Crystal structure and DFT study of (E)-2-chloro-4-{[2-(2,4-di­nitro­phen­yl)hydrazin-1-yl­idene]meth­yl}phenol aceto­nitrile hemisolvate

The title Schiff base compound, C(13)H(9)ClN(4)O(5)·0.5CH(3)CN, crystallizes as an aceto­nitrile hemisolvate; the solvent mol­ecule being located on a twofold rotation axis. The mol­ecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)°. The configuration about the C=N bond is E, and there is an intra­molecular N—H⋯O(nitro) hydrogen bond present forming an S(6) ring motif. In the crystal, mol­ecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming layers lying parallel to (10[Image: see text]). The layers are linked by C—H⋯Cl hydrogen bonds, forming a supra­molecular framework. Within the framework there are offset π–π stacking inter­actions [inter­centroid distance = 3.833 (2) Å] present involving inversion-related mol­ecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-di­nitro­benzene ring, and the HOMO–LUMO gap is found to be 0.13061 a.u.