Research Article: 8-Methyl-2-oxo-4-(thio­phen-2-yl)-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Abdullah M. Asiri, Hassan M. Faidallah, Alaa Anwar Ahmad Saqer, Seik Weng Ng, Edward R. T. Tiekink.


In the title compound, C15H14N2OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclo­hexene ring has a twisted half-boat conformation with the methyl­ene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649 (4):0.351 (4) ratio, and forms dihedral angles of 51.4 (3) (major component) and 54.2 (3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol­ecules associate via an eight-membered {⋯HNCO}2 synthon and these are linked into a linear supra­molecular chain along the a axis by weak π–π inter­actions that occur between centrosymmetrically related pyridinone rings [centroid–centroid distance = 3.889 (2) Å].

Partial Text

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005 ▶); Girgis et al. (2007 ▶). For a related structure, see: Asiri et al. (2011 ▶).




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