rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thia­zol-5-yl)-2-hydroxy­indane-1,3-dione

Penthala, N.R.; Reddy, T.R.Y.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536809025574

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1877

doi:10.1107/S1600536809025574

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rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-1,3-dione

Narsimha Reddy Penthala,^a Thirupathi Reddy Yerram Reddy,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pcrooks@email.uky.edu

(Received 25 June 2009; accepted 1 July 2009; online 18 July 2009)

In the crystal of the title compound, C₁₂H₈N₂O₄S, molecules are linked into chains by a series of intermolecular O—H⋯O, N—H⋯O and N—H⋯N hydrogen bonds. The ninhydrin and aminothiazolidine units make a dihedral angle of 66.41 (3)°. The crystal structure indicates the presence of equimolar R and S enantiomers in the crystal lattice, due to the presence of a chiral centre in the title compound.

Related literature

The NADPH-dependent oxidase activity of 2-indol-3-yl- methylenequinuclidin-3-ols has been reported by Sekhar et al. (2003 ) and novel substituted (Z)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-ol derivatives have been identified as potent thermal sensitizing agents (Sonar et al., 2007 ). The crystal structure and bond-length data for ninhydrin have been described by Medrud (1969 ) and Fun et al. (2009 ).

Experimental

Crystal data

C₁₂H₈N₂O₄S
M_r = 276.26
Monoclinic, P 2₁ /n
a = 14.1702 (2) Å
b = 5.6713 (1) Å
c = 14.8296 (3) Å
β = 114.0171 (9)°
V = 1088.58 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 90 K
0.25 × 0.12 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.927, T_max = 0.985
23811 measured reflections
2498 independent reflections
2268 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.06
2498 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.84	1.99	2.8225 (13)	170
N2—H2A⋯N1ⁱⁱ	0.88	2.07	2.9372 (15)	168
N2—H2B⋯O2ⁱⁱⁱ	0.88	2.14	2.9629 (14)	155
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025574/hg2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025574/hg2529Isup2.hkl

checkCIF report

Comment top

In continuing studies on the design and synthesis of novel radiosensitizers such as (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-ol derivatives (Sekhar et al., 2003; Sonar et al., 2007), we have undertaken the design, synthesis and structural analysis of a series of ninhydrin analogs with a variety of active methylene compounds. The X-ray analysis of the title compound was carried out to confirm stereochemistry and to obtain detailed information on the structural conformation of the molecule, that might be useful in structure-activity relationship (SAR) studies. The title compound was prepared by the condensation of ninhydrin with 2-aminothiazol-4(5H)-one in ethanol at reflux temperature. The compound was crystallized from ethanol. The molecular structure and the atom-numbering scheme are shown in Fig.1. The ninhydrin ring is planar (r.m.s. deviation = 0.0255 (10) Å) with bond distances and angles comparable with those previously reported for ninhydrin (Medrud, 1969 and Fun et al. (2009). The title compound has a chiral centre at C₁₀ and the X-ray data indicate that the compound is racemic (Fig. 2). The ninhydrin and 2-aminothiazol- 4(5H)-one moieties make a dihedral angle of 66.41 (3)°. Intermolecular O—H···O, N—H···O and N—H···N hydrogen bonds stabilize the crystal structure, and form a three-dimensional network.

Related literature top

The NADPH-dependent oxidase activity of 2-indol-3-yl- methylenequinuclidin-3-ols has been reported by Sekhar et al. (2003) and novel substituted (Z)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-ol derivatives have been identified as potent thermal sensitizing agents (Sonar et al., 2007). The crystal structure and bond-length data for ninhydrin has been described by Medrud (1969) and Fun et al. (2009).

Experimental top

A mixture of ninhydrin (1 mmol) and 2-aminothiazol-4(5H)-one (1.1 mmol) was stirred under reflux in ethanol for 6 hrs. After the reaction was complete, the reaction mixture was cooled to room temperature. The precipitate thus obtained was collected by filtration, washed with cold ethanol and dried, to afford the crude product. Crystallization from ethanol afforded a light yellow crystalline product of 2-(2-amino-4-oxo-4,5-dihydrothiazol-5-yl)-2-hydroxy -1H-indene-1,3(2H)-dione that was suitable for X-ray analysis. ¹H NMR (DMSO-d₆): δ 5.01 (s, 1H, CH), 7.10 (s, 1H, OH), 7.93–8.03 (m, 4H, Ar—H), 8.94–9.06 (bd, 2H, NH₂), p.p.m.; ¹³C NMR (DMSO-d₆): δ 62.15, 73.62, 123.47, 123.57, 136.67, 137.26, 140.68, 141.09, 182.49, 185.12, 197.48, 198.25 p.p.m..

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and local procedures.

Figures top

	Fig. 1. A view of the molecule with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the molecule viewed along the a axis. H atoms have been omitted for clarity.

rac-2-(2-amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane- 1,3-dione top

Crystal data top

C₁₂H₈N₂O₄S	F(000) = 568
M_r = 276.26	D_x = 1.686 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2750 reflections
a = 14.1702 (2) Å	θ = 1.0–27.5°
b = 5.6713 (1) Å	µ = 0.31 mm⁻¹
c = 14.8296 (3) Å	T = 90 K
β = 114.0171 (9)°	Tablet, pale yellow
V = 1088.58 (3) Å³	0.25 × 0.12 × 0.05 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2498 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 9.1 pixels mm^-1	θ_max = 27.5°, θ_min = 1.7°
ω scans at fixed χ = 55°	h = −18→18
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −7→7
T_min = 0.927, T_max = 0.985	l = −19→19
23811 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0342P)² + 0.6796P], where P = (F_o² + 2F_c²)/3
2498 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₈N₂O₄S	V = 1088.58 (3) Å³
M_r = 276.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.1702 (2) Å	µ = 0.31 mm⁻¹
b = 5.6713 (1) Å	T = 90 K
c = 14.8296 (3) Å	0.25 × 0.12 × 0.05 mm
β = 114.0171 (9)°

Data collection top

Nonius KappaCCD diffractometer	2498 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2268 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.985	R_int = 0.035
23811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
2498 reflections	Δρ_min = −0.26 e Å⁻³
173 parameters

Special details top

Geometry. 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.

Refinement. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.66382 (2)	0.49412 (5)	0.17138 (2)	0.01284 (10)
O1	0.42723 (7)	0.96668 (16)	0.23512 (7)	0.0153 (2)
N1	0.49352 (8)	0.24974 (19)	0.06881 (8)	0.0125 (2)
C1	0.45157 (9)	0.7729 (2)	0.27136 (9)	0.0120 (2)
O2	0.63896 (6)	0.76852 (16)	0.33559 (7)	0.01299 (19)
H2	0.6250	0.9129	0.3335	0.019*
N2	0.64515 (8)	0.0977 (2)	0.06834 (8)	0.0143 (2)
H2A	0.6112	−0.0200	0.0303	0.017*
H2B	0.7125	0.1084	0.0878	0.017*
C2	0.54859 (9)	0.6411 (2)	0.27535 (9)	0.0111 (2)
O3	0.61330 (7)	0.25829 (17)	0.35097 (7)	0.0167 (2)
C3	0.54791 (9)	0.4118 (2)	0.33094 (9)	0.0120 (2)
O4	0.37082 (7)	0.45803 (17)	0.10054 (7)	0.0162 (2)
C4	0.45890 (10)	0.4216 (2)	0.35841 (9)	0.0127 (2)
C5	0.42889 (10)	0.2577 (2)	0.41132 (9)	0.0153 (3)
H5	0.4654	0.1135	0.4326	0.018*
C6	0.34424 (10)	0.3100 (3)	0.43217 (9)	0.0178 (3)
H6	0.3220	0.1996	0.4676	0.021*
C7	0.29109 (10)	0.5234 (3)	0.40164 (10)	0.0180 (3)
H7	0.2348	0.5578	0.4186	0.022*
C8	0.31936 (10)	0.6860 (3)	0.34679 (9)	0.0158 (3)
H8	0.2823	0.8293	0.3248	0.019*
C9	0.40390 (9)	0.6314 (2)	0.32529 (9)	0.0130 (2)
C10	0.54450 (9)	0.6061 (2)	0.17129 (9)	0.0116 (2)
H10	0.5296	0.7620	0.1368	0.014*
C11	0.45938 (9)	0.4304 (2)	0.10930 (9)	0.0121 (2)
C12	0.59513 (9)	0.2577 (2)	0.09614 (9)	0.0121 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)

Geometric parameters (Å, º) top

S1—C12	1.7623 (13)	C3—C4	1.4759 (17)
S1—C10	1.8056 (12)	O4—C11	1.2180 (16)
O1—C1	1.2101 (16)	C4—C5	1.3903 (18)
N1—C12	1.3283 (16)	C4—C9	1.3973 (18)
N1—C11	1.3715 (17)	C5—C6	1.3873 (19)
C1—C9	1.4764 (17)	C5—H5	0.9500
C1—C2	1.5449 (17)	C6—C7	1.400 (2)
O2—C2	1.4245 (14)	C6—H6	0.9500
O2—H2	0.8400	C7—C8	1.3922 (19)
N2—C12	1.3166 (16)	C7—H7	0.9500
N2—H2A	0.8800	C8—C9	1.3942 (18)
N2—H2B	0.8800	C8—H8	0.9500
C2—C10	1.5334 (17)	C10—C11	1.5460 (17)
C2—C3	1.5418 (17)	C10—H10	1.0000
O3—C3	1.2167 (16)

C12—S1—C10	89.51 (6)	C5—C6—C7	120.88 (12)
C12—N1—C11	111.88 (11)	C5—C6—H6	119.6
O1—C1—C9	128.58 (12)	C7—C6—H6	119.6
O1—C1—C2	123.02 (11)	C8—C7—C6	121.13 (12)
C9—C1—C2	108.20 (10)	C8—C7—H7	119.4
C2—O2—H2	109.5	C6—C7—H7	119.4
C12—N2—H2A	120.0	C7—C8—C9	117.69 (13)
C12—N2—H2B	120.0	C7—C8—H8	121.2
H2A—N2—H2B	120.0	C9—C8—H8	121.2
O2—C2—C10	110.66 (10)	C8—C9—C4	121.14 (12)
O2—C2—C3	107.00 (9)	C8—C9—C1	128.92 (12)
C10—C2—C3	115.04 (10)	C4—C9—C1	109.91 (11)
O2—C2—C1	109.71 (10)	C2—C10—C11	112.48 (10)
C10—C2—C1	110.82 (10)	C2—C10—S1	113.13 (8)
C3—C2—C1	103.28 (10)	C11—C10—S1	106.11 (8)
O3—C3—C4	127.68 (12)	C2—C10—H10	108.3
O3—C3—C2	124.33 (11)	C11—C10—H10	108.3
C4—C3—C2	107.91 (10)	S1—C10—H10	108.3
C5—C4—C9	120.86 (12)	O4—C11—N1	125.52 (12)
C5—C4—C3	128.50 (12)	O4—C11—C10	120.08 (11)
C9—C4—C3	110.63 (11)	N1—C11—C10	114.40 (10)
C6—C5—C4	118.26 (12)	N2—C12—N1	122.39 (12)
C6—C5—H5	120.9	N2—C12—S1	119.58 (9)
C4—C5—H5	120.9	N1—C12—S1	118.02 (10)

O1—C1—C2—O2	64.08 (15)	C5—C4—C9—C1	−179.91 (11)
C9—C1—C2—O2	−111.21 (11)	C3—C4—C9—C1	1.32 (14)
O1—C1—C2—C10	−58.41 (15)	O1—C1—C9—C8	0.5 (2)
C9—C1—C2—C10	126.30 (11)	C2—C1—C9—C8	175.40 (12)
O1—C1—C2—C3	177.88 (11)	O1—C1—C9—C4	−177.45 (12)
C9—C1—C2—C3	2.59 (12)	C2—C1—C9—C4	−2.51 (14)
O2—C2—C3—O3	−63.22 (15)	O2—C2—C10—C11	169.35 (10)
C10—C2—C3—O3	60.14 (16)	C3—C2—C10—C11	47.95 (14)
C1—C2—C3—O3	−178.97 (12)	C1—C2—C10—C11	−68.72 (13)
O2—C2—C3—C4	113.91 (10)	O2—C2—C10—S1	49.13 (12)
C10—C2—C3—C4	−122.72 (11)	C3—C2—C10—S1	−72.27 (12)
C1—C2—C3—C4	−1.84 (12)	C1—C2—C10—S1	171.06 (8)
O3—C3—C4—C5	−1.2 (2)	C12—S1—C10—C2	124.72 (9)
C2—C3—C4—C5	−178.24 (12)	C12—S1—C10—C11	0.93 (9)
O3—C3—C4—C9	177.42 (12)	C12—N1—C11—O4	−176.05 (12)
C2—C3—C4—C9	0.41 (14)	C12—N1—C11—C10	3.27 (15)
C9—C4—C5—C6	−1.35 (18)	C2—C10—C11—O4	52.60 (16)
C3—C4—C5—C6	177.19 (12)	S1—C10—C11—O4	176.80 (10)
C4—C5—C6—C7	−0.65 (19)	C2—C10—C11—N1	−126.76 (11)
C5—C6—C7—C8	2.1 (2)	S1—C10—C11—N1	−2.56 (13)
C6—C7—C8—C9	−1.44 (19)	C11—N1—C12—N2	178.04 (12)
C7—C8—C9—C4	−0.56 (19)	C11—N1—C12—S1	−2.57 (14)
C7—C8—C9—C1	−178.27 (12)	C10—S1—C12—N2	−179.74 (11)
C5—C4—C9—C8	1.99 (19)	C10—S1—C12—N1	0.85 (10)
C3—C4—C9—C8	−176.79 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84	1.99	2.8225 (13)	170
N2—H2A···N1ⁱⁱ	0.88	2.07	2.9372 (15)	168
N2—H2B···O2ⁱⁱⁱ	0.88	2.14	2.9629 (14)	155

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈N₂O₄S
M_r	276.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	90
a, b, c (Å)	14.1702 (2), 5.6713 (1), 14.8296 (3)
β (°)	114.0171 (9)
V (Å³)	1088.58 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.12 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.927, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	23811, 2498, 2268
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.06
No. of reflections	2498
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.26

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84	1.99	2.8225 (13)	170.0
N2—H2A···N1ⁱⁱ	0.88	2.07	2.9372 (15)	168.4
N2—H2B···O2ⁱⁱⁱ	0.88	2.14	2.9629 (14)	154.6

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA104457 (PAC) and by NSF MRI grant CHE 0319176 (SP).

References

Fun, H.-K., Quah, C. K., Parveen, M., Ghalib, R. M. & Mehdi, S. H. (2009). Acta Cryst. E65, o1209. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Nonius (1998). COLLECT and DENZO. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sekhar, K. R., Crooks, P. A., Sonar, V. N., Friedman, D. B., Chan, J. Y., Meredith, M. J., Stames, J. H., Kelton, K. R., Summar, S. R., Sasi, S. & Freeman, M. L. (2003). Cancer Res. 63, 5636–5645. Web of Science PubMed CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-2-(2-Amino-4-oxo-4,5-di­hydro-1,3-thia­zol-5-yl)-2-hy­droxy­indane-1,3-dione

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rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)-2-hydroxyindane-1,3-dione