#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:11:07 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/22/1572240.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_1572240
loop_
_publ_author_name
'Zhao, Zhengxing'
'Li, Yingxin'
'Jia, Shiqi'
'Peng, Lei'
'Zhang, Zian'
'Wu, Fengdi'
'Wang, Pengfei'
'Qin, Wenling'
'Lan, Yu'
'Yan, Hailong'
_publ_section_title
;
 Catalytic asymmetric functionalization and dearomatization of thiophenes.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              14295
_journal_page_last               14303
_journal_paper_doi               10.1039/d4sc03530e
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H13 Br O S'
_chemical_formula_sum            'C22 H13 Br O S'
_chemical_formula_weight         405.29
_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     dual
_audit_creation_date             2022-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.132(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0211(4)
_cell_length_b                   8.9321(3)
_cell_length_c                   11.4528(6)
_cell_measurement_reflns_used    6955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9720
_cell_measurement_theta_min      1.9200
_cell_volume                     848.64(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  87.00   1.00    3.29    --   18.89 178.00   0.00   40
  2  ω      5.00  31.00   1.00    3.29    --   18.89  77.00  60.00   26
  3  ω    -52.00  74.00   1.00    3.29    --   18.89   0.00  90.00  126
  4  ω    -27.00  -1.00   1.00    3.29    --  -18.78  19.00-150.00   26
  5  ω     39.00  64.00   1.00    3.29    --   18.58 178.00  30.00   25
  6  ω    -30.00  18.00   1.00    3.29    --   18.58 -57.00  60.00   48
  7  ω     15.00  62.00   1.00    3.29    --   18.58-109.00 178.00   47
  8  ω      8.00  54.00   1.00    3.29    --  -18.78   0.00 -90.00   46
  9  ω    -37.00  50.00   1.00    3.29    --  -18.78  57.00   0.00   87
 10  ω    -42.00  11.00   1.00    3.29    --  -18.78 -77.00 -60.00   53
 11  ω    -88.00   3.00   1.00    3.29    --  -18.78 -57.00  90.00   91
 12  ω    -88.00   3.00   1.00    3.29    --  -18.78 -57.00-150.00   91
 13  ω    -74.00 -42.00   1.00    3.29    --  -18.78 121.00  13.74   32
 14  ω    -81.00 -44.00   1.00    3.29    --  -18.78 132.00-156.47   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0307967000
_diffrn_orient_matrix_UB_12      0.0214887000
_diffrn_orient_matrix_UB_13      0.0457706000
_diffrn_orient_matrix_UB_21      0.0616022000
_diffrn_orient_matrix_UB_22      -0.0418567000
_diffrn_orient_matrix_UB_23      0.0469792000
_diffrn_orient_matrix_UB_31      0.0506574000
_diffrn_orient_matrix_UB_32      0.0639646000
_diffrn_orient_matrix_UB_33      0.0153448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.340
_diffrn_reflns_theta_min         1.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0347
_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)+(0.0419P)²+0.0955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                3564
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03530e2.cif
_cod_data_source_block           20220613-zzx-1290
_cod_depositor_comments
'Adding full bibliography for 1572238--1572242.cif.'
_cod_original_cell_volume        848.64(7)
_cod_database_code               1572240
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H13 Br O S'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C19(H19), C20(H20), C9(H9), C2(H2), C12(H12), C18(H18),
 C7(H7), C10(H10), C1(H1), C11(H11)
;
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.766
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.88946(5) 0.62366(5) 0.15419(4) 0.04533(14) Uani 1 1 d . . . . .
S1 S 0.37436(16) 0.37207(19) 0.41225(14) 0.0619(4) Uani 1 1 d . . . . .
O1 O 0.6924(3) 0.3769(4) 0.4794(2) 0.0416(7) Uani 1 1 d . . . . .
C17 C 0.6088(5) 0.7259(5) 0.1973(4) 0.0305(8) Uani 1 1 d . . . . .
C22 C 0.5002(5) 0.6757(4) 0.2483(4) 0.0291(9) Uani 1 1 d . . . . .
C8 C 0.9256(4) 0.1169(6) 0.3018(3) 0.0337(8) Uani 1 1 d . . . . .
C14 C 0.7534(4) 0.3333(4) 0.2949(3) 0.0274(8) Uani 1 1 d . . . . .
C21 C 0.3927(5) 0.7742(5) 0.2652(4) 0.0369(9) Uani 1 1 d . . . . .
H21 H 0.318556 0.741647 0.297680 0.044 Uiso 1 1 calc R U . . .
C5 C 0.7589(5) 0.2919(5) 0.4128(4) 0.0319(8) Uani 1 1 d . . . . .
C13 C 0.8293(4) 0.2398(4) 0.2338(4) 0.0270(8) Uani 1 1 d . . . . .
C16 C 0.7123(4) 0.5986(4) 0.2002(3) 0.0290(9) Uani 1 1 d . . . . .
C3 C 0.5245(5) 0.5095(5) 0.2764(4) 0.0286(8) Uani 1 1 d . . . . .
C4 C 0.5550(5) 0.4674(5) 0.4157(4) 0.0332(9) Uani 1 1 d . . . . .
H4 H 0.567409 0.560407 0.464017 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8501(5) 0.1683(5) 0.4780(4) 0.0429(11) Uani 1 1 d . . . . .
H6 H 0.852535 0.142830 0.557497 0.051 Uiso 1 1 calc R U . . .
C19 C 0.5036(6) 0.9721(5) 0.1812(5) 0.0433(11) Uani 1 1 d . . . . .
H19 H 0.503181 1.072291 0.159040 0.052 Uiso 1 1 calc R U . . .
C20 C 0.3978(5) 0.9225(5) 0.2329(4) 0.0410(10) Uani 1 1 d . . . . .
H20 H 0.328109 0.990669 0.246309 0.049 Uiso 1 1 calc R U . . .
C9 C 1.0031(5) 0.0264(5) 0.2433(4) 0.0385(10) Uani 1 1 d . . . . .
H9 H 1.069972 -0.050696 0.289155 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3805(5) 0.4194(5) 0.1916(4) 0.0372(9) Uani 1 1 d . . . . .
H2 H 0.351716 0.413330 0.104368 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8072(5) 0.2587(4) 0.1049(4) 0.0314(9) Uani 1 1 d . . . . .
H12 H 0.741554 0.335562 0.057376 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6108(5) 0.8731(5) 0.1620(4) 0.0365(9) Uani 1 1 d . . . . .
H18 H 0.681841 0.905253 0.126404 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9337(5) 0.0867(5) 0.4265(4) 0.0440(12) Uani 1 1 d . . . . .
H7 H 0.998295 0.008681 0.472966 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6738(5) 0.4754(4) 0.2486(4) 0.0279(8) Uani 1 1 d . . . . .
C10 C 0.9818(5) 0.0498(5) 0.1196(5) 0.0399(10) Uani 1 1 d . . . . .
H10 H 1.034028 -0.011020 0.081835 0.048 Uiso 1 1 calc R U . . .
C1 C 0.2996(5) 0.3510(5) 0.2473(5) 0.0479(11) Uani 1 1 d . . . . .
H1 H 0.208042 0.294702 0.202621 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8809(5) 0.1657(4) 0.0502(4) 0.0356(10) Uani 1 1 d . . . . .
H11 H 0.864079 0.179315 -0.034607 0.043 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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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
C1 S1 C4 92.0(2) . . ?
C5 O1 C4 121.0(3) . . ?
C22 C17 C16 106.7(3) . . ?
C18 C17 C22 121.4(4) . . ?
C18 C17 C16 131.8(4) . . ?
C17 C22 C3 109.6(3) . . ?
C21 C22 C17 120.1(4) . . ?
C21 C22 C3 130.2(4) . . ?
C9 C8 C13 119.6(4) . . ?
C9 C8 C7 122.1(4) . . ?
C7 C8 C13 118.3(4) . . ?
C5 C14 C13 118.9(3) . . ?
C5 C14 C15 114.4(3) . . ?
C13 C14 C15 126.6(3) . . ?
C22 C21 H21 120.8 . . ?
C22 C21 C20 118.3(4) . . ?
C20 C21 H21 120.8 . . ?
O1 C5 C14 122.7(3) . . ?
O1 C5 C6 115.6(4) . . ?
C14 C5 C6 121.3(4) . . ?
C14 C13 C8 119.3(4) . . ?
C12 C13 C8 117.8(3) . . ?
C12 C13 C14 122.8(3) . . ?
C17 C16 Br1 120.4(3) . . ?
C15 C16 Br1 127.0(3) . . ?
C15 C16 C17 112.4(3) . . ?
C22 C3 C4 114.0(3) . . ?
C22 C3 C15 102.5(3) . . ?
C2 C3 C22 111.6(3) . . ?
C2 C3 C4 106.9(3) . . ?
C2 C3 C15 111.3(3) . . ?
C15 C3 C4 110.5(3) . . ?
S1 C4 H4 108.1 . . ?
O1 C4 S1 109.7(3) . . ?
O1 C4 C3 115.6(3) . . ?
O1 C4 H4 108.1 . . ?
C3 C4 S1 107.1(3) . . ?
C3 C4 H4 108.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C20 C19 H19 119.8 . . ?
C20 C19 C18 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C21 C20 H20 119.2 . . ?
C19 C20 C21 121.7(4) . . ?
C19 C20 H20 119.2 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C3 C2 H2 121.9 . . ?
C1 C2 C3 116.3(4) . . ?
C1 C2 H2 121.9 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C17 C18 C19 118.1(4) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C14 C15 C3 116.6(3) . . ?
C16 C15 C14 134.3(4) . . ?
C16 C15 C3 108.4(3) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
S1 C1 H1 122.3 . . ?
C2 C1 S1 115.4(4) . . ?
C2 C1 H1 122.3 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
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
Br1 C16 1.882(4) . ?
S1 C4 1.826(4) . ?
S1 C1 1.749(5) . ?
O1 C5 1.370(5) . ?
O1 C4 1.418(5) . ?
C17 C22 1.397(6) . ?
C17 C16 1.464(5) . ?
C17 C18 1.377(6) . ?
C22 C21 1.379(6) . ?
C22 C3 1.517(6) . ?
C8 C13 1.427(6) . ?
C8 C9 1.400(6) . ?
C8 C7 1.426(6) . ?
C14 C5 1.382(5) . ?
C14 C13 1.426(5) . ?
C14 C15 1.452(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(6) . ?
C5 C6 1.404(6) . ?
C13 C12 1.419(6) . ?
C16 C15 1.338(5) . ?
C3 C4 1.554(5) . ?
C3 C2 1.513(6) . ?
C3 C15 1.531(5) . ?
C4 H4 0.9800 . ?
C6 H6 0.9300 . ?
C6 C7 1.341(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(7) . ?
C19 C18 1.391(6) . ?
C20 H20 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.369(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.295(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.362(5) . ?
C18 H18 0.9300 . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.402(6) . ?
C1 H1 0.9300 . ?
C11 H11 0.9300 . ?
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 C16 C15 C14 8.2(7) . . . . ?
Br1 C16 C15 C3 177.5(3) . . . . ?
O1 C5 C6 C7 -173.3(4) . . . . ?
C17 C22 C21 C20 -1.2(6) . . . . ?
C17 C22 C3 C4 125.5(4) . . . . ?
C17 C22 C3 C2 -113.2(4) . . . . ?
C17 C22 C3 C15 6.1(4) . . . . ?
C17 C16 C15 C14 -165.6(4) . . . . ?
C17 C16 C15 C3 3.7(5) . . . . ?
C22 C17 C16 Br1 -174.0(3) . . . . ?
C22 C17 C16 C15 0.3(5) . . . . ?
C22 C17 C18 C19 1.4(6) . . . . ?
C22 C21 C20 C19 1.9(7) . . . . ?
C22 C3 C4 S1 108.6(3) . . . . ?
C22 C3 C4 O1 -128.8(4) . . . . ?
C22 C3 C2 C1 -114.1(5) . . . . ?
C22 C3 C15 C14 165.6(3) . . . . ?
C22 C3 C15 C16 -5.8(4) . . . . ?
C8 C13 C12 C11 -2.5(6) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C14 C5 C6 C7 -0.4(7) . . . . ?
C14 C13 C12 C11 -179.3(4) . . . . ?
C21 C22 C3 C4 -54.7(6) . . . . ?
C21 C22 C3 C2 66.6(6) . . . . ?
C21 C22 C3 C15 -174.1(4) . . . . ?
C5 O1 C4 S1 99.9(4) . . . . ?
C5 O1 C4 C3 -21.3(5) . . . . ?
C5 C14 C13 C8 -7.8(5) . . . . ?
C5 C14 C13 C12 169.0(4) . . . . ?
C5 C14 C15 C16 130.2(5) . . . . ?
C5 C14 C15 C3 -38.5(5) . . . . ?
C5 C6 C7 C8 -3.6(7) . . . . ?
C13 C8 C9 C10 -3.1(7) . . . . ?
C13 C8 C7 C6 1.8(7) . . . . ?
C13 C14 C5 O1 178.5(4) . . . . ?
C13 C14 C5 C6 6.1(6) . . . . ?
C13 C14 C15 C16 -47.0(7) . . . . ?
C13 C14 C15 C3 144.3(4) . . . . ?
C13 C12 C11 C10 -0.6(6) . . . . ?
C16 C17 C22 C21 176.0(4) . . . . ?
C16 C17 C22 C3 -4.2(5) . . . . ?
C16 C17 C18 C19 -174.1(4) . . . . ?
C3 C22 C21 C20 179.0(4) . . . . ?
C3 C2 C1 S1 -1.3(6) . . . . ?
C4 S1 C1 C2 -7.4(4) . . . . ?
C4 O1 C5 C14 30.4(6) . . . . ?
C4 O1 C5 C6 -156.8(4) . . . . ?
C4 C3 C2 C1 11.3(5) . . . . ?
C4 C3 C15 C14 43.8(5) . . . . ?
C4 C3 C15 C16 -127.7(4) . . . . ?
C20 C19 C18 C17 -0.7(7) . . . . ?
C9 C8 C13 C14 -178.8(4) . . . . ?
C9 C8 C13 C12 4.3(6) . . . . ?
C9 C8 C7 C6 -175.5(5) . . . . ?
C9 C10 C11 C12 2.0(6) . . . . ?
C2 C3 C4 S1 -15.3(4) . . . . ?
C2 C3 C4 O1 107.3(4) . . . . ?
C2 C3 C15 C14 -74.9(4) . . . . ?
C2 C3 C15 C16 113.6(4) . . . . ?
C18 C17 C22 C21 -0.5(6) . . . . ?
C18 C17 C22 C3 179.3(4) . . . . ?
C18 C17 C16 Br1 1.9(6) . . . . ?
C18 C17 C16 C15 176.3(4) . . . . ?
C18 C19 C20 C21 -1.0(7) . . . . ?
C7 C8 C13 C14 4.0(6) . . . . ?
C7 C8 C13 C12 -173.0(4) . . . . ?
C7 C8 C9 C10 174.1(4) . . . . ?
C15 C14 C5 O1 1.0(5) . . . . ?
C15 C14 C5 C6 -171.4(4) . . . . ?
C15 C14 C13 C8 169.3(4) . . . . ?
C15 C14 C13 C12 -13.9(6) . . . . ?
C15 C3 C4 S1 -136.6(3) . . . . ?
C15 C3 C4 O1 -14.0(5) . . . . ?
C15 C3 C2 C1 132.0(4) . . . . ?
C1 S1 C4 O1 -113.2(3) . . . . ?
C1 S1 C4 C3 13.0(3) . . . . ?
