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Volume 69 
Part 1 
Pages o140-o141  
January 2013  

Received 25 November 2012
Accepted 17 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.126
Data-to-parameter ratio = 19.4
Details
Open access

rac-5''-(4-Fluorobenzylidene)-1'-(4-fluorophenyl)-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 E isomer of the racemic compound, C37H32F2N2O2, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by -0.355 (3) Å and with the methylene C atom next to octahydroindolizine moiety deviating by 0.415 (3) Å from the mean plane defined by other four atoms. In the octahydroindolizine system, the pyrrolidine ring exhibits an envelope conformation with the fused methyne C atom deviating by 0.6496 (1) Å from the mean plane defined by four other atoms, and the piperidine ring exhibits a distorted chair conformation as evident from the puckering parameters Q = 0.568 (2) Å, [theta] = 1.0 (2) and [Phi] = 256 (11)°. In the crystal, C-H...O interactions connect the molecules into chains along [101].

Related literature

For general properties of indolizines, see: Malonne et al. (1998[Malonne, H., Hanuise, J. & Fontaine, J. (1998). Pharm. Pharmacol. Commun. 4, 241-243.]); Medda et al. (2003[Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target. 11, 123-128.]); Pearson & Guo (2001[Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.]). 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
  • C37H32F2N2O2

  • Mr = 574.65

  • Monoclinic, P 21 /n

  • a = 10.2716 (4) Å

  • b = 20.0353 (7) Å

  • c = 14.3790 (6) Å

  • [beta] = 97.047 (1)°

  • V = 2936.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 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

  • 33177 measured reflections

  • 7519 independent reflections

  • 4823 reflections with I > 2[sigma](I)

  • Rint = 0.033

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

  • wR(F2) = 0.126

  • S = 1.01

  • 7519 reflections

  • 388 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11A...O1i 0.97 2.49 3.352 (2) 148
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: LD2088 ).


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]
Malonne, H., Hanuise, J. & Fontaine, J. (1998). Pharm. Pharmacol. Commun. 4, 241-243.  [ChemPort]
Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target. 11, 123-128.  [CrossRef] [PubMed] [ChemPort]
Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.  [ISI] [CrossRef] [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 (2013). E69, o140-o141   [ doi:10.1107/S1600536812051094 ]

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