Crystal structure of tetraisobutylthiuram disulfide

Abstract

Tetrakis(2-methylpropyl)thioperoxydicarbonic diamide, or tetraisobutylthiuram disulfide, C18H36N2S4, crystallizes in a general position in the triclinic space groupP-1 but shows pseudo-C2symmetry about the disulfide bond. The C—S—S—C torsion angle [−85.81 (2)°] and the dihedral angle between the two NCS2mean planes [85.91 (5)°] are within the range observed for this compound type. Multiple intra- and intermolecular S...H—C close contacts appear to play a role in assisting the specific conformation of the pendant isobutyl groups and the packing arrangement of molecules within the cell. Tetraisobutylthiuram disulfide molecules of one optical configuration form sheets in the plane of theaandbaxes. Inversion centers exist between adjoining sheets, which stack along thecaxis and alternate in the handedness of their constituent molecules.