3-(2-Methyl-phen-yl)-2-thioxo-1,3-thia-zolidin-4-one.

In the title compound, C(10)H(9)NOS(2), the 1,3-thia-zolidine and 2-methyl-phenyl rings are oriented at a dihedral angle of 84.44 (9)°. In the crystal, an unusual bifurcated C-H⋯(O,π) inter-action leads to zigzag chains of mol-ecules.

Related literature

For background to rhodanine derivatives, see: Cutshall et al. (2005 ▶). For related structures, see: Shahwar et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C10H9NOS2

M = 223.30

Monoclinic,

a = 23.690 (5) Å

b = 7.1401 (17) Å

c = 14.628 (3) Å

β = 122.215 (6)°

V = 2093.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.47 mm−1

T = 296 K

0.34 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.914, T max = 0.934

10878 measured reflections

2661 independent reflections

1436 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.189

S = 1.02

2661 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045814/hb5205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045814/hb5205Isup2.hkl

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

C10H9NOS2	F(000) = 928
Mr = 223.30	Dx = 1.417 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2661 reflections
a = 23.690 (5) Å	θ = 2.8–28.7°
b = 7.1401 (17) Å	µ = 0.47 mm−1
c = 14.628 (3) Å	T = 296 K
β = 122.215 (6)°	Cut needle, dark yellow
V = 2093.5 (8) Å3	0.34 × 0.16 × 0.14 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	1436 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 2.8°
ω scans	h = −31→30
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→5
Tmin = 0.914, Tmax = 0.934	l = −17→19
10878 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0949P)2 + 0.6816P] where P = (Fo2 + 2Fc2)/3
2661 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 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.

	x	y	z	Uiso*/Ueq
S1	0.21396 (5)	−0.00494 (13)	−0.00417 (7)	0.0612 (3)
S2	0.07182 (5)	0.09169 (18)	−0.10373 (8)	0.0903 (4)
O1	0.26644 (11)	0.2834 (4)	0.24779 (19)	0.0733 (9)
N1	0.17183 (11)	0.1968 (3)	0.09176 (18)	0.0475 (8)
C1	0.12842 (14)	0.2941 (4)	0.1167 (2)	0.0499 (10)
C2	0.11018 (15)	0.4752 (5)	0.0824 (2)	0.0527 (10)
C3	0.06977 (17)	0.5655 (6)	0.1131 (3)	0.0672 (12)
C4	0.05067 (19)	0.4719 (7)	0.1737 (3)	0.0768 (16)
C5	0.0691 (2)	0.2946 (7)	0.2068 (3)	0.0779 (16)
C6	0.10811 (17)	0.2011 (6)	0.1777 (3)	0.0660 (14)
C7	0.23984 (15)	0.1956 (5)	0.1655 (2)	0.0509 (11)
C8	0.27516 (16)	0.0721 (5)	0.1295 (3)	0.0555 (11)
C9	0.14858 (16)	0.1022 (4)	−0.0033 (3)	0.0537 (11)
C10	0.1303 (2)	0.5694 (6)	0.0175 (3)	0.0726 (14)
H3	0.05615	0.68853	0.09201	0.0808*
H4	0.02385	0.53341	0.19283	0.0918*
H5	0.05568	0.23555	0.24881	0.0933*
H6	0.12066	0.07745	0.19869	0.0793*
H8A	0.29480	−0.03430	0.17767	0.0668*
H8B	0.31039	0.14084	0.12918	0.0668*
H10A	0.11483	0.50009	−0.04790	0.1090*
H10B	0.17806	0.57808	0.05699	0.1090*
H10C	0.11140	0.69291	0.00017	0.1090*

	U11	U22	U33	U12	U13	U23
S1	0.0782 (6)	0.0598 (6)	0.0604 (5)	0.0158 (4)	0.0468 (5)	0.0023 (4)
S2	0.0723 (7)	0.0974 (9)	0.0678 (7)	0.0173 (6)	0.0150 (5)	−0.0333 (6)
O1	0.0542 (14)	0.097 (2)	0.0562 (14)	0.0095 (13)	0.0211 (12)	−0.0126 (14)
N1	0.0499 (14)	0.0541 (16)	0.0422 (13)	0.0081 (11)	0.0271 (12)	−0.0011 (11)
C1	0.0464 (16)	0.0565 (19)	0.0440 (16)	0.0030 (13)	0.0222 (14)	−0.0077 (14)
C2	0.0533 (18)	0.064 (2)	0.0423 (16)	0.0056 (14)	0.0265 (15)	−0.0023 (14)
C3	0.060 (2)	0.075 (2)	0.057 (2)	0.0178 (17)	0.0247 (17)	−0.0056 (18)
C4	0.057 (2)	0.121 (4)	0.061 (2)	0.002 (2)	0.0373 (19)	−0.013 (2)
C5	0.076 (3)	0.103 (3)	0.074 (2)	−0.016 (2)	0.053 (2)	−0.012 (2)
C6	0.066 (2)	0.086 (3)	0.0577 (19)	−0.0094 (18)	0.0409 (18)	−0.0094 (18)
C7	0.0538 (18)	0.059 (2)	0.0442 (17)	0.0084 (15)	0.0291 (15)	0.0084 (15)
C8	0.0607 (19)	0.063 (2)	0.0565 (18)	0.0147 (15)	0.0404 (17)	0.0164 (16)
C9	0.069 (2)	0.0464 (18)	0.0475 (17)	0.0080 (14)	0.0323 (16)	−0.0041 (14)
C10	0.089 (3)	0.062 (2)	0.079 (2)	0.0073 (19)	0.053 (2)	0.008 (2)

S1—C8	1.790 (4)	C4—C5	1.343 (7)
S1—C9	1.734 (4)	C5—C6	1.379 (7)
S2—C9	1.619 (4)	C7—C8	1.492 (6)
O1—C7	1.196 (4)	C3—H3	0.9300
N1—C1	1.440 (4)	C4—H4	0.9300
N1—C7	1.381 (4)	C5—H5	0.9300
N1—C9	1.370 (4)	C6—H6	0.9300
C1—C2	1.371 (5)	C8—H8A	0.9700
C1—C6	1.388 (5)	C8—H8B	0.9700
C2—C3	1.412 (6)	C10—H10A	0.9600
C2—C10	1.436 (6)	C10—H10B	0.9600
C3—C4	1.366 (6)	C10—H10C	0.9600
C8—S1—C9	93.61 (19)	S2—C9—N1	126.4 (3)
C1—N1—C7	119.9 (2)	C2—C3—H3	120.00
C1—N1—C9	122.7 (3)	C4—C3—H3	120.00
C7—N1—C9	117.4 (3)	C3—C4—H4	119.00
N1—C1—C2	119.4 (3)	C5—C4—H4	119.00
N1—C1—C6	118.1 (3)	C4—C5—H5	120.00
C2—C1—C6	122.5 (3)	C6—C5—H5	120.00
C1—C2—C3	116.7 (3)	C1—C6—H6	120.00
C1—C2—C10	122.2 (4)	C5—C6—H6	120.00
C3—C2—C10	121.1 (4)	S1—C8—H8A	110.00
C2—C3—C4	119.9 (4)	S1—C8—H8B	110.00
C3—C4—C5	122.6 (5)	C7—C8—H8A	110.00
C4—C5—C6	119.2 (4)	C7—C8—H8B	110.00
C1—C6—C5	119.1 (4)	H8A—C8—H8B	109.00
O1—C7—N1	123.5 (3)	C2—C10—H10A	109.00
O1—C7—C8	124.9 (3)	C2—C10—H10B	109.00
N1—C7—C8	111.6 (3)	C2—C10—H10C	109.00
S1—C8—C7	106.7 (3)	H10A—C10—H10B	110.00
S1—C9—S2	123.3 (2)	H10A—C10—H10C	110.00
S1—C9—N1	110.4 (3)	H10B—C10—H10C	110.00
C9—S1—C8—C7	−4.5 (3)	C7—N1—C9—S2	−177.0 (3)
C8—S1—C9—S2	−179.4 (2)	N1—C1—C2—C3	−177.5 (3)
C8—S1—C9—N1	1.8 (3)	N1—C1—C2—C10	3.1 (4)
C7—N1—C1—C2	94.3 (3)	C6—C1—C2—C3	0.6 (5)
C7—N1—C1—C6	−84.0 (4)	C6—C1—C2—C10	−178.8 (3)
C9—N1—C1—C2	−86.2 (4)	N1—C1—C6—C5	177.0 (3)
C9—N1—C1—C6	95.6 (4)	C2—C1—C6—C5	−1.2 (5)
C1—N1—C7—O1	−5.7 (5)	C1—C2—C3—C4	−0.2 (5)
C1—N1—C7—C8	174.3 (3)	C10—C2—C3—C4	179.2 (4)
C9—N1—C7—O1	174.7 (3)	C2—C3—C4—C5	0.4 (6)
C9—N1—C7—C8	−5.4 (4)	C3—C4—C5—C6	−0.9 (7)
C1—N1—C9—S1	−177.9 (2)	C4—C5—C6—C1	1.3 (6)
C1—N1—C9—S2	3.4 (4)	O1—C7—C8—S1	−173.9 (3)
C7—N1—C9—S1	1.8 (3)	N1—C7—C8—S1	6.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.58	3.214 (5)	123
C8—H8A···Cg2i	0.97	2.65	3.420 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.58	3.214 (5)	123
C8—H8A⋯Cg2i	0.97	2.65	3.420 (4)	137

Symmetry code: (i) . Cg2 is the centroid of the C1–C6 ring.