One-pot synthesis, structure, theoretical study and vibrational spectroscopy of 5-amino-4-cyano-3H-1,2-dithiole-3-thione

A novel D3T derivative, 5-amino-4-cyano-3H-1,2-dithiole-3-thione (compound 1) has been obtained in one-pot reaction. The crystal is orthorhombic, space group Pbca, with a = 10.3667(4) Å, b = 10.8898(4) Å, c = 11.4942(5) Å, V = 1297.60(9) Å3, and Z = 8. In the crystal, molecules are firstly self-assembled into a complex sheet parallel to the (0 0 1) plane containing centrosymmetric R24 (16) and R44 (24) rings, and then the interconnection of molecular sheets through S···S interactions forms a three-dimensional supramolecular assembly. The DFT calculations are performed for isolated molecule using the B3LYP/6-31+G(d,p) methods. The frontier orbital properties of compound 1 have been reported and discussed. Moreover, a detailed assignment of the fundamental vibrational modes is proposed on the basis of the calculated results.