#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:14:58 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/34/7133415.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_7133415
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         'C21 H15 Br O2'
_chemical_formula_sum            'C21 H15 Br O2'
_chemical_formula_weight         379.24
_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             2021-11-17
_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                 114.336(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8697(4)
_cell_length_b                   22.6968(7)
_cell_length_c                   8.9630(5)
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8520
_cell_measurement_theta_min      4.2130
_cell_volume                     1644.05(15)
_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 0.997
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  95.00   1.00    4.00    --   18.74-178.00 -90.00   57
  2  ω    -12.00  91.00   1.00    4.00    --   18.74  19.00-120.00  103
  3  ω     48.00  83.00   1.00    4.00    --   18.74  57.00-120.00   35
  4  ω     46.00  72.00   1.00    4.00    --   18.74 178.00 -30.00   26
  5  ω    -64.00  25.00   1.00    4.00    --  -18.85 -19.00 -30.00   89
  6  ω    -41.00  36.00   1.00    4.00    --  -18.85  38.00 120.00   77
;
_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      -0.0574829000
_diffrn_orient_matrix_UB_12      0.0048946000
_diffrn_orient_matrix_UB_13      -0.0819763000
_diffrn_orient_matrix_UB_21      0.0469931000
_diffrn_orient_matrix_UB_22      0.0245828000
_diffrn_orient_matrix_UB_23      -0.0051090000
_diffrn_orient_matrix_UB_31      0.0468252000
_diffrn_orient_matrix_UB_32      -0.0186635000
_diffrn_orient_matrix_UB_33      -0.0282931000
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.012
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66447
_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    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0472
_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)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                5045
_reflns_number_total             7480
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20211117-zzx-968
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133415
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H15 Br O2'
_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:
 C13(H13), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C14(H14A,H14B), C35(H35A,H35B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C2(H2), C23(H23), C24(H24), C28(H28), C19(H19), C37(H37), C7(H7),
 C40(H40), C25(H25), C8(H8), C38(H38), C26(H26), C5(H5), C39(H39), C16(H16),
 C3(H3), C18(H18), C17(H17), C4(H4)
;
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.799
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
Br2 Br 0.94095(9) 0.72651(3) 0.65062(9) 0.0649(2) Uani 1 1 d . . . . .
Br1 Br -0.15153(8) 0.36277(3) 0.74383(9) 0.0656(2) Uani 1 1 d . . . . .
O1 O 0.0977(6) 0.27525(18) 0.9404(6) 0.0635(13) Uani 1 1 d . . . . .
O2 O 0.2835(7) 0.4419(2) 0.6904(6) 0.0656(14) Uani 1 1 d . . . . .
O4 O 0.5786(6) 0.62980(18) 0.7940(6) 0.0557(12) Uani 1 1 d . . . . .
O3 O 1.0046(6) 0.6053(2) 0.5634(6) 0.0679(14) Uani 1 1 d . . . . .
C11 C 0.0904(6) 0.3685(3) 0.8086(6) 0.0376(12) Uani 1 1 d . . . . .
C22 C 0.5565(7) 0.6804(2) 0.3940(7) 0.0372(13) Uani 1 1 d . . . . .
C27 C 0.3845(8) 0.6917(2) 0.3174(8) 0.0466(16) Uani 1 1 d . . . . .
C29 C 0.3575(8) 0.6659(3) 0.5638(9) 0.0509(17) Uani 1 1 d . . . . .
H29 H 0.292086 0.660171 0.621223 0.061 Uiso 1 1 calc R U . . .
C30 C 0.5278(8) 0.6536(2) 0.6400(8) 0.0405(14) Uani 1 1 d . . . . .
C2 C 0.0629(8) 0.4209(3) 1.1075(7) 0.0483(16) Uani 1 1 d . . . . .
H2 H 0.026023 0.382608 1.076451 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1525(7) 0.4289(2) 0.8781(7) 0.0374(14) Uani 1 1 d . . . . .
C32 C 0.8155(7) 0.6545(2) 0.6544(7) 0.0396(14) Uani 1 1 d . . . . .
C23 C 0.6448(9) 0.6822(2) 0.2932(8) 0.0492(16) Uani 1 1 d . . . . .
H23 H 0.758534 0.675816 0.340243 0.059 Uiso 1 1 calc R U . . .
C1 C 0.1343(7) 0.4524(2) 1.0184(7) 0.0405(14) Uani 1 1 d . . . . .
C41 C 0.7665(7) 0.5509(2) 0.5323(8) 0.0449(16) Uani 1 1 d . . . . .
C24 C 0.5672(11) 0.6930(3) 0.1286(9) 0.061(2) Uani 1 1 d . . . . .
H24 H 0.627582 0.692168 0.064929 0.073 Uiso 1 1 calc R U . . .
C28 C 0.2885(8) 0.6856(3) 0.4095(9) 0.0551(18) Uani 1 1 d . . . . .
H28 H 0.176748 0.695299 0.362417 0.066 Uiso 1 1 calc R U . . .
C33 C 0.8612(8) 0.6433(3) 0.8366(7) 0.0504(17) Uani 1 1 d . . . . .
H33A H 0.970756 0.625978 0.886264 0.060 Uiso 1 1 calc R U . . .
H33B H 0.864254 0.680575 0.890950 0.060 Uiso 1 1 calc R U . . .
C31 C 0.6312(7) 0.6643(2) 0.5634(7) 0.0336(13) Uani 1 1 d . . . . .
C13 C 0.2745(9) 0.3801(3) 0.6610(8) 0.0556(18) Uani 1 1 d . . . . .
H13 H 0.273436 0.374836 0.552087 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2391(8) 0.4612(3) 0.8099(8) 0.0494(17) Uani 1 1 d . . . . .
C19 C 0.4104(10) 0.3088(2) 1.1892(8) 0.0553(18) Uani 1 1 d . . . . .
H19 H 0.336115 0.295546 1.230711 0.066 Uiso 1 1 calc R U . . .
C36 C 0.6872(8) 0.5269(2) 0.6233(9) 0.0460(16) Uani 1 1 d . . . . .
C15 C 0.4669(8) 0.3422(2) 0.9593(8) 0.0487(16) Uani 1 1 d . . . . .
C20 C 0.3554(7) 0.3234(2) 1.0238(8) 0.0413(14) Uani 1 1 d . . . . .
C37 C 0.5709(8) 0.4827(3) 0.5514(10) 0.061(2) Uani 1 1 d . . . . .
H37 H 0.515397 0.466282 0.609585 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2644(9) 0.5430(3) 0.9861(11) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.297149 0.581640 1.017964 0.086 Uiso 1 1 calc R U . . .
C40 C 0.7314(9) 0.5294(3) 0.3752(9) 0.0611(19) Uani 1 1 d . . . . .
H40 H 0.784935 0.545470 0.314766 0.073 Uiso 1 1 calc R U . . .
C25 C 0.3988(12) 0.7052(3) 0.0562(10) 0.071(2) Uani 1 1 d . . . . .
H25 H 0.347353 0.713203 -0.055401 0.086 Uiso 1 1 calc R U . . .
C21 C 0.1735(7) 0.3173(2) 0.9255(7) 0.0403(14) Uani 1 1 d . . . . .
C6 C 0.1896(8) 0.5110(3) 1.0698(9) 0.0518(17) Uani 1 1 d . . . . .
C8 C 0.2906(9) 0.5200(3) 0.8615(12) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.342115 0.542262 0.808832 0.085 Uiso 1 1 calc R U . . .
C38 C 0.5364(10) 0.4627(3) 0.3949(13) 0.081(3) Uani 1 1 d . . . . .
H38 H 0.456073 0.433938 0.347776 0.097 Uiso 1 1 calc R U . . .
C14 C 0.4279(9) 0.3482(3) 0.7806(9) 0.0618(19) Uani 1 1 d . . . . .
H14A H 0.423639 0.308593 0.738408 0.074 Uiso 1 1 calc R U . . .
H14B H 0.522472 0.367349 0.773379 0.074 Uiso 1 1 calc R U . . .
C34 C 0.7396(9) 0.6031(3) 0.8610(8) 0.0540(17) Uani 1 1 d . . . . .
H34 H 0.772804 0.600780 0.979501 0.065 Uiso 1 1 calc R U . . .
C26 C 0.3096(10) 0.7055(2) 0.1470(9) 0.064(2) Uani 1 1 d . . . . .
H26 H 0.197670 0.714965 0.097849 0.076 Uiso 1 1 calc R U . . .
C35 C 0.7328(9) 0.5399(3) 0.8016(9) 0.0593(19) Uani 1 1 d . . . . .
H35A H 0.840782 0.522540 0.863193 0.071 Uiso 1 1 calc R U . . .
H35B H 0.654948 0.518785 0.832564 0.071 Uiso 1 1 calc R U . . .
C42 C 0.8769(8) 0.6028(2) 0.5830(8) 0.0451(15) Uani 1 1 d . . . . .
C5 C 0.1691(10) 0.5343(3) 1.2068(10) 0.073(2) Uani 1 1 d . . . . .
H5 H 0.204297 0.572553 1.239961 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1102(8) 0.3585(3) 0.6497(7) 0.0575(16) Uani 1 1 d . . . . .
H12A H 0.099973 0.316704 0.624292 0.069 Uiso 1 1 calc R U . . .
H12B H 0.022296 0.378822 0.561151 0.069 Uiso 1 1 calc R U . . .
C39 C 0.6195(11) 0.4851(3) 0.3096(11) 0.076(2) Uani 1 1 d . . . . .
H39 H 0.600144 0.470132 0.206675 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6313(9) 0.3476(3) 1.0684(12) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.707038 0.361258 1.029204 0.087 Uiso 1 1 calc R U . . .
C3 C 0.0461(8) 0.4458(3) 1.2411(9) 0.0634(19) Uani 1 1 d . . . . .
H3 H -0.001844 0.424306 1.298455 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5775(12) 0.3142(3) 1.2910(10) 0.078(3) Uani 1 1 d . . . . .
H18 H 0.615083 0.304503 1.401262 0.093 Uiso 1 1 calc R U . . .
C17 C 0.6874(10) 0.3338(3) 1.2309(13) 0.085(3) Uani 1 1 d . . . . .
H17 H 0.799041 0.337673 1.299761 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1015(10) 0.5035(4) 1.2900(11) 0.082(3) Uani 1 1 d . . . . .
H4 H 0.090939 0.520192 1.379999 0.099 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
C9 O2 C13 116.9(5) . . ?
C30 O4 C34 116.4(4) . . ?
C10 C11 Br1 110.3(4) . . ?
C10 C11 C21 114.5(5) . . ?
C10 C11 C12 111.0(5) . . ?
C21 C11 Br1 107.9(4) . . ?
C12 C11 Br1 104.1(4) . . ?
C12 C11 C21 108.5(5) . . ?
C27 C22 C23 117.0(6) . . ?
C27 C22 C31 119.8(5) . . ?
C23 C22 C31 123.1(5) . . ?
C22 C27 C28 119.1(6) . . ?
C22 C27 C26 119.5(7) . . ?
C28 C27 C26 121.2(7) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.7(6) . . ?
O4 C30 C29 114.1(5) . . ?
O4 C30 C31 124.1(6) . . ?
C31 C30 C29 121.8(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.2(6) . . ?
C1 C10 C11 123.0(5) . . ?
C9 C10 C11 118.4(5) . . ?
C9 C10 C1 118.5(5) . . ?
C33 C32 Br2 104.5(4) . . ?
C33 C32 C42 109.4(5) . . ?
C31 C32 Br2 111.1(4) . . ?
C31 C32 C33 110.5(5) . . ?
C31 C32 C42 112.1(5) . . ?
C42 C32 Br2 108.9(4) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.8(7) . . ?
C24 C23 H23 119.1 . . ?
C2 C1 C10 123.4(5) . . ?
C2 C1 C6 117.8(6) . . ?
C6 C1 C10 118.8(6) . . ?
C36 C41 C40 119.8(6) . . ?
C36 C41 C42 124.3(6) . . ?
C40 C41 C42 115.6(6) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(7) . . ?
C25 C24 H24 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(6) . . ?
C29 C28 H28 119.8 . . ?
C32 C33 H33A 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
C34 C33 C32 111.5(5) . . ?
C34 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C22 C31 C32 122.3(5) . . ?
C30 C31 C22 117.5(5) . . ?
C30 C31 C32 120.0(5) . . ?
O2 C13 H13 106.4 . . ?
O2 C13 C14 111.9(6) . . ?
O2 C13 C12 108.3(5) . . ?
C14 C13 H13 106.4 . . ?
C12 C13 H13 106.4 . . ?
C12 C13 C14 116.9(5) . . ?
O2 C9 C10 125.2(6) . . ?
O2 C9 C8 113.6(6) . . ?
C10 C9 C8 121.2(6) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(7) . . ?
C41 C36 C37 117.9(7) . . ?
C41 C36 C35 124.5(6) . . ?
C37 C36 C35 117.2(6) . . ?
C20 C15 C14 125.2(6) . . ?
C16 C15 C20 116.9(7) . . ?
C16 C15 C14 117.3(7) . . ?
C19 C20 C15 120.9(6) . . ?
C19 C20 C21 115.1(6) . . ?
C15 C20 C21 124.0(6) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 C36 121.2(7) . . ?
C38 C37 H37 119.4 . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C8 C7 C6 122.0(7) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 C41 120.8(7) . . ?
C39 C40 H40 119.6 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(7) . . ?
C26 C25 H25 119.9 . . ?
O1 C21 C11 122.8(5) . . ?
O1 C21 C20 121.6(5) . . ?
C20 C21 C11 115.5(5) . . ?
C7 C6 C1 119.3(6) . . ?
C7 C6 C5 122.1(7) . . ?
C5 C6 C1 118.6(7) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.7(7) . . ?
C7 C8 H8 120.2 . . ?
C37 C38 H38 119.9 . . ?
C39 C38 C37 120.2(7) . . ?
C39 C38 H38 119.9 . . ?
C13 C14 H14A 106.6 . . ?
C13 C14 H14B 106.6 . . ?
C15 C14 C13 122.7(5) . . ?
C15 C14 H14A 106.6 . . ?
C15 C14 H14B 106.6 . . ?
H14A C14 H14B 106.6 . . ?
O4 C34 C33 109.5(5) . . ?
O4 C34 H34 106.2 . . ?
O4 C34 C35 111.2(6) . . ?
C33 C34 H34 106.2 . . ?
C33 C34 C35 116.8(6) . . ?
C35 C34 H34 106.2 . . ?
C27 C26 H26 119.5 . . ?
C25 C26 C27 121.0(7) . . ?
C25 C26 H26 119.5 . . ?
C36 C35 C34 120.6(5) . . ?
C36 C35 H35A 107.2 . . ?
C36 C35 H35B 107.2 . . ?
C34 C35 H35A 107.2 . . ?
C34 C35 H35B 107.2 . . ?
H35A C35 H35B 106.8 . . ?
O3 C42 C32 122.2(6) . . ?
O3 C42 C41 122.1(6) . . ?
C41 C42 C32 115.6(5) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.6(7) . . ?
C4 C5 H5 118.7 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 C11 111.7(5) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C40 C39 H39 120.0 . . ?
C38 C39 C40 119.9(8) . . ?
C38 C39 H39 120.0 . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.1(8) . . ?
C17 C16 H16 118.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.7(8) . . ?
C17 C18 H18 119.6 . . ?
C16 C17 C18 119.2(8) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C5 C4 C3 119.6(7) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
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
Br2 C32 1.984(5) . ?
Br1 C11 1.983(5) . ?
O1 C21 1.206(6) . ?
O2 C13 1.424(7) . ?
O2 C9 1.356(7) . ?
O4 C30 1.374(7) . ?
O4 C34 1.436(8) . ?
O3 C42 1.217(7) . ?
C11 C10 1.513(8) . ?
C11 C21 1.535(8) . ?
C11 C12 1.523(7) . ?
C22 C27 1.414(8) . ?
C22 C23 1.420(8) . ?
C22 C31 1.432(7) . ?
C27 C28 1.416(9) . ?
C27 C26 1.428(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.405(8) . ?
C29 C28 1.338(9) . ?
C30 C31 1.375(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.403(8) . ?
C2 C3 1.386(8) . ?
C10 C1 1.435(8) . ?
C10 C9 1.375(8) . ?
C32 C33 1.533(8) . ?
C32 C31 1.512(8) . ?
C32 C42 1.541(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(9) . ?
C1 C6 1.427(8) . ?
C41 C36 1.390(9) . ?
C41 C40 1.399(9) . ?
C41 C42 1.478(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(11) . ?
C28 H28 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.496(9) . ?
C13 H13 0.9800 . ?
C13 C14 1.524(9) . ?
C13 C12 1.501(8) . ?
C9 C8 1.424(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(9) . ?
C19 C18 1.389(10) . ?
C36 C37 1.392(9) . ?
C36 C35 1.507(9) . ?
C15 C20 1.401(8) . ?
C15 C14 1.500(9) . ?
C15 C16 1.386(9) . ?
C20 C21 1.492(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.383(11) . ?
C7 H7 0.9300 . ?
C7 C6 1.394(10) . ?
C7 C8 1.338(10) . ?
C40 H40 0.9300 . ?
C40 C39 1.364(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.349(10) . ?
C6 C5 1.415(10) . ?
C8 H8 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.360(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C34 H34 0.9800 . ?
C34 C35 1.524(9) . ?
C26 H26 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.331(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C39 H39 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.367(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.368(11) . ?
C17 H17 0.9300 . ?
C4 H4 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
Br2 C32 C33 C34 161.8(4) . . . . ?
Br2 C32 C31 C22 59.3(6) . . . . ?
Br2 C32 C31 C30 -125.3(5) . . . . ?
Br2 C32 C42 O3 14.2(7) . . . . ?
Br2 C32 C42 C41 -162.9(4) . . . . ?
Br1 C11 C10 C1 58.9(6) . . . . ?
Br1 C11 C10 C9 -125.2(5) . . . . ?
Br1 C11 C21 O1 15.2(7) . . . . ?
Br1 C11 C21 C20 -163.4(4) . . . . ?
Br1 C11 C12 C13 161.5(5) . . . . ?
O2 C13 C14 C15 69.0(8) . . . . ?
O2 C13 C12 C11 -61.7(7) . . . . ?
O2 C9 C8 C7 -175.6(7) . . . . ?
O4 C30 C31 C22 170.2(5) . . . . ?
O4 C30 C31 C32 -5.4(8) . . . . ?
O4 C34 C35 C36 65.6(8) . . . . ?
C11 C10 C1 C2 2.3(9) . . . . ?
C11 C10 C1 C6 -176.9(5) . . . . ?
C11 C10 C9 O2 -4.4(9) . . . . ?
C11 C10 C9 C8 175.4(6) . . . . ?
C22 C27 C28 C29 -4.1(9) . . . . ?
C22 C27 C26 C25 3.3(8) . . . . ?
C22 C23 C24 C25 2.9(9) . . . . ?
C27 C22 C23 C24 -1.5(8) . . . . ?
C27 C22 C31 C30 7.6(7) . . . . ?
C27 C22 C31 C32 -176.9(5) . . . . ?
C29 C30 C31 C22 -8.7(8) . . . . ?
C29 C30 C31 C32 175.7(5) . . . . ?
C30 O4 C34 C33 46.8(7) . . . . ?
C30 O4 C34 C35 -83.8(6) . . . . ?
C30 C29 C28 C27 3.2(9) . . . . ?
C2 C1 C6 C7 178.6(6) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C3 C4 C5 0.4(12) . . . . ?
C10 C11 C21 O1 138.4(6) . . . . ?
C10 C11 C21 C20 -40.2(6) . . . . ?
C10 C11 C12 C13 42.8(7) . . . . ?
C10 C1 C6 C7 -2.2(9) . . . . ?
C10 C1 C6 C5 179.0(6) . . . . ?
C10 C9 C8 C7 4.6(11) . . . . ?
C32 C33 C34 O4 -61.5(7) . . . . ?
C32 C33 C34 C35 66.1(7) . . . . ?
C23 C22 C27 C28 174.8(5) . . . . ?
C23 C22 C27 C26 -1.5(7) . . . . ?
C23 C22 C31 C30 -168.3(5) . . . . ?
C23 C22 C31 C32 7.2(8) . . . . ?
C23 C24 C25 C26 -1.1(10) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
C1 C10 C9 O2 171.6(6) . . . . ?
C1 C10 C9 C8 -8.6(9) . . . . ?
C1 C6 C5 C4 0.4(10) . . . . ?
C41 C36 C37 C38 0.7(9) . . . . ?
C41 C36 C35 C34 54.7(9) . . . . ?
C41 C40 C39 C38 2.3(10) . . . . ?
C24 C25 C26 C27 -1.9(9) . . . . ?
C28 C27 C26 C25 -173.0(6) . . . . ?
C28 C29 C30 O4 -175.6(5) . . . . ?
C28 C29 C30 C31 3.5(9) . . . . ?
C33 C32 C31 C22 174.9(5) . . . . ?
C33 C32 C31 C30 -9.8(7) . . . . ?
C33 C32 C42 O3 -99.5(7) . . . . ?
C33 C32 C42 C41 83.4(6) . . . . ?
C33 C34 C35 C36 -61.2(9) . . . . ?
C31 C22 C27 C28 -1.4(8) . . . . ?
C31 C22 C27 C26 -177.7(5) . . . . ?
C31 C22 C23 C24 174.6(5) . . . . ?
C31 C32 C33 C34 42.3(7) . . . . ?
C31 C32 C42 O3 137.5(6) . . . . ?
C31 C32 C42 C41 -39.6(7) . . . . ?
C13 O2 C9 C10 -15.5(9) . . . . ?
C13 O2 C9 C8 164.6(6) . . . . ?
C9 O2 C13 C14 -82.7(7) . . . . ?
C9 O2 C13 C12 47.5(7) . . . . ?
C9 C10 C1 C2 -173.6(6) . . . . ?
C9 C10 C1 C6 7.3(8) . . . . ?
C19 C20 C21 O1 -43.3(8) . . . . ?
C19 C20 C21 C11 135.3(5) . . . . ?
C19 C18 C17 C16 -0.5(11) . . . . ?
C36 C41 C40 C39 0.2(9) . . . . ?
C36 C41 C42 O3 139.3(7) . . . . ?
C36 C41 C42 C32 -43.6(8) . . . . ?
C36 C37 C38 C39 1.8(11) . . . . ?
C15 C20 C21 O1 136.6(6) . . . . ?
C15 C20 C21 C11 -44.8(7) . . . . ?
C15 C16 C17 C18 -0.7(11) . . . . ?
C20 C19 C18 C17 0.1(10) . . . . ?
C20 C15 C14 C13 48.6(9) . . . . ?
C20 C15 C16 C17 2.1(9) . . . . ?
C37 C36 C35 C34 -133.1(6) . . . . ?
C37 C38 C39 C40 -3.3(11) . . . . ?
C7 C6 C5 C4 -178.3(8) . . . . ?
C40 C41 C36 C37 -1.7(8) . . . . ?
C40 C41 C36 C35 170.4(6) . . . . ?
C40 C41 C42 O3 -46.7(8) . . . . ?
C40 C41 C42 C32 130.4(6) . . . . ?
C21 C11 C10 C1 -63.0(7) . . . . ?
C21 C11 C10 C9 112.9(6) . . . . ?
C21 C11 C12 C13 -83.7(6) . . . . ?
C6 C7 C8 C9 0.8(11) . . . . ?
C6 C5 C4 C3 -0.6(12) . . . . ?
C8 C7 C6 C1 -1.9(11) . . . . ?
C8 C7 C6 C5 176.8(7) . . . . ?
C14 C13 C12 C11 65.7(7) . . . . ?
C14 C15 C20 C19 168.0(6) . . . . ?
C14 C15 C20 C21 -11.8(8) . . . . ?
C14 C15 C16 C17 -169.1(6) . . . . ?
C34 O4 C30 C29 165.0(5) . . . . ?
C34 O4 C30 C31 -14.0(8) . . . . ?
C26 C27 C28 C29 172.2(5) . . . . ?
C35 C36 C37 C38 -172.0(6) . . . . ?
C42 C32 C33 C34 -81.6(6) . . . . ?
C42 C32 C31 C22 -62.8(6) . . . . ?
C42 C32 C31 C30 112.6(6) . . . . ?
C42 C41 C36 C37 172.1(5) . . . . ?
C42 C41 C36 C35 -15.8(9) . . . . ?
C42 C41 C40 C39 -174.1(6) . . . . ?
C12 C11 C10 C1 173.8(5) . . . . ?
C12 C11 C10 C9 -10.3(7) . . . . ?
C12 C11 C21 O1 -97.0(6) . . . . ?
C12 C11 C21 C20 84.4(6) . . . . ?
C12 C13 C14 C15 -56.7(8) . . . . ?
C16 C15 C20 C19 -2.4(8) . . . . ?
C16 C15 C20 C21 177.7(5) . . . . ?
C16 C15 C14 C13 -141.0(6) . . . . ?
C3 C2 C1 C10 -179.1(6) . . . . ?
C3 C2 C1 C6 0.1(9) . . . . ?
C18 C19 C20 C15 1.4(8) . . . . ?
C18 C19 C20 C21 -178.7(6) . . . . ?
