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Volume 69 
Part 2 
Pages o299-o300  
February 2013  

Received 12 December 2012
Accepted 22 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.167
Data-to-parameter ratio = 16.0
Details
Open access

Ethyl 4-anilino-2,6-bis(4-fluorophenyl)-1-phenyl-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 compound, C32H28F2N2O2, the tetrahydropyridine ring adopts a distorted boat conformation. The two fluorophenyl groups are attached to the tetrahydropyridine ring in a trans orientation. The dihedral angle between the planes of the fluoro-substituted rings is 57.0 (1)°. The amino group and carbonyl O atom are involved in intramolecular hydrogen bonding. In the crystal, weak C-H...O, C-H...F and C-H...[pi] interactions link the molecules into columns along [010].

Related literature

For the crystal structures of related densely functionalized piperidine derivatives, 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. (2008[Khan, T. K., Parvin, T. & Choudhury, L. H. (2008). J. Org. Chem. 73, 8398-8402.], 2010[Khan, T. K., Khan, Md. M. & Bannuru, K. K. R. (2010). Tetrahedron, 66, 7762-7772.]). For general background to functionalized piperidines, see: Desai et al. (1992[Desai, M. C., Lefkowitz, S. L., Thadeio, P. F., Longo, K. P. & Srider, R. M. (1992). J. Med. Chem. 35, 4911-4913.]). For applications of functionalized piperidines, see: Jaen et al. (1988[Jaen, J. C., Wise, L. D., Heffner, T. G., Pugsley, T. A. & Meltzer, L. T. (1988). J. Med. Chem. 31, 1621-1625.]); Schotte et al. (1996[Schotte, A., Janssen, P. F. M., Gommeren, W., Luyten, W. H. M. L., Gompel, P., Lasage, A. S., Loore, De. K. & Leysen, J. E. (1996). Psychopharmacology, 124, 57-73.]); Agrawal & Somani (2009[Agrawal, A. G. & Somani, R. R. (2009). Mini Rev. Med. Chem. 9, 638-52.]). For bond-length data in organic compounds, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C32H28F2N2O2

  • Mr = 510.56

  • Triclinic, [P \overline 1]

  • a = 10.0432 (4) Å

  • b = 10.4646 (4) Å

  • c = 13.9932 (6) Å

  • [alpha] = 105.422 (4)°

  • [beta] = 105.982 (4)°

  • [gamma] = 96.407 (4)°

  • V = 1335.53 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 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, Oxfordshire, England.]) Tmin = 0.846, Tmax = 1.000

  • 19971 measured reflections

  • 5521 independent reflections

  • 3372 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.167

  • S = 1.03

  • 5521 reflections

  • 344 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-H...A D-H H...A D...A D-H...A
N2-H2...O1 0.86 2.01 2.672 (3) 133
C11-H11...O1i 0.93 2.46 3.298 (3) 150
C9-H9A...F1ii 0.96 2.55 3.412 (3) 148
C26-H26...Cg1ii 0.93 2.66 3.470 (3) 146
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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 (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: CV5374 ).


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].

References

Agrawal, A. G. & Somani, R. R. (2009). Mini Rev. Med. Chem. 9, 638-52.  [CrossRef] [PubMed] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.  [ISI] [CSD] [CrossRef] [ChemPort]
Desai, M. C., Lefkowitz, S. L., Thadeio, P. F., Longo, K. P. & Srider, R. M. (1992). J. Med. Chem. 35, 4911-4913.  [CrossRef] [PubMed] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jaen, J. C., Wise, L. D., Heffner, T. G., Pugsley, T. A. & Meltzer, L. T. (1988). J. Med. Chem. 31, 1621-1625.  [CrossRef] [ChemPort] [PubMed]
Khan, T. K., Khan, Md. M. & Bannuru, K. K. R. (2010). Tetrahedron, 66, 7762-7772.  [ISI] [CSD] [CrossRef] [ChemPort]
Khan, T. K., Parvin, T. & Choudhury, L. H. (2008). J. Org. Chem. 73, 8398-8402.  [CSD] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sambyal, A., Bamezai, R. K., Razdan, T. K. & Gupta, V. K. (2011). J. Chem. Crystallogr. 41, 868-873.  [ISI] [CSD] [CrossRef] [ChemPort]
Schotte, A., Janssen, P. F. M., Gommeren, W., Luyten, W. H. M. L., Gompel, P., Lasage, A. S., Loore, De. K. & Leysen, J. E. (1996). Psychopharmacology, 124, 57-73.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o299-o300   [ doi:10.1107/S1600536813002158 ]

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