Bis(N-methyl-N-phenyl­carbamo­yl)disulfane

The title compound, C₁₆H₁₆N₂O₂S₂, has been synthesized by several different high-yield routes, and has been encountered as a co-product in a number of reaction pathways, ever since it became of inter­est to our research program over 30 years ago. We now confirm the proposed mol­ecular structure in which the mol­ecule exhibits a twofold axis of symmetry through the mid-point of the S-S bond and the two planes defined by the (carbamo­yl)sulfenyl moieties are essentially perpendicular to each other [dihedral angle = 81.55 (14)°].

Bis[(methyl­sulfan­yl)carbon­yl]disulfane

The title compound, C₄H₆O₂S₄, was prepared by repeating, with subtle improvements, a multi-step route originally described by Mott & Barany [J. Chem. Soc. Perkin Trans. 1 (1984), pp. 2615-2621]. The title compound was obtained for the first time as a crystalline material. The two [(methyl­sulfan­yl)carbon­yl]sulfenyl moieties are essentially perpendic­ular to each other, each approximately planar (r.m.s. deviations of 0.02 and 0.01 Å) and with a C-S-S-C torsion angle = 90.99 (6)°, which compares well with the theoretical value of 90°.