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

Shao, Y.; An, D.; Zhou, M.; Liu, L.; Sun, X.-Q.

doi:10.1107/S160053681105327X

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.161
Data-to-parameter ratio = 13.8
Details

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

Ying Shao,^a ^* Dong An,^a Mi Zhou,^a Li Liu ^b and Xiao-Qiang Sun ^a

^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-HN 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). For the preparation, see: Ghosh et al. (2010).

Experimental

Crystal data

C₁₆H₂₁N₃O₃
M_r = 303.36
Monoclinic, P 2₁ /n
a = 5.8109 (6) Å
b = 37.012 (4) Å
c = 7.3537 (8) Å
= 95.634 (2)°
V = 1573.9 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.978, T_max = 0.982
8562 measured reflections
2775 independent reflections
2537 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.161
S = 1.00
2775 reflections
201 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AN3ⁱ	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, Z., Wei, X., Liang, J., Liu, R. & Zhang, Y. (2011). Yingyong Huagong, 40, 1648-1652.

organic compounds