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

In the title compound, C(10)H(9)NOS(2), the dihedral angle between the rhodanine (2-thioxo-1,3-thia-zolidin-4-one) and 3-methyl-phenyl rings is 83.30 (3)°. The H atoms of the methyl group are disordered over two set of sites with an occupancy ratio of 0.58 (3):0.42 (3). In the crystal, the mol-ecules inter-act by way of C-H⋯π and C=O⋯π inter-actions.

Related literature

For related structures, see: Shahwar et al. (2009a ▶,b ▶,c ▶,d ▶,e ▶).

Experimental

Crystal data

C10H9NOS2

M = 223.3

Monoclinic,

a = 8.0775 (3) Å

b = 6.4058 (2) Å

c = 21.4715 (7) Å

β = 106.068 (2)°

V = 1067.59 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.849, T max = 0.897

11841 measured reflections

2666 independent reflections

2116 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.03

2666 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 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 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/S1600536809045863/hb5208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045863/hb5208Isup2.hkl

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

C10H9NOS2	F(000) = 464
Mr = 223.3	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2666 reflections
a = 8.0775 (3) Å	θ = 2.6–28.3°
b = 6.4058 (2) Å	µ = 0.46 mm−1
c = 21.4715 (7) Å	T = 296 K
β = 106.068 (2)°	Prism, light yellow
V = 1067.59 (6) Å3	0.32 × 0.24 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2666 independent reflections
Radiation source: fine-focus sealed tube	2116 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.849, Tmax = 0.897	l = −28→28
11841 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2635P] where P = (Fo2 + 2Fc2)/3
2666 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 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	Occ. (<1)
S1	0.90452 (5)	0.42703 (7)	0.26996 (2)	0.0484 (1)
S2	0.85641 (6)	0.38555 (7)	0.12935 (2)	0.0511 (2)
O1	0.54228 (16)	0.04248 (19)	0.26950 (6)	0.0537 (4)
N1	0.67528 (14)	0.18699 (18)	0.19889 (5)	0.0324 (3)
C1	0.56186 (18)	0.0913 (2)	0.14230 (7)	0.0337 (4)
C2	0.5937 (2)	−0.1103 (2)	0.12588 (8)	0.0419 (5)
C3	0.4818 (2)	−0.1972 (3)	0.07148 (8)	0.0501 (6)
C4	0.3436 (2)	−0.0858 (3)	0.03533 (8)	0.0518 (6)
C5	0.3103 (2)	0.1156 (3)	0.05186 (7)	0.0461 (5)
C6	0.42217 (18)	0.2036 (3)	0.10687 (7)	0.0391 (5)
C7	0.65129 (19)	0.1553 (2)	0.26005 (7)	0.0363 (4)
C8	0.77847 (19)	0.2774 (3)	0.31088 (7)	0.0410 (5)
C9	0.80207 (17)	0.3243 (2)	0.19488 (7)	0.0342 (4)
C10	0.1604 (2)	0.2403 (4)	0.01220 (10)	0.0730 (8)
H2	0.68758	−0.18517	0.15069	0.0502*
H3	0.50036	−0.33254	0.05925	0.0602*
H4	0.27025	−0.14709	−0.00126	0.0621*
H6	0.40257	0.33792	0.11964	0.0469*
H8A	0.85188	0.18403	0.34219	0.0492*
H8B	0.71912	0.36922	0.33352	0.0492*
H10A	0.06610	0.23026	0.03116	0.1095*	0.58 (3)
H10B	0.12550	0.18649	−0.03121	0.1095*	0.58 (3)
H10C	0.19388	0.38382	0.01132	0.1095*	0.58 (3)
H10D	0.19424	0.31376	−0.02127	0.1095*	0.42 (3)
H10E	0.12470	0.33875	0.03963	0.1095*	0.42 (3)
H10F	0.06653	0.14807	−0.00708	0.1095*	0.42 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0426 (2)	0.0565 (3)	0.0445 (2)	−0.0166 (2)	0.0092 (2)	−0.0128 (2)
S2	0.0545 (3)	0.0578 (3)	0.0449 (2)	−0.0180 (2)	0.0202 (2)	−0.0016 (2)
O1	0.0636 (8)	0.0544 (7)	0.0476 (7)	−0.0196 (6)	0.0227 (6)	0.0006 (5)
N1	0.0328 (6)	0.0310 (5)	0.0331 (6)	−0.0024 (5)	0.0088 (5)	−0.0023 (5)
C1	0.0341 (7)	0.0342 (7)	0.0343 (7)	−0.0077 (6)	0.0120 (6)	−0.0027 (6)
C2	0.0433 (8)	0.0364 (8)	0.0482 (9)	−0.0029 (6)	0.0166 (7)	−0.0041 (7)
C3	0.0592 (10)	0.0442 (9)	0.0529 (10)	−0.0167 (8)	0.0253 (8)	−0.0169 (8)
C4	0.0521 (10)	0.0673 (11)	0.0375 (8)	−0.0261 (9)	0.0150 (7)	−0.0131 (8)
C5	0.0379 (8)	0.0627 (10)	0.0371 (8)	−0.0096 (7)	0.0094 (6)	0.0066 (7)
C6	0.0385 (8)	0.0399 (8)	0.0395 (8)	−0.0039 (6)	0.0119 (6)	0.0011 (6)
C7	0.0395 (8)	0.0343 (7)	0.0359 (7)	0.0028 (6)	0.0118 (6)	0.0018 (6)
C8	0.0388 (8)	0.0481 (9)	0.0351 (7)	0.0015 (7)	0.0087 (6)	−0.0026 (7)
C9	0.0314 (7)	0.0319 (7)	0.0389 (7)	−0.0006 (5)	0.0091 (6)	−0.0025 (6)
C10	0.0505 (11)	0.0965 (17)	0.0611 (12)	−0.0013 (11)	−0.0027 (9)	0.0161 (11)

S1—C8	1.7952 (17)	C7—C8	1.496 (2)
S1—C9	1.7258 (15)	C2—H2	0.9300
S2—C9	1.6335 (15)	C3—H3	0.9300
O1—C7	1.199 (2)	C4—H4	0.9300
N1—C1	1.4406 (18)	C6—H6	0.9300
N1—C7	1.3943 (18)	C8—H8A	0.9700
N1—C9	1.3707 (18)	C8—H8B	0.9700
C1—C2	1.3814 (19)	C10—H10A	0.9600
C1—C6	1.376 (2)	C10—H10B	0.9600
C2—C3	1.381 (2)	C10—H10C	0.9600
C3—C4	1.371 (2)	C10—H10D	0.9600
C4—C5	1.384 (3)	C10—H10E	0.9600
C5—C6	1.392 (2)	C10—H10F	0.9600
C5—C10	1.503 (3)
C8—S1—C9	93.63 (7)	C2—C3—H3	120.00
C1—N1—C7	120.71 (12)	C4—C3—H3	120.00
C1—N1—C9	122.13 (11)	C3—C4—H4	119.00
C7—N1—C9	116.98 (11)	C5—C4—H4	119.00
N1—C1—C2	119.55 (13)	C1—C6—H6	120.00
N1—C1—C6	118.46 (13)	C5—C6—H6	120.00
C2—C1—C6	121.98 (14)	S1—C8—H8A	110.00
C1—C2—C3	117.92 (15)	S1—C8—H8B	110.00
C2—C3—C4	120.60 (17)	C7—C8—H8A	110.00
C3—C4—C5	121.72 (16)	C7—C8—H8B	110.00
C4—C5—C6	117.93 (16)	H8A—C8—H8B	109.00
C4—C5—C10	122.24 (16)	C5—C10—H10A	109.00
C6—C5—C10	119.83 (17)	C5—C10—H10B	109.00
C1—C6—C5	119.84 (16)	C5—C10—H10C	109.00
O1—C7—N1	123.17 (14)	C5—C10—H10D	109.00
O1—C7—C8	125.44 (14)	C5—C10—H10E	109.00
N1—C7—C8	111.39 (12)	C5—C10—H10F	109.00
S1—C8—C7	106.86 (10)	H10A—C10—H10B	109.00
S1—C9—S2	122.64 (8)	H10A—C10—H10C	109.00
S1—C9—N1	111.07 (10)	H10B—C10—H10C	109.00
S2—C9—N1	126.29 (11)	H10D—C10—H10E	109.00
C1—C2—H2	121.00	H10D—C10—H10F	109.00
C3—C2—H2	121.00	H10E—C10—H10F	109.00
C9—S1—C8—C7	−2.42 (12)	C7—N1—C9—S2	179.24 (11)
C8—S1—C9—S2	−177.72 (10)	N1—C1—C2—C3	179.72 (14)
C8—S1—C9—N1	1.42 (11)	C6—C1—C2—C3	1.1 (2)
C7—N1—C1—C2	−85.14 (18)	N1—C1—C6—C5	179.89 (14)
C7—N1—C1—C6	93.56 (16)	C2—C1—C6—C5	−1.5 (2)
C9—N1—C1—C2	99.88 (17)	C1—C2—C3—C4	−0.2 (2)
C9—N1—C1—C6	−81.42 (18)	C2—C3—C4—C5	−0.4 (3)
C1—N1—C7—O1	3.2 (2)	C3—C4—C5—C6	0.0 (3)
C1—N1—C7—C8	−177.29 (12)	C3—C4—C5—C10	179.27 (17)
C9—N1—C7—O1	178.41 (14)	C4—C5—C6—C1	0.9 (2)
C9—N1—C7—C8	−2.06 (18)	C10—C5—C6—C1	−178.41 (15)
C1—N1—C9—S1	175.30 (10)	O1—C7—C8—S1	−177.61 (13)
C1—N1—C9—S2	−5.60 (19)	N1—C7—C8—S1	2.88 (16)
C7—N1—C9—S1	0.14 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg2i	0.97	2.59	3.5219 (17)	162
C7—O1···Cg1i	1.199 (2)	2.9413 (14)	4.1070 (16)	163.94 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg2i	0.97	2.59	3.5219 (17)	162
C7—O1⋯Cg1i	1.20 (1)	2.94 (1)	4.1070 (16)	164 (1)

Symmetry code: (i) . Cg1 and Cg2 are the centroids of the S1/C8/C7/N1/C9 and C1—C6 rings, respectively.