##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     'RAELSPUB and manual entry'
_journal_date_recd_electronic     2011-09-19
_journal_date_accepted     2012-01-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o526
_journal_page_last     o527
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812002206
_journal_coeditor_code     QK2025
_publ_contact_author_name     'Dr. Karren Beattie'
_publ_contact_author_address
;
Cetre for Phytochemistry and Pharmacology
Southern Cross University
Lismroe, NSW 2480, Australia
;
_publ_contact_author_email     'karren.beattie@hotmail.com'
_publ_contact_author_fax     '61266201048'
_publ_contact_author_phone     '61266223459'
_publ_section_title
;\
(3R,4S,5S,8S,10R,13R)-3-Hydroxykaura-\
9(11),16-dien-18-oic acid
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Beattie, Karren D.' ?
;
Centre for Phytochemistry and Pharmacology
Southern Cross University, Lismore Campus
NSW 2480, Australia
;
    'Bhadbhade, Mohan M.' .
;
School of Chemistry
University of New South Wales, Sydney
NSW 2052, Australia
;
    'Craig, Donald C.' .
;
School of Chemistry
University of New South Wales, Sydney
NSW 2052, Australia
;
    'Leach, David N.' .
;
Centre for Phytochemistry and Pharmacology
Southern Cross University, Lismore Campus
NSW 2480, Australia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(3R,4S,5S,8S,10R,13R)-
3-Hydroxykaura-9(11),16-dien-18-oic acid
;
_chemical_formula_moiety     'C20 H28 O3'
_chemical_formula_sum     'C20 H28 O3'
_chemical_formula_iupac     'C20 H28 O3'
_chemical_formula_weight     316.4
_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     8.064(2)
_cell_length_b     10.775(3)
_cell_length_c     10.462(4)
_cell_angle_alpha     90.00
_cell_angle_beta     109.70(2)
_cell_angle_gamma     90.00
_cell_volume     855.8(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     11
_cell_measurement_theta_min     10
_cell_measurement_theta_max     11
_cell_measurement_temperature     296.0(10)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.228
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     344
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     296.0(10)
_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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω--2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1586
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0430
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     1
_diffrn_standards_interval_time     30
_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     1586
_reflns_number_gt     1254
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0689
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1080
_refine_ls_wR_factor_ref     0.1119
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     1586
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0704P)²+0.0000P] 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     0.154
_refine_diff_density_min     -0.171
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'deduced from optical rotation'
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.3554(4) 0.4597(3) 0.9863(3) 0.0658(8) Uani d . 1 1 . .
    O O2 0.4220(4) 0.2189(3) 0.9850(2) 0.0620(7) Uani d . 1 1 . .
    O O3 0.5758(4) 0.1598(3) 0.8595(3) 0.0678(9) Uani d . 1 1 . .
    C C1 0.0447(4) 0.3543(4) 0.6459(4) 0.0521(10) Uani d . 1 1 . .
    C C2 0.1154(5) 0.3753(4) 0.7994(4) 0.0511(9) Uani d . 1 1 . .
    C C3 0.2956(5) 0.4335(3) 0.8438(3) 0.0473(9) Uani d . 1 1 . .
    C C4 0.4293(4) 0.3558(3) 0.8032(3) 0.0395(8) Uani d . 1 1 . .
    C C5 0.3551(4) 0.3369(3) 0.6461(3) 0.0359(7) Uani d . 1 1 . .
    C C6 0.4877(5) 0.2789(4) 0.5853(3) 0.0520(9) Uani d . 1 1 . .
    C C7 0.4047(5) 0.2222(4) 0.4458(3) 0.0572(10) Uani d . 1 1 . .
    C C8 0.2344(4) 0.2860(4) 0.3602(3) 0.0460(8) Uani d . 1 1 . .
    C C9 0.1005(4) 0.2857(3) 0.4348(3) 0.0435(8) Uani d . 1 1 . .
    C C10 0.1677(4) 0.2779(3) 0.5907(3) 0.0399(8) Uani d . 1 1 . .
    C C11 -0.0703(5) 0.2924(4) 0.3625(4) 0.0587(10) Uani d . 1 1 . .
    C C12 -0.1416(5) 0.3019(4) 0.2107(4) 0.0667(12) Uani d . 1 1 . .
    C C13 0.0059(6) 0.3158(4) 0.1511(4) 0.0609(11) Uani d . 1 1 . .
    C C14 0.1503(6) 0.2238(4) 0.2209(4) 0.0645(11) Uani d . 1 1 . .
    C C15 0.2579(5) 0.4187(4) 0.3156(3) 0.0499(9) Uani d . 1 1 . .
    C C16 0.0971(5) 0.4395(4) 0.1910(3) 0.0485(9) Uani d . 1 1 . .
    C C17 0.0429(5) 0.5449(4) 0.1297(4) 0.0567(10) Uani d . 1 1 . .
    C C18 0.4701(4) 0.2379(3) 0.8902(3) 0.0422(8) Uani d . 1 1 . .
    C C19 0.6049(5) 0.4288(4) 0.8399(4) 0.0578(10) Uani d . 1 1 . .
    C C20 0.1658(5) 0.1410(4) 0.6329(4) 0.0518(9) Uani d . 1 1 . .
    H H1A 0.0241 0.4344 0.6009 0.062 Uiso calc R 1 1 . .
    H H1B -0.0679 0.3121 0.6225 0.062 Uiso calc R 1 1 . .
    H H1O1 0.353(7) 0.381(6) 1.029(6) 0.11(2) Uiso d . 1 1 . .
    H H1O3 0.598(6) 0.104(5) 0.916(5) 0.070(14) Uiso d . 1 1 . .
    H H2A 0.0352 0.4289 0.8251 0.061 Uiso calc R 1 1 . .
    H H2B 0.1212 0.2965 0.8455 0.061 Uiso calc R 1 1 . .
    H H3A 0.2844 0.5133 0.7966 0.057 Uiso calc R 1 1 . .
    H H5 0.3378 0.4215 0.6096 0.043 Uiso calc R 1 1 . .
    H H6A 0.5700 0.3427 0.5799 0.062 Uiso calc R 1 1 . .
    H H6B 0.5545 0.2152 0.6467 0.062 Uiso calc R 1 1 . .
    H H7A 0.3802 0.1353 0.4561 0.069 Uiso calc R 1 1 . .
    H H7B 0.4886 0.2262 0.3977 0.069 Uiso calc R 1 1 . .
    H H11 -0.1504 0.2912 0.4089 0.070 Uiso calc R 1 1 . .
    H H12A -0.2197 0.3730 0.1847 0.080 Uiso calc R 1 1 . .
    H H12B -0.2097 0.2281 0.1736 0.080 Uiso calc R 1 1 . .
    H H13 -0.0373 0.3044 0.0524 0.073 Uiso calc R 1 1 . .
    H H14A 0.2340 0.2154 0.1732 0.077 Uiso calc R 1 1 . .
    H H14B 0.1024 0.1429 0.2294 0.077 Uiso calc R 1 1 . .
    H H15A 0.2618 0.4781 0.3863 0.060 Uiso calc R 1 1 . .
    H H15B 0.3652 0.4260 0.2937 0.060 Uiso calc R 1 1 . .
    H H17A -0.0600 0.5480 0.0549 0.068 Uiso calc R 1 1 . .
    H H17B 0.1071 0.6171 0.1610 0.068 Uiso calc R 1 1 . .
    H H19A 0.6417 0.4530 0.9336 0.087 Uiso calc R 1 1 . .
    H H19B 0.5881 0.5014 0.7839 0.087 Uiso calc R 1 1 . .
    H H19C 0.6936 0.3771 0.8250 0.087 Uiso calc R 1 1 . .
    H H20A 0.0491 0.1080 0.5929 0.078 Uiso calc R 1 1 . .
    H H20B 0.2006 0.1356 0.7300 0.078 Uiso calc R 1 1 . .
    H H20C 0.2464 0.0942 0.6021 0.078 Uiso calc R 1 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 . 1.432(4) ?
    O1 H1O1 . 0.96(7) ?
    O2 C18 . 1.198(4) ?
    O3 C18 . 1.312(4) ?
    O3 H1O3 . 0.82(5) ?
    C1 C2 . 1.529(5) ?
    C1 C10 . 1.544(5) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.505(5) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.534(5) ?
    C3 H3A . 0.9800 ?
    C4 C18 . 1.532(5) ?
    C4 C19 . 1.551(5) ?
    C4 C5 . 1.562(4) ?
    C5 C6 . 1.549(5) ?
    C5 C10 . 1.559(4) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.514(5) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.527(5) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.531(5) ?
    C8 C15 . 1.536(5) ?
    C8 C14 . 1.538(5) ?
    C9 C11 . 1.331(5) ?
    C9 C10 . 1.537(4) ?
    C10 C20 . 1.541(5) ?
    C11 C12 . 1.499(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.525(6) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C16 . 1.511(6) ?
    C13 C14 . 1.516(6) ?
    C13 H13 . 0.9800 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.514(5) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.305(6) ?
    C17 H17A . 0.9300 ?
    C17 H17B . 0.9300 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
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 H1O1 . . 105(4) ?
    C18 O3 H1O3 . . 107(3) ?
    C2 C1 C10 . . 114.4(3) ?
    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 . . 111.4(3) ?
    C3 C2 H2A . . 109.3 ?
    C1 C2 H2A . . 109.3 ?
    C3 C2 H2B . . 109.3 ?
    C1 C2 H2B . . 109.3 ?
    H2A C2 H2B . . 108.0 ?
    O1 C3 C2 . . 110.8(3) ?
    O1 C3 C4 . . 112.0(3) ?
    C2 C3 C4 . . 112.5(3) ?
    O1 C3 H3A . . 107.1 ?
    C2 C3 H3A . . 107.1 ?
    C4 C3 H3A . . 107.1 ?
    C18 C4 C3 . . 108.6(3) ?
    C18 C4 C19 . . 106.2(3) ?
    C3 C4 C19 . . 108.8(3) ?
    C18 C4 C5 . . 116.5(3) ?
    C3 C4 C5 . . 107.9(3) ?
    C19 C4 C5 . . 108.7(3) ?
    C6 C5 C10 . . 113.6(3) ?
    C6 C5 C4 . . 114.4(3) ?
    C10 C5 C4 . . 115.1(2) ?
    C6 C5 H5 . . 104.0 ?
    C10 C5 H5 . . 104.0 ?
    C4 C5 H5 . . 104.0 ?
    C7 C6 C5 . . 114.6(3) ?
    C7 C6 H6A . . 108.6 ?
    C5 C6 H6A . . 108.6 ?
    C7 C6 H6B . . 108.6 ?
    C5 C6 H6B . . 108.6 ?
    H6A C6 H6B . . 107.6 ?
    C6 C7 C8 . . 113.7(3) ?
    C6 C7 H7A . . 108.8 ?
    C8 C7 H7A . . 108.8 ?
    C6 C7 H7B . . 108.8 ?
    C8 C7 H7B . . 108.8 ?
    H7A C7 H7B . . 107.7 ?
    C7 C8 C9 . . 110.5(3) ?
    C7 C8 C15 . . 114.8(3) ?
    C9 C8 C15 . . 109.7(3) ?
    C7 C8 C14 . . 112.5(3) ?
    C9 C8 C14 . . 108.7(3) ?
    C15 C8 C14 . . 100.2(3) ?
    C11 C9 C8 . . 118.8(3) ?
    C11 C9 C10 . . 122.3(3) ?
    C8 C9 C10 . . 118.9(3) ?
    C9 C10 C20 . . 108.8(3) ?
    C9 C10 C1 . . 109.0(3) ?
    C20 C10 C1 . . 109.5(3) ?
    C9 C10 C5 . . 108.8(2) ?
    C20 C10 C5 . . 112.7(3) ?
    C1 C10 C5 . . 107.9(3) ?
    C9 C11 C12 . . 124.1(4) ?
    C9 C11 H11 . . 118.0 ?
    C12 C11 H11 . . 118.0 ?
    C11 C12 C13 . . 111.5(3) ?
    C11 C12 H12A . . 109.3 ?
    C13 C12 H12A . . 109.3 ?
    C11 C12 H12B . . 109.3 ?
    C13 C12 H12B . . 109.3 ?
    H12A C12 H12B . . 108.0 ?
    C16 C13 C14 . . 102.7(3) ?
    C16 C13 C12 . . 110.4(3) ?
    C14 C13 C12 . . 108.5(3) ?
    C16 C13 H13 . . 111.6 ?
    C14 C13 H13 . . 111.6 ?
    C12 C13 H13 . . 111.6 ?
    C13 C14 C8 . . 101.2(3) ?
    C13 C14 H14A . . 111.5 ?
    C8 C14 H14A . . 111.5 ?
    C13 C14 H14B . . 111.5 ?
    C8 C14 H14B . . 111.5 ?
    H14A C14 H14B . . 109.4 ?
    C16 C15 C8 . . 104.0(3) ?
    C16 C15 H15A . . 111.0 ?
    C8 C15 H15A . . 111.0 ?
    C16 C15 H15B . . 111.0 ?
    C8 C15 H15B . . 111.0 ?
    H15A C15 H15B . . 109.0 ?
    C17 C16 C13 . . 125.5(3) ?
    C17 C16 C15 . . 126.8(4) ?
    C13 C16 C15 . . 107.7(3) ?
    C16 C17 H17A . . 120.0 ?
    C16 C17 H17B . . 120.0 ?
    H17A C17 H17B . . 120.0 ?
    O2 C18 O3 . . 120.7(3) ?
    O2 C18 C4 . . 124.7(3) ?
    O3 C18 C4 . . 114.4(3) ?
    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 ?
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 . . . . 54.8(4) ?
    C1 C2 C3 O1 . . . . 176.4(3) ?
    C1 C2 C3 C4 . . . . -57.4(4) ?
    O1 C3 C4 C18 . . . . 55.0(3) ?
    C2 C3 C4 C18 . . . . -70.5(3) ?
    O1 C3 C4 C19 . . . . -60.1(4) ?
    C2 C3 C4 C19 . . . . 174.4(3) ?
    O1 C3 C4 C5 . . . . -177.9(3) ?
    C2 C3 C4 C5 . . . . 56.6(3) ?
    C18 C4 C5 C6 . . . . -67.3(4) ?
    C3 C4 C5 C6 . . . . 170.3(3) ?
    C19 C4 C5 C6 . . . . 52.5(4) ?
    C18 C4 C5 C10 . . . . 66.8(4) ?
    C3 C4 C5 C10 . . . . -55.6(3) ?
    C19 C4 C5 C10 . . . . -173.4(3) ?
    C10 C5 C6 C7 . . . . 26.2(5) ?
    C4 C5 C6 C7 . . . . 161.1(3) ?
    C5 C6 C7 C8 . . . . 30.5(5) ?
    C6 C7 C8 C9 . . . . -56.6(4) ?
    C6 C7 C8 C15 . . . . 68.0(4) ?
    C6 C7 C8 C14 . . . . -178.2(3) ?
    C7 C8 C9 C11 . . . . -154.9(4) ?
    C15 C8 C9 C11 . . . . 77.6(4) ?
    C14 C8 C9 C11 . . . . -31.1(5) ?
    C7 C8 C9 C10 . . . . 25.3(4) ?
    C15 C8 C9 C10 . . . . -102.2(3) ?
    C14 C8 C9 C10 . . . . 149.1(3) ?
    C11 C9 C10 C20 . . . . 85.3(5) ?
    C8 C9 C10 C20 . . . . -94.8(4) ?
    C11 C9 C10 C1 . . . . -34.0(5) ?
    C8 C9 C10 C1 . . . . 145.8(3) ?
    C11 C9 C10 C5 . . . . -151.5(4) ?
    C8 C9 C10 C5 . . . . 28.3(4) ?
    C2 C1 C10 C9 . . . . -168.8(3) ?
    C2 C1 C10 C20 . . . . 72.3(4) ?
    C2 C1 C10 C5 . . . . -50.7(4) ?
    C6 C5 C10 C9 . . . . -55.0(4) ?
    C4 C5 C10 C9 . . . . 170.5(3) ?
    C6 C5 C10 C20 . . . . 65.7(4) ?
    C4 C5 C10 C20 . . . . -68.7(3) ?
    C6 C5 C10 C1 . . . . -173.2(3) ?
    C4 C5 C10 C1 . . . . 52.3(4) ?
    C8 C9 C11 C12 . . . . -0.8(6) ?
    C10 C9 C11 C12 . . . . 179.1(4) ?
    C9 C11 C12 C13 . . . . -5.6(6) ?
    C11 C12 C13 C16 . . . . -67.3(5) ?
    C11 C12 C13 C14 . . . . 44.5(5) ?
    C16 C13 C14 C8 . . . . 42.4(4) ?
    C12 C13 C14 C8 . . . . -74.4(4) ?
    C7 C8 C14 C13 . . . . -171.1(3) ?
    C9 C8 C14 C13 . . . . 66.3(4) ?
    C15 C8 C14 C13 . . . . -48.7(4) ?
    C7 C8 C15 C16 . . . . 156.9(3) ?
    C9 C8 C15 C16 . . . . -78.1(3) ?
    C14 C8 C15 C16 . . . . 36.2(3) ?
    C14 C13 C16 C17 . . . . 161.6(4) ?
    C12 C13 C16 C17 . . . . -82.9(5) ?
    C14 C13 C16 C15 . . . . -19.9(4) ?
    C12 C13 C16 C15 . . . . 95.6(4) ?
    C8 C15 C16 C17 . . . . 167.9(3) ?
    C8 C15 C16 C13 . . . . -10.5(4) ?
    C3 C4 C18 O2 . . . . -8.6(4) ?
    C19 C4 C18 O2 . . . . 108.2(4) ?
    C5 C4 C18 O2 . . . . -130.6(4) ?
    C3 C4 C18 O3 . . . . 176.3(3) ?
    C19 C4 C18 O3 . . . . -66.9(4) ?
    C5 C4 C18 O3 . . . . 54.3(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
    O3 H1O3 O1 2_647 0.82(5) 1.83(5) 2.637(4) 169(5)
    O1 H1O1 O2 . 0.96(7) 1.94(6) 2.651(4) 129(5)
