##############################################################################
###                                                                        ###
###           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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(+-)-2,3,4,4a,5,6,7,8-Octahydro-2-oxonaphthalene-1-acetic acid monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 O3, H2 O'
_chemical_formula_sum     'C12 H18 O4'
_chemical_formula_iupac     'C12 H16 O3, H2 O'
_chemical_formula_weight     226.26
_chemical_melting_point     368
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.153(6)
_cell_length_b     9.386(3)
_cell_length_c     17.122(6)
_cell_angle_alpha     90.00
_cell_angle_beta     93.629(14)
_cell_angle_gamma     90.00
_cell_volume     2430.2(15)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     37
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     10.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'pyramid frustum'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.237
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     'numerical'
_exptl_absorpt_process_details     '(SHELXTL; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.94
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
;
crystal mounted on glass fiber using cyanoacrylate cement
;
_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     'Siemens P4'
_diffrn_measurement_method     2θ/θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5434
_diffrn_reflns_av_R_equivalents     0.031
_diffrn_reflns_av_sigmaI/netI     0.051
_diffrn_reflns_theta_min     2.38
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     1
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     'variation < 1.9'
_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     4273
_reflns_number_gt     2276
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.120
_refine_ls_R_factor_gt     0.055
_refine_ls_wR_factor_gt     0.113
_refine_ls_wR_factor_ref     0.140
_refine_ls_goodness_of_fit_ref     1.01
_refine_ls_restrained_S_all     1.01
_refine_ls_number_reflns     4273
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0463P)²+0.7730P] 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     0.00
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.16
_refine_ls_extinction_method     'SHELXL97 in SHELXTL'
_refine_ls_extinction_coef     0.0011(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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 (Siemens, 1996)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXS97 in SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 in SHELXTL'
_computing_molecular_graphics     'SHELXP97 in SHELXTL'
_computing_publication_material     'SHELXL97 in 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_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 0.26215(15) 0.9816(2) 0.37815(13) 0.0713(7) Uani d . 1 . . O
    O2 0.03598(13) 0.9225(2) 0.29939(11) 0.0602(6) Uani d . 1 . . O
    O3 -0.00080(15) 1.0538(2) 0.40079(12) 0.0598(6) Uani d . 1 . . O
    O4 -0.10169(15) 1.2220(2) 0.30984(13) 0.0619(6) Uani d . 1 . . O
    O1' 0.76558(16) 1.1173(2) 0.87722(14) 0.0761(7) Uani d . 1 . . O
    O2' 0.53650(13) 1.0622(2) 0.79772(11) 0.0589(6) Uani d . 1 . . O
    O3' 0.49506(14) 1.1832(2) 0.90148(12) 0.0577(6) Uani d . 1 . . O
    O4' 0.39593(15) 1.3572(2) 0.81181(13) 0.0606(6) Uani d . 1 . . O
    C1 0.17217(17) 0.7789(3) 0.39256(14) 0.0405(7) Uani d . 1 . . C
    C2 0.25204(19) 0.8522(3) 0.36719(16) 0.0491(8) Uani d . 1 . . C
    C3 0.3156(2) 0.7674(3) 0.3217(2) 0.0658(9) Uani d . 1 . . C
    C4 0.32025(19) 0.6149(4) 0.3469(2) 0.0647(9) Uani d . 1 . . C
    C4A 0.22998(18) 0.5433(3) 0.34476(17) 0.0497(8) Uani d . 1 . . C
    C5 0.2357(2) 0.4001(3) 0.38760(19) 0.0671(9) Uani d . 1 . . C
    C6 0.1472(2) 0.3253(3) 0.3924(2) 0.0713(10) Uani d . 1 . . C
    C7 0.0815(2) 0.4229(3) 0.4297(2) 0.0695(10) Uani d . 1 . . C
    C8 0.07255(19) 0.5638(3) 0.38615(18) 0.0551(8) Uani d . 1 . . C
    C8A 0.15972(17) 0.6384(3) 0.37723(15) 0.0420(7) Uani d . 1 . . C
    C9 0.10520(18) 0.8751(3) 0.42767(15) 0.0470(7) Uani d . 1 . . C
    C10 0.04437(17) 0.9512(3) 0.36851(17) 0.0413(7) Uani d . 1 . . C
    C1' 0.67417(17) 0.9178(3) 0.89103(14) 0.0398(7) Uani d . 1 . . C
    C2' 0.75437(18) 0.9886(3) 0.86581(16) 0.0476(7) Uani d . 1 . . C
    C3' 0.81756(19) 0.9020(3) 0.82110(19) 0.0600(9) Uani d . 1 . . C
    C4' 0.82305(18) 0.7501(3) 0.85118(18) 0.0581(8) Uani d . 1 . . C
    C4'A 0.73266(18) 0.6793(3) 0.84857(17) 0.0494(8) Uani d . 1 . . C
    C5' 0.7370(2) 0.5382(3) 0.8940(2) 0.0738(10) Uani d . 1 . . C
    C6' 0.6485(3) 0.4644(4) 0.8966(2) 0.0901(13) Uani d . 1 . . C
    C7' 0.5815(3) 0.5629(4) 0.9315(2) 0.0825(12) Uani d . 1 . . C
    C8' 0.5736(2) 0.7027(3) 0.88656(19) 0.0628(9) Uani d . 1 . . C
    C8'A 0.66143(17) 0.7765(3) 0.87760(15) 0.0430(7) Uani d . 1 . . C
    C9' 0.60735(18) 1.0151(3) 0.92552(15) 0.0485(7) Uani d . 1 . . C
    C10' 0.54332(17) 1.0873(3) 0.86724(16) 0.0409(7) Uani d . 1 . . C
    H3 -0.029(2) 1.095(4) 0.3671(19) 0.080 Uiso d . 1 . . H
    H4A -0.141(2) 1.271(4) 0.3316(19) 0.080 Uiso d . 1 . . H
    H4B -0.083(2) 1.277(4) 0.2745(19) 0.080 Uiso d . 1 . . H
    H3' 0.459(2) 1.231(4) 0.8688(18) 0.080 Uiso d . 1 . . H
    H4'A 0.356(2) 1.412(4) 0.8335(19) 0.080 Uiso d . 1 . . H
    H4'B 0.416(2) 1.411(4) 0.7806(19) 0.080 Uiso d . 1 . . H
    H3A 0.2972 0.7719 0.2665 0.079 Uiso calc R 1 . . H
    H3B 0.3740 0.8096 0.3288 0.079 Uiso calc R 1 . . H
    H4C 0.3472 0.6099 0.3998 0.078 Uiso calc R 1 . . H
    H4D 0.3579 0.5632 0.3130 0.078 Uiso calc R 1 . . H
    H4AA 0.2120 0.5240 0.2898 0.060 Uiso calc R 1 . . H
    H5A 0.2752 0.3379 0.3610 0.081 Uiso calc R 1 . . H
    H5B 0.2613 0.4155 0.4403 0.081 Uiso calc R 1 . . H
    H6A 0.1551 0.2390 0.4233 0.086 Uiso calc R 1 . . H
    H6B 0.1242 0.2986 0.3403 0.086 Uiso calc R 1 . . H
    H7A 0.0243 0.3765 0.4290 0.083 Uiso calc R 1 . . H
    H7B 0.1012 0.4404 0.4838 0.083 Uiso calc R 1 . . H
    H8A 0.0443 0.5468 0.3346 0.066 Uiso calc R 1 . . H
    H8B 0.0343 0.6263 0.4140 0.066 Uiso calc R 1 . . H
    H9A 0.0697 0.8185 0.4613 0.056 Uiso calc R 1 . . H
    H9B 0.1365 0.9456 0.4602 0.056 Uiso calc R 1 . . H
    H3'A 0.8758 0.9452 0.8262 0.072 Uiso calc R 1 . . H
    H3'B 0.7980 0.9015 0.7660 0.072 Uiso calc R 1 . . H
    H4'C 0.8484 0.7502 0.9047 0.070 Uiso calc R 1 . . H
    H4'D 0.8619 0.6955 0.8196 0.070 Uiso calc R 1 . . H
    H4'E 0.7161 0.6567 0.7937 0.059 Uiso calc R 1 . . H
    H5'A 0.7779 0.4747 0.8700 0.089 Uiso calc R 1 . . H
    H5'B 0.7601 0.5566 0.9471 0.089 Uiso calc R 1 . . H
    H6'A 0.6551 0.3786 0.9280 0.108 Uiso calc R 1 . . H
    H6'B 0.6273 0.4370 0.8441 0.108 Uiso calc R 1 . . H
    H7'A 0.5242 0.5164 0.9299 0.099 Uiso calc R 1 . . H
    H7'B 0.5997 0.5821 0.9858 0.099 Uiso calc R 1 . . H
    H8'A 0.5459 0.6842 0.8350 0.075 Uiso calc R 1 . . H
    H8'B 0.5352 0.7664 0.9134 0.075 Uiso calc R 1 . . H
    H9'A 0.5737 0.9600 0.9612 0.058 Uiso calc R 1 . . H
    H9'B 0.6391 1.0881 0.9560 0.058 Uiso calc R 1 . . H
_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
    O1 C2 . 1.237(3) ?
    O2 C10 . 1.213(3) Y
    O3 C10 . 1.322(3) Y
    O1' C2' . 1.234(3) ?
    O2' C10' . 1.211(3) Y
    O3' C10' . 1.320(3) Y
    C1 C8A . 1.355(4) ?
    C1 C2 . 1.481(4) ?
    C1 C9 . 1.511(4) ?
    C2 C3 . 1.503(4) ?
    C3 C4 . 1.495(4) ?
    C4 C4A . 1.522(4) ?
    C4A C8A . 1.521(4) ?
    C4A C5 . 1.532(4) ?
    C5 C6 . 1.520(4) ?
    C6 C7 . 1.522(4) ?
    C7 C8 . 1.520(4) ?
    C8 C8A . 1.511(4) ?
    C9 C10 . 1.506(4) ?
    C1' C8'A . 1.358(4) ?
    C1' C2' . 1.473(4) ?
    C1' C9' . 1.511(4) ?
    C2' C3' . 1.502(4) ?
    C3' C4' . 1.516(4) ?
    C4' C4'A . 1.520(4) ?
    C4'A C8'A . 1.521(4) ?
    C4'A C5' . 1.535(4) ?
    C5' C6' . 1.513(5) ?
    C6' C7' . 1.523(5) ?
    C7' C8' . 1.522(4) ?
    C8' C8'A . 1.517(4) ?
    C9' C10' . 1.508(4) ?
    O3 H3 . 0.80(3) ?
    O4 H4A . 0.86(3) ?
    O4 H4B . 0.86(3) ?
    O3' H3' . 0.89(3) ?
    O4' H4'A . 0.89(3) ?
    O4' H4'B . 0.81(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 H4C . 0.9700 ?
    C4 H4D . 0.9700 ?
    C4A H4AA . 0.9800 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C3' H3'A . 0.9700 ?
    C3' H3'B . 0.9700 ?
    C4' H4'C . 0.9700 ?
    C4' H4'D . 0.9700 ?
    C4'A H4'E . 0.9800 ?
    C5' H5'A . 0.9700 ?
    C5' H5'B . 0.9700 ?
    C6' H6'A . 0.9700 ?
    C6' H6'B . 0.9700 ?
    C7' H7'A . 0.9700 ?
    C7' H7'B . 0.9700 ?
    C8' H8'A . 0.9700 ?
    C8' H8'B . 0.9700 ?
    C9' H9'A . 0.9700 ?
    C9' H9'B . 0.9700 ?
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
    C8A C1 C2 . . 120.1(3) ?
    C8A C1 C9 . . 124.7(3) ?
    C2 C1 C9 . . 114.9(2) ?
    O1 C2 C1 . . 120.5(3) ?
    O1 C2 C3 . . 121.4(3) ?
    C1 C2 C3 . . 117.9(3) ?
    C4 C3 C2 . . 112.2(3) ?
    C3 C4 C4A . . 112.9(3) ?
    C8A C4A C4 . . 112.4(3) ?
    C8A C4A C5 . . 111.1(2) ?
    C4 C4A C5 . . 110.7(3) ?
    C6 C5 C4A . . 114.1(3) ?
    C5 C6 C7 . . 110.3(3) ?
    C8 C7 C6 . . 111.0(3) ?
    C8A C8 C7 . . 113.7(3) ?
    C1 C8A C8 . . 122.9(3) ?
    C1 C8A C4A . . 123.3(3) ?
    C8 C8A C4A . . 113.7(2) ?
    C10 C9 C1 . . 114.4(2) ?
    O2 C10 O3 . . 123.0(3) ?
    O2 C10 C9 . . 125.0(3) Y
    O3 C10 C9 . . 112.0(2) Y
    C8'A C1' C2' . . 120.1(3) ?
    C8'A C1' C9' . . 124.4(3) ?
    C2' C1' C9' . . 115.3(2) ?
    O1' C2' C1' . . 120.2(3) ?
    O1' C2' C3' . . 121.7(3) ?
    C1' C2' C3' . . 118.0(3) ?
    C2' C3' C4' . . 111.0(2) ?
    C3' C4' C4'A . . 111.8(2) ?
    C4' C4'A C8'A . . 112.6(2) ?
    C4' C4'A C5' . . 110.7(3) ?
    C8'A C4'A C5' . . 111.1(2) ?
    C6' C5' C4'A . . 113.6(3) ?
    C5' C6' C7' . . 110.3(3) ?
    C8' C7' C6' . . 111.0(3) ?
    C8'A C8' C7' . . 113.8(3) ?
    C1' C8'A C8' . . 123.1(3) ?
    C1' C8'A C4'A . . 123.1(3) ?
    C8' C8'A C4'A . . 113.8(3) ?
    C10' C9' C1' . . 115.6(2) ?
    O2' C10' O3' . . 123.6(3) ?
    O2' C10' C9' . . 125.0(3) Y
    O3' C10' C9' . . 111.3(2) Y
    C10 O3 H3 . . 109(3) ?
    H4A O4 H4B . . 105(3) ?
    C10' O3' H3' . . 114(2) ?
    H4'A O4' H4'B . . 102(3) ?
    C4 C3 H3A . . 109.2 ?
    C2 C3 H3A . . 109.2 ?
    C4 C3 H3B . . 109.2 ?
    C2 C3 H3B . . 109.2 ?
    H3A C3 H3B . . 107.9 ?
    C3 C4 H4C . . 109.0 ?
    C4A C4 H4C . . 109.0 ?
    C3 C4 H4D . . 109.0 ?
    C4A C4 H4D . . 109.0 ?
    H4C C4 H4D . . 107.8 ?
    C8A C4A H4AA . . 107.5 ?
    C4 C4A H4AA . . 107.5 ?
    C5 C4A H4AA . . 107.5 ?
    C6 C5 H5A . . 108.7 ?
    C4A C5 H5A . . 108.7 ?
    C6 C5 H5B . . 108.7 ?
    C4A C5 H5B . . 108.7 ?
    H5A C5 H5B . . 107.6 ?
    C5 C6 H6A . . 109.6 ?
    C7 C6 H6A . . 109.6 ?
    C5 C6 H6B . . 109.6 ?
    C7 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.1 ?
    C8 C7 H7A . . 109.4 ?
    C6 C7 H7A . . 109.4 ?
    C8 C7 H7B . . 109.4 ?
    C6 C7 H7B . . 109.4 ?
    H7A C7 H7B . . 108.0 ?
    C8A C8 H8A . . 108.8 ?
    C7 C8 H8A . . 108.8 ?
    C8A C8 H8B . . 108.8 ?
    C7 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    C10 C9 H9A . . 108.7 ?
    C1 C9 H9A . . 108.7 ?
    C10 C9 H9B . . 108.7 ?
    C1 C9 H9B . . 108.7 ?
    H9A C9 H9B . . 107.6 ?
    C2' C3' H3'A . . 109.4 ?
    C4' C3' H3'A . . 109.4 ?
    C2' C3' H3'B . . 109.4 ?
    C4' C3' H3'B . . 109.4 ?
    H3'A C3' H3'B . . 108.0 ?
    C3' C4' H4'C . . 109.3 ?
    C4'A C4' H4'C . . 109.3 ?
    C3' C4' H4'D . . 109.3 ?
    C4'A C4' H4'D . . 109.3 ?
    H4'C C4' H4'D . . 107.9 ?
    C4' C4'A H4'E . . 107.4 ?
    C8'A C4'A H4'E . . 107.4 ?
    C5' C4'A H4'E . . 107.4 ?
    C6' C5' H5'A . . 108.8 ?
    C4'A C5' H5'A . . 108.8 ?
    C6' C5' H5'B . . 108.8 ?
    C4'A C5' H5'B . . 108.8 ?
    H5'A C5' H5'B . . 107.7 ?
    C5' C6' H6'A . . 109.6 ?
    C7' C6' H6'A . . 109.6 ?
    C5' C6' H6'B . . 109.6 ?
    C7' C6' H6'B . . 109.6 ?
    H6'A C6' H6'B . . 108.1 ?
    C8' C7' H7'A . . 109.4 ?
    C6' C7' H7'A . . 109.4 ?
    C8' C7' H7'B . . 109.4 ?
    C6' C7' H7'B . . 109.4 ?
    H7'A C7' H7'B . . 108.0 ?
    C8'A C8' H8'A . . 108.8 ?
    C7' C8' H8'A . . 108.8 ?
    C8'A C8' H8'B . . 108.8 ?
    C7' C8' H8'B . . 108.8 ?
    H8'A C8' H8'B . . 107.7 ?
    C10' C9' H9'A . . 108.4 ?
    C1' C9' H9'A . . 108.4 ?
    C10' C9' H9'B . . 108.4 ?
    C1' C9' H9'B . . 108.4 ?
    H9'A C9' H9'B . . 107.4 ?
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
    C8A C1 C2 O1 . . . . 177.1(3) ?
    C9 C1 C2 O1 . . . . 2.9(4) ?
    C8A C1 C2 C3 . . . . 2.4(4) ?
    C9 C1 C2 C3 . . . . -171.7(2) ?
    O1 C2 C3 C4 . . . . 151.8(3) ?
    C1 C2 C3 C4 . . . . -33.7(4) ?
    C2 C3 C4 C4A . . . . 53.7(4) ?
    C3 C4 C4A C8A . . . . -42.7(4) ?
    C3 C4 C4A C5 . . . . -167.5(3) ?
    C8A C4A C5 C6 . . . . 51.0(4) ?
    C4 C4A C5 C6 . . . . 176.6(3) ?
    C4A C5 C6 C7 . . . . -55.3(4) ?
    C5 C6 C7 C8 . . . . 55.1(4) ?
    C6 C7 C8 C8A . . . . -53.7(4) ?
    C2 C1 C8A C8 . . . . -167.2(2) ?
    C9 C1 C8A C8 . . . . 6.4(4) ?
    C2 C1 C8A C4A . . . . 8.9(4) ?
    C9 C1 C8A C4A . . . . -177.5(2) ?
    C7 C8 C8A C1 . . . . -133.2(3) ?
    C7 C8 C8A C4A . . . . 50.3(3) ?
    C4 C4A C8A C1 . . . . 11.4(4) ?
    C5 C4A C8A C1 . . . . 136.0(3) ?
    C4 C4A C8A C8 . . . . -172.1(2) ?
    C5 C4A C8A C8 . . . . -47.6(3) ?
    C8A C1 C9 C10 . . . . -91.8(3) ?
    C2 C1 C9 C10 . . . . 82.0(3) ?
    C1 C9 C10 O2 . . . . 13.2(4) ?
    C1 C9 C10 O3 . . . . -167.7(2) ?
    C8'A C1' C2' O1' . . . . 179.2(3) ?
    C9' C1' C2' O1' . . . . 3.8(4) ?
    C8'A C1' C2' C3' . . . . 3.6(4) ?
    C9' C1' C2' C3' . . . . -171.8(2) ?
    O1' C2' C3' C4' . . . . 148.1(3) ?
    C1' C2' C3' C4' . . . . -36.4(4) ?
    C2' C3' C4' C4'A . . . . 56.1(3) ?
    C3' C4' C4'A C8'A . . . . -43.6(3) ?
    C3' C4' C4'A C5' . . . . -168.7(3) ?
    C4' C4'A C5' C6' . . . . 177.7(3) ?
    C8'A C4'A C5' C6' . . . . 51.8(4) ?
    C4'A C5' C6' C7' . . . . -56.6(4) ?
    C5' C6' C7' C8' . . . . 55.7(4) ?
    C6' C7' C8' C8'A . . . . -52.7(4) ?
    C2' C1' C8'A C8' . . . . -167.3(3) ?
    C9' C1' C8'A C8' . . . . 7.7(4) ?
    C2' C1' C8'A C4'A . . . . 9.8(4) ?
    C9' C1' C8'A C4'A . . . . -175.2(2) ?
    C7' C8' C8'A C1' . . . . -133.8(3) ?
    C7' C8' C8'A C4'A . . . . 48.9(4) ?
    C4' C4'A C8'A C1' . . . . 10.9(4) ?
    C5' C4'A C8'A C1' . . . . 135.7(3) ?
    C4' C4'A C8'A C8' . . . . -171.8(2) ?
    C5' C4'A C8'A C8' . . . . -47.0(3) ?
    C8'A C1' C9' C10' . . . . -90.3(3) ?
    C2' C1' C9' C10' . . . . 84.9(3) ?
    C1' C9' C10' O2' . . . . 7.6(4) ?
    C1' C9' C10' O3' . . . . -172.1(2) ?
data_global
_journal_date_recd_electronic     2002-06-05
_journal_date_accepted     2002-07-01
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue      8
_journal_page_first     o491
_journal_page_last     o493
_journal_paper_category     FO
_publ_contact_author_name     'Roger A. Lalancette'
_publ_contact_author_address
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark
NJ 07102
USA
;
_publ_contact_author_email     rogerlal@andromeda.rutgers.edu
_publ_contact_author_fax     973-353-1264
_publ_contact_author_phone     973-353-5646
_publ_section_title
;
(+-)-2,3,4,4a,5,6,7,8-Octahydro-2-oxonaphthalene-1-acetic acid:
hydrogen-bonding pattern of the monohydrate of an unsaturated bicyclic
γ-keto acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Lalancette, Roger A.'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark, NJ 07102, USA
;
    'Brunskill, Andrew P. J.'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark, NJ 07102, USA
;
    'Thompson, Hugh W.'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark, NJ 07102, USA
;
