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###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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                #
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##############################################################################
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2004-06-09
_journal_date_accepted     2004-07-20
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue     11
_journal_page_first     o798
_journal_page_last     o800
_journal_paper_category     FO
_publ_contact_author_name     'Professor Mohammed Bakir'
_publ_contact_author_address
;  Department of Chemistry
 The University of the West Indies
 Mona Campus, Kingston 7
 Jamaica
;
_publ_contact_author_email     mohammed.bakir@uwimona.edu.jm
_publ_contact_author_fax     '876 977 1835'
_publ_contact_author_phone     '876 935 8164'
_publ_section_title
;
Mikanolide from Jamaican Mikania micrantha
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bakir, Mohammed' .
;
Department of Chemistry
The University of the West Indies
Mona Campus, Kingston 7
Jamaica
;
    'Facey, Petrea C.' .
;
 Department of Chemistry
 The University of the West Indies
 Mona Campus, Kingston 7
 Jamaica
;
    'Hassan, Ishmael' .
;
 Department of Chemistry
 The University of the West Indies
 Mona Campus, Kingston 7
 Jamaica
;
    'Mulder, Willem H.' .
;
 Department of Chemistry
 The University of the West Indies
 Mona Campus, Kingston 7
 Jamaica
;
    'Porter, Roy B.' .
;
 Department of Chemistry
 The University of the West Indies
 Mona Campus, Kingston 7
 Jamaica
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
7,10a-dimethyl-1a,1b,2a,6a,7,9a,10,10a-octahydro-4H-6,3-
methenofuro[3,2-c]bisoxireno[f,h]oxacycloundecin-4,8(6H)-dione
or
1,10:2,3-diepoxy-6,8-dihydroxygermacr-4-ene-11-vinyl-12,14-
di-γ-lactone
;
_chemical_name_common     Mikanolide
_chemical_formula_moiety     'C15 H14 O6'
_chemical_formula_sum     'C15 H14 O6'
_chemical_formula_iupac     'C15 H14 O6'
_chemical_formula_weight     290.26
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.9090(12)
_cell_length_b     7.1840(8)
_cell_length_c     10.4940(11)
_cell_angle_alpha     90.00
_cell_angle_beta     98.830(9)
_cell_angle_gamma     90.00
_cell_volume     663.60(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     43
_cell_measurement_theta_min     9.5
_cell_measurement_theta_max     24.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'rectangular prism'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.452
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     304
_exptl_absorpt_coefficient_mu     0.113
_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     'Bruker P4'
_diffrn_measurement_method     '2θ/ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1782
_diffrn_reflns_av_R_equivalents     0.028
_diffrn_reflns_av_sigmaI/netI     0.036
_diffrn_reflns_theta_min     1.96
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     1
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
  ?
;
_reflns_number_total     1483
_reflns_number_gt     1269
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0457
_refine_ls_R_factor_gt     0.0369
_refine_ls_wR_factor_gt     0.0931
_refine_ls_wR_factor_ref     0.0980
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     1483
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.049P)²+0.069P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.13
_refine_diff_density_min     -0.11
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.028(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     'not reliably determined'
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     'XSCANS (Bruker, 1997)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                                'SHELXTL (Bruker, 1997) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_type_symbol
    O1 0.5920(3) 0.0333(4) 0.4209(2) 0.0852(10) Uani . . 1.000 O
    O2 0.3885(3) 0.5396(5) 0.2236(2) 0.0851(10) Uani . . 1.000 O
    O3 0.5364(2) 0.4654(4) 0.07723(18) 0.0692(9) Uani . . 1.000 O
    O4 1.1290(3) 0.3778(4) -0.0908(3) 0.0934(11) Uani . . 1.000 O
    O5 1.0709(2) 0.3466(4) 0.1070(2) 0.0720(9) Uani . . 1.000 O
    O6 0.9159(3) 0.3606(5) 0.51889(19) 0.0823(9) Uani . . 1.000 O
    C1 0.8165(4) 0.2399(6) 0.4363(3) 0.0636(11) Uani . . 1.000 C
    C2 0.6632(4) 0.2007(6) 0.4739(3) 0.0686(13) Uani . . 1.000 C
    C3 0.5248(4) 0.2058(5) 0.3769(3) 0.0624(11) Uani . . 1.000 C
    C4 0.5427(3) 0.2613(5) 0.2457(3) 0.0512(10) Uani . . 1.000 C
    C5 0.6328(3) 0.1907(5) 0.1694(3) 0.0534(9) Uani . . 1.000 C
    C6 0.6465(3) 0.3220(5) 0.0634(3) 0.0583(10) Uani . . 1.000 C
    C7 0.8046(3) 0.4124(5) 0.0706(2) 0.0494(9) Uani . . 1.000 C
    C8 0.9358(3) 0.3340(5) 0.1703(3) 0.0526(10) Uani . . 1.000 C
    C9 0.9779(3) 0.4304(6) 0.2996(3) 0.0628(10) Uani . . 1.000 C
    C10 0.8584(3) 0.4230(5) 0.3877(2) 0.0551(10) Uani . . 1.000 C
    C11 0.8706(4) 0.4031(5) -0.0531(3) 0.0592(11) Uani . . 1.000 C
    C12 1.0341(4) 0.3768(5) -0.0215(4) 0.0681(11) Uani . . 1.000 C
    C13 0.8000(5) 0.4149(7) -0.1742(3) 0.0855(15) Uani . . 1.000 C
    C14 0.4773(3) 0.4340(6) 0.1874(3) 0.0602(12) Uani . . 1.000 C
    C15 0.7570(4) 0.5868(5) 0.3851(3) 0.0647(11) Uani . . 1.000 C
    H1 0.86590 0.13260 0.40260 0.0930 Uiso calc R 1.000 H
    H2 0.65090 0.23090 0.56280 0.1090 Uiso calc R 1.000 H
    H3 0.42960 0.24020 0.40690 0.0920 Uiso calc R 1.000 H
    H5 0.68070 0.07550 0.18060 0.0810 Uiso calc R 1.000 H
    H6 0.61910 0.25910 -0.01980 0.0850 Uiso calc R 1.000 H
    H7 0.79340 0.54440 0.09090 0.0810 Uiso calc R 1.000 H
    H8 0.91530 0.20250 0.18560 0.0750 Uiso calc R 1.000 H
    H9A 0.99990 0.55990 0.28400 0.0730 Uiso calc R 1.000 H
    H9B 1.07030 0.37440 0.34410 0.0730 Uiso calc R 1.000 H
    H13A 0.85550 0.40630 -0.24220 0.1350 Uiso calc R 1.000 H
    H13B 0.69540 0.43170 -0.19090 0.1350 Uiso calc R 1.000 H
    H15A 0.68610 0.56760 0.44410 0.0930 Uiso calc R 1.000 H
    H15B 0.70260 0.60310 0.29950 0.0930 Uiso calc R 1.000 H
    H15C 0.81660 0.69590 0.40990 0.0930 Uiso calc R 1.000 H
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 . . 1.432(5) No
    O1 C3 . . 1.422(5) No
    O2 C14 . . 1.199(5) No
    O3 C6 . . 1.445(4) No
    O3 C14 . . 1.361(4) No
    O4 C12 . . 1.197(5) No
    O5 C8 . . 1.464(3) No
    O5 C12 . . 1.355(5) No
    O6 C1 . . 1.432(5) No
    O6 C10 . . 1.464(3) No
    C1 C2 . . 1.505(5) no
    C1 C10 . . 1.479(5) no
    C2 C3 . . 1.474(5) no
    C3 C4 . . 1.465(4) no
    C4 C5 . . 1.319(4) no
    C4 C14 . . 1.464(5) no
    C5 C6 . . 1.478(5) no
    C6 C7 . . 1.542(4) no
    C7 C8 . . 1.550(4) no
    C7 C11 . . 1.507(4) no
    C8 C9 . . 1.518(5) no
    C9 C10 . . 1.514(4) no
    C10 C15 . . 1.481(5) no
    C11 C12 . . 1.456(5) no
    C11 C13 . . 1.331(5) no
    C1 H1 . . 0.9802 no
    C2 H2 . . 0.9802 no
    C3 H3 . . 0.9806 no
    C5 H5 . . 0.9303 no
    C6 H6 . . 0.9801 no
    C7 H7 . . 0.9804 no
    C8 H8 . . 0.9801 no
    C9 H9A . . 0.9698 no
    C9 H9B . . 0.9693 no
    C13 H13A . . 0.9305 no
    C13 H13B . . 0.9293 no
    C15 H15A . . 0.9599 no
    C15 H15B . . 0.9601 no
    C15 H15C . . 0.9600 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 C3 . . . 62.2(2) No
    C6 O3 C14 . . . 108.9(3) No
    C8 O5 C12 . . . 111.8(2) No
    C1 O6 C10 . . . 61.4(2) No
    O6 C1 C2 . . . 117.1(3) No
    O6 C1 C10 . . . 60.3(2) No
    C2 C1 C10 . . . 123.0(3) no
    O1 C2 C1 . . . 114.9(3) No
    O1 C2 C3 . . . 58.6(2) No
    C1 C2 C3 . . . 120.7(3) no
    O1 C3 C2 . . . 59.2(2) No
    O1 C3 C4 . . . 116.2(3) No
    C2 C3 C4 . . . 117.1(3) no
    C3 C4 C5 . . . 129.0(3) no
    C3 C4 C14 . . . 122.0(3) no
    C5 C4 C14 . . . 108.2(3) no
    C4 C5 C6 . . . 109.9(3) no
    O3 C6 C5 . . . 104.1(2) No
    O3 C6 C7 . . . 108.9(3) No
    C5 C6 C7 . . . 114.4(2) no
    C6 C7 C8 . . . 117.9(3) no
    C6 C7 C11 . . . 114.4(2) no
    C8 C7 C11 . . . 102.2(2) no
    O5 C8 C7 . . . 105.0(2) No
    O5 C8 C9 . . . 105.7(2) No
    C7 C8 C9 . . . 119.7(3) no
    C8 C9 C10 . . . 115.4(2) no
    O6 C10 C1 . . . 58.3(2) No
    O6 C10 C9 . . . 114.1(2) No
    O6 C10 C15 . . . 112.7(2) No
    C1 C10 C9 . . . 118.7(3) no
    C1 C10 C15 . . . 121.8(3) no
    C9 C10 C15 . . . 116.4(3) no
    C7 C11 C12 . . . 108.6(3) no
    C7 C11 C13 . . . 129.1(3) no
    C12 C11 C13 . . . 122.4(3) no
    O4 C12 O5 . . . 121.3(3) No
    O4 C12 C11 . . . 129.5(4) No
    O5 C12 C11 . . . 109.2(3) No
    O2 C14 O3 . . . 121.6(4) No
    O2 C14 C4 . . . 130.0(3) No
    O3 C14 C4 . . . 108.3(3) No
    O6 C1 H1 . . . 115.10 no
    C2 C1 H1 . . . 115.03 no
    C10 C1 H1 . . . 115.08 no
    O1 C2 H2 . . . 116.62 no
    C1 C2 H2 . . . 116.52 no
    C3 C2 H2 . . . 116.61 no
    O1 C3 H3 . . . 117.20 no
    C2 C3 H3 . . . 117.23 no
    C4 C3 H3 . . . 117.21 no
    C4 C5 H5 . . . 125.13 no
    C6 C5 H5 . . . 125.01 no
    O3 C6 H6 . . . 109.76 no
    C5 C6 H6 . . . 109.77 no
    C7 C6 H6 . . . 109.78 no
    C6 C7 H7 . . . 107.18 no
    C8 C7 H7 . . . 107.23 no
    C11 C7 H7 . . . 107.24 no
    O5 C8 H8 . . . 108.71 no
    C7 C8 H8 . . . 108.70 no
    C9 C8 H8 . . . 108.66 no
    C8 C9 H9A . . . 108.38 no
    C8 C9 H9B . . . 108.44 no
    C10 C9 H9A . . . 108.42 no
    C10 C9 H9B . . . 108.42 no
    H9A C9 H9B . . . 107.50 no
    C11 C13 H13A . . . 119.93 no
    C11 C13 H13B . . . 120.10 no
    H13A C13 H13B . . . 119.97 no
    C10 C15 H15A . . . 109.50 no
    C10 C15 H15B . . . 109.45 no
    C10 C15 H15C . . . 109.47 no
    H15A C15 H15B . . . 109.47 no
    H15A C15 H15C . . . 109.50 no
    H15B C15 H15C . . . 109.44 no
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
    C3 O1 C2 C1 . . . . -112.1(3) no
    C2 O1 C3 C4 . . . . 107.3(3) no
    C14 O3 C6 C5 . . . . 6.3(3) yes
    C14 O3 C6 C7 . . . . -116.0(3) no
    C6 O3 C14 O2 . . . . 176.3(3) no
    C6 O3 C14 C4 . . . . -2.9(3) no
    C12 O5 C8 C7 . . . . -14.7(4) no
    C12 O5 C8 C9 . . . . -142.0(3) no
    C8 O5 C12 O4 . . . . -174.6(3) no
    C8 O5 C12 C11 . . . . 4.9(4) no
    C10 O6 C1 C2 . . . . -114.3(4) no
    C1 O6 C10 C9 . . . . -110.0(3) no
    C1 O6 C10 C15 . . . . 114.4(3) no
    O6 C1 C10 C15 . . . . -98.6(3) no
    C2 C1 C10 O6 . . . . 104.9(3) no
    O6 C1 C10 C9 . . . . 102.0(3) no
    C2 C1 C10 C15 . . . . 6.3(4) no
    O6 C1 C2 C3 . . . . 135.3(4) no
    C10 C1 C2 O1 . . . . 131.5(3) no
    C10 C1 C2 C3 . . . . 64.6(5) no
    O6 C1 C2 O1 . . . . -157.8(3) no
    C2 C1 C10 C9 . . . . -153.1(3) no
    O1 C2 C3 C4 . . . . -105.8(3) no
    C1 C2 C3 C4 . . . . -3.6(5) no
    C1 C2 C3 O1 . . . . 102.2(4) no
    O1 C3 C4 C14 . . . . 179.0(3) no
    O1 C3 C4 C5 . . . . -12.4(5) no
    C2 C3 C4 C5 . . . . 54.7(5) no
    C2 C3 C4 C14 . . . . -113.9(4) no
    C3 C4 C14 O3 . . . . 168.4(3) no
    C3 C4 C5 C6 . . . . -163.5(3) no
    C5 C4 C14 O2 . . . . 178.7(4) no
    C5 C4 C14 O3 . . . . -2.2(4) no
    C14 C4 C5 C6 . . . . 6.3(4) no
    C3 C4 C14 O2 . . . . -10.7(6) yes
    C4 C5 C6 O3 . . . . -7.9(3) no
    C4 C5 C6 C7 . . . . 110.8(3) no
    O3 C6 C7 C8 . . . . 126.1(3) no
    O3 C6 C7 C11 . . . . -113.6(3) no
    C5 C6 C7 C11 . . . . 130.4(3) no
    C5 C6 C7 C8 . . . . 10.2(4) yes
    C6 C7 C8 C9 . . . . -97.7(4) no
    C6 C7 C8 O5 . . . . 144.1(3) no
    C8 C7 C11 C13 . . . . 164.3(4) no
    C11 C7 C8 C9 . . . . 135.9(3) no
    C6 C7 C11 C12 . . . . -144.1(3) no
    C11 C7 C8 O5 . . . . 17.6(3) no
    C8 C7 C11 C12 . . . . -15.4(4) no
    C6 C7 C11 C13 . . . . 35.7(6) yes
    C7 C8 C9 C10 . . . . 66.3(4) no
    O5 C8 C9 C10 . . . . -175.8(3) no
    C8 C9 C10 C1 . . . . 64.3(4) no
    C8 C9 C10 C15 . . . . -96.3(4) no
    C8 C9 C10 O6 . . . . 129.9(3) no
    C13 C11 C12 O4 . . . . 7.1(7) yes
    C13 C11 C12 O5 . . . . -172.4(4) yes
    C7 C11 C12 O4 . . . . -173.2(4) no
    C7 C11 C12 O5 . . . . 7.4(4) no
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
    C5 H5 O4 2_745 0.93 2.50 3.282(4) 141 yes
    C7 H7 O4 2_755 0.98 2.49 3.396(4) 153 yes
    C8 H8 O4 2_745 0.98 2.54 3.409(4) 147 yes
