(E)-N-(1-Benzothiophen-3-ylmethylidene)-2,6-dimethylaniline

In the title compound, C17H15NS, the benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 61.99 (7)°. An intermolecular C—H⋯π interaction contributes to the stability of the crystal structure.

In the title compound, C 17 H 15 NS, the benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 61.99 (7) . An intermolecular C-HÁ Á Á interaction contributes to the stability of the crystal structure.
Cg2 is the centroid of the C1-C6 ring.
Schiff bases, i.e., compounds having a double C=N bond, are used as starting materials in the synthesis of important drugs, such as antibiotics and antiallergic, antiphlogistic, and antitumor substances (Barton & Ollis, 1979;Layer, 1963;Ingold 1969). On the industrial scale, they have a wide range of applications, such as dyes and pigments (Taggi et al., 2002). They are also used as components of rubber compounds (Novopoltseva, 1995). Schiff base compounds display interesting photochromic and thermochromic features in the solid state and can be classified in terms of these properties (Cohen et al., 1964). Photo-and thermochromism arise via H-atom transfer from the hydroxy O atom to the imine N atom (Hadjoudis et al., 1987;Xu et al., 1994). Such proton-exchanging materials can be utilized for the design of various molecular electronic devices (Alarcon et al., 1999). In general, Schiff bases display two possible tautomeric forms, the phenol-imine (OH) and the keto-amine (NH) forms. Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O-H···N in phenol-imine (Köysal et al., 2007) and N-H···O in keto-amine tautomers. By means of increasing development of computational chemistry in the past decade, the research of theoretical modeling of drug design, functional material design, etc., has become more mature than ever. Many important chemical and physical properties of biological and chemical systems can be predicted from the first principles by various computational techniques (Zhang et al., 2001). Schiff bases have also been employed as ligands for the complexation of metal ions (Aydoğan et al., 2001).

Refinement
All hydrogen atoms were positioned geometrically [C-H=0.930 and 0.960] and treated as riding with U iso (H)=1.2U eq (C) or 1.5U eq (C methyl ).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.