Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromo-phen-yl)imidazo[1,2-a]pyridine.

ABSTRACT: The title imidazo[1,2-a] pyridine derivative, C13H8Br2N2, was synthesized via a single-step reaction method. The title mol-ecule is planar, showing a dihedral angle of 0.62?(17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intra-molecular C-H?N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H?H contact links adjacent mol-ecules into inversion-related dimers. The dimers are linked in turn by weak C-H?? and slipped ?-? stacking inter-actions, forming layers parallel to (110). The layers are connected into a three-dimensional network by short Br?H contacts. Two-dimensional fingerprint plots and three-dimensional Hirshfeld surface analysis of the inter-molecular contacts reveal that the most important contributions for the crystal packing are from H?Br/Br?H (26.1%), H?H (21.7%), H?C/C?H (21.3%) and C?C (6.5%) inter-actions. Energy framework calculations suggest that the contacts formed between mol-ecules are largely dispersive in nature. Analysis of HOMO-LUMO energies from a DFT calculation reveals the pure ? character of the aromatic rings with the highest electron density on the phenyl ring, and ? character of the electron density on the Br atoms. The HOMO-LUMO gap was found to be 4.343?eV.

SUBMITTER: Khamees HA 

PROVIDER: S-EPMC6829731 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature