##############################################################################
###                                                                        ###
###        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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-01-14
_journal_date_accepted     2008-02-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o783
_journal_page_last     o783
_journal_paper_category     QO
_journal_coeditor_code     WN2237
_publ_contact_author_name     'Hongqi Li'
_publ_contact_author_address
; Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education,
  College of Chemistry and Chemical Engineering, Donghua University,
  Shanghai 201620,
  People's Republic of China
;
_publ_contact_author_email     hongqili@dhu.edu.cn
_publ_contact_author_fax     '8621 6779 2608'
_publ_contact_author_phone     '8621 6779 2612'
_publ_section_title
;
17α-Ethynyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li, Hongqi' .
; College of Chemistry and Chemical Engineering, Donghua University
  Shanghai 201620
  People's Republic of China
;
    'Song, Yanxi' .
; College of Environmental Science and Engineering, Donghua University
  Shanghai 201620
  People's Republic of China
;
    'Ge, Fengyan' .
; College of Chemistry and Chemical Engineering, Donghua University
  Shanghai 201620
  People's Republic of China
;
_chemical_name_systematic
;
17α-Ethinyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol
;
_exptl_special_details
;
Spectroscopic analysis of the title compound: ¹H NMR
(CDCl₃, δ, p.p.m.)
0.91 (s, 3H), 2.60 (s, 1H), 3.83 (s, 3H), 6.17 (t, 1H), 6.60 (brs, 1H),
6.72 (dd, J~1 = 2.5 Hz, J~2 = 8.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 1H);
IR (KBr pellet) 3463, 3254, 2972, 2927, 2890, 2874, 2833, 1606, 1499, 1295,
1230, 1111, 1057, 1032.
;
data_I
_chemical_name_systematic
;
17α-Ethynyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 O2'
_chemical_formula_sum     'C21 H24 O2'
_chemical_formula_iupac     'C21 H24 O2'
_chemical_formula_weight     308.40
_chemical_melting_point     145
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
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     7.3773(6)
_cell_length_b     10.7430(9)
_cell_length_c     21.2555(18)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1684.6(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3971
_cell_measurement_theta_min     5.386
_cell_measurement_theta_max     53.384
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.499
_exptl_crystal_size_mid     0.427
_exptl_crystal_size_min     0.345
_exptl_crystal_density_diffrn     1.216
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.8238
_exptl_absorpt_correction_T_max     1.0000
_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     'Rigaku FCR CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9960
_diffrn_reflns_av_R_equivalents     0.0705
_diffrn_reflns_av_sigmaI/netI     0.0377
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     27
_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 > 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     2127
_reflns_number_gt     1884
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0490
_refine_ls_R_factor_gt     0.0435
_refine_ls_wR_factor_gt     0.1105
_refine_ls_wR_factor_ref     0.1141
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     2127
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0757P)²+0.0067P] 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     0.199
_refine_diff_density_min     -0.244
_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 0.0000
                         '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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (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 0.3222(3) 0.77612(18) 0.73106(7) 0.0684(5) Uani d . 1 . .
    O O2 0.5307(3) 0.26039(16) 1.17027(8) 0.0583(5) Uani d . 1 . .
    C C1 0.2555(3) 0.6031(2) 0.87459(10) 0.0502(5) Uani d . 1 . .
    H H1 0.1618 0.5584 0.8932 0.060 Uiso calc R 1 . .
    C C2 0.2245(3) 0.6607(2) 0.81810(10) 0.0556(6) Uani d . 1 . .
    H H2 0.1108 0.6561 0.7994 0.067 Uiso calc R 1 . .
    C C3 0.3626(3) 0.7256(2) 0.78916(10) 0.0497(5) Uani d . 1 . .
    C C4 0.5296(3) 0.7326(2) 0.81737(10) 0.0503(5) Uani d . 1 . .
    H H4 0.6227 0.7762 0.7978 0.060 Uiso calc R 1 . .
    C C5 0.5612(3) 0.67502(19) 0.87522(10) 0.0422(5) Uani d . 1 . .
    C C6 0.7485(3) 0.6809(2) 0.90286(11) 0.0548(6) Uani d . 1 . .
    H H6A 0.7993 0.7628 0.8951 0.066 Uiso calc R 1 . .
    H H6B 0.8250 0.6203 0.8820 0.066 Uiso calc R 1 . .
    C C7 0.7495(3) 0.6558(2) 0.97282(11) 0.0496(5) Uani d . 1 . .
    H H7A 0.6936 0.7251 0.9947 0.059 Uiso calc R 1 . .
    H H7B 0.8737 0.6487 0.9873 0.059 Uiso calc R 1 . .
    C C8 0.6478(2) 0.53696(19) 0.98837(9) 0.0362(4) Uani d . 1 . .
    H H8 0.7043 0.4684 0.9652 0.043 Uiso calc R 1 . .
    C C9 0.4518(3) 0.54791(17) 0.96698(9) 0.0345(4) Uani d . 1 . .
    C C10 0.4221(3) 0.60908(18) 0.90521(9) 0.0380(4) Uani d . 1 . .
    C C11 0.3154(3) 0.50772(19) 1.00285(9) 0.0376(4) Uani d . 1 . .
    H H11 0.1985 0.5207 0.9878 0.045 Uiso calc R 1 . .
    C C12 0.3331(3) 0.44369(19) 1.06504(9) 0.0379(4) Uani d . 1 . .
    H H12A 0.2522 0.3726 1.0663 0.045 Uiso calc R 1 . .
    H H12B 0.2980 0.5004 1.0984 0.045 Uiso calc R 1 . .
    C C13 0.5267(3) 0.40034(17) 1.07587(8) 0.0358(4) Uani d . 1 . .
    C C14 0.6545(3) 0.50617(18) 1.05775(9) 0.0369(4) Uani d . 1 . .
    H H14 0.6133 0.5804 1.0804 0.044 Uiso calc R 1 . .
    C C15 0.8389(3) 0.4696(2) 1.08594(10) 0.0517(6) Uani d . 1 . .
    H H15A 0.9140 0.4288 1.0547 0.062 Uiso calc R 1 . .
    H H15B 0.9023 0.5424 1.1015 0.062 Uiso calc R 1 . .
    C C16 0.7939(3) 0.3803(3) 1.13995(11) 0.0572(6) Uani d . 1 . .
    H H16A 0.8467 0.4097 1.1790 0.069 Uiso calc R 1 . .
    H H16B 0.8408 0.2978 1.1311 0.069 Uiso calc R 1 . .
    C C17 0.5855(3) 0.3774(2) 1.14476(10) 0.0447(5) Uani d . 1 . .
    C C18 0.5615(3) 0.28188(19) 1.03758(9) 0.0471(5) Uani d . 1 . .
    H H18A 0.5295 0.2962 0.9944 0.071 Uiso calc R 1 . .
    H H18B 0.4893 0.2151 1.0541 0.071 Uiso calc R 1 . .
    H H18C 0.6874 0.2601 1.0402 0.071 Uiso calc R 1 . .
    C C20 0.4291(5) 0.8770(3) 0.70975(14) 0.0782(9) Uani d . 1 . .
    H H19A 0.5512 0.8493 0.7030 0.117 Uiso calc R 1 . .
    H H19B 0.4284 0.9419 0.7408 0.117 Uiso calc R 1 . .
    H H19C 0.3801 0.9083 0.6710 0.117 Uiso calc R 1 . .
    C C21 0.5210(3) 0.4781(2) 1.18698(9) 0.0500(5) Uani d . 1 . .
    C C22 0.4707(4) 0.5547(3) 1.22112(11) 0.0644(7) Uani d . 1 . .
    H H21 0.4303 0.6162 1.2485 0.077 Uiso calc R 1 . .
    H H3 0.425(5) 0.260(3) 1.1812(13) 0.079(11) Uiso 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
    O1 C3 . 1.381(3) ?
    O1 C20 . 1.415(4) ?
    O2 C17 . 1.428(3) ?
    O2 H3 . 0.82(4) ?
    C1 C2 . 1.370(3) ?
    C1 C10 . 1.392(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.379(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.373(3) ?
    C4 C5 . 1.396(3) ?
    C4 H4 . 0.9300 ?
    C5 C10 . 1.400(3) ?
    C5 C6 . 1.503(3) ?
    C6 C7 . 1.511(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.517(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C14 . 1.512(3) ?
    C8 C9 . 1.520(2) ?
    C8 H8 . 0.9800 ?
    C9 C11 . 1.334(3) ?
    C9 C10 . 1.484(3) ?
    C11 C12 . 1.496(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.520(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C14 . 1.526(3) ?
    C13 C18 . 1.532(3) ?
    C13 C17 . 1.547(3) ?
    C14 C15 . 1.538(3) ?
    C14 H14 . 0.9800 ?
    C15 C16 . 1.532(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.542(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C21 . 1.483(3) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C20 H19A . 0.9600 ?
    C20 H19B . 0.9600 ?
    C20 H19C . 0.9600 ?
    C21 C22 . 1.159(3) ?
    C22 H21 . 0.9300 ?
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 C20 . . 117.8(2) ?
    C17 O2 H3 . . 113(2) ?
    C2 C1 C10 . . 122.4(2) ?
    C2 C1 H1 . . 118.8 ?
    C10 C1 H1 . . 118.8 ?
    C1 C2 C3 . . 119.7(2) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 119.7(2) ?
    C4 C3 O1 . . 124.2(2) ?
    C2 C3 O1 . . 116.0(2) ?
    C3 C4 C5 . . 120.7(2) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C4 C5 C10 . . 120.2(2) ?
    C4 C5 C6 . . 118.6(2) ?
    C10 C5 C6 . . 121.13(19) ?
    C5 C6 C7 . . 112.43(18) ?
    C5 C6 H6A . . 109.1 ?
    C7 C6 H6A . . 109.1 ?
    C5 C6 H6B . . 109.1 ?
    C7 C6 H6B . . 109.1 ?
    H6A C6 H6B . . 107.9 ?
    C6 C7 C8 . . 111.26(18) ?
    C6 C7 H7A . . 109.4 ?
    C8 C7 H7A . . 109.4 ?
    C6 C7 H7B . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    H7A C7 H7B . . 108.0 ?
    C14 C8 C7 . . 112.36(16) ?
    C14 C8 C9 . . 109.86(15) ?
    C7 C8 C9 . . 109.89(17) ?
    C14 C8 H8 . . 108.2 ?
    C7 C8 H8 . . 108.2 ?
    C9 C8 H8 . . 108.2 ?
    C11 C9 C10 . . 122.52(17) ?
    C11 C9 C8 . . 121.42(17) ?
    C10 C9 C8 . . 116.03(16) ?
    C1 C10 C5 . . 117.21(18) ?
    C1 C10 C9 . . 121.55(18) ?
    C5 C10 C9 . . 121.24(17) ?
    C9 C11 C12 . . 126.00(18) ?
    C9 C11 H11 . . 117.0 ?
    C12 C11 H11 . . 117.0 ?
    C11 C12 C13 . . 110.91(15) ?
    C11 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.0 ?
    C12 C13 C14 . . 108.29(15) ?
    C12 C13 C18 . . 109.35(17) ?
    C14 C13 C18 . . 112.42(16) ?
    C12 C13 C17 . . 117.09(16) ?
    C14 C13 C17 . . 100.62(15) ?
    C18 C13 C17 . . 108.90(16) ?
    C8 C14 C13 . . 112.88(15) ?
    C8 C14 C15 . . 117.70(17) ?
    C13 C14 C15 . . 104.93(16) ?
    C8 C14 H14 . . 106.9 ?
    C13 C14 H14 . . 106.9 ?
    C15 C14 H14 . . 106.9 ?
    C16 C15 C14 . . 105.10(17) ?
    C16 C15 H15A . . 110.7 ?
    C14 C15 H15A . . 110.7 ?
    C16 C15 H15B . . 110.7 ?
    C14 C15 H15B . . 110.7 ?
    H15A C15 H15B . . 108.8 ?
    C15 C16 C17 . . 106.14(18) ?
    C15 C16 H16A . . 110.5 ?
    C17 C16 H16A . . 110.5 ?
    C15 C16 H16B . . 110.5 ?
    C17 C16 H16B . . 110.5 ?
    H16A C16 H16B . . 108.7 ?
    O2 C17 C21 . . 108.75(17) ?
    O2 C17 C16 . . 109.0(2) ?
    C21 C17 C16 . . 110.2(2) ?
    O2 C17 C13 . . 114.86(18) ?
    C21 C17 C13 . . 111.54(17) ?
    C16 C17 C13 . . 102.34(18) ?
    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 ?
    O1 C20 H19A . . 109.5 ?
    O1 C20 H19B . . 109.5 ?
    H19A C20 H19B . . 109.5 ?
    O1 C20 H19C . . 109.5 ?
    H19A C20 H19C . . 109.5 ?
    H19B C20 H19C . . 109.5 ?
    C22 C21 C17 . . 178.4(2) ?
    C21 C22 H21 . . 180.0 ?
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 . . . . 1.2(4) ?
    C1 C2 C3 C4 . . . . -0.4(4) ?
    C1 C2 C3 O1 . . . . 177.2(2) ?
    C20 O1 C3 C4 . . . . -24.5(3) ?
    C20 O1 C3 C2 . . . . 158.0(2) ?
    C2 C3 C4 C5 . . . . -0.2(4) ?
    O1 C3 C4 C5 . . . . -177.6(2) ?
    C3 C4 C5 C10 . . . . 0.0(3) ?
    C3 C4 C5 C6 . . . . 177.5(2) ?
    C4 C5 C6 C7 . . . . 160.3(2) ?
    C10 C5 C6 C7 . . . . -22.3(3) ?
    C5 C6 C7 C8 . . . . 50.9(3) ?
    C6 C7 C8 C14 . . . . 177.20(18) ?
    C6 C7 C8 C9 . . . . -60.2(2) ?
    C14 C8 C9 C11 . . . . -13.5(3) ?
    C7 C8 C9 C11 . . . . -137.59(19) ?
    C14 C8 C9 C10 . . . . 164.70(15) ?
    C7 C8 C9 C10 . . . . 40.6(2) ?
    C2 C1 C10 C5 . . . . -1.3(3) ?
    C2 C1 C10 C9 . . . . 178.8(2) ?
    C4 C5 C10 C1 . . . . 0.7(3) ?
    C6 C5 C10 C1 . . . . -176.7(2) ?
    C4 C5 C10 C9 . . . . -179.47(17) ?
    C6 C5 C10 C9 . . . . 3.1(3) ?
    C11 C9 C10 C1 . . . . -14.8(3) ?
    C8 C9 C10 C1 . . . . 167.05(19) ?
    C11 C9 C10 C5 . . . . 165.4(2) ?
    C8 C9 C10 C5 . . . . -12.8(3) ?
    C10 C9 C11 C12 . . . . 179.06(17) ?
    C8 C9 C11 C12 . . . . -2.9(3) ?
    C9 C11 C12 C13 . . . . -14.1(3) ?
    C11 C12 C13 C14 . . . . 45.3(2) ?
    C11 C12 C13 C18 . . . . -77.5(2) ?
    C11 C12 C13 C17 . . . . 158.11(17) ?
    C7 C8 C14 C13 . . . . 170.07(16) ?
    C9 C8 C14 C13 . . . . 47.4(2) ?
    C7 C8 C14 C15 . . . . -67.4(2) ?
    C9 C8 C14 C15 . . . . 169.92(17) ?
    C12 C13 C14 C8 . . . . -65.2(2) ?
    C18 C13 C14 C8 . . . . 55.8(2) ?
    C17 C13 C14 C8 . . . . 171.47(15) ?
    C12 C13 C14 C15 . . . . 165.44(16) ?
    C18 C13 C14 C15 . . . . -73.6(2) ?
    C17 C13 C14 C15 . . . . 42.07(18) ?
    C8 C14 C15 C16 . . . . -149.88(18) ?
    C13 C14 C15 C16 . . . . -23.4(2) ?
    C14 C15 C16 C17 . . . . -4.8(2) ?
    C15 C16 C17 O2 . . . . 152.64(18) ?
    C15 C16 C17 C21 . . . . -88.1(2) ?
    C15 C16 C17 C13 . . . . 30.6(2) ?
    C12 C13 C17 O2 . . . . 80.7(2) ?
    C14 C13 C17 O2 . . . . -162.21(17) ?
    C18 C13 C17 O2 . . . . -43.9(2) ?
    C12 C13 C17 C21 . . . . -43.6(3) ?
    C14 C13 C17 C21 . . . . 73.5(2) ?
    C18 C13 C17 C21 . . . . -168.21(19) ?
    C12 C13 C17 C16 . . . . -161.36(18) ?
    C14 C13 C17 C16 . . . . -44.3(2) ?
    C18 C13 C17 C16 . . . . 74.0(2) ?
    O2 C17 C21 C22 . . . . 25(10) ?
    C16 C17 C21 C22 . . . . -95(10) ?
    C13 C17 C21 C22 . . . . 152(10) ?
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
    O2 H3 O1 2_565 0.82(4) 2.14(4) 2.933(3) 163(3)
