[Journal logo]

Volume 68 
Part 11 
Pages o3128-o3129  
November 2012  

Received 10 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 = 0.036
wR = 0.099
Data-to-parameter ratio = 17.2
Details
Open access

5-(4-Hexyl-1H-1,2,3-triazol-1-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: michael.ferguson@ualberta.ca

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-H...N 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 [pi]-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.

Related literature

For the synthesis of the title compound and related benzoxadiazole analogs, see: Key & Cairo (2011[Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.]). For computational studies of the absorption and fluorescence properties of this series of compounds, 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 1-aryl-substituted 1,2,3-triazole rings, see: Costa et al. (2006[Costa, M. S., Boechat, N., Ferreira, V. F., Wardell, S. M. S. V. & Skakle, J. M. S. (2006). Acta Cryst. E62, o2048-o2050.]). For the use of fluorophores as chemical or biological probes, see: Cairo et al. (2010[Cairo, C. W., Key, J. A. & Sadek, C. M. (2010). Curr. Opin. Chem. Biol. 14, 57-63.]); Lavis & Raines (2008[Lavis, L. D. & Raines, R. T. (2008). ACS Chem. Biol. 3, 142-155.]). For related benzoxadiazole structures, see: Key et al. (2012a[Key, J. A., Cairo, C. W. & McDonald, R. (2012a). Acta Cryst. E68, o3130-o3131.],b[Key, J. A., Cairo, C. W. & McDonald, R. (2012b). Acta Cryst. E68, o3132.]). For triazole-substituted coumarin derivatives, see: Key et al. (2009[Key, J. A., Koh, S., Timerghazin, Q. K., Brown, A. & Cairo, C. W. (2009). Dyes Pigm. 82, 196-203.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17N5O

  • Mr = 271.33

  • Triclinic, [P \overline 1]

  • a = 5.3604 (8) Å

  • b = 7.8585 (11) Å

  • c = 16.357 (2) Å

  • [alpha] = 87.4656 (17)°

  • [beta] = 86.2519 (16)°

  • [gamma] = 85.6240 (17)°

  • V = 685.04 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 1.02 × 0.35 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.915, Tmax = 0.997

  • 6114 measured reflections

  • 3120 independent reflections

  • 2568 reflections with I > 2[sigma](I)

  • Rint = 0.013

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.099

  • S = 1.04

  • 3120 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 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 2.52 3.4674 (15) 177
C5-H5...N4ii 0.95 2.46 3.3445 (15) 154
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x-1, -y+1, -z+1.

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


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2081 ).


Acknowledgements

This work was supported by the Natural Science and Engineering Research Council of Canada and the Alberta Glycomics Centre.

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 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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Costa, M. S., Boechat, N., Ferreira, V. F., Wardell, S. M. S. V. & Skakle, J. M. S. (2006). Acta Cryst. E62, o2048-o2050.  [CSD] [CrossRef] [details]
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.  [CrossRef] [ChemPort]
Key, J. A., Cairo, C. W. & McDonald, R. (2012a). Acta Cryst. E68, o3130-o3131.  [CrossRef] [details]
Key, J. A., Cairo, C. W. & McDonald, R. (2012b). 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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3128-o3129   [ doi:10.1107/S1600536812041815 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.