Whole-molecule disorder of the Schiff base compound 4-chloro-N-(4-nitrobenzylidene)aniline: crystal structure and Hirshfeld surface analysis

Abstract

In the crystal of the title Schiff base compound, C13H9ClN2O2, [CNBA; systematic name: (E)-N-(4-chloro­phen­yl)-1-(4-nitro­phen­yl)methanimine], the CNBA mol­ecule shows whole-mol­ecule disorder (occupancy ratio 0.65:0.35), with the disorder components related by a twofold rotation about the shorter axis of the mol­ecule. The aromatic rings are inclined to each other by 39.3 (5)° in the major component and by 35.7 (9)° in the minor component. In the crystal, C—H...O hydrogen bonds predominate in linking the major components, while weak C—H...Cl inter­actions predominate in linking the minor components. The result is the formation of corrugated layers lying parallel to the ac plane. The crystal packing was analysed using Hirshfeld surface analysis and compared with related structures