#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:12:08 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/93/7709317.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_7709317
loop_
_publ_author_name
'Laskova, Julia'
'Ananiev, Ivan'
'Kosenko, Irina'
'Serdyukov, Alexander'
'Stogniy, Marina'
'Sivaev, Igor'
'Grin, Mikhail'
'Semioshkin, Andrey'
'Bregadze, Vladimir I.'
_publ_section_title
;
 Nucleophilic addition reactions to nitrilium derivatives
 [B₁₂H₁₁NCCH₃]⁻ and
 [B₁₂H₁₁NCCH₂CH₃]⁻.
 Synthesis and structures of closo-dodecaborate-based iminols,
 amides and amidines.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3051
_journal_page_last               3059
_journal_paper_doi               10.1039/d1dt04174f
_journal_volume                  51
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_sum            'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_weight         727.50
_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
_audit_creation_date             2021-01-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-06-21 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                107.288(2)
_cell_angle_beta                 98.865(3)
_cell_angle_gamma                96.501(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2437(8)
_cell_length_b                   12.7062(10)
_cell_length_c                   13.7867(10)
_cell_measurement_reflns_used    6615
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.489
_cell_volume                     1505.8(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13774
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.915
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0905 before and 0.0697 after correction.
The Ratio of minimum to maximum transmission is 0.7570.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0425
_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)+(0.0407P)²+0.9211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5680
_reflns_number_total             6792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt04174f2.cif
_cod_data_source_block           a_sq
_cod_depositor_comments
'Adding full bibliography for 7709314--7709317.cif.'
_cod_database_code               7709317
_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   0.770
_shelx_estimated_absorpt_t_min   0.733
_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.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br 0.65775(4) 0.31820(3) -0.11485(2) 0.04239(10) Uani 1 1 d . . . . .
Br2 Br 0.75220(4) -0.10994(3) 0.36791(3) 0.04926(11) Uani 1 1 d . . . . .
F1 F 0.2128(2) 0.15748(13) 0.10722(12) 0.0344(4) Uani 1 1 d . . . . .
F2 F 0.25324(18) 0.12486(13) 0.30378(12) 0.0300(3) Uani 1 1 d . . . . .
F3 F 0.0833(2) 0.57611(15) 0.19965(14) 0.0416(4) Uani 1 1 d . . . . .
F4 F -0.08356(19) 0.43208(17) 0.20075(13) 0.0417(4) Uani 1 1 d . . . . .
F5 F 0.27230(17) 0.37199(13) 0.63786(11) 0.0281(3) Uani 1 1 d . . . . .
F6 F 0.48581(18) 0.49115(13) 0.66475(11) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.4278(2) 0.22313(14) 0.23963(13) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.3983(3) 0.29164(17) 0.08914(15) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.1548(2) 0.39282(19) 0.15600(16) 0.0260(5) Uani 1 1 d . . . . .
N3 N 0.2406(2) 0.34528(18) 0.22019(15) 0.0225(4) Uani 1 1 d . . . . .
N4 N 0.1482(2) 0.47995(18) 0.32742(16) 0.0218(4) Uani 1 1 d . . . . .
N5 N 0.3017(2) 0.45448(17) 0.50297(15) 0.0208(4) Uani 1 1 d . . . . .
N6 N 0.3868(2) 0.30305(17) 0.41594(15) 0.0211(4) Uani 1 1 d . . . . .
N7 N 0.4407(2) 0.31908(17) 0.52040(15) 0.0223(4) Uani 1 1 d . . . . .
N8 N 0.5127(2) 0.13680(17) 0.37034(16) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.6354(3) 0.2103(2) 0.0817(2) 0.0330(6) Uani 1 1 d . . . . .
H1A H 0.628656 0.207337 0.149646 0.049 Uiso 1 1 calc R U . . .
H1B H 0.731731 0.249062 0.083610 0.049 Uiso 1 1 calc R U . . .
H1C H 0.620866 0.135662 0.034159 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5168(3) 0.2717(2) 0.04636(19) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.5084(3) 0.3151(2) -0.0373(2) 0.0301(6) Uani 1 1 d . . . . .
C4 C 0.3819(3) 0.3601(2) -0.04821(19) 0.0295(6) Uani 1 1 d . . . . .
C5 C 0.3269(4) 0.4134(3) -0.1263(2) 0.0400(7) Uani 1 1 d . . . . .
H5A H 0.409852 0.452791 -0.142630 0.060 Uiso 1 1 calc R U . . .
H5B H 0.263953 0.465054 -0.098492 0.060 Uiso 1 1 calc R U . . .
H5C H 0.271580 0.356893 -0.188012 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3134(3) 0.3472(2) 0.03341(19) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.1952(3) 0.3912(2) 0.06739(19) 0.0275(5) Uani 1 1 d . . . . .
H7 H 0.138660 0.422635 0.025051 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2333(3) 0.4000(2) 0.31716(18) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.3089(3) 0.3834(2) 0.41110(17) 0.0194(5) Uani 1 1 d . . . . .
C10 C 0.1400(3) 0.5534(2) 0.42328(19) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.2208(3) 0.5423(2) 0.51321(19) 0.0215(5) Uani 1 1 d . . . . .
C12 C 0.2179(3) 0.6156(2) 0.6099(2) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.272080 0.608185 0.669542 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1336(3) 0.6997(2) 0.6167(2) 0.0335(6) Uani 1 1 d . . . . .
H13 H 0.131452 0.749557 0.681194 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0518(3) 0.7100(2) 0.5274(2) 0.0326(6) Uani 1 1 d . . . . .
H14 H -0.005661 0.766285 0.532990 0.039 Uiso 1 1 calc R U . . .
C15 C 0.0543(3) 0.6388(2) 0.4314(2) 0.0288(6) Uani 1 1 d . . . . .
H15 H -0.000188 0.646910 0.372210 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5315(3) 0.2548(2) 0.54616(19) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.570178 0.269602 0.616162 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5728(3) 0.1670(2) 0.47601(19) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.6670(3) 0.0913(2) 0.4933(2) 0.0284(6) Uani 1 1 d . . . . .
C19 C 0.6582(3) 0.0157(2) 0.3965(2) 0.0317(6) Uani 1 1 d . . . . .
C20 C 0.5625(3) 0.0437(2) 0.3215(2) 0.0281(5) Uani 1 1 d . . . . .
C21 C 0.5122(4) -0.0189(2) 0.2076(2) 0.0343(6) Uani 1 1 d . . . . .
H21A H 0.410157 -0.053606 0.194188 0.051 Uiso 1 1 calc R U . . .
H21B H 0.572420 -0.075252 0.187090 0.051 Uiso 1 1 calc R U . . .
H21C H 0.521853 0.032237 0.168970 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7554(4) 0.0947(3) 0.5950(2) 0.0395(7) Uani 1 1 d . . . . .
H22A H 0.740898 0.158400 0.648780 0.059 Uiso 1 1 calc R U . . .
H22B H 0.858826 0.100143 0.591642 0.059 Uiso 1 1 calc R U . . .
H22C H 0.723225 0.027616 0.609915 0.059 Uiso 1 1 calc R U . . .
B1 B 0.3912(3) 0.1920(2) 0.3234(2) 0.0222(5) Uani 1 1 d . . . . .
B2 B 0.3252(3) 0.2458(2) 0.1663(2) 0.0233(6) Uani 1 1 d . . . . .
B3 B 0.0633(3) 0.4755(3) 0.2178(2) 0.0288(6) Uani 1 1 d . . . . .
B4 B 0.3759(3) 0.4134(2) 0.5922(2) 0.0218(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 0.0033 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'
Br Br -0.2901 2.4595 '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
B2 O1 B1 124.0(2) . . ?
C2 N1 C6 107.7(2) . . ?
C2 N1 B2 133.4(2) . . ?
C6 N1 B2 117.3(2) . . ?
N3 N2 B3 111.75(19) . . ?
C7 N2 N3 117.4(2) . . ?
C7 N2 B3 127.0(2) . . ?
N2 N3 B2 118.23(19) . . ?
C8 N3 N2 107.0(2) . . ?
C8 N3 B2 134.8(2) . . ?
C8 N4 C10 122.7(2) . . ?
C8 N4 B3 110.0(2) . . ?
C10 N4 B3 127.2(2) . . ?
C9 N5 C11 122.8(2) . . ?
C9 N5 B4 109.9(2) . . ?
C11 N5 B4 126.8(2) . . ?
N7 N6 B1 124.09(19) . . ?
C9 N6 N7 107.49(19) . . ?
C9 N6 B1 127.19(19) . . ?
N6 N7 B4 111.72(19) . . ?
C16 N7 N6 119.5(2) . . ?
C16 N7 B4 128.7(2) . . ?
C17 N8 B1 124.2(2) . . ?
C20 N8 C17 108.1(2) . . ?
C20 N8 B1 127.0(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 124.8(2) . . ?
N1 C2 C3 108.0(2) . . ?
C3 C2 C1 127.3(3) . . ?
C2 C3 Br1 124.0(2) . . ?
C4 C3 Br1 125.6(2) . . ?
C4 C3 C2 110.3(3) . . ?
C3 C4 C5 128.8(3) . . ?
C3 C4 C6 104.6(2) . . ?
C6 C4 C5 126.6(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C4 109.4(2) . . ?
C7 C6 N1 121.0(2) . . ?
C7 C6 C4 129.1(2) . . ?
N2 C7 C6 125.2(2) . . ?
N2 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
N3 C8 N4 114.8(2) . . ?
N3 C8 C9 127.1(2) . . ?
N4 C8 C9 118.0(2) . . ?
N5 C9 C8 118.9(2) . . ?
N6 C9 N5 114.7(2) . . ?
N6 C9 C8 126.4(2) . . ?
N4 C10 C11 119.0(2) . . ?
N4 C10 C15 121.5(2) . . ?
C11 C10 C15 119.6(2) . . ?
N5 C11 C10 118.3(2) . . ?
C12 C11 N5 121.2(2) . . ?
C12 C11 C10 120.5(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.4 . . ?
C14 C15 C10 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
N7 C16 H16 117.9 . . ?
N7 C16 C17 124.1(2) . . ?
C17 C16 H16 117.9 . . ?
N8 C17 C18 109.4(2) . . ?
C16 C17 N8 120.7(2) . . ?
C16 C17 C18 129.7(2) . . ?
C17 C18 C22 126.8(3) . . ?
C19 C18 C17 104.5(2) . . ?
C19 C18 C22 128.7(3) . . ?
C18 C19 Br2 125.5(2) . . ?
C18 C19 C20 110.2(2) . . ?
C20 C19 Br2 124.3(2) . . ?
N8 C20 C19 107.7(2) . . ?
N8 C20 C21 123.5(2) . . ?
C19 C20 C21 128.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F2 B1 O1 115.5(2) . . ?
F2 B1 N6 105.8(2) . . ?
F2 B1 N8 109.5(2) . . ?
O1 B1 N6 108.7(2) . . ?
O1 B1 N8 112.2(2) . . ?
N8 B1 N6 104.31(18) . . ?
F1 B2 O1 116.0(2) . . ?
F1 B2 N1 107.01(19) . . ?
F1 B2 N3 105.2(2) . . ?
O1 B2 N1 113.2(2) . . ?
O1 B2 N3 111.4(2) . . ?
N1 B2 N3 102.94(19) . . ?
F3 B3 N2 111.1(2) . . ?
F3 B3 N4 113.4(2) . . ?
F4 B3 F3 111.5(2) . . ?
F4 B3 N2 113.2(3) . . ?
F4 B3 N4 111.8(2) . . ?
N2 B3 N4 94.78(19) . . ?
F5 B4 F6 111.1(2) . . ?
F5 B4 N5 111.4(2) . . ?
F5 B4 N7 112.1(2) . . ?
F6 B4 N5 114.4(2) . . ?
F6 B4 N7 111.7(2) . . ?
N7 B4 N5 95.25(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
Br1 C3 1.876(3) . ?
Br2 C19 1.873(3) . ?
F1 B2 1.391(3) . ?
F2 B1 1.392(3) . ?
F3 B3 1.372(4) . ?
F4 B3 1.363(4) . ?
F5 B4 1.364(3) . ?
F6 B4 1.371(3) . ?
O1 B1 1.402(3) . ?
O1 B2 1.395(3) . ?
N1 C2 1.336(4) . ?
N1 C6 1.403(3) . ?
N1 B2 1.559(3) . ?
N2 N3 1.410(3) . ?
N2 C7 1.327(3) . ?
N2 B3 1.560(4) . ?
N3 C8 1.327(3) . ?
N3 B2 1.614(4) . ?
N4 C8 1.342(3) . ?
N4 C10 1.392(3) . ?
N4 B3 1.574(3) . ?
N5 C9 1.335(3) . ?
N5 C11 1.397(3) . ?
N5 B4 1.568(3) . ?
N6 N7 1.395(3) . ?
N6 C9 1.326(3) . ?
N6 B1 1.607(3) . ?
N7 C16 1.317(3) . ?
N7 B4 1.553(3) . ?
N8 C17 1.396(3) . ?
N8 C20 1.345(3) . ?
N8 B1 1.548(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.518(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.490(4) . ?
C4 C6 1.414(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.366(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.458(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.402(4) . ?
C11 C12 1.387(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 C18 1.416(4) . ?
C18 C19 1.377(4) . ?
C18 C22 1.496(4) . ?
C19 C20 1.410(4) . ?
C20 C21 1.503(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
Br1 C3 C4 C5 4.8(4) . . . . ?
Br1 C3 C4 C6 -174.04(19) . . . . ?
Br2 C19 C20 N8 178.3(2) . . . . ?
Br2 C19 C20 C21 2.0(4) . . . . ?
N1 C2 C3 Br1 174.69(18) . . . . ?
N1 C2 C3 C4 -1.4(3) . . . . ?
N1 C6 C7 N2 4.3(4) . . . . ?
N2 N3 C8 N4 1.3(3) . . . . ?
N2 N3 C8 C9 -177.5(2) . . . . ?
N2 N3 B2 F1 -65.6(3) . . . . ?
N2 N3 B2 O1 168.0(2) . . . . ?
N2 N3 B2 N1 46.4(3) . . . . ?
N3 N2 C7 C6 0.0(4) . . . . ?
N3 N2 B3 F3 129.5(2) . . . . ?
N3 N2 B3 F4 -104.0(2) . . . . ?
N3 N2 B3 N4 12.2(3) . . . . ?
N3 C8 C9 N5 172.7(2) . . . . ?
N3 C8 C9 N6 -7.2(4) . . . . ?
N4 C8 C9 N5 -6.1(3) . . . . ?
N4 C8 C9 N6 173.9(2) . . . . ?
N4 C10 C11 N5 -2.6(3) . . . . ?
N4 C10 C11 C12 178.6(2) . . . . ?
N4 C10 C15 C14 -179.0(2) . . . . ?
N5 C11 C12 C13 -178.4(2) . . . . ?
N6 N7 C16 C17 -3.4(4) . . . . ?
N6 N7 B4 F5 106.4(2) . . . . ?
N6 N7 B4 F6 -128.2(2) . . . . ?
N6 N7 B4 N5 -9.3(2) . . . . ?
N7 N6 C9 N5 -0.6(3) . . . . ?
N7 N6 C9 C8 179.4(2) . . . . ?
N7 N6 B1 F2 95.1(3) . . . . ?
N7 N6 B1 O1 -140.2(2) . . . . ?
N7 N6 B1 N8 -20.4(3) . . . . ?
N7 C16 C17 N8 -3.3(4) . . . . ?
N7 C16 C17 C18 -179.1(3) . . . . ?
N8 C17 C18 C19 -1.1(3) . . . . ?
N8 C17 C18 C22 178.7(3) . . . . ?
C1 C2 C3 Br1 -6.8(4) . . . . ?
C1 C2 C3 C4 177.1(2) . . . . ?
C2 N1 C6 C4 1.1(3) . . . . ?
C2 N1 C6 C7 -171.5(2) . . . . ?
C2 N1 B2 F1 -94.7(3) . . . . ?
C2 N1 B2 O1 34.4(4) . . . . ?
C2 N1 B2 N3 154.8(2) . . . . ?
C2 C3 C4 C5 -179.2(3) . . . . ?
C2 C3 C4 C6 2.0(3) . . . . ?
C3 C4 C6 N1 -1.9(3) . . . . ?
C3 C4 C6 C7 169.9(3) . . . . ?
C4 C6 C7 N2 -166.6(3) . . . . ?
C5 C4 C6 N1 179.3(3) . . . . ?
C5 C4 C6 C7 -8.9(5) . . . . ?
C6 N1 C2 C1 -178.4(2) . . . . ?
C6 N1 C2 C3 0.2(3) . . . . ?
C6 N1 B2 F1 69.3(3) . . . . ?
C6 N1 B2 O1 -161.7(2) . . . . ?
C6 N1 B2 N3 -41.3(3) . . . . ?
C7 N2 N3 C8 150.0(2) . . . . ?
C7 N2 N3 B2 -28.4(3) . . . . ?
C7 N2 B3 F3 -27.6(4) . . . . ?
C7 N2 B3 F4 98.9(3) . . . . ?
C7 N2 B3 N4 -144.9(2) . . . . ?
C8 N3 B2 F1 116.6(3) . . . . ?
C8 N3 B2 O1 -9.8(4) . . . . ?
C8 N3 B2 N1 -131.5(3) . . . . ?
C8 N4 C10 C11 -1.6(4) . . . . ?
C8 N4 C10 C15 177.6(2) . . . . ?
C8 N4 B3 F3 -126.7(2) . . . . ?
C8 N4 B3 F4 106.2(3) . . . . ?
C8 N4 B3 N2 -11.2(3) . . . . ?
C9 N5 C11 C10 2.3(3) . . . . ?
C9 N5 C11 C12 -178.9(2) . . . . ?
C9 N5 B4 F5 -107.4(2) . . . . ?
C9 N5 B4 F6 125.4(2) . . . . ?
C9 N5 B4 N7 8.8(2) . . . . ?
C9 N6 N7 C16 -174.9(2) . . . . ?
C9 N6 N7 B4 7.0(3) . . . . ?
C9 N6 B1 F2 -70.6(3) . . . . ?
C9 N6 B1 O1 54.0(3) . . . . ?
C9 N6 B1 N8 173.8(2) . . . . ?
C10 N4 C8 N3 -173.1(2) . . . . ?
C10 N4 C8 C9 5.9(3) . . . . ?
C10 N4 B3 F3 53.6(4) . . . . ?
C10 N4 B3 F4 -73.5(3) . . . . ?
C10 N4 B3 N2 169.1(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 N5 C9 N6 -178.0(2) . . . . ?
C11 N5 C9 C8 2.1(3) . . . . ?
C11 N5 B4 F5 64.2(3) . . . . ?
C11 N5 B4 F6 -63.0(3) . . . . ?
C11 N5 B4 N7 -179.6(2) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C15 C10 C11 N5 178.1(2) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C16 N7 B4 F5 -71.5(3) . . . . ?
C16 N7 B4 F6 53.9(3) . . . . ?
C16 N7 B4 N5 172.8(2) . . . . ?
C16 C17 C18 C19 175.0(3) . . . . ?
C16 C17 C18 C22 -5.1(5) . . . . ?
C17 N8 C20 C19 -1.4(3) . . . . ?
C17 N8 C20 C21 175.2(3) . . . . ?
C17 N8 B1 F2 -99.3(3) . . . . ?
C17 N8 B1 O1 131.0(2) . . . . ?
C17 N8 B1 N6 13.6(3) . . . . ?
C17 C18 C19 Br2 -177.3(2) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 N8 0.7(3) . . . . ?
C18 C19 C20 C21 -175.6(3) . . . . ?
C20 N8 C17 C16 -174.9(3) . . . . ?
C20 N8 C17 C18 1.6(3) . . . . ?
C20 N8 B1 F2 70.3(3) . . . . ?
C20 N8 B1 O1 -59.4(3) . . . . ?
C20 N8 B1 N6 -176.9(2) . . . . ?
C22 C18 C19 Br2 2.9(5) . . . . ?
C22 C18 C19 C20 -179.6(3) . . . . ?
B1 O1 B2 F1 -62.3(3) . . . . ?
B1 O1 B2 N1 173.4(2) . . . . ?
B1 O1 B2 N3 57.9(3) . . . . ?
B1 N6 N7 C16 17.0(3) . . . . ?
B1 N6 N7 B4 -161.1(2) . . . . ?
B1 N6 C9 N5 167.1(2) . . . . ?
B1 N6 C9 C8 -12.9(4) . . . . ?
B1 N8 C17 C16 -3.7(4) . . . . ?
B1 N8 C17 C18 172.9(2) . . . . ?
B1 N8 C20 C19 -172.3(2) . . . . ?
B1 N8 C20 C21 4.2(4) . . . . ?
B2 O1 B1 F2 35.4(3) . . . . ?
B2 O1 B1 N6 -83.3(3) . . . . ?
B2 O1 B1 N8 161.9(2) . . . . ?
B2 N1 C2 C1 -13.3(4) . . . . ?
B2 N1 C2 C3 165.2(2) . . . . ?
B2 N1 C6 C4 -166.8(2) . . . . ?
B2 N1 C6 C7 20.7(3) . . . . ?
B2 N3 C8 N4 179.3(2) . . . . ?
B2 N3 C8 C9 0.5(4) . . . . ?
B3 N2 N3 C8 -9.5(3) . . . . ?
B3 N2 N3 B2 172.1(2) . . . . ?
B3 N2 C7 C6 156.0(3) . . . . ?
B3 N4 C8 N3 7.2(3) . . . . ?
B3 N4 C8 C9 -173.8(2) . . . . ?
B3 N4 C10 C11 178.0(2) . . . . ?
B3 N4 C10 C15 -2.7(4) . . . . ?
B4 N5 C9 N6 -6.0(3) . . . . ?
B4 N5 C9 C8 174.1(2) . . . . ?
B4 N5 C11 C10 -168.3(2) . . . . ?
B4 N5 C11 C12 10.5(4) . . . . ?
B4 N7 C16 C17 174.3(3) . . . . ?
