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

The reaction of 2,20-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 degrees about the S-S bond. The N-furanoylbenzenamine units are planar (maximum deviations = 0.316 and 0.132 angstrom). Each electron-deficient acylfuran stacks (centroid-centroid separations of the two pairs of pi-pi stacked aromatic rings are 3.918 and 3.953 angstrom) 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 center dot center dot center dot (O,S) interactions.