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5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole

The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal­ysed azide–alkyne cyclo­addition (CuAAC) from the corres­ponding n-octyne and 4-azido­benzoxadiazole. The benz­oxa­diazole and triazole rings show a roughly planar orien...

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Detalles Bibliográficos
Autores principales: Key, Jessie A., Cairo, Christopher W., Ferguson, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515233/
https://www.ncbi.nlm.nih.gov/pubmed/23284453
http://dx.doi.org/10.1107/S1600536812041815
Descripción
Sumario:The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal­ysed azide–alkyne cyclo­addition (CuAAC) from the corres­ponding n-octyne and 4-azido­benzoxadiazole. The benz­oxa­diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C—H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter­actions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid–centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å.