3-Phenyl-2-thioxo-1,3-thiazolidin-4-one

In the molecule of the title compound, C9H7NOS2, the heterocycle and the phenyl ring are oriented at a dihedral angle of 72.3 (1)°. Adjacent molecules are connected through C—H⋯O interactions.

In the molecule of the title compound, C 9 H 7 NOS 2 , the heterocycle and the phenyl ring are oriented at a dihedral angle of 72.3 (1) . Adjacent molecules are connected through C-HÁ Á ÁO interactions.

Experimental
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2120).  (Momose et al., 1991). As an extension of these studies, we report herein on the structure of 3-phenylrhodanine (3-phenyl-2-thioxothiazolidin-4-one).

Structure Reports Online
A 3-phenylrhodanine molecule, which is the asymmetric unit of the structure, is shown in Fig. 1. All the bond distances and bond angles are within the normal ranges. The two parts of the molecule, the five-member heterocycle and the phenyl ring, are oriented at a dihedral angle of 72.3 (1)°. Adjacent molecules are connected through C-H-O hydrogen bonds (Table 1).
Experimental 3-phenylrhodanine was synthesized according to the literature (Brown et al., 1956), and was recrystallized using a mixed solvent of ether and 95% ethanol (1:1 by volume). Yellow sheet crystals are obtained.

Refinement
All non-hydrogen atoms were found in Fourier maps, and were refined anisotropically. Hydrogen atoms were positioned geometrically, and the isotropic vibration parameters related to the atoms which they are bonded to with U iso = 1.2 U eq . Fig. 1. The asymmetric unit of 3-benzylrhodanine with atom labels and 50% probability displacement ellipsoids for non-H atoms.

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 > 2sigma(F 2 ) is used only for calculating R-factors(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.