##############################################################################
###                                                                        ###
###        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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-31
_journal_date_accepted     2010-08-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2265
_journal_page_last     o2265
_journal_paper_category     QO
_journal_coeditor_code     HB5593
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
3-Methyl-5α-cholest-2-ene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ketuly, Kamal Aziz'
;
Additional correspondence author, e-mail: kketuly@um.edu.my.
;
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Hadi, A. Hamid A.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1S,2S,7R,10R,11R,14R,15R)-
2,5,10,15-tetramethyl-14-[(2R)-6-methylheptan-2-
yl]tetracyclo[8.7.0.0^2,7^.0^11,15^]heptadec-4-ene
;
_chemical_name_common     '3-Methyl-5α-cholest-2-ene'
_chemical_formula_moiety     'C28 H48'
_chemical_formula_sum     'C28 H48'
_chemical_formula_weight     384.66
_chemical_melting_point     ?
_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     22.216(3)
_cell_length_b     11.7576(15)
_cell_length_c     9.6335(13)
_cell_angle_alpha     90
_cell_angle_beta     106.652(2)
_cell_angle_gamma     90
_cell_volume     2410.9(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1712
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     22.9
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.060
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     0.058
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.786
_exptl_absorpt_correction_T_max     0.862
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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 SMART APEX CCD'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11615
_diffrn_reflns_av_R_equivalents     0.060
_diffrn_reflns_av_sigmaI/netI     0.053
_diffrn_reflns_theta_min     1.9
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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     2902
_reflns_number_gt     2379
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.064
_refine_ls_R_factor_gt     0.047
_refine_ls_wR_factor_gt     0.112
_refine_ls_wR_factor_ref     0.121
_refine_ls_goodness_of_fit_ref     1.02
_refine_ls_restrained_S_all     1.02
_refine_ls_number_reflns     2902
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0616P)²+0.7202P] 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_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.24
_refine_diff_density_min     -0.20
_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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and
Qmol (Gans & Shalloway, 2001)
;
_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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.25641(12) 0.4995(2) 0.1799(3) 0.0211(6) Uani d . 1 . .
    H H1A 0.2370 0.5179 0.0752 0.025 Uiso calc R 1 . .
    C C2 0.22521(14) 0.3904(3) 0.2106(3) 0.0259(6) Uani d . 1 . .
    H H2A 0.2276 0.3322 0.1382 0.031 Uiso calc R 1 . .
    H H2B 0.2488 0.3614 0.3074 0.031 Uiso calc R 1 . .
    C C3 0.15797(13) 0.4068(3) 0.2063(3) 0.0226(6) Uani d . 1 . .
    C C4 0.12007(14) 0.3006(3) 0.2017(3) 0.0289(7) Uani d . 1 . .
    H H4A 0.0771 0.3210 0.2002 0.043 Uiso calc R 1 . .
    H H4B 0.1392 0.2543 0.2876 0.043 Uiso calc R 1 . .
    H H4C 0.1191 0.2572 0.1142 0.043 Uiso calc R 1 . .
    C C5 0.13404(13) 0.5112(3) 0.2097(3) 0.0241(6) Uani d . 1 . .
    H H5A 0.0909 0.5172 0.2052 0.029 Uiso calc R 1 . .
    C C6 0.17105(12) 0.6191(3) 0.2201(3) 0.0226(6) Uani d . 1 . .
    H H6A 0.1598 0.6704 0.2902 0.027 Uiso calc R 1 . .
    H H6B 0.1588 0.6572 0.1245 0.027 Uiso calc R 1 . .
    C C7 0.24280(12) 0.6016(2) 0.2674(3) 0.0178(5) Uani d . 1 . .
    C C8 0.26358(13) 0.5758(3) 0.4308(3) 0.0238(6) Uani d . 1 . .
    H H8A 0.2421 0.5073 0.4498 0.036 Uiso calc R 1 . .
    H H8B 0.2527 0.6402 0.4837 0.036 Uiso calc R 1 . .
    H H8C 0.3091 0.5636 0.4631 0.036 Uiso calc R 1 . .
    C C9 0.27602(13) 0.7082(2) 0.2307(3) 0.0175(6) Uani d . 1 . .
    H H9A 0.2565 0.7224 0.1250 0.021 Uiso calc R 1 . .
    C C10 0.34646(12) 0.6901(2) 0.2494(3) 0.0181(6) Uani d . 1 . .
    H H10A 0.3679 0.6750 0.3541 0.022 Uiso calc R 1 . .
    C C11 0.35657(12) 0.5880(2) 0.1617(3) 0.0233(6) Uani d . 1 . .
    H H11A 0.3387 0.6045 0.0572 0.028 Uiso calc R 1 . .
    H H11B 0.4022 0.5747 0.1804 0.028 Uiso calc R 1 . .
    C C12 0.32603(13) 0.4813(2) 0.1997(3) 0.0224(6) Uani d . 1 . .
    H H12A 0.3316 0.4178 0.1369 0.027 Uiso calc R 1 . .
    H H12B 0.3470 0.4600 0.3015 0.027 Uiso calc R 1 . .
    C C13 0.26474(12) 0.8173(2) 0.3085(3) 0.0204(6) Uani d . 1 . .
    H H13A 0.2189 0.8302 0.2868 0.025 Uiso calc R 1 . .
    H H13B 0.2819 0.8064 0.4144 0.025 Uiso calc R 1 . .
    C C14 0.29511(12) 0.9230(2) 0.2637(3) 0.0193(6) Uani d . 1 . .
    H H14A 0.2748 0.9393 0.1600 0.023 Uiso calc R 1 . .
    H H14B 0.2883 0.9892 0.3207 0.023 Uiso calc R 1 . .
    C C15 0.36558(12) 0.9056(2) 0.2883(3) 0.0173(6) Uani d . 1 . .
    C C16 0.39946(13) 0.8959(3) 0.4510(3) 0.0222(6) Uani d . 1 . .
    H H16A 0.4446 0.8853 0.4651 0.033 Uiso calc R 1 . .
    H H16B 0.3828 0.8307 0.4915 0.033 Uiso calc R 1 . .
    H H16C 0.3926 0.9656 0.5003 0.033 Uiso calc R 1 . .
    C C17 0.37381(12) 0.7980(2) 0.2051(3) 0.0169(5) Uani d . 1 . .
    H H17A 0.3499 0.8119 0.1016 0.020 Uiso calc R 1 . .
    C C18 0.44307(12) 0.7989(2) 0.2104(3) 0.0210(6) Uani d . 1 . .
    H H18A 0.4504 0.7547 0.1292 0.025 Uiso calc R 1 . .
    H H18B 0.4696 0.7676 0.3031 0.025 Uiso calc R 1 . .
    C C19 0.45632(13) 0.9275(2) 0.1962(3) 0.0217(6) Uani d . 1 . .
    H H19A 0.4954 0.9500 0.2705 0.026 Uiso calc R 1 . .
    H H19B 0.4614 0.9437 0.0993 0.026 Uiso calc R 1 . .
    C C20 0.39944(12) 0.9943(2) 0.2177(3) 0.0189(6) Uani d . 1 . .
    H H20A 0.3708 1.0120 0.1193 0.023 Uiso calc R 1 . .
    C C21 0.41998(12) 1.1083(3) 0.2951(3) 0.0216(6) Uani d . 1 . .
    H H21A 0.4519 1.0910 0.3894 0.026 Uiso calc R 1 . .
    C C22 0.36660(14) 1.1740(3) 0.3294(3) 0.0284(7) Uani d . 1 . .
    H H22A 0.3830 1.2450 0.3792 0.043 Uiso calc R 1 . .
    H H22B 0.3485 1.1276 0.3919 0.043 Uiso calc R 1 . .
    H H22C 0.3341 1.1914 0.2391 0.043 Uiso calc R 1 . .
    C C23 0.45225(13) 1.1824(3) 0.2065(3) 0.0228(6) Uani d . 1 . .
    H H23A 0.4762 1.1323 0.1590 0.027 Uiso calc R 1 . .
    H H23B 0.4194 1.2209 0.1291 0.027 Uiso calc R 1 . .
    C C24 0.49675(14) 1.2726(3) 0.2937(3) 0.0263(7) Uani d . 1 . .
    H H24A 0.4731 1.3236 0.3410 0.032 Uiso calc R 1 . .
    H H24B 0.5301 1.2349 0.3708 0.032 Uiso calc R 1 . .
    C C25 0.52703(13) 1.3430(2) 0.1990(3) 0.0216(6) Uani d . 1 . .
    H H25A 0.4936 1.3870 0.1297 0.026 Uiso calc R 1 . .
    H H25B 0.5452 1.2902 0.1418 0.026 Uiso calc R 1 . .
    C C26 0.57833(12) 1.4256(2) 0.2788(3) 0.0205(6) Uani d . 1 . .
    H H26A 0.6114 1.3814 0.3508 0.025 Uiso calc R 1 . .
    C C27 0.60833(15) 1.4801(3) 0.1707(3) 0.0307(7) Uani d . 1 . .
    H H27A 0.6407 1.5342 0.2215 0.046 Uiso calc R 1 . .
    H H27B 0.5761 1.5201 0.0958 0.046 Uiso calc R 1 . .
    H H27C 0.6274 1.4208 0.1256 0.046 Uiso calc R 1 . .
    C C28 0.55335(14) 1.5163(3) 0.3599(3) 0.0330(7) Uani d . 1 . .
    H H28A 0.5876 1.5674 0.4094 0.049 Uiso calc R 1 . .
    H H28B 0.5359 1.4800 0.4315 0.049 Uiso calc R 1 . .
    H H28C 0.5204 1.5600 0.2913 0.049 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 C12 . 1.519(4) ?
    C1 C2 . 1.528(4) ?
    C1 C7 . 1.545(4) ?
    C1 H1A . 1.0000 ?
    C2 C3 . 1.495(4) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C5 . 1.342(4) ?
    C3 C4 . 1.499(4) ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C5 C6 . 1.499(4) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.541(3) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.539(3) ?
    C7 C9 . 1.546(4) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.538(4) ?
    C9 C13 . 1.542(4) ?
    C9 H9A . 1.0000 ?
    C10 C17 . 1.520(4) ?
    C10 C11 . 1.521(4) ?
    C10 H10A . 1.0000 ?
    C11 C12 . 1.520(4) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.534(4) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.529(3) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C17 . 1.537(4) ?
    C15 C16 . 1.537(3) ?
    C15 C20 . 1.552(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.525(3) ?
    C17 H17A . 1.0000 ?
    C18 C19 . 1.554(4) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.552(4) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 C21 . 1.538(4) ?
    C20 H20A . 1.0000 ?
    C21 C22 . 1.529(4) ?
    C21 C23 . 1.533(4) ?
    C21 H21A . 1.0000 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 C24 . 1.527(4) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 C25 . 1.524(4) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C25 C26 . 1.527(4) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C26 C28 . 1.518(4) ?
    C26 C27 . 1.528(4) ?
    C26 H26A . 1.0000 ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
    C28 H28A . 0.9800 ?
    C28 H28B . 0.9800 ?
    C28 H28C . 0.9800 ?
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
    C12 C1 C2 . . 111.0(2) ?
    C12 C1 C7 . . 113.1(2) ?
    C2 C1 C7 . . 112.1(2) ?
    C12 C1 H1A . . 106.7 ?
    C2 C1 H1A . . 106.7 ?
    C7 C1 H1A . . 106.7 ?
    C3 C2 C1 . . 113.0(2) ?
    C3 C2 H2A . . 109.0 ?
    C1 C2 H2A . . 109.0 ?
    C3 C2 H2B . . 109.0 ?
    C1 C2 H2B . . 109.0 ?
    H2A C2 H2B . . 107.8 ?
    C5 C3 C4 . . 122.7(3) ?
    C5 C3 C2 . . 121.1(3) ?
    C4 C3 C2 . . 116.2(3) ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C3 C5 C6 . . 124.2(2) ?
    C3 C5 H5A . . 117.9 ?
    C6 C5 H5A . . 117.9 ?
    C5 C6 C7 . . 114.1(2) ?
    C5 C6 H6A . . 108.7 ?
    C7 C6 H6A . . 108.7 ?
    C5 C6 H6B . . 108.7 ?
    C7 C6 H6B . . 108.7 ?
    H6A C6 H6B . . 107.6 ?
    C8 C7 C6 . . 108.1(2) ?
    C8 C7 C1 . . 110.9(2) ?
    C6 C7 C1 . . 106.8(2) ?
    C8 C7 C9 . . 111.8(2) ?
    C6 C7 C9 . . 110.2(2) ?
    C1 C7 C9 . . 108.90(19) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C10 C9 C13 . . 111.1(2) ?
    C10 C9 C7 . . 113.4(2) ?
    C13 C9 C7 . . 114.1(2) ?
    C10 C9 H9A . . 105.8 ?
    C13 C9 H9A . . 105.8 ?
    C7 C9 H9A . . 105.8 ?
    C17 C10 C11 . . 111.6(2) ?
    C17 C10 C9 . . 109.1(2) ?
    C11 C10 C9 . . 110.6(2) ?
    C17 C10 H10A . . 108.5 ?
    C11 C10 H10A . . 108.5 ?
    C9 C10 H10A . . 108.5 ?
    C12 C11 C10 . . 111.7(2) ?
    C12 C11 H11A . . 109.3 ?
    C10 C11 H11A . . 109.3 ?
    C12 C11 H11B . . 109.3 ?
    C10 C11 H11B . . 109.3 ?
    H11A C11 H11B . . 107.9 ?
    C1 C12 C11 . . 111.2(2) ?
    C1 C12 H12A . . 109.4 ?
    C11 C12 H12A . . 109.4 ?
    C1 C12 H12B . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    H12A C12 H12B . . 108.0 ?
    C14 C13 C9 . . 113.1(2) ?
    C14 C13 H13A . . 109.0 ?
    C9 C13 H13A . . 109.0 ?
    C14 C13 H13B . . 109.0 ?
    C9 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    C15 C14 C13 . . 111.2(2) ?
    C15 C14 H14A . . 109.4 ?
    C13 C14 H14A . . 109.4 ?
    C15 C14 H14B . . 109.4 ?
    C13 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
    C14 C15 C17 . . 107.4(2) ?
    C14 C15 C16 . . 110.4(2) ?
    C17 C15 C16 . . 112.0(2) ?
    C14 C15 C20 . . 116.5(2) ?
    C17 C15 C20 . . 100.38(19) ?
    C16 C15 C20 . . 109.9(2) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C10 C17 C18 . . 118.5(2) ?
    C10 C17 C15 . . 115.10(19) ?
    C18 C17 C15 . . 104.3(2) ?
    C10 C17 H17A . . 106.0 ?
    C18 C17 H17A . . 106.0 ?
    C15 C17 H17A . . 106.0 ?
    C17 C18 C19 . . 102.6(2) ?
    C17 C18 H18A . . 111.2 ?
    C19 C18 H18A . . 111.2 ?
    C17 C18 H18B . . 111.2 ?
    C19 C18 H18B . . 111.2 ?
    H18A C18 H18B . . 109.2 ?
    C20 C19 C18 . . 107.4(2) ?
    C20 C19 H19A . . 110.2 ?
    C18 C19 H19A . . 110.2 ?
    C20 C19 H19B . . 110.2 ?
    C18 C19 H19B . . 110.2 ?
    H19A C19 H19B . . 108.5 ?
    C21 C20 C19 . . 111.5(2) ?
    C21 C20 C15 . . 119.2(2) ?
    C19 C20 C15 . . 103.5(2) ?
    C21 C20 H20A . . 107.4 ?
    C19 C20 H20A . . 107.4 ?
    C15 C20 H20A . . 107.4 ?
    C22 C21 C20 . . 113.8(2) ?
    C22 C21 C23 . . 110.4(2) ?
    C20 C21 C23 . . 110.3(2) ?
    C22 C21 H21A . . 107.3 ?
    C20 C21 H21A . . 107.3 ?
    C23 C21 H21A . . 107.3 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C24 C23 C21 . . 114.9(2) ?
    C24 C23 H23A . . 108.5 ?
    C21 C23 H23A . . 108.5 ?
    C24 C23 H23B . . 108.5 ?
    C21 C23 H23B . . 108.5 ?
    H23A C23 H23B . . 107.5 ?
    C25 C24 C23 . . 112.0(2) ?
    C25 C24 H24A . . 109.2 ?
    C23 C24 H24A . . 109.2 ?
    C25 C24 H24B . . 109.2 ?
    C23 C24 H24B . . 109.2 ?
    H24A C24 H24B . . 107.9 ?
    C24 C25 C26 . . 116.0(2) ?
    C24 C25 H25A . . 108.3 ?
    C26 C25 H25A . . 108.3 ?
    C24 C25 H25B . . 108.3 ?
    C26 C25 H25B . . 108.3 ?
    H25A C25 H25B . . 107.4 ?
    C28 C26 C27 . . 110.6(2) ?
    C28 C26 C25 . . 112.1(2) ?
    C27 C26 C25 . . 109.4(2) ?
    C28 C26 H26A . . 108.2 ?
    C27 C26 H26A . . 108.2 ?
    C25 C26 H26A . . 108.2 ?
    C26 C27 H27A . . 109.5 ?
    C26 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C26 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C26 C28 H28A . . 109.5 ?
    C26 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C26 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 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
    C12 C1 C2 C3 . . . . 174.5(2) ?
    C7 C1 C2 C3 . . . . 46.9(3) ?
    C1 C2 C3 C5 . . . . -14.8(4) ?
    C1 C2 C3 C4 . . . . 166.6(2) ?
    C4 C3 C5 C6 . . . . 177.6(3) ?
    C2 C3 C5 C6 . . . . -1.0(4) ?
    C3 C5 C6 C7 . . . . -15.5(4) ?
    C5 C6 C7 C8 . . . . -74.9(3) ?
    C5 C6 C7 C1 . . . . 44.6(3) ?
    C5 C6 C7 C9 . . . . 162.8(2) ?
    C12 C1 C7 C8 . . . . -70.1(3) ?
    C2 C1 C7 C8 . . . . 56.4(3) ?
    C12 C1 C7 C6 . . . . 172.3(2) ?
    C2 C1 C7 C6 . . . . -61.1(3) ?
    C12 C1 C7 C9 . . . . 53.3(3) ?
    C2 C1 C7 C9 . . . . 179.8(2) ?
    C8 C7 C9 C10 . . . . 70.0(3) ?
    C6 C7 C9 C10 . . . . -169.8(2) ?
    C1 C7 C9 C10 . . . . -52.9(3) ?
    C8 C7 C9 C13 . . . . -58.6(3) ?
    C6 C7 C9 C13 . . . . 61.6(3) ?
    C1 C7 C9 C13 . . . . 178.5(2) ?
    C13 C9 C10 C17 . . . . -52.1(3) ?
    C7 C9 C10 C17 . . . . 177.8(2) ?
    C13 C9 C10 C11 . . . . -175.1(2) ?
    C7 C9 C10 C11 . . . . 54.7(3) ?
    C17 C10 C11 C12 . . . . -176.7(2) ?
    C9 C10 C11 C12 . . . . -55.2(3) ?
    C2 C1 C12 C11 . . . . 177.1(2) ?
    C7 C1 C12 C11 . . . . -55.8(3) ?
    C10 C11 C12 C1 . . . . 56.1(3) ?
    C10 C9 C13 C14 . . . . 53.5(3) ?
    C7 C9 C13 C14 . . . . -176.7(2) ?
    C9 C13 C14 C15 . . . . -56.0(3) ?
    C13 C14 C15 C17 . . . . 55.7(3) ?
    C13 C14 C15 C16 . . . . -66.6(3) ?
    C13 C14 C15 C20 . . . . 167.2(2) ?
    C11 C10 C17 C18 . . . . -55.8(3) ?
    C9 C10 C17 C18 . . . . -178.2(2) ?
    C11 C10 C17 C15 . . . . 179.9(2) ?
    C9 C10 C17 C15 . . . . 57.4(3) ?
    C14 C15 C17 C10 . . . . -58.9(3) ?
    C16 C15 C17 C10 . . . . 62.4(3) ?
    C20 C15 C17 C10 . . . . 178.9(2) ?
    C14 C15 C17 C18 . . . . 169.6(2) ?
    C16 C15 C17 C18 . . . . -69.1(3) ?
    C20 C15 C17 C18 . . . . 47.4(2) ?
    C10 C17 C18 C19 . . . . -166.5(2) ?
    C15 C17 C18 C19 . . . . -37.0(2) ?
    C17 C18 C19 C20 . . . . 12.3(3) ?
    C18 C19 C20 C21 . . . . 145.7(2) ?
    C18 C19 C20 C15 . . . . 16.4(3) ?
    C14 C15 C20 C21 . . . . 81.9(3) ?
    C17 C15 C20 C21 . . . . -162.6(2) ?
    C16 C15 C20 C21 . . . . -44.5(3) ?
    C14 C15 C20 C19 . . . . -153.6(2) ?
    C17 C15 C20 C19 . . . . -38.1(2) ?
    C16 C15 C20 C19 . . . . 79.9(3) ?
    C19 C20 C21 C22 . . . . -175.7(2) ?
    C15 C20 C21 C22 . . . . -55.2(3) ?
    C19 C20 C21 C23 . . . . 59.6(3) ?
    C15 C20 C21 C23 . . . . -180.0(2) ?
    C22 C21 C23 C24 . . . . 76.7(3) ?
    C20 C21 C23 C24 . . . . -156.7(2) ?
    C21 C23 C24 C25 . . . . -179.9(2) ?
    C23 C24 C25 C26 . . . . -172.8(3) ?
    C24 C25 C26 C28 . . . . -62.8(3) ?
    C24 C25 C26 C27 . . . . 174.2(2) ?
