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

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

doi:10.1107/S1600536812041839

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.091
Data-to-parameter ratio = 15.3
Details

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

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

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-HN interactions connect translationally-related triazole rings, while another set of C-HN 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); Li et al. (2010). For two related benzoxadiazole-triazole structures, see: Key, Cairo & Ferguson (2012); Key, Cairo & McDonald (2012). 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); Huang et al. (2010); Dong & Cheng (2011); Jia & Lu (2011); Menendez et al. (2012).

Experimental

Crystal data

C₁₅H₁₇N₅O₂
M_r = 299.34
Monoclinic, P 2₁ /c
a = 16.5752 (16) Å
b = 5.5429 (5) Å
c = 16.2452 (16) Å
= 91.3612 (13)°
V = 1492.1 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.935, T_max = 0.995
45733 measured reflections
3079 independent reflections
2413 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.091
S = 1.03
3079 reflections
201 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N2ⁱ	0.95	2.58	3.475 (2)	158
C8-H8N5ⁱⁱ	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); 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: 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.
Harju, K., Vahermo, M., Mutikainen, I. & Yli-Kauhaluoma, J. (2003). J. Comb. Chem. 5, 826-833.
Huang, C.-C., Wu, F.-L., Lo, Y. H., Lai, W.-R. & Lin, C.-H. (2010). Acta Cryst. E66, o1690.
Jia, J. & Lu, D. (2011). Acta Cryst. E67, o127.
Key, J. A. & Cairo, C. W. (2011). Dyes Pigm. 88, 95-102.
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, o3130-o3131.
Li, C., Henry, E., Mani, N. K., Tang, J., Brochon, J.-C., Deprez, E. & Xie, J. (2010). Eur. J. Org. Chem. pp. 2395-2405.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds