Research Article: 4-(4-Meth­oxy­phen­yl)naphtho­[2,3-b]thio­phene

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): S. Vasudhevan, G. Puthilibai, R. Joel Karunakaran.


In the title compound, C19H14OS, the naphtho­thio­phene moiety is almost planar except for the S atom of the five-membered ring, which is situated 0.047 (6) Å out of the C4 plane (with an r.m.s. deviation of fitted atoms = 0.0009 Å). The dihedral angle between the naphtho­thio­phene plane and the attached meth­oxy­phenyl ring is 67.6 (2)°. In the crystal, a C—H⋯π inter­action is observed between a meth­oxy­phenyl C—H group and the outer benzene ring of the naphtho­thio­phene moiety. The five-membered ring of the naphtho­thio­phene moiety is disordered, with the S and opposite non-fused C atom approximately exchanging positions, with a site-occupancy factors of 0.808 (3) and 0.187 (3).

Partial Text

For related thio­phene structures, see: Labat & Halfpenny (2005 ▶); Thenmozhi et al. (2008 ▶). For related heterocyclic compounds, see: Jones et al. (1984 ▶); Palani et al. (2006 ▶). For biological activity of naphtho­thio­phenes, see: Zuse et al. (2007 ▶, 2006 ▶); Dallemagne et al. (2003 ▶); Misra & Amin (1990 ▶).