N-[(2S)-2-(4-Bromophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide

In the title compound, C15H12BrN3O2S, the dihedral angle between the pyridine and benzene rings is 73.17 (19)°. The five-membered 1,3-thiazolidine ring has an envelope conformation, with the S atom displaced by 0.196 (1) Å from the mean plane of the four other ring atoms. An intramolecular C—H⋯N interaction occurs. The crystal structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions. In addition, a weak π–π stacking interaction is also observed between the 1,3-thiazolidine and pyridine rings [centroid–centroid distance = 3.805 (2) Å].

In the title compound, C 15 H 12 BrN 3 O 2 S, the dihedral angle between the pyridine and benzene rings is 73.17 (19) . The five-membered 1,3-thiazolidine ring has an envelope conformation, with the S atom displaced by 0.196 (1) Å from the mean plane of the four other ring atoms. An intramolecular C-HÁ Á ÁN interaction occurs. The crystal structure is stabilized by intermolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions. In addition, a weakstacking interaction is also observed between the 1,3-thiazolidine and pyridine rings [centroid-centroid distance = 3.805 (2) Å ].
Cg3 is the centroid of the C1-C6 benzene ring.
A number of diverse chemical structures have been shown to be potent RT Inhibitors. Nicotinamide is gaining attention for its cytoprotective and antiviral properties (Gaudineau et al., 2004). Antiviral effect of nicotinamide and its inhibitory effect on enterovirus induced chemokine secretion have been recently shown (Moell et al., 2009). Furthermore, 3-pyridinecarboxamide derivatives with antitumor activity have been reported (Elbaum et al., 2003). Thiazolidinones exhibit various biological activities such as antifungal (Capan et al., 1999;Ozkırımlı et al., 2009); antituberculosis (Guzel et al., 2006); RT Inhibitor (Rawal et al., 2007); antiviral (Vanderlinden et al., 2010). We combine these two moities as part of an ongoing project directed towards the design and synthesis of bioactive molecules bearing 4-thiazolidinone and pyridine-3-carboxamide scaffolds together.
In the title molecule (I) shown in Fig. 1, the bond lengths and the bond angles are in the normal ranges (Allen et al., 1987).

Fig. 2) and a C-H···π interactions
Experimental 0.01 mol of N'-(4-bromobenzylidine)pyridine-3-carbohydrazide was reacted with 0.03 mol of mercaptoacetic acid in anhydrous benzene for 8 h using a Dean-Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The C-bound H atoms were geometrically placed (C-H = 0.93-0.97 Å) and refined as riding with U iso (H) = 1.2U eq (C). The N-bound H atoms were located from the Fourier synthesis and restrained to 0.86 (2) Å, and refined with U iso (H) = 1.5U eq (N). Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Fig. 2. View of the packing and hydrogen bonding interactions of (I). All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.