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

Zhang, B.; Damu, G.L.V.; Lv, J.-S.; Zhou, C.-H.

doi:10.1107/S1600536811052597

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 (C-C) = 0.003 Å
R = 0.031
wR = 0.086
Data-to-parameter ratio = 10.6
Details

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

Bo Zhang,^a Guri L. V. Damu,^a Jing-Song Lv ^a and Cheng-He Zhou ^a ^*

^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). For applications of piperazine derivatives, see: Gan, Cai & Zhou (2009); Cai et al. (2009); Gan, Lu, & Zhou (2009).

Experimental

Crystal data

C₁₃H₁₅ClF₂N₂O
M_r = 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 radiation
= 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) T_min = 0.915, T_max = 0.931
5743 measured reflections
2324 independent reflections
2238 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 938 Friedel pairs
Flack parameter: 0.05 (7)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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

organic compounds