Crystal Structure and Computational Study of 2,4-di-chloro-N-[(E)-(5-nitro-thio-phen-2-yl)methyl-idene]aniline

Abstract

The title compound, C<inf>11</inf>H<inf>6</inf>ClR<inf>2</inf>NR<inf>2</inf>OR<inf>2</inf>S, 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)Å for the C=N N atom. The dihedral angle between the benzene and thiophene rings is 9.7(2)°. The C=N double bond has an E configuration. The crystal structure features C - H···O hydrogen bonds,forming sheets parallel to (10-1), and π-π stacking interactions between symmetry-related thiophene and benzene rings, in which the distance between adjacent ring centroids is 3.707(4)Å, forming a three-dimensional supramolecular structure. Geometric parameters from quantum-chemical calculations are in good agreement with experimental X-ray diffraction results.