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Volume 69 
Part 7 
Page o1071  
July 2013  

Received 13 May 2013
Accepted 1 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.169
Data-to-parameter ratio = 23.4
Details
Open access

(3E,5E)-1-Allyl-3,5-bis(4-methoxybenzylidene)piperidin-4-one

aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and bDepartment of Physics, The Madura College, Madurai 625 011, India
Correspondence e-mail: ambujasureshj@yahoo.com

The piperidine ring in the title compound, C24H25NO3, adopts an envelope conformation with the N atom being the flap atom, and each C=C double bond exhibits an E conformation. In the crystal, C-H...O hydrogen bonds link the molecules, forming supramolecular layers that stack along the a axis.

Related literature

For background to piperidine ring systems, see: Guengerich et al. (1973[Guengerich, F. P., DiMari, S. J. & Broquist, H. P. (1973). J. Am. Chem. Soc. 95, 2055-2056.]); Puder et al. (2000[Puder, C., Krastel, P. & Zeeck, A. (2000). J. Nat. Prod. 63, 1258-1260.]). For the biological importance of the title compound, see: Dimmock, Elias et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Dimmock, Kandepu et al. (1999[Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P. A., Audette, G. F., Prasad, L., Perjési, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.]). For a similar structure, see: Suresh et al. (2007[Suresh, J., Suresh Kumar, R., Perumal, S. & Natarajan, S. (2007). Acta Cryst. C63, o315-o318.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25NO3

  • Mr = 375.45

  • Monoclinic, P 21 /c

  • a = 19.2409 (15) Å

  • b = 6.8457 (6) Å

  • c = 15.6393 (13) Å

  • [beta] = 98.255 (2)°

  • V = 2038.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.34 × 0.33 × 0.21 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.984

  • 22074 measured reflections

  • 5935 independent reflections

  • 3680 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.169

  • S = 1.03

  • 5935 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10A...O3i 0.97 2.59 3.3710 (18) 138
C21-H21C...O2ii 0.96 2.54 3.466 (2) 163
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5227 ).


Acknowledgements

This project was supported by the Research Center, Deanship of Scientific Research, College of Science, King Saud University.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.  [Web of Science] [PubMed] [ChemPort]
Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P. A., Audette, G. F., Prasad, L., Perjési, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Guengerich, F. P., DiMari, S. J. & Broquist, H. P. (1973). J. Am. Chem. Soc. 95, 2055-2056.  [CrossRef] [ChemPort] [Web of Science]
Puder, C., Krastel, P. & Zeeck, A. (2000). J. Nat. Prod. 63, 1258-1260.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suresh, J., Suresh Kumar, R., Perumal, S. & Natarajan, S. (2007). Acta Cryst. C63, o315-o318.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1071  [ doi:10.1107/S1600536813015195 ]

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