Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromo-hex-yl)-2-[4-(di-methyl-amino)-phen-yl]-3 H-imidazo[4,5- b]pyridine

Zainab Jabri; Nada Kheira Sebbar; Tuncer Hökelek; Joel T Mague; Safia Sabir; Youssef Kandri Rodi; Khalid Misbahi

doi:10.1107/S2056989020008889

Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromo-hex-yl)-2-[4-(di-methyl-amino)-phen-yl]-3 H-imidazo[4,5- b]pyridine

Acta Crystallogr E Crystallogr Commun. 2020 Jul 10;76(Pt 8):1234-1238. doi: 10.1107/S2056989020008889. eCollection 2020 Aug 1.

Authors

Zainab Jabri¹, Nada Kheira Sebbar^{2

3}, Tuncer Hökelek⁴, Joel T Mague⁵, Safia Sabir¹, Youssef Kandri Rodi¹, Khalid Misbahi¹

Affiliations

¹ Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, Road Immouzer, BP 2202 Fez, Morocco.
² Laboratoire de Chimie Bioorganique Appliquée et Environnement Equipe de Chimie, Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco.
³ Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
⁴ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁵ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

In the title mol-ecule, C₂₀H₂₄Br₂N₄, the imidazo-pyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)° between the constituent rings; the 4-di-methyl-amino-phenyl 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) inter-actions form stacks of mol-ecules 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%) inter-actions. 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: C—H⋯π(ring) interaction; DFT calculation; Hirshfeld surface analysis; crystal structure; imidazopyridine.

Grants and funding

This work was funded by Tulane University grant . Hacettepe University Scientific Research Project Unit grant 013 D04 602 004 to T. Hökelek.