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

The title compound, C 11 H 6 Cl 2 N 2 O 2 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.