Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromo-dodec-yl)-2-(4-nitro-phen-yl)-4H-imidazo[4,5-b]pyridine.
Acta Crystallogr E Crystallogr Commun
; 76(Pt 5): 677-682, 2020 May 01.
Article
em En
| MEDLINE
| ID: mdl-32431932
ABSTRACT
The title compound, C24H30Br2N4O2, consists of a 2-(4-nitro-phen-yl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromo-dodecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09â
(1)â
Å and makes a dihedral angle of 21.9â
(8)° with the mean plane of the imidazolo-pyridine moiety, giving the mol-ecule a V-shape. In the crystal, the imidazolo-pyridine units are associated through slipped π-π stacking inter-actions together with weak C-HPyrâ¯ONtr and C-HBrmdc-ylâ¯ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromo-dodec-yl) hydrogen bonds. The 12-bromo-dodecyl chains overlap with each other between the stacks. The terminal -CH2Br group of the side chain shows disorder over two resolved sites in a 0.902â
(3)0.098â
(3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from Hâ¯H (48.1%), Hâ¯Br/Brâ¯H (15.0%) and Hâ¯O/Oâ¯H (12.8%) inter-actions. The optimized mol-ecular structure, using density functional theory at the B3LYP/ 6-311â
G(d,p) level, is compared with the experimentally determined structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
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MEDLINE
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article