2-(2-Chloro-3-quinol­yl)-3-phenyl­thia­zolidin-4-one

Wei-Wei Liu; Ji-You Sun; Li-Juan Tang; Yue-Qiang Zhao; Hong-Wen Hu

doi:10.1107/S1600536809041543

. 2009 Oct 17;65(Pt 11):o2753. doi: 10.1107/S1600536809041543

2-(2-Chloro-3-quinolyl)-3-phenylthiazolidin-4-one

Wei-Wei Liu ^a,^*, Ji-You Sun ^a, Li-Juan Tang ^a, Yue-Qiang Zhao ^a, Hong-Wen Hu ^b

PMCID: PMC2971196 PMID: 21578347

Abstract

In the title compound, C₁₈H₁₃ClN₂OS, the thiazolidinone ring is slightly distorted and adopts a envelope conformation. The basal plane is nearly perpendicular to the quinoline ring, forming a dihedral angle of 86.1 (1)°, and makes a dihedral angle of 14.9 (1)° to the benzene ring. The benzene ring is also nearly perpendicular to the quinoline ring, forming a dihedral angle of 89.4 (1)°. In the crystal, non-classical C—H⋯O and C—H⋯N hydrogen bonds link the molecules, forming polymers along b.

Related literature

For the biological activity of thiazolidinone derivatives, see: Abd Elhafez et al. (2003 ▶); Kuecuekguezel et al. (2006 ▶); Shih & Ke (2004 ▶); Subudhi et al. (2007 ▶); Srivastava et al. (2006 ▶).

Experimental

Crystal data

C₁₈H₁₃ClN₂OS
M _r = 340.81
Monoclinic,
a = 16.1192 (6) Å
b = 12.7502 (5) Å
c = 16.8949 (6) Å
β = 110.379 (2)°
V = 3255.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
12810 measured reflections
2883 independent reflections
2165 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.098
S = 1.05
2883 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041543/gw2069sup1.cif

e-65-o2753-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041543/gw2069Isup2.hkl

e-65-o2753-Isup2.hkl^{(141.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯N1ⁱ	0.93	2.63	3.514 (3)	158
C3—H3A⋯O1ⁱⁱ	0.93	2.35	3.192 (2)	151

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Six Kinds of Professional Elite Foundation of Jiangsu Province (No. 07-A-024), the Education Department Natural Science Foundation of Jiangsu Province (No. 08KJB150002), the Key Laboratory of the Marine Biotechnology Foundation of Jiangsu Province (No. 2006HS014) and the Science and Technology Critical Project Foundation of Lianyungang Municipality (CG0803–2).

supplementary crystallographic information

Comment

Thiazolidinone derivatives are important heterocyclic nitrogen compounds which display a wide range of biological activity. Some synthetic thiazolidinones have been used as antiviral (Abd Elhafez et al., 2003), antioxidant (Shih and Ke, 2004), antimycobacterial (Kuecuekguezel et al., 2006), antimicrobial (Subudhi et al., 2007), and also as antiinflammatory (Srivastava et al., 2006). We report here the structure of 2-(2-chloroquinolin-3-yl)- 3-phenylthiazolidin-4-one, (I).

In (I), the thiazolidinone ring is slightly distorted and adopts a envelope conformation: the atoms of C11, C12, N2 and C10 are coplanar, with S1 deviating from the defined plane by 0.673 Å. The basal plane is nearly perpendicular to the quinoline ring, forming a dihedral angle of 86.1 (1) °, and makes a dihedral angle of 14.9 (1) ° to benzene ring. The benzene ring is also nearly to perpendicular to the quinoline ring, forming a dihedral angle of 89.4 (1) °.

There are two non-classical hydrogen bonds of C3—H3A···O1 and C8—H8A···N1 in the crystal structure. The former links the adjacent molecules forming dimmers, while the latter also links another adjacent molecules forming polymers. The two above mentioned non-classical hydrogen bonds link the molecules forming polymers along b.

Experimental

A solution of 2-chloroquinoline-3-carbadehyde (1.92 g, 10 mmol) and 5 mmol aniline (0.5 ml, 5.5 mmol) in anhydrous THF (30 ml) was stirred under ice-cold conditions for 5 min, followed by addition of mercapto acid (1.1 ml, 15 mmol). Dicyclohexylcarbodiimide (DCC) (6 mmol) was added to the reaction mixture 5 min later, the resulting mixture was stirred at ambient temperature for 1 h. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was concentrated under reduced pressure and the residue was taken up in some ethyl acetate. The organic layer was successively washed with 5% aq. citric acid, water, 5% aq. sodium hydrogen carbonate, and then finally with brine. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to get a crude product that was purified by column chromatography on silica gel with petroleum ether and ethyl acetate as eluents for stepwise elution. The colorless single crystals of the title compound suitable for X-raycrystallographic analysis were obtained by recrystallization from a mixture of petroleum ether and ethyl acetate. m.p.426–428 K.