Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4H-immazo[4,5-b]pyridine


Bourichi S., Kandri Rodi Y., HÖKELEK T., Haoudi A., Renard C., Capet F.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.43-53, 2019 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989018017322
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index, Scopus
  • Page Numbers: pp.43-53

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)degrees to the ring system. In the crystal, molecules are linked via a pair of weak intermolecular C-H center dot center dot center dot N hydrogen bonds, forming an inversion dimer with an R-2(2)(20) ring motif. The dimers are further connected by pi-pi stacking interactions between the imidazo[4,5-b]pyridine ring systems [centroid-centroid distances = 3.7161 (13) and 3.8478 (13) angstrom]. The important contributions to the Hirshfeld surface are H center dot center dot center dot H (35.9%), H center dot center dot center dot Cl/Cl center dot center dot center dot H (15.0%), H center dot center dot center dot C/C center dot center dot center dot H (12.4%), H center dot center dot center dot Br/Br center dot center dot center dot H (10.8%), H center dot center dot center dot N/N center dot center dot center dot H (7.5%), C center dot center dot center dot Br/Br center dot center dot center dot C (5.9%), C center dot center dot center dot C (5.5%) and C center dot center dot center dot N/N center dot center dot center dot C (4.0%) contacts.