##############################################################################
###                                                                        ###
###        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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-11-22
_journal_date_accepted     2009-12-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      1
_journal_page_first     o103
_journal_page_last     o103
_journal_paper_category     QO
_journal_coeditor_code     ZS2022
_publ_contact_author_name     'Fu-Lin Yan'
_publ_contact_author_address
; School of Pharmacy
  Xinxiang Medical University
  Xinxiang, Henan 453003
  China
;
_publ_contact_author_email     yanfulin03@xxmu.edu.cn
_publ_contact_author_fax     '+086-0373-3029882'
_publ_contact_author_phone     '+086-0373-3029882'
_publ_section_title
;
1α,6β,7β,14β,15β-Pentahydroxy-7α,20-epoxy-ent-kaur-16-ene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Feng, Chuang' .
; School of Pharmacy
  Xinxiang Medical University
  Xinxiang, Henan 453003
  People's Republic of China
;
    'Yan, Fu-Lin' .
; School of Pharmacy
  Xinxiang Medical University
  Xinxiang, Henan 453003
  People's Republic of China
;
    'Di, Xue-Mei' .
; School of Pharmacy
  Xinxiang Medical University
  Xinxiang, Henan 453003
  People's Republic of China
;
    'Sun, Peng-Li' .
; School of Pharmacy
  Xinxiang Medical University
  Xinxiang, Henan 453003
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1α,6β,7β,14β,15β-Pentahydroxy-7α,20-epoxy-ent-kaur-16-ene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H30 O6'
_chemical_formula_sum     'C20 H30 O6'
_chemical_formula_iupac     'C20 H30 O6'
_chemical_formula_weight     366.44
_chemical_melting_point     ?
_chemical_melting_point_gt     527
_chemical_melting_point_lt     529
_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     8.0007(3)
_cell_length_b     10.7161(6)
_cell_length_c     20.7759(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1781.25(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6155
_cell_measurement_theta_min     3.18
_cell_measurement_theta_max     27.47
_cell_measurement_temperature     93(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.37
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.100
_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     93(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC10 Saturn724+'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     14459
_diffrn_reflns_av_R_equivalents     0.0286
_diffrn_reflns_av_sigmaI/netI     0.0192
_diffrn_reflns_theta_min     3.18
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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     2336
_reflns_number_gt     2263
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0334
_refine_ls_R_factor_gt     0.0311
_refine_ls_wR_factor_gt     0.0696
_refine_ls_wR_factor_ref     0.0709
_refine_ls_goodness_of_fit_ref     1.008
_refine_ls_restrained_S_all     1.008
_refine_ls_number_reflns     2336
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0336P)²+0.690P] 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     0.283
_refine_diff_density_min     -0.170
_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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Rigaku, 2008)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2008)'
_computing_data_reduction     'CrystalClear (Rigaku, 2008)'
_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 0.65937(15) 0.64947(11) 0.44833(6) 0.0133(3) Uani d . 1 . .
    O O2 0.13629(15) 0.61728(12) 0.40576(6) 0.0146(3) Uani d . 1 . .
    H H2O 0.0696 0.5924 0.4355 0.018 Uiso d R 1 . .
    O O3 0.75905(16) 0.31571(12) 0.43788(6) 0.0137(3) Uani d . 1 . .
    O O4 0.86693(15) 0.54558(12) 0.49981(7) 0.0145(3) Uani d . 1 . .
    O O5 0.70889(15) 0.63306(12) 0.60424(6) 0.0152(3) Uani d . 1 . .
    H H5O 0.6992 0.7126 0.6054 0.018 Uiso d R 1 . .
    O O6 0.58870(16) 0.25696(11) 0.54382(6) 0.0128(3) Uani d . 1 . .
    C C1 0.2461(2) 0.51713(16) 0.38625(8) 0.0117(3) Uani d . 1 . .
    H H1 0.1907 0.4359 0.3966 0.014 Uiso calc R 1 . .
    C C2 0.2581(2) 0.52931(17) 0.31315(8) 0.0161(4) Uani d . 1 . .
    H H2A 0.1461 0.5145 0.2943 0.019 Uiso calc R 1 . .
    H H2B 0.2914 0.6158 0.3023 0.019 Uiso calc R 1 . .
    C C3 0.3817(2) 0.43951(19) 0.28259(8) 0.0175(4) Uani d . 1 . .
    H H3A 0.3854 0.4548 0.2356 0.021 Uiso calc R 1 . .
    H H3B 0.3422 0.3529 0.2894 0.021 Uiso calc R 1 . .
    C C4 0.5584(2) 0.45268(18) 0.31027(8) 0.0154(4) Uani d . 1 . .
    C C5 0.5441(2) 0.43633(16) 0.38459(8) 0.0109(3) Uani d . 1 . .
    H H5 0.5023 0.3493 0.3910 0.013 Uiso calc R 1 . .
    C C6 0.7153(2) 0.44034(16) 0.41879(8) 0.0118(3) Uani d . 1 . .
    H H6 0.8011 0.4716 0.3877 0.014 Uiso calc R 1 . .
    C C7 0.7053(2) 0.53030(16) 0.47533(8) 0.0111(3) Uani d . 1 . .
    C C8 0.5752(2) 0.49180(16) 0.52654(8) 0.0108(3) Uani d . 1 . .
    C C9 0.4051(2) 0.46841(16) 0.49127(8) 0.0096(3) Uani d . 1 . .
    H H9 0.3899 0.3760 0.4878 0.012 Uiso calc R 1 . .
    C C10 0.4175(2) 0.52120(15) 0.42116(8) 0.0104(3) Uani d . 1 . .
    C C11 0.2560(2) 0.51986(16) 0.53022(8) 0.0129(3) Uani d . 1 . .
    H H11A 0.1528 0.4783 0.5150 0.015 Uiso calc R 1 . .
    H H11B 0.2447 0.6101 0.5209 0.015 Uiso calc R 1 . .
    C C12 0.2689(2) 0.50260(18) 0.60383(8) 0.0147(4) Uani d . 1 . .
    H H12A 0.2307 0.4175 0.6152 0.018 Uiso calc R 1 . .
    H H12B 0.1935 0.5629 0.6252 0.018 Uiso calc R 1 . .
    C C13 0.4496(2) 0.52170(17) 0.62953(8) 0.0138(3) Uani d . 1 . .
    H H13 0.4503 0.5653 0.6721 0.017 Uiso calc R 1 . .
    C C14 0.5502(2) 0.59337(16) 0.57895(8) 0.0124(3) Uani d . 1 . .
    H H14 0.4851 0.6658 0.5618 0.015 Uiso calc R 1 . .
    C C15 0.6290(2) 0.37800(16) 0.56886(8) 0.0121(3) Uani d . 1 . .
    H H15 0.7524 0.3825 0.5763 0.014 Uiso calc R 1 . .
    C C16 0.5398(2) 0.39814(17) 0.63254(8) 0.0134(3) Uani d . 1 . .
    C C17 0.5401(2) 0.31766(18) 0.68075(9) 0.0172(4) Uani d . 1 . .
    H H17A 0.4786 0.3353 0.7188 0.021 Uiso calc R 1 . .
    H H17B 0.6018 0.2422 0.6774 0.021 Uiso calc R 1 . .
    C C18 0.6668(2) 0.34633(19) 0.28388(9) 0.0206(4) Uani d . 1 . .
    H H18A 0.6680 0.3500 0.2368 0.025 Uiso calc R 1 . .
    H H18B 0.6205 0.2661 0.2978 0.025 Uiso calc R 1 . .
    H H18C 0.7811 0.3550 0.3002 0.025 Uiso calc R 1 . .
    C C19 0.6374(3) 0.57664(19) 0.28789(9) 0.0206(4) Uani d . 1 . .
    H H19A 0.5595 0.6453 0.2962 0.025 Uiso calc R 1 . .
    H H19B 0.6613 0.5722 0.2417 0.025 Uiso calc R 1 . .
    H H19C 0.7415 0.5911 0.3116 0.025 Uiso calc R 1 . .
    C C20 0.4872(2) 0.65416(16) 0.42727(9) 0.0124(3) Uani d . 1 . .
    H H20A 0.4802 0.6970 0.3851 0.015 Uiso calc R 1 . .
    H H20B 0.4198 0.7020 0.4587 0.015 Uiso calc R 1 . .
    H H3O 0.858(4) 0.310(2) 0.4432(12) 0.028(7) Uiso d . 1 . .
    H H4O 0.860(3) 0.577(2) 0.5363(12) 0.031(7) Uiso d . 1 . .
    H H6O 0.641(3) 0.254(2) 0.5097(11) 0.015(5) Uiso d . 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 C7 . 1.442(2) ?
    O1 C20 . 1.447(2) ?
    O2 C1 . 1.445(2) ?
    O2 H2O . 0.8580 ?
    O3 C6 . 1.437(2) ?
    O3 H3O . 0.80(3) ?
    O4 C7 . 1.399(2) ?
    O4 H4O . 0.83(3) ?
    O5 C14 . 1.439(2) ?
    O5 H5O . 0.8566 ?
    O6 C15 . 1.434(2) ?
    O6 H6O . 0.83(2) ?
    C1 C2 . 1.527(2) ?
    C1 C10 . 1.552(2) ?
    C1 H1 . 1.0000 ?
    C2 C3 . 1.519(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.533(3) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C18 . 1.533(3) ?
    C4 C19 . 1.543(3) ?
    C4 C5 . 1.558(2) ?
    C5 C6 . 1.543(2) ?
    C5 C10 . 1.559(2) ?
    C5 H5 . 1.0000 ?
    C6 C7 . 1.522(2) ?
    C6 H6 . 1.0000 ?
    C7 C8 . 1.545(2) ?
    C8 C14 . 1.553(2) ?
    C8 C15 . 1.564(2) ?
    C8 C9 . 1.566(2) ?
    C9 C11 . 1.543(2) ?
    C9 C10 . 1.566(2) ?
    C9 H9 . 1.0000 ?
    C10 C20 . 1.535(2) ?
    C11 C12 . 1.544(2) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.555(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C16 . 1.509(2) ?
    C13 C14 . 1.530(2) ?
    C13 H13 . 1.0000 ?
    C14 H14 . 1.0000 ?
    C15 C16 . 1.519(2) ?
    C15 H15 . 1.0000 ?
    C16 C17 . 1.322(2) ?
    C17 H17A . 0.9500 ?
    C17 H17B . 0.9500 ?
    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 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
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
    C7 O1 C20 . . 113.03(13) ?
    C1 O2 H2O . . 110.4 ?
    C6 O3 H3O . . 110.8(18) ?
    C7 O4 H4O . . 108.3(18) ?
    C14 O5 H5O . . 103.0 ?
    C15 O6 H6O . . 103.4(17) ?
    O2 C1 C2 . . 104.68(14) ?
    O2 C1 C10 . . 112.67(13) ?
    C2 C1 C10 . . 114.03(14) ?
    O2 C1 H1 . . 108.4 ?
    C2 C1 H1 . . 108.4 ?
    C10 C1 H1 . . 108.4 ?
    C3 C2 C1 . . 113.72(15) ?
    C3 C2 H2A . . 108.8 ?
    C1 C2 H2A . . 108.8 ?
    C3 C2 H2B . . 108.8 ?
    C1 C2 H2B . . 108.8 ?
    H2A C2 H2B . . 107.7 ?
    C2 C3 C4 . . 112.67(15) ?
    C2 C3 H3A . . 109.1 ?
    C4 C3 H3A . . 109.1 ?
    C2 C3 H3B . . 109.1 ?
    C4 C3 H3B . . 109.1 ?
    H3A C3 H3B . . 107.8 ?
    C3 C4 C18 . . 108.61(15) ?
    C3 C4 C19 . . 110.12(15) ?
    C18 C4 C19 . . 107.50(15) ?
    C3 C4 C5 . . 107.07(14) ?
    C18 C4 C5 . . 108.20(15) ?
    C19 C4 C5 . . 115.19(15) ?
    C6 C5 C4 . . 112.82(14) ?
    C6 C5 C10 . . 109.63(13) ?
    C4 C5 C10 . . 117.72(14) ?
    C6 C5 H5 . . 105.2 ?
    C4 C5 H5 . . 105.2 ?
    C10 C5 H5 . . 105.2 ?
    O3 C6 C7 . . 112.87(14) ?
    O3 C6 C5 . . 108.51(13) ?
    C7 C6 C5 . . 109.07(13) ?
    O3 C6 H6 . . 108.8 ?
    C7 C6 H6 . . 108.8 ?
    C5 C6 H6 . . 108.8 ?
    O4 C7 O1 . . 105.86(13) ?
    O4 C7 C6 . . 107.85(13) ?
    O1 C7 C6 . . 105.90(13) ?
    O4 C7 C8 . . 113.82(14) ?
    O1 C7 C8 . . 109.42(13) ?
    C6 C7 C8 . . 113.43(14) ?
    C7 C8 C14 . . 112.50(14) ?
    C7 C8 C15 . . 114.19(13) ?
    C14 C8 C15 . . 100.83(13) ?
    C7 C8 C9 . . 107.83(13) ?
    C14 C8 C9 . . 109.18(13) ?
    C15 C8 C9 . . 112.19(13) ?
    C11 C9 C10 . . 114.06(13) ?
    C11 C9 C8 . . 111.66(13) ?
    C10 C9 C8 . . 108.81(13) ?
    C11 C9 H9 . . 107.3 ?
    C10 C9 H9 . . 107.3 ?
    C8 C9 H9 . . 107.3 ?
    C20 C10 C1 . . 112.68(13) ?
    C20 C10 C5 . . 110.23(13) ?
    C1 C10 C5 . . 109.26(13) ?
    C20 C10 C9 . . 106.35(14) ?
    C1 C10 C9 . . 111.64(13) ?
    C5 C10 C9 . . 106.48(13) ?
    C9 C11 C12 . . 115.16(14) ?
    C9 C11 H11A . . 108.5 ?
    C12 C11 H11A . . 108.5 ?
    C9 C11 H11B . . 108.5 ?
    C12 C11 H11B . . 108.5 ?
    H11A C11 H11B . . 107.5 ?
    C11 C12 C13 . . 112.73(14) ?
    C11 C12 H12A . . 109.0 ?
    C13 C12 H12A . . 109.0 ?
    C11 C12 H12B . . 109.0 ?
    C13 C12 H12B . . 109.0 ?
    H12A C12 H12B . . 107.8 ?
    C16 C13 C14 . . 102.54(14) ?
    C16 C13 C12 . . 110.09(14) ?
    C14 C13 C12 . . 108.62(14) ?
    C16 C13 H13 . . 111.7 ?
    C14 C13 H13 . . 111.7 ?
    C12 C13 H13 . . 111.7 ?
    O5 C14 C13 . . 111.21(14) ?
    O5 C14 C8 . . 110.47(13) ?
    C13 C14 C8 . . 101.39(13) ?
    O5 C14 H14 . . 111.1 ?
    C13 C14 H14 . . 111.1 ?
    C8 C14 H14 . . 111.1 ?
    O6 C15 C16 . . 109.80(14) ?
    O6 C15 C8 . . 116.06(13) ?
    C16 C15 C8 . . 104.45(14) ?
    O6 C15 H15 . . 108.8 ?
    C16 C15 H15 . . 108.8 ?
    C8 C15 H15 . . 108.8 ?
    C17 C16 C13 . . 127.20(17) ?
    C17 C16 C15 . . 124.52(17) ?
    C13 C16 C15 . . 108.26(14) ?
    C16 C17 H17A . . 120.0 ?
    C16 C17 H17B . . 120.0 ?
    H17A C17 H17B . . 120.0 ?
    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 ?
    O1 C20 C10 . . 109.79(13) ?
    O1 C20 H20A . . 109.7 ?
    C10 C20 H20A . . 109.7 ?
    O1 C20 H20B . . 109.7 ?
    C10 C20 H20B . . 109.7 ?
    H20A C20 H20B . . 108.2 ?
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
    O2 C1 C2 C3 . . . . 174.61(14) ?
    C10 C1 C2 C3 . . . . 51.0(2) ?
    C1 C2 C3 C4 . . . . -56.8(2) ?
    C2 C3 C4 C18 . . . . 171.78(15) ?
    C2 C3 C4 C19 . . . . -70.76(19) ?
    C2 C3 C4 C5 . . . . 55.2(2) ?
    C3 C4 C5 C6 . . . . 176.91(14) ?
    C18 C4 C5 C6 . . . . 60.02(19) ?
    C19 C4 C5 C6 . . . . -60.3(2) ?
    C3 C4 C5 C10 . . . . -53.8(2) ?
    C18 C4 C5 C10 . . . . -170.73(14) ?
    C19 C4 C5 C10 . . . . 69.0(2) ?
    C4 C5 C6 O3 . . . . -105.74(16) ?
    C10 C5 C6 O3 . . . . 120.97(14) ?
    C4 C5 C6 C7 . . . . 130.94(15) ?
    C10 C5 C6 C7 . . . . -2.36(18) ?
    C20 O1 C7 O4 . . . . -173.34(13) ?
    C20 O1 C7 C6 . . . . 72.31(16) ?
    C20 O1 C7 C8 . . . . -50.29(17) ?
    O3 C6 C7 O4 . . . . 67.47(17) ?
    C5 C6 C7 O4 . . . . -171.83(13) ?
    O3 C6 C7 O1 . . . . -179.55(13) ?
    C5 C6 C7 O1 . . . . -58.86(16) ?
    O3 C6 C7 C8 . . . . -59.54(18) ?
    C5 C6 C7 C8 . . . . 61.16(18) ?
    O4 C7 C8 C14 . . . . 63.85(19) ?
    O1 C7 C8 C14 . . . . -54.34(17) ?
    C6 C7 C8 C14 . . . . -172.34(14) ?
    O4 C7 C8 C15 . . . . -50.29(19) ?
    O1 C7 C8 C15 . . . . -168.48(13) ?
    C6 C7 C8 C15 . . . . 73.52(18) ?
    O4 C7 C8 C9 . . . . -175.70(13) ?
    O1 C7 C8 C9 . . . . 66.11(16) ?
    C6 C7 C8 C9 . . . . -51.89(18) ?
    C7 C8 C9 C11 . . . . -139.59(14) ?
    C14 C8 C9 C11 . . . . -17.08(18) ?
    C15 C8 C9 C11 . . . . 93.82(16) ?
    C7 C8 C9 C10 . . . . -12.81(17) ?
    C14 C8 C9 C10 . . . . 109.70(15) ?
    C15 C8 C9 C10 . . . . -139.41(14) ?
    O2 C1 C10 C20 . . . . -41.24(19) ?
    C2 C1 C10 C20 . . . . 77.89(18) ?
    O2 C1 C10 C5 . . . . -164.13(13) ?
    C2 C1 C10 C5 . . . . -45.00(19) ?
    O2 C1 C10 C9 . . . . 78.35(17) ?
    C2 C1 C10 C9 . . . . -162.51(14) ?
    C6 C5 C10 C20 . . . . 55.37(17) ?
    C4 C5 C10 C20 . . . . -75.36(18) ?
    C6 C5 C10 C1 . . . . 179.71(13) ?
    C4 C5 C10 C1 . . . . 48.98(19) ?
    C6 C5 C10 C9 . . . . -59.58(16) ?
    C4 C5 C10 C9 . . . . 169.69(14) ?
    C11 C9 C10 C20 . . . . 76.19(16) ?
    C8 C9 C10 C20 . . . . -49.19(16) ?
    C11 C9 C10 C1 . . . . -47.07(18) ?
    C8 C9 C10 C1 . . . . -172.46(13) ?
    C11 C9 C10 C5 . . . . -166.25(14) ?
    C8 C9 C10 C5 . . . . 68.36(15) ?
    C10 C9 C11 C12 . . . . -162.27(14) ?
    C8 C9 C11 C12 . . . . -38.4(2) ?
    C9 C11 C12 C13 . . . . 38.2(2) ?
    C11 C12 C13 C16 . . . . -93.00(18) ?
    C11 C12 C13 C14 . . . . 18.5(2) ?
    C16 C13 C14 O5 . . . . -73.63(16) ?
    C12 C13 C14 O5 . . . . 169.86(13) ?
    C16 C13 C14 C8 . . . . 43.82(16) ?
    C12 C13 C14 C8 . . . . -72.69(16) ?
    C7 C8 C14 O5 . . . . -50.02(18) ?
    C15 C8 C14 O5 . . . . 72.05(16) ?
    C9 C8 C14 O5 . . . . -169.69(13) ?
    C7 C8 C14 C13 . . . . -168.00(14) ?
    C15 C8 C14 C13 . . . . -45.94(16) ?
    C9 C8 C14 C13 . . . . 72.33(16) ?
    C7 C8 C15 O6 . . . . -87.44(17) ?
    C14 C8 C15 O6 . . . . 151.70(14) ?
    C9 C8 C15 O6 . . . . 35.65(19) ?
    C7 C8 C15 C16 . . . . 151.54(14) ?
    C14 C8 C15 C16 . . . . 30.67(16) ?
    C9 C8 C15 C16 . . . . -85.38(16) ?
    C14 C13 C16 C17 . . . . 156.98(18) ?
    C12 C13 C16 C17 . . . . -87.6(2) ?
    C14 C13 C16 C15 . . . . -24.71(17) ?
    C12 C13 C16 C15 . . . . 90.74(16) ?
    O6 C15 C16 C17 . . . . 49.2(2) ?
    C8 C15 C16 C17 . . . . 174.27(17) ?
    O6 C15 C16 C13 . . . . -129.19(14) ?
    C8 C15 C16 C13 . . . . -4.09(17) ?
    C7 O1 C20 C10 . . . . -16.70(18) ?
    C1 C10 C20 O1 . . . . -168.75(13) ?
    C5 C10 C20 O1 . . . . -46.40(18) ?
    C9 C10 C20 O1 . . . . 68.64(16) ?
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
    O3 H3O O6 4_556 0.80(3) 2.00(3) 2.7761(18) 164(3)
    O4 H4O O5 . 0.83(3) 1.95(3) 2.6806(18) 146(2)
    O5 H5O O2 4_566 0.86 1.90 2.7455(18) 166.7
    O6 H6O O3 . 0.83(2) 1.88(2) 2.6642(18) 157(2)
