#------------------------------------------------------------------------------
#$Date: 2023-10-05 01:55:07 +0300 (Thu, 05 Oct 2023) $
#$Revision: 286662 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/41/7714116.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7714116
loop_
_publ_author_name
'Yoshino, Junro'
'Hirono, Yoshito'
'Kaneda, Ayako'
'Hayashi, Naoto'
_publ_section_title
;
 Synthesis, Structures, and Solid-State Photoresponsive Color Change
 Behavior of Boronium Complexes Bearing a Pyridine-Imine, Diimine, or
 Pyridine-Ketone Bidentate Ligand
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02332J
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H38 B F3 N2 O3 S'
_chemical_formula_sum            'C23 H38 B F3 N2 O3 S'
_chemical_formula_weight         490.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-06-03 deposited with the CCDC.	2023-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.550(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   6.5214(2)
_cell_length_b                   20.7113(6)
_cell_length_c                   9.6322(3)
_cell_measurement_reflns_used    11529
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.97
_cell_volume                     1247.09(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         2.206
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524.00
_exptl_crystal_size_max          0.678
_exptl_crystal_size_mid          0.405
_exptl_crystal_size_min          0.338
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
;
 Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                5047
_reflns_number_total             5353
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d3dt02332j2.cif
_cod_data_source_block           dichexbbnotf
_cod_database_code               7714116
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
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 0.94091(12) 0.32662(3) 0.88364(8) 0.0409(2) Uani 1 1 d . . . . .
F1 F 0.9625(3) 0.44579(9) 0.97620(19) 0.0502(5) Uani 1 1 d . . . . .
F2 F 0.9789(7) 0.43696(12) 0.7607(3) 0.1023(12) Uani 1 1 d . . . . .
F3 F 0.6785(4) 0.42488(13) 0.8107(3) 0.0946(11) Uani 1 1 d . . . . .
O1 O 0.8310(4) 0.30979(12) 0.9869(3) 0.0534(6) Uani 1 1 d . . . . .
O2 O 1.1672(4) 0.32453(16) 0.9376(4) 0.0827(10) Uani 1 1 d . . . . .
O3 O 0.8502(6) 0.29997(13) 0.7420(3) 0.0816(10) Uani 1 1 d . . . . .
N1 N 0.2986(3) 0.28613(9) 0.5482(2) 0.0225(4) Uani 1 1 d . . . . .
N2 N 0.4197(3) 0.19864(9) 0.70774(19) 0.0218(4) Uani 1 1 d . . . . .
C1 C 0.1318(3) 0.16953(12) 0.4524(2) 0.0236(4) Uani 1 1 d . . . . .
H1 H 0.016733 0.177445 0.500289 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0515(4) 0.19251(13) 0.2933(2) 0.0282(5) Uani 1 1 d . . . . .
H2A H -0.066499 0.163789 0.240808 0.034 Uiso 1 1 calc R U . . .
H2B H -0.008394 0.236496 0.292122 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2215(4) 0.19393(14) 0.2105(2) 0.0315(5) Uani 1 1 d . . . . .
H3A H 0.167884 0.221675 0.124066 0.038 Uiso 1 1 calc R U . . .
H3B H 0.236657 0.149680 0.175834 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4455(4) 0.21835(13) 0.2963(2) 0.0293(5) Uani 1 1 d . . . . .
H4A H 0.443846 0.266149 0.295412 0.035 Uiso 1 1 calc R U . . .
H4B H 0.549843 0.204139 0.245409 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5250(3) 0.19533(12) 0.4558(2) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.657576 0.219905 0.505574 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5779(4) 0.12285(12) 0.4663(3) 0.0268(5) Uani 1 1 d . . . . .
H6A H 0.653867 0.112489 0.568318 0.032 Uiso 1 1 calc R U . . .
H6B H 0.677373 0.113892 0.407824 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3825(4) 0.07708(12) 0.4151(3) 0.0305(5) Uani 1 1 d . . . . .
H7A H 0.341744 0.074590 0.308030 0.037 Uiso 1 1 calc R U . . .
H7B H 0.426877 0.033267 0.452959 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1844(4) 0.09644(12) 0.4609(3) 0.0286(5) Uani 1 1 d . . . . .
H8A H 0.204660 0.081888 0.561855 0.034 Uiso 1 1 calc R U . . .
H8B H 0.059256 0.073011 0.398935 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3449(4) 0.30440(12) 0.6814(2) 0.0294(5) Uani 1 1 d . . . . .
H9 H 0.332291 0.347520 0.711547 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4186(4) 0.25085(12) 0.7789(2) 0.0284(5) Uani 1 1 d . . . . .
H10 H 0.460426 0.253911 0.881534 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2169(3) 0.33519(11) 0.4320(2) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.192893 0.313130 0.336340 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0021(4) 0.36218(13) 0.4401(3) 0.0301(5) Uani 1 1 d . . . . .
H12A H 0.019485 0.382120 0.536221 0.036 Uiso 1 1 calc R U . . .
H12B H -0.103371 0.326723 0.427780 0.036 Uiso 1 1 calc R U . . .
C13 C -0.0791(4) 0.41286(15) 0.3209(3) 0.0372(6) Uani 1 1 d . . . . .
H13A H -0.110833 0.391691 0.224970 0.045 Uiso 1 1 calc R U . . .
H13B H -0.213441 0.432069 0.330411 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0848(4) 0.46579(14) 0.3302(3) 0.0365(6) Uani 1 1 d . . . . .
H14A H 0.108469 0.489298 0.422914 0.044 Uiso 1 1 calc R U . . .
H14B H 0.030398 0.496933 0.250194 0.044 Uiso 1 1 calc R U . . .
C15 C 0.2960(4) 0.43720(13) 0.3205(3) 0.0324(5) Uani 1 1 d . . . . .
H15A H 0.273694 0.415661 0.225573 0.039 Uiso 1 1 calc R U . . .
H15B H 0.401661 0.472252 0.327576 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3824(4) 0.38851(12) 0.4416(3) 0.0293(5) Uani 1 1 d . . . . .
H16A H 0.412884 0.410373 0.536757 0.035 Uiso 1 1 calc R U . . .
H16B H 0.517425 0.369585 0.432616 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4850(3) 0.13773(11) 0.7897(2) 0.0221(4) Uani 1 1 d . . . . .
H17 H 0.487061 0.102786 0.718499 0.027 Uiso 1 1 calc R U . . .
C18 C 0.7104(3) 0.14326(11) 0.8944(3) 0.0260(5) Uani 1 1 d . . . . .
H18A H 0.814032 0.153863 0.840073 0.031 Uiso 1 1 calc R U . . .
H18B H 0.714408 0.178238 0.965190 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7709(4) 0.07895(12) 0.9739(3) 0.0296(5) Uani 1 1 d . . . . .
H19A H 0.778456 0.044991 0.903172 0.036 Uiso 1 1 calc R U . . .
H19B H 0.914229 0.082864 1.044440 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6096(4) 0.05917(14) 1.0530(3) 0.0348(6) Uani 1 1 d . . . . .
H20A H 0.649369 0.016410 1.098706 0.042 Uiso 1 1 calc R U . . .
H20B H 0.612682 0.090779 1.130709 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3855(4) 0.05589(14) 0.9500(3) 0.0339(5) Uani 1 1 d . . . . .
H21A H 0.283028 0.045638 1.005498 0.041 Uiso 1 1 calc R U . . .
H21B H 0.378593 0.020682 0.879351 0.041 Uiso 1 1 calc R U . . .
C22 C 0.3205(4) 0.11916(12) 0.8689(2) 0.0278(5) Uani 1 1 d . . . . .
H22A H 0.311702 0.153673 0.938117 0.033 Uiso 1 1 calc R U . . .
H22B H 0.177706 0.114383 0.798163 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8875(6) 0.41281(16) 0.8564(3) 0.0436(7) Uani 1 1 d . . . . .
B1 B 0.3423(4) 0.21086(12) 0.5371(3) 0.0206(4) Uani 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 114.48(19) . . ?
O2 S1 O3 116.2(2) . . ?
O1 S1 O3 114.62(18) . . ?
O2 S1 C23 102.64(18) . . ?
O1 S1 C23 103.10(15) . . ?
O3 S1 C23 103.28(16) . . ?
C9 N1 C11 118.6(2) . . ?
C9 N1 B1 111.00(19) . . ?
C11 N1 B1 130.38(18) . . ?
C10 N2 C17 118.49(18) . . ?
C10 N2 B1 111.63(19) . . ?
C17 N2 B1 129.87(18) . . ?
C2 C1 C8 111.14(19) . . ?
C2 C1 B1 109.53(18) . . ?
C8 C1 B1 110.21(18) . . ?
C2 C1 H1 108.6 . . ?
C8 C1 H1 108.6 . . ?
B1 C1 H1 108.6 . . ?
C3 C2 C1 115.38(18) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 116.10(19) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 C5 115.34(19) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 111.80(19) . . ?
C6 C5 B1 109.95(18) . . ?
C4 C5 B1 109.32(17) . . ?
C6 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
B1 C5 H5 108.6 . . ?
C5 C6 C7 115.29(19) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 115.6(2) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 C1 115.6(2) . . ?
C7 C8 H8A 108.4 . . ?
C1 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
N1 C9 C10 111.2(2) . . ?
N1 C9 H9 124.4 . . ?
C10 C9 H9 124.4 . . ?
N2 C10 C9 110.6(2) . . ?
N2 C10 H10 124.7 . . ?
C9 C10 H10 124.7 . . ?
N1 C11 C16 110.57(17) . . ?
N1 C11 C12 110.26(17) . . ?
C16 C11 C12 111.9(2) . . ?
N1 C11 H11 108.0 . . ?
C16 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C11 C12 C13 109.71(19) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.3(2) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.4(2) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.7(2) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 109.32(19) . . ?
C15 C16 H16A 109.8 . . ?
C11 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C11 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N2 C17 C18 111.27(18) . . ?
N2 C17 C22 110.04(17) . . ?
C18 C17 C22 111.58(18) . . ?
N2 C17 H17 107.9 . . ?
C18 C17 H17 107.9 . . ?
C22 C17 H17 107.9 . . ?
C19 C18 C17 109.05(19) . . ?
C19 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 C18 111.6(2) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C19 111.1(2) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 111.9(2) . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C17 109.85(19) . . ?
C21 C22 H22A 109.7 . . ?
C17 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C17 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
F1 C23 F2 106.6(3) . . ?
F1 C23 F3 106.5(3) . . ?
F2 C23 F3 108.6(3) . . ?
F1 C23 S1 112.0(2) . . ?
F2 C23 S1 111.3(3) . . ?
F3 C23 S1 111.5(2) . . ?
N1 B1 N2 95.52(16) . . ?
N1 B1 C1 114.00(17) . . ?
N2 B1 C1 114.03(18) . . ?
N1 B1 C5 113.18(18) . . ?
N2 B1 C5 113.75(17) . . ?
C1 B1 C5 106.42(18) . . ?
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 O2 1.419(3) . ?
S1 O1 1.425(2) . ?
S1 O3 1.434(3) . ?
S1 C23 1.823(3) . ?
F1 C23 1.310(3) . ?
F2 C23 1.330(4) . ?
F3 C23 1.331(4) . ?
N1 C9 1.288(3) . ?
N1 C11 1.493(3) . ?
N1 B1 1.594(3) . ?
N2 C10 1.281(3) . ?
N2 C17 1.485(3) . ?
N2 B1 1.596(3) . ?
C1 C2 1.546(3) . ?
C1 C8 1.549(3) . ?
C1 B1 1.626(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.539(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.545(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.549(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.537(3) . ?
C5 B1 1.634(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.552(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.444(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.528(3) . ?
C11 C12 1.531(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.534(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.516(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.532(3) . ?
C17 C22 1.532(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.531(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.521(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.523(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
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
C8 C1 C2 C3 -69.9(3) . . . . ?
B1 C1 C2 C3 52.1(3) . . . . ?
C1 C2 C3 C4 -40.2(3) . . . . ?
C2 C3 C4 C5 40.1(3) . . . . ?
C3 C4 C5 C6 70.3(2) . . . . ?
C3 C4 C5 B1 -51.7(3) . . . . ?
C4 C5 C6 C7 -69.2(2) . . . . ?
B1 C5 C6 C7 52.4(3) . . . . ?
C5 C6 C7 C8 -41.3(3) . . . . ?
C6 C7 C8 C1 40.6(3) . . . . ?
C2 C1 C8 C7 70.2(2) . . . . ?
B1 C1 C8 C7 -51.5(3) . . . . ?
C11 N1 C9 C10 179.27(18) . . . . ?
B1 N1 C9 C10 -1.0(3) . . . . ?
C17 N2 C10 C9 -178.27(19) . . . . ?
B1 N2 C10 C9 0.6(3) . . . . ?
N1 C9 C10 N2 0.2(3) . . . . ?
C9 N1 C11 C16 60.7(3) . . . . ?
B1 N1 C11 C16 -119.1(2) . . . . ?
C9 N1 C11 C12 -63.6(3) . . . . ?
B1 N1 C11 C12 116.6(2) . . . . ?
N1 C11 C12 C13 179.6(2) . . . . ?
C16 C11 C12 C13 56.1(3) . . . . ?
C11 C12 C13 C14 -55.6(3) . . . . ?
C12 C13 C14 C15 57.3(3) . . . . ?
C13 C14 C15 C16 -58.7(3) . . . . ?
C14 C15 C16 C11 58.1(3) . . . . ?
N1 C11 C16 C15 179.15(19) . . . . ?
C12 C11 C16 C15 -57.5(3) . . . . ?
C10 N2 C17 C18 -57.7(3) . . . . ?
B1 N2 C17 C18 123.6(2) . . . . ?
C10 N2 C17 C22 66.5(3) . . . . ?
B1 N2 C17 C22 -112.2(2) . . . . ?
N2 C17 C18 C19 -179.02(17) . . . . ?
C22 C17 C18 C19 57.7(3) . . . . ?
C17 C18 C19 C20 -56.8(3) . . . . ?
C18 C19 C20 C21 56.1(3) . . . . ?
C19 C20 C21 C22 -55.4(3) . . . . ?
C20 C21 C22 C17 55.6(3) . . . . ?
N2 C17 C22 C21 178.72(19) . . . . ?
C18 C17 C22 C21 -57.3(3) . . . . ?
O2 S1 C23 F1 -58.1(3) . . . . ?
O1 S1 C23 F1 61.1(3) . . . . ?
O3 S1 C23 F1 -179.3(3) . . . . ?
O2 S1 C23 F2 61.1(3) . . . . ?
O1 S1 C23 F2 -179.7(3) . . . . ?
O3 S1 C23 F2 -60.0(3) . . . . ?
O2 S1 C23 F3 -177.4(3) . . . . ?
O1 S1 C23 F3 -58.2(3) . . . . ?
O3 S1 C23 F3 61.5(3) . . . . ?
C9 N1 B1 N2 1.2(2) . . . . ?
C11 N1 B1 N2 -179.09(18) . . . . ?
C9 N1 B1 C1 120.6(2) . . . . ?
C11 N1 B1 C1 -59.7(3) . . . . ?
C9 N1 B1 C5 -117.6(2) . . . . ?
C11 N1 B1 C5 62.1(3) . . . . ?
C10 N2 B1 N1 -1.0(2) . . . . ?
C17 N2 B1 N1 177.70(19) . . . . ?
C10 N2 B1 C1 -120.4(2) . . . . ?
C17 N2 B1 C1 58.3(3) . . . . ?
C10 N2 B1 C5 117.3(2) . . . . ?
C17 N2 B1 C5 -64.0(3) . . . . ?
C2 C1 B1 N1 63.3(2) . . . . ?
C8 C1 B1 N1 -174.16(18) . . . . ?
C2 C1 B1 N2 171.56(18) . . . . ?
C8 C1 B1 N2 -65.9(2) . . . . ?
C2 C1 B1 C5 -62.2(2) . . . . ?
C8 C1 B1 C5 60.4(2) . . . . ?
C6 C5 B1 N1 172.94(17) . . . . ?
C4 C5 B1 N1 -64.0(2) . . . . ?
C6 C5 B1 N2 65.3(2) . . . . ?
C4 C5 B1 N2 -171.60(19) . . . . ?
C6 C5 B1 C1 -61.1(2) . . . . ?
C4 C5 B1 C1 62.0(2) . . . . ?
