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Volume 69 
Part 1 
Page o63  
January 2013  

Received 7 November 2012
Accepted 30 November 2012
Online 8 December 2012

[zq2188sup1]
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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 16.1
Details
Open access

(3E,5E)-3,5-Bis(2-chlorobenzylidene)-1-propylpiperidin-4-one

Quanzhi Yang,a Lingzi Chen,a Bixia Weng,a Lei Fana and Xiaoping Wua*

aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China
Correspondence e-mail: wjzwzmc@126.com

The title compound, C22H21Cl2NO, is a derivative of mono-carbonyl analogues of curcumin (MACs). The molecule has an E conformation for each of the olefinic bonds. The 1-propylpiperidin-4-one ring has a distorted chair conformation with the ring N and the C and O atoms of the carbonyl group deviating from the mean plane of the remaining four ring C atoms by 0.682 (2), -0.134 (3) and -0.340 (4) Å, respectively. The dihedral angle between the benzene rings is 26.5 (1)°. In the crystal, molecules are connected by weak C-H...O and C-H...[pi] interactions.

Related literature

For related structures, see: Agrawal & Mishra (2010[Agrawal, D. K. & Mishra, P. K. (2010). Med. Res. Rev. 30, 818-860.]); Liang et al. (2008[Liang, G., Yang, S. L., Shao, L. L., Zhao, C. G., Xiao, J., Lv, Y. X., Yang, J., Zhao, Y. & Li, X. K. (2008). J. Asian Nat. Prod. Res. 10, 957-965.], 2009[Liang, G., Yang, S., Zhou, H., Shao, L., Huang, K., Xiao, J., Huang, Z. & Li, X. (2009). Eur. J. Med. Chem. 44, 915-919.]); Wu et al. (2010[Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.], 2011[Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.]); Zhao et al. (2010[Zhao, C., Cai, Y., He, X., Li, J., Zhang, L., Wu, J., Zhao, Y., Yang, S., Li, X., Li, W. & Liang, G. (2010). Eur. J. Med. Chem. 45, 5773-5780.], 2012[Zhao, C., Liu, Z. & Liang, G. (2012). Curr. Pharm. Des. In the press.]). For background to and applications of chalcones, see: Agrawal & Mishra (2010[Agrawal, D. K. & Mishra, P. K. (2010). Med. Res. Rev. 30, 818-860.]); Wu et al. (2010[Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.], 2011[Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.]); Zhao et al. (2012[Zhao, C., Liu, Z. & Liang, G. (2012). Curr. Pharm. Des. In the press.]).

[Scheme 1]

Experimental

Crystal data

  • C22H21Cl2NO

  • Mr = 386.30

  • Orthorhombic, P c a 21

  • a = 18.0123 (15) Å

  • b = 7.0128 (6) Å

  • c = 15.4364 (13) Å

  • V = 1949.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.29 × 0.21 × 0.11 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.759, Tmax = 1.000

  • 11133 measured reflections

  • 3807 independent reflections

  • 3508 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.04

  • 3807 reflections

  • 236 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1812 Friedel pairs

  • Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14-C19 ring.
D-H...A D-H H...A D...A D-H...A
C20-H20A...O1i 0.97 2.64 3.607 (3) 174
C8-H8...Cg1ii 0.93 2.89 3.568 131
C21-H21B...Cg1iii 0.97 3.01 3.613 121
Symmetry codes: (i) x, y+1, z; (ii) [x+{\script{1\over 2}}, -y, z]; (iii) [-x+1, -y, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2188 ).

Acknowledgements

This study was partially supported by the Technology Foundation for Medical Science of Zhejiang Province (grant No. 2012KYA129) and University Students in Zhejiang Science and Technology Innovation Projects (grant No. 2012R413020). The authors are grateful to the associate researcher Sun Jie from Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, for testing and crystal analysis.

References

Agrawal, D. K. & Mishra, P. K. (2010). Med. Res. Rev. 30, 818-860.  [ISI] [ChemPort] [PubMed]
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Liang, G., Yang, S. L., Shao, L. L., Zhao, C. G., Xiao, J., Lv, Y. X., Yang, J., Zhao, Y. & Li, X. K. (2008). J. Asian Nat. Prod. Res. 10, 957-965.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Liang, G., Yang, S., Zhou, H., Shao, L., Huang, K., Xiao, J., Huang, Z. & Li, X. (2009). Eur. J. Med. Chem. 44, 915-919.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.  [ISI] [CrossRef] [ChemPort] [PubMed]
Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.
Zhao, C., Cai, Y., He, X., Li, J., Zhang, L., Wu, J., Zhao, Y., Yang, S., Li, X., Li, W. & Liang, G. (2010). Eur. J. Med. Chem. 45, 5773-5780.  [ISI] [CrossRef] [ChemPort] [PubMed]
Zhao, C., Liu, Z. & Liang, G. (2012). Curr. Pharm. Des. In the press.

Acta Cryst (2013). E69, o63  [ doi:10.1107/S1600536812049252 ]

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