Acta Cryst. (2008). E64, o983-o984  [ doi:10.1107/S1600536808012531 ]

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

M. V. Capparelli, A. R. Barazarte and J. E. Charris

Abstract: The title compound, C₁₇H₁₄Cl₂N₂O₂S₂, 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-CN group, the putative single bond shows a significant shortening [1.418 (3) Å]. The molecule has a six-membered ring involving an intramolecular N-HO(sulfonyl) bond, which is an example of resonance-assisted hydrogen bonding. In the crystal structure, bonds of the C-HO(sulfonyl) and C-HN(cyano) types form double layers of molecules parallel to (01). Within these layers there are - interactions between benzene rings of pairs of centrosymmetrically related molecules, with distances of 3.7969 (12) Å between centroids. C-H interactions are also present.

Online 3 May 2008

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