Abstract
The title compound, C15H11BrClN3, is built up from a planar imidazo[4,5-b]pyridine unit linked to phenyl and allyl substituents. The allyl substituent is rotated significantly out of the imidazo[4,5-b]pyridine plane, while the benzene ring is inclined by 3.84 (6)° to the ring system. In the crystal, mol-ecules are linked via a pair of weak inter-molecular C-H⋯N hydrogen bonds, forming an inversion dimer with an R 2 2(20) ring motif. The dimers are further connected by π-π stacking inter-actions between the imidazo[4,5-b]pyridine ring systems [centroid-centroid distances = 3.7161 (13) and 3.8478 (13) Å]. The important contributions to the Hirshfeld surface are H⋯H (35.9%), H⋯Cl/Cl⋯H (15.0%), H⋯C/C⋯H (12.4%), H⋯Br/Br⋯H (10.8%), H⋯N/N⋯H (7.5%), C⋯Br/Br⋯C (5.9%), C⋯C (5.5%) and C⋯N/N⋯C (4.0%) contacts.
Highlights
The important contributions to the Hirshfeld surface are HÁ Á ÁH (35.9%), HÁ Á ÁCl/ClÁ Á ÁH (15.0%), HÁ Á ÁC/CÁ Á ÁH (12.4%), HÁ Á ÁBr/BrÁ Á ÁH (10.8%), HÁ Á ÁN/NÁ Á ÁH (7.5%), CÁ Á ÁBr/BrÁ Á ÁC (5.9%), CÁ Á ÁC (5.5%) and CÁ Á ÁN/NÁ Á ÁC (4.0%) contacts
Heterocyclic ring systems having an imidazo[4,5-b]pyridine unit can be considered as structural analogues of purines and have shown diverse biological activity depending on the substituents of the heterocyclic ring
Some imidazo[4,5-b]pyridine derivatives have been reported as corrosion inhibitors for steel in acidic medium (Bouayad et al, 2018; Sikine et al, 2016), and some of them can be used to treat peptic ulcers, diabetes and mental illness (Scribner et al, 2007; Liang et al, 2007)
Summary
Heterocyclic ring systems having an imidazo[4,5-b]pyridine unit can be considered as structural analogues of purines and have shown diverse biological activity depending on the substituents of the heterocyclic ring. Their activities include anticancer (Zhiqiang et al, 2005), tuberculostatic (Bukowski & Janowiec, 1989) and antimitotic (Parthiban et al, 2006) actions. Some imidazo[4,5-b]pyridine derivatives have been reported as corrosion inhibitors for steel in acidic medium (Bouayad et al, 2018; Sikine et al, 2016), and some of them can be used to treat peptic ulcers, diabetes and mental illness (Scribner et al, 2007; Liang et al, 2007). Yl)-4H-imidazo[4,5-b]pyridine in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions
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