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Volume 69 
Part 3 
Pages o454-o455  
March 2013  

Received 6 February 2013
Accepted 22 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.053
wR = 0.109
Data-to-parameter ratio = 14.6
Details
Open access

Ethyl 2,6-bis(4-chlorophenyl)-4-(4-methylanilino)-1-(4-methylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bLaboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati University, Santiniketan 731 235, West Bengal, India
Correspondence e-mail: vivek_gupta2k2@hotmail.com

In the title molecule, C34H32Cl2N2O2, the tetrahydropyridine ring adopts a distorted boat conformation and both 4-chlorophenyl substituents are in axial positions. An intramolecular N-H...O hydrogen bond is formed by the amino group and carbonyl O atom. In the crystal, weak C-H...Cl interactions link the molecules into chains along [010].

Related literature

For general background to functionalized piperidines, see: Pinder (1992[Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.]); Watson et al. (2000[Watson, P. S., Jiang, B. & Scott, B. (2000). Org. Lett. 2, 3679-3681.]); Breman et al. (2001[Breman, J., Egan, A. & Keusch, G. (2001). Am. J. Trop. Med. Hyg. 64, iv-vii.]); Kamei et al. (2005[Kamei, K., Maeda, N., Katswagi-Ogino, R., Koyamaa, M., Nakajima, M., Tatsuoka, T., Ohno, T. & Inoue, T. (2005). Bioorg. Med. Chem. Lett. 15, 2990-2993.]). For related structures, see: Sambyal et al. (2011[Sambyal, A., Bamezai, R. K., Razdan, T. K. & Gupta, V. K. (2011). J. Chem. Crystallogr. 41, 868-873.]); Brahmachari & Das (2012[Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.]); Khan et al. (2010[Khan, T. K., Khan, Md. M. & Bannuru, K. K. R. (2010). Tetrahedron, 66, 7762-7772.]); Anthal et al. (2013[Anthal, S., Brahmachari, G., Das, S., Kant, R. & Gupta, V. K. (2013). Acta Cryst. E69, o299-o300.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C34H32Cl2N2O2

  • Mr = 571.52

  • Triclinic, [P \overline 1]

  • a = 10.0851 (6) Å

  • b = 12.4340 (8) Å

  • c = 14.2414 (10) Å

  • [alpha] = 113.405 (6)°

  • [beta] = 102.233 (5)°

  • [gamma] = 101.194 (5)°

  • V = 1522.63 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.853, Tmax = 1.000

  • 13336 measured reflections

  • 5342 independent reflections

  • 2181 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.109

  • S = 0.89

  • 5342 reflections

  • 365 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 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
N2-H2...O1 0.86 2.10 2.707 (4) 127
C9-H9A...Cl2i 0.96 2.74 3.698 (4) 173
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2555 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. GB is thankful to the CSIR, New Delhi, for financial support [grant No. 02 (110)/12/EMR-II]. VKG is thankful to the University of Jammu, Jammu, for financial support.

References

Anthal, S., Brahmachari, G., Das, S., Kant, R. & Gupta, V. K. (2013). Acta Cryst. E69, o299-o300.  [CrossRef] [details]
Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.  [ISI] [CSD] [CrossRef] [ChemPort]
Breman, J., Egan, A. & Keusch, G. (2001). Am. J. Trop. Med. Hyg. 64, iv-vii.  [PubMed] [ChemPort]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kamei, K., Maeda, N., Katswagi-Ogino, R., Koyamaa, M., Nakajima, M., Tatsuoka, T., Ohno, T. & Inoue, T. (2005). Bioorg. Med. Chem. Lett. 15, 2990-2993.  [CrossRef] [PubMed] [ChemPort]
Khan, T. K., Khan, Md. M. & Bannuru, K. K. R. (2010). Tetrahedron, 66, 7762-7772.  [ISI] [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.  [CrossRef] [ChemPort]
Sambyal, A., Bamezai, R. K., Razdan, T. K. & Gupta, V. K. (2011). J. Chem. Crystallogr. 41, 868-873.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Watson, P. S., Jiang, B. & Scott, B. (2000). Org. Lett. 2, 3679-3681.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o454-o455   [ doi:10.1107/S1600536813005126 ]

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