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Volume 68 
Part 1 
Page o123  
January 2012  

Received 13 November 2011
Accepted 8 December 2011
Online 14 December 2011

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.093
Data-to-parameter ratio = 14.4
Details
Open access

Ethyl 2-{[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate

Xiao-Li Yanga*

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: yangxl@jit.edu.cn

The title compound, C19H17ClN2O3, was synthesized by the reaction of 5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-ol and ethyl 2-bromoacetate. In the crystal, the C- and N-linked benzene rings are twisted by 45.15 (3) and 53.55 (3)°, respectively, from the plane of the bridging 1H-pyrazole ring.

Related literature

For 1H-pyrazol-3-oxy derivatives, see: Li et al. (2010[Li, Y., Liu, R., Yan, Z., Zhang, X. & Zhu, H. (2010). Bull. Korean Chem. Soc. 31, 3341-3347.]). For alkyloxyacetates as bioactive groups, see: Tohyama & Sanemitsu (2001[Tohyama, Y. & Sanemitsu, Y. (2001). EP Patent No. 1122244.]). For bond-length data, see: Allen et al. (1987[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.]). For the synthetic procedure, see: Liu et al. (2011[Liu, Y., He, G., Chen, K., Jin, Y., Li, Y. & Zhu, H. (2011). Eur. J. Org. Chem. pp. 5323-5330.]);

[Scheme 1]

Experimental

Crystal data

  • C19H17ClN2O3

  • Mr = 356.80

  • Orthorhombic, P b c a

  • a = 11.6158 (11) Å

  • b = 15.9119 (16) Å

  • c = 19.302 (2) Å

  • V = 3567.6 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.10 mm
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.933, Tmax = 0.977

  • 6360 measured reflections

  • 3244 independent reflections

  • 1787 reflections with I > 2[sigma](I)

  • Rint = 0.092

  • 3 standard reflections every 200 reflections intensity decay: 1%
Refinement

  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.093

  • S = 1.01

  • 3244 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2274 ).

Acknowledgements

This work was supported by the Industrialization of Scientific Research Promotion Projects of Colleges and Universities in Jiangsu Province. The author also thanks the Center of Testing and Analysis, Nanjing University, for the data collection.

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.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Li, Y., Liu, R., Yan, Z., Zhang, X. & Zhu, H. (2010). Bull. Korean Chem. Soc. 31, 3341-3347.  [ChemPort]
Liu, Y., He, G., Chen, K., Jin, Y., Li, Y. & Zhu, H. (2011). Eur. J. Org. Chem. pp. 5323-5330.  [CSD] [CrossRef]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tohyama, Y. & Sanemitsu, Y. (2001). EP Patent No. 1122244.

Acta Cryst (2012). E68, o123  [ doi:10.1107/S1600536811052937 ]

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