3-Benzyl-2-(furan-2-yl)-1,3-thia-zolidin-4-one.

In the title compound, C(14)H(13)NO(2)S, the thia-zolidine ring is approximately planar with a maximum deviation of 0.112 (1) Å. The furan ring is disordered over two orientations, with an occupancy ratio of 0.901 (5):0.099 (5). The central thia-zolidine ring makes dihedral angles of 85.43 (8), 87.50 (11) and 87.9 (9)° with the phenyl ring and the major and minor components of the disordered furan ring, respectively. In the crystal, mol-ecules are connected by weak inter-molecular C-H⋯O hydrogen bonds, forming supra-molecular chains parallel to the b axis.

Related literature

For details and applications of thia­zolidine-4-ones, see: Dutta et al. (1990 ▶); Jadhav & Ingle (1978 ▶); Gursoy et al. (2005 ▶); Rawal et al. (2007 ▶); Shrivastava et al. (2005 ▶); Look et al. (1996 ▶); Anders et al. (2001 ▶); Barreca et al. (2001 ▶); Diurno et al. (1992 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H13NO2S

M = 259.31

Monoclinic,

a = 13.2901 (2) Å

b = 9.6360 (1) Å

c = 9.9152 (1) Å

β = 102.855 (1)°

V = 1237.95 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.30 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.961

13239 measured reflections

3551 independent reflections

2794 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.104

S = 1.07

3551 reflections

180 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039432/rz2640sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039432/rz2640Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039432/rz2640Isup3.cml

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

C14H13NO2S	F(000) = 544
Mr = 259.31	Dx = 1.391 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5111 reflections
a = 13.2901 (2) Å	θ = 2.6–29.8°
b = 9.6360 (1) Å	µ = 0.25 mm−1
c = 9.9152 (1) Å	T = 100 K
β = 102.855 (1)°	Block, colourless
V = 1237.95 (3) Å3	0.30 × 0.18 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	2794 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 29.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.928, Tmax = 0.961	k = −9→13
13239 measured reflections	l = −10→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0277P)2 + 1.0975P] where P = (Fo2 + 2Fc2)/3
3551 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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	0.94899 (3)	0.23126 (5)	0.26095 (5)	0.02134 (12)
O2	0.82632 (10)	0.47724 (13)	−0.03755 (13)	0.0249 (3)
N1	0.78175 (10)	0.28671 (15)	0.07263 (15)	0.0176 (3)
C1	0.85886 (16)	−0.1044 (3)	−0.0489 (2)	0.0257 (6)	0.901 (5)
H1A	0.8838	−0.1380	−0.1231	0.031*	0.901 (5)
C2	0.8142 (2)	−0.1838 (3)	0.0346 (3)	0.0234 (7)	0.901 (5)
H2A	0.8031	−0.2791	0.0288	0.028*	0.901 (5)
C3	0.78759 (17)	−0.0901 (2)	0.1338 (2)	0.0218 (5)	0.901 (5)
H3A	0.7556	−0.1132	0.2051	0.026*	0.901 (5)
O1	0.86228 (11)	0.0324 (2)	−0.00892 (16)	0.0228 (4)	0.901 (5)
C1X	0.7671 (17)	−0.190 (2)	0.096 (2)	0.030 (5)*	0.099 (5)
H1XA	0.7404	−0.2758	0.1125	0.036*	0.099 (5)
C2X	0.828 (2)	−0.160 (3)	0.004 (3)	0.016 (6)*	0.099 (5)
H2XA	0.8446	−0.2253	−0.0560	0.019*	0.099 (5)
C3X	0.8599 (19)	−0.030 (3)	0.009 (3)	0.031 (6)*	0.099 (5)
H3XA	0.9034	0.0087	−0.0426	0.037*	0.099 (5)
O1X	0.7542 (15)	−0.060 (2)	0.1596 (18)	0.038 (5)*	0.099 (5)
C4	0.81768 (12)	0.03740 (19)	0.10405 (18)	0.0188 (3)
C5	0.81880 (12)	0.17612 (18)	0.17059 (18)	0.0174 (3)
H5A	0.7748	0.1722	0.2378	0.021*
C6	0.95721 (13)	0.3595 (2)	0.1314 (2)	0.0241 (4)
H6A	0.9851	0.4456	0.1751	0.029*
H6B	1.0020	0.3270	0.0730	0.029*
C7	0.84910 (12)	0.38244 (18)	0.04616 (17)	0.0177 (3)
C8	0.67229 (12)	0.29307 (19)	0.00708 (18)	0.0196 (4)
H8A	0.6477	0.2000	−0.0195	0.024*
H8B	0.6634	0.3482	−0.0766	0.024*
C9	0.60718 (12)	0.35483 (17)	0.09945 (17)	0.0164 (3)
C10	0.64856 (13)	0.44688 (19)	0.20516 (18)	0.0209 (4)
H10A	0.7185	0.4682	0.2227	0.025*
C11	0.58667 (13)	0.50767 (19)	0.28530 (18)	0.0218 (4)
H11A	0.6152	0.5694	0.3555	0.026*
C12	0.48236 (13)	0.4757 (2)	0.25993 (19)	0.0229 (4)
H12A	0.4407	0.5156	0.3134	0.027*
C13	0.44033 (13)	0.3840 (2)	0.1546 (2)	0.0257 (4)
H13A	0.3704	0.3625	0.1374	0.031*
C14	0.50243 (13)	0.32405 (19)	0.07495 (19)	0.0213 (4)
H14A	0.4737	0.2627	0.0045	0.026*

	U11	U22	U33	U12	U13	U23
S1	0.01828 (19)	0.0221 (2)	0.0216 (2)	0.00020 (16)	0.00008 (15)	−0.00073 (18)
O2	0.0310 (7)	0.0178 (7)	0.0270 (7)	0.0029 (5)	0.0089 (5)	0.0037 (5)
N1	0.0153 (6)	0.0165 (7)	0.0208 (7)	0.0019 (5)	0.0037 (5)	0.0018 (6)
C1	0.0270 (10)	0.0223 (12)	0.0268 (11)	0.0083 (9)	0.0033 (9)	−0.0086 (10)
C2	0.0199 (12)	0.0136 (13)	0.0337 (17)	−0.0003 (9)	−0.0006 (11)	0.0005 (11)
C3	0.0173 (9)	0.0179 (11)	0.0290 (11)	−0.0006 (8)	0.0021 (8)	0.0011 (9)
O1	0.0266 (8)	0.0204 (10)	0.0232 (8)	0.0048 (7)	0.0093 (6)	−0.0014 (7)
C4	0.0153 (7)	0.0204 (9)	0.0202 (8)	0.0026 (6)	0.0027 (6)	0.0002 (7)
C5	0.0155 (7)	0.0170 (8)	0.0203 (8)	0.0019 (6)	0.0051 (6)	0.0021 (7)
C6	0.0187 (8)	0.0208 (10)	0.0330 (10)	−0.0017 (7)	0.0061 (7)	0.0024 (8)
C7	0.0206 (7)	0.0131 (8)	0.0204 (8)	0.0020 (6)	0.0069 (6)	−0.0021 (7)
C8	0.0159 (7)	0.0207 (9)	0.0211 (8)	0.0018 (6)	0.0018 (6)	−0.0019 (7)
C9	0.0176 (7)	0.0118 (8)	0.0189 (8)	0.0022 (6)	0.0020 (6)	0.0031 (6)
C10	0.0160 (7)	0.0223 (9)	0.0230 (9)	0.0014 (6)	0.0011 (6)	−0.0005 (7)
C11	0.0238 (8)	0.0201 (9)	0.0206 (8)	0.0029 (7)	0.0026 (7)	−0.0028 (7)
C12	0.0232 (8)	0.0204 (9)	0.0266 (9)	0.0070 (7)	0.0089 (7)	0.0035 (7)
C13	0.0174 (8)	0.0254 (10)	0.0355 (10)	−0.0007 (7)	0.0081 (7)	0.0001 (8)
C14	0.0200 (8)	0.0151 (9)	0.0277 (9)	−0.0039 (6)	0.0032 (7)	−0.0031 (7)

S1—C6	1.8032 (19)	O1X—C4	1.453 (18)
S1—C5	1.8410 (16)	C4—C5	1.489 (2)
O2—C7	1.226 (2)	C5—H5A	0.9800
N1—C7	1.351 (2)	C6—C7	1.512 (2)
N1—C5	1.452 (2)	C6—H6A	0.9700
N1—C8	1.457 (2)	C6—H6B	0.9700
C1—C2	1.357 (4)	C8—C9	1.515 (2)
C1—O1	1.375 (3)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.436 (4)	C9—C10	1.390 (2)
C2—H2A	0.9300	C9—C14	1.391 (2)
C3—C4	1.344 (3)	C10—C11	1.394 (2)
C3—H3A	0.9300	C10—H10A	0.9300
O1—C4	1.380 (2)	C11—C12	1.387 (2)
C1X—C2X	1.37 (3)	C11—H11A	0.9300
C1X—O1X	1.43 (3)	C12—C13	1.387 (3)
C1X—H1XA	0.9300	C12—H12A	0.9300
C2X—C3X	1.32 (4)	C13—C14	1.389 (3)
C2X—H2XA	0.9300	C13—H13A	0.9300
C3X—C4	1.36 (3)	C14—H14A	0.9300
C3X—H3XA	0.9300
C6—S1—C5	92.90 (8)	C4—C5—H5A	108.6
C7—N1—C5	119.36 (13)	S1—C5—H5A	108.6
C7—N1—C8	121.58 (15)	C7—C6—S1	107.31 (12)
C5—N1—C8	119.06 (14)	C7—C6—H6A	110.3
C2—C1—O1	110.8 (2)	S1—C6—H6A	110.3
C2—C1—H1A	124.6	C7—C6—H6B	110.3
O1—C1—H1A	124.6	S1—C6—H6B	110.3
C1—C2—C3	105.7 (2)	H6A—C6—H6B	108.5
C1—C2—H2A	127.1	O2—C7—N1	124.45 (15)
C3—C2—H2A	127.1	O2—C7—C6	123.23 (16)
C4—C3—C2	107.1 (2)	N1—C7—C6	112.32 (15)
C4—C3—H3A	126.5	N1—C8—C9	113.27 (14)
C2—C3—H3A	126.5	N1—C8—H8A	108.9
C1—O1—C4	105.93 (18)	C9—C8—H8A	108.9
C2X—C1X—O1X	105 (2)	N1—C8—H8B	108.9
C2X—C1X—H1XA	127.6	C9—C8—H8B	108.9
O1X—C1X—H1XA	127.6	H8A—C8—H8B	107.7
C3X—C2X—C1X	114 (3)	C10—C9—C14	118.73 (16)
C3X—C2X—H2XA	122.9	C10—C9—C8	121.56 (15)
C1X—C2X—H2XA	122.9	C14—C9—C8	119.66 (15)
C2X—C3X—C4	107 (2)	C9—C10—C11	120.90 (16)
C2X—C3X—H3XA	126.4	C9—C10—H10A	119.5
C4—C3X—H3XA	126.4	C11—C10—H10A	119.5
C1X—O1X—C4	105.1 (15)	C12—C11—C10	119.73 (17)
C3—C4—C3X	84.6 (13)	C12—C11—H11A	120.1
C3—C4—O1	110.41 (18)	C10—C11—H11A	120.1
C3X—C4—O1X	108.5 (14)	C13—C12—C11	119.79 (16)
O1—C4—O1X	132.6 (8)	C13—C12—H12A	120.1
C3—C4—C5	134.18 (18)	C11—C12—H12A	120.1
C3X—C4—C5	140.1 (13)	C12—C13—C14	120.16 (16)
O1—C4—C5	115.28 (16)	C12—C13—H13A	119.9
O1X—C4—C5	111.3 (8)	C14—C13—H13A	119.9
N1—C5—C4	113.19 (14)	C13—C14—C9	120.68 (17)
N1—C5—S1	104.82 (11)	C13—C14—H14A	119.7
C4—C5—S1	112.97 (11)	C9—C14—H14A	119.7
N1—C5—H5A	108.6
O1—C1—C2—C3	0.1 (2)	O1—C4—C5—N1	49.22 (19)
C1—C2—C3—C4	−0.1 (2)	O1X—C4—C5—N1	−121.5 (8)
C2—C1—O1—C4	0.0 (2)	C3—C4—C5—S1	105.7 (2)
O1X—C1X—C2X—C3X	4(3)	C3X—C4—C5—S1	−57.9 (17)
C1X—C2X—C3X—C4	−2(3)	O1—C4—C5—S1	−69.72 (17)
C2X—C1X—O1X—C4	−4(2)	O1X—C4—C5—S1	119.6 (8)
C2—C3—C4—C3X	−6.0 (11)	C6—S1—C5—N1	−16.21 (12)
C2—C3—C4—O1	0.1 (2)	C6—S1—C5—C4	107.48 (13)
C2—C3—C4—O1X	153.3 (18)	C5—S1—C6—C7	15.65 (13)
C2—C3—C4—C5	−175.46 (19)	C5—N1—C7—O2	177.75 (16)
C2X—C3X—C4—C3	8.7 (19)	C8—N1—C7—O2	−3.4 (3)
C2X—C3X—C4—O1	−159 (4)	C5—N1—C7—C6	−2.0 (2)
C2X—C3X—C4—O1X	−1(2)	C8—N1—C7—C6	176.90 (15)
C2X—C3X—C4—C5	177.0 (13)	S1—C6—C7—O2	169.34 (14)
C1—O1—C4—C3	0.0 (2)	S1—C6—C7—N1	−10.94 (18)
C1—O1—C4—C3X	14 (2)	C7—N1—C8—C9	−99.90 (19)
C1—O1—C4—O1X	−15.4 (10)	C5—N1—C8—C9	78.97 (19)
C1—O1—C4—C5	176.43 (14)	N1—C8—C9—C10	25.8 (2)
C1X—O1X—C4—C3	−18.8 (11)	N1—C8—C9—C14	−157.01 (16)
C1X—O1X—C4—C3X	3.0 (18)	C14—C9—C10—C11	−0.1 (3)
C1X—O1X—C4—O1	16.1 (18)	C8—C9—C10—C11	177.10 (16)
C1X—O1X—C4—C5	−175.3 (11)	C9—C10—C11—C12	0.3 (3)
C7—N1—C5—C4	−110.10 (17)	C10—C11—C12—C13	−0.3 (3)
C8—N1—C5—C4	70.99 (19)	C11—C12—C13—C14	0.1 (3)
C7—N1—C5—S1	13.44 (18)	C12—C13—C14—C9	0.1 (3)
C8—N1—C5—S1	−165.46 (12)	C10—C9—C14—C13	−0.1 (3)
C3—C4—C5—N1	−135.4 (2)	C8—C9—C14—C13	−177.32 (17)
C3X—C4—C5—N1	61.0 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.48	3.355 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.48	3.355 (3)	158

Symmetry code: (i) .