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

ABSTRACT: 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-catal-ysed azide-alkyne cyclo-addition (CuAAC) from the corres-ponding n-octyne and 4-azido-benzoxadiazole. The benz-oxa-diazole 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 inter-actions of the triazole and benzoxadiazole rings. The centroid of the extended ?-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.

SUBMITTER: Key JA 

PROVIDER: S-EPMC3515233 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature