Ethyl 1-(2,6-difluoro­benz­yl)-1H-1,2,3-triazole-4-carboxyl­ate

Jia, J.; Lu, D.

doi:10.1107/S1600536810050014

Volume 67
Part 1
Page o127
January 2011

Received 25 November 2010
Accepted 30 November 2010
Online 15 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.055
wR = 0.163
Data-to-parameter ratio = 13.3
Details

Ethyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate

Jing Jia ^a and Dingqiang Lu ^a ^*

^aSchool of Pharmaceutical Sciences, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China and Jiangsu Provincial Institute of Materia Medica, Nanjing University of Technology, No. 26 Majia Street, Nanjing 210009, People's Republic of China
Correspondence e-mail: jiajing.jj@gmail.com

In the title compound, C₁₂H₁₁F₂N₃O₂, the dihedral angle between the triazole and phenyl rings is 73.74 (9)°. In the crystal, molecules are linked into chains along [010] via weak C-HO and C-HN hydrogen bonds.

Related literature

The title compound is an intermediate in the synthesis of rufinamide, a new anti-epilepsy drug (Herranz, 2008). For synthetic procedures, see: Abu-Orabi et al. (1989); Wang & Xie (2004). For a related structure, see: Xiao et al. (2008).

Experimental

Crystal data

C₁₂H₁₁F₂N₃O₂
M_r = 267.24
Monoclinic, P 2₁ /c
a = 9.4540 (19) Å
b = 10.963 (2) Å
c = 12.167 (2) Å
= 93.21 (3)°
V = 1259.1 (4) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.965, T_max = 0.977
3270 measured reflections
2316 independent reflections
1629 reflections with I > 2(I)
R_int = 0.026
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.163
S = 1.03
2316 reflections
174 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BO1ⁱ	0.97	2.47	3.415 (3)	166
C8-H8N3ⁱ	0.93	2.61	3.536 (3)	172
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2364 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Abu-Orabi, S. T., Atfah, M. A., Jibril, I., Mari'i, F. M. & Ali, A. A.-S. (1989). J. Heterocycl. Chem. 26, 1461-1468.
Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Herranz, J. L. (2008). Rev. Neurol. 47, 369-373.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, J. M. & Xie, Z. F. (2004). J. Med. Sci. Yanbian Univ. 27, 264-266.
Xiao, J., Wang, W. X. & Zhao, H. (2008). Acta Cryst. E64, o2085.

organic compounds