(2) . . . . ?
F4 C15 C16 F3 0.4(4) . . . . ?
F4 C15 C16 C17 -179.4(2) . . . . ?
F5 C14 C15 F4 2.9(3) . . . . ?
F5 C14 C15 C16 -176.3(2) . . . . ?
F6 C26 C27 F7 1.4(4) . . . . ?
F6 C26 C27 C22 -178.8(3) . . . . ?
F8 C25 C26 F6 0.3(4) . . . . ?
F8 C25 C26 C27 179.5(2) . . . . ?
F9 C24 C25 F8 0.6(4) . . . . ?
F9 C24 C25 C26 -178.4(2) . . . . ?
F10 C23 C24 F9 -2.6(3) . . . . ?
F10 C23 C24 C25 178.0(2) . . . . ?
N1 C4 C31 C32 179.7(3) . . . . ?
N1 B5 C13 C14 -162.2(2) . . . . ?
N1 B5 C13 C18 27.2(3) . . . . ?
N1 B5 C22 C23 136.9(2) . . . . ?
N1 B5 C22 C27 -51.7(3) . . . . ?
N1 C28 C29 C30 179.1(2) . . . . ?
N2 B5 C13 C14 -46.1(3) . . . . ?
N2 B5 C13 C18 143.4(2) . . . . ?
N2 B5 C22 C23 21.1(3) . . . . ?
N2 B5 C22 C27 -167.6(2) . . . . ?
N2 C6 C7 C8 0.4(4) . . . . ?
N2 C19 C20 C8 -0.7(4) . . . . ?
N3 C8 C20 C19 179.2(2) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C12 177.4(3) . . . . ?
C2 C1 C32 C31 1.0(5) . . . . ?
C2 C3 C4 N1 -178.9(2) . . . . ?
C2 C3 C4 C31 3.1(4) . . . . ?
C2 C3 C12 C11 -0.8(5) . . . . ?
C2 C3 C12 C28 -179.1(3) . . . . ?
C3 C4 C31 C32 -2.7(4) . . . . ?
C3 C12 C28 N1 -1.7(3) . . . . ?
C3 C12 C28 C29 177.3(2) . . . . ?
C4 N1 B5 N2 90.5(3) . . . . ?
C4 N1 B5 C13 -147.7(2) . . . . ?
C4 N1 B5 C22 -30.0(3) . . . . ?
C4 N1 C28 C12 2.9(3) . . . . ?
C4 N1 C28 C29 -175.9(2) . . . . ?
C4 C3 C12 C11 178.0(3) . . . . ?
C4 C3 C12 C28 -0.2(3) . . . . ?
C4 C31 C32 C1 0.7(4) . . . . ?
B5 N1 C4 C3 -166.0(2) . . . . ?
B5 N1 C4 C31 11.7(4) . . . . ?
B5 N1 C28 C12 167.3(2) . . . . ?
B5 N1 C28 C29 -11.6(4) . . . . ?
B5 N2 C6 C7 -173.6(2) . . . . ?
B5 N2 C19 C20 174.5(2) . . . . ?
B5 C13 C14 F5 3.9(3) . . . . ?
B5 C13 C14 C15 -175.3(2) . . . . ?
B5 C13 C18 F2 -6.1(4) . . . . ?
B5 C13 C18 C17 173.4(2) . . . . ?
B5 C22 C23 F10 -5.8(4) . . . . ?
B5 C22 C23 C24 173.1(2) . . . . ?
B5 C22 C27 F7 5.5(4) . . . . ?
B5 C22 C27 C26 -174.2(3) . . . . ?
C6 N2 B5 N1 102.3(2) . . . . ?
C6 N2 B5 C13 -20.5(3) . . . . ?
C6 N2 B5 C22 -134.3(2) . . . . ?
C6 N2 C19 C20 2.3(3) . . . . ?
C6 C7 C8 N3 -179.1(2) . . . . ?
C6 C7 C8 C20 1.3(4) . . . . ?
C7 C8 C20 C19 -1.2(3) . . . . ?
C9 N3 C8 C7 179.6(3) . . . . ?
C9 N3 C8 C20 -0.8(4) . . . . ?
C10 C11 C12 C3 -176.6(3) . . . . ?
C10 C11 C12 C28 1.4(4) . . . . ?
C11 C10 C30 C29 0.0(5) . . . . ?
C11 C12 C28 N1 179.8(2) . . . . ?
C11 C12 C28 C29 -1.2(4) . . . . ?
C12 C3 C4 N1 2.1(3) . . . . ?
C12 C3 C4 C31 -176.0(2) . . . . ?
C12 C28 C29 C30 0.3(4) . . . . ?
C13 B5 C22 C23 -99.0(3) . . . . ?
C13 B5 C22 C27 72.4(3) . . . . ?
C13 C14 C15 F4 -177.9(2) . . . . ?
C13 C14 C15 C16 2.9(4) . . . . ?
C14 C13 C18 F2 -177.4(2) . . . . ?
C14 C13 C18 C17 2.1(4) . . . . ?
C14 C15 C16 F3 179.6(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 F1 178.0(2) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 F2 179.8(2) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?
C18 C13 C14 F5 175.5(2) . . . . ?
C18 C13 C14 C15 -3.7(3) . . . . ?
C19 N2 B5 N1 -69.0(2) . . . . ?
C19 N2 B5 C13 168.2(2) . . . . ?
C19 N2 B5 C22 54.4(3) . . . . ?
C19 N2 C6 C7 -2.2(4) . . . . ?
C21 N3 C8 C7 5.8(4) . . . . ?
C21 N3 C8 C20 -174.6(2) . . . . ?
C22 B5 C13 C14 72.8(3) . . . . ?
C22 B5 C13 C18 -97.7(3) . . . . ?
C22 C23 C24 F9 178.4(2) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C22 C27 F7 178.0(2) . . . . ?
C23 C22 C27 C26 -1.8(4) . . . . ?
C23 C24 C25 F8 -180.0(2) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C25 C26 F6 179.3(2) . . . . ?
C24 C25 C26 C27 -1.5(4) . . . . ?
C25 C26 C27 F7 -177.8(2) . . . . ?
C25 C26 C27 C22 2.0(4) . . . . ?
C27 C22 C23 F10 -177.6(2) . . . . ?
C27 C22 C23 C24 1.3(3) . . . . ?
C28 N1 C4 C3 -3.1(3) . . . . ?
C28 N1 C4 C31 174.7(3) . . . . ?
C28 N1 B5 N2 -70.0(3) . . . . ?
C28 N1 B5 C13 51.8(3) . . . . ?
C28 N1 B5 C22 169.5(2) . . . . ?
C28 C29 C30 C10 0.3(4) . . . . ?
C30 C10 C11 C12 -0.8(5) . . . . ?
C32 C1 C2 C3 -0.7(5) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 508 electrons were 
found in a volume of 1686Å³ in 1 void per unit cell. 
This is consistent with the presence of 3[C6H6] per Asymmetric Unit which account for 504 electrons per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.092 842.7 253.5 '6 benzene'
2 0.500 0.000 -0.638 842.7 253.5 '6 benzene'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_jnb035cc_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068071'
loop_
_audit_author_name
_audit_author_address
'Christopher Caputo'
;York University
Canada
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-17
_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         'C18 H18 B F10 N Si2'
_chemical_formula_sum            'C18 H18 B F10 N Si2'
_chemical_formula_weight         505.32
_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'
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'
Si Si 0.0817 0.0704 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0755(10)
_cell_length_b                   11.2327(11)
_cell_length_c                   18.6587(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.827(3)
_cell_angle_gamma                90
_cell_volume                     2233.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9539
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1405 before and 0.0703 after correction.
The Ratio of minimum to maximum transmission is 0.8378.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            76348
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.628
_diffrn_reflns_theta_min         2.139
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                4641
_reflns_number_total             5127
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.485
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.060
_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)+(0.0337P)²+2.3209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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
Si1 Si 0.77815(5) 0.12152(5) 0.28866(3) 0.03504(14) Uani 1 1 d . . . . .
Si2 Si 0.95072(5) 0.26085(5) 0.41882(4) 0.04078(16) Uani 1 1 d . . . . .
F1 F 0.24499(11) -0.02194(12) 0.34563(8) 0.0478(3) Uani 1 1 d . . . . .
F2 F 0.65506(13) 0.73027(10) 0.49822(8) 0.0508(3) Uani 1 1 d . . . . .
F3 F 0.23103(10) 0.19938(11) 0.28624(7) 0.0437(3) Uani 1 1 d . . . . .
F4 F 0.44102(10) 0.33002(9) 0.30394(6) 0.0330(2) Uani 1 1 d . . . . .
F5 F 0.46748(13) -0.10699(11) 0.42922(9) 0.0539(4) Uani 1 1 d . . . . .
F6 F 0.67642(11) 0.02492(11) 0.45164(7) 0.0470(3) Uani 1 1 d . . . . .
F7 F 0.68965(14) 0.69678(11) 0.36075(8) 0.0530(4) Uani 1 1 d . . . . .
F8 F 0.63953(13) 0.54199(12) 0.58400(7) 0.0484(3) Uani 1 1 d . . . . .
F9 F 0.65479(12) 0.31879(10) 0.53368(6) 0.0412(3) Uani 1 1 d . . . . .
F10 F 0.70799(12) 0.47579(11) 0.31048(6) 0.0436(3) Uani 1 1 d . . . . .
N1 N 0.79684(13) 0.21674(13) 0.36779(8) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.34824(16) 0.04476(16) 0.35685(10) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.46182(18) 0.00112(16) 0.39855(11) 0.0332(4) Uani 1 1 d . . . . .
C3 C 0.56829(16) 0.07014(16) 0.40841(10) 0.0297(4) Uani 1 1 d . . . . .
C4 C 0.56687(15) 0.18184(14) 0.37725(9) 0.0229(3) Uani 1 1 d . . . . .
B5 B 0.69137(17) 0.25867(16) 0.38790(10) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.68547(14) 0.38894(14) 0.42106(9) 0.0232(3) Uani 1 1 d . . . . .
C7 C 0.66461(16) 0.41083(15) 0.48974(9) 0.0265(3) Uani 1 1 d . . . . .
C8 C 0.65557(16) 0.52385(17) 0.51620(10) 0.0301(4) Uani 1 1 d . . . . .
C9 C 0.66399(16) 0.62041(16) 0.47271(11) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.34168(15) 0.15702(16) 0.32663(10) 0.0284(3) Uani 1 1 d . . . . .
C11 C 0.44968(15) 0.22281(14) 0.33698(9) 0.0242(3) Uani 1 1 d . . . . .
C12 C 0.69295(16) 0.48888(16) 0.37930(9) 0.0278(3) Uani 1 1 d . . . . .
C13 C 0.68230(17) 0.60355(16) 0.40360(11) 0.0319(4) Uani 1 1 d . . . . .
C14 C 0.8099(3) -0.0364(2) 0.31607(18) 0.0630(7) Uani 1 1 d . . . . .
H14A H 0.895099 -0.043924 0.349096 0.094 Uiso 1 1 calc R U . . .
H14B H 0.802039 -0.085098 0.271440 0.094 Uiso 1 1 calc R U . . .
H14C H 0.749277 -0.063796 0.342170 0.094 Uiso 1 1 calc R U . . .
C15 C 0.6170(2) 0.1365(3) 0.22480(12) 0.0558(7) Uani 1 1 d . . . . .
H15A H 0.558420 0.088523 0.243681 0.084 Uiso 1 1 calc R U . . .
H15B H 0.616666 0.108544 0.174979 0.084 Uiso 1 1 calc R U . . .
H15C H 0.591303 0.220186 0.222150 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8853(2) 0.1743(3) 0.23361(14) 0.0565(6) Uani 1 1 d . . . . .
H16A H 0.868586 0.258464 0.220887 0.085 Uiso 1 1 calc R U . . .
H16B H 0.870995 0.127318 0.187793 0.085 Uiso 1 1 calc R U . . .
H16C H 0.972628 0.164842 0.263215 0.085 Uiso 1 1 calc R U . . .
C17 C 0.9553(2) 0.2991(4) 0.51630(16) 0.0833(12) Uani 1 1 d . . . . .
H17A H 0.920233 0.378895 0.517730 0.125 Uiso 1 1 calc R U . . .
H17B H 1.042372 0.297592 0.547272 0.125 Uiso 1 1 calc R U . . .
H17C H 0.905691 0.241033 0.535358 0.125 Uiso 1 1 calc R U . . .
C18 C 1.0087(3) 0.3883(2) 0.3736(2) 0.0747(9) Uani 1 1 d . . . . .
H18A H 0.999885 0.369442 0.321144 0.112 Uiso 1 1 calc R U . . .
H18B H 1.097299 0.402941 0.399001 0.112 Uiso 1 1 calc R U . . .
H18C H 0.959499 0.459598 0.376884 0.112 Uiso 1 1 calc R U . . .
C19 C 1.0575(2) 0.1312(2) 0.42649(15) 0.0514(6) Uani 1 1 d . . . . .
H19A H 1.027360 0.065674 0.451733 0.077 Uiso 1 1 calc R U . . .
H19B H 1.142280 0.153904 0.455241 0.077 Uiso 1 1 calc R U . . .
H19C H 1.059085 0.105598 0.376555 0.077 Uiso 1 1 calc R U . . .


_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
Si1 N1 1.7888(15) . ?
Si1 C14 1.853(3) . ?
Si1 C15 1.863(2) . ?
Si1 C16 1.866(2) . ?
Si2 N1 1.7809(15) . ?
Si2 C17 1.856(3) . ?
Si2 C18 1.863(3) . ?
Si2 C19 1.856(2) . ?
F1 C1 1.335(2) . ?
F2 C9 1.336(2) . ?
F3 C10 1.339(2) . ?
F4 C11 1.3443(19) . ?
F5 C2 1.337(2) . ?
F6 C3 1.348(2) . ?
F7 C13 1.333(2) . ?
F8 C8 1.340(2) . ?
F9 C7 1.342(2) . ?
F10 C12 1.347(2) . ?
N1 B5 1.402(2) . ?
C1 C2 1.376(3) . ?
C1 C10 1.375(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.381(2) . ?
C4 B5 1.593(2) . ?
C4 C11 1.389(2) . ?
B5 C6 1.597(2) . ?
C6 C7 1.385(2) . ?
C6 C12 1.382(2) . ?
C7 C8 1.376(2) . ?
C8 C9 1.373(3) . ?
C9 C13 1.372(3) . ?
C10 C11 1.374(2) . ?
C12 C13 1.381(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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N1 Si1 C14 111.97(11) . . ?
N1 Si1 C15 110.43(9) . . ?
N1 Si1 C16 108.46(10) . . ?
C14 Si1 C15 109.83(14) . . ?
C14 Si1 C16 110.79(14) . . ?
C15 Si1 C16 105.15(12) . . ?
N1 Si2 C17 110.78(11) . . ?
N1 Si2 C18 111.70(12) . . ?
N1 Si2 C19 108.63(9) . . ?
C17 Si2 C18 110.20(18) . . ?
C17 Si2 C19 105.04(14) . . ?
C19 Si2 C18 110.29(13) . . ?
Si2 N1 Si1 119.09(8) . . ?
B5 N1 Si1 120.29(11) . . ?
B5 N1 Si2 120.60(12) . . ?
F1 C1 C2 120.03(17) . . ?
F1 C1 C10 120.21(17) . . ?
C10 C1 C2 119.76(16) . . ?
F5 C2 C1 119.64(17) . . ?
F5 C2 C3 120.96(17) . . ?
C1 C2 C3 119.40(16) . . ?
F6 C3 C2 117.08(16) . . ?
F6 C3 C4 120.04(16) . . ?
C2 C3 C4 122.86(16) . . ?
C3 C4 B5 121.99(15) . . ?
C3 C4 C11 115.50(15) . . ?
C11 C4 B5 122.51(14) . . ?
N1 B5 C4 122.73(15) . . ?
N1 B5 C6 122.45(15) . . ?
C4 B5 C6 114.79(14) . . ?
C7 C6 B5 123.78(15) . . ?
C12 C6 B5 120.72(14) . . ?
C12 C6 C7 115.36(15) . . ?
F9 C7 C6 119.36(15) . . ?
F9 C7 C8 117.75(15) . . ?
C8 C7 C6 122.87(16) . . ?
F8 C8 C7 121.36(17) . . ?
F8 C8 C9 119.06(16) . . ?
C9 C8 C7 119.59(16) . . ?
F2 C9 C8 119.71(18) . . ?
F2 C9 C13 120.44(18) . . ?
C13 C9 C8 119.85(16) . . ?
F3 C10 C1 119.64(16) . . ?
F3 C10 C11 121.07(16) . . ?
C11 C10 C1 119.27(16) . . ?
F4 C11 C4 118.96(14) . . ?
F4 C11 C10 117.83(15) . . ?
C10 C11 C4 123.16(16) . . ?
F10 C12 C6 119.39(16) . . ?
F10 C12 C13 117.29(16) . . ?
C13 C12 C6 123.29(16) . . ?
F7 C13 C9 120.26(17) . . ?
F7 C13 C12 120.73(17) . . ?
C9 C13 C12 119.01(16) . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si2 C17 H17A 109.5 . . ?
Si2 C17 H17B 109.5 . . ?
Si2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si2 C18 H18A 109.5 . . ?
Si2 C18 H18B 109.5 . . ?
Si2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si2 C19 H19A 109.5 . . ?
Si2 C19 H19B 109.5 . . ?
Si2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
Si1 N1 B5 C4 34.2(2) . . . . ?
Si1 N1 B5 C6 -143.97(13) . . . . ?
Si2 N1 B5 C4 -147.70(13) . . . . ?
Si2 N1 B5 C6 34.2(2) . . . . ?
F1 C1 C2 F5 -1.7(3) . . . . ?
F1 C1 C2 C3 178.67(17) . . . . ?
F1 C1 C10 F3 0.4(3) . . . . ?
F1 C1 C10 C11 -178.07(16) . . . . ?
F2 C9 C13 F7 -0.9(3) . . . . ?
F2 C9 C13 C12 179.07(16) . . . . ?
F3 C10 C11 F4 -1.4(2) . . . . ?
F3 C10 C11 C4 -178.80(15) . . . . ?
F5 C2 C3 F6 -1.7(3) . . . . ?
F5 C2 C3 C4 179.46(17) . . . . ?
F6 C3 C4 B5 2.6(2) . . . . ?
F6 C3 C4 C11 -176.68(15) . . . . ?
F8 C8 C9 F2 -0.6(3) . . . . ?
F8 C8 C9 C13 179.02(16) . . . . ?
F9 C7 C8 F8 1.1(3) . . . . ?
F9 C7 C8 C9 -179.42(16) . . . . ?
F10 C12 C13 F7 -1.5(3) . . . . ?
F10 C12 C13 C9 178.52(15) . . . . ?
N1 B5 C6 C7 -121.87(18) . . . . ?
N1 B5 C6 C12 62.5(2) . . . . ?
C1 C2 C3 F6 177.95(17) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C10 C11 F4 177.07(15) . . . . ?
C1 C10 C11 C4 -0.4(3) . . . . ?
C2 C1 C10 F3 -179.83(16) . . . . ?
C2 C1 C10 C11 1.7(3) . . . . ?
C2 C3 C4 B5 -178.62(17) . . . . ?
C2 C3 C4 C11 2.1(3) . . . . ?
C3 C4 B5 N1 56.5(2) . . . . ?
C3 C4 B5 C6 -125.23(17) . . . . ?
C3 C4 C11 F4 -178.92(14) . . . . ?
C3 C4 C11 C10 -1.5(2) . . . . ?
C4 B5 C6 C7 59.9(2) . . . . ?
C4 B5 C6 C12 -115.72(17) . . . . ?
B5 C4 C11 F4 1.8(2) . . . . ?
B5 C4 C11 C10 179.26(15) . . . . ?
B5 C6 C7 F9 3.5(2) . . . . ?
B5 C6 C7 C8 -177.69(16) . . . . ?
B5 C6 C12 F10 -1.4(2) . . . . ?
B5 C6 C12 C13 176.76(16) . . . . ?
C6 C7 C8 F8 -177.73(16) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C6 C12 C13 F7 -179.66(16) . . . . ?
C6 C12 C13 C9 0.3(3) . . . . ?
C7 C6 C12 F10 -177.33(15) . . . . ?
C7 C6 C12 C13 0.8(2) . . . . ?
C7 C8 C9 F2 179.90(16) . . . . ?
C7 C8 C9 C13 -0.5(3) . . . . ?
C8 C9 C13 F7 179.49(16) . . . . ?
C8 C9 C13 C12 -0.5(3) . . . . ?
C10 C1 C2 F5 178.54(17) . . . . ?
C10 C1 C2 C3 -1.1(3) . . . . ?
C11 C4 B5 N1 -124.29(18) . . . . ?
C11 C4 B5 C6 54.0(2) . . . . ?
C12 C6 C7 F9 179.34(15) . . . . ?
C12 C6 C7 C8 -1.9(2) . . . . ?
C14 Si1 N1 Si2 79.71(14) . . . . ?
C14 Si1 N1 B5 -102.12(17) . . . . ?
C15 Si1 N1 Si2 -157.58(13) . . . . ?
C15 Si1 N1 B5 20.60(18) . . . . ?
C16 Si1 N1 Si2 -42.85(14) . . . . ?
C16 Si1 N1 B5 135.32(16) . . . . ?
C17 Si2 N1 Si1 -155.06(15) . . . . ?
C17 Si2 N1 B5 26.8(2) . . . . ?
C18 Si2 N1 Si1 81.69(15) . . . . ?
C18 Si2 N1 B5 -96.48(18) . . . . ?
C19 Si2 N1 Si1 -40.18(14) . . . . ?
C19 Si2 N1 B5 141.65(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
