#------------------------------------------------------------------------------
#$Date: 2020-12-02 07:37:30 +0200 (Wed, 02 Dec 2020) $
#$Revision: 259461 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157787.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_7157787
loop_
_publ_author_name
'Gadigennavar, Savita'
'Ranganathan, Madhav'
'Sankararaman, Sethuraman'
_publ_section_title
;
 Which isomer is it, 1,2,5,6- or 1,4,5,8-tetrasubstituted
 cycloocta-1,3,5,7-tetraene? Synthesis of symmetrically tetrasubstituted
 cycloocta-1,3,5,7-tetraene derivatives
;
_journal_issue                   45
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              9284
_journal_page_last               9291
_journal_paper_doi               10.1039/D0OB01871F
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C12 H12 Br4'
_chemical_formula_sum            'C12 H12 Br4'
_chemical_formula_weight         475.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-29 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.823(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.8169(9)
_cell_length_b                   23.1350(15)
_cell_length_c                   13.2408(7)
_cell_measurement_reflns_used    4613
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.70
_cell_measurement_theta_min      2.76
_cell_volume                     4522.7(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker apex 2'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1794
_diffrn_reflns_av_unetI/netI     0.1802
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43078
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.379
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    10.652
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_description       Block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.784
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.0739
_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)+(0.1037P)²+2.9041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3286
_reflns_number_total             7895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01871f2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157787
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.176
_shelx_estimated_absorpt_t_max   0.416
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.3560(9) 0.6599(6) 0.0451(11) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.3403(10) 0.6337(6) -0.0396(10) 0.044(4) Uani 1 1 d . . . . .
H2 H 0.377101 0.602120 -0.050589 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2715(10) 0.6477(5) -0.1203(11) 0.042(4) Uani 1 1 d . . . . .
H3 H 0.291656 0.657282 -0.182776 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1800(10) 0.6481(5) -0.1136(10) 0.038(4) Uani 1 1 d . . . . .
C5 C 0.1392(9) 0.6334(6) -0.0200(11) 0.039(4) Uani 1 1 d . . . . .
C6 C 0.1563(9) 0.6603(6) 0.0706(10) 0.040(4) Uani 1 1 d . . . . .
H6 H 0.127830 0.646242 0.125660 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2162(10) 0.7096(6) 0.0869(10) 0.044(4) Uani 1 1 d . . . . .
H7 H 0.190512 0.743709 0.107907 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3024(10) 0.7107(6) 0.0748(9) 0.039(4) Uani 1 1 d . U . . .
C9 C 0.3531(11) 0.7666(8) 0.0965(12) 0.077(6) Uani 1 1 d . U . . .
H9A H 0.402282 0.760104 0.148304 0.093 Uiso 1 1 calc R U . . .
H9B H 0.312522 0.795004 0.122038 0.093 Uiso 1 1 calc R U . . .
C10 C 0.4303(10) 0.6397(7) 0.1160(11) 0.062(5) Uani 1 1 d . . . . .
H10A H 0.467530 0.672348 0.139464 0.074 Uiso 1 1 calc R U . . .
H10B H 0.468007 0.613099 0.081620 0.074 Uiso 1 1 calc R U . . .
C11 C 0.0721(9) 0.5832(6) -0.0248(11) 0.051(4) Uani 1 1 d . . . . .
H11A H 0.023295 0.590925 -0.076514 0.062 Uiso 1 1 calc R U . . .
H11B H 0.046080 0.579699 0.039779 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1179(12) 0.6648(7) -0.1985(12) 0.079(6) Uani 1 1 d . . . . .
H12A H 0.066970 0.638310 -0.204540 0.095 Uiso 1 1 calc R U . . .
H12B H 0.148239 0.662681 -0.260490 0.095 Uiso 1 1 calc R U . . .
Br1 Br 0.13141(14) 0.51122(8) -0.05552(16) 0.0809(7) Uani 1 1 d . . . . .
Br2 Br 0.07364(12) 0.74427(8) -0.17996(13) 0.0699(6) Uani 1 1 d . . . . .
Br3 Br 0.40083(15) 0.79595(8) -0.0227(2) 0.1031(8) Uani 1 1 d . . . . .
Br4 Br 0.38312(15) 0.60098(11) 0.23214(14) 0.1011(9) Uani 1 1 d . . . . .
C13 C 0.2075(9) 0.5514(5) 0.4405(9) 0.028(3) Uani 1 1 d . . . . .
C14 C 0.2973(9) 0.5459(5) 0.4453(9) 0.032(3) Uani 1 1 d . . . . .
H14 H 0.329972 0.579758 0.437917 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3506(8) 0.4928(6) 0.4607(10) 0.033(3) Uani 1 1 d . . . . .
H15 H 0.381454 0.480088 0.406625 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3586(8) 0.4625(5) 0.5410(10) 0.030(3) Uani 1 1 d . . . . .
C17 C 0.3107(10) 0.4779(6) 0.6301(10) 0.040(4) Uani 1 1 d . . . . .
C18 C 0.2217(9) 0.4809(6) 0.6296(10) 0.038(4) Uani 1 1 d . . . . .
H18 H 0.198211 0.491933 0.689656 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1559(8) 0.4683(5) 0.5421(9) 0.029(3) Uani 1 1 d . . . . .
H19 H 0.118510 0.436152 0.545346 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1479(8) 0.5012(5) 0.4581(9) 0.028(3) Uani 1 1 d . . . . .
C21 C 0.1662(10) 0.6077(6) 0.4178(10) 0.044(4) Uani 1 1 d . . . . .
H21A H 0.128938 0.605369 0.354113 0.053 Uiso 1 1 calc R U . . .
H21B H 0.213578 0.635846 0.409823 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0711(8) 0.4906(6) 0.3797(9) 0.034(3) Uani 1 1 d . . . . .
H22A H 0.028347 0.522301 0.381041 0.041 Uiso 1 1 calc R U . . .
H22B H 0.039926 0.455530 0.396956 0.041 Uiso 1 1 calc R U . . .
C23 C 0.4240(9) 0.4127(5) 0.5498(10) 0.043(4) Uani 1 1 d . . . . .
H23A H 0.473389 0.421759 0.600054 0.051 Uiso 1 1 calc R U . . .
H23B H 0.449188 0.406847 0.485336 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3632(10) 0.4909(7) 0.7273(10) 0.054(4) Uani 1 1 d . . . . .
H24A H 0.403491 0.458964 0.746361 0.064 Uiso 1 1 calc R U . . .
H24B H 0.322467 0.496157 0.780170 0.064 Uiso 1 1 calc R U . . .
Br5 Br 0.10812(13) 0.48314(9) 0.24476(13) 0.0793(7) Uani 1 1 d . . . . .
Br6 Br 0.09213(12) 0.63378(7) 0.52325(13) 0.0615(5) Uani 1 1 d . . . . .
Br7 Br 0.43438(12) 0.56212(9) 0.71186(14) 0.0789(7) Uani 1 1 d . . . . .
Br8 Br 0.36447(14) 0.34165(8) 0.58891(17) 0.0874(7) Uani 1 1 d . . . . .
C25 C 0.1472(8) 0.2088(6) 0.4503(11) 0.035(3) Uani 1 1 d . . . . .
C26 C 0.1992(9) 0.1889(5) 0.3678(10) 0.032(3) Uani 1 1 d . . . . .
C27 C 0.2892(9) 0.1819(6) 0.3797(10) 0.039(4) Uani 1 1 d . . . . .
H27 H 0.315696 0.167664 0.323530 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3522(8) 0.1937(5) 0.4695(10) 0.032(3) Uani 1 1 d . . . . .
H28 H 0.394600 0.222907 0.463785 0.038 Uiso 1 1 calc R U . . .
C29 C 0.3537(8) 0.1669(6) 0.5564(10) 0.031(3) Uani 1 1 d . . . . .
C30 C 0.2903(8) 0.1222(5) 0.5801(9) 0.027(3) Uani 1 1 d . . . . .
C31 C 0.2020(9) 0.1293(6) 0.5743(9) 0.043(4) Uani 1 1 d . . . . .
H31 H 0.167849 0.097601 0.591575 0.052 Uiso 1 1 calc R U . . .
C32 C 0.1504(9) 0.1831(7) 0.5428(11) 0.047(4) Uani 1 1 d . . . . .
H32 H 0.117464 0.200468 0.591234 0.057 Uiso 1 1 calc R U . . .
C33 C 0.0814(9) 0.2568(6) 0.4308(11) 0.055(5) Uani 1 1 d . . . . .
H33A H 0.056485 0.267168 0.493783 0.066 Uiso 1 1 calc R U . . .
H33B H 0.031903 0.243715 0.383814 0.066 Uiso 1 1 calc R U . . .
C34 C 0.1496(10) 0.1788(7) 0.2638(10) 0.059(5) Uani 1 1 d . . . . .
H34A H 0.192875 0.168724 0.215564 0.071 Uiso 1 1 calc R U . . .
H34B H 0.118770 0.213906 0.240528 0.071 Uiso 1 1 calc R U . . .
C35 C 0.3248(8) 0.0658(6) 0.6181(9) 0.037(4) Uani 1 1 d . . . . .
H35A H 0.274197 0.040556 0.629015 0.044 Uiso 1 1 calc R U . . .
H35B H 0.359986 0.071075 0.682582 0.044 Uiso 1 1 calc R U . . .
C36 C 0.4334(9) 0.1791(6) 0.6335(10) 0.046(4) Uani 1 1 d . . . . .
H36A H 0.467722 0.211588 0.610476 0.055 Uiso 1 1 calc R U . . .
H36B H 0.473099 0.145712 0.638535 0.055 Uiso 1 1 calc R U . . .
Br9 Br 0.39358(14) 0.19651(9) 0.76630(13) 0.0807(7) Uani 1 1 d . . . . .
Br10 Br 0.40054(11) 0.02982(7) 0.52124(14) 0.0631(6) Uani 1 1 d . . . . .
Br11 Br 0.06270(11) 0.11716(7) 0.27090(12) 0.0594(5) Uani 1 1 d . . . . .
Br12 Br 0.13616(14) 0.32497(8) 0.37510(18) 0.0880(7) Uani 1 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'
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
C2 C1 C10 118.8(14) . . ?
C2 C1 C8 123.0(13) . . ?
C10 C1 C8 118.2(13) . . ?
C1 C2 C3 127.2(14) . . ?
C1 C2 H2 116.4 . . ?
C3 C2 H2 116.4 . . ?
C4 C3 C2 126.4(13) . . ?
C4 C3 H3 116.8 . . ?
C2 C3 H3 116.8 . . ?
C3 C4 C12 121.5(14) . . ?
C3 C4 C5 122.4(13) . . ?
C12 C4 C5 116.1(14) . . ?
C6 C5 C4 125.7(13) . . ?
C6 C5 C11 117.2(13) . . ?
C4 C5 C11 117.1(12) . . ?
C5 C6 C7 123.9(13) . . ?
C5 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C8 C7 C6 126.4(15) . . ?
C8 C7 H7 116.8 . . ?
C6 C7 H7 116.8 . . ?
C7 C8 C1 124.6(14) . . ?
C7 C8 C9 118.1(14) . . ?
C1 C8 C9 117.2(13) . . ?
C8 C9 Br3 111.1(10) . . ?
C8 C9 H9A 109.4 . . ?
Br3 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
Br3 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C10 Br4 110.5(10) . . ?
C1 C10 H10A 109.5 . . ?
Br4 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
Br4 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C5 C11 Br1 110.9(9) . . ?
C5 C11 H11A 109.5 . . ?
Br1 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
Br1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C4 C12 Br2 110.4(10) . . ?
C4 C12 H12A 109.6 . . ?
Br2 C12 H12A 109.6 . . ?
C4 C12 H12B 109.6 . . ?
Br2 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C21 119.6(13) . . ?
C14 C13 C20 121.4(12) . . ?
C21 C13 C20 119.0(12) . . ?
C13 C14 C15 127.6(12) . . ?
C13 C14 H14 116.2 . . ?
C15 C14 H14 116.2 . . ?
C16 C15 C14 126.3(13) . . ?
C16 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C15 C16 C17 121.2(12) . . ?
C15 C16 C23 120.2(12) . . ?
C17 C16 C23 118.4(11) . . ?
C18 C17 C16 123.9(12) . . ?
C18 C17 C24 116.6(14) . . ?
C16 C17 C24 119.5(13) . . ?
C17 C18 C19 125.9(13) . . ?
C17 C18 H18 117.1 . . ?
C19 C18 H18 117.1 . . ?
C20 C19 C18 122.8(12) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C13 124.0(11) . . ?
C19 C20 C22 119.4(12) . . ?
C13 C20 C22 116.5(11) . . ?
C13 C21 Br6 112.5(9) . . ?
C13 C21 H21A 109.1 . . ?
Br6 C21 H21A 109.1 . . ?
C13 C21 H21B 109.1 . . ?
Br6 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C20 C22 Br5 113.6(8) . . ?
C20 C22 H22A 108.8 . . ?
Br5 C22 H22A 108.8 . . ?
C20 C22 H22B 108.8 . . ?
Br5 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C16 C23 Br8 111.3(9) . . ?
C16 C23 H23A 109.4 . . ?
Br8 C23 H23A 109.4 . . ?
C16 C23 H23B 109.4 . . ?
Br8 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C17 C24 Br7 109.0(9) . . ?
C17 C24 H24A 109.9 . . ?
Br7 C24 H24A 109.9 . . ?
C17 C24 H24B 109.9 . . ?
Br7 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C32 C25 C26 123.7(13) . . ?
C32 C25 C33 117.2(13) . . ?
C26 C25 C33 119.0(12) . . ?
C27 C26 C25 122.1(13) . . ?
C27 C26 C34 119.2(13) . . ?
C25 C26 C34 118.7(12) . . ?
C26 C27 C28 129.0(13) . . ?
C26 C27 H27 115.5 . . ?
C28 C27 H27 115.5 . . ?
C29 C28 C27 125.9(13) . . ?
C29 C28 H28 117.1 . . ?
C27 C28 H28 117.1 . . ?
C28 C29 C30 124.5(12) . . ?
C28 C29 C36 117.3(12) . . ?
C30 C29 C36 117.9(11) . . ?
C31 C30 C29 123.9(12) . . ?
C31 C30 C35 116.4(12) . . ?
C29 C30 C35 119.6(11) . . ?
C30 C31 C32 126.9(14) . . ?
C30 C31 H31 116.5 . . ?
C32 C31 H31 116.5 . . ?
C25 C32 C31 126.3(13) . . ?
C25 C32 H32 116.8 . . ?
C31 C32 H32 116.8 . . ?
C25 C33 Br12 112.6(9) . . ?
C25 C33 H33A 109.1 . . ?
Br12 C33 H33A 109.1 . . ?
C25 C33 H33B 109.1 . . ?
Br12 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C26 C34 Br11 110.0(9) . . ?
C26 C34 H34A 109.7 . . ?
Br11 C34 H34A 109.7 . . ?
C26 C34 H34B 109.7 . . ?
Br11 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
C30 C35 Br10 110.7(9) . . ?
C30 C35 H35A 109.5 . . ?
Br10 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
Br10 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C29 C36 Br9 111.6(9) . . ?
C29 C36 H36A 109.3 . . ?
Br9 C36 H36A 109.3 . . ?
C29 C36 H36B 109.3 . . ?
Br9 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
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
C1 C2 1.279(17) . ?
C1 C10 1.462(17) . ?
C1 C8 1.489(19) . ?
C2 C3 1.450(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(19) . ?
C3 H3 0.9300 . ?
C4 C12 1.444(18) . ?
C4 C5 1.463(19) . ?
C5 C6 1.357(17) . ?
C5 C11 1.526(18) . ?
C6 C7 1.451(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.300(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.51(2) . ?
C9 Br3 1.907(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 Br4 1.960(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 Br1 1.942(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 Br2 1.974(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.333(16) . ?
C13 C21 1.460(17) . ?
C13 C20 1.488(17) . ?
C14 C15 1.465(17) . ?
C14 H14 0.9300 . ?
C15 C16 1.271(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.472(18) . ?
C16 C23 1.503(17) . ?
C17 C18 1.320(18) . ?
C17 C24 1.477(17) . ?
C18 C19 1.478(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.346(16) . ?
C19 H19 0.9300 . ?
C20 C22 1.495(15) . ?
C21 Br6 1.943(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 Br5 1.920(12) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 Br8 1.955(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 Br7 1.976(15) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C32 1.358(18) . ?
C25 C26 1.463(18) . ?
C25 C33 1.486(17) . ?
C26 C27 1.340(17) . ?
C26 C34 1.523(18) . ?
C27 C28 1.474(17) . ?
C27 H27 0.9300 . ?
C28 C29 1.305(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.449(17) . ?
C29 C36 1.521(16) . ?
C30 C31 1.315(17) . ?
C30 C35 1.475(17) . ?
C31 C32 1.501(18) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 Br12 1.946(14) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 Br11 1.928(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 Br10 1.960(12) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 Br9 1.944(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10B Br10 0.97 3.13 4.100(17) 176.6 2_655 yes
C12 H12B Br6 0.97 2.99 3.742(15) 135.3 1_554 yes
C22 H22B Br6 0.97 3.09 4.037(13) 165.1 3_566 yes
C23 H23A Br4 0.97 2.99 3.901(13) 157.0 3_666 yes
C33 H33B Br2 0.97 3.02 3.877(14) 148.5 3_565 yes
C34 H34B Br2 0.97 3.05 3.838(14) 138.9 3_565 yes
C34 H34B Br12 0.97 3.13 3.702(16) 119.6 . yes
C35 H35A Br5 0.97 3.06 3.912(13) 147.9 4_566 yes
C35 H35B Br9 0.97 3.13 3.701(13) 119.1 . yes
C36 H36A Br3 0.97 3.05 4.011(14) 169.0 2_645 yes
C36 H36B Br7 0.97 3.01 3.832(14) 142.8 2_646 yes
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
C10 C1 C2 C3 -178.6(13) . . . . ?
C8 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C4 -61(2) . . . . ?
C2 C3 C4 C12 177.7(13) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 58(2) . . . . ?
C12 C4 C5 C6 -120.3(15) . . . . ?
C3 C4 C5 C11 -121.6(14) . . . . ?
C12 C4 C5 C11 60.0(17) . . . . ?
C4 C5 C6 C7 2(2) . . . . ?
C11 C5 C6 C7 -178.2(13) . . . . ?
C5 C6 C7 C8 -62(2) . . . . ?
C6 C7 C8 C1 -2(2) . . . . ?
C6 C7 C8 C9 -179.6(13) . . . . ?
C2 C1 C8 C7 62(2) . . . . ?
C10 C1 C8 C7 -118.1(15) . . . . ?
C2 C1 C8 C9 -120.1(16) . . . . ?
C10 C1 C8 C9 59.3(17) . . . . ?
C7 C8 C9 Br3 -117.1(13) . . . . ?
C1 C8 C9 Br3 65.3(15) . . . . ?
C2 C1 C10 Br4 -107.8(14) . . . . ?
C8 C1 C10 Br4 72.7(15) . . . . ?
C6 C5 C11 Br1 -115.8(12) . . . . ?
C4 C5 C11 Br1 63.8(14) . . . . ?
C3 C4 C12 Br2 -102.6(15) . . . . ?
C5 C4 C12 Br2 75.7(14) . . . . ?
C21 C13 C14 C15 -176.0(12) . . . . ?
C20 C13 C14 C15 4(2) . . . . ?
C13 C14 C15 C16 -67(2) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
C14 C15 C16 C23 -173.1(12) . . . . ?
C15 C16 C17 C18 61(2) . . . . ?
C23 C16 C17 C18 -124.3(15) . . . . ?
C15 C16 C17 C24 -119.5(15) . . . . ?
C23 C16 C17 C24 55.4(18) . . . . ?
C16 C17 C18 C19 1(2) . . . . ?
C24 C17 C18 C19 -178.3(12) . . . . ?
C17 C18 C19 C20 -67(2) . . . . ?
C18 C19 C20 C13 4.1(19) . . . . ?
C18 C19 C20 C22 -171.1(11) . . . . ?
C14 C13 C20 C19 55.3(18) . . . . ?
C21 C13 C20 C19 -124.5(14) . . . . ?
C14 C13 C20 C22 -129.3(13) . . . . ?
C21 C13 C20 C22 50.9(15) . . . . ?
C14 C13 C21 Br6 -122.2(11) . . . . ?
C20 C13 C21 Br6 57.5(14) . . . . ?
C19 C20 C22 Br5 -129.7(11) . . . . ?
C13 C20 C22 Br5 54.7(13) . . . . ?
C15 C16 C23 Br8 -127.5(12) . . . . ?
C17 C16 C23 Br8 57.6(14) . . . . ?
C18 C17 C24 Br7 -114.6(13) . . . . ?
C16 C17 C24 Br7 65.7(14) . . . . ?
C32 C25 C26 C27 -54(2) . . . . ?
C33 C25 C26 C27 130.8(14) . . . . ?
C32 C25 C26 C34 129.0(14) . . . . ?
C33 C25 C26 C34 -46.0(18) . . . . ?
C25 C26 C27 C28 -2(2) . . . . ?
C34 C26 C27 C28 174.4(13) . . . . ?
C26 C27 C28 C29 65(2) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
C27 C28 C29 C36 170.4(12) . . . . ?
C28 C29 C30 C31 -57(2) . . . . ?
C36 C29 C30 C31 129.7(14) . . . . ?
C28 C29 C30 C35 126.0(14) . . . . ?
C36 C29 C30 C35 -47.1(17) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C35 C30 C31 C32 177.1(12) . . . . ?
C26 C25 C32 C31 -4(2) . . . . ?
C33 C25 C32 C31 171.4(13) . . . . ?
C30 C31 C32 C25 63(2) . . . . ?
C32 C25 C33 Br12 130.8(12) . . . . ?
C26 C25 C33 Br12 -53.9(16) . . . . ?
C27 C26 C34 Br11 119.3(12) . . . . ?
C25 C26 C34 Br11 -63.8(14) . . . . ?
C31 C30 C35 Br10 124.9(11) . . . . ?
C29 C30 C35 Br10 -58.1(14) . . . . ?
C28 C29 C36 Br9 131.4(11) . . . . ?
C30 C29 C36 Br9 -55.0(14) . . . . ?
