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Volume 68 
Part 1 
Page o70  
January 2012  

Received 30 November 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.086
Data-to-parameter ratio = 10.6
Details
Open access

2-Chloro-1-[4-(2,4-difluorobenzyl)piperazin-1-yl]ethanone

aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
Correspondence e-mail: zhouch@swu.edu.cn

In the title molecule, C13H15ClF2N2O, the piperazine ring is in a chair conformation with the 2,4-difluorobenzyl and chloroacetyl substituents in equatorial positions.

Related literature

For the synthesis, see: Gan et al. (2010[Gan, L.-L., Fang, B. & Zhou, C.-H. (2010). Bull. Korean Chem. Soc. 31, 3684-3693.]). For applications of piperazine derivatives, see: Gan, Cai & Zhou (2009[Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009). Chin. Pharm. J. 44, 1361-1368.]); Cai et al. (2009[Cai, J.-L., Lu, Y.-H., Gan, L.-L. & Zhou, C.-H. (2009). Chin. J. Antibiot. 34, 454-462.]); Gan, Lu, & Zhou (2009[Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009). Chin. J. Biochem. Pharm. 30, 127-131.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15ClF2N2O

  • Mr = 288.72

  • Orthorhombic, P 21 21 21

  • a = 7.895 (2) Å

  • b = 8.512 (2) Å

  • c = 19.884 (5) Å

  • V = 1336.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.24 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.915, Tmax = 0.931

  • 5743 measured reflections

  • 2324 independent reflections

  • 2238 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.086

  • S = 1.07

  • 2324 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 938 Friedel pairs

  • Flack parameter: 0.05 (7)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5389 ).


Acknowledgements

This work was partially supported by the Natural Science Foundation of China (21172181), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Fundamental Research Funds for the Central Universities (XDJK2011D007).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, J.-L., Lu, Y.-H., Gan, L.-L. & Zhou, C.-H. (2009). Chin. J. Antibiot. 34, 454-462.  [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009). Chin. Pharm. J. 44, 1361-1368.  [ChemPort]
Gan, L.-L., Fang, B. & Zhou, C.-H. (2010). Bull. Korean Chem. Soc. 31, 3684-3693.  [ChemPort]
Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009). Chin. J. Biochem. Pharm. 30, 127-131.  [ChemPort]
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o70  [ doi:10.1107/S1600536811052597 ]

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