##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-02-26
_journal_date_accepted     2009-03-19
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o214
_journal_page_last     o216
_journal_paper_category     FO
_journal_coeditor_code     SK3302
_publ_contact_author_name     'J.A. Paixão'
_publ_contact_author_address
;
     Faculdade Ciências e Tecnologia
     Departamento de Física
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
_publ_contact_author_email     jap@pollux.fis.uc.pt
_publ_contact_author_fax     351-239-829158
_publ_contact_author_phone     351-239-410644
_publ_section_title
;
6β-Hydroxy-5β-methyl-20-oxo-19-norpregn-9(10)-en-3β-yl acetate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Pinto, R. M. A.' .
;
     Laboratório de Química Farmacêutica
     Faculdade de Farmácia
     Universidade de Coimbra
     P-3000-295 Coimbra
     Portugal
;
    'Ramos Silva, M.' .
;
     CEMDRX
     Departamento de Física
     Faculdade de Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
    'Matos Beja, A.' .
;
     CEMDRX
     Departamento de Física
     Faculdade de Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
    'Salvador, J. A. R.' .
;
     Laboratório de Química Farmacêutica
     Faculdade de Farmácia
     Universidade de Coimbra
     P-3000-295 Coimbra
     Portugal
;
    'Paixão, J.A.' .
;
     CEMDRX
     Departamento de Física
     Faculdade de Ciências e Tecnologia
     Universidade de Coimbra
     P-3004-516 Coimbra
     Portugal
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6β-Hydroxy-5β-methyl-20-oxo-19-norpregn-9(10)-en-3β-yl acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H34 O4'
_chemical_formula_sum     'C23 H34 O4'
_chemical_formula_iupac     'C23 H34 O4'
_chemical_formula_weight     374.50
_chemical_melting_point     411
_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     5.8903(2)
_cell_length_b     9.6929(2)
_cell_length_c     36.9988(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2112.41(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6566
_cell_measurement_theta_min     2.3722
_cell_measurement_theta_max     26.2890
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'flat hexagonal prism'
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.178
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     816
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2000)'
_exptl_absorpt_correction_T_min     0.882
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     59317
_diffrn_reflns_av_R_equivalents     0.0412
_diffrn_reflns_av_sigmaI/netI     0.0183
_diffrn_reflns_theta_min     2.17
_diffrn_reflns_theta_max     30.54
_diffrn_reflns_theta_full     30.54
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -52
_diffrn_reflns_limit_l_max     52
_diffrn_standards_number     ?
_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     3729
_reflns_number_gt     2885
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0623
_refine_ls_R_factor_gt     0.0440
_refine_ls_wR_factor_gt     0.1211
_refine_ls_wR_factor_ref     0.1331
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     3729
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0779P)²+0.1174P] 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     0.177
_refine_diff_density_min     -0.174
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_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     'SMART (Bruker, 2003)'
_computing_cell_refinement     'SAINT (Bruker, 2003)'
_computing_data_reduction     'SAINT (Bruker, 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_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
    C C1 0.4722(4) 0.12481(19) 0.12583(5) 0.0490(5) Uani d . 1 . .
    H H1A 0.5308 0.1163 0.1502 0.059 Uiso calc R 1 . .
    H H1B 0.5598 0.0636 0.1105 0.059 Uiso calc R 1 . .
    C C2 0.2256(4) 0.0786(2) 0.12548(5) 0.0525(5) Uani d . 1 . .
    H H2A 0.2163 -0.0171 0.1330 0.063 Uiso calc R 1 . .
    H H2B 0.1391 0.1337 0.1425 0.063 Uiso calc R 1 . .
    C C3 0.1252(4) 0.0935(2) 0.08821(5) 0.0489(4) Uani d . 1 . .
    H H3 -0.0358 0.0680 0.0887 0.059 Uiso calc R 1 . .
    O O3A 0.2516(3) -0.00496(14) 0.06584(4) 0.0515(3) Uani d . 1 . .
    C C3A 0.1608(4) -0.0463(2) 0.03472(5) 0.0527(5) Uani d . 1 . .
    O O3B -0.0239(3) -0.0109(2) 0.02454(4) 0.0742(5) Uani d . 1 . .
    C C3B 0.3192(5) -0.1385(2) 0.01506(6) 0.0689(7) Uani d . 1 . .
    H H3B1 0.3134 -0.2292 0.0254 0.103 Uiso calc R 1 . .
    H H3B2 0.4708 -0.1029 0.0169 0.103 Uiso calc R 1 . .
    H H3B3 0.2758 -0.1432 -0.0099 0.103 Uiso calc R 1 . .
    C C4 0.1503(3) 0.2403(2) 0.07486(5) 0.0462(4) Uani d . 1 . .
    H H4A 0.0467 0.2979 0.0886 0.055 Uiso calc R 1 . .
    H H4B 0.1014 0.2431 0.0498 0.055 Uiso calc R 1 . .
    C C5 0.3888(3) 0.30562(18) 0.07705(4) 0.0402(4) Uani d . 1 . .
    C C5A 0.5356(3) 0.2532(2) 0.04534(4) 0.0476(4) Uani d . 1 . .
    H H5A1 0.4563 0.2678 0.0230 0.071 Uiso calc R 1 . .
    H H5A2 0.5650 0.1565 0.0484 0.071 Uiso calc R 1 . .
    H H5A3 0.6767 0.3026 0.0449 0.071 Uiso calc R 1 . .
    C C6 0.3567(4) 0.4633(2) 0.07496(4) 0.0443(4) Uani d . 1 . .
    H H6 0.2593 0.4887 0.0954 0.053 Uiso calc R 1 . .
    O O6 0.2385(3) 0.50490(16) 0.04296(3) 0.0568(4) Uani d . 1 . .
    H H6A 0.3248 0.5008 0.0256 0.085 Uiso calc R 1 . .
    C C7 0.5771(4) 0.5393(2) 0.08019(5) 0.0499(5) Uani d . 1 . .
    H H7A 0.5502 0.6377 0.0780 0.060 Uiso calc R 1 . .
    H H7B 0.6828 0.5126 0.0614 0.060 Uiso calc R 1 . .
    C C8 0.6829(3) 0.50866(19) 0.11734(4) 0.0417(4) Uani d . 1 . .
    H H8 0.8477 0.5173 0.1146 0.050 Uiso calc R 1 . .
    C C9 0.6366(3) 0.36341(18) 0.13065(4) 0.0409(4) Uani d . 1 . .
    C C10 0.5061(3) 0.27213(18) 0.11307(4) 0.0412(4) Uani d . 1 . .
    C C11 0.7514(4) 0.3358(2) 0.16667(5) 0.0503(5) Uani d . 1 . .
    H H11A 0.9147 0.3379 0.1634 0.060 Uiso calc R 1 . .
    H H11B 0.7102 0.2442 0.1749 0.060 Uiso calc R 1 . .
    C C12 0.6851(4) 0.44162(18) 0.19574(5) 0.0453(4) Uani d . 1 . .
    H H12A 0.5245 0.4332 0.2011 0.054 Uiso calc R 1 . .
    H H12B 0.7690 0.4230 0.2178 0.054 Uiso calc R 1 . .
    C C13 0.7360(3) 0.58741(19) 0.18293(4) 0.0397(4) Uani d . 1 . .
    C C14 0.6117(3) 0.61062(17) 0.14663(4) 0.0384(3) Uani d . 1 . .
    H H14 0.4508 0.5924 0.1514 0.046 Uiso calc R 1 . .
    C C15 0.6307(5) 0.7650(2) 0.14027(5) 0.0604(6) Uani d . 1 . .
    H H15A 0.5101 0.7974 0.1246 0.073 Uiso calc R 1 . .
    H H15B 0.7760 0.7883 0.1295 0.073 Uiso calc R 1 . .
    C C16 0.6084(6) 0.8276(2) 0.17831(6) 0.0710(7) Uani d . 1 . .
    H H16A 0.4628 0.8732 0.1809 0.085 Uiso calc R 1 . .
    H H16B 0.7277 0.8947 0.1825 0.085 Uiso calc R 1 . .
    C C17 0.6286(4) 0.7076(2) 0.20541(5) 0.0492(4) Uani d . 1 . .
    H H17 0.4743 0.6795 0.2120 0.059 Uiso calc R 1 . .
    C C18 0.9926(4) 0.6111(3) 0.18014(7) 0.0648(6) Uani d . 1 . .
    H H18A 1.0619 0.5940 0.2032 0.097 Uiso calc R 1 . .
    H H18B 1.0211 0.7048 0.1730 0.097 Uiso calc R 1 . .
    H H18C 1.0555 0.5495 0.1625 0.097 Uiso calc R 1 . .
    C C20 0.7519(5) 0.7448(3) 0.23992(6) 0.0668(6) Uani d . 1 . .
    O O20 0.8547(6) 0.8505(2) 0.24285(6) 0.1158(10) Uani d . 1 . .
    C C21 0.7429(7) 0.6458(3) 0.27057(6) 0.0921(11) Uani d . 1 . .
    H H21A 0.8692 0.5834 0.2690 0.138 Uiso calc R 1 . .
    H H21B 0.6037 0.5944 0.2695 0.138 Uiso calc R 1 . .
    H H21C 0.7501 0.6955 0.2930 0.138 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
    C1 C10 . 1.517(3) ?
    C1 C2 . 1.520(3) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.507(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 O3A . 1.467(2) ?
    C3 C4 . 1.513(3) ?
    C3 H3 . 0.9800 ?
    O3A C3A . 1.331(2) ?
    C3A O3B . 1.201(3) yes
    C3A C3B . 1.483(3) ?
    C3B H3B1 . 0.9600 ?
    C3B H3B2 . 0.9600 ?
    C3B H3B3 . 0.9600 ?
    C4 C5 . 1.543(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C10 . 1.536(2) ?
    C5 C6 . 1.542(3) ?
    C5 C5A . 1.543(2) ?
    C5A H5A1 . 0.9600 ?
    C5A H5A2 . 0.9600 ?
    C5A H5A3 . 0.9600 ?
    C6 O6 . 1.432(2) yes
    C6 C7 . 1.506(3) ?
    C6 H6 . 0.9800 ?
    O6 H6A . 0.8200 ?
    C7 C8 . 1.538(2) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.516(3) ?
    C8 C14 . 1.525(2) ?
    C8 H8 . 0.9800 ?
    C9 C10 . 1.341(3) ?
    C9 C11 . 1.518(2) ?
    C11 C12 . 1.536(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.520(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C18 . 1.532(3) ?
    C13 C14 . 1.546(2) ?
    C13 C17 . 1.565(3) ?
    C14 C15 . 1.519(3) ?
    C14 H14 . 0.9800 ?
    C15 C16 . 1.538(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.540(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C20 . 1.513(3) ?
    C17 H17 . 0.9800 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C20 O20 . 1.195(3) ?
    C20 C21 . 1.487(4) yes
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 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
    C10 C1 C2 . . 113.60(17) ?
    C10 C1 H1A . . 108.8 ?
    C2 C1 H1A . . 108.8 ?
    C10 C1 H1B . . 108.8 ?
    C2 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    C3 C2 C1 . . 110.77(17) ?
    C3 C2 H2A . . 109.5 ?
    C1 C2 H2A . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 108.1 ?
    O3A C3 C2 . . 104.73(16) ?
    O3A C3 C4 . . 112.22(16) ?
    C2 C3 C4 . . 110.54(17) ?
    O3A C3 H3 . . 109.8 ?
    C2 C3 H3 . . 109.8 ?
    C4 C3 H3 . . 109.8 ?
    C3A O3A C3 . . 118.69(17) ?
    O3B C3A O3A . . 123.3(2) ?
    O3B C3A C3B . . 126.0(2) ?
    O3A C3A C3B . . 110.7(2) ?
    C3A C3B H3B1 . . 109.5 ?
    C3A C3B H3B2 . . 109.5 ?
    H3B1 C3B H3B2 . . 109.5 ?
    C3A C3B H3B3 . . 109.5 ?
    H3B1 C3B H3B3 . . 109.5 ?
    H3B2 C3B H3B3 . . 109.5 ?
    C3 C4 C5 . . 117.24(16) ?
    C3 C4 H4A . . 108.0 ?
    C5 C4 H4A . . 108.0 ?
    C3 C4 H4B . . 108.0 ?
    C5 C4 H4B . . 108.0 ?
    H4A C4 H4B . . 107.2 ?
    C10 C5 C6 . . 107.94(14) ?
    C10 C5 C4 . . 111.61(15) ?
    C6 C5 C4 . . 107.01(15) ?
    C10 C5 C5A . . 109.75(14) ?
    C6 C5 C5A . . 110.92(16) ?
    C4 C5 C5A . . 109.58(14) ?
    C5 C5A H5A1 . . 109.5 ?
    C5 C5A H5A2 . . 109.5 ?
    H5A1 C5A H5A2 . . 109.5 ?
    C5 C5A H5A3 . . 109.5 ?
    H5A1 C5A H5A3 . . 109.5 ?
    H5A2 C5A H5A3 . . 109.5 ?
    O6 C6 C7 . . 112.78(16) ?
    O6 C6 C5 . . 112.36(15) ?
    C7 C6 C5 . . 111.91(16) ?
    O6 C6 H6 . . 106.4 ?
    C7 C6 H6 . . 106.4 ?
    C5 C6 H6 . . 106.4 ?
    C6 O6 H6A . . 109.5 ?
    C6 C7 C8 . . 111.68(15) ?
    C6 C7 H7A . . 109.3 ?
    C8 C7 H7A . . 109.3 ?
    C6 C7 H7B . . 109.3 ?
    C8 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 107.9 ?
    C9 C8 C14 . . 108.75(14) ?
    C9 C8 C7 . . 113.39(16) ?
    C14 C8 C7 . . 113.47(15) ?
    C9 C8 H8 . . 106.9 ?
    C14 C8 H8 . . 106.9 ?
    C7 C8 H8 . . 106.9 ?
    C10 C9 C8 . . 123.94(15) ?
    C10 C9 C11 . . 124.41(17) ?
    C8 C9 C11 . . 111.64(16) ?
    C9 C10 C1 . . 123.06(15) ?
    C9 C10 C5 . . 122.66(16) ?
    C1 C10 C5 . . 114.20(16) ?
    C9 C11 C12 . . 112.56(15) ?
    C9 C11 H11A . . 109.1 ?
    C12 C11 H11A . . 109.1 ?
    C9 C11 H11B . . 109.1 ?
    C12 C11 H11B . . 109.1 ?
    H11A C11 H11B . . 107.8 ?
    C13 C12 C11 . . 110.63(15) ?
    C13 C12 H12A . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C12 C13 C18 . . 110.81(19) ?
    C12 C13 C14 . . 108.20(14) ?
    C18 C13 C14 . . 112.74(17) ?
    C12 C13 C17 . . 116.53(16) ?
    C18 C13 C17 . . 108.85(18) ?
    C14 C13 C17 . . 99.30(14) ?
    C15 C14 C8 . . 120.53(16) ?
    C15 C14 C13 . . 104.06(15) ?
    C8 C14 C13 . . 113.12(14) ?
    C15 C14 H14 . . 106.0 ?
    C8 C14 H14 . . 106.0 ?
    C13 C14 H14 . . 106.0 ?
    C14 C15 C16 . . 103.91(16) ?
    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 . . 106.95(17) ?
    C15 C16 H16A . . 110.3 ?
    C17 C16 H16A . . 110.3 ?
    C15 C16 H16B . . 110.3 ?
    C17 C16 H16B . . 110.3 ?
    H16A C16 H16B . . 108.6 ?
    C20 C17 C16 . . 114.02(18) ?
    C20 C17 C13 . . 115.56(18) ?
    C16 C17 C13 . . 104.32(16) ?
    C20 C17 H17 . . 107.5 ?
    C16 C17 H17 . . 107.5 ?
    C13 C17 H17 . . 107.5 ?
    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 ?
    O20 C20 C21 . . 120.2(2) ?
    O20 C20 C17 . . 121.6(2) ?
    C21 C20 C17 . . 118.3(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 ?
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 . . . . 57.1(2) ?
    C1 C2 C3 O3A . . . . 65.3(2) ?
    C1 C2 C3 C4 . . . . -55.8(2) ?
    C2 C3 O3A C3A . . . . 160.07(17) ?
    C4 C3 O3A C3A . . . . -80.0(2) ?
    C3 O3A C3A O3B . . . . -2.8(3) ?
    C3 O3A C3A C3B . . . . 176.56(18) ?
    O3A C3 C4 C5 . . . . -65.7(2) ?
    C2 C3 C4 C5 . . . . 50.8(2) ?
    C3 C4 C5 C10 . . . . -42.8(2) ?
    C3 C4 C5 C6 . . . . -160.68(15) ?
    C3 C4 C5 C5A . . . . 78.98(19) ?
    C10 C5 C6 O6 . . . . -177.28(15) ?
    C4 C5 C6 O6 . . . . -57.0(2) ?
    C5A C5 C6 O6 . . . . 62.5(2) ?
    C10 C5 C6 C7 . . . . 54.64(19) ?
    C4 C5 C6 C7 . . . . 174.89(14) ?
    C5A C5 C6 C7 . . . . -65.63(18) ?
    O6 C6 C7 C8 . . . . 171.59(15) ?
    C5 C6 C7 C8 . . . . -60.55(19) ?
    C6 C7 C8 C9 . . . . 33.1(2) ?
    C6 C7 C8 C14 . . . . -91.64(19) ?
    C14 C8 C9 C10 . . . . 123.64(19) ?
    C7 C8 C9 C10 . . . . -3.6(3) ?
    C14 C8 C9 C11 . . . . -54.9(2) ?
    C7 C8 C9 C11 . . . . 177.84(16) ?
    C8 C9 C10 C1 . . . . 176.61(18) ?
    C11 C9 C10 C1 . . . . -5.0(3) ?
    C8 C9 C10 C5 . . . . 0.2(3) ?
    C11 C9 C10 C5 . . . . 178.57(18) ?
    C2 C1 C10 C9 . . . . 133.5(2) ?
    C2 C1 C10 C5 . . . . -49.8(2) ?
    C6 C5 C10 C9 . . . . -25.0(2) ?
    C4 C5 C10 C9 . . . . -142.35(18) ?
    C5A C5 C10 C9 . . . . 96.0(2) ?
    C6 C5 C10 C1 . . . . 158.26(17) ?
    C4 C5 C10 C1 . . . . 40.9(2) ?
    C5A C5 C10 C1 . . . . -80.7(2) ?
    C10 C9 C11 C12 . . . . -123.2(2) ?
    C8 C9 C11 C12 . . . . 55.3(2) ?
    C9 C11 C12 C13 . . . . -55.9(2) ?
    C11 C12 C13 C18 . . . . -68.3(2) ?
    C11 C12 C13 C14 . . . . 55.7(2) ?
    C11 C12 C13 C17 . . . . 166.49(17) ?
    C9 C8 C14 C15 . . . . -177.80(19) ?
    C7 C8 C14 C15 . . . . -50.6(3) ?
    C9 C8 C14 C13 . . . . 58.2(2) ?
    C7 C8 C14 C13 . . . . -174.57(15) ?
    C12 C13 C14 C15 . . . . 168.39(18) ?
    C18 C13 C14 C15 . . . . -68.7(2) ?
    C17 C13 C14 C15 . . . . 46.4(2) ?
    C12 C13 C14 C8 . . . . -59.0(2) ?
    C18 C13 C14 C8 . . . . 63.9(2) ?
    C17 C13 C14 C8 . . . . 178.92(16) ?
    C8 C14 C15 C16 . . . . -164.8(2) ?
    C13 C14 C15 C16 . . . . -36.6(3) ?
    C14 C15 C16 C17 . . . . 11.7(3) ?
    C15 C16 C17 C20 . . . . 144.0(2) ?
    C15 C16 C17 C13 . . . . 17.0(3) ?
    C12 C13 C17 C20 . . . . 80.0(2) ?
    C18 C13 C17 C20 . . . . -46.1(2) ?
    C14 C13 C17 C20 . . . . -164.15(18) ?
    C12 C13 C17 C16 . . . . -153.96(19) ?
    C18 C13 C17 C16 . . . . 79.9(2) ?
    C14 C13 C17 C16 . . . . -38.1(2) ?
    C16 C17 C20 O20 . . . . -11.5(4) ?
    C13 C17 C20 O20 . . . . 109.4(3) ?
    C16 C17 C20 C21 . . . . 168.6(3) ?
    C13 C17 C20 C21 . . . . -70.5(3) yes
    C5A C5 C13 C18 . . . . -0.9(2) yes
    C1 C10 C9 C11 . . . . -5.0(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
    O6 H6A O3B 3 0.82 2.06 2.863(2) 166
    C5A H5A2 O3A . 0.96 2.50 3.104(3) 121
    C16 H16B O20 . 0.97 2.39 2.803(3) 105
