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Volume 69 
Part 4 
Page o466  
April 2013  

Received 11 February 2013
Accepted 25 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.090
Data-to-parameter ratio = 14.6
Details
Open access

(1'S,12'R,13'S,17'S)-15',15'-Dimethyl-1,2-dihydro-11',14',16',18'-tetraoxa-7'-azaspiro[indole-3,8'-pentacyclo[10.6.0.02,9.03,7.013,17]octadecane]-2,10'-dione

aDepartment of Physics, Presidency College, Chennai 600 005, India,bDepartment of Computer Science & Engineering, Madha Engineering College, Kundrathur, Chennai 600 069, India, and cDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C22H24N2O6, the indole ring has a twist conformation and the tetrahydro-2H-pyran-2-one ring a half-chair conformation. One of the pyrrolidine rings adopts an envelope conformation on the N atom, while the other has a twist conformation; the `butterfly' angle between their mean planes is 62.98 (11)°. The dioxolane ring adopts a twist conformation and the tetrahydrofuran ring has an envelope conformation on the C atom in the fused tetrahydro-2H-pyran-2-one ring adjacent to the O atom of the tetrahydrofuran ring. The `butterfly' angle between the mean planes of these two five-membered rings is 69.14 (10)°. In the crystal, molecules are linked by N-H...O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of indole derivatives, see: Stevenson et al. (2000[Stevenson, G. I., Smith, A. L., Lewis, S. G., Nedevelil, J. G., Patel, S., Marwood, R. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697-2704.]); Rajeswaran et al. (1999[Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369-1371.]); Amal Raj et al. (2003[Amal Raj, A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.]). For a related structure, see: Jagadeesan et al. (2012[Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012). Acta Cryst. E68, o2505-o2506.]).

[Scheme 1]

Experimental

Crystal data
  • C22H24N2O6

  • Mr = 412.43

  • Orthorhombic, P 21 21 21

  • a = 9.2737 (5) Å

  • b = 11.6543 (8) Å

  • c = 18.8489 (14) Å

  • V = 2037.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]) Tmin = 0.922, Tmax = 0.947

  • 21465 measured reflections

  • 4717 independent reflections

  • 3800 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.090

  • S = 1.04

  • 4717 reflections

  • 324 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.86 2.06 2.8849 (19) 161
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and 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: SU2563 ).


Acknowledgements

SA and VS thank the UGC, India, for financial support. The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Amal Raj, A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.  [PubMed]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012). Acta Cryst. E68, o2505-o2506.  [CSD] [CrossRef] [ChemPort] [details]
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369-1371.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stevenson, G. I., Smith, A. L., Lewis, S. G., Nedevelil, J. G., Patel, S., Marwood, R. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697-2704.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o466  [ doi:10.1107/S1600536813005436 ]

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