Acta Cryst. (2009). E65, o16  [ doi:10.1107/S1600536808038828 ]

N,N'-(2,2'-Dithiodi-o-phenylene)bis(furan-2-carboxamide)

J. Raftery, H. Lallbeeharry, M. G. Bhowon, S. J. Laulloo and J. A. Joule

Abstract: The reaction of 2,2'-dithiobis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C₂₂H₁₆N₂O₄S₂, which, in the crystal, formed a helix; the structure consists of two planar furanoylbenzenamines related by an improper rotation of 96.3° about the S-S bond. The N-furanoylbenzenamine units are planar (maximum deviations = 0.316 and 0.132 Å). Each electron-deficient acylfuran stacks (centroid-centroid separations of the two pairs of - stacked aromatic rings are 3.918 and 3.953 Å) with the electron-rich benzenamine of the other N-furanoylbenzenamine unit, leading to a spiral structure. The conformation is stabilized by two bifurcated intramolecular N-H(O,S) interactions.

Online 3 December 2008

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