##############################################################################
###                                                                        ###
###        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     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2007-03-26
_journal_date_accepted     2007-05-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o3032
_journal_page_last     o3033
_journal_paper_category     EO
_journal_coeditor_code     EZ2076
_publ_contact_author_name     'Lemmerer, Andreas'
_publ_contact_author_address
;
School of Chemistry
University of the Witwatersrand
Private Bag 3
PO Wits 2050
South Africa
;
_publ_contact_author_email     anderl@chem.wits.ac.za
_publ_contact_author_fax     '27(11)7176749'
_publ_contact_author_phone     '27(11)7176755'
_publ_section_title
;
β-Amyrin benzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Perold, Guido W.'
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
Johannesburg
PO Wits 2050
South Africa
;
    'Black, Robert S.'
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
Johannesburg
PO Wits 2050
South Africa
;
    'Lemmerer, Andreas'
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
Johannesburg
PO Wits 2050
South Africa
;
    'Michael, Joseph P.'
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
Johannesburg
PO Wits 2050
South Africa
;
    'Otterlo, Willem A. L. van'
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
Johannesburg
PO Wits 2050
South Africa
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
β-Amyrin benzoate
;
_chemical_formula_moiety     'C37 H54 O2'
_chemical_formula_sum     'C37 H54 O2'
_chemical_formula_iupac     'C37 H54 O2'
_chemical_formula_weight     530.8
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     6.78970(10)
_cell_length_b     12.0370(2)
_cell_length_c     37.8246(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3091.31(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6693
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     30.6
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.64
_exptl_crystal_size_mid     0.56
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.141
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1168
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0.00 0.00 -1.00 0.0800
    0.00 0.00 1.00 0.0800
    0.00 -1.00 0.00 0.2800
    0.00 1.00 0.00 0.2800
    1.00 0.00 0.00 0.3200
    -1.00 0.00 0.00 0.3200
_exptl_absorpt_coefficient_mu     0.068
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(XPREP; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.960
_exptl_absorpt_correction_T_max     0.989
_exptl_special_details
;
Numerical integration absorption corrections based on indexed
crystal faces
were applied using the XPREP routine (Bruker, 1999)
;
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_reflns_number     45207
_diffrn_reflns_av_R_equivalents     0.065
_diffrn_reflns_theta_min     2.0
_diffrn_reflns_theta_max     28
_diffrn_reflns_theta_full     28
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -48
_diffrn_reflns_limit_l_max     49
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     4236
_reflns_number_gt     3995
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.041
_refine_ls_R_factor_gt     0.039
_refine_ls_wR_factor_gt     0.099
_refine_ls_wR_factor_ref     0.101
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.06
_refine_ls_number_reflns     4236
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0631P)²+0.3893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.30
_refine_diff_density_min     -0.24
_refine_ls_extinction_method     none
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
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 0.2238(2) 0.66959(13) 0.22612(4) 0.0203(3) Uani d . 1 . .
    H H1A 0.1128 0.72 0.2317 0.024 Uiso calc R 1 . .
    H H1B 0.3448 0.7024 0.2363 0.024 Uiso calc R 1 . .
    C C2 0.2468(2) 0.66287(13) 0.18584(4) 0.0212(3) Uani d . 1 . .
    H H2A 0.1222 0.637 0.175 0.025 Uiso calc R 1 . .
    H H2B 0.2779 0.7373 0.1762 0.025 Uiso calc R 1 . .
    C C3 0.4108(2) 0.58281(13) 0.17718(4) 0.0197(3) Uani d . 1 . .
    H H3 0.5332 0.6087 0.1893 0.024 Uiso calc R 1 . .
    C C4 0.3688(2) 0.46299(13) 0.18896(4) 0.0194(3) Uani d . 1 . .
    C C5 0.3393(2) 0.47086(13) 0.22985(3) 0.0175(3) Uani d . 1 . .
    H H5 0.4683 0.4991 0.2389 0.021 Uiso calc R 1 . .
    C C6 0.3117(2) 0.35937(13) 0.24870(4) 0.0220(3) Uani d . 1 . .
    H H6A 0.3941 0.3019 0.2372 0.026 Uiso calc R 1 . .
    H H6B 0.1723 0.3358 0.2471 0.026 Uiso calc R 1 . .
    C C7 0.3717(2) 0.37190(13) 0.28754(4) 0.0211(3) Uani d . 1 . .
    H H7A 0.5141 0.3893 0.2887 0.025 Uiso calc R 1 . .
    H H7B 0.3509 0.3001 0.2997 0.025 Uiso calc R 1 . .
    C C8 0.2561(2) 0.46341(12) 0.30742(4) 0.0178(3) Uani d . 1 . .
    C C9 0.2326(2) 0.57017(12) 0.28433(4) 0.0170(3) Uani d . 1 . .
    H H9 0.365 0.6064 0.285 0.02 Uiso calc R 1 . .
    C C10 0.1859(2) 0.55592(13) 0.24388(4) 0.0171(3) Uani d . 1 . .
    C C11 0.0954(2) 0.65227(13) 0.30325(4) 0.0215(3) Uani d . 1 . .
    H H11A 0.1115 0.7267 0.2925 0.026 Uiso calc R 1 . .
    H H11B -0.0428 0.6288 0.2996 0.026 Uiso calc R 1 . .
    C C12 0.1347(2) 0.66015(13) 0.34210(4) 0.0212(3) Uani d . 1 . .
    H H12 0.0685 0.717 0.3548 0.025 Uiso calc R 1 . .
    C C13 0.2550(2) 0.59397(13) 0.36035(4) 0.0188(3) Uani d . 1 . .
    C C14 0.3695(2) 0.50043(13) 0.34219(4) 0.0185(3) Uani d . 1 . .
    C C15 0.3964(3) 0.39984(14) 0.36740(4) 0.0258(3) Uani d . 1 . .
    H H15A 0.273 0.356 0.3676 0.031 Uiso calc R 1 . .
    H H15B 0.502 0.3516 0.3579 0.031 Uiso calc R 1 . .
    C C16 0.4483(3) 0.43141(14) 0.40553(4) 0.0268(3) Uani d . 1 . .
    H H16A 0.5804 0.4662 0.4059 0.032 Uiso calc R 1 . .
    H H16B 0.4544 0.3631 0.4201 0.032 Uiso calc R 1 . .
    C C17 0.2984(3) 0.51200(15) 0.42198(4) 0.0256(3) Uani d . 1 . .
    C C18 0.2908(2) 0.61864(14) 0.39938(4) 0.0219(3) Uani d . 1 . .
    H H18 0.1751 0.6626 0.4079 0.026 Uiso calc R 1 . .
    C C19 0.4737(3) 0.69286(15) 0.40412(4) 0.0256(3) Uani d . 1 . .
    H H19A 0.5889 0.654 0.3939 0.031 Uiso calc R 1 . .
    H H19B 0.4538 0.7621 0.3905 0.031 Uiso calc R 1 . .
    C C20 0.5215(3) 0.72395(16) 0.44263(4) 0.0290(4) Uani d . 1 . .
    C C21 0.5376(3) 0.61569(17) 0.46385(4) 0.0327(4) Uani d . 1 . .
    H H21A 0.6552 0.5742 0.4558 0.039 Uiso calc R 1 . .
    H H21B 0.5569 0.6341 0.4891 0.039 Uiso calc R 1 . .
    C C22 0.3576(3) 0.54134(17) 0.46027(4) 0.0322(4) Uani d . 1 . .
    H H22A 0.2446 0.5786 0.4718 0.039 Uiso calc R 1 . .
    H H22B 0.3829 0.4714 0.4733 0.039 Uiso calc R 1 . .
    C C23 0.5541(2) 0.39306(14) 0.18158(4) 0.0252(3) Uani d . 1 . .
    H H23A 0.5268 0.3149 0.1869 0.038 Uiso calc R 1 . .
    H H23B 0.6625 0.4193 0.1965 0.038 Uiso calc R 1 . .
    H H23C 0.5909 0.4005 0.1566 0.038 Uiso calc R 1 . .
    C C24 0.1971(3) 0.41062(15) 0.16858(4) 0.0261(3) Uani d . 1 . .
    H H24A 0.1638 0.3387 0.1792 0.039 Uiso calc R 1 . .
    H H24B 0.2353 0.3998 0.1438 0.039 Uiso calc R 1 . .
    H H24C 0.0823 0.4599 0.1697 0.039 Uiso calc R 1 . .
    C C25 -0.0304(2) 0.52403(15) 0.23597(4) 0.0235(3) Uani d . 1 . .
    H H25A -0.0474 0.4438 0.2391 0.035 Uiso calc R 1 . .
    H H25B -0.0628 0.5444 0.2116 0.035 Uiso calc R 1 . .
    H H25C -0.1179 0.5637 0.2522 0.035 Uiso calc R 1 . .
    C C26 0.0536(2) 0.41393(14) 0.31691(4) 0.0237(3) Uani d . 1 . .
    H H26A -0.0134 0.4629 0.3338 0.036 Uiso calc R 1 . .
    H H26B 0.0716 0.3404 0.3276 0.036 Uiso calc R 1 . .
    H H26C -0.0263 0.407 0.2954 0.036 Uiso calc R 1 . .
    C C27 0.5789(2) 0.54578(15) 0.33350(4) 0.0243(3) Uani d . 1 . .
    H H27A 0.5692 0.6238 0.3263 0.036 Uiso calc R 1 . .
    H H27B 0.6365 0.5021 0.3142 0.036 Uiso calc R 1 . .
    H H27C 0.6626 0.54 0.3545 0.036 Uiso calc R 1 . .
    C C28 0.0943(3) 0.45846(19) 0.42306(5) 0.0358(4) Uani d . 1 . .
    H H28A 0.0015 0.509 0.4347 0.054 Uiso calc R 1 . .
    H H28B 0.101 0.3886 0.4363 0.054 Uiso calc R 1 . .
    H H28C 0.0495 0.4435 0.3989 0.054 Uiso calc R 1 . .
    C C29 0.7185(3) 0.7853(2) 0.44317(5) 0.0414(5) Uani d . 1 . .
    H H29A 0.7493 0.8078 0.4674 0.062 Uiso calc R 1 . .
    H H29B 0.7102 0.8513 0.4281 0.062 Uiso calc R 1 . .
    H H29C 0.8224 0.736 0.4343 0.062 Uiso calc R 1 . .
    C C30 0.3647(4) 0.80080(18) 0.45799(5) 0.0383(5) Uani d . 1 . .
    H H30A 0.2391 0.761 0.4595 0.057 Uiso calc R 1 . .
    H H30B 0.3493 0.8658 0.4427 0.057 Uiso calc R 1 . .
    H H30C 0.4049 0.825 0.4817 0.057 Uiso calc R 1 . .
    C C31 0.6289(2) 0.60710(14) 0.12809(4) 0.0239(3) Uani d . 1 . .
    C C32 0.6434(3) 0.61319(15) 0.08868(4) 0.0276(4) Uani d . 1 . .
    C C33 0.4794(3) 0.61160(18) 0.06693(5) 0.0372(4) Uani d . 1 . .
    H H33 0.3514 0.6053 0.0769 0.045 Uiso calc R 1 . .
    C C34 0.5026(4) 0.6193(2) 0.03050(5) 0.0512(6) Uani d . 1 . .
    H H34 0.3903 0.6181 0.0155 0.061 Uiso calc R 1 . .
    C C35 0.6872(4) 0.6287(2) 0.01612(5) 0.0568(7) Uani d . 1 . .
    H H35 0.7023 0.633 -0.0088 0.068 Uiso calc R 1 . .
    C C36 0.8492(4) 0.6317(3) 0.03738(6) 0.0606(7) Uani d . 1 . .
    H H36 0.9764 0.639 0.0272 0.073 Uiso calc R 1 . .
    C C37 0.8293(3) 0.6243(2) 0.07390(5) 0.0453(5) Uani d . 1 . .
    H H37 0.9425 0.6268 0.0887 0.054 Uiso calc R 1 . .
    O O1 0.44441(16) 0.58696(10) 0.13894(3) 0.0235(2) Uani d . 1 . .
    O O2 0.76870(18) 0.61892(13) 0.14734(3) 0.0347(3) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.5335(19) ?
    C1 C10 . 1.546(2) ?
    C1 H1A . 0.99 ?
    C1 H1B . 0.99 ?
    C2 C3 . 1.508(2) ?
    C2 H2A . 0.99 ?
    C2 H2B . 0.99 ?
    C3 O1 . 1.4652(16) ?
    C3 C4 . 1.536(2) ?
    C3 H3 . 1 ?
    C4 C24 . 1.533(2) ?
    C4 C23 . 1.539(2) ?
    C4 C5 . 1.5626(18) ?
    C5 C6 . 1.531(2) ?
    C5 C10 . 1.554(2) ?
    C5 H5 . 1 ?
    C6 C7 . 1.5318(19) ?
    C6 H6A . 0.99 ?
    C6 H6B . 0.99 ?
    C7 C8 . 1.547(2) ?
    C7 H7A . 0.99 ?
    C7 H7B . 0.99 ?
    C8 C26 . 1.541(2) ?
    C8 C9 . 1.562(2) ?
    C8 C14 . 1.5877(19) ?
    C9 C11 . 1.535(2) ?
    C9 C10 . 1.5719(18) ?
    C9 H9 . 1 ?
    C10 C25 . 1.547(2) ?
    C11 C12 . 1.4967(19) ?
    C11 H11A . 0.99 ?
    C11 H11B . 0.99 ?
    C12 C13 . 1.333(2) ?
    C12 H12 . 0.95 ?
    C13 C18 . 1.5256(19) ?
    C13 C14 . 1.531(2) ?
    C14 C15 . 1.552(2) ?
    C14 C27 . 1.558(2) ?
    C15 C16 . 1.532(2) ?
    C15 H15A . 0.99 ?
    C15 H15B . 0.99 ?
    C16 C17 . 1.538(2) ?
    C16 H16A . 0.99 ?
    C16 H16B . 0.99 ?
    C17 C28 . 1.529(3) ?
    C17 C18 . 1.543(2) ?
    C17 C22 . 1.544(2) ?
    C18 C19 . 1.540(2) ?
    C18 H18 . 1 ?
    C19 C20 . 1.538(2) ?
    C19 H19A . 0.99 ?
    C19 H19B . 0.99 ?
    C20 C30 . 1.526(3) ?
    C20 C29 . 1.528(3) ?
    C20 C21 . 1.534(3) ?
    C21 C22 . 1.521(3) ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C22 H22A . 0.99 ?
    C22 H22B . 0.99 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
    C24 H24A . 0.98 ?
    C24 H24B . 0.98 ?
    C24 H24C . 0.98 ?
    C25 H25A . 0.98 ?
    C25 H25B . 0.98 ?
    C25 H25C . 0.98 ?
    C26 H26A . 0.98 ?
    C26 H26B . 0.98 ?
    C26 H26C . 0.98 ?
    C27 H27A . 0.98 ?
    C27 H27B . 0.98 ?
    C27 H27C . 0.98 ?
    C28 H28A . 0.98 ?
    C28 H28B . 0.98 ?
    C28 H28C . 0.98 ?
    C29 H29A . 0.98 ?
    C29 H29B . 0.98 ?
    C29 H29C . 0.98 ?
    C30 H30A . 0.98 ?
    C30 H30B . 0.98 ?
    C30 H30C . 0.98 ?
    C31 O2 . 1.204(2) ?
    C31 O1 . 1.341(2) ?
    C31 C32 . 1.496(2) ?
    C32 C33 . 1.385(3) ?
    C32 C37 . 1.387(3) ?
    C33 C34 . 1.390(2) ?
    C33 H33 . 0.95 ?
    C34 C35 . 1.371(4) ?
    C34 H34 . 0.95 ?
    C35 C36 . 1.363(4) ?
    C35 H35 . 0.95 ?
    C36 C37 . 1.391(3) ?
    C36 H36 . 0.95 ?
    C37 H37 . 0.95 ?
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 . . 113.70(12) ?
    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 . . 108.94(12) ?
    C3 C2 H2A . . 109.9 ?
    C1 C2 H2A . . 109.9 ?
    C3 C2 H2B . . 109.9 ?
    C1 C2 H2B . . 109.9 ?
    H2A C2 H2B . . 108.3 ?
    O1 C3 C2 . . 107.92(12) ?
    O1 C3 C4 . . 110.32(12) ?
    C2 C3 C4 . . 113.58(12) ?
    O1 C3 H3 . . 108.3 ?
    C2 C3 H3 . . 108.3 ?
    C4 C3 H3 . . 108.3 ?
    C24 C4 C3 . . 112.42(13) ?
    C24 C4 C23 . . 107.79(12) ?
    C3 C4 C23 . . 108.01(12) ?
    C24 C4 C5 . . 115.15(12) ?
    C3 C4 C5 . . 104.71(11) ?
    C23 C4 C5 . . 108.51(12) ?
    C6 C5 C10 . . 109.68(12) ?
    C6 C5 C4 . . 115.05(12) ?
    C10 C5 C4 . . 117.63(12) ?
    C6 C5 H5 . . 104.3 ?
    C10 C5 H5 . . 104.3 ?
    C4 C5 H5 . . 104.3 ?
    C5 C6 C7 . . 109.14(12) ?
    C5 C6 H6A . . 109.9 ?
    C7 C6 H6A . . 109.9 ?
    C5 C6 H6B . . 109.9 ?
    C7 C6 H6B . . 109.9 ?
    H6A C6 H6B . . 108.3 ?
    C6 C7 C8 . . 113.66(12) ?
    C6 C7 H7A . . 108.8 ?
    C8 C7 H7A . . 108.8 ?
    C6 C7 H7B . . 108.8 ?
    C8 C7 H7B . . 108.8 ?
    H7A C7 H7B . . 107.7 ?
    C26 C8 C7 . . 106.90(12) ?
    C26 C8 C9 . . 110.91(12) ?
    C7 C8 C9 . . 111.46(11) ?
    C26 C8 C14 . . 110.37(11) ?
    C7 C8 C14 . . 110.87(11) ?
    C9 C8 C14 . . 106.38(11) ?
    C11 C9 C8 . . 109.33(11) ?
    C11 C9 C10 . . 113.69(11) ?
    C8 C9 C10 . . 118.36(12) ?
    C11 C9 H9 . . 104.7 ?
    C8 C9 H9 . . 104.7 ?
    C10 C9 H9 . . 104.7 ?
    C1 C10 C25 . . 107.07(13) ?
    C1 C10 C5 . . 108.87(12) ?
    C25 C10 C5 . . 114.00(12) ?
    C1 C10 C9 . . 107.02(12) ?
    C25 C10 C9 . . 114.00(11) ?
    C5 C10 C9 . . 105.61(11) ?
    C12 C11 C9 . . 112.99(12) ?
    C12 C11 H11A . . 109 ?
    C9 C11 H11A . . 109 ?
    C12 C11 H11B . . 109 ?
    C9 C11 H11B . . 109 ?
    H11A C11 H11B . . 107.8 ?
    C13 C12 C11 . . 125.41(14) ?
    C13 C12 H12 . . 117.3 ?
    C11 C12 H12 . . 117.3 ?
    C12 C13 C18 . . 118.82(14) ?
    C12 C13 C14 . . 121.21(13) ?
    C18 C13 C14 . . 119.78(13) ?
    C13 C14 C15 . . 110.97(12) ?
    C13 C14 C27 . . 107.47(13) ?
    C15 C14 C27 . . 107.19(12) ?
    C13 C14 C8 . . 109.38(12) ?
    C15 C14 C8 . . 110.32(12) ?
    C27 C14 C8 . . 111.47(11) ?
    C16 C15 C14 . . 114.33(13) ?
    C16 C15 H15A . . 108.7 ?
    C14 C15 H15A . . 108.7 ?
    C16 C15 H15B . . 108.7 ?
    C14 C15 H15B . . 108.7 ?
    H15A C15 H15B . . 107.6 ?
    C15 C16 C17 . . 112.65(13) ?
    C15 C16 H16A . . 109.1 ?
    C17 C16 H16A . . 109.1 ?
    C15 C16 H16B . . 109.1 ?
    C17 C16 H16B . . 109.1 ?
    H16A C16 H16B . . 107.8 ?
    C28 C17 C16 . . 110.18(15) ?
    C28 C17 C18 . . 109.57(14) ?
    C16 C17 C18 . . 108.84(12) ?
    C28 C17 C22 . . 107.88(14) ?
    C16 C17 C22 . . 110.60(14) ?
    C18 C17 C22 . . 109.76(14) ?
    C13 C18 C19 . . 110.72(12) ?
    C13 C18 C17 . . 112.31(13) ?
    C19 C18 C17 . . 113.01(13) ?
    C13 C18 H18 . . 106.8 ?
    C19 C18 H18 . . 106.8 ?
    C17 C18 H18 . . 106.8 ?
    C20 C19 C18 . . 114.93(13) ?
    C20 C19 H19A . . 108.5 ?
    C18 C19 H19A . . 108.5 ?
    C20 C19 H19B . . 108.5 ?
    C18 C19 H19B . . 108.5 ?
    H19A C19 H19B . . 107.5 ?
    C30 C20 C29 . . 108.24(16) ?
    C30 C20 C21 . . 111.43(15) ?
    C29 C20 C21 . . 109.93(16) ?
    C30 C20 C19 . . 111.15(15) ?
    C29 C20 C19 . . 108.37(14) ?
    C21 C20 C19 . . 107.69(14) ?
    C22 C21 C20 . . 113.31(15) ?
    C22 C21 H21A . . 108.9 ?
    C20 C21 H21A . . 108.9 ?
    C22 C21 H21B . . 108.9 ?
    C20 C21 H21B . . 108.9 ?
    H21A C21 H21B . . 107.7 ?
    C21 C22 C17 . . 115.29(14) ?
    C21 C22 H22A . . 108.5 ?
    C17 C22 H22A . . 108.5 ?
    C21 C22 H22B . . 108.5 ?
    C17 C22 H22B . . 108.5 ?
    H22A C22 H22B . . 107.5 ?
    C4 C23 H23A . . 109.5 ?
    C4 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C4 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C4 C24 H24A . . 109.5 ?
    C4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C10 C25 H25A . . 109.5 ?
    C10 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C10 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C8 C26 H26A . . 109.5 ?
    C8 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C8 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C14 C27 H27A . . 109.5 ?
    C14 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C14 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C17 C28 H28A . . 109.5 ?
    C17 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C17 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C20 C29 H29A . . 109.5 ?
    C20 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    C20 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    C20 C30 H30A . . 109.5 ?
    C20 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C20 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    O2 C31 O1 . . 124.94(14) ?
    O2 C31 C32 . . 123.02(15) ?
    O1 C31 C32 . . 112.04(14) ?
    C33 C32 C37 . . 119.60(16) ?
    C33 C32 C31 . . 122.59(16) ?
    C37 C32 C31 . . 117.77(16) ?
    C32 C33 C34 . . 119.8(2) ?
    C32 C33 H33 . . 120.1 ?
    C34 C33 H33 . . 120.1 ?
    C35 C34 C33 . . 120.2(2) ?
    C35 C34 H34 . . 119.9 ?
    C33 C34 H34 . . 119.9 ?
    C36 C35 C34 . . 120.37(18) ?
    C36 C35 H35 . . 119.8 ?
    C34 C35 H35 . . 119.8 ?
    C35 C36 C37 . . 120.4(2) ?
    C35 C36 H36 . . 119.8 ?
    C37 C36 H36 . . 119.8 ?
    C32 C37 C36 . . 119.6(2) ?
    C32 C37 H37 . . 120.2 ?
    C36 C37 H37 . . 120.2 ?
    C31 O1 C3 . . 117.01(12) ?
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 . . . . -56.44(17) ?
    C1 C2 C3 O1 . . . . -173.90(12) ?
    C1 C2 C3 C4 . . . . 63.46(16) ?
    O1 C3 C4 C24 . . . . -55.10(16) ?
    C2 C3 C4 C24 . . . . 66.20(16) ?
    O1 C3 C4 C23 . . . . 63.70(15) ?
    C2 C3 C4 C23 . . . . -175.00(12) ?
    O1 C3 C4 C5 . . . . 179.20(11) ?
    C2 C3 C4 C5 . . . . -59.50(15) ?
    C24 C4 C5 C6 . . . . 60.88(18) ?
    C3 C4 C5 C6 . . . . -175.15(12) ?
    C23 C4 C5 C6 . . . . -60.00(16) ?
    C24 C4 C5 C10 . . . . -70.76(17) ?
    C3 C4 C5 C10 . . . . 53.22(16) ?
    C23 C4 C5 C10 . . . . 168.37(13) ?
    C10 C5 C6 C7 . . . . -68.60(15) ?
    C4 C5 C6 C7 . . . . 156.08(12) ?
    C5 C6 C7 C8 . . . . 57.32(17) ?
    C6 C7 C8 C26 . . . . 78.92(15) ?
    C6 C7 C8 C9 . . . . -42.43(17) ?
    C6 C7 C8 C14 . . . . -160.73(13) ?
    C26 C8 C9 C11 . . . . 53.90(15) ?
    C7 C8 C9 C11 . . . . 172.89(12) ?
    C14 C8 C9 C11 . . . . -66.14(14) ?
    C26 C8 C9 C10 . . . . -78.43(15) ?
    C7 C8 C9 C10 . . . . 40.56(17) ?
    C14 C8 C9 C10 . . . . 161.53(12) ?
    C2 C1 C10 C25 . . . . -75.01(15) ?
    C2 C1 C10 C5 . . . . 48.67(16) ?
    C2 C1 C10 C9 . . . . 162.37(12) ?
    C6 C5 C10 C1 . . . . 176.78(11) ?
    C4 C5 C10 C1 . . . . -49.20(16) ?
    C6 C5 C10 C25 . . . . -63.77(15) ?
    C4 C5 C10 C25 . . . . 70.26(17) ?
    C6 C5 C10 C9 . . . . 62.16(14) ?
    C4 C5 C10 C9 . . . . -163.82(12) ?
    C11 C9 C10 C1 . . . . 63.99(15) ?
    C8 C9 C10 C1 . . . . -165.63(12) ?
    C11 C9 C10 C25 . . . . -54.20(18) ?
    C8 C9 C10 C25 . . . . 76.17(17) ?
    C11 C9 C10 C5 . . . . 179.88(12) ?
    C8 C9 C10 C5 . . . . -49.74(16) ?
    C8 C9 C11 C12 . . . . 42.11(17) ?
    C10 C9 C11 C12 . . . . 176.84(13) ?
    C9 C11 C12 C13 . . . . -8.9(2) ?
    C11 C12 C13 C18 . . . . 175.42(15) ?
    C11 C12 C13 C14 . . . . 0.4(2) ?
    C12 C13 C14 C15 . . . . -147.13(15) ?
    C18 C13 C14 C15 . . . . 37.92(19) ?
    C12 C13 C14 C27 . . . . 95.96(17) ?
    C18 C13 C14 C27 . . . . -78.98(16) ?
    C12 C13 C14 C8 . . . . -25.20(19) ?
    C18 C13 C14 C8 . . . . 159.86(13) ?
    C26 C8 C14 C13 . . . . -63.91(15) ?
    C7 C8 C14 C13 . . . . 177.83(12) ?
    C9 C8 C14 C13 . . . . 56.48(14) ?
    C26 C8 C14 C15 . . . . 58.41(16) ?
    C7 C8 C14 C15 . . . . -59.85(16) ?
    C9 C8 C14 C15 . . . . 178.81(12) ?
    C26 C8 C14 C27 . . . . 177.38(13) ?
    C7 C8 C14 C27 . . . . 59.12(16) ?
    C9 C8 C14 C27 . . . . -62.22(15) ?
    C13 C14 C15 C16 . . . . -41.70(19) ?
    C27 C14 C15 C16 . . . . 75.37(17) ?
    C8 C14 C15 C16 . . . . -163.09(14) ?
    C14 C15 C16 C17 . . . . 55.2(2) ?
    C15 C16 C17 C28 . . . . 60.95(18) ?
    C15 C16 C17 C18 . . . . -59.21(19) ?
    C15 C16 C17 C22 . . . . -179.86(14) ?
    C12 C13 C18 C19 . . . . -92.59(17) ?
    C14 C13 C18 C19 . . . . 82.48(17) ?
    C12 C13 C18 C17 . . . . 140.04(15) ?
    C14 C13 C18 C17 . . . . -44.89(19) ?
    C28 C17 C18 C13 . . . . -67.93(17) ?
    C16 C17 C18 C13 . . . . 52.61(17) ?
    C22 C17 C18 C13 . . . . 173.78(14) ?
    C28 C17 C18 C19 . . . . 165.93(14) ?
    C16 C17 C18 C19 . . . . -73.53(16) ?
    C22 C17 C18 C19 . . . . 47.64(18) ?
    C13 C18 C19 C20 . . . . 179.30(14) ?
    C17 C18 C19 C20 . . . . -53.72(19) ?
    C18 C19 C20 C30 . . . . -67.9(2) ?
    C18 C19 C20 C29 . . . . 173.33(16) ?
    C18 C19 C20 C21 . . . . 54.5(2) ?
    C30 C20 C21 C22 . . . . 68.38(19) ?
    C29 C20 C21 C22 . . . . -171.62(15) ?
    C19 C20 C21 C22 . . . . -53.75(19) ?
    C20 C21 C22 C17 . . . . 54.3(2) ?
    C28 C17 C22 C21 . . . . -168.41(16) ?
    C16 C17 C22 C21 . . . . 71.0(2) ?
    C18 C17 C22 C21 . . . . -49.1(2) ?
    O2 C31 C32 C33 . . . . -172.78(19) ?
    O1 C31 C32 C33 . . . . 7.4(3) ?
    O2 C31 C32 C37 . . . . 5.2(3) ?
    O1 C31 C32 C37 . . . . -174.68(19) ?
    C37 C32 C33 C34 . . . . 1.0(3) ?
    C31 C32 C33 C34 . . . . 179.0(2) ?
    C32 C33 C34 C35 . . . . -0.1(4) ?
    C33 C34 C35 C36 . . . . -0.7(4) ?
    C34 C35 C36 C37 . . . . 0.6(4) ?
    C33 C32 C37 C36 . . . . -1.1(4) ?
    C31 C32 C37 C36 . . . . -179.2(2) ?
    C35 C36 C37 C32 . . . . 0.3(4) ?
    O2 C31 O1 C3 . . . . 2.1(3) ?
    C32 C31 O1 C3 . . . . -178.04(13) ?
    C2 C3 O1 C31 . . . . 126.23(15) ?
    C4 C3 O1 C31 . . . . -109.16(15) ?
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
    C3 H3 O2 . 1.00 2.26 2.7148(19) 106.4
    C23 H23C O1 . 0.98 2.54 2.933(2) 103.5
