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

Suresh, J.; Kumar, R.S.; Rajapriya, A.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S160053680804141X

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 (C-C) = 0.005 Å
R = 0.053
wR = 0.157
Data-to-parameter ratio = 13.9
Details

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

J. Suresh,^a R. Suresh Kumar,^b A. Rajapriya,^a S. Perumal ^b and P. L. Nilantha Lakshman ^c ^*

^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-HO hydrogen bond is observed. The crystal packing is stabilized by intermolecular N-HO hydrogen bonds and C-H [pi] interactions.

Related literature

For the biological activities of oxindole derivatives, see: Bhattacharya et al. (1982); Glover et al. (1998); Govind et al. (2004); Hilton et al. (2000); Jeyabharathi et al. (2001); Kirsch et al. (2004); Klumpp et al. (1998); Kumar et al. (1993, 2006); Medvedev et al. (1996). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₃₄H₃₁N₃O₂
M_r = 513.62
Triclinic, $[P \overline 1]$
a = 10.8575 (3) Å
b = 13.7909 (5) Å
c = 20.5053 (9) Å
= 89.767 (6)°
= 75.056 (4)°
= 71.846 (3)°
V = 2809.1 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.17 × 0.13 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.988, T_max = 0.992
11592 measured reflections
9879 independent reflections
4342 reflections with I > 2(I)
R_int = 0.026
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2(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
_max = 0.26 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O4	0.86	2.03	2.881 (3)	169
N6-H6O2	0.86	2.05	2.896 (3)	170
C40-H40AO4	0.97	2.35	2.925 (4)	118
C12-H12Cg1ⁱ	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); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); 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

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organic compounds