(E)-1-(2,6-Di-chloro-phen-yl)-2-(3-nitro-benzyl-idene)hydrazine: crystal structure and Hirshfeld surface analysis.

Zeliha Atioğlu,Gulnare V Babayeva,Mehmet Akkurt,Namiq Q Shikhaliyev,Gulnar T Suleymanova,Gunay Z Mammadova,Nurana V Gurbanova,Sixberth Mlowe

doi:10.1107/s2056989020009433

Abstract

The stabilized conformation of the title compound, C13H9Cl2N3O2, is similar to that of the isomeric compound (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine. The 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25 (16)°. In the crystal, face-to-face π-π stacking inter-actions along the a-axis direction occur between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. The mol-ecules are further linked by C-H⋯O contacts and N-H⋯O and C-H⋯Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular 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%) inter-actions.

Highlights

Face-to-face - stacking interactions along the a-axis direction occur between the centroids of the 2,6dichlorophenyl ring and the nitro-substituted benzene ring
The molecules are further linked by C—HÁ Á ÁO contacts and N—HÁ Á ÁO and C—HÁ Á ÁCl 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 HÁ Á ÁH (22.1%), ClÁ Á ÁH/ HÁ Á ÁCl (20.5%), OÁ Á ÁH/HÁ Á ÁO (19.7%), CÁ Á ÁC (11.1%) and CÁ Á ÁH/HÁ Á ÁC (8.3%) interactions

Summary

Chemical context

Schiff bases as well as hydrazone ligands and their complexes have attracted much attention because of their high synthetic potential for organic and inorganic chemistry and their diverse useful properties (Maharramov et al, 2018; Mahmudov et al, 2014). Intermolecular interactions organize molecular architectures, which play a critical role in synthesis, catalysis, micellization, etc (Akbari et al, 2017; Gurbanov et al, 2018; Mahmoudi et al, 2018 and references cited therein). New types of weak interactions such as halogen, chalcogen, pnictogen and tetrel bonds or their cooperation with hydrogen bonds are able to drive the synthesis and catalysis, as well as improve properties of materials (Mizar et al, 2012; Mahmudov et al, 2019 and references cited therein). Symmetry code: (i) Àx þ 1; y À 12; Àz þ 2

Structural commentary

Supramolecular features

Hirshfeld surface analysis

Database survey

Findings

Synthesis and crystallization