3-Benzyl-2-phenyl-1,3-thia­zolidin-4-one

Hoong-Kun Fun; Madhukar Hemamalini; Poovan Shanmugavelan; Alagusundaram Ponnuswamy; Rathinavel Jagatheesan

doi:10.1107/S1600536811037706

. 2011 Sep 30;67(Pt 10):o2706. doi: 10.1107/S1600536811037706

3-Benzyl-2-phenyl-1,3-thiazolidin-4-one

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Poovan Shanmugavelan ^b, Alagusundaram Ponnuswamy ^b, Rathinavel Jagatheesan ^c

PMCID: PMC3201390 PMID: 22064819

Abstract

In the title compound, C₁₆H₁₅NOS, the thiazolidine ring, which is essentially planar [maximum deviation = 0.071 (2) Å], makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45 (5)°. In the crystal, molecules are linked by a weak intermolecular C—H⋯O hydrogen bond, forming a supramolecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C—H⋯π interaction.

Related literature

For details and applications of thiazolidine-4-ones, see: Dutta et al. (1990 ▶); Jadhav & Ingle (1978 ▶); Gursoy & Terzioglu (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 ▶).

Experimental

Crystal data

C₁₆H₁₅NOS
M _r = 269.35
Monoclinic,
a = 13.5734 (15) Å
b = 10.1402 (11) Å
c = 10.1496 (11) Å
β = 104.305 (2)°
V = 1353.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.41 × 0.19 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.913, T _max = 0.985
21164 measured reflections
3990 independent reflections
2813 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.112
S = 1.05
3990 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037706/is2778sup1.cif

e-67-o2706-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037706/is2778Isup2.hkl

e-67-o2706-Isup2.hkl^{(191.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037706/is2778Isup3.cml

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

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

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1ⁱ	0.93	2.47	3.323 (2)	153
C2—H2A⋯Cg1ⁱⁱ	0.93	2.99	3.705 (3)	134

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

One of the main objectives of organic and medicinal chemistry is the design, synthesis and production of molecules having value as human therapeutic agents. During the past decade, combinatorial chemistry has provided access to chemical libraries based on privileged structures with heterocyclic moiety receiving special attention as they belong to a class of compounds with proven utility in medicinal chemistry. There are numerous biologically active molecules with five-membered rings, containing two hetero atoms. Among them, thiazolidin-4-ones are the most extensively investigated class of compounds, which have many interesting activity profiles namely bactericidal (Dutta et al., 1990), antifungal (Jadhav & Ingle, 1978), anticonvulsant (Gursoy & Terzioglu, 2005), anti-HIV (Rawal et al., 2007), antituberculotic (Shrivastava et al., 2005), COX-1 inhibitors (Look et al., 1996), inhibitors of the bacterial enzyme MurB (Anders et al., 2001), non-nucleoside inhibitors of HIV-RT (Barreca et al., 2001) and anti-histaminic agents (Diurno et al., 1992).

The asymmetric unit of the title compound is shown in Fig. 1. The thiazolidine (S1/N1/C8–C10) ring is essentially planar, with a maximum deviation of 0.071 (2) Å for atom C10. The central thiazolidine (S1/N1/C8–C10) ring makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl (C1–C6) and (C11–C16) rings, respectively. The dihedral angle between the phenyl (C1–C6) and (C11–C16) rings is 49.45 (5)°.

In the crystal structure, (Fig. 2), the molecules are linked by intermolecular weak C—H···O hydrogen bonds forming supramolecular chains along the b-axis. Furthermore, the crystal packing is stabilized by weak C—H···π interactions involving the C11–C16 ring.

Experimental

To a well ground intimate mixture of triphenyl phosphine (0.43 g, 1.6 mmol) and benzaldehyde, (0.15 g, 1.5 mmol) in a microwave vial (10 ml) equipped with a magnetic stirring bar, benzylazide, (0.2 g, 1.5 mmol) was added in drop with stirring. Stirring was continued until liberation of nitrogen ceased and then mercaptoacetic acid, (0.15 g, 1.6 mmol) was added to the above mixture and the reaction vessel was sealed with a septum. It was then placed into the cavity of a focused monomode microwave reactor (CEM Discover, benchmate) and operated at 150°C (temperature monitored by a built-in IR sensor), power 80W for 10 minutes. The reaction temperature was maintained by modulating the power level of the reactor. The reaction mixture was allowed to stand at room temperature. Then the residue was purified by column chromatography on silica (petrolium ether–ethyl acetate, 94:6) to afford the 3-benzyl-2-phenylthiazolidin-4-one. Yield: 0.38g (95%); m.p. 152–155°C.