(E)-1-Methyl-5-(3-methyl-4-chloro­phen­oxy)-3-trifluoro­meth­yl-1H-pyrazole-4-carbaldehyde O-acetyl­oxime

Dai, H.; Shen, Y.-F.; Chen, J.; Chen, H.-L.; Shen, Y.-J.

doi:10.1107/S1600536811006696

Volume 67
Part 3
Page o726
March 2011

Received 16 February 2011
Accepted 22 February 2011
Online 26 February 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.115
Data-to-parameter ratio = 16.1
Details

(E)-1-Methyl-5-(3-methyl-4-chlorophenoxy)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-acetyloxime

Hong Dai,^a Yan-Fei Shen,^a Jiao Chen,^a Hong-Lian Chen ^a and Yong-Jun Shen ^a ^*

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
Correspondence e-mail: gaofz2005@yahoo.com.cn

In the title molecule, C₁₅H₁₃ClF₃N₃O₃, the pyrazole and benzene rings form a dihedral angle of 77.6 (3)°. In the crystal, molecules related by translation along the a axis are linked into chains via C-HO hydrogen bonds. The crystal packing is stabilized further by weak [pi] - [pi] [centroid-centroid distance = 3.734 (6) Å] and dipole-dipole interactions [CO = 3.174 (2) Å].

Related literature

For the bioactivity of pyrazole derivatives, see: Hagiwara & Suzuki (1996); Ranatunge et al. (2004). For related structures, see: Fu et al. (2008); Li et al. (2006). For the biological activity of compounds containing an oxime ester fragment, see: Vonhoff et al. (1999); Wood et al. (1997).

Experimental

Crystal data

C₁₅H₁₃ClF₃N₃O₃
M_r = 375.73
Orthorhombic, P b c n
a = 11.951 (2) Å
b = 19.549 (4) Å
c = 13.726 (3) Å
V = 3206.8 (11) Å³
Z = 8
Mo K radiation
= 0.29 mm^-1
T = 113 K
0.16 × 0.12 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) T_min = 0.955, T_max = 0.977
21575 measured reflections
3686 independent reflections
3208 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.115
S = 1.10
3686 reflections
229 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5BO3ⁱ	0.96	2.55	3.102 (2)	117
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2008); 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: CV5055 ).

Acknowledgements

This work was supported by the Science and Technology Projects Fund of Nantong City (grant Nos. K2010016, AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010, 09 C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

Fu, N., Zou, X.-M., Lin, D.-Y., Zhu, Y.-Q. & Yang, H.-Z. (2008). Acta Cryst. E64, o192.
Hagiwara, K. & Suzuki, H. (1996). Jpn Patent No. 08193067.
Li, Y., Yang, X.-P., Zhang, H.-Q., Meng, X.-G. & Liu, Z.-J. (2006). Acta Cryst. E62, o2027-o2029.
Ranatunge, R. R., Augustyniak, M., Bandarage, U. K., Earl, R. A., Ellis, J. L., Garvey, D. S., Janero, D. R., Letts, L. G., Martino, A. M., Murty, M. G., Richardson, S. K., Schroeder, J. D., Shumway, M. J., Tam, S. W., Trocha, A. M. & Young, D. V. (2004). J. Med. Chem. 47, 2180-2193.
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vonhoff, S., Piens, K., Pipelier, M., Braet, C., Claeyssens, M. & Vasella, A. (1999). Helv. Chim. Acta, 82, 963-980.
Wood, J. L., Stoltz, B. M., Goodman, S. N. & Onwueme, K. (1997). J. Am. Chem. Soc. 119, 9652-9661.

organic compounds