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

Key, J.A.; Cairo, C.W.; McDonald, R.

doi:10.1107/S1600536812041827

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 15.1
Details

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

Jessie A. Key,^a Christopher W. Cairo ^a and Robert McDonald ^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: 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-HN 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). For computational studies of the absorption and fluorescence of the title compound, see: Brown et al. (2012). For structures with 4-aryl substituted 1-benzyl-1,2,3-triazole rings, see: Key et al. (2008); Li et al. (2011); Raghavendra & Lam (2004); Sarmiento-Sánchez et al. (2011). For two related benzoxadiazole structures, see: Key, Cairo & Ferguson (2012); Key, Cairo & McDonald (2012). For the synthesis of analogous triazole-substituted coumarin structures, see: Key et al. (2009). For information on reactive chromophores, see: Cairo et al. (2010). For recent work on small molecule fluorophores, see: Lavis & Raines (2008).

Experimental

Crystal data

C₁₅H₁₁N₅O
M_r = 277.29
Triclinic, $[P \overline 1]$
a = 5.7526 (4) Å
b = 9.9261 (6) Å
c = 11.7012 (8) Å
= 90.3799 (7)°
= 99.2517 (7)°
= 103.2900 (7)°
V = 641.14 (7) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.953, T_max = 0.978
5667 measured reflections
2879 independent reflections
2489 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.096
S = 1.06
2879 reflections
191 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5N3ⁱ	0.95	2.50	3.3483 (15)	148
C8-H8N2ⁱⁱ	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); 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: 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.
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.
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2008). Acta Cryst. E64, o1910.
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2012). Acta Cryst. E68, o3128-o3129.
Key, J. A., Cairo, C. W. & McDonald, R. (2012). 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.
Li, L., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. (2011). Dalton Trans. 40, 3365-3380.
Raghavendra, M. S. & Lam, Y. (2004). Tetrahedron Lett. 45, 6129-6132.
Sarmiento-Sánchez, J. I., Aguirre, G. & Rivero, I. A. (2011). Acta Cryst. E67, o1856.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References