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Volume 68 
Part 1 
Page o173  
January 2012  

Received 10 December 2011
Accepted 10 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.161
Data-to-parameter ratio = 13.8
Details
Open access

N-{2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethyl}phthalimide

aKey Laboratory of Fine Petrohemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China, and bAnalytical Center, Changzhou University, Changzhou 213164, People's Republic of China
Correspondence e-mail: yingshao@cczu.edu.cn

In the title compound, C16H21N3O3, the piperazine ring adopts a chair conformation, with its N-C bonds in pseudo-equatorial orientations. In the crystal, molecules are linked by O-H...N hydrogen bonds, generating C(5) chains propagating in [101]. Weak aromatic [pi]-[pi] stacking interactions also occur [centroid-centroid separation = 3.899 (1) Å].

Related literature

For general background to piperazine derivatives, see: Tian et al. (2011[Tian, Z., Wei, X., Liang, J., Liu, R. & Zhang, Y. (2011). Yingyong Huagong, 40, 1648-1652.]). For the preparation, see: Ghosh et al. (2010[Ghosh, B., Antonio, T., Zhen, J., Kharkar, P., Reith, M. E. A. & Dutta, A. K. (2010). J. Med. Chem. 53, 1023-1037.]).

[Scheme 1]

Experimental

Crystal data
  • C16H21N3O3

  • Mr = 303.36

  • Monoclinic, P 21 /n

  • a = 5.8109 (6) Å

  • b = 37.012 (4) Å

  • c = 7.3537 (8) Å

  • [beta] = 95.634 (2)°

  • V = 1573.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.25 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.982

  • 8562 measured reflections

  • 2775 independent reflections

  • 2537 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.161

  • S = 1.00

  • 2775 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...N3i 0.82 2.00 2.811 (3) 171
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. 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: 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: HB6564 ).


Acknowledgements

We gratefully acknowledge the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and Changzhou University (ZMF10020010) for financial support.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ghosh, B., Antonio, T., Zhen, J., Kharkar, P., Reith, M. E. A. & Dutta, A. K. (2010). J. Med. Chem. 53, 1023-1037.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tian, Z., Wei, X., Liang, J., Liu, R. & Zhang, Y. (2011). Yingyong Huagong, 40, 1648-1652.  [ChemPort]


Acta Cryst (2012). E68, o173  [ doi:10.1107/S160053681105327X ]

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