##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2003-10-07
_journal_date_accepted     2003-10-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     11
_journal_page_first     o1745
_journal_page_last     o1747
_journal_paper_category     EO
_publ_contact_author_name     'Professor Fun Hoong-Kun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6533888  Ext. 3690'
_publ_section_title
;
17-Ethynyl-3,17α-dimethyoxy-5β-estra-1,3,5(10)-triene
;
loop_
    _publ_author_name
    _publ_author_address
    'Choudhary, M. Iqbal'
;
HEJ Research Institute of Chemistry
International Centre for Chemical Sciences
University of Karachi
Karachi 75270
Pakistan
;
    'Musharraf, Syed Ghulam'
;
HEJ Research Institute of Chemistry
International Centre for Chemical Sciences
University of Karachi
Karachi 75270
Pakistan
;
    'Anjum, Shazia'
;
HEJ Research Institute of Chemistry
International Centre for Chemical Sciences
University of Karachi
Karachi 75270
Pakistan
;
    'Rahman, Azhar Abul'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Fun, Hoong-Kun'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Atta-ur-Rahman'
;
HEJ Research Institute of Chemistry
International Centre for Chemical Sciences
University of Karachi
Karachi 75270
Pakistan
;
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
17-Ethynyl-3,17α-dimethyoxy-5β-estra-1,3,5(10)-triene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H28 O2'
_chemical_formula_sum     'C22 H28 O2'
_chemical_formula_iupac     'C22 H28 O2'
_chemical_formula_weight     324.44
_chemical_melting_point     '387-388 K'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2'
_symmetry_space_group_name_Hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     12.340(2)
_cell_length_b     6.8289(13)
_cell_length_c     21.710(4)
_cell_angle_alpha     90
_cell_angle_beta     100.037(4)
_cell_angle_gamma     90
_cell_volume     1801.4(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4503
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     27.6
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.57
_exptl_crystal_size_mid     0.51
_exptl_crystal_size_min     0.39
_exptl_crystal_density_diffrn     1.196
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.074
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.959
_exptl_absorpt_correction_T_max     0.972
_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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     6003
_diffrn_reflns_av_R_equivalents     0.018
_diffrn_reflns_av_sigmaI/netI     0.021
_diffrn_reflns_theta_min     2.86
_diffrn_reflns_theta_max     27.57
_diffrn_reflns_theta_full     27.57
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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 > 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     2221
_reflns_number_gt     2141
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.059
_refine_ls_R_factor_gt     0.058
_refine_ls_wR_factor_gt     0.149
_refine_ls_wR_factor_ref     0.151
_refine_ls_goodness_of_fit_ref     1.195
_refine_ls_restrained_S_all     1.195
_refine_ls_number_reflns     2221
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0874P)²+0.3877P] 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     0.27
_refine_diff_density_min     -0.23
_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 (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material
                       'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
loop_
    _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
    _atom_site_type_symbol
    O1 1.07278(18) 0.1921(4) 0.43064(9) 0.0533(5) Uani d . 1 . . O
    O2 0.63488(14) 0.5061(4) -0.03606(8) 0.0481(5) Uani d . 1 . . O
    C1 0.70259(17) 0.5009(4) 0.13210(11) 0.0369(5) Uani d . 1 . . C
    H1 0.6646 0.5002 0.1655 0.044 Uiso calc R 1 . . H
    C2 0.64337(18) 0.5044(5) 0.07211(12) 0.0408(5) Uani d . 1 . . C
    H2 0.5669 0.5056 0.0653 0.049 Uiso calc R 1 . . H
    C3 0.69928(18) 0.5059(4) 0.02198(10) 0.0360(5) Uani d . 1 . . C
    C4 0.81273(19) 0.5081(4) 0.03285(11) 0.0367(5) Uani d . 1 . . C
    H4 0.8501 0.5107 -0.0008 0.044 Uiso calc R 1 . . H
    C5 0.87201(17) 0.5065(4) 0.09336(10) 0.0338(5) Uani d . 1 . . C
    C6 0.99630(18) 0.5103(5) 0.10107(11) 0.0431(6) Uani d . 1 . . C
    H6A 1.0179 0.6130 0.0748 0.052 Uiso calc R 1 . . H
    H6B 1.0214 0.3866 0.0867 0.052 Uiso calc R 1 . . H
    C7 1.0527(2) 0.5448(5) 0.16791(13) 0.0471(7) Uani d . 1 . . C
    H7A 1.0471 0.6821 0.1784 0.057 Uiso calc R 1 . . H
    H7B 1.1301 0.5119 0.1722 0.057 Uiso calc R 1 . . H
    C8 0.99971(18) 0.4203(4) 0.21248(11) 0.0349(5) Uani d . 1 . . C
    H8 0.9978 0.2841 0.1981 0.042 Uiso calc R 1 . . H
    C9 0.88100(17) 0.4899(4) 0.21110(10) 0.0345(5) Uani d . 1 . . C
    H9 0.8853 0.6242 0.2272 0.041 Uiso calc R 1 . . H
    C10 0.81769(16) 0.4984(4) 0.14467(10) 0.0324(4) Uani d . 1 . . C
    C11 0.82461(19) 0.3673(5) 0.25512(11) 0.0432(6) Uani d . 1 . . C
    H11A 0.8166 0.2340 0.2396 0.052 Uiso calc R 1 . . H
    H11B 0.7515 0.4194 0.2553 0.052 Uiso calc R 1 . . H
    C12 0.8887(2) 0.3654(5) 0.32208(11) 0.0448(6) Uani d . 1 . . C
    H12A 0.8886 0.4958 0.3398 0.054 Uiso calc R 1 . . H
    H12B 0.8528 0.2779 0.3474 0.054 Uiso calc R 1 . . H
    C13 1.0067(2) 0.2988(4) 0.32385(11) 0.0373(5) Uani d . 1 . . C
    C14 1.05987(19) 0.4277(4) 0.27932(11) 0.0380(5) Uani d . 1 . . C
    H14 1.0549 0.5631 0.2935 0.046 Uiso calc R 1 . . H
    C15 1.1822(2) 0.3706(6) 0.29429(13) 0.0513(7) Uani d . 1 . . C
    H15A 1.2285 0.4787 0.2859 0.062 Uiso calc R 1 . . H
    H15B 1.1970 0.2584 0.2696 0.062 Uiso calc R 1 . . H
    C16 1.2023(2) 0.3202(6) 0.36451(14) 0.0567(8) Uani d . 1 . . C
    H16A 1.2542 0.4115 0.3878 0.068 Uiso calc R 1 . . H
    H16B 1.2317 0.1888 0.3713 0.068 Uiso calc R 1 . . H
    C17 1.0883(2) 0.3355(4) 0.38596(12) 0.0433(6) Uani d . 1 . . C
    C18 1.0083(3) 0.0803(5) 0.30757(14) 0.0501(7) Uani d . 1 . . C
    H18A 0.9695 0.0602 0.2657 0.075 Uiso calc R 1 . . H
    H18B 0.9733 0.0068 0.3363 0.075 Uiso calc R 1 . . H
    H18C 1.0831 0.0373 0.3105 0.075 Uiso calc R 1 . . H
    C19 1.0742(3) 0.5336(5) 0.40979(13) 0.0564(8) Uani d . 1 . . C
    C20 1.0653(4) 0.6923(7) 0.42686(18) 0.0822(13) Uani d . 1 . . C
    H20 1.0601 0.8228 0.4375 0.099 Uiso d R 1 . . H
    C21 1.1435(3) 0.2127(7) 0.48961(15) 0.0730(11) Uani d . 1 . . C
    H21A 1.1312 0.1062 0.5164 0.110 Uiso calc R 1 . . H
    H21B 1.1281 0.3344 0.5085 0.110 Uiso calc R 1 . . H
    H21C 1.2188 0.2114 0.4836 0.110 Uiso calc R 1 . . H
    C22 0.6893(2) 0.5038(5) -0.08813(11) 0.0473(6) Uani d . 1 . . C
    H22A 0.6359 0.5038 -0.1260 0.071 Uiso calc R 1 . . H
    H22B 0.7340 0.3883 -0.0867 0.071 Uiso calc R 1 . . H
    H22C 0.7351 0.6178 -0.0871 0.071 Uiso calc R 1 . . H
_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 C17 . 1.415(3) y
    O1 C21 . 1.425(3) y
    O2 C3 . 1.368(3) y
    O2 C22 . 1.412(3) y
    C1 C2 . 1.378(3) ?
    C1 C10 . 1.399(3) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.386(3) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.379(3) ?
    C4 C5 . 1.388(3) ?
    C4 H4 . 0.93 ?
    C5 C10 . 1.398(3) ?
    C5 C6 . 1.514(3) ?
    C6 C7 . 1.514(3) ?
    C6 H6A . 0.97 ?
    C6 H6B . 0.97 ?
    C7 C8 . 1.519(3) ?
    C7 H7A . 0.97 ?
    C7 H7B . 0.97 ?
    C8 C14 . 1.511(3) ?
    C8 C9 . 1.535(3) ?
    C8 H8 . 0.98 ?
    C9 C10 . 1.517(3) ?
    C9 C11 . 1.527(3) ?
    C9 H9 . 0.98 ?
    C11 C12 . 1.529(3) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 C13 . 1.519(3) ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 C18 . 1.534(4) ?
    C13 C14 . 1.537(3) ?
    C13 C17 . 1.556(3) ?
    C14 C15 . 1.538(3) ?
    C14 H14 . 0.98 ?
    C15 C16 . 1.540(4) ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C16 C17 . 1.561(4) ?
    C16 H16A . 0.97 ?
    C16 H16B . 0.97 ?
    C17 C19 . 1.469(5) y
    C18 H18A . 0.96 ?
    C18 H18B . 0.96 ?
    C18 H18C . 0.96 ?
    C19 C20 . 1.156(6) y
    C20 H20 . 0.93 ?
    C21 H21A . 0.96 ?
    C21 H21B . 0.96 ?
    C21 H21C . 0.96 ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
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
    C17 O1 C21 . . 114.4(3) y
    C3 O2 C22 . . 117.15(18) y
    C2 C1 C10 . . 122.52(19) ?
    C2 C1 H1 . . 118.7 ?
    C10 C1 H1 . . 118.7 ?
    C1 C2 C3 . . 119.2(2) ?
    C1 C2 H2 . . 120.4 ?
    C3 C2 H2 . . 120.4 ?
    O2 C3 C4 . . 124.6(2) ?
    O2 C3 C2 . . 115.76(19) ?
    C4 C3 C2 . . 119.7(2) ?
    C3 C4 C5 . . 120.9(2) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    C4 C5 C10 . . 120.52(19) ?
    C4 C5 C6 . . 117.46(18) ?
    C10 C5 C6 . . 122.0(2) ?
    C5 C6 C7 . . 113.32(19) ?
    C5 C6 H6A . . 108.9 ?
    C7 C6 H6A . . 108.9 ?
    C5 C6 H6B . . 108.9 ?
    C7 C6 H6B . . 108.9 ?
    H6A C6 H6B . . 107.7 ?
    C6 C7 C8 . . 110.3(2) ?
    C6 C7 H7A . . 109.6 ?
    C8 C7 H7A . . 109.6 ?
    C6 C7 H7B . . 109.6 ?
    C8 C7 H7B . . 109.6 ?
    H7A C7 H7B . . 108.1 ?
    C14 C8 C7 . . 113.53(19) ?
    C14 C8 C9 . . 108.40(18) ?
    C7 C8 C9 . . 109.2(2) ?
    C14 C8 H8 . . 108.5 ?
    C7 C8 H8 . . 108.5 ?
    C9 C8 H8 . . 108.5 ?
    C10 C9 C11 . . 113.63(18) ?
    C10 C9 C8 . . 111.22(17) ?
    C11 C9 C8 . . 110.8(2) ?
    C10 C9 H9 . . 106.9 ?
    C11 C9 H9 . . 106.9 ?
    C8 C9 H9 . . 106.9 ?
    C5 C10 C1 . . 117.1(2) ?
    C5 C10 C9 . . 121.34(18) ?
    C1 C10 C9 . . 121.54(18) ?
    C9 C11 C12 . . 112.5(2) ?
    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 . . 111.20(19) ?
    C13 C12 H12A . . 109.4 ?
    C11 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    H12A C12 H12B . . 108.0 ?
    C12 C13 C18 . . 109.6(2) ?
    C12 C13 C14 . . 109.0(2) ?
    C18 C13 C14 . . 112.8(2) ?
    C12 C13 C17 . . 116.5(2) ?
    C18 C13 C17 . . 108.9(2) ?
    C14 C13 C17 . . 99.8(2) ?
    C8 C14 C13 . . 113.14(19) ?
    C8 C14 C15 . . 119.6(2) ?
    C13 C14 C15 . . 103.5(2) ?
    C8 C14 H14 . . 106.6 ?
    C13 C14 H14 . . 106.6 ?
    C15 C14 H14 . . 106.6 ?
    C14 C15 C16 . . 104.4(2) ?
    C14 C15 H15A . . 110.9 ?
    C16 C15 H15A . . 110.9 ?
    C14 C15 H15B . . 110.9 ?
    C16 C15 H15B . . 110.9 ?
    H15A C15 H15B . . 108.9 ?
    C15 C16 C17 . . 106.4(2) ?
    C15 C16 H16A . . 110.4 ?
    C17 C16 H16A . . 110.4 ?
    C15 C16 H16B . . 110.4 ?
    C17 C16 H16B . . 110.4 ?
    H16A C16 H16B . . 108.6 ?
    O1 C17 C19 . . 111.0(2) ?
    O1 C17 C13 . . 109.8(2) ?
    C19 C17 C13 . . 110.8(2) ?
    O1 C17 C16 . . 113.3(2) ?
    C19 C17 C16 . . 109.5(3) ?
    C13 C17 C16 . . 102.2(2) ?
    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 ?
    C20 C19 C17 . . 177.4(4) y
    C19 C20 H20 . . 175.2 ?
    O1 C21 H21A . . 109.5 ?
    O1 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O1 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    O2 C22 H22A . . 109.5 ?
    O2 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O2 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 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 . . . . -0.1(4) ?
    C22 O2 C3 C4 . . . . 1.6(4) y
    C22 O2 C3 C2 . . . . -178.8(3) y
    C1 C2 C3 O2 . . . . 179.0(3) ?
    C1 C2 C3 C4 . . . . -1.4(4) ?
    O2 C3 C4 C5 . . . . -179.6(2) ?
    C2 C3 C4 C5 . . . . 0.8(4) ?
    C3 C4 C5 C10 . . . . 1.4(4) ?
    C3 C4 C5 C6 . . . . -179.7(3) ?
    C4 C5 C6 C7 . . . . 169.7(2) ?
    C10 C5 C6 C7 . . . . -11.4(4) ?
    C5 C6 C7 C8 . . . . 44.3(4) ?
    C6 C7 C8 C14 . . . . 173.0(2) ?
    C6 C7 C8 C9 . . . . -65.9(3) ?
    C14 C8 C9 C10 . . . . 176.4(2) ?
    C7 C8 C9 C10 . . . . 52.3(3) ?
    C14 C8 C9 C11 . . . . -56.2(3) ?
    C7 C8 C9 C11 . . . . 179.7(2) ?
    C4 C5 C10 C1 . . . . -2.8(4) ?
    C6 C5 C10 C1 . . . . 178.3(3) ?
    C4 C5 C10 C9 . . . . 178.0(2) ?
    C6 C5 C10 C9 . . . . -0.9(4) ?
    C2 C1 C10 C5 . . . . 2.2(4) ?
    C2 C1 C10 C9 . . . . -178.6(2) ?
    C11 C9 C10 C5 . . . . -145.7(3) ?
    C8 C9 C10 C5 . . . . -19.8(3) ?
    C11 C9 C10 C1 . . . . 35.1(4) ?
    C8 C9 C10 C1 . . . . 161.0(3) ?
    C10 C9 C11 C12 . . . . -178.6(2) ?
    C8 C9 C11 C12 . . . . 55.3(3) ?
    C9 C11 C12 C13 . . . . -54.7(3) ?
    C11 C12 C13 C18 . . . . -69.6(3) ?
    C11 C12 C13 C14 . . . . 54.4(3) ?
    C11 C12 C13 C17 . . . . 166.2(2) ?
    C7 C8 C14 C13 . . . . -179.1(2) ?
    C9 C8 C14 C13 . . . . 59.3(3) ?
    C7 C8 C14 C15 . . . . -56.8(3) ?
    C9 C8 C14 C15 . . . . -178.4(3) ?
    C12 C13 C14 C8 . . . . -58.8(3) ?
    C18 C13 C14 C8 . . . . 63.2(3) ?
    C17 C13 C14 C8 . . . . 178.6(2) ?
    C12 C13 C14 C15 . . . . 170.3(2) ?
    C18 C13 C14 C15 . . . . -67.7(3) ?
    C17 C13 C14 C15 . . . . 47.7(3) ?
    C8 C14 C15 C16 . . . . -159.3(3) ?
    C13 C14 C15 C16 . . . . -32.4(3) ?
    C14 C15 C16 C17 . . . . 4.1(4) ?
    C21 O1 C17 C19 . . . . -57.0(3) ?
    C21 O1 C17 C13 . . . . -179.8(3) y
    C21 O1 C17 C16 . . . . 66.7(3) y
    C12 C13 C17 O1 . . . . 78.4(3) ?
    C18 C13 C17 O1 . . . . -46.2(3) ?
    C14 C13 C17 O1 . . . . -164.6(2) ?
    C12 C13 C17 C19 . . . . -44.5(3) ?
    C18 C13 C17 C19 . . . . -169.1(3) ?
    C14 C13 C17 C19 . . . . 72.5(3) ?
    C12 C13 C17 C16 . . . . -161.2(3) ?
    C18 C13 C17 C16 . . . . 74.3(3) ?
    C14 C13 C17 C16 . . . . -44.1(3) ?
    C15 C16 C17 O1 . . . . 143.0(3) ?
    C15 C16 C17 C19 . . . . -92.5(3) ?
    C15 C16 C17 C13 . . . . 25.0(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C2 H2 O2 . . 2_655 0.93 2.46 3.386(3) 174 yes
    C20 H20 O1 . . 1_565 0.93 2.53 3.415(6) 159 yes
