Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3H-imidazo[4,5-b]pyridine

Acta Crystallographica Section E: Crystallographic Communications

Joel T. Mague¹  Tuncer Hökelek²  Nada Kheira Sebbar³  Youssef Kandri Rodi⁴  Khalid Misbahi⁴  Safia Sabir⁴  Zainab Jabri⁴ 

[1] Department of Chemistry, Tulane University, New Orleans, LA 70118, USA;Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;Laboratoire de Chimie Bioorganique Appliquée et Environnement Equipe de Chimie, Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco;Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, Road Immouzer, BP 2202 Fez, Morocco;

关键词: crystal structure;    c—h...π(ring) interaction;    imidazopyridine;    dft calculation;    hirshfeld surface analysis;   

DOI  :  10.1107/S2056989020008889

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown