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Volume 68 
Part 11 
Page o3132  
November 2012  

Received 21 August 2012
Accepted 5 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.091
Data-to-parameter ratio = 15.3
Details
Open access

1-[1-(2,1,3-Benzoxadiazol-5-ylmethyl)-1H-1,2,3-triazol-4-yl]hexan-1-one

aAlberta Glycomics Centre, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada, and bX-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada
Correspondence e-mail: Bob.McDonald@ualberta.ca

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-H...N interactions connect translationally-related triazole rings, while another set of C-H...N 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).

Related literature

For the synthesis of similar benzoxadiazole compounds, see: Key & Cairo (2011[Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.]); Li et al. (2010[Li, C., Henry, E., Mani, N. K., Tang, J., Brochon, J.-C., Deprez, E. & Xie, J. (2010). Eur. J. Org. Chem. pp. 2395-2405.]). For two related benzoxadiazole-triazole structures, see: Key, Cairo & Ferguson (2012[Key, J. A., Cairo, C. W. & Ferguson, M. J. (2012). Acta Cryst. E68, o3128-o3129.]); Key, Cairo & McDonald (2012[Key, J. A., Cairo, C. W. & McDonald, R. (2012). Acta Cryst. E68, o3130-o3131.]). 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[Harju, K., Vahermo, M., Mutikainen, I. & Yli-Kauhaluoma, J. (2003). J. Comb. Chem. 5, 826-833.]); Huang et al. (2010[Huang, C.-C., Wu, F.-L., Lo, Y. H., Lai, W.-R. & Lin, C.-H. (2010). Acta Cryst. E66, o1690.]); Dong & Cheng (2011[Dong, S.-L. & Cheng, X.-C. (2011). Acta Cryst. E67, o769.]); Jia & Lu (2011[Jia, J. & Lu, D. (2011). Acta Cryst. E67, o127.]); Menendez et al. (2012[Menendez, C., Gau1, S., Ladeira, S., Lherbet, C. & Baltas, M. (2012). Eur. J. Org. Chem. pp. 409-416.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17N5O2

  • Mr = 299.34

  • Monoclinic, P 21 /c

  • a = 16.5752 (16) Å

  • b = 5.5429 (5) Å

  • c = 16.2452 (16) Å

  • [beta] = 91.3612 (13)°

  • V = 1492.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.74 × 0.14 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.995

  • 45733 measured reflections

  • 3079 independent reflections

  • 2413 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.091

  • S = 1.03

  • 3079 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N2i 0.95 2.58 3.475 (2) 158
C8-H8...N5ii 0.95 2.41 3.350 (2) 171
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXD (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2084 ).


Acknowledgements

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.

References

Bruker (2008). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dong, S.-L. & Cheng, X.-C. (2011). Acta Cryst. E67, o769.  [CSD] [CrossRef] [details]
Harju, K., Vahermo, M., Mutikainen, I. & Yli-Kauhaluoma, J. (2003). J. Comb. Chem. 5, 826-833.  [ISI] [CrossRef] [PubMed] [ChemPort]
Huang, C.-C., Wu, F.-L., Lo, Y. H., Lai, W.-R. & Lin, C.-H. (2010). Acta Cryst. E66, o1690.  [CSD] [CrossRef] [details]
Jia, J. & Lu, D. (2011). Acta Cryst. E67, o127.  [CrossRef] [details]
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.  [CrossRef] [ChemPort]
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2012). Acta Cryst. E68, o3128-o3129.  [CrossRef] [details]
Key, J. A., Cairo, C. W. & McDonald, R. (2012). Acta Cryst. E68, o3130-o3131.  [CrossRef] [details]
Li, C., Henry, E., Mani, N. K., Tang, J., Brochon, J.-C., Deprez, E. & Xie, J. (2010). Eur. J. Org. Chem. pp. 2395-2405.  [CrossRef]
Menendez, C., Gau1, S., Ladeira, S., Lherbet, C. & Baltas, M. (2012). Eur. J. Org. Chem. pp. 409-416.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3132  [ doi:10.1107/S1600536812041839 ]

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