Acta Cryst. (2008). E64, o981-o982  [ doi:10.1107/S160053680801252X ]

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

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

Abstract: The title compound, C₁₇H₁₄Cl₂N₂O₃S₂, and the 4-methylanilino analogue reported in the following 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 [1.421 (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. There is also an intramolecular N-HCl hydrogen bond. In the crystal structure, bonds of the C-HO(sulfonyl) type form chains that run along [101], while N-HO(sulfonyl) bonds connect centrosymmetrically related molecules in pairs of these chains, forming ribbons. Comparison of the NO distances in the intra- and intermolecular N-HO(sulfonyl) bonds reveals that the -bond co-operativity results in a strengthening of the intramolecular hydrogen bond. There are also - interactions between benzene rings of pairs of centrosymmetrically related molecules [centroid-centroid distance = 3.8612 (13) Å], as well as C-H interactions.

Online 3 May 2008

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