학술논문

Crystal structure and Hirshfeld surface analysis of two imidazo[1,2-a]pyridine derivatives: N-tert-butyl-2-(4-methoxyphenyl)-5-methylimidazo[1,2-a]pyridin-3-amine and N-tert-butyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-amine
Document Type
article
Source
Acta Crystallographica Section E: Crystallographic Communications, Vol 74, Iss 12, Pp 1913-1918 (2018)
Subject
crystal structure
imidazole
imidazo[1,2-a]pyridine derivatives
N—H...N hydrogen bonding
C—H...π interactions
offset π–π interactions
Hirshfeld surface analysis
fingerprint plots
Crystallography
QD901-999
Language
English
ISSN
2056-9890
20569890
Abstract
In the title imidazo[1,2-a]pyridine derivatives, N-tert-butyl-2-(4-methoxyphenyl)-5-methylimidazo[1,2-a]pyridin-3-amine, C19H23N3O, (I), and N-tert-butyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-amine, C19H24N4, (II), the 4-methoxyphenyl ring in (I) and the 4-(dimethylamino)phenyl ring in (II) are inclined to the respective imidazole rings by 26.69 (9) and 31.35 (10)°. In the crystal of (I), molecules are linked by N—H...N hydrogen bonds, forming chains propagating along the [001] direction. The chains are linked by C—H...π interactions, forming layers parallel to the (010) plane. In (II), the crystal packing also features N—H...N hydrogen bonds, which together with C—H...N hydrogen bonds link molecules to form chains propagating along the c-axis direction. The chains are linked by C—H...π interactions to form layers parallel to the (100) plane. Inversion-related layers are linked by offset π–π interactions [intercentroid distance = 3.577 (1) Å]. The intermolecular interactions of both compounds were analyzed using Hirshfeld surface analysis and two-dimensional fingerprint plots.