3-Phenyl-2-thioxo-1,3-thia-zolidin-4-one.

In the mol-ecule of the title compound, C(9)H(7)NOS(2), the heterocycle and the phenyl ring are oriented at a dihedral angle of 72.3 (1)°. Adjacent mol-ecules are connected through C-H⋯O inter-actions.

Related literature

For the synthesis of 3-phenyl­rhodanine, see: Brown et al. (1956 ▶). For the therapeutic properties of rhodanine-based mol­ecules, including anti­convulsant, anti­bacterial, anti­viral and anti­diabetic properties, see: Momose et al. (1991 ▶); HCV protease, Sudo et al. (1997 ▶); HCV NS3 protease, Sing et al. (2001 ▶); aldols reductase, Bruno et al. (2002 ▶); factor protease, Sherida et al. (2006 ▶).

Experimental

Crystal data

C9H7NOS2

M = 209.28

Monoclinic,

a = 12.9941 (13) Å

b = 5.6111 (6) Å

c = 12.7271 (13) Å

β = 93.847 (3)°

V = 925.86 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 296 (2) K

0.20 × 0.15 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.91, T max = 0.97

10918 measured reflections

1800 independent reflections

1146 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.080

S = 1.00

1800 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030079/pk2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030079/pk2120Isup2.hkl

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

C9H7NOS2	F(000) = 432
Mr = 209.28	Dx = 1.501 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1321 reflections
a = 12.9941 (13) Å	θ = 3.1–21.1°
b = 5.6111 (6) Å	µ = 0.53 mm−1
c = 12.7271 (13) Å	T = 296 K
β = 93.847 (3)°	Plate, yellow
V = 925.86 (17) Å3	0.20 × 0.15 × 0.05 mm
Z = 4

Bruker APEXII diffractometer	1800 independent reflections
Radiation source: fine-focus sealed tube	1146 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 8 pixels mm-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −6→6
Tmin = 0.91, Tmax = 0.97	l = −15→15
10918 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0272P)2 + 0.2182P] where P = (Fo2 + 2Fc2)/3
1800 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. 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.

Refinement. 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.

	x	y	z	Uiso*/Ueq
C1	0.35704 (19)	0.8242 (4)	0.64373 (18)	0.0412 (6)
C2	0.2485 (2)	0.5060 (4)	0.58348 (17)	0.0413 (6)
C3	0.32529 (19)	0.5020 (4)	0.50099 (19)	0.0495 (7)
H3A	0.2908	0.5231	0.4317	0.059*
H3B	0.3616	0.3508	0.5024	0.059*
C4	0.20680 (17)	0.7118 (4)	0.74476 (17)	0.0351 (6)
C5	0.13898 (18)	0.8984 (4)	0.74630 (18)	0.0433 (6)
H5	0.1376	1.0140	0.6938	0.052*
C6	0.07285 (19)	0.9134 (5)	0.8263 (2)	0.0478 (7)
H6	0.0262	1.0389	0.8275	0.057*
C7	0.0756 (2)	0.7437 (5)	0.90434 (19)	0.0484 (7)
H7	0.0309	0.7549	0.9582	0.058*
C8	0.1438 (2)	0.5586 (5)	0.90295 (19)	0.0512 (7)
H8	0.1455	0.4441	0.9559	0.061*
C9	0.21025 (19)	0.5414 (4)	0.82277 (18)	0.0444 (6)
H9	0.2569	0.4158	0.8216	0.053*
N1	0.27190 (14)	0.6844 (3)	0.65849 (14)	0.0364 (5)
O1	0.17588 (14)	0.3754 (3)	0.58706 (13)	0.0541 (5)
S1	0.41400 (5)	0.74161 (13)	0.52991 (6)	0.0566 (2)
S2	0.40143 (5)	1.03944 (13)	0.71931 (6)	0.0583 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0359 (15)	0.0436 (15)	0.0446 (14)	0.0026 (12)	0.0059 (11)	0.0053 (12)
C2	0.0456 (16)	0.0411 (15)	0.0378 (13)	0.0024 (13)	0.0066 (12)	0.0023 (12)
C3	0.0501 (16)	0.0522 (17)	0.0475 (14)	0.0041 (14)	0.0124 (12)	−0.0048 (13)
C4	0.0342 (14)	0.0356 (14)	0.0362 (12)	−0.0006 (11)	0.0077 (11)	−0.0010 (11)
C5	0.0440 (16)	0.0407 (15)	0.0458 (15)	0.0024 (13)	0.0069 (13)	0.0055 (11)
C6	0.0403 (16)	0.0461 (16)	0.0577 (16)	0.0089 (13)	0.0089 (13)	−0.0033 (13)
C7	0.0474 (16)	0.0539 (17)	0.0458 (14)	−0.0049 (15)	0.0182 (12)	−0.0063 (14)
C8	0.0614 (18)	0.0489 (16)	0.0445 (15)	−0.0046 (15)	0.0125 (14)	0.0097 (13)
C9	0.0497 (16)	0.0370 (14)	0.0472 (14)	0.0093 (12)	0.0090 (12)	0.0044 (12)
N1	0.0359 (12)	0.0356 (11)	0.0386 (11)	−0.0007 (9)	0.0088 (9)	−0.0003 (9)
O1	0.0594 (13)	0.0506 (11)	0.0532 (11)	−0.0147 (10)	0.0107 (9)	−0.0059 (9)
S1	0.0465 (4)	0.0673 (5)	0.0588 (4)	−0.0072 (4)	0.0228 (3)	−0.0061 (4)
S2	0.0511 (5)	0.0561 (5)	0.0682 (5)	−0.0128 (4)	0.0081 (4)	−0.0131 (4)

C1—N1	1.379 (3)	C4—N1	1.439 (3)
C1—S2	1.626 (3)	C5—C6	1.378 (3)
C1—S1	1.733 (2)	C5—H5	0.9300
C2—O1	1.198 (3)	C6—C7	1.375 (3)
C2—N1	1.402 (3)	C6—H6	0.9300
C2—C3	1.496 (3)	C7—C8	1.366 (3)
C3—S1	1.793 (3)	C7—H7	0.9300
C3—H3A	0.9700	C8—C9	1.384 (3)
C3—H3B	0.9700	C8—H8	0.9300
C4—C5	1.370 (3)	C9—H9	0.9300
C4—C9	1.377 (3)
N1—C1—S2	126.73 (18)	C6—C5—H5	120.3
N1—C1—S1	110.68 (17)	C7—C6—C5	120.3 (2)
S2—C1—S1	122.59 (15)	C7—C6—H6	119.9
O1—C2—N1	123.1 (2)	C5—C6—H6	119.9
O1—C2—C3	125.5 (2)	C8—C7—C6	120.2 (2)
N1—C2—C3	111.4 (2)	C8—C7—H7	119.9
C2—C3—S1	107.11 (17)	C6—C7—H7	119.9
C2—C3—H3A	110.3	C7—C8—C9	120.0 (2)
S1—C3—H3A	110.3	C7—C8—H8	120.0
C2—C3—H3B	110.3	C9—C8—H8	120.0
S1—C3—H3B	110.3	C4—C9—C8	119.5 (2)
H3A—C3—H3B	108.5	C4—C9—H9	120.3
C5—C4—C9	120.7 (2)	C8—C9—H9	120.3
C5—C4—N1	120.3 (2)	C1—N1—C2	116.9 (2)
C9—C4—N1	118.9 (2)	C1—N1—C4	124.14 (19)
C4—C5—C6	119.4 (2)	C2—N1—C4	119.0 (2)
C4—C5—H5	120.3	C1—S1—C3	93.86 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.51	3.410 (3)	163.
C8—H8···O1ii	0.93	2.46	3.386 (3)	171.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.51	3.410 (3)	163
C8—H8⋯O1ii	0.93	2.46	3.386 (3)	171

Symmetry codes: (i) ; (ii) .