Crystal Structure, Spectroscopic and DFT Computational Studies of N-(4-Fluorophenyl)-1-(5-Nitrothiophen-2-yl)methanimine

Abstract

A novel Schiff base compound was synthesized and characterized by IR spectroscopy and X-ray diffraction method. The compound crystallizes in monoclinic space group P21/c with Z = 4 in the unit cell. The ring systems are perfectly planar but the whole molecule is not planar. The dihedral angle between the thiophene and phenyl rings is 38.7(3)°. In the crystal, intermolecular C–H⋅⋅⋅O interactions link the molecules into a C(7) chain along the [20 $$\bar {1}$$ ] direction. The crystal packing is also stabilized by N–O⋅⋅⋅π interaction. The molecular structure and vibrational frequencies of the title compound were calculated using the DFT/B3LYP method with the 6-311++G(d,p) basis set. The calculated results show that the optimized geometry can well reproduce the crystal structure, and the theoretical vibrational frequencies show good agreement with experimental results.