3-Benzyl-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

In the title compound, C(10)H(9)NOS(2), the five-membered heterocyclic ring and the benzyl moiety are oriented at a dihedral angle of 77.25 (4)°. In the crystal, infinite polymeric C(6) chains extending along [001] are formed due to C-H⋯O hydrogen bonds. C-H⋯π inter-actions link the chains, building up a three-dimensional network.

Related literature

For background to our inter­est in the sythesis of thia­zolidin derivatives and related structures, see: Shahwar et al. (2009a ▶,b ▶, 2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9NOS2

M = 223.30

Monoclinic,

a = 13.3271 (4) Å

b = 5.9025 (2) Å

c = 13.0396 (4) Å

β = 92.812 (1)°

V = 1024.50 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.25 × 0.20 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

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

7899 measured reflections

1818 independent reflections

1594 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.07

1818 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.14 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/S1600536810051548/dn2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051548/dn2634Isup2.hkl

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

C10H9NOS2	F(000) = 464
Mr = 223.30	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1594 reflections
a = 13.3271 (4) Å	θ = 3.1–25.3°
b = 5.9025 (2) Å	µ = 0.48 mm−1
c = 13.0396 (4) Å	T = 296 K
β = 92.812 (1)°	Plate, light yellow
V = 1024.50 (6) Å3	0.25 × 0.20 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1818 independent reflections
Radiation source: fine-focus sealed tube	1594 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→7
Tmin = 0.939, Tmax = 0.950	l = −15→15
7899 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.031P)2 + 0.4046P] where P = (Fo2 + 2Fc2)/3
1818 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.14 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	0.06040 (4)	0.13455 (10)	0.18585 (4)	0.0638 (2)
S2	0.09221 (4)	0.28252 (9)	−0.02729 (3)	0.0557 (2)
O1	0.28194 (12)	0.7373 (2)	0.06176 (11)	0.0697 (5)
N1	0.18237 (9)	0.4684 (2)	0.12987 (9)	0.0396 (4)
C1	0.30044 (11)	0.3660 (3)	0.27679 (11)	0.0376 (5)
C2	0.33354 (12)	0.1781 (3)	0.22537 (13)	0.0443 (5)
C3	0.40774 (14)	0.0402 (3)	0.26955 (15)	0.0565 (6)
C4	0.44939 (15)	0.0897 (4)	0.36558 (16)	0.0632 (7)
C5	0.41747 (15)	0.2765 (4)	0.41688 (15)	0.0625 (7)
C6	0.34380 (14)	0.4147 (3)	0.37321 (13)	0.0509 (6)
C7	0.21689 (12)	0.5173 (3)	0.23542 (12)	0.0424 (5)
C8	0.11439 (12)	0.3010 (3)	0.10525 (13)	0.0437 (5)
C9	0.16998 (14)	0.5229 (3)	−0.05169 (13)	0.0531 (6)
C10	0.21917 (13)	0.5926 (3)	0.04939 (13)	0.0458 (5)
H2	0.30574	0.14374	0.16042	0.0531*
H3	0.42949	−0.08609	0.23425	0.0678*
H4	0.49897	−0.00340	0.39547	0.0758*
H5	0.44570	0.31047	0.48170	0.0749*
H6	0.32296	0.54169	0.40864	0.0611*
H7A	0.16040	0.50313	0.27915	0.0509*
H7B	0.23972	0.67325	0.23923	0.0509*
H9A	0.22040	0.48311	−0.09975	0.0637*
H9B	0.12960	0.64606	−0.08070	0.0637*

	U11	U22	U33	U12	U13	U23
S1	0.0582 (3)	0.0707 (4)	0.0624 (3)	−0.0218 (3)	0.0027 (2)	0.0073 (3)
S2	0.0562 (3)	0.0648 (3)	0.0451 (3)	−0.0033 (2)	−0.0074 (2)	−0.0115 (2)
O1	0.0892 (10)	0.0615 (9)	0.0584 (8)	−0.0281 (8)	0.0049 (7)	0.0054 (7)
N1	0.0425 (7)	0.0405 (7)	0.0354 (7)	−0.0013 (6)	−0.0010 (5)	−0.0012 (5)
C1	0.0404 (8)	0.0379 (8)	0.0347 (8)	−0.0064 (7)	0.0044 (6)	−0.0013 (6)
C2	0.0463 (9)	0.0459 (9)	0.0407 (9)	0.0003 (7)	0.0033 (7)	−0.0057 (7)
C3	0.0555 (10)	0.0499 (11)	0.0648 (12)	0.0086 (9)	0.0100 (9)	−0.0004 (9)
C4	0.0541 (11)	0.0672 (13)	0.0675 (13)	0.0063 (10)	−0.0052 (9)	0.0162 (11)
C5	0.0660 (12)	0.0712 (13)	0.0483 (11)	−0.0066 (10)	−0.0159 (9)	0.0056 (10)
C6	0.0612 (11)	0.0503 (10)	0.0407 (9)	−0.0039 (8)	−0.0029 (8)	−0.0065 (8)
C7	0.0502 (9)	0.0407 (9)	0.0363 (8)	0.0017 (7)	0.0020 (7)	−0.0064 (7)
C8	0.0395 (8)	0.0464 (9)	0.0448 (9)	0.0005 (7)	−0.0018 (7)	−0.0047 (7)
C9	0.0587 (10)	0.0617 (12)	0.0387 (9)	0.0052 (9)	0.0020 (8)	0.0030 (8)
C10	0.0516 (9)	0.0426 (9)	0.0433 (9)	0.0018 (8)	0.0035 (7)	0.0014 (7)

S1—C8	1.6315 (18)	C4—C5	1.368 (3)
S2—C8	1.7424 (17)	C5—C6	1.378 (3)
S2—C9	1.7947 (19)	C9—C10	1.501 (2)
O1—C10	1.201 (2)	C2—H2	0.9300
N1—C7	1.459 (2)	C3—H3	0.9300
N1—C8	1.368 (2)	C4—H4	0.9300
N1—C10	1.389 (2)	C5—H5	0.9300
C1—C2	1.380 (2)	C6—H6	0.9300
C1—C6	1.388 (2)	C7—H7A	0.9700
C1—C7	1.507 (2)	C7—H7B	0.9700
C2—C3	1.384 (2)	C9—H9A	0.9700
C3—C4	1.376 (3)	C9—H9B	0.9700
C8—S2—C9	93.15 (8)	C1—C2—H2	120.00
C7—N1—C8	122.61 (13)	C3—C2—H2	120.00
C7—N1—C10	120.12 (13)	C2—C3—H3	120.00
C8—N1—C10	117.27 (13)	C4—C3—H3	120.00
C2—C1—C6	118.55 (15)	C3—C4—H4	120.00
C2—C1—C7	123.43 (14)	C5—C4—H4	120.00
C6—C1—C7	117.98 (15)	C4—C5—H5	120.00
C1—C2—C3	120.62 (16)	C6—C5—H5	120.00
C2—C3—C4	120.13 (18)	C1—C6—H6	120.00
C3—C4—C5	119.66 (19)	C5—C6—H6	120.00
C4—C5—C6	120.49 (18)	N1—C7—H7A	109.00
C1—C6—C5	120.55 (17)	N1—C7—H7B	109.00
N1—C7—C1	114.46 (13)	C1—C7—H7A	109.00
S1—C8—S2	122.86 (10)	C1—C7—H7B	109.00
S1—C8—N1	126.28 (13)	H7A—C7—H7B	108.00
S2—C8—N1	110.86 (12)	S2—C9—H9A	110.00
S2—C9—C10	106.99 (12)	S2—C9—H9B	110.00
O1—C10—N1	122.91 (16)	C10—C9—H9A	110.00
O1—C10—C9	125.76 (16)	C10—C9—H9B	110.00
N1—C10—C9	111.33 (14)	H9A—C9—H9B	109.00
C9—S2—C8—S1	176.53 (12)	C6—C1—C2—C3	0.6 (2)
C9—S2—C8—N1	−4.19 (13)	C7—C1—C2—C3	−177.17 (16)
C8—S2—C9—C10	5.77 (13)	C2—C1—C6—C5	−0.7 (3)
C8—N1—C7—C1	82.66 (18)	C7—C1—C6—C5	177.15 (17)
C10—N1—C7—C1	−96.82 (17)	C2—C1—C7—N1	−8.0 (2)
C7—N1—C8—S1	0.9 (2)	C6—C1—C7—N1	174.18 (14)
C7—N1—C8—S2	−178.35 (11)	C1—C2—C3—C4	−0.1 (3)
C10—N1—C8—S1	−179.60 (13)	C2—C3—C4—C5	−0.4 (3)
C10—N1—C8—S2	1.15 (18)	C3—C4—C5—C6	0.2 (3)
C7—N1—C10—O1	2.5 (2)	C4—C5—C6—C1	0.4 (3)
C7—N1—C10—C9	−177.06 (14)	S2—C9—C10—O1	174.34 (16)
C8—N1—C10—O1	−177.01 (16)	S2—C9—C10—N1	−6.12 (17)
C8—N1—C10—C9	3.4 (2)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.47	3.338 (2)	156
C3—H3···Cgii	0.93	2.95	3.674 (2)	136
C9—H9a···Cgiii	0.97	2.66	3.588 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.47	3.338 (2)	156
C3—H3⋯Cgii	0.93	2.95	3.674 (2)	136
C9—H9a⋯Cgiii	0.97	2.66	3.588 (2)	160

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