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Volume 69 
Part 6 
Pages o947-o948  
June 2013  

Received 6 May 2013
Accepted 17 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.070
wR = 0.310
Data-to-parameter ratio = 13.9
Details
Open access

Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

aDepartment of Chemistry, College of Science, China University of Petroleum, Qingdao 266555, People's Republic of China, and bState Key Laboratory of Heavy Oil Processing, China University of Petroleum, Qingdao 266555, People's Republic of China
Correspondence e-mail: zfyancat@163.com

The title compound, C32H28Cl2N2O2, was synthesized by a multicomponent reaction of 4-chlorobenzaldehyde, aniline and ethyl acetoacetate. The central 1,2,5,6-tetrahydropyridine ring exhibits a distorted boat conformation and the two chlorophenyl rings attached to the central ring at positions 2 and 6 are oriented in opposite directions. The two O atoms of the ethoxycarbonyl group are involved in intramolecular N-H...O and C-H...O hydrogen bonds. In the crystal, weak C-H...O hydrogen bonds link molecules related by translation along the b axis into chains.

Related literature

For applications of functionalized piperidines, see: Viegas et al. (2004[Viegas, C., Bolzani, J. V. S., Furlan, M., Barreiro, E. J., Young, M. C. M., Tomazela, D. & Eberlin, M. N. (2004). J. Nat. Prod. 67, 908-910.]); Kobayashi et al. (1999[Kobayashi, S., Ueno, M., Suzuki, R., Ishitani, H., Kim, H. S. & Wataya, Y. (1999). J. Org. Chem. 64, 6833-6841.]). For the crystal structures of related compounds, see: Khan et al. (2008[Khan, A. T., Parvin, T. & Choudhury, L. H. (2008). J. Org. Chem. 73, 8398-8402.]); Brahmachari & Das (2012[Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.]).

[Scheme 1]

Experimental

Crystal data
  • C32H28Cl2N2O2

  • Mr = 543.46

  • Triclinic, [P \overline 1]

  • a = 9.559 (4) Å

  • b = 9.656 (3) Å

  • c = 16.392 (6) Å

  • [alpha] = 78.584 (6)°

  • [beta] = 82.056 (6)°

  • [gamma] = 68.390 (6)°

  • V = 1375.3 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 296 K

  • 0.26 × 0.22 × 0.19 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.934, Tmax = 0.951

  • 6863 measured reflections

  • 4767 independent reflections

  • 3177 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.310

  • S = 1.08

  • 4767 reflections

  • 344 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.86 2.02 2.659 (5) 130
C4-H4...O2 0.98 2.30 2.761 (5) 108
C22-H22...O1i 0.93 2.69 3.287 (6) 122
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: 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: CV5409 ).


Acknowledgements

The authors gratefully acknowledge financial support by the Fundamental Research Funds for the Central Universities (grant No. 12CX04091A).

References

Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Khan, A. T., Parvin, T. & Choudhury, L. H. (2008). J. Org. Chem. 73, 8398-8402.  [CSD] [CrossRef] [PubMed] [ChemPort]
Kobayashi, S., Ueno, M., Suzuki, R., Ishitani, H., Kim, H. S. & Wataya, Y. (1999). J. Org. Chem. 64, 6833-6841.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Viegas, C., Bolzani, J. V. S., Furlan, M., Barreiro, E. J., Young, M. C. M., Tomazela, D. & Eberlin, M. N. (2004). J. Nat. Prod. 67, 908-910.  [ISI] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o947-o948   [ doi:10.1107/S1600536813013573 ]

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