##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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                #
#                                                                            #
##############################################################################
data_default
_audit_creation_method     'manual editing of SHELXL97.CIF'
_journal_date_recd_electronic     2000-12-04
_journal_date_accepted     2001-02-16
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      5
_journal_page_first     646
_journal_page_last     648
_journal_paper_category     FO
_publ_contact_author_name     'Professor J. Zukerman-Schpector'
_publ_contact_author_address
;
Departamento Quimica
Universidade Federal de Sao Carlos
Caixa Postal 676
13565-905 - Sao Carlos, SP
Brazil
;
_publ_contact_author_email     julio@power.ufscar.br
_publ_contact_author_fax     '55(16)2608350'
_publ_contact_author_phone     '55(16)2727344'
_publ_section_title
;
Two polycyclic compounds derived from a Diels-Alder reaction
;
loop_
    _publ_author_name
    _publ_author_address
    'Zukerman-Schpector, J.'
;
Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular
Departamento Química
Universidade Federal de São Carlos
Caixa Postal 676
13565-905 - São Carlos, SP
Brazil
and Instituto de Química
Universidade de São Paulo
São Paulo, SP
Brazil
;
    'Caracelli, I.'
;
Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular
Departamento Química
Universidade Federal de São Carlos
Caixa Postal 676
13565-905 - São Carlos, SP
Brazil
;
    'Vega, Mauricio'
;
Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular
Departamento Química
Universidade Federal de São Carlos
Caixa Postal 676
13565-905 - São Carlos, SP
Brazil
;
    'Constantino, Mauricio Gomes'
;
Departamento de Química
Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto
USP
Ribeirão Preto, SP
Brazil
;
    'Beatriz, Adilson'
;
Departamento de Química
Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto
USP
Ribeirão Preto, SP
Brazil
;
    'da Silva, Gil Valdo'
;
Departamento de Química
Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto
USP
Ribeirão Preto, SP
Brazil
;
data_I
_chemical_name_systematic
;
9,10-dimethoxy-11-oxatricyclo[6.2.1.0^2,7^]undeca-4,9-diene-3,6-diol
;
_chemical_formula_moiety     'C12 H16 O5'
_chemical_formula_sum     'C12 H16 O5'
_chemical_formula_weight     240.25
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'
_cell_length_a     8.0796(4)
_cell_length_b     10.1970(7)
_cell_length_c     13.7534(9)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1133.11(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.98
_cell_measurement_theta_max     18.42
_cell_measurement_temperature     293
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .20
_exptl_crystal_size_mid      .10
_exptl_crystal_size_min      .05
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu      .110
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     1235
_diffrn_reflns_av_R_equivalents     ?
_diffrn_reflns_theta_max     25.45
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     30
_diffrn_standards_decay_%     1.0
_refine_special_details
;
Refinement on F² for ALL reflections. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional R-factors R are based on F,
with F set to zero for negative F². The observed criterion of F² >
2sigma(F²) is used only for calculating R-factor-obs 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     1235
_reflns_number_gt     1131
_reflns_threshold_expression     F²>2\sF²
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .034
_refine_ls_R_factor_gt      .028
_refine_ls_wR_factor_all      .073
_refine_ls_wR_factor_ref      .071
_refine_ls_goodness_of_fit_all     1.054
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.054
_refine_ls_restrained_S_obs     1.054
_refine_ls_number_reflns     1235
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0386P)²+0.2105P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_diff_density_max      .13
_refine_diff_density_min      -.12
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf-Nonius,1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1985)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ZORTEP (Zsolnai, 1995)'
_computing_publication_material
      'PARST95 (Nardelli, 1995), PLATON (Spek, 1998) and WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1  .3506(2)  .67628(13)  .90520(10)  .0405(4) Uani 1 d 1 . . O
    O2  .2964(2)  .84561(16)  .63248(10)  .0475(4) Uani 1 d 1 . . O
    H2O  .2920  .9069  .5802  .057 Uiso 1 d 1 R . H
    O3  .04948(19)  .99741(16)  .99053(11)  .0466(4) Uani 1 d 1 . . O
    H3O  -.0239  .9414 1.0217  .056 Uiso 1 d 1 R . H
    O4  .42929(19)  .99291(15)  .99572(10)  .0437(4) Uani 1 d 1 . . O
    O5  .57015(19)  .94012(14)  .78760(11)  .0417(4) Uani 1 d 1 . . O
    C1  .3791(3)  .74063(19)  .81226(14)  .0353(5) Uani 1 d 1 . . C
    H1  .4377  .6869  .7642  .042 Uiso 1 calc 1 R . H
    C2  .1975(3)  .77429(19)  .78484(14)  .0335(5) Uani 1 d 1 . . C
    H2  .1428  .6937  .7631  .040 Uiso 1 calc 1 R . H
    C3  .1784(3)  .8779(2)  .70497(13)  .0364(5) Uani 1 d 1 . . C
    H3  .0678  .8687  .6766  .044 Uiso 1 calc 1 R . H
    C4  .1948(3) 1.0150(2)  .74374(15)  .0407(5) Uani 1 d 1 . . C
    H4  .2481 1.0783  .7064  .049 Uiso 1 calc 1 R . H
    C5  .1349(3) 1.0474(2)  .82980(15)  .0421(5) Uani 1 d 1 . . C
    H5  .1467 1.1332  .8517  .051 Uiso 1 calc 1 R . H
    C6  .0491(3)  .9499(2)  .89263(15)  .0381(5) Uani 1 d 1 . . C
    H6  -.0662  .9440  .8710  .046 Uiso 1 calc 1 R . H
    C7  .1255(3)  .8125(2)  .88593(14)  .0345(5) Uani 1 d 1 . . C
    H7  .0407  .7481  .9038  .041 Uiso 1 calc 1 R . H
    C8  .2795(3)  .7905(2)  .95180(13)  .0357(5) Uani 1 d 1 . . C
    H8  .2535  .7782 1.0208  .043 Uiso 1 calc 1 R . H
    C9  .4108(3)  .89169(19)  .93237(14)  .0334(4) Uani 1 d 1 . . C
    C10  .4725(2)  .86280(19)  .84497(13)  .0322(4) Uani 1 d 1 . . C
    C11  .5495(4) 1.0897(3)  .97103(18)  .0638(8) Uani 1 d 1 . . C
    H11A  .5468 1.1590 1.0182  .096 Uiso 1 calc 1 R . H
    H11B  .5252 1.1247  .9078  .096 Uiso 1 calc 1 R . H
    H11C  .6575 1.0505  .9704  .096 Uiso 1 calc 1 R . H
    C12  .6722(3)  .8738(2)  .71896(16)  .0475(6) Uani 1 d 1 . . C
    H12A  .6038  .8304  .6718  .071 Uiso 1 calc 1 R . H
    H12B  .7392  .8101  .7521  .071 Uiso 1 calc 1 R . H
    H12C  .7423  .9361  .6867  .071 Uiso 1 calc 1 R . H
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  .0568(9)  .0323(7)  .0325(7)  .0042(7)  -.0020(7)  .0081(6)
    O2  .0607(10)  .0526(9)  .0294(7)  .0118(9)  .0070(7)  .0078(6)
    O3  .0514(9)  .0510(10)  .0374(8)  -.0111(8)  .0095(7)  -.0091(8)
    O4  .0484(8)  .0499(10)  .0329(7)  -.0113(8)  .0031(7)  -.0096(8)
    O5  .0456(8)  .0376(7)  .0419(8)  -.0002(7)  .0139(7)  -.0015(7)
    C1  .0468(13)  .0318(10)  .0273(9)  .0029(10)  -.0006(9)  .0035(8)
    C2  .0392(11)  .0323(9)  .0290(9)  -.0058(9)  -.0013(9)  .0000(8)
    C3  .0358(10)  .0464(12)  .0270(9)  .0045(10)  -.0031(9)  .0044(9)
    C4  .0473(12)  .0380(10)  .0367(10)  .0078(10)  .0033(10)  .0131(9)
    C5  .0468(13)  .0359(10)  .0437(11)  .0073(10)  .0015(10)  .0039(9)
    C6  .0344(11)  .0458(11)  .0340(10)  -.0002(10)  .0028(9)  -.0030(9)
    C7  .0367(11)  .0374(10)  .0294(9)  -.0098(9)  .0017(9)  .0029(8)
    C8  .0453(12)  .0374(10)  .0245(8)  .0003(10)  .0014(8)  .0058(8)
    C9  .0349(10)  .0369(10)  .0283(9)  .0015(9)  -.0052(8)  .0006(8)
    C10  .0326(10)  .0330(9)  .0309(9)  .0020(9)  -.0012(8)  .0028(9)
    C11  .080(2)  .0637(16)  .0481(13)  -.0316(16)  .0129(14)  -.0151(12)
    C12  .0440(12)  .0519(13)  .0465(12)  .0005(11)  .0117(11)  -.0062(11)
_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_distance
    _geom_bond_publ_flag
    O1 C8 1.448(2) yes
    O1 C1 1.455(2) yes
    O2 C3 1.418(2) yes
    O3 C6 1.431(2) yes
    O4 C9 1.359(2) no
    O4 C11 1.426(3) no
    O5 C10 1.366(2) no
    O5 C12 1.424(3) no
    C1 C10 1.524(3) no
    C1 C2 1.554(3) no
    C2 C3 1.532(3) no
    C2 C7 1.557(3) no
    C3 C4 1.502(3) no
    C4 C5 1.321(3) yes
    C5 C6 1.488(3) no
    C6 C7 1.534(3) no
    C7 C8 1.556(3) no
    C8 C9 1.504(3) no
    C9 C10 1.334(3) yes
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_publ_flag
    C8 O1 C1 95.09(13) yes
    C9 O4 C11 116.61(16) yes
    C10 O5 C12 116.29(16) yes
    O1 C1 C10 100.82(14) yes
    O1 C1 C2 99.41(15) yes
    C10 C1 C2 111.03(16) no
    C3 C2 C1 114.91(17) no
    C3 C2 C7 115.49(16) no
    C1 C2 C7 101.04(15) no
    O2 C3 C4 113.99(19) no
    O2 C3 C2 106.04(16) no
    C4 C3 C2 112.25(16) no
    C5 C4 C3 121.2(2) yes
    C4 C5 C6 121.6(2) yes
    O3 C6 C5 108.64(17) no
    O3 C6 C7 111.40(17) no
    C5 C6 C7 112.82(17) no
    C6 C7 C8 114.74(16) no
    C6 C7 C2 115.63(16) no
    C8 C7 C2 100.66(16) no
    O1 C8 C9 101.15(15) yes
    O1 C8 C7 100.12(15) yes
    C9 C8 C7 111.22(16) yes
    C10 C9 O4 134.8(2) no
    C10 C9 C8 105.80(17) no
    O4 C9 C8 119.00(17) no
    C9 C10 O5 127.49(19) no
    C9 C10 C1 105.14(17) no
    O5 C10 C1 125.95(16) 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
    C12 H12A O2 1_555  .96 2.55 3.273(3) 133 yes
    O2 H2O O3 4_574  .95 2.03 2.815(2) 139 yes
    O2 H2O O4 4_574  .95 2.36 3.094(2) 133 yes
    O3 H3O O1 2_467  .93 1.87 2.788(2) 173 yes
    C1 H1 O5 3_646  .98 2.62 3.383(2) 135 yes
data_II
_chemical_name_systematic
;
5,6-dimethoxy-3,7-dioxatetracyclo[6.4.0.0^2,6^0^4,12^]dodec-9-en-11-ol
;
_chemical_formula_moiety     'C12 H16 O5'
_chemical_formula_sum     'C12 H16 O5'
_chemical_formula_weight     240.25
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     7.5450(10)
_cell_length_b     10.7500(10)
_cell_length_c     27.336(3)
_cell_angle_alpha     90
_cell_angle_beta     94.69(2)
_cell_angle_gamma     90
_cell_volume     2209.8(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.90
_cell_measurement_theta_max     18.15
_cell_measurement_temperature     293
_exptl_crystal_description     irregular
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .25
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .16
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.444
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1024.0
_exptl_absorpt_coefficient_mu      .112
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     4326
_diffrn_reflns_av_R_equivalents      .026
_diffrn_reflns_theta_max     25.5
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     30
_diffrn_standards_decay_%     1.1
_refine_special_details
;
Refinement on F² for ALL reflections. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional R-factors R are based on F,
with F set to zero for negative F². The observed criterion of F² >
2sigma(F²) is used only for calculating R-factor-obs 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     2038
_reflns_number_gt     1513
_reflns_threshold_expression     F²>2\sF²
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .061
_refine_ls_R_factor_gt      .040
_refine_ls_wR_factor_all      .111
_refine_ls_wR_factor_ref      .100
_refine_ls_goodness_of_fit_all     1.055
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.055
_refine_ls_restrained_S_obs     1.055
_refine_ls_number_reflns     2038
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0465P)²+1.8597P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_diff_density_max      .190
_refine_diff_density_min      -.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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf-Nonius,1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ZORTEP (Zsolnai, 1995)'
_computing_publication_material
         'PARST95 (Nardelli, 1995), PLATON (Spek, 1998), WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1  .5145(2)  .37746(15)  .12294(6)  .0487(4) Uani 1 d 1 . . O
    O2  .40985(17)  .06233(14)  .11975(5)  .0384(4) Uani 1 d 1 . . O
    O3  .96747(18)  .16362(17)  .17533(6)  .0534(5) Uani 1 d 1 . . O
    H3O  .9372  .1178  .1411  .064 Uiso 1 d 1 R . H
    O4  .32909(16)  .17881(16)  .05138(5)  .0432(4) Uani 1 d 1 . . O
    O5  .74248(17)  .10451(15)  .08970(5)  .0416(4) Uani 1 d 1 . . O
    C1  .4723(2)  .2171(2)  .18084(7)  .0382(5) Uani 1 d 1 . . C
    H1  .4188  .2488  .2098  .046 Uiso 1 calc 1 R . H
    C2  .3940(3)  .2797(2)  .13359(7)  .0409(5) Uani 1 d 1 . . C
    H2  .2692  .3049  .1337  .049 Uiso 1 calc 1 R . H
    C4  .6745(3)  .3031(2)  .12733(8)  .0426(5) Uani 1 d 1 . . C
    H4  .7819  .3506  .1219  .051 Uiso 1 calc 1 R . H
    C5  .6264(2)  .2071(2)  .08736(7)  .0375(5) Uani 1 d 1 . . C
    H5  .6294  .2471  .0552  .045 Uiso 1 calc 1 R . H
    C6  .4300(2)  .1778(2)  .09652(7)  .0354(5) Uani 1 d 1 . . C
    C8  .4345(3)  .0799(2)  .17260(7)  .0379(5) Uani 1 d 1 . . C
    H8  .3237  .0585  .1870  .046 Uiso 1 calc 1 R . H
    C9  .5782(3)  -.0054(2)  .19291(7)  .0420(5) Uani 1 d 1 . . C
    H9  .5506  -.0887  .1974  .050 Uiso 1 calc 1 R . H
    C10  .7427(3)  .0320(2)  .20482(7)  .0441(5) Uani 1 d 1 . . C
    H10  .8241  -.0281  .2166  .053 Uiso 1 calc 1 R . H
    C11  .8095(3)  .1612(2)  .20115(7)  .0427(5) Uani 1 d 1 . . C
    H11  .8453  .1878  .2348  .051 Uiso 1 calc 1 R . H
    C12  .6707(3)  .2561(2)  .18038(7)  .0400(5) Uani 1 d 1 . . C
    H12  .6857  .3297  .2014  .048 Uiso 1 calc 1 R . H
    C13  .7111(3)  .0236(3)  .04885(8)  .0539(6) Uani 1 d 1 . . C
    H13A  .7997  -.0407  .0505  .081 Uiso 1 calc 1 R . H
    H13B  .7169  .0700  .0190  .081 Uiso 1 calc 1 R . H
    H13C  .5953  -.0132  .0494  .081 Uiso 1 calc 1 R . H
    C14  .1424(3)  .1584(3)  .05426(8)  .0519(6) Uani 1 d 1 . . C
    H14A  .0831  .1598  .0218  .078 Uiso 1 calc 1 R . H
    H14B  .0949  .2228  .0737  .078 Uiso 1 calc 1 R . H
    H14C  .1244  .0791  .0692  .078 Uiso 1 calc 1 R . H
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  .0493(9)  .0391(9)  .0568(9)  .0008(7)  -.0013(7)  .0039(7)
    O2  .0425(8)  .0446(9)  .0275(7)  -.0091(7)  -.0008(5)  .0011(6)
    O3  .0306(7)  .0782(13)  .0509(9)  -.0031(8)  .0001(6)  -.0055(8)
    O4  .0293(7)  .0698(11)  .0298(7)  -.0035(7)  -.0028(5)  .0050(7)
    O5  .0311(7)  .0576(10)  .0353(7)  .0040(7)  -.0015(5)  -.0042(7)
    C1  .0343(10)  .0497(13)  .0304(10)  .0031(9)  .0023(8)  -.0057(9)
    C2  .0339(10)  .0476(14)  .0410(11)  .0034(9)  .0021(8)  -.0002(10)
    C4  .0347(10)  .0444(13)  .0477(12)  -.0075(9)  -.0022(8)  .0029(10)
    C5  .0311(10)  .0489(13)  .0323(10)  -.0024(9)  .0016(7)  .0064(9)
    C6  .0294(9)  .0469(13)  .0292(9)  -.0019(9)  -.0019(7)  .0055(9)
    C8  .0345(10)  .0521(14)  .0273(9)  -.0042(9)  .0031(7)  .0017(9)
    C9  .0474(12)  .0442(13)  .0344(10)  -.0013(10)  .0029(8)  .0078(9)
    C10  .0449(12)  .0539(15)  .0326(10)  .0095(10)  -.0029(8)  .0041(10)
    C11  .0350(10)  .0599(15)  .0319(10)  .0020(10)  -.0046(8)  -.0071(10)
    C12  .0384(10)  .0423(13)  .0384(11)  -.0029(9)  -.0025(8)  -.0101(9)
    C13  .0531(13)  .0686(18)  .0393(12)  .0112(12)  -.0012(9)  -.0111(12)
    C14  .0316(10)  .0800(19)  .0427(12)  -.0059(11)  -.0053(9)  .0036(12)
_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_distance
    _geom_bond_publ_flag
    O1 C2 1.435(3) yes
    O1 C4 1.444(3) yes
    O2 C6 1.408(2) yes
    O2 C8 1.454(2) yes
    O3 C11 1.434(2) no
    O4 C6 1.396(2) no
    O4 C14 1.434(2) no
    O5 C5 1.406(3) no
    O5 C13 1.420(3) no
    C1 C8 1.516(3) no
    C1 C2 1.531(3) no
    C1 C12 1.555(3) no
    C2 C6 1.532(3) no
    C4 C5 1.525(3) no
    C4 C12 1.538(3) no
    C5 C6 1.555(2) no
    C8 C9 1.492(3) no
    C9 C10 1.319(3) yes
    C10 C11 1.483(3) no
    C11 C12 1.537(3) no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 C4 96.72(15) yes
    C6 O2 C8 108.91(15) yes
    C6 O4 C14 114.67(15) yes
    C5 O5 C13 112.42(15) yes
    C8 C1 C2 104.31(16) no
    C8 C1 C12 115.46(17) no
    C2 C1 C12 100.39(16) no
    O1 C2 C1 106.58(16) yes
    O1 C2 C6 103.88(16) yes
    C1 C2 C6 99.60(17) yes
    O1 C4 C5 99.60(15) yes
    O1 C4 C12 100.40(16) yes
    C5 C4 C12 115.55(18) yes
    O5 C5 C4 112.80(15) no
    O5 C5 C6 115.55(17) no
    C4 C5 C6 101.29(16) no
    O4 C6 O2 109.54(16) no
    O4 C6 C2 117.74(17) no
    O2 C6 C2 107.49(15) no
    O4 C6 C5 108.31(15) no
    O2 C6 C5 113.01(16) no
    C2 C6 C5 100.63(16) no
    O2 C8 C9 108.69(16) no
    O2 C8 C1 106.33(16) no
    C9 C8 C1 114.86(16) no
    C10 C9 C8 123.0(2) yes
    C9 C10 C11 125.9(2) yes
    O3 C11 C10 110.56(18) no
    O3 C11 C12 111.99(18) no
    C10 C11 C12 114.92(17) no
    C11 C12 C4 120.12(17) no
    C11 C12 C1 116.46(18) no
    C4 C12 C1 100.85(15) 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
    O3 H3O O5 1_555 1.06 1.95 2.849(2) 140 yes
    C13 H13C O2 1_555  .96 2.60 3.133(3) 115 yes
    C13 H13A O1 3_545  .96 2.61 3.325(3) 132 yes
    C4 H4 O2 3_555  .98 2.47 3.320(3) 144 yes
    C11 H11 O3 2_755  .98 2.74 3.648(3) 154 yes
