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N,N'-(2,2'-Dithiodi-o-phenyl-ene)bis-(furan-2-carboxamide).

ABSTRACT: The reaction of 2,2'-dithio-bis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C(22)H(16)N(2)O(4)S(2), 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 acyl-furan stacks (centroid-centroid separations of the two pairs of π-π stacked aromatic rings are 3.918 and 3.953 Å) with the electron-rich benzenamine of the other N-furan-oyl-benzenamine unit, leading to a spiral structure. The conformation is stabilized by two bifurcated intramolecular N-H⋯(O,S) interactions.

SUBMITTER: Raftery J 

PROVIDER: S-EPMC2967937 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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N,N'-(2,2'-Dithiodi-o-phenyl-ene)bis-(furan-2-carboxamide).

Raftery James J   Lallbeeharry Hiteyeshi H   Bhowon Minu G MG   Laulloo Sabina J SJ   Joule John A JA  

Acta crystallographica. Section E, Structure reports online 20081203 Pt 1

The reaction of 2,2'-dithio-bis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C(22)H(16)N(2)O(4)S(2), 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 acyl-furan stacks (centroid-centroid separations of the two pairs of π-π stacked aromatic ring  ...[more]

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