#------------------------------------------------------------------------------
#$Date: 2024-10-04 00:13:05 +0200 (Fri 04 de Oct de 2024) $
#$Revision: 295024 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/27/1572770.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_1572770
loop_
_publ_author_name
'Zhang, Chonghe'
'Gilliard, Robert J.'
'Cummins, Christopher'
_publ_section_title
;
 Arene extrusion as an approach to reductive elimination at boron:
 Implication of carbene-ligated haloborylene as a transient reactive
 intermediate
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC05524A
_journal_year                    2024
_chemical_formula_moiety         'Cl, 3(C H2 Cl2), C33 H42 B N2'
_chemical_formula_sum            'C36 H48 B Cl7 N2'
_chemical_formula_weight         767.72
_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             2023-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-26 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                108.946(3)
_cell_angle_beta                 93.723(2)
_cell_angle_gamma                95.092(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7206(8)
_cell_length_b                   12.0045(8)
_cell_length_c                   15.0853(10)
_cell_measurement_reflns_used    28584
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      61.557
_cell_measurement_theta_min      15.598
_cell_volume                     1989.7(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28466
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.070
_diffrn_reflns_theta_min         1.434
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.9142.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.023
_refine_diff_density_max         1.699
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         12481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0413P)²+1.4508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11008
_reflns_number_total             12481
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05524a3.cif
_cod_data_source_block           6
_cod_database_code               1572770
_shelx_shelxl_version_number     2016/6
_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   0.939
_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:
 C35(H35A,H35B), C34(H34A,H34B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C20(H20), C29(H29), C27(H27), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C31(H31A,H31B,H31C),
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C33(H33A,H33B,H33C), C24(H24A,H24B,
 H24C)
;
_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
Cl1 Cl 0.51728(3) 0.17021(3) -0.08149(2) 0.01752(6) Uani 1 1 d . . . . .
Cl7 Cl 0.18882(3) 0.90692(3) 0.92651(2) 0.02470(7) Uani 1 1 d . . . . .
Cl6 Cl 0.32687(3) 0.78034(3) 0.77978(3) 0.02739(8) Uani 1 1 d . . . . .
Cl5 Cl 0.51423(3) 0.23229(3) -0.33548(3) 0.03059(8) Uani 1 1 d . . . . .
Cl4 Cl 0.42736(4) -0.00973(4) -0.35423(5) 0.04763(13) Uani 1 1 d . . . . .
Cl2 Cl 0.18202(4) 0.10850(5) -0.20591(4) 0.04894(12) Uani 1 1 d . . . . .
Cl3 Cl 0.21374(6) 0.31990(6) -0.26116(5) 0.06589(18) Uani 1 1 d . . . . .
N2 N 0.30785(8) 0.26231(9) 0.14738(7) 0.01192(17) Uani 1 1 d . . . . .
N1 N 0.29476(8) 0.14875(9) 0.23253(7) 0.01201(17) Uani 1 1 d . . . . .
C5 C 0.08656(10) 0.31918(10) 0.35257(8) 0.01272(19) Uani 1 1 d . . . . .
C13 C 0.26353(10) 0.25241(10) 0.22559(8) 0.01147(19) Uani 1 1 d . . . . .
C1 C 0.06984(10) 0.40557(10) 0.29991(8) 0.0131(2) Uani 1 1 d . . . . .
C30 C 0.37504(10) 0.43895(11) 0.10863(8) 0.0140(2) Uani 1 1 d . . . . .
C26 C 0.17860(10) 0.33850(10) 0.05418(8) 0.0136(2) Uani 1 1 d . . . . .
C25 C 0.28651(10) 0.35081(10) 0.10447(8) 0.01237(19) Uani 1 1 d . . . . .
C2 C 0.16641(10) 0.48919(10) 0.31892(8) 0.0134(2) Uani 1 1 d . . . . .
C15 C 0.36621(10) 0.16634(11) 0.10587(8) 0.0142(2) Uani 1 1 d . . . . .
H15 H 0.404492 0.152879 0.050357 0.017 Uiso 1 1 calc R U . . .
C14 C 0.35837(10) 0.09530(11) 0.15944(8) 0.0145(2) Uani 1 1 d . . . . .
H14 H 0.390394 0.022657 0.148889 0.017 Uiso 1 1 calc R U . . .
C21 C 0.30692(10) 0.14815(10) 0.39566(8) 0.0143(2) Uani 1 1 d . . . . .
C17 C 0.18145(10) -0.00650(11) 0.27145(8) 0.0149(2) Uani 1 1 d . . . . .
C16 C 0.26054(10) 0.09653(10) 0.30207(8) 0.01263(19) Uani 1 1 d . . . . .
C22 C 0.40040(11) 0.25099(11) 0.42785(9) 0.0176(2) Uani 1 1 d . . . . .
H22A H 0.430745 0.264849 0.372835 0.026 Uiso 1 1 calc R U . . .
H22B H 0.462538 0.232983 0.465874 0.026 Uiso 1 1 calc R U . . .
H22C H 0.368826 0.322136 0.465806 0.026 Uiso 1 1 calc R U . . .
C8 C 0.37557(11) 0.52637(11) 0.39224(9) 0.0182(2) Uani 1 1 d . . . . .
H8A H 0.397592 0.516639 0.328822 0.027 Uiso 1 1 calc R U . . .
H8B H 0.429525 0.491001 0.424594 0.027 Uiso 1 1 calc R U . . .
H8C H 0.377639 0.610991 0.427798 0.027 Uiso 1 1 calc R U . . .
C6 C 0.00393(10) 0.20594(11) 0.32027(9) 0.0167(2) Uani 1 1 d . . . . .
H6A H -0.073968 0.224882 0.334226 0.025 Uiso 1 1 calc R U . . .
H6B H 0.027751 0.152573 0.353439 0.025 Uiso 1 1 calc R U . . .
H6C H 0.004601 0.167161 0.252283 0.025 Uiso 1 1 calc R U . . .
C7 C 0.25506(10) 0.46531(10) 0.38531(8) 0.0132(2) Uani 1 1 d . . . . .
C20 C 0.26651(11) 0.09771(12) 0.46097(9) 0.0183(2) Uani 1 1 d . . . . .
H20 H 0.294607 0.133203 0.525530 0.022 Uiso 1 1 calc R U . . .
C10 C 0.20778(11) 0.46159(11) 0.47552(8) 0.0149(2) Uani 1 1 d . . . . .
C9 C 0.11545(10) 0.38105(11) 0.45750(8) 0.0142(2) Uani 1 1 d . . . . .
C29 C 0.34978(11) 0.52352(11) 0.06678(9) 0.0164(2) Uani 1 1 d . . . . .
H29 H 0.407672 0.585759 0.070105 0.020 Uiso 1 1 calc R U . . .
C27 C 0.15787(10) 0.42446(11) 0.01334(8) 0.0157(2) Uani 1 1 d . . . . .
H27 H 0.084977 0.419139 -0.020144 0.019 Uiso 1 1 calc R U . . .
C28 C 0.24158(11) 0.51847(11) 0.02032(9) 0.0165(2) Uani 1 1 d . . . . .
C31 C 0.09200(11) 0.23161(11) 0.03905(9) 0.0170(2) Uani 1 1 d . . . . .
H31A H 0.121585 0.160541 -0.001221 0.026 Uiso 1 1 calc R U . . .
H31B H 0.019348 0.242402 0.008594 0.026 Uiso 1 1 calc R U . . .
H31C H 0.078844 0.222476 0.099938 0.026 Uiso 1 1 calc R U . . .
C18 C 0.14608(11) -0.05455(11) 0.33905(9) 0.0183(2) Uani 1 1 d . . . . .
H18 H 0.092989 -0.124521 0.319908 0.022 Uiso 1 1 calc R U . . .
C3 C -0.02970(11) 0.39536(12) 0.22905(9) 0.0177(2) Uani 1 1 d . . . . .
H3A H -0.064277 0.312585 0.202948 0.027 Uiso 1 1 calc R U . . .
H3B H -0.002564 0.421634 0.178182 0.027 Uiso 1 1 calc R U . . .
H3C H -0.087336 0.445188 0.259670 0.027 Uiso 1 1 calc R U . . .
C4 C 0.18396(12) 0.58347(11) 0.27419(9) 0.0189(2) Uani 1 1 d . . . . .
H4A H 0.133455 0.560996 0.215291 0.028 Uiso 1 1 calc R U . . .
H4B H 0.264377 0.592040 0.260849 0.028 Uiso 1 1 calc R U . . .
H4C H 0.165509 0.658959 0.317228 0.028 Uiso 1 1 calc R U . . .
C35 C 0.32942(12) 0.89554(13) 0.88928(10) 0.0219(2) Uani 1 1 d . . . . .
H35A H 0.360605 0.971728 0.883033 0.026 Uiso 1 1 calc R U . . .
H35B H 0.380702 0.879314 0.937314 0.026 Uiso 1 1 calc R U . . .
C32 C 0.49526(11) 0.44109(12) 0.15143(9) 0.0184(2) Uani 1 1 d . . . . .
H32A H 0.491731 0.411631 0.204761 0.028 Uiso 1 1 calc R U . . .
H32B H 0.533603 0.522555 0.173398 0.028 Uiso 1 1 calc R U . . .
H32C H 0.538694 0.390463 0.103990 0.028 Uiso 1 1 calc R U . . .
C23 C 0.13473(12) -0.06398(12) 0.16953(9) 0.0215(2) Uani 1 1 d . . . . .
H23A H 0.110351 -0.003261 0.144327 0.032 Uiso 1 1 calc R U . . .
H23B H 0.068666 -0.122453 0.164684 0.032 Uiso 1 1 calc R U . . .
H23C H 0.194807 -0.103580 0.133367 0.032 Uiso 1 1 calc R U . . .
C11 C 0.03981(12) 0.35409(12) 0.52612(9) 0.0196(2) Uani 1 1 d . . . . .
H11A H -0.039185 0.367960 0.511186 0.029 Uiso 1 1 calc R U . . .
H11B H 0.068159 0.405687 0.590157 0.029 Uiso 1 1 calc R U . . .
H11C H 0.041024 0.270999 0.521878 0.029 Uiso 1 1 calc R U . . .
C12 C 0.25821(12) 0.54926(13) 0.56882(9) 0.0226(3) Uani 1 1 d . . . . .
H12A H 0.339460 0.539347 0.579690 0.034 Uiso 1 1 calc R U . . .
H12B H 0.216186 0.535644 0.619135 0.034 Uiso 1 1 calc R U . . .
H12C H 0.251890 0.629980 0.568473 0.034 Uiso 1 1 calc R U . . .
C19 C 0.18643(11) -0.00285(12) 0.43414(9) 0.0196(2) Uani 1 1 d . . . . .
C33 C 0.21694(12) 0.61089(13) -0.02396(11) 0.0233(3) Uani 1 1 d . . . . .
H33A H 0.273410 0.681178 0.003674 0.035 Uiso 1 1 calc R U . . .
H33B H 0.139363 0.632867 -0.012345 0.035 Uiso 1 1 calc R U . . .
H33C H 0.222052 0.578684 -0.091975 0.035 Uiso 1 1 calc R U . . .
C34 C 0.54575(13) 0.09938(13) -0.31772(11) 0.0245(3) Uani 1 1 d . . . . .
H34A H 0.611176 0.069842 -0.353304 0.029 Uiso 1 1 calc R U . . .
H34B H 0.569092 0.115665 -0.250039 0.029 Uiso 1 1 calc R U . . .
C24 C 0.14635(15) -0.05684(16) 0.50595(11) 0.0314(3) Uani 1 1 d . . . . .
H24A H 0.189123 -0.123962 0.504115 0.047 Uiso 1 1 calc R U . . .
H24B H 0.063903 -0.084515 0.491370 0.047 Uiso 1 1 calc R U . . .
H24C H 0.160009 0.002920 0.568936 0.047 Uiso 1 1 calc R U . . .
B1 B 0.20214(11) 0.34131(11) 0.30396(9) 0.0122(2) Uani 1 1 d . . . . .
C36 C 0.27116(15) 0.24031(17) -0.19270(12) 0.0340(3) Uani 1 1 d . . . . .
H36A H 0.280636 0.290791 -0.125565 0.041 Uiso 1 1 calc R U . . .
H36B H 0.348189 0.220529 -0.211583 0.041 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
C13 N2 C25 125.96(10) . . ?
C13 N2 C15 110.60(10) . . ?
C15 N2 C25 122.99(10) . . ?
C13 N1 C14 110.39(10) . . ?
C13 N1 C16 125.45(10) . . ?
C14 N1 C16 124.03(10) . . ?
C1 C5 C6 116.09(10) . . ?
C1 C5 B1 69.82(8) . . ?
C6 C5 B1 125.09(10) . . ?
C9 C5 C1 112.43(10) . . ?
C9 C5 C6 117.99(10) . . ?
C9 C5 B1 106.17(9) . . ?
N2 C13 N1 105.21(10) . . ?
N2 C13 B1 131.53(10) . . ?
N1 C13 B1 122.85(10) . . ?
C5 C1 B1 57.92(7) . . ?
C2 C1 C5 110.21(10) . . ?
C2 C1 C3 124.20(11) . . ?
C2 C1 B1 67.56(8) . . ?
C3 C1 C5 125.25(10) . . ?
C3 C1 B1 137.77(10) . . ?
C25 C30 C29 117.41(11) . . ?
C25 C30 C32 122.26(11) . . ?
C29 C30 C32 120.25(11) . . ?
C25 C26 C31 121.11(11) . . ?
C27 C26 C25 117.32(11) . . ?
C27 C26 C31 121.42(11) . . ?
C30 C25 N2 119.55(10) . . ?
C30 C25 C26 122.88(11) . . ?
C26 C25 N2 117.40(10) . . ?
C1 C2 C7 110.04(10) . . ?
C1 C2 C4 125.17(11) . . ?
C1 C2 B1 66.97(8) . . ?
C7 C2 B1 58.12(7) . . ?
C4 C2 C7 124.63(11) . . ?
C4 C2 B1 139.65(10) . . ?
N2 C15 H15 126.5 . . ?
C14 C15 N2 106.92(10) . . ?
C14 C15 H15 126.5 . . ?
N1 C14 H14 126.6 . . ?
C15 C14 N1 106.88(10) . . ?
C15 C14 H14 126.6 . . ?
C16 C21 C22 123.09(11) . . ?
C16 C21 C20 117.51(11) . . ?
C20 C21 C22 119.36(11) . . ?
C16 C17 C23 122.07(11) . . ?
C18 C17 C16 117.59(11) . . ?
C18 C17 C23 120.34(11) . . ?
C21 C16 N1 119.82(10) . . ?
C21 C16 C17 122.44(11) . . ?
C17 C16 N1 117.74(10) . . ?
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 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 C8 116.10(10) . . ?
C2 C7 C10 112.57(10) . . ?
C2 C7 B1 70.19(8) . . ?
C8 C7 C10 117.96(10) . . ?
C8 C7 B1 124.83(10) . . ?
C10 C7 B1 106.11(9) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 C21 121.94(12) . . ?
C19 C20 H20 119.0 . . ?
C9 C10 C7 111.15(10) . . ?
C9 C10 C12 128.30(11) . . ?
C12 C10 C7 120.31(11) . . ?
C10 C9 C5 111.29(10) . . ?
C10 C9 C11 128.14(11) . . ?
C11 C9 C5 120.46(11) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 C30 121.54(11) . . ?
C28 C29 H29 119.2 . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.78(11) . . ?
C28 C27 H27 119.1 . . ?
C29 C28 C27 118.83(11) . . ?
C29 C28 C33 120.31(11) . . ?
C27 C28 C33 120.84(11) . . ?
C26 C31 H31A 109.5 . . ?
C26 C31 H31B 109.5 . . ?
C26 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.87(11) . . ?
C19 C18 H18 119.1 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Cl7 C35 H35A 109.5 . . ?
Cl7 C35 H35B 109.5 . . ?
Cl6 C35 Cl7 110.80(7) . . ?
Cl6 C35 H35A 109.5 . . ?
Cl6 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C19 C18 118.55(11) . . ?
C20 C19 C24 120.74(12) . . ?
C18 C19 C24 120.70(12) . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Cl5 C34 H34A 109.3 . . ?
Cl5 C34 H34B 109.3 . . ?
Cl4 C34 Cl5 111.70(8) . . ?
Cl4 C34 H34A 109.3 . . ?
Cl4 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 B1 C1 52.26(7) . . ?
C5 B1 C2 88.02(8) . . ?
C5 B1 C7 96.78(9) . . ?
C13 B1 C5 130.35(10) . . ?
C13 B1 C1 132.23(10) . . ?
C13 B1 C2 131.86(10) . . ?
C13 B1 C7 129.77(10) . . ?
C1 B1 C2 45.47(6) . . ?
C7 B1 C1 87.61(8) . . ?
C7 B1 C2 51.69(7) . . ?
Cl2 C36 H36A 109.2 . . ?
Cl2 C36 H36B 109.2 . . ?
Cl3 C36 Cl2 111.87(10) . . ?
Cl3 C36 H36A 109.2 . . ?
Cl3 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
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
Cl7 C35 1.7777(15) . ?
Cl6 C35 1.7734(14) . ?
Cl5 C34 1.7674(15) . ?
Cl4 C34 1.7476(16) . ?
Cl2 C36 1.763(2) . ?
Cl3 C36 1.7599(18) . ?
N2 C13 1.3549(14) . ?
N2 C25 1.4433(15) . ?
N2 C15 1.3836(15) . ?
N1 C13 1.3616(15) . ?
N1 C14 1.3840(15) . ?
N1 C16 1.4460(14) . ?
C5 C1 1.5151(16) . ?
C5 C6 1.5160(16) . ?
C5 C9 1.5147(16) . ?
C5 B1 1.6232(17) . ?
C13 B1 1.5753(17) . ?
C1 C2 1.3929(16) . ?
C1 C3 1.4989(17) . ?
C1 B1 1.7983(18) . ?
C30 C25 1.3977(16) . ?
C30 C29 1.4007(16) . ?
C30 C32 1.5059(17) . ?
C26 C25 1.4023(16) . ?
C26 C27 1.3933(16) . ?
C26 C31 1.5091(17) . ?
C2 C7 1.5063(16) . ?
C2 C4 1.5003(17) . ?
C2 B1 1.8061(17) . ?
C15 H15 0.9500 . ?
C15 C14 1.3535(16) . ?
C14 H14 0.9500 . ?
C21 C16 1.3947(16) . ?
C21 C22 1.5039(17) . ?
C21 C20 1.3995(17) . ?
C17 C16 1.4044(16) . ?
C17 C18 1.3925(17) . ?
C17 C23 1.5080(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C7 1.5135(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C10 1.5146(17) . ?
C7 B1 1.6302(17) . ?
C20 H20 0.9500 . ?
C20 C19 1.3907(18) . ?
C10 C9 1.3360(17) . ?
C10 C12 1.5025(17) . ?
C9 C11 1.4994(17) . ?
C29 H29 0.9500 . ?
C29 C28 1.3952(17) . ?
C27 H27 0.9500 . ?
C27 C28 1.4000(17) . ?
C28 C33 1.5077(17) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.3958(18) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C19 C24 1.5107(19) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
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
N2 C13 B1 C5 135.07(13) . . . . ?
N2 C13 B1 C1 63.35(19) . . . . ?
N2 C13 B1 C2 0.6(2) . . . . ?
N2 C13 B1 C7 -69.66(18) . . . . ?
N2 C15 C14 N1 0.33(13) . . . . ?
N1 C13 B1 C5 -53.40(17) . . . . ?
N1 C13 B1 C1 -125.13(13) . . . . ?
N1 C13 B1 C2 172.16(11) . . . . ?
N1 C13 B1 C7 101.87(14) . . . . ?
C5 C1 C2 C7 0.12(13) . . . . ?
C5 C1 C2 C4 175.66(11) . . . . ?
C5 C1 C2 B1 40.14(9) . . . . ?
C5 C1 B1 C13 113.77(14) . . . . ?
C5 C1 B1 C2 -134.43(10) . . . . ?
C5 C1 B1 C7 -100.47(9) . . . . ?
C13 N2 C25 C30 110.31(13) . . . . ?
C13 N2 C25 C26 -74.21(15) . . . . ?
C13 N2 C15 C14 -0.16(13) . . . . ?
C13 N1 C14 C15 -0.39(13) . . . . ?
C13 N1 C16 C21 -71.77(15) . . . . ?
C13 N1 C16 C17 108.86(13) . . . . ?
C1 C5 C9 C10 -55.43(13) . . . . ?
C1 C5 C9 C11 121.04(12) . . . . ?
C1 C5 B1 C13 -117.24(13) . . . . ?
C1 C5 B1 C2 30.62(7) . . . . ?
C1 C5 B1 C7 81.66(9) . . . . ?
C1 C2 C7 C8 164.14(10) . . . . ?
C1 C2 C7 C10 -55.58(13) . . . . ?
C1 C2 C7 B1 44.18(10) . . . . ?
C1 C2 B1 C5 -34.40(8) . . . . ?
C1 C2 B1 C13 112.61(13) . . . . ?
C1 C2 B1 C7 -134.65(10) . . . . ?
C30 C29 C28 C27 -1.88(19) . . . . ?
C30 C29 C28 C33 179.94(12) . . . . ?
C26 C27 C28 C29 2.19(18) . . . . ?
C26 C27 C28 C33 -179.63(12) . . . . ?
C25 N2 C13 N1 172.38(10) . . . . ?
C25 N2 C13 B1 -14.98(19) . . . . ?
C25 N2 C15 C14 -172.89(10) . . . . ?
C25 C30 C29 C28 -1.78(18) . . . . ?
C25 C26 C27 C28 1.17(18) . . . . ?
C2 C1 B1 C5 134.43(10) . . . . ?
C2 C1 B1 C13 -111.80(14) . . . . ?
C2 C1 B1 C7 33.97(8) . . . . ?
C2 C7 C10 C9 56.42(13) . . . . ?
C2 C7 C10 C12 -118.36(12) . . . . ?
C2 C7 B1 C5 -82.05(9) . . . . ?
C2 C7 B1 C13 116.68(13) . . . . ?
C2 C7 B1 C1 -30.50(7) . . . . ?
C15 N2 C13 N1 -0.08(12) . . . . ?
C15 N2 C13 B1 172.55(11) . . . . ?
C15 N2 C25 C30 -78.11(14) . . . . ?
C15 N2 C25 C26 97.38(13) . . . . ?
C14 N1 C13 N2 0.29(12) . . . . ?
C14 N1 C13 B1 -173.14(10) . . . . ?
C14 N1 C16 C21 112.69(13) . . . . ?
C14 N1 C16 C17 -66.69(15) . . . . ?
C21 C20 C19 C18 0.3(2) . . . . ?
C21 C20 C19 C24 178.66(14) . . . . ?
C17 C18 C19 C20 -1.7(2) . . . . ?
C17 C18 C19 C24 179.87(14) . . . . ?
C16 N1 C13 N2 -175.77(10) . . . . ?
C16 N1 C13 B1 10.79(17) . . . . ?
C16 N1 C14 C15 175.73(10) . . . . ?
C16 C21 C20 C19 2.44(19) . . . . ?
C16 C17 C18 C19 0.39(19) . . . . ?
C22 C21 C16 N1 -5.71(18) . . . . ?
C22 C21 C16 C17 173.63(11) . . . . ?
C22 C21 C20 C19 -175.16(12) . . . . ?
C8 C7 C10 C9 -164.11(11) . . . . ?
C8 C7 C10 C12 21.11(17) . . . . ?
C8 C7 B1 C5 169.34(11) . . . . ?
C8 C7 B1 C13 8.07(19) . . . . ?
C8 C7 B1 C1 -139.11(11) . . . . ?
C8 C7 B1 C2 -108.61(13) . . . . ?
C6 C5 C1 C2 -164.82(10) . . . . ?
C6 C5 C1 C3 8.71(16) . . . . ?
C6 C5 C1 B1 -120.13(11) . . . . ?
C6 C5 C9 C10 165.27(11) . . . . ?
C6 C5 C9 C11 -18.26(16) . . . . ?
C6 C5 B1 C13 -8.91(19) . . . . ?
C6 C5 B1 C1 108.33(13) . . . . ?
C6 C5 B1 C2 138.95(11) . . . . ?
C6 C5 B1 C7 -170.01(11) . . . . ?
C7 C2 B1 C5 100.24(9) . . . . ?
C7 C2 B1 C13 -112.75(14) . . . . ?
C7 C2 B1 C1 134.65(10) . . . . ?
C7 C10 C9 C5 -0.31(14) . . . . ?
C7 C10 C9 C11 -176.44(12) . . . . ?
C20 C21 C16 N1 176.79(11) . . . . ?
C20 C21 C16 C17 -3.87(18) . . . . ?
C10 C7 B1 C5 26.64(11) . . . . ?
C10 C7 B1 C13 -134.62(12) . . . . ?
C10 C7 B1 C1 78.19(9) . . . . ?
C10 C7 B1 C2 108.69(10) . . . . ?
C9 C5 C1 C2 55.06(13) . . . . ?
C9 C5 C1 C3 -131.41(12) . . . . ?
C9 C5 C1 B1 99.75(10) . . . . ?
C9 C5 B1 C13 134.30(12) . . . . ?
C9 C5 B1 C1 -108.46(10) . . . . ?
C9 C5 B1 C2 -77.84(9) . . . . ?
C9 C5 B1 C7 -26.80(11) . . . . ?
C29 C30 C25 N2 -179.38(10) . . . . ?
C29 C30 C25 C26 5.40(17) . . . . ?
C27 C26 C25 N2 179.58(10) . . . . ?
C27 C26 C25 C30 -5.10(17) . . . . ?
C31 C26 C25 N2 -4.79(16) . . . . ?
C31 C26 C25 C30 170.53(11) . . . . ?
C31 C26 C27 C28 -174.45(11) . . . . ?
C18 C17 C16 N1 -178.14(11) . . . . ?
C18 C17 C16 C21 2.50(18) . . . . ?
C3 C1 C2 C7 -173.49(11) . . . . ?
C3 C1 C2 C4 2.05(19) . . . . ?
C3 C1 C2 B1 -133.47(12) . . . . ?
C3 C1 B1 C5 -108.83(16) . . . . ?
C3 C1 B1 C13 4.9(2) . . . . ?
C3 C1 B1 C2 116.74(16) . . . . ?
C3 C1 B1 C7 150.70(14) . . . . ?
C4 C2 C7 C8 -11.42(17) . . . . ?
C4 C2 C7 C10 128.85(12) . . . . ?
C4 C2 C7 B1 -131.39(12) . . . . ?
C4 C2 B1 C5 -152.21(15) . . . . ?
C4 C2 B1 C13 -5.2(2) . . . . ?
C4 C2 B1 C1 -117.80(17) . . . . ?
C4 C2 B1 C7 107.55(17) . . . . ?
C32 C30 C25 N2 3.84(17) . . . . ?
C32 C30 C25 C26 -171.39(11) . . . . ?
C32 C30 C29 C28 175.08(12) . . . . ?
C23 C17 C16 N1 1.42(17) . . . . ?
C23 C17 C16 C21 -177.94(12) . . . . ?
C23 C17 C18 C19 -179.18(13) . . . . ?
C12 C10 C9 C5 173.95(12) . . . . ?
C12 C10 C9 C11 -2.2(2) . . . . ?
B1 C5 C1 C2 -44.69(10) . . . . ?
B1 C5 C1 C3 128.84(12) . . . . ?
B1 C5 C9 C10 18.97(13) . . . . ?
B1 C5 C9 C11 -164.55(11) . . . . ?
B1 C1 C2 C7 -40.02(9) . . . . ?
B1 C1 C2 C4 135.52(13) . . . . ?
B1 C2 C7 C8 119.96(12) . . . . ?
B1 C2 C7 C10 -99.77(10) . . . . ?
B1 C7 C10 C9 -18.39(13) . . . . ?
B1 C7 C10 C12 166.83(11) . . . . ?
