Title of article :
Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-chloro­phen­yl)-5-cyclo­propyl-1-(4-meth­­oxy­phen­yl)-1H-1,2,3-triazole-4-carboxamide
Author/Authors :
Pokhodylo, Nazariy Department of Organic Chemistry, Ivan Frank - National University of Lviv, Ukraine , Slyvka, Yurii Department of Inorganic Chemistry - Ivan Franko National University of Lviv, Ukraine , Pavlyuk, Volodymyr Department of Inorganic Chemistry - Ivan Franko National University of Lviv, Ukraine
Pages :
10
From page :
1
To page :
10
Abstract :
The title compound, C19H17ClN4O2, was obtained via a two-step synthesis involving the enol-mediated click Dimroth reaction of 4-azido­anisole with methyl 3-cyclo­propyl-3-oxo­propano­ate leading to the 5-cyclo­propyl-1-(4-meth­oxy­phen­yl)-1H-1,2,3-triazole-4-carb­oxy­lic acid and subsequent acid amidation with 4-chloro­aniline by 1,1′-carbonyl­diimidazole (CDI). It crystallizes in space group P21/n, with one mol­ecule in the asymmetric unit. In the extended structure, two mol­ecules arranged in a near coplanar fashion relative to the triazole ring planes are inter­connected by N—H⋯N and C—H⋯N hydrogen bonds into a homodimer. The formation of dimers is a consequence of the above inter­action and the edge-to-face stacking of aromatic rings, which are turned by 58.0 (3)° relative to each other. The dimers are linked by C—H⋯O inter­actions into ribbons. DFT calculations demonstrate that the frontier mol­ecular orbitals are well separated in energy and the HOMO is largely localized on the 4-chloro­phenyl amide motif while the LUMO is associated with aryl­triazole grouping. A Hirshfeld surface analysis was performed to further analyse the inter­molecular inter­actions.
Keywords :
crystal structure , 1,2,3-triazole , DFT calculation , Hirshfeld surface analysis
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
Serial Year :
2020
Full Text URL :
Record number :
2624113
Link To Document :
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