Received 10 August 2012
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-HN 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 -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.
For the synthesis of the title compound and related benzoxadiazole analogs, see: Key & Cairo (2011). For computational studies of the absorption and fluorescence properties of this series of compounds, see: Brown et al. (2012). For structures with 1-aryl-substituted 1,2,3-triazole rings, see: Costa et al. (2006). For the use of fluorophores as chemical or biological probes, see: Cairo et al. (2010); Lavis & Raines (2008). For related benzoxadiazole structures, see: Key et al. (2012a,b). For triazole-substituted coumarin derivatives, see: Key et al. (2009).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2081 ).
This work was supported by the Natural Science and Engineering Research Council of Canada and the Alberta Glycomics Centre.
Brown, A., Ngai, T. Y., Key, J. A. & Cairo, C. W. (2012). J. Phys. Chem. A, 116, 46-54.
Bruker (2008). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.
Cairo, C. W., Key, J. A. & Sadek, C. M. (2010). Curr. Opin. Chem. Biol. 14, 57-63.
Costa, M. S., Boechat, N., Ferreira, V. F., Wardell, S. M. S. V. & Skakle, J. M. S. (2006). Acta Cryst. E62, o2048-o2050.
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.
Key, J. A., Cairo, C. W. & McDonald, R. (2012a). Acta Cryst. E68, o3130-o3131.
Key, J. A., Cairo, C. W. & McDonald, R. (2012b). Acta Cryst. E68, o3132.
Key, J. A., Koh, S., Timerghazin, Q. K., Brown, A. & Cairo, C. W. (2009). Dyes Pigm. 82, 196-203.
Lavis, L. D. & Raines, R. T. (2008). ACS Chem. Biol. 3, 142-155.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.