5-(4-Ethoxy­benzyl)-1H-tetra­zole

Gao, Y.-L.; Zhao, G.-L.; Shao, H.; Liu, W.; Wang, J.

doi:10.1107/S1600536809055597

Volume 66
Part 2
Page o322
February 2010

Received 26 December 2009
Accepted 28 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.103
Data-to-parameter ratio = 12.5
Details

5-(4-Ethoxybenzyl)-1H-tetrazole

Yun-Long Gao,^a Gui-Long Zhao,^b Hua Shao,^b Wei Liu ^a and Jian-wu Wang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
Correspondence e-mail: yugp2005@yahoo.com.cn

In the title molecule, C₁₀H₁₂N₄O, the tetrazole and benzene rings form a dihedral angle of 67.52 (2)°. In the crystal, intermolecular N-HN hydrogen bonds link the molecules into chains along the a axis. The relatively short distance of 3.760 (3) Å between the centroids of the tetrazole rings suggests the existence of [pi] - [pi] interactions.

Related literature

For details of the biological activities of sodium-glucose co-transporter 2 (SGLT2) inhibitors, see: Arakawa et al. (2001); Meng et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₁₂N₄O
M_r = 204.24
Monoclinic, P 2₁ /n
a = 4.9291 (10) Å
b = 18.145 (4) Å
c = 11.363 (2) Å
= 99.19 (3)°
V = 1003.2 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 113 K
0.34 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007) T_min = 0.969, T_max = 0.996
6870 measured reflections
1768 independent reflections
1487 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.103
S = 1.10
1768 reflections
142 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N4ⁱ	0.91 (1)	1.90 (1)	2.7897 (16)	166 (1)
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (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: CV2684 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arakawa, K., Ishihara, T., Oku, A., Nawano, M., Ueta, K., Kitamura, K., Matsumoto, M. & Saito, A. (2001). Br. J. Pharmacol. 132, 578-586.
Meng, M., Ellsworth, B. A., Nirschl, A. A., McCann, P. J., Patel, M., Girotra, R. N., Wu, G., Sher, P. M., Morrison, E. P., Biller, S. A., Zahler, R., Deshpande, P. P., Pullockaran, A., Hagan, D. L., Morgan, N. N., Taylor, J. R., Obermeier, M. T., Humphreys, W. G., Khanna, A., Discenza, L., Robertson, J. M., Wang, A., Han, S., Wetterau, J. R., Janovitz, E. B., Flint, O. P., Whaley, J. M. & Washburn, W. N. (2008). J. Med. Chem. 51, 1145-1149.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds