##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2009-06-25
_journal_date_accepted     2009-07-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1877
_journal_page_last     o1877
_journal_paper_category     QO
_journal_coeditor_code     HG2529
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
_publ_contact_author_email     'pcrooks@email.uky.edu'
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;\
rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-1,3-\
dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Narsimha Reddy Penthala'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Thirupathi Reddy Yerram Reddy'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
rac-2-(2-amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-
1,3-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H8 N2 O4 S'
_chemical_formula_sum     'C12 H8 N2 O4 S'
_chemical_formula_iupac     'C12 H8 N2 O4 S'
_chemical_formula_weight     276.26
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     14.1702(2)
_cell_length_b     5.67130(10)
_cell_length_c     14.8296(3)
_cell_angle_alpha     90.00
_cell_angle_beta     114.0171(9)
_cell_angle_gamma     90.00
_cell_volume     1088.58(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2750
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     tablet
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.686
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.310
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.927
_exptl_absorpt_correction_T_max     0.985
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(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     'Nonius KappaCCD'
_diffrn_measurement_method     'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean     9.1
_diffrn_reflns_number     23811
_diffrn_reflns_av_R_equivalents     0.0350
_diffrn_reflns_av_sigmaI/netI     0.0238
_diffrn_reflns_theta_min     1.68
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F\^2\^ against ALL reflections. The weighted
R-factor wR and goodness of fit S are based on
F\^2\^, conventional R-factors R are based on F,
with F set to zero for negative F\^2\^. The threshold expression
of F\^2\^ > 2σ(F\^2\^) is used only for calculating
R-factors(gt) etc. and is not relevant to the choice of
reflections for refinement. R-factors based on F\^2\^ 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     2498
_reflns_number_gt     2268
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0328
_refine_ls_R_factor_gt     0.0290
_refine_ls_wR_factor_gt     0.0737
_refine_ls_wR_factor_ref     0.0760
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_restrained_S_all     1.064
_refine_ls_number_reflns     2498
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0342P)²+0.6796P], 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     0.376
_refine_diff_density_min     -0.262
_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'
    'N' 'N' 0.0061 0.0033
                         '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
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
    S S1 0.66382(2) 0.49412(5) 0.17138(2) 0.01284(10) Uani d . 1 . .
    O O1 0.42723(7) 0.96668(16) 0.23512(7) 0.0153(2) Uani d . 1 . .
    N N1 0.49352(8) 0.24974(19) 0.06881(8) 0.0125(2) Uani d . 1 . .
    C C1 0.45157(9) 0.7729(2) 0.27136(9) 0.0120(2) Uani d . 1 . .
    O O2 0.63896(6) 0.76852(16) 0.33559(7) 0.01299(19) Uani d . 1 . .
    H H2 0.6250 0.9129 0.3335 0.019 Uiso calc R 1 . .
    N N2 0.64515(8) 0.0977(2) 0.06834(8) 0.0143(2) Uani d . 1 . .
    H H2A 0.6112 -0.0200 0.0303 0.017 Uiso calc R 1 . .
    H H2B 0.7125 0.1084 0.0878 0.017 Uiso calc R 1 . .
    C C2 0.54859(9) 0.6411(2) 0.27535(9) 0.0111(2) Uani d . 1 . .
    O O3 0.61330(7) 0.25829(17) 0.35097(7) 0.0167(2) Uani d . 1 . .
    C C3 0.54791(9) 0.4118(2) 0.33094(9) 0.0120(2) Uani d . 1 . .
    O O4 0.37082(7) 0.45803(17) 0.10054(7) 0.0162(2) Uani d . 1 . .
    C C4 0.45890(10) 0.4216(2) 0.35841(9) 0.0127(2) Uani d . 1 . .
    C C5 0.42889(10) 0.2577(2) 0.41132(9) 0.0153(3) Uani d . 1 . .
    H H5 0.4654 0.1135 0.4326 0.018 Uiso calc R 1 . .
    C C6 0.34424(10) 0.3100(3) 0.43217(9) 0.0178(3) Uani d . 1 . .
    H H6 0.3220 0.1996 0.4676 0.021 Uiso calc R 1 . .
    C C7 0.29109(10) 0.5234(3) 0.40164(10) 0.0180(3) Uani d . 1 . .
    H H7 0.2348 0.5578 0.4186 0.022 Uiso calc R 1 . .
    C C8 0.31936(10) 0.6860(3) 0.34679(9) 0.0158(3) Uani d . 1 . .
    H H8 0.2823 0.8293 0.3248 0.019 Uiso calc R 1 . .
    C C9 0.40390(9) 0.6314(2) 0.32529(9) 0.0130(2) Uani d . 1 . .
    C C10 0.54450(9) 0.6061(2) 0.17129(9) 0.0116(2) Uani d . 1 . .
    H H10 0.5296 0.7620 0.1368 0.014 Uiso calc R 1 . .
    C C11 0.45938(9) 0.4304(2) 0.10930(9) 0.0121(2) Uani d . 1 . .
    C C12 0.59513(9) 0.2577(2) 0.09614(9) 0.0121(2) Uani d . 1 . .
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
    S1 0.01022(15) 0.01467(17) 0.01409(16) -0.00198(11) 0.00543(12) -0.00411(11)
    O1 0.0149(4) 0.0140(5) 0.0158(4) 0.0023(4) 0.0051(4) 0.0012(4)
    N1 0.0116(5) 0.0137(5) 0.0120(5) -0.0008(4) 0.0046(4) -0.0010(4)
    C1 0.0101(5) 0.0138(6) 0.0107(5) -0.0008(5) 0.0027(4) -0.0026(5)
    O2 0.0108(4) 0.0104(4) 0.0154(4) -0.0007(3) 0.0030(3) -0.0023(3)
    N2 0.0109(5) 0.0154(5) 0.0162(5) -0.0014(4) 0.0051(4) -0.0049(4)
    C2 0.0098(5) 0.0113(6) 0.0117(5) -0.0005(4) 0.0038(4) -0.0009(5)
    O3 0.0153(4) 0.0131(5) 0.0209(5) 0.0027(4) 0.0065(4) 0.0013(4)
    C3 0.0123(6) 0.0118(6) 0.0101(5) -0.0012(5) 0.0029(5) -0.0015(5)
    O4 0.0112(4) 0.0197(5) 0.0176(4) 0.0001(4) 0.0056(4) -0.0015(4)
    C4 0.0133(6) 0.0139(6) 0.0108(6) -0.0017(5) 0.0047(5) -0.0029(5)
    C5 0.0180(6) 0.0150(6) 0.0125(6) -0.0023(5) 0.0056(5) -0.0005(5)
    C6 0.0193(6) 0.0234(7) 0.0113(6) -0.0065(5) 0.0071(5) -0.0021(5)
    C7 0.0131(6) 0.0278(8) 0.0136(6) -0.0039(5) 0.0060(5) -0.0046(5)
    C8 0.0122(6) 0.0199(7) 0.0140(6) -0.0001(5) 0.0041(5) -0.0026(5)
    C9 0.0123(6) 0.0146(6) 0.0109(5) -0.0022(5) 0.0035(5) -0.0017(5)
    C10 0.0109(5) 0.0125(6) 0.0119(5) -0.0002(4) 0.0051(4) -0.0006(5)
    C11 0.0126(6) 0.0133(6) 0.0095(5) -0.0006(5) 0.0035(5) 0.0009(5)
    C12 0.0137(6) 0.0128(6) 0.0096(5) -0.0017(5) 0.0046(4) 0.0004(5)
_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
    S1 C12 . 1.7623(13) ?
    S1 C10 . 1.8056(12) ?
    O1 C1 . 1.2101(16) ?
    N1 C12 . 1.3283(16) ?
    N1 C11 . 1.3715(17) ?
    C1 C9 . 1.4764(17) ?
    C1 C2 . 1.5449(17) ?
    O2 C2 . 1.4245(14) ?
    O2 H2 . 0.8400 ?
    N2 C12 . 1.3166(16) ?
    N2 H2A . 0.8800 ?
    N2 H2B . 0.8800 ?
    C2 C10 . 1.5334(17) ?
    C2 C3 . 1.5418(17) ?
    O3 C3 . 1.2167(16) ?
    C3 C4 . 1.4759(17) ?
    O4 C11 . 1.2180(16) ?
    C4 C5 . 1.3903(18) ?
    C4 C9 . 1.3973(18) ?
    C5 C6 . 1.3873(19) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.400(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3922(19) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.3942(18) ?
    C8 H8 . 0.9500 ?
    C10 C11 . 1.5460(17) ?
    C10 H10 . 1.0000 ?
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
    C12 S1 C10 . . 89.51(6) ?
    C12 N1 C11 . . 111.88(11) ?
    O1 C1 C9 . . 128.58(12) ?
    O1 C1 C2 . . 123.02(11) ?
    C9 C1 C2 . . 108.20(10) ?
    C2 O2 H2 . . 109.5 ?
    C12 N2 H2A . . 120.0 ?
    C12 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O2 C2 C10 . . 110.66(10) ?
    O2 C2 C3 . . 107.00(9) ?
    C10 C2 C3 . . 115.04(10) ?
    O2 C2 C1 . . 109.71(10) ?
    C10 C2 C1 . . 110.82(10) ?
    C3 C2 C1 . . 103.28(10) ?
    O3 C3 C4 . . 127.68(12) ?
    O3 C3 C2 . . 124.33(11) ?
    C4 C3 C2 . . 107.91(10) ?
    C5 C4 C9 . . 120.86(12) ?
    C5 C4 C3 . . 128.50(12) ?
    C9 C4 C3 . . 110.63(11) ?
    C6 C5 C4 . . 118.26(12) ?
    C6 C5 H5 . . 120.9 ?
    C4 C5 H5 . . 120.9 ?
    C5 C6 C7 . . 120.88(12) ?
    C5 C6 H6 . . 119.6 ?
    C7 C6 H6 . . 119.6 ?
    C8 C7 C6 . . 121.13(12) ?
    C8 C7 H7 . . 119.4 ?
    C6 C7 H7 . . 119.4 ?
    C7 C8 C9 . . 117.69(13) ?
    C7 C8 H8 . . 121.2 ?
    C9 C8 H8 . . 121.2 ?
    C8 C9 C4 . . 121.14(12) ?
    C8 C9 C1 . . 128.92(12) ?
    C4 C9 C1 . . 109.91(11) ?
    C2 C10 C11 . . 112.48(10) ?
    C2 C10 S1 . . 113.13(8) ?
    C11 C10 S1 . . 106.11(8) ?
    C2 C10 H10 . . 108.3 ?
    C11 C10 H10 . . 108.3 ?
    S1 C10 H10 . . 108.3 ?
    O4 C11 N1 . . 125.52(12) ?
    O4 C11 C10 . . 120.08(11) ?
    N1 C11 C10 . . 114.40(10) ?
    N2 C12 N1 . . 122.39(12) ?
    N2 C12 S1 . . 119.58(9) ?
    N1 C12 S1 . . 118.02(10) ?
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
    O1 C1 C2 O2 . . . . 64.08(15) ?
    C9 C1 C2 O2 . . . . -111.21(11) ?
    O1 C1 C2 C10 . . . . -58.41(15) ?
    C9 C1 C2 C10 . . . . 126.30(11) ?
    O1 C1 C2 C3 . . . . 177.88(11) ?
    C9 C1 C2 C3 . . . . 2.59(12) ?
    O2 C2 C3 O3 . . . . -63.22(15) ?
    C10 C2 C3 O3 . . . . 60.14(16) ?
    C1 C2 C3 O3 . . . . -178.97(12) ?
    O2 C2 C3 C4 . . . . 113.91(10) ?
    C10 C2 C3 C4 . . . . -122.72(11) ?
    C1 C2 C3 C4 . . . . -1.84(12) ?
    O3 C3 C4 C5 . . . . -1.2(2) ?
    C2 C3 C4 C5 . . . . -178.24(12) ?
    O3 C3 C4 C9 . . . . 177.42(12) ?
    C2 C3 C4 C9 . . . . 0.41(14) ?
    C9 C4 C5 C6 . . . . -1.35(18) ?
    C3 C4 C5 C6 . . . . 177.19(12) ?
    C4 C5 C6 C7 . . . . -0.65(19) ?
    C5 C6 C7 C8 . . . . 2.1(2) ?
    C6 C7 C8 C9 . . . . -1.44(19) ?
    C7 C8 C9 C4 . . . . -0.56(19) ?
    C7 C8 C9 C1 . . . . -178.27(12) ?
    C5 C4 C9 C8 . . . . 1.99(19) ?
    C3 C4 C9 C8 . . . . -176.79(11) ?
    C5 C4 C9 C1 . . . . -179.91(11) ?
    C3 C4 C9 C1 . . . . 1.32(14) ?
    O1 C1 C9 C8 . . . . 0.5(2) ?
    C2 C1 C9 C8 . . . . 175.40(12) ?
    O1 C1 C9 C4 . . . . -177.45(12) ?
    C2 C1 C9 C4 . . . . -2.51(14) ?
    O2 C2 C10 C11 . . . . 169.35(10) ?
    C3 C2 C10 C11 . . . . 47.95(14) ?
    C1 C2 C10 C11 . . . . -68.72(13) ?
    O2 C2 C10 S1 . . . . 49.13(12) ?
    C3 C2 C10 S1 . . . . -72.27(12) ?
    C1 C2 C10 S1 . . . . 171.06(8) ?
    C12 S1 C10 C2 . . . . 124.72(9) ?
    C12 S1 C10 C11 . . . . 0.93(9) ?
    C12 N1 C11 O4 . . . . -176.05(12) ?
    C12 N1 C11 C10 . . . . 3.27(15) ?
    C2 C10 C11 O4 . . . . 52.60(16) ?
    S1 C10 C11 O4 . . . . 176.80(10) ?
    C2 C10 C11 N1 . . . . -126.76(11) ?
    S1 C10 C11 N1 . . . . -2.56(13) ?
    C11 N1 C12 N2 . . . . 178.04(12) ?
    C11 N1 C12 S1 . . . . -2.57(14) ?
    C10 S1 C12 N2 . . . . -179.74(11) ?
    C10 S1 C12 N1 . . . . 0.85(10) ?
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
    O2 H2 O3 1_565 0.84 1.99 2.8225(13) 170.0
    N2 H2A N1 3_655 0.88 2.07 2.9372(15) 168.4
    N2 H2B O2 2_645 0.88 2.14 2.9629(14) 154.6
