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Volume 68 
Part 12 
Pages o3315-o3316  
December 2012  

Received 2 November 2012
Accepted 3 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 18.8
Details
Open access

5''-(4-Chlorobenzylidene)-1'-(4-chlorophenyl)-1''-methyl-1',2',3',5',6',7',8',8a'-octahydrodispiro[acenaphthylene-1,3'-indolizine-2',3''-piperidine]-2,4''(1H)-dione

aDepartment of Physics, The Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C37H32Cl2N2O2, the pyridinone ring adopts a twisted half-chair conformation. The fused pyrrolidine and piperidine rings of the octahydroindolizine unit exhibit envelope (with the C atom bound to the C atom bearing the chlorobenzene ring being the flap atom) and chair conformations, respectively. The dihedral angle between the chlorobenzene rings is 84.03 (1)°. In the crystal, C-H...[pi] interactions lead to supramolecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl...Cl [3.4065 (8) Å].

Related literature

For general properties of indolizines, see: Gundersen et al. (2007[Gundersen, L.-L., Charnock, C., Negussie, A. H., Rise, F. & Teklu, S. (2007). Eur. J. Pharm. Sci. 30, 26-35.]). For related structures, see: Sussman & Wodak (1973[Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918-2926.]); Wodak (1975[Wodak, S. J. (1975). Acta Cryst. B31, 569-573.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C37H32Cl2N2O2

  • Mr = 607.55

  • Monoclinic, P 21 /n

  • a = 14.1346 (5) Å

  • b = 15.2184 (6) Å

  • c = 14.5603 (6) Å

  • [beta] = 102.337 (1)°

  • V = 3059.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 32144 measured reflections

  • 7321 independent reflections

  • 4492 reflections with I > 2[sigma](I)

  • Rint = 0.041

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

  • wR(F2) = 0.113

  • S = 1.01

  • 7321 reflections

  • 389 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C52-C57 benzene ring.

D-H...A D-H H...A D...A D-H...A
C75-H75...Cg1i 0.93 2.88 3.669 (2) 144
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5167 ).


Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (grant No. SR/FT/CS-073/2009).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Gundersen, L.-L., Charnock, C., Negussie, A. H., Rise, F. & Teklu, S. (2007). Eur. J. Pharm. Sci. 30, 26-35.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918-2926.  [CrossRef] [ChemPort] [details] [ISI]
Wodak, S. J. (1975). Acta Cryst. B31, 569-573.  [CrossRef] [details] [ISI]


Acta Cryst (2012). E68, o3315-o3316   [ doi:10.1107/S160053681204545X ]

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