3-Cyclo-hexyl-2-thioxo-1,3-thia-zolidin-4-one.

In the title compound, C(9)H(13)NOS(2), the complete mol-ecule is generated by crystallographic mirror symmetry, with all the non-H atoms of the rhodanine (2-thioxo-1,3-thia-zolidin-4-one) system and two C atoms of the cyclo-hexyl ring lying on the reflecting plane. The conformation is stabilized by intra-molecular C-H⋯O and C-H⋯S inter-actions. In the crystal, weak π-π inter-actions at a distance of 3.8140 (5) Å between the centroids of the heterocyclic rings occur.

Related literature

For related structures, see: Shahwar et al. (2009a ▶,b ▶,c ▶,d ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H13NOS2

M = 215.32

Monoclinic,

a = 7.3897 (3) Å

b = 7.0999 (4) Å

c = 10.3399 (5) Å

β = 107.535 (2)°

V = 517.29 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.36 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

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

5969 measured reflections

1390 independent reflections

1194 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.07

1390 reflections

76 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.23 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/S1600536809045851/hb5207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045851/hb5207Isup2.hkl

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

C9H13NOS2	F(000) = 228
Mr = 215.32	Dx = 1.382 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1390 reflections
a = 7.3897 (3) Å	θ = 2.9–28.4°
b = 7.0999 (4) Å	µ = 0.48 mm−1
c = 10.3399 (5) Å	T = 296 K
β = 107.535 (2)°	Prism, colourless
V = 517.29 (4) Å3	0.36 × 0.25 × 0.23 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1390 independent reflections
Radiation source: fine-focus sealed tube	1194 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.4°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.849, Tmax = 0.897	l = −13→12
5969 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.1418P] where P = (Fo2 + 2Fc2)/3
1390 reflections	(Δ/σ)max < 0.001
76 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.23 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	0.01379 (9)	0.25000	0.58014 (6)	0.0511 (2)
S2	0.41214 (8)	0.25000	0.58341 (6)	0.0543 (2)
O1	−0.1794 (2)	0.25000	0.19333 (18)	0.0591 (6)
N1	0.1088 (2)	0.25000	0.35969 (16)	0.0351 (4)
C1	0.1866 (3)	0.25000	0.4967 (2)	0.0363 (5)
C2	−0.1778 (3)	0.25000	0.4253 (3)	0.0477 (7)
C3	−0.0908 (3)	0.25000	0.3109 (2)	0.0412 (6)
C4	0.2266 (2)	0.25000	0.26546 (19)	0.0356 (5)
C5	0.1971 (2)	0.0715 (2)	0.18098 (16)	0.0450 (4)
C6	0.3246 (2)	0.0739 (3)	0.08896 (17)	0.0527 (5)
C7	0.2925 (4)	0.25000	0.0025 (3)	0.0590 (8)
H2	−0.255 (2)	0.142 (3)	0.4183 (17)	0.0573*
H4	0.35945	0.25000	0.32201	0.0427*
H51	0.06529	0.06226	0.12627	0.0540*
H52	0.22695	−0.03748	0.24022	0.0540*
H61	0.45638	0.06820	0.14408	0.0633*
H62	0.29826	−0.03620	0.03070	0.0633*
H71	0.16366	0.25000	−0.05835	0.0707*
H72	0.37843	0.25000	−0.05230	0.0707*

	U11	U22	U33	U12	U13	U23
S1	0.0636 (4)	0.0480 (3)	0.0539 (3)	0.0000	0.0361 (3)	0.0000
S2	0.0461 (3)	0.0671 (4)	0.0438 (3)	0.0000	0.0046 (2)	0.0000
O1	0.0307 (7)	0.0850 (13)	0.0582 (10)	0.0000	0.0084 (7)	0.0000
N1	0.0300 (7)	0.0394 (8)	0.0382 (8)	0.0000	0.0138 (6)	0.0000
C1	0.0431 (9)	0.0288 (8)	0.0401 (10)	0.0000	0.0173 (8)	0.0000
C2	0.0417 (10)	0.0390 (11)	0.0722 (15)	0.0000	0.0318 (10)	0.0000
C3	0.0303 (8)	0.0395 (10)	0.0554 (12)	0.0000	0.0153 (8)	0.0000
C4	0.0273 (7)	0.0445 (10)	0.0365 (9)	0.0000	0.0121 (7)	0.0000
C5	0.0444 (7)	0.0422 (8)	0.0528 (8)	0.0012 (6)	0.0213 (6)	−0.0023 (6)
C6	0.0485 (8)	0.0602 (10)	0.0554 (9)	0.0028 (7)	0.0246 (7)	−0.0120 (8)
C7	0.0561 (13)	0.0816 (18)	0.0456 (12)	0.0000	0.0250 (10)	0.0000

S1—C1	1.743 (2)	C6—C7	1.514 (3)
S1—C2	1.789 (3)	C2—H2	0.95 (2)
S2—C1	1.637 (2)	C2—H2i	0.95 (2)
O1—C3	1.195 (3)	C4—H4	0.9800
N1—C1	1.359 (3)	C5—H51	0.9700
N1—C3	1.408 (3)	C5—H52	0.9700
N1—C4	1.489 (2)	C6—H61	0.9700
C2—C3	1.507 (3)	C6—H62	0.9700
C4—C5	1.5172 (18)	C7—H71	0.9700
C4—C5i	1.5172 (18)	C7—H72	0.9700
C5—C6	1.528 (2)
C1—S1—C2	93.28 (11)	C3—C2—H2i	109.3 (10)
C1—N1—C3	116.24 (17)	H2—C2—H2i	108.4 (16)
C1—N1—C4	122.34 (16)	N1—C4—H4	107.00
C3—N1—C4	121.43 (15)	C5—C4—H4	107.00
S1—C1—S2	120.37 (12)	C5i—C4—H4	107.00
S1—C1—N1	111.90 (16)	C4—C5—H51	110.00
S2—C1—N1	127.73 (17)	C4—C5—H52	110.00
S1—C2—C3	107.02 (16)	C6—C5—H51	110.00
O1—C3—N1	124.0 (2)	C6—C5—H52	110.00
O1—C3—C2	124.5 (2)	H51—C5—H52	108.00
N1—C3—C2	111.56 (18)	C5—C6—H61	109.00
N1—C4—C5	111.45 (9)	C5—C6—H62	109.00
N1—C4—C5i	111.45 (9)	C7—C6—H61	109.00
C5—C4—C5i	113.30 (14)	C7—C6—H62	109.00
C4—C5—C6	109.92 (13)	H61—C6—H62	108.00
C5—C6—C7	111.15 (17)	C6—C7—H71	109.00
C6—C7—C6i	111.4 (2)	C6—C7—H72	109.00
S1—C2—H2	111.4 (11)	H71—C7—H72	108.00
S1—C2—H2i	111.4 (11)	C6i—C7—H71	109.00
C3—C2—H2	109.3 (10)	C6i—C7—H72	109.00
C2—S1—C1—S2	180.00 (1)	C4—N1—C3—C2	180.00 (1)
C2—S1—C1—N1	0.00 (1)	C1—N1—C4—C5	116.17 (11)
C1—S1—C2—C3	0.00 (1)	C3—N1—C4—C5	−63.83 (11)
C3—N1—C1—S1	0.00 (1)	S1—C2—C3—O1	180.00 (1)
C3—N1—C1—S2	180.00 (1)	S1—C2—C3—N1	0.00 (1)
C4—N1—C1—S1	180.00 (1)	N1—C4—C5—C6	−178.24 (13)
C4—N1—C1—S2	0.00 (1)	C5i—C4—C5—C6	55.10 (17)
C1—N1—C3—O1	180.00 (1)	C4—C5—C6—C7	−54.99 (19)
C1—N1—C3—C2	0.00 (1)	C5—C6—C7—C6i	56.9 (2)
C4—N1—C3—O1	0.00 (1)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S2	0.98	2.61	3.158 (2)	115
C5—H51···O1	0.97	2.51	3.095 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯S2	0.98	2.61	3.158 (2)	115
C5—H51⋯O1	0.97	2.51	3.095 (2)	119