#------------------------------------------------------------------------------
#$Date: 2022-06-02 00:58:02 +0300 (Thu, 02 Jun 2022) $
#$Revision: 275721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130173.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_7130173
loop_
_publ_author_name
'Cao, Jing-Si'
'Zeng, Jing'
'Xiao, Jian'
'Wang, Xiao-Han'
'Wang, Yawen'
'Peng, Yu'
_publ_section_title
;
 Total synthesis of linoxepin facilitated by Ni-catalyzed tandem reductive
 cyclization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02221D
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 Br O6'
_chemical_formula_sum            'C21 H19 Br O6'
_chemical_formula_weight         447.27
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2022-02-20 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                98.172(17)
_cell_angle_beta                 100.703(11)
_cell_angle_gamma                94.856(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6456(9)
_cell_length_b                   8.944(3)
_cell_length_c                   13.8908(19)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6030
_cell_measurement_theta_min      3.6990
_cell_volume                     917.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 13

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   10.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   57.0000  -30.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 15

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   91.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00  -22.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  120.0000 13
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0084001000
_diffrn_orient_matrix_UB_12      -0.0788143000
_diffrn_orient_matrix_UB_13      -0.0029846000
_diffrn_orient_matrix_UB_21      0.0003019000
_diffrn_orient_matrix_UB_22      0.0053599000
_diffrn_orient_matrix_UB_23      0.0514705000
_diffrn_orient_matrix_UB_31      -0.0946633000
_diffrn_orient_matrix_UB_32      -0.0162203000
_diffrn_orient_matrix_UB_33      -0.0106993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1670
_reflns_number_gt                1957
_reflns_number_total             3599
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc02221d2.cif
_cod_data_source_block           wangxh_0531
_cod_original_cell_volume        917.9(3)
_cod_database_code               7130173
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C2(H2), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C10(H10A,H10B), C14(H14A,H14B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2017-06-01
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.16048(9) 0.68810(9) 0.52317(5) 0.0600(3) Uani 1 d . . .
O1 O -0.3164(6) 0.8589(7) -0.0868(4) 0.0777(17) Uani 1 d . . .
O2 O -0.1565(7) 0.7995(6) -0.2014(3) 0.0677(15) Uani 1 d . . .
O3 O 0.3726(5) 0.5743(5) 0.3153(3) 0.0506(12) Uani 1 d . . .
O4 O 0.0689(4) 0.6879(4) 0.2483(3) 0.0336(10) Uani 1 d . . .
O5 O -0.2361(5) 0.9570(5) 0.2570(3) 0.0470(12) Uani 1 d . . .
O6 O -0.4693(5) 0.9744(5) 0.3406(3) 0.0528(13) Uani 1 d . . .
C1 C -0.0096(10) 0.7109(10) -0.2141(5) 0.066(2) Uani 1 d . . .
H1A H 0.0810 0.7699 -0.2380 0.079 Uiso 1 calc . . R
H1B H -0.0528 0.6197 -0.2624 0.079 Uiso 1 calc . . R
C2 C 0.0705(8) 0.6685(9) -0.1135(4) 0.0538(19) Uani 1 d . . .
H2 H 0.0819 0.5593 -0.1224 0.065 Uiso 1 calc . . R
C3 C 0.2470(8) 0.7527(9) -0.0643(5) 0.057(2) Uani 1 d . . .
H3A H 0.2409 0.8613 -0.0600 0.068 Uiso 1 calc . . R
H3B H 0.3370 0.7252 -0.1024 0.068 Uiso 1 calc . . R
C4 C 0.2962(7) 0.7120(8) 0.0388(4) 0.0434(17) Uani 1 d . . .
C5 C 0.4569(8) 0.6593(8) 0.0748(5) 0.0529(19) Uani 1 d . . .
H5 H 0.5452 0.6556 0.0370 0.064 Uiso 1 calc . . R
C6 C 0.4876(7) 0.6120(8) 0.1669(5) 0.0494(18) Uani 1 d . . .
H6 H 0.5954 0.5757 0.1899 0.059 Uiso 1 calc . . R
C7 C 0.3587(7) 0.6189(8) 0.2241(4) 0.0404(16) Uani 1 d . . .
C8 C 0.1991(7) 0.6788(7) 0.1901(4) 0.0327(14) Uani 1 d . . .
C9 C 0.1661(7) 0.7201(8) 0.0973(4) 0.0404(16) Uani 1 d . . .
C10 C -0.0082(7) 0.7772(8) 0.0526(4) 0.0477(18) Uani 1 d . . .
H10A H -0.0976 0.7575 0.0919 0.057 Uiso 1 calc . . R
H10B H 0.0116 0.8861 0.0542 0.057 Uiso 1 calc . . R
C11 C -0.0761(8) 0.6999(8) -0.0525(4) 0.0491(18) Uani 1 d . . .
H11 H -0.1457 0.6030 -0.0518 0.059 Uiso 1 calc . . R
C12 C -0.1974(9) 0.7969(9) -0.1116(6) 0.058(2) Uani 1 d . . .
C13 C 0.5140(9) 0.4859(8) 0.3428(5) 0.067(2) Uani 1 d . . .
H13A H 0.4998 0.3945 0.2952 0.101 Uiso 1 calc . . GR
H13B H 0.5109 0.4600 0.4073 0.101 Uiso 1 calc . . GR
H13C H 0.6267 0.5433 0.3446 0.101 Uiso 1 calc . . GR
C14 C 0.1032(7) 0.8267(7) 0.3192(4) 0.0363(15) Uani 1 d . . .
H14A H 0.1079 0.9138 0.2850 0.044 Uiso 1 calc . . R
H14B H 0.2173 0.8296 0.3641 0.044 Uiso 1 calc . . R
C15 C -0.0449(7) 0.8316(7) 0.3761(4) 0.0327(14) Uani 1 d . . .
C16 C -0.0426(7) 0.7796(7) 0.4666(5) 0.0375(15) Uani 1 d . . .
C17 C -0.1804(8) 0.7886(8) 0.5172(5) 0.0457(17) Uani 1 d . . .
H17 H -0.1721 0.7506 0.5766 0.055 Uiso 1 calc . . R
C18 C -0.3316(8) 0.8536(8) 0.4805(5) 0.0479(18) Uani 1 d . . .
H18 H -0.4248 0.8620 0.5148 0.057 Uiso 1 calc . . R
C19 C -0.3387(7) 0.9049(7) 0.3920(5) 0.0378(15) Uani 1 d . . .
C20 C -0.4110(7) 1.0067(8) 0.2538(5) 0.0461(17) Uani 1 d . . .
H20A H -0.4051 1.1150 0.2518 0.055 Uiso 1 calc . . R
H20B H -0.4938 0.9536 0.1950 0.055 Uiso 1 calc . . R
C21 C -0.1988(7) 0.8941(7) 0.3426(4) 0.0356(15) Uani 1 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'
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
C12 O2 C1 111.1(6) . . ?
C7 O3 C13 116.2(5) . . ?
C8 O4 C14 111.2(4) . . ?
C21 O5 C20 105.8(4) . . ?
C19 O6 C20 107.1(4) . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
O2 C1 C2 108.2(5) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
C1 C2 H2 108.8 . . ?
C1 C2 C11 102.8(5) . . ?
C3 C2 C1 115.0(6) . . ?
C3 C2 H2 108.8 . . ?
C3 C2 C11 112.3(5) . . ?
C11 C2 H2 108.8 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C2 C3 C4 108.3(6) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C5 C4 C3 123.7(6) . . ?
C5 C4 C9 119.0(6) . . ?
C9 C4 C3 117.2(5) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C6 125.5(5) . . ?
O3 C7 C8 115.1(5) . . ?
C6 C7 C8 119.4(6) . . ?
O4 C8 C7 119.7(5) . . ?
C9 C8 O4 119.9(5) . . ?
C9 C8 C7 120.3(5) . . ?
C4 C9 C10 116.3(5) . . ?
C8 C9 C4 120.2(5) . . ?
C8 C9 C10 123.5(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.9(5) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C2 C11 H11 108.6 . . ?
C10 C11 C2 115.1(5) . . ?
C10 C11 H11 108.6 . . ?
C10 C11 C12 111.3(6) . . ?
C12 C11 C2 104.6(5) . . ?
C12 C11 H11 108.6 . . ?
O1 C12 O2 122.2(7) . . ?
O1 C12 C11 127.2(7) . . ?
O2 C12 C11 110.6(6) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 110.0 . . ?
O4 C14 H14B 110.0 . . ?
O4 C14 C15 108.3(4) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C16 C15 C14 125.5(5) . . ?
C21 C15 C14 121.0(5) . . ?
C21 C15 C16 113.5(5) . . ?
C15 C16 Br1 118.9(4) . . ?
C17 C16 Br1 117.5(5) . . ?
C17 C16 C15 123.6(5) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 121.3 . . ?
C19 C18 C17 117.4(6) . . ?
C19 C18 H18 121.3 . . ?
O6 C19 C18 129.3(5) . . ?
O6 C19 C21 109.8(5) . . ?
C18 C19 C21 120.9(5) . . ?
O5 C20 H20A 110.2 . . ?
O5 C20 H20B 110.2 . . ?
O6 C20 O5 107.5(4) . . ?
O6 C20 H20A 110.2 . . ?
O6 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C15 C21 O5 126.2(5) . . ?
C19 C21 O5 109.7(5) . . ?
C19 C21 C15 124.1(6) . . ?
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 1.909(6) . ?
O1 C12 1.184(8) . ?
O2 C1 1.451(8) . ?
O2 C12 1.344(8) . ?
O3 C7 1.370(7) . ?
O3 C13 1.420(7) . ?
O4 C8 1.395(6) . ?
O4 C14 1.442(6) . ?
O5 C20 1.439(6) . ?
O5 C21 1.379(7) . ?
O6 C19 1.363(7) . ?
O6 C20 1.419(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.532(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.481(8) . ?
C2 C11 1.546(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.515(8) . ?
C4 C5 1.386(8) . ?
C4 C9 1.397(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(8) . ?
C7 C8 1.403(7) . ?
C8 C9 1.374(8) . ?
C9 C10 1.523(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.500(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.530(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.497(7) . ?
C15 C16 1.398(8) . ?
C15 C21 1.377(7) . ?
C16 C17 1.373(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(8) . ?
C19 C21 1.377(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 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 C16 C17 C18 179.9(5) . . . . ?
O2 C1 C2 C3 -106.7(7) . . . . ?
O2 C1 C2 C11 15.8(7) . . . . ?
O3 C7 C8 O4 -0.5(8) . . . . ?
O3 C7 C8 C9 -176.6(6) . . . . ?
O4 C8 C9 C4 179.7(5) . . . . ?
O4 C8 C9 C10 0.1(10) . . . . ?
O4 C14 C15 C16 93.1(6) . . . . ?
O4 C14 C15 C21 -88.5(7) . . . . ?
O6 C19 C21 O5 0.0(7) . . . . ?
O6 C19 C21 C15 179.0(6) . . . . ?
C1 O2 C12 O1 -178.1(7) . . . . ?
C1 O2 C12 C11 -0.5(8) . . . . ?
C1 C2 C3 C4 173.1(6) . . . . ?
C1 C2 C11 C10 -137.8(6) . . . . ?
C1 C2 C11 C12 -15.4(7) . . . . ?
C2 C3 C4 C5 126.9(7) . . . . ?
C2 C3 C4 C9 -49.1(8) . . . . ?
C2 C11 C12 O1 -172.0(8) . . . . ?
C2 C11 C12 O2 10.6(8) . . . . ?
C3 C2 C11 C10 -13.6(9) . . . . ?
C3 C2 C11 C12 108.8(6) . . . . ?
C3 C4 C5 C6 -174.6(6) . . . . ?
C3 C4 C9 C8 177.3(6) . . . . ?
C3 C4 C9 C10 -3.1(9) . . . . ?
C4 C5 C6 C7 -0.8(11) . . . . ?
C4 C9 C10 C11 46.7(8) . . . . ?
C5 C4 C9 C8 1.2(10) . . . . ?
C5 C4 C9 C10 -179.2(6) . . . . ?
C5 C6 C7 O3 179.3(6) . . . . ?
C5 C6 C7 C8 -2.2(10) . . . . ?
C6 C7 C8 O4 -179.2(5) . . . . ?
C6 C7 C8 C9 4.7(10) . . . . ?
C7 C8 C9 C4 -4.2(10) . . . . ?
C7 C8 C9 C10 176.3(6) . . . . ?
C8 O4 C14 C15 177.8(4) . . . . ?
C8 C9 C10 C11 -133.7(7) . . . . ?
C9 C4 C5 C6 1.3(11) . . . . ?
C9 C10 C11 C2 -37.1(8) . . . . ?
C9 C10 C11 C12 -155.8(6) . . . . ?
C10 C11 C12 O1 -47.1(10) . . . . ?
C10 C11 C12 O2 135.4(6) . . . . ?
C11 C2 C3 C4 56.0(8) . . . . ?
C12 O2 C1 C2 -10.1(8) . . . . ?
C13 O3 C7 C6 -13.7(9) . . . . ?
C13 O3 C7 C8 167.7(6) . . . . ?
C14 O4 C8 C7 86.1(7) . . . . ?
C14 O4 C8 C9 -97.7(6) . . . . ?
C14 C15 C16 Br1 -2.1(8) . . . . ?
C14 C15 C16 C17 178.9(6) . . . . ?
C14 C15 C21 O5 0.1(10) . . . . ?
C14 C15 C21 C19 -178.7(5) . . . . ?
C15 C16 C17 C18 -1.0(10) . . . . ?
C16 C15 C21 O5 178.6(6) . . . . ?
C16 C15 C21 C19 -0.2(9) . . . . ?
C16 C17 C18 C19 1.2(10) . . . . ?
C17 C18 C19 O6 -179.1(6) . . . . ?
C17 C18 C19 C21 -1.0(9) . . . . ?
C18 C19 C21 O5 -178.4(6) . . . . ?
C18 C19 C21 C15 0.5(10) . . . . ?
C19 O6 C20 O5 -1.6(7) . . . . ?
C20 O5 C21 C15 -179.9(6) . . . . ?
C20 O5 C21 C19 -1.0(7) . . . . ?
C20 O6 C19 C18 179.2(7) . . . . ?
C20 O6 C19 C21 1.0(7) . . . . ?
C21 O5 C20 O6 1.5(6) . . . . ?
C21 C15 C16 Br1 179.5(4) . . . . ?
C21 C15 C16 C17 0.4(9) . . . . ?
