(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine: crystal structure and Hirshfeld surface analysis

Abstract

The stabilized conformation of the title compound, C13H9Cl2N3O2, is similar to that of the isomeric compound (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine. The 2,6-dichlorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25 (16)°. In the crystal, face-to-face π-π stacking interactions along the a-axis direction occur between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring. The molecules are further linked by C—H...O contacts and N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (100). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (22.1%), Cl...H/H...Cl (20.5%), O...H/H...O (19.7%), C...C (11.1%) and C...H/H...C (8.3%) interactions.

Keywords

• crystal structure
• isomer
• 2,6-dichlorophenyl ring
• 3-nitrobenzylidene ring
• hirshfeld surface analysis