3-Butyl-2-phenyl-1,3-thiazolidine-1,4-dione

In the title compound, C13H17NO2S, the thiazolidine-1,4-dione ring adopts an envelope conformation with the S atom lying 0.631 (4) Å out of the plane formed by the other four ring atoms; the phenyl ring is almost perpendicular [88.74 (8)°] with respect to the ring C—C—N—C atoms and the butyl chain is in a fully extended conformation. In the crystal, a supramolecular two-dimensional arrangement arises from weak intermolecular C—H⋯O interactions.

In the title compound, C 13 H 17 NO 2 S, the thiazolidine-1,4-dione ring adopts an envelope conformation with the S atom lying 0.631 (4) Å out of the plane formed by the other four ring atoms; the phenyl ring is almost perpendicular [88.74 (8) ] with respect to the ring C-C-N-C atoms and the butyl chain is in a fully extended conformation. In the crystal, a supramolecular two-dimensional arrangement arises from weak intermolecular C-HÁ Á ÁO interactions.   Table 1 Hydrogen-bond geometry (Å , ). 3-Butyl-2-phenyl-1,3-thiazolidine-1,4-dione Q. Wang, Z. Xu and Y. Sun Comment As a part of our programme studying the new applications of cyclic sulfoxide derivatives in medicne (Wang, et al., 2009;Xu, et al., 2009), we report herein the crystal structure of the title compounds.

Related literature
The molecular structure of the title compound is shown in Fig. 1. The thiazolidin-4-one ring adopts an envelope conformation with S lying 0.631 (4) Å out of the plane formed by the rest of the ring atoms; the phenyl ring is oriented at right angles (88.74 (8)°) with respect to the ring (C2/C3/N1/C1) atoms. The butyl chain is in a fully extended conformation. The crystal packing (Fig. 2) consists of a two-dimensional network in the a-c-plane generated by intermolecular interactions of the weak C-H···O hydrogen bonds.

Experimental
All reagents were of analytical grade. The title compound was prepared according to literature methods (Srivastava et al., 2002;Johnson et al., 1983). It was characterized by recording its infrared spectra and elemental analyses. Single crystals of the title compound were obtained by slow evaporation of its chloroform solution at room temperature.

Refinement
All H atoms bonded to C atoms were calculated in idealized position with C-H = 0.93-0.98 Å and refined in riding mode on their parent atoms with U iso (H) values of 1.2U eq (C). Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > σ(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.