##############################################################################
###                                                                        ###
###        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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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-07-17
_journal_date_accepted     2009-08-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     10
_journal_page_first     o2330
_journal_page_last     o2330
_journal_paper_category     QO
_journal_coeditor_code     HG2542
_publ_contact_author_name     'Professor Mat\\'ias L\\'opez'
_publ_contact_author_address
;
Instituto de Bioorg\\'anica A. Gonz\\'alez
Universidad de La Laguna
Astrof\\'isico F. S\\'anchez,#2
38206 La Laguna, Tenerife
Spain
;
_publ_contact_author_email     'malopez@ull.es'
_publ_contact_author_fax     '34 922 318570'
_publ_contact_author_phone     '34 922 318588'
_publ_section_title
;
(-)-Istanbulin A
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'L\'opez-Rodr\'iguez, Mat\'ias' .
;
Instituto de Bioorg\'anica "A. Gonz\'alez"
Universidad de La Laguna
Astrof\'isico Francisco S\'anchez, 2
38206 La Laguna, Tenerife
Spain
;
    'Reina, Mat\'ias' .
;
Instituto de Productos Naturales y Agrobiolog\'ia (IPNA-CSIC)
Astrof\'isico Francisco S\'anchez, 3
38206 La Laguna, Tenerife
Spain
;
    'Dom\'inguez-D\'iaz, D.M.' .
;
Instituto de Productos Naturales y Agrobiolog\'ia (IPNA-CSIC)
Astrof\'isico Francisco S\'anchez, 3
38206 La Laguna, Tenerife
Spain
;
    'Fajardo, V.' .
;
Facultad de Ciencias
Universidad de Magallanes (UMAG)
Punta Arenas
Chile
;
    'Villarroel, L.' .
;
Facultad de Qu\'imica y Biolog\'ia
Universidad de Santiago de Chile
Chile
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4<i>H</i>,5<i>H</i>-
naphtho[2,3-<i>b</i>]furan-2,8-dione
;
_chemical_name_common     '(-)-Istanbulin A'
_chemical_formula_moiety     'C15 H20 O4'
_chemical_formula_sum     'C15 H20 O4'
_chemical_formula_iupac     'C15 H20 O4'
_chemical_formula_weight     264.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     7.432(4)
_cell_length_b     13.010(6)
_cell_length_c     8.161(6)
_cell_angle_alpha     90.00
_cell_angle_beta     115.47(4)
_cell_angle_gamma     90.00
_cell_volume     712.4(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     297
_cell_measurement_theta_min     4.3
_cell_measurement_theta_max     23.7
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.232
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     284
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCDcamera on \\k goniostat'
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     4410
_diffrn_reflns_av_R_equivalents     0.0180
_diffrn_reflns_av_sigmaI/netI     0.0217
_diffrn_reflns_theta_min     6.41
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     1678
_reflns_number_gt     1485
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0451
_refine_ls_R_factor_gt     0.0378
_refine_ls_wR_factor_gt     0.0912
_refine_ls_wR_factor_ref     0.0951
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     1678
_refine_ls_number_parameters     186
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.0898P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.196
_refine_diff_density_min     -0.115
_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 0.0000
                         '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     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare <i>et al.</i>, 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008 )'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     '<i>Win</i>GX (Farrugia,1999)'
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 0.4955(3) 0.50383(14) 0.8319(2) 0.0568(5) Uani d . 1 . .
    O O2 0.5421(4) 0.5731(2) 0.6018(3) 0.0869(7) Uani d . 1 . .
    O O3 0.6082(2) 0.37119(15) 1.04064(19) 0.0521(4) Uani d . 1 . .
    H H3 0.713(5) 0.354(3) 1.018(4) 0.079(9) Uiso d . 1 . .
    O O4 -0.0560(2) 0.35876(16) 0.9801(3) 0.0635(5) Uani d . 1 . .
    C C1 0.0324(3) 0.28290(19) 0.9675(3) 0.0456(5) Uani d . 1 . .
    C C2 -0.0216(4) 0.1763(2) 0.9971(4) 0.0635(7) Uani d . 1 . .
    H H2A -0.1422 0.1778 1.0153 0.079(9) Uiso calc R 1 . .
    H H2B 0.0844 0.1476 1.1053 0.073(9) Uiso calc R 1 . .
    C C3 -0.0542(4) 0.1087(2) 0.8333(4) 0.0643(7) Uani d . 1 . .
    H H3A -0.1759 0.1299 0.7312 0.074(9) Uiso calc R 1 . .
    H H3B -0.0713 0.0379 0.8615 0.059(8) Uiso calc R 1 . .
    C C4 0.1189(4) 0.11441(18) 0.7792(3) 0.0518(6) Uani d . 1 . .
    H H4 0.2377 0.0891 0.8827 0.059(7) Uiso calc R 1 . .
    C C5 0.1632(3) 0.22659(16) 0.7435(3) 0.0375(4) Uani d . 1 . .
    C C6 0.3567(3) 0.22904(18) 0.7137(3) 0.0448(5) Uani d . 1 . .
    H H6A 0.4602 0.1896 0.8084 0.057(7) Uiso calc R 1 . .
    H H6B 0.3309 0.1977 0.5979 0.050(7) Uiso calc R 1 . .
    C C7 0.4259(3) 0.33673(18) 0.7168(3) 0.0422(5) Uani d . 1 . .
    C C8 0.4541(3) 0.40177(17) 0.8797(3) 0.0412(5) Uani d . 1 . .
    C C9 0.2648(3) 0.40183(17) 0.9078(3) 0.0407(5) Uani d . 1 . .
    H H9A 0.1589 0.4368 0.8076 0.036(5) Uiso calc R 1 . .
    H H9B 0.2875 0.4377 1.0192 0.043(6) Uiso calc R 1 . .
    C C10 0.2059(3) 0.29068(16) 0.9181(3) 0.0372(4) Uani d . 1 . .
    H H10 0.3200 0.2583 1.0170 0.044(6) Uiso calc R 1 . .
    C C11 0.4554(3) 0.3931(2) 0.5961(3) 0.0488(6) Uani d . 1 . .
    C C12 0.5040(4) 0.4988(3) 0.6676(4) 0.0588(6) Uani d . 1 . .
    C C13 0.4395(4) 0.3664(3) 0.4119(3) 0.0668(8) Uani d . 1 . .
    H H13A 0.5521 0.3940 0.3982 0.090 Uiso calc R 1 . .
    H H13B 0.3190 0.3950 0.3207 0.090 Uiso calc R 1 . .
    H H13C 0.4374 0.2930 0.3988 0.090 Uiso calc R 1 . .
    C C14 -0.0102(3) 0.27228(19) 0.5782(3) 0.0512(5) Uani d . 1 . .
    H H14A 0.0173 0.3431 0.5648 0.090 Uiso calc R 1 . .
    H H14B -0.1303 0.2676 0.5947 0.090 Uiso calc R 1 . .
    H H14C -0.0266 0.2348 0.4713 0.090 Uiso calc R 1 . .
    C C15 0.0800(5) 0.0415(2) 0.6210(5) 0.0771(9) Uani d . 1 . .
    H H15A 0.1886 0.0454 0.5872 0.090 Uiso calc R 1 . .
    H H15B -0.0415 0.0607 0.5195 0.090 Uiso calc R 1 . .
    H H15C 0.0685 -0.0276 0.6569 0.090 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 0.0612(10) 0.0542(10) 0.0633(10) -0.0224(8) 0.0348(8) -0.0122(8)
    O2 0.0968(16) 0.0837(16) 0.0944(16) -0.0249(13) 0.0548(14) 0.0156(13)
    O3 0.0339(7) 0.0817(12) 0.0434(7) -0.0078(8) 0.0194(6) -0.0091(8)
    O4 0.0465(9) 0.0680(12) 0.0928(12) -0.0034(9) 0.0460(9) -0.0125(10)
    C1 0.0355(10) 0.0562(14) 0.0480(11) -0.0048(10) 0.0208(9) -0.0015(11)
    C2 0.0559(14) 0.0680(18) 0.0766(17) -0.0052(13) 0.0378(13) 0.0159(15)
    C3 0.0604(15) 0.0452(14) 0.0848(18) -0.0128(12) 0.0289(14) 0.0092(14)
    C4 0.0517(12) 0.0354(11) 0.0592(13) 0.0019(10) 0.0153(11) 0.0043(11)
    C5 0.0343(9) 0.0339(10) 0.0398(9) 0.0004(8) 0.0118(8) -0.0005(9)
    C6 0.0463(11) 0.0476(12) 0.0440(10) 0.0054(10) 0.0228(9) -0.0063(10)
    C7 0.0325(9) 0.0558(13) 0.0408(10) -0.0020(9) 0.0183(8) -0.0071(10)
    C8 0.0384(10) 0.0472(12) 0.0423(10) -0.0099(9) 0.0213(8) -0.0077(9)
    C9 0.0367(9) 0.0430(12) 0.0488(11) -0.0050(8) 0.0244(9) -0.0109(9)
    C10 0.0282(8) 0.0438(11) 0.0407(10) 0.0015(8) 0.0161(7) 0.0002(9)
    C11 0.0378(10) 0.0703(16) 0.0414(10) -0.0015(10) 0.0201(8) 0.0010(11)
    C12 0.0495(13) 0.0745(18) 0.0584(13) -0.0133(12) 0.0290(11) 0.0039(13)
    C13 0.0641(14) 0.099(2) 0.0423(11) -0.0002(16) 0.0278(11) 0.0043(14)
    C14 0.0465(12) 0.0464(13) 0.0465(11) 0.0016(10) 0.0066(9) 0.0057(11)
    C15 0.089(2) 0.0412(14) 0.093(2) -0.0098(14) 0.0316(18) -0.0157(14)
_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 C12 . 1.371(3) ?
    O1 C8 . 1.454(3) ?
    O2 C12 . 1.198(4) ?
    O3 C8 . 1.379(3) ?
    O3 H3 . 0.90(4) ?
    O4 C1 . 1.214(3) ?
    C1 C2 . 1.493(4) ?
    C1 C10 . 1.511(3) ?
    C2 C3 . 1.530(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.532(4) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C15 . 1.526(4) ?
    C4 C5 . 1.551(3) ?
    C4 H4 . 0.9800 ?
    C5 C14 . 1.529(3) ?
    C5 C6 . 1.558(3) ?
    C5 C10 . 1.561(3) ?
    C6 C7 . 1.489(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C11 . 1.320(3) ?
    C7 C8 . 1.512(3) ?
    C8 C9 . 1.519(3) ?
    C9 C10 . 1.524(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10 . 0.9800 ?
    C11 C12 . 1.477(4) ?
    C11 C13 . 1.497(3) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
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
    C12 O1 C8 . . 108.86(19) ?
    C8 O3 H3 . . 108(2) ?
    O4 C1 C2 . . 123.30(19) ?
    O4 C1 C10 . . 121.5(2) ?
    C2 C1 C10 . . 115.2(2) ?
    C1 C2 C3 . . 110.2(2) ?
    C1 C2 H2A . . 109.6 ?
    C3 C2 H2A . . 109.6 ?
    C1 C2 H2B . . 109.6 ?
    C3 C2 H2B . . 109.6 ?
    H2A C2 H2B . . 108.1 ?
    C2 C3 C4 . . 112.8(2) ?
    C2 C3 H3A . . 109.0 ?
    C4 C3 H3A . . 109.0 ?
    C2 C3 H3B . . 109.0 ?
    C4 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    C15 C4 C3 . . 109.7(2) ?
    C15 C4 C5 . . 113.8(2) ?
    C3 C4 C5 . . 111.89(19) ?
    C15 C4 H4 . . 107.0 ?
    C3 C4 H4 . . 107.0 ?
    C5 C4 H4 . . 107.0 ?
    C14 C5 C4 . . 111.40(18) ?
    C14 C5 C6 . . 109.80(18) ?
    C4 C5 C6 . . 109.48(18) ?
    C14 C5 C10 . . 111.15(18) ?
    C4 C5 C10 . . 107.89(17) ?
    C6 C5 C10 . . 106.99(16) ?
    C7 C6 C5 . . 110.60(17) ?
    C7 C6 H6A . . 109.5 ?
    C5 C6 H6A . . 109.5 ?
    C7 C6 H6B . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 108.1 ?
    C11 C7 C6 . . 132.6(2) ?
    C11 C7 C8 . . 109.9(2) ?
    C6 C7 C8 . . 117.24(18) ?
    O3 C8 O1 . . 109.53(17) ?
    O3 C8 C7 . . 114.85(19) ?
    O1 C8 C7 . . 103.91(17) ?
    O3 C8 C9 . . 107.47(17) ?
    O1 C8 C9 . . 110.88(18) ?
    C7 C8 C9 . . 110.20(16) ?
    C8 C9 C10 . . 108.33(16) ?
    C8 C9 H9A . . 110.0 ?
    C10 C9 H9A . . 110.0 ?
    C8 C9 H9B . . 110.0 ?
    C10 C9 H9B . . 110.0 ?
    H9A C9 H9B . . 108.4 ?
    C1 C10 C9 . . 112.13(17) ?
    C1 C10 C5 . . 110.24(17) ?
    C9 C10 C5 . . 114.02(16) ?
    C1 C10 H10 . . 106.7 ?
    C9 C10 H10 . . 106.7 ?
    C5 C10 H10 . . 106.7 ?
    C7 C11 C12 . . 108.2(2) ?
    C7 C11 C13 . . 130.8(3) ?
    C12 C11 C13 . . 120.9(2) ?
    O2 C12 O1 . . 121.3(3) ?
    O2 C12 C11 . . 129.7(2) ?
    O1 C12 C11 . . 108.9(2) ?
    C11 C13 H13A . . 109.5 ?
    C11 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C11 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C5 C14 H14A . . 109.5 ?
    C5 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C5 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C4 C15 H15A . . 109.5 ?
    C4 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C4 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 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
    O4 C1 C2 C3 . . . . 126.2(3) ?
    C10 C1 C2 C3 . . . . -53.2(3) ?
    C1 C2 C3 C4 . . . . 51.1(3) ?
    C2 C3 C4 C15 . . . . 177.4(2) ?
    C2 C3 C4 C5 . . . . -55.3(3) ?
    C15 C4 C5 C14 . . . . 59.4(3) ?
    C3 C4 C5 C14 . . . . -65.6(3) ?
    C15 C4 C5 C6 . . . . -62.2(3) ?
    C3 C4 C5 C6 . . . . 172.73(19) ?
    C15 C4 C5 C10 . . . . -178.3(2) ?
    C3 C4 C5 C10 . . . . 56.6(2) ?
    C14 C5 C6 C7 . . . . 69.0(2) ?
    C4 C5 C6 C7 . . . . -168.42(18) ?
    C10 C5 C6 C7 . . . . -51.8(2) ?
    C5 C6 C7 C11 . . . . -120.6(2) ?
    C5 C6 C7 C8 . . . . 53.2(2) ?
    C12 O1 C8 O3 . . . . 119.6(2) ?
    C12 O1 C8 C7 . . . . -3.5(2) ?
    C12 O1 C8 C9 . . . . -121.9(2) ?
    C11 C7 C8 O3 . . . . -117.3(2) ?
    C6 C7 C8 O3 . . . . 67.5(2) ?
    C11 C7 C8 O1 . . . . 2.3(2) ?
    C6 C7 C8 O1 . . . . -172.85(17) ?
    C11 C7 C8 C9 . . . . 121.1(2) ?
    C6 C7 C8 C9 . . . . -54.0(2) ?
    O3 C8 C9 C10 . . . . -72.0(2) ?
    O1 C8 C9 C10 . . . . 168.34(16) ?
    C7 C8 C9 C10 . . . . 53.8(2) ?
    O4 C1 C10 C9 . . . . 6.0(3) ?
    C2 C1 C10 C9 . . . . -174.5(2) ?
    O4 C1 C10 C5 . . . . -122.1(2) ?
    C2 C1 C10 C5 . . . . 57.3(2) ?
    C8 C9 C10 C1 . . . . 173.39(16) ?
    C8 C9 C10 C5 . . . . -60.4(2) ?
    C14 C5 C10 C1 . . . . 66.0(2) ?
    C4 C5 C10 C1 . . . . -56.4(2) ?
    C6 C5 C10 C1 . . . . -174.11(18) ?
    C14 C5 C10 C9 . . . . -61.1(2) ?
    C4 C5 C10 C9 . . . . 176.45(16) ?
    C6 C5 C10 C9 . . . . 58.7(2) ?
    C6 C7 C11 C12 . . . . 173.9(2) ?
    C8 C7 C11 C12 . . . . -0.3(2) ?
    C6 C7 C11 C13 . . . . -3.7(4) ?
    C8 C7 C11 C13 . . . . -177.9(2) ?
    C8 O1 C12 O2 . . . . -177.8(2) ?
    C8 O1 C12 C11 . . . . 3.5(3) ?
    C7 C11 C12 O2 . . . . 179.5(3) ?
    C13 C11 C12 O2 . . . . -2.6(4) ?
    C7 C11 C12 O1 . . . . -2.0(3) ?
    C13 C11 C12 O1 . . . . 175.8(2) ?
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
    O3 H3 O4 1_655 0.90(4) 1.87(4) 2.750(3) 164(4)