##############################################################################
###                                                                        ###
###        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                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of SHELXTL-NT created .cif'
_journal_date_recd_electronic     2001-02-06
_journal_date_accepted     2001-02-14
_journal_paper_category     EO
_publ_contact_author_name     'Dr Prakas R Maulik'
_publ_contact_author_address
;
Division of Membrane Biology
Central Drug Research Institute
Chatter Manzil Palace, Post Box No. 173
Lucknow 226 001
India
;
_publ_contact_author_email     maulik_prakas@yahoo.com
_publ_contact_author_fax     '91(0522)223405'
_publ_contact_author_phone     '91(0522)212411-18'
_publ_section_title
;
Guggulsterone E, a lipid lowering agent from Commiphora mukul
;
_publ_section_title_footnote
;
CDRI communication No. 6135.
;
loop_
    _publ_author_name
    _publ_author_address
    'Sarkhel, Sanjay'
; Membrane Biology Division
  Central Drug Research Institute
  Lucknow 226 001
  India
;
    'Yadava, Umesh'
; Membrane Biology Division
  Central Drug Research Institute
  Lucknow 226 001
  India
;
    'Prakash, Prem'
; Division of Pharmaceutics
  Central Drug Research Institute
  Lucknow 226 001
  India
;
    'Jain, Girish K.'
; Division of Pharmaceutics
  Central Drug Research Institute
  Lucknow 226 001
  India
;
    'Singh, Satywan'
; Division of Pharmaceutics
  Central Drug Research Institute
  Lucknow 226 001
  India
;
    'Maulik, Prakash R.'
; Membrane Biology Division
  Central Drug Research Institute
  Lucknow 226 001
  India
;
data_I
_chemical_name_systematic
;
4,17(20)-(cis)-pregnadiene-3,16-dione
;
_chemical_name_common     'Guggulsterone E'
_chemical_formula_moiety     'C21 H28 O2'
_chemical_formula_sum     'C21 H28 O2'
_chemical_formula_weight     312.44
_chemical_melting_point        '168-170'
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     7.4634(11)
_cell_length_b     13.747(2)
_cell_length_c     17.352(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.862(12)
_cell_angle_gamma     90.00
_cell_volume     1773.8(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     50
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     12.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .35
_exptl_crystal_size_mid      .25
_exptl_crystal_size_min      .20
_exptl_crystal_density_diffrn     1.170
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu      .073
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker P4'
_diffrn_measurement_method     θ-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4388
_diffrn_reflns_av_R_equivalents      .0305
_diffrn_reflns_av_sigmaI/netI      .0604
_diffrn_reflns_theta_min     1.89
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     60
_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     3522
_reflns_number_gt     2257
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .1106
_refine_ls_R_factor_gt      .0633
_refine_ls_wR_factor_ref      .2367
_refine_ls_goodness_of_fit_ref      .921
_refine_ls_restrained_S_all      .921
_refine_ls_number_reflns     3522
_refine_ls_number_parameters     421
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.1494P)²+1.4424P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .000
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .200
_refine_diff_density_min      -.202
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     -1(4)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XSCANS (Siemens, 1996)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXTL-NT (Bruker, 1997)'
_computing_structure_refinement     'SHELXTL-NT'
_computing_molecular_graphics
; NRCVAX (Gabe et al., 1989) and ORTEP (Johnson, 1965)
;
_computing_publication_material     'SHELXTL-NT'
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
    C1  .1816(10)  .7886(6)  .7295(4)  .0565(18) Uani d . 1 . . C
    H1A  .0856  .7895  .6882  .068 Uiso calc R 1 . . H
    H1B  .1541  .7380  .7656  .068 Uiso calc R 1 . . H
    C2  .1855(11)  .8856(6)  .7708(4)  .063(2) Uani d . 1 . . C
    H2A  .1902  .9374  .7331  .075 Uiso calc R 1 . . H
    H2B  .0753  .8932  .7961  .075 Uiso calc R 1 . . H
    C3  .3441(13)  .8951(6)  .8304(4)  .071(2) Uani d . 1 . . C
    C4  .5048(11)  .8412(7)  .8150(5)  .068(2) Uani d . 1 . . C
    H4  .6047  .8473  .8505  .081 Uiso calc R 1 . . H
    C5  .5204(8)  .7839(6)  .7542(4)  .0484(16) Uani d . 1 . . C
    C6  .6961(10)  .7412(7)  .7382(5)  .072(2) Uani d . 1 . . C
    H6A  .7800  .7492  .7836  .086 Uiso calc R 1 . . H
    H6B  .7433  .7767  .6961  .086 Uiso calc R 1 . . H
    C7  .6847(9)  .6335(6)  .7172(5)  .062(2) Uani d . 1 . . C
    H7A  .6578  .5962  .7622  .074 Uiso calc R 1 . . H
    H7B  .8000  .6118  .7017  .074 Uiso calc R 1 . . H
    C8  .5387(8)  .6148(5)  .6509(4)  .0428(16) Uani d . 1 . . C
    H8  .5699  .6494  .6045  .051 Uiso calc R 1 . . H
    C9  .3583(8)  .6532(5)  .6749(4)  .0391(14) Uani d . 1 . . C
    H9  .3352  .6183  .7223  .047 Uiso calc R 1 . . H
    C10  .3575(8)  .7631(5)  .6953(4)  .0422(15) Uani d . 1 . . C
    C11  .2015(8)  .6266(5)  .6142(4)  .0473(17) Uani d . 1 . . C
    H11A  .0884  .6439  .6344  .057 Uiso calc R 1 . . H
    H11B  .2124  .6647  .5677  .057 Uiso calc R 1 . . H
    C12  .1980(8)  .5186(5)  .5932(4)  .0490(17) Uani d . 1 . . C
    H12A  .1700  .4810  .6379  .059 Uiso calc R 1 . . H
    H12B  .1034  .5072  .5523  .059 Uiso calc R 1 . . H
    C13  .3734(8)  .4840(5)  .5669(4)  .0406(15) Uani d . 1 . . C
    C14  .5201(7)  .5081(5)  .6333(4)  .0407(15) Uani d . 1 . . C
    H14  .4771  .4789  .6798  .049 Uiso calc R 1 . . H
    C15  .6806(9)  .4463(6)  .6148(4)  .0559(19) Uani d . 1 . . C
    H15A  .7487  .4776  .5765  .067 Uiso calc R 1 . . H
    H15B  .7598  .4333  .6609  .067 Uiso calc R 1 . . H
    C16  .5906(11)  .3540(6)  .5832(4)  .060(2) Uani d . 1 . . C
    C17  .4013(10)  .3753(5)  .5586(4)  .0486(17) Uani d . 1 . . C
    C18  .2919(12)  .3046(6)  .5319(4)  .061(2) Uani d . 1 . . C
    H18  .3404  .2422  .5344  .073 Uiso calc R 1 . . H
    C19  .1031(13)  .3116(7)  .4985(5)  .087(3) Uani d . 1 . . C
    H19A  .0238  .3045  .5390  .130 Uiso calc R 1 . . H
    H19B  .0793  .2611  .4609  .130 Uiso calc R 1 . . H
    H19C  .0838  .3739  .4742  .130 Uiso calc R 1 . . H
    C20  .3779(13)  .8276(6)  .6235(4)  .075(3) Uani d . 1 . . C
    H20A  .3689  .8949  .6375  .112 Uiso calc R 1 . . H
    H20B  .2845  .8121  .5839  .112 Uiso calc R 1 . . H
    H20C  .4931  .8159  .6044  .112 Uiso calc R 1 . . H
    C21  .4116(11)  .5306(6)  .4891(4)  .061(2) Uani d . 1 . . C
    H21A  .3417  .4983  .4477  .091 Uiso calc R 1 . . H
    H21B  .5371  .5243  .4818  .091 Uiso calc R 1 . . H
    H21C  .3798  .5983  .4894  .091 Uiso calc R 1 . . H
    O1  .3400(11)  .9490(6)  .8865(4)  .113(3) Uani d . 1 . . O
    O2  .6718(9)  .2766(5)  .5802(4)  .0865(19) Uani d . 1 . . O
    C31  -.0048(10)  .2322(6)  .7183(4)  .0568(19) Uani d . 1 . . C
    H31A  -.1165  .2497  .7396  .068 Uiso calc R 1 . . H
    H31B  .0239  .2836  .6831  .068 Uiso calc R 1 . . H
    C32  -.0335(10)  .1371(6)  .6725(5)  .064(2) Uani d . 1 . . C
    H32A  -.0776  .0871  .7055  .076 Uiso calc R 1 . . H
    H32B  -.1228  .1471  .6292  .076 Uiso calc R 1 . . H
    C33  .1420(12)  .1047(6)  .6430(5)  .066(2) Uani d . 1 . . C
    C34  .3048(11)  .1251(6)  .6894(5)  .062(2) Uani d . 1 . . C
    H34  .4121  .1011  .6734  .075 Uiso calc R 1 . . H
    C35  .3106(9)  .1770(5)  .7550(4)  .0525(18) Uani d . 1 . . C
    C36  .4773(9)  .1844(6)  .8060(5)  .063(2) Uani d . 1 . . C
    H36A  .5743  .1550  .7804  .076 Uiso calc R 1 . . H
    H36B  .4632  .1475  .8527  .076 Uiso calc R 1 . . H
    C37  .5307(9)  .2899(7)  .8288(4)  .060(2) Uani d . 1 . . C
    H37A  .6353  .2894  .8660  .072 Uiso calc R 1 . . H
    H37B  .5612  .3255  .7834  .072 Uiso calc R 1 . . H
    C38  .3728(8)  .3396(5)  .8641(4)  .0475(17) Uani d . 1 . . C
    H38  .3515  .3072  .9128  .057 Uiso calc R 1 . . H
    C39  .1998(8)  .3340(5)  .8083(4)  .0437(16) Uani d . 1 . . C
    H39  .2286  .3663  .7606  .052 Uiso calc R 1 . . H
    C40  .1453(8)  .2271(5)  .7848(4)  .0442(16) Uani d . 1 . . C
    C41  .0478(8)  .3928(6)  .8385(4)  .0532(18) Uani d . 1 . . C
    H41A  .0088  .3601  .8837  .064 Uiso calc R 1 . . H
    H41B  -.0529  .3930  .7994  .064 Uiso calc R 1 . . H
    C42  .0940(10)  .4989(6)  .8605(4)  .0550(18) Uani d . 1 . . C
    H42A  .1164  .5354  .8145  .066 Uiso calc R 1 . . H
    H42B  -.0066  .5287  .8834  .066 Uiso calc R 1 . . H
    C43  .2589(9)  .5017(6)  .9174(4)  .0493(17) Uani d . 1 . . C
    C44  .4137(9)  .4481(6)  .8801(4)  .0532(18) Uani d . 1 . . C
    H44  .4185  .4779  .8290  .064 Uiso calc R 1 . . H
    C45  .5892(10)  .4783(7)  .9261(5)  .064(2) Uani d . 1 . . C
    H45A  .6094  .4414  .9737  .076 Uiso calc R 1 . . H
    H45B  .6917  .4706  .8958  .076 Uiso calc R 1 . . H
    C46  .5524(11)  .5838(7)  .9419(4)  .071(2) Uani d . 1 . . C
    C47  .3530(11)  .6003(6)  .9359(4)  .059(2) Uani d . 1 . . C
    C48  .2849(11)  .6891(7)  .9477(4)  .065(2) Uani d . 1 . . C
    H48  .3697  .7381  .9577  .078 Uiso calc R 1 . . H
    C49  .0969(12)  .7203(7)  .9472(5)  .080(3) Uani d . 1 . . C
    H49A  .0568  .7450  .8970  .120 Uiso calc R 1 . . H
    H49B  .0873  .7705  .9852  .120 Uiso calc R 1 . . H
    H49C  .0236  .6659  .9593  .120 Uiso calc R 1 . . H
    C50  .0823(11)  .1704(6)  .8531(4)  .064(2) Uani d . 1 . . C
    H50A  -.0405  .1868  .8598  .095 Uiso calc R 1 . . H
    H50B  .1564  .1868  .8992  .095 Uiso calc R 1 . . H
    H50C  .0913  .1019  .8434  .095 Uiso calc R 1 . . H
    C51  .2240(12)  .4579(7)  .9977(4)  .073(2) Uani d . 1 . . C
    H51A  .1321  .4948 1.0199  .110 Uiso calc R 1 . . H
    H51B  .3328  .4604 1.0314  .110 Uiso calc R 1 . . H
    H51C  .1856  .3915  .9912  .110 Uiso calc R 1 . . H
    O31  .1349(10)  .0565(5)  .5829(4)  .098(2) Uani d . 1 . . O
    O32  .6673(8)  .6438(6)  .9587(4)  .093(2) Uani d . 1 . . O
_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
    C1 C2 . 1.513(11) ?
    C1 C10 . 1.526(9) ?
    C1 H1A .  .970 ?
    C1 H1B .  .970 ?
    C2 C3 . 1.510(11) ?
    C2 H2A .  .970 ?
    C2 H2B .  .970 ?
    C3 O1 . 1.227(9) ?
    C3 C4 . 1.453(12) ?
    C4 C5 . 1.330(10) ?
    C4 H4 .  .930 ?
    C5 C6 . 1.484(10) ?
    C5 C10 . 1.546(9) ?
    C6 C7 . 1.525(12) ?
    C6 H6A .  .970 ?
    C6 H6B .  .970 ?
    C7 C8 . 1.537(9) ?
    C7 H7A .  .970 ?
    C7 H7B .  .970 ?
    C8 C14 . 1.503(10) ?
    C8 C9 . 1.536(8) ?
    C8 H8 .  .980 ?
    C9 C11 . 1.551(9) ?
    C9 C10 . 1.552(9) ?
    C9 H9 .  .980 ?
    C10 C20 . 1.549(10) ?
    C11 C12 . 1.530(10) ?
    C11 H11A .  .970 ?
    C11 H11B .  .970 ?
    C12 C13 . 1.499(9) ?
    C12 H12A .  .970 ?
    C12 H12B .  .970 ?
    C13 C17 . 1.517(10) ?
    C13 C21 . 1.543(9) ?
    C13 C14 . 1.556(8) ?
    C14 C15 . 1.524(10) ?
    C14 H14 .  .980 ?
    C15 C16 . 1.518(11) ?
    C15 H15A .  .970 ?
    C15 H15B .  .970 ?
    C16 O2 . 1.228(9) ?
    C16 C17 . 1.470(11) ?
    C17 C18 . 1.328(10) ?
    C18 C19 . 1.480(12) ?
    C18 H18 .  .930 ?
    C19 H19A .  .960 ?
    C19 H19B .  .960 ?
    C19 H19C .  .960 ?
    C20 H20A .  .960 ?
    C20 H20B .  .960 ?
    C20 H20C .  .960 ?
    C21 H21A .  .960 ?
    C21 H21B .  .960 ?
    C21 H21C .  .960 ?
    C31 C32 . 1.536(11) ?
    C31 C40 . 1.540(9) ?
    C31 H31A .  .970 ?
    C31 H31B .  .970 ?
    C32 C33 . 1.513(11) ?
    C32 H32A .  .970 ?
    C32 H32B .  .970 ?
    C33 O31 . 1.233(10) ?
    C33 C34 . 1.428(11) ?
    C34 C35 . 1.340(10) ?
    C34 H34 .  .930 ?
    C35 C36 . 1.468(10) ?
    C35 C40 . 1.541(9) ?
    C36 C37 . 1.546(11) ?
    C36 H36A .  .970 ?
    C36 H36B .  .970 ?
    C37 C38 . 1.534(9) ?
    C37 H37A .  .970 ?
    C37 H37B .  .970 ?
    C38 C44 . 1.542(11) ?
    C38 C39 . 1.548(9) ?
    C38 H38 .  .980 ?
    C39 C41 . 1.522(10) ?
    C39 C40 . 1.570(10) ?
    C39 H39 .  .980 ?
    C40 C50 . 1.526(10) ?
    C41 C42 . 1.539(11) ?
    C41 H41A .  .970 ?
    C41 H41B .  .970 ?
    C42 C43 . 1.511(10) ?
    C42 H42A .  .970 ?
    C42 H42B .  .970 ?
    C43 C47 . 1.548(11) ?
    C43 C44 . 1.557(10) ?
    C43 C51 . 1.560(10) ?
    C44 C45 . 1.532(10) ?
    C44 H44 .  .980 ?
    C45 C46 . 1.506(13) ?
    C45 H45A .  .970 ?
    C45 H45B .  .970 ?
    C46 O32 . 1.207(10) ?
    C46 C47 . 1.500(12) ?
    C47 C48 . 1.345(12) ?
    C48 C49 . 1.466(12) ?
    C48 H48 .  .930 ?
    C49 H49A .  .960 ?
    C49 H49B .  .960 ?
    C49 H49C .  .960 ?
    C50 H50A .  .960 ?
    C50 H50B .  .960 ?
    C50 H50C .  .960 ?
    C51 H51A .  .960 ?
    C51 H51B .  .960 ?
    C51 H51C .  .960 ?
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
    C2 C1 C10 . . 113.8(6) ?
    C2 C1 H1A . . 108.8 ?
    C10 C1 H1A . . 108.8 ?
    C2 C1 H1B . . 108.8 ?
    C10 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    C3 C2 C1 . . 112.6(7) ?
    C3 C2 H2A . . 109.1 ?
    C1 C2 H2A . . 109.1 ?
    C3 C2 H2B . . 109.1 ?
    C1 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.8 ?
    O1 C3 C4 . . 122.1(8) ?
    O1 C3 C2 . . 121.7(8) ?
    C4 C3 C2 . . 116.2(6) ?
    C5 C4 C3 . . 125.3(7) ?
    C5 C4 H4 . . 117.4 ?
    C3 C4 H4 . . 117.4 ?
    C4 C5 C6 . . 121.4(6) ?
    C4 C5 C10 . . 121.1(6) ?
    C6 C5 C10 . . 117.5(6) ?
    C5 C6 C7 . . 113.3(6) ?
    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 . . 111.3(7) ?
    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 C9 . . 108.8(5) ?
    C14 C8 C7 . . 111.3(6) ?
    C9 C8 C7 . . 108.8(5) ?
    C14 C8 H8 . . 109.3 ?
    C9 C8 H8 . . 109.3 ?
    C7 C8 H8 . . 109.3 ?
    C8 C9 C11 . . 111.3(5) ?
    C8 C9 C10 . . 114.6(5) ?
    C11 C9 C10 . . 111.5(5) ?
    C8 C9 H9 . . 106.2 ?
    C11 C9 H9 . . 106.2 ?
    C10 C9 H9 . . 106.2 ?
    C1 C10 C5 . . 110.8(5) ?
    C1 C10 C20 . . 109.1(6) ?
    C5 C10 C20 . . 107.5(6) ?
    C1 C10 C9 . . 109.4(6) ?
    C5 C10 C9 . . 108.2(5) ?
    C20 C10 C9 . . 111.8(5) ?
    C12 C11 C9 . . 112.8(5) ?
    C12 C11 H11A . . 109.0 ?
    C9 C11 H11A . . 109.0 ?
    C12 C11 H11B . . 109.0 ?
    C9 C11 H11B . . 109.0 ?
    H11A C11 H11B . . 107.8 ?
    C13 C12 C11 . . 112.5(6) ?
    C13 C12 H12A . . 109.1 ?
    C11 C12 H12A . . 109.1 ?
    C13 C12 H12B . . 109.1 ?
    C11 C12 H12B . . 109.1 ?
    H12A C12 H12B . . 107.8 ?
    C12 C13 C17 . . 118.1(6) ?
    C12 C13 C21 . . 111.4(6) ?
    C17 C13 C21 . . 106.8(6) ?
    C12 C13 C14 . . 106.6(5) ?
    C17 C13 C14 . . 100.8(5) ?
    C21 C13 C14 . . 112.9(5) ?
    C8 C14 C15 . . 121.7(6) ?
    C8 C14 C13 . . 113.9(5) ?
    C15 C14 C13 . . 104.0(5) ?
    C8 C14 H14 . . 105.3 ?
    C15 C14 H14 . . 105.3 ?
    C13 C14 H14 . . 105.3 ?
    C16 C15 C14 . . 102.1(6) ?
    C16 C15 H15A . . 111.3 ?
    C14 C15 H15A . . 111.3 ?
    C16 C15 H15B . . 111.3 ?
    C14 C15 H15B . . 111.3 ?
    H15A C15 H15B . . 109.2 ?
    O2 C16 C17 . . 128.8(8) ?
    O2 C16 C15 . . 122.4(7) ?
    C17 C16 C15 . . 108.9(6) ?
    C18 C17 C16 . . 120.2(7) ?
    C18 C17 C13 . . 132.0(7) ?
    C16 C17 C13 . . 107.7(6) ?
    C17 C18 C19 . . 128.7(8) ?
    C17 C18 H18 . . 115.7 ?
    C19 C18 H18 . . 115.7 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C10 C20 H20A . . 109.5 ?
    C10 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C10 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C13 C21 H21A . . 109.5 ?
    C13 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C13 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C32 C31 C40 . . 114.2(6) ?
    C32 C31 H31A . . 108.7 ?
    C40 C31 H31A . . 108.7 ?
    C32 C31 H31B . . 108.7 ?
    C40 C31 H31B . . 108.7 ?
    H31A C31 H31B . . 107.6 ?
    C33 C32 C31 . . 109.8(6) ?
    C33 C32 H32A . . 109.7 ?
    C31 C32 H32A . . 109.7 ?
    C33 C32 H32B . . 109.7 ?
    C31 C32 H32B . . 109.7 ?
    H32A C32 H32B . . 108.2 ?
    O31 C33 C34 . . 123.8(8) ?
    O31 C33 C32 . . 117.9(8) ?
    C34 C33 C32 . . 118.1(7) ?
    C35 C34 C33 . . 123.3(7) ?
    C35 C34 H34 . . 118.4 ?
    C33 C34 H34 . . 118.4 ?
    C34 C35 C36 . . 120.9(7) ?
    C34 C35 C40 . . 123.7(6) ?
    C36 C35 C40 . . 115.3(6) ?
    C35 C36 C37 . . 114.0(6) ?
    C35 C36 H36A . . 108.8 ?
    C37 C36 H36A . . 108.8 ?
    C35 C36 H36B . . 108.8 ?
    C37 C36 H36B . . 108.8 ?
    H36A C36 H36B . . 107.6 ?
    C38 C37 C36 . . 109.2(6) ?
    C38 C37 H37A . . 109.8 ?
    C36 C37 H37A . . 109.8 ?
    C38 C37 H37B . . 109.8 ?
    C36 C37 H37B . . 109.8 ?
    H37A C37 H37B . . 108.3 ?
    C37 C38 C44 . . 110.8(6) ?
    C37 C38 C39 . . 110.9(6) ?
    C44 C38 C39 . . 107.6(5) ?
    C37 C38 H38 . . 109.1 ?
    C44 C38 H38 . . 109.1 ?
    C39 C38 H38 . . 109.1 ?
    C41 C39 C38 . . 111.4(5) ?
    C41 C39 C40 . . 113.7(5) ?
    C38 C39 C40 . . 113.1(5) ?
    C41 C39 H39 . . 105.9 ?
    C38 C39 H39 . . 105.9 ?
    C40 C39 H39 . . 105.9 ?
    C50 C40 C31 . . 110.6(6) ?
    C50 C40 C35 . . 109.9(6) ?
    C31 C40 C35 . . 108.7(5) ?
    C50 C40 C39 . . 111.5(6) ?
    C31 C40 C39 . . 107.9(5) ?
    C35 C40 C39 . . 108.0(6) ?
    C39 C41 C42 . . 115.5(6) ?
    C39 C41 H41A . . 108.4 ?
    C42 C41 H41A . . 108.4 ?
    C39 C41 H41B . . 108.4 ?
    C42 C41 H41B . . 108.4 ?
    H41A C41 H41B . . 107.5 ?
    C43 C42 C41 . . 109.8(6) ?
    C43 C42 H42A . . 109.7 ?
    C41 C42 H42A . . 109.7 ?
    C43 C42 H42B . . 109.7 ?
    C41 C42 H42B . . 109.7 ?
    H42A C42 H42B . . 108.2 ?
    C42 C43 C47 . . 119.2(7) ?
    C42 C43 C44 . . 108.0(6) ?
    C47 C43 C44 . . 99.3(6) ?
    C42 C43 C51 . . 112.7(6) ?
    C47 C43 C51 . . 105.1(6) ?
    C44 C43 C51 . . 112.0(7) ?
    C45 C44 C38 . . 120.2(6) ?
    C45 C44 C43 . . 106.7(6) ?
    C38 C44 C43 . . 112.9(6) ?
    C45 C44 H44 . . 105.3 ?
    C38 C44 H44 . . 105.3 ?
    C43 C44 H44 . . 105.3 ?
    C46 C45 C44 . . 101.3(7) ?
    C46 C45 H45A . . 111.5 ?
    C44 C45 H45A . . 111.5 ?
    C46 C45 H45B . . 111.5 ?
    C44 C45 H45B . . 111.5 ?
    H45A C45 H45B . . 109.3 ?
    O32 C46 C47 . . 126.4(9) ?
    O32 C46 C45 . . 124.4(8) ?
    C47 C46 C45 . . 109.1(7) ?
    C48 C47 C46 . . 120.8(7) ?
    C48 C47 C43 . . 131.0(7) ?
    C46 C47 C43 . . 108.2(7) ?
    C47 C48 C49 . . 129.7(8) ?
    C47 C48 H48 . . 115.1 ?
    C49 C48 H48 . . 115.1 ?
    C48 C49 H49A . . 109.5 ?
    C48 C49 H49B . . 109.5 ?
    H49A C49 H49B . . 109.5 ?
    C48 C49 H49C . . 109.5 ?
    H49A C49 H49C . . 109.5 ?
    H49B C49 H49C . . 109.5 ?
    C40 C50 H50A . . 109.5 ?
    C40 C50 H50B . . 109.5 ?
    H50A C50 H50B . . 109.5 ?
    C40 C50 H50C . . 109.5 ?
    H50A C50 H50C . . 109.5 ?
    H50B C50 H50C . . 109.5 ?
    C43 C51 H51A . . 109.5 ?
    C43 C51 H51B . . 109.5 ?
    H51A C51 H51B . . 109.5 ?
    C43 C51 H51C . . 109.5 ?
    H51A C51 H51C . . 109.5 ?
    H51B C51 H51C . . 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 . . . . -52.0(8) yes
    C1 C2 C3 O1 . . . . -154.1(9) ?
    C1 C2 C3 C4 . . . . 29.3(10) yes
    O1 C3 C4 C5 . . . . -177.9(9) ?
    C2 C3 C4 C5 . . . . -1.3(13) yes
    C3 C4 C5 C6 . . . . 172.5(8) ?
    C3 C4 C5 C10 . . . . -4.6(13) yes
    C4 C5 C6 C7 . . . . 134.8(8) ?
    C10 C5 C6 C7 . . . . -48.0(10) yes
    C5 C6 C7 C8 . . . . 52.5(9) yes
    C6 C7 C8 C14 . . . . -176.7(6) ?
    C6 C7 C8 C9 . . . . -56.8(8) yes
    C14 C8 C9 C11 . . . . -52.5(7) ?
    C7 C8 C9 C11 . . . . -173.9(6) ?
    C14 C8 C9 C10 . . . . 179.7(5) ?
    C7 C8 C9 C10 . . . . 58.3(7) yes
    C2 C1 C10 C5 . . . . 45.3(8) yes
    C2 C1 C10 C20 . . . . -72.9(8) yes
    C2 C1 C10 C9 . . . . 164.5(6) ?
    C4 C5 C10 C1 . . . . -17.5(10) yes
    C6 C5 C10 C1 . . . . 165.3(7) ?
    C4 C5 C10 C20 . . . . 101.7(8) ?
    C6 C5 C10 C20 . . . . -75.5(8) ?
    C4 C5 C10 C9 . . . . -137.4(7) ?
    C6 C5 C10 C9 . . . . 45.3(8) yes
    C8 C9 C10 C1 . . . . -171.6(5) ?
    C11 C9 C10 C1 . . . . 60.8(7) ?
    C8 C9 C10 C5 . . . . -50.8(7) yes
    C11 C9 C10 C5 . . . . -178.4(5) ?
    C8 C9 C10 C20 . . . . 67.4(8) ?
    C11 C9 C10 C20 . . . . -60.2(8) ?
    C8 C9 C11 C12 . . . . 50.9(8) ?
    C10 C9 C11 C12 . . . . -179.7(6) ?
    C9 C11 C12 C13 . . . . -54.5(8) ?
    C11 C12 C13 C17 . . . . 168.8(6) ?
    C11 C12 C13 C21 . . . . -67.0(8) yes
    C11 C12 C13 C14 . . . . 56.5(7) ?
    C9 C8 C14 C15 . . . . -174.3(6) ?
    C7 C8 C14 C15 . . . . -54.5(8) ?
    C9 C8 C14 C13 . . . . 59.8(7) ?
    C7 C8 C14 C13 . . . . 179.7(5) ?
    C12 C13 C14 C8 . . . . -61.4(7) ?
    C17 C13 C14 C8 . . . . 174.7(5) ?
    C21 C13 C14 C8 . . . . 61.2(7) ?
    C12 C13 C14 C15 . . . . 163.9(6) ?
    C17 C13 C14 C15 . . . . 40.0(6) yes
    C21 C13 C14 C15 . . . . -73.5(7) ?
    C8 C14 C15 C16 . . . . -167.1(6) ?
    C13 C14 C15 C16 . . . . -36.8(7) yes
    C14 C15 C16 O2 . . . . -160.5(7) ?
    C14 C15 C16 C17 . . . . 19.7(8) yes
    O2 C16 C17 C18 . . . . 3.2(12) ?
    C15 C16 C17 C18 . . . . -177.1(6) ?
    O2 C16 C17 C13 . . . . -174.2(8) ?
    C15 C16 C17 C13 . . . . 5.6(8) yes
    C12 C13 C17 C18 . . . . 39.7(11) ?
    C21 C13 C17 C18 . . . . -86.7(9) ?
    C14 C13 C17 C18 . . . . 155.3(7) ?
    C12 C13 C17 C16 . . . . -143.3(6) ?
    C21 C13 C17 C16 . . . . 90.3(7) ?
    C14 C13 C17 C16 . . . . -27.8(6) yes
    C16 C17 C18 C19 . . . . -174.5(7) yes
    C13 C17 C18 C19 . . . . 2.1(13) ?
    C40 C31 C32 C33 . . . . -54.8(9) yes
    C31 C32 C33 O31 . . . . -151.6(8) ?
    C31 C32 C33 C34 . . . . 33.3(10) yes
    O31 C33 C34 C35 . . . . -179.5(9) ?
    C32 C33 C34 C35 . . . . -4.6(12) yes
    C33 C34 C35 C36 . . . . 171.5(8) ?
    C33 C34 C35 C40 . . . . -4.7(12) yes
    C34 C35 C36 C37 . . . . 129.3(8) ?
    C40 C35 C36 C37 . . . . -54.2(9) yes
    C35 C36 C37 C38 . . . . 54.4(9) yes
    C36 C37 C38 C44 . . . . -174.3(6) ?
    C36 C37 C38 C39 . . . . -54.9(8) yes
    C37 C38 C39 C41 . . . . -173.6(6) ?
    C44 C38 C39 C41 . . . . -52.2(7) ?
    C37 C38 C39 C40 . . . . 56.8(8) yes
    C44 C38 C39 C40 . . . . 178.2(6) ?
    C32 C31 C40 C50 . . . . -75.4(8) yes
    C32 C31 C40 C35 . . . . 45.4(8) yes
    C32 C31 C40 C39 . . . . 162.4(6) ?
    C34 C35 C40 C50 . . . . 105.4(8) ?
    C36 C35 C40 C50 . . . . -70.9(8) ?
    C34 C35 C40 C31 . . . . -15.8(10) yes
    C36 C35 C40 C31 . . . . 167.8(6) ?
    C34 C35 C40 C39 . . . . -132.7(7) ?
    C36 C35 C40 C39 . . . . 50.9(8) yes
    C41 C39 C40 C50 . . . . -59.5(7) ?
    C38 C39 C40 C50 . . . . 68.9(7) ?
    C41 C39 C40 C31 . . . . 62.2(7) ?
    C38 C39 C40 C31 . . . . -169.4(5) ?
    C41 C39 C40 C35 . . . . 179.6(5) ?
    C38 C39 C40 C35 . . . . -52.0(7) yes
    C38 C39 C41 C42 . . . . 52.1(8) ?
    C40 C39 C41 C42 . . . . -178.6(6) ?
    C39 C41 C42 C43 . . . . -54.2(8) ?
    C41 C42 C43 C47 . . . . 168.3(6) ?
    C41 C42 C43 C44 . . . . 56.2(8) ?
    C41 C42 C43 C51 . . . . -68.0(8) yes
    C37 C38 C44 C45 . . . . -51.6(9) ?
    C39 C38 C44 C45 . . . . -173.0(6) ?
    C37 C38 C44 C43 . . . . -179.0(6) ?
    C39 C38 C44 C43 . . . . 59.6(7) ?
    C42 C43 C44 C45 . . . . 163.0(6) ?
    C47 C43 C44 C45 . . . . 38.1(7) yes
    C51 C43 C44 C45 . . . . -72.4(8) ?
    C42 C43 C44 C38 . . . . -62.8(8) ?
    C47 C43 C44 C38 . . . . 172.3(6) ?
    C51 C43 C44 C38 . . . . 61.8(8) ?
    C38 C44 C45 C46 . . . . -168.2(6) ?
    C43 C44 C45 C46 . . . . -38.0(8) yes
    C44 C45 C46 O32 . . . . -159.7(8) ?
    C44 C45 C46 C47 . . . . 22.2(8) yes
    O32 C46 C47 C48 . . . . 1.7(13) ?
    C45 C46 C47 C48 . . . . 179.8(7) ?
    O32 C46 C47 C43 . . . . -176.9(8) ?
    C45 C46 C47 C43 . . . . 1.2(8) yes
    C42 C43 C47 C48 . . . . 41.4(11) ?
    C44 C43 C47 C48 . . . . 158.1(8) ?
    C51 C43 C47 C48 . . . . -86.0(10) ?
    C42 C43 C47 C46 . . . . -140.2(6) ?
    C44 C43 C47 C46 . . . . -23.5(7) yes
    C51 C43 C47 C46 . . . . 92.4(7) ?
    C46 C47 C48 C49 . . . . -177.8(7) yes
    C43 C47 C48 C49 . . . .  .4(14) ?
    C16 C17 C18 C19 . . . . -174.5(7) ?
    C46 C47 C48 C49 . . . . -177.8(7) ?
    H9 C9 C8 H8 . . . . -178.0 yes
    H39 C39 C38 H38 . . . . -179.1 yes
    C21 C13 C14 H14 . . . . 176.0 yes
    C51 C43 C44 H44 . . . . 176.1 yes
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
    C21 H21C O2 2_656  .96 2.745 3.625(10) 153 yes
    C21 H21B O31 2_656  .96 2.813 3.723(10) 159 yes
    C32 H32B O2 1_455  .97 2.453 3.237(10) 138 yes
    C45 H45A O1 2_647  .97 2.425 3.274(11) 146 yes
    C50 H50B O32 2_647  .96 2.759 3.641(10) 153 yes
    C51 H51B O1 2_647  .96 2.725 3.678(12) 172 yes
