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Volume 70 
Part 1 
Pages o22-o23  
January 2014  

Received 2 December 2013
Accepted 2 December 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.137
Data-to-parameter ratio = 17.9
Details
Open access

5''-Benzyl­idene-5-chloro-1',1''-dimethyl-4'-phenyl­dispiro­[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione

aSolid State Department, Physics Division, National Research Centre, Dokki, Giza, Egypt,bPesticide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt,cPhysics Department, Faculty of Science, Helwan University, Helwan, Cairo, Egypt, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The title compound, C30H28ClN3O2, features two spiro links, one connecting the piperidine and pyrrolidine rings, and the other connecting the pyrrolidine ring and indole residue. The configuration about the ethene bond is E. The piperidine ring adopts a half-chair conformation where the C atom connected to the spiro-C atom lies 0.713 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.086 Å). The pyrrolidine ring has an envelope conformation with the flap atom being the methyl­ene C atom. Centrosymmetric eight-membered {...HNCO}2 amide synthons feature in the crystal packing. These are consolidated into a three-dimensional architecture by phen­yl-pyrrolidine C-H...N and chloro­benzene-pyrrolidine-bound phenyl C-H...[pi] inter­actions.

Related literature

For the biological activity of related spiro­pyrrolidine analogues, see: Girgis et al. (2012[Girgis, A. S., Tala, S. R., Oliferenko, P. V., Oliferenko, A. A. & Katritzky, A. R. (2012). Eur. J. Med. Chem. 50 1-8.]); Kumar et al. (2008[Kumar, R. R., Perumal, S., Senthilkumar, P., Yoeeswair, P. & Sriram, D. (2008). J. Med. Chem. 51, 5731-5735.]). For related structural studies, see: Moustafa et al. (2012[Moustafa, A. M., Girgis, A. S., Shalaby, S. M. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2197-o2198.]). For the synthesis of the precursor mol­ecule, see: Al-Omary et al. (2012[Al-Omary, F. A. M., Hassan, G. S., El-Messery, S. M. & El-Subbagh, H. I. (2012). Eur. J. Med. Chem. 47, 65-72.]).

[Scheme 1]

Experimental

Crystal data
  • C30H28ClN3O2

  • Mr = 498.00

  • Monoclinic, P 21 /n

  • a = 10.5028 (3) Å

  • b = 20.4117 (6) Å

  • c = 11.9951 (4) Å

  • [beta] = 94.877 (1)°

  • V = 2562.20 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.52 × 0.22 × 0.15 mm

Data collection
  • Nonius 590 KappaCCD diffractometer

  • 10395 measured reflections

  • 5842 independent reflections

  • 2547 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.137

  • S = 0.94

  • 5842 reflections

  • 327 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C25-C30 ring.

D-H...A D-H H...A D...A D-H...A
N3-H3n...O2i 0.86 2.01 2.854 (3) 165
C14-H14...N2ii 0.93 2.58 3.480 (4) 163
C20-H20...Cg1iii 0.93 2.70 3.268 (3) 121
Symmetry codes: (i) -x+2, -y, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x+1, y, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5367 ).


Acknowledgements

This study was supported financially by the Science and Technology Development Fund (STDF), Egypt (grant No. 1133).

References

Al-Omary, F. A. M., Hassan, G. S., El-Messery, S. M. & El-Subbagh, H. I. (2012). Eur. J. Med. Chem. 47, 65-72.  [Web of Science] [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Girgis, A. S., Tala, S. R., Oliferenko, P. V., Oliferenko, A. A. & Katritzky, A. R. (2012). Eur. J. Med. Chem. 50 1-8.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Kumar, R. R., Perumal, S., Senthilkumar, P., Yoeeswair, P. & Sriram, D. (2008). J. Med. Chem. 51, 5731-5735.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Moustafa, A. M., Girgis, A. S., Shalaby, S. M. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2197-o2198.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o22-o23   [ doi:10.1107/S1600536813032765 ]

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