#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:14:58 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294429 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133420.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_7133420
loop_
_publ_author_name
'Li, Kai'
'Zhao, Zhengxing'
'Qin, Wenling'
'Liu, Yidong'
'Yan, Hailong'
_publ_section_title
;
 Catalytic asymmetric construction of bridged bicyclo[m.3.1] rings
 using an intramolecular Diels-Alder reaction.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9570
_journal_page_last               9573
_journal_paper_doi               10.1039/d4cc02850c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 Br O'
_chemical_formula_sum            'C22 H17 Br O'
_chemical_formula_weight         377.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6693(2)
_cell_length_b                   13.0042(5)
_cell_length_c                   17.0867(8)
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4730
_cell_measurement_theta_min      3.8920
_cell_volume                     1704.11(11)
_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 0.996
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  25.00   1.00    6.70    --   18.74  77.00-150.00   36
  2  ω    -50.00  12.00   1.00    6.70    --   18.74 -57.00 -60.00   62
  3  ω     -2.00  91.00   1.00    6.70    --   18.74  38.00 -60.00   93
;
_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      -0.0770358000
_diffrn_orient_matrix_UB_12      -0.0020302000
_diffrn_orient_matrix_UB_13      0.0229426000
_diffrn_orient_matrix_UB_21      0.0511518000
_diffrn_orient_matrix_UB_22      -0.0064591000
_diffrn_orient_matrix_UB_23      0.0342314000
_diffrn_orient_matrix_UB_31      0.0031716000
_diffrn_orient_matrix_UB_32      0.0541095000
_diffrn_orient_matrix_UB_33      0.0049384000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6671
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.983
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82436
_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    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(7)
_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     217
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0458
_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)+(0.0267P)²+0.2819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                2775
_reflns_number_total             3886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20220111-lk-zzx-483
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133420
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br'
_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, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C3(H3), C17(H17), C15(H15), C4(H4), C18(H18), C16(H16),
 C1(H1), C2(H2)
;
_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.779
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.71057(6) 0.49154(4) 0.56831(3) 0.0606(2) Uani 1 1 d . . . . .
O1 O 0.3927(5) 0.7881(2) 0.6484(2) 0.0552(10) Uani 1 1 d . . . . .
C14 C 0.7235(6) 0.6305(3) 0.7492(3) 0.0395(11) Uani 1 1 d . . . . .
C8 C 0.4530(6) 0.5865(3) 0.6628(3) 0.0357(11) Uani 1 1 d . . . . .
C22 C 0.5367(7) 0.7591(4) 0.6905(3) 0.0445(12) Uani 1 1 d . . . . .
C7 C 0.4789(6) 0.5208(3) 0.6045(3) 0.0399(11) Uani 1 1 d . . . . .
C13 C 0.5801(6) 0.6569(3) 0.7000(3) 0.0393(11) Uani 1 1 d . . . . .
C19 C 0.8277(7) 0.7102(3) 0.7812(3) 0.0427(12) Uani 1 1 d . . . . .
C21 C 0.6449(8) 0.8376(4) 0.7194(3) 0.0513(14) Uani 1 1 d . . . . .
H21 H 0.618705 0.906023 0.708792 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2725(6) 0.6177(3) 0.6873(3) 0.0469(12) Uani 1 1 d . . . . .
H9A H 0.264241 0.619265 0.743900 0.056 Uiso 1 1 calc R U . . .
H9B H 0.187798 0.568681 0.667586 0.056 Uiso 1 1 calc R U . . .
C20 C 0.7875(8) 0.8137(3) 0.7627(3) 0.0518(13) Uani 1 1 d . . . . .
H20 H 0.859880 0.866050 0.780578 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0732(7) 0.3945(4) 0.4632(3) 0.0584(15) Uani 1 1 d . . . . .
H3 H -0.016273 0.367274 0.432908 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3391(6) 0.4768(3) 0.5548(3) 0.0406(11) Uani 1 1 d . . . . .
C5 C 0.2295(7) 0.5430(3) 0.5125(3) 0.0448(12) Uani 1 1 d . . . . .
C17 C 0.9950(7) 0.5847(4) 0.8540(3) 0.0532(14) Uani 1 1 d . . . . .
H17 H 1.083995 0.569343 0.889049 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7621(6) 0.5278(3) 0.7711(3) 0.0487(13) Uani 1 1 d . . . . .
H15 H 0.697436 0.474080 0.749935 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0958(6) 0.4998(4) 0.4679(3) 0.0536(13) Uani 1 1 d . . . . .
H4 H 0.020224 0.542879 0.440740 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2547(7) 0.6592(3) 0.5109(3) 0.0530(15) Uani 1 1 d . . . . .
H12A H 0.219473 0.683934 0.459682 0.064 Uiso 1 1 calc R U . . .
H12B H 0.378338 0.673366 0.516337 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2359(7) 0.7248(4) 0.6535(3) 0.0521(14) Uani 1 1 d . . . . .
H10 H 0.153231 0.759546 0.688347 0.063 Uiso 1 1 calc R U . . .
C18 C 0.9645(7) 0.6835(4) 0.8331(3) 0.0530(14) Uani 1 1 d . . . . .
H18 H 1.035178 0.735173 0.853369 0.064 Uiso 1 1 calc R U . . .
C16 C 0.8933(6) 0.5066(4) 0.8231(3) 0.0540(13) Uani 1 1 d . . . . .
H16 H 0.914396 0.438900 0.837811 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3160(7) 0.3704(3) 0.5490(3) 0.0489(13) Uani 1 1 d . . . . .
H1 H 0.390582 0.326546 0.576036 0.059 Uiso 1 1 calc R U . . .
C2 C 0.1845(8) 0.3296(4) 0.5039(3) 0.0553(15) Uani 1 1 d . . . . .
H2 H 0.170332 0.258679 0.500604 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1574(7) 0.7220(3) 0.5727(4) 0.0613(15) Uani 1 1 d . . . . .
H11A H 0.147679 0.792115 0.553879 0.074 Uiso 1 1 calc R U . . .
H11B H 0.039990 0.694722 0.576929 0.074 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'
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
C22 O1 C10 118.5(4) . . ?
C19 C14 C13 119.1(4) . . ?
C19 C14 C15 117.9(4) . . ?
C15 C14 C13 122.9(4) . . ?
C7 C8 C13 128.5(4) . . ?
C7 C8 C9 121.3(4) . . ?
C13 C8 C9 108.7(4) . . ?
O1 C22 C13 121.4(5) . . ?
O1 C22 C21 117.4(4) . . ?
C13 C22 C21 121.1(5) . . ?
C8 C7 Br1 120.5(4) . . ?
C8 C7 C6 124.8(4) . . ?
C6 C7 Br1 114.1(3) . . ?
C14 C13 C8 127.7(4) . . ?
C22 C13 C14 119.1(4) . . ?
C22 C13 C8 112.8(4) . . ?
C20 C19 C14 119.0(5) . . ?
C20 C19 C18 122.2(5) . . ?
C18 C19 C14 118.7(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.1(5) . . ?
C20 C21 H21 120.0 . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
C8 C9 C10 108.0(4) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C5 C6 C7 119.4(4) . . ?
C1 C6 C7 121.0(4) . . ?
C1 C6 C5 119.6(4) . . ?
C6 C5 C12 122.8(4) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 C12 118.8(4) . . ?
C18 C17 H17 120.1 . . ?
C18 C17 C16 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.5 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C5 C12 H12A 108.0 . . ?
C5 C12 H12B 108.0 . . ?
C5 C12 C11 117.0(4) . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
O1 C10 C9 112.6(4) . . ?
O1 C10 H10 108.0 . . ?
O1 C10 C11 106.8(4) . . ?
C9 C10 H10 108.0 . . ?
C11 C10 C9 113.3(4) . . ?
C11 C10 H10 108.0 . . ?
C19 C18 H18 119.2 . . ?
C17 C18 C19 121.7(5) . . ?
C17 C18 H18 119.2 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(5) . . ?
C15 C16 H16 119.6 . . ?
C6 C1 H1 119.5 . . ?
C2 C1 C6 120.9(5) . . ?
C2 C1 H1 119.5 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2 120.1 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C10 C11 C12 116.8(4) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
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 C7 1.920(4) . ?
O1 C22 1.371(6) . ?
O1 C10 1.460(6) . ?
C14 C13 1.427(6) . ?
C14 C19 1.418(6) . ?
C14 C15 1.419(6) . ?
C8 C7 1.327(6) . ?
C8 C13 1.480(6) . ?
C8 C9 1.502(6) . ?
C22 C13 1.380(6) . ?
C22 C21 1.405(7) . ?
C7 C6 1.481(6) . ?
C19 C20 1.417(6) . ?
C19 C18 1.417(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.357(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.533(6) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(7) . ?
C3 C2 1.387(7) . ?
C6 C5 1.403(6) . ?
C6 C1 1.400(6) . ?
C5 C4 1.396(6) . ?
C5 C12 1.524(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(7) . ?
C17 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(6) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.529(7) . ?
C10 H10 0.9800 . ?
C10 C11 1.508(7) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.376(7) . ?
C2 H2 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
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 C7 C6 C5 -112.9(4) . . . . ?
Br1 C7 C6 C1 66.5(5) . . . . ?
O1 C22 C13 C14 -175.3(4) . . . . ?
O1 C22 C13 C8 -2.0(7) . . . . ?
O1 C22 C21 C20 178.8(4) . . . . ?
O1 C10 C11 C12 71.4(5) . . . . ?
C14 C19 C20 C21 4.4(7) . . . . ?
C14 C19 C18 C17 -1.5(7) . . . . ?
C14 C15 C16 C17 -1.8(7) . . . . ?
C8 C7 C6 C5 58.2(6) . . . . ?
C8 C7 C6 C1 -122.4(5) . . . . ?
C8 C9 C10 O1 -32.3(6) . . . . ?
C8 C9 C10 C11 89.0(5) . . . . ?
C22 O1 C10 C9 -16.6(6) . . . . ?
C22 O1 C10 C11 -141.5(4) . . . . ?
C22 C21 C20 C19 -1.5(7) . . . . ?
C7 C8 C13 C14 -70.5(7) . . . . ?
C7 C8 C13 C22 117.0(5) . . . . ?
C7 C8 C9 C10 -102.0(5) . . . . ?
C7 C6 C5 C4 -178.2(4) . . . . ?
C7 C6 C5 C12 4.2(7) . . . . ?
C7 C6 C1 C2 179.0(4) . . . . ?
C13 C14 C19 C20 -0.6(7) . . . . ?
C13 C14 C19 C18 177.0(4) . . . . ?
C13 C14 C15 C16 -175.2(4) . . . . ?
C13 C8 C7 Br1 10.2(7) . . . . ?
C13 C8 C7 C6 -160.4(4) . . . . ?
C13 C8 C9 C10 65.1(5) . . . . ?
C13 C22 C21 C20 -5.3(8) . . . . ?
C19 C14 C13 C8 -178.1(4) . . . . ?
C19 C14 C13 C22 -6.0(7) . . . . ?
C19 C14 C15 C16 1.6(7) . . . . ?
C21 C22 C13 C14 9.0(7) . . . . ?
C21 C22 C13 C8 -177.7(4) . . . . ?
C9 C8 C7 Br1 174.5(3) . . . . ?
C9 C8 C7 C6 4.0(7) . . . . ?
C9 C8 C13 C14 123.6(5) . . . . ?
C9 C8 C13 C22 -48.9(5) . . . . ?
C9 C10 C11 C12 -53.1(6) . . . . ?
C20 C19 C18 C17 176.0(5) . . . . ?
C6 C5 C4 C3 -1.8(7) . . . . ?
C6 C5 C12 C11 -91.4(6) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C5 C6 C1 C2 -1.6(7) . . . . ?
C5 C12 C11 C10 79.4(6) . . . . ?
C15 C14 C13 C8 -1.3(7) . . . . ?
C15 C14 C13 C22 170.8(5) . . . . ?
C15 C14 C19 C20 -177.5(4) . . . . ?
C15 C14 C19 C18 0.0(7) . . . . ?
C4 C3 C2 C1 0.4(8) . . . . ?
C4 C5 C12 C11 91.0(5) . . . . ?
C12 C5 C4 C3 175.9(5) . . . . ?
C10 O1 C22 C13 36.9(7) . . . . ?
C10 O1 C22 C21 -147.2(4) . . . . ?
C18 C19 C20 C21 -173.1(5) . . . . ?
C18 C17 C16 C15 0.3(8) . . . . ?
C16 C17 C18 C19 1.4(8) . . . . ?
C1 C6 C5 C4 2.3(6) . . . . ?
C1 C6 C5 C12 -175.3(4) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
