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Volume 68 
Part 12 
Pages o3327-o3328  
December 2012  

Received 11 September 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 14.5
Details
Open access

(5S,11aS)-5-Hydroperoxy-1,5,11,11a-tetrahydro[1]benzothieno[3,2-f]indolizin-3(2H)-one

aInstitute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and bInstitute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
Correspondence e-mail: viktor.vrabel@stuba.sk

The absolute configuration of the title compound, C14H13NO3S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviation from the mean plane of the ring being 0.661 (2) Å for the bridgehead C atom. The benzothiene ring attached to the indolizine ring system is planar to within 0.008 (2) Å. In the crystal, molecules form chains parallel to the b axis via O-H...O hydrogen bonds.

Related literature

For background to indolizines and their biological activity, 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.]); Sonnet et al. (2000[Sonnet, P., Dallemagne, P., Guillom, J., Engueard, C., Stiebing, S., Tangue, J., Bureau, B., Rault, S., Auvray, P., Moslemi, S., Sourdaine, P. & Seralini, G. E. (2000). Bioorg. Med. Chem. 8, 945-955.]); Campagna et al. (1990[Campagna, F., Carotti, A., Casini, G. & Macripo, M. (1990). Heterocycles, 31, 97-107.]); Pearson & Guo (2001[Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.]). For their synthesis, see: Safár et al. (2009a[Safár, P., Zúziová, J., Marchalín, S., Tóthová, E., Prónayová, N., Svorc, L., Vrábel, V. & Daich, A. (2009a). Tetrahedron Asymmetry, 20, 626-634.],b[Safár, P., Zúziová, J., Bobosíková, M., Marchalín, S., Prónayová, N., Comesse, S. & Daich, A. (2009b). Tetrahedron Asymmetry, 20, 2137-2144.]). For compounds with similar properties, see: Svorc et al. (2008[Svorc, L., Vrábel, V., Kozísek, J., Marchalín, S. & Safár, P. (2008). Acta Cryst. E64, o1164-o1165.], 2009[Svorc, L., Vrábel, V., Kozísek, J., Marchalín, S. & Safár, P. (2009). Acta Cryst. E65, o695-o696.]). For IR spectroscopy on similar compounds, see: Safár et al. (2009a[Safár, P., Zúziová, J., Marchalín, S., Tóthová, E., Prónayová, N., Svorc, L., Vrábel, V. & Daich, A. (2009a). Tetrahedron Asymmetry, 20, 626-634.]). For conformational analysis, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO3S

  • Mr = 275.31

  • Monoclinic, P 21

  • a = 7.8040 (5) Å

  • b = 7.9800 (4) Å

  • c = 10.2903 (5) Å

  • [beta] = 99.458 (5)°

  • V = 632.13 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 295 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur (Ruby, Gemi) diffractometer

  • Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.947, Tmax = 0.974

  • 21595 measured reflections

  • 2555 independent reflections

  • 2162 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.068

  • S = 1.00

  • 2555 reflections

  • 176 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1185 Friedel pairs

  • Flack parameter: -0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O1i 0.84 (1) 1.86 (1) 2.6962 (19) 173 (2)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); 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: DIAMOND, (Brandenburg, 2001[Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2481 ).


Acknowledgements

The authors thank the Grant Agency of Slovak Republic, Grant Nos. 1/0429/11, 1/0679/11 and the Slovak Research and Development Agency under contract Nos. APVV-0797-11 and APVV-0204-10 for financial support for this research program.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Campagna, F., Carotti, A., Casini, G. & Macripo, M. (1990). Heterocycles, 31, 97-107.  [CrossRef] [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.  [ISI] [CrossRef] [ChemPort]
Safár, P., Zúziová, J., Bobosíková, M., Marchalín, S., Prónayová, N., Comesse, S. & Daich, A. (2009b). Tetrahedron Asymmetry, 20, 2137-2144.
Safár, P., Zúziová, J., Marchalín, S., Tóthová, E., Prónayová, N., Svorc, L., Vrábel, V. & Daich, A. (2009a). Tetrahedron Asymmetry, 20, 626-634.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sonnet, P., Dallemagne, P., Guillom, J., Engueard, C., Stiebing, S., Tangue, J., Bureau, B., Rault, S., Auvray, P., Moslemi, S., Sourdaine, P. & Seralini, G. E. (2000). Bioorg. Med. Chem. 8, 945-955.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Svorc, L., Vrábel, V., Kozísek, J., Marchalín, S. & Safár, P. (2008). Acta Cryst. E64, o1164-o1165.  [CrossRef] [details]
Svorc, L., Vrábel, V., Kozísek, J., Marchalín, S. & Safár, P. (2009). Acta Cryst. E65, o695-o696.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3327-o3328   [ doi:10.1107/S1600536812045394 ]

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