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

In the title compound, C(10)H(9)NOS(2), the toluene group and the 2-thioxo-1,3-thia-zolidin-4-one unit are planar with r.m.s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between them is 71.20 (9)°. In the crystal, the mol-ecules are stabilized through inter-molecular C-H⋯O contacts, forming polymeric sheets extending parallel to the (01) plane. C-H⋯π contacts also occur.

Related literature

For related structures and the preparation, see: Shahwar et al. (2009a ▶,b ▶).

Experimental

Crystal data

C10H9NOS2

M = 223.30

Monoclinic,

a = 14.5885 (18) Å

b = 5.5766 (6) Å

c = 12.9910 (15) Å

β = 100.603 (6)°

V = 1038.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.939, T max = 0.950

7426 measured reflections

1871 independent reflections

1371 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.191

S = 1.07

1871 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) 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/S1600536810029569/si2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029569/si2279Isup2.hkl

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

C10H9NOS2	F(000) = 464
Mr = 223.30	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1371 reflections
a = 14.5885 (18) Å	θ = 3.3–25.2°
b = 5.5766 (6) Å	µ = 0.48 mm−1
c = 12.9910 (15) Å	T = 296 K
β = 100.603 (6)°	Prism, light yellow
V = 1038.8 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1871 independent reflections
Radiation source: fine-focus sealed tube	1371 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 8.10 pixels mm-1	θmax = 25.2°, θmin = 3.2°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.939, Tmax = 0.950	l = −14→15
7426 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1099P)2 + 0.6595P] where P = (Fo2 + 2Fc2)/3
1871 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.45 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	0.07809 (7)	0.7565 (2)	0.48054 (8)	0.0640 (4)
S2	0.08797 (7)	0.4645 (2)	0.29429 (9)	0.0645 (4)
O1	0.29145 (18)	1.1330 (5)	0.45318 (19)	0.0576 (9)
N1	0.20548 (18)	0.8215 (5)	0.3708 (2)	0.0419 (8)
C1	0.2640 (2)	0.7927 (6)	0.2936 (2)	0.0422 (10)
C2	0.3229 (2)	0.5995 (7)	0.2997 (3)	0.0486 (11)
C3	0.3830 (3)	0.5829 (7)	0.2290 (3)	0.0559 (12)
C4	0.3849 (3)	0.7554 (7)	0.1539 (3)	0.0522 (11)
C5	0.3251 (3)	0.9453 (8)	0.1489 (3)	0.0638 (14)
C6	0.2640 (3)	0.9667 (7)	0.2192 (3)	0.0561 (14)
C7	0.4528 (3)	0.7357 (9)	0.0792 (3)	0.0774 (18)
C8	0.2270 (2)	0.9984 (6)	0.4471 (3)	0.0455 (11)
C9	0.1587 (3)	0.9972 (8)	0.5211 (3)	0.0559 (12)
C10	0.1289 (2)	0.6787 (6)	0.3748 (3)	0.0470 (11)
H2	0.32242	0.48179	0.35029	0.0584*
H3	0.42296	0.45210	0.23248	0.0672*
H5	0.32517	1.06212	0.09782	0.0767*
H6	0.22378	1.09710	0.21555	0.0676*
H7A	0.48304	0.88736	0.07508	0.1162*
H7B	0.41973	0.69135	0.01101	0.1162*
H7C	0.49876	0.61574	0.10415	0.1162*
H9A	0.12591	1.14909	0.51789	0.0672*
H9B	0.19110	0.97175	0.59244	0.0672*

	U11	U22	U33	U12	U13	U23
S1	0.0506 (6)	0.0820 (8)	0.0656 (7)	−0.0038 (5)	0.0268 (5)	−0.0086 (5)
S2	0.0524 (6)	0.0690 (8)	0.0715 (8)	−0.0092 (5)	0.0097 (5)	−0.0155 (5)
O1	0.0639 (16)	0.0610 (17)	0.0485 (15)	−0.0104 (14)	0.0122 (12)	−0.0037 (12)
N1	0.0403 (14)	0.0497 (16)	0.0369 (14)	0.0036 (12)	0.0106 (11)	−0.0002 (12)
C1	0.0431 (18)	0.050 (2)	0.0345 (16)	0.0003 (14)	0.0098 (13)	−0.0013 (14)
C2	0.051 (2)	0.052 (2)	0.0429 (19)	0.0044 (16)	0.0093 (15)	0.0068 (16)
C3	0.051 (2)	0.066 (2)	0.052 (2)	0.0110 (18)	0.0132 (16)	−0.0024 (19)
C4	0.049 (2)	0.070 (2)	0.0395 (18)	−0.0142 (18)	0.0133 (15)	−0.0076 (17)
C5	0.089 (3)	0.063 (2)	0.044 (2)	−0.003 (2)	0.024 (2)	0.0133 (18)
C6	0.075 (3)	0.049 (2)	0.047 (2)	0.0102 (18)	0.0185 (18)	0.0057 (17)
C7	0.060 (3)	0.123 (4)	0.055 (2)	−0.022 (2)	0.026 (2)	−0.019 (2)
C8	0.052 (2)	0.0459 (19)	0.0391 (18)	0.0040 (16)	0.0099 (15)	0.0013 (14)
C9	0.056 (2)	0.069 (2)	0.045 (2)	0.0045 (18)	0.0150 (16)	−0.0037 (17)
C10	0.0400 (18)	0.053 (2)	0.048 (2)	0.0015 (15)	0.0080 (14)	0.0010 (15)

S1—C9	1.798 (5)	C4—C7	1.513 (6)
S1—C10	1.732 (4)	C5—C6	1.394 (6)
S2—C10	1.627 (4)	C8—C9	1.507 (5)
O1—C8	1.194 (4)	C2—H2	0.9300
N1—C1	1.441 (4)	C3—H3	0.9300
N1—C8	1.393 (4)	C5—H5	0.9300
N1—C10	1.381 (4)	C6—H6	0.9300
C1—C2	1.371 (5)	C7—H7A	0.9600
C1—C6	1.370 (5)	C7—H7B	0.9600
C2—C3	1.385 (5)	C7—H7C	0.9600
C3—C4	1.374 (5)	C9—H9A	0.9700
C4—C5	1.366 (6)	C9—H9B	0.9700
S1···N1	2.568 (3)	C6···H9Bvii	3.0300
S1···S1i	3.7490 (16)	C7···H3viii	3.0200
S1···S1ii	3.6396 (16)	C8···H6	3.0500
S2···C2	3.497 (3)	C8···H7Bv	2.9800
S2···C8iii	3.651 (4)	C10···H2	3.1000
S1···H9Aii	3.0300	H2···O1iii	2.4500
S2···H6iii	3.1500	H2···C10	3.1000
O1···C2iv	3.360 (5)	H3···H7C	2.3500
O1···C6	3.132 (5)	H3···C7ix	3.0200
O1···C7v	3.321 (5)	H5···H7A	2.5700
O1···H2iv	2.4500	H5···O1x	2.5100
O1···H5vi	2.5100	H6···S2iv	3.1500
O1···H7Bv	2.6100	H6···C8	3.0500
N1···S1	2.568 (3)	H7A···H5	2.5700
C2···S2	3.497 (3)	H7A···H7Axi	2.4500
C2···O1iii	3.360 (5)	H7B···O1vii	2.6100
C4···C8vii	3.500 (5)	H7B···C2vii	3.0800
C6···O1	3.132 (5)	H7B···C8vii	2.9800
C7···O1vii	3.321 (5)	H7C···H3	2.3500
C8···S2iv	3.651 (4)	H9A···S1ii	3.0300
C8···C4v	3.500 (5)	H9B···C1v	3.0200
C1···H9Bvii	3.0200	H9B···C2v	3.0300
C2···H9Bvii	3.0300	H9B···C3v	3.0400
C2···H7Bv	3.0800	H9B···C4v	3.0700
C3···H9Bvii	3.0400	H9B···C5v	3.0400
C4···H9Bvii	3.0700	H9B···C6v	3.0300
C5···H9Bvii	3.0400
C9—S1—C10	93.85 (18)	S2—C10—N1	127.1 (3)
C1—N1—C8	119.3 (3)	C1—C2—H2	121.00
C1—N1—C10	123.3 (3)	C3—C2—H2	121.00
C8—N1—C10	117.4 (3)	C2—C3—H3	119.00
N1—C1—C2	119.5 (3)	C4—C3—H3	119.00
N1—C1—C6	119.3 (3)	C4—C5—H5	120.00
C2—C1—C6	121.1 (3)	C6—C5—H5	119.00
C1—C2—C3	118.7 (3)	C1—C6—H6	121.00
C2—C3—C4	121.5 (4)	C5—C6—H6	120.00
C3—C4—C5	118.7 (4)	C4—C7—H7A	109.00
C3—C4—C7	120.4 (4)	C4—C7—H7B	109.00
C5—C4—C7	120.9 (4)	C4—C7—H7C	109.00
C4—C5—C6	121.0 (4)	H7A—C7—H7B	109.00
C1—C6—C5	119.0 (4)	H7A—C7—H7C	109.00
O1—C8—N1	124.3 (3)	H7B—C7—H7C	109.00
O1—C8—C9	124.5 (3)	S1—C9—H9A	110.00
N1—C8—C9	111.2 (3)	S1—C9—H9B	110.00
S1—C9—C8	106.9 (3)	C8—C9—H9A	110.00
S1—C10—S2	122.26 (19)	C8—C9—H9B	110.00
S1—C10—N1	110.7 (2)	H9A—C9—H9B	109.00
C9—S1—C10—N1	1.8 (3)	C10—N1—C8—C9	−0.3 (4)
C10—S1—C9—C8	−1.9 (3)	N1—C1—C6—C5	176.0 (3)
C9—S1—C10—S2	−178.1 (3)	C6—C1—C2—C3	0.1 (5)
C10—N1—C1—C2	−72.1 (4)	N1—C1—C2—C3	−175.8 (3)
C8—N1—C10—S2	178.7 (3)	C2—C1—C6—C5	0.0 (5)
C8—N1—C1—C6	−69.3 (4)	C1—C2—C3—C4	0.3 (6)
C10—N1—C1—C6	111.9 (4)	C2—C3—C4—C7	178.6 (4)
C8—N1—C1—C2	106.7 (4)	C2—C3—C4—C5	−0.7 (6)
C1—N1—C10—S1	177.6 (2)	C3—C4—C5—C6	0.9 (6)
C8—N1—C10—S1	−1.2 (4)	C7—C4—C5—C6	−178.5 (4)
C1—N1—C10—S2	−2.5 (5)	C4—C5—C6—C1	−0.5 (6)
C1—N1—C8—O1	0.7 (5)	O1—C8—C9—S1	−178.3 (3)
C10—N1—C8—O1	179.5 (3)	N1—C8—C9—S1	1.5 (4)
C1—N1—C8—C9	−179.1 (3)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1iii	0.93	2.45	3.360 (5)	167
C5—H5···O1x	0.93	2.51	3.432 (5)	169
C9—H9B···Cg2v	0.97	2.71	3.565 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.45	3.360 (5)	167
C5—H5⋯O1ii	0.93	2.51	3.432 (5)	169
C9—H9B⋯Cg2iii	0.97	2.71	3.565 (4)	147

Symmetry codes: (i) ; (ii) ; (iii) .