##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-07-14
_journal_date_accepted     2009-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1942
_journal_page_last     o1943
_journal_paper_category     QO
_journal_coeditor_code     FJ2239
_publ_contact_author_name     'Dr. Kurt Mereiter'
_publ_contact_author_address
;
Institute of Chemical Technologies and Analytics
Vienna University of Technology
Getreidemarkt 9/164SC
A-1060 Vienna
Austria
;
_publ_contact_author_email     kurt.mereiter@tuwien.ac.at
_publ_contact_author_fax     '43 1 58801 17199'
_publ_contact_author_phone     '43 1 58801 17111'
_publ_section_title
;
6α-Acetoxygedunin
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hofer, Margit' .
; Comparative and Ecological Phytochemistry
  University of Vienna
  Rennweg 14
  A-1030 Vienna
  Austria
;
    'Greger, Harald' .
; Comparative and Ecological Phytochemistry
  University of Vienna
  Rennweg 14
  A-1030 Vienna
  Austria
;
    'Mereiter*, Kurt' .
;
Institute of Chemical Technologies and Analytics
Vienna University of Technology
Getreidemarkt 9/164SC
A-1060 Vienna
Austria
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;\
(1S,3aS,4aR,4bS,5S,6R,
6aR,10aR,10bR,12aS)-5,6-bis(acetyloxy)-
1-(3-furyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-
pentamethyloxireno[c]phenanthro[1,2-d]pyran-
3,8(3aH,4bH)-dione
;
_chemical_name_common     '6-α-acetoxygedunin'
_chemical_formula_moiety     'C30 H36 O9'
_chemical_formula_sum     'C30 H36 O9'
_chemical_formula_iupac     'C30 H36 O9'
_chemical_formula_weight     540.59
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     6.475(2)
_cell_length_b     14.914(5)
_cell_length_c     28.713(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2772.8(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     852
_cell_measurement_theta_min     2.42
_cell_measurement_theta_max     29.76
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.62
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.295
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1152
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.89
_exptl_absorpt_correction_T_max     0.98
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     39048
_diffrn_reflns_av_R_equivalents     0.0306
_diffrn_reflns_av_sigmaI/netI     0.0175
_diffrn_reflns_theta_min     2.53
_diffrn_reflns_theta_max     29.98
_diffrn_reflns_theta_full     29.98
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -40
_diffrn_reflns_limit_l_max     40
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4509
_reflns_number_gt     4077
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0438
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.0956
_refine_ls_wR_factor_ref     0.0994
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     4509
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0617P)²+0.3403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.259
_refine_diff_density_min     -0.244
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2003)'
_computing_data_reduction     'SAINT, SADABS and XPREP (Bruker, 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.0587(3) 0.73999(11) 0.23019(6) 0.0535(4) Uani d . 1 . .
    O O2 0.3222(2) 0.68452(7) 0.40284(4) 0.0308(3) Uani d . 1 . .
    O O3 0.21379(17) 0.50631(7) 0.42004(3) 0.0218(2) Uani d . 1 . .
    O O4 0.67376(18) 0.33557(9) 0.41784(4) 0.0303(3) Uani d . 1 . .
    O O5 0.3916(2) 0.20217(8) 0.45502(4) 0.0311(3) Uani d . 1 . .
    O O6 0.3600(2) 0.29114(9) 0.51630(4) 0.0371(3) Uani d . 1 . .
    O O7 0.3049(7) -0.02998(11) 0.35841(9) 0.1021(11) Uani d . 1 . .
    O O8 0.6555(3) 0.70255(12) 0.42549(6) 0.0546(4) Uani d . 1 . .
    O O9 0.3152(3) 0.55979(10) 0.49051(4) 0.0413(3) Uani d . 1 . .
    C C1 0.1155(3) 0.51480(13) 0.26444(5) 0.0295(3) Uani d . 1 . .
    H H1 0.0712 0.4558 0.2569 0.035 Uiso calc R 1 . .
    C C2 0.0178(3) 0.58569(14) 0.24571(6) 0.0342(4) Uani d . 1 . .
    H H2 -0.0937 0.5765 0.2247 0.041 Uiso calc R 1 . .
    C C3 0.0830(3) 0.67781(14) 0.25763(6) 0.0354(4) Uani d . 1 . .
    C C4 0.1727(3) 0.69563(11) 0.30666(6) 0.0289(3) Uani d . 1 . .
    C C5 0.2297(2) 0.60496(10) 0.33182(5) 0.0220(3) Uani d . 1 . .
    H H5 0.0998 0.5837 0.3471 0.026 Uiso calc R 1 . .
    C C6 0.3893(2) 0.61484(10) 0.37098(5) 0.0230(3) Uani d . 1 . .
    H H6 0.5258 0.6318 0.3573 0.028 Uiso calc R 1 . .
    C C7 0.4135(2) 0.52809(10) 0.39934(5) 0.0210(3) Uani d . 1 . .
    H H7 0.5176 0.5376 0.4246 0.025 Uiso calc R 1 . .
    C C8 0.4803(2) 0.44830(10) 0.36887(5) 0.0198(3) Uani d . 1 . .
    C C9 0.3279(2) 0.43982(10) 0.32698(5) 0.0208(3) Uani d . 1 . .
    H H9 0.1901 0.4274 0.3413 0.025 Uiso calc R 1 . .
    C C10 0.2973(2) 0.52800(10) 0.29783(5) 0.0217(3) Uani d . 1 . .
    C C11 0.3781(3) 0.35593(11) 0.29761(5) 0.0302(3) Uani d . 1 . .
    H H11A 0.4995 0.3692 0.2778 0.036 Uiso calc R 1 . .
    H H11B 0.2600 0.3436 0.2767 0.036 Uiso calc R 1 . .
    C C12 0.4241(3) 0.27008(11) 0.32647(6) 0.0300(3) Uani d . 1 . .
    H H12A 0.3503 0.2188 0.3122 0.036 Uiso calc R 1 . .
    H H12B 0.5739 0.2572 0.3249 0.036 Uiso calc R 1 . .
    C C13 0.3597(2) 0.27762(10) 0.37810(5) 0.0230(3) Uani d . 1 . .
    C C14 0.4749(2) 0.35925(10) 0.39801(5) 0.0210(3) Uani d . 1 . .
    C C15 0.5091(2) 0.35775(11) 0.44934(5) 0.0248(3) Uani d . 1 . .
    H H15 0.5181 0.4171 0.4654 0.030 Uiso calc R 1 . .
    C C16 0.4171(3) 0.28141(11) 0.47670(5) 0.0268(3) Uani d . 1 . .
    C C17 0.4394(3) 0.19354(11) 0.40509(6) 0.0325(4) Uani d . 1 . .
    H H17 0.5926 0.1892 0.4012 0.039 Uiso calc R 1 . .
    C C18 0.1228(2) 0.28506(11) 0.38491(5) 0.0254(3) Uani d . 1 . .
    H H18A 0.0824 0.3484 0.3851 0.038 Uiso calc R 1 . .
    H H18B 0.0840 0.2574 0.4146 0.038 Uiso calc R 1 . .
    H H18C 0.0522 0.2541 0.3594 0.038 Uiso calc R 1 . .
    C C19 0.4839(3) 0.55432(12) 0.26637(5) 0.0286(3) Uani d . 1 . .
    H H19A 0.5308 0.5016 0.2490 0.043 Uiso calc R 1 . .
    H H19B 0.5969 0.5767 0.2859 0.043 Uiso calc R 1 . .
    H H19C 0.4413 0.6012 0.2445 0.043 Uiso calc R 1 . .
    C C20 0.3434(4) 0.10558(12) 0.39106(7) 0.0455(5) Uani d . 1 . .
    C C21 0.4335(7) 0.04307(15) 0.36416(10) 0.0767(11) Uani d . 1 . .
    H H21 0.5673 0.0484 0.3509 0.092 Uiso calc R 1 . .
    C C22 0.1459(5) 0.06906(14) 0.40432(10) 0.0588(7) Uani d . 1 . .
    H H22 0.0451 0.0969 0.4235 0.071 Uiso calc R 1 . .
    C C23 0.1322(8) -0.01205(18) 0.38421(13) 0.0876(13) Uani d . 1 . .
    H H23 0.0181 -0.0516 0.3875 0.105 Uiso calc R 1 . .
    C C24 -0.0104(3) 0.74131(13) 0.33278(7) 0.0399(4) Uani d . 1 . .
    H H24A -0.0409 0.7993 0.3182 0.060 Uiso calc R 1 . .
    H H24B 0.0274 0.7507 0.3655 0.060 Uiso calc R 1 . .
    H H24C -0.1327 0.7027 0.3311 0.060 Uiso calc R 1 . .
    C C25 0.3518(3) 0.76299(12) 0.30263(7) 0.0367(4) Uani d . 1 . .
    H H25A 0.3057 0.8158 0.2852 0.055 Uiso calc R 1 . .
    H H25B 0.4678 0.7348 0.2863 0.055 Uiso calc R 1 . .
    H H25C 0.3961 0.7813 0.3339 0.055 Uiso calc R 1 . .
    C C26 0.7086(2) 0.46280(12) 0.35367(6) 0.0269(3) Uani d . 1 . .
    H H26A 0.7211 0.5204 0.3375 0.040 Uiso calc R 1 . .
    H H26B 0.7507 0.4142 0.3327 0.040 Uiso calc R 1 . .
    H H26C 0.7978 0.4629 0.3813 0.040 Uiso calc R 1 . .
    C C27 0.4760(4) 0.72270(14) 0.42919(7) 0.0419(5) Uani d . 1 . .
    C C28 0.3892(6) 0.79118(17) 0.46226(9) 0.0655(8) Uani d . 1 . .
    H H28A 0.4966 0.8349 0.4702 0.098 Uiso calc R 1 . .
    H H28B 0.3415 0.7612 0.4907 0.098 Uiso calc R 1 . .
    H H28C 0.2729 0.8221 0.4475 0.098 Uiso calc R 1 . .
    C C29 0.1864(3) 0.52448(11) 0.46639(5) 0.0268(3) Uani d . 1 . .
    C C30 -0.0241(3) 0.49403(14) 0.48189(6) 0.0382(4) Uani d . 1 . .
    H H30A -0.0316 0.4956 0.5160 0.057 Uiso calc R 1 . .
    H H30B -0.0485 0.4327 0.4710 0.057 Uiso calc R 1 . .
    H H30C -0.1294 0.5340 0.4688 0.057 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C3 . 1.227(2) ?
    O2 C27 . 1.374(3) ?
    O2 C6 . 1.4510(18) ?
    O3 C29 . 1.3697(18) ?
    O3 C7 . 1.4600(18) ?
    O4 C15 . 1.436(2) ?
    O4 C14 . 1.4517(18) ?
    O5 C16 . 1.346(2) ?
    O5 C17 . 1.472(2) ?
    O6 C16 . 1.204(2) ?
    O7 C23 . 1.368(6) ?
    O7 C21 . 1.381(5) ?
    O8 C27 . 1.205(3) ?
    O9 C29 . 1.205(2) ?
    C1 C2 . 1.344(2) ?
    C1 C10 . 1.531(2) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.478(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.546(3) ?
    C4 C25 . 1.539(3) ?
    C4 C24 . 1.560(3) ?
    C4 C5 . 1.577(2) ?
    C5 C6 . 1.534(2) ?
    C5 C10 . 1.569(2) ?
    C5 H5 . 1.0000 ?
    C6 C7 . 1.537(2) ?
    C6 H6 . 1.0000 ?
    C7 C8 . 1.539(2) ?
    C7 H7 . 1.0000 ?
    C8 C26 . 1.557(2) ?
    C8 C9 . 1.561(2) ?
    C8 C14 . 1.570(2) ?
    C9 C11 . 1.544(2) ?
    C9 C10 . 1.571(2) ?
    C9 H9 . 1.0000 ?
    C10 C19 . 1.559(2) ?
    C11 C12 . 1.554(2) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.544(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.538(2) ?
    C13 C18 . 1.551(2) ?
    C13 C17 . 1.562(2) ?
    C14 C15 . 1.491(2) ?
    C15 C16 . 1.506(2) ?
    C15 H15 . 1.0000 ?
    C17 C20 . 1.507(3) ?
    C17 H17 . 1.0000 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 C21 . 1.344(3) ?
    C20 C22 . 1.441(4) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.343(4) ?
    C22 H22 . 0.9500 ?
    C23 H23 . 0.9500 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 0.9800 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C27 C28 . 1.504(3) ?
    C28 H28A . 0.9800 ?
    C28 H28B . 0.9800 ?
    C28 H28C . 0.9800 ?
    C29 C30 . 1.504(3) ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C27 O2 C6 . . 115.28(15) ?
    C29 O3 C7 . . 117.80(12) ?
    C15 O4 C14 . . 62.14(9) ?
    C16 O5 C17 . . 120.09(12) ?
    C23 O7 C21 . . 105.9(2) ?
    C2 C1 C10 . . 120.74(16) ?
    C2 C1 H1 . . 119.6 ?
    C10 C1 H1 . . 119.6 ?
    C1 C2 C3 . . 120.26(16) ?
    C1 C2 H2 . . 119.9 ?
    C3 C2 H2 . . 119.9 ?
    O1 C3 C2 . . 121.14(18) ?
    O1 C3 C4 . . 120.21(19) ?
    C2 C3 C4 . . 118.58(14) ?
    C25 C4 C3 . . 109.08(14) ?
    C25 C4 C24 . . 108.90(16) ?
    C3 C4 C24 . . 103.16(15) ?
    C25 C4 C5 . . 114.70(14) ?
    C3 C4 C5 . . 110.96(14) ?
    C24 C4 C5 . . 109.39(13) ?
    C6 C5 C10 . . 109.77(12) ?
    C6 C5 C4 . . 114.27(13) ?
    C10 C5 C4 . . 114.05(12) ?
    C6 C5 H5 . . 106.0 ?
    C10 C5 H5 . . 106.0 ?
    C4 C5 H5 . . 106.0 ?
    O2 C6 C5 . . 109.22(12) ?
    O2 C6 C7 . . 107.43(12) ?
    C5 C6 C7 . . 112.10(12) ?
    O2 C6 H6 . . 109.3 ?
    C5 C6 H6 . . 109.3 ?
    C7 C6 H6 . . 109.3 ?
    O3 C7 C6 . . 108.21(12) ?
    O3 C7 C8 . . 107.95(11) ?
    C6 C7 C8 . . 112.24(12) ?
    O3 C7 H7 . . 109.5 ?
    C6 C7 H7 . . 109.5 ?
    C8 C7 H7 . . 109.5 ?
    C7 C8 C26 . . 108.58(13) ?
    C7 C8 C9 . . 108.85(12) ?
    C26 C8 C9 . . 113.32(11) ?
    C7 C8 C14 . . 110.18(11) ?
    C26 C8 C14 . . 106.74(12) ?
    C9 C8 C14 . . 109.15(12) ?
    C11 C9 C8 . . 110.69(12) ?
    C11 C9 C10 . . 114.45(11) ?
    C8 C9 C10 . . 114.98(12) ?
    C11 C9 H9 . . 105.2 ?
    C8 C9 H9 . . 105.2 ?
    C10 C9 H9 . . 105.2 ?
    C1 C10 C19 . . 105.40(12) ?
    C1 C10 C5 . . 105.61(13) ?
    C19 C10 C5 . . 113.12(13) ?
    C1 C10 C9 . . 108.83(13) ?
    C19 C10 C9 . . 114.95(13) ?
    C5 C10 C9 . . 108.42(11) ?
    C9 C11 C12 . . 114.64(12) ?
    C9 C11 H11A . . 108.6 ?
    C12 C11 H11A . . 108.6 ?
    C9 C11 H11B . . 108.6 ?
    C12 C11 H11B . . 108.6 ?
    H11A C11 H11B . . 107.6 ?
    C13 C12 C11 . . 113.60(13) ?
    C13 C12 H12A . . 108.8 ?
    C11 C12 H12A . . 108.8 ?
    C13 C12 H12B . . 108.8 ?
    C11 C12 H12B . . 108.8 ?
    H12A C12 H12B . . 107.7 ?
    C14 C13 C12 . . 106.49(13) ?
    C14 C13 C18 . . 112.10(13) ?
    C12 C13 C18 . . 113.16(13) ?
    C14 C13 C17 . . 106.91(13) ?
    C12 C13 C17 . . 109.19(13) ?
    C18 C13 C17 . . 108.77(14) ?
    O4 C14 C15 . . 58.43(9) ?
    O4 C14 C13 . . 112.54(12) ?
    C15 C14 C13 . . 115.33(12) ?
    O4 C14 C8 . . 113.27(12) ?
    C15 C14 C8 . . 122.44(13) ?
    C13 C14 C8 . . 118.83(12) ?
    O4 C15 C14 . . 59.43(9) ?
    O4 C15 C16 . . 116.61(14) ?
    C14 C15 C16 . . 117.91(14) ?
    O4 C15 H15 . . 116.8 ?
    C14 C15 H15 . . 116.8 ?
    C16 C15 H15 . . 116.8 ?
    O6 C16 O5 . . 120.32(15) ?
    O6 C16 C15 . . 121.52(16) ?
    O5 C16 C15 . . 118.11(14) ?
    O5 C17 C20 . . 104.45(14) ?
    O5 C17 C13 . . 110.09(13) ?
    C20 C17 C13 . . 115.47(15) ?
    O5 C17 H17 . . 108.9 ?
    C20 C17 H17 . . 108.9 ?
    C13 C17 H17 . . 108.9 ?
    C13 C18 H18A . . 109.5 ?
    C13 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C13 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C10 C19 H19A . . 109.5 ?
    C10 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C10 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C21 C20 C22 . . 106.0(3) ?
    C21 C20 C17 . . 125.3(3) ?
    C22 C20 C17 . . 128.7(2) ?
    C20 C21 O7 . . 110.8(4) ?
    C20 C21 H21 . . 124.6 ?
    O7 C21 H21 . . 124.6 ?
    C23 C22 C20 . . 106.6(3) ?
    C23 C22 H22 . . 126.7 ?
    C20 C22 H22 . . 126.7 ?
    C22 C23 O7 . . 110.8(4) ?
    C22 C23 H23 . . 124.6 ?
    O7 C23 H23 . . 124.6 ?
    C4 C24 H24A . . 109.5 ?
    C4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C4 C25 H25A . . 109.5 ?
    C4 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C4 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C8 C26 H26A . . 109.5 ?
    C8 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C8 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    O8 C27 O2 . . 123.16(18) ?
    O8 C27 C28 . . 125.8(2) ?
    O2 C27 C28 . . 111.0(2) ?
    C27 C28 H28A . . 109.5 ?
    C27 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C27 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    O9 C29 O3 . . 123.71(16) ?
    O9 C29 C30 . . 126.10(15) ?
    O3 C29 C30 . . 110.19(14) ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 C1 C2 C3 . . . . -0.8(3) ?
    C1 C2 C3 O1 . . . . 151.7(2) ?
    C1 C2 C3 C4 . . . . -31.5(3) ?
    O1 C3 C4 C25 . . . . -41.8(2) ?
    C2 C3 C4 C25 . . . . 141.42(17) ?
    O1 C3 C4 C24 . . . . 73.9(2) ?
    C2 C3 C4 C24 . . . . -102.93(18) ?
    O1 C3 C4 C5 . . . . -169.06(17) ?
    C2 C3 C4 C5 . . . . 14.1(2) ?
    C25 C4 C5 C6 . . . . 33.94(19) ?
    C3 C4 C5 C6 . . . . 158.10(13) ?
    C24 C4 C5 C6 . . . . -88.73(17) ?
    C25 C4 C5 C10 . . . . -93.47(17) ?
    C3 C4 C5 C10 . . . . 30.69(18) ?
    C24 C4 C5 C10 . . . . 143.86(15) ?
    C27 O2 C6 C5 . . . . -157.85(14) ?
    C27 O2 C6 C7 . . . . 80.34(16) ?
    C10 C5 C6 O2 . . . . -178.48(11) ?
    C4 C5 C6 O2 . . . . 51.94(16) ?
    C10 C5 C6 C7 . . . . -59.54(15) ?
    C4 C5 C6 C7 . . . . 170.89(12) ?
    C29 O3 C7 C6 . . . . -103.01(14) ?
    C29 O3 C7 C8 . . . . 135.29(13) ?
    O2 C6 C7 O3 . . . . 59.79(15) ?
    C5 C6 C7 O3 . . . . -60.21(15) ?
    O2 C6 C7 C8 . . . . 178.81(12) ?
    C5 C6 C7 C8 . . . . 58.81(16) ?
    O3 C7 C8 C26 . . . . -170.06(11) ?
    C6 C7 C8 C26 . . . . 70.76(15) ?
    O3 C7 C8 C9 . . . . 66.16(14) ?
    C6 C7 C8 C9 . . . . -53.01(16) ?
    O3 C7 C8 C14 . . . . -53.49(14) ?
    C6 C7 C8 C14 . . . . -172.67(12) ?
    C7 C8 C9 C11 . . . . -175.38(12) ?
    C26 C8 C9 C11 . . . . 63.71(16) ?
    C14 C8 C9 C11 . . . . -55.09(15) ?
    C7 C8 C9 C10 . . . . 53.01(15) ?
    C26 C8 C9 C10 . . . . -67.90(16) ?
    C14 C8 C9 C10 . . . . 173.30(12) ?
    C2 C1 C10 C19 . . . . -75.97(19) ?
    C2 C1 C10 C5 . . . . 44.02(19) ?
    C2 C1 C10 C9 . . . . 160.24(15) ?
    C6 C5 C10 C1 . . . . 172.32(12) ?
    C4 C5 C10 C1 . . . . -57.99(16) ?
    C6 C5 C10 C19 . . . . -72.91(15) ?
    C4 C5 C10 C19 . . . . 56.78(17) ?
    C6 C5 C10 C9 . . . . 55.81(15) ?
    C4 C5 C10 C9 . . . . -174.49(12) ?
    C11 C9 C10 C1 . . . . 61.00(17) ?
    C8 C9 C10 C1 . . . . -169.21(12) ?
    C11 C9 C10 C19 . . . . -56.92(18) ?
    C8 C9 C10 C19 . . . . 72.88(16) ?
    C11 C9 C10 C5 . . . . 175.40(13) ?
    C8 C9 C10 C5 . . . . -54.81(16) ?
    C8 C9 C11 C12 . . . . 43.91(19) ?
    C10 C9 C11 C12 . . . . 175.79(14) ?
    C9 C11 C12 C13 . . . . 14.2(2) ?
    C11 C12 C13 C14 . . . . -57.29(18) ?
    C11 C12 C13 C18 . . . . 66.3(2) ?
    C11 C12 C13 C17 . . . . -172.40(15) ?
    C15 O4 C14 C13 . . . . -106.78(14) ?
    C15 O4 C14 C8 . . . . 114.90(14) ?
    C12 C13 C14 O4 . . . . -90.70(14) ?
    C18 C13 C14 O4 . . . . 145.05(12) ?
    C17 C13 C14 O4 . . . . 25.94(16) ?
    C12 C13 C14 C15 . . . . -155.18(13) ?
    C18 C13 C14 C15 . . . . 80.56(16) ?
    C17 C13 C14 C15 . . . . -38.54(18) ?
    C12 C13 C14 C8 . . . . 45.10(17) ?
    C18 C13 C14 C8 . . . . -79.16(16) ?
    C17 C13 C14 C8 . . . . 161.74(13) ?
    C7 C8 C14 O4 . . . . -95.19(14) ?
    C26 C8 C14 O4 . . . . 22.52(16) ?
    C9 C8 C14 O4 . . . . 145.34(12) ?
    C7 C8 C14 C15 . . . . -28.89(19) ?
    C26 C8 C14 C15 . . . . 88.82(16) ?
    C9 C8 C14 C15 . . . . -148.36(14) ?
    C7 C8 C14 C13 . . . . 129.32(13) ?
    C26 C8 C14 C13 . . . . -112.97(14) ?
    C9 C8 C14 C13 . . . . 9.85(17) ?
    C14 O4 C15 C16 . . . . 108.19(15) ?
    C13 C14 C15 O4 . . . . 101.94(14) ?
    C8 C14 C15 O4 . . . . -99.15(15) ?
    O4 C14 C15 C16 . . . . -106.01(16) ?
    C13 C14 C15 C16 . . . . -4.1(2) ?
    C8 C14 C15 C16 . . . . 154.85(14) ?
    C17 O5 C16 O6 . . . . 172.96(16) ?
    C17 O5 C16 C15 . . . . -4.3(2) ?
    O4 C15 C16 O6 . . . . 143.88(16) ?
    C14 C15 C16 O6 . . . . -148.35(16) ?
    O4 C15 C16 O5 . . . . -38.9(2) ?
    C14 C15 C16 O5 . . . . 28.8(2) ?
    C16 O5 C17 C20 . . . . -166.21(16) ?
    C16 O5 C17 C13 . . . . -41.7(2) ?
    C14 C13 C17 O5 . . . . 61.47(17) ?
    C12 C13 C17 O5 . . . . 176.30(14) ?
    C18 C13 C17 O5 . . . . -59.77(18) ?
    C14 C13 C17 C20 . . . . 179.41(16) ?
    C12 C13 C17 C20 . . . . -65.8(2) ?
    C18 C13 C17 C20 . . . . 58.2(2) ?
    O5 C17 C20 C21 . . . . -135.9(2) ?
    C13 C17 C20 C21 . . . . 103.1(3) ?
    O5 C17 C20 C22 . . . . 41.4(3) ?
    C13 C17 C20 C22 . . . . -79.6(2) ?
    C22 C20 C21 O7 . . . . 1.5(3) ?
    C17 C20 C21 O7 . . . . 179.3(2) ?
    C23 O7 C21 C20 . . . . -2.0(3) ?
    C21 C20 C22 C23 . . . . -0.3(3) ?
    C17 C20 C22 C23 . . . . -178.1(2) ?
    C20 C22 C23 O7 . . . . -0.9(3) ?
    C21 O7 C23 C22 . . . . 1.8(4) ?
    C6 O2 C27 O8 . . . . 2.3(3) ?
    C6 O2 C27 C28 . . . . -177.72(17) ?
    C7 O3 C29 O9 . . . . 2.3(2) ?
    C7 O3 C29 C30 . . . . -177.55(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C11 H11B O1 3_545 0.99 2.59 3.410(3) 141
    C18 H18C O1 3_545 0.98 2.68 3.571(2) 152
    C18 H18B O6 4_456 0.98 2.56 3.497(2) 160
    C22 H22 O6 4_456 0.95 2.69 3.601(3) 162
    C24 H24B O2 . 0.98 2.40 3.066(3) 125
    C25 H25C O2 . 0.98 2.50 3.112(2) 121
    C5 H5 O3 . 1.00 2.50 2.931(2) 105
    C9 H9 O3 . 1.00 2.55 2.944(2) 103
    C18 H18B O5 . 0.98 2.45 2.934(2) 110
    C7 H7 O9 . 1.00 2.33 2.735(2) 103
