#------------------------------------------------------------------------------
#$Date: 2021-11-03 22:25:43 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270230 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519091.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_4519091
loop_
_publ_author_name
'Yoshida, Yasushi'
'Mino, Takashi'
'Sakamoto, Masami'
_publ_section_title
;
 Chiral Hypervalent Bromine(III) (Bromonium Salt): Hydrogen- and
 Halogen-Bonding Bifunctional Asymmetric Catalysis by Diaryl-λ3-bromanes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13028
_journal_page_last               13033
_journal_paper_doi               10.1021/acscatal.1c04070
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C32 H26 B Br Cl3 F4 N O'
_chemical_formula_weight         713.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 104.181(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7600(3)
_cell_length_b                   10.7865(3)
_cell_length_c                   13.7635(4)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.5460
_cell_measurement_theta_min      3.3120
_cell_volume                     1548.75(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25852
_diffrn_reflns_theta_full        66.694
_diffrn_reflns_theta_max         66.694
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    4.639
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details
;
Flack x determined using 2239 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.686
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.686
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0310
_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)+(0.1000P)²+0.5425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                5146
_reflns_number_total             5382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c04070_si_002.cif
_cod_data_source_block           I
_cod_database_code               4519091
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.54242(3) 0.55006(3) 0.37742(3) 0.03294(13) Uani d . . . 1 . .
Cl Cl5 0.91787(14) 0.96243(17) 0.12940(10) 0.0645(4) Uani d . . . 1 . .
Cl Cl7 0.82558(16) 0.74947(15) 0.21544(14) 0.0692(4) Uani d . . . 1 . .
Cl Cl6 0.65872(14) 0.95966(18) 0.15112(13) 0.0721(4) Uani d . . . 1 . .
F F3 0.7035(3) 0.9214(4) 0.5503(2) 0.0595(8) Uani d . . . 1 . .
F F4 0.7537(4) 0.9465(5) 0.4051(3) 0.0829(12) Uani d . . . 1 . .
O O1 -0.0681(3) 0.4512(4) 0.1310(2) 0.0489(8) Uani d . . . 1 . .
C C18 0.3085(4) 0.5057(4) 0.1828(3) 0.0278(8) Uani d . . . 1 . .
F F1 0.5559(4) 0.8851(5) 0.4052(3) 0.0772(11) Uani d . . . 1 . .
N N1 0.1206(3) 0.4731(3) 0.2471(2) 0.0317(7) Uani d . . . 1 . .
H H1 0.162 0.4568 0.3092 0.038 Uiso calc U . R 1 . .
C C8 0.3693(3) 0.3928(4) 0.2358(3) 0.0247(7) Uani d . . . 1 . .
C C3 0.1871(4) 0.1368(5) 0.0827(3) 0.0392(10) Uani d . . . 1 . .
H H3 0.1171 0.1258 0.026 0.047 Uiso calc U . R 1 . .
F F2 0.7172(5) 0.7527(4) 0.4565(4) 0.0956(16) Uani d . . . 1 . .
C C7 0.3276(4) 0.2712(4) 0.2003(3) 0.0267(8) Uani d . . . 1 . .
C C2 0.2236(4) 0.2536(4) 0.1149(3) 0.0307(8) Uani d . . . 1 . .
H H2 0.1798 0.3232 0.0805 0.037 Uiso calc U . R 1 . .
C C6 0.3917(4) 0.1650(4) 0.2499(3) 0.0297(8) Uani d . . . 1 . .
C C5 0.3510(4) 0.0452(5) 0.2130(3) 0.0371(8) Uani d . . . 1 . .
H H5 0.394 -0.0261 0.2453 0.045 Uiso calc U . R 1 . .
C C21 0.1853(4) 0.7072(4) 0.0706(3) 0.0362(9) Uani d . . . 1 . .
H H21 0.1423 0.7745 0.0319 0.043 Uiso calc U . R 1 . .
C C19 0.1861(3) 0.5403(5) 0.1862(2) 0.0295(7) Uani d . . . 1 . .
C C20 0.1246(4) 0.6419(4) 0.1291(3) 0.0326(8) Uani d . . . 1 . .
H H20 0.0401 0.6643 0.1318 0.039 Uiso calc U . R 1 . .
C C24 0.4986(4) 0.5406(5) 0.1123(3) 0.0349(8) Uani d . . . 1 . .
H H24 0.5404 0.4705 0.1475 0.042 Uiso calc U . R 1 . .
C C9 0.4709(4) 0.3961(3) 0.3180(3) 0.0263(7) Uani d . . . 1 . .
C C14 0.7448(4) 0.5017(5) 0.5585(3) 0.0416(10) Uani d . . . 1 . .
H H14 0.7532 0.5887 0.5685 0.05 Uiso calc U . R 1 . .
C C28 -0.0029(4) 0.4320(4) 0.2153(3) 0.0348(9) Uani d . . . 1 . .
C C4 0.2511(4) 0.0320(4) 0.1320(3) 0.0414(10) Uani d . . . 1 . .
H H4 0.2239 -0.0486 0.1081 0.05 Uiso calc U . R 1 . .
C C22 0.3122(4) 0.6771(4) 0.0660(3) 0.0347(9) Uani d . . . 1 . .
C C23 0.3743(4) 0.5739(3) 0.1215(3) 0.0291(9) Uani d . . . 1 . .
C C13 0.6580(4) 0.4507(4) 0.4790(3) 0.0331(8) Uani d . . . 1 . .
C C26 0.4987(6) 0.7126(5) 0.0013(4) 0.0500(12) Uani d . . . 1 . .
H H26 0.5422 0.76 -0.0383 0.06 Uiso calc U . R 1 . .
C C27 0.3781(5) 0.7470(5) 0.0069(3) 0.0454(11) Uani d . . . 1 . .
H H27 0.3386 0.8177 -0.0289 0.054 Uiso calc U . R 1 . .
C C10 0.5357(3) 0.2946(4) 0.3705(3) 0.0289(8) Uani d . . . 1 . .
C C29 -0.0524(4) 0.3579(5) 0.2938(3) 0.0429(10) Uani d . . . 1 . .
C C11 0.4958(4) 0.1787(4) 0.3351(3) 0.0318(8) Uani d . . . 1 . .
H H11 0.5381 0.1074 0.3679 0.038 Uiso calc U . R 1 . .
C C25 0.5590(5) 0.6085(5) 0.0531(4) 0.0457(11) Uani d . . . 1 . .
H H25 0.6419 0.5849 0.0473 0.055 Uiso calc U . R 1 . .
C C12 0.6377(4) 0.3256(4) 0.4591(3) 0.0330(8) Uani d . . . 1 . .
C C17 0.7177(4) 0.2449(5) 0.5249(4) 0.0406(10) Uani d . . . 1 . .
H H17 0.711 0.1581 0.5136 0.049 Uiso calc U . R 1 . .
C C15 0.8198(5) 0.4172(6) 0.6237(3) 0.0495(12) Uani d . . . 1 . .
H H15 0.881 0.4469 0.6809 0.059 Uiso calc U . R 1 . .
C C16 0.8072(5) 0.2916(5) 0.6072(4) 0.0491(12) Uani d . . . 1 . .
H H16 0.8604 0.236 0.6526 0.059 Uiso calc U . R 1 . .
C C31 -0.0448(6) 0.4412(6) 0.3861(4) 0.0575(14) Uani d . . . 1 . .
H H31A -0.0796 0.3965 0.4355 0.086 Uiso calc U . R 1 . .
H H31B -0.0947 0.5168 0.3656 0.086 Uiso calc U . R 1 . .
H H31C 0.0449 0.4631 0.4158 0.086 Uiso calc U . R 1 . .
C C30 0.0297(5) 0.2425(5) 0.3233(4) 0.0536(12) Uani d . . . 1 . .
H H30A -0.0049 0.1929 0.3703 0.08 Uiso calc U . R 1 . .
H H30B 0.1179 0.267 0.3553 0.08 Uiso calc U . R 1 . .
H H30C 0.0288 0.1932 0.2633 0.08 Uiso calc U . R 1 . .
B B1 0.6834(6) 0.8743(5) 0.4533(4) 0.0410(11) Uani d . . . 1 . .
C C101 0.8152(4) 0.9105(6) 0.2044(3) 0.0457(10) Uani d . . . 1 . .
H H101 0.8445 0.9479 0.2726 0.055 Uiso calc U . R 1 . .
C C32 -0.1909(6) 0.3185(9) 0.2490(6) 0.074(2) Uani d . . . 1 . .
H H32A -0.1949 0.2668 0.1897 0.112 Uiso calc U . R 1 . .
H H32B -0.2444 0.3923 0.2297 0.112 Uiso calc U . R 1 . .
H H32C -0.2224 0.271 0.2988 0.112 Uiso calc U . R 1 . .
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 Br1 C13 . . 87.07(17) ?
C19 C18 C23 . . 119.7(4) ?
C19 C18 C8 . . 120.9(4) ?
C23 C18 C8 . . 119.3(3) ?
C28 N1 C19 . . 124.1(3) ?
C28 N1 H1 . . 118.0 ?
C19 N1 H1 . . 118.0 ?
C9 C8 C7 . . 115.2(3) ?
C9 C8 C18 . . 123.4(3) ?
C7 C8 C18 . . 121.3(3) ?
C2 C3 C4 . . 121.2(4) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C6 C7 C2 . . 118.7(4) ?
C6 C7 C8 . . 119.9(3) ?
C2 C7 C8 . . 121.4(4) ?
C3 C2 C7 . . 119.9(4) ?
C3 C2 H2 . . 120.0 ?
C7 C2 H2 . . 120.0 ?
C11 C6 C5 . . 120.2(4) ?
C11 C6 C7 . . 120.4(4) ?
C5 C6 C7 . . 119.4(4) ?
C4 C5 C6 . . 120.2(5) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C20 C21 C22 . . 121.2(4) ?
C20 C21 H21 . . 119.4 ?
C22 C21 H21 . . 119.4 ?
C18 C19 C20 . . 120.7(4) ?
C18 C19 N1 . . 119.9(4) ?
C20 C19 N1 . . 119.4(3) ?
C21 C20 C19 . . 120.4(4) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C25 C24 C23 . . 120.8(5) ?
C25 C24 H24 . . 119.6 ?
C23 C24 H24 . . 119.6 ?
C8 C9 C10 . . 127.1(4) ?
C8 C9 Br1 . . 121.9(3) ?
C10 C9 Br1 . . 111.0(3) ?
C13 C14 C15 . . 115.3(5) ?
C13 C14 H14 . . 122.3 ?
C15 C14 H14 . . 122.3 ?
O1 C28 N1 . . 122.6(4) ?
O1 C28 C29 . . 122.6(4) ?
N1 C28 C29 . . 114.8(4) ?
C5 C4 C3 . . 120.6(4) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C21 C22 C27 . . 121.7(4) ?
C21 C22 C23 . . 119.1(4) ?
C27 C22 C23 . . 119.2(4) ?
C24 C23 C22 . . 118.7(4) ?
C24 C23 C18 . . 122.4(4) ?
C22 C23 C18 . . 119.0(4) ?
C14 C13 C12 . . 126.4(4) ?
C14 C13 Br1 . . 122.9(4) ?
C12 C13 Br1 . . 110.6(3) ?
C27 C26 C25 . . 121.0(4) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C22 . . 120.1(5) ?
C26 C27 H27 . . 120.0 ?
C22 C27 H27 . . 120.0 ?
C11 C10 C9 . . 117.1(3) ?
C11 C10 C12 . . 127.5(4) ?
C9 C10 C12 . . 115.4(4) ?
C30 C29 C32 . . 109.0(5) ?
C30 C29 C28 . . 109.5(4) ?
C32 C29 C28 . . 109.4(4) ?
C30 C29 C31 . . 110.3(4) ?
C32 C29 C31 . . 110.1(5) ?
C28 C29 C31 . . 108.5(4) ?
C10 C11 C6 . . 120.3(4) ?
C10 C11 H11 . . 119.9 ?
C6 C11 H11 . . 119.9 ?
C24 C25 C26 . . 120.2(5) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C13 C12 C17 . . 116.1(4) ?
C13 C12 C10 . . 115.9(4) ?
C17 C12 C10 . . 128.1(4) ?
C16 C17 C12 . . 119.9(5) ?
C16 C17 H17 . . 120.0 ?
C12 C17 H17 . . 120.0 ?
C16 C15 C14 . . 121.4(4) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
C15 C16 C17 . . 120.8(5) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C29 C31 H31A . . 109.5 ?
C29 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C29 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
F2 B1 F4 . . 113.0(5) ?
F2 B1 F1 . . 108.9(5) ?
F4 B1 F1 . . 108.9(5) ?
F2 B1 F3 . . 110.1(5) ?
F4 B1 F3 . . 106.5(5) ?
F1 B1 F3 . . 109.4(4) ?
Cl7 C101 Cl6 . . 111.9(3) ?
Cl7 C101 Cl5 . . 109.2(3) ?
Cl6 C101 Cl5 . . 109.5(3) ?
Cl7 C101 H101 . . 108.7 ?
Cl6 C101 H101 . . 108.7 ?
Cl5 C101 H101 . . 108.7 ?
C29 C32 H32A . . 109.5 ?
C29 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C29 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.927(4) ?
Br1 C13 . 1.949(4) ?
Cl5 C101 . 1.777(5) ?
Cl7 C101 . 1.745(6) ?
Cl6 C101 . 1.746(5) ?
F3 B1 . 1.394(6) ?
F4 B1 . 1.365(7) ?
O1 C28 . 1.217(5) ?
C18 C19 . 1.381(5) ?
C18 C23 . 1.431(6) ?
C18 C8 . 1.487(6) ?
F1 B1 . 1.375(7) ?
N1 C28 . 1.366(6) ?
N1 C19 . 1.419(5) ?
N1 H1 . 0.88 ?
C8 C9 . 1.367(5) ?
C8 C7 . 1.433(5) ?
C3 C2 . 1.361(6) ?
C3 C4 . 1.408(7) ?
C3 H3 . 0.95 ?
F2 B1 . 1.358(7) ?
C7 C6 . 1.422(6) ?
C7 C2 . 1.422(6) ?
C2 H2 . 0.95 ?
C6 C11 . 1.418(6) ?
C6 C5 . 1.418(7) ?
C5 C4 . 1.353(6) ?
C5 H5 . 0.95 ?
C21 C20 . 1.353(7) ?
C21 C22 . 1.419(7) ?
C21 H21 . 0.95 ?
C19 C20 . 1.415(6) ?
C20 H20 . 0.95 ?
C24 C25 . 1.371(7) ?
C24 C23 . 1.420(6) ?
C24 H24 . 0.95 ?
C9 C10 . 1.400(6) ?
C14 C13 . 1.368(6) ?
C14 C15 . 1.390(7) ?
C14 H14 . 0.95 ?
C28 C29 . 1.541(6) ?
C4 H4 . 0.95 ?
C22 C27 . 1.420(7) ?
C22 C23 . 1.422(6) ?
C13 C12 . 1.383(7) ?
C26 C27 . 1.369(8) ?
C26 C25 . 1.401(8) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C10 C11 . 1.372(6) ?
C10 C12 . 1.466(6) ?
C29 C30 . 1.522(8) ?
C29 C32 . 1.527(8) ?
C29 C31 . 1.542(8) ?
C11 H11 . 0.95 ?
C25 H25 . 0.95 ?
C12 C17 . 1.391(6) ?
C17 C16 . 1.389(7) ?
C17 H17 . 0.95 ?
C15 C16 . 1.375(9) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C101 H101 . 1.0 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 C18 C8 C9 . . . . -111.1(4) ?
C23 C18 C8 C9 . . . . 73.5(5) ?
C19 C18 C8 C7 . . . . 71.8(5) ?
C23 C18 C8 C7 . . . . -103.5(4) ?
C9 C8 C7 C6 . . . . -0.3(5) ?
C18 C8 C7 C6 . . . . 177.0(3) ?
C9 C8 C7 C2 . . . . -179.5(3) ?
C18 C8 C7 C2 . . . . -2.2(5) ?
C4 C3 C2 C7 . . . . -0.5(6) ?
C6 C7 C2 C3 . . . . 0.3(6) ?
C8 C7 C2 C3 . . . . 179.5(4) ?
C2 C7 C6 C11 . . . . 180.0(3) ?
C8 C7 C6 C11 . . . . 0.8(5) ?
C2 C7 C6 C5 . . . . 0.3(5) ?
C8 C7 C6 C5 . . . . -178.9(3) ?
C11 C6 C5 C4 . . . . 179.6(4) ?
C7 C6 C5 C4 . . . . -0.7(6) ?
C23 C18 C19 C20 . . . . 0.5(6) ?
C8 C18 C19 C20 . . . . -174.8(3) ?
C23 C18 C19 N1 . . . . -179.8(3) ?
C8 C18 C19 N1 . . . . 4.8(6) ?
C28 N1 C19 C18 . . . . -132.3(4) ?
C28 N1 C19 C20 . . . . 47.4(6) ?
C22 C21 C20 C19 . . . . -0.9(6) ?
C18 C19 C20 C21 . . . . -0.4(6) ?
N1 C19 C20 C21 . . . . 179.9(4) ?
C7 C8 C9 C10 . . . . -0.9(5) ?
C18 C8 C9 C10 . . . . -178.1(4) ?
C7 C8 C9 Br1 . . . . 179.7(2) ?
C18 C8 C9 Br1 . . . . 2.5(5) ?
C19 N1 C28 O1 . . . . -0.8(7) ?
C19 N1 C28 C29 . . . . 178.3(4) ?
C6 C5 C4 C3 . . . . 0.6(6) ?
C2 C3 C4 C5 . . . . 0.0(7) ?
C20 C21 C22 C27 . . . . -178.4(4) ?
C20 C21 C22 C23 . . . . 2.0(6) ?
C25 C24 C23 C22 . . . . 1.7(6) ?
C25 C24 C23 C18 . . . . -179.7(4) ?
C21 C22 C23 C24 . . . . 176.8(3) ?
C27 C22 C23 C24 . . . . -2.8(6) ?
C21 C22 C23 C18 . . . . -1.9(5) ?
C27 C22 C23 C18 . . . . 178.5(4) ?
C19 C18 C23 C24 . . . . -177.9(4) ?
C8 C18 C23 C24 . . . . -2.5(5) ?
C19 C18 C23 C22 . . . . 0.6(5) ?
C8 C18 C23 C22 . . . . 176.0(3) ?
C15 C14 C13 C12 . . . . 0.9(7) ?
C15 C14 C13 Br1 . . . . -179.9(3) ?
C25 C26 C27 C22 . . . . 0.2(8) ?
C21 C22 C27 C26 . . . . -177.6(4) ?
C23 C22 C27 C26 . . . . 1.9(7) ?
C8 C9 C10 C11 . . . . 1.6(6) ?
Br1 C9 C10 C11 . . . . -179.0(3) ?
C8 C9 C10 C12 . . . . -177.2(4) ?
Br1 C9 C10 C12 . . . . 2.2(4) ?
O1 C28 C29 C30 . . . . 118.1(5) ?
N1 C28 C29 C30 . . . . -60.9(5) ?
O1 C28 C29 C32 . . . . -1.3(7) ?
N1 C28 C29 C32 . . . . 179.7(5) ?
O1 C28 C29 C31 . . . . -121.5(5) ?
N1 C28 C29 C31 . . . . 59.5(5) ?
C9 C10 C11 C6 . . . . -1.0(6) ?
C12 C10 C11 C6 . . . . 177.6(4) ?
C5 C6 C11 C10 . . . . 179.6(4) ?
C7 C6 C11 C10 . . . . -0.1(6) ?
C23 C24 C25 C26 . . . . 0.4(7) ?
C27 C26 C25 C24 . . . . -1.4(8) ?
C14 C13 C12 C17 . . . . -2.8(7) ?
Br1 C13 C12 C17 . . . . 178.0(3) ?
C14 C13 C12 C10 . . . . 178.0(4) ?
Br1 C13 C12 C10 . . . . -1.2(4) ?
C11 C10 C12 C13 . . . . -179.3(4) ?
C9 C10 C12 C13 . . . . -0.7(5) ?
C11 C10 C12 C17 . . . . 1.5(7) ?
C9 C10 C12 C17 . . . . -179.8(4) ?
C13 C12 C17 C16 . . . . 2.8(6) ?
C10 C12 C17 C16 . . . . -178.1(4) ?
C13 C14 C15 C16 . . . . 0.8(7) ?
C14 C15 C16 C17 . . . . -0.7(8) ?
C12 C17 C16 C15 . . . . -1.2(8) ?
