#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:36:17 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038833.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_4038833
loop_
_publ_author_name
'Yang, Tianbao'
'Cao, Xin'
'Zhang, Xing-Xing'
'Ou, Yifeng'
'Au, Chak-Tong'
'Yin, Shuang-Feng'
'Qiu, Renhua'
_publ_section_title
;
 Iodine-Catalyzed Synthesis of N,N'-Chelate Organoboron
 Aminoquinolate.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12430
_journal_page_last               12443
_journal_paper_doi               10.1021/acs.joc.0c01649
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C23 H16 B F3 N2 O'
_chemical_formula_sum            'C23 H16 B F3 N2 O'
_chemical_formula_weight         404.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-22
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.707(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6380(9)
_cell_length_b                   16.4283(14)
_cell_length_c                   12.1516(13)
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      27.8300
_cell_measurement_theta_min      2.4780
_cell_volume                     1852.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     10.00  65.00   1.00    5.50    --  -11.59  19.00 -60.00   55
  2  ω    -89.00  59.00   1.00    5.50    --  -11.59   0.00 -90.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706125000
_diffrn_orient_matrix_UB_12      0.0157547000
_diffrn_orient_matrix_UB_13      -0.0222338000
_diffrn_orient_matrix_UB_21      -0.0243206000
_diffrn_orient_matrix_UB_22      -0.0240073000
_diffrn_orient_matrix_UB_23      0.0395270000
_diffrn_orient_matrix_UB_31      0.0161818000
_diffrn_orient_matrix_UB_32      0.0323043000
_diffrn_orient_matrix_UB_33      0.0402207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8292
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0656
_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)+(0.0973P)²+0.7374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2568
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01649_si_004.cif
_cod_data_source_block           ytb
_cod_depositor_comments
'Adding full bibliography for 4038833--4038834.cif.'
_cod_database_code               4038833
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C13(H13), C17(H17), C20(H20), C7(H7), C23(H23), C21(H21), C16(H16),
 C1(H1), C22(H22), C2(H2), C3(H3), C9(H9), C15(H15), C14(H14), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.573
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'
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
F3 F 0.01969(17) 0.31134(10) 0.76920(14) 0.0297(4) Uani 1 1 d . . . . .
F1 F 0.20789(16) 0.24250(9) 0.76310(14) 0.0294(4) Uani 1 1 d . . . . .
F2 F -0.00061(19) 0.20558(10) 0.66195(15) 0.0373(5) Uani 1 1 d . . . . .
O1 O -0.0027(2) 0.31333(13) 0.50865(18) 0.0360(6) Uani 1 1 d . . . . .
N2 N 0.1979(2) 0.38001(13) 0.61537(18) 0.0197(5) Uani 1 1 d . . . . .
N1 N 0.3911(2) 0.47713(12) 0.67234(19) 0.0188(5) Uani 1 1 d . . . . .
C6 C 0.1964(3) 0.43662(16) 0.5259(2) 0.0203(6) Uani 1 1 d . . . . .
C18 C 0.2852(3) 0.42772(15) 0.8368(2) 0.0191(6) Uani 1 1 d . . . . .
C19 C 0.2977(3) 0.37882(16) 0.9332(2) 0.0220(6) Uani 1 1 d . . . . .
H19 H 0.339808 0.327680 0.935862 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4614(3) 0.33129(15) 0.7452(2) 0.0195(6) Uani 1 1 d . . . . .
C5 C 0.3100(3) 0.49309(15) 0.5647(2) 0.0191(6) Uani 1 1 d . . . . .
C13 C 0.4674(3) 0.27271(15) 0.6633(2) 0.0210(6) Uani 1 1 d . . . . .
H13 H 0.389725 0.267454 0.598786 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5801(3) 0.33568(16) 0.8417(2) 0.0220(6) Uani 1 1 d . . . . .
H17 H 0.579439 0.373582 0.898448 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3364(3) 0.55887(16) 0.5000(2) 0.0215(6) Uani 1 1 d . . . . .
C11 C 0.0808(3) 0.27087(16) 0.6986(3) 0.0250(7) Uani 1 1 d . . . . .
C20 C 0.2491(3) 0.40437(17) 1.0248(2) 0.0268(7) Uani 1 1 d . . . . .
H20 H 0.257434 0.369967 1.087079 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1076(3) 0.44719(17) 0.4177(2) 0.0251(7) Uani 1 1 d . . . . .
H7 H 0.031871 0.411335 0.388467 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0911(3) 0.32380(16) 0.5975(2) 0.0231(6) Uani 1 1 d . . . . .
C23 C 0.2243(3) 0.50485(17) 0.8401(2) 0.0220(6) Uani 1 1 d . . . . .
H23 H 0.215405 0.539563 0.778063 0.026 Uiso 1 1 calc R U . . .
C21 C 0.1883(3) 0.48059(17) 1.0245(2) 0.0256(7) Uani 1 1 d . . . . .
H21 H 0.155261 0.497534 1.086004 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6994(3) 0.28471(16) 0.8551(2) 0.0249(7) Uani 1 1 d . . . . .
H16 H 0.776616 0.288704 0.920124 0.030 Uiso 1 1 calc R U . . .
C1 C 0.5024(3) 0.52465(16) 0.7206(2) 0.0221(6) Uani 1 1 d . . . . .
H1 H 0.557692 0.513731 0.794535 0.027 Uiso 1 1 calc R U . . .
C22 C 0.1770(3) 0.53146(17) 0.9316(2) 0.0258(7) Uani 1 1 d . . . . .
H22 H 0.137859 0.583259 0.930749 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5371(3) 0.59092(16) 0.6610(2) 0.0234(6) Uani 1 1 d . . . . .
H2 H 0.616538 0.623041 0.695073 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4553(3) 0.60897(16) 0.5533(2) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.477603 0.654006 0.514907 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2420(3) 0.56872(18) 0.3893(2) 0.0283(7) Uani 1 1 d . . . . .
H9 H 0.253774 0.611912 0.343168 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7025(3) 0.22820(16) 0.7713(2) 0.0251(7) Uani 1 1 d . . . . .
H15 H 0.782362 0.194669 0.779499 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5869(3) 0.22168(16) 0.6757(3) 0.0248(7) Uani 1 1 d . . . . .
H14 H 0.588379 0.183483 0.619496 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1328(3) 0.51360(18) 0.3511(2) 0.0287(7) Uani 1 1 d . . . . .
H8 H 0.072257 0.520049 0.277703 0.034 Uiso 1 1 calc R U . . .
B1 B 0.3343(3) 0.39814(17) 0.7261(3) 0.0194(7) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C6 N2 B1 110.4(2) . . ?
C10 N2 C6 118.1(2) . . ?
C10 N2 B1 131.5(2) . . ?
C5 N1 B1 112.1(2) . . ?
C1 N1 C5 119.9(2) . . ?
C1 N1 B1 128.0(2) . . ?
C5 C6 N2 109.0(2) . . ?
C7 C6 N2 133.4(2) . . ?
C7 C6 C5 117.5(3) . . ?
C19 C18 C23 116.0(2) . . ?
C19 C18 B1 123.1(2) . . ?
C23 C18 B1 120.9(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 H19 119.1 . . ?
C13 C12 C17 116.7(2) . . ?
C13 C12 B1 122.8(2) . . ?
C17 C12 B1 120.1(2) . . ?
N1 C5 C6 112.8(2) . . ?
N1 C5 C4 123.1(2) . . ?
C4 C5 C6 124.1(2) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.9(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C5 C4 C3 116.1(2) . . ?
C5 C4 C9 117.0(2) . . ?
C9 C4 C3 126.9(2) . . ?
F3 C11 F1 106.7(2) . . ?
F3 C11 C10 111.5(2) . . ?
F1 C11 C10 114.7(2) . . ?
F2 C11 F3 107.0(2) . . ?
F2 C11 F1 106.1(2) . . ?
F2 C11 C10 110.4(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
O1 C10 N2 126.0(3) . . ?
O1 C10 C11 115.9(2) . . ?
N2 C10 C11 118.0(2) . . ?
C18 C23 H23 118.7 . . ?
C22 C23 C18 122.7(3) . . ?
C22 C23 H23 118.7 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C9 H9 120.5 . . ?
C8 C9 C4 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 H8 118.3 . . ?
N1 B1 N2 95.66(19) . . ?
N1 B1 C18 107.6(2) . . ?
N1 B1 C12 106.1(2) . . ?
C18 B1 N2 112.9(2) . . ?
C12 B1 N2 113.9(2) . . ?
C12 B1 C18 117.8(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
F3 C11 1.341(3) . ?
F1 C11 1.346(3) . ?
F2 C11 1.333(3) . ?
O1 C10 1.218(3) . ?
N2 C6 1.428(3) . ?
N2 C10 1.355(3) . ?
N2 B1 1.634(4) . ?
N1 C5 1.355(3) . ?
N1 C1 1.328(3) . ?
N1 B1 1.614(4) . ?
C6 C5 1.415(4) . ?
C6 C7 1.372(4) . ?
C18 C19 1.398(4) . ?
C18 C23 1.401(4) . ?
C18 B1 1.617(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(4) . ?
C12 C13 1.397(4) . ?
C12 C17 1.401(4) . ?
C12 B1 1.615(4) . ?
C5 C4 1.400(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.396(4) . ?
C4 C3 1.417(4) . ?
C4 C9 1.415(4) . ?
C11 C10 1.531(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.418(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.397(4) . ?
C22 H22 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.370(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(4) . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?
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
F3 C11 C10 O1 -98.7(3) . . . . ?
F3 C11 C10 N2 78.3(3) . . . . ?
F1 C11 C10 O1 139.8(3) . . . . ?
F1 C11 C10 N2 -43.2(3) . . . . ?
F2 C11 C10 O1 20.1(3) . . . . ?
F2 C11 C10 N2 -162.9(2) . . . . ?
N2 C6 C5 N1 2.2(3) . . . . ?
N2 C6 C5 C4 -177.5(2) . . . . ?
N2 C6 C7 C8 176.8(3) . . . . ?
N1 C5 C4 C3 0.4(4) . . . . ?
N1 C5 C4 C9 -179.3(2) . . . . ?
N1 C1 C2 C3 1.4(4) . . . . ?
C6 N2 C10 O1 4.9(4) . . . . ?
C6 N2 C10 C11 -171.8(2) . . . . ?
C6 N2 B1 N1 2.6(2) . . . . ?
C6 N2 B1 C18 114.5(2) . . . . ?
C6 N2 B1 C12 -107.8(2) . . . . ?
C6 C5 C4 C3 -180.0(2) . . . . ?
C6 C5 C4 C9 0.3(4) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C18 C23 C22 C21 -0.5(4) . . . . ?
C19 C18 C23 C22 -0.9(4) . . . . ?
C19 C18 B1 N2 108.2(3) . . . . ?
C19 C18 B1 N1 -147.6(2) . . . . ?
C19 C18 B1 C12 -27.8(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C12 C17 C16 C15 0.3(4) . . . . ?
C5 N1 C1 C2 -0.3(4) . . . . ?
C5 N1 B1 N2 -1.4(3) . . . . ?
C5 N1 B1 C18 -117.6(2) . . . . ?
C5 N1 B1 C12 115.5(2) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C5 C4 C9 C8 -1.0(4) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
C13 C12 B1 N2 11.7(4) . . . . ?
C13 C12 B1 N1 -92.2(3) . . . . ?
C13 C12 B1 C18 147.2(2) . . . . ?
C17 C12 C13 C14 -1.1(4) . . . . ?
C17 C12 B1 N2 -175.2(2) . . . . ?
C17 C12 B1 N1 80.9(3) . . . . ?
C17 C12 B1 C18 -39.7(3) . . . . ?
C17 C16 C15 C14 -0.9(4) . . . . ?
C4 C9 C8 C7 1.0(4) . . . . ?
C20 C21 C22 C23 1.1(4) . . . . ?
C7 C6 C5 N1 -180.0(2) . . . . ?
C7 C6 C5 C4 0.4(4) . . . . ?
C10 N2 C6 C5 175.8(2) . . . . ?
C10 N2 C6 C7 -1.6(4) . . . . ?
C10 N2 B1 N1 -176.1(2) . . . . ?
C10 N2 B1 C18 -64.3(3) . . . . ?
C10 N2 B1 C12 73.5(4) . . . . ?
C23 C18 C19 C20 1.7(4) . . . . ?
C23 C18 B1 N2 -70.7(3) . . . . ?
C23 C18 B1 N1 33.6(3) . . . . ?
C23 C18 B1 C12 153.4(2) . . . . ?
C16 C15 C14 C13 0.5(4) . . . . ?
C1 N1 C5 C6 179.7(2) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C1 N1 B1 N2 178.6(2) . . . . ?
C1 N1 B1 C18 62.4(3) . . . . ?
C1 N1 B1 C12 -64.5(3) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C3 C4 C9 C8 179.3(3) . . . . ?
C9 C4 C3 C2 -179.6(3) . . . . ?
B1 N2 C6 C5 -3.1(3) . . . . ?
B1 N2 C6 C7 179.5(3) . . . . ?
B1 N2 C10 O1 -176.5(3) . . . . ?
B1 N2 C10 C11 6.8(4) . . . . ?
B1 N1 C5 C6 -0.3(3) . . . . ?
B1 N1 C5 C4 179.4(2) . . . . ?
B1 N1 C1 C2 179.7(2) . . . . ?
B1 C18 C19 C20 -177.2(2) . . . . ?
B1 C18 C23 C22 178.0(2) . . . . ?
B1 C12 C13 C14 172.2(2) . . . . ?
B1 C12 C17 C16 -172.8(2) . . . . ?
