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Volume 69 
Part 3 
Pages o373-o374  
March 2013  

Received 24 January 2013
Accepted 6 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.118
Data-to-parameter ratio = 15.3
Details
Open access

Methyl 4-(4-fluoroanilino)-1,2,6-tris(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: vivek_gupta2k2@hotmail.com

In the title molecule, C31H24F4N2O2, the tetrahydropyridine ring adopts a distorted boat conformation. An intramolecular N-H...O hydrogen bond is formed by the amino group and ccarboxyl C=O atom. The crystal structure features weak C-H...F and C-H...O interactions.

Related literature

For 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, 638-652.]); 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.]). For general background to functionalized piperidines, see: 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 asymmetry parameters, see: Duax et al. (1975[Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C31H24F4N2O2

  • Mr = 532.52

  • Triclinic, [P \overline 1]

  • a = 9.7990 (2) Å

  • b = 10.7316 (4) Å

  • c = 13.7395 (4) Å

  • [alpha] = 110.797 (3)°

  • [beta] = 100.338 (2)°

  • [gamma] = 96.323 (2)°

  • V = 1304.81 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.899, Tmax = 1.000

  • 42990 measured reflections

  • 5413 independent reflections

  • 3730 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.118

  • S = 1.05

  • 5413 reflections

  • 353 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N9-H9...O1 0.86 2.05 2.695 (2) 131
C20-H20...F2i 0.93 2.54 3.384 (2) 152
C32-H32...O1ii 0.93 2.47 3.311 (3) 151
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x, -y, -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 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: GK2551 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for a 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 thanks the University of Jammu for financial support.

References

Agrawal, A. G. & Somani, R. R. (2009). Mini Rev. Med. Chem. 9, 638-652.  [CrossRef] [PubMed] [ChemPort]
Anthal, S., Brahmachari, G., Das, S., Kant, R. & Gupta, V. K. (2013). Acta Cryst. E69, o299-o300.  [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]
Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
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]
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]
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, Oxfordshire, England.
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]
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, o373-o374   [ doi:10.1107/S160053681300370X ]

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