Title of article :
Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine
Author/Authors :
Khamees, Hussien Ahmed Department of Studies in Physics - Manasagangotri - University of Mysore, Karnataka, India , Chaluvaiah, Kumara Department of Chemistry - Mangalore University - Mangalagangothri, Karnataka, India , El-khatatneh, Nasseem Ahmed Department of Studies in Physics - Manasagangotri - University of Mysore, Karnataka, India , Swamynayaka, Ananda Department of Studies in Physics - Manasagangotri - University of Mysore, Karnataka, India , Huey Chong, Kwong Department of Chemistry, Faculty of Science - Universiti Putra Malaysia 43400 - UPM Serdang - Selangor Darul Ehsan, Malaysia , Prasad Dasappa, Jagadeesh Department of Chemistry - Mangalore University - Mangalagangothri, Karnataka, India , Khamees, Hussien Ahmed Department of Studies in Physics - Manasagangotri - University of Mysore, Karnataka, India , Madegowda, Mahendra Department of Studies in Physics - Manasagangotri - University of Mysore, Karnataka, India
Abstract :
The title imidazo[1,2-a] pyridine derivative, C13H8Br2N2, was synthesized via a single-step reaction method. The title molecule is planar, showing a dihedral angle of 0.62 (17)° between the phenyl and the imidazo[1,2-a] pyridine rings. An intramolecular C—H⋯N hydrogen bond with an S(5) ring motif is present. In the crystal, a short H⋯H contact links adjacent molecules into inversion-related dimers. The dimers are linked in turn by weak C—H⋯π and slipped π–π stacking interactions, 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 intermolecular 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%) interactions. Energy framework calculations suggest that the contacts formed between molecules are largely dispersive in nature. Analysis of HOMO–LUMO energies from a DFT calculation reveals the pure π character of the aromatic rings with the highest electron density on the phenyl ring, and σ character of the electron density on the Br atoms. The HOMO–LUMO gap was found to be 4.343 eV.
Keywords :
crystal structure , imidazole-pyridine derivative , π–π interactions , DFT calculation , Hirshfeld surface analysis , energy framework , frontier molecular orbitals
