##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1R,5R,7R,8S)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8-methyl-1,5,7-tris(3-
methyl-2-butenyl)-8-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione
;
_chemical_name_common     'Guttiferone A'
_chemical_formula_moiety     'C38 H50 O6'
_chemical_formula_sum     'C38 H50 O6'
_chemical_formula_iupac     'C38 H50 O6'
_chemical_formula_weight     602.78
_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+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     8.7860(10)
_cell_length_b     11.4490(10)
_cell_length_c     34.306(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3450.9(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4991
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     29.131
_cell_measurement_temperature     173(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.160
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1304
_exptl_absorpt_coefficient_mu     0.077
_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     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker--Nonius KappaCCD'
_diffrn_measurement_method     φ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9050
_diffrn_reflns_av_R_equivalents     0.0360
_diffrn_reflns_av_sigmaI/netI     0.0568
_diffrn_reflns_theta_min     1.88
_diffrn_reflns_theta_max     29.13
_diffrn_reflns_theta_full     29.13
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -46
_diffrn_reflns_limit_l_max     46
_diffrn_standards_number     ?
_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     5171
_reflns_number_gt     3899
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0717
_refine_ls_R_factor_gt     0.0471
_refine_ls_wR_factor_gt     0.0968
_refine_ls_wR_factor_ref     0.1052
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     5171
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0482P)²+0.2481P] 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     0.192
_refine_diff_density_min     -0.184
_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     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON98 (Spek, 1998)'
_computing_publication_material     SHELXL97
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 O1A 0.67799(18) -0.21629(16) -0.07016(4) 0.0375(4) Uani d . 1 . .
    H H1O 0.7458 -0.2652 -0.0757 0.056 Uiso calc R 1 . .
    O O2 0.5018(2) -0.03885(17) -0.04626(4) 0.0466(5) Uani d . 1 . .
    H H2O 0.5171 -0.0656 -0.0687 0.070 Uiso calc R 1 . .
    O O3A 0.86545(17) -0.06552(16) 0.09727(4) 0.0375(4) Uani d . 1 . .
    H H3O 0.8665 -0.0425 0.1205 0.056 Uiso calc R 1 . .
    O O4 0.40429(17) -0.11708(13) 0.07929(4) 0.0299(3) Uani d . 1 . .
    O O5 0.34069(17) 0.21458(13) 0.15260(4) 0.0325(4) Uani d . 1 . .
    O O6 0.78963(16) 0.01873(14) 0.15805(4) 0.0299(3) Uani d . 1 . .
    C C1 0.8115(3) -0.1848(2) 0.03061(6) 0.0334(5) Uani d . 1 . .
    H H1 0.8856 -0.2158 0.0479 0.040 Uiso calc . 1 . .
    C C2 0.8022(3) -0.2267(2) -0.00734(6) 0.0355(5) Uani d . 1 . .
    H H2 0.8678 -0.2876 -0.0158 0.043 Uiso calc . 1 . .
    C C3 0.6972(3) -0.17935(19) -0.03258(6) 0.0290(5) Uani d . 1 . .
    C C4 0.6032(3) -0.0881(2) -0.02065(6) 0.0304(5) Uani d . 1 . .
    C C5 0.6089(3) -0.04798(19) 0.01720(6) 0.0293(5) Uani d . 1 . .
    H H5 0.5428 0.0128 0.0255 0.035 Uiso calc . 1 . .
    C C6 0.7129(2) -0.09752(19) 0.04335(6) 0.0268(4) Uani d . 1 . .
    C C7 0.7288(2) -0.05943(19) 0.08380(6) 0.0271(5) Uani d . 1 . .
    C C8 0.6099(2) -0.01620(17) 0.10850(5) 0.0226(4) Uani d . 1 . .
    C C9 0.4490(2) -0.04212(18) 0.10227(5) 0.0236(4) Uani d . 1 . .
    C C10 0.3308(2) 0.01980(18) 0.12740(5) 0.0236(4) Uani d . 1 . .
    C C11 0.3997(2) 0.11934(18) 0.15022(5) 0.0241(4) Uani d . 1 . .
    C C12 0.5401(2) 0.08585(18) 0.17339(5) 0.0237(4) Uani d . 1 . .
    C C13 0.6530(2) 0.02649(18) 0.14614(5) 0.0242(4) Uani d . 1 . .
    C C14 0.1972(2) 0.0602(2) 0.10136(6) 0.0307(5) Uani d . 1 . .
    H H14A 0.1484 -0.0093 0.0896 0.037 Uiso calc . 1 . .
    H H14B 0.1204 0.0996 0.1179 0.037 Uiso calc . 1 . .
    C C15 0.2445(3) 0.1424(2) 0.06917(7) 0.0386(6) Uani d . 1 . .
    H H15 0.2975 0.2108 0.0770 0.046 Uiso calc . 1 . .
    C C16 0.2207(3) 0.1299(2) 0.03130(7) 0.0438(6) Uani d . 1 . .
    C C17 0.2746(4) 0.2221(3) 0.00251(9) 0.0731(10) Uani d . 1 . .
    H H17A 0.3229 0.2864 0.0167 0.110 Uiso calc . 1 . .
    H H17B 0.1873 0.2519 -0.0122 0.110 Uiso calc . 1 . .
    H H17C 0.3483 0.1873 -0.0155 0.110 Uiso calc . 1 . .
    C C18 0.1421(4) 0.0284(3) 0.01271(8) 0.0608(8) Uani d . 1 . .
    H H18A 0.1231 -0.0320 0.0324 0.091 Uiso calc . 1 . .
    H H18B 0.2067 -0.0037 -0.0080 0.091 Uiso calc . 1 . .
    H H18C 0.0452 0.0543 0.0016 0.091 Uiso calc . 1 . .
    C C19 0.6197(3) 0.19799(19) 0.18872(6) 0.0284(5) Uani d . 1 . .
    H H19A 0.5452 0.2453 0.2036 0.034 Uiso calc . 1 . .
    H H19B 0.7026 0.1756 0.2068 0.034 Uiso calc . 1 . .
    C C20 0.6844(3) 0.27072(19) 0.15624(6) 0.0304(5) Uani d . 1 . .
    H H20 0.6140 0.2953 0.1369 0.036 Uiso calc . 1 . .
    C C21 0.8268(3) 0.30484(19) 0.15114(7) 0.0337(5) Uani d . 1 . .
    C C22 0.9540(3) 0.2781(3) 0.17891(8) 0.0461(7) Uani d . 1 . .
    H H22A 0.9572 0.3379 0.1993 0.069 Uiso calc . 1 . .
    H H22B 1.0509 0.2777 0.1648 0.069 Uiso calc . 1 . .
    H H22C 0.9370 0.2014 0.1908 0.069 Uiso calc . 1 . .
    C C23 0.8743(3) 0.3757(2) 0.11631(7) 0.0512(7) Uani d . 1 . .
    H H23A 0.7903 0.3787 0.0975 0.077 Uiso calc . 1 . .
    H H23B 0.9633 0.3395 0.1041 0.077 Uiso calc . 1 . .
    H H23C 0.9001 0.4552 0.1246 0.077 Uiso calc . 1 . .
    C C24 0.2731(2) -0.06685(18) 0.15917(6) 0.0252(4) Uani d . 1 . .
    H H24A 0.1885 -0.0293 0.1735 0.030 Uiso calc . 1 . .
    H H24B 0.2314 -0.1368 0.1460 0.030 Uiso calc . 1 . .
    C C25 0.3940(3) -0.10702(18) 0.18896(5) 0.0258(4) Uani d . 1 . .
    H H25 0.3340 -0.1402 0.2111 0.031 Uiso calc . 1 . .
    C C26 0.4825(2) -0.00143(18) 0.20710(5) 0.0249(4) Uani d . 1 . .
    C C27 0.4929(2) -0.20993(18) 0.17429(6) 0.0275(5) Uani d . 1 . .
    H H27A 0.5497 -0.1848 0.1508 0.033 Uiso calc . 1 . .
    H H27B 0.5681 -0.2305 0.1946 0.033 Uiso calc . 1 . .
    C C28 0.4004(3) -0.3162(2) 0.16449(7) 0.0357(5) Uani d . 1 . .
    H H28 0.3182 -0.3329 0.1816 0.043 Uiso calc . 1 . .
    C C29 0.4191(3) -0.3898(2) 0.13499(7) 0.0415(6) Uani d . 1 . .
    C C30 0.5374(3) -0.3773(2) 0.10369(8) 0.0522(7) Uani d . 1 . .
    H H30A 0.5846 -0.3000 0.1055 0.078 Uiso calc . 1 . .
    H H30B 0.4894 -0.3862 0.0781 0.078 Uiso calc . 1 . .
    H H30C 0.6154 -0.4377 0.1070 0.078 Uiso calc . 1 . .
    C C31 0.3210(4) -0.4970(2) 0.13093(10) 0.0644(9) Uani d . 1 . .
    H H31A 0.2451 -0.4982 0.1519 0.097 Uiso calc . 1 . .
    H H31B 0.3848 -0.5670 0.1327 0.097 Uiso calc . 1 . .
    H H31C 0.2692 -0.4955 0.1056 0.097 Uiso calc . 1 . .
    C C32 0.6170(3) -0.0437(2) 0.23204(6) 0.0318(5) Uani d . 1 . .
    H H32A 0.6614 0.0227 0.2460 0.048 Uiso calc . 1 . .
    H H32B 0.6944 -0.0790 0.2151 0.048 Uiso calc . 1 . .
    H H32C 0.5811 -0.1019 0.2509 0.048 Uiso calc . 1 . .
    C C33 0.3751(3) 0.06942(19) 0.23428(5) 0.0297(5) Uani d . 1 . .
    H H33A 0.4368 0.1281 0.2484 0.036 Uiso calc . 1 . .
    H H33B 0.3014 0.1124 0.2178 0.036 Uiso calc . 1 . .
    C C34 0.2854(3) -0.0028(2) 0.26450(6) 0.0343(5) Uani d . 1 . .
    H H34A 0.1970 -0.0402 0.2516 0.041 Uiso calc . 1 . .
    H H34B 0.3515 -0.0654 0.2750 0.041 Uiso calc . 1 . .
    C C35 0.2300(3) 0.0736(2) 0.29769(6) 0.0317(5) Uani d . 1 . .
    H H35 0.2998 0.0862 0.3184 0.038 Uiso calc . 1 . .
    C C36 0.0972(3) 0.1241(2) 0.30112(6) 0.0397(6) Uani d . 1 . .
    C C37 0.0612(3) 0.2007(3) 0.33590(8) 0.0531(7) Uani d . 1 . .
    H H37A 0.1488 0.2021 0.3536 0.080 Uiso calc . 1 . .
    H H37B -0.0276 0.1694 0.3496 0.080 Uiso calc . 1 . .
    H H37C 0.0392 0.2802 0.3270 0.080 Uiso calc . 1 . .
    C C38 -0.0300(4) 0.1075(4) 0.27284(9) 0.0936(15) Uani d . 1 . .
    H H38A 0.0097 0.0732 0.2487 0.140 Uiso calc . 1 . .
    H H38B -0.0768 0.1832 0.2671 0.140 Uiso calc . 1 . .
    H H38C -0.1064 0.0552 0.2842 0.140 Uiso calc . 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
    O1A C3 . 1.367(2) ?
    O1A H1O . 0.8400 ?
    O2 C4 . 1.373(3) ?
    O2 H2O . 0.8400 ?
    O3A C7 . 1.289(3) y
    O3A H3O . 0.8400 ?
    O4 C9 . 1.230(2) y
    O5 C11 . 1.210(3) y
    O6 C13 . 1.271(2) y
    C1 C2 . 1.390(3) ?
    C1 C6 . 1.393(3) y
    C1 H1 . 0.9500 ?
    C2 C3 . 1.377(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.393(3) ?
    C4 C5 . 1.378(3) ?
    C5 C6 . 1.400(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.461(3) y
    C7 C8 . 1.433(3) y
    C8 C13 . 1.432(3) y
    C8 C9 . 1.460(3) y
    C9 C10 . 1.524(3) y
    C10 C11 . 1.510(3) y
    C10 C14 . 1.546(3) ?
    C10 C24 . 1.558(3) y
    C11 C12 . 1.517(3) y
    C12 C13 . 1.523(3) ?
    C12 C19 . 1.554(3) ?
    C12 C26 . 1.610(3) ?
    C14 C15 . 1.509(3) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.324(3) y
    C15 H15 . 0.9500 ?
    C16 C18 . 1.494(4) ?
    C16 C17 . 1.521(4) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 C20 . 1.503(3) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 C21 . 1.322(3) y
    C20 H20 . 0.9500 ?
    C21 C22 . 1.500(4) ?
    C21 C23 . 1.504(3) ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 C25 . 1.544(3) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C25 C27 . 1.548(3) ?
    C25 C26 . 1.566(3) ?
    C25 H25 . 1.0000 ?
    C26 C32 . 1.538(3) ?
    C26 C33 . 1.555(3) ?
    C27 C28 . 1.501(3) ?
    C27 H27A . 0.9900 ?
    C27 H27B . 0.9900 ?
    C28 C29 . 1.327(3) y
    C28 H28 . 0.9500 ?
    C29 C30 . 1.501(4) ?
    C29 C31 . 1.506(4) ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 0.9800 ?
    C33 C34 . 1.543(3) y
    C33 H33A . 0.9900 ?
    C33 H33B . 0.9900 ?
    C34 C35 . 1.516(3) ?
    C34 H34A . 0.9900 ?
    C34 H34B . 0.9900 ?
    C35 C36 . 1.307(4) y
    C35 H35 . 0.9500 ?
    C36 C38 . 1.492(4) ?
    C36 C37 . 1.514(4) ?
    C37 H37A . 0.9800 ?
    C37 H37B . 0.9800 ?
    C37 H37C . 0.9800 ?
    C38 H38A . 0.9800 ?
    C38 H38B . 0.9800 ?
    C38 H38C . 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
    C3 O1A H1O . . 109.5 ?
    C4 O2 H2O . . 109.5 ?
    C7 O3A H3O . . 109.5 ?
    C2 C1 C6 . . 120.3(2) ?
    C2 C1 H1 . . 119.8 ?
    C6 C1 H1 . . 119.8 ?
    C3 C2 C1 . . 119.5(2) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    O1A C3 C2 . . 123.7(2) ?
    O1A C3 C4 . . 115.8(2) ?
    C2 C3 C4 . . 120.5(2) ?
    O2 C4 C5 . . 119.3(2) ?
    O2 C4 C3 . . 120.34(19) ?
    C5 C4 C3 . . 120.3(2) ?
    C4 C5 C6 . . 119.5(2) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C1 C6 C5 . . 119.70(18) ?
    C1 C6 C7 . . 116.9(2) ?
    C5 C6 C7 . . 123.4(2) ?
    O3A C7 C8 . . 119.07(18) ?
    O3A C7 C6 . . 114.42(19) ?
    C8 C7 C6 . . 126.50(19) ?
    C13 C8 C7 . . 117.27(18) ?
    C13 C8 C9 . . 117.24(18) ?
    C7 C8 C9 . . 123.29(18) y
    O4 C9 C8 . . 123.01(18) ?
    O4 C9 C10 . . 118.00(18) ?
    C8 C9 C10 . . 118.83(17) ?
    C11 C10 C9 . . 111.78(17) y
    C11 C10 C14 . . 112.22(18) ?
    C9 C10 C14 . . 109.25(15) ?
    C11 C10 C24 . . 104.38(15) y
    C9 C10 C24 . . 108.72(16) y
    C14 C10 C24 . . 110.35(17) ?
    O5 C11 C10 . . 122.92(19) ?
    O5 C11 C12 . . 122.74(19) ?
    C10 C11 C12 . . 114.03(18) ?
    C11 C12 C13 . . 108.73(15) y
    C11 C12 C19 . . 109.54(18) ?
    C13 C12 C19 . . 106.48(17) y
    C11 C12 C26 . . 106.10(16) ?
    C13 C12 C26 . . 111.64(17) ?
    C19 C12 C26 . . 114.27(16) ?
    O6 C13 C8 . . 121.07(19) ?
    O6 C13 C12 . . 116.68(17) ?
    C8 C13 C12 . . 122.23(18) ?
    C15 C14 C10 . . 113.59(18) ?
    C15 C14 H14A . . 108.8 ?
    C10 C14 H14A . . 108.8 ?
    C15 C14 H14B . . 108.8 ?
    C10 C14 H14B . . 108.8 ?
    H14A C14 H14B . . 107.7 ?
    C16 C15 C14 . . 127.4(2) ?
    C16 C15 H15 . . 116.3 ?
    C14 C15 H15 . . 116.3 ?
    C15 C16 C18 . . 125.2(3) ?
    C15 C16 C17 . . 120.9(3) ?
    C18 C16 C17 . . 114.0(2) ?
    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 ?
    C20 C19 C12 . . 112.16(16) ?
    C20 C19 H19A . . 109.2 ?
    C12 C19 H19A . . 109.2 ?
    C20 C19 H19B . . 109.2 ?
    C12 C19 H19B . . 109.2 ?
    H19A C19 H19B . . 107.9 ?
    C21 C20 C19 . . 128.3(2) ?
    C21 C20 H20 . . 115.8 ?
    C19 C20 H20 . . 115.8 ?
    C20 C21 C22 . . 124.1(2) ?
    C20 C21 C23 . . 121.8(2) ?
    C22 C21 C23 . . 114.1(2) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C25 C24 C10 . . 115.40(17) ?
    C25 C24 H24A . . 108.4 ?
    C10 C24 H24A . . 108.4 ?
    C25 C24 H24B . . 108.4 ?
    C10 C24 H24B . . 108.4 ?
    H24A C24 H24B . . 107.5 ?
    C24 C25 C27 . . 113.43(17) ?
    C24 C25 C26 . . 112.00(17) ?
    C27 C25 C26 . . 115.97(18) ?
    C24 C25 H25 . . 104.7 ?
    C27 C25 H25 . . 104.7 ?
    C26 C25 H25 . . 104.7 ?
    C32 C26 C33 . . 107.30(16) ?
    C32 C26 C25 . . 111.07(17) ?
    C33 C26 C25 . . 109.86(17) ?
    C32 C26 C12 . . 110.70(17) ?
    C33 C26 C12 . . 107.32(16) ?
    C25 C26 C12 . . 110.47(15) ?
    C28 C27 C25 . . 112.70(18) ?
    C28 C27 H27A . . 109.1 ?
    C25 C27 H27A . . 109.1 ?
    C28 C27 H27B . . 109.1 ?
    C25 C27 H27B . . 109.1 ?
    H27A C27 H27B . . 107.8 ?
    C29 C28 C27 . . 128.2(2) ?
    C29 C28 H28 . . 115.9 ?
    C27 C28 H28 . . 115.9 ?
    C28 C29 C30 . . 124.8(2) ?
    C28 C29 C31 . . 121.1(3) ?
    C30 C29 C31 . . 114.1(2) ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C29 C31 H31A . . 109.5 ?
    C29 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C29 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C26 C32 H32A . . 109.5 ?
    C26 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    C26 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
    C34 C33 C26 . . 115.68(18) ?
    C34 C33 H33A . . 108.4 ?
    C26 C33 H33A . . 108.4 ?
    C34 C33 H33B . . 108.4 ?
    C26 C33 H33B . . 108.4 ?
    H33A C33 H33B . . 107.4 ?
    C35 C34 C33 . . 111.06(19) ?
    C35 C34 H34A . . 109.4 ?
    C33 C34 H34A . . 109.4 ?
    C35 C34 H34B . . 109.4 ?
    C33 C34 H34B . . 109.4 ?
    H34A C34 H34B . . 108.0 ?
    C36 C35 C34 . . 127.6(2) ?
    C36 C35 H35 . . 116.2 ?
    C34 C35 H35 . . 116.2 ?
    C35 C36 C38 . . 123.6(2) ?
    C35 C36 C37 . . 120.9(2) ?
    C38 C36 C37 . . 115.5(2) ?
    C36 C37 H37A . . 109.5 ?
    C36 C37 H37B . . 109.5 ?
    H37A C37 H37B . . 109.5 ?
    C36 C37 H37C . . 109.5 ?
    H37A C37 H37C . . 109.5 ?
    H37B C37 H37C . . 109.5 ?
    C36 C38 H38A . . 109.5 ?
    C36 C38 H38B . . 109.5 ?
    H38A C38 H38B . . 109.5 ?
    C36 C38 H38C . . 109.5 ?
    H38A C38 H38C . . 109.5 ?
    H38B C38 H38C . . 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 . . . . 1.6(4) ?
    C1 C2 C3 O1A . . . . -178.8(2) ?
    C1 C2 C3 C4 . . . . 1.6(4) ?
    O1A C3 C4 O2 . . . . -1.6(3) ?
    C2 C3 C4 O2 . . . . 178.1(2) ?
    O1A C3 C4 C5 . . . . 177.1(2) ?
    C2 C3 C4 C5 . . . . -3.2(3) ?
    O2 C4 C5 C6 . . . . -179.6(2) ?
    C3 C4 C5 C6 . . . . 1.7(3) ?
    C2 C1 C6 C5 . . . . -3.1(3) ?
    C2 C1 C6 C7 . . . . 179.2(2) ?
    C4 C5 C6 C1 . . . . 1.5(3) ?
    C4 C5 C6 C7 . . . . 179.0(2) ?
    C1 C6 C7 O3A . . . . 31.4(3) ?
    C5 C6 C7 O3A . . . . -146.2(2) ?
    C1 C6 C7 C8 . . . . -149.5(2) ?
    C5 C6 C7 C8 . . . . 32.9(3) ?
    O3A C7 C8 C13 . . . . 4.7(3) ?
    C6 C7 C8 C13 . . . . -174.4(2) ?
    O3A C7 C8 C9 . . . . -157.9(2) y
    C6 C7 C8 C9 . . . . 23.0(3) y
    C13 C8 C9 O4 . . . . -150.92(19) ?
    C7 C8 C9 O4 . . . . 11.7(3) ?
    C13 C8 C9 C10 . . . . 24.5(3) ?
    C7 C8 C9 C10 . . . . -172.91(19) ?
    O4 C9 C10 C11 . . . . -172.73(17) y
    C8 C9 C10 C11 . . . . 11.7(3) ?
    O4 C9 C10 C14 . . . . -47.9(2) ?
    C8 C9 C10 C14 . . . . 136.48(19) y
    O4 C9 C10 C24 . . . . 72.6(2) ?
    C8 C9 C10 C24 . . . . -103.0(2) ?
    C9 C10 C11 O5 . . . . 134.6(2) ?
    C14 C10 C11 O5 . . . . 11.4(3) ?
    C24 C10 C11 O5 . . . . -108.1(2) ?
    C9 C10 C11 C12 . . . . -51.6(2) y
    C14 C10 C11 C12 . . . . -174.77(16) ?
    C24 C10 C11 C12 . . . . 65.7(2) ?
    O5 C11 C12 C13 . . . . -133.6(2) ?
    C10 C11 C12 C13 . . . . 52.6(2) ?
    O5 C11 C12 C19 . . . . -17.6(3) ?
    C10 C11 C12 C19 . . . . 168.63(15) ?
    O5 C11 C12 C26 . . . . 106.2(2) ?
    C10 C11 C12 C26 . . . . -67.6(2) ?
    C7 C8 C13 O6 . . . . -4.7(3) y
    C9 C8 C13 O6 . . . . 158.98(19) ?
    C7 C8 C13 C12 . . . . 173.66(19) ?
    C9 C8 C13 C12 . . . . -22.6(3) ?
    C11 C12 C13 O6 . . . . 163.19(18) ?
    C19 C12 C13 O6 . . . . 45.2(2) ?
    C26 C12 C13 O6 . . . . -80.1(2) ?
    C11 C12 C13 C8 . . . . -15.3(3) ?
    C19 C12 C13 C8 . . . . -133.2(2) ?
    C26 C12 C13 C8 . . . . 101.4(2) ?
    C11 C10 C14 C15 . . . . 65.4(2) ?
    C9 C10 C14 C15 . . . . -59.1(2) ?
    C24 C10 C14 C15 . . . . -178.62(18) ?
    C10 C14 C15 C16 . . . . 124.4(3) ?
    C14 C15 C16 C18 . . . . -0.9(5) ?
    C14 C15 C16 C17 . . . . 179.3(3) ?
    C11 C12 C19 C20 . . . . -66.6(2) ?
    C13 C12 C19 C20 . . . . 50.8(2) ?
    C26 C12 C19 C20 . . . . 174.53(18) ?
    C12 C19 C20 C21 . . . . -122.6(2) ?
    C19 C20 C21 C22 . . . . -1.8(4) ?
    C19 C20 C21 C23 . . . . 178.6(2) ?
    C11 C10 C24 C25 . . . . -55.1(2) ?
    C9 C10 C24 C25 . . . . 64.3(2) ?
    C14 C10 C24 C25 . . . . -175.85(17) ?
    C10 C24 C25 C27 . . . . -83.4(2) ?
    C10 C24 C25 C26 . . . . 50.3(2) ?
    C24 C25 C26 C32 . . . . -171.79(15) ?
    C27 C25 C26 C32 . . . . -39.4(2) ?
    C24 C25 C26 C33 . . . . 69.7(2) ?
    C27 C25 C26 C33 . . . . -157.99(17) ?
    C24 C25 C26 C12 . . . . -48.6(2) ?
    C27 C25 C26 C12 . . . . 83.8(2) ?
    C11 C12 C26 C32 . . . . 178.64(16) ?
    C13 C12 C26 C32 . . . . 60.3(2) ?
    C19 C12 C26 C32 . . . . -60.6(2) ?
    C11 C12 C26 C33 . . . . -64.6(2) ?
    C13 C12 C26 C33 . . . . 177.14(17) ?
    C19 C12 C26 C33 . . . . 56.2(2) ?
    C11 C12 C26 C25 . . . . 55.2(2) ?
    C13 C12 C26 C25 . . . . -63.1(2) ?
    C19 C12 C26 C25 . . . . 175.99(17) ?
    C24 C25 C27 C28 . . . . -59.3(2) ?
    C26 C25 C27 C28 . . . . 169.03(17) ?
    C25 C27 C28 C29 . . . . 140.8(2) ?
    C27 C28 C29 C30 . . . . -2.6(4) ?
    C27 C28 C29 C31 . . . . 176.2(2) ?
    C32 C26 C33 C34 . . . . -71.1(2) ?
    C25 C26 C33 C34 . . . . 49.8(2) ?
    C12 C26 C33 C34 . . . . 169.90(18) ?
    C26 C33 C34 C35 . . . . 160.03(18) ?
    C33 C34 C35 C36 . . . . 94.7(3) ?
    C34 C35 C36 C38 . . . . 4.3(5) ?
    C34 C35 C36 C37 . . . . -178.4(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
    O1A H1O O4 3_545 0.84 1.94 2.7732(19) 171
    O3A H3O O6 1_555 0.84 1.62 2.3934(18) 153
data_global
_journal_date_recd_electronic     2007-01-12
_journal_date_accepted     2007-02-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1282
_journal_page_last     o1284
_journal_paper_category     EO
_journal_coeditor_code     LH2291
_publ_contact_author_name
;
Bruno Ndjakou Lenta
;
_publ_contact_author_address
;
Chemistry Department, Bielefeld University, POBox 100131, 33615
 Bielefeld,Germany
;
_publ_contact_author_email     lentabruno@yahoo.fr
_publ_contact_author_fax     '05211068094'
_publ_contact_author_phone     '05211062147'
_publ_section_title
;\
(1R,5R,7R,8S)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8-\
methyl-1,5,7-tris(3-
methyl-2-butenyl)-8-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ndjakou Lenta, Bruno' .
;
 Department of Chemistry
 Bielefeld University
 PO Box 100131
 33501 Bieleleld
 Germany
;
    'Diderot Tchamo Noungoue' .
;
Department of Organic Chemistry
 Faculty of Science, PO Box 812
 University of Yaounde
 Cameroon
;
    'Krishna Prasad Devkota' .
;Department of Chemistry
 Bielefeld University
 PO Box 100131
 33501 Bieleleld
 Germany
;
    'Patrice Aime Fokou' .
;Department of Chemistry
 Bielefeld University
 PO Box 100131
 33501 Bieleleld
 Germany
;
    'Silvere Ngouela ' .
;Department of Organic Chemistry
 Faculty of Science, PO Box 812
 University of Yaounde
 Cameroon
;
    'Etienne Tsamo ' .
;Department of Organic Chemistry
 Faculty of Science, PO Box 812
 University of Yaounde
 Cameroon
;
    'Norbert Sewald' .
;
Department of Chemistry
 Bielefeld University
 PO Box 100131
 33501 Bieleleld
 Germany
;
