# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_20211021tn_01_098
_database_code_depnum_ccdc_archive 'CCDC 2333166'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B C14 F16 N O4 S2'
_chemical_formula_sum            'C14 B F16 N O4 S2'
_chemical_formula_weight         625.08
_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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6324(9)
_cell_length_b                   10.7924(10)
_cell_length_c                   10.8665(10)
_cell_angle_alpha                65.7390(10)
_cell_angle_beta                 86.565(2)
_cell_angle_gamma                69.970(2)
_cell_volume                     963.27(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6691
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.377
_cell_measurement_theta_min      2.209
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0452 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.9522.
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    2.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0610
0.00 1.00 1.00 0.0610
0.00 1.00 0.00 0.0530
0.00 -1.00 0.00 0.0900
-1.00 -1.00 -1.00 0.0560
1.00 1.00 1.00 0.0540
0.00 1.00 -1.00 0.0580
0.00 -1.00 1.00 0.0860
-1.00 0.00 -1.00 0.0750
-1.00 0.00 0.00 0.0900
-1.00 -1.00 0.00 0.0880
-1.00 1.00 1.00 0.0870
1.00 -1.00 -1.00 0.0940
1.00 1.00 -1.00 0.0530
-1.00 -1.00 1.00 0.0900

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.113
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.049
_diffrn_reflns_theta_min         2.065
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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           30.0
_diffrn_source_power             1.5
_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                3862
_reflns_number_total             5136
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.030
_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)+(0.0412P)²+0.3377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
S1 S 0.69569(5) 0.72023(5) 0.39393(4) 0.02022(11) Uani 1 1 d . . . . .
S2 S 0.88292(5) 0.67907(5) 0.20010(5) 0.02075(11) Uani 1 1 d . . . . .
F5 F 0.97302(14) 0.33616(13) 0.24422(12) 0.0349(3) Uani 1 1 d . . . . .
F1 F 0.65463(14) 0.39853(13) 0.57836(12) 0.0342(3) Uani 1 1 d . . . . .
F10 F 0.47749(15) 0.77596(12) 0.08805(13) 0.0377(3) Uani 1 1 d . . . . .
F8 F 0.20754(14) 0.52051(16) 0.01831(13) 0.0402(3) Uani 1 1 d . . . . .
O2 O 0.78210(14) 0.60910(13) 0.17888(12) 0.0200(3) Uani 1 1 d . . . . .
O1 O 0.61978(14) 0.64246(13) 0.35184(12) 0.0201(3) Uani 1 1 d . . . . .
F6 F 0.62469(15) 0.26684(12) 0.33179(14) 0.0405(3) Uani 1 1 d . . . . .
F4 F 1.15074(14) 0.08656(14) 0.43097(15) 0.0412(3) Uani 1 1 d . . . . .
F3 F 1.08140(16) -0.01307(13) 0.69137(14) 0.0469(4) Uani 1 1 d . . . . .
F2 F 0.83083(17) 0.14609(15) 0.76254(12) 0.0457(4) Uani 1 1 d . . . . .
F7 F 0.39579(16) 0.26939(15) 0.20477(15) 0.0471(4) Uani 1 1 d . . . . .
F14 F 0.70350(16) 0.91258(15) 0.00953(13) 0.0468(4) Uani 1 1 d . . . . .
F13 F 0.52664(17) 0.96267(14) 0.20394(14) 0.0501(4) Uani 1 1 d . . . . .
F9 F 0.24914(16) 0.77398(15) -0.03802(14) 0.0496(4) Uani 1 1 d . . . . .
O3 O 0.72845(17) 0.67117(16) 0.53420(13) 0.0306(3) Uani 1 1 d . . . . .
O4 O 1.03660(15) 0.60157(16) 0.21849(15) 0.0310(3) Uani 1 1 d . . . . .
F12 F 0.60239(18) 0.98126(14) 0.37400(17) 0.0550(4) Uani 1 1 d . . . . .
F15 F 0.91551(19) 0.91874(17) 0.04388(15) 0.0620(5) Uani 1 1 d . . . . .
F11 F 0.43189(16) 0.89257(16) 0.39137(18) 0.0599(4) Uani 1 1 d . . . . .
F16 F 0.8930(2) 0.79328(17) -0.05837(14) 0.0611(5) Uani 1 1 d . . . . .
N N 0.82959(18) 0.73963(18) 0.30942(16) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.8084(2) 0.38272(19) 0.40355(18) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.5628(2) 0.5217(2) 0.21636(17) 0.0195(4) Uani 1 1 d . . . . .
C6 C 0.9359(2) 0.2959(2) 0.37214(19) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.5347(2) 0.3960(2) 0.24157(19) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.7783(2) 0.3259(2) 0.53787(19) 0.0230(4) Uani 1 1 d . . . . .
C12 C 0.4609(2) 0.6471(2) 0.12039(19) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.3206(2) 0.5212(2) 0.0833(2) 0.0274(4) Uani 1 1 d . . . . .
C5 C 1.0282(2) 0.1647(2) 0.4672(2) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.4164(2) 0.3939(2) 0.1776(2) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.3419(2) 0.6495(2) 0.0547(2) 0.0290(4) Uani 1 1 d . . . . .
C4 C 0.9932(2) 0.1143(2) 0.5985(2) 0.0295(5) Uani 1 1 d . . . . .
C3 C 0.8675(2) 0.1945(2) 0.63441(19) 0.0291(5) Uani 1 1 d . . . . .
C13 C 0.5533(2) 0.9034(2) 0.3354(2) 0.0310(5) Uani 1 1 d . . . . .
C14 C 0.8449(3) 0.8387(2) 0.0358(2) 0.0311(5) Uani 1 1 d . . . . .
B B 0.6953(2) 0.5296(2) 0.2904(2) 0.0179(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
S1 O1 1.4914(13) . ?
S1 O3 1.4083(14) . ?
S1 N 1.5607(17) . ?
S1 C13 1.846(2) . ?
S2 O2 1.4963(13) . ?
S2 O4 1.4074(15) . ?
S2 N 1.5612(17) . ?
S2 C14 1.846(2) . ?
F5 C6 1.341(2) . ?
F1 C2 1.345(2) . ?
F10 C12 1.352(2) . ?
F8 C10 1.337(2) . ?
O2 B 1.556(2) . ?
O1 B 1.569(2) . ?
F6 C8 1.344(2) . ?
F4 C5 1.340(2) . ?
F3 C4 1.339(2) . ?
F2 C3 1.344(2) . ?
F7 C9 1.334(2) . ?
F14 C14 1.299(3) . ?
F13 C13 1.302(2) . ?
F9 C11 1.338(2) . ?
F12 C13 1.300(2) . ?
F15 C14 1.299(3) . ?
F11 C13 1.304(3) . ?
F16 C14 1.305(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.388(3) . ?
C1 B 1.609(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.391(3) . ?
C7 B 1.592(3) . ?
C6 C5 1.381(3) . ?
C8 C9 1.381(3) . ?
C2 C3 1.378(3) . ?
C12 C11 1.373(3) . ?
C10 C9 1.371(3) . ?
C10 C11 1.374(3) . ?
C5 C4 1.370(3) . ?
C4 C3 1.367(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
O1 S1 N 111.15(8) . . ?
O1 S1 C13 101.59(9) . . ?
O3 S1 O1 116.68(8) . . ?
O3 S1 N 113.71(9) . . ?
O3 S1 C13 106.72(9) . . ?
N S1 C13 105.50(10) . . ?
O2 S2 N 111.22(8) . . ?
O2 S2 C14 100.69(9) . . ?
O4 S2 O2 117.47(8) . . ?
O4 S2 N 112.66(9) . . ?
O4 S2 C14 107.23(10) . . ?
N S2 C14 106.14(10) . . ?
S2 O2 B 124.84(11) . . ?
S1 O1 B 125.57(11) . . ?
S1 N S2 124.76(10) . . ?
C6 C1 B 122.63(16) . . ?
C2 C1 C6 114.78(17) . . ?
C2 C1 B 122.30(17) . . ?
C8 C7 C12 114.17(17) . . ?
C8 C7 B 125.16(16) . . ?
C12 C7 B 120.66(16) . . ?
F5 C6 C1 120.30(16) . . ?
F5 C6 C5 116.71(18) . . ?
C5 C6 C1 122.98(18) . . ?
F6 C8 C7 120.46(17) . . ?
F6 C8 C9 116.04(17) . . ?
C9 C8 C7 123.49(18) . . ?
F1 C2 C1 119.78(17) . . ?
F1 C2 C3 116.75(17) . . ?
C3 C2 C1 123.45(19) . . ?
F10 C12 C7 119.19(17) . . ?
F10 C12 C11 116.72(17) . . ?
C11 C12 C7 124.09(18) . . ?
F8 C10 C9 120.07(19) . . ?
F8 C10 C11 120.1(2) . . ?
C9 C10 C11 119.84(18) . . ?
F4 C5 C6 120.20(19) . . ?
F4 C5 C4 120.14(18) . . ?
C4 C5 C6 119.66(19) . . ?
F7 C9 C8 120.89(19) . . ?
F7 C9 C10 119.71(18) . . ?
C10 C9 C8 119.39(19) . . ?
F9 C11 C12 120.96(19) . . ?
F9 C11 C10 120.02(19) . . ?
C12 C11 C10 119.01(19) . . ?
F3 C4 C5 120.2(2) . . ?
F3 C4 C3 120.10(19) . . ?
C3 C4 C5 119.73(18) . . ?
F2 C3 C2 120.1(2) . . ?
F2 C3 C4 120.49(18) . . ?
C4 C3 C2 119.40(18) . . ?
F13 C13 S1 110.72(14) . . ?
F13 C13 F11 109.6(2) . . ?
F12 C13 S1 107.94(15) . . ?
F12 C13 F13 110.17(19) . . ?
F12 C13 F11 109.77(19) . . ?
F11 C13 S1 108.59(15) . . ?
F14 C14 S2 110.59(14) . . ?
F14 C14 F15 109.80(19) . . ?
F14 C14 F16 109.88(19) . . ?
F15 C14 S2 107.70(15) . . ?
F15 C14 F16 110.56(19) . . ?
F16 C14 S2 108.28(15) . . ?
O2 B O1 102.33(13) . . ?
O2 B C1 110.26(15) . . ?
O2 B C7 107.74(14) . . ?
O1 B C1 110.43(14) . . ?
O1 B C7 105.48(14) . . ?
C7 B C1 119.21(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
S1 O1 B O2 -47.95(18) . . . . ?
S1 O1 B C1 69.41(18) . . . . ?
S1 O1 B C7 -160.54(12) . . . . ?
S2 O2 B O1 49.49(18) . . . . ?
S2 O2 B C1 -67.99(18) . . . . ?
S2 O2 B C7 160.39(12) . . . . ?
F5 C6 C5 F4 2.3(3) . . . . ?
F5 C6 C5 C4 -177.18(18) . . . . ?
F1 C2 C3 F2 -1.4(3) . . . . ?
F1 C2 C3 C4 178.67(18) . . . . ?
F10 C12 C11 F9 1.0(3) . . . . ?
F10 C12 C11 C10 179.55(18) . . . . ?
F8 C10 C9 F7 -0.4(3) . . . . ?
F8 C10 C9 C8 178.53(18) . . . . ?
F8 C10 C11 F9 0.2(3) . . . . ?
F8 C10 C11 C12 -178.46(17) . . . . ?
O2 S2 N S1 4.26(16) . . . . ?
O2 S2 C14 F14 54.07(17) . . . . ?
O2 S2 C14 F15 174.06(16) . . . . ?
O2 S2 C14 F16 -66.36(17) . . . . ?
O1 S1 N S2 -2.91(16) . . . . ?
O1 S1 C13 F13 -63.35(17) . . . . ?
O1 S1 C13 F12 175.98(15) . . . . ?
O1 S1 C13 F11 57.04(16) . . . . ?
F6 C8 C9 F7 -0.5(3) . . . . ?
F6 C8 C9 C10 -179.38(18) . . . . ?
F4 C5 C4 F3 0.2(3) . . . . ?
F4 C5 C4 C3 -179.65(18) . . . . ?
F3 C4 C3 F2 -0.4(3) . . . . ?
F3 C4 C3 C2 179.53(18) . . . . ?
O3 S1 O1 B -104.20(15) . . . . ?
O3 S1 N S2 131.17(13) . . . . ?
O3 S1 C13 F13 173.95(15) . . . . ?
O3 S1 C13 F12 53.29(18) . . . . ?
O3 S1 C13 F11 -65.65(17) . . . . ?
O4 S2 O2 B 100.34(15) . . . . ?
O4 S2 N S1 -130.05(13) . . . . ?
O4 S2 C14 F14 177.45(15) . . . . ?
O4 S2 C14 F15 -62.57(19) . . . . ?
O4 S2 C14 F16 57.01(18) . . . . ?
N S1 O1 B 28.39(16) . . . . ?
N S1 C13 F13 52.69(18) . . . . ?
N S1 C13 F12 -67.97(17) . . . . ?
N S1 C13 F11 173.09(15) . . . . ?
N S2 O2 B -31.55(16) . . . . ?
N S2 C14 F14 -61.91(17) . . . . ?
N S2 C14 F15 58.08(18) . . . . ?
N S2 C14 F16 177.65(15) . . . . ?
C1 C6 C5 F4 -179.23(17) . . . . ?
C1 C6 C5 C4 1.3(3) . . . . ?
C1 C2 C3 F2 -179.71(18) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C7 C8 C9 F7 179.24(18) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C12 C11 F9 -179.08(19) . . . . ?
C7 C12 C11 C10 -0.5(3) . . . . ?
C6 C1 C2 F1 -177.60(17) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C1 B O2 -36.4(2) . . . . ?
C6 C1 B O1 -148.79(17) . . . . ?
C6 C1 B C7 88.9(2) . . . . ?
C6 C5 C4 F3 179.66(17) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C8 C7 C12 F10 179.93(17) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C7 B O2 126.80(18) . . . . ?
C8 C7 B O1 -124.47(18) . . . . ?
C8 C7 B C1 0.3(3) . . . . ?
C2 C1 C6 F5 176.96(16) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C1 B O2 150.12(16) . . . . ?
C2 C1 B O1 37.8(2) . . . . ?
C2 C1 B C7 -84.5(2) . . . . ?
C12 C7 C8 F6 179.81(17) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C12 C7 B O2 -55.0(2) . . . . ?
C12 C7 B O1 53.7(2) . . . . ?
C12 C7 B C1 178.43(17) . . . . ?
C5 C4 C3 F2 179.47(18) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C9 C10 C11 F9 179.53(18) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C11 C10 C9 F7 -179.78(18) . . . . ?
C11 C10 C9 C8 -0.8(3) . . . . ?
C13 S1 O1 B 140.22(14) . . . . ?
C13 S1 N S2 -112.22(13) . . . . ?
C14 S2 O2 B -143.69(14) . . . . ?
C14 S2 N S1 112.89(13) . . . . ?
B C1 C6 F5 3.1(3) . . . . ?
B C1 C6 C5 -175.39(17) . . . . ?
B C1 C2 F1 -3.7(3) . . . . ?
B C1 C2 C3 174.57(18) . . . . ?
B C7 C8 F6 -1.9(3) . . . . ?
B C7 C8 C9 178.39(18) . . . . ?
B C7 C12 F10 1.6(3) . . . . ?
B C7 C12 C11 -178.39(18) . . . . ?

_olex2_submission_original_sample_id TN_01_098
_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_tn02187
_database_code_depnum_ccdc_archive 'CCDC 2333168'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C68 H26 B2 F20 N4'
_chemical_formula_sum            'C68 H26 B2 F20 N4'
_chemical_formula_weight         1300.55
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   10.2642(5)
_cell_length_b                   10.8711(6)
_cell_length_c                   12.8590(7)
_cell_angle_alpha                71.888(4)
_cell_angle_beta                 78.885(4)
_cell_angle_gamma                84.992(4)
_cell_volume                     1337.60(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.34
_cell_measurement_theta_min      3.67
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0852 after correction.
The Ratio of minimum to maximum transmission is 0.8430.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             652
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0490
0.00 -1.00 -1.00 0.0510
0.00 0.00 -1.00 0.0180
0.00 0.00 1.00 0.0180
0.00 1.00 -1.00 0.0350
-1.00 1.00 1.00 0.0180
1.00 0.00 -1.00 0.0430
-1.00 0.00 1.00 0.0340
-1.00 -1.00 1.00 0.0450
1.00 -1.00 0.00 0.0080
-1.00 1.00 0.00 0.0190
1.00 0.00 0.00 0.0490
-1.00 0.00 0.00 0.0470
-1.00 -1.00 0.00 0.0530
1.00 1.00 0.00 0.0640

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22874
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        66.943
_diffrn_reflns_theta_max         66.943
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.028576
_diffrn_source_voltage           44.65
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2832
_reflns_number_total             4575
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      0.996
_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)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1717
_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:
 C2(H2), C3(H3), C10(H10), C21(H21), C9(H9), C7(H7), C20(H20), C18(H18),
 C19(H19), C12(H12), C13(H13), C15(H15), C14(H14)
;
_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
F10 F 0.3129(2) 0.5169(2) 0.24405(19) 0.0382(5) Uani 1 1 d . . . . .
F1 F 0.3746(2) 0.6207(2) -0.00246(19) 0.0394(5) Uani 1 1 d . . . . .
F5 F 0.3539(3) 0.9426(2) 0.17911(19) 0.0464(6) Uani 1 1 d . . . . .
F6 F -0.0567(2) 0.6895(2) 0.0681(2) 0.0502(6) Uani 1 1 d . . . . .
F9 F 0.2143(3) 0.2831(2) 0.3056(2) 0.0560(7) Uani 1 1 d . . . . .
F7 F -0.1436(3) 0.4517(3) 0.1193(2) 0.0582(7) Uani 1 1 d . . . . .
F8 F -0.0133(3) 0.2458(3) 0.2437(2) 0.0633(8) Uani 1 1 d . . . . .
F2 F 0.6322(3) 0.6581(3) -0.0711(3) 0.0648(8) Uani 1 1 d . . . . .
F4 F 0.6119(3) 0.9664(3) 0.1197(2) 0.0645(9) Uani 1 1 d . . . . .
F3 F 0.7545(3) 0.8343(3) -0.0143(3) 0.0794(11) Uani 1 1 d . . . . .
N1 N -0.1238(3) 1.1335(3) -0.0326(2) 0.0235(6) Uani 1 1 d . . . . .
N2 N 0.2185(3) 0.7040(3) 0.5282(2) 0.0357(7) Uani 1 1 d . . . . .
C4 C -0.0201(3) 0.9710(3) 0.1559(3) 0.0224(7) Uani 1 1 d . . . . .
C1 C -0.0265(3) 1.0412(3) -0.0472(3) 0.0209(7) Uani 1 1 d . . . . .
C2 C -0.1680(3) 1.1409(3) 0.0694(3) 0.0289(7) Uani 1 1 d . . . . .
H2 H -0.234154 1.202709 0.078587 0.035 Uiso 1 1 calc R U . . .
C28 C 0.1335(3) 0.6179(3) 0.1528(3) 0.0266(7) Uani 1 1 d . . . . .
C5 C 0.0353(3) 0.8958(3) 0.2532(3) 0.0254(7) Uani 1 1 d . . . . .
C3 C -0.1218(3) 1.0627(3) 0.1624(3) 0.0267(7) Uani 1 1 d . . . . .
H3 H -0.159826 1.071453 0.231538 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1346(3) 0.7999(3) 0.2449(3) 0.0283(7) Uani 1 1 d . . . . .
C22 C 0.3484(3) 0.7768(3) 0.0953(3) 0.0267(7) Uani 1 1 d . . . . .
C33 C 0.1956(4) 0.5081(4) 0.2140(3) 0.0321(8) Uani 1 1 d . . . . .
C00M C 0.2916(4) 0.7682(4) 0.5761(3) 0.0325(8) Uani 1 1 d . . . . .
C10 C -0.0057(4) 0.9227(4) 0.3549(3) 0.0327(8) Uani 1 1 d . . . . .
H10 H -0.072460 0.985010 0.360773 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3064(4) 0.8989(4) 0.5553(3) 0.0330(8) Uani 1 1 d . . . . .
H21 H 0.263623 0.959845 0.503295 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0522(4) 0.8574(4) 0.4469(3) 0.0356(8) Uani 1 1 d . . . . .
H9 H 0.023696 0.875113 0.514063 0.043 Uiso 1 1 calc R U . . .
C30 C -0.0333(4) 0.4686(4) 0.1533(3) 0.0400(9) Uani 1 1 d . . . . .
C7 C 0.1904(4) 0.7362(3) 0.3388(3) 0.0317(8) Uani 1 1 d . . . . .
H7 H 0.255085 0.671552 0.334858 0.038 Uiso 1 1 calc R U . . .
C27 C 0.4191(4) 0.8632(4) 0.1215(3) 0.0354(8) Uani 1 1 d . . . . .
C29 C 0.0167(4) 0.5919(4) 0.1259(3) 0.0326(8) Uani 1 1 d . . . . .
C17 C 0.3610(4) 0.6744(4) 0.6510(3) 0.0371(9) Uani 1 1 d . . . . .
C32 C 0.1480(4) 0.3838(4) 0.2463(3) 0.0383(9) Uani 1 1 d . . . . .
C8 C 0.1525(4) 0.7658(4) 0.4378(3) 0.0330(8) Uani 1 1 d . . . . .
C31 C 0.0333(4) 0.3655(4) 0.2146(3) 0.0425(10) Uani 1 1 d . . . . .
C23 C 0.4287(4) 0.7087(4) 0.0308(3) 0.0323(8) Uani 1 1 d . . . . .
C16 C 0.3316(5) 0.5489(4) 0.6444(3) 0.0442(10) Uani 1 1 d . . . . .
C11 C 0.2455(4) 0.5708(4) 0.5684(3) 0.0408(9) Uani 1 1 d . . . . .
C25 C 0.6255(4) 0.8133(4) 0.0238(4) 0.0511(12) Uani 1 1 d . . . . .
C20 C 0.3868(4) 0.9367(4) 0.6141(3) 0.0410(9) Uani 1 1 d . . . . .
H20 H 0.397552 1.024451 0.601634 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5520(4) 0.8809(4) 0.0903(4) 0.0458(11) Uani 1 1 d . . . . .
C24 C 0.5634(4) 0.7256(4) -0.0055(4) 0.0458(10) Uani 1 1 d . . . . .
C18 C 0.4401(4) 0.7157(5) 0.7096(4) 0.0470(10) Uani 1 1 d . . . . .
H18 H 0.484624 0.655313 0.760663 0.056 Uiso 1 1 calc R U . . .
C19 C 0.4523(4) 0.8456(5) 0.6919(4) 0.0465(10) Uani 1 1 d . . . . .
H19 H 0.504162 0.873291 0.731685 0.056 Uiso 1 1 calc R U . . .
B1 B 0.1868(4) 0.7637(4) 0.1326(3) 0.0256(8) Uani 1 1 d . . . . .
C12 C 0.1967(5) 0.4699(4) 0.5432(4) 0.0571(13) Uani 1 1 d . . . . .
H12 H 0.137925 0.485801 0.493500 0.068 Uiso 1 1 calc R U . . .
C13 C 0.2383(8) 0.3463(5) 0.5944(5) 0.083(2) Uani 1 1 d . . . . .
H13 H 0.208318 0.276951 0.578540 0.100 Uiso 1 1 calc R U . . .
C15 C 0.3714(6) 0.4225(5) 0.6961(4) 0.0702(16) Uani 1 1 d . . . . .
H15 H 0.428324 0.405852 0.747377 0.084 Uiso 1 1 calc R U . . .
C14 C 0.3255(8) 0.3231(6) 0.6703(5) 0.095(3) Uani 1 1 d . . . . .
H14 H 0.352656 0.238482 0.703850 0.114 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
F10 C33 1.353(4) . ?
F1 C23 1.358(4) . ?
F5 C27 1.359(5) . ?
F6 C29 1.353(4) . ?
F9 C32 1.340(5) . ?
F7 C30 1.335(4) . ?
F8 C31 1.342(4) . ?
F2 C24 1.346(5) . ?
F4 C26 1.338(5) . ?
F3 C25 1.334(5) . ?
N1 C1 1.382(4) . ?
N1 C2 1.328(4) . ?
N1 B1 1.619(4) 2_575 ?
N2 C00M 1.403(5) . ?
N2 C8 1.414(4) . ?
N2 C11 1.400(5) . ?
C4 C1 1.431(4) 2_575 ?
C4 C5 1.453(4) . ?
C4 C3 1.388(5) . ?
C1 C1 1.437(6) 2_575 ?
C2 H2 0.9300 . ?
C2 C3 1.376(5) . ?
C28 C33 1.388(5) . ?
C28 C29 1.384(5) . ?
C28 B1 1.650(5) . ?
C5 C6 1.407(5) . ?
C5 C10 1.407(5) . ?
C3 H3 0.9300 . ?
C6 C7 1.393(5) . ?
C6 B1 1.596(5) . ?
C22 C27 1.390(5) . ?
C22 C23 1.389(5) . ?
C22 B1 1.641(5) . ?
C33 C32 1.387(5) . ?
C00M C21 1.378(5) . ?
C00M C17 1.415(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.390(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.382(5) . ?
C30 C29 1.394(5) . ?
C30 C31 1.367(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(5) . ?
C27 C26 1.359(6) . ?
C17 C16 1.453(6) . ?
C17 C18 1.393(6) . ?
C32 C31 1.367(6) . ?
C23 C24 1.381(5) . ?
C16 C11 1.395(5) . ?
C16 C15 1.391(6) . ?
C11 C12 1.392(6) . ?
C25 C26 1.373(7) . ?
C25 C24 1.371(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.400(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(6) . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.372(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.368(7) . ?
C14 H14 0.9300 . ?

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
C1 N1 B1 124.3(3) . 2_575 ?
C2 N1 C1 118.6(3) . . ?
C2 N1 B1 117.1(3) . 2_575 ?
C00M N2 C8 124.5(3) . . ?
C11 N2 C00M 108.4(3) . . ?
C11 N2 C8 125.8(3) . . ?
C1 C4 C5 123.3(3) 2_575 . ?
C3 C4 C1 115.1(3) . 2_575 ?
C3 C4 C5 121.6(3) . . ?
N1 C1 C4 119.6(3) . 2_575 ?
N1 C1 C1 119.5(4) . 2_575 ?
C4 C1 C1 120.9(4) 2_575 2_575 ?
N1 C2 H2 118.0 . . ?
N1 C2 C3 123.9(3) . . ?
C3 C2 H2 118.0 . . ?
C33 C28 B1 121.0(3) . . ?
C29 C28 C33 113.2(3) . . ?
C29 C28 B1 125.2(3) . . ?
C6 C5 C4 120.3(3) . . ?
C10 C5 C4 120.1(3) . . ?
C10 C5 C6 119.5(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C5 C6 B1 122.7(3) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 B1 119.3(3) . . ?
C27 C22 B1 122.8(3) . . ?
C23 C22 C27 112.5(3) . . ?
C23 C22 B1 124.6(3) . . ?
F10 C33 C28 120.3(3) . . ?
F10 C33 C32 115.0(3) . . ?
C32 C33 C28 124.6(3) . . ?
N2 C00M C17 108.5(3) . . ?
C21 C00M N2 129.8(3) . . ?
C21 C00M C17 121.6(3) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C00M C21 H21 121.0 . . ?
C00M C21 C20 117.9(4) . . ?
C20 C21 H21 121.0 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
F7 C30 C29 120.4(4) . . ?
F7 C30 C31 120.9(3) . . ?
C31 C30 C29 118.7(4) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(3) . . ?
C8 C7 H7 118.9 . . ?
F5 C27 C22 119.9(3) . . ?
C26 C27 F5 114.6(4) . . ?
C26 C27 C22 125.5(4) . . ?
F6 C29 C28 120.2(3) . . ?
F6 C29 C30 115.4(3) . . ?
C28 C29 C30 124.4(4) . . ?
C00M C17 C16 106.6(3) . . ?
C18 C17 C00M 118.9(4) . . ?
C18 C17 C16 134.5(4) . . ?
F9 C32 C33 120.8(4) . . ?
F9 C32 C31 120.4(4) . . ?
C31 C32 C33 118.8(4) . . ?
C9 C8 N2 120.5(3) . . ?
C9 C8 C7 119.8(3) . . ?
C7 C8 N2 119.7(3) . . ?
F8 C31 C30 120.2(4) . . ?
F8 C31 C32 119.6(4) . . ?
C30 C31 C32 120.2(3) . . ?
F1 C23 C22 119.8(3) . . ?
F1 C23 C24 115.9(4) . . ?
C24 C23 C22 124.3(4) . . ?
C11 C16 C17 107.3(4) . . ?
C15 C16 C17 133.5(4) . . ?
C15 C16 C11 119.2(4) . . ?
C16 C11 N2 109.1(3) . . ?
C12 C11 N2 128.8(4) . . ?
C12 C11 C16 122.1(4) . . ?
F3 C25 C26 121.0(4) . . ?
F3 C25 C24 120.1(5) . . ?
C24 C25 C26 119.0(4) . . ?
C21 C20 H20 119.3 . . ?
C21 C20 C19 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
F4 C26 C27 121.4(5) . . ?
F4 C26 C25 119.3(4) . . ?
C27 C26 C25 119.3(4) . . ?
F2 C24 C23 119.9(4) . . ?
F2 C24 C25 120.6(4) . . ?
C25 C24 C23 119.5(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
N1 B1 C28 109.4(3) 2_575 . ?
N1 B1 C22 105.7(3) 2_575 . ?
C6 B1 N1 109.2(3) . 2_575 ?
C6 B1 C28 106.8(3) . . ?
C6 B1 C22 111.4(3) . . ?
C22 B1 C28 114.3(3) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F10 C33 C32 F9 1.9(5) . . . . ?
F10 C33 C32 C31 -176.9(3) . . . . ?
F1 C23 C24 F2 0.9(5) . . . . ?
F1 C23 C24 C25 179.6(4) . . . . ?
F5 C27 C26 F4 2.9(5) . . . . ?
F5 C27 C26 C25 -174.6(3) . . . . ?
F9 C32 C31 F8 0.2(6) . . . . ?
F9 C32 C31 C30 -179.5(4) . . . . ?
F7 C30 C29 F6 2.6(5) . . . . ?
F7 C30 C29 C28 -176.8(4) . . . . ?
F7 C30 C31 F8 -1.5(6) . . . . ?
F7 C30 C31 C32 178.2(4) . . . . ?
F3 C25 C26 F4 -1.9(6) . . . . ?
F3 C25 C26 C27 175.6(3) . . . . ?
F3 C25 C24 F2 1.4(6) . . . . ?
F3 C25 C24 C23 -177.4(3) . . . . ?
N1 C2 C3 C4 2.3(5) . . . . ?
N2 C00M C21 C20 -179.1(4) . . . . ?
N2 C00M C17 C16 2.0(4) . . . . ?
N2 C00M C17 C18 -179.5(4) . . . . ?
N2 C11 C12 C13 -179.8(5) . . . . ?
C4 C5 C6 C7 176.0(3) . . . . ?
C4 C5 C6 B1 -2.9(5) . . . . ?
C4 C5 C10 C9 -175.9(3) . . . . ?
C1 N1 C2 C3 0.7(5) . . . . ?
C1 C4 C5 C6 -3.8(5) 2_575 . . . ?
C1 C4 C5 C10 173.2(3) 2_575 . . . ?
C1 C4 C3 C2 -3.7(4) 2_575 . . . ?
C2 N1 C1 C4 178.3(3) . . . 2_575 ?
C2 N1 C1 C1 -1.8(5) . . . 2_575 ?
C28 C33 C32 F9 -179.8(3) . . . . ?
C28 C33 C32 C31 1.3(6) . . . . ?
C5 C4 C3 C2 175.1(3) . . . . ?
C5 C6 C7 C8 -1.0(5) . . . . ?
C5 C6 B1 N1 8.0(4) . . . 2_575 ?
C5 C6 B1 C28 -110.1(4) . . . . ?
C5 C6 B1 C22 124.4(3) . . . . ?
C5 C10 C9 C8 0.8(6) . . . . ?
C3 C4 C5 C6 177.4(3) . . . . ?
C3 C4 C5 C10 -5.6(5) . . . . ?
C6 C5 C10 C9 1.1(5) . . . . ?
C6 C7 C8 N2 -175.9(4) . . . . ?
C6 C7 C8 C9 2.9(6) . . . . ?
C22 C27 C26 F4 -179.9(3) . . . . ?
C22 C27 C26 C25 2.6(6) . . . . ?
C22 C23 C24 F2 -177.7(4) . . . . ?
C22 C23 C24 C25 1.1(6) . . . . ?
C33 C28 C29 F6 178.7(3) . . . . ?
C33 C28 C29 C30 -2.0(5) . . . . ?
C33 C28 B1 N1 164.4(3) . . . 2_575 ?
C33 C28 B1 C6 -77.6(4) . . . . ?
C33 C28 B1 C22 46.1(4) . . . . ?
C33 C32 C31 F8 179.0(3) . . . . ?
C33 C32 C31 C30 -0.6(6) . . . . ?
C00M N2 C8 C9 -61.1(5) . . . . ?
C00M N2 C8 C7 117.7(4) . . . . ?
C00M N2 C11 C16 2.0(5) . . . . ?
C00M N2 C11 C12 -179.4(5) . . . . ?
C00M C21 C20 C19 0.5(6) . . . . ?
C00M C17 C16 C11 -0.8(5) . . . . ?
C00M C17 C16 C15 179.0(6) . . . . ?
C00M C17 C18 C19 -1.7(6) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C10 C5 C6 B1 -179.9(3) . . . . ?
C10 C9 C8 N2 176.1(4) . . . . ?
C10 C9 C8 C7 -2.7(6) . . . . ?
C21 C00M C17 C16 -174.7(4) . . . . ?
C21 C00M C17 C18 3.8(6) . . . . ?
C21 C20 C19 C18 1.5(6) . . . . ?
C7 C6 B1 N1 -170.9(3) . . . 2_575 ?
C7 C6 B1 C28 70.9(4) . . . . ?
C7 C6 B1 C22 -54.6(4) . . . . ?
C27 C22 C23 F1 -179.7(3) . . . . ?
C27 C22 C23 C24 -1.2(5) . . . . ?
C27 C22 B1 N1 89.6(4) . . . 2_575 ?
C27 C22 B1 C28 -150.0(3) . . . . ?
C27 C22 B1 C6 -28.9(4) . . . . ?
C29 C28 C33 F10 178.1(3) . . . . ?
C29 C28 C33 C32 -0.1(5) . . . . ?
C29 C28 B1 N1 -24.8(5) . . . 2_575 ?
C29 C28 B1 C6 93.2(4) . . . . ?
C29 C28 B1 C22 -143.1(3) . . . . ?
C29 C30 C31 F8 179.1(4) . . . . ?
C29 C30 C31 C32 -1.2(6) . . . . ?
C17 C00M C21 C20 -3.1(5) . . . . ?
C17 C16 C11 N2 -0.8(5) . . . . ?
C17 C16 C11 C12 -179.5(5) . . . . ?
C17 C16 C15 C14 -179.4(6) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C8 N2 C00M C21 6.1(6) . . . . ?
C8 N2 C00M C17 -170.3(4) . . . . ?
C8 N2 C11 C16 169.6(4) . . . . ?
C8 N2 C11 C12 -11.8(7) . . . . ?
C31 C30 C29 F6 -178.0(3) . . . . ?
C31 C30 C29 C28 2.7(6) . . . . ?
C23 C22 C27 F5 176.4(3) . . . . ?
C23 C22 C27 C26 -0.6(5) . . . . ?
C23 C22 B1 N1 -87.5(4) . . . 2_575 ?
C23 C22 B1 C28 32.9(5) . . . . ?
C23 C22 B1 C6 154.1(3) . . . . ?
C16 C17 C18 C19 176.3(5) . . . . ?
C16 C11 C12 C13 -1.3(8) . . . . ?
C16 C15 C14 C13 -0.8(11) . . . . ?
C11 N2 C00M C21 173.9(4) . . . . ?
C11 N2 C00M C17 -2.5(4) . . . . ?
C11 N2 C8 C9 133.2(4) . . . . ?
C11 N2 C8 C7 -48.0(6) . . . . ?
C11 C16 C15 C14 0.4(9) . . . . ?
C11 C12 C13 C14 0.8(10) . . . . ?
C26 C25 C24 F2 179.6(4) . . . . ?
C26 C25 C24 C23 0.9(6) . . . . ?
C24 C25 C26 F4 179.8(3) . . . . ?
C24 C25 C26 C27 -2.6(6) . . . . ?
C18 C17 C16 C11 -179.0(5) . . . . ?
C18 C17 C16 C15 0.8(9) . . . . ?
B1 N1 C1 C4 -2.7(4) 2_575 . . 2_575 ?
B1 N1 C1 C1 177.1(3) 2_575 . . 2_575 ?
B1 N1 C2 C3 -178.3(3) 2_575 . . . ?
B1 C28 C33 F10 -10.0(5) . . . . ?
B1 C28 C33 C32 171.8(3) . . . . ?
B1 C28 C29 F6 7.3(5) . . . . ?
B1 C28 C29 C30 -173.4(4) . . . . ?
B1 C6 C7 C8 177.9(3) . . . . ?
B1 C22 C27 F5 -1.0(5) . . . . ?
B1 C22 C27 C26 -178.0(3) . . . . ?
B1 C22 C23 F1 -2.3(5) . . . . ?
B1 C22 C23 C24 176.1(3) . . . . ?
C12 C13 C14 C15 0.2(12) . . . . ?
C15 C16 C11 N2 179.5(4) . . . . ?
C15 C16 C11 C12 0.7(8) . . . . ?

_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_cu_20221012TN02168X_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333174'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2024-02-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C Cl3), C44 H10 B2 F22 N2'
_chemical_formula_sum            'C46 H12 B2 Cl6 F22 N2'
_chemical_formula_weight         1244.90
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   14.8212(13)
_cell_length_b                   10.0171(8)
_cell_length_c                   17.0876(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.304(6)
_cell_angle_gamma                90
_cell_volume                     2293.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5638
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.619
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.7160.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.037
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16361
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.316
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3141
_reflns_number_total             4017
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.613
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.063
_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)+(0.1138P)²+2.4354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1985
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl4)
\\sim Ueq, Uanis(Cl5) \\sim Ueq, Uanis(Cl6) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C8(H8), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.0850(5) 0.1372(4) 0.5194(3) 0.0934(18) Uani 0.605(7) 1 d . U P A 1
Cl2 Cl -0.0013(3) 0.3715(3) 0.42299(16) 0.0856(12) Uani 0.605(7) 1 d . U P A 1
Cl3 Cl 0.2025(3) 0.3769(7) 0.5425(4) 0.140(2) Uani 0.605(7) 1 d . U P A 1
F6 F 0.10287(17) 0.6847(3) 0.39896(16) 0.0535(6) Uani 1 1 d . . . . .
N1 N 0.3869(2) 0.8975(3) 0.45163(16) 0.0284(6) Uani 1 1 d . . . . .
C21 C 0.1910(3) 0.8820(4) 0.39753(19) 0.0316(7) Uani 1 1 d . . . . .
B1 B 0.2996(3) 0.8258(4) 0.4699(2) 0.0288(8) Uani 1 1 d . . . . .
F7 F -0.07247(17) 0.7873(3) 0.29537(16) 0.0589(7) Uani 1 1 d . . . . .
C20 C 0.1021(3) 0.8111(4) 0.3709(2) 0.0365(8) Uani 1 1 d . . . . .
F8 F -0.08719(17) 1.0427(3) 0.23727(15) 0.0549(7) Uani 1 1 d . . . . .
C19 C 0.0102(3) 0.8623(5) 0.3176(2) 0.0418(9) Uani 1 1 d . . . . .
Cl4 Cl 0.0395(7) 0.1550(10) 0.4932(6) 0.122(3) Uani 0.395(7) 1 d . U P A 2
Cl5 Cl 0.2318(4) 0.2684(11) 0.5799(5) 0.135(3) Uani 0.395(7) 1 d . U P A 2
Cl6 Cl 0.0787(9) 0.4077(7) 0.4438(5) 0.139(4) Uani 0.395(7) 1 d . U P A 2
F9 F 0.0817(2) 1.1929(3) 0.28620(17) 0.0573(7) Uani 1 1 d . . . . .
C18 C 0.0021(3) 0.9908(4) 0.2883(2) 0.0406(9) Uani 1 1 d . . . . .
F10 F 0.25709(18) 1.0947(2) 0.39053(16) 0.0520(6) Uani 1 1 d . . . . .
C11 C 0.0870(3) 1.0656(4) 0.3131(2) 0.0405(8) Uani 1 1 d . . . . .
F5 F 0.43899(16) 0.6645(2) 0.61308(12) 0.0390(5) Uani 1 1 d . . . . .
C12 C 0.1784(3) 1.0115(4) 0.3669(2) 0.0342(7) Uani 1 1 d . . . . .
F4 F 0.48705(17) 0.4103(2) 0.60904(13) 0.0417(5) Uani 1 1 d . . . . .
C13 C 0.3219(2) 0.6655(3) 0.4655(2) 0.0293(7) Uani 1 1 d . . . . .
F3 F 0.40683(18) 0.2690(2) 0.46084(15) 0.0479(6) Uani 1 1 d . . . . .
C22 C 0.3909(3) 0.5994(4) 0.5378(2) 0.0304(7) Uani 1 1 d . . . . .
F2 F 0.2710(2) 0.3872(2) 0.31387(15) 0.0561(7) Uani 1 1 d . . . . .
C17 C 0.4183(3) 0.4678(4) 0.5378(2) 0.0333(7) Uani 1 1 d . . . . .
F1 F 0.22004(17) 0.6400(2) 0.31453(12) 0.0448(6) Uani 1 1 d . . . . .
C16 C 0.3775(3) 0.3953(3) 0.4623(2) 0.0364(8) Uani 1 1 d . . . . .
F11 F 0.6931(3) 0.9879(5) 0.2107(2) 0.0936(13) Uani 1 1 d . . . . .
C15 C 0.3096(3) 0.4554(4) 0.3881(2) 0.0377(8) Uani 1 1 d . . . . .
C14 C 0.2839(3) 0.5873(4) 0.3910(2) 0.0339(7) Uani 1 1 d . . . . .
C1 C 0.4614(2) 0.9751(3) 0.51029(19) 0.0258(6) Uani 1 1 d . . . . .
C2 C 0.3865(3) 0.8754(4) 0.3750(2) 0.0334(7) Uani 1 1 d . . . . .
H2 H 0.334427 0.825297 0.334955 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4583(3) 0.9218(3) 0.3512(2) 0.0345(8) Uani 1 1 d . . . . .
H3 H 0.452224 0.904985 0.295649 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5398(2) 0.9935(3) 0.4086(2) 0.0284(7) Uani 1 1 d . . . . .
C5 C 0.6209(3) 1.0355(3) 0.3856(2) 0.0318(7) Uani 1 1 d . . . . .
C10 C 0.6232(3) 0.9859(4) 0.3094(3) 0.0456(9) Uani 1 1 d . . . . .
H10 H 0.576813 0.922798 0.275785 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6948(3) 1.0319(5) 0.2856(3) 0.0507(10) Uani 1 1 d . . . . .
C8 C 0.7647(3) 1.1268(5) 0.3337(3) 0.0461(9) Uani 1 1 d . . . . .
H8 H 0.811469 1.159312 0.315545 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7626(3) 1.1714(4) 0.4090(2) 0.0370(8) Uani 1 1 d . . . . .
H7 H 0.809605 1.234181 0.442227 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6928(3) 1.1259(3) 0.4376(2) 0.0299(7) Uani 1 1 d . . . . .
C23 C 0.0937(4) 0.3065(5) 0.5247(3) 0.0592(12) Uani 1 1 d . . . . .
H23 H 0.076001 0.335555 0.571080 0.071 Uiso 1 1 calc R U . A 1


_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
Cl1 C23 1.700(6) . ?
Cl2 C23 1.826(6) . ?
Cl3 C23 1.664(6) . ?
F6 C20 1.352(4) . ?
N1 B1 1.623(5) . ?
N1 C1 1.371(4) . ?
N1 C2 1.325(4) . ?
C21 B1 1.655(5) . ?
C21 C20 1.390(5) . ?
C21 C12 1.381(5) . ?
B1 C13 1.647(5) . ?
B1 C6 1.611(5) 3_676 ?
F7 C19 1.346(5) . ?
C20 C19 1.375(5) . ?
F8 C18 1.340(4) . ?
C19 C18 1.367(6) . ?
Cl4 C23 1.693(9) . ?
Cl5 C23 1.890(8) . ?
Cl6 C23 1.651(6) . ?
F9 C11 1.347(5) . ?
C18 C11 1.368(6) . ?
F10 C12 1.348(4) . ?
C11 C12 1.382(5) . ?
F5 C22 1.343(4) . ?
F4 C17 1.338(4) . ?
C13 C22 1.390(5) . ?
C13 C14 1.391(5) . ?
F3 C16 1.341(4) . ?
C22 C17 1.380(5) . ?
F2 C15 1.335(4) . ?
C17 C16 1.376(5) . ?
F1 C14 1.351(4) . ?
C16 C15 1.375(5) . ?
F11 C9 1.344(5) . ?
C15 C14 1.382(5) . ?
C1 C1 1.424(7) 3_676 ?
C1 C4 1.429(4) 3_676 ?
C2 H2 0.9300 . ?
C2 C3 1.373(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
C4 C5 1.477(5) . ?
C5 C10 1.408(5) . ?
C5 C6 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.368(6) . ?
C9 C8 1.388(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.375(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.396(5) . ?
C23 H23 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
C1 N1 B1 124.7(3) . . ?
C2 N1 B1 116.7(3) . . ?
C2 N1 C1 118.7(3) . . ?
C20 C21 B1 123.6(3) . . ?
C12 C21 B1 122.2(3) . . ?
C12 C21 C20 113.6(3) . . ?
N1 B1 C21 107.9(3) . . ?
N1 B1 C13 103.3(3) . . ?
C13 B1 C21 116.6(3) . . ?
C6 B1 N1 109.2(3) 3_676 . ?
C6 B1 C21 105.6(3) 3_676 . ?
C6 B1 C13 114.0(3) 3_676 . ?
F6 C20 C21 120.0(3) . . ?
F6 C20 C19 116.1(3) . . ?
C19 C20 C21 123.9(4) . . ?
F7 C19 C20 120.2(4) . . ?
F7 C19 C18 119.7(3) . . ?
C18 C19 C20 120.1(4) . . ?
F8 C18 C19 120.8(4) . . ?
F8 C18 C11 120.7(4) . . ?
C19 C18 C11 118.5(3) . . ?
F9 C11 C18 120.1(3) . . ?
F9 C11 C12 119.8(4) . . ?
C18 C11 C12 120.1(4) . . ?
C21 C12 C11 123.8(3) . . ?
F10 C12 C21 120.5(3) . . ?
F10 C12 C11 115.7(3) . . ?
C22 C13 B1 120.6(3) . . ?
C22 C13 C14 113.6(3) . . ?
C14 C13 B1 125.5(3) . . ?
F5 C22 C13 120.6(3) . . ?
F5 C22 C17 115.3(3) . . ?
C17 C22 C13 124.1(3) . . ?
F4 C17 C22 121.4(3) . . ?
F4 C17 C16 119.0(3) . . ?
C16 C17 C22 119.5(3) . . ?
F3 C16 C17 119.9(3) . . ?
F3 C16 C15 120.7(3) . . ?
C15 C16 C17 119.3(3) . . ?
F2 C15 C16 120.0(3) . . ?
F2 C15 C14 120.7(3) . . ?
C16 C15 C14 119.3(3) . . ?
F1 C14 C13 120.4(3) . . ?
F1 C14 C15 115.4(3) . . ?
C15 C14 C13 124.2(3) . . ?
N1 C1 C1 119.9(3) . 3_676 ?
N1 C1 C4 119.6(3) . 3_676 ?
C1 C1 C4 120.4(3) 3_676 3_676 ?
N1 C2 H2 118.0 . . ?
N1 C2 C3 124.0(3) . . ?
C3 C2 H2 118.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C1 C4 C5 123.0(3) 3_676 . ?
C3 C4 C1 115.6(3) . 3_676 ?
C3 C4 C5 121.4(3) . . ?
C10 C5 C4 119.3(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 C10 120.4(3) . . ?
C5 C10 H10 120.5 . . ?
C9 C10 C5 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
F11 C9 C10 118.2(4) . . ?
F11 C9 C8 119.6(4) . . ?
C10 C9 C8 122.1(4) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 C9 117.8(4) . . ?
C7 C8 H8 121.1 . . ?
C8 C7 H7 118.7 . . ?
C8 C7 C6 122.6(3) . . ?
C6 C7 H7 118.7 . . ?
C5 C6 B1 122.3(3) . 3_676 ?
C5 C6 C7 118.0(3) . . ?
C7 C6 B1 119.7(3) . 3_676 ?
Cl1 C23 Cl2 107.1(3) . . ?
Cl1 C23 H23 107.4 . . ?
Cl2 C23 H23 107.4 . . ?
Cl3 C23 Cl1 118.6(4) . . ?
Cl3 C23 Cl2 108.4(3) . . ?
Cl3 C23 H23 107.4 . . ?
Cl4 C23 Cl5 104.1(5) . . ?
Cl6 C23 Cl4 114.1(6) . . ?
Cl6 C23 Cl5 105.7(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
F6 C20 C19 F7 -0.6(5) . . . . ?
F6 C20 C19 C18 178.0(3) . . . . ?
N1 B1 C13 C22 84.5(3) . . . . ?
N1 B1 C13 C14 -88.8(4) . . . . ?
N1 C2 C3 C4 2.1(6) . . . . ?
C21 B1 C13 C22 -157.3(3) . . . . ?
C21 B1 C13 C14 29.3(5) . . . . ?
C21 C20 C19 F7 -179.5(3) . . . . ?
C21 C20 C19 C18 -0.9(6) . . . . ?
B1 N1 C1 C1 175.2(3) . . . 3_676 ?
B1 N1 C1 C4 -5.4(4) . . . 3_676 ?
B1 N1 C2 C3 -176.0(3) . . . . ?
B1 C21 C20 F6 -5.6(5) . . . . ?
B1 C21 C20 C19 173.2(3) . . . . ?
B1 C21 C12 F10 5.0(5) . . . . ?
B1 C21 C12 C11 -173.4(3) . . . . ?
B1 C13 C22 F5 1.5(5) . . . . ?
B1 C13 C22 C17 -175.7(3) . . . . ?
B1 C13 C14 F1 -2.7(5) . . . . ?
B1 C13 C14 C15 175.1(3) . . . . ?
F7 C19 C18 F8 -0.5(5) . . . . ?
F7 C19 C18 C11 178.8(3) . . . . ?
C20 C21 B1 N1 154.4(3) . . . . ?
C20 C21 B1 C13 38.8(5) . . . . ?
C20 C21 B1 C6 -88.9(4) . . . 3_676 ?
C20 C21 C12 F10 176.9(3) . . . . ?
C20 C21 C12 C11 -1.6(5) . . . . ?
C20 C19 C18 F8 -179.1(3) . . . . ?
C20 C19 C18 C11 0.2(6) . . . . ?
F8 C18 C11 F9 -0.1(6) . . . . ?
F8 C18 C11 C12 178.9(3) . . . . ?
C19 C18 C11 F9 -179.4(3) . . . . ?
C19 C18 C11 C12 -0.3(6) . . . . ?
F9 C11 C12 C21 -179.8(3) . . . . ?
F9 C11 C12 F10 1.6(5) . . . . ?
C18 C11 C12 C21 1.1(6) . . . . ?
C18 C11 C12 F10 -177.4(3) . . . . ?
F5 C22 C17 F4 1.1(5) . . . . ?
F5 C22 C17 C16 -176.1(3) . . . . ?
C12 C21 B1 N1 -34.6(4) . . . . ?
C12 C21 B1 C13 -150.2(3) . . . . ?
C12 C21 B1 C6 82.1(4) . . . 3_676 ?
C12 C21 C20 F6 -177.3(3) . . . . ?
C12 C21 C20 C19 1.5(5) . . . . ?
F4 C17 C16 F3 -0.1(5) . . . . ?
F4 C17 C16 C15 -177.6(3) . . . . ?
C13 C22 C17 F4 178.4(3) . . . . ?
C13 C22 C17 C16 1.1(6) . . . . ?
F3 C16 C15 F2 1.0(6) . . . . ?
F3 C16 C15 C14 -177.4(3) . . . . ?
C22 C13 C14 F1 -176.5(3) . . . . ?
C22 C13 C14 C15 1.3(5) . . . . ?
C22 C17 C16 F3 177.2(3) . . . . ?
C22 C17 C16 C15 -0.3(6) . . . . ?
F2 C15 C14 C13 -179.0(4) . . . . ?
F2 C15 C14 F1 -1.1(5) . . . . ?
C17 C16 C15 F2 178.5(3) . . . . ?
C17 C16 C15 C14 0.1(6) . . . . ?
C16 C15 C14 C13 -0.6(6) . . . . ?
C16 C15 C14 F1 177.3(3) . . . . ?
F11 C9 C8 C7 178.6(4) . . . . ?
C14 C13 C22 F5 175.6(3) . . . . ?
C14 C13 C22 C17 -1.6(5) . . . . ?
C1 N1 B1 C21 120.8(3) . . . . ?
C1 N1 B1 C13 -115.2(3) . . . . ?
C1 N1 B1 C6 6.5(4) . . . 3_676 ?
C1 N1 C2 C3 2.3(5) . . . . ?
C1 C4 C5 C10 171.7(3) 3_676 . . . ?
C1 C4 C5 C6 -9.9(5) 3_676 . . . ?
C2 N1 B1 C21 -61.1(4) . . . . ?
C2 N1 B1 C13 62.9(3) . . . . ?
C2 N1 B1 C6 -175.4(3) . . . 3_676 ?
C2 N1 C1 C1 -2.8(5) . . . 3_676 ?
C2 N1 C1 C4 176.5(3) . . . 3_676 ?
C2 C3 C4 C1 -5.4(5) . . . 3_676 ?
C2 C3 C4 C5 175.6(3) . . . . ?
C3 C4 C5 C10 -9.3(5) . . . . ?
C3 C4 C5 C6 169.0(3) . . . . ?
C4 C5 C10 C9 175.8(4) . . . . ?
C4 C5 C6 B1 8.1(5) . . . 3_676 ?
C4 C5 C6 C7 -174.5(3) . . . . ?
C5 C10 C9 F11 -177.1(4) . . . . ?
C5 C10 C9 C8 -0.6(7) . . . . ?
C10 C5 C6 B1 -173.6(3) . . . 3_676 ?
C10 C5 C6 C7 3.9(5) . . . . ?
C10 C9 C8 C7 2.2(7) . . . . ?
C9 C8 C7 C6 -0.8(6) . . . . ?
C8 C7 C6 B1 175.3(3) . . . 3_676 ?
C8 C7 C6 C5 -2.2(5) . . . . ?
C6 B1 C13 C22 -33.9(4) 3_676 . . . ?
C6 B1 C13 C14 152.7(3) 3_676 . . . ?
C6 C5 C10 C9 -2.5(6) . . . . ?

_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_cu_20230703tn232_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333175'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C84 H57.03 B2 F20 N4, 2(C3 H5 O), 2.813(C3 H6 O), 1.187(C3 H3 O)'
_chemical_formula_sum            'C102 H87.47 B2 F20 N4 O6'
_chemical_formula_weight         1866.84
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.2106(9)
_cell_length_b                   10.7119(7)
_cell_length_c                   32.530(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.306(4)
_cell_angle_gamma                90
_cell_volume                     4583.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0882 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9359.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1931
_exptl_crystal_size_max          0.535
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.206
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            26188
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.703
_diffrn_reflns_theta_min         3.360
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6845
_reflns_number_total             8811
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.114
_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)+(0.1441P)²+2.3043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2417
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C44-C45
 1.5 with sigma of 0.02
 C44-O2
 1.15 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C45 \\sim C44 \\sim C53 \\sim C43 \\sim C46 \\sim C57: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim O2: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=1-FVAR(1)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C40)=
 Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
 Sof(O1)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C43)=Sof(C57)=1-FVAR(2)
 Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(H45D)=Sof(H45E)=Sof(H45F)=0.5*FVAR(3)
 Sof(O2)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(C45)=Sof(C44)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C27(H27), C28(H28), C30(H30),
 C31(H31), C33(H33), C34(H34)
5.b X=CH2 refined with riding coordinates:
 C54(H54A,H54B), C49(H49A,H49B)
5.c Disordered Me refined with riding coordinates:
 C45(H45A,H45B,H45C,H45D,H45E,H45F)
5.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C), C55(H55A,H55B,
 H55C), C56(H56A,H56B,H56C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C53(H53A,H53B,H53C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C),
 C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.82592(13) 0.55553(15) 0.46625(5) 0.0496(4) Uani 1 1 d . . . . .
N1 N 0.40358(14) 0.62423(17) 0.49447(6) 0.0273(4) Uani 1 1 d . . . . .
C16 C 0.84331(19) 0.5082(2) 0.50458(8) 0.0369(6) Uani 1 1 d . . . . .
B1 B 0.70101(19) 0.3317(2) 0.48698(8) 0.0281(5) Uani 1 1 d . . . . .
F2 F 0.96337(14) 0.67179(17) 0.51602(7) 0.0616(5) Uani 1 1 d . . . . .
N2 N 0.68845(16) 0.4782(2) 0.31413(6) 0.0356(5) Uani 1 1 d . . . . .
C13 C 0.9158(2) 0.5723(3) 0.53010(10) 0.0450(7) Uani 1 1 d . . . . .
F3 F 1.00748(16) 0.5944(2) 0.59541(7) 0.0750(6) Uani 1 1 d . . . . .
O3 O 0.8538(3) 0.0215(4) 0.40926(13) 0.1155(14) Uani 1 1 d . . . . .
C14 C 0.9386(2) 0.5331(3) 0.57018(10) 0.0515(8) Uani 1 1 d . . . . .
F4 F 0.91107(16) 0.3904(2) 0.62279(6) 0.0722(6) Uani 1 1 d . . . . .
O4 O 0.3955(3) 0.7728(5) 0.36541(11) 0.1239(16) Uani 1 1 d . . . . .
C15 C 0.8900(2) 0.4306(3) 0.58377(9) 0.0499(7) Uani 1 1 d . . . . .
F5 F 0.77715(13) 0.26692(18) 0.57320(5) 0.0545(5) Uani 1 1 d . . . . .
C12 C 0.8195(2) 0.3683(3) 0.55728(9) 0.0415(6) Uani 1 1 d . . . . .
F6 F 0.87925(12) 0.15951(17) 0.51115(6) 0.0567(5) Uani 1 1 d . . . . .
C11 C 0.79159(17) 0.4035(2) 0.51643(8) 0.0332(5) Uani 1 1 d . . . . .
F7 F 0.87539(19) -0.0867(2) 0.50531(10) 0.0917(8) Uani 1 1 d . . . . .
C6 C 0.69585(17) 0.3721(2) 0.43963(7) 0.0291(5) Uani 1 1 d . . . . .
F8 F 0.7023(2) -0.20863(19) 0.47650(10) 0.0923(8) Uani 1 1 d . . . . .
C7 C 0.76080(19) 0.3175(2) 0.41326(8) 0.0360(5) Uani 1 1 d . . . . .
H8 H 0.806498 0.256611 0.423577 0.043 Uiso 1 1 calc R U . . .
F9 F 0.53056(16) -0.07418(18) 0.45356(7) 0.0645(5) Uani 1 1 d . . . . .
C8 C 0.7589(2) 0.3514(2) 0.37244(8) 0.0372(6) Uani 1 1 d . . . . .
H9 H 0.803558 0.314301 0.355611 0.045 Uiso 1 1 calc R U . . .
F10 F 0.53173(12) 0.17196(15) 0.46037(5) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.69036(19) 0.4412(2) 0.35631(7) 0.0325(5) Uani 1 1 d . . . . .
C10 C 0.62472(18) 0.4967(2) 0.38151(7) 0.0321(5) Uani 1 1 d . . . . .
H11 H 0.578471 0.556349 0.370735 0.038 Uiso 1 1 calc R U . . .
C5 C 0.62764(17) 0.4634(2) 0.42319(7) 0.0282(5) Uani 1 1 d . . . . .
C2 C 0.43034(18) 0.6768(2) 0.46002(7) 0.0314(5) Uani 1 1 d . . . . .
H13 H 0.395711 0.748063 0.450331 0.038 Uiso 1 1 calc R U . . .
C3 C 0.50633(18) 0.6316(2) 0.43797(7) 0.0319(5) Uani 1 1 d . . . . .
H14 H 0.522463 0.674021 0.414497 0.038 Uiso 1 1 calc R U . . .
C4 C 0.55919(17) 0.5244(2) 0.44998(7) 0.0274(5) Uani 1 1 d . . . . .
C1 C 0.46039(16) 0.5251(2) 0.51096(7) 0.0265(5) Uani 1 1 d . . . . .
C17 C 0.70412(18) 0.1789(2) 0.48828(8) 0.0333(5) Uani 1 1 d . . . . .
C18 C 0.7890(2) 0.1065(3) 0.49842(9) 0.0427(6) Uani 1 1 d . . . . .
C19 C 0.7894(3) -0.0228(3) 0.49536(13) 0.0600(9) Uani 1 1 d . . . . .
C20 C 0.7024(3) -0.0840(3) 0.48032(12) 0.0604(9) Uani 1 1 d . . . . .
C21 C 0.6161(2) -0.0169(3) 0.46898(10) 0.0479(7) Uani 1 1 d . . . . .
C22 C 0.6187(2) 0.1120(2) 0.47290(8) 0.0370(6) Uani 1 1 d . . . . .
C23 C 0.7613(2) 0.5544(2) 0.29858(8) 0.0357(5) Uani 1 1 d . . . . .
C24 C 0.7256(2) 0.5932(2) 0.25845(8) 0.0372(6) Uani 1 1 d . . . . .
C25 C 0.6259(2) 0.5388(2) 0.24963(8) 0.0356(5) Uani 1 1 d . . . . .
C26 C 0.6051(2) 0.4701(2) 0.28467(8) 0.0359(5) Uani 1 1 d . . . . .
C27 C 0.8547(2) 0.5937(3) 0.31718(9) 0.0417(6) Uani 1 1 d . . . . .
H27 H 0.877979 0.568104 0.343702 0.050 Uiso 1 1 calc R U . . .
C28 C 0.9120(2) 0.6725(3) 0.29463(10) 0.0472(7) Uani 1 1 d . . . . .
H28 H 0.974851 0.699494 0.306597 0.057 Uiso 1 1 calc R U . . .
C29 C 0.8794(2) 0.7133(3) 0.25472(9) 0.0466(7) Uani 1 1 d . . . . .
C30 C 0.7859(2) 0.6720(3) 0.23649(9) 0.0428(6) Uani 1 1 d . . . . .
H30 H 0.763579 0.696597 0.209768 0.051 Uiso 1 1 calc R U . . .
C31 C 0.5532(2) 0.5429(3) 0.21528(8) 0.0404(6) Uani 1 1 d . . . . .
H31 H 0.566045 0.589556 0.192218 0.049 Uiso 1 1 calc R U . . .
C32 C 0.4628(2) 0.4781(3) 0.21548(8) 0.0439(6) Uani 1 1 d . . . . .
C33 C 0.4453(2) 0.4090(3) 0.25138(9) 0.0480(7) Uani 1 1 d . . . . .
H33 H 0.384456 0.365614 0.251811 0.058 Uiso 1 1 calc R U . . .
C34 C 0.5151(2) 0.4036(3) 0.28576(9) 0.0437(6) Uani 1 1 d . . . . .
H34 H 0.502272 0.357001 0.308826 0.052 Uiso 1 1 calc R U . . .
C35 C 0.9465(3) 0.8008(4) 0.23117(13) 0.0671(10) Uani 1 1 d . . . . .
C37 C 0.3797(2) 0.4811(3) 0.17906(10) 0.0534(8) Uani 1 1 d . . . . .
C38 C 0.4127(3) 0.5551(4) 0.14271(10) 0.0647(10) Uani 1 1 d . . . . .
H38A H 0.470657 0.515601 0.132551 0.097 Uiso 1 1 calc R U . . .
H38B H 0.430283 0.638522 0.151468 0.097 Uiso 1 1 calc R U . . .
H38C H 0.357933 0.557852 0.121166 0.097 Uiso 1 1 calc R U . . .
C54 C 0.9010(9) 0.8485(15) 0.1932(4) 0.101(5) Uani 0.485(10) 1 d . . P A 1
H54A H 0.834659 0.826397 0.183969 0.121 Uiso 0.485(10) 1 calc R U P A 1
H54B H 0.937475 0.901802 0.177489 0.121 Uiso 0.485(10) 1 calc R U P A 1
C36 C 1.0479(7) 0.7339(10) 0.2242(3) 0.084(3) Uani 0.485(10) 1 d . . P A 1
H36A H 1.034222 0.664067 0.206040 0.126 Uiso 0.485(10) 1 calc R U P A 1
H36B H 1.079680 0.704964 0.250211 0.126 Uiso 0.485(10) 1 calc R U P A 1
H36C H 1.092399 0.791249 0.212106 0.126 Uiso 0.485(10) 1 calc R U P A 1
C40 C 0.9797(9) 0.9121(9) 0.2626(3) 0.077(3) Uani 0.485(10) 1 d . . P A 1
H40A H 1.024400 0.968009 0.249958 0.116 Uiso 0.485(10) 1 calc R U P A 1
H40B H 1.014261 0.878036 0.287364 0.116 Uiso 0.485(10) 1 calc R U P A 1
H40C H 0.920411 0.956690 0.269299 0.116 Uiso 0.485(10) 1 calc R U P A 1
C55 C 0.9667(9) 0.7324(12) 0.1899(3) 0.104(4) Uani 0.515(10) 1 d . . P A 2
H55A H 0.904408 0.727303 0.172220 0.156 Uiso 0.515(10) 1 calc R U P A 2
H55B H 0.991821 0.649772 0.196027 0.156 Uiso 0.515(10) 1 calc R U P A 2
H55C H 1.016080 0.778416 0.176161 0.156 Uiso 0.515(10) 1 calc R U P A 2
C56 C 1.0421(8) 0.8358(13) 0.2521(4) 0.101(5) Uani 0.515(10) 1 d . . P A 2
H56A H 1.074104 0.896909 0.236041 0.151 Uiso 0.515(10) 1 calc R U P A 2
H56B H 1.084985 0.763571 0.255820 0.151 Uiso 0.515(10) 1 calc R U P A 2
H56C H 1.031475 0.870507 0.278595 0.151 Uiso 0.515(10) 1 calc R U P A 2
C39 C 0.8785(9) 0.9158(11) 0.2132(4) 0.091(4) Uani 0.515(10) 1 d . . P A 2
H39A H 0.864736 0.970470 0.235373 0.137 Uiso 0.515(10) 1 calc R U P A 2
H39B H 0.815592 0.884971 0.199840 0.137 Uiso 0.515(10) 1 calc R U P A 2
H39C H 0.914500 0.960779 0.193569 0.137 Uiso 0.515(10) 1 calc R U P A 2
C41 C 0.3548(4) 0.3483(4) 0.16460(15) 0.0912(15) Uani 1 1 d . . . . .
H41A H 0.303818 0.350559 0.141595 0.137 Uiso 1 1 calc R U . . .
H41B H 0.329913 0.301677 0.186756 0.137 Uiso 1 1 calc R U . . .
H41C H 0.415104 0.309182 0.156345 0.137 Uiso 1 1 calc R U . . .
C42 C 0.2849(3) 0.5452(7) 0.19332(13) 0.0996(19) Uani 1 1 d . . . . .
H42A H 0.302710 0.627101 0.203601 0.149 Uiso 1 1 calc R U . . .
H42B H 0.259025 0.496669 0.214831 0.149 Uiso 1 1 calc R U . . .
H42C H 0.233860 0.551945 0.170440 0.149 Uiso 1 1 calc R U . . .
O2 O 0.3391(7) 0.3676(10) 0.4439(3) 0.105(4) Uani 0.406(9) 1 d D U P B 2
C53 C 0.270(2) 0.203(3) 0.4171(9) 0.155(8) Uani 0.406(9) 1 d . U P B 2
H53A H 0.212434 0.214912 0.432786 0.233 Uiso 0.406(9) 1 calc R U P B 2
H53B H 0.316405 0.145292 0.431278 0.233 Uiso 0.406(9) 1 calc R U P B 2
H53C H 0.247212 0.170775 0.390350 0.233 Uiso 0.406(9) 1 calc R U P B 2
C45 C 0.3447(13) 0.395(2) 0.3762(5) 0.139(7) Uani 0.406(9) 1 d D U P B 2
H45A H 0.326058 0.347651 0.351601 0.209 Uiso 0.203(4) 1 calc R U P B 2
H45B H 0.307493 0.471888 0.375244 0.209 Uiso 0.203(4) 1 calc R U P B 2
H45C H 0.416283 0.412226 0.378210 0.209 Uiso 0.203(4) 1 calc R U P B 2
H45D H 0.373831 0.473525 0.385102 0.209 Uiso 0.203(4) 1 calc R U P B 2
H45E H 0.392397 0.349289 0.361459 0.209 Uiso 0.203(4) 1 calc R U P B 2
H45F H 0.283607 0.408951 0.358493 0.209 Uiso 0.203(4) 1 calc R U P B 2
C44 C 0.321(4) 0.322(4) 0.4126(6) 0.182(14) Uani 0.406(9) 1 d D U P B 2
O1 O 0.3596(7) 0.2493(9) 0.3563(2) 0.141(4) Uani 0.594(9) 1 d . U P B 1
C46 C 0.3115(12) 0.1290(19) 0.4014(6) 0.156(6) Uani 0.594(9) 1 d . U P B 1
H46A H 0.257729 0.130695 0.419381 0.233 Uiso 0.594(9) 1 calc R U P B 1
H46B H 0.371941 0.095785 0.416094 0.233 Uiso 0.594(9) 1 calc R U P B 1
H46C H 0.291742 0.077176 0.377965 0.233 Uiso 0.594(9) 1 calc R U P B 1
C43 C 0.3314(6) 0.2571(10) 0.3874(3) 0.088(3) Uani 0.594(9) 1 d . U P B 1
C57 C 0.3267(10) 0.3239(18) 0.4162(4) 0.122(6) Uani 0.594(9) 1 d . U P B 1
C47 C 0.9166(5) -0.1822(6) 0.41019(19) 0.120(2) Uani 1 1 d . . . . .
H47A H 0.944431 -0.222437 0.387385 0.181 Uiso 1 1 calc R U . . .
H47B H 0.846622 -0.205848 0.410699 0.181 Uiso 1 1 calc R U . . .
H47C H 0.954139 -0.207327 0.435522 0.181 Uiso 1 1 calc R U . . .
C48 C 0.9236(4) -0.0468(5) 0.40558(14) 0.0887(15) Uani 1 1 d . . . . .
C49 C 1.0203(7) 0.0024(12) 0.3953(3) 0.181(4) Uani 1 1 d . . . . .
H49A H 1.028104 0.087841 0.391542 0.217 Uiso 1 1 calc R U . . .
H49B H 1.074435 -0.051335 0.392470 0.217 Uiso 1 1 calc R U . . .
C50 C 0.3556(7) 0.7081(6) 0.2959(2) 0.129(2) Uani 1 1 d . . . . .
H50A H 0.349477 0.765446 0.273163 0.193 Uiso 1 1 calc R U . . .
H50B H 0.305641 0.643273 0.291258 0.193 Uiso 1 1 calc R U . . .
H50C H 0.422318 0.671905 0.298395 0.193 Uiso 1 1 calc R U . . .
C51 C 0.3388(3) 0.7761(4) 0.33482(13) 0.0758(12) Uani 1 1 d . . . . .
C52 C 0.2492(5) 0.8565(7) 0.3330(2) 0.120(2) Uani 1 1 d . . . . .
H52A H 0.249302 0.911275 0.309611 0.180 Uiso 1 1 calc R U . . .
H52B H 0.250545 0.905067 0.357803 0.180 Uiso 1 1 calc R U . . .
H52C H 0.188946 0.805975 0.330246 0.180 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 C16 1.346(3) . ?
N1 B1 1.628(3) 3_666 ?
N1 C2 1.331(3) . ?
N1 C1 1.380(3) . ?
C16 C13 1.389(4) . ?
C16 C11 1.387(4) . ?
B1 C11 1.652(3) . ?
B1 C6 1.595(3) . ?
B1 C17 1.638(3) . ?
F2 C13 1.339(4) . ?
N2 C9 1.426(3) . ?
N2 C23 1.392(3) . ?
N2 C26 1.393(3) . ?
C13 C14 1.376(5) . ?
F3 C14 1.340(3) . ?
O3 C48 1.192(6) . ?
C14 C15 1.366(5) . ?
F4 C15 1.345(4) . ?
O4 C51 1.190(5) . ?
C15 C12 1.381(4) . ?
F5 C12 1.347(3) . ?
C12 C11 1.398(4) . ?
F6 C18 1.350(3) . ?
F7 C19 1.340(4) . ?
C6 C7 1.397(3) . ?
C6 C5 1.402(3) . ?
F8 C20 1.340(4) . ?
C7 H8 0.9300 . ?
C7 C8 1.375(4) . ?
F9 C21 1.342(4) . ?
C8 H9 0.9300 . ?
C8 C9 1.390(4) . ?
F10 C22 1.346(3) . ?
C9 C10 1.382(3) . ?
C10 H11 0.9300 . ?
C10 C5 1.399(3) . ?
C5 C4 1.466(3) . ?
C2 H13 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H14 0.9300 . ?
C3 C4 1.381(3) . ?
C4 C1 1.422(3) 3_666 ?
C1 C1 1.425(5) 3_666 ?
C17 C18 1.379(4) . ?
C17 C22 1.391(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.373(5) . ?
C20 C21 1.370(5) . ?
C21 C22 1.386(4) . ?
C23 C24 1.409(4) . ?
C23 C27 1.388(4) . ?
C24 C25 1.443(4) . ?
C24 C30 1.401(4) . ?
C25 C26 1.405(4) . ?
C25 C31 1.405(4) . ?
C26 C34 1.389(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.400(4) . ?
C29 C30 1.392(4) . ?
C29 C35 1.542(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.382(4) . ?
C32 C33 1.419(4) . ?
C32 C37 1.539(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.383(4) . ?
C34 H34 0.9300 . ?
C35 C54 1.418(12) . ?
C35 C36 1.554(10) . ?
C35 C40 1.605(10) . ?
C35 C55 1.575(11) . ?
C35 C56 1.429(10) . ?
C35 C39 1.603(12) . ?
C37 C38 1.520(5) . ?
C37 C41 1.525(6) . ?
C37 C42 1.537(6) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C54 H54A 0.9300 . ?
C54 H54B 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
O2 C44 1.13(2) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C53 C44 1.45(4) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C45 H45D 0.9600 . ?
C45 H45E 0.9600 . ?
C45 H45F 0.9600 . ?
C45 C44 1.48(2) . ?
O1 C43 1.113(10) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C46 C43 1.48(2) . ?
C43 C57 1.187(16) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C47 C48 1.462(8) . ?
C48 C49 1.449(10) . ?
C49 H49A 0.9300 . ?
C49 H49B 0.9300 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C50 C51 1.494(8) . ?
C51 C52 1.460(8) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 B1 119.35(19) . 3_666 ?
C2 N1 C1 118.4(2) . . ?
C1 N1 B1 121.92(18) . 3_666 ?
F1 C16 C13 114.6(2) . . ?
F1 C16 C11 121.1(2) . . ?
C11 C16 C13 124.3(3) . . ?
N1 B1 C11 104.13(18) 3_666 . ?
N1 B1 C17 107.48(18) 3_666 . ?
C6 B1 N1 108.50(18) . 3_666 ?
C6 B1 C11 113.4(2) . . ?
C6 B1 C17 107.14(19) . . ?
C17 B1 C11 115.80(19) . . ?
C23 N2 C9 124.1(2) . . ?
C23 N2 C26 108.3(2) . . ?
C26 N2 C9 125.9(2) . . ?
F2 C13 C16 120.5(3) . . ?
F2 C13 C14 119.9(3) . . ?
C14 C13 C16 119.6(3) . . ?
F3 C14 C13 120.5(3) . . ?
F3 C14 C15 120.6(3) . . ?
C15 C14 C13 118.9(3) . . ?
C14 C15 C12 119.8(3) . . ?
F4 C15 C14 120.0(3) . . ?
F4 C15 C12 120.2(3) . . ?
C15 C12 C11 124.5(3) . . ?
F5 C12 C15 115.5(3) . . ?
F5 C12 C11 120.0(2) . . ?
C16 C11 B1 124.4(2) . . ?
C16 C11 C12 112.9(2) . . ?
C12 C11 B1 122.6(2) . . ?
C7 C6 B1 120.4(2) . . ?
C7 C6 C5 117.9(2) . . ?
C5 C6 B1 121.7(2) . . ?
C6 C7 H8 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H8 119.1 . . ?
C7 C8 H9 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H9 120.0 . . ?
C8 C9 N2 120.5(2) . . ?
C10 C9 N2 119.7(2) . . ?
C10 C9 C8 119.8(2) . . ?
C9 C10 H11 119.9 . . ?
C9 C10 C5 120.2(2) . . ?
C5 C10 H11 119.9 . . ?
C6 C5 C4 119.6(2) . . ?
C10 C5 C6 120.4(2) . . ?
C10 C5 C4 119.9(2) . . ?
N1 C2 H13 118.2 . . ?
N1 C2 C3 123.7(2) . . ?
C3 C2 H13 118.2 . . ?
C2 C3 H14 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H14 119.4 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 C1 115.7(2) . 3_666 ?
C1 C4 C5 122.5(2) 3_666 . ?
N1 C1 C4 119.8(2) . 3_666 ?
N1 C1 C1 119.6(3) . 3_666 ?
C4 C1 C1 120.6(3) 3_666 3_666 ?
C18 C17 B1 125.9(2) . . ?
C18 C17 C22 114.3(2) . . ?
C22 C17 B1 119.2(2) . . ?
F6 C18 C17 120.8(2) . . ?
F6 C18 C19 115.6(3) . . ?
C17 C18 C19 123.6(3) . . ?
F7 C19 C18 120.1(3) . . ?
F7 C19 C20 120.3(3) . . ?
C20 C19 C18 119.6(3) . . ?
F8 C20 C19 120.2(3) . . ?
F8 C20 C21 120.2(3) . . ?
C21 C20 C19 119.6(3) . . ?
F9 C21 C20 120.8(3) . . ?
F9 C21 C22 120.2(3) . . ?
C20 C21 C22 119.0(3) . . ?
F10 C22 C17 120.3(2) . . ?
F10 C22 C21 115.7(2) . . ?
C21 C22 C17 124.0(3) . . ?
N2 C23 C24 109.0(2) . . ?
C27 C23 N2 129.5(2) . . ?
C27 C23 C24 121.5(2) . . ?
C23 C24 C25 106.6(2) . . ?
C30 C24 C23 119.5(2) . . ?
C30 C24 C25 133.9(2) . . ?
C26 C25 C24 107.0(2) . . ?
C26 C25 C31 119.4(2) . . ?
C31 C25 C24 133.6(2) . . ?
N2 C26 C25 108.9(2) . . ?
C34 C26 N2 129.6(2) . . ?
C34 C26 C25 121.4(2) . . ?
C23 C27 H27 121.3 . . ?
C28 C27 C23 117.4(3) . . ?
C28 C27 H27 121.3 . . ?
C27 C28 H28 118.5 . . ?
C27 C28 C29 123.0(3) . . ?
C29 C28 H28 118.5 . . ?
C28 C29 C35 120.6(3) . . ?
C30 C29 C28 118.7(3) . . ?
C30 C29 C35 120.7(3) . . ?
C24 C30 H30 120.0 . . ?
C29 C30 C24 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
C25 C31 H31 119.7 . . ?
C32 C31 C25 120.5(3) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C33 118.2(3) . . ?
C31 C32 C37 122.7(3) . . ?
C33 C32 C37 119.0(3) . . ?
C32 C33 H33 118.7 . . ?
C34 C33 C32 122.7(3) . . ?
C34 C33 H33 118.7 . . ?
C26 C34 H34 121.1 . . ?
C33 C34 C26 117.8(3) . . ?
C33 C34 H34 121.1 . . ?
C29 C35 C36 109.6(5) . . ?
C29 C35 C40 105.7(4) . . ?
C29 C35 C55 106.9(5) . . ?
C29 C35 C39 108.7(4) . . ?
C54 C35 C29 115.8(5) . . ?
C54 C35 C36 109.9(8) . . ?
C54 C35 C40 110.9(8) . . ?
C36 C35 C40 104.3(7) . . ?
C55 C35 C39 100.3(8) . . ?
C56 C35 C29 116.5(5) . . ?
C56 C35 C55 108.5(8) . . ?
C56 C35 C39 114.4(8) . . ?
C38 C37 C32 112.0(3) . . ?
C38 C37 C41 108.4(3) . . ?
C38 C37 C42 107.6(3) . . ?
C41 C37 C32 109.6(3) . . ?
C41 C37 C42 110.6(4) . . ?
C42 C37 C32 108.7(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C54 H54A 120.0 . . ?
C35 C54 H54B 120.0 . . ?
H54A C54 H54B 120.0 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C35 C55 H55A 109.5 . . ?
C35 C55 H55B 109.5 . . ?
C35 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C35 C56 H56A 109.5 . . ?
C35 C56 H56B 109.5 . . ?
C35 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C44 C53 H53A 109.5 . . ?
C44 C53 H53B 109.5 . . ?
C44 C53 H53C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
H45D C45 H45E 109.5 . . ?
H45D C45 H45F 109.5 . . ?
H45E C45 H45F 109.5 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
C44 C45 H45D 109.5 . . ?
C44 C45 H45E 109.5 . . ?
C44 C45 H45F 109.5 . . ?
O2 C44 C53 111(2) . . ?
O2 C44 C45 117(3) . . ?
C53 C44 C45 133(2) . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
O1 C43 C46 107.2(11) . . ?
O1 C43 C57 144.2(15) . . ?
C57 C43 C46 107.0(14) . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C48 C47 H47A 109.5 . . ?
C48 C47 H47B 109.5 . . ?
C48 C47 H47C 109.5 . . ?
O3 C48 C47 122.8(6) . . ?
O3 C48 C49 120.4(7) . . ?
C49 C48 C47 116.8(7) . . ?
C48 C49 H49A 120.0 . . ?
C48 C49 H49B 120.0 . . ?
H49A C49 H49B 120.0 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
C51 C50 H50C 109.5 . . ?
O4 C51 C50 124.2(6) . . ?
O4 C51 C52 119.8(6) . . ?
C52 C51 C50 115.8(5) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 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
F1 C16 C13 F2 -0.8(4) . . . . ?
F1 C16 C13 C14 179.1(2) . . . . ?
F1 C16 C11 B1 -3.6(4) . . . . ?
F1 C16 C11 C12 -179.9(2) . . . . ?
N1 B1 C11 C16 -103.5(3) 3_666 . . . ?
N1 B1 C11 C12 72.4(3) 3_666 . . . ?
N1 B1 C6 C7 -162.3(2) 3_666 . . . ?
N1 B1 C6 C5 18.4(3) 3_666 . . . ?
N1 B1 C17 C18 -140.7(3) 3_666 . . . ?
N1 B1 C17 C22 48.4(3) 3_666 . . . ?
N1 C2 C3 C4 1.6(4) . . . . ?
C16 C13 C14 F3 -179.3(3) . . . . ?
C16 C13 C14 C15 0.8(4) . . . . ?
B1 N1 C2 C3 -168.0(2) 3_666 . . . ?
B1 N1 C1 C4 -13.4(3) 3_666 . . 3_666 ?
B1 N1 C1 C1 167.8(2) 3_666 . . 3_666 ?
B1 C6 C7 C8 -179.2(2) . . . . ?
B1 C6 C5 C10 -179.9(2) . . . . ?
B1 C6 C5 C4 0.3(3) . . . . ?
B1 C17 C18 F6 4.4(4) . . . . ?
B1 C17 C18 C19 -173.8(3) . . . . ?
B1 C17 C22 F10 -5.6(4) . . . . ?
B1 C17 C22 C21 173.8(3) . . . . ?
F2 C13 C14 F3 0.6(4) . . . . ?
F2 C13 C14 C15 -179.3(3) . . . . ?
N2 C9 C10 C5 -178.4(2) . . . . ?
N2 C23 C24 C25 0.7(3) . . . . ?
N2 C23 C24 C30 179.6(2) . . . . ?
N2 C23 C27 C28 -178.7(3) . . . . ?
N2 C26 C34 C33 -178.1(3) . . . . ?
C13 C16 C11 B1 176.6(2) . . . . ?
C13 C16 C11 C12 0.3(4) . . . . ?
C13 C14 C15 F4 179.9(3) . . . . ?
C13 C14 C15 C12 0.2(5) . . . . ?
F3 C14 C15 F4 0.0(5) . . . . ?
F3 C14 C15 C12 -179.7(3) . . . . ?
C14 C15 C12 F5 178.7(3) . . . . ?
C14 C15 C12 C11 -1.0(5) . . . . ?
F4 C15 C12 F5 -1.1(4) . . . . ?
F4 C15 C12 C11 179.2(3) . . . . ?
C15 C12 C11 C16 0.8(4) . . . . ?
C15 C12 C11 B1 -175.6(3) . . . . ?
F5 C12 C11 C16 -178.9(2) . . . . ?
F5 C12 C11 B1 4.7(4) . . . . ?
F6 C18 C19 F7 0.9(5) . . . . ?
F6 C18 C19 C20 -176.2(3) . . . . ?
C11 C16 C13 F2 179.0(2) . . . . ?
C11 C16 C13 C14 -1.1(4) . . . . ?
C11 B1 C6 C7 82.5(3) . . . . ?
C11 B1 C6 C5 -96.8(3) . . . . ?
C11 B1 C17 C18 -24.9(4) . . . . ?
C11 B1 C17 C22 164.3(2) . . . . ?
F7 C19 C20 F8 1.7(6) . . . . ?
F7 C19 C20 C21 -177.8(3) . . . . ?
C6 B1 C11 C16 14.2(3) . . . . ?
C6 B1 C11 C12 -169.9(2) . . . . ?
C6 B1 C17 C18 102.8(3) . . . . ?
C6 B1 C17 C22 -68.0(3) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C6 C5 C4 C3 166.2(2) . . . . ?
C6 C5 C4 C1 -16.4(3) . . . 3_666 ?
F8 C20 C21 F9 -0.6(5) . . . . ?
F8 C20 C21 C22 -179.4(3) . . . . ?
C7 C6 C5 C10 0.8(3) . . . . ?
C7 C6 C5 C4 -179.1(2) . . . . ?
C7 C8 C9 N2 179.3(2) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
F9 C21 C22 F10 -0.1(4) . . . . ?
F9 C21 C22 C17 -179.6(3) . . . . ?
C8 C9 C10 C5 0.4(4) . . . . ?
C9 N2 C23 C24 -167.8(2) . . . . ?
C9 N2 C23 C27 10.8(4) . . . . ?
C9 N2 C26 C25 167.7(2) . . . . ?
C9 N2 C26 C34 -15.1(4) . . . . ?
C9 C10 C5 C6 -1.1(3) . . . . ?
C9 C10 C5 C4 178.8(2) . . . . ?
C10 C5 C4 C3 -13.6(3) . . . . ?
C10 C5 C4 C1 163.7(2) . . . 3_666 ?
C5 C6 C7 C8 0.1(4) . . . . ?
C2 N1 C1 C4 173.2(2) . . . 3_666 ?
C2 N1 C1 C1 -5.5(4) . . . 3_666 ?
C2 C3 C4 C5 169.3(2) . . . . ?
C2 C3 C4 C1 -8.2(3) . . . 3_666 ?
C1 N1 C2 C3 5.6(4) . . . . ?
C17 B1 C11 C16 138.7(2) . . . . ?
C17 B1 C11 C12 -45.4(3) . . . . ?
C17 B1 C6 C7 -46.5(3) . . . . ?
C17 B1 C6 C5 134.1(2) . . . . ?
C17 C18 C19 F7 179.2(3) . . . . ?
C17 C18 C19 C20 2.1(6) . . . . ?
C18 C17 C22 F10 -177.5(2) . . . . ?
C18 C17 C22 C21 1.9(4) . . . . ?
C18 C19 C20 F8 178.8(3) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
C19 C20 C21 F9 178.9(3) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 F10 178.7(3) . . . . ?
C20 C21 C22 C17 -0.8(5) . . . . ?
C22 C17 C18 F6 175.6(2) . . . . ?
C22 C17 C18 C19 -2.6(4) . . . . ?
C23 N2 C9 C8 -74.5(3) . . . . ?
C23 N2 C9 C10 104.3(3) . . . . ?
C23 N2 C26 C25 1.6(3) . . . . ?
C23 N2 C26 C34 178.8(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 C31 -179.9(3) . . . . ?
C23 C24 C30 C29 -1.3(4) . . . . ?
C23 C27 C28 C29 0.2(5) . . . . ?
C24 C23 C27 C28 -0.2(4) . . . . ?
C24 C25 C26 N2 -1.2(3) . . . . ?
C24 C25 C26 C34 -178.6(3) . . . . ?
C24 C25 C31 C32 178.9(3) . . . . ?
C25 C24 C30 C29 177.2(3) . . . . ?
C25 C26 C34 C33 -1.2(4) . . . . ?
C25 C31 C32 C33 0.7(4) . . . . ?
C25 C31 C32 C37 178.8(3) . . . . ?
C26 N2 C9 C8 121.5(3) . . . . ?
C26 N2 C9 C10 -59.7(3) . . . . ?
C26 N2 C23 C24 -1.4(3) . . . . ?
C26 N2 C23 C27 177.2(3) . . . . ?
C26 C25 C31 C32 -1.3(4) . . . . ?
C27 C23 C24 C25 -178.1(2) . . . . ?
C27 C23 C24 C30 0.8(4) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C27 C28 C29 C35 -179.9(3) . . . . ?
C28 C29 C30 C24 1.3(4) . . . . ?
C28 C29 C35 C54 -172.5(9) . . . . ?
C28 C29 C35 C36 62.5(6) . . . . ?
C28 C29 C35 C40 -49.3(6) . . . . ?
C28 C29 C35 C55 122.0(6) . . . . ?
C28 C29 C35 C56 0.5(9) . . . . ?
C28 C29 C35 C39 -130.5(7) . . . . ?
C30 C24 C25 C26 -178.3(3) . . . . ?
C30 C24 C25 C31 1.5(5) . . . . ?
C30 C29 C35 C54 8.3(10) . . . . ?
C30 C29 C35 C36 -116.6(6) . . . . ?
C30 C29 C35 C40 131.5(6) . . . . ?
C30 C29 C35 C55 -57.1(7) . . . . ?
C30 C29 C35 C56 -178.6(8) . . . . ?
C30 C29 C35 C39 50.4(7) . . . . ?
C31 C25 C26 N2 179.0(2) . . . . ?
C31 C25 C26 C34 1.5(4) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C31 C32 C37 C38 4.1(5) . . . . ?
C31 C32 C37 C41 124.4(4) . . . . ?
C31 C32 C37 C42 -114.6(4) . . . . ?
C32 C33 C34 C26 0.7(5) . . . . ?
C33 C32 C37 C38 -177.9(3) . . . . ?
C33 C32 C37 C41 -57.5(4) . . . . ?
C33 C32 C37 C42 63.4(4) . . . . ?
C35 C29 C30 C24 -179.5(3) . . . . ?
C37 C32 C33 C34 -178.6(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_tn02_154
_database_code_depnum_ccdc_archive 'CCDC 2333167'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2022-07-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B C13 F13 O3 S'
_chemical_formula_sum            'C13 B F13 O3 S'
_chemical_formula_weight         494.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   33.0522(15)
_cell_length_b                   11.2332(6)
_cell_length_c                   8.4733(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3146.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.742
_shelx_estimated_absorpt_T_min   0.245
_exptl_absorpt_coefficient_mu    3.450
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1360 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.5747.
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    2.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 2.00 1.00 0.1270
-1.00 1.00 0.00 0.0390
1.00 1.00 0.00 0.0480
-1.00 -1.00 0.00 0.0210
-1.00 0.00 0.00 0.0240
1.00 0.00 0.00 0.0520
2.00 1.00 -1.00 0.2400
-1.00 -1.00 1.00 0.2030
-1.00 2.00 -1.00 0.1670
-1.00 -1.00 -1.00 0.1980
0.00 -1.00 0.00 0.0260

_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17899
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.679
_diffrn_reflns_theta_max         66.679
_diffrn_reflns_theta_min         2.674
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.0285952
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2548
_reflns_number_total             2781
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.050
_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)+(0.0476P)²+1.9080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
S1 S 0.61118(2) 0.39930(4) 0.38741(6) 0.02674(15) Uani 1 1 d . . . . .
F5 F 0.66285(3) 0.84382(10) 0.20215(14) 0.0315(3) Uani 1 1 d . . . . .
F10 F 0.68540(3) 0.45021(10) 0.23282(13) 0.0324(3) Uani 1 1 d . . . . .
F6 F 0.68334(3) 0.80725(10) 0.52781(14) 0.0333(3) Uani 1 1 d . . . . .
F1 F 0.55057(3) 0.68357(10) 0.47500(15) 0.0356(3) Uani 1 1 d . . . . .
F7 F 0.76378(4) 0.80642(11) 0.53307(14) 0.0393(3) Uani 1 1 d . . . . .
F9 F 0.76526(4) 0.44871(11) 0.24599(14) 0.0395(3) Uani 1 1 d . . . . .
F2 F 0.51017(3) 0.88490(11) 0.42518(16) 0.0397(3) Uani 1 1 d . . . . .
F4 F 0.62152(4) 1.04414(11) 0.15317(17) 0.0425(3) Uani 1 1 d . . . . .
F3 F 0.54519(4) 1.06680(11) 0.26465(17) 0.0442(3) Uani 1 1 d . . . . .
F8 F 0.80569(3) 0.62775(13) 0.39249(15) 0.0438(3) Uani 1 1 d . . . . .
F11 F 0.55289(4) 0.43937(12) 0.58993(15) 0.0428(3) Uani 1 1 d . . . . .
O1 O 0.60781(4) 0.53600(11) 0.35649(16) 0.0271(3) Uani 1 1 d . . . . .
F12 F 0.53286(4) 0.40736(14) 0.35369(16) 0.0527(4) Uani 1 1 d . . . . .
F13 F 0.55582(4) 0.26314(12) 0.49503(18) 0.0543(4) Uani 1 1 d . . . . .
O2 O 0.63795(4) 0.37549(13) 0.51402(18) 0.0349(3) Uani 1 1 d . . . . .
O3 O 0.61310(4) 0.33767(14) 0.24251(19) 0.0403(4) Uani 1 1 d . . . . .
C6 C 0.62552(5) 0.85121(17) 0.2620(2) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.68002(5) 0.62812(16) 0.3806(2) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.60918(5) 0.75469(17) 0.3429(2) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.56954(5) 0.77065(17) 0.3962(2) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.70232(5) 0.71741(16) 0.4552(2) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.70337(5) 0.53866(16) 0.3126(2) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.74391(6) 0.71788(17) 0.4605(2) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.60477(6) 0.95525(17) 0.2345(2) 0.0292(4) Uani 1 1 d . . . . .
C3 C 0.54823(5) 0.87439(18) 0.3723(2) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.74487(6) 0.53698(17) 0.3163(2) 0.0272(4) Uani 1 1 d . . . . .
C4 C 0.56575(6) 0.96675(17) 0.2908(2) 0.0308(4) Uani 1 1 d . . . . .
C10 C 0.76547(6) 0.62715(19) 0.3901(2) 0.0288(4) Uani 1 1 d . . . . .
C13 C 0.55935(6) 0.37772(19) 0.4610(2) 0.0334(5) Uani 1 1 d . . . . .
B B 0.63299(6) 0.63567(19) 0.3634(2) 0.0230(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
S1 O1 1.5618(13) . ?
S1 O2 1.4162(14) . ?
S1 O3 1.4110(15) . ?
S1 C13 1.839(2) . ?
F5 C6 1.336(2) . ?
F10 C12 1.340(2) . ?
F6 C8 1.338(2) . ?
F1 C2 1.340(2) . ?
F7 C9 1.341(2) . ?
F9 C11 1.339(2) . ?
F2 C3 1.341(2) . ?
F4 C5 1.333(2) . ?
F3 C4 1.332(2) . ?
F8 C10 1.330(2) . ?
F11 C13 1.311(3) . ?
O1 B 1.396(2) . ?
F12 C13 1.305(2) . ?
F13 C13 1.324(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.375(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.392(3) . ?
C7 B 1.564(3) . ?
C1 C2 1.397(3) . ?
C1 B 1.561(3) . ?
C2 C3 1.377(3) . ?
C8 C9 1.375(3) . ?
C12 C11 1.372(3) . ?
C9 C10 1.379(3) . ?
C5 C4 1.381(3) . ?
C3 C4 1.374(3) . ?
C11 C10 1.371(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
O1 S1 C13 96.89(8) . . ?
O2 S1 O1 110.94(8) . . ?
O2 S1 C13 107.48(9) . . ?
O3 S1 O1 109.86(9) . . ?
O3 S1 O2 122.57(10) . . ?
O3 S1 C13 105.79(9) . . ?
B O1 S1 137.63(12) . . ?
F5 C6 C1 119.79(16) . . ?
F5 C6 C5 116.67(16) . . ?
C5 C6 C1 123.51(17) . . ?
C8 C7 B 121.88(16) . . ?
C12 C7 C8 114.42(16) . . ?
C12 C7 B 123.49(16) . . ?
C6 C1 C2 115.04(17) . . ?
C6 C1 B 121.74(16) . . ?
C2 C1 B 123.14(17) . . ?
F1 C2 C1 120.40(17) . . ?
F1 C2 C3 116.87(16) . . ?
C3 C2 C1 122.73(18) . . ?
F6 C8 C7 120.16(16) . . ?
F6 C8 C9 116.79(16) . . ?
C9 C8 C7 123.04(17) . . ?
F10 C12 C7 119.88(16) . . ?
F10 C12 C11 116.38(16) . . ?
C11 C12 C7 123.69(17) . . ?
F7 C9 C8 120.48(17) . . ?
F7 C9 C10 119.56(17) . . ?
C8 C9 C10 119.96(17) . . ?
F4 C5 C6 121.13(18) . . ?
F4 C5 C4 119.76(17) . . ?
C6 C5 C4 119.11(17) . . ?
F2 C3 C2 120.36(18) . . ?
F2 C3 C4 119.78(17) . . ?
C4 C3 C2 119.84(18) . . ?
F9 C11 C12 120.21(17) . . ?
F9 C11 C10 120.00(17) . . ?
C10 C11 C12 119.79(17) . . ?
F3 C4 C5 119.84(18) . . ?
F3 C4 C3 120.39(18) . . ?
C3 C4 C5 119.77(17) . . ?
F8 C10 C9 120.42(18) . . ?
F8 C10 C11 120.47(18) . . ?
C11 C10 C9 119.11(17) . . ?
F11 C13 S1 111.37(13) . . ?
F11 C13 F13 108.49(17) . . ?
F12 C13 S1 110.81(14) . . ?
F12 C13 F11 109.66(18) . . ?
F12 C13 F13 109.92(17) . . ?
F13 C13 S1 106.51(15) . . ?
O1 B C7 123.58(17) . . ?
O1 B C1 112.43(15) . . ?
C1 B C7 123.92(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O1 B C7 12.3(3) . . . . ?
S1 O1 B C1 -170.75(14) . . . . ?
F5 C6 C1 C2 -178.10(16) . . . . ?
F5 C6 C1 B -1.3(3) . . . . ?
F5 C6 C5 F4 -0.6(3) . . . . ?
F5 C6 C5 C4 178.68(17) . . . . ?
F10 C12 C11 F9 -1.6(3) . . . . ?
F10 C12 C11 C10 177.35(17) . . . . ?
F6 C8 C9 F7 -1.3(3) . . . . ?
F6 C8 C9 C10 179.11(17) . . . . ?
F1 C2 C3 F2 -0.7(3) . . . . ?
F1 C2 C3 C4 -179.26(17) . . . . ?
F7 C9 C10 F8 -0.7(3) . . . . ?
F7 C9 C10 C11 179.98(17) . . . . ?
F9 C11 C10 F8 0.0(3) . . . . ?
F9 C11 C10 C9 179.36(17) . . . . ?
F2 C3 C4 F3 0.3(3) . . . . ?
F2 C3 C4 C5 -179.08(18) . . . . ?
F4 C5 C4 F3 -0.5(3) . . . . ?
F4 C5 C4 C3 178.91(18) . . . . ?
O1 S1 C13 F11 -61.94(15) . . . . ?
O1 S1 C13 F12 60.42(16) . . . . ?
O1 S1 C13 F13 179.94(14) . . . . ?
O2 S1 O1 B 34.8(2) . . . . ?
O2 S1 C13 F11 52.60(17) . . . . ?
O2 S1 C13 F12 174.96(15) . . . . ?
O2 S1 C13 F13 -65.51(16) . . . . ?
O3 S1 O1 B -103.9(2) . . . . ?
O3 S1 C13 F11 -174.89(14) . . . . ?
O3 S1 C13 F12 -52.53(18) . . . . ?
O3 S1 C13 F13 67.00(16) . . . . ?
C6 C1 C2 F1 179.68(16) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C1 B O1 -143.84(17) . . . . ?
C6 C1 B C7 33.1(3) . . . . ?
C6 C5 C4 F3 -179.76(18) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C7 C8 C9 F7 179.55(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C12 C11 F9 -178.94(17) . . . . ?
C7 C12 C11 C10 0.0(3) . . . . ?
C1 C6 C5 F4 -178.49(17) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 F2 179.62(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C1 B O1 32.7(3) . . . . ?
C2 C1 B C7 -150.33(18) . . . . ?
C2 C3 C4 F3 178.87(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C8 C7 C12 F10 -177.71(16) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C7 B O1 -150.77(18) . . . . ?
C8 C7 B C1 32.6(3) . . . . ?
C8 C9 C10 F8 178.95(18) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C12 C7 C8 F6 -178.70(16) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C12 C7 B O1 34.8(3) . . . . ?
C12 C7 B C1 -141.83(19) . . . . ?
C12 C11 C10 F8 -178.90(17) . . . . ?
C12 C11 C10 C9 0.4(3) . . . . ?
C5 C6 C1 C2 -0.3(3) . . . . ?
C5 C6 C1 B 176.55(18) . . . . ?
C13 S1 O1 B 146.6(2) . . . . ?
B C7 C8 F6 6.4(3) . . . . ?
B C7 C8 C9 -174.45(18) . . . . ?
B C7 C12 F10 -2.9(3) . . . . ?
B C7 C12 C11 174.41(18) . . . . ?
B C1 C2 F1 2.9(3) . . . . ?
B C1 C2 C3 -177.43(18) . . . . ?

_olex2_submission_original_sample_id TN02-154
_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_cu_20220922TN02157_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333170'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2022-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H10 B2 F22 N2, 2(C3 H6 O)'
_chemical_formula_sum            'C50 H22 B2 F22 N2 O2'
_chemical_formula_weight         1122.31
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0598(6)
_cell_length_b                   10.5792(7)
_cell_length_c                   12.1126(8)
_cell_angle_alpha                94.889(5)
_cell_angle_beta                 97.993(5)
_cell_angle_gamma                102.729(5)
_cell_volume                     1113.31(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5578
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.63
_cell_measurement_theta_min      3.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0964 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.8888.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.053
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12542
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.576
_diffrn_reflns_theta_max         66.576
_diffrn_reflns_theta_min         3.712
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3791
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.087
_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)+(0.0686P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1380
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C17(H17), C20(H20), C21(H21)
1.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61019(17) 0.48268(13) 0.76130(11) 0.0330(4) Uani 1 1 d . . . . .
O1 O 1.0045(3) 1.1122(2) 0.3323(2) 0.0617(6) Uani 1 1 d . . . . .
N1 N 0.4719(2) 0.36650(18) 0.38654(15) 0.0232(4) Uani 1 1 d . . . . .
C22 C 0.5356(3) 0.6719(2) 0.83257(19) 0.0264(5) Uani 1 1 d . . . . .
B1 B 0.4489(3) 0.6947(3) 0.7091(2) 0.0231(6) Uani 1 1 d . . . . .
F2 F 0.74831(18) 0.44969(14) 0.96026(13) 0.0416(4) Uani 1 1 d . . . . .
C21 C 0.6078(3) 0.5694(2) 0.8488(2) 0.0274(5) Uani 1 1 d . . . . .
F3 F 0.7425(2) 0.61067(16) 1.14739(12) 0.0473(4) Uani 1 1 d . . . . .
C20 C 0.6793(3) 0.5490(2) 0.9520(2) 0.0317(6) Uani 1 1 d . . . . .
F4 F 0.59103(19) 0.80406(16) 1.12842(12) 0.0444(4) Uani 1 1 d . . . . .
C19 C 0.6760(3) 0.6296(3) 1.0460(2) 0.0343(6) Uani 1 1 d . . . . .
F5 F 0.46059(17) 0.84660(14) 0.92945(12) 0.0376(4) Uani 1 1 d . . . . .
C18 C 0.5997(3) 0.7278(3) 1.0357(2) 0.0333(6) Uani 1 1 d . . . . .
F6 F 0.69760(17) 0.93470(13) 0.81781(13) 0.0380(4) Uani 1 1 d . . . . .
C13 C 0.5325(3) 0.7468(2) 0.9316(2) 0.0295(5) Uani 1 1 d . . . . .
F7 F 0.70839(19) 1.17820(14) 0.77694(14) 0.0459(4) Uani 1 1 d . . . . .
C14 C 0.4667(3) 0.8490(2) 0.68750(19) 0.0260(5) Uani 1 1 d . . . . .
F8 F 0.4952(2) 1.23364(14) 0.61923(14) 0.0469(4) Uani 1 1 d . . . . .
C15 C 0.5827(3) 0.9544(2) 0.7410(2) 0.0293(5) Uani 1 1 d . . . . .
F9 F 0.26939(19) 1.03579(14) 0.50071(13) 0.0433(4) Uani 1 1 d . . . . .
C16 C 0.5936(3) 1.0820(2) 0.7206(2) 0.0334(6) Uani 1 1 d . . . . .
F10 F 0.25388(17) 0.79048(13) 0.53982(12) 0.0363(4) Uani 1 1 d . . . . .
C17 C 0.4870(3) 1.1101(2) 0.6412(2) 0.0346(6) Uani 1 1 d . . . . .
F11 F -0.05557(18) 0.63600(16) 0.83189(13) 0.0456(4) Uani 1 1 d . . . . .
C11 C 0.3707(3) 1.0099(2) 0.5824(2) 0.0315(6) Uani 1 1 d . . . . .
C12 C 0.3651(3) 0.8839(2) 0.6058(2) 0.0277(5) Uani 1 1 d . . . . .
C6 C 0.2725(3) 0.6179(2) 0.69673(19) 0.0250(5) Uani 1 1 d . . . . .
C7 C 0.1804(3) 0.6609(2) 0.7677(2) 0.0294(5) Uani 1 1 d . . . . .
H14 H 0.219269 0.736051 0.818256 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0314(3) 0.5914(3) 0.7623(2) 0.0308(6) Uani 1 1 d . . . . .
C9 C -0.0322(3) 0.4790(2) 0.6898(2) 0.0303(6) Uani 1 1 d . . . . .
H16 H -0.132317 0.432724 0.689347 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0573(3) 0.4375(2) 0.6178(2) 0.0277(5) Uani 1 1 d . . . . .
H17 H 0.016042 0.363178 0.566707 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2100(3) 0.5057(2) 0.62035(19) 0.0230(5) Uani 1 1 d . . . . .
C4 C 0.3016(3) 0.4599(2) 0.54162(18) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.2412(3) 0.3518(2) 0.46300(19) 0.0260(5) Uani 1 1 d . . . . .
H20 H 0.139933 0.306884 0.460185 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3260(3) 0.3089(2) 0.3891(2) 0.0260(5) Uani 1 1 d . . . . .
H21 H 0.279385 0.235699 0.337826 0.031 Uiso 1 1 calc R U . . .
C1 C 0.5418(3) 0.4763(2) 0.46048(18) 0.0211(5) Uani 1 1 d . . . . .
C23 C 0.9659(3) 1.0104(3) 0.2714(3) 0.0469(7) Uani 1 1 d . . . . .
C24 C 0.9496(4) 0.8827(3) 0.3175(3) 0.0567(9) Uani 1 1 d . . . . .
H24A H 0.845381 0.833170 0.297173 0.085 Uiso 1 1 calc R U . . .
H24B H 0.976174 0.897723 0.397868 0.085 Uiso 1 1 calc R U . . .
H24C H 1.016556 0.835101 0.287319 0.085 Uiso 1 1 calc R U . . .
C25 C 0.9335(5) 1.0083(4) 0.1472(3) 0.0682(10) Uani 1 1 d . . . . .
H25A H 0.973575 0.941321 0.111826 0.102 Uiso 1 1 calc R U . . .
H25B H 0.981411 1.091435 0.126801 0.102 Uiso 1 1 calc R U . . .
H25C H 0.824772 0.990734 0.122898 0.102 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 C21 1.348(3) . ?
O1 C23 1.206(4) . ?
N1 B1 1.607(3) 2_666 ?
N1 C2 1.334(3) . ?
N1 C1 1.376(3) . ?
C22 B1 1.652(3) . ?
C22 C21 1.399(3) . ?
C22 C13 1.387(3) . ?
B1 C14 1.652(3) . ?
B1 C6 1.605(4) . ?
F2 C20 1.340(3) . ?
C21 C20 1.382(3) . ?
F3 C19 1.342(3) . ?
C20 C19 1.371(4) . ?
F4 C18 1.348(3) . ?
C19 C18 1.373(4) . ?
F5 C13 1.358(3) . ?
C18 C13 1.373(3) . ?
F6 C15 1.361(3) . ?
F7 C16 1.342(3) . ?
C14 C15 1.392(3) . ?
C14 C12 1.386(3) . ?
F8 C17 1.344(3) . ?
C15 C16 1.378(3) . ?
F9 C11 1.342(3) . ?
C16 C17 1.365(4) . ?
F10 C12 1.354(3) . ?
C17 C11 1.383(4) . ?
F11 C8 1.355(3) . ?
C11 C12 1.378(3) . ?
C6 C7 1.393(3) . ?
C6 C5 1.399(3) . ?
C7 H14 0.9300 . ?
C7 C8 1.377(4) . ?
C8 C9 1.377(4) . ?
C9 H16 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H17 0.9300 . ?
C10 C5 1.407(3) . ?
C5 C4 1.467(3) . ?
C4 C3 1.381(3) . ?
C4 C1 1.436(3) 2_666 ?
C3 H20 0.9300 . ?
C3 C2 1.369(3) . ?
C2 H21 0.9300 . ?
C1 C1 1.424(4) 2_666 ?
C23 C24 1.491(4) . ?
C23 C25 1.489(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 B1 116.48(19) . 2_666 ?
C2 N1 C1 118.9(2) . . ?
C1 N1 B1 124.50(19) . 2_666 ?
C21 C22 B1 123.5(2) . . ?
C13 C22 B1 122.8(2) . . ?
C13 C22 C21 113.5(2) . . ?
N1 B1 C22 108.18(18) 2_666 . ?
N1 B1 C14 104.71(18) 2_666 . ?
C22 B1 C14 114.93(19) . . ?
C6 B1 N1 109.87(19) . 2_666 ?
C6 B1 C22 107.09(19) . . ?
C6 B1 C14 111.96(19) . . ?
F1 C21 C22 120.3(2) . . ?
F1 C21 C20 115.8(2) . . ?
C20 C21 C22 123.9(2) . . ?
F2 C20 C21 120.3(2) . . ?
F2 C20 C19 120.4(2) . . ?
C19 C20 C21 119.4(2) . . ?
F3 C19 C20 120.6(2) . . ?
F3 C19 C18 120.2(2) . . ?
C20 C19 C18 119.2(2) . . ?
F4 C18 C19 119.4(2) . . ?
F4 C18 C13 120.7(2) . . ?
C13 C18 C19 119.9(2) . . ?
F5 C13 C22 120.1(2) . . ?
F5 C13 C18 115.8(2) . . ?
C18 C13 C22 124.1(2) . . ?
C15 C14 B1 126.3(2) . . ?
C12 C14 B1 120.6(2) . . ?
C12 C14 C15 113.0(2) . . ?
F6 C15 C14 120.1(2) . . ?
F6 C15 C16 115.3(2) . . ?
C16 C15 C14 124.6(2) . . ?
F7 C16 C15 120.8(2) . . ?
F7 C16 C17 119.9(2) . . ?
C17 C16 C15 119.3(2) . . ?
F8 C17 C16 120.6(2) . . ?
F8 C17 C11 120.0(2) . . ?
C16 C17 C11 119.4(2) . . ?
F9 C11 C17 119.8(2) . . ?
F9 C11 C12 121.1(2) . . ?
C12 C11 C17 119.0(2) . . ?
F10 C12 C14 119.9(2) . . ?
F10 C12 C11 115.5(2) . . ?
C11 C12 C14 124.6(2) . . ?
C7 C6 B1 119.0(2) . . ?
C7 C6 C5 118.9(2) . . ?
C5 C6 B1 122.1(2) . . ?
C6 C7 H14 120.2 . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H14 120.2 . . ?
F11 C8 C7 118.2(2) . . ?
F11 C8 C9 118.9(2) . . ?
C7 C8 C9 122.9(2) . . ?
C8 C9 H16 121.1 . . ?
C8 C9 C10 117.8(2) . . ?
C10 C9 H16 121.1 . . ?
C9 C10 H17 119.4 . . ?
C9 C10 C5 121.1(2) . . ?
C5 C10 H17 119.4 . . ?
C6 C5 C10 119.7(2) . . ?
C6 C5 C4 120.5(2) . . ?
C10 C5 C4 119.8(2) . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 C1 115.3(2) . 2_666 ?
C1 C4 C5 123.0(2) 2_666 . ?
C4 C3 H20 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H20 119.0 . . ?
N1 C2 C3 123.6(2) . . ?
N1 C2 H21 118.2 . . ?
C3 C2 H21 118.2 . . ?
N1 C1 C4 119.7(2) . 2_666 ?
N1 C1 C1 119.4(3) . 2_666 ?
C1 C1 C4 120.9(3) 2_666 2_666 ?
O1 C23 C24 121.3(3) . . ?
O1 C23 C25 120.9(3) . . ?
C25 C23 C24 117.8(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
F1 C21 C20 F2 1.5(3) . . . . ?
F1 C21 C20 C19 -177.2(2) . . . . ?
N1 B1 C14 C15 -95.2(3) 2_666 . . . ?
N1 B1 C14 C12 81.3(3) 2_666 . . . ?
N1 B1 C6 C7 -176.16(19) 2_666 . . . ?
N1 B1 C6 C5 6.8(3) 2_666 . . . ?
C22 B1 C14 C15 23.3(3) . . . . ?
C22 B1 C14 C12 -160.1(2) . . . . ?
C22 B1 C6 C7 66.6(3) . . . . ?
C22 B1 C6 C5 -110.5(2) . . . . ?
C22 C21 C20 F2 -178.8(2) . . . . ?
C22 C21 C20 C19 2.5(4) . . . . ?
B1 N1 C2 C3 -177.9(2) 2_666 . . . ?
B1 N1 C1 C4 -3.1(3) 2_666 . . 2_666 ?
B1 N1 C1 C1 178.0(2) 2_666 . . 2_666 ?
B1 C22 C21 F1 0.3(4) . . . . ?
B1 C22 C21 C20 -179.4(2) . . . . ?
B1 C22 C13 F5 -2.3(4) . . . . ?
B1 C22 C13 C18 178.1(2) . . . . ?
B1 C14 C15 F6 1.4(4) . . . . ?
B1 C14 C15 C16 180.0(2) . . . . ?
B1 C14 C12 F10 -2.6(3) . . . . ?
B1 C14 C12 C11 179.6(2) . . . . ?
B1 C6 C7 C8 -176.2(2) . . . . ?
B1 C6 C5 C10 176.0(2) . . . . ?
B1 C6 C5 C4 -5.0(3) . . . . ?
F2 C20 C19 F3 0.4(4) . . . . ?
F2 C20 C19 C18 -177.7(2) . . . . ?
C21 C22 B1 N1 -27.1(3) . . . 2_666 ?
C21 C22 B1 C14 -143.7(2) . . . . ?
C21 C22 B1 C6 91.2(3) . . . . ?
C21 C22 C13 F5 -177.3(2) . . . . ?
C21 C22 C13 C18 3.1(4) . . . . ?
C21 C20 C19 F3 179.0(2) . . . . ?
C21 C20 C19 C18 1.0(4) . . . . ?
F3 C19 C18 F4 -0.6(4) . . . . ?
F3 C19 C18 C13 179.8(2) . . . . ?
C20 C19 C18 F4 177.4(2) . . . . ?
C20 C19 C18 C13 -2.2(4) . . . . ?
F4 C18 C13 C22 -179.6(2) . . . . ?
F4 C18 C13 F5 0.8(4) . . . . ?
C19 C18 C13 C22 0.1(4) . . . . ?
C19 C18 C13 F5 -179.5(2) . . . . ?
F6 C15 C16 F7 -2.1(4) . . . . ?
F6 C15 C16 C17 177.2(2) . . . . ?
C13 C22 B1 N1 158.4(2) . . . 2_666 ?
C13 C22 B1 C14 41.8(3) . . . . ?
C13 C22 B1 C6 -83.3(3) . . . . ?
C13 C22 C21 F1 175.3(2) . . . . ?
C13 C22 C21 C20 -4.4(4) . . . . ?
F7 C16 C17 F8 -0.4(4) . . . . ?
F7 C16 C17 C11 179.0(2) . . . . ?
C14 B1 C6 C7 -60.3(3) . . . . ?
C14 B1 C6 C5 122.7(2) . . . . ?
C14 C15 C16 F7 179.2(2) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
F8 C17 C11 F9 2.4(4) . . . . ?
F8 C17 C11 C12 179.5(2) . . . . ?
C15 C14 C12 F10 174.3(2) . . . . ?
C15 C14 C12 C11 -3.4(4) . . . . ?
C15 C16 C17 F8 -179.7(2) . . . . ?
C15 C16 C17 C11 -0.4(4) . . . . ?
F9 C11 C12 C14 179.0(2) . . . . ?
F9 C11 C12 F10 1.2(4) . . . . ?
C16 C17 C11 F9 -177.0(2) . . . . ?
C16 C17 C11 C12 0.2(4) . . . . ?
C17 C11 C12 C14 1.9(4) . . . . ?
C17 C11 C12 F10 -175.9(2) . . . . ?
F11 C8 C9 C10 178.4(2) . . . . ?
C12 C14 C15 F6 -175.4(2) . . . . ?
C12 C14 C15 C16 3.2(4) . . . . ?
C6 B1 C14 C15 145.8(2) . . . . ?
C6 B1 C14 C12 -37.7(3) . . . . ?
C6 C7 C8 F11 -179.7(2) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C6 C5 C4 C3 -177.9(2) . . . . ?
C6 C5 C4 C1 1.4(3) . . . 2_666 ?
C7 C6 C5 C10 -1.1(3) . . . . ?
C7 C6 C5 C4 177.9(2) . . . . ?
C7 C8 C9 C10 -1.8(4) . . . . ?
C8 C9 C10 C5 1.6(4) . . . . ?
C9 C10 C5 C6 -0.3(3) . . . . ?
C9 C10 C5 C4 -179.2(2) . . . . ?
C10 C5 C4 C3 1.0(3) . . . . ?
C10 C5 C4 C1 -179.6(2) . . . 2_666 ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C4 C3 C2 179.8(2) . . . . ?
C4 C3 C2 N1 0.1(4) . . . . ?
C2 N1 C1 C4 -179.5(2) . . . 2_666 ?
C2 N1 C1 C1 1.6(4) . . . 2_666 ?
C1 N1 C2 C3 -1.1(3) . . . . ?
C1 C4 C3 C2 0.4(3) 2_666 . . . ?

_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_tn_01_097
_database_code_depnum_ccdc_archive 'CCDC 2333171'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H36 B2 F20 N2'
_chemical_formula_sum            'C56 H36 B2 F20 N2'
_chemical_formula_weight         1138.49
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   16.8525(4)
_cell_length_b                   15.3208(5)
_cell_length_c                   9.5674(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.2810(10)
_cell_angle_gamma                90
_cell_volume                     2437.91(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      72.43
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.701
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 24006 reflections, Rint = 0.0470
 (12253 with I > 3sig(I), Rint = 0.0415)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0210
0.00 0.00 -1.00 0.0130
0.00 0.00 1.00 0.0040
0.00 1.00 1.00 0.0620
0.00 -1.00 -1.00 0.0190
-1.00 1.00 -1.00 0.1290
-1.00 0.00 0.00 0.1430
1.00 0.00 0.00 0.1470

_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.667
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6626
_reflns_number_total             7899
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         7899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.061
_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)+(0.0994P)²+0.5823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.22662(9) 0.33190(10) 0.35802(14) 0.0307(3) Uani 1 1 d . . . . .
F1 F 0.07405(9) 0.57530(10) 0.47060(15) 0.0342(3) Uani 1 1 d . . . . .
F6 F 0.32306(9) 0.48274(11) 0.41592(18) 0.0388(4) Uani 1 1 d . . . . .
F10 F 0.18270(11) 0.48622(13) -0.05459(16) 0.0438(4) Uani 1 1 d . . . . .
F4 F 0.20553(11) 0.25661(11) 0.59646(15) 0.0424(4) Uani 1 1 d . . . . .
F2 F 0.05747(10) 0.50016(12) 0.71127(16) 0.0424(4) Uani 1 1 d . . . . .
F3 F 0.11918(12) 0.33695(13) 0.77702(17) 0.0500(5) Uani 1 1 d . . . . .
F7 F 0.45782(10) 0.44611(14) 0.3190(2) 0.0566(5) Uani 1 1 d . . . . .
F9 F 0.31781(15) 0.44693(17) -0.1481(2) 0.0672(6) Uani 1 1 d . . . . .
F8 F 0.45784(13) 0.42559(15) 0.0363(3) 0.0676(6) Uani 1 1 d . . . . .
N1 N -0.08440(12) 0.53133(14) -0.1379(2) 0.0243(4) Uani 1 1 d . . . . .
C1 C -0.03097(13) 0.47975(16) -0.0492(2) 0.0234(5) Uani 1 1 d . . . . .
C4 C 0.03846(14) 0.61280(16) 0.0570(2) 0.0255(5) Uani 1 1 d . . . . .
C6 C 0.15562(14) 0.61007(17) 0.2521(2) 0.0263(5) Uani 1 1 d . . . . .
C22 C 0.18498(14) 0.37781(17) 0.4423(2) 0.0277(5) Uani 1 1 d . . . . .
C18 C 0.11066(15) 0.49718(17) 0.4975(3) 0.0290(5) Uani 1 1 d . . . . .
C17 C 0.15339(14) 0.45979(16) 0.4005(2) 0.0256(5) Uani 1 1 d . . . . .
C5 C 0.09850(14) 0.65811(16) 0.1605(2) 0.0267(5) Uani 1 1 d . . . . .
C2 C -0.07538(15) 0.61717(17) -0.1306(3) 0.0303(5) Uani 1 1 d . . . . .
H2 H -0.111388 0.651337 -0.191230 0.036 Uiso 1 1 calc R U . . .
C3 C -0.01595(16) 0.65909(17) -0.0389(3) 0.0307(5) Uani 1 1 d . . . . .
H3 H -0.012399 0.719625 -0.041503 0.037 Uiso 1 1 calc R U . . .
C23 C 0.24383(15) 0.48107(16) 0.1868(3) 0.0284(5) Uani 1 1 d . . . . .
C8 C 0.21279(15) 0.74666(17) 0.3569(2) 0.0300(5) Uani 1 1 d . . . . .
C7 C 0.21202(14) 0.65653(17) 0.3483(2) 0.0289(5) Uani 1 1 d . . . . .
H7 H 0.250541 0.625288 0.408847 0.035 Uiso 1 1 calc R U . . .
C24 C 0.31797(16) 0.47250(18) 0.2745(3) 0.0333(6) Uani 1 1 d . . . . .
C21 C 0.17467(16) 0.33669(18) 0.5663(3) 0.0325(5) Uani 1 1 d . . . . .
C19 C 0.10019(16) 0.4587(2) 0.6238(3) 0.0345(6) Uani 1 1 d . . . . .
C10 C 0.09822(17) 0.74980(18) 0.1692(3) 0.0357(6) Uani 1 1 d . . . . .
H10 H 0.059897 0.781648 0.109275 0.043 Uiso 1 1 calc R U . . .
C12 C 0.33910(16) 0.74678(18) 0.5516(2) 0.0337(5) Uani 1 1 d . . . . .
H12A H 0.369080 0.712825 0.492279 0.040 Uiso 1 1 calc R U . . .
H12B H 0.315275 0.706712 0.611550 0.040 Uiso 1 1 calc R U . . .
C28 C 0.24877(17) 0.47314(18) 0.0440(3) 0.0349(6) Uani 1 1 d . . . . .
C13 C 0.39587(16) 0.80890(19) 0.6436(3) 0.0366(6) Uani 1 1 d . . . . .
H13A H 0.416125 0.851172 0.582589 0.044 Uiso 1 1 calc R U . . .
H13B H 0.365456 0.840617 0.704987 0.044 Uiso 1 1 calc R U . . .
C11 C 0.27304(16) 0.79766(18) 0.4590(3) 0.0343(6) Uani 1 1 d . . . . .
H11A H 0.243713 0.830462 0.520786 0.041 Uiso 1 1 calc R U . . .
H11B H 0.298504 0.839709 0.404667 0.041 Uiso 1 1 calc R U . . .
C20 C 0.13179(17) 0.37736(19) 0.6584(3) 0.0355(6) Uani 1 1 d . . . . .
C9 C 0.15393(17) 0.79254(18) 0.2654(3) 0.0363(6) Uani 1 1 d . . . . .
H9 H 0.152667 0.853144 0.269966 0.044 Uiso 1 1 calc R U . . .
C14 C 0.46692(17) 0.7652(2) 0.7347(3) 0.0408(6) Uani 1 1 d . . . . .
H14A H 0.497056 0.732349 0.674166 0.049 Uiso 1 1 calc R U . . .
H14B H 0.447156 0.724299 0.798414 0.049 Uiso 1 1 calc R U . . .
C25 C 0.38925(17) 0.4541(2) 0.2273(4) 0.0418(7) Uani 1 1 d . . . . .
C27 C 0.3190(2) 0.4543(2) -0.0080(3) 0.0448(7) Uani 1 1 d . . . . .
C26 C 0.38957(19) 0.4441(2) 0.0843(4) 0.0478(7) Uani 1 1 d . . . . .
C15 C 0.52288(18) 0.8304(2) 0.8213(3) 0.0461(7) Uani 1 1 d . . . . .
H15A H 0.538680 0.874334 0.758078 0.055 Uiso 1 1 calc R U . . .
H15B H 0.493827 0.859634 0.887421 0.055 Uiso 1 1 calc R U . . .
B1 B 0.16045(15) 0.50606(18) 0.2468(3) 0.0245(5) Uani 1 1 d . . . . .
C16 C 0.5979(2) 0.7887(3) 0.9030(5) 0.0727(12) Uani 1 1 d . . . . .
H16A H 0.626970 0.759513 0.838320 0.109 Uiso 1 1 calc R U . . .
H16B H 0.582869 0.747185 0.969254 0.109 Uiso 1 1 calc R U . . .
H16C H 0.631287 0.832997 0.953324 0.109 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
F5 C22 1.349(3) . ?
F1 C18 1.352(3) . ?
F6 C24 1.351(3) . ?
F10 C28 1.353(3) . ?
F4 C21 1.345(3) . ?
F2 C19 1.348(3) . ?
F3 C20 1.340(3) . ?
F7 C25 1.339(3) . ?
F9 C27 1.342(4) . ?
F8 C26 1.336(3) . ?
N1 C1 1.382(3) . ?
N1 C2 1.324(3) . ?
N1 B1 1.620(3) 3_565 ?
C1 C1 1.430(4) 3_565 ?
C1 C4 1.424(3) 3_565 ?
C4 C5 1.471(3) . ?
C4 C3 1.383(3) . ?
C6 C5 1.402(3) . ?
C6 C7 1.405(3) . ?
C6 B1 1.597(4) . ?
C22 C17 1.397(3) . ?
C22 C21 1.378(3) . ?
C18 C17 1.387(3) . ?
C18 C19 1.381(4) . ?
C17 B1 1.654(3) . ?
C5 C10 1.407(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C23 C24 1.394(4) . ?
C23 C28 1.388(4) . ?
C23 B1 1.646(3) . ?
C8 C7 1.383(4) . ?
C8 C11 1.508(3) . ?
C8 C9 1.402(4) . ?
C7 H7 0.9300 . ?
C24 C25 1.379(4) . ?
C21 C20 1.376(4) . ?
C19 C20 1.375(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.370(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.525(3) . ?
C12 C11 1.521(4) . ?
C28 C27 1.386(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.518(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 H9 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(4) . ?
C25 C26 1.378(5) . ?
C27 C26 1.371(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.516(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 124.2(2) . 3_565 ?
C2 N1 C1 118.5(2) . . ?
C2 N1 B1 117.2(2) . 3_565 ?
N1 C1 C1 119.4(3) . 3_565 ?
N1 C1 C4 119.6(2) . 3_565 ?
C4 C1 C1 121.0(3) 3_565 3_565 ?
C1 C4 C5 123.4(2) 3_565 . ?
C3 C4 C1 115.6(2) . 3_565 ?
C3 C4 C5 121.0(2) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 B1 122.5(2) . . ?
C7 C6 B1 119.6(2) . . ?
F5 C22 C17 120.5(2) . . ?
F5 C22 C21 115.2(2) . . ?
C21 C22 C17 124.2(2) . . ?
F1 C18 C17 120.6(2) . . ?
F1 C18 C19 115.2(2) . . ?
C19 C18 C17 124.2(2) . . ?
C22 C17 B1 124.2(2) . . ?
C18 C17 C22 113.2(2) . . ?
C18 C17 B1 122.5(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C10 119.7(2) . . ?
C10 C5 C4 120.2(2) . . ?
N1 C2 H2 117.9 . . ?
N1 C2 C3 124.1(2) . . ?
C3 C2 H2 117.9 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C24 C23 B1 123.0(2) . . ?
C28 C23 C24 113.2(2) . . ?
C28 C23 B1 123.6(2) . . ?
C7 C8 C11 123.7(2) . . ?
C7 C8 C9 117.7(2) . . ?
C9 C8 C11 118.6(2) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 H7 118.5 . . ?
F6 C24 C23 119.9(2) . . ?
F6 C24 C25 115.7(2) . . ?
C25 C24 C23 124.4(3) . . ?
F4 C21 C22 120.2(2) . . ?
F4 C21 C20 120.0(2) . . ?
C20 C21 C22 119.7(3) . . ?
F2 C19 C18 119.9(3) . . ?
F2 C19 C20 120.2(2) . . ?
C20 C19 C18 119.9(2) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.4(2) . . ?
F10 C28 C23 120.0(2) . . ?
F10 C28 C27 115.8(2) . . ?
C27 C28 C23 124.2(3) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 114.8(2) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C8 C11 C12 117.7(2) . . ?
C8 C11 H11A 107.9 . . ?
C8 C11 H11B 107.9 . . ?
C12 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
F3 C20 C21 120.3(3) . . ?
F3 C20 C19 121.0(3) . . ?
C19 C20 C21 118.7(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C13 C14 C15 112.6(3) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
F7 C25 C24 120.7(3) . . ?
F7 C25 C26 119.9(3) . . ?
C26 C25 C24 119.4(3) . . ?
F9 C27 C28 120.0(3) . . ?
F9 C27 C26 120.3(3) . . ?
C26 C27 C28 119.6(3) . . ?
F8 C26 C25 120.4(3) . . ?
F8 C26 C27 120.6(3) . . ?
C27 C26 C25 119.0(3) . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.3(3) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N1 B1 C17 104.90(19) 3_565 . ?
N1 B1 C23 108.96(19) 3_565 . ?
C6 B1 N1 109.53(19) . 3_565 ?
C6 B1 C17 112.82(19) . . ?
C6 B1 C23 107.1(2) . . ?
C23 B1 C17 113.45(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
F5 C22 C17 C18 178.5(2) . . . . ?
F5 C22 C17 B1 2.2(3) . . . . ?
F5 C22 C21 F4 0.4(3) . . . . ?
F5 C22 C21 C20 -178.8(2) . . . . ?
F1 C18 C17 C22 -177.9(2) . . . . ?
F1 C18 C17 B1 -1.5(4) . . . . ?
F1 C18 C19 F2 -1.5(3) . . . . ?
F1 C18 C19 C20 177.0(2) . . . . ?
F6 C24 C25 F7 1.0(4) . . . . ?
F6 C24 C25 C26 -179.0(3) . . . . ?
F10 C28 C27 F9 -2.4(4) . . . . ?
F10 C28 C27 C26 177.0(3) . . . . ?
F4 C21 C20 F3 -1.3(4) . . . . ?
F4 C21 C20 C19 -179.2(2) . . . . ?
F2 C19 C20 F3 1.7(4) . . . . ?
F2 C19 C20 C21 179.6(2) . . . . ?
F7 C25 C26 F8 0.6(5) . . . . ?
F7 C25 C26 C27 -178.7(3) . . . . ?
F9 C27 C26 F8 -0.8(5) . . . . ?
F9 C27 C26 C25 178.5(3) . . . . ?
N1 C2 C3 C4 -1.8(4) . . . . ?
C1 N1 C2 C3 -0.5(4) . . . . ?
C1 C4 C5 C6 4.2(3) 3_565 . . . ?
C1 C4 C5 C10 -175.0(2) 3_565 . . . ?
C1 C4 C3 C2 2.8(4) 3_565 . . . ?
C4 C5 C10 C9 -180.0(2) . . . . ?
C6 C5 C10 C9 0.8(4) . . . . ?
C22 C17 B1 N1 86.2(3) . . . 3_565 ?
C22 C17 B1 C6 -154.6(2) . . . . ?
C22 C17 B1 C23 -32.6(3) . . . . ?
C22 C21 C20 F3 177.9(2) . . . . ?
C22 C21 C20 C19 0.0(4) . . . . ?
C18 C17 B1 N1 -89.7(3) . . . 3_565 ?
C18 C17 B1 C6 29.5(3) . . . . ?
C18 C17 B1 C23 151.5(2) . . . . ?
C18 C19 C20 F3 -176.8(2) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C17 C22 C21 F4 178.3(2) . . . . ?
C17 C22 C21 C20 -0.9(4) . . . . ?
C17 C18 C19 F2 -179.9(2) . . . . ?
C17 C18 C19 C20 -1.4(4) . . . . ?
C5 C4 C3 C2 -176.2(2) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C5 C6 B1 N1 -7.3(3) . . . 3_565 ?
C5 C6 B1 C17 -123.8(2) . . . . ?
C5 C6 B1 C23 110.7(2) . . . . ?
C5 C10 C9 C8 0.3(4) . . . . ?
C2 N1 C1 C1 1.4(4) . . . 3_565 ?
C2 N1 C1 C4 -178.8(2) . . . 3_565 ?
C3 C4 C5 C6 -176.9(2) . . . . ?
C3 C4 C5 C10 3.9(4) . . . . ?
C23 C24 C25 F7 -179.3(3) . . . . ?
C23 C24 C25 C26 0.8(5) . . . . ?
C23 C28 C27 F9 179.2(3) . . . . ?
C23 C28 C27 C26 -1.3(5) . . . . ?
C7 C6 C5 C4 179.5(2) . . . . ?
C7 C6 C5 C10 -1.3(3) . . . . ?
C7 C6 B1 N1 175.0(2) . . . 3_565 ?
C7 C6 B1 C17 58.5(3) . . . . ?
C7 C6 B1 C23 -67.0(3) . . . . ?
C7 C8 C11 C12 3.4(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C24 C23 C28 F10 -175.2(2) . . . . ?
C24 C23 C28 C27 3.0(4) . . . . ?
C24 C23 B1 N1 -154.5(2) . . . 3_565 ?
C24 C23 B1 C6 87.1(3) . . . . ?
C24 C23 B1 C17 -38.0(3) . . . . ?
C24 C25 C26 F8 -179.5(3) . . . . ?
C24 C25 C26 C27 1.2(5) . . . . ?
C21 C22 C17 C18 0.7(3) . . . . ?
C21 C22 C17 B1 -175.6(2) . . . . ?
C19 C18 C17 C22 0.5(4) . . . . ?
C19 C18 C17 B1 176.8(2) . . . . ?
C12 C13 C14 C15 178.4(3) . . . . ?
C28 C23 C24 F6 176.9(2) . . . . ?
C28 C23 C24 C25 -2.8(4) . . . . ?
C28 C23 B1 N1 30.7(3) . . . 3_565 ?
C28 C23 B1 C6 -87.7(3) . . . . ?
C28 C23 B1 C17 147.2(2) . . . . ?
C28 C27 C26 F8 179.7(3) . . . . ?
C28 C27 C26 C25 -1.0(5) . . . . ?
C13 C12 C11 C8 177.9(2) . . . . ?
C13 C14 C15 C16 -175.0(3) . . . . ?
C11 C8 C7 C6 -179.7(2) . . . . ?
C11 C8 C9 C10 179.2(3) . . . . ?
C11 C12 C13 C14 -176.8(2) . . . . ?
C9 C8 C7 C6 0.4(4) . . . . ?
C9 C8 C11 C12 -176.7(2) . . . . ?
B1 N1 C1 C1 -175.9(2) 3_565 . . 3_565 ?
B1 N1 C1 C4 3.9(3) 3_565 . . 3_565 ?
B1 N1 C2 C3 177.0(2) 3_565 . . . ?
B1 C6 C5 C4 1.8(3) . . . . ?
B1 C6 C5 C10 -179.0(2) . . . . ?
B1 C6 C7 C8 178.5(2) . . . . ?
B1 C23 C24 F6 1.7(4) . . . . ?
B1 C23 C24 C25 -178.0(3) . . . . ?
B1 C23 C28 F10 0.0(4) . . . . ?
B1 C23 C28 C27 178.3(3) . . . . ?

_olex2_submission_original_sample_id TN_01_097
_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_tn02203_sq
_database_code_depnum_ccdc_archive 'CCDC 2333172'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C84 H58 B2 F20 N4, 4(C3 H6 O)'
_chemical_formula_sum            'C96 H82 B2 F20 N4 O4'
_chemical_formula_weight         1757.27
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.9839(7)
_cell_length_b                   13.2502(10)
_cell_length_c                   17.5105(12)
_cell_angle_alpha                71.475(4)
_cell_angle_beta                 77.749(4)
_cell_angle_gamma                70.273(4)
_cell_volume                     2258.8(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      66.805
_cell_measurement_theta_min      2.680
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.7237
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1428 before and 0.1073 after correction.
The Ratio of minimum to maximum transmission is 0.7949.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0420
0.00 1.00 0.00 0.0540
-1.00 1.00 -1.00 0.0620
1.00 -1.00 1.00 0.0650
-1.00 -1.00 -1.00 0.0850
1.00 1.00 1.00 0.0820
-1.00 0.00 0.00 0.0210
1.00 0.00 0.00 0.0170
1.00 0.00 -1.00 0.0540
0.00 1.00 1.00 0.0860
0.00 0.00 1.00 0.1040

_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27687
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        66.824
_diffrn_reflns_theta_max         66.824
_diffrn_reflns_theta_min         2.680
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.028608000000000005
_diffrn_source_voltage           44.7
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6483
_reflns_number_total             7665
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         7665
_refine_ls_number_restraints     348
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.079
_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)+(0.1896P)²+0.5388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2629
_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. Uiso/Uaniso restraints and constraints
O2 \\sim C4 \\sim C5 \\sim C6 \\sim O2A \\sim C4A \\sim C5A \\sim C6A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim C1 \\sim C2 \\sim C3 \\sim O1A \\sim C1A \\sim C2A \\sim C3A \\sim O2
\\sim C4 \\sim C5 \\sim C6 \\sim O2A \\sim C4A \\sim C5A \\sim C6A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F2A \\sim F2B \\sim F3A \\sim F3B \\sim C39 \\sim C40: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(O2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(O2A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq,
Uanis(C6A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(O1A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq,
Uanis(C3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2B) \\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
3. Others
 Sof(O2A)=Sof(C4A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C6A)=Sof(H6AA)=
 Sof(H6AB)=Sof(H6AC)=1-FVAR(1)
 Sof(O2)=Sof(C4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=FVAR(1)
 Sof(C7A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(2)
 Sof(C7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
 Sof(O1A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(H3AC)=1-FVAR(3)
 Sof(O1)=Sof(C1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=FVAR(3)
 Sof(F2B)=Sof(F3B)=1-FVAR(4)
 Sof(F2A)=Sof(F3A)=FVAR(4)
4.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C22(H22), C24(H24), C25(H25), C28(H28),
 C30(H30), C31(H31), C34(H34), C35(H35)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC),
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C2A(H2AA,H2AB,
 H2AC), C3A(H3AA,H3AB,H3AC), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C5A(H5AA,H5AB,
 H5AC), C6A(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.51901(19) 0.26586(15) 0.57425(12) 0.0377(5) Uani 1 1 d . . . . .
F2A F 0.4449(13) 0.0864(7) 0.6549(9) 0.047(3) Uani 0.70(4) 1 d . U P A 1
F2B F 0.476(2) 0.0726(14) 0.628(2) 0.050(4) Uani 0.30(4) 1 d . U P A 2
F3A F 0.5504(11) -0.0550(8) 0.7920(9) 0.049(2) Uani 0.70(4) 1 d . U P A 1
F3B F 0.572(2) -0.0702(16) 0.7665(19) 0.052(4) Uani 0.30(4) 1 d . U P A 2
F4 F 0.7243(2) -0.00675(17) 0.84868(12) 0.0455(5) Uani 1 1 d . . . . .
F5 F 0.79285(17) 0.17782(13) 0.77672(9) 0.0289(4) Uani 1 1 d . . . . .
F6 F 0.93056(17) 0.14621(14) 0.63006(12) 0.0376(5) Uani 1 1 d . . . . .
F7 F 1.1774(2) 0.1395(2) 0.61008(18) 0.0674(8) Uani 1 1 d . . . . .
F8 F 1.2456(2) 0.3280(3) 0.5884(2) 0.0790(10) Uani 1 1 d . . . . .
F9 F 1.0566(3) 0.5240(2) 0.58392(16) 0.0611(7) Uani 1 1 d . . . . .
F10 F 0.80757(18) 0.53329(15) 0.60184(12) 0.0363(5) Uani 1 1 d . . . . .
N2 N 0.3566(2) 0.53336(18) 0.10596(13) 0.0187(5) Uani 1 1 d . . . . .
N1 N 0.64793(19) 0.41353(16) 0.54759(12) 0.0129(4) Uani 1 1 d . . . . .
C28 C 0.1432(14) 0.9271(11) -0.1356(8) 0.025(2) Uani 0.533(9) 1 d . . P B 1
C7A C 0.1665(19) 0.9130(14) -0.1573(9) 0.028(3) Uani 0.467(9) 1 d . . P B 2
C29 C 0.0882(11) 0.8998(7) -0.1981(5) 0.048(2) Uani 0.533(9) 1 d . . P B 1
H8A H 0.159089 0.852799 -0.227194 0.072 Uiso 0.533(9) 1 calc R U P B 1
H8B H 0.046942 0.969064 -0.236822 0.072 Uiso 0.533(9) 1 calc R U P B 1
H8C H 0.023415 0.860336 -0.170095 0.072 Uiso 0.533(9) 1 calc R U P B 1
C8A C 0.0303(11) 0.9254(8) -0.1620(8) 0.051(3) Uani 0.467(9) 1 d . . P B 2
H8AA H 0.022867 0.855239 -0.165172 0.077 Uiso 0.467(9) 1 calc R U P B 2
H8AB H 0.000753 0.984586 -0.210343 0.077 Uiso 0.467(9) 1 calc R U P B 2
H8AC H -0.023880 0.944692 -0.113489 0.077 Uiso 0.467(9) 1 calc R U P B 2
C30 C 0.2435(10) 0.9848(8) -0.1762(5) 0.051(2) Uani 0.533(9) 1 d . . P B 1
H9A H 0.276386 1.002517 -0.135663 0.077 Uiso 0.533(9) 1 calc R U P B 1
H9B H 0.204984 1.053746 -0.216090 0.077 Uiso 0.533(9) 1 calc R U P B 1
H9C H 0.315473 0.936397 -0.203651 0.077 Uiso 0.533(9) 1 calc R U P B 1
C9A C 0.2557(9) 0.8909(6) -0.2331(4) 0.043(2) Uani 0.467(9) 1 d . . P B 2
H9AA H 0.346640 0.871604 -0.223657 0.064 Uiso 0.467(9) 1 calc R U P B 2
H9AB H 0.236231 0.957726 -0.278576 0.064 Uiso 0.467(9) 1 calc R U P B 2
H9AC H 0.241946 0.829055 -0.245965 0.064 Uiso 0.467(9) 1 calc R U P B 2
C31 C 0.0264(8) 1.0061(6) -0.0960(5) 0.051(2) Uani 0.533(9) 1 d . . P B 1
H10A H -0.039714 0.967862 -0.068715 0.076 Uiso 0.533(9) 1 calc R U P B 1
H10B H -0.011215 1.072706 -0.137995 0.076 Uiso 0.533(9) 1 calc R U P B 1
H10C H 0.056316 1.027751 -0.056318 0.076 Uiso 0.533(9) 1 calc R U P B 1
C10A C 0.1729(12) 1.0260(7) -0.1494(6) 0.046(2) Uani 0.467(9) 1 d . . P B 2
H10D H 0.109396 1.047262 -0.104489 0.069 Uiso 0.467(9) 1 calc R U P B 2
H10E H 0.152844 1.084045 -0.199967 0.069 Uiso 0.467(9) 1 calc R U P B 2
H10F H 0.260625 1.016962 -0.138814 0.069 Uiso 0.467(9) 1 calc R U P B 2
C11 C 0.3180(3) 0.2533(2) -0.07317(16) 0.0265(6) Uani 1 1 d . . . . .
C12 C 0.1779(4) 0.2486(4) -0.0540(3) 0.0567(11) Uani 1 1 d . . . . .
H12A H 0.159822 0.214715 0.004102 0.085 Uiso 1 1 calc R U . . .
H12B H 0.165002 0.203882 -0.085068 0.085 Uiso 1 1 calc R U . . .
H12C H 0.118550 0.324159 -0.068723 0.085 Uiso 1 1 calc R U . . .
C13 C 0.4097(4) 0.1337(3) -0.0517(2) 0.0419(8) Uani 1 1 d . . . . .
H13A H 0.499885 0.135948 -0.059623 0.063 Uiso 1 1 calc R U . . .
H13B H 0.400593 0.092669 -0.086814 0.063 Uiso 1 1 calc R U . . .
H13C H 0.386947 0.096529 0.005115 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3483(4) 0.3035(3) -0.16386(19) 0.0434(9) Uani 1 1 d . . . . .
H14A H 0.285054 0.376651 -0.180776 0.065 Uiso 1 1 calc R U . . .
H14B H 0.343041 0.254433 -0.193994 0.065 Uiso 1 1 calc R U . . .
H14C H 0.436273 0.311619 -0.175032 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3044(2) 0.6378(2) 0.05241(14) 0.0174(5) Uani 1 1 d . . . . .
C16 C 0.2926(3) 0.7436(2) 0.05618(16) 0.0231(6) Uani 1 1 d . . . . .
H16 H 0.317162 0.754650 0.101064 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2436(3) 0.8328(2) -0.00774(18) 0.0261(6) Uani 1 1 d . . . . .
H17 H 0.235023 0.905821 -0.005907 0.031 Uiso 1 1 calc R U . . .
C18 C 0.2062(3) 0.8195(2) -0.07539(18) 0.0280(6) Uani 1 1 d . . . . .
C19 C 0.2200(3) 0.7128(2) -0.07794(15) 0.0208(5) Uani 1 1 d . . . . .
H19 H 0.195204 0.701690 -0.122733 0.025 Uiso 1 1 calc R U . . .
C20 C 0.2705(2) 0.6214(2) -0.01476(15) 0.0170(5) Uani 1 1 d . . . . .
C21 C 0.3053(2) 0.5025(2) -0.00302(14) 0.0166(5) Uani 1 1 d . . . . .
C22 C 0.2936(2) 0.4390(2) -0.04982(14) 0.0193(5) Uani 1 1 d . . . . .
H22 H 0.256922 0.474517 -0.099542 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3360(3) 0.3232(2) -0.02323(15) 0.0209(5) Uani 1 1 d . . . . .
C24 C 0.3876(3) 0.2745(2) 0.05081(16) 0.0237(6) Uani 1 1 d . . . . .
H24 H 0.415708 0.195581 0.069188 0.028 Uiso 1 1 calc R U . . .
C25 C 0.4000(3) 0.3350(2) 0.09895(15) 0.0224(5) Uani 1 1 d . . . . .
H25 H 0.435066 0.299162 0.149194 0.027 Uiso 1 1 calc R U . . .
C26 C 0.3586(2) 0.4512(2) 0.07029(14) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.3801(2) 0.56960(19) 0.30399(14) 0.0145(5) Uani 1 1 d . . . . .
C7 C 0.3333(2) 0.5808(2) 0.23289(14) 0.0171(5) Uani 1 1 d . . . . .
H28 H 0.251640 0.633516 0.220556 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4028(2) 0.5170(2) 0.17922(15) 0.0181(5) Uani 1 1 d . . . . .
C9 C 0.5206(3) 0.4358(2) 0.19887(15) 0.0203(5) Uani 1 1 d . . . . .
H30 H 0.567360 0.389826 0.163875 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5683(2) 0.4229(2) 0.26890(15) 0.0199(5) Uani 1 1 d . . . . .
H31 H 0.648173 0.367713 0.281897 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5009(2) 0.4902(2) 0.32194(14) 0.0169(5) Uani 1 1 d . . . . .
C4 C 0.5533(2) 0.47320(19) 0.39622(14) 0.0156(5) Uani 1 1 d . . . . .
C3 C 0.6805(2) 0.4112(2) 0.40902(15) 0.0191(5) Uani 1 1 d . . . . .
H34 H 0.739733 0.388672 0.365238 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7229(2) 0.3814(2) 0.48375(15) 0.0170(5) Uani 1 1 d . . . . .
H35 H 0.809772 0.335809 0.490279 0.020 Uiso 1 1 calc R U . . .
C1 C 0.5247(2) 0.48451(19) 0.53746(13) 0.0136(5) Uani 1 1 d . . . . .
C37 C 0.6592(2) 0.2346(2) 0.67164(14) 0.0181(5) Uani 1 1 d . . . . .
C38 C 0.5735(3) 0.2031(2) 0.64241(18) 0.0261(6) Uani 1 1 d . . . . .
C39 C 0.5371(3) 0.1065(3) 0.6797(2) 0.0404(8) Uani 1 1 d . U . . .
C40 C 0.5875(3) 0.0357(3) 0.7491(2) 0.0413(8) Uani 1 1 d . U . . .
C41 C 0.6735(3) 0.0620(2) 0.78134(18) 0.0315(7) Uani 1 1 d . . . . .
C42 C 0.7069(3) 0.1590(2) 0.74269(15) 0.0222(6) Uani 1 1 d . . . . .
C43 C 0.8545(2) 0.3391(2) 0.62224(14) 0.0181(5) Uani 1 1 d . . . . .
C44 C 0.9554(3) 0.2422(3) 0.62219(16) 0.0277(6) Uani 1 1 d . . . . .
C45 C 1.0855(3) 0.2367(3) 0.6113(2) 0.0415(8) Uani 1 1 d . . . . .
C46 C 1.1202(3) 0.3310(4) 0.5999(2) 0.0457(9) Uani 1 1 d . . . . .
C47 C 1.0239(4) 0.4306(4) 0.5973(2) 0.0412(8) Uani 1 1 d . . . . .
C48 C 0.8959(3) 0.4321(3) 0.60817(16) 0.0263(6) Uani 1 1 d . . . . .
B1 B 0.6974(3) 0.3527(2) 0.63571(15) 0.0147(5) Uani 1 1 d . . . . .
O1 O 0.9951(19) 0.7804(14) 0.5615(10) 0.078(4) Uani 0.624(9) 1 d . U P C 1
C36 C 0.9897(11) 0.8555(9) 0.5867(7) 0.081(2) Uani 0.624(9) 1 d . U P C 1
C35 C 0.8852(17) 0.9044(14) 0.6414(10) 0.116(4) Uani 0.624(9) 1 d . U P C 1
H2A H 0.846792 0.983155 0.614992 0.175 Uiso 0.624(9) 1 calc R U P C 1
H2B H 0.919307 0.897574 0.690705 0.175 Uiso 0.624(9) 1 calc R U P C 1
H2C H 0.818449 0.865517 0.655513 0.175 Uiso 0.624(9) 1 calc R U P C 1
C34 C 1.1086(12) 0.8917(10) 0.5802(8) 0.096(3) Uani 0.624(9) 1 d . U P C 1
H3A H 1.184690 0.841871 0.556553 0.144 Uiso 0.624(9) 1 calc R U P C 1
H3B H 1.122964 0.888912 0.634246 0.144 Uiso 0.624(9) 1 calc R U P C 1
H3C H 1.095365 0.968011 0.545382 0.144 Uiso 0.624(9) 1 calc R U P C 1
O1A O 0.994(4) 0.796(3) 0.545(2) 0.085(5) Uani 0.376(9) 1 d . U P C 2
C1A C 0.915(2) 0.8154(16) 0.6063(11) 0.086(3) Uani 0.376(9) 1 d . U P C 2
C2A C 0.787(3) 0.790(2) 0.6083(18) 0.133(8) Uani 0.376(9) 1 d . U P C 2
H2AA H 0.801318 0.742490 0.572717 0.199 Uiso 0.376(9) 1 calc R U P C 2
H2AB H 0.719939 0.860234 0.589656 0.199 Uiso 0.376(9) 1 calc R U P C 2
H2AC H 0.759548 0.752443 0.663933 0.199 Uiso 0.376(9) 1 calc R U P C 2
C3A C 0.903(3) 0.851(3) 0.6767(19) 0.129(7) Uani 0.376(9) 1 d . U P C 2
H3AA H 0.897788 0.789887 0.725216 0.193 Uiso 0.376(9) 1 calc R U P C 2
H3AB H 0.823574 0.913796 0.678151 0.193 Uiso 0.376(9) 1 calc R U P C 2
H3AC H 0.978787 0.875334 0.675077 0.193 Uiso 0.376(9) 1 calc R U P C 2
O2 O 1.1103(16) 0.6126(13) 0.7677(9) 0.080(4) Uani 0.694(16) 1 d . U P D 1
C33 C 1.0150(8) 0.5918(10) 0.8060(5) 0.055(2) Uani 0.694(16) 1 d . U P D 1
C32 C 0.9560(11) 0.5133(13) 0.7847(7) 0.094(3) Uani 0.694(16) 1 d . U P D 1
H5A H 0.975528 0.440521 0.824555 0.141 Uiso 0.694(16) 1 calc R U P D 1
H5B H 0.994186 0.504386 0.730450 0.141 Uiso 0.694(16) 1 calc R U P D 1
H5C H 0.861465 0.545947 0.785654 0.141 Uiso 0.694(16) 1 calc R U P D 1
C27 C 0.9666(16) 0.5971(14) 0.8902(10) 0.065(3) Uani 0.694(16) 1 d . U P D 1
H6A H 0.874551 0.640587 0.893311 0.097 Uiso 0.694(16) 1 calc R U P D 1
H6B H 1.017093 0.632588 0.907525 0.097 Uiso 0.694(16) 1 calc R U P D 1
H6C H 0.975871 0.521582 0.925654 0.097 Uiso 0.694(16) 1 calc R U P D 1
O2A O 1.101(3) 0.643(2) 0.7626(18) 0.051(4) Uani 0.306(16) 1 d . U P D 2
C4A C 0.990(2) 0.625(3) 0.7811(16) 0.067(4) Uani 0.306(16) 1 d . U P D 2
C5A C 0.9187(19) 0.595(2) 0.7505(11) 0.070(4) Uani 0.306(16) 1 d . U P D 2
H5AA H 0.969063 0.566563 0.704432 0.104 Uiso 0.306(16) 1 calc R U P D 2
H5AB H 0.844406 0.658842 0.731698 0.104 Uiso 0.306(16) 1 calc R U P D 2
H5AC H 0.887021 0.536338 0.791302 0.104 Uiso 0.306(16) 1 calc R U P D 2
C6A C 0.949(3) 0.625(3) 0.874(2) 0.060(5) Uani 0.306(16) 1 d . U P D 2
H6AA H 1.027202 0.608249 0.899797 0.090 Uiso 0.306(16) 1 calc R U P D 2
H6AB H 0.903398 0.569153 0.901903 0.090 Uiso 0.306(16) 1 calc R U P D 2
H6AC H 0.891362 0.698939 0.877527 0.090 Uiso 0.306(16) 1 calc R U P D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C38 1.346(3) . ?
F2A C39 1.315(7) . ?
F2B C39 1.48(2) . ?
F3A C40 1.342(7) . ?
F3B C40 1.40(2) . ?
F4 C41 1.336(3) . ?
F5 C42 1.342(3) . ?
F6 C44 1.348(4) . ?
F7 C45 1.345(4) . ?
F8 C46 1.339(4) . ?
F9 C47 1.340(4) . ?
F10 C48 1.350(4) . ?
N2 C15 1.411(3) . ?
N2 C26 1.409(3) . ?
N2 C8 1.406(3) . ?
N1 C2 1.335(3) . ?
N1 C1 1.373(3) . ?
N1 B1 1.611(3) . ?
C28 C29 1.541(14) . ?
C28 C30 1.481(17) . ?
C28 C31 1.549(13) . ?
C28 C18 1.520(14) . ?
C7A C8A 1.47(2) . ?
C7A C9A 1.520(14) . ?
C7A C10A 1.572(18) . ?
C7A C18 1.598(17) . ?
C29 H8A 0.9800 . ?
C29 H8B 0.9800 . ?
C29 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C30 H9A 0.9800 . ?
C30 H9B 0.9800 . ?
C30 H9C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C31 H10A 0.9800 . ?
C31 H10B 0.9800 . ?
C31 H10C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11 C12 1.522(5) . ?
C11 C13 1.539(4) . ?
C11 C14 1.526(4) . ?
C11 C23 1.542(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.385(4) . ?
C15 C20 1.404(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.412(4) . ?
C18 C19 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.398(3) . ?
C20 C21 1.446(4) . ?
C21 C22 1.398(4) . ?
C21 C26 1.396(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(4) . ?
C23 C24 1.397(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.401(4) . ?
C6 C7 1.392(3) . ?
C6 C5 1.411(3) . ?
C6 B1 1.618(3) 2_666 ?
C7 H28 0.9500 . ?
C7 C8 1.395(4) . ?
C8 C9 1.401(4) . ?
C9 H30 0.9500 . ?
C9 C10 1.373(4) . ?
C10 H31 0.9500 . ?
C10 C5 1.412(4) . ?
C5 C4 1.455(3) . ?
C4 C3 1.385(4) . ?
C4 C1 1.437(3) 2_666 ?
C3 H34 0.9500 . ?
C3 C2 1.375(4) . ?
C2 H35 0.9500 . ?
C1 C1 1.412(5) 2_666 ?
C37 C38 1.388(4) . ?
C37 C42 1.398(4) . ?
C37 B1 1.652(4) . ?
C38 C39 1.389(4) . ?
C39 C40 1.368(5) . ?
C40 C41 1.381(5) . ?
C41 C42 1.381(4) . ?
C43 C44 1.384(4) . ?
C43 C48 1.388(4) . ?
C43 B1 1.646(3) . ?
C44 C45 1.381(4) . ?
C45 C46 1.369(6) . ?
C46 C47 1.379(6) . ?
C47 C48 1.373(5) . ?
O1 C36 1.19(2) . ?
C36 C35 1.441(15) . ?
C36 C34 1.507(17) . ?
C35 H2A 0.9800 . ?
C35 H2B 0.9800 . ?
C35 H2C 0.9800 . ?
C34 H3A 0.9800 . ?
C34 H3B 0.9800 . ?
C34 H3C 0.9800 . ?
O1A C1A 1.27(4) . ?
C1A C2A 1.54(4) . ?
C1A C3A 1.42(4) . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
O2 C33 1.184(17) . ?
C33 C32 1.563(15) . ?
C33 C27 1.472(18) . ?
C32 H5A 0.9800 . ?
C32 H5B 0.9800 . ?
C32 H5C 0.9800 . ?
C27 H6A 0.9800 . ?
C27 H6B 0.9800 . ?
C27 H6C 0.9800 . ?
O2A C4A 1.28(4) . ?
C4A C5A 1.25(3) . ?
C4A C6A 1.60(4) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 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
C26 N2 C15 107.3(2) . . ?
C8 N2 C15 125.2(2) . . ?
C8 N2 C26 127.4(2) . . ?
C2 N1 C1 118.7(2) . . ?
C2 N1 B1 118.25(19) . . ?
C1 N1 B1 122.35(19) . . ?
C29 C28 C31 105.9(10) . . ?
C30 C28 C29 110.6(10) . . ?
C30 C28 C31 109.3(10) . . ?
C30 C28 C18 108.4(10) . . ?
C18 C28 C29 109.2(9) . . ?
C18 C28 C31 113.4(9) . . ?
C8A C7A C9A 112.8(12) . . ?
C8A C7A C10A 107.7(12) . . ?
C8A C7A C18 106.8(13) . . ?
C9A C7A C10A 107.0(14) . . ?
C9A C7A C18 114.3(10) . . ?
C10A C7A C18 107.9(9) . . ?
C28 C29 H8A 109.5 . . ?
C28 C29 H8B 109.5 . . ?
C28 C29 H8C 109.5 . . ?
H8A C29 H8B 109.5 . . ?
H8A C29 H8C 109.5 . . ?
H8B C29 H8C 109.5 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C28 C30 H9A 109.5 . . ?
C28 C30 H9B 109.5 . . ?
C28 C30 H9C 109.5 . . ?
H9A C30 H9B 109.5 . . ?
H9A C30 H9C 109.5 . . ?
H9B C30 H9C 109.5 . . ?
C7A C9A H9AA 109.5 . . ?
C7A C9A H9AB 109.5 . . ?
C7A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C28 C31 H10A 109.5 . . ?
C28 C31 H10B 109.5 . . ?
C28 C31 H10C 109.5 . . ?
H10A C31 H10B 109.5 . . ?
H10A C31 H10C 109.5 . . ?
H10B C31 H10C 109.5 . . ?
C7A C10A H10D 109.5 . . ?
C7A C10A H10E 109.5 . . ?
C7A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C12 C11 C13 108.7(3) . . ?
C12 C11 C14 110.0(3) . . ?
C12 C11 C23 108.5(2) . . ?
C13 C11 C23 111.2(2) . . ?
C14 C11 C13 107.4(3) . . ?
C14 C11 C23 111.0(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N2 129.7(2) . . ?
C16 C15 C20 121.0(2) . . ?
C20 C15 N2 109.1(2) . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.8(2) . . ?
C17 C16 H16 121.1 . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.7(3) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C28 115.2(5) . . ?
C17 C18 C7A 127.2(6) . . ?
C19 C18 C28 126.3(5) . . ?
C19 C18 C7A 114.0(6) . . ?
C19 C18 C17 118.3(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C21 106.9(2) . . ?
C19 C20 C15 120.1(2) . . ?
C19 C20 C21 133.0(2) . . ?
C22 C21 C20 132.0(2) . . ?
C26 C21 C20 107.4(2) . . ?
C26 C21 C22 120.7(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C11 119.6(2) . . ?
C22 C23 C24 118.2(2) . . ?
C24 C23 C11 122.1(2) . . ?
C23 C24 H24 118.2 . . ?
C25 C24 C23 123.6(2) . . ?
C25 C24 H24 118.2 . . ?
C24 C25 H25 121.4 . . ?
C24 C25 C26 117.1(2) . . ?
C26 C25 H25 121.4 . . ?
C21 C26 N2 109.3(2) . . ?
C21 C26 C25 120.7(2) . . ?
C25 C26 N2 130.0(2) . . ?
C7 C6 C5 118.4(2) . . ?
C7 C6 B1 122.0(2) . 2_666 ?
C5 C6 B1 119.6(2) . 2_666 ?
C6 C7 H28 119.0 . . ?
C6 C7 C8 121.9(2) . . ?
C8 C7 H28 119.0 . . ?
C7 C8 N2 120.9(2) . . ?
C7 C8 C9 119.2(2) . . ?
C9 C8 N2 119.9(2) . . ?
C8 C9 H30 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H30 120.1 . . ?
C9 C10 H31 119.4 . . ?
C9 C10 C5 121.3(2) . . ?
C5 C10 H31 119.4 . . ?
C6 C5 C10 119.3(2) . . ?
C6 C5 C4 120.8(2) . . ?
C10 C5 C4 119.8(2) . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 C1 115.4(2) . 2_666 ?
C1 C4 C5 122.4(2) 2_666 . ?
C4 C3 H34 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H34 119.3 . . ?
N1 C2 C3 123.3(2) . . ?
N1 C2 H35 118.4 . . ?
C3 C2 H35 118.4 . . ?
N1 C1 C4 119.4(2) . 2_666 ?
N1 C1 C1 120.2(3) . 2_666 ?
C1 C1 C4 120.4(3) 2_666 2_666 ?
C38 C37 C42 113.6(2) . . ?
C38 C37 B1 126.8(2) . . ?
C42 C37 B1 119.4(2) . . ?
F1 C38 C37 121.5(2) . . ?
F1 C38 C39 114.7(3) . . ?
C37 C38 C39 123.8(3) . . ?
F2A C39 C38 121.5(4) . . ?
F2A C39 C40 118.3(4) . . ?
C38 C39 F2B 114.6(9) . . ?
C40 C39 F2B 123.1(8) . . ?
C40 C39 C38 119.9(3) . . ?
F3A C40 C39 123.6(5) . . ?
F3A C40 C41 117.0(5) . . ?
C39 C40 F3B 113.0(12) . . ?
C39 C40 C41 119.2(3) . . ?
C41 C40 F3B 125.4(10) . . ?
F4 C41 C40 120.0(3) . . ?
F4 C41 C42 120.9(3) . . ?
C42 C41 C40 119.2(3) . . ?
F5 C42 C37 119.9(2) . . ?
F5 C42 C41 115.7(2) . . ?
C41 C42 C37 124.3(3) . . ?
C44 C43 C48 113.7(3) . . ?
C44 C43 B1 127.0(2) . . ?
C48 C43 B1 119.3(2) . . ?
F6 C44 C43 120.6(3) . . ?
F6 C44 C45 115.6(3) . . ?
C45 C44 C43 123.8(3) . . ?
F7 C45 C44 119.8(4) . . ?
F7 C45 C46 120.4(3) . . ?
C46 C45 C44 119.7(3) . . ?
F8 C46 C45 120.9(4) . . ?
F8 C46 C47 120.0(4) . . ?
C45 C46 C47 119.1(3) . . ?
F9 C47 C46 119.7(3) . . ?
F9 C47 C48 121.1(4) . . ?
C48 C47 C46 119.1(3) . . ?
F10 C48 C43 119.9(3) . . ?
F10 C48 C47 115.6(3) . . ?
C47 C48 C43 124.5(3) . . ?
N1 B1 C6 108.68(18) . 2_666 ?
N1 B1 C37 108.36(19) . . ?
N1 B1 C43 105.90(18) . . ?
C6 B1 C37 107.71(18) 2_666 . ?
C6 B1 C43 111.2(2) 2_666 . ?
C43 B1 C37 114.8(2) . . ?
O1 C36 C35 126.0(16) . . ?
O1 C36 C34 121.3(13) . . ?
C35 C36 C34 111.2(11) . . ?
C36 C35 H2A 109.5 . . ?
C36 C35 H2B 109.5 . . ?
C36 C35 H2C 109.5 . . ?
H2A C35 H2B 109.5 . . ?
H2A C35 H2C 109.5 . . ?
H2B C35 H2C 109.5 . . ?
C36 C34 H3A 109.5 . . ?
C36 C34 H3B 109.5 . . ?
C36 C34 H3C 109.5 . . ?
H3A C34 H3B 109.5 . . ?
H3A C34 H3C 109.5 . . ?
H3B C34 H3C 109.5 . . ?
O1A C1A C2A 111(2) . . ?
O1A C1A C3A 142(3) . . ?
C3A C1A C2A 107(2) . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C1A C3A H3AA 109.5 . . ?
C1A C3A H3AB 109.5 . . ?
C1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
O2 C33 C32 120.7(11) . . ?
O2 C33 C27 126.4(13) . . ?
C27 C33 C32 109.4(10) . . ?
C33 C32 H5A 109.5 . . ?
C33 C32 H5B 109.5 . . ?
C33 C32 H5C 109.5 . . ?
H5A C32 H5B 109.5 . . ?
H5A C32 H5C 109.5 . . ?
H5B C32 H5C 109.5 . . ?
C33 C27 H6A 109.5 . . ?
C33 C27 H6B 109.5 . . ?
C33 C27 H6C 109.5 . . ?
H6A C27 H6B 109.5 . . ?
H6A C27 H6C 109.5 . . ?
H6B C27 H6C 109.5 . . ?
O2A C4A C6A 105(2) . . ?
C5A C4A O2A 138(2) . . ?
C5A C4A C6A 116(2) . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 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
F1 C38 C39 F2A -7.7(11) . . . . ?
F1 C38 C39 F2B 16.5(12) . . . . ?
F1 C38 C39 C40 179.3(3) . . . . ?
F2A C39 C40 F3A 1.8(7) . . . . ?
F2A C39 C40 C41 -172.7(10) . . . . ?
F2B C39 C40 F3B -1.7(11) . . . . ?
F2B C39 C40 C41 161.8(14) . . . . ?
F3A C40 C41 F4 5.6(10) . . . . ?
F3A C40 C41 C42 -175.1(9) . . . . ?
F3B C40 C41 F4 -18.3(16) . . . . ?
F3B C40 C41 C42 161.0(16) . . . . ?
F4 C41 C42 F5 0.6(4) . . . . ?
F4 C41 C42 C37 179.3(2) . . . . ?
F6 C44 C45 F7 -0.8(5) . . . . ?
F6 C44 C45 C46 177.7(3) . . . . ?
F7 C45 C46 F8 -0.9(6) . . . . ?
F7 C45 C46 C47 176.7(3) . . . . ?
F8 C46 C47 F9 -0.6(6) . . . . ?
F8 C46 C47 C48 179.2(3) . . . . ?
F9 C47 C48 F10 2.1(4) . . . . ?
F9 C47 C48 C43 -180.0(3) . . . . ?
N2 C15 C16 C17 176.4(3) . . . . ?
N2 C15 C20 C19 -178.1(2) . . . . ?
N2 C15 C20 C21 -1.1(3) . . . . ?
N2 C8 C9 C10 177.4(2) . . . . ?
C28 C18 C19 C20 -174.7(7) . . . . ?
C7A C18 C19 C20 171.8(8) . . . . ?
C29 C28 C18 C17 -171.0(8) . . . . ?
C29 C28 C18 C19 3.6(13) . . . . ?
C8A C7A C18 C17 -116.9(10) . . . . ?
C8A C7A C18 C19 71.9(10) . . . . ?
C30 C28 C18 C17 68.4(9) . . . . ?
C30 C28 C18 C19 -116.9(8) . . . . ?
C9A C7A C18 C17 117.6(10) . . . . ?
C9A C7A C18 C19 -53.6(15) . . . . ?
C31 C28 C18 C17 -53.2(11) . . . . ?
C31 C28 C18 C19 121.5(8) . . . . ?
C10A C7A C18 C17 -1.3(16) . . . . ?
C10A C7A C18 C19 -172.5(8) . . . . ?
C11 C23 C24 C25 -177.2(3) . . . . ?
C12 C11 C23 C22 -80.0(4) . . . . ?
C12 C11 C23 C24 96.5(4) . . . . ?
C13 C11 C23 C22 160.5(3) . . . . ?
C13 C11 C23 C24 -23.0(4) . . . . ?
C14 C11 C23 C22 41.0(4) . . . . ?
C14 C11 C23 C24 -142.5(3) . . . . ?
C15 N2 C26 C21 -1.7(3) . . . . ?
C15 N2 C26 C25 -179.4(3) . . . . ?
C15 N2 C8 C7 44.2(4) . . . . ?
C15 N2 C8 C9 -135.6(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C15 C20 C21 C22 179.8(3) . . . . ?
C15 C20 C21 C26 0.0(3) . . . . ?
C16 C15 C20 C19 -2.1(4) . . . . ?
C16 C15 C20 C21 174.9(2) . . . . ?
C16 C17 C18 C28 174.6(7) . . . . ?
C16 C17 C18 C7A -171.4(9) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C18 C19 C20 C15 1.5(4) . . . . ?
C18 C19 C20 C21 -174.5(3) . . . . ?
C19 C20 C21 C22 -3.9(5) . . . . ?
C19 C20 C21 C26 176.4(3) . . . . ?
C20 C15 C16 C17 1.3(4) . . . . ?
C20 C21 C22 C23 -179.9(2) . . . . ?
C20 C21 C26 N2 1.1(3) . . . . ?
C20 C21 C26 C25 179.0(2) . . . . ?
C21 C22 C23 C11 177.5(2) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C22 C21 C26 N2 -178.7(2) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 N2 178.5(3) . . . . ?
C24 C25 C26 C21 1.1(4) . . . . ?
C26 N2 C15 C16 -173.8(3) . . . . ?
C26 N2 C15 C20 1.8(3) . . . . ?
C26 N2 C8 C7 -139.1(3) . . . . ?
C26 N2 C8 C9 41.2(4) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
C6 C7 C8 N2 -177.0(2) . . . . ?
C6 C7 C8 C9 2.7(4) . . . . ?
C6 C5 C4 C3 -168.3(2) . . . . ?
C6 C5 C4 C1 14.5(4) . . . 2_666 ?
C7 C6 C5 C10 -1.7(3) . . . . ?
C7 C6 C5 C4 -178.7(2) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C8 N2 C15 C16 3.5(4) . . . . ?
C8 N2 C15 C20 179.1(2) . . . . ?
C8 N2 C26 C21 -179.0(2) . . . . ?
C8 N2 C26 C25 3.4(4) . . . . ?
C8 C9 C10 C5 -0.1(4) . . . . ?
C9 C10 C5 C6 2.1(4) . . . . ?
C9 C10 C5 C4 179.1(2) . . . . ?
C10 C5 C4 C3 14.8(4) . . . . ?
C10 C5 C4 C1 -162.5(2) . . . 2_666 ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C5 C4 C3 C2 -169.8(2) . . . . ?
C4 C3 C2 N1 -3.0(4) . . . . ?
C2 N1 C1 C4 -175.1(2) . . . 2_666 ?
C2 N1 C1 C1 5.0(4) . . . 2_666 ?
C2 N1 B1 C6 161.1(2) . . . 2_666 ?
C2 N1 B1 C37 -82.1(2) . . . . ?
C2 N1 B1 C43 41.5(3) . . . . ?
C1 N1 C2 C3 -3.6(4) . . . . ?
C1 N1 B1 C6 -28.6(3) . . . 2_666 ?
C1 N1 B1 C37 88.1(3) . . . . ?
C1 N1 B1 C43 -148.2(2) . . . . ?
C1 C4 C3 C2 7.6(4) 2_666 . . . ?
C37 C38 C39 F2A 172.4(11) . . . . ?
C37 C38 C39 F2B -163.4(12) . . . . ?
C37 C38 C39 C40 -0.6(6) . . . . ?
C38 C37 C42 F5 178.6(2) . . . . ?
C38 C37 C42 C41 0.0(4) . . . . ?
C38 C37 B1 N1 -14.2(3) . . . . ?
C38 C37 B1 C6 103.2(3) . . . 2_666 ?
C38 C37 B1 C43 -132.3(3) . . . . ?
C38 C39 C40 F3A 175.0(10) . . . . ?
C38 C39 C40 F3B -162.9(12) . . . . ?
C38 C39 C40 C41 0.5(6) . . . . ?
C39 C40 C41 F4 -179.5(3) . . . . ?
C39 C40 C41 C42 -0.2(5) . . . . ?
C40 C41 C42 F5 -178.7(3) . . . . ?
C40 C41 C42 C37 0.0(5) . . . . ?
C42 C37 C38 F1 -179.6(2) . . . . ?
C42 C37 C38 C39 0.4(4) . . . . ?
C42 C37 B1 N1 171.5(2) . . . . ?
C42 C37 B1 C6 -71.0(3) . . . 2_666 ?
C42 C37 B1 C43 53.4(3) . . . . ?
C43 C44 C45 F7 -178.3(3) . . . . ?
C43 C44 C45 C46 0.2(5) . . . . ?
C44 C43 C48 F10 176.1(2) . . . . ?
C44 C43 C48 C47 -1.7(4) . . . . ?
C44 C43 B1 N1 -105.7(3) . . . . ?
C44 C43 B1 C6 136.4(2) . . . 2_666 ?
C44 C43 B1 C37 13.8(3) . . . . ?
C44 C45 C46 F8 -179.4(3) . . . . ?
C44 C45 C46 C47 -1.8(5) . . . . ?
C45 C46 C47 F9 -178.2(3) . . . . ?
C45 C46 C47 C48 1.6(5) . . . . ?
C46 C47 C48 F10 -177.7(3) . . . . ?
C46 C47 C48 C43 0.2(5) . . . . ?
C48 C43 C44 F6 -175.9(2) . . . . ?
C48 C43 C44 C45 1.5(4) . . . . ?
C48 C43 B1 N1 73.4(3) . . . . ?
C48 C43 B1 C6 -44.5(3) . . . 2_666 ?
C48 C43 B1 C37 -167.1(2) . . . . ?
B1 N1 C2 C3 167.1(2) . . . . ?
B1 N1 C1 C4 14.7(3) . . . 2_666 ?
B1 N1 C1 C1 -165.3(2) . . . 2_666 ?
B1 C6 C7 C8 177.3(2) 2_666 . . . ?
B1 C6 C5 C10 -179.8(2) 2_666 . . . ?
B1 C6 C5 C4 3.3(3) 2_666 . . . ?
B1 C37 C38 F1 5.9(4) . . . . ?
B1 C37 C38 C39 -174.2(3) . . . . ?
B1 C37 C42 F5 -6.4(3) . . . . ?
B1 C37 C42 C41 174.9(2) . . . . ?
B1 C43 C44 F6 3.3(4) . . . . ?
B1 C43 C44 C45 -179.3(3) . . . . ?
B1 C43 C48 F10 -3.1(3) . . . . ?
B1 C43 C48 C47 179.0(3) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.017 0.722 0.226 7 0 ' '
2 0.500 1.000 0.500 121 29 ' '
3 0.983 0.278 0.774 7 0 ' '

_platon_squeeze_void_probe_radius 1.20
_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_cu_20230824tn02251_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333173'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C46 H10 B2 F20 N4, C45 H10 B2 F20 N3, 0.5(C2 N2)'
_chemical_formula_sum            'C92 H20 B4 F40 N8'
_chemical_formula_weight         2040.40
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   24.0995(17)
_cell_length_b                   31.488(3)
_cell_length_c                   12.9587(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9833.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8170
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.80
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.810
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1106 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.8055.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             4032
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 0.00 0.0320
1.00 1.00 0.00 0.0690
1.00 -1.00 -1.00 0.0370
-1.00 1.00 1.00 0.0080
0.00 -1.00 1.00 0.0130
0.00 1.00 -1.00 0.0320
0.00 -1.00 0.00 0.0290
0.00 1.00 0.00 0.0250

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26063
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.230
_diffrn_reflns_theta_min         4.120
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                5395
_reflns_number_total             9346
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.8(4)
_refine_ls_extinction_coef       0.00019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         9346
_refine_ls_number_restraints     1523
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      1.063
_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)+(0.1124P)²+5.3036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2420
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.2(4)
 0.8(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C43-C58
 1.4 with sigma of 0.02
 B2-C45
 1.6 with sigma of 0.02
 N29-C49
 1.165 with sigma of 0.02
 N29-C48
 2.562 with sigma of 0.02
 N29-C48_$1
 1.318 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Others
 Fixed Sof: H44(0.5) C40(0.5) C39(0.5) C38(0.5) F11(0.5) F13(0.5) F14(0.5)
 C24(0.5) C27(0.5) C29(0.5) C51(0.5) H51(0.5) C45(0.5) C46(0.5) C47(0.5)
 H47(0.5) C48(0.5) C36(0.5) H36(0.5) C37(0.5) H37(0.5) C34(0.5) C33(0.5)
 F23(0.5) F24(0.5) F26(0.5) C41(0.5) C42(0.5) C43(0.5) N28(0.5) C49(0.5)
 N29(0.5) C63(0.5) C62(0.5) H62(0.5) F18(0.5) F17(0.5) F12(0.5) F15(0.5)
 C25(0.5) C28(0.5) C30(0.5) C50(0.5) H50(0.5) C35(0.5) F21(0.5) F22(0.5)
 F27(0.5) B3(0.5) C52(0.5) C53(0.5) C54(0.5) H54(0.5) C55(0.5) H55(0.5)
 C56(0.5) C57(0.5) H57(0.5) N3(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C44(H44), C51(H51), C47(H47),
 C36(H36), C37(H37), C62(H62), C50(H50), C54(H54), C55(H55), C57(H57)
6.b Fitted hexagon refined as free rotating group:
 C60(C40,C39,C38,C58,C59), C52(C53,C54,C55,C56,C57)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.3914(2) 0.34238(18) 0.8583(4) 0.0539(14) Uani 1 1 d . U . . .
N1 N 0.5760(2) 0.2532(2) 0.7581(4) 0.0225(12) Uani 1 1 d . U . . .
C4 C 0.4822(3) 0.2530(2) 0.8914(5) 0.0239(14) Uani 1 1 d . U . . .
B1 B 0.3663(3) 0.2564(3) 0.8056(5) 0.0210(14) Uani 1 1 d . U . . .
F2 F 0.3436(3) 0.41283(19) 0.7863(6) 0.081(2) Uani 1 1 d . U . . .
N2 N 0.4216(4) 0.2565(4) 1.3343(6) 0.084(3) Uani 1 1 d . U . . .
C1 C 0.5230(3) 0.2535(2) 0.7159(5) 0.0197(14) Uani 1 1 d . U . . .
B2 B 0.3820(8) 0.500000 0.500000 0.062(3) Uani 1 2 d DS TU P B .
F3 F 0.2624(3) 0.4067(2) 0.6410(7) 0.105(3) Uani 1 1 d . U . . .
C6 C 0.3815(3) 0.2592(3) 0.9256(5) 0.0263(14) Uani 1 1 d . U . . .
F4 F 0.2328(2) 0.3312(2) 0.5664(4) 0.0655(17) Uani 1 1 d . U . . .
N4 N 0.1740(5) 0.500000 0.500000 0.052(3) Uani 1 2 d S TU P . .
C2 C 0.5809(3) 0.2513(3) 0.8613(5) 0.0283(15) Uani 1 1 d . U . . .
H4 H 0.616409 0.250382 0.889264 0.034 Uiso 1 1 calc R U . . .
F5 F 0.28289(18) 0.26150(16) 0.6310(3) 0.0378(11) Uani 1 1 d . U . . .
C3 C 0.5360(3) 0.2505(3) 0.9290(5) 0.0277(15) Uani 1 1 d . U . . .
H5 H 0.542057 0.248400 0.999646 0.033 Uiso 1 1 calc R U . . .
F6 F 0.24507(17) 0.24271(17) 0.8272(3) 0.0388(11) Uani 1 1 d . U . . .
C5 C 0.4345(3) 0.2554(3) 0.9619(5) 0.0291(15) Uani 1 1 d . U . . .
F7 F 0.1932(2) 0.1691(2) 0.8273(5) 0.0740(19) Uani 1 1 d . U . . .
C10 C 0.4441(3) 0.2536(3) 1.0686(5) 0.0327(17) Uani 1 1 d . U . . .
H7 H 0.479804 0.249260 1.093809 0.039 Uiso 1 1 calc R U . . .
F8 F 0.2467(3) 0.0971(2) 0.8036(6) 0.093(2) Uani 1 1 d . U . . .
C9 C 0.3997(3) 0.2586(3) 1.1365(5) 0.0382(18) Uani 1 1 d . U . . .
F9 F 0.3582(3) 0.0969(2) 0.7571(8) 0.102(3) Uani 1 1 d . U . . .
C8 C 0.3461(3) 0.2624(3) 1.0997(5) 0.0388(19) Uani 1 1 d . U . . .
H9 H 0.316218 0.263471 1.145048 0.047 Uiso 1 1 calc R U . . .
F10 F 0.4142(2) 0.16983(17) 0.7591(5) 0.0579(15) Uani 1 1 d . U . . .
C7 C 0.3377(3) 0.2647(3) 0.9949(5) 0.0367(18) Uani 1 1 d . U . . .
H10 H 0.302278 0.269948 0.969690 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3356(3) 0.2971(2) 0.7579(5) 0.0231(13) Uani 1 1 d . U . . .
C12 C 0.3504(4) 0.3385(3) 0.7931(6) 0.0406(18) Uani 1 1 d . U . . .
C13 C 0.3256(4) 0.3747(3) 0.7532(9) 0.052(2) Uani 1 1 d . U . . .
C14 C 0.2868(5) 0.3712(3) 0.6770(9) 0.061(2) Uani 1 1 d . U . . .
C15 C 0.2720(3) 0.3339(3) 0.6370(7) 0.0386(17) Uani 1 1 d . U . . .
C16 C 0.2968(3) 0.2983(3) 0.6806(6) 0.0312(16) Uani 1 1 d . U . . .
C11 C 0.4097(4) 0.2578(4) 1.2489(6) 0.055(2) Uani 1 1 d . U . . .
C18 C 0.3326(3) 0.2113(2) 0.7885(5) 0.0229(14) Uani 1 1 d . U . . .
F19 F 0.3949(3) 0.3428(2) 0.5145(5) 0.073(2) Uani 1 1 d . U . . .
C19 C 0.2767(3) 0.2070(3) 0.8098(6) 0.0322(16) Uani 1 1 d . U . . .
F20 F 0.0038(3) 0.3412(2) 0.4498(6) 0.082(2) Uani 1 1 d . U . . .
C20 C 0.2496(3) 0.1696(3) 0.8123(7) 0.0444(19) Uani 1 1 d . U . . .
C21 C 0.2743(4) 0.1338(3) 0.7970(9) 0.059(2) Uani 1 1 d . U . . .
C22 C 0.3297(4) 0.1338(3) 0.7740(7) 0.049(2) Uani 1 1 d . U . . .
C23 C 0.3586(3) 0.1724(3) 0.7736(6) 0.0386(18) Uani 1 1 d . U . . .
F25 F 0.0126(5) 0.4884(3) 0.4006(7) 0.137(4) Uani 1 1 d . U . . .
C26 C 0.4150(4) 0.4562(3) 0.5257(7) 0.047(2) Uani 1 1 d . U . . .
C31 C 0.4173(4) 0.3799(3) 0.5340(7) 0.047(2) Uani 1 1 d . U . . .
C32 C 0.3956(4) 0.4169(3) 0.5088(7) 0.048(2) Uani 1 1 d . U . . .
C44 C 0.2751(5) 0.500000 0.500000 0.038(2) Uani 1 2 d S TU P . .
H44 H 0.272590 0.497657 0.571382 0.045 Uiso 0.5 1 calc R U P A -1
C60 C 0.0312(4) 0.3791(2) 0.4561(8) 0.069(3) Uani 1 1 d G U . . .
C40 C 0.0882(4) 0.3797(3) 0.4719(9) 0.062(3) Uani 0.5 1 d G U P B -1
C39 C 0.1172(3) 0.4178(4) 0.4660(11) 0.062(4) Uani 0.5 1 d G U P B -1
C38 C 0.0891(4) 0.4553(3) 0.4442(9) 0.058(3) Uani 0.5 1 d G U P B -1
C58 C 0.0321(4) 0.4547(2) 0.4284(8) 0.082(3) Uani 1 1 d DG U . B .
C59 C 0.0031(3) 0.4167(3) 0.4343(7) 0.087(3) Uani 1 1 d G U . B .
F11 F 0.4663(4) 0.4926(4) 0.6486(8) 0.052(2) Uani 0.5 1 d . U P C 2
F16 F 0.500000 0.4216(3) 0.750000 0.092(3) Uani 1 2 d S TU P C 2
F13 F 0.4788(5) 0.3430(3) 0.6593(8) 0.056(3) Uani 0.5 1 d . U P C 2
F14 F 0.3599(4) 0.4067(4) 0.4229(9) 0.056(3) Uani 0.5 1 d . U P D 2
C24 C 0.4517(8) 0.4542(6) 0.6064(13) 0.043(3) Uani 0.5 1 d . U P C 2
C27 C 0.4727(8) 0.4187(6) 0.6459(15) 0.051(3) Uani 0.5 1 d . U P C 2
C29 C 0.4585(8) 0.3776(6) 0.6177(13) 0.043(3) Uani 0.5 1 d . U P C 2
C51 C 0.3061(7) 0.4906(6) 0.2092(12) 0.039(3) Uani 0.5 1 d . U P B 2
H51 H 0.269899 0.489190 0.184379 0.046 Uiso 0.5 1 calc R U P B 2
C45 C 0.3706(7) 0.4908(6) 0.3620(12) 0.043(3) Uani 0.5 1 d D U P B 2
C46 C 0.4133(7) 0.4865(6) 0.2810(13) 0.043(3) Uani 0.5 1 d . U P B 2
C47 C 0.4051(7) 0.4837(6) 0.1743(13) 0.044(3) Uani 0.5 1 d . U P B 2
H47 H 0.434157 0.479067 0.128482 0.052 Uiso 0.5 1 calc R U P B 2
C48 C 0.3489(8) 0.4886(6) 0.1405(11) 0.048(3) Uani 0.5 1 d D U P B 2
C36 C 0.2139(8) 0.4930(7) 0.3458(16) 0.039(3) Uani 0.5 1 d . U P B 2
H36 H 0.207752 0.491451 0.275030 0.047 Uiso 0.5 1 calc R U P B 2
C37 C 0.1709(7) 0.4941(6) 0.4115(13) 0.043(3) Uani 0.5 1 d . U P B 2
H37 H 0.135656 0.489795 0.384076 0.052 Uiso 0.5 1 calc R U P B 2
C34 C 0.2675(7) 0.4942(5) 0.3841(12) 0.035(2) Uani 0.5 1 d . U P B 2
C33 C 0.3141(8) 0.4944(6) 0.3114(15) 0.036(3) Uani 0.5 1 d . U P B 2
F23 F 0.0860(7) 0.3375(5) 0.5948(12) 0.096(4) Uani 0.5 1 d . U P B 2
F24 F 0.1394(6) 0.4073(4) 0.6469(11) 0.082(4) Uani 0.5 1 d . U P B 2
F26 F -0.0212(7) 0.4162(6) 0.3548(13) 0.093(5) Uani 0.5 1 d . U P B 2
C41 C 0.0712(10) 0.3755(7) 0.5456(18) 0.064(4) Uani 0.5 1 d . U P B 2
C42 C 0.0988(10) 0.4133(8) 0.5661(17) 0.064(3) Uani 0.5 1 d . U P B 2
C43 C 0.0780(9) 0.4523(7) 0.5206(16) 0.067(4) Uani 0.5 1 d D U P B 2
N28 N 0.1669(9) 0.4945(8) 0.1054(14) 0.076(5) Uani 0.5 1 d . U P E 2
C61 C 0.1640(9) 0.500000 0.000000 0.098(5) Uani 1 2 d S TU P E 2
C49 C 0.3313(11) 0.5111(8) 0.0540(16) 0.060(4) Uani 0.5 1 d D U P B 2
N29 N 0.3368(8) 0.5114(7) -0.0388(11) 0.060(4) Uani 0.5 1 d D U P B 2
C63 C 0.2344(8) 0.5000(7) 0.3303(15) 0.039(3) Uani 0.5 1 d . U P B -1
C62 C 0.3309(8) 0.4950(6) 0.3575(15) 0.037(3) Uani 0.5 1 d . U P B -1
H62 H 0.365661 0.489614 0.329051 0.044 Uiso 0.5 1 calc R U P B -1
F18 F 0.5004(6) 0.3446(4) 0.5365(11) 0.077(3) Uani 0.5 1 d . U P C -1
F17 F 0.5588(4) 0.4226(4) 0.5583(9) 0.061(3) Uani 0.5 1 d . U P C -1
F12 F 0.5034(4) 0.4942(3) 0.5445(8) 0.050(2) Uani 0.5 1 d . U P C -1
F15 F 0.3353(4) 0.4180(3) 0.5037(9) 0.053(3) Uani 0.5 1 d . U P D -1
C25 C 0.4732(8) 0.4581(6) 0.5340(14) 0.044(3) Uani 0.5 1 d . U P C -1
C28 C 0.5062(8) 0.4199(6) 0.5387(14) 0.048(3) Uani 0.5 1 d . U P C -1
C30 C 0.4740(8) 0.3821(6) 0.5350(14) 0.047(3) Uani 0.5 1 d . U P C -1
C50 C 0.2845(8) 0.4963(6) 0.2938(14) 0.038(3) Uani 0.5 1 d . U P B -1
H50 H 0.289463 0.494606 0.222781 0.045 Uiso 0.5 1 calc R U P B -1
C35 C 0.2242(6) 0.5021(6) 0.4430(12) 0.036(3) Uani 0.5 1 d . U P B -1
F21 F 0.1666(5) 0.4208(4) 0.4789(8) 0.057(3) Uani 0.5 1 d . U P B -1
F22 F 0.1107(5) 0.3473(4) 0.4921(9) 0.064(3) Uani 0.5 1 d . U P B -1
F27 F -0.0559(7) 0.4175(6) 0.3969(14) 0.100(5) Uani 0.5 1 d . U P B -1
B3 B 0.1178(9) 0.5038(8) 0.4217(16) 0.049(3) Uani 0.5 1 d . U P B -1
C52 C 0.1855(4) 0.5053(5) 0.2619(8) 0.046(3) Uani 0.5 1 d G U P B -1
C53 C 0.1313(5) 0.5090(4) 0.2975(7) 0.045(3) Uani 0.5 1 d G U P B -1
C54 C 0.0880(4) 0.5141(5) 0.2277(9) 0.052(4) Uani 0.5 1 d G U P B -1
H54 H 0.051735 0.516573 0.251496 0.062 Uiso 0.5 1 calc R U P B -1
C55 C 0.0989(5) 0.5155(5) 0.1224(8) 0.063(4) Uani 0.5 1 d G U P B -1
H55 H 0.069915 0.518909 0.075780 0.075 Uiso 0.5 1 calc R U P B -1
C56 C 0.1531(6) 0.5118(6) 0.0869(7) 0.073(5) Uani 0.5 1 d G U P B -1
C57 C 0.1964(4) 0.5067(5) 0.1566(9) 0.064(4) Uani 0.5 1 d G U P B -1
H57 H 0.232676 0.504210 0.132863 0.076 Uiso 0.5 1 calc R U P B -1
N3 N 0.3263(5) 0.5012(4) 0.4586(9) 0.036(2) Uani 0.5 1 d . U P B -1


_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 C12 1.308(9) . ?
N1 B1 1.621(8) 3_656 ?
N1 C1 1.389(8) . ?
N1 C2 1.344(8) . ?
C4 C1 1.397(9) 3_656 ?
C4 C3 1.385(10) . ?
C4 C5 1.470(9) . ?
B1 C6 1.600(9) . ?
B1 C17 1.605(10) . ?
B1 C18 1.652(11) . ?
F2 C13 1.346(10) . ?
N2 C11 1.144(11) . ?
C1 C1 1.417(12) 3_656 ?
B2 C26 1.626(13) . ?
B2 C26 1.626(13) 4_566 ?
B2 C45 1.832(15) . ?
B2 C45 1.832(15) 4_566 ?
B2 N3 1.44(2) . ?
F3 C14 1.347(11) . ?
C6 C5 1.368(9) . ?
C6 C7 1.395(9) . ?
F4 C15 1.317(9) . ?
N4 C37 1.165(17) 4_566 ?
N4 C37 1.164(17) . ?
N4 C35 1.419(17) . ?
N4 B3 1.70(2) . ?
C2 H4 0.9300 . ?
C2 C3 1.393(9) . ?
F5 C16 1.367(9) . ?
C3 H5 0.9300 . ?
F6 C19 1.376(9) . ?
C5 C10 1.403(9) . ?
F7 C20 1.374(10) . ?
C10 H7 0.9300 . ?
C10 C9 1.394(9) . ?
F8 C21 1.336(11) . ?
C9 C8 1.383(10) . ?
C9 C11 1.477(11) . ?
F9 C22 1.367(11) . ?
C8 H9 0.9300 . ?
C8 C7 1.375(10) . ?
F10 C23 1.355(9) . ?
C7 H10 0.9300 . ?
C17 C12 1.424(11) . ?
C17 C16 1.371(9) . ?
C12 C13 1.387(12) . ?
C13 C14 1.365(15) . ?
C14 C15 1.333(14) . ?
C15 C16 1.391(10) . ?
C18 C19 1.382(10) . ?
C18 C23 1.390(11) . ?
F19 C31 1.310(11) . ?
C19 C20 1.349(12) . ?
F20 C60 1.367(9) . ?
C20 C21 1.290(14) . ?
C21 C22 1.368(13) . ?
C22 C23 1.399(12) . ?
F25 C58 1.212(12) . ?
C26 C32 1.340(14) . ?
C26 C24 1.372(19) . ?
C26 C25 1.41(2) . ?
C31 C32 1.320(14) . ?
C31 C29 1.472(18) . ?
C31 C30 1.37(2) . ?
C32 F14 1.442(13) . ?
C32 F15 1.455(13) . ?
C44 H44 0.9300 . ?
C44 C34 1.524(16) . ?
C44 C34 1.524(16) 4_566 ?
C44 C35 1.433(19) . ?
C44 N3 1.345(16) . ?
C60 C40 1.3900 . ?
C60 C59 1.3900 . ?
C60 C41 1.51(3) . ?
C40 C39 1.3900 . ?
C40 F22 1.184(14) . ?
C39 C38 1.3900 . ?
C39 F21 1.206(13) . ?
C38 C58 1.3900 . ?
C38 B3 1.70(3) . ?
C58 C59 1.3900 . ?
C58 C43 1.63(2) . ?
C59 F26 1.185(17) . ?
C59 F27 1.503(17) . ?
F11 C24 1.37(2) . ?
F11 C46 1.70(2) 4_566 ?
F16 C27 1.503(18) . ?
F16 C27 1.503(18) 3_656 ?
F13 C29 1.310(19) . ?
C24 C27 1.33(3) . ?
C27 C29 1.39(3) . ?
C51 H51 0.9300 . ?
C51 C48 1.36(2) . ?
C51 C33 1.34(2) . ?
C45 C46 1.48(2) . ?
C45 C33 1.52(2) . ?
C46 C47 1.40(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.43(2) . ?
C48 C49 1.39(3) . ?
C48 N29 1.35(2) 4_565 ?
C36 H36 0.9300 . ?
C36 C37 1.34(2) . ?
C36 C34 1.38(2) . ?
C37 H37 0.9300 . ?
C34 C33 1.47(2) . ?
F23 C41 1.40(3) . ?
F24 C42 1.45(2) . ?
C41 C42 1.39(3) . ?
C42 C43 1.45(3) . ?
N28 C61 1.379(18) . ?
C49 C49 1.57(4) 4_565 ?
C49 N29 0.75(3) 4_565 ?
C49 N29 1.209(18) . ?
N29 N29 1.23(3) 4_565 ?
C63 C50 1.30(3) . ?
C63 C35 1.48(3) . ?
C63 C52 1.48(2) . ?
C62 H62 0.9300 . ?
C62 C50 1.39(2) . ?
C62 N3 1.33(2) . ?
F18 C30 1.34(2) . ?
F17 C28 1.30(2) . ?
F12 C25 1.36(2) . ?
C25 C28 1.44(2) . ?
C28 C30 1.42(3) . ?
C50 H50 0.9300 . ?
B3 C53 1.65(2) . ?
C52 C53 1.3900 . ?
C52 C57 1.3900 . ?
C53 C54 1.3900 . ?
C54 H54 0.9300 . ?
C54 C55 1.3900 . ?
C55 H55 0.9300 . ?
C55 C56 1.3900 . ?
C56 C57 1.3900 . ?
C57 H57 0.9300 . ?

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
C1 N1 B1 126.1(5) . 3_656 ?
C2 N1 B1 115.7(5) . 3_656 ?
C2 N1 C1 118.2(6) . . ?
C1 C4 C5 123.2(6) 3_656 . ?
C3 C4 C1 115.8(6) . 3_656 ?
C3 C4 C5 121.0(6) . . ?
N1 B1 C18 107.4(5) 3_656 . ?
C6 B1 N1 107.6(5) . 3_656 ?
C6 B1 C17 115.9(6) . . ?
C6 B1 C18 106.8(6) . . ?
C17 B1 N1 104.5(5) . 3_656 ?
C17 B1 C18 114.1(6) . . ?
N1 C1 C4 118.3(6) . 3_656 ?
N1 C1 C1 118.3(7) . 3_656 ?
C4 C1 C1 123.3(8) 3_656 3_656 ?
C26 B2 C26 121.4(13) 4_566 . ?
C26 B2 C45 90.4(7) . 4_566 ?
C26 B2 C45 90.4(7) 4_566 . ?
C26 B2 C45 98.0(7) . . ?
C26 B2 C45 98.0(7) 4_566 4_566 ?
C45 B2 C45 162.8(16) 4_566 . ?
N3 B2 C26 110.9(7) . 4_566 ?
N3 B2 C26 123.5(8) . . ?
N3 B2 C45 102.7(11) . 4_566 ?
C5 C6 B1 122.9(6) . . ?
C5 C6 C7 119.7(6) . . ?
C7 C6 B1 117.4(6) . . ?
C35 N4 B3 111.5(10) . . ?
N1 C2 H4 118.0 . . ?
N1 C2 C3 124.0(6) . . ?
C3 C2 H4 118.0 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H5 119.9 . . ?
C2 C3 H5 119.9 . . ?
C6 C5 C4 121.4(6) . . ?
C6 C5 C10 119.8(6) . . ?
C10 C5 C4 118.8(6) . . ?
C5 C10 H7 120.3 . . ?
C9 C10 C5 119.4(7) . . ?
C9 C10 H7 120.3 . . ?
C10 C9 C11 119.8(7) . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 C11 119.6(6) . . ?
C9 C8 H9 120.6 . . ?
C7 C8 C9 118.8(7) . . ?
C7 C8 H9 120.6 . . ?
C6 C7 H10 119.4 . . ?
C8 C7 C6 121.3(7) . . ?
C8 C7 H10 119.4 . . ?
C12 C17 B1 119.4(6) . . ?
C16 C17 B1 128.1(7) . . ?
C16 C17 C12 112.4(7) . . ?
F1 C12 C17 118.9(7) . . ?
F1 C12 C13 119.2(8) . . ?
C13 C12 C17 121.7(8) . . ?
F2 C13 C12 118.5(9) . . ?
F2 C13 C14 121.4(9) . . ?
C14 C13 C12 119.9(9) . . ?
F3 C14 C13 118.9(10) . . ?
C15 C14 F3 118.7(10) . . ?
C15 C14 C13 122.4(9) . . ?
F4 C15 C14 121.4(8) . . ?
F4 C15 C16 122.5(8) . . ?
C14 C15 C16 115.9(8) . . ?
F5 C16 C17 119.2(7) . . ?
F5 C16 C15 112.8(6) . . ?
C17 C16 C15 127.7(8) . . ?
N2 C11 C9 174.7(9) . . ?
C19 C18 B1 122.4(6) . . ?
C19 C18 C23 112.5(7) . . ?
C23 C18 B1 123.7(7) . . ?
F6 C19 C18 119.6(7) . . ?
C20 C19 F6 116.2(7) . . ?
C20 C19 C18 124.1(8) . . ?
C19 C20 F7 119.5(9) . . ?
C21 C20 F7 118.0(9) . . ?
C21 C20 C19 122.4(8) . . ?
F8 C21 C22 120.0(10) . . ?
C20 C21 F8 121.0(10) . . ?
C20 C21 C22 119.0(10) . . ?
F9 C22 C23 119.2(8) . . ?
C21 C22 F9 121.6(9) . . ?
C21 C22 C23 119.1(9) . . ?
F10 C23 C18 121.1(7) . . ?
F10 C23 C22 116.2(8) . . ?
C18 C23 C22 122.6(8) . . ?
C32 C26 B2 125.4(9) . . ?
C32 C26 C24 107.8(11) . . ?
C32 C26 C25 113.4(12) . . ?
C24 C26 B2 120.7(11) . . ?
C25 C26 B2 117.9(12) . . ?
F19 C31 C32 125.2(10) . . ?
F19 C31 C29 112.1(11) . . ?
F19 C31 C30 117.4(12) . . ?
C32 C31 C29 119.5(11) . . ?
C32 C31 C30 110.6(12) . . ?
C26 C32 F14 122.6(9) . . ?
C26 C32 F15 109.5(10) . . ?
C31 C32 C26 129.6(9) . . ?
C31 C32 F14 103.3(10) . . ?
C31 C32 F15 115.3(10) . . ?
C34 C44 C34 166.1(17) 4_566 . ?
C35 C44 H44 117.3 . . ?
C35 C44 C34 113.5(12) . 4_566 ?
N3 C44 H44 117.3 . . ?
N3 C44 C34 120.0(11) . 4_566 ?
N3 C44 C35 125.3(8) . . ?
F20 C60 C40 119.9(8) . . ?
F20 C60 C59 119.7(8) . . ?
F20 C60 C41 106.6(11) . . ?
C40 C60 C59 120.0 . . ?
C59 C60 C41 122.1(10) . . ?
C39 C40 C60 120.0 . . ?
F22 C40 C60 118.3(11) . . ?
F22 C40 C39 121.7(11) . . ?
C40 C39 C38 120.0 . . ?
F21 C39 C40 123.7(11) . . ?
F21 C39 C38 116.3(11) . . ?
C39 C38 B3 126.8(11) . . ?
C58 C38 C39 120.0 . . ?
C58 C38 B3 112.9(11) . . ?
F25 C58 C38 114.5(10) . . ?
F25 C58 C59 125.2(10) . . ?
F25 C58 C43 121.4(13) . . ?
C38 C58 C59 120.0 . . ?
C59 C58 C43 105.0(9) . . ?
C60 C59 F27 122.8(10) . . ?
C58 C59 C60 120.0 . . ?
C58 C59 F27 116.2(10) . . ?
F26 C59 C60 114.0(12) . . ?
F26 C59 C58 102.1(12) . . ?
C26 C24 F11 115.3(15) . . ?
C27 C24 C26 125.4(17) . . ?
C27 C24 F11 119.3(17) . . ?
C24 C27 F16 117.4(17) . . ?
C24 C27 C29 126.0(17) . . ?
C29 C27 F16 113.8(16) . . ?
F13 C29 C31 126.5(15) . . ?
F13 C29 C27 125.0(16) . . ?
C27 C29 C31 108.4(15) . . ?
C48 C51 H51 118.7 . . ?
C33 C51 H51 118.7 . . ?
C33 C51 C48 122.6(17) . . ?
C46 C45 B2 127.2(14) . . ?
C46 C45 C33 109.0(13) . . ?
C33 C45 B2 123.1(14) . . ?
C47 C46 C45 127.5(16) . . ?
C46 C47 H47 122.3 . . ?
C46 C47 C48 115.4(16) . . ?
C48 C47 H47 122.3 . . ?
C51 C48 C47 121.4(14) . . ?
C51 C48 C49 105.8(18) . . ?
C49 C48 C47 126.0(18) . . ?
N29 C48 C51 118.4(17) 4_565 . ?
N29 C48 C47 120.2(17) 4_565 . ?
N29 C48 C49 31.6(11) 4_565 . ?
C37 C36 H36 120.3 . . ?
C37 C36 C34 119.5(18) . . ?
C34 C36 H36 120.3 . . ?
N4 C37 C36 125.4(19) . . ?
N4 C37 H37 117.3 . . ?
C36 C37 H37 117.3 . . ?
C36 C34 C44 118.0(15) . . ?
C36 C34 C33 119.0(16) . . ?
C33 C34 C44 122.7(15) . . ?
C51 C33 C45 123.4(17) . . ?
C51 C33 C34 121.5(18) . . ?
C34 C33 C45 114.2(16) . . ?
F23 C41 C60 125.2(18) . . ?
C42 C41 C60 113(2) . . ?
C42 C41 F23 121(2) . . ?
F24 C42 C43 130(2) . . ?
C41 C42 F24 111(2) . . ?
C41 C42 C43 119(2) . . ?
C42 C43 C58 124.9(18) . . ?
N29 C49 C48 71(2) 4_565 . ?
N29 C49 C48 140(3) . . ?
N29 C49 N29 74(3) 4_565 . ?
C49 N29 C49 104(3) 4_565 . ?
C49 N29 N29 70(3) 4_565 4_565 ?
C49 N29 N29 35.7(13) . 4_565 ?
C50 C63 C35 121.0(18) . . ?
C50 C63 C52 122.0(17) . . ?
C35 C63 C52 116.9(15) . . ?
C50 C62 H62 119.6 . . ?
N3 C62 H62 119.6 . . ?
N3 C62 C50 120.9(17) . . ?
C26 C25 C28 121.2(16) . . ?
F12 C25 C26 125.2(15) . . ?
F12 C25 C28 113.4(15) . . ?
F17 C28 C25 119.6(17) . . ?
F17 C28 C30 126.5(17) . . ?
C30 C28 C25 113.3(16) . . ?
C31 C30 C28 126.0(17) . . ?
F18 C30 C31 115.3(16) . . ?
F18 C30 C28 118.6(16) . . ?
C63 C50 C62 122.2(18) . . ?
C63 C50 H50 118.9 . . ?
C62 C50 H50 118.9 . . ?
N4 C35 C44 117.4(12) . . ?
N4 C35 C63 130.7(14) . . ?
C44 C35 C63 111.3(13) . . ?
N4 B3 C38 99.1(13) . . ?
C53 B3 N4 115.6(13) . . ?
C53 B3 C38 109.6(14) . . ?
C53 C52 C63 123.9(11) . . ?
C53 C52 C57 120.0 . . ?
C57 C52 C63 116.1(11) . . ?
C52 C53 B3 120.0(11) . . ?
C54 C53 B3 119.8(11) . . ?
C54 C53 C52 120.0 . . ?
C53 C54 H54 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C54 C55 H55 120.0 . . ?
C54 C55 C56 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C57 120.0 . . ?
C52 C57 H57 120.0 . . ?
C56 C57 C52 120.0 . . ?
C56 C57 H57 120.0 . . ?
C44 N3 B2 134.6(10) . . ?
C62 N3 B2 106.5(13) . . ?
C62 N3 C44 117.8(13) . . ?

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 C12 C13 F2 -2.4(14) . . . . ?
F1 C12 C13 C14 173.0(9) . . . . ?
N1 B1 C6 C5 -5.2(11) 3_656 . . . ?
N1 B1 C6 C7 176.4(7) 3_656 . . . ?
N1 B1 C17 C12 -82.0(8) 3_656 . . . ?
N1 B1 C17 C16 94.5(8) 3_656 . . . ?
N1 B1 C18 C19 -163.4(6) 3_656 . . . ?
N1 B1 C18 C23 31.1(8) 3_656 . . . ?
N1 C2 C3 C4 -1.8(14) . . . . ?
C4 C5 C10 C9 175.9(8) . . . . ?
B1 N1 C1 C4 5.6(11) 3_656 . . 3_656 ?
B1 N1 C1 C1 -175.4(5) 3_656 . . 3_656 ?
B1 N1 C2 C3 176.6(7) 3_656 . . . ?
B1 C6 C5 C4 6.7(13) . . . . ?
B1 C6 C5 C10 -173.3(8) . . . . ?
B1 C6 C7 C8 172.3(8) . . . . ?
B1 C17 C12 F1 4.7(11) . . . . ?
B1 C17 C12 C13 179.0(8) . . . . ?
B1 C17 C16 F5 -3.9(11) . . . . ?
B1 C17 C16 C15 -177.2(7) . . . . ?
B1 C18 C19 F6 12.6(10) . . . . ?
B1 C18 C19 C20 -169.3(7) . . . . ?
B1 C18 C23 F10 -8.5(11) . . . . ?
B1 C18 C23 C22 170.6(7) . . . . ?
F2 C13 C14 F3 -6.1(17) . . . . ?
F2 C13 C14 C15 174.1(10) . . . . ?
C1 N1 C2 C3 -1.5(13) . . . . ?
C1 C4 C3 C2 3.9(12) 3_656 . . . ?
C1 C4 C5 C6 -1.6(13) 3_656 . . . ?
C1 C4 C5 C10 178.5(7) 3_656 . . . ?
B2 C26 C32 C31 -174.3(9) . . . . ?
B2 C26 C32 F14 33.6(15) . . . . ?
B2 C26 C32 F15 -22.4(13) . . . . ?
B2 C26 C24 F11 -12.4(19) . . . . ?
B2 C26 C24 C27 166.7(17) . . . . ?
B2 C26 C25 F12 15(2) . . . . ?
B2 C26 C25 C28 -169.1(13) . . . . ?
B2 C45 C46 F11 -16.3(19) . . . 4_566 ?
B2 C45 C46 C47 -173.0(16) . . . . ?
B2 C45 C33 C51 175.4(15) . . . . ?
B2 C45 C33 C34 -16(2) . . . . ?
F3 C14 C15 F4 -2.5(16) . . . . ?
F3 C14 C15 C16 -177.1(9) . . . . ?
C6 B1 C17 C12 36.2(9) . . . . ?
C6 B1 C17 C16 -147.3(7) . . . . ?
C6 B1 C18 C19 81.4(8) . . . . ?
C6 B1 C18 C23 -84.1(8) . . . . ?
C6 C5 C10 C9 -4.1(14) . . . . ?
F4 C15 C16 F5 10.1(11) . . . . ?
F4 C15 C16 C17 -176.3(8) . . . . ?
N4 B3 C53 C52 7(2) . . . . ?
N4 B3 C53 C54 -177.4(11) . . . . ?
C2 N1 C1 C4 -176.5(7) . . . 3_656 ?
C2 N1 C1 C1 2.5(8) . . . 3_656 ?
C3 C4 C5 C6 177.9(8) . . . . ?
C3 C4 C5 C10 -2.1(12) . . . . ?
F6 C19 C20 F7 2.6(12) . . . . ?
F6 C19 C20 C21 179.8(9) . . . . ?
C5 C4 C3 C2 -175.6(8) . . . . ?
C5 C6 C7 C8 -6.1(13) . . . . ?
C5 C10 C9 C8 4.1(15) . . . . ?
C5 C10 C9 C11 -178.6(9) . . . . ?
F7 C20 C21 F8 -5.2(16) . . . . ?
F7 C20 C21 C22 175.0(9) . . . . ?
C10 C9 C8 C7 -5.0(15) . . . . ?
F8 C21 C22 F9 0.1(16) . . . . ?
F8 C21 C22 C23 -176.2(9) . . . . ?
C9 C8 C7 C6 6.0(14) . . . . ?
F9 C22 C23 F10 -1.9(13) . . . . ?
F9 C22 C23 C18 179.0(8) . . . . ?
C7 C6 C5 C4 -175.0(8) . . . . ?
C7 C6 C5 C10 5.0(13) . . . . ?
C17 B1 C6 C5 -121.7(8) . . . . ?
C17 B1 C6 C7 59.9(10) . . . . ?
C17 B1 C18 C19 -48.1(8) . . . . ?
C17 B1 C18 C23 146.4(6) . . . . ?
C17 C12 C13 F2 -176.8(9) . . . . ?
C17 C12 C13 C14 -1.3(15) . . . . ?
C12 C17 C16 F5 172.8(7) . . . . ?
C12 C17 C16 C15 -0.5(12) . . . . ?
C12 C13 C14 F3 178.5(10) . . . . ?
C12 C13 C14 C15 -1.2(17) . . . . ?
C13 C14 C15 F4 177.2(9) . . . . ?
C13 C14 C15 C16 2.6(16) . . . . ?
C14 C15 C16 F5 -175.4(8) . . . . ?
C14 C15 C16 C17 -1.8(13) . . . . ?
C16 C17 C12 F1 -172.4(7) . . . . ?
C16 C17 C12 C13 2.0(12) . . . . ?
C11 C9 C8 C7 177.6(10) . . . . ?
C18 B1 C6 C5 109.8(8) . . . . ?
C18 B1 C6 C7 -68.5(9) . . . . ?
C18 B1 C17 C12 161.0(6) . . . . ?
C18 B1 C17 C16 -22.5(10) . . . . ?
C18 C19 C20 F7 -175.5(7) . . . . ?
C18 C19 C20 C21 1.6(14) . . . . ?
F19 C31 C32 C26 179.6(10) . . . . ?
F19 C31 C32 F14 -24.3(13) . . . . ?
F19 C31 C32 F15 29.0(14) . . . . ?
F19 C31 C29 F13 11(2) . . . . ?
F19 C31 C29 C27 -169.4(14) . . . . ?
F19 C31 C30 F18 -13(2) . . . . ?
F19 C31 C30 C28 169.7(15) . . . . ?
C19 C18 C23 F10 -175.3(7) . . . . ?
C19 C18 C23 C22 3.8(11) . . . . ?
C19 C20 C21 F8 177.6(9) . . . . ?
C19 C20 C21 C22 -2.2(16) . . . . ?
F20 C60 C40 C39 172.2(9) . . . . ?
F20 C60 C40 F22 -9.0(12) . . . . ?
F20 C60 C59 C58 -172.3(9) . . . . ?
F20 C60 C59 F26 -50.7(13) . . . . ?
F20 C60 C59 F27 -4.1(13) . . . . ?
F20 C60 C41 F23 14(2) . . . . ?
F20 C60 C41 C42 -175.2(16) . . . . ?
C20 C21 C22 F9 179.9(10) . . . . ?
C20 C21 C22 C23 3.7(15) . . . . ?
C21 C22 C23 F10 174.5(9) . . . . ?
C21 C22 C23 C18 -4.7(14) . . . . ?
C23 C18 C19 F6 179.6(6) . . . . ?
C23 C18 C19 C20 -2.3(11) . . . . ?
F25 C58 C59 C60 172.8(11) . . . . ?
F25 C58 C59 F26 45.5(13) . . . . ?
F25 C58 C59 F27 3.8(13) . . . . ?
F25 C58 C43 C42 172.9(17) . . . . ?
C26 B2 C26 C32 -152.6(10) 4_566 . . . ?
C26 B2 C26 C24 58.2(11) 4_566 . . . ?
C26 B2 C26 C25 5.5(10) 4_566 . . . ?
C26 B2 C45 C46 58.9(18) 4_566 . . . ?
C26 B2 C45 C46 -63.0(18) . . . . ?
C26 B2 C45 C33 -109.8(16) 4_566 . . . ?
C26 B2 C45 C33 128.3(16) . . . . ?
C26 B2 N3 C44 85.8(15) . . . . ?
C26 B2 N3 C44 -117.1(14) 4_566 . . . ?
C26 B2 N3 C62 75.9(12) 4_566 . . . ?
C26 B2 N3 C62 -81.3(13) . . . . ?
C26 C24 C27 F16 -164.4(14) . . . . ?
C26 C24 C27 C29 -5(3) . . . . ?
C26 C25 C28 F17 -172.0(15) . . . . ?
C26 C25 C28 C30 -1(2) . . . . ?
C32 C26 C24 F11 -166.4(12) . . . . ?
C32 C26 C24 C27 13(2) . . . . ?
C32 C26 C25 F12 175.6(13) . . . . ?
C32 C26 C25 C28 -8(2) . . . . ?
C32 C31 C29 F13 171.6(15) . . . . ?
C32 C31 C29 C27 -9(2) . . . . ?
C32 C31 C30 F18 -165.6(13) . . . . ?
C32 C31 C30 C28 17(2) . . . . ?
C44 C34 C33 C51 -177.8(15) . . . . ?
C44 C34 C33 C45 13(2) . . . . ?
C60 C40 C39 C38 0.0 . . . . ?
C60 C40 C39 F21 179.9(14) . . . . ?
C60 C41 C42 F24 -175.7(15) . . . . ?
C60 C41 C42 C43 15(3) . . . . ?
C40 C60 C59 C58 0.0 . . . . ?
C40 C60 C59 F27 168.2(12) . . . . ?
C40 C39 C38 C58 0.0 . . . . ?
C40 C39 C38 B3 -173.2(12) . . . . ?
C39 C38 C58 F25 -173.5(10) . . . . ?
C39 C38 C58 C59 0.0 . . . . ?
C39 C38 B3 N4 -32.7(14) . . . . ?
C39 C38 B3 C53 88.8(15) . . . . ?
C38 C58 C59 C60 0.0 . . . . ?
C38 C58 C59 F27 -168.9(12) . . . . ?
C38 B3 C53 C52 -103.9(14) . . . . ?
C38 B3 C53 C54 71.7(16) . . . . ?
C58 C38 B3 N4 153.7(8) . . . . ?
C58 C38 B3 C53 -84.8(14) . . . . ?
C59 C60 C40 C39 0.0 . . . . ?
C59 C60 C40 F22 178.7(12) . . . . ?
C59 C60 C41 F23 156.6(16) . . . . ?
C59 C60 C41 C42 -32(2) . . . . ?
C59 C58 C43 C42 23(2) . . . . ?
F11 C24 C27 F16 15(3) . . . . ?
F11 C24 C27 C29 174.2(19) . . . . ?
F11 C46 C47 C48 -144.0(17) 4_566 . . . ?
F16 C27 C29 C31 162.0(12) . . . . ?
F16 C27 C29 F13 -18(3) . . . . ?
C24 C26 C32 C31 -21.9(16) . . . . ?
C24 C26 C32 F14 -174.0(12) . . . . ?
C24 C27 C29 C31 2(3) . . . . ?
C24 C27 C29 F13 -178.4(19) . . . . ?
C29 C31 C32 C26 21.4(18) . . . . ?
C29 C31 C32 F14 177.6(11) . . . . ?
C51 C48 C49 C49 -124.1(15) . . . 4_565 ?
C51 C48 C49 N29 -119(3) . . . 4_565 ?
C51 C48 C49 N29 -148(4) . . . . ?
C45 B2 C26 C32 107.7(11) 4_566 . . . ?
C45 B2 C26 C32 -57.2(13) . . . . ?
C45 B2 C26 C24 153.6(12) . . . . ?
C45 B2 C26 C24 -41.4(15) 4_566 . . . ?
C45 B2 C45 C46 178.5(17) 4_566 . . . ?
C45 B2 C45 C33 9.8(14) 4_566 . . . ?
C45 C46 C47 C48 4(3) . . . . ?
C46 F11 C24 C26 72.9(16) 4_566 . . . ?
C46 F11 C24 C27 -106.3(19) 4_566 . . . ?
C46 C45 C33 C51 5(3) . . . . ?
C46 C45 C33 C34 173.6(16) . . . . ?
C46 C47 C48 C51 -8(3) . . . . ?
C46 C47 C48 C49 139(2) . . . . ?
C46 C47 C48 N29 176.7(19) . . . 4_565 ?
C47 C48 C49 C49 85(2) . . . 4_565 ?
C47 C48 C49 N29 90(3) . . . 4_565 ?
C47 C48 C49 N29 61(5) . . . . ?
C48 C51 C33 C45 -9(3) . . . . ?
C48 C51 C33 C34 -176.7(17) . . . . ?
C48 C49 N29 C49 50(7) . . . 4_565 ?
C48 C49 N29 N29 29(3) . . . 4_565 ?
C36 C34 C33 C51 -5(3) . . . . ?
C36 C34 C33 C45 -173.6(17) . . . . ?
C37 C36 C34 C44 -4(3) . . . . ?
C37 C36 C34 C33 -177.9(19) . . . . ?
C34 C44 C34 C36 1.1(14) 4_566 . . . ?
C34 C44 C34 C33 174.4(16) 4_566 . . . ?
C34 C36 C37 N4 8(3) . . . . ?
C33 C51 C48 C47 10(3) . . . . ?
C33 C51 C48 C49 -143(2) . . . . ?
C33 C51 C48 N29 -174.1(19) . . . 4_565 ?
C33 C45 C46 F11 153.7(13) . . . 4_566 ?
C33 C45 C46 C47 -3(3) . . . . ?
F23 C41 C42 F24 -4(3) . . . . ?
F23 C41 C42 C43 -174(2) . . . . ?
F24 C42 C43 C58 179.5(17) . . . . ?
C41 C60 C59 C58 49.5(11) . . . . ?
C41 C60 C59 F26 171.0(15) . . . . ?
C41 C42 C43 C58 -13(3) . . . . ?
C43 C58 C59 C60 -39.0(8) . . . . ?
C43 C58 C59 F26 -166.3(13) . . . . ?
C49 C49 N29 N29 -21(6) 4_565 . . 4_565 ?
N29 C48 C49 C49 -5(2) 4_565 . . 4_565 ?
N29 C48 C49 N29 -29(3) 4_565 . . . ?
N29 C49 N29 C49 21(6) 4_565 . . 4_565 ?
C63 C52 C53 B3 -4.8(19) . . . . ?
C63 C52 C53 C54 179.7(16) . . . . ?
C63 C52 C57 C56 -179.7(15) . . . . ?
F17 C28 C30 C31 166.6(17) . . . . ?
F17 C28 C30 F18 -11(3) . . . . ?
F12 C25 C28 F17 4(2) . . . . ?
F12 C25 C28 C30 175.8(15) . . . . ?
C25 C26 C32 C31 26.8(17) . . . . ?
C25 C26 C32 F15 178.7(11) . . . . ?
C25 C28 C30 C31 -4(3) . . . . ?
C25 C28 C30 F18 178.6(17) . . . . ?
C30 C31 C32 C26 -30.3(16) . . . . ?
C30 C31 C32 F15 179.1(12) . . . . ?
C50 C63 C35 N4 -170.0(18) . . . . ?
C50 C63 C35 C44 1(3) . . . . ?
C50 C63 C52 C53 179.5(16) . . . . ?
C50 C63 C52 C57 -1(3) . . . . ?
C50 C62 N3 B2 -176.8(15) . . . . ?
C50 C62 N3 C44 14(2) . . . . ?
C35 N4 B3 C38 117.1(11) . . . . ?
C35 N4 B3 C53 0.1(19) . . . . ?
C35 C44 N3 B2 179.3(13) . . . . ?
C35 C44 N3 C62 -14.7(18) . . . . ?
C35 C63 C50 C62 -1(3) . . . . ?
C35 C63 C52 C53 -5(2) . . . . ?
C35 C63 C52 C57 175.0(13) . . . . ?
F21 C39 C38 C58 -179.9(13) . . . . ?
F21 C39 C38 B3 6.9(14) . . . . ?
F22 C40 C39 C38 -178.7(13) . . . . ?
F22 C40 C39 F21 1.2(13) . . . . ?
B3 N4 C35 C44 178.9(13) . . . . ?
B3 N4 C35 C63 -11(2) . . . . ?
B3 C38 C58 F25 0.6(12) . . . . ?
B3 C38 C58 C59 174.1(11) . . . . ?
B3 C53 C54 C55 -175.5(15) . . . . ?
C52 C63 C50 C62 174.5(17) . . . . ?
C52 C63 C35 N4 14(3) . . . . ?
C52 C63 C35 C44 -175.2(14) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C52 C57 C56 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C57 0.0 . . . . ?
C55 C56 C57 C52 0.0 . . . . ?
C57 C52 C53 B3 175.5(15) . . . . ?
C57 C52 C53 C54 0.0 . . . . ?
N3 B2 C26 C32 2.2(14) . . . . ?
N3 B2 C26 C25 160.3(12) . . . . ?
N3 C44 C35 N4 179.5(10) . . . . ?
N3 C44 C35 C63 7.5(18) . . . . ?
N3 C62 C50 C63 -6(3) . . . . ?

_smtbx_masks_special_details     ?
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 -0.531 0.137 0.281 537.7 150.3 ?
2 -0.499 0.363 0.251 537.7 150.4 ?
3 -0.548 0.637 0.798 537.7 150.3 ?
4 0.175 0.863 0.425 537.7 150.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.2(4)
2 0.8(4)

####################################################################### 
# 
# 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_TN02221
_database_code_depnum_ccdc_archive 'CCDC 2333169'
loop_
_audit_author_name
_audit_author_address
'Wen Zhou'
;University of Calgary
Canada
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C46 H10 B2 F20 N4, 4(C2 H3 N)'
_chemical_formula_sum            'C54 H22 B2 F20 N8'
_chemical_formula_weight         1184.447
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07536 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.4453(13)
_cell_length_b                   20.727(3)
_cell_length_c                   12.4957(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.146(8)
_cell_angle_gamma                90
_cell_volume                     2408.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8483
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.430
_cell_measurement_theta_min      4.179
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1219 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8112.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       plate
_exptl_crystal_F_000             1189.655
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0550
0.00 1.00 0.00 0.0650
1.00 1.00 1.00 0.0690
0.00 1.00 -1.00 0.0510
0.00 -1.00 1.00 0.0720
0.00 1.00 1.00 0.0630
1.00 1.00 -1.00 0.0490
-1.00 -1.00 1.00 0.1030
1.00 -1.00 -1.00 0.0470
-1.00 1.00 1.00 0.0890
-1.00 -1.00 0.00 0.0950
1.00 1.00 0.00 0.0690
-1.00 0.00 0.00 0.0910
0.00 0.00 -1.00 0.0210
0.00 0.00 1.00 0.0720

_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.126
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.9915
_diffrn_reflns_Laue_measured_fraction_max 0.9809
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17519
_diffrn_reflns_point_group_measured_fraction_full 0.9915
_diffrn_reflns_point_group_measured_fraction_max 0.9809
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.18
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.9915
_diffrn_measured_fraction_theta_max 0.9809
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source_current           0.64
_diffrn_source_power             0.0285952
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                3802
_reflns_number_total             4682
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3925
_refine_diff_density_min         -0.5269
_refine_diff_density_rms         0.0788
_refine_ls_d_res_high            0.8084
_refine_ls_d_res_low             10.5779
_refine_ls_goodness_of_fit_ref   1.0618
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     439
_refine_ls_number_reflns         4682
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.0521
_refine_ls_shift/su_max          -0.0038
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1034P)²+1.3367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1787
_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. Uiso/Uaniso restraints and constraints
N4 \\sim C26 \\sim C27 \\sim N4A \\sim C26A \\sim C27A: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
N3 \\sim C24 \\sim C25 \\sim N3a \\sim C24a \\sim C25a: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
3. Others
 Sof(N4A)=Sof(C26A)=Sof(C27A)=Sof(H27d)=Sof(H27e)=Sof(H27f)=1-FVAR(1)
 Sof(N4)=Sof(C26)=Sof(C27)=Sof(H27a)=Sof(H27b)=Sof(H27c)=FVAR(1)
 Sof(N3a)=Sof(C24a)=Sof(C25a)=Sof(H25d)=Sof(H25e)=Sof(H25f)=1-FVAR(2)
 Sof(N3)=Sof(C24)=Sof(C25)=Sof(H25a)=Sof(H25b)=Sof(H25c)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C5(H5), C4(H4)
4.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C27(H27a,H27b,H27c), C27A(H27d,H27e,H27f), C25a(H25d,
 H25e,H25f)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
F1 F 0.14035(15) 0.64183(6) 0.23123(13) 0.0365(4) Uani 1.000000 . . . .
F2 F -0.10159(19) 0.68346(8) 0.28467(19) 0.0645(6) Uani 1.000000 . . . .
F3 F -0.26619(18) 0.60331(10) 0.38487(18) 0.0652(6) Uani 1.000000 . . . .
F4 F -0.18839(17) 0.47809(10) 0.41974(15) 0.0544(5) Uani 1.000000 . . . .
F5 F 0.05751(16) 0.43543(7) 0.37217(13) 0.0423(4) Uani 1.000000 . . . .
F6 F 0.56524(14) 0.52484(8) 0.23559(13) 0.0426(4) Uani 1.000000 . . . .
F7 F 0.65270(19) 0.57536(10) 0.06337(16) 0.0627(6) Uani 1.000000 . . . .
F8 F 0.4569(2) 0.61294(11) -0.11309(16) 0.0713(6) Uani 1.000000 . . . .
F9 F 0.1710(2) 0.59931(11) -0.11002(14) 0.0624(5) Uani 1.000000 . . . .
F10 F 0.08189(15) 0.55351(7) 0.06472(12) 0.0371(4) Uani 1.000000 . . . .
N1 N 0.38276(18) 0.53120(8) 0.37783(14) 0.0208(4) Uani 1.000000 . . . .
N2 N 0.9540(4) 0.71263(13) 1.0244(3) 0.0705(10) Uani 1.000000 . . . .
C6 C 0.7237(2) 0.56642(10) 0.74466(17) 0.0227(4) Uani 1.000000 . . . .
C7 C 0.8062(2) 0.59471(11) 0.83681(19) 0.0285(5) Uani 1.000000 . . . .
H2 H 0.8698(2) 0.56864(11) 0.88616(19) 0.0342(6) Uiso 1.000000 R . . .
C8 C 0.7965(3) 0.66008(11) 0.8571(2) 0.0321(5) Uani 1.000000 . . . .
C9 C 0.7005(3) 0.69905(11) 0.7876(2) 0.0366(6) Uani 1.000000 . . . .
H4 H 0.6912(3) 0.74356(11) 0.8031(2) 0.0439(7) Uiso 1.000000 R . . .
C10 C 0.6201(3) 0.67196(11) 0.6965(2) 0.0338(5) Uani 1.000000 . . . .
H5 H 0.5549(3) 0.69816(11) 0.6486(2) 0.0406(6) Uiso 1.000000 R . . .
C5 C 0.6324(2) 0.60642(10) 0.67303(18) 0.0241(5) Uani 1.000000 . . . .
C4 C 0.5512(2) 0.57944(10) 0.57147(17) 0.0221(4) Uani 1.000000 . . . .
C3 C 0.4796(2) 0.61895(10) 0.49122(19) 0.0262(5) Uani 1.000000 . . . .
H8 H 0.4860(2) 0.66441(10) 0.50054(19) 0.0315(6) Uiso 1.000000 R . . .
C2 C 0.3990(2) 0.59407(10) 0.39760(19) 0.0266(5) Uani 1.000000 . . . .
H9 H 0.3524(2) 0.62340(10) 0.34436(19) 0.0319(6) Uiso 1.000000 R . . .
C1 C 0.4571(2) 0.48813(9) 0.45126(16) 0.0195(4) Uani 1.000000 . . . .
C11 C 0.8841(3) 0.68869(12) 0.9512(2) 0.0444(7) Uani 1.000000 . . . .
C12 C 0.1118(2) 0.53559(11) 0.29565(18) 0.0249(5) Uani 1.000000 . . . .
C13 C 0.0626(2) 0.59834(11) 0.2768(2) 0.0310(5) Uani 1.000000 . . . .
C14 C -0.0631(3) 0.62143(13) 0.3039(3) 0.0422(6) Uani 1.000000 . . . .
C15 C -0.1471(3) 0.58121(15) 0.3532(2) 0.0434(7) Uani 1.000000 . . . .
C16 C -0.1060(3) 0.51813(14) 0.3720(2) 0.0389(6) Uani 1.000000 . . . .
C17 C 0.0214(2) 0.49701(12) 0.34476(19) 0.0308(5) Uani 1.000000 . . . .
C18 C 0.3185(2) 0.54181(10) 0.16335(18) 0.0242(4) Uani 1.000000 . . . .
C19 C 0.4632(3) 0.54628(12) 0.1547(2) 0.0310(5) Uani 1.000000 . . . .
C20 C 0.5113(3) 0.57113(14) 0.0641(2) 0.0423(6) Uani 1.000000 . . . .
C21 C 0.4137(3) 0.58959(15) -0.0241(2) 0.0463(7) Uani 1.000000 . . . .
C22 C 0.2688(3) 0.58355(14) -0.0222(2) 0.0407(6) Uani 1.000000 . . . .
C23 C 0.2247(3) 0.55983(11) 0.0702(2) 0.0300(5) Uani 1.000000 . . . .
B1 B 0.2685(2) 0.50997(11) 0.27100(19) 0.0215(5) Uani 1.000000 . . . .
N3 N 0.1491(6) 0.6899(2) 0.4829(4) 0.0894(11) Uani 0.821(5) . U P 3
C24 C 0.1813(7) 0.6853(3) 0.5748(5) 0.0882(11) Uani 0.821(5) . U P 3
C25 C 0.2209(7) 0.6787(4) 0.6888(5) 0.0893(11) Uani 0.821(5) . U P 3
H25a H 0.299(4) 0.6473(17) 0.7054(5) 0.1340(17) Uiso 0.821(5) GR . P 3
H25b H 0.253(5) 0.7205(6) 0.7209(6) 0.1340(17) Uiso 0.821(5) GR . P 3
H25c H 0.1380(16) 0.664(2) 0.7192(6) 0.1340(17) Uiso 0.821(5) GR . P 3
N3a N 0.017(4) 0.7963(16) 0.748(2) 0.0894(17) Uani 0.179(5) . U P 4
C24a C 0.048(4) 0.7578(19) 0.700(3) 0.0891(12) Uani 0.179(5) . U P 4
C25a C 0.075(3) 0.7191(15) 0.596(2) 0.0890(11) Uani 0.179(5) . U P 4
H25d H 0.05(2) 0.673(2) 0.604(8) 0.1336(17) Uiso 0.179(5) GR . P 4
H25e H 0.013(17) 0.736(7) 0.531(3) 0.1336(17) Uiso 0.179(5) GR . P 4
H25f H 0.176(6) 0.723(9) 0.588(10) 0.1336(17) Uiso 0.179(5) GR . P 4
N4 N -0.0462(8) 0.7939(3) 0.7075(7) 0.0943(14) Uani 0.741(6) . U P 1
C26 C -0.1047(8) 0.7725(3) 0.6260(7) 0.0927(14) Uani 0.741(6) . U P 1
C27 C -0.1773(7) 0.7462(3) 0.5246(6) 0.0934(14) Uani 0.741(6) . U P 1
H27a H -0.117(3) 0.752(2) 0.4689(12) 0.140(2) Uiso 0.741(6) GR . P 1
H27b H -0.195(5) 0.7001(6) 0.5335(12) 0.140(2) Uiso 0.741(6) GR . P 1
H27c H -0.269(3) 0.7686(17) 0.502(2) 0.140(2) Uiso 0.741(6) GR . P 1
N4A N 0.009(2) 0.7820(9) 0.7839(19) 0.0954(16) Uani 0.259(6) . U P 2
C26A C 0.082(3) 0.7517(12) 0.734(2) 0.0951(16) Uani 0.259(6) . U P 2
C27A C 0.155(3) 0.7124(10) 0.681(2) 0.0952(16) Uani 0.259(6) . U P 2
H27d H 0.230(12) 0.691(6) 0.732(2) 0.143(2) Uiso 0.259(6) GR . P 2
H27e H 0.090(4) 0.680(5) 0.641(11) 0.143(2) Uiso 0.259(6) GR . P 2
H27f H 0.199(15) 0.7372(15) 0.629(10) 0.143(2) Uiso 0.259(6) GR . P 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.350(3) . ?
F2 C14 1.346(3) . ?
F3 C15 1.337(3) . ?
F4 C16 1.347(3) . ?
F5 C17 1.350(3) . ?
F6 C19 1.344(3) . ?
F7 C20 1.340(3) . ?
F8 C21 1.340(3) . ?
F9 C22 1.344(3) . ?
F10 C23 1.345(3) . ?
N1 C2 1.330(3) . ?
N1 C1 1.380(3) . ?
N1 B1 1.622(3) . ?
N2 C11 1.142(4) . ?
C6 C7 1.400(3) . ?
C6 C5 1.400(3) . ?
C6 B1 1.599(3) 3_666 ?
C7 H2 0.9500 . ?
C7 C8 1.385(3) . ?
C8 C9 1.397(3) . ?
C8 C11 1.441(3) . ?
C9 H4 0.9500 . ?
C9 C10 1.372(3) . ?
C10 H5 0.9500 . ?
C10 C5 1.399(3) . ?
C5 C4 1.473(3) . ?
C4 C3 1.376(3) . ?
C4 C1 1.428(3) 3_666 ?
C3 H8 0.9500 . ?
C3 C2 1.379(3) . ?
C2 H9 0.9500 . ?
C1 C1 1.426(4) 3_666 ?
C12 C13 1.387(3) . ?
C12 C17 1.389(3) . ?
C12 B1 1.652(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.370(4) . ?
C15 C16 1.373(4) . ?
C16 C17 1.378(3) . ?
C18 C19 1.393(3) . ?
C18 C23 1.384(3) . ?
C18 B1 1.640(3) . ?
C19 C20 1.391(4) . ?
C20 C21 1.362(4) . ?
C21 C22 1.378(4) . ?
C22 C23 1.385(4) . ?
N3 C24 1.139(7) . ?
C24 C25 1.414(8) . ?
C25 H25a 0.9800 . ?
C25 H25b 0.9800 . ?
C25 H25c 0.9800 . ?
N3a C24a 1.07(5) . ?
C24a C25a 1.59(5) . ?
C25a H25d 0.9800 . ?
C25a H25e 0.9800 . ?
C25a H25f 0.9800 . ?
N4 C26 1.158(10) . ?
C26 C27 1.438(10) . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
N4A C26A 1.19(3) . ?
C26A C27A 1.32(3) . ?
C27A H27d 0.9800 . ?
C27A H27e 0.9800 . ?
C27A H27f 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
C1 N1 C2 118.80(18) . . ?
B1 N1 C2 117.16(17) . . ?
B1 N1 C1 123.94(16) . . ?
C5 C6 C7 117.94(19) . . ?
B1 C6 C7 118.99(19) 3_666 . ?
B1 C6 C5 122.99(19) 3_666 . ?
H2 C7 C6 119.49(13) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H2 119.49(14) . . ?
C9 C8 C7 120.6(2) . . ?
C11 C8 C7 120.3(2) . . ?
C11 C8 C9 119.1(2) . . ?
H4 C9 C8 120.55(14) . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 H4 120.55(14) . . ?
H5 C10 C9 119.44(14) . . ?
C5 C10 C9 121.1(2) . . ?
C5 C10 H5 119.44(14) . . ?
C10 C5 C6 120.4(2) . . ?
C4 C5 C6 119.65(19) . . ?
C4 C5 C10 120.0(2) . . ?
C3 C4 C5 121.08(19) . . ?
C1 C4 C5 123.07(19) 3_666 . ?
C1 C4 C3 115.84(19) 3_666 . ?
H8 C3 C4 119.24(13) . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H8 119.24(13) . . ?
C3 C2 N1 123.5(2) . . ?
H9 C2 N1 118.24(12) . . ?
H9 C2 C3 118.24(13) . . ?
C4 C1 N1 119.89(18) 3_666 . ?
C1 C1 N1 119.4(2) 3_666 . ?
C1 C1 C4 120.7(2) 3_666 3_666 ?
C8 C11 N2 178.4(3) . . ?
C17 C12 C13 113.7(2) . . ?
B1 C12 C13 123.64(19) . . ?
B1 C12 C17 122.6(2) . . ?
C12 C13 F1 120.5(2) . . ?
C14 C13 F1 115.4(2) . . ?
C14 C13 C12 124.2(2) . . ?
C13 C14 F2 120.4(3) . . ?
C15 C14 F2 120.1(2) . . ?
C15 C14 C13 119.5(3) . . ?
C14 C15 F3 120.6(3) . . ?
C16 C15 F3 120.2(3) . . ?
C16 C15 C14 119.2(2) . . ?
C15 C16 F4 119.6(2) . . ?
C17 C16 F4 120.8(3) . . ?
C17 C16 C15 119.6(2) . . ?
C12 C17 F5 120.6(2) . . ?
C16 C17 F5 115.5(2) . . ?
C16 C17 C12 123.9(2) . . ?
C23 C18 C19 114.1(2) . . ?
B1 C18 C19 121.2(2) . . ?
B1 C18 C23 124.35(19) . . ?
C18 C19 F6 120.2(2) . . ?
C20 C19 F6 116.2(2) . . ?
C20 C19 C18 123.6(2) . . ?
C19 C20 F7 119.9(3) . . ?
C21 C20 F7 120.7(2) . . ?
C21 C20 C19 119.4(2) . . ?
C20 C21 F8 120.7(3) . . ?
C22 C21 F8 119.7(3) . . ?
C22 C21 C20 119.5(2) . . ?
C21 C22 F9 120.3(2) . . ?
C23 C22 F9 120.2(2) . . ?
C23 C22 C21 119.5(2) . . ?
C18 C23 F10 120.3(2) . . ?
C22 C23 F10 116.0(2) . . ?
C22 C23 C18 123.7(2) . . ?
C6 B1 N1 109.34(17) 3_666 . ?
C12 B1 N1 104.31(16) . . ?
C12 B1 C6 113.77(17) . 3_666 ?
C18 B1 N1 108.66(16) . . ?
C18 B1 C6 105.79(17) . 3_666 ?
C18 B1 C12 114.85(17) . . ?
C25 C24 N3 179.2(7) . . ?
H25a C25 C24 109.5 . . ?
H25b C25 C24 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C24 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
C25a C24a N3a 159(3) . . ?
H25d C25a C24a 109.5 . . ?
H25e C25a C24a 109.5 . . ?
H25e C25a H25d 109.5 . . ?
H25f C25a C24a 109.5 . . ?
H25f C25a H25d 109.5 . . ?
H25f C25a H25e 109.5 . . ?
C27 C26 N4 179.6(8) . . ?
H27a C27 C26 109.5 . . ?
H27b C27 C26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
C27A C26A N4A 174(3) . . ?
H27d C27A C26A 109.5 . . ?
H27e C27A C26A 109.5 . . ?
H27e C27A H27d 109.5 . . ?
H27f C27A C26A 109.5 . . ?
H27f C27A H27d 109.5 . . ?
H27f C27A H27e 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
F1 C13 C12 C17 178.8(2) . . . . ?
F1 C13 C12 B1 3.2(3) . . . . ?
F1 C13 C14 F2 0.1(3) . . . . ?
F1 C13 C14 C15 -178.3(2) . . . . ?
F2 C14 C13 C12 178.7(2) . . . . ?
F2 C14 C15 F3 -1.5(3) . . . . ?
F2 C14 C15 C16 180.0(3) . . . . ?
F3 C15 C14 C13 176.9(3) . . . . ?
F3 C15 C16 F4 1.9(3) . . . . ?
F3 C15 C16 C17 -176.2(3) . . . . ?
F4 C16 C15 C14 -179.6(3) . . . . ?
F4 C16 C17 F5 -1.9(3) . . . . ?
F4 C16 C17 C12 -179.9(2) . . . . ?
F5 C17 C12 C13 -177.4(2) . . . . ?
F5 C17 C12 B1 -1.7(3) . . . . ?
F5 C17 C16 C15 176.1(2) . . . . ?
F6 C19 C18 C23 -174.1(2) . . . . ?
F6 C19 C18 B1 -0.6(3) . . . . ?
F6 C19 C20 F7 -3.1(3) . . . . ?
F6 C19 C20 C21 175.5(2) . . . . ?
F7 C20 C19 C18 178.2(2) . . . . ?
F7 C20 C21 F8 -0.6(3) . . . . ?
F7 C20 C21 C22 178.7(3) . . . . ?
F8 C21 C20 C19 -179.1(3) . . . . ?
F8 C21 C22 F9 1.8(3) . . . . ?
F8 C21 C22 C23 -179.5(3) . . . . ?
F9 C22 C21 C20 -177.6(3) . . . . ?
F9 C22 C23 F10 0.6(3) . . . . ?
F9 C22 C23 C18 179.2(2) . . . . ?
F10 C23 C18 C19 175.3(2) . . . . ?
F10 C23 C18 B1 2.0(3) . . . . ?
F10 C23 C22 C21 -178.1(2) . . . . ?
N1 C2 C3 C4 0.6(3) . . . . ?
N1 C1 C4 C5 2.3(2) . . 3_666 3_666 ?
N1 C1 C4 C3 -176.78(19) . . 3_666 3_666 ?
N1 C1 C1 N1 -180.0(2) . . 3_666 3_666 ?
N1 C1 C1 C4 0.7(2) . . 3_666 . ?
N1 B1 C6 C7 -175.41(16) . . 3_666 3_666 ?
N1 B1 C6 C5 1.3(2) . . 3_666 3_666 ?
N1 B1 C12 C13 83.1(2) . . . . ?
N1 B1 C12 C17 -92.18(19) . . . . ?
N1 B1 C18 C19 37.9(2) . . . . ?
N1 B1 C18 C23 -149.28(17) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C6 C7 C8 C11 -178.8(2) . . . . ?
C6 C5 C10 C9 2.5(3) . . . . ?
C6 C5 C4 C3 -169.1(2) . . . . ?
C6 C5 C4 C1 9.9(2) . . . 3_666 ?
C6 B1 C12 C13 -157.83(19) 3_666 . . . ?
C6 B1 C12 C17 26.9(2) 3_666 . . . ?
C6 B1 C18 C19 -79.4(2) 3_666 . . . ?
C6 B1 C18 C23 93.41(19) 3_666 . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C9 C10 C5 C4 -176.3(2) . . . . ?
C10 C5 C4 C3 9.7(3) . . . . ?
C10 C5 C4 C1 -171.3(2) . . . 3_666 ?
C5 C4 C3 C2 -177.5(2) . . . . ?
C5 C4 C1 C1 177.0(2) . . 3_666 . ?
C4 C1 C1 C4 180.0(3) . 3_666 . 3_666 ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C17 C16 C15 -1.8(3) . . . . ?
C12 B1 C18 C19 154.26(19) . . . . ?
C12 B1 C18 C23 -32.9(2) . . . . ?
C13 C14 C15 C16 -1.6(3) . . . . ?
C14 C15 C16 C17 2.4(3) . . . . ?
C18 C19 C20 C21 -3.3(3) . . . . ?
C18 C23 C22 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
N3 C24 0.0020
N3 C25a 0.0020
C24 C25 0.0010
C24 C25a 0.0010
C25 C25a 0.0010
N3a C24a 0.0020
C24a C25a 0.0010
N4 C26 0.0020
N4 N4A 0.0020
N4 C26A 0.0020
C26 C27 0.0010
N4A C26A 0.0020
C26A C27A 0.0010

