Received 21 August 2012
The title compound, C15H17N5O2, was synthesized as part of a series of benzoxadiazole analogs which were examined for fluorescent properties by Cu-catalysed azide-alkyne cycloaddition (CuAAC) of a 4-azidomethyl-benzoxadiazole substrate. The structure shows a nearly coplanar orientation of the hexanone keto group and the 1,2,3-triazole ring [dihedral angle = 4.3 (3)°], while the benzoxadiazole and triazole groups are much more severely inclined [dihedral angle = 70.87 (4)°]. In the crystal, weak C-HN interactions connect translationally-related triazole rings, while another set of C-HN interactions is formed between inversion-related benzoxadiazole units, forming a three-dimensional network. The crystal studied was a non-merohedral twin with refined value of the twin fraction of 0.2289 (16).
For the synthesis of similar benzoxadiazole compounds, see: Key & Cairo (2011); Li et al. (2010). For two related benzoxadiazole-triazole structures, see: Key, Cairo & Ferguson (2012); Key, Cairo & McDonald (2012). For structures of 1-(aryl)methyl-1,2,3-triazole compounds with 4-carbonyl substituents [RC(O) or ROC(O)], see: Harju et al. (2003); Huang et al. (2010); Dong & Cheng (2011); Jia & Lu (2011); Menendez et al. (2012).
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: MW2084 ).
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.
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