##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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          #
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#                                                                            #
# 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     2008-06-25
_journal_date_accepted     2008-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1643
_journal_page_last     o1644
_journal_paper_category     QO
_journal_coeditor_code     HB2752
_publ_contact_author
;
Frank R. Fronczek
Department of Chemistry
Louisiana State University
Baton Rouge
LA  70803-1804
USA
;
_publ_contact_author_email     ffroncz@lsu.edu
_publ_contact_author_fax     '(225) 578 3458'
_publ_contact_author_phone     '(225) 578 8270'
_publ_section_title
;
Hoodigogenin A from Hoodia gordonii
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shukla, Yatin J.' .
; Department of Pharmacognosy
  School of Pharmacy
  University of Mississippi
  University
  MS 38677
  USA
;
    'Fronczek, Frank R.' .
;    Department of Chemistry
     Louisiana State University
     Baton Rouge
     LA 70803-1804
     USA
;
    'Pawar, Rahul S.' .
; National Center for Natural Products Research
  Research Institute for Pharmaceutical Sciences
  University of Mississippi
  University
  MS 38677
  USA
;
    'Khan, Ikhlas A.' .
; Department of Pharmacognosy
  School of Pharmacy
  University of Mississippi
  University
  MS 38677
  USA
  and
  National Center for Natural Products Research
  Research Institute for Pharmaceutical Sciences
  University of Mississippi
  University
  MS 38677
  USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
12-O-β-tigloyl-3β,1β-dihydroxypregn-5-en-20-one
;
_chemical_name_common
;
Hoodigogenin A
;
_chemical_formula_moiety     'C26 H38 O5'
_chemical_formula_sum     'C26 H38 O5'
_chemical_formula_iupac     'C26 H38 O5'
_chemical_formula_weight     430.56
_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+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     7.6523(9)
_cell_length_b     10.6885(12)
_cell_length_c     27.705(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2266.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2446
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     26.6
_cell_measurement_temperature     100
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.262
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.086
_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     100
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device
                'Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9377
_diffrn_reflns_av_R_equivalents     0.030
_diffrn_reflns_av_sigmaI/netI     0.0422
_diffrn_reflns_theta_min     2.7
_diffrn_reflns_theta_max     26.7
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -34
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <2
_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     2677
_reflns_number_gt     2156
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.058
_refine_ls_R_factor_gt     0.040
_refine_ls_wR_factor_gt     0.092
_refine_ls_wR_factor_ref     0.100
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     2677
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0516P)²+0.3846P] 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     0.20
_refine_diff_density_min     -0.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_reduction     'SCALEPACK and DENZO (Otwinowski & Minor 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (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 0.9957(2) 0.46948(17) 0.91649(6) 0.0407(5) Uani d . 1 . .
    H H10H 1.0621 0.4080 0.9120 0.061 Uiso calc R 1 . .
    O O2 0.3082(2) 0.30783(16) 0.67021(6) 0.0341(4) Uani d . 1 . .
    H H20H 0.2534 0.3094 0.6439 0.051 Uiso calc R 1 . .
    O O3 0.2237(2) 0.30076(18) 0.56873(6) 0.0436(5) Uani d . 1 . .
    O O4 0.7859(2) 0.53134(15) 0.59363(6) 0.0305(4) Uani d . 1 . .
    O O5 0.7923(2) 0.74167(16) 0.59427(6) 0.0369(4) Uani d . 1 . .
    C C1 0.9214(3) 0.5459(3) 0.78456(8) 0.0302(5) Uani d . 1 . .
    H H1A 1.0060 0.5598 0.7581 0.036 Uiso calc R 1 . .
    H H1B 0.8524 0.6236 0.7884 0.036 Uiso calc R 1 . .
    C C2 1.0228(3) 0.5220(3) 0.83123(9) 0.0342(6) Uani d . 1 . .
    H H2A 1.1021 0.4498 0.8266 0.041 Uiso calc R 1 . .
    H H2B 1.0951 0.5962 0.8389 0.041 Uiso calc R 1 . .
    C C3 0.9010(4) 0.4954(2) 0.87292(8) 0.0338(6) Uani d . 1 . .
    H H3 0.8282 0.5718 0.8785 0.041 Uiso calc R 1 . .
    C C4 0.7785(3) 0.3879(2) 0.86049(9) 0.0329(6) Uani d . 1 . .
    H H4A 0.8471 0.3095 0.8585 0.039 Uiso calc R 1 . .
    H H4B 0.6921 0.3780 0.8868 0.039 Uiso calc R 1 . .
    C C5 0.6821(3) 0.4070(2) 0.81332(9) 0.0291(5) Uani d . 1 . .
    C C6 0.5095(3) 0.3951(2) 0.81037(9) 0.0329(6) Uani d . 1 . .
    H H6 0.4469 0.3787 0.8393 0.039 Uiso calc R 1 . .
    C C7 0.4070(3) 0.4058(3) 0.76433(9) 0.0349(6) Uani d . 1 . .
    H H7A 0.3450 0.4871 0.7638 0.042 Uiso calc R 1 . .
    H H7B 0.3182 0.3385 0.7632 0.042 Uiso calc R 1 . .
    C C8 0.5244(3) 0.3962(2) 0.71992(8) 0.0289(5) Uani d . 1 . .
    H H8 0.5711 0.3089 0.7191 0.035 Uiso calc R 1 . .
    C C9 0.6822(3) 0.4840(2) 0.72681(8) 0.0273(5) Uani d . 1 . .
    H H9 0.6346 0.5680 0.7358 0.033 Uiso calc R 1 . .
    C C10 0.7967(3) 0.4390(2) 0.76984(8) 0.0276(5) Uani d . 1 . .
    C C11 0.7907(3) 0.5023(2) 0.68051(8) 0.0292(6) Uani d . 1 . .
    H H11A 0.8714 0.5738 0.6850 0.035 Uiso calc R 1 . .
    H H11B 0.8622 0.4266 0.6747 0.035 Uiso calc R 1 . .
    C C12 0.6770(3) 0.5265(2) 0.63685(8) 0.0284(5) Uani d . 1 . .
    H H12 0.6155 0.6084 0.6409 0.034 Uiso calc R 1 . .
    C C13 0.5413(3) 0.4230(2) 0.62780(8) 0.0282(5) Uani d . 1 . .
    C C14 0.4220(3) 0.4154(2) 0.67314(9) 0.0283(5) Uani d . 1 . .
    C C15 0.3094(3) 0.5331(2) 0.66889(9) 0.0324(6) Uani d . 1 . .
    H H15A 0.3745 0.6079 0.6798 0.039 Uiso calc R 1 . .
    H H15B 0.2013 0.5250 0.6883 0.039 Uiso calc R 1 . .
    C C16 0.2667(3) 0.5414(3) 0.61473(9) 0.0361(6) Uani d . 1 . .
    H H16A 0.2616 0.6299 0.6044 0.043 Uiso calc R 1 . .
    H H16B 0.1522 0.5019 0.6080 0.043 Uiso calc R 1 . .
    C C17 0.4140(3) 0.4716(2) 0.58736(9) 0.0311(5) Uani d . 1 . .
    H H17 0.4780 0.5329 0.5666 0.037 Uiso calc R 1 . .
    C C18 0.6315(3) 0.2983(2) 0.61696(9) 0.0324(6) Uani d . 1 . .
    H H18A 0.6999 0.2722 0.6451 0.049 Uiso calc R 1 . .
    H H18B 0.7093 0.3083 0.5891 0.049 Uiso calc R 1 . .
    H H18C 0.5431 0.2347 0.6097 0.049 Uiso calc R 1 . .
    C C19 0.9048(3) 0.3220(2) 0.75633(9) 0.0306(6) Uani d . 1 . .
    H H19A 0.9960 0.3454 0.7332 0.046 Uiso calc R 1 . .
    H H19B 0.8279 0.2592 0.7418 0.046 Uiso calc R 1 . .
    H H19C 0.9590 0.2873 0.7854 0.046 Uiso calc R 1 . .
    C C20 0.3456(3) 0.3660(2) 0.55563(9) 0.0336(6) Uani d . 1 . .
    C C21 0.4373(4) 0.3454(3) 0.50851(9) 0.0427(7) Uani d . 1 . .
    H H21A 0.5622 0.3317 0.5144 0.064 Uiso calc R 1 . .
    H H21B 0.4221 0.4191 0.4879 0.064 Uiso calc R 1 . .
    H H21C 0.3877 0.2719 0.4924 0.064 Uiso calc R 1 . .
    C C22 0.8251(3) 0.6433(2) 0.57417(9) 0.0296(5) Uani d . 1 . .
    C C23 0.9065(3) 0.6338(2) 0.52566(9) 0.0301(6) Uani d . 1 . .
    C C24 0.9321(4) 0.7573(3) 0.50011(11) 0.0379(6) Uani d . 1 . .
    H H24A 1.0187 0.8073 0.5176 0.057 Uiso calc R 1 . .
    H H24B 0.8209 0.8026 0.4990 0.057 Uiso calc R 1 . .
    H H24C 0.9735 0.7420 0.4672 0.057 Uiso calc R 1 . .
    C C25 0.9463(3) 0.5220(3) 0.50738(9) 0.0344(6) Uani d . 1 . .
    H H25 0.9221 0.4519 0.5274 0.041 Uiso calc R 1 . .
    C C26 1.0243(4) 0.4940(3) 0.45924(9) 0.0412(7) Uani d . 1 . .
    H H26A 1.0654 0.5719 0.4444 0.062 Uiso calc R 1 . .
    H H26B 0.9359 0.4553 0.4385 0.062 Uiso calc R 1 . .
    H H26C 1.1230 0.4364 0.4632 0.062 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 . 1.435(3) ?
    O1 H10H . 0.8400 ?
    O2 C14 . 1.445(3) ?
    O2 H20H . 0.8400 ?
    O3 C20 . 1.220(3) ?
    O4 C22 . 1.347(3) ?
    O4 C12 . 1.460(3) ?
    O5 C22 . 1.216(3) ?
    C1 C2 . 1.530(3) ?
    C1 C10 . 1.543(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.511(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.523(4) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.515(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.329(3) ?
    C5 C10 . 1.529(3) ?
    C6 C7 . 1.502(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.527(3) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C14 . 1.528(3) ?
    C8 C9 . 1.542(3) ?
    C8 H8 . 1.0000 ?
    C9 C11 . 1.540(3) ?
    C9 C10 . 1.555(3) ?
    C9 H9 . 1.0000 ?
    C10 C19 . 1.545(3) ?
    C11 C12 . 1.512(3) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.538(3) ?
    C12 H12 . 1.0000 ?
    C13 C18 . 1.530(3) ?
    C13 C14 . 1.555(3) ?
    C13 C17 . 1.573(3) ?
    C14 C15 . 1.529(3) ?
    C15 C16 . 1.538(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.550(3) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C20 . 1.523(4) ?
    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 . 1.498(4) ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 C23 . 1.485(3) ?
    C23 C25 . 1.333(4) ?
    C23 C24 . 1.511(4) ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 C26 . 1.492(4) ?
    C25 H25 . 0.9500 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 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
    C3 O1 H10H . . 109.5 ?
    C14 O2 H20H . . 109.5 ?
    C22 O4 C12 . . 119.14(18) ?
    C2 C1 C10 . . 114.4(2) ?
    C2 C1 H1A . . 108.7 ?
    C10 C1 H1A . . 108.7 ?
    C2 C1 H1B . . 108.7 ?
    C10 C1 H1B . . 108.7 ?
    H1A C1 H1B . . 107.6 ?
    C3 C2 C1 . . 111.38(19) ?
    C3 C2 H2A . . 109.4 ?
    C1 C2 H2A . . 109.4 ?
    C3 C2 H2B . . 109.4 ?
    C1 C2 H2B . . 109.4 ?
    H2A C2 H2B . . 108.0 ?
    O1 C3 C2 . . 111.6(2) ?
    O1 C3 C4 . . 110.8(2) ?
    C2 C3 C4 . . 110.4(2) ?
    O1 C3 H3 . . 108.0 ?
    C2 C3 H3 . . 108.0 ?
    C4 C3 H3 . . 108.0 ?
    C5 C4 C3 . . 113.1(2) ?
    C5 C4 H4A . . 109.0 ?
    C3 C4 H4A . . 109.0 ?
    C5 C4 H4B . . 109.0 ?
    C3 C4 H4B . . 109.0 ?
    H4A C4 H4B . . 107.8 ?
    C6 C5 C4 . . 121.6(2) ?
    C6 C5 C10 . . 122.9(2) ?
    C4 C5 C10 . . 115.52(19) ?
    C5 C6 C7 . . 124.3(2) ?
    C5 C6 H6 . . 117.8 ?
    C7 C6 H6 . . 117.8 ?
    C6 C7 C8 . . 111.86(19) ?
    C6 C7 H7A . . 109.2 ?
    C8 C7 H7A . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    C8 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    C7 C8 C14 . . 111.91(18) ?
    C7 C8 C9 . . 108.7(2) ?
    C14 C8 C9 . . 115.15(19) ?
    C7 C8 H8 . . 106.9 ?
    C14 C8 H8 . . 106.9 ?
    C9 C8 H8 . . 106.9 ?
    C11 C9 C8 . . 113.34(18) ?
    C11 C9 C10 . . 111.96(18) ?
    C8 C9 C10 . . 110.35(19) ?
    C11 C9 H9 . . 106.9 ?
    C8 C9 H9 . . 106.9 ?
    C10 C9 H9 . . 106.9 ?
    C5 C10 C1 . . 108.17(19) ?
    C5 C10 C19 . . 108.47(19) ?
    C1 C10 C19 . . 109.41(19) ?
    C5 C10 C9 . . 110.49(19) ?
    C1 C10 C9 . . 108.76(19) ?
    C19 C10 C9 . . 111.48(19) ?
    C12 C11 C9 . . 112.20(18) ?
    C12 C11 H11A . . 109.2 ?
    C9 C11 H11A . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    C9 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    O4 C12 C11 . . 109.50(17) ?
    O4 C12 C13 . . 106.10(18) ?
    C11 C12 C13 . . 113.3(2) ?
    O4 C12 H12 . . 109.3 ?
    C11 C12 H12 . . 109.3 ?
    C13 C12 H12 . . 109.3 ?
    C18 C13 C12 . . 110.73(19) ?
    C18 C13 C14 . . 112.2(2) ?
    C12 C13 C14 . . 107.59(19) ?
    C18 C13 C17 . . 115.3(2) ?
    C12 C13 C17 . . 107.28(19) ?
    C14 C13 C17 . . 103.22(18) ?
    O2 C14 C8 . . 104.46(18) ?
    O2 C14 C15 . . 108.09(18) ?
    C8 C14 C15 . . 117.7(2) ?
    O2 C14 C13 . . 110.49(19) ?
    C8 C14 C13 . . 113.02(17) ?
    C15 C14 C13 . . 103.07(19) ?
    C14 C15 C16 . . 104.0(2) ?
    C14 C15 H15A . . 111.0 ?
    C16 C15 H15A . . 111.0 ?
    C14 C15 H15B . . 111.0 ?
    C16 C15 H15B . . 111.0 ?
    H15A C15 H15B . . 109.0 ?
    C15 C16 C17 . . 107.2(2) ?
    C15 C16 H16A . . 110.3 ?
    C17 C16 H16A . . 110.3 ?
    C15 C16 H16B . . 110.3 ?
    C17 C16 H16B . . 110.3 ?
    H16A C16 H16B . . 108.5 ?
    C20 C17 C16 . . 112.9(2) ?
    C20 C17 C13 . . 112.3(2) ?
    C16 C17 C13 . . 105.12(19) ?
    C20 C17 H17 . . 108.8 ?
    C16 C17 H17 . . 108.8 ?
    C13 C17 H17 . . 108.8 ?
    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 ?
    O3 C20 C21 . . 122.2(2) ?
    O3 C20 C17 . . 121.0(2) ?
    C21 C20 C17 . . 116.8(2) ?
    C20 C21 H21A . . 109.5 ?
    C20 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O5 C22 O4 . . 122.6(2) ?
    O5 C22 C23 . . 124.1(2) ?
    O4 C22 C23 . . 113.2(2) ?
    C25 C23 C22 . . 120.1(2) ?
    C25 C23 C24 . . 125.1(2) ?
    C22 C23 C24 . . 114.7(2) ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C23 C25 C26 . . 127.7(2) ?
    C23 C25 H25 . . 116.2 ?
    C26 C25 H25 . . 116.2 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 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 . . . . -56.4(3) ?
    C1 C2 C3 O1 . . . . 178.4(2) ?
    C1 C2 C3 C4 . . . . 54.7(3) ?
    O1 C3 C4 C5 . . . . -176.92(19) ?
    C2 C3 C4 C5 . . . . -52.8(3) ?
    C3 C4 C5 C6 . . . . -128.9(3) ?
    C3 C4 C5 C10 . . . . 51.8(3) ?
    C4 C5 C6 C7 . . . . -176.5(2) ?
    C10 C5 C6 C7 . . . . 2.7(4) ?
    C5 C6 C7 C8 . . . . 15.6(4) ?
    C6 C7 C8 C14 . . . . -176.4(2) ?
    C6 C7 C8 C9 . . . . -48.1(3) ?
    C7 C8 C9 C11 . . . . -168.6(2) ?
    C14 C8 C9 C11 . . . . -42.2(3) ?
    C7 C8 C9 C10 . . . . 64.9(2) ?
    C14 C8 C9 C10 . . . . -168.70(19) ?
    C6 C5 C10 C1 . . . . 131.8(3) ?
    C4 C5 C10 C1 . . . . -48.9(3) ?
    C6 C5 C10 C19 . . . . -109.6(3) ?
    C4 C5 C10 C19 . . . . 69.7(3) ?
    C6 C5 C10 C9 . . . . 12.9(3) ?
    C4 C5 C10 C9 . . . . -167.9(2) ?
    C2 C1 C10 C5 . . . . 51.3(3) ?
    C2 C1 C10 C19 . . . . -66.7(3) ?
    C2 C1 C10 C9 . . . . 171.30(19) ?
    C11 C9 C10 C5 . . . . -173.29(19) ?
    C8 C9 C10 C5 . . . . -46.0(2) ?
    C11 C9 C10 C1 . . . . 68.1(2) ?
    C8 C9 C10 C1 . . . . -164.62(18) ?
    C11 C9 C10 C19 . . . . -52.6(3) ?
    C8 C9 C10 C19 . . . . 74.7(2) ?
    C8 C9 C11 C12 . . . . 45.5(3) ?
    C10 C9 C11 C12 . . . . 171.1(2) ?
    C22 O4 C12 C11 . . . . -102.8(2) ?
    C22 O4 C12 C13 . . . . 134.6(2) ?
    C9 C11 C12 O4 . . . . -174.75(19) ?
    C9 C11 C12 C13 . . . . -56.5(3) ?
    O4 C12 C13 C18 . . . . 57.3(2) ?
    C11 C12 C13 C18 . . . . -62.9(2) ?
    O4 C12 C13 C14 . . . . -179.76(17) ?
    C11 C12 C13 C14 . . . . 60.1(2) ?
    O4 C12 C13 C17 . . . . -69.3(2) ?
    C11 C12 C13 C17 . . . . 170.54(19) ?
    C7 C8 C14 O2 . . . . -67.2(2) ?
    C9 C8 C14 O2 . . . . 168.12(18) ?
    C7 C8 C14 C15 . . . . 52.7(3) ?
    C9 C8 C14 C15 . . . . -72.1(3) ?
    C7 C8 C14 C13 . . . . 172.7(2) ?
    C9 C8 C14 C13 . . . . 48.0(3) ?
    C18 C13 C14 O2 . . . . -49.4(2) ?
    C12 C13 C14 O2 . . . . -171.42(18) ?
    C17 C13 C14 O2 . . . . 75.3(2) ?
    C18 C13 C14 C8 . . . . 67.3(3) ?
    C12 C13 C14 C8 . . . . -54.8(2) ?
    C17 C13 C14 C8 . . . . -168.0(2) ?
    C18 C13 C14 C15 . . . . -164.7(2) ?
    C12 C13 C14 C15 . . . . 73.3(2) ?
    C17 C13 C14 C15 . . . . -39.9(2) ?
    O2 C14 C15 C16 . . . . -76.7(2) ?
    C8 C14 C15 C16 . . . . 165.4(2) ?
    C13 C14 C15 C16 . . . . 40.3(2) ?
    C14 C15 C16 C17 . . . . -25.1(3) ?
    C15 C16 C17 C20 . . . . 122.9(2) ?
    C15 C16 C17 C13 . . . . 0.2(3) ?
    C18 C13 C17 C20 . . . . 23.8(3) ?
    C12 C13 C17 C20 . . . . 147.6(2) ?
    C14 C13 C17 C20 . . . . -98.9(2) ?
    C18 C13 C17 C16 . . . . 147.0(2) ?
    C12 C13 C17 C16 . . . . -89.2(2) ?
    C14 C13 C17 C16 . . . . 24.2(2) ?
    C16 C17 C20 O3 . . . . -37.5(3) ?
    C13 C17 C20 O3 . . . . 81.1(3) ?
    C16 C17 C20 C21 . . . . 143.6(2) ?
    C13 C17 C20 C21 . . . . -97.7(2) ?
    C12 O4 C22 O5 . . . . 9.5(3) ?
    C12 O4 C22 C23 . . . . -168.83(18) ?
    O5 C22 C23 C25 . . . . 176.5(3) ?
    O4 C22 C23 C25 . . . . -5.2(3) ?
    O5 C22 C23 C24 . . . . -5.4(4) ?
    O4 C22 C23 C24 . . . . 172.9(2) ?
    C22 C23 C25 C26 . . . . 178.5(2) ?
    C24 C23 C25 C26 . . . . 0.6(4) ?
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
    O1 H10H O5 4_746 0.84 2.11 2.941(3) 173
    O2 H20H O3 . 0.84 2.10 2.886(2) 156
