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


Çelikesir S. T. , AKKURT M. , Shikhaliyev N. Q. , Suleymanova G. T. , Babayeva G. V. , Gurbanova N. V. , ...More

Acta Crystallographica Section E: Crystallographic Communications, vol.76, pp.1173-1178, 2020 (Journal Indexed in ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 76
  • Publication Date: 2020
  • Doi Number: 10.1107/s2056989020008567
  • Title of Journal : Acta Crystallographica Section E: Crystallographic Communications
  • Page Numbers: pp.1173-1178
  • Keywords: crystal structure, face-to-face pi-pi stacking interactions, 2,6-dichlorophenyl ring, nitro-substituted benzene ring, Hirshfeld surface analysis, CATALYTIC-ACTIVITY, HYDROGEN-BONDS, X-RAY, COMPLEXES, ARYLHYDRAZONES, CYANOSILYLATION, HALOGEN, TETREL, ALDEHYDES

Abstract

In the title compound, C13H9Cl2N3O2, the 2,6-dichlorophenyl ring and the nitrosubstituted benzene ring form a dihedral angle of 21.16 (14)degrees. In the crystal, face-to-face pi-pi 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 center dot center dot center dot Cl and C-H center dot center dot center dot O contacts and are linked by intermolecular N-H center dot center dot center dot O and C-H center dot center dot center dot Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (20 (2) over bar). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H center dot center dot center dot H (23.0%), O center dot center dot center dot H/H center dot center dot center dot O (20.1%), Cl center dot center dot center dot H/H center dot center dot center dot Cl (19.0%), C center dot center dot center dot C (11.2%) and H center dot center dot center dot C/C center dot center dot center dot H (8.0%) interactions.