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.
Highlights
Numerous drugs contain N-heterocycles as the core structure, including imidazo[1,2-a]pyridine and its derivatives, which are used in medicinal chemistry (Swainston Harrison & Keating, 2005; Deep et al, 2017) or that exhibit diverse biological properties, such as antibacterial (Mishra et al, 2021), antitubercular (Wang et al, 2019), tyrosinase inhibitory (Damghani et al, 2020), HIV inhibitory (Bode et al, 2011), antidiabetic (Saeedi et al, 2021), anti-inflammatory (Gundlewad et al, 2020) or anticancer activities (Yu et al, 2020; Sigalapalli et al, 2021)
The molecular conformation is stabilized by two weak intramolecular C9—H9Á Á ÁO1 and C1—H1Á Á ÁN1 hydrogen bonds, generating S(6) ring motifs (Table 1, Fig. 1)
Molecules are linked by C9—H9Á Á ÁO2iii and C10—H10Á Á ÁO2iii hydrogen bonds, forming chains that propagate parallel to the b axis and enclose R12(5) ring motifs (Table 1, Fig. 2)
Summary
Numerous drugs contain N-heterocycles as the core structure, including imidazo[1,2-a]pyridine and its derivatives, which are used in medicinal chemistry (Swainston Harrison & Keating, 2005; Deep et al, 2017) or that exhibit diverse biological properties, such as antibacterial (Mishra et al, 2021), antitubercular (Wang et al, 2019), tyrosinase inhibitory (Damghani et al, 2020), HIV inhibitory (Bode et al, 2011), antidiabetic (Saeedi et al, 2021), anti-inflammatory (Gundlewad et al, 2020) or anticancer activities (Yu et al, 2020; Sigalapalli et al, 2021) Encouraged by these features and in a continuation of our exploration of the synthesis, molecular structures and Hirshfeld surface analysis of new Nheterocyclic compounds (Daoui et al, 2021, 2022; El Kalai et al, 2021a,b), we report the crystal structure and Hirshfeld surface analysis of 2-oxo-2-phenylethyl 3-nitroso-2phenylimidazo[1,2-a]pyridine-8-carboxylate, C22H15N3O4 (I). Symmetry codes: (i) x; Ày þ 12; z þ 12; (ii) Àx þ 1; y þ 12; Àz þ 12; (iii) Àx þ 1; y À 12; Àz þ 12; (iv) x; Ày þ 12; z À 12
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