(Z)-3-(2-Hy­droxy­eth­yl)-2-(phenyl­imino)-1,3-thia­zolidin-4-one

Shaaban K Mohamed; Antar A Abdelhamid; Sabry H H Younes; Mahmoud A A Elremaily; Jim Simpson

doi:10.1107/S1600536812030243

. 2012 Jul 7;68(Pt 8):o2371–o2372. doi: 10.1107/S1600536812030243

(Z)-3-(2-Hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one

Shaaban K Mohamed ^a, Antar A Abdelhamid ^a, Sabry H H Younes ^b, Mahmoud A A Elremaily ^b, Jim Simpson ^c,^*

PMCID: PMC3414302 PMID: 22904835

Abstract

In the title compound, C₁₁H₁₂N₂O₂S, the thiazole and phenyl rings are inclined at 56.99 (6)° to one another. The thiazole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The presence of the phenylimine substituent is confirmed with the C=N distance to the thiazole ring of 1.2638 (19) Å. The molecule adopts a Z conformation with respect to this bond. The –OH group of the hydroxyethyl 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 molecules 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 _r = 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
Δρ_max = 0.79 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-68-o2371-sup1.cif^{(20KB, cif)}

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

e-68-o2371-Isup2.hkl^{(125.1KB, hkl)}

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

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

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⋯S1^iv	0.99	2.92	3.613 (2)	128
C1—H1B⋯N5^v	0.99	2.57	3.519 (3)	162
C9—H9⋯Cg2^vi	0.95	2.77	3.5731 (16)	142

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

Acknowledgments

The financial support of the Egyptian Higher Education authority is gratefully acknowledged. We extend also our thanks to Manchester Metropolitan University for supporting this study and the University of Otago for the purchase of the diffractometer.

supplementary crystallographic information

Comment

Compounds incorporating the thiazolidinone core structure are of great interest to chemists and biologists due to their extensive bioactivities (Shah & Desai, 2007). These include anti-microbial (Subudhi et al., 2007), anti-mycobacterial (Kuecuekguezel et al., 2006), anti-inflammatory (Srivastava et al., 2006), anti-fungal (Mehta et al., 2006) and anti-cancer effects (Zhou et al., 2008). In this context and following our on-going study of the synthesis of bio-selective molecules we were interested in investigating the microbial inhibiting effect of a newly synthesized series of compounds incorporating thiazolidinone ring systems. The synthesis of such compounds was carried out via a three component reaction technique using amino alcohols as precursors (Mohamed et al., 2012). In this study, the crystal structure determination of the title compound (I) was undertaken to investigate the relationship between its structure and anti-bacterial activity.

The title compound (I), a phenylimino-thiazolidinone derivative, crystallizes with the S1/C1/C2/N1/C4 thiazole and C6···C11 phenyl rings inclined at 56.99 (6) ° to one another. The thiazole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The C4═N5 distance, 1.2638 (19) Å, confirms this as a double bond and the molecule adopts a Z conformation with respect to this bond. The OH group of the hydroxyethyl substituent is disordered over two positions with relative occupancies 0.517 (4) for O2–H2 and 0.483 (4) for O3–H3. Bond distances (Allen et al., 1987) and angles in the molecule are normal and similar to those found in related structures (Bally & Mornon, 1973; Moghaddam & Hojabri, 2007; Yella et al., 2008; Abdel-Aziz et al., 2012).

In the crystal structure head to tail dimers are formed from O2–H2···O1 hydrogen bonds, bolstered by weaker C1–H1B···N1 interactions, Table 1, forming R²₂(11) rings (Bernstein et al., 1995). These also link pairs of molecules into chains along b. Weak C12–H1B···S1 contacts join each chain to an equivalent one progressing in the opposite direction, Fig. 2. Two additional C–H···O hydrogen bonds together with C9–H9···π contacts further consolidate the structure forming stacks along b, Fig. 3.

Experimental

To a well stirred mixture of 135 mg (1 mmol) phenylisothiocyanate and 61 mg (1 mmol) 2-aminoethanol in 50 ml dioxane, 167 mg (1 mmol) of bromo ethylacetate was added. The reaction mixture was refluxed and monitored by TLC until completion after 3 h. A solid product was deposited on cooling to room temperature and collected by filtration. The crude product was recrystallized from ethanol to give a high quality crystals (M.p. 327 K) suitable for X-ray analysis in an excellent yield (92%).