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Volume 69 
Part 11 
Page o1601  
November 2013  

Received 27 August 2013
Accepted 21 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.042
wR = 0.104
Data-to-parameter ratio = 10.9
Details
Open access

(1S,1'S,2'R,4a'S,9a'S,9b'R)-1'-Acet­yloxy-2,4'-dioxo-2',4',4a',7',8',9',9a',9b'-octa­hydro-1'H,2H-spiro­[ace­naphthyl­ene-1,5'-pyrano[4,3-a]pyrrolizin]-2'-ylmethyl acetate

aResearch Department of Physics, SDNB Vaishnav College for Women, Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Guindy, Chennai 600 025, India
Correspondence e-mail: lakssdnbvc@gmail.com

In the title compound C26H25NO7, the mean plane through the lactone-substituted ring of the pyrrolizidine moiety forms dihedral angles of 78.46 (6) and 58.28 (8)° with the ace­naphthyl­ene moiety and the sugar based-lactone ring, respectively. The sum of the angles at the the N atom of the pyrrolizidine ring (335.0°) is in accordance with sp3 hybridization. Some atoms of the acetate group are disordered and were refined using a split model [occupancy ratio 0.673 (10):0.327 (10)].

Related literature

For the importance of pyrrolidine and pyrrolizidine compounds and background to this work, see: Boido et al. (1994[Boido, A., Vazzana, I. & Sparatore, F. (1994). Il Farmaco, 49, 97-104.]); Cravotto et al. (2001[Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.]); Gershbein (1975[Gershbein, L. L. (1975). Res. Commun. Chem. Pathol. Pharmacol. 11, 445-466.]); Govind et al. (2003[Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sridhar, G. & Raghunathan, R. (2003). Acta Cryst. E59, o1680-o1681.]); Jellimann et al. (2000[Jellimann, C., Allainmat, M., Andrieux, J., Kloubert, S., Boutin, J. A., Nicolas, J. P., Bennejean, C., Delagrange, P. & Langlois, M. (2000). J. Med. Chem. 43, 4051-4062.]); Nishimura et al. (1985[Nishimura, Y., Kondo, S. & Umezawa, H. (1985). J. Org. Chem. 50, 5210-5214.]); Selvanayagam et al. (2004[Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jayashankaran, J., Durga, R. R. & Raghunathan, R. (2004). Acta Cryst. E60, o2216-o2218.]); Usha et al. (2005[Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Durga, R. R. & Raghunathan, R. (2005). Acta Cryst. E61, o2267-o2269.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25NO7

  • Mr = 463.47

  • Tetragonal, P 43 21 2

  • a = 13.6792 (3) Å

  • c = 24.9625 (13) Å

  • V = 4671.0 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.902, Tmax = 0.976

  • 21173 measured reflections

  • 4010 independent reflections

  • 2923 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.104

  • S = 1.06

  • 4010 reflections

  • 367 parameters

  • 138 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2316 ).


References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Boido, A., Vazzana, I. & Sparatore, F. (1994). Il Farmaco, 49, 97-104.  [ChemPort] [PubMed]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.  [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gershbein, L. L. (1975). Res. Commun. Chem. Pathol. Pharmacol. 11, 445-466.  [PubMed] [ChemPort]
Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sridhar, G. & Raghunathan, R. (2003). Acta Cryst. E59, o1680-o1681.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Jellimann, C., Allainmat, M., Andrieux, J., Kloubert, S., Boutin, J. A., Nicolas, J. P., Bennejean, C., Delagrange, P. & Langlois, M. (2000). J. Med. Chem. 43, 4051-4062.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Nishimura, Y., Kondo, S. & Umezawa, H. (1985). J. Org. Chem. 50, 5210-5214.  [CrossRef] [ChemPort]
Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jayashankaran, J., Durga, R. R. & Raghunathan, R. (2004). Acta Cryst. E60, o2216-o2218.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Durga, R. R. & Raghunathan, R. (2005). Acta Cryst. E61, o2267-o2269.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1601  [ doi:10.1107/S1600536813026111 ]

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