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Volume 69 
Part 12 
Page o1764  
December 2013  

Received 27 August 2013
Accepted 30 October 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.146
Data-to-parameter ratio = 20.0
Details
Open access

(4'-Acet­yloxy-1,3,1'-trioxo-1,3,4,4a,4b,5,6,7,9,9a-deca­hydro­spiro­[indene-2,9'-pyrano[4,3-a]pyrrolizin]-3'-yl)methyl acetate

aResearch Department of Physics, SDNB Vaishnav College for Women, Chennai 600 044, India, and bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: lakssdnbvc@gmail.com

In the title compound, C23H23NO8, the dihedral angle between the five- and six-membered rings of the indene-dione moiety is 3.09 (13)°. The mean plane of the five-membered ring (which has a flat envelope conformation with the spiro C atom as the flap) is inclined to the mean plane of the central five-membered ring of the pyrrolizine unit by 76.48 (12)°. This central ring has a twist conformation on the N-C(spiro) bond. The outer ring of the pyrrolizine unit has an envelope conformation with the N atom as the flap. The mean planes of these two fused rings are inclined to one another by 65.28 (15)°. The pyran ring has a screw-boat conformation and its mean plane makes a dihedral angle of 29.50 (11)° with the mean plane of the central five-membered ring of the pyrrolizine unit. In the crystal, mol­ecules are linked via C-H...O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

Related literature

For related structures, see: Gayathri et al. (2005[Gayathri, D., Aravindan, P. G., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2005). Acta Cryst. E61, o3124-o3126.]); Govind et al. (2004[Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54-o56.]); Kalyanasundaram et al. (2005[Kalyanasundaram, S., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Poornachandran, M. & Raghunathan, R. (2005). Acta Cryst. E61, o2158-o2160.]); Kumar et al. (2006[Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821-o4823.]); Satis Kumar et al. (2007[Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.]) Selvanayagam et al. (2005[Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jayashankaran, J. & Raghunathan, R. (2005). Acta Cryst. E61, o1582-o1584.]); Seshadri et al. (2003[Seshadri, P. R., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2003). Acta Cryst. E59, o1458-o1460.]).

[Scheme 1]

Experimental

Crystal data
  • C23H23NO8

  • Mr = 441.42

  • Orthorhombic, P 21 21 21

  • a = 10.4817 (4) Å

  • b = 13.4904 (5) Å

  • c = 15.1639 (5) Å

  • V = 2144.21 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.35 × 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 = 0.964, Tmax = 0.974

  • 15087 measured reflections

  • 5845 independent reflections

  • 4256 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.146

  • S = 1.03

  • 5845 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 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
C3-H3...O6i 0.93 2.59 3.401 (4) 147
C14-H14...O2ii 0.98 2.33 3.310 (3) 178
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

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: ZS2277 ).


References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gayathri, D., Aravindan, P. G., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2005). Acta Cryst. E61, o3124-o3126.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Govind, M. M., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2004). Acta Cryst. E60, o54-o56.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kalyanasundaram, S., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Poornachandran, M. & Raghunathan, R. (2005). Acta Cryst. E61, o2158-o2160.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kumar, R. G., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o4821-o4823.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.  [CSD] [CrossRef] [IUCr Journals]
Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jayashankaran, J. & Raghunathan, R. (2005). Acta Cryst. E61, o1582-o1584.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Seshadri, P. R., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Sureshbabu, A. R. & Raghunathan, R. (2003). Acta Cryst. E59, o1458-o1460.  [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]


Acta Cryst (2013). E69, o1764  [ doi:10.1107/S1600536813029826 ]

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