Crystal structure and computational study of 2,4-dichloro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline

Abstract

The title compound, C11H6Cl2N2O2S, is a Schiff base that incorporates an N-bound 2,4-dichlorophenyl and a C-bound 5-nitrothiophene ring. The molecule is approximately planar, the maximum deviation from the mean plane being 0.233 (4) angstrom for the C=N N atom. The dihedral angle between the benzene and thiophene rings is 9.7 (2)degrees. The C=N double bond has an E configuration. The crystal structure features C-H center dot center dot center dot O hydrogen bonds, forming sheets parallel to (10 (1) over bar), and pi-pi stacking interactions between symmetry-related thiophene and benzene rings, in which the distance between adjacent ring centroids is 3.707 (4) angstrom, forming a three-dimensional supramolecular structure. Geometric parameters from quantum-chemical calculations are in good agreement with experimental X-ray diffraction results.