#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:24:04 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158044.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_7158044
loop_
_publ_author_name
'Nakamura, Tenma'
'Pitna, Dinda B.'
'Kimura, Kogaku'
'Yoshimoto, Yukiko'
'Uchiyama, Tomoya'
'Mori, Takaya'
'Kondo, Ryosuke'
'Hara, Shihori'
'Egoshi, Yuki'
'Yamaguchi, Shoya'
'Suzuki, Noriyuki'
'Suzuki, Yumiko'
'Usuki, Toyonobu'
_publ_section_title
;
 Total synthesis of cynaropicrin.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6038
_journal_page_last               6044
_journal_paper_doi               10.1039/d1ob00657f
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C24 H31 Br O5'
_chemical_formula_sum            'C24 H31 Br O5'
_chemical_formula_weight         479.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                94.13(3)
_cell_angle_beta                 91.26(3)
_cell_angle_gamma                90.13(2)
_cell_formula_units_Z            2
_cell_length_a                   8.703(13)
_cell_length_b                   9.329(14)
_cell_length_c                   14.17(2)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.71
_cell_volume                     1147(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10727
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.706
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             500.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.73
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3296 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.032(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7316
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2234
_reflns_d_resolution_high        0.8410
_reflns_number_gt                3598
_reflns_number_total             7316
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1ob00657f2.cif
_cod_data_source_block           mori160121a
_cod_depositor_comments          'Adding full bibliography for 7158044.cif.'
_cod_database_code               7158044
_shelx_title                     ' mori160121a'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            126.81
_shelx_f_squared_multiplier      1.000
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21825(18) 0.32770(13) -0.11701(9) 0.1325(6) Uani 1 1 d . . .
Br2 Br 0.75905(19) 0.15410(13) 0.71146(9) 0.1366(7) Uani 1 1 d . . .
O1 O 0.4033(7) -0.1273(8) 0.1234(5) 0.0801(18) Uani 1 1 d . . .
O2 O 0.2117(6) 0.0130(6) 0.1679(4) 0.0590(15) Uani 1 1 d . . .
O3 O 0.2355(9) -0.1115(8) -0.0763(6) 0.088(2) Uani 1 1 d . . .
O4 O -0.2477(7) -0.0146(6) 0.3370(4) 0.0647(16) Uani 1 1 d . . .
O5 O -0.7839(10) -0.1000(8) 0.6075(6) 0.098(2) Uani 1 1 d . . .
O6 O 0.9149(7) 0.6092(7) 0.4711(5) 0.0754(17) Uani 1 1 d . . .
O7 O 0.7232(6) 0.4661(6) 0.4258(4) 0.0559(14) Uani 1 1 d . . .
O8 O 0.7556(9) 0.5923(8) 0.6694(5) 0.083(2) Uani 1 1 d . . .
O9 O 0.2486(7) 0.4966(6) 0.2607(4) 0.0620(15) Uani 1 1 d . . .
O10 O -0.3022(10) 0.5805(8) -0.0152(6) 0.101(3) Uani 1 1 d . . .
C1 C 0.3250(10) -0.0274(10) 0.1097(7) 0.068(2) Uani 1 1 d . . .
C2 C 0.3331(11) 0.0686(10) 0.0308(6) 0.070(2) Uani 1 1 d . . .
H2 H 0.4197 0.1367 0.0437 0.084 Uiso 1 1 calc R . .
C3 C 0.1834(10) 0.1510(8) 0.0383(6) 0.058(2) Uani 1 1 d . . .
H3 H 0.1027 0.1018 -0.0025 0.069 Uiso 1 1 calc R . .
C4 C 0.1467(9) 0.1447(8) 0.1382(6) 0.057(2) Uani 1 1 d . . .
H4 H 0.1952 0.2273 0.1754 0.068 Uiso 1 1 calc R . .
C5 C -0.0247(9) 0.1404(8) 0.1590(6) 0.0541(19) Uani 1 1 d . . .
H5 H -0.0683 0.2356 0.1472 0.065 Uiso 1 1 calc R . .
C6 C -0.0549(9) 0.1127(8) 0.2596(5) 0.0488(18) Uani 1 1 d . . .
H6 H 0.0406 0.0557 0.2628 0.059 Uiso 1 1 calc R . .
C7 C -0.1491(11) -0.0214(9) 0.2588(6) 0.064(2) Uani 1 1 d . . .
H7 H -0.0806 -0.1056 0.2616 0.077 Uiso 1 1 calc R . .
C8 C -0.2333(10) -0.0273(9) 0.1635(6) 0.055(2) Uani 1 1 d . . .
H8A H -0.2652 -0.1257 0.1433 0.066 Uiso 1 1 calc R . .
H8B H -0.3241 0.0347 0.1659 0.066 Uiso 1 1 calc R . .
C9 C -0.1155(9) 0.0269(7) 0.0978(5) 0.0501(18) Uani 1 1 d . . .
H9 H -0.0447 -0.0535 0.0812 0.060 Uiso 1 1 calc R . .
C10 C 0.3614(13) -0.0185(12) -0.0591(7) 0.085(3) Uani 1 1 d . . .
H10A H 0.3714 0.0442 -0.1113 0.102 Uiso 1 1 calc R . .
H10B H 0.4564 -0.0737 -0.0536 0.102 Uiso 1 1 calc R . .
C11 C 0.2467(19) -0.2050(15) -0.1581(9) 0.125(5) Uani 1 1 d . . .
H11A H 0.3460 -0.2520 -0.1582 0.150 Uiso 1 1 calc R . .
H11B H 0.2359 -0.1507 -0.2137 0.150 Uiso 1 1 calc R . .
H11C H 0.1659 -0.2769 -0.1590 0.150 Uiso 1 1 calc R . .
C12 C 0.1989(14) 0.3055(10) 0.0153(7) 0.081(3) Uani 1 1 d . . .
H12A H 0.2894 0.3478 0.0491 0.097 Uiso 1 1 calc R . .
H12B H 0.1085 0.3588 0.0381 0.097 Uiso 1 1 calc R . .
C13 C -0.0120(10) 0.1904(11) 0.3344(7) 0.070(2) Uani 1 1 d . . .
H13A H -0.0401 0.1640 0.3945 0.084 Uiso 1 1 calc R . .
H13B H 0.0474 0.2736 0.3289 0.084 Uiso 1 1 calc R . .
C14 C -0.1873(10) 0.0702(8) 0.0089(6) 0.056(2) Uani 1 1 d . . .
C15 C -0.2353(12) 0.1976(11) -0.0045(8) 0.081(3) Uani 1 1 d . . .
H15A H -0.2258 0.2710 0.0443 0.097 Uiso 1 1 calc R . .
H15B H -0.2799 0.2174 -0.0632 0.097 Uiso 1 1 calc R . .
C16 C -0.1966(14) -0.0473(10) -0.0667(7) 0.082(3) Uani 1 1 d . . .
H16A H -0.2604 -0.0174 -0.1187 0.098 Uiso 1 1 calc R . .
H16B H -0.2413 -0.1318 -0.0420 0.098 Uiso 1 1 calc R . .
H16C H -0.0943 -0.0697 -0.0891 0.098 Uiso 1 1 calc R . .
C17 C -0.3181(14) -0.1501(9) 0.3470(8) 0.086(3) Uani 1 1 d . . .
H17A H -0.2423 -0.2173 0.3703 0.103 Uiso 1 1 calc R . .
H17B H -0.3585 -0.1900 0.2855 0.103 Uiso 1 1 calc R . .
C18 C -0.4451(12) -0.1301(8) 0.4148(6) 0.066(3) Uani 1 1 d . . .
C19 C -0.4188(11) -0.1617(9) 0.5064(6) 0.064(2) Uani 1 1 d . . .
H19 H -0.3214 -0.1933 0.5259 0.076 Uiso 1 1 calc R . .
C20 C -0.5362(11) -0.1468(10) 0.5701(7) 0.069(3) Uani 1 1 d . . .
H20 H -0.5182 -0.1647 0.6338 0.083 Uiso 1 1 calc R . .
C21 C -0.6770(11) -0.1065(9) 0.5406(7) 0.065(2) Uani 1 1 d . . .
C22 C -0.7059(13) -0.0722(9) 0.4472(8) 0.073(3) Uani 1 1 d . . .
H22 H -0.8031 -0.0410 0.4272 0.087 Uiso 1 1 calc R . .
C23 C -0.5880(13) -0.0861(10) 0.3874(7) 0.072(3) Uani 1 1 d . . .
H23 H -0.6046 -0.0646 0.3242 0.087 Uiso 1 1 calc R . .
C24 C -0.9370(14) -0.0724(13) 0.5745(12) 0.129(6) Uani 1 1 d . . .
H24A H -0.9697 -0.1491 0.5286 0.154 Uiso 1 1 calc R . .
H24B H -0.9391 0.0184 0.5451 0.154 Uiso 1 1 calc R . .
H24C H -1.0059 -0.0677 0.6276 0.154 Uiso 1 1 calc R . .
C25 C 0.8409(11) 0.5086(11) 0.4868(7) 0.068(2) Uani 1 1 d . . .
C26 C 0.8537(10) 0.4169(10) 0.5668(7) 0.067(2) Uani 1 1 d . . .
H26 H 0.9417 0.3512 0.5560 0.080 Uiso 1 1 calc R . .
C27 C 0.7053(11) 0.3277(9) 0.5578(6) 0.060(2) Uani 1 1 d . . .
H27 H 0.6273 0.3771 0.5981 0.072 Uiso 1 1 calc R . .
C28 C 0.6564(10) 0.3363(8) 0.4570(5) 0.057(2) Uani 1 1 d . . .
H28 H 0.7002 0.2532 0.4195 0.069 Uiso 1 1 calc R . .
C29 C 0.4865(9) 0.3404(8) 0.4364(6) 0.056(2) Uani 1 1 d . . .
H29 H 0.4438 0.2451 0.4484 0.068 Uiso 1 1 calc R . .
C30 C 0.4474(9) 0.3676(8) 0.3362(6) 0.0546(19) Uani 1 1 d . . .
H30 H 0.5423 0.4257 0.3330 0.066 Uiso 1 1 calc R . .
C31 C 0.3524(10) 0.5021(8) 0.3371(6) 0.059(2) Uani 1 1 d . . .
H31 H 0.4208 0.5866 0.3343 0.071 Uiso 1 1 calc R . .
C32 C 0.2738(10) 0.5081(9) 0.4344(6) 0.058(2) Uani 1 1 d . . .
H32A H 0.2434 0.6064 0.4548 0.069 Uiso 1 1 calc R . .
H32B H 0.1832 0.4454 0.4326 0.069 Uiso 1 1 calc R . .
C33 C 0.4023(10) 0.4533(8) 0.5000(6) 0.0554(19) Uani 1 1 d . . .
H33 H 0.4746 0.5341 0.5158 0.067 Uiso 1 1 calc R . .
C34 C 0.8818(12) 0.5022(12) 0.6544(8) 0.088(3) Uani 1 1 d . . .
H34A H 0.8944 0.4398 0.7068 0.106 Uiso 1 1 calc R . .
H34B H 0.9758 0.5594 0.6506 0.106 Uiso 1 1 calc R . .
C35 C 0.7676(18) 0.6855(19) 0.7525(11) 0.136(6) Uani 1 1 d . . .
H35A H 0.8718 0.7222 0.7600 0.163 Uiso 1 1 calc R . .
H35B H 0.7422 0.6332 0.8068 0.163 Uiso 1 1 calc R . .
H35C H 0.6969 0.7650 0.7475 0.163 Uiso 1 1 calc R . .
C36 C 0.7148(12) 0.1734(9) 0.5830(7) 0.069(3) Uani 1 1 d . . .
H36A H 0.7946 0.1244 0.5452 0.083 Uiso 1 1 calc R . .
H36B H 0.6166 0.1255 0.5660 0.083 Uiso 1 1 calc R . .
C37 C 0.4854(10) 0.2922(10) 0.2618(7) 0.069(2) Uani 1 1 d . . .
H37A H 0.5448 0.2089 0.2668 0.083 Uiso 1 1 calc R . .
H37B H 0.4541 0.3199 0.2018 0.083 Uiso 1 1 calc R . .
C38 C 0.3359(10) 0.4128(8) 0.5889(6) 0.060(2) Uani 1 1 d . . .
C39 C 0.2856(12) 0.2821(11) 0.6017(8) 0.084(3) Uani 1 1 d . . .
H39A H 0.2440 0.2620 0.6599 0.100 Uiso 1 1 calc R . .
H39B H 0.2914 0.2093 0.5525 0.100 Uiso 1 1 calc R . .
C40 C 0.3287(12) 0.5264(10) 0.6626(7) 0.075(3) Uani 1 1 d . . .
H40A H 0.2767 0.4921 0.7165 0.090 Uiso 1 1 calc R . .
H40B H 0.2724 0.6069 0.6394 0.090 Uiso 1 1 calc R . .
H40C H 0.4320 0.5572 0.6816 0.090 Uiso 1 1 calc R . .
C41 C 0.1689(14) 0.6316(9) 0.2502(8) 0.084(3) Uani 1 1 d . . .
H41A H 0.1268 0.6667 0.3111 0.101 Uiso 1 1 calc R . .
H41B H 0.2418 0.7036 0.2308 0.101 Uiso 1 1 calc R . .
C42 C 0.0492(13) 0.6133(8) 0.1823(6) 0.065(2) Uani 1 1 d . . .
C43 C 0.0711(12) 0.6424(9) 0.0905(7) 0.072(3) Uani 1 1 d . . .
H43 H 0.1684 0.6699 0.0704 0.086 Uiso 1 1 calc R . .
C44 C -0.0573(12) 0.6301(10) 0.0255(6) 0.070(3) Uani 1 1 d . . .
H44 H -0.0461 0.6531 -0.0375 0.084 Uiso 1 1 calc R . .
C45 C -0.1929(11) 0.5858(9) 0.0547(8) 0.067(3) Uani 1 1 d . . .
C46 C -0.2175(14) 0.5571(10) 0.1444(8) 0.079(3) Uani 1 1 d . . .
H46 H -0.3154 0.5303 0.1638 0.095 Uiso 1 1 calc R . .
C47 C -0.0901(14) 0.5686(9) 0.2094(7) 0.074(3) Uani 1 1 d . . .
H47 H -0.1029 0.5448 0.2721 0.089 Uiso 1 1 calc R . .
C48 C -0.4568(13) 0.5492(15) 0.0200(12) 0.129(6) Uani 1 1 d . . .
H48A H -0.4838 0.6223 0.0689 0.155 Uiso 1 1 calc R . .
H48B H -0.4562 0.4558 0.0459 0.155 Uiso 1 1 calc R . .
H48C H -0.5315 0.5491 -0.0318 0.155 Uiso 1 1 calc R . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(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
C1 O2 C4 108.7(7) . . ?
C10 O3 C11 114.4(9) . . ?
C7 O4 C17 110.9(6) . . ?
C21 O5 C24 115.2(10) . . ?
C25 O7 C28 108.5(7) . . ?
C34 O8 C35 114.2(9) . . ?
C31 O9 C41 113.4(6) . . ?
C45 O10 C48 112.3(10) . . ?
O1 C1 O2 121.4(9) . . ?
O1 C1 C2 127.9(9) . . ?
O2 C1 C2 110.7(8) . . ?
C1 C2 C10 109.6(9) . . ?
C1 C2 C3 102.9(7) . . ?
C10 C2 C3 117.6(8) . . ?
C1 C2 H2 108.8 . . ?
C10 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C4 C3 C12 109.7(7) . . ?
C4 C3 C2 102.6(7) . . ?
C12 C3 C2 113.2(8) . . ?
C4 C3 H3 110.4 . . ?
C12 C3 H3 110.4 . . ?
C2 C3 H3 110.4 . . ?
O2 C4 C3 106.5(7) . . ?
O2 C4 C5 106.9(6) . . ?
C3 C4 C5 115.1(7) . . ?
O2 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C6 C5 C4 112.6(7) . . ?
C6 C5 C9 106.3(6) . . ?
C4 C5 C9 114.3(7) . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
C9 C5 H5 107.8 . . ?
C13 C6 C7 125.2(8) . . ?
C13 C6 C5 127.2(8) . . ?
C7 C6 C5 107.6(6) . . ?
C13 C6 H6 90.5 . . ?
C7 C6 H6 90.5 . . ?
C5 C6 H6 90.5 . . ?
O4 C7 C6 110.2(6) . . ?
O4 C7 C8 113.9(8) . . ?
C6 C7 C8 103.7(7) . . ?
O4 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C9 C8 C7 103.6(7) . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C14 C9 C8 111.7(7) . . ?
C14 C9 C5 117.8(6) . . ?
C8 C9 C5 104.3(7) . . ?
C14 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C5 C9 H9 107.5 . . ?
O3 C10 C2 107.3(7) . . ?
O3 C10 H10A 110.2 . . ?
C2 C10 H10A 110.2 . . ?
O3 C10 H10B 110.2 . . ?
C2 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 Br1 113.2(7) . . ?
C3 C12 H12A 108.9 . . ?
Br1 C12 H12A 108.9 . . ?
C3 C12 H12B 108.9 . . ?
Br1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C6 C13 H13A 120.0 . . ?
C6 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C9 124.7(8) . . ?
C15 C14 C16 121.7(8) . . ?
C9 C14 C16 113.6(7) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C18 108.7(7) . . ?
O4 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O4 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C23 119.5(8) . . ?
C19 C18 C17 118.5(10) . . ?
C23 C18 C17 121.9(9) . . ?
C18 C19 C20 119.5(9) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 119.7(9) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O5 C21 C20 114.9(10) . . ?
O5 C21 C22 123.5(10) . . ?
C20 C21 C22 121.6(8) . . ?
C23 C22 C21 116.9(9) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
C22 C23 C18 122.7(9) . . ?
C22 C23 H23 118.6 . . ?
C18 C23 H23 118.6 . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 O7 119.0(9) . . ?
O6 C25 C26 129.0(10) . . ?
O7 C25 C26 111.9(8) . . ?
C34 C26 C25 110.9(9) . . ?
C34 C26 C27 117.4(8) . . ?
C25 C26 C27 103.2(7) . . ?
C34 C26 H26 108.3 . . ?
C25 C26 H26 108.3 . . ?
C27 C26 H26 108.3 . . ?
C28 C27 C36 111.0(7) . . ?
C28 C27 C26 103.6(7) . . ?
C36 C27 C26 117.3(8) . . ?
C28 C27 H27 108.2 . . ?
C36 C27 H27 108.2 . . ?
C26 C27 H27 108.2 . . ?
O7 C28 C27 106.9(6) . . ?
O7 C28 C29 107.8(6) . . ?
C27 C28 C29 116.7(7) . . ?
O7 C28 H28 108.4 . . ?
C27 C28 H28 108.4 . . ?
C29 C28 H28 108.4 . . ?
C30 C29 C28 113.3(7) . . ?
C30 C29 C33 107.4(7) . . ?
C28 C29 C33 113.2(7) . . ?
C30 C29 H29 107.5 . . ?
C28 C29 H29 107.5 . . ?
C33 C29 H29 107.5 . . ?
C37 C30 C29 127.4(8) . . ?
C37 C30 C31 124.8(8) . . ?
C29 C30 C31 107.8(7) . . ?
C37 C30 H30 90.1 . . ?
C29 C30 H30 90.1 . . ?
C31 C30 H30 90.1 . . ?
O9 C31 C30 111.0(6) . . ?
O9 C31 C32 113.4(8) . . ?
C30 C31 C32 103.8(6) . . ?
O9 C31 H31 109.5 . . ?
C30 C31 H31 109.5 . . ?
C32 C31 H31 109.5 . . ?
C33 C32 C31 102.3(7) . . ?
C33 C32 H32A 111.3 . . ?
C31 C32 H32A 111.3 . . ?
C33 C32 H32B 111.3 . . ?
C31 C32 H32B 111.3 . . ?
H32A C32 H32B 109.2 . . ?
C38 C33 C29 119.8(7) . . ?
C38 C33 C32 109.7(7) . . ?
C29 C33 C32 103.9(7) . . ?
C38 C33 H33 107.6 . . ?
C29 C33 H33 107.6 . . ?
C32 C33 H33 107.6 . . ?
O8 C34 C26 107.5(8) . . ?
O8 C34 H34A 110.2 . . ?
C26 C34 H34A 110.2 . . ?
O8 C34 H34B 110.2 . . ?
C26 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
O8 C35 H35A 109.5 . . ?
O8 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O8 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C27 C36 Br2 113.5(6) . . ?
C27 C36 H36A 108.9 . . ?
Br2 C36 H36A 108.9 . . ?
C27 C36 H36B 108.9 . . ?
Br2 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C30 C37 H37A 120.0 . . ?
C30 C37 H37B 120.0 . . ?
H37A C37 H37B 120.0 . . ?
C39 C38 C40 121.4(9) . . ?
C39 C38 C33 123.4(9) . . ?
C40 C38 C33 115.2(7) . . ?
C38 C39 H39A 120.0 . . ?
C38 C39 H39B 120.0 . . ?
H39A C39 H39B 120.0 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 O9 110.7(7) . . ?
C42 C41 H41A 109.5 . . ?
O9 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
O9 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C47 C42 C43 120.1(9) . . ?
C47 C42 C41 119.0(9) . . ?
C43 C42 C41 120.9(11) . . ?
C42 C43 C44 118.5(10) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
C45 C44 C43 119.7(9) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 122.8(10) . . ?
C44 C45 O10 112.3(10) . . ?
C46 C45 O10 124.8(10) . . ?
C45 C46 C47 117.7(11) . . ?
C45 C46 H46 121.1 . . ?
C47 C46 H46 121.1 . . ?
C42 C47 C46 121.0(9) . . ?
C42 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
O10 C48 H48A 109.5 . . ?
O10 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O10 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
Br1 C12 1.912(10) . ?
Br2 C36 1.874(10) . ?
O1 C1 1.181(11) . ?
O2 C1 1.337(11) . ?
O2 C4 1.440(9) . ?
O3 C10 1.402(12) . ?
O3 C11 1.406(12) . ?
O4 C7 1.414(10) . ?
O4 C17 1.421(10) . ?
O5 C21 1.341(11) . ?
O5 C24 1.432(14) . ?
O6 C25 1.174(11) . ?
O7 C25 1.365(12) . ?
O7 C28 1.444(9) . ?
O8 C34 1.395(12) . ?
O8 C35 1.415(12) . ?
O9 C31 1.392(10) . ?
O9 C41 1.455(10) . ?
O10 C45 1.357(12) . ?
O10 C48 1.480(15) . ?
C1 C2 1.484(13) . ?
C2 C10 1.486(13) . ?
C2 C3 1.516(14) . ?
C2 H2 0.9900 . ?
C3 C4 1.464(12) . ?
C3 C12 1.507(11) . ?
C3 H3 0.9900 . ?
C4 C5 1.528(11) . ?
C4 H4 0.9900 . ?
C5 C6 1.496(11) . ?
C5 C9 1.527(10) . ?
C5 H5 0.9900 . ?
C6 C13 1.288(11) . ?
C6 C7 1.493(11) . ?
C6 H6 0.9900 . ?
C7 C8 1.520(12) . ?
C7 H7 0.9900 . ?
C8 C9 1.509(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C14 1.477(11) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9400 . ?
C13 H13B 0.9400 . ?
C14 C15 1.287(12) . ?
C14 C16 1.477(12) . ?
C15 H15A 0.9400 . ?
C15 H15B 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.484(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.366(13) . ?
C18 C23 1.368(14) . ?
C19 C20 1.378(13) . ?
C19 H19 0.9400 . ?
C20 C21 1.349(13) . ?
C20 H20 0.9400 . ?
C21 C22 1.401(14) . ?
C22 C23 1.345(14) . ?
C22 H22 0.9400 . ?
C23 H23 0.9400 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C26 1.471(13) . ?
C26 C34 1.441(14) . ?
C26 C27 1.532(13) . ?
C26 H26 0.9900 . ?
C27 C28 1.490(11) . ?
C27 C36 1.510(12) . ?
C27 H27 0.9900 . ?
C28 C29 1.502(12) . ?
C28 H28 0.9900 . ?
C29 C30 1.493(12) . ?
C29 C33 1.534(11) . ?
C29 H29 0.9900 . ?
C30 C37 1.276(11) . ?
C30 C31 1.504(11) . ?
C30 H30 0.9900 . ?
C31 C32 1.551(12) . ?
C31 H31 0.9900 . ?
C32 C33 1.549(12) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C33 C38 1.472(12) . ?
C33 H33 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C37 H37A 0.9400 . ?
C37 H37B 0.9400 . ?
C38 C39 1.320(12) . ?
C38 C40 1.436(13) . ?
C39 H39A 0.9400 . ?
C39 H39B 0.9400 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 0.9700 . ?
C41 C42 1.404(14) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C42 C47 1.354(14) . ?
C42 C43 1.365(13) . ?
C43 C44 1.431(13) . ?
C43 H43 0.9400 . ?
C44 C45 1.334(14) . ?
C44 H44 0.9400 . ?
C45 C46 1.339(15) . ?
C46 C47 1.425(15) . ?
C46 H46 0.9400 . ?
C47 H47 0.9400 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C48 H48C 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
C4 O2 C1 O1 174.6(9) . . . . ?
C4 O2 C1 C2 -5.5(10) . . . . ?
O1 C1 C2 C10 41.1(14) . . . . ?
O2 C1 C2 C10 -138.7(8) . . . . ?
O1 C1 C2 C3 167.0(10) . . . . ?
O2 C1 C2 C3 -12.9(10) . . . . ?
C1 C2 C3 C4 25.2(9) . . . . ?
C10 C2 C3 C4 145.7(8) . . . . ?
C1 C2 C3 C12 143.3(8) . . . . ?
C10 C2 C3 C12 -96.2(10) . . . . ?
C1 O2 C4 C3 22.6(9) . . . . ?
C1 O2 C4 C5 146.2(7) . . . . ?
C12 C3 C4 O2 -149.9(8) . . . . ?
C2 C3 C4 O2 -29.4(8) . . . . ?
C12 C3 C4 C5 91.8(9) . . . . ?
C2 C3 C4 C5 -147.6(7) . . . . ?
O2 C4 C5 C6 53.6(8) . . . . ?
C3 C4 C5 C6 171.7(6) . . . . ?
O2 C4 C5 C9 -67.8(8) . . . . ?
C3 C4 C5 C9 50.2(9) . . . . ?
C4 C5 C6 C13 60.6(11) . . . . ?
C9 C5 C6 C13 -173.5(8) . . . . ?
C4 C5 C6 C7 -120.9(7) . . . . ?
C9 C5 C6 C7 5.0(8) . . . . ?
C17 O4 C7 C6 -169.7(8) . . . . ?
C17 O4 C7 C8 74.3(10) . . . . ?
C13 C6 C7 O4 29.9(12) . . . . ?
C5 C6 C7 O4 -148.6(7) . . . . ?
C13 C6 C7 C8 152.1(8) . . . . ?
C5 C6 C7 C8 -26.4(8) . . . . ?
O4 C7 C8 C9 157.5(6) . . . . ?
C6 C7 C8 C9 37.7(8) . . . . ?
C7 C8 C9 C14 -163.0(6) . . . . ?
C7 C8 C9 C5 -34.6(8) . . . . ?
C6 C5 C9 C14 143.1(7) . . . . ?
C4 C5 C9 C14 -92.0(8) . . . . ?
C6 C5 C9 C8 18.6(8) . . . . ?
C4 C5 C9 C8 143.5(7) . . . . ?
C11 O3 C10 C2 -178.2(10) . . . . ?
C1 C2 C10 O3 62.4(11) . . . . ?
C3 C2 C10 O3 -54.6(12) . . . . ?
C4 C3 C12 Br1 -171.8(7) . . . . ?
C2 C3 C12 Br1 74.3(10) . . . . ?
C8 C9 C14 C15 90.8(11) . . . . ?
C5 C9 C14 C15 -30.0(13) . . . . ?
C8 C9 C14 C16 -90.6(9) . . . . ?
C5 C9 C14 C16 148.6(8) . . . . ?
C7 O4 C17 C18 -167.3(8) . . . . ?
O4 C17 C18 C19 -99.1(9) . . . . ?
O4 C17 C18 C23 83.2(11) . . . . ?
C23 C18 C19 C20 -0.8(12) . . . . ?
C17 C18 C19 C20 -178.6(8) . . . . ?
C18 C19 C20 C21 2.5(12) . . . . ?
C24 O5 C21 C20 -173.6(9) . . . . ?
C24 O5 C21 C22 7.5(13) . . . . ?
C19 C20 C21 O5 177.9(8) . . . . ?
C19 C20 C21 C22 -3.2(13) . . . . ?
O5 C21 C22 C23 -179.0(9) . . . . ?
C20 C21 C22 C23 2.2(13) . . . . ?
C21 C22 C23 C18 -0.6(13) . . . . ?
C19 C18 C23 C22 -0.1(13) . . . . ?
C17 C18 C23 C22 177.6(8) . . . . ?
C28 O7 C25 O6 176.6(8) . . . . ?
C28 O7 C25 C26 -4.4(9) . . . . ?
O6 C25 C26 C34 41.4(14) . . . . ?
O7 C25 C26 C34 -137.5(8) . . . . ?
O6 C25 C26 C27 168.0(10) . . . . ?
O7 C25 C26 C27 -10.9(9) . . . . ?
C34 C26 C27 C28 143.4(8) . . . . ?
C25 C26 C27 C28 21.1(9) . . . . ?
C34 C26 C27 C36 -94.0(10) . . . . ?
C25 C26 C27 C36 143.7(8) . . . . ?
C25 O7 C28 C27 18.5(8) . . . . ?
C25 O7 C28 C29 144.7(7) . . . . ?
C36 C27 C28 O7 -151.1(7) . . . . ?
C26 C27 C28 O7 -24.4(8) . . . . ?
C36 C27 C28 C29 88.2(9) . . . . ?
C26 C27 C28 C29 -145.1(7) . . . . ?
O7 C28 C29 C30 52.5(8) . . . . ?
C27 C28 C29 C30 172.7(7) . . . . ?
O7 C28 C29 C33 -70.2(8) . . . . ?
C27 C28 C29 C33 50.0(9) . . . . ?
C28 C29 C30 C37 59.2(12) . . . . ?
C33 C29 C30 C37 -175.0(9) . . . . ?
C28 C29 C30 C31 -121.1(7) . . . . ?
C33 C29 C30 C31 4.8(9) . . . . ?
C41 O9 C31 C30 -171.8(8) . . . . ?
C41 O9 C31 C32 71.9(9) . . . . ?
C37 C30 C31 O9 30.8(12) . . . . ?
C29 C30 C31 O9 -148.9(7) . . . . ?
C37 C30 C31 C32 153.0(9) . . . . ?
C29 C30 C31 C32 -26.8(9) . . . . ?
O9 C31 C32 C33 158.4(6) . . . . ?
C30 C31 C32 C33 37.9(8) . . . . ?
C30 C29 C33 C38 142.0(8) . . . . ?
C28 C29 C33 C38 -92.1(9) . . . . ?
C30 C29 C33 C32 19.1(9) . . . . ?
C28 C29 C33 C32 145.1(7) . . . . ?
C31 C32 C33 C38 -164.0(7) . . . . ?
C31 C32 C33 C29 -34.8(8) . . . . ?
C35 O8 C34 C26 -178.8(12) . . . . ?
C25 C26 C34 O8 62.2(11) . . . . ?
C27 C26 C34 O8 -56.0(12) . . . . ?
C28 C27 C36 Br2 -175.0(6) . . . . ?
C26 C27 C36 Br2 66.2(9) . . . . ?
C29 C33 C38 C39 -29.4(13) . . . . ?
C32 C33 C38 C39 90.6(10) . . . . ?
C29 C33 C38 C40 150.8(8) . . . . ?
C32 C33 C38 C40 -89.3(9) . . . . ?
C31 O9 C41 C42 -170.5(9) . . . . ?
O9 C41 C42 C47 86.0(11) . . . . ?
O9 C41 C42 C43 -95.3(10) . . . . ?
C47 C42 C43 C44 2.4(12) . . . . ?
C41 C42 C43 C44 -176.3(8) . . . . ?
C42 C43 C44 C45 -2.4(12) . . . . ?
C43 C44 C45 C46 2.8(14) . . . . ?
C43 C44 C45 O10 179.8(7) . . . . ?
C48 O10 C45 C44 -172.8(9) . . . . ?
C48 O10 C45 C46 4.1(13) . . . . ?
C44 C45 C46 C47 -3.0(14) . . . . ?
O10 C45 C46 C47 -179.6(8) . . . . ?
C43 C42 C47 C46 -2.7(13) . . . . ?
C41 C42 C47 C46 176.0(8) . . . . ?
C45 C46 C47 C42 2.9(13) . . . . ?
