#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/06/7150690.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_7150690
loop_
_publ_author_name
'Simpson, Denise S.'
'Lovell, Kimberly M.'
'Lozama, Anthony'
'Han, Nina'
'Day, Victor W.'
'Dersch, Christina M.'
'Rothman, Richard B.'
'Prisinzano, Thomas E.'
_publ_section_title
;
 Synthetic studies of neoclerodane diterpenes from Salvia divinorum:
 role of the furan in affinity for opioid receptors
;
_journal_issue                   18
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3748
_journal_page_last               3756
_journal_paper_doi               10.1039/b905148a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C33 H39 F3 O10'
_chemical_formula_weight         652.64
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6372(4)
_cell_length_b                   18.6367(12)
_cell_length_c                   12.6435(8)
_cell_measurement_reflns_used    8976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.72
_cell_volume                     1561.45(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18602
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         9099
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                8245
_reflns_number_total             9099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905148a.txt
_cod_data_source_block           k89e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.60434(17) -0.15104(5) 0.64898(8) 0.0342(2) Uani 1 1 d . . .
F2 F 0.59491(16) -0.03987(6) 0.69227(8) 0.0354(2) Uani 1 1 d . . .
F3 F 0.82098(18) -0.10944(7) 0.76552(8) 0.0427(3) Uani 1 1 d . . .
O1 O 0.48846(16) 0.06179(6) 0.38468(9) 0.0244(2) Uani 1 1 d . . .
O2 O 0.57436(18) 0.17508(6) 0.37952(10) 0.0313(3) Uani 1 1 d . . .
O3 O 0.14563(18) 0.25558(6) -0.14415(9) 0.0287(2) Uani 1 1 d . . .
O4 O -0.1843(2) 0.26927(7) -0.12053(11) 0.0359(3) Uani 1 1 d . . .
O5 O -0.37957(19) 0.01128(6) -0.03961(10) 0.0324(3) Uani 1 1 d . . .
O6 O -0.2233(2) -0.09430(7) -0.00778(12) 0.0426(3) Uani 1 1 d . . .
O7 O -0.22939(16) 0.02737(6) 0.16012(9) 0.0256(2) Uani 1 1 d . . .
O8 O 0.57530(15) -0.06558(6) 0.47140(8) 0.0220(2) Uani 1 1 d . . .
O9 O 0.87894(16) -0.07373(6) 0.40078(9) 0.0264(2) Uani 1 1 d . . .
O10 O 1.03061(18) -0.12485(6) 0.59423(10) 0.0312(3) Uani 1 1 d . . .
C1 C 0.4792(2) 0.12718(8) 0.33841(12) 0.0221(3) Uani 1 1 d . . .
C2 C 0.3598(2) 0.13371(7) 0.23253(12) 0.0194(3) Uani 1 1 d . . .
H2 H 0.4462 0.1126 0.1782 0.023 Uiso 1 1 calc R . .
C3 C 0.3229(2) 0.21141(7) 0.20074(12) 0.0203(3) Uani 1 1 d . . .
H3A H 0.4517 0.2383 0.2067 0.024 Uiso 1 1 calc R . .
H3B H 0.2290 0.2338 0.2491 0.024 Uiso 1 1 calc R . .
C4 C 0.2335(2) 0.21536(7) 0.08740(12) 0.0207(3) Uani 1 1 d . . .
H4A H 0.3334 0.1966 0.0392 0.025 Uiso 1 1 calc R . .
H4B H 0.2076 0.2663 0.0687 0.025 Uiso 1 1 calc R . .
C5 C 0.0351(2) 0.17269(7) 0.06958(11) 0.0189(3) Uani 1 1 d . . .
C6 C -0.0127(2) 0.16314(8) -0.05194(12) 0.0224(3) Uani 1 1 d . . .
H6 H 0.1023 0.1366 -0.0814 0.027 Uiso 1 1 calc R . .
C7 C -0.2052(3) 0.11957(8) -0.07680(13) 0.0270(3) Uani 1 1 d . . .
H7A H -0.3225 0.1454 -0.0502 0.032 Uiso 1 1 calc R . .
H7B H -0.2275 0.1140 -0.1544 0.032 Uiso 1 1 calc R . .
C8 C -0.1869(2) 0.04586(8) -0.02481(13) 0.0252(3) Uani 1 1 d . . .
H8 H -0.0831 0.0170 -0.0602 0.030 Uiso 1 1 calc R . .
C9 C -0.1267(2) 0.05242(7) 0.09368(12) 0.0201(3) Uani 1 1 d . . .
C10 C 0.0676(2) 0.09453(7) 0.11556(11) 0.0180(2) Uani 1 1 d . . .
H10 H 0.1673 0.0718 0.0695 0.022 Uiso 1 1 calc R . .
C11 C 0.1650(2) 0.08844(7) 0.23002(11) 0.0175(2) Uani 1 1 d . . .
C12 C 0.2360(2) 0.01069(7) 0.25013(11) 0.0191(3) Uani 1 1 d . . .
H12A H 0.1177 -0.0218 0.2465 0.023 Uiso 1 1 calc R . .
H12B H 0.3263 -0.0039 0.1942 0.023 Uiso 1 1 calc R . .
C13 C 0.3481(2) 0.00348(7) 0.35843(12) 0.0206(3) Uani 1 1 d . . .
H13 H 0.2463 0.0015 0.4137 0.025 Uiso 1 1 calc R . .
C14 C 0.4732(2) -0.06481(8) 0.36562(11) 0.0206(3) Uani 1 1 d . . .
H14 H 0.5749 -0.0646 0.3102 0.025 Uiso 1 1 calc R . .
C15 C 0.3404(2) -0.13178(8) 0.35395(14) 0.0252(3) Uani 1 1 d . . .
H15A H 0.2119 -0.1222 0.3875 0.030 Uiso 1 1 calc R . .
H15B H 0.3079 -0.1402 0.2776 0.030 Uiso 1 1 calc R . .
C16 C 0.4314(3) -0.19903(10) 0.40133(17) 0.0354(4) Uani 1 1 d . . .
H16 H 0.489(5) -0.1991(17) 0.486(3) 0.067(8) Uiso 1 1 d . . .
C17 C 0.4561(3) -0.25909(11) 0.3508(2) 0.0430(5) Uani 1 1 d . . .
H17A H 0.520(4) -0.2955(14) 0.399(2) 0.046(6) Uiso 1 1 d . . .
H17B H 0.415(3) -0.2627(13) 0.2669(19) 0.038(6) Uiso 1 1 d . . .
C18 C -0.1382(2) 0.21325(8) 0.11960(13) 0.0241(3) Uani 1 1 d . . .
H18A H -0.1870 0.2517 0.0718 0.036 Uiso 1 1 calc R . .
H18B H -0.0890 0.2340 0.1874 0.036 Uiso 1 1 calc R . .
H18C H -0.2488 0.1799 0.1314 0.036 Uiso 1 1 calc R . .
C19 C -0.0315(3) 0.23492(8) -0.10819(12) 0.0261(3) Uani 1 1 d . . .
C20 C 0.1425(3) 0.32232(9) -0.20333(15) 0.0369(4) Uani 1 1 d . . .
H20A H 0.2810 0.3364 -0.2168 0.055 Uiso 1 1 calc R . .
H20B H 0.0793 0.3599 -0.1623 0.055 Uiso 1 1 calc R . .
H20C H 0.0651 0.3157 -0.2709 0.055 Uiso 1 1 calc R . .
C21 C -0.3743(3) -0.06134(10) -0.02691(14) 0.0378(4) Uani 1 1 d . . .
C22 C -0.5825(4) -0.09296(13) -0.04155(19) 0.0553(6) Uani 1 1 d . . .
H22A H -0.5915 -0.1357 0.0031 0.083 Uiso 1 1 calc R . .
H22B H -0.6093 -0.1063 -0.1160 0.083 Uiso 1 1 calc R . .
H22C H -0.6822 -0.0575 -0.0213 0.083 Uiso 1 1 calc R . .
C23 C 0.0285(2) 0.11139(8) 0.31851(11) 0.0208(3) Uani 1 1 d . . .
H23A H 0.1091 0.1149 0.3857 0.031 Uiso 1 1 calc R . .
H23B H -0.0785 0.0757 0.3252 0.031 Uiso 1 1 calc R . .
H23C H -0.0321 0.1582 0.3010 0.031 Uiso 1 1 calc R . .
C24 C 0.7751(2) -0.07164(7) 0.47532(11) 0.0194(3) Uani 1 1 d . . .
C25 C 0.8712(2) -0.07504(8) 0.58918(12) 0.0226(3) Uani 1 1 d . . .
C26 C 0.9617(2) -0.00170(9) 0.61727(12) 0.0252(3) Uani 1 1 d . . .
C27 C 1.1398(3) 0.00216(12) 0.67962(18) 0.0439(5) Uani 1 1 d . . .
H27 H 1.2065 -0.0405 0.7033 0.053 Uiso 1 1 calc R . .
C28 C 1.2199(3) 0.06873(15) 0.7071(2) 0.0597(7) Uani 1 1 d . . .
H28 H 1.3416 0.0717 0.7503 0.072 Uiso 1 1 calc R . .
C29 C 1.1235(3) 0.13079(13) 0.6720(2) 0.0520(6) Uani 1 1 d . . .
H29 H 1.1795 0.1762 0.6910 0.062 Uiso 1 1 calc R . .
C30 C 0.9473(3) 0.12725(10) 0.60987(16) 0.0383(4) Uani 1 1 d . . .
H30 H 0.8818 0.1700 0.5855 0.046 Uiso 1 1 calc R . .
C31 C 0.8653(3) 0.06061(9) 0.58283(13) 0.0290(3) Uani 1 1 d . . .
H31 H 0.7427 0.0578 0.5405 0.035 Uiso 1 1 calc R . .
C32 C 0.7195(3) -0.09408(9) 0.67352(13) 0.0296(3) Uani 1 1 d . . .
C33 C 0.9888(3) -0.19658(9) 0.55809(15) 0.0355(4) Uani 1 1 d . . .
H33A H 1.1122 -0.2254 0.5660 0.053 Uiso 1 1 calc R . .
H33B H 0.9410 -0.1954 0.4833 0.053 Uiso 1 1 calc R . .
H33C H 0.8847 -0.2178 0.6002 0.053 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 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'
F F 0.0171 0.0103 '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
C1 O1 C13 124.10(11) . . ?
C19 O3 C20 115.70(13) . . ?
C21 O5 C8 114.43(14) . . ?
C24 O8 C14 116.37(11) . . ?
C25 O10 C33 117.97(13) . . ?
O2 C1 O1 118.36(13) . . ?
O2 C1 C2 123.99(13) . . ?
O1 C1 C2 117.49(12) . . ?
C3 C2 C1 112.16(12) . . ?
C3 C2 C11 113.16(11) . . ?
C1 C2 C11 111.62(11) . . ?
C3 C2 H2 106.4 . . ?
C1 C2 H2 106.4 . . ?
C11 C2 H2 106.4 . . ?
C2 C3 C4 110.11(12) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 113.37(11) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C18 C5 C4 109.73(12) . . ?
C18 C5 C6 110.16(12) . . ?
C4 C5 C6 109.07(11) . . ?
C18 C5 C10 113.02(11) . . ?
C4 C5 C10 108.89(11) . . ?
C6 C5 C10 105.85(11) . . ?
C19 C6 C7 109.01(13) . . ?
C19 C6 C5 111.57(12) . . ?
C7 C6 C5 112.54(12) . . ?
C19 C6 H6 107.8 . . ?
C7 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C8 C7 C6 110.13(12) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O5 C8 C7 107.45(13) . . ?
O5 C8 C9 110.17(12) . . ?
C7 C8 C9 111.05(12) . . ?
O5 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
O7 C9 C10 125.45(13) . . ?
O7 C9 C8 121.55(13) . . ?
C10 C9 C8 112.98(12) . . ?
C9 C10 C11 115.78(11) . . ?
C9 C10 C5 108.18(11) . . ?
C11 C10 C5 116.81(11) . . ?
C9 C10 H10 104.9 . . ?
C11 C10 H10 104.9 . . ?
C5 C10 H10 104.9 . . ?
C23 C11 C12 109.18(11) . . ?
C23 C11 C2 111.11(11) . . ?
C12 C11 C2 105.23(11) . . ?
C23 C11 C10 115.15(11) . . ?
C12 C11 C10 109.23(11) . . ?
C2 C11 C10 106.44(11) . . ?
C13 C12 C11 111.09(11) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 C14 105.71(11) . . ?
O1 C13 C12 114.29(11) . . ?
C14 C13 C12 111.36(11) . . ?
O1 C13 H13 108.4 . . ?
C14 C13 H13 108.4 . . ?
C12 C13 H13 108.4 . . ?
O8 C14 C13 106.62(11) . . ?
O8 C14 C15 108.31(11) . . ?
C13 C14 C15 111.58(11) . . ?
O8 C14 H14 110.1 . . ?
C13 C14 H14 110.1 . . ?
C15 C14 H14 110.1 . . ?
C16 C15 C14 115.22(13) . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 125.4(2) . . ?
C17 C16 H16 115.0(16) . . ?
C15 C16 H16 119.5(16) . . ?
C16 C17 H17A 110.4(15) . . ?
C16 C17 H17B 120.1(13) . . ?
H17A C17 H17B 129(2) . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O3 123.56(14) . . ?
O4 C19 C6 125.24(15) . . ?
O3 C19 C6 111.20(13) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 O5 123.59(17) . . ?
O6 C21 C22 125.49(19) . . ?
O5 C21 C22 110.92(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O9 C24 O8 126.15(14) . . ?
O9 C24 C25 120.43(13) . . ?
O8 C24 C25 113.41(12) . . ?
O10 C25 C26 107.17(12) . . ?
O10 C25 C24 109.86(12) . . ?
C26 C25 C24 108.48(12) . . ?
O10 C25 C32 109.52(12) . . ?
C26 C25 C32 107.91(13) . . ?
C24 C25 C32 113.67(12) . . ?
C31 C26 C27 119.99(17) . . ?
C31 C26 C25 120.60(14) . . ?
C27 C26 C25 119.40(16) . . ?
C26 C27 C28 119.5(2) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 120.49(19) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.49(19) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C26 C31 C30 120.30(17) . . ?
C26 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
F1 C32 F2 106.90(14) . . ?
F1 C32 F3 106.55(13) . . ?
F2 C32 F3 107.05(14) . . ?
F1 C32 C25 114.10(14) . . ?
F2 C32 C25 112.46(13) . . ?
F3 C32 C25 109.38(13) . . ?
O10 C33 H33A 109.5 . . ?
O10 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O10 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
F1 C32 1.334(2) . ?
F2 C32 1.335(2) . ?
F3 C32 1.342(2) . ?
O1 C1 1.3518(18) . ?
O1 C13 1.4575(18) . ?
O2 C1 1.1955(18) . ?
O3 C19 1.341(2) . ?
O3 C20 1.4510(19) . ?
O4 C19 1.202(2) . ?
O5 C21 1.363(2) . ?
O5 C8 1.4345(19) . ?
O6 C21 1.188(3) . ?
O7 C9 1.2055(18) . ?
O8 C24 1.3292(17) . ?
O8 C14 1.4650(17) . ?
O9 C24 1.1991(18) . ?
O10 C25 1.4064(17) . ?
O10 C33 1.435(2) . ?
C1 C2 1.521(2) . ?
C2 C3 1.5192(19) . ?
C2 C11 1.5426(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.522(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5436(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C18 1.5417(19) . ?
C5 C6 1.561(2) . ?
C5 C10 1.5787(19) . ?
C6 C19 1.517(2) . ?
C6 C7 1.531(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.525(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.534(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.5216(19) . ?
C10 C11 1.556(2) . ?
C10 H10 1.0000 . ?
C11 C23 1.5396(19) . ?
C11 C12 1.5403(18) . ?
C12 C13 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5194(19) . ?
C13 H13 1.0000 . ?
C14 C15 1.530(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.501(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.304(3) . ?
C16 H16 1.12(3) . ?
C17 H17A 0.99(3) . ?
C17 H17B 1.08(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.504(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.542(2) . ?
C25 C26 1.527(2) . ?
C25 C32 1.548(2) . ?
C26 C31 1.384(2) . ?
C26 C27 1.385(2) . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.373(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
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
C13 O1 C1 O2 165.30(14) . . . . ?
C13 O1 C1 C2 -19.11(19) . . . . ?
O2 C1 C2 C3 -17.0(2) . . . . ?
O1 C1 C2 C3 167.66(12) . . . . ?
O2 C1 C2 C11 -145.21(15) . . . . ?
O1 C1 C2 C11 39.47(17) . . . . ?
C1 C2 C3 C4 170.97(11) . . . . ?
C11 C2 C3 C4 -61.65(15) . . . . ?
C2 C3 C4 C5 57.34(15) . . . . ?
C3 C4 C5 C18 74.13(14) . . . . ?
C3 C4 C5 C6 -165.11(11) . . . . ?
C3 C4 C5 C10 -50.04(15) . . . . ?
C18 C5 C6 C19 61.97(15) . . . . ?
C4 C5 C6 C19 -58.52(15) . . . . ?
C10 C5 C6 C19 -175.54(12) . . . . ?
C18 C5 C6 C7 -60.94(16) . . . . ?
C4 C5 C6 C7 178.57(12) . . . . ?
C10 C5 C6 C7 61.56(15) . . . . ?
C19 C6 C7 C8 177.72(13) . . . . ?
C5 C6 C7 C8 -57.95(17) . . . . ?
C21 O5 C8 C7 161.19(14) . . . . ?
C21 O5 C8 C9 -77.70(17) . . . . ?
C6 C7 C8 O5 172.91(13) . . . . ?
C6 C7 C8 C9 52.36(17) . . . . ?
O5 C8 C9 O7 3.6(2) . . . . ?
C7 C8 C9 O7 122.48(15) . . . . ?
O5 C8 C9 C10 -174.91(11) . . . . ?
C7 C8 C9 C10 -55.98(16) . . . . ?
O7 C9 C10 C11 15.4(2) . . . . ?
C8 C9 C10 C11 -166.20(11) . . . . ?
O7 C9 C10 C5 -117.89(15) . . . . ?
C8 C9 C10 C5 60.50(15) . . . . ?
C18 C5 C10 C9 59.87(15) . . . . ?
C4 C5 C10 C9 -177.92(11) . . . . ?
C6 C5 C10 C9 -60.79(14) . . . . ?
C18 C5 C10 C11 -72.88(15) . . . . ?
C4 C5 C10 C11 49.32(15) . . . . ?
C6 C5 C10 C11 166.46(11) . . . . ?
C3 C2 C11 C23 -69.02(15) . . . . ?
C1 C2 C11 C23 58.64(15) . . . . ?
C3 C2 C11 C12 172.93(11) . . . . ?
C1 C2 C11 C12 -59.41(14) . . . . ?
C3 C2 C11 C10 57.06(14) . . . . ?
C1 C2 C11 C10 -175.27(11) . . . . ?
C9 C10 C11 C23 -57.57(16) . . . . ?
C5 C10 C11 C23 71.65(15) . . . . ?
C9 C10 C11 C12 65.68(14) . . . . ?
C5 C10 C11 C12 -165.10(11) . . . . ?
C9 C10 C11 C2 178.83(11) . . . . ?
C5 C10 C11 C2 -51.95(15) . . . . ?
C23 C11 C12 C13 -57.88(14) . . . . ?
C2 C11 C12 C13 61.47(14) . . . . ?
C10 C11 C12 C13 175.40(11) . . . . ?
C1 O1 C13 C14 143.49(13) . . . . ?
C1 O1 C13 C12 20.66(19) . . . . ?
C11 C12 C13 O1 -42.59(16) . . . . ?
C11 C12 C13 C14 -162.29(11) . . . . ?
C24 O8 C14 C13 -124.56(12) . . . . ?
C24 O8 C14 C15 115.23(13) . . . . ?
O1 C13 C14 O8 54.56(13) . . . . ?
C12 C13 C14 O8 179.22(11) . . . . ?
O1 C13 C14 C15 172.64(12) . . . . ?
C12 C13 C14 C15 -62.70(15) . . . . ?
O8 C14 C15 C16 -39.63(18) . . . . ?
C13 C14 C15 C16 -156.69(15) . . . . ?
C14 C15 C16 C17 -124.1(2) . . . . ?
C20 O3 C19 O4 -1.9(2) . . . . ?
C20 O3 C19 C6 177.48(14) . . . . ?
C7 C6 C19 O4 36.6(2) . . . . ?
C5 C6 C19 O4 -88.34(19) . . . . ?
C7 C6 C19 O3 -142.82(14) . . . . ?
C5 C6 C19 O3 92.28(15) . . . . ?
C8 O5 C21 O6 -1.8(2) . . . . ?
C8 O5 C21 C22 178.82(15) . . . . ?
C14 O8 C24 O9 3.0(2) . . . . ?
C14 O8 C24 C25 -177.76(11) . . . . ?
C33 O10 C25 C26 -172.30(13) . . . . ?
C33 O10 C25 C24 -54.64(17) . . . . ?
C33 O10 C25 C32 70.89(17) . . . . ?
O9 C24 C25 O10 -39.90(19) . . . . ?
O8 C24 C25 O10 140.85(13) . . . . ?
O9 C24 C25 C26 76.95(16) . . . . ?
O8 C24 C25 C26 -102.29(14) . . . . ?
O9 C24 C25 C32 -163.02(14) . . . . ?
O8 C24 C25 C32 17.74(17) . . . . ?
O10 C25 C26 C31 155.94(14) . . . . ?
C24 C25 C26 C31 37.37(18) . . . . ?
C32 C25 C26 C31 -86.19(17) . . . . ?
O10 C25 C26 C27 -25.4(2) . . . . ?
C24 C25 C26 C27 -143.93(16) . . . . ?
C32 C25 C26 C27 92.50(18) . . . . ?
C31 C26 C27 C28 0.1(3) . . . . ?
C25 C26 C27 C28 -178.61(19) . . . . ?
C26 C27 C28 C29 -0.4(4) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C27 C26 C31 C30 0.5(2) . . . . ?
C25 C26 C31 C30 179.16(15) . . . . ?
C29 C30 C31 C26 -0.7(3) . . . . ?
O10 C25 C32 F1 -74.40(17) . . . . ?
C26 C25 C32 F1 169.26(13) . . . . ?
C24 C25 C32 F1 48.90(17) . . . . ?
O10 C25 C32 F2 163.62(13) . . . . ?
C26 C25 C32 F2 47.27(17) . . . . ?
C24 C25 C32 F2 -73.08(17) . . . . ?
O10 C25 C32 F3 44.82(17) . . . . ?
C26 C25 C32 F3 -71.53(16) . . . . ?
C24 C25 C32 F3 168.12(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653385
