##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
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data_global
_audit_creation_method     'manual edited SHELXL-97 .cif file'
_journal_date_recd_electronic     2009-02-11
_journal_date_accepted     2009-02-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o545
_journal_page_last     o545
_journal_paper_category     QO
_journal_coeditor_code     BT2871
_publ_contact_author_name     'Ferdinand Belaj'
_publ_contact_author_address
; Institute of Chemistry,
  Karl-Franzens University Graz,
  Schubertstr. 1,
  A-8010 Graz,
  Austria
;
_publ_contact_author_email     ferdinand.belaj@uni-graz.at
_publ_contact_author_fax     '43(316)3809835'
_publ_contact_author_phone     '43(316)3805288'
_publ_section_title
;
<i>E</i>-Notopterol
;
loop_
    _publ_author_name
    _publ_author_address
    'Andreas Schinkovitz'
; Institute of Pharmaceutical Sciences, Department of Pharmacognosy,
  Karl-Franzens University Graz,
  Universit\"atsplatz 4,
  A-8010 Graz,
  Austria
;
    'Ferdinand Belaj'
; Institute of Chemistry,
  Karl-Franzens University Graz,
  Schubertstrasse 1,
  A-8010 Graz,
  Austria
;
    'Olaf Kunert'
; Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry,
  Karl-Franzens University Graz,
  Universit\"atsplatz 1,
  A-8010 Graz,
  Austria
;
    'Rudolf Bauer'
; Institute of Pharmaceutical Sciences, Department of Pharmacognosy,
  Karl-Franzens University Graz,
  Universit\"atsplatz 4,
  A-8010 Graz,
  Austria
;
data_I
_chemical_name_systematic
;
4-{[(2E)-5-hydroxy-3,7-dimethyl-
octa-2,6-dien-1-yl]oxy}-7<i>H</i>-furo[3,2-<i>g</i>][1]benzopyran-7-one
;
_chemical_name_common     'E-Notopterol'
_chemical_formula_moiety     'C21 H22 O5'
_chemical_formula_sum     'C21 H22 O5'
_chemical_formula_iupac     'C21 H22 O5'
_chemical_formula_weight     354.39
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.4317(10)
_cell_length_b     8.0912(16)
_cell_length_c     17.206(3)
_cell_angle_alpha     91.802(15)
_cell_angle_beta     94.240(13)
_cell_angle_gamma     97.473(15)
_cell_volume     884.6(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     60
_cell_measurement_theta_min     15.96
_cell_measurement_theta_max     19.80
_cell_measurement_temperature     95(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.44
_exptl_crystal_size_min     0.32
_exptl_crystal_density_diffrn     1.330
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.094
_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     95(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe four-circle'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     '\w-2\q'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4234
_diffrn_reflns_av_R_equivalents     0.0227
_diffrn_reflns_av_sigmaI/netI     0.0464
_diffrn_reflns_theta_min     2.54
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     3
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0.36
_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.
The non-hydrogen atoms were refined with anisotropic displacement parameters
without any constraints. The H atoms of the
7<i>H</i>-Furo[3,2-<i>g</i>][1]benzopyran-7-one ring system were put at the
external bisector of the C---C---C angle at a C---H distance of 0.95 \%A and a
common isotropic displacement parameter was refined (AFIX 43 of
<i>SHELXL97</i>). The H atoms of the CH~2~ groups were refined with common
isotropic displacement parameters for the H atoms of the same group and
idealized geometry with approximately tetrahedral angles and C---H distances
of 0.99 \%A (AFIX 23 of <i>SHELXL97</i>). The H atoms bonded to a C atom of a
C=C double bond were put at the external bisector of the C---C---C angle at a
C---H distance of 0.95 \%A but the individual isotropic displacement
parameters are free to refine (AFIX 43 of <i>SHELXL97</i>). The H atom of the
tertiary C---H group was refined with an individual isotropic displacement
parameter and all <i>X</i>---C---H angles equal at a C---H distance of 1.00
\%A (AFIX 13 of <i>SHELXL97</i>). The H atoms of the methyl groups were
refined with common isotropic displacement parameters for the H atoms of the
same group and idealized geometry with tetrahedral angles, enabling rotation
around the <i>X</i>---C bond, and C---H distances of 0.98 \%A (AFIX 137 of
<i>SHELXL97</i>). The H atom of the OH group was refined with a tetrahedral
C---O---H angle, enabling rotation around the C---O bond, O---H distance of
0.84 \%A, and with an individual isotropic displacement parameter (AFIX 147 of
<i>SHELXL97</i>).
;
_reflns_number_total     3462
_reflns_number_gt     2941
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0525
_refine_ls_R_factor_gt     0.0434
_refine_ls_wR_factor_gt     0.1061
_refine_ls_wR_factor_ref     0.1125
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     3462
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refU
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.2588P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.384
_refine_diff_density_min     -0.214
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'local software'
_computing_cell_refinement     'local software'
_computing_data_reduction     'local software'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'modified ORTEP (Johnson, 1965)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.08010(16) 1.43591(14) 0.41654(6) 0.0244(3) Uani d . 1 . .
    C C2 0.0927(2) 1.43677(19) 0.33658(9) 0.0246(3) Uani d . 1 . .
    H H2 -0.0037 1.4827 0.3016 0.028(2) Uiso calc R 1 . .
    C C3 0.2568(2) 1.36524(19) 0.31406(9) 0.0226(3) Uani d . 1 . .
    H H3 0.2957 1.3524 0.2622 0.028(2) Uiso calc R 1 . .
    C C4 0.5403(2) 1.23232(17) 0.40535(8) 0.0177(3) Uani d . 1 . .
    C C5 0.7767(2) 1.13743(18) 0.51262(9) 0.0202(3) Uani d . 1 . .
    H H5 0.8670 1.1018 0.4760 0.028(2) Uiso calc R 1 . .
    C C6 0.8224(2) 1.11882(19) 0.58937(9) 0.0225(3) Uani d . 1 . .
    H H6 0.9445 1.0707 0.6059 0.028(2) Uiso calc R 1 . .
    C C7 0.6889(2) 1.17088(19) 0.64707(9) 0.0228(3) Uani d . 1 . .
    O O7 0.71375(18) 1.15883(16) 0.71723(6) 0.0305(3) Uani d . 1 . .
    O O8 0.51411(17) 1.24050(14) 0.62003(6) 0.0231(3) Uani d . 1 . .
    C C9 0.2897(2) 1.33880(19) 0.52396(9) 0.0216(3) Uani d . 1 . .
    H H9 0.2045 1.3732 0.5626 0.028(2) Uiso calc R 1 . .
    C C13 0.3631(2) 1.31129(18) 0.38445(8) 0.0185(3) Uani d . 1 . .
    C C14 0.5942(2) 1.21012(17) 0.48527(8) 0.0179(3) Uani d . 1 . .
    C C18 0.4657(2) 1.26325(18) 0.54174(8) 0.0189(3) Uani d . 1 . .
    C C19 0.2464(2) 1.36067(18) 0.44558(9) 0.0200(3) Uani d . 1 . .
    O O4 0.66912(16) 1.17002(14) 0.35580(6) 0.0223(3) Uani d . 1 . .
    C C41 0.6201(2) 1.17328(19) 0.27226(8) 0.0206(3) Uani d . 1 . .
    H H411 0.6516 1.2880 0.2540 0.022(3) Uiso calc R 1 . .
    H H412 0.4695 1.1328 0.2584 0.022(3) Uiso calc R 1 . .
    C C42 0.7567(2) 1.05985(18) 0.23652(8) 0.0197(3) Uani d . 1 . .
    H H42 0.8956 1.0633 0.2601 0.030(5) Uiso calc R 1 . .
    C C43 0.7031(2) 0.95436(18) 0.17484(8) 0.0198(3) Uani d . 1 . .
    C C44 0.8569(2) 0.84090(19) 0.14954(9) 0.0215(3) Uani d . 1 . .
    H H441 0.9936 0.8725 0.1801 0.031(3) Uiso calc R 1 . .
    H H442 0.8797 0.8576 0.0939 0.031(3) Uiso calc R 1 . .
    C C45 0.7817(3) 0.6553(2) 0.16021(9) 0.0247(4) Uani d . 1 . .
    H H45 0.6569 0.6179 0.1228 0.026(4) Uiso calc R 1 . .
    O O5 0.7265(2) 0.62481(16) 0.23818(7) 0.0342(3) Uani d . 1 . .
    H H51 0.6537 0.6973 0.2528 0.068(8) Uiso calc R 1 . .
    C C46 0.9538(3) 0.5518(2) 0.14538(9) 0.0246(3) Uani d . 1 . .
    H H46 1.0863 0.5869 0.1731 0.022(4) Uiso calc R 1 . .
    C C47 0.9430(3) 0.4165(2) 0.09793(9) 0.0251(3) Uani d . 1 . .
    C C48 1.1328(3) 0.3278(2) 0.08976(10) 0.0322(4) Uani d . 1 . .
    H H481 1.2543 0.3891 0.1207 0.042(3) Uiso calc R 1 . .
    H H482 1.1628 0.3221 0.0348 0.042(3) Uiso calc R 1 . .
    H H483 1.1048 0.2146 0.1085 0.042(3) Uiso calc R 1 . .
    C C49 0.4927(3) 0.9353(2) 0.12808(9) 0.0248(3) Uani d . 1 . .
    H H491 0.4120 1.0230 0.1448 0.043(3) Uiso calc R 1 . .
    H H492 0.4150 0.8258 0.1365 0.043(3) Uiso calc R 1 . .
    H H493 0.5146 0.9448 0.0725 0.043(3) Uiso calc R 1 . .
    C C50 0.7499(3) 0.3374(2) 0.04907(10) 0.0335(4) Uani d . 1 . .
    H H501 0.6298 0.3945 0.0608 0.058(4) Uiso calc R 1 . .
    H H502 0.7204 0.2194 0.0609 0.058(4) Uiso calc R 1 . .
    H H503 0.7737 0.3470 -0.0063 0.058(4) 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 0.0215(5) 0.0223(6) 0.0295(6) 0.0061(4) -0.0006(4) -0.0023(5)
    C2 0.0264(8) 0.0193(8) 0.0272(8) 0.0028(6) -0.0037(6) 0.0002(6)
    C3 0.0268(8) 0.0172(7) 0.0236(8) 0.0043(6) -0.0013(6) -0.0002(6)
    C4 0.0202(7) 0.0113(7) 0.0212(7) 0.0004(6) 0.0036(6) -0.0027(6)
    C5 0.0224(8) 0.0142(7) 0.0234(8) 0.0002(6) 0.0025(6) -0.0003(6)
    C6 0.0241(8) 0.0178(7) 0.0247(8) 0.0007(6) -0.0012(6) 0.0025(6)
    C7 0.0239(8) 0.0191(8) 0.0227(8) -0.0053(6) -0.0015(6) 0.0015(6)
    O7 0.0328(6) 0.0363(7) 0.0199(6) -0.0044(5) -0.0006(5) 0.0032(5)
    O8 0.0251(6) 0.0251(6) 0.0183(5) 0.0006(5) 0.0026(4) -0.0005(4)
    C9 0.0199(7) 0.0190(8) 0.0254(8) -0.0001(6) 0.0053(6) -0.0041(6)
    C13 0.0212(7) 0.0118(7) 0.0217(7) 0.0011(6) 0.0005(6) -0.0018(6)
    C14 0.0201(7) 0.0120(7) 0.0208(7) -0.0001(6) 0.0014(6) -0.0016(6)
    C18 0.0224(7) 0.0144(7) 0.0185(7) -0.0026(6) 0.0014(6) -0.0013(6)
    C19 0.0180(7) 0.0131(7) 0.0283(8) 0.0016(6) 0.0001(6) -0.0014(6)
    O4 0.0263(6) 0.0255(6) 0.0168(5) 0.0100(5) 0.0020(4) -0.0023(4)
    C41 0.0266(8) 0.0184(7) 0.0167(7) 0.0033(6) 0.0014(6) 0.0002(6)
    C42 0.0217(7) 0.0186(7) 0.0192(7) 0.0032(6) 0.0022(6) 0.0020(6)
    C43 0.0255(8) 0.0163(7) 0.0181(7) 0.0032(6) 0.0037(6) 0.0038(6)
    C44 0.0277(8) 0.0195(8) 0.0180(7) 0.0043(6) 0.0043(6) -0.0008(6)
    C45 0.0281(8) 0.0212(8) 0.0256(8) 0.0058(7) 0.0039(6) 0.0000(6)
    O5 0.0427(7) 0.0292(7) 0.0366(7) 0.0163(6) 0.0186(6) 0.0099(5)
    C46 0.0267(8) 0.0224(8) 0.0253(8) 0.0058(7) 0.0028(6) 0.0017(6)
    C47 0.0329(9) 0.0202(8) 0.0233(8) 0.0049(7) 0.0062(6) 0.0053(6)
    C48 0.0444(10) 0.0266(9) 0.0290(9) 0.0141(8) 0.0090(7) 0.0005(7)
    C49 0.0306(9) 0.0237(8) 0.0200(7) 0.0047(7) -0.0004(6) -0.0013(6)
    C50 0.0424(10) 0.0243(9) 0.0322(9) -0.0008(8) 0.0030(8) -0.0013(7)
_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 C19 . 1.3688(18) ?
    O1 C2 . 1.3843(19) ?
    C2 C3 . 1.343(2) ?
    C2 H2 . 0.95 ?
    C3 C13 . 1.454(2) ?
    C3 H3 . 0.95 ?
    C4 O4 . 1.3613(18) ?
    C4 C13 . 1.407(2) ?
    C4 C14 . 1.416(2) ?
    C5 C6 . 1.349(2) ?
    C5 C14 . 1.436(2) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.447(2) ?
    C6 H6 . 0.95 ?
    C7 O7 . 1.2145(19) ?
    C7 O8 . 1.3788(19) ?
    O8 C18 . 1.3834(18) ?
    C9 C18 . 1.375(2) ?
    C9 C19 . 1.378(2) ?
    C9 H9 . 0.95 ?
    C13 C19 . 1.413(2) ?
    C14 C18 . 1.413(2) ?
    O4 C41 . 1.4504(17) ?
    C41 C42 . 1.499(2) ?
    C41 H411 . 0.99 ?
    C41 H412 . 0.99 ?
    C42 C43 . 1.336(2) ?
    C42 H42 . 0.95 ?
    C43 C49 . 1.509(2) ?
    C43 C44 . 1.512(2) ?
    C44 C45 . 1.537(2) ?
    C44 H441 . 0.99 ?
    C44 H442 . 0.99 ?
    C45 O5 . 1.4336(19) ?
    C45 C46 . 1.504(2) ?
    C45 H45 . 1.00 ?
    O5 H51 . 0.84 ?
    C46 C47 . 1.337(2) ?
    C46 H46 . 0.95 ?
    C47 C50 . 1.504(2) ?
    C47 C48 . 1.507(2) ?
    C48 H481 . 0.98 ?
    C48 H482 . 0.98 ?
    C48 H483 . 0.98 ?
    C49 H491 . 0.98 ?
    C49 H492 . 0.98 ?
    C49 H493 . 0.98 ?
    C50 H501 . 0.98 ?
    C50 H502 . 0.98 ?
    C50 H503 . 0.98 ?
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
    C19 O1 C2 . . 105.94(12) ?
    C3 C2 O1 . . 112.26(14) ?
    C3 C2 H2 . . 123.9 ?
    O1 C2 H2 . . 123.9 ?
    C2 C3 C13 . . 106.62(14) ?
    C2 C3 H3 . . 126.7 ?
    C13 C3 H3 . . 126.7 ?
    O4 C4 C13 . . 126.59(13) ?
    O4 C4 C14 . . 114.47(13) ?
    C13 C4 C14 . . 118.94(13) ?
    C6 C5 C14 . . 121.15(14) ?
    C6 C5 H5 . . 119.4 ?
    C14 C5 H5 . . 119.4 ?
    C5 C6 C7 . . 121.23(15) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    O7 C7 O8 . . 116.20(14) ?
    O7 C7 C6 . . 126.77(15) ?
    O8 C7 C6 . . 117.03(13) ?
    C7 O8 C18 . . 122.82(12) ?
    C18 C9 C19 . . 114.72(14) ?
    C18 C9 H9 . . 122.6 ?
    C19 C9 H9 . . 122.6 ?
    C4 C13 C19 . . 117.12(13) ?
    C4 C13 C3 . . 138.18(14) ?
    C19 C13 C3 . . 104.68(13) ?
    C18 C14 C4 . . 119.34(13) ?
    C18 C14 C5 . . 117.56(13) ?
    C4 C14 C5 . . 123.09(13) ?
    C9 C18 O8 . . 116.11(13) ?
    C9 C18 C14 . . 123.71(14) ?
    O8 C18 C14 . . 120.18(13) ?
    O1 C19 C9 . . 123.36(14) ?
    O1 C19 C13 . . 110.49(13) ?
    C9 C19 C13 . . 126.15(14) ?
    C4 O4 C41 . . 119.53(11) ?
    O4 C41 C42 . . 105.47(12) ?
    O4 C41 H411 . . 110.6 ?
    C42 C41 H411 . . 110.6 ?
    O4 C41 H412 . . 110.6 ?
    C42 C41 H412 . . 110.6 ?
    H411 C41 H412 . . 108.8 ?
    C43 C42 C41 . . 126.62(14) ?
    C43 C42 H42 . . 116.7 ?
    C41 C42 H42 . . 116.7 ?
    C42 C43 C49 . . 124.47(14) ?
    C42 C43 C44 . . 119.56(14) ?
    C49 C43 C44 . . 115.95(13) ?
    C43 C44 C45 . . 113.08(13) ?
    C43 C44 H441 . . 109.0 ?
    C45 C44 H441 . . 109.0 ?
    C43 C44 H442 . . 109.0 ?
    C45 C44 H442 . . 109.0 ?
    H441 C44 H442 . . 107.8 ?
    O5 C45 C46 . . 106.58(13) ?
    O5 C45 C44 . . 111.88(13) ?
    C46 C45 C44 . . 110.45(13) ?
    O5 C45 H45 . . 109.3 ?
    C46 C45 H45 . . 109.3 ?
    C44 C45 H45 . . 109.3 ?
    C45 O5 H51 . . 109.5 ?
    C47 C46 C45 . . 127.87(15) ?
    C47 C46 H46 . . 116.1 ?
    C45 C46 H46 . . 116.1 ?
    C46 C47 C50 . . 125.44(16) ?
    C46 C47 C48 . . 120.82(15) ?
    C50 C47 C48 . . 113.73(15) ?
    C47 C48 H481 . . 109.5 ?
    C47 C48 H482 . . 109.5 ?
    H481 C48 H482 . . 109.5 ?
    C47 C48 H483 . . 109.5 ?
    H481 C48 H483 . . 109.5 ?
    H482 C48 H483 . . 109.5 ?
    C43 C49 H491 . . 109.5 ?
    C43 C49 H492 . . 109.5 ?
    H491 C49 H492 . . 109.5 ?
    C43 C49 H493 . . 109.5 ?
    H491 C49 H493 . . 109.5 ?
    H492 C49 H493 . . 109.5 ?
    C47 C50 H501 . . 109.5 ?
    C47 C50 H502 . . 109.5 ?
    H501 C50 H502 . . 109.5 ?
    C47 C50 H503 . . 109.5 ?
    H501 C50 H503 . . 109.5 ?
    H502 C50 H503 . . 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
    C19 O1 C2 C3 . . . . 0.41(17) ?
    O1 C2 C3 C13 . . . . 0.19(18) ?
    C14 C5 C6 C7 . . . . 0.2(2) ?
    C5 C6 C7 O7 . . . . 179.33(15) ?
    C5 C6 C7 O8 . . . . -0.2(2) ?
    O7 C7 O8 C18 . . . . 179.60(13) ?
    C6 C7 O8 C18 . . . . -0.8(2) ?
    O4 C4 C13 C19 . . . . 177.50(13) ?
    C14 C4 C13 C19 . . . . -1.4(2) ?
    O4 C4 C13 C3 . . . . -4.3(3) ?
    C14 C4 C13 C3 . . . . 176.88(16) ?
    C2 C3 C13 C4 . . . . -179.08(17) ?
    C2 C3 C13 C19 . . . . -0.70(16) ?
    O4 C4 C14 C18 . . . . -177.18(12) ?
    C13 C4 C14 C18 . . . . 1.8(2) ?
    O4 C4 C14 C5 . . . . 3.7(2) ?
    C13 C4 C14 C5 . . . . -177.31(13) ?
    C6 C5 C14 C18 . . . . 0.8(2) ?
    C6 C5 C14 C4 . . . . 179.90(14) ?
    C19 C9 C18 O8 . . . . 179.60(12) ?
    C19 C9 C18 C14 . . . . -0.4(2) ?
    C7 O8 C18 C9 . . . . -178.14(13) ?
    C7 O8 C18 C14 . . . . 1.8(2) ?
    C4 C14 C18 C9 . . . . -0.9(2) ?
    C5 C14 C18 C9 . . . . 178.22(14) ?
    C4 C14 C18 O8 . . . . 179.09(12) ?
    C5 C14 C18 O8 . . . . -1.7(2) ?
    C2 O1 C19 C9 . . . . 178.89(14) ?
    C2 O1 C19 C13 . . . . -0.87(16) ?
    C18 C9 C19 O1 . . . . -178.88(13) ?
    C18 C9 C19 C13 . . . . 0.9(2) ?
    C4 C13 C19 O1 . . . . 179.76(12) ?
    C3 C13 C19 O1 . . . . 0.98(16) ?
    C4 C13 C19 C9 . . . . 0.0(2) ?
    C3 C13 C19 C9 . . . . -178.78(14) ?
    C13 C4 O4 C41 . . . . -3.8(2) ?
    C14 C4 O4 C41 . . . . 175.09(12) ?
    C4 O4 C41 C42 . . . . -166.21(12) ?
    O4 C41 C42 C43 . . . . 141.31(15) ?
    C41 C42 C43 C49 . . . . 2.1(2) ?
    C41 C42 C43 C44 . . . . -176.19(14) ?
    C42 C43 C44 C45 . . . . 113.54(16) ?
    C49 C43 C44 C45 . . . . -64.89(17) ?
    C43 C44 C45 O5 . . . . -53.12(17) ?
    C43 C44 C45 C46 . . . . -171.68(13) ?
    O5 C45 C46 C47 . . . . 109.83(18) ?
    C44 C45 C46 C47 . . . . -128.43(17) ?
    C45 C46 C47 C50 . . . . -0.7(3) ?
    C45 C46 C47 C48 . . . . 179.69(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
    O5 H51 O8 2_676 0.84 2.57 3.2193(16) 134.5