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Volume 69 
Part 2 
Pages o256-o257  
February 2013  

Received 28 December 2012
Accepted 11 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.066
wR = 0.183
Data-to-parameter ratio = 13.6
Details
Open access

5''-(4-Methoxybenzylidene)-1'-(4-methoxyphenyl)-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, C39H38N2O4, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by 0.3304 (1) and with the methylene C atom adjacent to the octahydroindolizine unit deviating by 0.444 (3) Å from the mean plane defined by the other four atoms. In the octahydroindolizine system, the pyrrolidine ring exhibits an envelope conformation, with the fused methyne C atom deviating by 0.6315 (1) Å from the mean plane defined by the other four atoms, and the piperidine ring exhibits a distorted chair conformation, as reflected in the puckering parameters Q = 0.568 (4) Å, [theta] = 1.5 (4) and [varphi] = 161 (16)°. In the crystal pairs of weak C-H...O interactions form centrosymmetric dimers, which are further connected by C-H...[pi] interactions. The crystal studied was a non-merohedral twin, with a domain ratio of 0.91:0.09.

Related literature

For general properties of indolizines, see: Weidner et al. (1989[Weidner, C. H., Wadsworth, D. H., Bender, S. L. & Beltman, D. J. (1989). J. Org. Chem. 54, 3660-3664.]); Katritzky et al. (1999[Katritzky, A. R., Qiu, G., Yang, B. & He, H.-Y. (1999). J. Org. Chem. 64, 7618-7621.]); Asano et al. (2000[Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymmetry, 11, 1645-1680.]); Gilchrist (2001[Gilchrist, T. L. (2001). J. Chem. Soc. Perkin Trans. 1, pp. 2491-2515.]); Sarkunam & Nallu (2005[Sarkunam, K. & Nallu, M. (2005). J. Heterocycl. Chem. 42, 5-11.]); Tielmann & Hoenke (2006[Tielmann, P. & Hoenke, C. (2006). Tetrahedron Lett. 47, 261-265.]); Oslund et al. (2008[Oslund, R. C., Cermak, N. & Gelb, M. H. (2008). J. Med. Chem. 51, 4708-4714.]); Vemula et al. (2011[Vemula, V. R., Vurukonda, S. & Bairi, C. K. (2011). Int. J. Pharm. Sci. Rev. Res. 11, 159-163.]); Singh & Mmatli (2011[Singh, G. S. & Mmatli, E. E. (2011). Eur. J. Med. Chem. 46, 5237-5257.]). For bond lengths and angles in a related structure, see: Suresh et al. (2011[Suresh, J., Vishnupriya, R., Kumar, R. R., Sivakumar, S. & Lakshman, P. L. N. (2011). Acta Cryst. E67, o3210.]). 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
  • C39H38N2O4

  • Mr = 598.71

  • Monoclinic, P 21 /n

  • a = 8.379 (5) Å

  • b = 16.958 (5) Å

  • c = 22.063 (5) Å

  • [beta] = 96.605 (5)°

  • V = 3114 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 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

  • 5537 measured reflections

  • 5537 independent reflections

  • 3900 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.183

  • S = 1.05

  • 5537 reflections

  • 407 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring (C52-C57) in the phenylmethylidene group.

D-H...A D-H H...A D...A D-H...A
C77-H77A...O2i 0.96 2.54 3.418 (5) 152
C58-H58C...Cg1ii 0.96 2.93 3.822 (5) 156
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z+1.

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: BH2471 ).


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

Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymmetry, 11, 1645-1680.  [ISI] [CrossRef] [ChemPort]
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]
Gilchrist, T. L. (2001). J. Chem. Soc. Perkin Trans. 1, pp. 2491-2515.  [CrossRef]
Katritzky, A. R., Qiu, G., Yang, B. & He, H.-Y. (1999). J. Org. Chem. 64, 7618-7621.  [CrossRef] [ChemPort]
Oslund, R. C., Cermak, N. & Gelb, M. H. (2008). J. Med. Chem. 51, 4708-4714.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sarkunam, K. & Nallu, M. (2005). J. Heterocycl. Chem. 42, 5-11.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, G. S. & Mmatli, E. E. (2011). Eur. J. Med. Chem. 46, 5237-5257.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suresh, J., Vishnupriya, R., Kumar, R. R., Sivakumar, S. & Lakshman, P. L. N. (2011). Acta Cryst. E67, o3210.  [CSD] [CrossRef] [details]
Tielmann, P. & Hoenke, C. (2006). Tetrahedron Lett. 47, 261-265.  [ISI] [CrossRef] [ChemPort]
Vemula, V. R., Vurukonda, S. & Bairi, C. K. (2011). Int. J. Pharm. Sci. Rev. Res. 11, 159-163.  [ChemPort]
Weidner, C. H., Wadsworth, D. H., Bender, S. L. & Beltman, D. J. (1989). J. Org. Chem. 54, 3660-3664.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o256-o257   [ doi:10.1107/S1600536813001177 ]

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