(2E)-2-(2,4-Dichloro­phenyl­sulfon­yl)-3-(4-methyl­anilino)-3-(methyl­sulfan­yl)acrylonitrile

The title compound, C(17)H(14)Cl(2)N(2)O(2)S(2), and the 3-methoxy­anilino analogue reported in the preceding paper have been used as starting materials to develop benzothia­zine derivatives with anti­malarial activity. The mol­ecule displays an E (trans) configuration about the central double bond. Due to conjugation in the C=C—C N group, the putative single bond shows a significant shortening [1.418 (3) Å]. The mol­ecule has a six-membered ring involving an intra­molecular N—H⋯O(sulfon­yl) bond, which is an example of resonance-assisted hydrogen bonding. In the crystal structure, bonds of the C—H⋯O(sulfon­yl) and C—H⋯N(cyano) types form double layers of mol­ecules parallel to ([Image: see text]01). Within these layers there are π–π inter­actions between benzene rings of pairs of centrosymmetrically related mol­ecules, with distances of 3.7969 (12) Å between centroids. C—H⋯π interactions are also present.