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

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

Jessie A Key, Christopher W Cairo, Michael J Ferguson

Acta Crystallogr Sect E Struct Rep Online. 2012 Nov 1;68(Pt 11):o3128-9.

PMID: 23284453

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 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP142246488	4-Chloro-7-chlorosulfonyl-2,1,3-benzoxadiazole		142246-48-8	Price

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