Synthesis, Characterization and Antibacterial Activity of N-(2,3,4-Trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine

Abstract

The title compound N-(2,3,4-trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine (C18H21NO3, M r = 299.36) was synthesized and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 7.2804(5), b = 8.5909(9), c = 26.117(3) A, β = 92.056(2)°, V = 1,632.4(3) A3, Z = 4, D c = 1.218 g cm−3, λ = 0.71073 A, μ(Mo Kα) = 0.083 mm−1, F(000) = 640. The final refinement gave R = 0.0497, wR(F 2) = 0.1157 for 2,879 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the dihedral angle between the two phenyl rings is 25.9 (2)°. The molecule adopts a trans configuration about the central C=N functional bond. The crystal structure is stabilized by C–H…O hydrogen bonds and π–π stacking interactions. The title compound possesses moderate antibacterial activity. The title compound N-(2,3,4-trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine (C18H21NO3, M r = 299.36) was synthesized and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 7.2804(5), b = 8.5909(9), c = 26.117(3) A, β = 92.056(2)°, V = 1,632.4(3) A3, Z = 4, D c = 1.218 g cm−3, λ = 0.71073 A, μ(Mo Kα) = 0.083 mm−1, F(000) = 640. The final refinement gave R = 0.0497, wR(F 2) = 0.1157 for 2,879 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the dihedral angle between the two phenyl rings is 25.9 (2)°. The molecule adopts a trans configuration about the central C=N functional bond. The crystal structure is stabilized by C–H…O hydrogen bonds and π–π stacking interactions. The title compound possesses moderate antibacterial activity.