Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine

• Main Authors: Sevim Türktekin Çelikesir, Mehmet Akkurt, Namiq Q. Shikhaliyev, Gulnar T. Suleymanova, Gulnare V. Babayeva, Nurana V. Gurbanova, Gunay Z. Mammadova, Ajaya Bhattarai
• Format: Article
• Language: English
• Published: International Union of Crystallography 2020-08-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; face-to-face π–π stacking interactions; 2,6-dichlorophenyl ring; nitro-substituted benzene ring; hirshfeld surface analysis
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989020008567
• ISSN: 2056-9890

In the title compound, C13H9Cl2N3O2, the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16 (14)°. In the crystal, face-to-face π–π stacking interactions occur along the a-axis direction between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring. Furthermore, these molecules show intramolecular N—H...Cl and C—H...O contacts and are linked by intermolecular N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (20\overline{2}). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (23.0%), O...H/H...O (20.1%), Cl...H/H...Cl (19.0%), C...C (11.2%) and H...C/C...H (8.0%) interactions.