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

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Jabri Z., Sebbar N. K., HÖKELEK T., Mague J. T., Sabir S., Rodi Y. K., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.1234-1245, 2020 (ESCI, Scopus)

• Publication Type: Article / Article
• Volume: 76
• Publication Date: 2020
• Doi Number: 10.1107/s2056989020008889
• Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
• Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
• Page Numbers: pp.1234-1245
• Open Archive Collection: AVESIS Open Access Collection
• Hacettepe University Affiliated: Yes

Abstract

In the title molecule, C20H24Br2N4, the imidazopyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)degrees between the constituent rings; the 4-dimethylaminophenyl ring is inclined to the mean plane of the imidazole ring by 27.4 (1)degrees. In the crystal, two sets of C-H center dot center dot center dot pi(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 center dot center dot center dot H (42.2%), H center dot center dot center dot C/C center dot center dot center dot H (23.1%) and H center dot center dot center dot Br/Br center dot center dot center dot 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.