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

Key, J.A.; Cairo, C.W.; Ferguson, M.J.

doi:10.1107/S1600536812041815

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 (C-C) = 0.002 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 17.2
Details

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

Jessie A. Key,^a Christopher W. Cairo ^a and Michael J. Ferguson ^b ^*

^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-HN 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). For computational studies of the absorption and fluorescence properties of this series of compounds, see: Brown et al. (2012). For structures with 1-aryl-substituted 1,2,3-triazole rings, see: Costa et al. (2006). For the use of fluorophores as chemical or biological probes, see: Cairo et al. (2010); Lavis & Raines (2008). For related benzoxadiazole structures, see: Key et al. (2012a,b). For triazole-substituted coumarin derivatives, see: Key et al. (2009).

Experimental

Crystal data

C₁₄H₁₇N₅O
M_r = 271.33
Triclinic, $[P \overline 1]$
a = 5.3604 (8) Å
b = 7.8585 (11) Å
c = 16.357 (2) Å
= 87.4656 (17)°
= 86.2519 (16)°
= 85.6240 (17)°
V = 685.04 (17) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.915, T_max = 0.997
6114 measured reflections
3120 independent reflections
2568 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.099
S = 1.04
3120 reflections
181 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N2ⁱ	0.95	2.52	3.4674 (15)	177
C5-H5N4ⁱⁱ	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); 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: 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.
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.
Costa, M. S., Boechat, N., Ferreira, V. F., Wardell, S. M. S. V. & Skakle, J. M. S. (2006). Acta Cryst. E62, o2048-o2050.
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.
Key, J. A., Cairo, C. W. & McDonald, R. (2012a). Acta Cryst. E68, o3130-o3131.
Key, J. A., Cairo, C. W. & McDonald, R. (2012b). 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References