Acta Crystallographica Section E

Structure Reports Online

Volume 68, Part 11 (November 2012)


organic compounds



mw2081 scheme

Acta Cryst. (2012). E68, o3128-o3129    [ doi:10.1107/S1600536812041815 ]

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

J. A. Key, C. W. Cairo and M. J. Ferguson

Abstract: The title compound, C14H17N5O, a 1,2,3-triazole derivative of benzoxadiazole (C14H17N5O), 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 [pi]-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.


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