Research Article: (E)-3-Anilino-2-benzoyl-3-(methyl­sulfan­yl)acrylonitrile

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Hatem A. Abdel-Aziz, Hazem A. Ghabbour, Suchada Chantrapromma, Hoong-Kun Fun.


In the title acrylonitrile derivative, C17H14N2OS, the central amino­acryl­aldehyde O=C—C=C—NH unit, wherein an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif, is approximately planar, with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms. This plane makes dihedral angles of 41.04 (9) and 84.86 (10)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 54.82 (10)°. An intra­molecular C—H⋯N hydrogen bond is also present. In the crystal, weak C—H⋯π and π–π inter­actions, with a centroid–centroid distance of 3.8526 (14) Å, are observed.

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002 ▶); Sączewski et al. (2004 ▶); Sommen et al. (2002 ▶, 2003 ▶); Rudorf & Augustin (1977 ▶).