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Volume 70 
Part 1 
Pages o43-o44  
January 2014  

Received 4 December 2013
Accepted 6 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.160
Data-to-parameter ratio = 18.3
Details
Open access

5-Chloro-5''-(4-chloro­benzyl­idene)-4'-(4-chloro­phen­yl)-1''-ethyl-1'-methyl­dispiro­[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

Two spiro links are found in the title compound, C31H28Cl3N3O2, one connecting the piperidine and pyrrolidine rings, and the other connecting the pyrrolidine ring and indole residue. The piperidine ring adopts a half-chair conformation, in which the C atom connected to the spiro-C atom lies 0.741 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.053 Å). The pyrrolidine ring has an envelope conformation with the flap atom being the methyl­ene C atom. Centrosymmetric eight-membered {...HNCO}2 amide dimers are the most significant feature of the crystal packing. These are connected into layers parallel to (-120) by C-H...O and [pi]-[pi] inter­actions between pyrrolidine-bound benzene rings [inter-centroid distance = 3.8348 (15) Å]. Slipped face-to-face inter­actions between the edges of pyrrolidine-bound benzene [shortest C...C separation = 3.484 (4) Å] connect the layers into a three-dimensional architecture.

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: Farag et al. (2013[Farag, I. S. A., Girgis, A. S., Ramadan, A. A., Moustafa, A. M. & Tiekink, E. R. T. (2014). Acta Cryst. E70, o22-o23.]). 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
  • C31H28Cl3N3O2

  • Mr = 580.91

  • Triclinic, [P \overline 1]

  • a = 11.1901 (2) Å

  • b = 11.6434 (3) Å

  • c = 12.4270 (3) Å

  • [alpha] = 99.477 (2)°

  • [beta] = 90.235 (2)°

  • [gamma] = 114.893 (1)°

  • V = 1443.77 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 293 K

  • 1.02 × 0.53 × 0.37 mm

Data collection
  • Nonius 590 KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.880, Tmax = 0.994

  • 11344 measured reflections

  • 6482 independent reflections

  • 4260 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.160

  • S = 1.00

  • 6482 reflections

  • 354 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.73 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3n...O2i 0.86 2.03 2.883 (3) 170
C31-H31...O1ii 0.93 2.47 3.160 (4) 131
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y, -z+1.

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: HB7170 ).


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.
Farag, I. S. A., Girgis, A. S., Ramadan, A. A., Moustafa, A. M. & Tiekink, E. R. T. (2014). Acta Cryst. E70, o22-o23.  [CSD] [CrossRef] [IUCr Journals]
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]
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. (1996). SADABS. University of Göttingen, Germany.
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, o43-o44   [ doi:10.1107/S1600536813033096 ]

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