(Z)-3-(2-Hy-droxy-eth-yl)-2-(phenyl-imino)-1,3-thia-zolidin-4-one.

In the title compound, C(11)H(12)N(2)O(2)S, the thia-zole and phenyl rings are inclined at 56.99 (6)° to one another. The thia-zole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The presence of the phenyl-imine substituent is confirmed with the C=N distance to the thia-zole ring of 1.2638 (19) Å. The mol-ecule adopts a Z conformation with respect to this bond. The -OH group of the hy-droxy-ethyl substituent is disordered over two positions with relative occupancies 0.517 (4) and 0.483 (4). In the crystal, O-H⋯O hydrogen bonds, augmented by C-H⋯N contacts, form dimers with R(2) (2)(11) rings and generate chains along the b axis. Parallel chains are linked in an obverse fashion by weak C-H⋯S hydrogen bonds. C-H⋯O hydrogen bonds together with C-H⋯π contacts further consolidate the structure, stacking mol-ecules along the b axis.

Related literature

For pharmaceutical background to thia­zolidinone compounds, see: Shah & Desai (2007 ▶); Subudhi et al. (2007 ▶); Kuecuekguezel et al. (2006 ▶); Mehta et al. (2006 ▶); Srivastava et al. (2006 ▶); Zhou et al. (2008 ▶). For our recent work on the synthesis of bio-selective mol­ecules, see: Mohamed et al. (2012 ▶). For related structures, see: Bally & Mornon (1973 ▶); Moghaddam & Hojabri (2007 ▶); Yella et al. (2008 ▶); Abdel-Aziz et al. (2012 ▶). For standard bond distances, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H12N2O2S

M = 236.29

Monoclinic,

a = 11.9612 (6) Å

b = 6.9478 (3) Å

c = 13.1554 (6) Å

β = 91.244 (2)°

V = 1093.01 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 91 K

0.40 × 0.26 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.693, T max = 0.746

17811 measured reflections

2547 independent reflections

2150 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.08

2547 reflections

157 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: APEX2 and SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030243/tk5126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030243/tk5126Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030243/tk5126Isup3.cml

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

C11H12N2O2S	F(000) = 496
Mr = 236.29	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5327 reflections
a = 11.9612 (6) Å	θ = 3.3–27.6°
b = 6.9478 (3) Å	µ = 0.28 mm−1
c = 13.1554 (6) Å	T = 91 K
β = 91.244 (2)°	Irregular block, yellow
V = 1093.01 (9) Å3	0.40 × 0.26 × 0.11 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	2150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.7°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −15→15
Tmin = 0.693, Tmax = 0.746	k = −9→9
17811 measured reflections	l = −17→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.9645P] where P = (Fo2 + 2Fc2)/3
2547 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.79 e Å−3
6 restraints	Δρmin = −0.68 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	0.27696 (4)	0.19764 (7)	0.90742 (4)	0.02132 (14)
C1	0.18673 (18)	0.0254 (3)	0.96766 (16)	0.0261 (4)
H1A	0.1232	−0.0083	0.9216	0.031*
H1B	0.2287	−0.0937	0.9843	0.031*
C2	0.14480 (17)	0.1172 (3)	1.06312 (15)	0.0248 (4)
O1	0.08555 (15)	0.0341 (2)	1.12382 (12)	0.0393 (4)
N1	0.17971 (13)	0.3030 (2)	1.07448 (12)	0.0204 (3)
C4	0.24668 (14)	0.3775 (3)	0.99792 (13)	0.0172 (4)
N5	0.28128 (12)	0.5494 (2)	1.00068 (11)	0.0180 (3)
C6	0.34388 (14)	0.6235 (3)	0.91831 (14)	0.0171 (4)
C7	0.29991 (15)	0.6270 (3)	0.81901 (14)	0.0196 (4)
H7	0.2298	0.5682	0.8039	0.023*
C8	0.35896 (16)	0.7167 (3)	0.74242 (15)	0.0213 (4)
H8	0.3292	0.7179	0.6749	0.026*
C9	0.46134 (17)	0.8049 (3)	0.76381 (15)	0.0234 (4)
H9	0.5014	0.8661	0.7113	0.028*
C10	0.50430 (16)	0.8025 (3)	0.86274 (15)	0.0233 (4)
H10	0.5742	0.8623	0.8777	0.028*
C11	0.44593 (15)	0.7135 (3)	0.94010 (14)	0.0201 (4)
H11	0.4755	0.7139	1.0077	0.024*
C12	0.14901 (17)	0.4171 (3)	1.16360 (15)	0.0255 (4)
H12A	0.2113	0.5057	1.1812	0.031*
H12B	0.1393	0.3292	1.2220	0.031*
C13	0.0447 (2)	0.5319 (4)	1.14846 (19)	0.0439 (6)
H13A	−0.0167	0.4364	1.1469	0.053*
H13B	0.0363	0.6054	1.2123	0.053*
O2	0.0188 (2)	0.6593 (4)	1.0724 (2)	0.0241 (8)	0.517 (4)
H2	0.0483	0.7663	1.0856	0.036*	0.517 (4)
O3	−0.0418 (2)	0.4527 (5)	1.1267 (2)	0.0316 (9)	0.483 (4)
H3	−0.0409	0.4168	1.0658	0.047*	0.483 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0221 (2)	0.0226 (3)	0.0195 (2)	0.00206 (18)	0.00538 (17)	−0.00315 (18)
C1	0.0326 (10)	0.0206 (10)	0.0254 (10)	−0.0003 (8)	0.0066 (8)	−0.0018 (8)
C2	0.0280 (10)	0.0244 (10)	0.0221 (10)	−0.0040 (8)	0.0038 (8)	−0.0013 (8)
O1	0.0548 (10)	0.0346 (9)	0.0292 (8)	−0.0195 (8)	0.0170 (7)	−0.0056 (7)
N1	0.0211 (8)	0.0236 (8)	0.0166 (8)	−0.0037 (6)	0.0043 (6)	−0.0034 (6)
C4	0.0140 (8)	0.0230 (9)	0.0146 (8)	0.0029 (7)	−0.0001 (6)	−0.0010 (7)
N5	0.0161 (7)	0.0229 (8)	0.0150 (7)	0.0014 (6)	0.0010 (6)	−0.0006 (6)
C6	0.0181 (8)	0.0163 (8)	0.0170 (9)	0.0037 (7)	0.0029 (7)	−0.0007 (7)
C7	0.0197 (8)	0.0203 (9)	0.0187 (9)	0.0040 (7)	0.0008 (7)	−0.0016 (7)
C8	0.0280 (9)	0.0186 (9)	0.0172 (9)	0.0058 (7)	0.0014 (7)	0.0014 (7)
C9	0.0302 (10)	0.0182 (9)	0.0220 (10)	0.0017 (8)	0.0066 (8)	0.0043 (8)
C10	0.0221 (9)	0.0205 (9)	0.0272 (10)	−0.0028 (7)	0.0018 (8)	0.0020 (8)
C11	0.0223 (9)	0.0191 (9)	0.0187 (9)	0.0009 (7)	−0.0014 (7)	0.0013 (7)
C12	0.0322 (10)	0.0290 (10)	0.0157 (9)	−0.0098 (8)	0.0084 (8)	−0.0067 (8)
C13	0.0564 (10)	0.0410 (10)	0.0346 (9)	0.0164 (8)	0.0045 (8)	−0.0037 (8)
O2	0.0295 (15)	0.0209 (14)	0.0217 (15)	−0.0021 (11)	−0.0001 (11)	−0.0017 (11)
O3	0.0208 (15)	0.054 (2)	0.0197 (16)	0.0020 (14)	0.0030 (11)	−0.0044 (15)

S1—C4	1.7689 (19)	C8—H8	0.9500
S1—C1	1.806 (2)	C9—C10	1.389 (3)
C1—C2	1.504 (3)	C9—H9	0.9500
C1—H1A	0.9900	C10—C11	1.392 (3)
C1—H1B	0.9900	C10—H10	0.9500
C2—O1	1.224 (2)	C11—H11	0.9500
C2—N1	1.364 (3)	C12—C13	1.490 (3)
N1—C4	1.400 (2)	C12—H12A	0.9900
N1—C12	1.469 (2)	C12—H12B	0.9900
C4—N5	1.264 (2)	C13—O3	1.202 (4)
N5—C6	1.427 (2)	C13—O2	1.367 (4)
C6—C11	1.396 (3)	C13—H13A	0.9900
C6—C7	1.398 (3)	C13—H13B	0.9900
C7—C8	1.391 (3)	O2—H2	0.8400
C7—H7	0.9500	O3—H3	0.8400
C8—C9	1.393 (3)
C4—S1—C1	92.29 (9)	C10—C9—C8	119.34 (18)
C2—C1—S1	107.38 (14)	C10—C9—H9	120.3
C2—C1—H1A	110.2	C8—C9—H9	120.3
S1—C1—H1A	110.2	C9—C10—C11	120.61 (18)
C2—C1—H1B	110.2	C9—C10—H10	119.7
S1—C1—H1B	110.2	C11—C10—H10	119.7
H1A—C1—H1B	108.5	C10—C11—C6	119.96 (17)
O1—C2—N1	123.72 (18)	C10—C11—H11	120.0
O1—C2—C1	123.58 (19)	C6—C11—H11	120.0
N1—C2—C1	112.69 (17)	N1—C12—C13	113.91 (18)
C2—N1—C4	116.73 (16)	N1—C12—H12A	108.8
C2—N1—C12	121.13 (16)	C13—C12—H12A	108.8
C4—N1—C12	122.13 (16)	N1—C12—H12B	108.8
N5—C4—N1	121.38 (16)	C13—C12—H12B	108.8
N5—C4—S1	127.96 (14)	H12A—C12—H12B	107.7
N1—C4—S1	110.59 (13)	O3—C13—O2	86.7 (3)
C4—N5—C6	119.74 (16)	O3—C13—C12	120.0 (3)
C11—C6—C7	119.60 (17)	O2—C13—C12	128.4 (2)
C11—C6—N5	118.48 (16)	O2—C13—H13A	105.2
C7—C6—N5	121.54 (16)	C12—C13—H13A	105.2
C8—C7—C6	119.88 (17)	O3—C13—H13B	109.6
C8—C7—H7	120.1	O2—C13—H13B	105.2
C6—C7—H7	120.1	C12—C13—H13B	105.2
C7—C8—C9	120.61 (18)	H13A—C13—H13B	105.9
C7—C8—H8	119.7	C13—O2—H2	109.5
C9—C8—H8	119.7	C13—O3—H3	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	1.98	2.802 (3)	168
C13—H13B···O1ii	0.99	2.67	3.407 (3)	131
C1—H1A···O1iii	0.99	2.56	3.472 (3)	153
C12—H12B···S1iv	0.99	2.92	3.613 (2)	128
C1—H1B···N5v	0.99	2.57	3.519 (3)	162
C9—H9···Cg2vi	0.95	2.77	3.5731 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C11 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	1.98	2.802 (3)	168
C13—H13B⋯O1ii	0.99	2.67	3.407 (3)	131
C1—H1A⋯O1iii	0.99	2.56	3.472 (3)	153
C12—H12B⋯S1iv	0.99	2.92	3.613 (2)	128
C1—H1B⋯N5v	0.99	2.57	3.519 (3)	162
C9—H9⋯Cg2vi	0.95	2.77	3.5731 (16)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .