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Volume 65 
Part 1 
Pages o147-o148  
January 2009  

Received 26 November 2008
Accepted 7 December 2008
Online 17 December 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.157
Data-to-parameter ratio = 13.9
Details
Open access

1-Benzyl-4',5'-diphenylpiperidine-3-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-4,2''-dione

aDepartment of Physics, The Madura College, Madurai 625011, India,bSchool of Chemistry, Madurai Kamaraj University, Madurai 625021, India, and cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: nilanthalakshman@yahoo.co.uk

The asymmetric unit of the title compound, C34H31N3O2, consists of two independent molecules which differ slightly in the orientations of the phenyl rings with respect to the pyrrolidine ring. In both molecules, the piperidin-4-one ring adopts a chair conformation, whereas the pyrrolidine ring adopts an envelope conformation in one of the molecules and a twisted conformation in the other. An intramolecular C-H...O hydrogen bond is observed. The crystal packing is stabilized by intermolecular N-H...O hydrogen bonds and C-H...[pi] interactions.

Related literature

For the biological activities of oxindole derivatives, see: Bhattacharya et al. (1982[Bhattacharya, S. K., Glover, V., McIntyre, I., Oxenkrug, G. & Sandler, M. (1982). Neurosci. Lett. 92, 218-221.]); Glover et al. (1998[Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem. 51, 656-659.]); Govind et al. (2004[Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54-o56.]); Hilton et al. (2000[Hilton, S. T., Ho, T. C., Pljevalijcic, G. & Jones, K. (2000). Org. Lett. 2, 17, 2639-2641.]); Jeyabharathi et al. (2001[Jeyabharathi, A., Ponnuswamy, M. N., Amal Raj, A., Raghunathan, R., Razak, I. A., Usman, A., Chantrapromma, S. & Fun, H.-K. (2001). Acta Cryst. E57, o901-o903.]); Kirsch et al. (2004[Kirsch, G., Hesse, S. & Comel, A. (2004). Curr. Org. Chem. 1, 47-63.]); Klumpp et al. (1998[Klumpp, D. A., Yeung, K. Y., Prakash, G. K. S. & Olah, G. A. (1998). J. Org. Chem. 63, 4481-4484.]); Kumar et al. (1993[Kumar, R., Bansal, R. C. & Mahmood, A. (1993). Biogenic Amines, 9, 281-289.], 2006[Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821-o4823.]); Medvedev et al. (1996[Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.]). For bond-length data, 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
  • C34H31N3O2

  • Mr = 513.62

  • Triclinic, [P \overline 1]

  • a = 10.8575 (3) Å

  • b = 13.7909 (5) Å

  • c = 20.5053 (9) Å

  • [alpha] = 89.767 (6)°

  • [beta] = 75.056 (4)°

  • [gamma] = 71.846 (3)°

  • V = 2809.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 (2) K

  • 0.17 × 0.13 × 0.11 mm

Data collection
  • Nonius MACH-3 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.988, Tmax = 0.992

  • 11592 measured reflections

  • 9879 independent reflections

  • 4342 reflections with I > 2[sigma](I)

  • Rint = 0.026

  • 2 standard reflections frequency: 60 min intensity decay: none

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

  • wR(F2) = 0.157

  • S = 0.99

  • 9879 reflections

  • 711 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O4 0.86 2.03 2.881 (3) 169
N6-H6...O2 0.86 2.05 2.896 (3) 170
C40-H40A...O4 0.97 2.35 2.925 (4) 118
C12-H12...Cg1i 0.93 2.80 3.586 (6) 144
Symmetry code: (i) x+1, y, z. Cg1 is the centroid of the C29-C34 ring.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2737 ).


Acknowledgements

SP thanks the CSIR for funding a major research project.

References

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.
Bhattacharya, S. K., Glover, V., McIntyre, I., Oxenkrug, G. & Sandler, M. (1982). Neurosci. Lett. 92, 218-221.  [CrossRef] [ISI]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem. 51, 656-659.  [CrossRef] [ISI]
Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54-o56.  [CrossRef] [details]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Hilton, S. T., Ho, T. C., Pljevalijcic, G. & Jones, K. (2000). Org. Lett. 2, 17, 2639-2641.
Jeyabharathi, A., Ponnuswamy, M. N., Amal Raj, A., Raghunathan, R., Razak, I. A., Usman, A., Chantrapromma, S. & Fun, H.-K. (2001). Acta Cryst. E57, o901-o903.  [CrossRef] [details]
Kirsch, G., Hesse, S. & Comel, A. (2004). Curr. Org. Chem. 1, 47-63.  [ChemPort]
Klumpp, D. A., Yeung, K. Y., Prakash, G. K. S. & Olah, G. A. (1998). J. Org. Chem. 63, 4481-4484.  [CrossRef] [ChemPort]
Kumar, R., Bansal, R. C. & Mahmood, A. (1993). Biogenic Amines, 9, 281-289.  [ChemPort]
Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821-o4823.  [CrossRef] [details]
Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.  [CrossRef] [ChemPort] [PubMed] [ISI]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2009). E65, o147-o148   [ doi:10.1107/S160053680804141X ]

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