Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine.

Sevim Türktekin Çelikesir,Nurana V Gurbanova,Ajaya Bhattarai,Gulnar T Suleymanova,Mehmet Akkurt,Gulnare V Babayeva,Namiq Q Shikhaliyev,Gunay Z Mammadova

doi:10.1107/s2056989020008567

Abstract

In the title compound, C13H9Cl2N3O2, the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16 (14)°. In the crystal, face-to-face π-π stacking inter-actions occur along the a-axis direction between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. Furthermore, these mol-ecules show intra-molecular N-H⋯Cl and C-H⋯O contacts and are linked by inter-molecular N-H⋯O and C-H⋯Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular layers parallel to (20). 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%) inter-actions.

Highlights

Sevim Turktekin Celikesir,a Mehmet Akkurt,a Namiq Q
Face-to-face – stacking interactions occur along the a-axis direction between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from HÁ Á ÁH (23.0%), OÁ Á ÁH/HÁ Á ÁO (20.1%), ClÁ Á ÁH/HÁ Á ÁCl (19.0%), CÁ Á ÁC (11.2%) and HÁ Á ÁC/ CÁ Á ÁH (8.0%) interactions

Summary

Chemical context

Arylhydrazones and their complexes have attracted much attention because of their high synthetic potential for organic and inorganic chemistry and diverse useful properties (Maharramov et al, 2009, 2010, 2018; Mahmudov et al, 2010, 2011, 2014a). The analytical and catalytic properties of this class of compounds are strongly dependent on the attached groups to the hydrazone moiety (Mahmudov et al, 2013; Shixaliyev et al, 2018, 2019). Intermolecular interactions organize the molecular architectures, which play a critical role in synthesis, catalysis, micellization, etc. New types of non-covalent bonds such as halogen, chalcogen, pnictogen and tetrel bonds or their cooperation with hydrogen bonds are able to contribute to the synthesis and catalysis, giving materials with improved properties (Mahmudov et al, 2013, 2014b, 2015, 2017a,b, 2019; Mizar et al, 2012; Shixaliyev et al, 2013, 2014). In a continuation of our work in this regard, we have functionalized a new azo dye, (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine, which provides intermolecular non-covalent interactions

Structural commentary

Supramolecular features and Hirshfeld surface analysis

Database survey

Findings

Synthesis and crystallization