Crystal structure of O-ethyl N-(ethoxycarbonyl)thiocarbamate

The title compound, C₆H₁₁NO₃S, provides entries to novel carbamoyl disulfanes and related compounds of interest to our laboratory. The atoms of the central O(C=S)N(C=O)O fragment have an r.m.s. deviation of 0.1077Å from the respective least-squares plane. While several conformational orientations are conceivable, the crystal structure shows only the one in which the carbonyl and the thiocarbonyl moieties are anti to each other across the central conjugated C - N - C moiety. Pairs of 2.54Å N - H⋯S=C hydrogen bonds between adjacent molecules form centrosymmetric dimers in the crystal.