Crystal structure and Hirshfeld surface analysis of 5-acetyl-2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Ibrahim G Mamedov,Khatira N Aliyeva,Anzurat A Akobirshoeva,Ayten R Asgarova,Anton P Novikov,Mehmet Akkurt,Victor N Khrustalev

doi:10.1107/s2056989022001232

Abstract

The crystal structure of the title compound, C20H16BrN3O2, was determined using an inversion twin. Its asymmetric unit comprises two crystallographically independent mol-ecules (A and B) being the stereoisomers. Both mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming a dimer with an R 2 2(16) ring motif. The dimers are connected by further N-H⋯O and N-H⋯N hydrogen bonds, forming chains along the c-axis direction·C-Br⋯π inter-actions between these chains contribute to the stabilization of the mol-ecular packing. Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, Br⋯H/H⋯Br and N⋯H/H⋯N inter-actions.

Highlights

Its asymmetric unit comprises two crystallographically independent molecules (A and B) being the stereoisomers. Both molecules are linked by pairs of N—HÁ Á ÁO hydrogen bonds, forming a dimer with an R22(16) ring motif
The dimers are connected by further N—HÁ Á ÁO and N—HÁ Á ÁN hydrogen bonds, forming chains along the c-axis directionÁC—BrÁ Á Á interactions between these chains contribute to the stabilization of the molecular packing
In the framework of our ongoing structural studies (Safarova et al, 2019; Naghiyev et al, 2020, 2021a,b; Maharramov et al, 2021), we report here the crystal structure and Hirshfeld surface analysis of the title compound, 5-acetyl-2amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile

Summary

Chemical context

Nitrogen-based heterocycles are an important class of organic molecules that are used extensively in different branches of chemistry (Yadigarov et al, 2009; Abdelhamid et al, 2011; Magerramov et al, 2018; Yin et al, 2020; Khalilov et al, 2021). The synthesis of heterocyclic systems comprising a bioactive pyridine core with a broad spectrum of biological activities is noteworthy (Mamedov et al, 2020; Wojcicka & Redzicka, 2021). The pyridine ring is an essential part of diverse natural products, such as nicotinic acid, nicotinamide, vitamin B3 and diverse alkaloids (Aida et al, 2009). In the framework of our ongoing structural studies (Safarova et al, 2019; Naghiyev et al, 2020, 2021a,b; Maharramov et al, 2021), we report here the crystal structure and Hirshfeld surface analysis of the title compound, 5-acetyl-2amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile. Symmetry codes: (i) x; Ày þ 1; z þ 12; (ii) x; y À 1; z; (iii) x; Ày þ 2; z þ 12; (iv) x; Ày þ 1; z À 12

Structural commentary

Supramolecular features

Hirshfeld surface analysis

Database survey

Synthesis and crystallization