##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-06-20
_journal_date_accepted     2006-07-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      8
_journal_page_first     o3269
_journal_page_last     o3270
_journal_paper_category     EO
_journal_coeditor_code     CV2078
_publ_contact_author_name     'Prof. Lu Yang'
_publ_contact_author_address
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong tan street, Beijing 100050
  People's Republic of China
;
_publ_contact_author_email     luy@imm.ac.cn
_publ_contact_author_fax     '86 10 6316 5212'
_publ_contact_author_phone     '86 10 6316 5212'
_publ_section_title
;
8α,9α-Epoxy-7-oxoroyleanon
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li Wu' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong tan street, Beijing 100050
  People's Republic of China
;
    'Yang Lu' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong tan street, Beijing 100050
  People's Republic of China
;
    'Qi-Tai Zheng' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong tan street, Beijing 100050
  People's Republic of China
;
    'Xiao-Li Li' .
; State Key Laboratory of Phytochemistry and Plant Resources in West China
  Kunming Institute of Botany
  Chinese Academy of Sciences, Kunming 650204, Yunnan
  People's Republic of China
;
    'Qin-Shi Zhao' .
; State Key Laboratory of Phytochemistry and Plant Resources in West China
  Kunming Institute of Botany
  Chinese Academy of Sciences, Kunming 650204, Yunnan
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
8α,9α-Epoxy-7-oxoroyleanon
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H26 O5'
_chemical_formula_sum     'C20 H26 O5'
_chemical_formula_iupac     'C20 H26 O5'
_chemical_formula_weight     346.41
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.336(2)
_cell_length_b     7.4770(15)
_cell_length_c     11.760(2)
_cell_angle_alpha     90.00
_cell_angle_beta     101.61(3)
_cell_angle_gamma     90.00
_cell_volume     890.2(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5289
_cell_measurement_theta_min     2.40
_cell_measurement_theta_max     27.10
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.292
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'MAC DIP 2030K'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5289
_diffrn_reflns_av_R_equivalents     0.0380
_diffrn_reflns_av_sigmaI/netI     0.0120
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     27.10
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 > 2sigma(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     2066
_reflns_number_gt     1845
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0654
_refine_ls_R_factor_gt     0.0599
_refine_ls_wR_factor_gt     0.1484
_refine_ls_wR_factor_ref     0.1524
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     2066
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.071P)²+0.3757P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.249
_refine_diff_density_min     -0.183
_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     'DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                               'ORTEPII (Johnson, 1976) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97'
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
    C C1 0.5603(4) 0.5027(6) -0.1434(3) 0.0601(10) Uani d . 1 . .
    H H1A 0.5932 0.3828 -0.1237 0.072 Uiso calc R 1 . .
    H H1B 0.5013 0.5338 -0.0919 0.072 Uiso calc R 1 . .
    C C2 0.4829(5) 0.5047(7) -0.2694(4) 0.0724(13) Uani d . 1 . .
    H H2A 0.5398 0.4633 -0.3203 0.087 Uiso calc R 1 . .
    H H2B 0.4089 0.4229 -0.2769 0.087 Uiso calc R 1 . .
    C C3 0.4323(4) 0.6895(8) -0.3067(4) 0.0660(12) Uani d . 1 . .
    H H3A 0.3693 0.7257 -0.2602 0.079 Uiso calc R 1 . .
    H H3B 0.3861 0.6848 -0.3871 0.079 Uiso calc R 1 . .
    C C4 0.5423(4) 0.8313(6) -0.2948(3) 0.0548(9) Uani d . 1 . .
    C C5 0.6237(3) 0.8211(5) -0.1668(3) 0.0456(8) Uani d . 1 . .
    H H5A 0.5595 0.8498 -0.1184 0.055 Uiso calc R 1 . .
    C C6 0.7271(5) 0.9698(7) -0.1404(3) 0.0694(13) Uani d . 1 . .
    H H6A 0.7746 0.9755 -0.2035 0.083 Uiso calc R 1 . .
    H H6B 0.6817 1.0830 -0.1385 0.083 Uiso calc R 1 . .
    C C7 0.8254(4) 0.9487(6) -0.0286(3) 0.0536(9) Uani d . 1 . .
    C C8 0.7966(3) 0.8170(5) 0.0587(3) 0.0412(7) Uani d . 1 . .
    C C9 0.7334(3) 0.6482(5) 0.0077(3) 0.0406(7) Uani d . 1 . .
    C C10 0.6777(3) 0.6346(5) -0.1240(3) 0.0417(8) Uani d . 1 . .
    C C11 0.7819(4) 0.4836(6) 0.0789(3) 0.0474(8) Uani d . 1 . .
    C C12 0.8710(4) 0.5051(5) 0.1954(3) 0.0461(8) Uani d . 1 . .
    C C13 0.9102(4) 0.6617(6) 0.2471(3) 0.0467(8) Uani d . 1 . .
    C C14 0.8759(3) 0.8261(6) 0.1823(3) 0.0442(8) Uani d . 1 . .
    C C15 0.9810(4) 0.6684(7) 0.3734(3) 0.0607(10) Uani d . 1 . .
    H H15A 0.9994 0.5434 0.3961 0.073 Uiso calc R 1 . .
    C C16 0.8894(5) 0.7348(9) 0.4491(4) 0.0799(17) Uani d . 1 . .
    H H16A 0.9356 0.7379 0.5285 0.120 Uiso calc R 1 . .
    H H16B 0.8149 0.6558 0.4419 0.120 Uiso calc R 1 . .
    H H16C 0.8593 0.8529 0.4250 0.120 Uiso calc R 1 . .
    C C17 1.1124(4) 0.7584(9) 0.3949(4) 0.0761(14) Uani d . 1 . .
    H H17A 1.1497 0.7570 0.4766 0.114 Uiso calc R 1 . .
    H H17B 1.1020 0.8799 0.3682 0.114 Uiso calc R 1 . .
    H H17C 1.1701 0.6963 0.3538 0.114 Uiso calc R 1 . .
    C C18 0.4767(6) 1.0156(8) -0.3122(5) 0.0850(17) Uani d . 1 . .
    H H18A 0.4262 1.0248 -0.3900 0.127 Uiso calc R 1 . .
    H H18B 0.5434 1.1068 -0.2995 0.127 Uiso calc R 1 . .
    H H18C 0.4193 1.0308 -0.2581 0.127 Uiso calc R 1 . .
    C C19 0.6226(5) 0.8076(9) -0.3901(3) 0.0745(14) Uani d . 1 . .
    H H19A 0.5648 0.8153 -0.4648 0.112 Uiso calc R 1 . .
    H H19B 0.6651 0.6929 -0.3819 0.112 Uiso calc R 1 . .
    H H19C 0.6883 0.9000 -0.3832 0.112 Uiso calc R 1 . .
    C C20 0.7906(4) 0.5657(8) -0.1790(3) 0.0662(13) Uani d . 1 . .
    H H20A 0.7606 0.5558 -0.2615 0.099 Uiso calc R 1 . .
    H H20B 0.8185 0.4504 -0.1473 0.099 Uiso calc R 1 . .
    H H20C 0.8634 0.6477 -0.1626 0.099 Uiso calc R 1 . .
    O O21 0.9324(3) 1.0220(6) -0.0125(3) 0.0772(10) Uani d . 1 . .
    O O22 0.6612(2) 0.7711(4) 0.0659(2) 0.0488(6) Uani d . 1 . .
    O O23 0.7526(3) 0.3336(4) 0.0465(3) 0.0703(9) Uani d . 1 . .
    O O24 0.9033(3) 0.3505(4) 0.2517(2) 0.0622(8) Uani d . 1 . .
    H H24A 0.8703 0.2670 0.2107 0.093 Uiso calc R 1 . .
    O O25 0.8999(3) 0.9757(4) 0.2247(2) 0.0606(8) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.536(5) ?
    C1 C10 . 1.544(5) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.511(8) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.540(7) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C18 . 1.532(7) ?
    C4 C19 . 1.534(6) ?
    C4 C5 . 1.572(4) ?
    C5 C6 . 1.530(6) ?
    C5 C10 . 1.547(5) ?
    C5 H5A . 0.9800 ?
    C6 C7 . 1.499(5) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 O21 . 1.215(5) ?
    C7 C8 . 1.495(5) ?
    C8 O22 . 1.460(4) yes
    C8 C9 . 1.491(5) ?
    C8 C14 . 1.520(4) ?
    C9 O22 . 1.441(4) yes
    C9 C11 . 1.517(5) ?
    C9 C10 . 1.543(4) ?
    C10 C20 . 1.533(5) ?
    C11 O23 . 1.204(5) ?
    C11 C12 . 1.498(5) ?
    C12 O24 . 1.341(5) ?
    C12 C13 . 1.343(6) ?
    C13 C14 . 1.452(6) ?
    C13 C15 . 1.519(5) ?
    C14 O25 . 1.229(5) ?
    C15 C17 . 1.491(6) ?
    C15 C16 . 1.508(7) ?
    C15 H15A . 0.9800 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 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 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    O24 H24A . 0.8200 ?
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
    C2 C1 C10 . . 112.1(3) ?
    C2 C1 H1A . . 109.2 ?
    C10 C1 H1A . . 109.2 ?
    C2 C1 H1B . . 109.2 ?
    C10 C1 H1B . . 109.2 ?
    H1A C1 H1B . . 107.9 ?
    C3 C2 C1 . . 111.8(4) ?
    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 . . 113.4(3) ?
    C2 C3 H3A . . 108.9 ?
    C4 C3 H3A . . 108.9 ?
    C2 C3 H3B . . 108.9 ?
    C4 C3 H3B . . 108.9 ?
    H3A C3 H3B . . 107.7 ?
    C18 C4 C19 . . 107.2(4) ?
    C18 C4 C3 . . 108.0(4) ?
    C19 C4 C3 . . 110.6(4) ?
    C18 C4 C5 . . 108.0(4) ?
    C19 C4 C5 . . 115.5(3) ?
    C3 C4 C5 . . 107.3(3) ?
    C6 C5 C10 . . 113.4(3) ?
    C6 C5 C4 . . 112.1(3) ?
    C10 C5 C4 . . 116.3(3) ?
    C6 C5 H5A . . 104.5 ?
    C10 C5 H5A . . 104.5 ?
    C4 C5 H5A . . 104.5 ?
    C7 C6 C5 . . 115.1(3) ?
    C7 C6 H6A . . 108.5 ?
    C5 C6 H6A . . 108.5 ?
    C7 C6 H6B . . 108.5 ?
    C5 C6 H6B . . 108.5 ?
    H6A C6 H6B . . 107.5 ?
    O21 C7 C8 . . 119.4(3) ?
    O21 C7 C6 . . 121.7(4) ?
    C8 C7 C6 . . 118.5(3) ?
    O22 C8 C9 . . 58.5(2) yes
    O22 C8 C7 . . 121.4(3) ?
    C9 C8 C7 . . 114.4(3) ?
    O22 C8 C14 . . 107.1(2) ?
    C9 C8 C14 . . 122.1(3) ?
    C7 C8 C14 . . 118.9(3) ?
    O22 C9 C8 . . 59.7(2) yes
    O22 C9 C11 . . 113.6(3) ?
    C8 C9 C11 . . 113.3(3) ?
    O22 C9 C10 . . 113.2(3) ?
    C8 C9 C10 . . 120.3(3) ?
    C11 C9 C10 . . 121.1(3) ?
    C20 C10 C9 . . 106.4(3) ?
    C20 C10 C1 . . 111.4(4) ?
    C9 C10 C1 . . 108.3(3) ?
    C20 C10 C5 . . 114.9(3) ?
    C9 C10 C5 . . 107.7(3) ?
    C1 C10 C5 . . 107.9(3) ?
    O23 C11 C12 . . 117.4(4) ?
    O23 C11 C9 . . 123.1(3) ?
    C12 C11 C9 . . 119.5(3) ?
    O24 C12 C13 . . 120.4(3) ?
    O24 C12 C11 . . 113.9(3) ?
    C13 C12 C11 . . 125.5(3) ?
    C12 C13 C14 . . 118.8(3) ?
    C12 C13 C15 . . 120.8(4) ?
    C14 C13 C15 . . 120.3(4) ?
    O25 C14 C13 . . 123.3(3) ?
    O25 C14 C8 . . 117.0(3) ?
    C13 C14 C8 . . 119.4(3) ?
    C17 C15 C16 . . 114.2(4) ?
    C17 C15 C13 . . 115.1(4) ?
    C16 C15 C13 . . 110.6(4) ?
    C17 C15 H15A . . 105.3 ?
    C16 C15 H15A . . 105.3 ?
    C13 C15 H15A . . 105.3 ?
    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 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 ?
    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 ?
    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 ?
    C9 O22 C8 . . 61.8(2) yes
    C12 O24 H24A . . 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 . . . . -57.2(5) ?
    C1 C2 C3 C4 . . . . 57.3(6) ?
    C2 C3 C4 C18 . . . . -169.2(4) ?
    C2 C3 C4 C19 . . . . 73.8(5) ?
    C2 C3 C4 C5 . . . . -53.0(5) ?
    C18 C4 C5 C6 . . . . -57.7(5) ?
    C19 C4 C5 C6 . . . . 62.3(5) ?
    C3 C4 C5 C6 . . . . -173.9(4) ?
    C18 C4 C5 C10 . . . . 169.5(4) ?
    C19 C4 C5 C10 . . . . -70.5(5) ?
    C3 C4 C5 C10 . . . . 53.3(4) ?
    C10 C5 C6 C7 . . . . -34.5(5) ?
    C4 C5 C6 C7 . . . . -168.8(4) ?
    C5 C6 C7 O21 . . . . 157.9(5) ?
    C5 C6 C7 C8 . . . . -14.8(6) ?
    O21 C7 C8 O22 . . . . 159.1(4) ?
    C6 C7 C8 O22 . . . . -28.1(6) ?
    O21 C7 C8 C9 . . . . -134.2(4) ?
    C6 C7 C8 C9 . . . . 38.6(5) ?
    O21 C7 C8 C14 . . . . 22.1(6) ?
    C6 C7 C8 C14 . . . . -165.0(4) ?
    C7 C8 C9 O22 . . . . -113.1(3) ?
    C14 C8 C9 O22 . . . . 91.3(3) ?
    O22 C8 C9 C11 . . . . -104.7(3) ?
    C7 C8 C9 C11 . . . . 142.2(3) ?
    C14 C8 C9 C11 . . . . -13.3(4) ?
    O22 C8 C9 C10 . . . . 100.8(3) ?
    C7 C8 C9 C10 . . . . -12.3(4) ?
    C14 C8 C9 C10 . . . . -167.9(3) ?
    O22 C9 C10 C20 . . . . 157.5(4) ?
    C8 C9 C10 C20 . . . . 90.2(4) ?
    C11 C9 C10 C20 . . . . -62.4(5) ?
    O22 C9 C10 C1 . . . . -82.6(4) ?
    C8 C9 C10 C1 . . . . -149.9(3) ?
    C11 C9 C10 C1 . . . . 57.5(4) ?
    O22 C9 C10 C5 . . . . 33.8(4) ?
    C8 C9 C10 C5 . . . . -33.5(4) ?
    C11 C9 C10 C5 . . . . 173.9(3) ?
    C2 C1 C10 C20 . . . . -73.3(5) ?
    C2 C1 C10 C9 . . . . 170.0(4) ?
    C2 C1 C10 C5 . . . . 53.7(5) ?
    C6 C5 C10 C20 . . . . -61.5(4) ?
    C4 C5 C10 C20 . . . . 70.8(4) ?
    C6 C5 C10 C9 . . . . 57.0(4) ?
    C4 C5 C10 C9 . . . . -170.8(3) ?
    C6 C5 C10 C1 . . . . 173.6(3) ?
    C4 C5 C10 C1 . . . . -54.2(4) ?
    O22 C9 C11 O23 . . . . 121.8(4) ?
    C8 C9 C11 O23 . . . . -172.5(4) ?
    C10 C9 C11 O23 . . . . -18.1(6) ?
    O22 C9 C11 C12 . . . . -58.4(4) ?
    C8 C9 C11 C12 . . . . 7.3(5) ?
    C10 C9 C11 C12 . . . . 161.6(3) ?
    O23 C11 C12 O24 . . . . -2.4(6) ?
    C9 C11 C12 O24 . . . . 177.8(3) ?
    O23 C11 C12 C13 . . . . -177.6(4) yes
    C9 C11 C12 C13 . . . . 2.6(6) ?
    O24 C12 C13 C14 . . . . 178.5(4) ?
    C11 C12 C13 C14 . . . . -6.6(6) ?
    O24 C12 C13 C15 . . . . -5.6(6) ?
    C11 C12 C13 C15 . . . . 169.3(4) ?
    C12 C13 C14 O25 . . . . 175.1(4) yes
    C15 C13 C14 O25 . . . . -0.8(5) ?
    C12 C13 C14 C8 . . . . 0.3(5) ?
    C15 C13 C14 C8 . . . . -175.7(3) ?
    O22 C8 C14 O25 . . . . -101.8(4) ?
    C9 C8 C14 O25 . . . . -164.9(3) ?
    C7 C8 C14 O25 . . . . 40.6(5) ?
    O22 C8 C14 C13 . . . . 73.3(4) ?
    C9 C8 C14 C13 . . . . 10.3(5) ?
    C7 C8 C14 C13 . . . . -144.2(4) ?
    C12 C13 C15 C17 . . . . 124.0(5) ?
    C14 C13 C15 C17 . . . . -60.2(6) ?
    C12 C13 C15 C16 . . . . -104.8(5) ?
    C14 C13 C15 C16 . . . . 71.1(5) ?
    C11 C9 O22 C8 . . . . 104.2(3) ?
    C10 C9 O22 C8 . . . . -112.7(3) ?
    C7 C8 O22 C9 . . . . 101.1(4) ?
    C14 C8 O22 C9 . . . . -117.6(3) ?
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
    _geom_hbond_publ_flag
    O24 H24A O25 1_545 0.82 2.20 2.820(4) 132.4 yes
