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

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.

In the title compound, C 16 H 15 NOS, 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-HÁ Á ÁO hydrogen bond, forming a supramolecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C-HÁ Á Á interaction.

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).
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.

Refinement
All hydrogen atoms were positioned geometrically (C-H = 0.93-0.98 Å) and were refined using a riding model, with U iso (H) = 1.2U eq (C). Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.04954 (