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Volume 68 
Part 11 
Pages o3130-o3131  
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 = 0.035
wR = 0.096
Data-to-parameter ratio = 15.1
Details
Open access

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

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

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-H...N interactions between adjacent benzoxadiazole and triazole rings, forming a chain that propagates in the [-110] direction parallel to the ab plane.

Related literature

For the synthesis of the title compound, see: Key & Cairo (2011[Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.]). For computational studies of the absorption and fluorescence of the title compound, see: Brown et al. (2012[Brown, A., Ngai, T. Y., Key, J. A. & Cairo, C. W. (2012). J. Phys. Chem. A, 116, 46-54.]). For structures with 4-aryl substituted 1-benzyl-1,2,3-triazole rings, see: Key et al. (2008)[Key, J. A., Cairo, C. W. & Ferguson, M. J. (2008). Acta Cryst. E64, o1910.]; Li et al. (2011[Li, L., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. (2011). Dalton Trans. 40, 3365-3380.]); Raghavendra & Lam (2004[Raghavendra, M. S. & Lam, Y. (2004). Tetrahedron Lett. 45, 6129-6132.]); Sarmiento-Sánchez et al. (2011)[Sarmiento-Sánchez, J. I., Aguirre, G. & Rivero, I. A. (2011). Acta Cryst. E67, o1856.]. For two related benzoxadiazole 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, o3132.]). For the synthesis of analogous triazole-substituted coumarin structures, see: Key et al. (2009[Key, J. A., Koh, S., Timerghazin, Q. K., Brown, A. & Cairo, C. W. (2009). Dyes Pigm. 82, 196-203.]). For information on reactive chromophores, see: Cairo et al. (2010[Cairo, C. W., Key, J. A. & Sadek, C. M. (2010). Curr. Opin. Chem. Biol. 14, 57-63.]). For recent work on small molecule fluorophores, see: Lavis & Raines (2008[Lavis, L. D. & Raines, R. T. (2008). ACS Chem. Biol. 3, 142-155.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11N5O

  • Mr = 277.29

  • Triclinic, [P \overline 1]

  • a = 5.7526 (4) Å

  • b = 9.9261 (6) Å

  • c = 11.7012 (8) Å

  • [alpha] = 90.3799 (7)°

  • [beta] = 99.2517 (7)°

  • [gamma] = 103.2900 (7)°

  • V = 641.14 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.50 × 0.29 × 0.23 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.953, Tmax = 0.978

  • 5667 measured reflections

  • 2879 independent reflections

  • 2489 reflections with I > 2[sigma](I)

  • Rint = 0.012

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.096

  • S = 1.06

  • 2879 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 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
C5-H5...N3i 0.95 2.50 3.3483 (15) 148
C8-H8...N2ii 0.95 2.57 3.4367 (15) 151
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT, SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT, SADABS. 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: MW2083 ).


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

Brown, A., Ngai, T. Y., Key, J. A. & Cairo, C. W. (2012). J. Phys. Chem. A, 116, 46-54.  [ISI] [CrossRef] [ChemPort] [PubMed]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.  [CrossRef] [ChemPort]
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2008). Acta Cryst. E64, o1910.  [CSD] [CrossRef] [details]
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, o3132.  [CrossRef] [details]
Key, J. A., Koh, S., Timerghazin, Q. K., Brown, A. & Cairo, C. W. (2009). Dyes Pigm. 82, 196-203.  [CrossRef] [ChemPort]
Lavis, L. D. & Raines, R. T. (2008). ACS Chem. Biol. 3, 142-155.  [CrossRef] [PubMed] [ChemPort]
Li, L., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. (2011). Dalton Trans. 40, 3365-3380.  [CSD] [CrossRef] [ChemPort] [PubMed]
Raghavendra, M. S. & Lam, Y. (2004). Tetrahedron Lett. 45, 6129-6132.  [ISI] [CSD] [CrossRef] [ChemPort]
Sarmiento-Sánchez, J. I., Aguirre, G. & Rivero, I. A. (2011). Acta Cryst. E67, o1856.  [CSD] [CrossRef] [details]
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, o3130-o3131   [ doi:10.1107/S1600536812041827 ]

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