rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thia-zol-5-yl)-2-hydroxy-indane-1,3-dione.

In the crystal of the title compound, C(12)H(8)N(2)O(4)S, mol-ecules are linked into chains by a series of inter-molecular O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds. The ninhydrin and amino-thia-zolidine units make a dihedral angle of 66.41 (3)°. The crystal structure indicates the presence of equimolar R and S enanti-omers 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 = 276.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.06

2498 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.26 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H8N2O4S	F(000) = 568
Mr = 276.26	Dx = 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

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

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(Fo2) + (0.0342P)2 + 0.6796P], where P = (Fo2 + 2Fc2)/3
2498 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .