Crystal structure and Hirshfeld surface analysis of phen-yl(5,7,8a-triphenyl-1,2,3,7,8,8a-hexa-hydro-imidazo[1,2-a]pyridin-6-yl)methanone with an unknown solvent.

Sevim Türktekin Çelikesir,Farid N Naghiyev,Ibrahim G Mamedov,Afet T Huseynova,Anzurat A Akobirshoeva,Mehmet Akkurt,Gunay Z Mammadova

doi:10.1107/s2056989020009871

Abstract

In the title compound, C32H28N2O, the imidazolidine and pyridine rings of the central hexa-hydro-imidazo[1,2-a]pyridine ring system adopt envelope and screw-boat conformations, respectively. The mol-ecule exhibits two weak intra-molecular π-π inter-actions between phenyl rings. In the crystal, mol-ecules are linked via pairs of C-H⋯ O hydrogen bonds, forming inversion dimers. The dimers are further linked by pairs of C-H⋯π inter-actions, forming infinite chains along the c-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (73.4%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (5.7%) contacts. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON. The solvent contribution was not included in the reported mol-ecular weight and density.

Highlights

In the title compound, C32H28N2O, the imidazolidine and pyridine rings of the central hexahydroimidazo[1,2-a]pyridine ring system adopt envelope and screwboat conformations, respectively
Molecules are linked via pairs of C—HÁ Á Á O hydrogen bonds, forming inversion dimers
A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from HÁ Á ÁH (73.4%), CÁ Á ÁH/HÁ Á ÁC (18.8%) and OÁ Á ÁH/HÁ Á ÁO (5.7%) contacts

Summary

Chemical context

Carbon–carbon and carbon–heteroatom bond-forming reactions are the most powerful and fundamental tools in synthetic organic chemistry. These synthetic approaches have successfully found applications in the construction of carbo- and heterocyclic ring systems (Khalilov et al, 2011; Yin et al, 2020). Bridgehead nitrogen heterocycles comprising imidazole rings are prevalent structural motifs in many compounds having applications in medicinal chemistry, coordination chemistry and material science (Afkhami et al, 2017; Mahmoudi et al, 2017a,b; Mahmudov et al, 2019, 2020). Various imidazo[1,2-a]pyridine moieties are included in synthetic drugs, such as alpidem, olprinone, saripidem, necopidem, miroprofen, zolimidine and zolpidem, which have already found use in medicinal practice. Symmetry codes: (i) Àx; Ày; Àz þ 2; (ii) Àx; Ày; Àz þ 1

Structural commentary

Supramolecular features and Hirshfeld surface analysis

Synthesis and crystallization

Findings

Database survey