Methyl 2-((2Z,5Z)-4-oxo-3-phenyl-2-{2-[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]hydrazin-1-ylidene}-1,3-thiazolidin-5-ylidene)acetate

In the title compound, C22H19N3O3S, the six-membered ring of the 1,2,3,4-tetrahydronaphthalene ring system adopts an envelope conformation with the central CH2 C atom as the flap. The molecular conformation is stabilized by an S⋯O contact, forming a pseudo-five-membered ring. In the crystal, molecules are linked via C—H⋯O hydrogen bonds into chains propagating along [102].

In the title compound, C 22 H 19 N 3 O 3 S, the six-membered ring of the 1,2,3,4-tetrahydronaphthalene ring system adopts an envelope conformation with the central CH 2 C atom as the flap. The molecular conformation is stabilized by an SÁ Á ÁO contact, forming a pseudo-five-membered ring. In the crystal, molecules are linked via C-HÁ Á ÁO hydrogen bonds into chains propagating along [102].

Comment
Thiazolidinediones (TZDs) are a pharmacological group of structurally related compounds characterized by a thiazolidinedione ring to which divergent molecular moieties are attached. Many methods have been reoprted for the synthesis of thiazolidinedione-containing compounds and their analogues (Patel et al., 2010;Aneja et al., 2011). The most beneficial effects of TZDs such as rosiglitazone and pioglitazone is the treatment of type II diabetes by lowering blood glucose levels via increasing insulin sensitivity with no hepatic side effects (Gillies & Dunn, 2000;Lenhard & Funk, 2001). They were shown also to reduce cardiovascular risk factors associated with this condition (Edelman, 2003).
Recently, an anti-inflammatory potential for TZDs has also been suggested (Desmet et al., 2005). In this context we synthesized the title compound as part of our on-going study in synthesis and biological reactivities of thiazolidinedione scaffold compounds.
The molecular conformation of the title compound is stabilized by a S1···O2 contact forming a pseudo five-membered ring. In the crystal packing, C-H···O hydrogen bonds connect the molecules generating chains running along [1 0 2] (Table 1, Fig. 2).

Experimental
The title compound was synthesized based on our previous reported method (Mague et al., 2014). Orange crystals (m.p.501-503 K) suitable for X-ray analysis were grown from an ethanolic solution at room temperature after two days.

Refinement
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C-H = 0.95-0.99 Å, with U iso (H) = 1.2 or 1.5 U iso (C).