Jeannie Bee-Jan Teh

S-Methyl 3-[4-(diethyl­amino)benzyl­idene]dithio­carbazate

Organic materials with delocalized -electron systems have aroused considerable interest as potential materials for nonlinear optical (NLO) studies. It has been found (Long, 1995) that the delocalized conjugated electrons contribute to enhancing the NLO response through their capability for hyperpolarization. Schiff base compounds having extensively conjugated -electron systems have been reported to display second harmonic generation (Messier et al., 1991; Zyss & Ledoux, 1994). We have synthesized the title compound, (I), to explore its potential as a prospective NLO material.

1-(4-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

The molecular strucure of (I) is shown in Fig. 1. Bond lengths and angles in (I) have normal values (Allen et al., 1987) and are comparable with those in related structures (Patil et al., 2006a,b,c; Patil, Ng et al., 2006; Patil, Rosli et al., 2006). The least-squares plane through the enone unit (C7– C9/O1) makes dihedral angles of 7.36 (6) and 14.84 (6) with the C1–C6 and C10–C15 benzene rings, respectively. The dihedral angle between the benzene rings is 7.59 (4) . An intramolecular C—H O hydrogen bond (Table 1) generates an S(5) ring motif (Bernstein et al., 1995). The crystal packing is stabilized by intermolecular N—H O hydrogen bonds (Fig. 2). In addition there are weak N—H (arene) interactions.