##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-07-02
_journal_date_accepted     2008-07-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1538
_journal_page_last     o1538
_journal_paper_category     QO
_journal_coeditor_code     BT2739
_publ_contact_author_name     'Jie Zeng'
_publ_contact_author_address
;School of Food Science,
 Henan Institute of Science & Technology ,
 Xinxiang 453003,
 People's Republic of China
;
_publ_contact_author_email     'j_zeng@yahoo.cn'
_publ_contact_author_fax     '86 373 3040709'
_publ_contact_author_phone     '86 373 3040674'
_publ_section_title
;
Arctigenin: a lignan from <i>Arctium lappa</i>
;
loop_
    _publ_author_name
    _publ_author_address
    'Gao, Haiyan'
;
 School of Food Science,
 Henan Institute of Science and Technology,
 Xinxiang 453003,
 People's Republic of China
;
    'Li, Guanglei'
;
 School of Food Science,
 Henan Institute of Science and Technology,
 Xinxiang 453003,
 People's Republic of China
;
    'Zhang, Junhe'
;
 School of Food Science,
 Henan Institute of Science and Technology,
 Xinxiang 453003,
 People's Republic of China
;
    'Zeng, Jie'
;
 School of Food Science,
 Henan Institute of Science and Technology,
 Xinxiang 453003,
 People's Republic of China
;
data_I
_chemical_name_systematic
;
(3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-
3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one
;
_chemical_name_common     Arctigenin
_chemical_formula_moiety     'C21 H24 O6'
_chemical_formula_sum     'C21 H24 O6'
_chemical_formula_iupac     'C21 H24 O6'
_chemical_formula_weight     372.40
_chemical_melting_point     ?
_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, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     9.4845(19)
_cell_length_b     10.065(2)
_cell_length_c     19.915(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1901.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5995
_cell_measurement_theta_min     2.267
_cell_measurement_theta_max     27.876
_cell_measurement_temperature     113(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.14
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.301
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_absorpt_correction_T_min     0.9868
_exptl_absorpt_correction_T_max     0.9906
_exptl_special_details
;
;
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     confocal
_diffrn_measurement_device_type     'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     13910
_diffrn_reflns_av_R_equivalents     0.0372
_diffrn_reflns_av_sigmaI/netI     0.0260
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     27.84
_diffrn_reflns_theta_full     27.84
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2581
_reflns_number_gt     2449
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0347
_refine_ls_R_factor_gt     0.0321
_refine_ls_wR_factor_gt     0.0773
_refine_ls_wR_factor_ref     0.0789
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     2581
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.1518P] where P=(Fo^2^+2Fc^2^)/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     0.199
_refine_diff_density_min     -0.153
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.032(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details     'none, Friedel Pairs merged'
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'CrystalStructure (Rigaku/MSC, 2005)'
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
    O O1 0.07380(13) 0.28900(13) 0.73971(6) 0.0287(3) Uani d . 1 . .
    O O2 0.23820(12) 0.17843(12) 0.82576(5) 0.0228(3) Uani d . 1 . .
    O O3 0.38552(14) 0.79457(13) 0.92594(6) 0.0329(3) Uani d . 1 . .
    O O4 0.34335(15) 0.69713(14) 1.02429(6) 0.0362(3) Uani d . 1 . .
    O O5 0.96166(13) 0.15373(12) 0.87738(6) 0.0226(3) Uani d . 1 . .
    H H5 1.036(2) 0.195(2) 0.8592(10) 0.034 Uiso d . 1 . .
    O O6 1.04322(12) 0.40766(12) 0.88872(6) 0.0241(3) Uani d . 1 . .
    C C1 0.44649(17) 0.48348(17) 0.79244(7) 0.0196(3) Uani d . 1 . .
    C C2 0.35798(18) 0.53926(18) 0.74441(8) 0.0230(3) Uani d . 1 . .
    H H2 0.3827 0.6219 0.7246 0.028 Uiso calc R 1 . .
    C C3 0.23339(18) 0.47622(18) 0.72471(8) 0.0247(4) Uani d . 1 . .
    H H3 0.1747 0.5159 0.6917 0.030 Uiso calc R 1 . .
    C C4 0.19554(17) 0.35649(18) 0.75310(8) 0.0226(3) Uani d . 1 . .
    C C5 0.28519(17) 0.29699(17) 0.80056(7) 0.0196(3) Uani d . 1 . .
    C C6 0.40879(17) 0.35955(17) 0.81937(7) 0.0192(3) Uani d . 1 . .
    H H6 0.4693 0.3180 0.8511 0.023 Uiso calc R 1 . .
    C C7 -0.0319(2) 0.3594(2) 0.70329(11) 0.0412(5) Uani d . 1 . .
    H H7A -0.0003 0.3730 0.6569 0.062 Uiso calc R 1 . .
    H H7B -0.0485 0.4458 0.7246 0.062 Uiso calc R 1 . .
    H H7C -0.1196 0.3079 0.7033 0.062 Uiso calc R 1 . .
    C C8 0.32263(19) 0.11735(19) 0.87673(9) 0.0276(4) Uani d . 1 . .
    H H8A 0.3305 0.1774 0.9153 0.041 Uiso calc R 1 . .
    H H8B 0.4168 0.0988 0.8588 0.041 Uiso calc R 1 . .
    H H8C 0.2784 0.0340 0.8910 0.041 Uiso calc R 1 . .
    C C9 0.57710(16) 0.55340(17) 0.81719(7) 0.0209(3) Uani d . 1 . .
    H H9A 0.6165 0.6068 0.7799 0.025 Uiso calc R 1 . .
    H H9B 0.6482 0.4855 0.8294 0.025 Uiso calc R 1 . .
    C C10 0.55425(17) 0.64553(16) 0.87818(8) 0.0213(3) Uani d . 1 . .
    H H10 0.6479 0.6827 0.8916 0.026 Uiso calc R 1 . .
    C C11 0.4557(2) 0.76166(18) 0.86314(9) 0.0287(4) Uani d . 1 . .
    H H11A 0.5100 0.8389 0.8464 0.034 Uiso calc R 1 . .
    H H11B 0.3856 0.7361 0.8286 0.034 Uiso calc R 1 . .
    C C12 0.39834(18) 0.69247(18) 0.96988(8) 0.0257(4) Uani d . 1 . .
    C C13 0.48662(16) 0.58224(16) 0.94058(8) 0.0192(3) Uani d . 1 . .
    H H13 0.4229 0.5086 0.9259 0.023 Uiso calc R 1 . .
    C C14 0.58852(17) 0.52865(17) 0.99399(7) 0.0211(3) Uani d . 1 . .
    H H14A 0.6435 0.6035 1.0129 0.025 Uiso calc R 1 . .
    H H14B 0.5334 0.4884 1.0310 0.025 Uiso calc R 1 . .
    C C15 0.68864(17) 0.42650(16) 0.96613(8) 0.0194(3) Uani d . 1 . .
    C C16 0.65324(16) 0.29296(17) 0.96147(7) 0.0205(3) Uani d . 1 . .
    H H16 0.5651 0.2633 0.9785 0.025 Uiso calc R 1 . .
    C C17 0.74541(16) 0.20166(17) 0.93208(7) 0.0206(3) Uani d . 1 . .
    H H17 0.7201 0.1105 0.9295 0.025 Uiso calc R 1 . .
    C C18 0.87370(16) 0.24419(16) 0.90675(7) 0.0188(3) Uani d . 1 . .
    C C19 0.91196(16) 0.37751(17) 0.91323(7) 0.0187(3) Uani d . 1 . .
    C C20 0.82073(16) 0.46753(17) 0.94260(7) 0.0192(3) Uani d . 1 . .
    H H20 0.8479 0.5580 0.9469 0.023 Uiso calc R 1 . .
    C C21 1.08409(19) 0.54337(18) 0.89079(10) 0.0329(4) Uani d . 1 . .
    H H21A 1.0905 0.5726 0.9376 0.049 Uiso calc R 1 . .
    H H21B 1.0139 0.5973 0.8671 0.049 Uiso calc R 1 . .
    H H21C 1.1761 0.5538 0.8691 0.049 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0263(6) 0.0277(7) 0.0322(6) -0.0037(6) -0.0070(5) 0.0021(5)
    O2 0.0269(6) 0.0178(6) 0.0237(5) 0.0014(5) 0.0016(5) 0.0025(4)
    O3 0.0430(7) 0.0206(6) 0.0353(7) 0.0115(6) 0.0054(6) 0.0006(5)
    O4 0.0416(7) 0.0322(8) 0.0349(7) 0.0107(7) 0.0139(6) -0.0030(6)
    O5 0.0210(5) 0.0180(6) 0.0288(6) 0.0004(5) 0.0004(5) -0.0031(5)
    O6 0.0187(5) 0.0194(6) 0.0342(6) -0.0017(5) 0.0050(5) -0.0041(5)
    C1 0.0205(7) 0.0212(8) 0.0171(7) 0.0035(7) 0.0033(6) 0.0004(6)
    C2 0.0258(8) 0.0209(8) 0.0222(8) 0.0017(7) 0.0033(6) 0.0036(6)
    C3 0.0247(8) 0.0270(9) 0.0222(8) 0.0030(7) -0.0030(6) 0.0041(7)
    C4 0.0225(7) 0.0241(9) 0.0214(7) 0.0008(7) -0.0002(6) -0.0028(6)
    C5 0.0250(8) 0.0159(7) 0.0179(7) 0.0034(7) 0.0053(6) 0.0007(6)
    C6 0.0218(7) 0.0200(8) 0.0158(7) 0.0060(7) 0.0023(6) -0.0002(6)
    C7 0.0310(10) 0.0340(11) 0.0584(12) -0.0034(10) -0.0192(9) 0.0041(10)
    C8 0.0271(8) 0.0259(9) 0.0297(9) 0.0047(8) 0.0052(7) 0.0108(7)
    C9 0.0193(7) 0.0229(8) 0.0206(7) 0.0009(7) 0.0030(6) 0.0030(6)
    C10 0.0223(7) 0.0177(8) 0.0237(7) -0.0003(7) 0.0015(6) 0.0014(6)
    C11 0.0358(9) 0.0193(8) 0.0308(9) 0.0049(8) 0.0032(7) 0.0029(7)
    C12 0.0250(8) 0.0215(8) 0.0307(8) 0.0035(7) 0.0022(7) -0.0025(7)
    C13 0.0187(7) 0.0162(8) 0.0227(8) 0.0006(6) 0.0017(6) -0.0015(6)
    C14 0.0213(7) 0.0222(8) 0.0198(7) 0.0007(7) 0.0028(6) 0.0000(6)
    C15 0.0208(7) 0.0223(8) 0.0149(7) 0.0024(7) -0.0018(6) 0.0008(6)
    C16 0.0192(7) 0.0220(8) 0.0204(7) -0.0012(7) 0.0001(6) 0.0027(6)
    C17 0.0218(7) 0.0182(8) 0.0218(7) -0.0020(7) -0.0035(6) 0.0019(6)
    C18 0.0193(7) 0.0182(8) 0.0190(7) 0.0037(6) -0.0036(6) -0.0017(6)
    C19 0.0163(7) 0.0217(8) 0.0183(7) -0.0010(6) -0.0018(6) 0.0009(6)
    C20 0.0204(7) 0.0186(8) 0.0188(7) -0.0003(7) -0.0023(6) -0.0009(6)
    C21 0.0260(9) 0.0208(9) 0.0519(11) -0.0064(8) 0.0114(8) -0.0055(8)
_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
    O1 C4 . 1.366(2) ?
    O1 C7 . 1.426(2) ?
    O2 C5 . 1.369(2) ?
    O2 C8 . 1.432(2) ?
    O3 C12 . 1.355(2) ?
    O3 C11 . 1.455(2) ?
    O4 C12 . 1.203(2) ?
    O5 C18 . 1.3665(19) ?
    O5 H5 . 0.90(2) ?
    O6 C19 . 1.3712(19) ?
    O6 C21 . 1.421(2) ?
    C1 C2 . 1.391(2) ?
    C1 C6 . 1.404(2) ?
    C1 C9 . 1.508(2) ?
    C2 C3 . 1.398(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.379(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.405(2) ?
    C5 C6 . 1.383(2) ?
    C6 H6 . 0.9500 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.543(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.526(2) ?
    C10 C13 . 1.537(2) ?
    C10 H10 . 1.0000 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.507(2) ?
    C13 C14 . 1.535(2) ?
    C13 H13 . 1.0000 ?
    C14 C15 . 1.506(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.389(2) ?
    C15 C20 . 1.400(2) ?
    C16 C17 . 1.397(2) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.385(2) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.396(2) ?
    C19 C20 . 1.383(2) ?
    C20 H20 . 0.9500 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4 O1 C7 . . 116.50(15) ?
    C5 O2 C8 . . 116.88(13) ?
    C12 O3 C11 . . 109.96(13) ?
    C18 O5 H5 . . 109.9(15) ?
    C19 O6 C21 . . 116.75(13) ?
    C2 C1 C6 . . 117.88(16) ?
    C2 C1 C9 . . 122.16(15) ?
    C6 C1 C9 . . 119.94(14) ?
    C1 C2 C3 . . 121.34(16) ?
    C1 C2 H2 . . 119.3 ?
    C3 C2 H2 . . 119.3 ?
    C4 C3 C2 . . 120.12(15) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    O1 C4 C3 . . 125.08(15) ?
    O1 C4 C5 . . 115.51(16) ?
    C3 C4 C5 . . 119.40(16) ?
    O2 C5 C6 . . 125.01(14) ?
    O2 C5 C4 . . 114.90(15) ?
    C6 C5 C4 . . 120.07(15) ?
    C5 C6 C1 . . 121.14(15) ?
    C5 C6 H6 . . 119.4 ?
    C1 C6 H6 . . 119.4 ?
    O1 C7 H7A . . 109.5 ?
    O1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O2 C8 H8A . . 109.5 ?
    O2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    O2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C1 C9 C10 . . 114.99(13) ?
    C1 C9 H9A . . 108.5 ?
    C10 C9 H9A . . 108.5 ?
    C1 C9 H9B . . 108.5 ?
    C10 C9 H9B . . 108.5 ?
    H9A C9 H9B . . 107.5 ?
    C11 C10 C13 . . 102.73(13) ?
    C11 C10 C9 . . 113.07(13) ?
    C13 C10 C9 . . 116.48(13) ?
    C11 C10 H10 . . 108.1 ?
    C13 C10 H10 . . 108.1 ?
    C9 C10 H10 . . 108.1 ?
    O3 C11 C10 . . 106.62(13) ?
    O3 C11 H11A . . 110.4 ?
    C10 C11 H11A . . 110.4 ?
    O3 C11 H11B . . 110.4 ?
    C10 C11 H11B . . 110.4 ?
    H11A C11 H11B . . 108.6 ?
    O4 C12 O3 . . 120.85(17) ?
    O4 C12 C13 . . 128.17(17) ?
    O3 C12 C13 . . 110.98(13) ?
    C12 C13 C14 . . 109.88(13) ?
    C12 C13 C10 . . 103.87(13) ?
    C14 C13 C10 . . 116.31(13) ?
    C12 C13 H13 . . 108.8 ?
    C14 C13 H13 . . 108.8 ?
    C10 C13 H13 . . 108.8 ?
    C15 C14 C13 . . 112.45(12) ?
    C15 C14 H14A . . 109.1 ?
    C13 C14 H14A . . 109.1 ?
    C15 C14 H14B . . 109.1 ?
    C13 C14 H14B . . 109.1 ?
    H14A C14 H14B . . 107.8 ?
    C16 C15 C20 . . 118.66(15) ?
    C16 C15 C14 . . 122.23(15) ?
    C20 C15 C14 . . 119.10(15) ?
    C15 C16 C17 . . 120.90(15) ?
    C15 C16 H16 . . 119.6 ?
    C17 C16 H16 . . 119.6 ?
    C18 C17 C16 . . 119.94(15) ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    O5 C18 C17 . . 119.10(15) ?
    O5 C18 C19 . . 121.42(15) ?
    C17 C18 C19 . . 119.46(15) ?
    O6 C19 C20 . . 125.01(15) ?
    O6 C19 C18 . . 114.57(14) ?
    C20 C19 C18 . . 120.42(15) ?
    C19 C20 C15 . . 120.55(15) ?
    C19 C20 H20 . . 119.7 ?
    C15 C20 H20 . . 119.7 ?
    O6 C21 H21A . . 109.5 ?
    O6 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O6 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 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
    C6 C1 C2 C3 . . . . 1.7(2) ?
    C9 C1 C2 C3 . . . . -176.52(14) ?
    C1 C2 C3 C4 . . . . 0.2(2) ?
    C7 O1 C4 C3 . . . . -11.9(2) ?
    C7 O1 C4 C5 . . . . 167.03(16) ?
    C2 C3 C4 O1 . . . . 177.18(15) ?
    C2 C3 C4 C5 . . . . -1.7(2) ?
    C8 O2 C5 C6 . . . . 1.7(2) ?
    C8 O2 C5 C4 . . . . -176.99(13) ?
    O1 C4 C5 O2 . . . . 1.0(2) ?
    C3 C4 C5 O2 . . . . 179.99(14) ?
    O1 C4 C5 C6 . . . . -177.79(13) ?
    C3 C4 C5 C6 . . . . 1.2(2) ?
    O2 C5 C6 C1 . . . . -177.86(14) ?
    C4 C5 C6 C1 . . . . 0.8(2) ?
    C2 C1 C6 C5 . . . . -2.2(2) ?
    C9 C1 C6 C5 . . . . 176.05(13) ?
    C2 C1 C9 C10 . . . . 89.17(18) ?
    C6 C1 C9 C10 . . . . -89.02(18) ?
    C1 C9 C10 C11 . . . . -63.25(19) ?
    C1 C9 C10 C13 . . . . 55.42(19) ?
    C12 O3 C11 C10 . . . . -17.30(19) yes
    C13 C10 C11 O3 . . . . 23.87(17) yes
    C9 C10 C11 O3 . . . . 150.24(14) ?
    C11 O3 C12 O4 . . . . -177.32(17) ?
    C11 O3 C12 C13 . . . . 2.8(2) yes
    O4 C12 C13 C14 . . . . -42.2(2) ?
    O3 C12 C13 C14 . . . . 137.62(14) ?
    O4 C12 C13 C10 . . . . -167.32(18) ?
    O3 C12 C13 C10 . . . . 12.54(18) yes
    C11 C10 C13 C12 . . . . -21.56(16) yes
    C9 C10 C13 C12 . . . . -145.71(14) ?
    C11 C10 C13 C14 . . . . -142.41(14) ?
    C9 C10 C13 C14 . . . . 93.44(17) ?
    C12 C13 C14 C15 . . . . -174.92(14) ?
    C10 C13 C14 C15 . . . . -57.32(19) ?
    C13 C14 C15 C16 . . . . -85.45(19) ?
    C13 C14 C15 C20 . . . . 93.00(17) ?
    C20 C15 C16 C17 . . . . -1.9(2) ?
    C14 C15 C16 C17 . . . . 176.52(14) ?
    C15 C16 C17 C18 . . . . -0.4(2) ?
    C16 C17 C18 O5 . . . . -179.14(13) ?
    C16 C17 C18 C19 . . . . 2.5(2) ?
    C21 O6 C19 C20 . . . . -3.5(2) ?
    C21 O6 C19 C18 . . . . 176.67(15) ?
    O5 C18 C19 O6 . . . . -0.7(2) ?
    C17 C18 C19 O6 . . . . 177.63(13) ?
    O5 C18 C19 C20 . . . . 179.43(14) ?
    C17 C18 C19 C20 . . . . -2.2(2) ?
    O6 C19 C20 C15 . . . . -179.96(14) ?
    C18 C19 C20 C15 . . . . -0.1(2) ?
    C16 C15 C20 C19 . . . . 2.2(2) ?
    C14 C15 C20 C19 . . . . -176.31(14) ?
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
    O5 H5 O2 1_655 0.90(2) 2.04(2) 2.8280(17) 146(2)
    O5 H5 O6 . 0.90(2) 2.22(2) 2.6799(18) 111.7(17)
    O5 H5 O1 1_655 0.90(2) 2.58(2) 3.2406(18) 130.8(16)
    C3 H3 O5 3_656 0.95 2.34 3.278(2) 168
    C14 H14A O4 4_567 0.99 2.86 3.687(2) 142
    C14 H14B O5 4_457 0.99 2.42 3.373(2) 162
    C20 H20 O4 4_567 0.95 2.53 3.446(2) 162