#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:02:38 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290125 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/06/1570694.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_1570694
loop_
_publ_author_name
'Chen, Zunsheng'
'Nie, Biao'
'Li, Xiaoning'
'Liu, Teng'
'Li, Chunsheng'
'Huang, Jiuzhong'
_publ_section_title
;
 Ligand-controlled regiodivergent Ni-catalyzed
 trans-hydroboration/carboboration of internal alkynes with
 B₂pin₂.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2236
_journal_page_last               2242
_journal_paper_doi               10.1039/d3sc04184k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H26 B N O2'
_chemical_formula_sum            'C23 H26 B N O2'
_chemical_formula_weight         359.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g18ph
_audit_creation_date             2022-10-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.101(4)
_cell_angle_beta                 103.862(4)
_cell_angle_gamma                102.475(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0732(3)
_cell_length_b                   12.8154(5)
_cell_length_c                   12.8838(5)
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.4160
_cell_measurement_theta_min      3.8450
_cell_volume                     1014.75(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     82.00 123.00   0.50    0.63    --   42.30  77.00 -30.00   82
  2  ω    -46.00  45.00   0.50    0.63    --   42.30 -77.00-180.00  182
  3  ω     86.00 127.00   0.50    0.63    --   42.30  77.00  30.00   82
  4  ω     91.00 117.00   0.50    0.63    --   42.30  77.00  90.00   52
  5  ω    -33.00  77.00   0.50    0.63    --   42.30 -82.00 -60.00  220
  6  ω     15.00 134.00   0.50    0.50    --  101.60 -64.00 -30.00  238
  7  ω     79.00 141.00   0.50    0.50    --  101.60 -77.00 120.00  124
  8  ω     34.00  98.00   0.50    0.50    --  101.60 -64.00 150.00  128
  9  ω    146.00 179.00   0.50    0.50    --  101.60  82.00   0.00   66
 10  ω     87.00 115.00   0.50    0.50    --  101.60  82.00   0.00   56
 11  ω     87.00 191.00   0.50    0.50    --  101.60  82.00 -90.00  208
 12  ω     87.00 126.00   0.50    0.50    --  101.60  82.00-120.00   78
 13  ω     99.00 126.00   0.50    0.50    --  101.60  50.00  60.00   54
 14  ω    150.00 183.00   0.50    0.50    --  101.60  50.00  60.00   66
 15  ω    105.00 131.00   0.50    0.50    --  101.60 -64.00 150.00   52
 16  ω    153.00 178.00   0.50    0.50    --  101.60 -25.00  90.00   50
 17  ω     38.00 124.00   0.50    0.50    --  101.60 -25.00  90.00  172
 18  ω     43.00  69.00   0.50    0.63    --   42.30  57.00-150.00   52
 19  ω     90.00 116.00   0.50    0.63    --   42.30  77.00-120.00   52
 20  ω     85.00 112.00   0.50    0.63    --   42.30  57.00-150.00   54
 21  ω    100.00 126.00   0.50    0.50    --  101.60 -50.00 150.00   52
 22  ω     42.00  68.00   0.50    0.50    --  101.60 -50.00 150.00   52
 23  ω    102.00 128.00   0.50    0.50    --  101.60 -12.00 -30.00   52
 24  ω     45.00  80.00   0.50    0.50    --  101.60 -12.00 -30.00   70
 25  ω    -20.00  71.00   0.50    0.50    --   42.30 -57.00  30.00  182
 26  ω     16.00  82.00   0.50    0.50    --   42.30 -82.00  30.00  132
 27  ω     50.00  76.00   0.50    0.50    --   42.30 -82.00-120.00   52
 28  ω     -4.00  27.00   0.50    0.50    --   42.30 -82.00-120.00   62
 29  ω     65.00 101.00   0.50    0.50    --  101.60 -82.00 120.00   72
 30  ω     14.00  40.00   0.50    0.50    --  101.60 -12.00  30.00   52
 31  ω     83.00 138.00   0.50    0.50    --  101.60 -82.00-180.00  110
 32  ω     82.00 108.00   0.50    0.50    --  101.60 -82.00   0.00   52
 33  ω     13.00  40.00   0.50    0.50    --  101.60 -82.00 120.00   54
 34  ω     64.00 110.00   0.50    0.50    --  101.60 -82.00-120.00   92
 35  ω     94.00 180.00   0.50    0.50    --  101.60 -12.00  30.00  172
 36  ω     73.00 109.00   0.50    0.50    --  101.60 -82.00  60.00   72
 37  ω     70.00 100.00   0.50    0.50    --  101.60  50.00 150.00   60
 38  ω    149.00 175.00   0.50    0.50    --  101.60  50.00 150.00   52
 39  ω     57.00 105.00   0.50    0.50    --  101.60 -50.00-150.00   96
 40  ω     64.00  90.00   0.50    0.50    --  101.60 -12.00  30.00   52
 41  ω     12.00 143.00   0.50    0.50    --  101.60 -82.00 -30.00  262
 42  ω    148.00 175.00   0.50    0.50    --  101.60  50.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495798000
_diffrn_orient_matrix_UB_12      -0.1044082000
_diffrn_orient_matrix_UB_13      0.0205444000
_diffrn_orient_matrix_UB_21      0.1031566000
_diffrn_orient_matrix_UB_22      0.0763793000
_diffrn_orient_matrix_UB_23      0.1314269000
_diffrn_orient_matrix_UB_31      -0.2073923000
_diffrn_orient_matrix_UB_32      -0.0362495000
_diffrn_orient_matrix_UB_33      0.0186915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10644
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.598
_diffrn_reflns_theta_min         3.854
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0838
_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)+(0.1384P)²+0.6023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3460
_reflns_number_total             3847
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04184k2.cif
_cod_data_source_block           99-1
_cod_depositor_comments
'Adding full bibliography for 1570693--1570697.cif.'
_cod_original_cell_volume        1014.75(8)
_cod_database_code               1570694
_shelx_shelxl_version_number     2017/1
_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   0.945
_shelx_estimated_absorpt_t_min   0.919
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;
_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 3.430
_oxdiff_exptl_absorpt_empirical_full_min 0.259
loop_
_space_group_symop_operation_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_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
O1 O 0.3731(2) 0.72155(15) 0.30405(15) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.6289(2) 0.65768(16) 0.37707(17) 0.0493(5) Uani 1 1 d . . . . .
N1 N 0.0086(4) 0.0116(2) 0.2362(2) 0.0678(7) Uani 1 1 d . . . . .
C1 C 0.1096(3) 0.40052(19) 0.23916(18) 0.0339(5) Uani 1 1 d . . . . .
C2 C 0.0956(3) 0.4406(2) 0.1501(2) 0.0418(5) Uani 1 1 d . . . . .
H2 H 0.116325 0.521124 0.168253 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0521(4) 0.3654(2) 0.0354(2) 0.0488(6) Uani 1 1 d . . . . .
H3 H 0.044060 0.394583 -0.023864 0.059 Uiso 1 1 calc R U . . .
C4 C 0.0205(4) 0.2478(2) 0.0079(2) 0.0490(6) Uani 1 1 d . . . . .
H4 H -0.007032 0.195992 -0.070100 0.059 Uiso 1 1 calc R U . . .
C5 C 0.0292(3) 0.2061(2) 0.0950(2) 0.0429(6) Uani 1 1 d . . . . .
H5 H 0.004878 0.125049 0.075515 0.051 Uiso 1 1 calc R U . . .
C6 C 0.0726(3) 0.2801(2) 0.21022(19) 0.0360(5) Uani 1 1 d . . . . .
C7 C 0.0870(3) 0.23585(19) 0.30654(19) 0.0397(5) Uani 1 1 d . . . . .
H7A H 0.227182 0.274929 0.364762 0.048 Uiso 1 1 calc R U . . .
H7B H -0.010773 0.258226 0.346173 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0431(4) 0.1095(2) 0.2665(2) 0.0486(6) Uani 1 1 d . . . . .
C9 C 0.1615(3) 0.48087(19) 0.36131(18) 0.0331(5) Uani 1 1 d . . . . .
H9 H 0.093637 0.452459 0.406663 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2944(3) 0.58994(18) 0.41547(17) 0.0316(5) Uani 1 1 d . . . . .
C11 C 0.3406(3) 0.65681(18) 0.54237(18) 0.0325(5) Uani 1 1 d . . . . .
C12 C 0.3502(3) 0.60222(19) 0.62047(19) 0.0344(5) Uani 1 1 d . . . . .
H12 H 0.319762 0.519981 0.591741 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4033(3) 0.6660(2) 0.73877(19) 0.0394(5) Uani 1 1 d . . . . .
H13 H 0.407551 0.626507 0.789753 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4506(3) 0.7868(2) 0.7850(2) 0.0416(5) Uani 1 1 d . . . . .
C15 C 0.4412(4) 0.8413(2) 0.7081(2) 0.0435(6) Uani 1 1 d . . . . .
H15 H 0.471751 0.923587 0.737431 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3878(3) 0.77821(19) 0.5888(2) 0.0385(5) Uani 1 1 d . . . . .
H16 H 0.383327 0.818037 0.538126 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5115(4) 0.8560(3) 0.9139(2) 0.0576(7) Uani 1 1 d . . . . .
H17A H 0.387929 0.860167 0.934674 0.086 Uiso 1 1 calc R U . . .
H17B H 0.600825 0.934909 0.934724 0.086 Uiso 1 1 calc R U . . .
H17C H 0.585292 0.817838 0.956516 0.086 Uiso 1 1 calc R U . . .
C18 C 0.5597(3) 0.7903(2) 0.2958(2) 0.0437(6) Uani 1 1 d . . . . .
C19 C 0.6376(5) 0.9092(3) 0.3967(3) 0.0654(8) Uani 1 1 d . . . . .
H19A H 0.529260 0.945728 0.393226 0.098 Uiso 1 1 calc R U . . .
H19B H 0.758381 0.958628 0.391257 0.098 Uiso 1 1 calc R U . . .
H19C H 0.675340 0.899895 0.470718 0.098 Uiso 1 1 calc R U . . .
C20 C 0.5041(4) 0.8065(3) 0.1842(3) 0.0641(9) Uani 1 1 d . . . . .
H20A H 0.445559 0.730148 0.118466 0.096 Uiso 1 1 calc R U . . .
H20B H 0.627504 0.852087 0.177432 0.096 Uiso 1 1 calc R U . . .
H20C H 0.402684 0.847890 0.183335 0.096 Uiso 1 1 calc R U . . .
C21 C 0.7059(4) 0.7188(2) 0.3103(3) 0.0502(6) Uani 1 1 d . . . . .
C22 C 0.9290(5) 0.7858(4) 0.3729(5) 0.0999(16) Uani 1 1 d . . . . .
H22A H 0.948340 0.838843 0.452101 0.150 Uiso 1 1 calc R U . . .
H22B H 0.978638 0.830930 0.330891 0.150 Uiso 1 1 calc R U . . .
H22C H 1.006356 0.731498 0.376937 0.150 Uiso 1 1 calc R U . . .
C23 C 0.6774(9) 0.6221(3) 0.1933(4) 0.1046(17) Uani 1 1 d . . . . .
H23A H 0.736996 0.563867 0.208099 0.157 Uiso 1 1 calc R U . . .
H23B H 0.746665 0.656132 0.149023 0.157 Uiso 1 1 calc R U . . .
H23C H 0.530457 0.584636 0.148332 0.157 Uiso 1 1 calc R U . . .
B1 B 0.4306(4) 0.6547(2) 0.3605(2) 0.0343(5) 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 0.0181 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'
O O 0.0492 0.0322 '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
B1 O1 C18 107.12(17) . . ?
B1 O2 C21 107.20(17) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C9 121.5(2) . . ?
C6 C1 C9 119.98(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 118.85(19) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 122.0(2) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C8 C7 179.4(3) . . ?
C1 C9 H9 116.5 . . ?
C10 C9 C1 127.03(19) . . ?
C10 C9 H9 116.5 . . ?
C9 C10 C11 120.20(18) . . ?
C9 C10 B1 126.00(19) . . ?
C11 C10 B1 113.51(17) . . ?
C12 C11 C10 121.58(19) . . ?
C12 C11 C16 117.4(2) . . ?
C16 C11 C10 120.88(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C17 121.3(2) . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C17 121.0(2) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C19 107.6(2) . . ?
O1 C18 C20 108.60(19) . . ?
O1 C18 C21 102.39(17) . . ?
C19 C18 C21 111.7(2) . . ?
C20 C18 C19 108.6(2) . . ?
C20 C18 C21 117.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C18 102.79(18) . . ?
O2 C21 C22 109.4(2) . . ?
O2 C21 C23 105.2(2) . . ?
C18 C21 C23 112.0(3) . . ?
C22 C21 C18 116.8(3) . . ?
C22 C21 C23 109.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 B1 C10 124.9(2) . . ?
O2 B1 O1 113.49(19) . . ?
O2 B1 C10 121.31(19) . . ?
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
O1 C18 1.467(3) . ?
O1 B1 1.358(3) . ?
O2 C21 1.460(3) . ?
O2 B1 1.357(3) . ?
N1 C8 1.134(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.412(3) . ?
C1 C9 1.473(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.464(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.343(3) . ?
C10 C11 1.490(3) . ?
C10 B1 1.576(3) . ?
C11 C12 1.398(3) . ?
C11 C16 1.400(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(3) . ?
C14 C15 1.383(4) . ?
C14 C17 1.503(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.521(4) . ?
C18 C20 1.492(3) . ?
C18 C21 1.540(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.493(4) . ?
C21 C23 1.541(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
O1 C18 C21 O2 -25.9(2) . . . . ?
O1 C18 C21 C22 -145.7(3) . . . . ?
O1 C18 C21 C23 86.5(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 C8 179.26(19) . . . . ?
C1 C9 C10 C11 -175.63(18) . . . . ?
C1 C9 C10 B1 -2.2(3) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
C2 C1 C6 C7 -179.85(19) . . . . ?
C2 C1 C9 C10 -36.8(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C5 C6 C7 C8 -2.4(3) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C1 C9 C10 143.2(2) . . . . ?
C9 C1 C2 C3 178.3(2) . . . . ?
C9 C1 C6 C5 -178.32(18) . . . . ?
C9 C1 C6 C7 0.1(3) . . . . ?
C9 C10 C11 C12 35.7(3) . . . . ?
C9 C10 C11 C16 -148.1(2) . . . . ?
C9 C10 B1 O1 90.6(3) . . . . ?
C9 C10 B1 O2 -96.6(3) . . . . ?
C10 C11 C12 C13 176.71(18) . . . . ?
C10 C11 C16 C15 -176.68(19) . . . . ?
C11 C10 B1 O1 -95.6(3) . . . . ?
C11 C10 B1 O2 77.2(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C17 -179.0(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C14 C15 C16 179.1(2) . . . . ?
C18 O1 B1 O2 -8.7(3) . . . . ?
C18 O1 B1 C10 164.6(2) . . . . ?
C19 C18 C21 O2 88.9(2) . . . . ?
C19 C18 C21 C22 -30.9(3) . . . . ?
C19 C18 C21 C23 -158.7(2) . . . . ?
C20 C18 C21 O2 -144.7(2) . . . . ?
C20 C18 C21 C22 95.5(3) . . . . ?
C20 C18 C21 C23 -32.3(3) . . . . ?
C21 O2 B1 O1 -9.2(3) . . . . ?
C21 O2 B1 C10 177.3(2) . . . . ?
B1 O1 C18 C19 -96.3(2) . . . . ?
B1 O1 C18 C20 146.4(2) . . . . ?
B1 O1 C18 C21 21.5(3) . . . . ?
B1 O2 C21 C18 21.9(3) . . . . ?
B1 O2 C21 C22 146.6(3) . . . . ?
B1 O2 C21 C23 -95.5(3) . . . . ?
B1 C10 C11 C12 -138.5(2) . . . . ?
B1 C10 C11 C16 37.7(3) . . . . ?
