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Volume 69 
Part 4 
Pages o506-o507  
April 2013  

Received 15 February 2013
Accepted 4 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.062
wR = 0.133
Data-to-parameter ratio = 14.5
Details
Open access

Ethyl 2,6-bis(4-chlorophenyl)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-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: brahmg2001@yahoo.co.in, vivek_gupta2k2@hotmail.com

In the title compound, C32H26Cl2F2N2O2, the tetrahydropyridine ring adopts a distorted boat conformation. The chlorophenyl rings are inclined to one another by 55.2 (1)°, while for the fluorophenyl rings the dihedral angle is 80.7 (1)°. The amino group and carbonyl O atom are involved in an intramolecular N-H...O hydrogen bond. In the crystal, weak C-H...O, C-H...F and C-H...Cl interactions link the molecules into a three-dimensional network.

Related literature

For the biological activity of functionalized piperidine derivatives, see: Zhou et al. (2007[Zhou, Y., Gregor, V. E., Ayida, B. K., Winters, G. C., Sun, Z., Murphy, D., Haley, G., Bailey, D., Froelich, J. M., Fish, S., Webber, S. E., Hermann, T. & Wall, D. (2007). Bioorg. Med. Chem. Lett. 17, 1206-1210.]); Misra et al. (2009[Misra, M., Pandey, S. K., Pandey, V. P., Pandey, J., Tripathi, R. & Tripathi, R. P. (2009). Bioorg. Med. Chem. 17, 625-633.]); Bin et al. (2001[Bin, H., Crider, A. M. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 265-286.]); Agrawal & Somani (2009[Agrawal, A. G. & Somani, R. R. (2009). Mini Rev. Med. Chem. 9, 638-52.]); Dekus et al. (2007[Dekus, J. A., Epperson, J. R., Charles, P. S., Joseph, A. C., Deextraze, P., Qian- Cutrone, J., Gao, Q., Ma, B., Beno, B. R., Mattson, G. K., Molski, T. F., Krause, R. G., Taber, M. T., Lodge, N. J. & Mattson, R. (2007). Bioorg. Med. Chem. Lett. 17, 3099-3104.]). For general applications of densely functionalized piperidines, see: Targum et al. (1995[Targum, S., Zboroaski, J., Henry, M., Schmitz, P., Sebree, T. & Wallin, B. (1995). Eur. Neuropsychopharmacol. 5, 4-71.]); Schotte et al. (1996[Schotte, A., Janssen, P. F. M., Gommeren, W., Luyten, W. H. M. L., van Gompel, P., Lasage, A. S., De Loore, K. & Leysen, J. E. (1996). Psychopharmacology, 124, 57-73.]). For general background to functionalized piperidiones, 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.]); 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. G., Egan, A. & Keusch, G. T. (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.]); Anthal et al. (2013[Anthal, S., Brahmachari, G., Das, S., Kant, R. & Gupta, V. K. (2013). Acta Cryst. E69, o299-o300.]). For asymmetry parameters, 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
  • C32H26Cl2F2N2O2

  • Mr = 579.45

  • Triclinic, [P \overline 1]

  • a = 10.3074 (7) Å

  • b = 10.7942 (5) Å

  • c = 13.9432 (10) Å

  • [alpha] = 103.554 (5)°

  • [beta] = 106.487 (6)°

  • [gamma] = 96.846 (5)°

  • V = 1417.12 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.15 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 = 0.881, Tmax = 1.000

  • 10718 measured reflections

  • 5248 independent reflections

  • 2169 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.133

  • S = 0.93

  • 5248 reflections

  • 363 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.26 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 2.01 2.674 (4) 134
C9-H9C...Cl1i 0.96 2.67 3.523 (5) 148
C11-H11...O1ii 0.93 2.52 3.250 (5) 135
C18-H18...F1iii 0.93 2.52 3.259 (5) 137
C20-H20...F2iv 0.93 2.48 3.411 (4) 179
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z+1; (iii) x-1, y-1, z; (iv) -x-1, -y, -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: BG2498 ).


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

Agrawal, A. G. & Somani, R. R. (2009). Mini Rev. Med. Chem. 9, 638-52.  [CrossRef] [PubMed] [ChemPort]
Anthal, S., Brahmachari, G., Das, S., Kant, R. & Gupta, V. K. (2013). Acta Cryst. E69, o299-o300.  [CSD] [CrossRef] [details]
Bin, H., Crider, A. M. & Stables, J. P. (2001). Eur. J. Med. Chem. 36, 265-286.  [ISI] [PubMed]
Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479-1484.  [ISI] [CSD] [CrossRef] [ChemPort]
Breman, J. G., Egan, A. & Keusch, G. T. (2001). Am. J. Trop. Med. Hyg. 64, iv-vii.  [PubMed] [ChemPort]
Dekus, J. A., Epperson, J. R., Charles, P. S., Joseph, A. C., Deextraze, P., Qian- Cutrone, J., Gao, Q., Ma, B., Beno, B. R., Mattson, G. K., Molski, T. F., Krause, R. G., Taber, M. T., Lodge, N. J. & Mattson, R. (2007). Bioorg. Med. Chem. Lett. 17, 3099-3104.  [PubMed]
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]
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]
Misra, M., Pandey, S. K., Pandey, V. P., Pandey, J., Tripathi, R. & Tripathi, R. P. (2009). Bioorg. Med. Chem. 17, 625-633.  [CrossRef] [PubMed] [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]
Schotte, A., Janssen, P. F. M., Gommeren, W., Luyten, W. H. M. L., van Gompel, P., Lasage, A. S., De Loore, 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]
Targum, S., Zboroaski, J., Henry, M., Schmitz, P., Sebree, T. & Wallin, B. (1995). Eur. Neuropsychopharmacol. 5, 4-71.  [CrossRef]
Watson, P. S., Jiang, B. & Scott, B. (2000). Org. Lett. 2, 3679-3681.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhou, Y., Gregor, V. E., Ayida, B. K., Winters, G. C., Sun, Z., Murphy, D., Haley, G., Bailey, D., Froelich, J. M., Fish, S., Webber, S. E., Hermann, T. & Wall, D. (2007). Bioorg. Med. Chem. Lett. 17, 1206-1210.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o506-o507   [ doi:10.1107/S1600536813006090 ]

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