##############################################################################
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-01-17
_journal_date_accepted     2012-01-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o520
_journal_page_last     o521
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812002565
_journal_coeditor_code     IS5054
_publ_contact_author_name     'Prof. 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 6533652'
_publ_section_title
;
ent-(15S)-Pimar-8(14)-ene-15,16-diol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Suchada Chantrapromma'
;
      Additional correspondence author, e-mail: suchada.c@psu.ac.th.
      Thomson Reuters ResearcherID: A-5085-2009.
;
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Charoen Pakhathirathien' ?
;     Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Chatchanok Karalai' ?
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Kan Chantrapromma' ?
;     Research Unit of Natural Products Utilization
      Walailak University
      Thasala
      Nakhon Si Thammarat 80160
      Thailand
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(S)-1-[(2S,4aR,8aR)-2,4b,8,8-tetramethyl-
2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl]ethane-1,2-diol
;
_chemical_name_common
;
ent-15S-prima-8(14)-ene-15,16-diol
Ceriotagalsin L
;
_chemical_formula_moiety     'C20 H34 O2'
_chemical_formula_sum     'C20 H34 O2'
_chemical_formula_iupac     'C20 H34 O2'
_chemical_formula_weight     306.47
_chemical_melting_point     ?
_chemical_melting_point_gt     377
_chemical_melting_point_lt     378
_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     11.5129(2)
_cell_length_b     7.09340(10)
_cell_length_c     22.3946(4)
_cell_angle_alpha     90.00
_cell_angle_beta     96.7500(10)
_cell_angle_gamma     90.00
_cell_volume     1816.19(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5205
_cell_measurement_theta_min     1.78
_cell_measurement_theta_max     29.00
_cell_measurement_temperature     273(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.56
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.121
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.070
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9618
_exptl_absorpt_correction_T_max     0.9831
_exptl_special_details     ?
_diffrn_ambient_temperature     273(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 APEX2 CCD area-detector
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     28246
_diffrn_reflns_av_R_equivalents     0.0307
_diffrn_reflns_av_sigmaI/netI     0.0233
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     29.00
_diffrn_reflns_theta_full     29.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_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     5205
_reflns_number_gt     4504
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0491
_refine_ls_R_factor_gt     0.0414
_refine_ls_wR_factor_gt     0.1008
_refine_ls_wR_factor_ref     0.1057
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     5205
_refine_ls_number_parameters     421
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0565P)²+0.1315P] 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     0.001
_refine_diff_density_max     0.165
_refine_diff_density_min     -0.157
_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     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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 O1A 0.81903(14) 0.4262(2) 0.07420(7) 0.0536(4) Uani d . 1 1 . .
    H H1OA 0.866(2) 0.351(4) 0.0679(11) 0.058(8) Uiso d . 1 1 . .
    O O2A 0.73660(18) 0.0232(3) 0.05561(9) 0.0749(5) Uani d . 1 1 . .
    H H1OB 0.799(3) 0.052(6) 0.0421(14) 0.098(11) Uiso d . 1 1 . .
    C C1A 0.72183(17) 0.3489(3) 0.35428(8) 0.0472(4) Uani d . 1 1 . .
    H H1AA 0.6477 0.4036 0.3617 0.057 Uiso calc R 1 1 . .
    H H1AB 0.7059 0.2259 0.3362 0.057 Uiso calc R 1 1 . .
    C C2A 0.7980(2) 0.3239(3) 0.41415(10) 0.0562(5) Uani d . 1 1 . .
    H H2AA 0.7571 0.2468 0.4407 0.067 Uiso calc R 1 1 . .
    H H2AB 0.8698 0.2595 0.4076 0.067 Uiso calc R 1 1 . .
    C C3A 0.82712(19) 0.5136(4) 0.44337(9) 0.0527(5) Uani d . 1 1 . .
    H H3AA 0.8753 0.4938 0.4814 0.063 Uiso calc R 1 1 . .
    H H3AB 0.7552 0.5737 0.4519 0.063 Uiso calc R 1 1 . .
    C C4A 0.89149(16) 0.6458(3) 0.40430(9) 0.0447(4) Uani d . 1 1 . .
    C C5A 0.81852(14) 0.6626(3) 0.34104(8) 0.0361(4) Uani d . 1 1 . .
    H H5AA 0.7460 0.7256 0.3488 0.043 Uiso calc R 1 1 . .
    C C6A 0.87199(17) 0.7930(3) 0.29730(9) 0.0455(4) Uani d . 1 1 . .
    H H6AA 0.8976 0.9089 0.3177 0.055 Uiso calc R 1 1 . .
    H H6AB 0.9398 0.7327 0.2837 0.055 Uiso calc R 1 1 . .
    C C7A 0.78277(18) 0.8383(3) 0.24320(9) 0.0465(4) Uani d . 1 1 . .
    H H7AA 0.7224 0.9188 0.2562 0.056 Uiso calc R 1 1 . .
    H H7AB 0.8214 0.9080 0.2139 0.056 Uiso calc R 1 1 . .
    C C8A 0.72631(15) 0.6656(3) 0.21346(8) 0.0390(4) Uani d . 1 1 . .
    C C9A 0.68153(13) 0.5262(3) 0.25669(8) 0.0364(4) Uani d . 1 1 . .
    H H9AA 0.6197 0.5917 0.2751 0.044 Uiso calc R 1 1 . .
    C C10A 0.77758(14) 0.4746(3) 0.30945(8) 0.0352(4) Uani d . 1 1 . .
    C C11A 0.71179(15) 0.6440(3) 0.15422(9) 0.0427(4) Uani d . 1 1 . .
    H H11A 0.7472 0.7324 0.1316 0.051 Uiso calc R 1 1 . .
    C C12A 0.64268(14) 0.4882(3) 0.12021(8) 0.0431(4) Uani d . 1 1 . .
    C C13A 0.56019(15) 0.4038(4) 0.16287(9) 0.0495(5) Uani d . 1 1 . .
    H H13A 0.4986 0.4938 0.1678 0.059 Uiso calc R 1 1 . .
    H H13B 0.5238 0.2910 0.1447 0.059 Uiso calc R 1 1 . .
    C C14A 0.62334(16) 0.3544(3) 0.22433(8) 0.0455(4) Uani d . 1 1 . .
    H H14A 0.6825 0.2600 0.2196 0.055 Uiso calc R 1 1 . .
    H H14B 0.5678 0.3003 0.2489 0.055 Uiso calc R 1 1 . .
    C C15A 0.72612(15) 0.3356(3) 0.10103(8) 0.0409(4) Uani d . 1 1 . .
    H H15A 0.7609 0.2706 0.1374 0.049 Uiso calc R 1 1 . .
    C C16A 0.6687(2) 0.1888(4) 0.05847(12) 0.0647(7) Uani d . 1 1 . .
    H H16A 0.5937 0.1551 0.0711 0.078 Uiso calc R 1 1 . .
    H H16B 0.6541 0.2430 0.0185 0.078 Uiso calc R 1 1 . .
    C C17A 0.5698(2) 0.5755(4) 0.06543(11) 0.0661(7) Uani d . 1 1 . .
    H H17A 0.5255 0.6797 0.0781 0.099 Uiso calc R 1 1 . .
    H H17B 0.5175 0.4823 0.0464 0.099 Uiso calc R 1 1 . .
    H H17C 0.6209 0.6192 0.0374 0.099 Uiso calc R 1 1 . .
    C C18A 0.8966(2) 0.8406(4) 0.43453(11) 0.0639(6) Uani d . 1 1 . .
    H H18A 0.9267 0.8278 0.4762 0.096 Uiso calc R 1 1 . .
    H H18B 0.8194 0.8936 0.4314 0.096 Uiso calc R 1 1 . .
    H H18C 0.9468 0.9220 0.4149 0.096 Uiso calc R 1 1 . .
    C C19A 1.01865(16) 0.5797(4) 0.40298(11) 0.0591(6) Uani d . 1 1 . .
    H H19A 1.0628 0.6036 0.4413 0.089 Uiso calc R 1 1 . .
    H H19B 1.0529 0.6472 0.3723 0.089 Uiso calc R 1 1 . .
    H H19C 1.0195 0.4470 0.3945 0.089 Uiso calc R 1 1 . .
    C C20A 0.87771(16) 0.3679(3) 0.28404(9) 0.0456(4) Uani d . 1 1 . .
    H H20A 0.8525 0.2422 0.2731 0.068 Uiso calc R 1 1 . .
    H H20B 0.9444 0.3623 0.3140 0.068 Uiso calc R 1 1 . .
    H H20C 0.8985 0.4326 0.2492 0.068 Uiso calc R 1 1 . .
    O O1B -0.02356(11) 0.1434(3) 0.04385(6) 0.0461(3) Uani d . 1 1 . .
    H H1OC -0.008(2) 0.172(4) 0.0131(10) 0.048(6) Uiso d . 1 1 . .
    O O2B -0.03925(16) -0.2575(3) 0.06519(7) 0.0609(5) Uani d . 1 1 . .
    H H1OD -0.082(2) -0.320(5) 0.0804(12) 0.068(9) Uiso d . 1 1 . .
    C C1B 0.27744(18) 0.3103(3) 0.34629(8) 0.0460(4) Uani d . 1 1 . .
    H H1BA 0.3426 0.3906 0.3392 0.055 Uiso calc R 1 1 . .
    H H1BB 0.2060 0.3815 0.3358 0.055 Uiso calc R 1 1 . .
    C C2B 0.2877(2) 0.2604(4) 0.41295(9) 0.0555(5) Uani d . 1 1 . .
    H H2BA 0.2885 0.3750 0.4366 0.067 Uiso calc R 1 1 . .
    H H2BB 0.2206 0.1860 0.4210 0.067 Uiso calc R 1 1 . .
    C C3B 0.39891(19) 0.1496(4) 0.43098(9) 0.0512(5) Uani d . 1 1 . .
    H H3BA 0.4028 0.1179 0.4733 0.061 Uiso calc R 1 1 . .
    H H3BB 0.4655 0.2294 0.4259 0.061 Uiso calc R 1 1 . .
    C C4B 0.40886(15) -0.0322(3) 0.39499(8) 0.0413(4) Uani d . 1 1 . .
    C C5B 0.38623(13) 0.0151(3) 0.32653(7) 0.0346(4) Uani d . 1 1 . .
    H H5BA 0.4526 0.0944 0.3190 0.041 Uiso calc R 1 1 . .
    C C6B 0.39381(17) -0.1555(3) 0.28551(8) 0.0463(4) Uani d . 1 1 . .
    H H6BA 0.3238 -0.2318 0.2854 0.056 Uiso calc R 1 1 . .
    H H6BB 0.4606 -0.2324 0.3005 0.056 Uiso calc R 1 1 . .
    C C7B 0.40626(16) -0.0902(4) 0.22146(8) 0.0497(5) Uani d . 1 1 . .
    H H7BA 0.4814 -0.0287 0.2209 0.060 Uiso calc R 1 1 . .
    H H7BB 0.4044 -0.1992 0.1952 0.060 Uiso calc R 1 1 . .
    C C8B 0.31058(14) 0.0438(3) 0.19795(8) 0.0387(4) Uani d . 1 1 . .
    C C9B 0.28974(14) 0.2057(3) 0.23949(7) 0.0352(4) Uani d . 1 1 . .
    H H9BA 0.3623 0.2793 0.2433 0.042 Uiso calc R 1 1 . .
    C C10B 0.27621(13) 0.1366(3) 0.30492(7) 0.0325(3) Uani d . 1 1 . .
    C C11B 0.25326(14) 0.0238(3) 0.14331(8) 0.0425(4) Uani d . 1 1 . .
    H H11B 0.2741 -0.0777 0.1205 0.051 Uiso calc R 1 1 . .
    C C12B 0.15718(15) 0.1514(3) 0.11489(7) 0.0399(4) Uani d . 1 1 . .
    C C13B 0.10155(15) 0.2509(3) 0.16542(8) 0.0441(4) Uani d . 1 1 . .
    H H13C 0.0479 0.3470 0.1481 0.053 Uiso calc R 1 1 . .
    H H13D 0.0570 0.1600 0.1857 0.053 Uiso calc R 1 1 . .
    C C14B 0.19380(16) 0.3423(3) 0.21132(8) 0.0447(4) Uani d . 1 1 . .
    H H14C 0.1548 0.3970 0.2433 0.054 Uiso calc R 1 1 . .
    H H14D 0.2309 0.4442 0.1918 0.054 Uiso calc R 1 1 . .
    C C15B 0.06752(14) 0.0294(3) 0.07492(7) 0.0395(4) Uani d . 1 1 . .
    H H15B 0.1092 -0.0318 0.0445 0.047 Uiso calc R 1 1 . .
    C C16B 0.00925(17) -0.1240(3) 0.10784(8) 0.0461(5) Uani d . 1 1 . .
    H H16C 0.0662 -0.1844 0.1371 0.055 Uiso calc R 1 1 . .
    H H16D -0.0517 -0.0702 0.1290 0.055 Uiso calc R 1 1 . .
    C C17B 0.20945(19) 0.2949(4) 0.07418(9) 0.0586(6) Uani d . 1 1 . .
    H H17D 0.2701 0.3653 0.0974 0.088 Uiso calc R 1 1 . .
    H H17E 0.1493 0.3795 0.0573 0.088 Uiso calc R 1 1 . .
    H H17F 0.2417 0.2297 0.0424 0.088 Uiso calc R 1 1 . .
    C C18B 0.53511(17) -0.1040(4) 0.40919(9) 0.0621(7) Uani d . 1 1 . .
    H H18D 0.5566 -0.1041 0.4519 0.093 Uiso calc R 1 1 . .
    H H18E 0.5870 -0.0228 0.3905 0.093 Uiso calc R 1 1 . .
    H H18F 0.5405 -0.2298 0.3940 0.093 Uiso calc R 1 1 . .
    C C19B 0.3277(2) -0.1827(4) 0.41623(10) 0.0555(5) Uani d . 1 1 . .
    H H19D 0.3560 -0.2201 0.4565 0.083 Uiso calc R 1 1 . .
    H H19E 0.3261 -0.2901 0.3901 0.083 Uiso calc R 1 1 . .
    H H19F 0.2502 -0.1321 0.4154 0.083 Uiso calc R 1 1 . .
    C C20B 0.15986(14) 0.0313(3) 0.30453(9) 0.0454(4) Uani d . 1 1 . .
    H H20D 0.0965 0.1142 0.2906 0.068 Uiso calc R 1 1 . .
    H H20E 0.1511 -0.0107 0.3445 0.068 Uiso calc R 1 1 . .
    H H20F 0.1591 -0.0756 0.2782 0.068 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
    O1A C15A . 1.439(2) ?
    O1A H1OA . 0.79(3) ?
    O2A C16A . 1.417(3) ?
    O2A H1OB . 0.84(3) ?
    C1A C2A . 1.524(3) ?
    C1A C10A . 1.538(2) ?
    C1A H1AA . 0.9700 ?
    C1A H1AB . 0.9700 ?
    C2A C3A . 1.516(3) ?
    C2A H2AA . 0.9700 ?
    C2A H2AB . 0.9700 ?
    C3A C4A . 1.532(3) ?
    C3A H3AA . 0.9700 ?
    C3A H3AB . 0.9700 ?
    C4A C18A . 1.537(3) ?
    C4A C19A . 1.541(3) ?
    C4A C5A . 1.564(3) ?
    C5A C6A . 1.528(3) ?
    C5A C10A . 1.556(2) ?
    C5A H5AA . 0.9800 ?
    C6A C7A . 1.528(3) ?
    C6A H6AA . 0.9700 ?
    C6A H6AB . 0.9700 ?
    C7A C8A . 1.505(3) ?
    C7A H7AA . 0.9700 ?
    C7A H7AB . 0.9700 ?
    C8A C11A . 1.326(3) ?
    C8A C9A . 1.516(2) ?
    C9A C14A . 1.531(3) ?
    C9A C10A . 1.564(2) ?
    C9A H9AA . 0.9800 ?
    C10A C20A . 1.543(2) ?
    C11A C12A . 1.514(3) ?
    C11A H11A . 0.9300 ?
    C12A C17A . 1.533(3) ?
    C12A C15A . 1.542(3) ?
    C12A C13A . 1.545(3) ?
    C13A C14A . 1.520(3) ?
    C13A H13A . 0.9700 ?
    C13A H13B . 0.9700 ?
    C14A H14A . 0.9700 ?
    C14A H14B . 0.9700 ?
    C15A C16A . 1.511(3) ?
    C15A H15A . 0.9800 ?
    C16A H16A . 0.9700 ?
    C16A H16B . 0.9700 ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C18A H18A . 0.9600 ?
    C18A H18B . 0.9600 ?
    C18A H18C . 0.9600 ?
    C19A H19A . 0.9600 ?
    C19A H19B . 0.9600 ?
    C19A H19C . 0.9600 ?
    C20A H20A . 0.9600 ?
    C20A H20B . 0.9600 ?
    C20A H20C . 0.9600 ?
    O1B C15B . 1.437(2) ?
    O1B H1OC . 0.76(2) ?
    O2B C16B . 1.412(3) ?
    O2B H1OD . 0.77(3) ?
    C1B C2B . 1.525(3) ?
    C1B C10B . 1.541(3) ?
    C1B H1BA . 0.9700 ?
    C1B H1BB . 0.9700 ?
    C2B C3B . 1.516(3) ?
    C2B H2BA . 0.9700 ?
    C2B H2BB . 0.9700 ?
    C3B C4B . 1.533(3) ?
    C3B H3BA . 0.9700 ?
    C3B H3BB . 0.9700 ?
    C4B C19B . 1.530(3) ?
    C4B C18B . 1.538(3) ?
    C4B C5B . 1.561(2) ?
    C5B C6B . 1.528(3) ?
    C5B C10B . 1.561(2) ?
    C5B H5BA . 0.9800 ?
    C6B C7B . 1.530(3) ?
    C6B H6BA . 0.9700 ?
    C6B H6BB . 0.9700 ?
    C7B C8B . 1.503(3) ?
    C7B H7BA . 0.9700 ?
    C7B H7BB . 0.9700 ?
    C8B C11B . 1.328(2) ?
    C8B C9B . 1.515(3) ?
    C9B C14B . 1.547(3) ?
    C9B C10B . 1.570(2) ?
    C9B H9BA . 0.9800 ?
    C10B C20B . 1.533(2) ?
    C11B C12B . 1.510(3) ?
    C11B H11B . 0.9300 ?
    C12B C17B . 1.536(3) ?
    C12B C13B . 1.536(2) ?
    C12B C15B . 1.549(3) ?
    C13B C14B . 1.532(3) ?
    C13B H13C . 0.9700 ?
    C13B H13D . 0.9700 ?
    C14B H14C . 0.9700 ?
    C14B H14D . 0.9700 ?
    C15B C16B . 1.514(3) ?
    C15B H15B . 0.9800 ?
    C16B H16C . 0.9700 ?
    C16B H16D . 0.9700 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    C18B H18D . 0.9600 ?
    C18B H18E . 0.9600 ?
    C18B H18F . 0.9600 ?
    C19B H19D . 0.9600 ?
    C19B H19E . 0.9600 ?
    C19B H19F . 0.9600 ?
    C20B H20D . 0.9600 ?
    C20B H20E . 0.9600 ?
    C20B H20F . 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
    C15A O1A H1OA . . 109(2) ?
    C16A O2A H1OB . . 108(3) ?
    C2A C1A C10A . . 113.59(16) ?
    C2A C1A H1AA . . 108.8 ?
    C10A C1A H1AA . . 108.8 ?
    C2A C1A H1AB . . 108.8 ?
    C10A C1A H1AB . . 108.8 ?
    H1AA C1A H1AB . . 107.7 ?
    C3A C2A C1A . . 110.60(19) ?
    C3A C2A H2AA . . 109.5 ?
    C1A C2A H2AA . . 109.5 ?
    C3A C2A H2AB . . 109.5 ?
    C1A C2A H2AB . . 109.5 ?
    H2AA C2A H2AB . . 108.1 ?
    C2A C3A C4A . . 113.19(17) ?
    C2A C3A H3AA . . 108.9 ?
    C4A C3A H3AA . . 108.9 ?
    C2A C3A H3AB . . 108.9 ?
    C4A C3A H3AB . . 108.9 ?
    H3AA C3A H3AB . . 107.8 ?
    C3A C4A C18A . . 107.15(17) ?
    C3A C4A C19A . . 110.44(18) ?
    C18A C4A C19A . . 107.15(19) ?
    C3A C4A C5A . . 108.64(15) ?
    C18A C4A C5A . . 108.61(17) ?
    C19A C4A C5A . . 114.58(16) ?
    C6A C5A C10A . . 110.52(14) ?
    C6A C5A C4A . . 114.37(15) ?
    C10A C5A C4A . . 116.62(16) ?
    C6A C5A H5AA . . 104.6 ?
    C10A C5A H5AA . . 104.6 ?
    C4A C5A H5AA . . 104.6 ?
    C7A C6A C5A . . 110.60(15) ?
    C7A C6A H6AA . . 109.5 ?
    C5A C6A H6AA . . 109.5 ?
    C7A C6A H6AB . . 109.5 ?
    C5A C6A H6AB . . 109.5 ?
    H6AA C6A H6AB . . 108.1 ?
    C8A C7A C6A . . 113.24(17) ?
    C8A C7A H7AA . . 108.9 ?
    C6A C7A H7AA . . 108.9 ?
    C8A C7A H7AB . . 108.9 ?
    C6A C7A H7AB . . 108.9 ?
    H7AA C7A H7AB . . 107.7 ?
    C11A C8A C7A . . 122.23(18) ?
    C11A C8A C9A . . 123.47(18) ?
    C7A C8A C9A . . 114.20(15) ?
    C8A C9A C14A . . 112.30(14) ?
    C8A C9A C10A . . 111.82(13) ?
    C14A C9A C10A . . 113.74(16) ?
    C8A C9A H9AA . . 106.1 ?
    C14A C9A H9AA . . 106.1 ?
    C10A C9A H9AA . . 106.1 ?
    C1A C10A C20A . . 110.07(16) ?
    C1A C10A C5A . . 109.12(14) ?
    C20A C10A C5A . . 112.87(14) ?
    C1A C10A C9A . . 108.45(13) ?
    C20A C10A C9A . . 109.19(14) ?
    C5A C10A C9A . . 107.01(14) ?
    C8A C11A C12A . . 125.74(18) ?
    C8A C11A H11A . . 117.1 ?
    C12A C11A H11A . . 117.1 ?
    C11A C12A C17A . . 108.28(19) ?
    C11A C12A C15A . . 110.18(14) ?
    C17A C12A C15A . . 111.15(17) ?
    C11A C12A C13A . . 107.27(15) ?
    C17A C12A C13A . . 109.46(16) ?
    C15A C12A C13A . . 110.40(17) ?
    C14A C13A C12A . . 112.70(14) ?
    C14A C13A H13A . . 109.1 ?
    C12A C13A H13A . . 109.1 ?
    C14A C13A H13B . . 109.1 ?
    C12A C13A H13B . . 109.1 ?
    H13A C13A H13B . . 107.8 ?
    C13A C14A C9A . . 112.39(18) ?
    C13A C14A H14A . . 109.1 ?
    C9A C14A H14A . . 109.1 ?
    C13A C14A H14B . . 109.1 ?
    C9A C14A H14B . . 109.1 ?
    H14A C14A H14B . . 107.9 ?
    O1A C15A C16A . . 109.64(16) ?
    O1A C15A C12A . . 108.71(17) ?
    C16A C15A C12A . . 114.79(16) ?
    O1A C15A H15A . . 107.8 ?
    C16A C15A H15A . . 107.8 ?
    C12A C15A H15A . . 107.8 ?
    O2A C16A C15A . . 113.41(19) ?
    O2A C16A H16A . . 108.9 ?
    C15A C16A H16A . . 108.9 ?
    O2A C16A H16B . . 108.9 ?
    C15A C16A H16B . . 108.9 ?
    H16A C16A H16B . . 107.7 ?
    C12A C17A H17A . . 109.5 ?
    C12A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C12A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C4A C18A H18A . . 109.5 ?
    C4A C18A H18B . . 109.5 ?
    H18A C18A H18B . . 109.5 ?
    C4A C18A H18C . . 109.5 ?
    H18A C18A H18C . . 109.5 ?
    H18B C18A H18C . . 109.5 ?
    C4A C19A H19A . . 109.5 ?
    C4A C19A H19B . . 109.5 ?
    H19A C19A H19B . . 109.5 ?
    C4A C19A H19C . . 109.5 ?
    H19A C19A H19C . . 109.5 ?
    H19B C19A H19C . . 109.5 ?
    C10A C20A H20A . . 109.5 ?
    C10A C20A H20B . . 109.5 ?
    H20A C20A H20B . . 109.5 ?
    C10A C20A H20C . . 109.5 ?
    H20A C20A H20C . . 109.5 ?
    H20B C20A H20C . . 109.5 ?
    C15B O1B H1OC . . 110.8(19) ?
    C16B O2B H1OD . . 108(2) ?
    C2B C1B C10B . . 113.41(17) ?
    C2B C1B H1BA . . 108.9 ?
    C10B C1B H1BA . . 108.9 ?
    C2B C1B H1BB . . 108.9 ?
    C10B C1B H1BB . . 108.9 ?
    H1BA C1B H1BB . . 107.7 ?
    C3B C2B C1B . . 110.31(17) ?
    C3B C2B H2BA . . 109.6 ?
    C1B C2B H2BA . . 109.6 ?
    C3B C2B H2BB . . 109.6 ?
    C1B C2B H2BB . . 109.6 ?
    H2BA C2B H2BB . . 108.1 ?
    C2B C3B C4B . . 114.15(17) ?
    C2B C3B H3BA . . 108.7 ?
    C4B C3B H3BA . . 108.7 ?
    C2B C3B H3BB . . 108.7 ?
    C4B C3B H3BB . . 108.7 ?
    H3BA C3B H3BB . . 107.6 ?
    C19B C4B C3B . . 109.71(16) ?
    C19B C4B C18B . . 107.55(19) ?
    C3B C4B C18B . . 107.29(18) ?
    C19B C4B C5B . . 114.69(16) ?
    C3B C4B C5B . . 108.75(17) ?
    C18B C4B C5B . . 108.59(14) ?
    C6B C5B C4B . . 113.92(16) ?
    C6B C5B C10B . . 110.64(13) ?
    C4B C5B C10B . . 117.31(13) ?
    C6B C5B H5BA . . 104.5 ?
    C4B C5B H5BA . . 104.5 ?
    C10B C5B H5BA . . 104.5 ?
    C5B C6B C7B . . 110.01(18) ?
    C5B C6B H6BA . . 109.7 ?
    C7B C6B H6BA . . 109.7 ?
    C5B C6B H6BB . . 109.7 ?
    C7B C6B H6BB . . 109.7 ?
    H6BA C6B H6BB . . 108.2 ?
    C8B C7B C6B . . 111.98(14) ?
    C8B C7B H7BA . . 109.2 ?
    C6B C7B H7BA . . 109.2 ?
    C8B C7B H7BB . . 109.2 ?
    C6B C7B H7BB . . 109.2 ?
    H7BA C7B H7BB . . 107.9 ?
    C11B C8B C7B . . 121.33(18) ?
    C11B C8B C9B . . 123.32(17) ?
    C7B C8B C9B . . 115.28(15) ?
    C8B C9B C14B . . 112.43(14) ?
    C8B C9B C10B . . 112.11(15) ?
    C14B C9B C10B . . 115.59(13) ?
    C8B C9B H9BA . . 105.2 ?
    C14B C9B H9BA . . 105.2 ?
    C10B C9B H9BA . . 105.2 ?
    C20B C10B C1B . . 109.83(14) ?
    C20B C10B C5B . . 114.16(15) ?
    C1B C10B C5B . . 107.78(14) ?
    C20B C10B C9B . . 109.23(13) ?
    C1B C10B C9B . . 108.46(15) ?
    C5B C10B C9B . . 107.21(12) ?
    C8B C11B C12B . . 125.76(18) ?
    C8B C11B H11B . . 117.1 ?
    C12B C11B H11B . . 117.1 ?
    C11B C12B C17B . . 109.18(15) ?
    C11B C12B C13B . . 108.25(14) ?
    C17B C12B C13B . . 111.03(19) ?
    C11B C12B C15B . . 108.32(17) ?
    C17B C12B C15B . . 107.96(14) ?
    C13B C12B C15B . . 112.04(14) ?
    C14B C13B C12B . . 111.87(14) ?
    C14B C13B H13C . . 109.2 ?
    C12B C13B H13C . . 109.2 ?
    C14B C13B H13D . . 109.2 ?
    C12B C13B H13D . . 109.2 ?
    H13C C13B H13D . . 107.9 ?
    C13B C14B C9B . . 114.45(17) ?
    C13B C14B H14C . . 108.6 ?
    C9B C14B H14C . . 108.6 ?
    C13B C14B H14D . . 108.6 ?
    C9B C14B H14D . . 108.6 ?
    H14C C14B H14D . . 107.6 ?
    O1B C15B C16B . . 107.45(14) ?
    O1B C15B C12B . . 111.38(17) ?
    C16B C15B C12B . . 115.05(13) ?
    O1B C15B H15B . . 107.6 ?
    C16B C15B H15B . . 107.6 ?
    C12B C15B H15B . . 107.6 ?
    O2B C16B C15B . . 108.37(14) ?
    O2B C16B H16C . . 110.0 ?
    C15B C16B H16C . . 110.0 ?
    O2B C16B H16D . . 110.0 ?
    C15B C16B H16D . . 110.0 ?
    H16C C16B H16D . . 108.4 ?
    C12B C17B H17D . . 109.5 ?
    C12B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C12B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    C4B C18B H18D . . 109.5 ?
    C4B C18B H18E . . 109.5 ?
    H18D C18B H18E . . 109.5 ?
    C4B C18B H18F . . 109.5 ?
    H18D C18B H18F . . 109.5 ?
    H18E C18B H18F . . 109.5 ?
    C4B C19B H19D . . 109.5 ?
    C4B C19B H19E . . 109.5 ?
    H19D C19B H19E . . 109.5 ?
    C4B C19B H19F . . 109.5 ?
    H19D C19B H19F . . 109.5 ?
    H19E C19B H19F . . 109.5 ?
    C10B C20B H20D . . 109.5 ?
    C10B C20B H20E . . 109.5 ?
    H20D C20B H20E . . 109.5 ?
    C10B C20B H20F . . 109.5 ?
    H20D C20B H20F . . 109.5 ?
    H20E C20B H20F . . 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
    C10A C1A C2A C3A . . . . 57.5(2) ?
    C1A C2A C3A C4A . . . . -58.9(2) ?
    C2A C3A C4A C18A . . . . 170.75(19) ?
    C2A C3A C4A C19A . . . . -72.9(2) ?
    C2A C3A C4A C5A . . . . 53.6(2) ?
    C3A C4A C5A C6A . . . . 179.29(16) ?
    C18A C4A C5A C6A . . . . 63.1(2) ?
    C19A C4A C5A C6A . . . . -56.7(2) ?
    C3A C4A C5A C10A . . . . -49.6(2) ?
    C18A C4A C5A C10A . . . . -165.82(16) ?
    C19A C4A C5A C10A . . . . 74.4(2) ?
    C10A C5A C6A C7A . . . . 59.7(2) ?
    C4A C5A C6A C7A . . . . -166.33(16) ?
    C5A C6A C7A C8A . . . . -51.7(2) ?
    C6A C7A C8A C11A . . . . -135.30(19) ?
    C6A C7A C8A C9A . . . . 48.2(2) ?
    C11A C8A C9A C14A . . . . 2.8(2) ?
    C7A C8A C9A C14A . . . . 179.18(15) ?
    C11A C8A C9A C10A . . . . 132.04(19) ?
    C7A C8A C9A C10A . . . . -51.6(2) ?
    C2A C1A C10A C20A . . . . 73.3(2) ?
    C2A C1A C10A C5A . . . . -51.1(2) ?
    C2A C1A C10A C9A . . . . -167.33(18) ?
    C6A C5A C10A C1A . . . . -178.74(15) ?
    C4A C5A C10A C1A . . . . 48.38(19) ?
    C6A C5A C10A C20A . . . . 58.6(2) ?
    C4A C5A C10A C20A . . . . -74.33(19) ?
    C6A C5A C10A C9A . . . . -61.59(17) ?
    C4A C5A C10A C9A . . . . 165.53(13) ?
    C8A C9A C10A C1A . . . . 174.49(15) ?
    C14A C9A C10A C1A . . . . -57.00(18) ?
    C8A C9A C10A C20A . . . . -65.57(19) ?
    C14A C9A C10A C20A . . . . 62.94(18) ?
    C8A C9A C10A C5A . . . . 56.90(17) ?
    C14A C9A C10A C5A . . . . -174.59(13) ?
    C7A C8A C11A C12A . . . . -171.68(17) ?
    C9A C8A C11A C12A . . . . 4.4(3) ?
    C8A C11A C12A C17A . . . . 137.0(2) ?
    C8A C11A C12A C15A . . . . -101.3(2) ?
    C8A C11A C12A C13A . . . . 19.0(3) ?
    C11A C12A C13A C14A . . . . -49.8(2) ?
    C17A C12A C13A C14A . . . . -167.1(2) ?
    C15A C12A C13A C14A . . . . 70.3(2) ?
    C12A C13A C14A C9A . . . . 59.8(2) ?
    C8A C9A C14A C13A . . . . -33.8(2) ?
    C10A C9A C14A C13A . . . . -162.06(14) ?
    C11A C12A C15A O1A . . . . -47.6(2) ?
    C17A C12A C15A O1A . . . . 72.4(2) ?
    C13A C12A C15A O1A . . . . -165.91(15) ?
    C11A C12A C15A C16A . . . . -170.79(18) ?
    C17A C12A C15A C16A . . . . -50.8(3) ?
    C13A C12A C15A C16A . . . . 70.9(2) ?
    O1A C15A C16A O2A . . . . 75.0(3) ?
    C12A C15A C16A O2A . . . . -162.28(18) ?
    C10B C1B C2B C3B . . . . 58.9(2) ?
    C1B C2B C3B C4B . . . . -57.5(3) ?
    C2B C3B C4B C19B . . . . -75.1(2) ?
    C2B C3B C4B C18B . . . . 168.35(18) ?
    C2B C3B C4B C5B . . . . 51.1(2) ?
    C19B C4B C5B C6B . . . . -56.8(2) ?
    C3B C4B C5B C6B . . . . 179.95(15) ?
    C18B C4B C5B C6B . . . . 63.5(2) ?
    C19B C4B C5B C10B . . . . 74.7(2) ?
    C3B C4B C5B C10B . . . . -48.5(2) ?
    C18B C4B C5B C10B . . . . -164.97(18) ?
    C4B C5B C6B C7B . . . . -163.57(14) ?
    C10B C5B C6B C7B . . . . 61.74(19) ?
    C5B C6B C7B C8B . . . . -54.2(2) ?
    C6B C7B C8B C11B . . . . -133.6(2) ?
    C6B C7B C8B C9B . . . . 49.5(2) ?
    C11B C8B C9B C14B . . . . 0.7(3) ?
    C7B C8B C9B C14B . . . . 177.58(16) ?
    C11B C8B C9B C10B . . . . 132.89(18) ?
    C7B C8B C9B C10B . . . . -50.2(2) ?
    C2B C1B C10B C20B . . . . 71.4(2) ?
    C2B C1B C10B C5B . . . . -53.5(2) ?
    C2B C1B C10B C9B . . . . -169.27(16) ?
    C6B C5B C10B C20B . . . . 60.38(19) ?
    C4B C5B C10B C20B . . . . -72.6(2) ?
    C6B C5B C10B C1B . . . . -177.32(15) ?
    C4B C5B C10B C1B . . . . 49.7(2) ?
    C6B C5B C10B C9B . . . . -60.74(18) ?
    C4B C5B C10B C9B . . . . 166.26(16) ?
    C8B C9B C10B C20B . . . . -70.25(18) ?
    C14B C9B C10B C20B . . . . 60.4(2) ?
    C8B C9B C10B C1B . . . . 170.06(14) ?
    C14B C9B C10B C1B . . . . -59.31(19) ?
    C8B C9B C10B C5B . . . . 53.94(17) ?
    C14B C9B C10B C5B . . . . -175.43(15) ?
    C7B C8B C11B C12B . . . . -179.05(18) ?
    C9B C8B C11B C12B . . . . -2.3(3) ?
    C8B C11B C12B C17B . . . . 97.3(2) ?
    C8B C11B C12B C13B . . . . -23.7(3) ?
    C8B C11B C12B C15B . . . . -145.38(19) ?
    C11B C12B C13B C14B . . . . 50.4(2) ?
    C17B C12B C13B C14B . . . . -69.4(2) ?
    C15B C12B C13B C14B . . . . 169.82(17) ?
    C12B C13B C14B C9B . . . . -55.3(2) ?
    C8B C9B C14B C13B . . . . 27.9(2) ?
    C10B C9B C14B C13B . . . . -102.53(18) ?
    C11B C12B C15B O1B . . . . -176.96(13) ?
    C17B C12B C15B O1B . . . . -58.86(19) ?
    C13B C12B C15B O1B . . . . 63.70(19) ?
    C11B C12B C15B C16B . . . . 60.46(19) ?
    C17B C12B C15B C16B . . . . 178.56(18) ?
    C13B C12B C15B C16B . . . . -58.9(2) ?
    O1B C15B C16B O2B . . . . 73.8(2) ?
    C12B C15B C16B O2B . . . . -161.55(17) ?
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
    _geom_hbond_publ_flag
    O1A H1OA O1B 1_655 0.78(3) 2.06(3) 2.839(2) 174(3) y
    O2A H1OB O1B 1_655 0.84(4) 2.14(4) 2.931(2) 158(3) y
    O1B H1OC O2B 2_555 0.76(2) 1.96(2) 2.719(2) 178(3) y
    O2B H1OD O1A 1_445 0.77(3) 2.13(3) 2.795(3) 145(3) y
