#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/48/4024893.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_4024893
loop_
_publ_author_name
'Junro Yoshino'
'Naokazu Kano'
'Takayuki Kawashima'
_publ_contact_author_address
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
_publ_contact_author_email       kano@chem.s.u-tokyo.ac.jp
_publ_contact_author_fax         +81-5800-6899
_publ_contact_author_name        'Naokazu Kano'
_publ_contact_author_phone       +81-5841-4341
_publ_section_title
;
Fluorescence Properties of Simple N-Substituted Aldimines with a B-N
Interaction and Their Fluorescence Quenching by a Cyanide Ion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7496
_journal_page_last               7503
_journal_paper_doi               10.1021/jo901733b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C27 H15 B F10 N2'
_chemical_formula_sum            'C27 H15 B F10 N2'
_chemical_formula_weight         568.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.499(3)
_cell_angle_beta                 99.863(3)
_cell_angle_gamma                116.313(4)
_cell_formula_units_Z            2
_cell_length_a                   10.685(2)
_cell_length_b                   10.787(2)
_cell_length_c                   12.3860(18)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.2438
_cell_volume                     1189.6(4)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 55.1086
              2theta: 24.6499
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 55.1086
              2theta: 24.6499
scan:
    Number of images: 600
               Slice: -65.0000 - 115.0000
         Image width: 0.3000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 55.1086
              2theta: 24.6499

;
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3-circle
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0758
_diffrn_orient_matrix_UB_12      -0.0786
_diffrn_orient_matrix_UB_13      0.0098
_diffrn_orient_matrix_UB_21      -0.0234
_diffrn_orient_matrix_UB_22      -0.0921
_diffrn_orient_matrix_UB_23      0.0545
_diffrn_orient_matrix_UB_31      -0.0195
_diffrn_orient_matrix_UB_32      -0.0628
_diffrn_orient_matrix_UB_33      -0.0567
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0256
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9632
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Private communication, Jacobson, R. (1998)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0465P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                3575
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901733b_si_003.cif
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4024893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.43951(18) 0.20785(17) 0.21271(13) 0.0193(3) Uani 1 1 d . . .
C1 C 0.61267(15) 0.27067(14) 0.23180(12) 0.0195(3) Uani 1 1 d . . .
C2 C 0.69409(16) 0.25030(15) 0.16046(12) 0.0228(3) Uani 1 1 d . . .
H1 H 0.6458 0.1810 0.0842 0.027 Uiso 1 1 calc R . .
C3 C 0.84651(17) 0.33190(16) 0.20117(13) 0.0257(3) Uani 1 1 d . . .
H2 H 0.9014 0.3161 0.1524 0.031 Uiso 1 1 calc R . .
C4 C 0.92040(16) 0.43607(16) 0.31161(13) 0.0255(3) Uani 1 1 d . . .
H3 H 1.0245 0.4912 0.3371 0.031 Uiso 1 1 calc R . .
C5 C 0.84244(16) 0.45949(15) 0.38443(12) 0.0223(3) Uani 1 1 d . . .
H4 H 0.8915 0.5304 0.4600 0.027 Uiso 1 1 calc R . .
C6 C 0.68988(15) 0.37590(14) 0.34365(12) 0.0195(3) Uani 1 1 d . . .
C7 C 0.58769(15) 0.37966(14) 0.40455(12) 0.0199(3) Uani 1 1 d . . .
H5 H 0.6170 0.4401 0.4827 0.024 Uiso 1 1 calc R . .
N1 N 0.45131(12) 0.29225(12) 0.34212(9) 0.0182(3) Uani 1 1 d . . .
C8 C 0.33080(15) 0.26255(14) 0.38750(12) 0.0190(3) Uani 1 1 d . . .
C9 C 0.34554(16) 0.26870(15) 0.50270(12) 0.0214(3) Uani 1 1 d . . .
H6 H 0.4379 0.2952 0.5526 0.026 Uiso 1 1 calc R . .
C10 C 0.22789(16) 0.23687(15) 0.54533(12) 0.0220(3) Uani 1 1 d . . .
H7 H 0.2414 0.2446 0.6248 0.026 Uiso 1 1 calc R . .
C11 C 0.08780(16) 0.19301(15) 0.47344(12) 0.0209(3) Uani 1 1 d . . .
C12 C 0.07511(16) 0.18844(16) 0.35706(12) 0.0228(3) Uani 1 1 d . . .
H8 H -0.0167 0.1627 0.3066 0.027 Uiso 1 1 calc R . .
C13 C 0.19372(16) 0.22072(15) 0.31531(12) 0.0218(3) Uani 1 1 d . . .
H9 H 0.1816 0.2143 0.2361 0.026 Uiso 1 1 calc R . .
N2 N -0.03076(13) 0.15381(14) 0.51413(10) 0.0264(3) Uani 1 1 d . . .
C14 C -0.01536(17) 0.16100(17) 0.63448(13) 0.0281(3) Uani 1 1 d . . .
H10 H 0.0459 0.1196 0.6576 0.042 Uiso 1 1 calc R . .
H11 H -0.1123 0.1048 0.6430 0.042 Uiso 1 1 calc R . .
H12 H 0.0307 0.2634 0.6840 0.042 Uiso 1 1 calc R . .
C15 C -0.17153(16) 0.12306(17) 0.44418(14) 0.0286(3) Uani 1 1 d . . .
H13 H -0.1616 0.2118 0.4288 0.043 Uiso 1 1 calc R . .
H14 H -0.2437 0.0915 0.4861 0.043 Uiso 1 1 calc R . .
H15 H -0.2043 0.0451 0.3704 0.043 Uiso 1 1 calc R . .
C16 C 0.33959(15) 0.03277(15) 0.19136(12) 0.0198(3) Uani 1 1 d . . .
C17 C 0.39236(16) -0.03219(16) 0.25822(12) 0.0238(3) Uani 1 1 d . . .
C18 C 0.31722(17) -0.17865(16) 0.24798(13) 0.0276(3) Uani 1 1 d . . .
C19 C 0.18106(17) -0.26874(15) 0.16747(14) 0.0281(4) Uani 1 1 d . . .
C20 C 0.12218(16) -0.21012(16) 0.10083(13) 0.0267(3) Uani 1 1 d . . .
C21 C 0.19979(16) -0.06285(16) 0.11418(12) 0.0235(3) Uani 1 1 d . . .
F1 F 0.52380(9) 0.05060(9) 0.34090(8) 0.0331(2) Uani 1 1 d . . .
F2 F 0.37484(11) -0.23251(10) 0.31722(9) 0.0427(3) Uani 1 1 d . . .
F3 F 0.10471(11) -0.41072(10) 0.15666(9) 0.0417(3) Uani 1 1 d . . .
F4 F -0.01305(10) -0.29631(10) 0.02340(8) 0.0398(3) Uani 1 1 d . . .
F5 F 0.13048(9) -0.01459(10) 0.04743(8) 0.0323(2) Uani 1 1 d . . .
C22 C 0.38512(15) 0.26943(15) 0.11570(12) 0.0201(3) Uani 1 1 d . . .
C23 C 0.37471(15) 0.39583(15) 0.13651(12) 0.0212(3) Uani 1 1 d . . .
C24 C 0.34089(15) 0.44895(15) 0.05040(13) 0.0225(3) Uani 1 1 d . . .
C25 C 0.31611(16) 0.37530(16) -0.06343(13) 0.0245(3) Uani 1 1 d . . .
C26 C 0.32870(16) 0.25118(16) -0.08878(12) 0.0257(3) Uani 1 1 d . . .
C27 C 0.36302(16) 0.20273(15) -0.00047(12) 0.0232(3) Uani 1 1 d . . .
F6 F 0.40052(10) 0.47726(9) 0.24613(7) 0.0282(2) Uani 1 1 d . . .
F7 F 0.33428(10) 0.57273(9) 0.07674(8) 0.0311(2) Uani 1 1 d . . .
F8 F 0.28474(10) 0.42568(10) -0.14800(8) 0.0348(2) Uani 1 1 d . . .
F9 F 0.30920(11) 0.18010(10) -0.19907(7) 0.0385(2) Uani 1 1 d . . .
F10 F 0.37620(10) 0.08162(9) -0.03166(7) 0.0303(2) 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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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 B1 N1 97.71(10) . . ?
C1 B1 C22 106.12(11) . . ?
N1 B1 C22 112.37(11) . . ?
C1 B1 C16 116.67(11) . . ?
N1 B1 C16 106.15(11) . . ?
C22 B1 C16 116.37(12) . . ?
C2 C1 C6 117.72(13) . . ?
C2 C1 B1 133.86(13) . . ?
C6 C1 B1 108.20(12) . . ?
C1 C2 C3 119.76(13) . . ?
C1 C2 H1 120.1 . . ?
C3 C2 H1 120.1 . . ?
C4 C3 C2 121.52(14) . . ?
C4 C3 H2 119.2 . . ?
C2 C3 H2 119.2 . . ?
C5 C4 C3 120.09(14) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C4 C5 C6 118.05(13) . . ?
C4 C5 H4 121.0 . . ?
C6 C5 H4 121.0 . . ?
C5 C6 C1 122.84(13) . . ?
C5 C6 C7 127.57(13) . . ?
C1 C6 C7 109.59(12) . . ?
N1 C7 C6 113.42(12) . . ?
N1 C7 H5 123.3 . . ?
C6 C7 H5 123.3 . . ?
C7 N1 C8 123.70(12) . . ?
C7 N1 B1 110.75(11) . . ?
C8 N1 B1 125.11(11) . . ?
C9 C8 C13 118.59(13) . . ?
C9 C8 N1 121.18(12) . . ?
C13 C8 N1 120.18(12) . . ?
C10 C9 C8 120.88(13) . . ?
C10 C9 H6 119.6 . . ?
C8 C9 H6 119.6 . . ?
C9 C10 C11 121.42(13) . . ?
C9 C10 H7 119.3 . . ?
C11 C10 H7 119.3 . . ?
N2 C11 C10 121.44(13) . . ?
N2 C11 C12 121.65(13) . . ?
C10 C11 C12 116.90(13) . . ?
C13 C12 C11 121.16(13) . . ?
C13 C12 H8 119.4 . . ?
C11 C12 H8 119.4 . . ?
C12 C13 C8 120.99(13) . . ?
C12 C13 H9 119.5 . . ?
C8 C13 H9 119.5 . . ?
C11 N2 C15 121.52(12) . . ?
C11 N2 C14 120.92(12) . . ?
C15 N2 C14 117.03(12) . . ?
N2 C14 H10 109.5 . . ?
N2 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
N2 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
N2 C15 H13 109.5 . . ?
N2 C15 H14 109.5 . . ?
H13 C15 H14 109.5 . . ?
N2 C15 H15 109.5 . . ?
H13 C15 H15 109.5 . . ?
H14 C15 H15 109.5 . . ?
C21 C16 C17 113.60(13) . . ?
C21 C16 B1 126.94(13) . . ?
C17 C16 B1 119.42(12) . . ?
F1 C17 C18 116.13(13) . . ?
F1 C17 C16 119.52(12) . . ?
C18 C17 C16 124.34(13) . . ?
F2 C18 C19 119.99(13) . . ?
F2 C18 C17 120.70(14) . . ?
C19 C18 C17 119.30(14) . . ?
F3 C19 C20 120.37(14) . . ?
F3 C19 C18 120.66(14) . . ?
C20 C19 C18 118.94(13) . . ?
F4 C20 C19 119.71(13) . . ?
F4 C20 C21 120.07(14) . . ?
C19 C20 C21 120.22(14) . . ?
F5 C21 C20 115.75(13) . . ?
F5 C21 C16 120.68(13) . . ?
C20 C21 C16 123.56(14) . . ?
C27 C22 C23 113.54(13) . . ?
C27 C22 B1 118.99(12) . . ?
C23 C22 B1 126.96(12) . . ?
F6 C23 C24 115.48(12) . . ?
F6 C23 C22 120.61(12) . . ?
C24 C23 C22 123.90(13) . . ?
F7 C24 C25 119.55(13) . . ?
F7 C24 C23 120.80(13) . . ?
C25 C24 C23 119.64(13) . . ?
F8 C25 C24 120.60(13) . . ?
F8 C25 C26 120.45(13) . . ?
C24 C25 C26 118.92(13) . . ?
F9 C26 C27 120.71(13) . . ?
F9 C26 C25 119.84(13) . . ?
C27 C26 C25 119.45(13) . . ?
F10 C27 C26 116.15(12) . . ?
F10 C27 C22 119.34(12) . . ?
C26 C27 C22 124.51(13) . . ?
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
B1 C1 1.615(2) . ?
B1 N1 1.6160(18) . ?
B1 C22 1.634(2) . ?
B1 C16 1.636(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.4093(19) . ?
C2 C3 1.392(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H2 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H3 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H4 0.9500 . ?
C6 C7 1.439(2) . ?
C7 N1 1.3003(18) . ?
C7 H5 0.9500 . ?
N1 C8 1.4272(18) . ?
C8 C9 1.3921(19) . ?
C8 C13 1.392(2) . ?
C9 C10 1.379(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.411(2) . ?
C10 H7 0.9500 . ?
C11 N2 1.3689(19) . ?
C11 C12 1.412(2) . ?
C12 C13 1.381(2) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
N2 C15 1.4525(19) . ?
N2 C14 1.4526(19) . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
C15 H13 0.9800 . ?
C15 H14 0.9800 . ?
C15 H15 0.9800 . ?
C16 C21 1.388(2) . ?
C16 C17 1.392(2) . ?
C17 F1 1.3484(16) . ?
C17 C18 1.382(2) . ?
C18 F2 1.3431(17) . ?
C18 C19 1.373(2) . ?
C19 F3 1.3399(17) . ?
C19 C20 1.370(2) . ?
C20 F4 1.3492(17) . ?
C20 C21 1.382(2) . ?
C21 F5 1.3496(17) . ?
C22 C27 1.389(2) . ?
C22 C23 1.389(2) . ?
C23 F6 1.3535(16) . ?
C23 C24 1.383(2) . ?
C24 F7 1.3406(16) . ?
C24 C25 1.375(2) . ?
C25 F8 1.3387(16) . ?
C25 C26 1.379(2) . ?
C26 F9 1.3434(17) . ?
C26 C27 1.373(2) . ?
C27 F10 1.3561(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
N1 B1 C1 C2 -179.81(14) . . . . ?
C22 B1 C1 C2 -63.78(19) . . . . ?
C16 B1 C1 C2 67.7(2) . . . . ?
N1 B1 C1 C6 -5.50(13) . . . . ?
C22 B1 C1 C6 110.53(12) . . . . ?
C16 B1 C1 C6 -117.97(13) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
B1 C1 C2 C3 174.45(14) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 178.73(13) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
B1 C1 C6 C5 -175.01(12) . . . . ?
C2 C1 C6 C7 -179.18(12) . . . . ?
B1 C1 C6 C7 5.46(15) . . . . ?
C5 C6 C7 N1 177.62(13) . . . . ?
C1 C6 C7 N1 -2.87(16) . . . . ?
C6 C7 N1 C8 171.56(11) . . . . ?
C6 C7 N1 B1 -1.12(16) . . . . ?
C1 B1 N1 C7 3.99(14) . . . . ?
C22 B1 N1 C7 -107.04(13) . . . . ?
C16 B1 N1 C7 124.70(12) . . . . ?
C1 B1 N1 C8 -168.57(11) . . . . ?
C22 B1 N1 C8 80.40(16) . . . . ?
C16 B1 N1 C8 -47.85(16) . . . . ?
C7 N1 C8 C9 -28.96(19) . . . . ?
B1 N1 C8 C9 142.67(13) . . . . ?
C7 N1 C8 C13 153.70(13) . . . . ?
B1 N1 C8 C13 -34.67(19) . . . . ?
C13 C8 C9 C10 -1.2(2) . . . . ?
N1 C8 C9 C10 -178.62(12) . . . . ?
C8 C9 C10 C11 1.8(2) . . . . ?
C9 C10 C11 N2 176.44(13) . . . . ?
C9 C10 C11 C12 -2.2(2) . . . . ?
N2 C11 C12 C13 -176.52(13) . . . . ?
C10 C11 C12 C13 2.1(2) . . . . ?
C11 C12 C13 C8 -1.7(2) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
N1 C8 C13 C12 178.57(12) . . . . ?
C10 C11 N2 C15 173.63(13) . . . . ?
C12 C11 N2 C15 -7.8(2) . . . . ?
C10 C11 N2 C14 2.2(2) . . . . ?
C12 C11 N2 C14 -179.19(13) . . . . ?
C1 B1 C16 C21 -140.36(14) . . . . ?
N1 B1 C16 C21 112.08(15) . . . . ?
C22 B1 C16 C21 -13.8(2) . . . . ?
C1 B1 C16 C17 42.27(18) . . . . ?
N1 B1 C16 C17 -65.29(16) . . . . ?
C22 B1 C16 C17 168.85(12) . . . . ?
C21 C16 C17 F1 -176.54(12) . . . . ?
B1 C16 C17 F1 1.2(2) . . . . ?
C21 C16 C17 C18 2.0(2) . . . . ?
B1 C16 C17 C18 179.72(13) . . . . ?
F1 C17 C18 F2 -0.3(2) . . . . ?
C16 C17 C18 F2 -178.92(13) . . . . ?
F1 C17 C18 C19 178.44(13) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
F2 C18 C19 F3 -0.3(2) . . . . ?
C17 C18 C19 F3 -179.06(13) . . . . ?
F2 C18 C19 C20 177.56(13) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
F3 C19 C20 F4 -0.4(2) . . . . ?
C18 C19 C20 F4 -178.31(13) . . . . ?
F3 C19 C20 C21 178.44(13) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
F4 C20 C21 F5 1.07(19) . . . . ?
C19 C20 C21 F5 -177.81(12) . . . . ?
F4 C20 C21 C16 -179.62(13) . . . . ?
C19 C20 C21 C16 1.5(2) . . . . ?
C17 C16 C21 F5 176.60(12) . . . . ?
B1 C16 C21 F5 -0.9(2) . . . . ?
C17 C16 C21 C20 -2.7(2) . . . . ?
B1 C16 C21 C20 179.83(13) . . . . ?
C1 B1 C22 C27 77.38(15) . . . . ?
N1 B1 C22 C27 -176.96(12) . . . . ?
C16 B1 C22 C27 -54.30(18) . . . . ?
C1 B1 C22 C23 -93.86(16) . . . . ?
N1 B1 C22 C23 11.8(2) . . . . ?
C16 B1 C22 C23 134.47(14) . . . . ?
C27 C22 C23 F6 -176.80(12) . . . . ?
B1 C22 C23 F6 -5.2(2) . . . . ?
C27 C22 C23 C24 2.0(2) . . . . ?
B1 C22 C23 C24 173.68(14) . . . . ?
F6 C23 C24 F7 -0.34(19) . . . . ?
C22 C23 C24 F7 -179.23(13) . . . . ?
F6 C23 C24 C25 178.58(12) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
F7 C24 C25 F8 -0.4(2) . . . . ?
C23 C24 C25 F8 -179.29(13) . . . . ?
F7 C24 C25 C26 177.58(13) . . . . ?
C23 C24 C25 C26 -1.4(2) . . . . ?
F8 C25 C26 F9 -0.1(2) . . . . ?
C24 C25 C26 F9 -178.03(13) . . . . ?
F8 C25 C26 C27 179.06(13) . . . . ?
C24 C25 C26 C27 1.1(2) . . . . ?
F9 C26 C27 F10 0.3(2) . . . . ?
C25 C26 C27 F10 -178.83(13) . . . . ?
F9 C26 C27 C22 179.96(14) . . . . ?
C25 C26 C27 C22 0.8(2) . . . . ?
C23 C22 C27 F10 177.33(12) . . . . ?
B1 C22 C27 F10 5.0(2) . . . . ?
C23 C22 C27 C26 -2.3(2) . . . . ?
B1 C22 C27 C26 -174.68(14) . . . . ?
