##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 990638'
_chemical_name_systematic
;\
9-(2-Chlorophenyl)-4a-hydroxy-3,4,4a,5,6,7,9,9a-octahydro-2H-\
xanthene-1,8-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 Cl O4'
_chemical_formula_sum     'C19 H19 Cl O4'
_chemical_formula_iupac     'C19 H19 Cl O4'
_chemical_formula_weight     346.79
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     15.3099(13)
_cell_length_b     9.2815(8)
_cell_length_c     12.3216(11)
_cell_angle_alpha     90.00
_cell_angle_beta     110.7160(10)
_cell_angle_gamma     90.00
_cell_volume     1637.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2557
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     22.60
_cell_measurement_temperature     291(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.406
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.254
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.94
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details     ?
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12319
_diffrn_reflns_av_R_equivalents     0.0367
_diffrn_reflns_av_sigmaI/netI     0.0376
_diffrn_reflns_theta_min     1.42
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_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 >
σ(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     3207
_reflns_number_gt     2208
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0764
_refine_ls_R_factor_gt     0.0415
_refine_ls_wR_factor_gt     0.1145
_refine_ls_wR_factor_ref     0.1371
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_restrained_S_all     1.001
_refine_ls_number_reflns     3207
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0852P)²+0.0000P] 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     0.240
_refine_diff_density_min     -0.239
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008'
_computing_publication_material     'SHELXTL (Sheldrick, 2008'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.36292(16) 0.6212(3) 0.22858(19) 0.0374(5) Uani d . 1 1 B .
    C C2 0.4586(2) 0.5704(3) 0.3045(3) 0.0679(9) Uani d . 1 1 . .
    H H2A 0.4519 0.5038 0.3618 0.082 Uiso calc R 1 1 A 1
    H H2B 0.4865 0.5178 0.2569 0.082 Uiso calc R 1 1 A 1
    C C3 0.5220(3) 0.6854(6) 0.3646(6) 0.0557(18) Uani d P 0.744(12) 1 B 1
    H H3A 0.5405 0.7363 0.3075 0.067 Uiso d PR 0.744(12) 1 B 1
    H H3B 0.5778 0.6441 0.4211 0.067 Uiso d PR 0.744(12) 1 B 1
    C C3' 0.4986(10) 0.6331(16) 0.4163(11) 0.048(4) Uani d P 0.256(12) 1 B 2
    H H3'A 0.5649 0.6240 0.4362 0.058 Uiso d PR 0.256(12) 1 B 2
    H H3'B 0.4820 0.5808 0.4733 0.058 Uiso d PR 0.256(12) 1 B 2
    C C4 0.48086(16) 0.7929(3) 0.4227(2) 0.0474(7) Uani d . 1 1 . .
    H H4A 0.5185 0.8798 0.4380 0.057 Uiso calc R 1 1 B 1
    H H4B 0.4826 0.7543 0.4966 0.057 Uiso calc R 1 1 B 1
    C C5 0.38240(15) 0.8304(2) 0.35106(17) 0.0325(5) Uani d . 1 1 B .
    C C6 0.32588(14) 0.7506(2) 0.26163(17) 0.0304(5) Uani d . 1 1 . .
    C C7 0.22743(14) 0.7965(2) 0.19183(17) 0.0294(5) Uani d . 1 1 B .
    H H7A 0.2224 0.7950 0.1103 0.035 Uiso calc R 1 1 . .
    C C8 0.21218(14) 0.9542(2) 0.21988(16) 0.0287(5) Uani d . 1 1 . .
    H H8A 0.1447 0.9677 0.1986 0.034 Uiso calc R 1 1 B .
    C C9 0.24489(16) 1.0626(3) 0.14999(18) 0.0368(5) Uani d . 1 1 B .
    C C10 0.2394(2) 1.2177(3) 0.1799(2) 0.0475(6) Uani d . 1 1 . .
    H H10A 0.1745 1.2456 0.1591 0.057 Uiso calc R 1 1 B .
    H H10B 0.2671 1.2769 0.1357 0.057 Uiso calc R 1 1 . .
    C C11 0.29051(17) 1.2435(3) 0.3093(2) 0.0408(6) Uani d . 1 1 B .
    H H11A 0.3568 1.2265 0.3284 0.049 Uiso calc R 1 1 . .
    H H11B 0.2822 1.3429 0.3278 0.049 Uiso calc R 1 1 . .
    C C12 0.25337(16) 1.1442(3) 0.38055(19) 0.0374(6) Uani d . 1 1 . .
    H H12A 0.2898 1.1578 0.4621 0.045 Uiso calc R 1 1 B .
    H H12B 0.1893 1.1705 0.3685 0.045 Uiso calc R 1 1 . .
    C C13 0.25672(14) 0.9869(2) 0.35002(17) 0.0296(5) Uani d . 1 1 B .
    C C14 0.15332(15) 0.6935(2) 0.20126(18) 0.0308(5) Uani d . 1 1 . .
    C C15 0.06507(16) 0.6870(2) 0.11488(19) 0.0364(5) Uani d . 1 1 B .
    C C16 -0.00219(17) 0.5888(3) 0.1178(2) 0.0461(6) Uani d . 1 1 . .
    H H16A -0.0601 0.5866 0.0582 0.055 Uiso calc R 1 1 B .
    C C17 0.01752(18) 0.4942(3) 0.2097(2) 0.0491(7) Uani d . 1 1 B .
    H H17A -0.0268 0.4268 0.2119 0.059 Uiso calc R 1 1 . .
    C C18 0.10288(18) 0.5000(3) 0.2982(2) 0.0450(6) Uani d . 1 1 . .
    H H18A 0.1157 0.4378 0.3611 0.054 Uiso calc R 1 1 B .
    C C19 0.17003(16) 0.5983(2) 0.29409(19) 0.0364(5) Uani d . 1 1 B .
    H H19A 0.2275 0.6007 0.3545 0.044 Uiso calc R 1 1 . .
    Cl Cl1 0.03711(4) 0.80536(8) -0.00262(5) 0.0547(2) Uani d . 1 1 . .
    O O1 0.35645(10) 0.95441(16) 0.38789(12) 0.0361(4) Uani d . 1 1 . .
    O O2 0.31864(12) 0.55190(18) 0.14146(13) 0.0472(5) Uani d . 1 1 . .
    O O3 0.27329(14) 1.0251(2) 0.07442(15) 0.0588(5) Uani d . 1 1 . .
    O O4 0.21588(11) 0.89704(16) 0.40837(12) 0.0387(4) Uani d . 1 1 . .
    H H4O 0.2496 0.8920 0.4769 0.058 Uiso calc R 1 1 B .
_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
    C1 O2 . 1.229(3) ?
    C1 C6 . 1.447(3) ?
    C1 C2 . 1.509(3) ?
    C2 C3' . 1.419(11) ?
    C2 C3 . 1.456(5) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.490(5) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C3 H3'A . 1.0608 ?
    C3' C4 . 1.514(13) ?
    C3' H3B . 1.1976 ?
    C3' H3'A . 0.9601 ?
    C3' H3'B . 0.9599 ?
    C4 C5 . 1.494(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 O1 . 1.348(3) ?
    C5 C6 . 1.355(3) ?
    C6 C7 . 1.509(3) ?
    C7 C14 . 1.519(3) ?
    C7 C8 . 1.541(3) ?
    C7 H7A . 0.9800 ?
    C8 C9 . 1.520(3) ?
    C8 C13 . 1.535(3) ?
    C8 H8A . 0.9800 ?
    C9 O3 . 1.210(3) ?
    C9 C10 . 1.495(3) ?
    C10 C11 . 1.526(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.515(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.513(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 O4 . 1.386(2) ?
    C13 O1 . 1.461(2) ?
    C14 C15 . 1.395(3) ?
    C14 C19 . 1.396(3) ?
    C15 C16 . 1.385(3) ?
    C15 Cl1 . 1.746(2) ?
    C16 C17 . 1.380(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.375(4) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.389(3) ?
    C18 H18A . 0.9300 ?
    C19 H19A . 0.9300 ?
    O4 H4O . 0.8200 ?
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
    O2 C1 C6 . . 122.0(2) ?
    O2 C1 C2 . . 119.5(2) ?
    C6 C1 C2 . . 118.4(2) ?
    C3' C2 C3 . . 39.2(6) ?
    C3' C2 C1 . . 117.7(5) ?
    C3 C2 C1 . . 114.3(3) ?
    C3' C2 H2A . . 71.1 ?
    C3 C2 H2A . . 108.7 ?
    C1 C2 H2A . . 108.7 ?
    C3' C2 H2B . . 131.5 ?
    C3 C2 H2B . . 108.7 ?
    C1 C2 H2B . . 108.7 ?
    H2A C2 H2B . . 107.6 ?
    C2 C3 C4 . . 114.6(4) ?
    C2 C3 H3A . . 107.5 ?
    C4 C3 H3A . . 107.7 ?
    C2 C3 H3B . . 109.5 ?
    C4 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 107.6 ?
    C2 C3 H3'A . . 97.7 ?
    C4 C3 H3'A . . 101.8 ?
    H3A C3 H3'A . . 127.7 ?
    H3B C3 H3'A . . 20.2 ?
    C2 C3' C4 . . 115.4(8) ?
    C2 C3' H3B . . 99.5 ?
    C4 C3' H3B . . 96.4 ?
    C2 C3' H3'A . . 105.4 ?
    C4 C3' H3'A . . 105.5 ?
    H3B C3' H3'A . . 15.0 ?
    C2 C3' H3'B . . 111.6 ?
    C4 C3' H3'B . . 111.0 ?
    H3B C3' H3'B . . 122.2 ?
    H3'A C3' H3'B . . 107.3 ?
    C3 C4 C5 . . 112.5(2) ?
    C3 C4 C3' . . 37.4(5) ?
    C5 C4 C3' . . 111.1(5) ?
    C3 C4 H4A . . 109.1 ?
    C5 C4 H4A . . 109.1 ?
    C3' C4 H4A . . 136.0 ?
    C3 C4 H4B . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    C3' C4 H4B . . 75.0 ?
    H4A C4 H4B . . 107.8 ?
    O1 C5 C6 . . 124.11(19) ?
    O1 C5 C4 . . 110.88(18) ?
    C6 C5 C4 . . 125.0(2) ?
    C5 C6 C1 . . 118.8(2) ?
    C5 C6 C7 . . 122.1(2) ?
    C1 C6 C7 . . 119.07(18) ?
    C6 C7 C14 . . 113.68(17) ?
    C6 C7 C8 . . 109.90(16) ?
    C14 C7 C8 . . 113.82(17) ?
    C6 C7 H7A . . 106.3 ?
    C14 C7 H7A . . 106.3 ?
    C8 C7 H7A . . 106.3 ?
    C9 C8 C13 . . 110.33(17) ?
    C9 C8 C7 . . 113.29(17) ?
    C13 C8 C7 . . 112.07(17) ?
    C9 C8 H8A . . 106.9 ?
    C13 C8 H8A . . 106.9 ?
    C7 C8 H8A . . 106.9 ?
    O3 C9 C10 . . 122.2(2) ?
    O3 C9 C8 . . 121.7(2) ?
    C10 C9 C8 . . 116.0(2) ?
    C9 C10 C11 . . 110.9(2) ?
    C9 C10 H10A . . 109.5 ?
    C11 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    C11 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    C12 C11 C10 . . 110.56(19) ?
    C12 C11 H11A . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    C13 C12 C11 . . 112.95(18) ?
    C13 C12 H12A . . 109.0 ?
    C11 C12 H12A . . 109.0 ?
    C13 C12 H12B . . 109.0 ?
    C11 C12 H12B . . 109.0 ?
    H12A C12 H12B . . 107.8 ?
    O4 C13 O1 . . 108.80(16) ?
    O4 C13 C12 . . 112.99(17) ?
    O1 C13 C12 . . 104.07(16) ?
    O4 C13 C8 . . 107.92(16) ?
    O1 C13 C8 . . 108.71(16) ?
    C12 C13 C8 . . 114.14(18) ?
    C15 C14 C19 . . 116.4(2) ?
    C15 C14 C7 . . 121.16(19) ?
    C19 C14 C7 . . 122.39(19) ?
    C16 C15 C14 . . 122.5(2) ?
    C16 C15 Cl1 . . 117.97(18) ?
    C14 C15 Cl1 . . 119.50(17) ?
    C17 C16 C15 . . 119.4(2) ?
    C17 C16 H16A . . 120.3 ?
    C15 C16 H16A . . 120.3 ?
    C18 C17 C16 . . 119.8(2) ?
    C18 C17 H17A . . 120.1 ?
    C16 C17 H17A . . 120.1 ?
    C17 C18 C19 . . 120.3(2) ?
    C17 C18 H18A . . 119.9 ?
    C19 C18 H18A . . 119.9 ?
    C18 C19 C14 . . 121.5(2) ?
    C18 C19 H19A . . 119.2 ?
    C14 C19 H19A . . 119.2 ?
    C5 O1 C13 . . 117.90(16) ?
    C13 O4 H4O . . 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
    O2 C1 C2 C3' . . . . -166.3(10) ?
    C6 C1 C2 C3' . . . . 13.3(10) ?
    O2 C1 C2 C3 . . . . 150.0(4) ?
    C6 C1 C2 C3 . . . . -30.3(5) ?
    C3' C2 C3 C4 . . . . -57.7(7) ?
    C1 C2 C3 C4 . . . . 46.9(7) ?
    C3 C2 C3' C4 . . . . 56.8(10) ?
    C1 C2 C3' C4 . . . . -38.5(17) ?
    C2 C3 C4 C5 . . . . -40.4(7) ?
    C2 C3 C4 C3' . . . . 55.3(7) ?
    C2 C3' C4 C3 . . . . -58.2(10) ?
    C2 C3' C4 C5 . . . . 41.6(15) ?
    C3 C4 C5 O1 . . . . -162.2(4) ?
    C3' C4 C5 O1 . . . . 157.5(8) ?
    C3 C4 C5 C6 . . . . 18.4(5) ?
    C3' C4 C5 C6 . . . . -22.0(9) ?
    O1 C5 C6 C1 . . . . 178.4(2) ?
    C4 C5 C6 C1 . . . . -2.2(3) ?
    O1 C5 C6 C7 . . . . 1.6(3) ?
    C4 C5 C6 C7 . . . . -179.0(2) ?
    O2 C1 C6 C5 . . . . -172.6(2) ?
    C2 C1 C6 C5 . . . . 7.7(3) ?
    O2 C1 C6 C7 . . . . 4.3(3) ?
    C2 C1 C6 C7 . . . . -175.3(2) ?
    C5 C6 C7 C14 . . . . -116.6(2) ?
    C1 C6 C7 C14 . . . . 66.6(2) ?
    C5 C6 C7 C8 . . . . 12.3(3) ?
    C1 C6 C7 C8 . . . . -164.54(18) ?
    C6 C7 C8 C9 . . . . 84.2(2) ?
    C14 C7 C8 C9 . . . . -147.02(17) ?
    C6 C7 C8 C13 . . . . -41.5(2) ?
    C14 C7 C8 C13 . . . . 87.3(2) ?
    C13 C8 C9 O3 . . . . 131.7(2) ?
    C7 C8 C9 O3 . . . . 5.1(3) ?
    C13 C8 C9 C10 . . . . -48.6(3) ?
    C7 C8 C9 C10 . . . . -175.13(18) ?
    O3 C9 C10 C11 . . . . -126.3(2) ?
    C8 C9 C10 C11 . . . . 53.9(3) ?
    C9 C10 C11 C12 . . . . -55.0(3) ?
    C10 C11 C12 C13 . . . . 54.7(3) ?
    C11 C12 C13 O4 . . . . -175.08(17) ?
    C11 C12 C13 O1 . . . . 67.1(2) ?
    C11 C12 C13 C8 . . . . -51.3(2) ?
    C9 C8 C13 O4 . . . . 172.60(17) ?
    C7 C8 C13 O4 . . . . -60.2(2) ?
    C9 C8 C13 O1 . . . . -69.5(2) ?
    C7 C8 C13 O1 . . . . 57.7(2) ?
    C9 C8 C13 C12 . . . . 46.1(2) ?
    C7 C8 C13 C12 . . . . 173.36(17) ?
    C6 C7 C14 C15 . . . . -156.35(19) ?
    C8 C7 C14 C15 . . . . 76.8(2) ?
    C6 C7 C14 C19 . . . . 21.9(3) ?
    C8 C7 C14 C19 . . . . -105.0(2) ?
    C19 C14 C15 C16 . . . . -2.0(3) ?
    C7 C14 C15 C16 . . . . 176.3(2) ?
    C19 C14 C15 Cl1 . . . . 178.38(16) ?
    C7 C14 C15 Cl1 . . . . -3.3(3) ?
    C14 C15 C16 C17 . . . . 0.7(3) ?
    Cl1 C15 C16 C17 . . . . -179.66(19) ?
    C15 C16 C17 C18 . . . . 1.1(4) ?
    C16 C17 C18 C19 . . . . -1.5(4) ?
    C17 C18 C19 C14 . . . . 0.1(3) ?
    C15 C14 C19 C18 . . . . 1.6(3) ?
    C7 C14 C19 C18 . . . . -176.7(2) ?
    C6 C5 O1 C13 . . . . 15.9(3) ?
    C4 C5 O1 C13 . . . . -163.57(18) ?
    O4 C13 O1 C5 . . . . 72.7(2) ?
    C12 C13 O1 C5 . . . . -166.63(17) ?
    C8 C13 O1 C5 . . . . -44.6(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
    O4 H4O O2 4_576 0.82 2.00 2.784(2) 161
data_New_Global_Publ_Block
_journal_date_recd_electronic     2014-03-02
_journal_date_accepted     2014-03-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      4
_journal_page_first     o442
_journal_page_last     o443
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814005297
_journal_coeditor_code     XU5775
_publ_contact_author_name     'Fang-Ming Wang'
_publ_contact_author_address
;
Jiangsu University of Science and Technology
Zhenjiang 212003
People's Republic of China
;
_publ_contact_author_email     'wangfmzj@just.edu.cn'
_publ_contact_author_fax     '+(86)-511-84401181'
_publ_contact_author_phone     '+(86)-511-84401181'
_publ_section_title
;\
9-(2-Chlorophenyl)-4a-hydroxy-3,4,4a,5,6,7,9,9a-octahydro-2H-xanthene-1,\
8-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Liu, Qiu-Ling'
;
Jiangsu University of Science and Technology, Zhenjiang 212003,
People's Republic of China
;
    'Wu, Xin-Yan'
;
Jiangsu University of Science and Technology, Zhenjiang 212003,
People's Republic of China
;
    'Gao, Feng'
;
Jiangsu University of Science and Technology, Zhenjiang 212003,
People's Republic of China
;
    'Bao, Dan'
;
Jiangsu University of Science and Technology, Zhenjiang 212003,
People's Republic of China
;
    'Wang, Fang-Ming'
;
Jiangsu University of Science and Technology, Zhenjiang 212003,
People's Republic of China
;
