##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-11-16
_journal_date_accepted     2005-11-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     12
_journal_page_first     o4376
_journal_page_last     o4378
_journal_paper_category     EO
_journal_coeditor_code     CI6713
_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 6577888  Ext. 3690'
_publ_section_title
;
1,6,7-Trihydroxy-3-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
chloroform solvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Nawong Boonnak' ?
;     Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Suchada Chantrapromma'
;
Additional correspondence author, email: suchada.c@psu.ac.th
;
;     Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Hoong-Kun Fun' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Chatchanok Karalai' ?
;     Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,6,7-Trihydroxy-3-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
chloroform solvate
;
_chemical_name_common
;
Prunifoxanthone A
;
_chemical_formula_moiety     'C24 H26 O6, C H Cl3'
_chemical_formula_sum     'C25 H27 Cl3 O6'
_chemical_formula_iupac     'C24 H26 O6, C H Cl3'
_chemical_formula_weight     529.82
_chemical_melting_point        .395E-305
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.90590(10)
_cell_length_b     23.3103(3)
_cell_length_c     18.4042(2)
_cell_angle_alpha     90.00
_cell_angle_beta     103.4380(10)
_cell_angle_gamma     90.00
_cell_volume     2464.31(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4316
_cell_measurement_theta_min     1.43
_cell_measurement_theta_max     26.00
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     Needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1104
_exptl_absorpt_coefficient_mu     0.411
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.897
_exptl_absorpt_correction_T_max     0.948
_exptl_special_details
;
;
_diffrn_ambient_temperature     297(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
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     38758
_diffrn_reflns_av_R_equivalents     0.0344
_diffrn_reflns_av_sigmaI/netI     0.0190
_diffrn_reflns_theta_min     1.43
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_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 > 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     4316
_reflns_number_gt     3713
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0740
_refine_ls_R_factor_gt     0.0634
_refine_ls_wR_factor_gt     0.2047
_refine_ls_wR_factor_ref     0.2183
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     4316
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.1248P)²+5.5318P] 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     0.785
_refine_diff_density_min     -0.744
_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 0.0016
                         '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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'APEX2'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material
;
SHELXTL and PLATON (Spek, 2003)
;
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cl1 1.0112(3) 0.48154(5) 0.40237(7) 0.0592(4) Uani d . 1 . . Cl
    Cl2 1.0310(3) 0.36816(6) 0.46764(7) 0.0565(4) Uani d . 1 . . Cl
    Cl3 0.5920(2) 0.42519(7) 0.41845(8) 0.0666(5) Uani d . 1 . . Cl
    C25 0.8704(8) 0.41528(19) 0.4016(2) 0.0395(10) Uani d . 1 . . C
    H25 0.8525 0.3981 0.3520 0.047 Uiso calc R 1 . . H
    O1 0.3494(4) 0.27247(10) 0.35848(12) 0.0188(5) Uani d . 1 . . O
    H1 0.2439 0.2961 0.3478 0.028 Uiso calc R 1 . . H
    O2 -0.0216(4) 0.31757(10) 0.28782(12) 0.0200(5) Uani d . 1 . . O
    O3 -0.0283(4) 0.20722(10) 0.11384(12) 0.0180(5) Uani d . 1 . . O
    O4 0.7020(4) 0.13068(10) 0.23917(13) 0.0224(5) Uani d . 1 . . O
    O5 -0.7695(4) 0.27110(11) -0.01993(13) 0.0218(5) Uani d . 1 . . O
    H5 -0.7272 0.2582 -0.0561 0.033 Uiso calc R 1 . . H
    O6 -0.8149(4) 0.33811(10) 0.09166(13) 0.0217(5) Uani d . 1 . . O
    H6 -0.8992 0.3324 0.0502 0.033 Uiso calc R 1 . . H
    C1 0.3427(6) 0.23721(14) 0.29880(17) 0.0173(7) Uani d . 1 . . C
    C2 0.5270(6) 0.20017(14) 0.29977(18) 0.0179(7) Uani d . 1 . . C
    C3 0.5139(6) 0.16527(14) 0.23659(19) 0.0189(7) Uani d . 1 . . C
    C4 0.3242(6) 0.16689(14) 0.17481(18) 0.0176(7) Uani d . 1 . . C
    H4 0.3174 0.1429 0.1340 0.021 Uiso calc R 1 . . H
    C5 0.1483(6) 0.20511(14) 0.17650(17) 0.0169(7) Uani d . 1 . . C
    C6 0.1479(6) 0.24141(14) 0.23682(17) 0.0168(7) Uani d . 1 . . C
    C7 -0.0363(6) 0.28225(13) 0.23531(17) 0.0166(7) Uani d . 1 . . C
    C8 -0.2331(6) 0.27977(13) 0.17045(17) 0.0163(7) Uani d . 1 . . C
    C9 -0.2171(5) 0.24270(13) 0.11215(18) 0.0157(6) Uani d . 1 . . C
    C10 -0.3900(6) 0.23814(14) 0.04687(17) 0.0180(7) Uani d . 1 . . C
    H10 -0.3730 0.2137 0.0086 0.022 Uiso calc R 1 . . H
    C11 -0.5877(6) 0.27097(14) 0.04063(18) 0.0181(7) Uani d . 1 . . C
    C12 -0.6128(5) 0.30731(14) 0.09907(18) 0.0163(7) Uani d . 1 . . C
    C13 -0.4392(6) 0.31281(14) 0.16351(17) 0.0168(7) Uani d . 1 . . C
    C14 -0.4790(6) 0.35472(14) 0.22252(18) 0.0175(7) Uani d . 1 . . C
    H14A -0.6450 0.3596 0.2178 0.021 Uiso calc R 1 . . H
    H14B -0.4122 0.3393 0.2718 0.021 Uiso calc R 1 . . H
    C15 -0.3701(6) 0.41234(14) 0.21442(17) 0.0181(7) Uani d . 1 . . C
    H15 -0.2139 0.4124 0.2128 0.022 Uiso calc R 1 . . H
    C16 -0.4763(6) 0.46262(15) 0.20939(19) 0.0222(7) Uani d . 1 . . C
    C17 -0.3506(7) 0.51769(15) 0.2028(2) 0.0296(8) Uani d . 1 . . C
    H17A -0.1957 0.5093 0.1979 0.044 Uiso calc R 1 . . H
    H17B -0.3429 0.5405 0.2467 0.044 Uiso calc R 1 . . H
    H17C -0.4327 0.5384 0.1596 0.044 Uiso calc R 1 . . H
    C18 -0.7293(6) 0.46924(17) 0.2106(2) 0.0329(9) Uani d . 1 . . C
    H18A -0.8196 0.4406 0.1792 0.049 Uiso calc R 1 . . H
    H18B -0.7824 0.5067 0.1926 0.049 Uiso calc R 1 . . H
    H18C -0.7470 0.4647 0.2609 0.049 Uiso calc R 1 . . H
    C19 0.7080(7) 0.09709(15) 0.1750(2) 0.0269(8) Uani d . 1 . . C
    H19A 0.8546 0.0775 0.1828 0.040 Uiso calc R 1 . . H
    H19B 0.6894 0.1216 0.1322 0.040 Uiso calc R 1 . . H
    H19C 0.5840 0.0695 0.1669 0.040 Uiso calc R 1 . . H
    C20 0.7353(6) 0.19688(14) 0.36579(18) 0.0190(7) Uani d . 1 . . C
    H20A 0.8732 0.1876 0.3480 0.023 Uiso calc R 1 . . H
    H20B 0.7597 0.2340 0.3901 0.023 Uiso calc R 1 . . H
    C21 0.7022(6) 0.15230(14) 0.42181(18) 0.0185(7) Uani d . 1 . . C
    H21 0.5721 0.1572 0.4416 0.022 Uiso calc R 1 . . H
    C22 0.8338(6) 0.10712(14) 0.44667(18) 0.0210(7) Uani d . 1 . . C
    C23 1.0530(7) 0.09147(16) 0.4224(2) 0.0306(9) Uani d . 1 . . C
    H23A 1.0705 0.1163 0.3824 0.046 Uiso calc R 1 . . H
    H23B 1.0432 0.0524 0.4056 0.046 Uiso calc R 1 . . H
    H23C 1.1849 0.0958 0.4638 0.046 Uiso calc R 1 . . H
    C24 0.7706(7) 0.06684(17) 0.5029(2) 0.0310(9) Uani d . 1 . . C
    H24A 0.6343 0.0808 0.5172 0.046 Uiso calc R 1 . . H
    H24B 0.8974 0.0646 0.5462 0.046 Uiso calc R 1 . . H
    H24C 0.7397 0.0294 0.4811 0.046 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C25 . 1.753(5) y
    Cl2 C25 . 1.746(4) y
    Cl3 C25 . 1.758(5) y
    C25 H25 . 0.98 ?
    O1 C1 . 1.365(4) y
    O1 H1 . 0.82 ?
    O2 C7 . 1.257(4) y
    O3 C5 . 1.364(4) y
    O3 C9 . 1.383(4) y
    O4 C3 . 1.364(4) y
    O4 C19 . 1.424(4) y
    O5 C11 . 1.356(4) y
    O5 H5 . 0.82 ?
    O6 C12 . 1.372(4) y
    O6 H6 . 0.82 ?
    C1 C2 . 1.386(5) ?
    C1 C6 . 1.423(5) ?
    C2 C3 . 1.407(5) ?
    C2 C20 . 1.517(4) ?
    C3 C4 . 1.399(5) ?
    C4 C5 . 1.375(5) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.396(5) ?
    C6 C7 . 1.441(5) ?
    C7 C8 . 1.461(4) ?
    C8 C9 . 1.398(5) ?
    C8 C13 . 1.421(5) ?
    C9 C10 . 1.388(5) ?
    C10 C11 . 1.378(5) ?
    C10 H10 . 0.93 ?
    C11 C12 . 1.404(5) ?
    C12 C13 . 1.382(5) ?
    C13 C14 . 1.519(4) ?
    C14 C15 . 1.512(5) ?
    C14 H14A . 0.97 ?
    C14 H14B . 0.97 ?
    C15 C16 . 1.323(5) y
    C15 H15 . 0.93 ?
    C16 C17 . 1.502(5) ?
    C16 C18 . 1.507(5) ?
    C17 H17A . 0.96 ?
    C17 H17B . 0.96 ?
    C17 H17C . 0.96 ?
    C18 H18A . 0.96 ?
    C18 H18B . 0.96 ?
    C18 H18C . 0.96 ?
    C19 H19A . 0.96 ?
    C19 H19B . 0.96 ?
    C19 H19C . 0.96 ?
    C20 C21 . 1.508(4) ?
    C20 H20A . 0.97 ?
    C20 H20B . 0.97 ?
    C21 C22 . 1.326(5) y
    C21 H21 . 0.93 ?
    C22 C24 . 1.507(5) ?
    C22 C23 . 1.509(5) ?
    C23 H23A . 0.96 ?
    C23 H23B . 0.96 ?
    C23 H23C . 0.96 ?
    C24 H24A . 0.96 ?
    C24 H24B . 0.96 ?
    C24 H24C . 0.96 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    Cl2 C25 Cl1 . . 111.6(3) ?
    Cl2 C25 Cl3 . . 109.8(2) ?
    Cl1 C25 Cl3 . . 110.1(3) ?
    Cl2 C25 H25 . . 108.4 ?
    Cl1 C25 H25 . . 108.4 ?
    Cl3 C25 H25 . . 108.4 ?
    C1 O1 H1 . . 109.5 ?
    C5 O3 C9 . . 119.6(2) ?
    C3 O4 C19 . . 118.2(3) ?
    C11 O5 H5 . . 109.5 ?
    C12 O6 H6 . . 109.5 ?
    O1 C1 C2 . . 119.3(3) ?
    O1 C1 C6 . . 118.0(3) ?
    C2 C1 C6 . . 122.7(3) ?
    C1 C2 C3 . . 117.2(3) ?
    C1 C2 C20 . . 122.0(3) ?
    C3 C2 C20 . . 120.7(3) ?
    O4 C3 C4 . . 122.4(3) ?
    O4 C3 C2 . . 115.2(3) ?
    C4 C3 C2 . . 122.4(3) ?
    C5 C4 C3 . . 117.8(3) ?
    C5 C4 H4 . . 121.1 ?
    C3 C4 H4 . . 121.1 ?
    O3 C5 C4 . . 116.0(3) y
    O3 C5 C6 . . 120.5(3) ?
    C4 C5 C6 . . 123.5(3) y
    C5 C6 C1 . . 116.4(3) y
    C5 C6 C7 . . 121.7(3) y
    C1 C6 C7 . . 121.8(3) ?
    O2 C7 C6 . . 120.1(3) ?
    O2 C7 C8 . . 123.6(3) ?
    C6 C7 C8 . . 116.3(3) ?
    C9 C8 C13 . . 118.4(3) ?
    C9 C8 C7 . . 118.0(3) y
    C13 C8 C7 . . 123.7(3) y
    O3 C9 C10 . . 113.6(3) y
    O3 C9 C8 . . 123.4(3) y
    C10 C9 C8 . . 123.0(3) ?
    C11 C10 C9 . . 117.9(3) ?
    C11 C10 H10 . . 121.0 ?
    C9 C10 H10 . . 121.0 ?
    O5 C11 C10 . . 124.3(3) ?
    O5 C11 C12 . . 115.1(3) ?
    C10 C11 C12 . . 120.6(3) ?
    O6 C12 C13 . . 119.5(3) ?
    O6 C12 C11 . . 118.9(3) ?
    C13 C12 C11 . . 121.6(3) ?
    C12 C13 C8 . . 118.4(3) ?
    C12 C13 C14 . . 117.8(3) ?
    C8 C13 C14 . . 123.8(3) ?
    C15 C14 C13 . . 111.1(3) ?
    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 ?
    C16 C15 C14 . . 126.1(3) y
    C16 C15 H15 . . 117.0 ?
    C14 C15 H15 . . 117.0 ?
    C15 C16 C17 . . 121.9(3) ?
    C15 C16 C18 . . 123.0(3) y
    C17 C16 C18 . . 115.1(3) y
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C16 C18 H18A . . 109.5 ?
    C16 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C16 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O4 C19 H19A . . 109.5 ?
    O4 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O4 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C21 C20 C2 . . 111.9(3) ?
    C21 C20 H20A . . 109.2 ?
    C2 C20 H20A . . 109.2 ?
    C21 C20 H20B . . 109.2 ?
    C2 C20 H20B . . 109.2 ?
    H20A C20 H20B . . 107.9 ?
    C22 C21 C20 . . 128.6(3) y
    C22 C21 H21 . . 115.7 ?
    C20 C21 H21 . . 115.7 ?
    C21 C22 C24 . . 120.8(3) ?
    C21 C22 C23 . . 124.4(3) y
    C24 C22 C23 . . 114.8(3) y
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C22 C24 H24A . . 109.5 ?
    C22 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C22 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 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
    O1 C1 C2 C3 . . . . -179.1(3) ?
    C6 C1 C2 C3 . . . . -1.0(5) ?
    O1 C1 C2 C20 . . . . 0.9(5) ?
    C6 C1 C2 C20 . . . . 179.0(3) ?
    C19 O4 C3 C4 . . . . 2.8(4) ?
    C19 O4 C3 C2 . . . . -175.8(3) ?
    C1 C2 C3 O4 . . . . 178.2(3) ?
    C20 C2 C3 O4 . . . . -1.7(4) ?
    C1 C2 C3 C4 . . . . -0.3(5) ?
    C20 C2 C3 C4 . . . . 179.7(3) ?
    O4 C3 C4 C5 . . . . -177.1(3) ?
    C2 C3 C4 C5 . . . . 1.3(5) ?
    C9 O3 C5 C4 . . . . 177.2(3) ?
    C9 O3 C5 C6 . . . . -4.6(4) ?
    C3 C4 C5 O3 . . . . 177.1(3) ?
    C3 C4 C5 C6 . . . . -1.1(5) ?
    O3 C5 C6 C1 . . . . -178.3(3) ?
    C4 C5 C6 C1 . . . . -0.2(5) ?
    O3 C5 C6 C7 . . . . -0.2(5) ?
    C4 C5 C6 C7 . . . . 177.9(3) ?
    O1 C1 C6 C5 . . . . 179.3(3) ?
    C2 C1 C6 C5 . . . . 1.2(5) ?
    O1 C1 C6 C7 . . . . 1.3(4) ?
    C2 C1 C6 C7 . . . . -176.8(3) ?
    C5 C6 C7 O2 . . . . -174.0(3) ?
    C1 C6 C7 O2 . . . . 3.9(5) ?
    C5 C6 C7 C8 . . . . 5.7(4) ?
    C1 C6 C7 C8 . . . . -176.4(3) ?
    O2 C7 C8 C9 . . . . 173.3(3) ?
    C6 C7 C8 C9 . . . . -6.4(4) ?
    O2 C7 C8 C13 . . . . -6.8(5) ?
    C6 C7 C8 C13 . . . . 173.5(3) ?
    C5 O3 C9 C10 . . . . -176.4(3) ?
    C5 O3 C9 C8 . . . . 3.7(4) ?
    C13 C8 C9 O3 . . . . -177.9(3) ?
    C7 C8 C9 O3 . . . . 2.0(5) ?
    C13 C8 C9 C10 . . . . 2.2(5) ?
    C7 C8 C9 C10 . . . . -177.9(3) ?
    O3 C9 C10 C11 . . . . 178.6(3) ?
    C8 C9 C10 C11 . . . . -1.4(5) ?
    C9 C10 C11 O5 . . . . 179.6(3) ?
    C9 C10 C11 C12 . . . . -0.6(5) ?
    O5 C11 C12 O6 . . . . 1.6(4) ?
    C10 C11 C12 O6 . . . . -178.2(3) ?
    O5 C11 C12 C13 . . . . -178.3(3) ?
    C10 C11 C12 C13 . . . . 2.0(5) ?
    O6 C12 C13 C8 . . . . 179.0(3) ?
    C11 C12 C13 C8 . . . . -1.2(5) ?
    O6 C12 C13 C14 . . . . -1.9(4) ?
    C11 C12 C13 C14 . . . . 178.0(3) ?
    C9 C8 C13 C12 . . . . -0.8(4) ?
    C7 C8 C13 C12 . . . . 179.3(3) ?
    C9 C8 C13 C14 . . . . -179.9(3) ?
    C7 C8 C13 C14 . . . . 0.2(5) ?
    C12 C13 C14 C15 . . . . -95.4(3) ?
    C8 C13 C14 C15 . . . . 83.7(4) ?
    C13 C14 C15 C16 . . . . 127.3(3) ?
    C14 C15 C16 C17 . . . . 178.9(3) ?
    C14 C15 C16 C18 . . . . -0.4(5) ?
    C1 C2 C20 C21 . . . . 91.1(4) ?
    C3 C2 C20 C21 . . . . -88.9(4) ?
    C2 C20 C21 C22 . . . . 122.1(4) ?
    C20 C21 C22 C24 . . . . -179.6(3) ?
    C20 C21 C22 C23 . . . . 0.4(6) ?
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
    O1 H1 O2 1_555 0.82 1.77 2.505(3) 149 y
    O5 H5 O1 4_465 0.82 1.88 2.695(3) 176 y
    O6 H6 O5 1_555 0.82 2.18 2.643(3) 116 y
    C14 H14A O6 1_555 0.97 2.36 2.769(4) 105 y
    C14 H14B O2 1_555 0.97 2.31 2.825(4) 112 y
    C25 H25 O2 1_655 0.98 2.42 3.256(5) 142 y
