Received 21 August 2012
In the title compound, C15H11N5O, which was prepared as part of a study to identify fluorogenic substrates for the Cu-catalysed azide-alkyne cycloaddition (CuAAC) reaction, the benzoxadiazole unit and the triazole ring are much more closely coplanar [dihedral angle = 10.92 (7)°] than either is to the benzyl group [dihedral angles = 69.13 (3)° and 78.20 (4)°, respectively]. The crystal structure features two different sets of weak intermolecular C-HN interactions between adjacent benzoxadiazole and triazole rings, forming a chain that propagates in the [-110] direction parallel to the ab plane.
For the synthesis of the title compound, see: Key & Cairo (2011). For computational studies of the absorption and fluorescence of the title compound, see: Brown et al. (2012). For structures with 4-aryl substituted 1-benzyl-1,2,3-triazole rings, see: Key et al. (2008); Li et al. (2011); Raghavendra & Lam (2004); Sarmiento-Sánchez et al. (2011). For two related benzoxadiazole structures, see: Key, Cairo & Ferguson (2012); Key, Cairo & McDonald (2012). For the synthesis of analogous triazole-substituted coumarin structures, see: Key et al. (2009). For information on reactive chromophores, see: Cairo et al. (2010). For recent work on small molecule fluorophores, see: Lavis & Raines (2008).
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: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2083 ).
We acknowledge the University of Alberta, the Natural Sciences and Engineering Research Council of Canada and the Alberta Glycomics Centre for funding of this work.
Brown, A., Ngai, T. Y., Key, J. A. & Cairo, C. W. (2012). J. Phys. Chem. A, 116, 46-54.
Bruker (2008). APEX2, SAINT, SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cairo, C. W., Key, J. A. & Sadek, C. M. (2010). Curr. Opin. Chem. Biol. 14, 57-63.
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2008). Acta Cryst. E64, o1910.
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2012). Acta Cryst. E68, o3128-o3129.
Key, J. A., Cairo, C. W. & McDonald, R. (2012). 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.
Li, L., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. (2011). Dalton Trans. 40, 3365-3380.
Raghavendra, M. S. & Lam, Y. (2004). Tetrahedron Lett. 45, 6129-6132.
Sarmiento-Sánchez, J. I., Aguirre, G. & Rivero, I. A. (2011). Acta Cryst. E67, o1856.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.