Synthesis, characterization, crystal structure and antioxidant activity of N-(3-chloropropionyl)-N'-(4-methoxyphenyl)thiourea

In the present work, a new carbonoyl thiourea derivative, N-(3-chloropropionyl)-N'-(4-methoxyphenyl)thiourea, was synthesized by the reaction of 3-chloropropionyl isothiocyanate with 4-methoxyaniline in acetone solution. The newly synthesized compound was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopic techniques. X-ray crystallographic studies indicate that the compound crystallized in the triclinic crystal system with space group P-1 and unit cell dimension are a = 10.2262(6) Å, b = 11.5007(7) Å, c = 12.6116(8) Å, α = 72.253(2)°, β = 66.348(2)°, γ = 88.099(2)°, Z = 4 and V = 1287.22 (14) Å3. Strong intramolecular O-H···N hydrogen bonds are present that form a six-member pseudo-ring S(6). In the crystal structure, the molecules are linked by N-H···O, N-H···S, and C-H···O intermolecular hydrogen bonding interactions formed infinite one-dimensional chains with an R22(8) and R22(12) rings motif of molecules. The antioxidant test using the DPPH method showed that the compound exhibits a good antioxidant activity of about 80%.