#------------------------------------------------------------------------------
#$Date: 2022-08-25 01:52:37 +0300 (Thu, 25 Aug 2022) $
#$Revision: 277395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/10/7711059.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_7711059
loop_
_publ_author_name
'Kundu, Gargi'
'Dixit, Ruchi'
'Tothadi, Srinu'
'Vanka, Kumar'
'Sen, Sakya Singha'
_publ_section_title
;
 Versatile chemistry of six-membered NHC with boranes: bromination at sp3
 borane, activation of B--H bond of HBpin, and ring expansion of NHC
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01707E
_journal_year                    2022
_chemical_formula_moiety         'C28 H42 B Br N2'
_chemical_formula_sum            'C28 H42 B Br N2'
_chemical_formula_weight         497.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-12 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.909(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3060(17)
_cell_length_b                   7.3776(6)
_cell_length_c                   20.0281(17)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.21
_cell_volume                     2729.3(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            60613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.286
_diffrn_reflns_theta_min         1.290
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1637 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.7059. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.488
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         8813
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+1.3013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6580
_reflns_number_total             8813
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01707e2.cif
_cod_data_source_block           gk_bh2br_0m_a
_cod_database_code               7711059
_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   0.888
_shelx_estimated_absorpt_t_min   0.730
_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. Restrained distances
 B1-H1E
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8), C11(H11), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C21(H21), C22(H22), C23(H23)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C),
 C20(H20A,H20B,H20C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br1A Br 0.58014(2) 0.81590(3) 0.39221(2) 0.02388(7) Uani 1 1 d . . . . .
N1 N 0.44750(7) 0.52140(19) 0.28119(7) 0.0118(3) Uani 1 1 d . . . . .
N2 N 0.55912(7) 0.40302(19) 0.28480(7) 0.0120(3) Uani 1 1 d . . . . .
C1 C 0.43737(11) 0.7436(4) 0.47335(10) 0.0317(5) Uani 1 1 d . . . . .
H1A H 0.465245 0.843901 0.461991 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.467195 0.679173 0.514493 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.394004 0.791493 0.483187 0.048 Uiso 1 1 calc GR . . . .
C2 C 0.41499(10) 0.6129(3) 0.41156(9) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.459561 0.550132 0.407671 0.024 Uiso 1 1 calc R . . . .
C3 C 0.38030(9) 0.7096(2) 0.34272(9) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.39772(9) 0.6691(2) 0.28079(9) 0.0131(3) Uani 1 1 d . . . . .
C5 C 0.51707(9) 0.5484(2) 0.28372(8) 0.0117(3) Uani 1 1 d . . . . .
C6 C 0.62742(9) 0.4150(2) 0.26799(9) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.69320(9) 0.4127(2) 0.32143(9) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.69816(9) 0.4101(3) 0.39855(9) 0.0180(3) Uani 1 1 d . . . . .
H8 H 0.648404 0.428023 0.403134 0.022 Uiso 1 1 calc R . . . .
C9 C 0.72712(11) 0.2273(3) 0.43194(11) 0.0270(4) Uani 1 1 d . . . . .
H9A H 0.694709 0.129850 0.408286 0.040 Uiso 1 1 calc GR . . . .
H9B H 0.729437 0.228953 0.481475 0.040 Uiso 1 1 calc GR . . . .
H9C H 0.775662 0.206510 0.427361 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.54441(12) 0.5831(3) 0.09549(11) 0.0319(5) Uani 1 1 d . . . . .
H10A H 0.548981 0.687938 0.126513 0.048 Uiso 1 1 calc GR . . . .
H10B H 0.496427 0.583734 0.061161 0.048 Uiso 1 1 calc GR . . . .
H10C H 0.581728 0.589366 0.071241 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.55396(10) 0.4082(3) 0.13859(9) 0.0225(4) Uani 1 1 d . . . . .
H11 H 0.513420 0.401572 0.160218 0.027 Uiso 1 1 calc R . . . .
C12 C 0.62454(10) 0.4116(2) 0.19735(9) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.68980(10) 0.4135(3) 0.18036(10) 0.0234(4) Uani 1 1 d . . . . .
H13 H 0.689102 0.413682 0.132741 0.028 Uiso 1 1 calc R . . . .
C14 C 0.75531(10) 0.4149(3) 0.23199(11) 0.0248(4) Uani 1 1 d . . . . .
H14 H 0.799308 0.417654 0.219778 0.030 Uiso 1 1 calc R . . . .
C15 C 0.75683(10) 0.4124(3) 0.30112(10) 0.0215(4) Uani 1 1 d . . . . .
H15 H 0.802275 0.410284 0.336052 0.026 Uiso 1 1 calc R . . . .
C16 C 0.74641(10) 0.5643(3) 0.43752(10) 0.0273(4) Uani 1 1 d . . . . .
H16A H 0.796330 0.544027 0.436719 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.744861 0.567552 0.485979 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.728904 0.679992 0.414777 0.041 Uiso 1 1 calc GR . . . .
C17 C 0.41528(9) 0.3388(2) 0.27271(9) 0.0163(3) Uani 1 1 d . . . . .
H17A H 0.400959 0.303980 0.222822 0.020 Uiso 1 1 calc R . . . .
H17B H 0.371394 0.338346 0.288780 0.020 Uiso 1 1 calc R . . . .
C18 C 0.46977(9) 0.2047(2) 0.31487(9) 0.0152(3) Uani 1 1 d . . . . .
H18A H 0.449295 0.080692 0.308170 0.018 Uiso 1 1 calc R . . . .
H18B H 0.482244 0.235040 0.365118 0.018 Uiso 1 1 calc R . . . .
C19 C 0.53662(9) 0.2143(2) 0.29013(9) 0.0163(3) Uani 1 1 d . . . . .
H19A H 0.576587 0.147373 0.323177 0.020 Uiso 1 1 calc R . . . .
H19B H 0.526527 0.155151 0.243912 0.020 Uiso 1 1 calc R . . . .
C20 C 0.36409(11) 0.4686(3) 0.42647(10) 0.0299(5) Uani 1 1 d . . . . .
H20A H 0.387978 0.407819 0.470679 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.352317 0.379280 0.388622 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.319493 0.526689 0.429617 0.045 Uiso 1 1 calc GR . . . .
C21 C 0.32798(9) 0.8431(3) 0.33976(10) 0.0198(4) Uani 1 1 d . . . . .
H21 H 0.315108 0.872501 0.380773 0.024 Uiso 1 1 calc R . . . .
C22 C 0.29462(9) 0.9329(3) 0.27806(10) 0.0212(4) Uani 1 1 d . . . . .
H22 H 0.259230 1.023237 0.276991 0.025 Uiso 1 1 calc R . . . .
C23 C 0.31292(9) 0.8911(3) 0.21797(9) 0.0195(4) Uani 1 1 d . . . . .
H23 H 0.289798 0.953905 0.176002 0.023 Uiso 1 1 calc R . . . .
C24 C 0.36442(9) 0.7590(3) 0.21746(9) 0.0150(3) Uani 1 1 d . . . . .
C25 C 0.38200(10) 0.7168(3) 0.14980(9) 0.0185(4) Uani 1 1 d . . . . .
H25 H 0.427230 0.642291 0.161740 0.022 Uiso 1 1 calc R . . . .
C26 C 0.32148(11) 0.6041(3) 0.10068(10) 0.0270(4) Uani 1 1 d . . . . .
H26A H 0.315542 0.490408 0.123699 0.041 Uiso 1 1 calc GR . . . .
H26B H 0.334186 0.577337 0.057767 0.041 Uiso 1 1 calc GR . . . .
H26C H 0.276063 0.672709 0.089189 0.041 Uiso 1 1 calc GR . . . .
C27 C 0.39623(11) 0.8894(3) 0.11303(10) 0.0254(4) Uani 1 1 d . . . . .
H27A H 0.352042 0.962822 0.099028 0.038 Uiso 1 1 calc GR . . . .
H27B H 0.410627 0.856253 0.071587 0.038 Uiso 1 1 calc GR . . . .
H27C H 0.435099 0.959413 0.145016 0.038 Uiso 1 1 calc GR . . . .
B1 B 0.54956(11) 0.7501(3) 0.28625(10) 0.0156(4) Uani 1 1 d D . . . .
C29 C 0.54901(13) 0.2403(4) 0.09226(11) 0.0333(5) Uani 1 1 d . . . . .
H29A H 0.500901 0.234874 0.058249 0.050 Uiso 1 1 calc GR . . . .
H29B H 0.557034 0.131071 0.121342 0.050 Uiso 1 1 calc GR . . . .
H29C H 0.585945 0.247762 0.067593 0.050 Uiso 1 1 calc GR . . . .
H1D H 0.5081(12) 0.850(3) 0.2611(11) 0.022(6) Uiso 1 1 d . . . . .
H1E H 0.5907(14) 0.783(4) 0.2563(14) 0.061(9) Uiso 1 1 d 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'
N N 0.0061 0.0033 '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
C4 N1 C17 115.43(13) . . ?
C5 N1 C4 122.81(14) . . ?
C5 N1 C17 121.58(14) . . ?
C5 N2 C6 122.19(14) . . ?
C5 N2 C19 124.57(13) . . ?
C6 N2 C19 112.37(13) . . ?
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 . . ?
C1 C2 H2 107.9 . . ?
C1 C2 C20 109.02(17) . . ?
C3 C2 C1 112.54(18) . . ?
C3 C2 H2 107.9 . . ?
C3 C2 C20 111.28(15) . . ?
C20 C2 H2 107.9 . . ?
C4 C3 C2 122.87(15) . . ?
C21 C3 C2 119.33(16) . . ?
C21 C3 C4 117.79(16) . . ?
C3 C4 N1 118.81(14) . . ?
C3 C4 C24 121.96(15) . . ?
C24 C4 N1 119.08(15) . . ?
N1 C5 B1 120.92(15) . . ?
N2 C5 N1 118.42(15) . . ?
N2 C5 B1 120.66(14) . . ?
C7 C6 N2 120.19(14) . . ?
C12 C6 N2 117.41(14) . . ?
C12 C6 C7 122.14(15) . . ?
C6 C7 C8 123.44(15) . . ?
C15 C7 C6 116.99(16) . . ?
C15 C7 C8 119.57(16) . . ?
C7 C8 H8 108.3 . . ?
C7 C8 C9 111.15(16) . . ?
C7 C8 C16 110.95(15) . . ?
C9 C8 H8 108.3 . . ?
C16 C8 H8 108.3 . . ?
C16 C8 C9 109.86(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
C10 C11 H11 107.7 . . ?
C10 C11 C29 111.27(16) . . ?
C12 C11 C10 110.84(17) . . ?
C12 C11 H11 107.7 . . ?
C12 C11 C29 111.48(16) . . ?
C29 C11 H11 107.7 . . ?
C6 C12 C11 123.10(15) . . ?
C13 C12 C6 118.18(16) . . ?
C13 C12 C11 118.71(16) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.80(17) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.98(16) . . ?
C15 C14 H14 120.0 . . ?
C7 C15 H15 119.1 . . ?
C14 C15 C7 121.86(17) . . ?
C14 C15 H15 119.1 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
N1 C17 C18 109.43(13) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18A 110.1 . . ?
C17 C18 H18B 110.1 . . ?
C17 C18 C19 107.94(14) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.1 . . ?
C19 C18 H18B 110.1 . . ?
N2 C19 C18 111.47(14) . . ?
N2 C19 H19A 109.3 . . ?
N2 C19 H19B 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21 119.4 . . ?
C22 C21 C3 121.15(17) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.92(17) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.68(16) . . ?
C24 C23 H23 119.2 . . ?
C4 C24 C25 122.92(16) . . ?
C23 C24 C4 117.50(16) . . ?
C23 C24 C25 119.58(15) . . ?
C24 C25 H25 107.8 . . ?
C24 C25 C26 110.87(15) . . ?
C24 C25 C27 112.00(16) . . ?
C26 C25 H25 107.8 . . ?
C26 C25 C27 110.53(15) . . ?
C27 C25 H25 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Br1A B1 H1D 105.3(11) . . ?
Br1A B1 H1E 116.6(15) . . ?
C5 B1 Br1A 103.85(11) . . ?
C5 B1 H1D 112.3(12) . . ?
C5 B1 H1E 119.9(16) . . ?
H1D B1 H1E 98.2(19) . . ?
C11 C29 H29A 109.5 . . ?
C11 C29 H29B 109.5 . . ?
C11 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
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
Br1A B1 2.0878(19) . ?
N1 C4 1.451(2) . ?
N1 C5 1.344(2) . ?
N1 C17 1.473(2) . ?
N2 C5 1.341(2) . ?
N2 C6 1.455(2) . ?
N2 C19 1.472(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.529(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.524(2) . ?
C2 C20 1.536(3) . ?
C3 C4 1.409(2) . ?
C3 C21 1.399(2) . ?
C4 C24 1.410(2) . ?
C5 B1 1.610(3) . ?
C6 C7 1.403(2) . ?
C6 C12 1.400(2) . ?
C7 C8 1.520(2) . ?
C7 C15 1.402(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.537(3) . ?
C8 C16 1.532(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.534(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.520(3) . ?
C11 C29 1.534(3) . ?
C12 C13 1.397(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.511(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.513(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(3) . ?
C24 C25 1.522(2) . ?
C25 H25 1.0000 . ?
C25 C26 1.535(3) . ?
C25 C27 1.536(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
B1 H1D 1.10(2) . ?
B1 H1E 1.151(17) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
N1 C4 C24 C23 175.36(15) . . . . ?
N1 C4 C24 C25 -4.2(2) . . . . ?
N1 C5 B1 Br1A 85.44(15) . . . . ?
N1 C17 C18 C19 -57.69(18) . . . . ?
N2 C5 B1 Br1A -93.88(15) . . . . ?
N2 C6 C7 C8 -4.0(3) . . . . ?
N2 C6 C7 C15 175.79(16) . . . . ?
N2 C6 C12 C11 4.0(3) . . . . ?
N2 C6 C12 C13 -176.72(16) . . . . ?
C1 C2 C3 C4 135.68(18) . . . . ?
C1 C2 C3 C21 -45.3(2) . . . . ?
C2 C3 C4 N1 3.9(2) . . . . ?
C2 C3 C4 C24 179.32(16) . . . . ?
C2 C3 C21 C22 -179.36(17) . . . . ?
C3 C4 C24 C23 0.0(3) . . . . ?
C3 C4 C24 C25 -179.61(16) . . . . ?
C3 C21 C22 C23 0.0(3) . . . . ?
C4 N1 C5 N2 179.14(14) . . . . ?
C4 N1 C5 B1 -0.2(2) . . . . ?
C4 N1 C17 C18 -145.79(14) . . . . ?
C4 C3 C21 C22 -0.3(3) . . . . ?
C4 C24 C25 C26 104.1(2) . . . . ?
C4 C24 C25 C27 -131.88(18) . . . . ?
C5 N1 C4 C3 -103.05(18) . . . . ?
C5 N1 C4 C24 81.41(19) . . . . ?
C5 N1 C17 C18 39.0(2) . . . . ?
C5 N2 C6 C7 102.89(19) . . . . ?
C5 N2 C6 C12 -82.9(2) . . . . ?
C5 N2 C19 C18 -16.4(2) . . . . ?
C6 N2 C5 N1 162.39(14) . . . . ?
C6 N2 C5 B1 -18.3(2) . . . . ?
C6 N2 C19 C18 174.12(14) . . . . ?
C6 C7 C8 C9 110.89(19) . . . . ?
C6 C7 C8 C16 -126.56(19) . . . . ?
C6 C7 C15 C14 0.3(3) . . . . ?
C6 C12 C13 C14 1.2(3) . . . . ?
C7 C6 C12 C11 178.08(17) . . . . ?
C7 C6 C12 C13 -2.6(3) . . . . ?
C8 C7 C15 C14 -179.91(18) . . . . ?
C10 C11 C12 C6 114.3(2) . . . . ?
C10 C11 C12 C13 -65.0(2) . . . . ?
C11 C12 C13 C14 -179.39(19) . . . . ?
C12 C6 C7 C8 -177.96(17) . . . . ?
C12 C6 C7 C15 1.8(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C7 -1.6(3) . . . . ?
C15 C7 C8 C9 -68.9(2) . . . . ?
C15 C7 C8 C16 53.7(2) . . . . ?
C17 N1 C4 C3 81.84(18) . . . . ?
C17 N1 C4 C24 -93.70(18) . . . . ?
C17 N1 C5 N2 -6.1(2) . . . . ?
C17 N1 C5 B1 174.61(14) . . . . ?
C17 C18 C19 N2 47.27(18) . . . . ?
C19 N2 C5 N1 -6.1(2) . . . . ?
C19 N2 C5 B1 173.25(15) . . . . ?
C19 N2 C6 C7 -87.35(19) . . . . ?
C19 N2 C6 C12 86.90(18) . . . . ?
C20 C2 C3 C4 -101.6(2) . . . . ?
C20 C2 C3 C21 77.4(2) . . . . ?
C21 C3 C4 N1 -175.13(15) . . . . ?
C21 C3 C4 C24 0.3(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C4 -0.2(3) . . . . ?
C22 C23 C24 C25 179.38(17) . . . . ?
C23 C24 C25 C26 -75.4(2) . . . . ?
C23 C24 C25 C27 48.5(2) . . . . ?
C29 C11 C12 C6 -121.1(2) . . . . ?
C29 C11 C12 C13 59.6(2) . . . . ?
