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.