Influence of polymorphism on N-thiophosphorylated thiourea 4-Me2NC6H4NHC(S)NHP(S)(OiPr)2 crystal design

The reaction between 4-(dimethylamino)aniline and O,O′-diisopropyl-isothiocyanatothiophosphoric acid (iPrO)2P(S)NCS gives the N-thiophosphorylated thiourea 4-Me2NC6H4NHC(S)NHP(S)(OiPr)2 (L). The structure of this compound was investigated by IR, 1H, 31P{1H} NMR spectroscopy; its composition was examined by microanalysis. Recrystallization of L from an acetone/n-hexane mixture leads to the formation of the triclinic polymorph L1 with cell parameters a = 7.6486(2), b = 9.8087(13), c = 13.7522(14) Å, α = 79.685(10), β = 84.090(7), γ = 70.463(8)°, V = 955.58(17) Å3, and Z = 2. Recrystallization of L from a CH2Cl2/n-hexane mixture leads to the formation of the triclinic polymorph L2 with cell parameters a = 10.2581(6), b = 13.1606(7), c = 14.9343(8) Å, α = 90.718(3), β = 107.751(3), γ = 93.285(2)°, V = 1916.07(18) Å3, and Z = 4.