# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kd2shape
_database_code_depnum_ccdc_archive 'CCDC 2088560'
loop_
_audit_author_name
_audit_author_address
'Tadeusz Muziol'
;Nicolaus Copernicus University in Torun, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H15 Br O5'
_chemical_formula_sum            'C19 H15 Br O5'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         403.22

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   17.401(8)
_cell_length_b                   5.9984(13)
_cell_length_c                   18.889(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.06(5)
_cell_angle_gamma                90
_cell_volume                     1786.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2406
_cell_measurement_theta_min      2.1760
_cell_measurement_theta_max      22.2770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.327
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.34a (2015)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11460
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             6739
_reflns_number_gt                3655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.822
_reflns_Friedel_fraction_full    0.844

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_cell_refinement       ?
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ciftab
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(13)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6739
_refine_ls_number_parameters     466
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.86774(9) 0.1259(2) 0.58360(7) 0.1155(5) Uani 1 1 d . . . . .
C1 C 0.8791(6) 0.1682(17) 0.4901(5) 0.076(3) Uani 1 1 d . . . . .
C2 C 0.9248(6) 0.0160(15) 0.4686(5) 0.077(3) Uani 1 1 d . . . . .
H2 H 0.948527 -0.107055 0.500323 0.093 Uiso 1 1 calc R U . . .
C3 C 0.9359(6) 0.0424(13) 0.4018(5) 0.073(3) Uani 1 1 d . . . . .
H3 H 0.966971 -0.060652 0.387892 0.087 Uiso 1 1 calc R U . . .
C4 C 0.8995(6) 0.2281(12) 0.3549(4) 0.056(2) Uani 1 1 d . . . . .
O5 O 0.9122(4) 0.2499(8) 0.2890(3) 0.0641(16) Uani 1 1 d . . . . .
C6 C 0.8808(6) 0.4318(13) 0.2411(4) 0.057(2) Uani 1 1 d . . . . .
C7 C 0.8377(5) 0.5906(12) 0.2586(4) 0.053(2) Uani 1 1 d . . . . .
O7 O 0.8105(4) 0.7736(10) 0.2100(4) 0.0646(16) Uani 1 1 d D . . . .
H7 H 0.776(5) 0.832(15) 0.218(5) 0.078 Uiso 1 1 d D U . . .
C8 C 0.8152(6) 0.5739(13) 0.3225(4) 0.058(2) Uani 1 1 d . . . . .
O8 O 0.7688(4) 0.7103(9) 0.3343(3) 0.0736(17) Uani 1 1 d . . . . .
C9 C 0.8524(5) 0.3835(13) 0.3740(5) 0.057(2) Uani 1 1 d . . . . .
C10 C 0.8408(6) 0.3505(14) 0.4430(5) 0.065(2) Uani 1 1 d . . . . .
H10 H 0.808151 0.449245 0.456605 0.078 Uiso 1 1 calc R U . . .
C11 C 0.9009(6) 0.4218(14) 0.1717(4) 0.057(2) Uani 1 1 d . . . . .
H11 H 0.872513 0.547562 0.137425 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8642(6) 0.2056(12) 0.1266(5) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.891696 0.079497 0.159883 0.078 Uiso 1 1 calc R U . . .
H12B H 0.804165 0.198052 0.114381 0.078 Uiso 1 1 calc R U . . .
O14 O 0.8721(6) 0.3371(16) 0.0110(4) 0.129(3) Uani 1 1 d . . . . .
C13 C 0.8750(7) 0.1873(17) 0.0534(5) 0.079(3) Uani 1 1 d . . . . .
O15 O 0.8878(5) -0.0217(12) 0.0388(4) 0.102(2) Uani 1 1 d . . . . .
C16 C 0.8954(10) -0.065(2) -0.0337(7) 0.154(6) Uani 1 1 d . . . . .
H16A H 0.846660 -0.006215 -0.076832 0.231 Uiso 1 1 calc R U . . .
H16B H 0.898840 -0.222799 -0.040312 0.231 Uiso 1 1 calc R U . . .
H16C H 0.945725 0.005560 -0.031935 0.231 Uiso 1 1 calc R U . . .
C21 C 0.9958(6) 0.4449(14) 0.1963(5) 0.062(2) Uani 1 1 d . . . . .
C22 C 1.0286(7) 0.6453(18) 0.1868(6) 0.091(3) Uani 1 1 d . . . . .
H22 H 0.991931 0.764463 0.164967 0.109 Uiso 1 1 calc R U . . .
C23 C 1.1134(9) 0.674(2) 0.2084(8) 0.113(4) Uani 1 1 d . . . . .
H23 H 1.133436 0.807598 0.197389 0.135 Uiso 1 1 calc R U . . .
C24 C 1.1694(9) 0.505(3) 0.2466(8) 0.117(5) Uani 1 1 d . . . . .
H24 H 1.227586 0.527925 0.266152 0.140 Uiso 1 1 calc R U . . .
C25 C 1.1381(9) 0.305(3) 0.2552(7) 0.117(4) Uani 1 1 d . . . . .
H25 H 1.175003 0.185800 0.277089 0.140 Uiso 1 1 calc R U . . .
C26 C 1.0528(8) 0.276(2) 0.2321(7) 0.096(3) Uani 1 1 d . . . . .
H26 H 1.032848 0.139088 0.240622 0.115 Uiso 1 1 calc R U . . .
Br2 Br 0.63966(8) 0.80185(18) -0.00810(6) 0.1019(4) Uani 1 1 d . . . . .
C31 C 0.6062(6) 0.7021(14) 0.0695(5) 0.067(3) Uani 1 1 d . . . . .
C32 C 0.5460(6) 0.8270(15) 0.0833(5) 0.074(2) Uani 1 1 d . . . . .
H32 H 0.523781 0.956810 0.055078 0.088 Uiso 1 1 calc R U . . .
C33 C 0.5201(6) 0.7572(14) 0.1381(5) 0.073(3) Uani 1 1 d . . . . .
H33 H 0.479829 0.838587 0.147432 0.088 Uiso 1 1 calc R U . . .
C34 C 0.5542(6) 0.5632(13) 0.1805(5) 0.063(2) Uani 1 1 d . . . . .
O35 O 0.5267(4) 0.5013(9) 0.2350(3) 0.0669(16) Uani 1 1 d . . . . .
C36 C 0.5590(5) 0.3169(15) 0.2795(5) 0.064(2) Uani 1 1 d . . . . .
C37 C 0.6198(6) 0.1893(13) 0.2723(5) 0.063(2) Uani 1 1 d . . . . .
O37 O 0.6497(5) 0.0121(10) 0.3202(4) 0.080(2) Uani 1 1 d D . . . .
H37 H 0.685(6) -0.054(16) 0.311(6) 0.096 Uiso 1 1 d D U . . .
C38 C 0.6506(6) 0.2408(12) 0.2143(5) 0.057(2) Uani 1 1 d . . . . .
O38 O 0.7074(4) 0.1240(9) 0.2086(3) 0.0626(14) Uani 1 1 d . . . . .
C39 C 0.6146(5) 0.4389(13) 0.1681(5) 0.056(2) Uani 1 1 d . . . . .
C40 C 0.6397(6) 0.5084(14) 0.1101(5) 0.063(2) Uani 1 1 d . . . . .
H40 H 0.678421 0.424793 0.099181 0.075 Uiso 1 1 calc R U . . .
C41 C 0.5230(6) 0.2727(15) 0.3377(5) 0.073(3) Uani 1 1 d . . . . .
H41 H 0.525249 0.110988 0.345832 0.088 Uiso 1 1 calc R U . . .
C42 C 0.4305(6) 0.340(2) 0.3079(6) 0.096(3) Uani 1 1 d . . . . .
H42A H 0.411827 0.312494 0.348776 0.115 Uiso 1 1 calc R U . . .
H42B H 0.426056 0.499341 0.297707 0.115 Uiso 1 1 calc R U . . .
C43 C 0.3735(10) 0.224(3) 0.2371(10) 0.157(8) Uani 1 1 d D U . . .
O44 O 0.3338(14) 0.365(3) 0.1812(14) 0.182(9) Uani 0.6 1 d D . P A 1
O45 O 0.3589(14) 0.028(3) 0.229(2) 0.168(9) Uani 0.6 1 d D . P A 1
C46 C 0.3056(17) -0.080(4) 0.1596(15) 0.127(8) Uani 0.6 1 d D . P A 1
H46A H 0.255587 0.008475 0.132748 0.191 Uiso 0.6 1 calc R U P A 1
H46B H 0.289772 -0.223534 0.171499 0.191 Uiso 0.6 1 calc R U P A 1
H46C H 0.335084 -0.097723 0.127032 0.191 Uiso 0.6 1 calc R U P A 1
O47 O 0.400(2) 0.035(5) 0.241(3) 0.168(9) Uani 0.4 1 d D . P A 2
O48 O 0.3074(19) 0.262(5) 0.179(2) 0.182(9) Uani 0.4 1 d D . P A 2
C49 C 0.269(3) 0.036(5) 0.151(3) 0.127(8) Uani 0.4 1 d D . P A 2
H49A H 0.223249 0.050082 0.099421 0.191 Uiso 0.4 1 calc R U P A 2
H49B H 0.247166 -0.022637 0.185930 0.191 Uiso 0.4 1 calc R U P A 2
H49C H 0.311179 -0.062579 0.148668 0.191 Uiso 0.4 1 calc R U P A 2
C51 C 0.5757(6) 0.3771(15) 0.4164(6) 0.073(3) Uani 1 1 d . . . . .
C52 C 0.6180(7) 0.577(2) 0.4238(7) 0.095(4) Uani 1 1 d . . . . .
H52 H 0.616007 0.649033 0.379450 0.114 Uiso 1 1 calc R U . . .
C53 C 0.6626(8) 0.669(3) 0.4954(10) 0.124(5) Uani 1 1 d . . . . .
H53 H 0.689405 0.805529 0.499498 0.149 Uiso 1 1 calc R U . . .
C54 C 0.6683(10) 0.562(4) 0.5616(10) 0.145(7) Uani 1 1 d . . . . .
H54 H 0.701596 0.623076 0.610391 0.174 Uiso 1 1 calc R U . . .
C55 C 0.6257(12) 0.368(4) 0.5565(9) 0.162(7) Uani 1 1 d . . . . .
H55 H 0.627204 0.299645 0.601225 0.194 Uiso 1 1 calc R U . . .
C56 C 0.5800(8) 0.275(2) 0.4834(8) 0.114(4) Uani 1 1 d . . . . .
H56 H 0.551598 0.141025 0.479501 0.136 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.876(9) . ?
C1 C2 1.379(13) . ?
C1 C10 1.389(12) . ?
C2 C3 1.363(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(10) . ?
C3 H3 0.9300 . ?
C4 O5 1.359(9) . ?
C4 C9 1.386(11) . ?
O5 C6 1.374(9) . ?
C6 C7 1.337(11) . ?
C6 C11 1.494(11) . ?
C7 O7 1.380(9) . ?
C7 C8 1.422(11) . ?
O7 H7 0.76(6) . ?
C8 O8 1.234(9) . ?
C8 C9 1.461(11) . ?
C9 C10 1.414(11) . ?
C10 H10 0.9300 . ?
C11 C21 1.521(12) . ?
C11 C12 1.534(11) . ?
C11 H11 0.9800 . ?
C12 C13 1.478(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O14 C13 1.190(12) . ?
C13 O15 1.323(11) . ?
O15 C16 1.454(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C21 C22 1.374(13) . ?
C21 C26 1.380(13) . ?
C22 C23 1.367(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(17) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(18) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(15) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
Br2 C31 1.888(9) . ?
C31 C40 1.378(11) . ?
C31 C32 1.400(12) . ?
C32 C33 1.359(12) . ?
C32 H32 0.9300 . ?
C33 C34 1.394(11) . ?
C33 H33 0.9300 . ?
C34 O35 1.358(9) . ?
C34 C39 1.387(11) . ?
O35 C36 1.359(10) . ?
C36 C37 1.359(11) . ?
C36 C41 1.502(11) . ?
C37 O37 1.349(10) . ?
C37 C38 1.442(11) . ?
O37 H37 0.81(6) . ?
C38 O38 1.253(9) . ?
C38 C39 1.450(11) . ?
C39 C40 1.404(11) . ?
C40 H40 0.9300 . ?
C41 C51 1.513(12) . ?
C41 C42 1.518(13) . ?
C41 H41 0.9800 . ?
C42 C43 1.46(2) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 O48 1.23(2) . ?
C43 O45 1.20(2) . ?
C43 O47 1.22(3) . ?
C43 O44 1.30(2) . ?
O45 C46 1.41(3) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
O48 C49 1.50(3) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C51 C56 1.379(14) . ?
C51 C52 1.384(14) . ?
C52 C53 1.359(16) . ?
C52 H52 0.9300 . ?
C53 C54 1.37(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.36(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.39(2) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?

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 120.8(8) . . ?
C2 C1 Br1 119.4(7) . . ?
C10 C1 Br1 119.7(8) . . ?
C3 C2 C1 121.3(8) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 118.4(9) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
O5 C4 C9 121.1(7) . . ?
O5 C4 C3 116.9(8) . . ?
C9 C4 C3 122.0(8) . . ?
C4 O5 C6 120.4(6) . . ?
C7 C6 O5 120.7(7) . . ?
C7 C6 C11 127.5(7) . . ?
O5 C6 C11 111.8(7) . . ?
C6 C7 O7 118.3(6) . . ?
C6 C7 C8 122.9(7) . . ?
O7 C7 C8 118.7(7) . . ?
C7 O7 H7 108(7) . . ?
O8 C8 C7 122.9(7) . . ?
O8 C8 C9 122.5(7) . . ?
C7 C8 C9 114.6(8) . . ?
C4 C9 C10 118.4(7) . . ?
C4 C9 C8 119.8(7) . . ?
C10 C9 C8 121.8(8) . . ?
C1 C10 C9 118.9(9) . . ?
C1 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C6 C11 C21 110.8(7) . . ?
C6 C11 C12 108.9(7) . . ?
C21 C11 C12 112.9(7) . . ?
C6 C11 H11 108.0 . . ?
C21 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C13 C12 C11 113.2(7) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
O14 C13 O15 122.6(9) . . ?
O14 C13 C12 126.0(9) . . ?
O15 C13 C12 111.4(8) . . ?
C13 O15 C16 117.1(9) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 C26 117.1(10) . . ?
C22 C21 C11 119.8(8) . . ?
C26 C21 C11 123.0(9) . . ?
C23 C22 C21 121.9(11) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 119.7(13) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.0(14) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 120.6(13) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 121.4(12) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C40 C31 C32 121.4(8) . . ?
C40 C31 Br2 120.2(7) . . ?
C32 C31 Br2 118.4(7) . . ?
C33 C32 C31 119.5(8) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 119.8(9) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
O35 C34 C33 117.5(8) . . ?
O35 C34 C39 121.1(7) . . ?
C33 C34 C39 121.4(8) . . ?
C34 O35 C36 120.3(6) . . ?
C37 C36 O35 122.2(7) . . ?
C37 C36 C41 123.9(8) . . ?
O35 C36 C41 113.9(7) . . ?
O37 C37 C36 118.2(7) . . ?
O37 C37 C38 121.1(8) . . ?
C36 C37 C38 120.7(8) . . ?
C37 O37 H37 111(7) . . ?
O38 C38 C39 124.2(7) . . ?
O38 C38 C37 120.4(7) . . ?
C39 C38 C37 115.4(8) . . ?
C34 C39 C40 118.7(7) . . ?
C34 C39 C38 120.3(7) . . ?
C40 C39 C38 121.0(8) . . ?
C31 C40 C39 119.1(8) . . ?
C31 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?
C36 C41 C51 112.3(8) . . ?
C36 C41 C42 112.8(8) . . ?
C51 C41 C42 111.1(8) . . ?
C36 C41 H41 106.8 . . ?
C51 C41 H41 106.8 . . ?
C42 C41 H41 106.8 . . ?
C43 C42 C41 114.5(10) . . ?
C43 C42 H42A 108.6 . . ?
C41 C42 H42A 108.6 . . ?
C43 C42 H42B 108.6 . . ?
C41 C42 H42B 108.6 . . ?
H42A C42 H42B 107.6 . . ?
O48 C43 O47 114(3) . . ?
O45 C43 O44 122(2) . . ?
O48 C43 C42 138(2) . . ?
O45 C43 C42 127(2) . . ?
O47 C43 C42 107(3) . . ?
O44 C43 C42 111.0(18) . . ?
C43 O45 C46 126(3) . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C43 O48 C49 105(3) . . ?
O48 C49 H49A 109.5 . . ?
O48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
O48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C56 C51 C52 118.2(10) . . ?
C56 C51 C41 119.6(10) . . ?
C52 C51 C41 122.2(9) . . ?
C53 C52 C51 120.5(12) . . ?
C53 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
C54 C53 C52 120.7(15) . . ?
C54 C53 H53 119.7 . . ?
C52 C53 H53 119.7 . . ?
C55 C54 C53 120.5(16) . . ?
C55 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?
C54 C55 C56 118.8(16) . . ?
C54 C55 H55 120.6 . . ?
C56 C55 H55 120.6 . . ?
C51 C56 C55 121.4(14) . . ?
C51 C56 H56 119.3 . . ?
C55 C56 H56 119.3 . . ?

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 1.8(15) . . . . ?
Br1 C1 C2 C3 -178.8(7) . . . . ?
C1 C2 C3 C4 -0.2(14) . . . . ?
C2 C3 C4 O5 179.7(8) . . . . ?
C2 C3 C4 C9 -0.5(13) . . . . ?
C9 C4 O5 C6 2.3(11) . . . . ?
C3 C4 O5 C6 -177.8(7) . . . . ?
C4 O5 C6 C7 0.3(12) . . . . ?
C4 O5 C6 C11 -179.3(7) . . . . ?
O5 C6 C7 O7 177.6(7) . . . . ?
C11 C6 C7 O7 -2.8(13) . . . . ?
O5 C6 C7 C8 -5.6(13) . . . . ?
C11 C6 C7 C8 173.9(8) . . . . ?
C6 C7 C8 O8 -173.1(8) . . . . ?
O7 C7 C8 O8 3.7(12) . . . . ?
C6 C7 C8 C9 7.7(12) . . . . ?
O7 C7 C8 C9 -175.5(7) . . . . ?
O5 C4 C9 C10 179.5(8) . . . . ?
C3 C4 C9 C10 -0.4(12) . . . . ?
O5 C4 C9 C8 0.3(12) . . . . ?
C3 C4 C9 C8 -179.6(8) . . . . ?
O8 C8 C9 C4 175.9(8) . . . . ?
C7 C8 C9 C4 -5.0(11) . . . . ?
O8 C8 C9 C10 -3.3(13) . . . . ?
C7 C8 C9 C10 175.9(7) . . . . ?
C2 C1 C10 C9 -2.7(14) . . . . ?
Br1 C1 C10 C9 178.0(7) . . . . ?
C4 C9 C10 C1 1.9(12) . . . . ?
C8 C9 C10 C1 -178.9(8) . . . . ?
C7 C6 C11 C21 113.3(10) . . . . ?
O5 C6 C11 C21 -67.1(9) . . . . ?
C7 C6 C11 C12 -121.9(10) . . . . ?
O5 C6 C11 C12 57.7(9) . . . . ?
C6 C11 C12 C13 175.7(8) . . . . ?
C21 C11 C12 C13 -60.8(10) . . . . ?
C11 C12 C13 O14 -35.2(17) . . . . ?
C11 C12 C13 O15 145.6(9) . . . . ?
O14 C13 O15 C16 -2.2(18) . . . . ?
C12 C13 O15 C16 177.1(10) . . . . ?
C6 C11 C21 C22 -102.0(9) . . . . ?
C12 C11 C21 C22 135.6(8) . . . . ?
C6 C11 C21 C26 74.7(10) . . . . ?
C12 C11 C21 C26 -47.8(11) . . . . ?
C26 C21 C22 C23 2.8(15) . . . . ?
C11 C21 C22 C23 179.7(9) . . . . ?
C21 C22 C23 C24 -5.3(17) . . . . ?
C22 C23 C24 C25 6.4(19) . . . . ?
C23 C24 C25 C26 -5.2(19) . . . . ?
C24 C25 C26 C21 2.9(18) . . . . ?
C22 C21 C26 C25 -1.6(15) . . . . ?
C11 C21 C26 C25 -178.3(9) . . . . ?
C40 C31 C32 C33 0.4(14) . . . . ?
Br2 C31 C32 C33 179.2(7) . . . . ?
C31 C32 C33 C34 0.5(14) . . . . ?
C32 C33 C34 O35 179.6(8) . . . . ?
C32 C33 C34 C39 0.2(13) . . . . ?
C33 C34 O35 C36 -178.4(8) . . . . ?
C39 C34 O35 C36 1.0(12) . . . . ?
C34 O35 C36 C37 0.7(12) . . . . ?
C34 O35 C36 C41 179.2(7) . . . . ?
O35 C36 C37 O37 178.4(8) . . . . ?
C41 C36 C37 O37 0.1(13) . . . . ?
O35 C36 C37 C38 -2.4(13) . . . . ?
C41 C36 C37 C38 179.3(8) . . . . ?
O37 C37 C38 O38 -1.6(13) . . . . ?
C36 C37 C38 O38 179.2(8) . . . . ?
O37 C37 C38 C39 -178.5(8) . . . . ?
C36 C37 C38 C39 2.3(12) . . . . ?
O35 C34 C39 C40 178.9(8) . . . . ?
C33 C34 C39 C40 -1.7(13) . . . . ?
O35 C34 C39 C38 -0.9(12) . . . . ?
C33 C34 C39 C38 178.5(8) . . . . ?
O38 C38 C39 C34 -177.5(8) . . . . ?
C37 C38 C39 C34 -0.7(12) . . . . ?
O38 C38 C39 C40 2.7(13) . . . . ?
C37 C38 C39 C40 179.5(8) . . . . ?
C32 C31 C40 C39 -1.9(13) . . . . ?
Br2 C31 C40 C39 179.3(7) . . . . ?
C34 C39 C40 C31 2.5(12) . . . . ?
C38 C39 C40 C31 -177.6(8) . . . . ?
C37 C36 C41 C51 86.0(11) . . . . ?
O35 C36 C41 C51 -92.5(9) . . . . ?
C37 C36 C41 C42 -147.6(9) . . . . ?
O35 C36 C41 C42 33.9(11) . . . . ?
C36 C41 C42 C43 60.4(14) . . . . ?
C51 C41 C42 C43 -172.5(11) . . . . ?
C41 C42 C43 O48 -148(3) . . . . ?
C41 C42 C43 O45 63(3) . . . . ?
C41 C42 C43 O47 35(3) . . . . ?
C41 C42 C43 O44 -121.3(19) . . . . ?
O44 C43 O45 C46 7(4) . . . . ?
C42 C43 O45 C46 -178(2) . . . . ?
O47 C43 O48 C49 21(5) . . . . ?
C42 C43 O48 C49 -156(3) . . . . ?
C36 C41 C51 C56 -148.5(10) . . . . ?
C42 C41 C51 C56 84.2(11) . . . . ?
C36 C41 C51 C52 33.7(13) . . . . ?
C42 C41 C51 C52 -93.6(11) . . . . ?
C56 C51 C52 C53 0.1(17) . . . . ?
C41 C51 C52 C53 177.9(10) . . . . ?
C51 C52 C53 C54 2(2) . . . . ?
C52 C53 C54 C55 -4(3) . . . . ?
C53 C54 C55 C56 3(3) . . . . ?
C52 C51 C56 C55 -0.4(18) . . . . ?
C41 C51 C56 C55 -178.3(13) . . . . ?
C54 C55 C56 C51 -1(2) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051

