Title of article :
Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3H-imidazo[4,5-b]pyridine
Author/Authors :
Jabri, Zainab Laboratory of Applied Organic Chemistry - Sidi Mohamed Ben Abdellah University- Faculty of Sciences and Techniques, Morocco , Sebbar, Nada Kheira Laboratoire de Chimie Bioorganique Appliquée et Environnement Equipe de Chimie - Bioorganique Appliquée - Faculté des Sciences - Université Ibn Zohr, Morocco , Hökelek, Tuncer Department of Physics - Hacettepe University, Turkey , Mague, Joel T. Department of Chemistry Tulane University, USA , Sabir, Safia Laboratory of Applied Organic Chemistry - Sidi Mohamed Ben Abdellah University- Faculty of Sciences and Techniques, Morocco , Rodi, Youssef Kandri Laboratory of Applied Organic Chemistry - Sidi Mohamed Ben Abdellah University- Faculty of Sciences and Techniques, Morocco , Misbahi, Khalid Laboratory of Applied Organic Chemistry - Sidi Mohamed Ben Abdellah University- Faculty of Sciences and Techniques, Morocco
Abstract :
In the title molecule, C20H24Br2N4, the imidazopyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)° between the constituent rings; the 4-dimethylaminophenyl ring is inclined to the mean plane of the imidazole ring by 27.4 (1)°. In the crystal, two sets of C—H⋯π(ring) interactions form stacks of molecules extending parallel to the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (42.2%), H⋯C/C⋯H (23.1%) and H⋯Br/Br⋯H (22.3%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 2.3591 eV.
Keywords :
Hirshfeld surface analysis , DFT calculation , imidazopyridine , C—H⋯π(ring) interaction , crystal structure
