Crystal structure and Hirshfeld surface analysis of 2-oxo-2-phenyl-ethyl 3-nitroso-2-phenyl-imidazo[1,2- a]pyridine-8-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2022 Feb 15;78(Pt 3):322-325. doi: 10.1107/S2056989022001517. eCollection 2022 Feb 1.

Abstract

The title compound, C22H15N3O4, is built up from a central imidazo[1,2-a]pyridine ring system connected to a nitroso group, a phenyl ring and a 2-oxo-2-phenyl-ethyl acetate group. The imidazo[1,2-a] pyridine ring system is almost planar (r.m.s. deviation = 0.017 Å) and forms dihedral angles of 22.74 (5) and 45.37 (5)°, respectively, with the phenyl ring and the 2-oxo-2-phenyl-ethyl acetate group. In the crystal, the mol-ecules are linked into chains parallel to the b axis by C-H⋯O hydrogen bonds, generating R 2 1 (5) and R 4 4 (28) graph-set motifs. The chains are further linked into a three-dimensional network by C-H⋯π and π-stacking inter-actions. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H⋯H (36.2%), H⋯C/C⋯H (20.5%), H⋯O/O⋯H (20.0%), C⋯O/O⋯C (6.5%), C⋯N/N⋯C (6.2%), H⋯N/N⋯H (4.5%) and C⋯C (4.3%) inter-actions.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bonding; imidazo[1,2-a]pyridine.