#------------------------------------------------------------------------------
#$Date: 2021-06-04 04:00:47 +0300 (Fri, 04 Jun 2021) $
#$Revision: 265755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/25/1562542.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_1562542
loop_
_publ_author_name
'Kadir, Abdukriem'
'Zheng, Guijuan'
'Zheng, Xiaofeng'
'Jin, Pengfei'
'Maiwulanjiang, Maitinuer'
'Gao, Biao'
'Aisa, Haji Akber'
'Yao, Guangmin'
_publ_section_title
;
 Structurally Diverse Diterpenoids from the Roots of Salvia deserta
 Based on Nine Different Skeletal Types.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1442
_journal_page_last               1452
_journal_paper_doi               10.1021/acs.jnatprod.0c01180
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H32 O6'
_chemical_formula_weight         380.46
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                96.6930(10)
_cell_angle_beta                 102.932(2)
_cell_angle_gamma                106.655(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8531(2)
_cell_length_b                   10.02640(10)
_cell_length_c                   11.2177(2)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.23
_cell_measurement_theta_min      3.67
_cell_volume                     1015.23(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21201
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.482
_diffrn_reflns_theta_max         67.482
_diffrn_reflns_theta_min         4.121
_exptl_absorpt_coefficient_mu    0.735
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.06(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7101
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0713P)²+0.0266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                6706
_reflns_number_total             7101
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c01180_si_005.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1562538--1562543.cif.'
_cod_database_code               1562542
_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   0.757
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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_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 0.7860(3) 0.1109(3) 0.5521(3) 0.0480(6) Uani 1 1 d . . . . .
H1A H 0.850021 0.132970 0.636143 0.058 Uiso 1 1 calc R U . . .
H1B H 0.694956 0.039078 0.550058 0.058 Uiso 1 1 calc R U . . .
C1' C 0.2606(3) 0.9324(3) 0.4561(3) 0.0571(7) Uani 1 1 d . . . . .
H1'A H 0.241258 0.964183 0.533722 0.068 Uiso 1 1 calc R U . . .
H1'B H 0.353211 0.997894 0.452983 0.068 Uiso 1 1 calc R U . . .
C2' C 0.1378(4) 0.9370(4) 0.3472(4) 0.0729(10) Uani 1 1 d . . . . .
H2'A H 0.043975 0.878358 0.354431 0.088 Uiso 1 1 calc R U . . .
H2'B H 0.135912 1.033604 0.351844 0.088 Uiso 1 1 calc R U . . .
C2 C 0.8593(4) 0.0510(4) 0.4625(3) 0.0646(8) Uani 1 1 d . . . . .
H2A H 0.953922 0.119761 0.468855 0.078 Uiso 1 1 calc R U . . .
H2B H 0.876320 -0.034158 0.485978 0.078 Uiso 1 1 calc R U . . .
C3' C 0.1574(4) 0.8857(4) 0.2221(3) 0.0679(9) Uani 1 1 d . . . . .
H3'A H 0.244591 0.952116 0.210626 0.082 Uiso 1 1 calc R U . . .
H3'B H 0.073651 0.885541 0.157235 0.082 Uiso 1 1 calc R U . . .
C3 C 0.7660(4) 0.0159(4) 0.3297(3) 0.0634(8) Uani 1 1 d . . . . .
H3A H 0.676948 -0.061599 0.321982 0.076 Uiso 1 1 calc R U . . .
H3B H 0.819248 -0.016950 0.275986 0.076 Uiso 1 1 calc R U . . .
C4' C 0.1719(3) 0.7381(3) 0.2066(3) 0.0515(6) Uani 1 1 d . . . . .
C4 C 0.7230(3) 0.1399(3) 0.2835(2) 0.0496(6) Uani 1 1 d . . . . .
C5 C 0.6555(3) 0.2005(3) 0.3824(2) 0.0392(5) Uani 1 1 d . . . . .
H5 H 0.574120 0.118183 0.384773 0.047 Uiso 1 1 calc R U . . .
C5' C 0.2937(3) 0.7374(3) 0.3224(2) 0.0415(5) Uani 1 1 d . . . . .
H5' H 0.379688 0.814346 0.319031 0.050 Uiso 1 1 calc R U . . .
C6' C 0.3440(3) 0.6079(3) 0.3108(2) 0.0435(5) Uani 1 1 d . . . . .
H6' H 0.356393 0.589629 0.226798 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5790(3) 0.3062(3) 0.3417(2) 0.0426(5) Uani 1 1 d . . . . .
H6 H 0.519772 0.269189 0.255086 0.051 Uiso 1 1 calc R U . . .
C7' C 0.3690(4) 0.9174(4) 0.7348(3) 0.0681(8) Uani 1 1 d . . . . .
H7' H 0.272412 0.898414 0.688270 0.082 Uiso 1 1 calc R U . . .
C7 C 0.8264(3) 0.2986(3) 0.8079(3) 0.0508(6) Uani 1 1 d . . . . .
H7 H 0.897404 0.292624 0.767033 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6877(3) 0.2992(3) 0.7333(2) 0.0400(5) Uani 1 1 d . . . . .
C8' C 0.4651(3) 0.8637(3) 0.6769(3) 0.0498(6) Uani 1 1 d . . . . .
C9 C 0.6563(3) 0.2875(2) 0.5993(2) 0.0371(5) Uani 1 1 d . . . . .
C9' C 0.4183(3) 0.7889(3) 0.5502(2) 0.0417(5) Uani 1 1 d . . . . .
C10' C 0.2753(3) 0.7824(3) 0.4548(2) 0.0431(5) Uani 1 1 d . . . . .
C10 C 0.7521(3) 0.2461(3) 0.5205(2) 0.0393(5) Uani 1 1 d . . . . .
C11 C 0.5313(3) 0.3161(3) 0.5428(2) 0.0386(5) Uani 1 1 d . . . . .
C11' C 0.5095(3) 0.7206(3) 0.5137(2) 0.0417(5) Uani 1 1 d . . . . .
C12' C 0.6461(3) 0.7289(3) 0.5935(2) 0.0424(5) Uani 1 1 d . . . . .
C12 C 0.4341(3) 0.3478(3) 0.6094(2) 0.0400(5) Uani 1 1 d . . . . .
C13' C 0.6977(3) 0.8073(3) 0.7137(2) 0.0474(6) Uani 1 1 d . . . . .
C13 C 0.4582(3) 0.3510(3) 0.7362(2) 0.0413(5) Uani 1 1 d . . . . .
C14 C 0.5868(3) 0.3273(3) 0.7965(2) 0.0407(5) Uani 1 1 d . . . . .
C14' C 0.6040(3) 0.8730(3) 0.7539(3) 0.0540(7) Uani 1 1 d . . . . .
C15' C 0.8414(3) 0.8134(3) 0.8021(3) 0.0571(7) Uani 1 1 d . . . . .
H15' H 0.851247 0.873903 0.880862 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3514(3) 0.3790(3) 0.8063(2) 0.0513(6) Uani 1 1 d . . . . .
H15 H 0.394434 0.381271 0.894510 0.062 Uiso 1 1 calc R U . . .
C16' C 0.8366(5) 0.6682(5) 0.8310(4) 0.0987(16) Uani 1 1 d . . . . .
H16A H 0.749441 0.627981 0.856537 0.148 Uiso 1 1 calc R U . . .
H16B H 0.921862 0.677385 0.896838 0.148 Uiso 1 1 calc R U . . .
H16C H 0.835566 0.607393 0.757791 0.148 Uiso 1 1 calc R U . . .
C16 C 0.3289(5) 0.5226(5) 0.7978(4) 0.0805(11) Uani 1 1 d . . . . .
H16D H 0.422866 0.595819 0.820721 0.121 Uiso 1 1 calc R U . . .
H16E H 0.272400 0.541182 0.853436 0.121 Uiso 1 1 calc R U . . .
H16F H 0.277366 0.521117 0.713954 0.121 Uiso 1 1 calc R U . . .
C17' C 0.9739(4) 0.8809(5) 0.7590(4) 0.0845(12) Uani 1 1 d . . . . .
H17A H 0.970948 0.822954 0.683415 0.127 Uiso 1 1 calc R U . . .
H17B H 1.061564 0.889838 0.822049 0.127 Uiso 1 1 calc R U . . .
H17C H 0.974116 0.973274 0.743856 0.127 Uiso 1 1 calc R U . . .
C17 C 0.2062(4) 0.2576(5) 0.7648(4) 0.0733(9) Uani 1 1 d . . . . .
H17D H 0.161367 0.250797 0.678007 0.110 Uiso 1 1 calc R U . . .
H17E H 0.141613 0.275121 0.812827 0.110 Uiso 1 1 calc R U . . .
H17F H 0.223968 0.170334 0.777237 0.110 Uiso 1 1 calc R U . . .
C18 C 0.8528(4) 0.2457(4) 0.2558(4) 0.0725(9) Uani 1 1 d . . . . .
H18D H 0.827327 0.328038 0.237532 0.109 Uiso 1 1 calc R U . . .
H18E H 0.875806 0.202349 0.185317 0.109 Uiso 1 1 calc R U . . .
H18F H 0.936735 0.273155 0.327050 0.109 Uiso 1 1 calc R U . . .
C18' C 0.0212(3) 0.6238(4) 0.1843(3) 0.0647(8) Uani 1 1 d . . . . .
H18A H 0.035077 0.534202 0.193335 0.097 Uiso 1 1 calc R U . . .
H18B H -0.037808 0.616256 0.101562 0.097 Uiso 1 1 calc R U . . .
H18C H -0.027476 0.649763 0.243967 0.097 Uiso 1 1 calc R U . . .
C19' C 0.2241(4) 0.7140(4) 0.0886(3) 0.0659(8) Uani 1 1 d . . . . .
H19A H 0.324284 0.773039 0.103540 0.099 Uiso 1 1 calc R U . . .
H19B H 0.162952 0.737594 0.020463 0.099 Uiso 1 1 calc R U . . .
H19C H 0.217457 0.616182 0.068405 0.099 Uiso 1 1 calc R U . . .
C19 C 0.6028(4) 0.0777(4) 0.1599(3) 0.0716(9) Uani 1 1 d . . . . .
H19D H 0.513869 0.022269 0.175780 0.107 Uiso 1 1 calc R U . . .
H19E H 0.634305 0.018422 0.105989 0.107 Uiso 1 1 calc R U . . .
H19F H 0.584939 0.153438 0.120667 0.107 Uiso 1 1 calc R U . . .
C20 C 0.8940(3) 0.3735(3) 0.5433(3) 0.0483(6) Uani 1 1 d . . . . .
H20D H 0.869187 0.451655 0.513212 0.072 Uiso 1 1 calc R U . . .
H20E H 0.958647 0.346833 0.499820 0.072 Uiso 1 1 calc R U . . .
H20F H 0.942183 0.401157 0.630955 0.072 Uiso 1 1 calc R U . . .
C20' C 0.1435(3) 0.6797(3) 0.4853(3) 0.0534(6) Uani 1 1 d . . . . .
H20A H 0.055595 0.701021 0.450477 0.080 Uiso 1 1 calc R U . . .
H20B H 0.160480 0.690378 0.574056 0.080 Uiso 1 1 calc R U . . .
H20C H 0.132216 0.583890 0.450234 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6306(5) 0.6602(5) 0.1219(5) 0.0868(11) Uani 1 1 d . . . . .
H21D H 0.707672 0.681047 0.080734 0.130 Uiso 1 1 calc R U . . .
H21E H 0.665967 0.715495 0.205023 0.130 Uiso 1 1 calc R U . . .
H21F H 0.548168 0.683076 0.076474 0.130 Uiso 1 1 calc R U . . .
C21' C 0.1532(8) 0.1899(6) 0.0799(5) 0.1143(18) Uani 1 1 d . . . . .
H21A H 0.231851 0.190342 0.042374 0.172 Uiso 1 1 calc R U . . .
H21B H 0.063548 0.120713 0.028570 0.172 Uiso 1 1 calc R U . . .
H21C H 0.175984 0.166416 0.160990 0.172 Uiso 1 1 calc R U . . .
O1 O 0.6756(2) 0.4411(2) 0.34785(17) 0.0518(4) Uani 1 1 d . . . . .
H1 H 0.646014 0.472089 0.286160 0.078 Uiso 1 1 calc R U . . .
O1' O 0.2478(2) 0.4836(2) 0.32857(17) 0.0532(5) Uani 1 1 d . . . . .
H1' H 0.217637 0.423903 0.263925 0.080 Uiso 1 1 calc R U . . .
O2 O 0.4816(2) 0.3155(2) 0.41731(15) 0.0496(4) Uani 1 1 d . . . . .
O2' O 0.48405(19) 0.6390(2) 0.39775(16) 0.0498(4) Uani 1 1 d . . . . .
O3 O 0.3126(2) 0.3721(2) 0.54623(16) 0.0529(5) Uani 1 1 d . . . . .
H3 H 0.316345 0.377060 0.474531 0.079 Uiso 1 1 calc R U . . .
O3' O 0.7308(2) 0.6613(2) 0.55126(18) 0.0533(5) Uani 1 1 d . . . . .
H3' H 0.686522 0.614311 0.481204 0.080 Uiso 1 1 calc R U . . .
O4' O 0.6513(3) 0.9464(3) 0.8724(2) 0.0820(8) Uani 1 1 d . . . . .
H4' H 0.587620 0.985695 0.897077 0.123 Uiso 1 1 d R U . . .
O4 O 0.6166(2) 0.3384(2) 0.92194(16) 0.0542(5) Uani 1 1 d . . . . .
H4 H 0.693258 0.321314 0.947926 0.081 Uiso 1 1 calc R U . . .
O5' O 0.4069(3) 0.9869(4) 0.8423(3) 0.0958(9) Uani 1 1 d . . . . .
O5 O 0.8594(2) 0.3054(3) 0.92228(19) 0.0656(6) Uani 1 1 d . . . . .
O6' O 0.1365(3) 0.3224(3) 0.0912(2) 0.0745(6) Uani 1 1 d . . . . .
H6'A H 0.057715 0.317733 0.044242 0.112 Uiso 1 1 calc R U . . .
O6 O 0.5874(4) 0.5170(3) 0.1270(2) 0.0827(7) Uani 1 1 d . . . . .
H6A H 0.596215 0.467694 0.066139 0.124 Uiso 1 1 d 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 113.0(2) . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C10 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C2' C1' C10' 113.0(3) . . ?
C2' C1' H1'A 109.0 . . ?
C10' C1' H1'A 109.0 . . ?
C2' C1' H1'B 109.0 . . ?
C10' C1' H1'B 109.0 . . ?
H1'A C1' H1'B 107.8 . . ?
C3' C2' C1' 112.5(2) . . ?
C3' C2' H2'A 109.1 . . ?
C1' C2' H2'A 109.1 . . ?
C3' C2' H2'B 109.1 . . ?
C1' C2' H2'B 109.1 . . ?
H2'A C2' H2'B 107.8 . . ?
C3 C2 C1 111.7(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2' C3' C4' 114.1(3) . . ?
C2' C3' H3'A 108.7 . . ?
C4' C3' H3'A 108.7 . . ?
C2' C3' H3'B 108.7 . . ?
C4' C3' H3'B 108.7 . . ?
H3'A C3' H3'B 107.6 . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3' C4' C18' 110.7(3) . . ?
C3' C4' C19' 107.9(3) . . ?
C18' C4' C19' 106.7(3) . . ?
C3' C4' C5' 107.0(2) . . ?
C18' C4' C5' 115.5(2) . . ?
C19' C4' C5' 108.8(2) . . ?
C18 C4 C3 111.0(3) . . ?
C18 C4 C19 107.2(3) . . ?
C3 C4 C19 107.0(3) . . ?
C18 C4 C5 116.0(2) . . ?
C3 C4 C5 106.4(2) . . ?
C19 C4 C5 108.9(2) . . ?
C6 C5 C10 113.25(19) . . ?
C6 C5 C4 114.5(2) . . ?
C10 C5 C4 117.1(2) . . ?
C6 C5 H5 103.2 . . ?
C10 C5 H5 103.2 . . ?
C4 C5 H5 103.2 . . ?
C6' C5' C4' 114.1(2) . . ?
C6' C5' C10' 113.2(2) . . ?
C4' C5' C10' 117.8(2) . . ?
C6' C5' H5' 103.0 . . ?
C4' C5' H5' 103.0 . . ?
C10' C5' H5' 103.0 . . ?
O1' C6' O2' 108.8(2) . . ?
O1' C6' C5' 115.3(2) . . ?
O2' C6' C5' 109.01(19) . . ?
O1' C6' H6' 107.8 . . ?
O2' C6' H6' 107.8 . . ?
C5' C6' H6' 107.8 . . ?
O1 C6 O2 110.01(19) . . ?
O1 C6 C5 113.8(2) . . ?
O2 C6 C5 108.48(18) . . ?
O1 C6 H6 108.1 . . ?
O2 C6 H6 108.1 . . ?
C5 C6 H6 108.1 . . ?
O5' C7' C8' 124.3(3) . . ?
O5' C7' H7' 117.9 . . ?
C8' C7' H7' 117.9 . . ?
O5 C7 C8 125.5(3) . . ?
O5 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C14 C8 C7 117.4(2) . . ?
C14 C8 C9 120.1(2) . . ?
C7 C8 C9 122.2(2) . . ?
C14' C8' C9' 119.7(2) . . ?
C14' C8' C7' 117.5(3) . . ?
C9' C8' C7' 122.4(3) . . ?
C11 C9 C8 115.8(2) . . ?
C11 C9 C10 119.93(19) . . ?
C8 C9 C10 124.3(2) . . ?
C11' C9' C8' 116.4(2) . . ?
C11' C9' C10' 119.4(2) . . ?
C8' C9' C10' 124.1(2) . . ?
C20' C10' C9' 108.7(2) . . ?
C20' C10' C1' 111.6(2) . . ?
C9' C10' C1' 110.8(2) . . ?
C20' C10' C5' 114.4(2) . . ?
C9' C10' C5' 106.60(18) . . ?
C1' C10' C5' 104.5(2) . . ?
C9 C10 C20 108.46(19) . . ?
C9 C10 C1 110.67(19) . . ?
C20 C10 C1 112.0(2) . . ?
C9 C10 C5 106.68(18) . . ?
C20 C10 C5 114.4(2) . . ?
C1 C10 C5 104.5(2) . . ?
C9 C11 O2 126.1(2) . . ?
C9 C11 C12 122.7(2) . . ?
O2 C11 C12 111.19(19) . . ?
C9' C11' O2' 126.2(2) . . ?
C9' C11' C12' 122.5(2) . . ?
O2' C11' C12' 111.3(2) . . ?
O3' C12' C13' 118.4(2) . . ?
O3' C12' C11' 119.5(2) . . ?
C13' C12' C11' 122.1(2) . . ?
O3 C12 C13 119.1(2) . . ?
O3 C12 C11 118.8(2) . . ?
C13 C12 C11 122.1(2) . . ?
C12' C13' C14' 116.1(2) . . ?
C12' C13' C15' 122.8(2) . . ?
C14' C13' C15' 120.9(2) . . ?
C12 C13 C14 116.4(2) . . ?
C12 C13 C15 122.1(2) . . ?
C14 C13 C15 121.6(2) . . ?
O4 C14 C13 117.2(2) . . ?
O4 C14 C8 119.9(2) . . ?
C13 C14 C8 122.8(2) . . ?
O4' C14' C13' 116.7(3) . . ?
O4' C14' C8' 120.3(3) . . ?
C13' C14' C8' 123.0(2) . . ?
C17' C15' C13' 113.3(3) . . ?
C17' C15' C16' 112.1(4) . . ?
C13' C15' C16' 111.1(3) . . ?
C17' C15' H15' 106.6 . . ?
C13' C15' H15' 106.6 . . ?
C16' C15' H15' 106.6 . . ?
C13 C15 C17 110.7(2) . . ?
C13 C15 C16 112.9(3) . . ?
C17 C15 C16 111.9(3) . . ?
C13 C15 H15 107.0 . . ?
C17 C15 H15 107.0 . . ?
C16 C15 H15 107.0 . . ?
C15' C16' H16A 109.5 . . ?
C15' C16' H16B 109.5 . . ?
H16A C16' H16B 109.5 . . ?
C15' C16' H16C 109.5 . . ?
H16A C16' H16C 109.5 . . ?
H16B C16' H16C 109.5 . . ?
C15 C16 H16D 109.5 . . ?
C15 C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
C15 C16 H16F 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C15' C17' H17A 109.5 . . ?
C15' C17' H17B 109.5 . . ?
H17A C17' H17B 109.5 . . ?
C15' C17' H17C 109.5 . . ?
H17A C17' H17C 109.5 . . ?
H17B C17' H17C 109.5 . . ?
C15 C17 H17D 109.5 . . ?
C15 C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
C15 C17 H17F 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C4 C18 H18D 109.5 . . ?
C4 C18 H18E 109.5 . . ?
H18D C18 H18E 109.5 . . ?
C4 C18 H18F 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C4' C18' H18A 109.5 . . ?
C4' C18' H18B 109.5 . . ?
H18A C18' H18B 109.5 . . ?
C4' C18' H18C 109.5 . . ?
H18A C18' H18C 109.5 . . ?
H18B C18' H18C 109.5 . . ?
C4' C19' H19A 109.5 . . ?
C4' C19' H19B 109.5 . . ?
H19A C19' H19B 109.5 . . ?
C4' C19' H19C 109.5 . . ?
H19A C19' H19C 109.5 . . ?
H19B C19' H19C 109.5 . . ?
C4 C19 H19D 109.5 . . ?
C4 C19 H19E 109.5 . . ?
H19D C19 H19E 109.5 . . ?
C4 C19 H19F 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C10 C20 H20D 109.5 . . ?
C10 C20 H20E 109.5 . . ?
H20D C20 H20E 109.5 . . ?
C10 C20 H20F 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C10' C20' H20A 109.5 . . ?
C10' C20' H20B 109.5 . . ?
H20A C20' H20B 109.5 . . ?
C10' C20' H20C 109.5 . . ?
H20A C20' H20C 109.5 . . ?
H20B C20' H20C 109.5 . . ?
O6 C21 H21D 109.5 . . ?
O6 C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
O6 C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
O6' C21' H21A 109.5 . . ?
O6' C21' H21B 109.5 . . ?
H21A C21' H21B 109.5 . . ?
O6' C21' H21C 109.5 . . ?
H21A C21' H21C 109.5 . . ?
H21B C21' H21C 109.5 . . ?
C6 O1 H1 109.5 . . ?
C6' O1' H1' 109.5 . . ?
C11 O2 C6 117.33(18) . . ?
C11' O2' C6' 118.07(18) . . ?
C12 O3 H3 109.5 . . ?
C12' O3' H3' 109.5 . . ?
C14' O4' H4' 115.1 . . ?
C14 O4 H4 109.5 . . ?
C21' O6' H6'A 109.5 . . ?
C21 O6 H6A 112.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.525(4) . ?
C1 C10 1.547(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1' C2' 1.530(5) . ?
C1' C10' 1.551(4) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C2' C3' 1.509(5) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2 C3 1.505(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3' C4' 1.521(4) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4' C18' 1.540(4) . ?
C4' C19' 1.541(4) . ?
C4' C5' 1.561(3) . ?
C4 C18 1.528(4) . ?
C4 C19 1.534(4) . ?
C4 C5 1.565(3) . ?
C5 C6 1.523(3) . ?
C5 C10 1.562(3) . ?
C5 H5 0.9800 . ?
C5' C6' 1.519(3) . ?
C5' C10' 1.567(4) . ?
C5' H5' 0.9800 . ?
C6' O1' 1.399(3) . ?
C6' O2' 1.426(3) . ?
C6' H6' 0.9800 . ?
C6 O1 1.396(3) . ?
C6 O2 1.430(3) . ?
C6 H6 0.9800 . ?
C7' O5' 1.238(4) . ?
C7' C8' 1.447(4) . ?
C7' H7' 0.9300 . ?
C7 O5 1.240(3) . ?
C7 C8 1.436(3) . ?
C7 H7 0.9300 . ?
C8 C14 1.415(3) . ?
C8 C9 1.448(3) . ?
C8' C14' 1.417(4) . ?
C8' C9' 1.433(4) . ?
C9 C11 1.377(3) . ?
C9 C10 1.536(3) . ?
C9' C11' 1.377(3) . ?
C9' C10' 1.546(3) . ?
C10' C20' 1.542(4) . ?
C10 C20 1.546(4) . ?
C11 O2 1.382(3) . ?
C11 C12 1.419(3) . ?
C11' O2' 1.383(3) . ?
C11' C12' 1.414(3) . ?
C12' O3' 1.344(3) . ?
C12' C13' 1.383(4) . ?
C12 O3 1.350(3) . ?
C12 C13 1.384(3) . ?
C13' C14' 1.398(4) . ?
C13' C15' 1.517(4) . ?
C13 C14 1.395(3) . ?
C13 C15 1.515(3) . ?
C14 O4 1.356(3) . ?
C14' O4' 1.351(3) . ?
C15' C17' 1.500(5) . ?
C15' C16' 1.518(5) . ?
C15' H15' 0.9800 . ?
C15 C17 1.522(5) . ?
C15 C16 1.528(5) . ?
C15 H15 0.9800 . ?
C16' H16A 0.9600 . ?
C16' H16B 0.9600 . ?
C16' H16C 0.9600 . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 0.9600 . ?
C17' H17A 0.9600 . ?
C17' H17B 0.9600 . ?
C17' H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C18' H18A 0.9600 . ?
C18' H18B 0.9600 . ?
C18' H18C 0.9600 . ?
C19' H19A 0.9600 . ?
C19' H19B 0.9600 . ?
C19' H19C 0.9600 . ?
C19 H19D 0.9600 . ?
C19 H19E 0.9600 . ?
C19 H19F 0.9600 . ?
C20 H20D 0.9600 . ?
C20 H20E 0.9600 . ?
C20 H20F 0.9600 . ?
C20' H20A 0.9600 . ?
C20' H20B 0.9600 . ?
C20' H20C 0.9600 . ?
C21 O6 1.388(5) . ?
C21 H21D 0.9600 . ?
C21 H21E 0.9600 . ?
C21 H21F 0.9600 . ?
C21' O6' 1.380(5) . ?
C21' H21A 0.9600 . ?
C21' H21B 0.9600 . ?
C21' H21C 0.9600 . ?
O1 H1 0.8200 . ?
O1' H1' 0.8200 . ?
O3 H3 0.8200 . ?
O3' H3' 0.8200 . ?
O4' H4' 0.9052 . ?
O4 H4 0.8200 . ?
O6' H6'A 0.8200 . ?
O6 H6A 0.8302 . ?
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' -57.3(4) . . . . ?
C10 C1 C2 C3 -58.0(4) . . . . ?
C1' C2' C3' C4' 55.1(4) . . . . ?
C1 C2 C3 C4 55.4(4) . . . . ?
C2' C3' C4' C18' 75.6(3) . . . . ?
C2' C3' C4' C19' -167.9(3) . . . . ?
C2' C3' C4' C5' -51.0(3) . . . . ?
C2 C3 C4 C18 75.6(3) . . . . ?
C2 C3 C4 C19 -167.7(3) . . . . ?
C2 C3 C4 C5 -51.5(3) . . . . ?
C18 C4 C5 C6 67.1(3) . . . . ?
C3 C4 C5 C6 -168.8(2) . . . . ?
C19 C4 C5 C6 -53.9(3) . . . . ?
C18 C4 C5 C10 -68.9(3) . . . . ?
C3 C4 C5 C10 55.2(3) . . . . ?
C19 C4 C5 C10 170.1(3) . . . . ?
C3' C4' C5' C6' -168.8(2) . . . . ?
C18' C4' C5' C6' 67.6(3) . . . . ?
C19' C4' C5' C6' -52.4(3) . . . . ?
C3' C4' C5' C10' 54.8(3) . . . . ?
C18' C4' C5' C10' -68.9(3) . . . . ?
C19' C4' C5' C10' 171.1(3) . . . . ?
C4' C5' C6' O1' -76.7(3) . . . . ?
C10' C5' C6' O1' 61.7(3) . . . . ?
C4' C5' C6' O2' 160.5(2) . . . . ?
C10' C5' C6' O2' -61.0(3) . . . . ?
C10 C5 C6 O1 60.8(2) . . . . ?
C4 C5 C6 O1 -76.9(3) . . . . ?
C10 C5 C6 O2 -62.0(3) . . . . ?
C4 C5 C6 O2 160.3(2) . . . . ?
O5 C7 C8 C14 8.2(4) . . . . ?
O5 C7 C8 C9 -178.4(3) . . . . ?
O5' C7' C8' C14' 9.8(5) . . . . ?
O5' C7' C8' C9' -177.2(4) . . . . ?
C14 C8 C9 C11 4.9(3) . . . . ?
C7 C8 C9 C11 -168.3(2) . . . . ?
C14 C8 C9 C10 -175.1(2) . . . . ?
C7 C8 C9 C10 11.7(4) . . . . ?
C14' C8' C9' C11' 4.7(4) . . . . ?
C7' C8' C9' C11' -168.1(3) . . . . ?
C14' C8' C9' C10' -174.8(2) . . . . ?
C7' C8' C9' C10' 12.4(4) . . . . ?
C11' C9' C10' C20' 105.5(3) . . . . ?
C8' C9' C10' C20' -75.1(3) . . . . ?
C11' C9' C10' C1' -131.5(3) . . . . ?
C8' C9' C10' C1' 48.0(3) . . . . ?
C11' C9' C10' C5' -18.4(3) . . . . ?
C8' C9' C10' C5' 161.1(2) . . . . ?
C2' C1' C10' C20' -69.8(3) . . . . ?
C2' C1' C10' C9' 168.9(2) . . . . ?
C2' C1' C10' C5' 54.4(3) . . . . ?
C6' C5' C10' C20' -70.5(3) . . . . ?
C4' C5' C10' C20' 66.3(3) . . . . ?
C6' C5' C10' C9' 49.7(3) . . . . ?
C4' C5' C10' C9' -173.5(2) . . . . ?
C6' C5' C10' C1' 167.1(2) . . . . ?
C4' C5' C10' C1' -56.1(3) . . . . ?
C11 C9 C10 C20 106.3(3) . . . . ?
C8 C9 C10 C20 -73.7(3) . . . . ?
C11 C9 C10 C1 -130.5(2) . . . . ?
C8 C9 C10 C1 49.5(3) . . . . ?
C11 C9 C10 C5 -17.4(3) . . . . ?
C8 C9 C10 C5 162.6(2) . . . . ?
C2 C1 C10 C9 170.6(2) . . . . ?
C2 C1 C10 C20 -68.2(3) . . . . ?
C2 C1 C10 C5 56.1(3) . . . . ?
C6 C5 C10 C9 48.9(3) . . . . ?
C4 C5 C10 C9 -174.6(2) . . . . ?
C6 C5 C10 C20 -71.0(2) . . . . ?
C4 C5 C10 C20 65.5(3) . . . . ?
C6 C5 C10 C1 166.1(2) . . . . ?
C4 C5 C10 C1 -57.4(3) . . . . ?
C8 C9 C11 O2 178.1(2) . . . . ?
C10 C9 C11 O2 -1.9(4) . . . . ?
C8 C9 C11 C12 -3.3(4) . . . . ?
C10 C9 C11 C12 176.7(2) . . . . ?
C8' C9' C11' O2' 177.9(2) . . . . ?
C10' C9' C11' O2' -2.6(4) . . . . ?
C8' C9' C11' C12' -3.3(4) . . . . ?
C10' C9' C11' C12' 176.2(2) . . . . ?
C9' C11' C12' O3' -179.0(3) . . . . ?
O2' C11' C12' O3' 0.0(3) . . . . ?
C9' C11' C12' C13' -0.4(4) . . . . ?
O2' C11' C12' C13' 178.6(2) . . . . ?
C9 C11 C12 O3 -178.8(2) . . . . ?
O2 C11 C12 O3 0.0(3) . . . . ?
C9 C11 C12 C13 -0.5(4) . . . . ?
O2 C11 C12 C13 178.3(2) . . . . ?
O3' C12' C13' C14' -178.7(3) . . . . ?
C11' C12' C13' C14' 2.7(4) . . . . ?
O3' C12' C13' C15' -3.5(4) . . . . ?
C11' C12' C13' C15' 177.9(3) . . . . ?
O3 C12 C13 C14 -179.0(2) . . . . ?
C11 C12 C13 C14 2.6(4) . . . . ?
O3 C12 C13 C15 0.9(4) . . . . ?
C11 C12 C13 C15 -177.5(3) . . . . ?
C12 C13 C14 O4 176.2(2) . . . . ?
C15 C13 C14 O4 -3.7(4) . . . . ?
C12 C13 C14 C8 -0.9(4) . . . . ?
C15 C13 C14 C8 179.2(2) . . . . ?
C7 C8 C14 O4 -6.5(4) . . . . ?
C9 C8 C14 O4 -179.9(2) . . . . ?
C7 C8 C14 C13 170.5(2) . . . . ?
C9 C8 C14 C13 -3.0(4) . . . . ?
C12' C13' C14' O4' 178.1(3) . . . . ?
C15' C13' C14' O4' 2.8(4) . . . . ?
C12' C13' C14' C8' -1.2(4) . . . . ?
C15' C13' C14' C8' -176.4(3) . . . . ?
C9' C8' C14' O4' 178.2(3) . . . . ?
C7' C8' C14' O4' -8.6(5) . . . . ?
C9' C8' C14' C13' -2.6(5) . . . . ?
C7' C8' C14' C13' 170.6(3) . . . . ?
C12' C13' C15' C17' 64.2(4) . . . . ?
C14' C13' C15' C17' -120.9(4) . . . . ?
C12' C13' C15' C16' -63.2(4) . . . . ?
C14' C13' C15' C16' 111.8(4) . . . . ?
C12 C13 C15 C17 66.8(3) . . . . ?
C14 C13 C15 C17 -113.3(3) . . . . ?
C12 C13 C15 C16 -59.5(4) . . . . ?
C14 C13 C15 C16 120.4(3) . . . . ?
C9 C11 O2 C6 -10.4(4) . . . . ?
C12 C11 O2 C6 170.8(2) . . . . ?
O1 C6 O2 C11 -84.5(2) . . . . ?
C5 C6 O2 C11 40.6(3) . . . . ?
C9' C11' O2' C6' -7.6(4) . . . . ?
C12' C11' O2' C6' 173.5(2) . . . . ?
O1' C6' O2' C11' -88.5(3) . . . . ?
C5' C6' O2' C11' 38.1(3) . . . . ?
