#------------------------------------------------------------------------------
#$Date: 2024-04-16 04:33:24 +0300 (Tue, 16 Apr 2024) $
#$Revision: 291219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248416.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_7248416
loop_
_publ_author_name
'Silber, Vincent'
'Gourlaouen, Christophe'
'Ruppert, Romain'
_publ_section_title
;
 Keto--enol equilibrium: stable tautomers of ortho-, meta-, and
 para-hydroquinones in large aromatics
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              11969
_journal_page_last               11976
_journal_paper_doi               10.1039/D4RA02202E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C28 H19 Br O2'
_chemical_formula_sum            'C28 H19 Br O2'
_chemical_formula_weight         467.34
_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_block_doi                 10.5517/ccdc.csd.cc287sx7
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-07 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6897(5)
_cell_length_b                   14.0457(6)
_cell_length_c                   20.6528(7)
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.43
_cell_volume                     4126.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91304
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.924
_diffrn_reflns_theta_min         2.036
_exptl_absorpt_coefficient_mu    2.016
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+3.7757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8445
_reflns_number_total             9892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02202e2.cif
_cod_data_source_block           mo_JWVS210111_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248416
_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   0.689
_shelx_estimated_absorpt_t_max   0.752
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 0.78280(11) 0.34557(12) 0.55939(8) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.87211(11) 0.30183(12) 0.58490(8) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.88982(11) 0.25500(13) 0.64529(8) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.82500(12) 0.25044(13) 0.68487(8) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.838500 0.215112 0.725370 0.021 Uiso 1 1 calc R U . . .
C5 C 0.74152(12) 0.29845(13) 0.66344(8) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.72067(11) 0.35019(12) 0.60216(8) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.64181(12) 0.41335(13) 0.58730(9) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.598097 0.413267 0.614319 0.021 Uiso 1 1 calc R U . . .
C8 C 0.62989(11) 0.47299(13) 0.53471(9) 0.0171(3) Uani 1 1 d . . . . .
H8 H 0.583388 0.521398 0.528960 0.021 Uiso 1 1 calc R U . . .
C9 C 0.68584(12) 0.46483(12) 0.48744(8) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.67048(12) 0.53010(13) 0.43322(9) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.622213 0.576566 0.428110 0.023 Uiso 1 1 calc R U . . .
C11 C 0.72442(13) 0.52632(13) 0.38878(9) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.719792 0.575383 0.356454 0.024 Uiso 1 1 calc R U . . .
C12 C 0.78778(12) 0.44965(13) 0.39015(8) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.84471(12) 0.44855(13) 0.34338(8) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.838807 0.498199 0.311359 0.023 Uiso 1 1 calc R U . . .
C14 C 0.90701(12) 0.37738(14) 0.34427(8) 0.0195(4) Uani 1 1 d . . . . .
H14 H 0.951810 0.382502 0.318282 0.023 Uiso 1 1 calc R U . . .
C15 C 0.90570(12) 0.29470(13) 0.38405(8) 0.0166(3) Uani 1 1 d . . . . .
C16 C 0.96567(12) 0.21611(14) 0.37916(9) 0.0210(4) Uani 1 1 d . . . . .
H16 H 1.010575 0.222551 0.353360 0.025 Uiso 1 1 calc R U . . .
C17 C 0.95945(12) 0.13282(14) 0.41068(9) 0.0212(4) Uani 1 1 d . . . . .
H17 H 1.003546 0.083484 0.410286 0.025 Uiso 1 1 calc R U . . .
C18 C 0.88658(12) 0.11883(13) 0.44462(8) 0.0177(3) Uani 1 1 d . . . . .
C19 C 0.87271(13) 0.02828(13) 0.47052(9) 0.0211(4) Uani 1 1 d . . . . .
H19 H 0.916109 -0.021528 0.469547 0.025 Uiso 1 1 calc R U . . .
C20 C 0.79734(13) 0.01141(13) 0.49705(9) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.790441 -0.048646 0.516445 0.026 Uiso 1 1 calc R U . . .
C21 C 0.73055(13) 0.08343(13) 0.49535(9) 0.0205(4) Uani 1 1 d . . . . .
H21 H 0.675778 0.070360 0.510406 0.025 Uiso 1 1 calc R U . . .
C22 C 0.74382(12) 0.17288(13) 0.47202(8) 0.0169(3) Uani 1 1 d . . . . .
H22 H 0.697862 0.220742 0.471221 0.020 Uiso 1 1 calc R U . . .
C23 C 0.82451(11) 0.19498(12) 0.44920(8) 0.0147(3) Uani 1 1 d . . . . .
C24 C 0.84232(11) 0.28885(12) 0.42552(8) 0.0147(3) Uani 1 1 d . . . . .
C25 C 0.79489(11) 0.37486(12) 0.43772(8) 0.0145(3) Uani 1 1 d . . . . .
C26 C 0.75464(11) 0.39257(12) 0.49417(8) 0.0136(3) Uani 1 1 d . . . . .
O1 O 0.94253(8) 0.30734(8) 0.55186(6) 0.0144(2) Uani 1 1 d . . . . .
C27 C 0.98439(12) 0.39991(13) 0.55512(10) 0.0224(4) Uani 1 1 d . . . . .
H27A H 0.935615 0.447252 0.537184 0.034 Uiso 1 1 calc R U . . .
H27B H 1.031262 0.400416 0.528666 0.034 Uiso 1 1 calc R U . . .
H27C H 1.014917 0.415374 0.601754 0.034 Uiso 1 1 calc R U . . .
Br1 Br 1.00749(2) 0.19373(2) 0.67886(2) 0.02717(6) Uani 1 1 d . . . . .
O2 O 0.67376(9) 0.30244(10) 0.69832(6) 0.0214(3) Uani 1 1 d . . . . .
C28 C 0.69728(13) 0.26522(15) 0.76501(9) 0.0236(4) Uani 1 1 d . . . . .
H28A H 0.708659 0.196582 0.763653 0.035 Uiso 1 1 calc R U . . .
H28B H 0.645193 0.276805 0.785812 0.035 Uiso 1 1 calc R U . . .
H28C H 0.754082 0.296802 0.791198 0.035 Uiso 1 1 calc R U . . .
C29 C 0.29080(11) 0.18347(12) 0.87065(8) 0.0146(3) Uani 1 1 d . . . . .
C30 C 0.37437(11) 0.23422(12) 0.90091(8) 0.0153(3) Uani 1 1 d . . . . .
C31 C 0.38083(12) 0.27802(13) 0.96141(9) 0.0188(3) Uani 1 1 d . . . . .
C32 C 0.31020(12) 0.27210(13) 0.99599(9) 0.0193(3) Uani 1 1 d . . . . .
H32 H 0.315502 0.306278 1.036459 0.023 Uiso 1 1 calc R U . . .
C33 C 0.23335(12) 0.21607(12) 0.97030(8) 0.0161(3) Uani 1 1 d . . . . .
C34 C 0.22401(12) 0.16711(12) 0.90865(8) 0.0156(3) Uani 1 1 d . . . . .
C35 C 0.15133(12) 0.09838(13) 0.88620(9) 0.0185(3) Uani 1 1 d . . . . .
H35 H 0.104401 0.090020 0.910105 0.022 Uiso 1 1 calc R U . . .
C36 C 0.14872(12) 0.04511(13) 0.83123(9) 0.0209(4) Uani 1 1 d . . . . .
H36 H 0.105693 -0.006440 0.820629 0.025 Uiso 1 1 calc R U . . .
C37 C 0.20989(12) 0.06531(13) 0.78878(9) 0.0192(3) Uani 1 1 d . . . . .
C38 C 0.20904(14) 0.00809(14) 0.73152(9) 0.0241(4) Uani 1 1 d . . . . .
H38 H 0.165638 -0.043046 0.720248 0.029 Uiso 1 1 calc R U . . .
C39 C 0.26978(14) 0.02611(14) 0.69296(9) 0.0250(4) Uani 1 1 d . . . . .
H39 H 0.276220 -0.018515 0.659820 0.030 Uiso 1 1 calc R U . . .
C40 C 0.32387(13) 0.11156(13) 0.70195(8) 0.0200(4) Uani 1 1 d . . . . .
C41 C 0.38801(13) 0.13269(14) 0.66218(9) 0.0237(4) Uani 1 1 d . . . . .
H41 H 0.395391 0.088779 0.628876 0.028 Uiso 1 1 calc R U . . .
C42 C 0.43859(13) 0.21454(15) 0.67124(9) 0.0235(4) Uani 1 1 d . . . . .
H42 H 0.487136 0.223456 0.648852 0.028 Uiso 1 1 calc R U . . .
C43 C 0.41941(12) 0.28735(13) 0.71415(8) 0.0190(3) Uani 1 1 d . . . . .
C44 C 0.46989(12) 0.37522(15) 0.72249(9) 0.0233(4) Uani 1 1 d . . . . .
H44 H 0.519287 0.383979 0.700875 0.028 Uiso 1 1 calc R U . . .
C45 C 0.44882(13) 0.44624(15) 0.76053(9) 0.0248(4) Uani 1 1 d . . . . .
H45 H 0.487789 0.501099 0.769354 0.030 Uiso 1 1 calc R U . . .
C46 C 0.36848(13) 0.43954(13) 0.78759(9) 0.0206(4) Uani 1 1 d . . . . .
C47 C 0.33839(16) 0.51809(14) 0.81985(10) 0.0278(4) Uani 1 1 d . . . . .
H47 H 0.376204 0.573769 0.828432 0.033 Uiso 1 1 calc R U . . .
C48 C 0.25549(16) 0.51495(14) 0.83888(10) 0.0288(4) Uani 1 1 d . . . . .
H48 H 0.237067 0.567357 0.861778 0.035 Uiso 1 1 calc R U . . .
C49 C 0.19800(14) 0.43419(14) 0.82445(9) 0.0245(4) Uani 1 1 d . . . . .
H49 H 0.138814 0.433597 0.835256 0.029 Uiso 1 1 calc R U . . .
C50 C 0.22650(12) 0.35572(13) 0.79478(9) 0.0183(3) Uani 1 1 d . . . . .
H50 H 0.186461 0.301732 0.785031 0.022 Uiso 1 1 calc R U . . .
C51 C 0.31478(12) 0.35426(12) 0.77854(8) 0.0160(3) Uani 1 1 d . . . . .
C52 C 0.34912(11) 0.27250(13) 0.74894(8) 0.0155(3) Uani 1 1 d . . . . .
C53 C 0.31447(12) 0.17706(13) 0.75210(8) 0.0163(3) Uani 1 1 d . . . . .
C54 C 0.27185(11) 0.14332(12) 0.80357(8) 0.0155(3) Uani 1 1 d . . . . .
O3 O 0.44865(8) 0.24154(9) 0.87172(6) 0.0181(2) Uani 1 1 d . . . . .
C55 C 0.50425(14) 0.15697(16) 0.87692(12) 0.0317(5) Uani 1 1 d . . . . .
H55A H 0.531367 0.142187 0.924174 0.048 Uiso 1 1 calc R U . . .
H55B H 0.554916 0.166885 0.854466 0.048 Uiso 1 1 calc R U . . .
H55C H 0.464573 0.103897 0.855674 0.048 Uiso 1 1 calc R U . . .
Br2 Br 0.49010(2) 0.34882(2) 1.00137(2) 0.03618(7) Uani 1 1 d . . . . .
O4 O 0.16214(9) 0.20227(10) 1.00090(6) 0.0214(3) Uani 1 1 d . . . . .
C56 C 0.16833(14) 0.25432(14) 1.06161(10) 0.0255(4) Uani 1 1 d . . . . .
H56A H 0.222357 0.231467 1.096193 0.038 Uiso 1 1 calc R U . . .
H56B H 0.110634 0.244805 1.076488 0.038 Uiso 1 1 calc R U . . .
H56C H 0.176211 0.322246 1.053620 0.038 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_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC01475K 2022
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
C6 C1 C2 117.68(14) . . ?
C6 C1 C26 118.25(14) . . ?
C2 C1 C26 123.87(14) . . ?
C3 C2 O1 118.73(14) . . ?
C3 C2 C1 119.31(15) . . ?
O1 C2 C1 121.93(14) . . ?
C2 C3 C4 123.20(15) . . ?
C2 C3 Br1 119.76(12) . . ?
C4 C3 Br1 117.04(12) . . ?
C5 C4 C3 118.13(15) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
O2 C5 C4 124.02(15) . . ?
O2 C5 C6 115.05(15) . . ?
C4 C5 C6 120.92(15) . . ?
C1 C6 C5 119.98(15) . . ?
C1 C6 C7 120.42(15) . . ?
C5 C6 C7 119.35(15) . . ?
C8 C7 C6 119.59(15) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.29(16) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C26 C9 C10 120.63(15) . . ?
C26 C9 C8 120.60(15) . . ?
C10 C9 C8 118.77(16) . . ?
C11 C10 C9 120.25(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.51(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C25 120.56(15) . . ?
C11 C12 C13 119.14(16) . . ?
C25 C12 C13 120.30(16) . . ?
C14 C13 C12 120.51(16) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.25(16) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C24 C15 C14 120.08(16) . . ?
C24 C15 C16 120.47(16) . . ?
C14 C15 C16 119.38(16) . . ?
C17 C16 C15 121.08(16) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.18(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C23 119.70(16) . . ?
C19 C18 C17 120.30(16) . . ?
C23 C18 C17 119.91(16) . . ?
C20 C19 C18 120.85(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.60(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.48(16) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 121.35(16) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 117.44(16) . . ?
C22 C23 C24 123.20(15) . . ?
C18 C23 C24 119.17(15) . . ?
C15 C24 C25 118.33(15) . . ?
C15 C24 C23 117.20(15) . . ?
C25 C24 C23 124.33(15) . . ?
C12 C25 C24 116.81(15) . . ?
C12 C25 C26 116.90(15) . . ?
C24 C25 C26 126.29(15) . . ?
C9 C26 C25 117.86(15) . . ?
C9 C26 C1 116.42(14) . . ?
C25 C26 C1 125.62(15) . . ?
C2 O1 C27 113.23(13) . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C5 O2 C28 117.31(13) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 118.56(15) . . ?
C34 C29 C54 117.94(15) . . ?
C30 C29 C54 123.44(15) . . ?
C31 C30 O3 118.84(15) . . ?
C31 C30 C29 118.68(15) . . ?
O3 C30 C29 122.48(15) . . ?
C30 C31 C32 123.01(16) . . ?
C30 C31 Br2 119.35(13) . . ?
C32 C31 Br2 117.64(13) . . ?
C33 C32 C31 118.69(16) . . ?
C33 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
O4 C33 C32 123.73(16) . . ?
O4 C33 C34 115.58(15) . . ?
C32 C33 C34 120.69(15) . . ?
C29 C34 C33 119.38(15) . . ?
C29 C34 C35 119.58(16) . . ?
C33 C34 C35 120.96(15) . . ?
C36 C35 C34 120.60(16) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 120.91(17) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C54 C37 C38 119.31(16) . . ?
C54 C37 C36 119.45(16) . . ?
C38 C37 C36 121.24(17) . . ?
C39 C38 C37 120.60(18) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.41(17) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C53 C40 C39 119.26(17) . . ?
C53 C40 C41 118.96(17) . . ?
C39 C40 C41 121.78(17) . . ?
C42 C41 C40 120.97(17) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C43 120.47(17) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C52 C43 C42 119.52(17) . . ?
C52 C43 C44 119.32(17) . . ?
C42 C43 C44 121.16(16) . . ?
C45 C44 C43 121.35(17) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C45 C46 120.62(18) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C47 C46 C51 119.39(17) . . ?
C47 C46 C45 121.19(18) . . ?
C51 C46 C45 119.32(17) . . ?
C48 C47 C46 120.93(19) . . ?
C48 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C47 C48 C49 119.77(18) . . ?
C47 C48 H48 120.1 . . ?
C49 C48 H48 120.1 . . ?
C50 C49 C48 120.59(18) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C49 C50 C51 120.97(18) . . ?
C49 C50 H50 119.5 . . ?
C51 C50 H50 119.5 . . ?
C50 C51 C46 117.85(16) . . ?
C50 C51 C52 123.10(16) . . ?
C46 C51 C52 118.90(15) . . ?
C43 C52 C53 118.14(16) . . ?
C43 C52 C51 118.22(16) . . ?
C53 C52 C51 123.64(15) . . ?
C40 C53 C52 118.08(15) . . ?
C40 C53 C54 117.70(16) . . ?
C52 C53 C54 124.22(15) . . ?
C37 C54 C53 118.15(16) . . ?
C37 C54 C29 117.86(15) . . ?
C53 C54 C29 123.97(15) . . ?
C30 O3 C55 113.93(14) . . ?
O3 C55 H55A 109.5 . . ?
O3 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
O3 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C33 O4 C56 116.35(14) . . ?
O4 C56 H56A 109.5 . . ?
O4 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
O4 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
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
C1 C6 1.421(2) . ?
C1 C2 1.425(2) . ?
C1 C26 1.464(2) . ?
C2 C3 1.376(2) . ?
C2 O1 1.3762(19) . ?
C3 C4 1.403(2) . ?
C3 Br1 1.9003(16) . ?
C4 C5 1.373(2) . ?
C4 H4 0.9500 . ?
C5 O2 1.368(2) . ?
C5 C6 1.425(2) . ?
C6 C7 1.430(2) . ?
C7 C8 1.348(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.429(2) . ?
C8 H8 0.9500 . ?
C9 C26 1.415(2) . ?
C9 C10 1.421(2) . ?
C10 C11 1.355(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(3) . ?
C11 H11 0.9500 . ?
C12 C25 1.424(2) . ?
C12 C13 1.427(2) . ?
C13 C14 1.352(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.425(2) . ?
C14 H14 0.9500 . ?
C15 C24 1.416(2) . ?
C15 C16 1.431(3) . ?
C16 C17 1.353(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.432(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.414(3) . ?
C18 C23 1.424(2) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.404(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.415(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.453(2) . ?
C24 C25 1.448(2) . ?
C25 C26 1.454(2) . ?
O1 C27 1.433(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O2 C28 1.433(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.420(2) . ?
C29 C30 1.422(2) . ?
C29 C54 1.457(2) . ?
C30 C31 1.375(2) . ?
C30 O3 1.3757(19) . ?
C31 C32 1.401(2) . ?
C31 Br2 1.8936(17) . ?
C32 C33 1.370(2) . ?
C32 H32 0.9500 . ?
C33 O4 1.3642(19) . ?
C33 C34 1.423(2) . ?
C34 C35 1.428(2) . ?
C35 C36 1.352(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.432(2) . ?
C36 H36 0.9500 . ?
C37 C54 1.408(2) . ?
C37 C38 1.427(3) . ?
C38 C39 1.360(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.426(3) . ?
C39 H39 0.9500 . ?
C40 C53 1.418(2) . ?
C40 C41 1.427(3) . ?
C41 C42 1.356(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.427(3) . ?
C42 H42 0.9500 . ?
C43 C52 1.413(2) . ?
C43 C44 1.428(3) . ?
C44 C45 1.353(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.429(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.415(3) . ?
C46 C51 1.421(3) . ?
C47 C48 1.370(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.401(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.376(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.418(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.449(2) . ?
C52 C53 1.441(2) . ?
C53 C54 1.442(2) . ?
O3 C55 1.430(2) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
O4 C56 1.435(2) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
