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Volume 69 
Part 12 
Pages o1819-o1820  
December 2013  

Received 12 November 2013
Accepted 20 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.040
wR = 0.065
Data-to-parameter ratio = 13.2
Details
Open access

(11aS)-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,bInstitute of Mathematics and Physics, Faculty of Mechanical Engineering, Slovak University of Technologyy, Námestie slobody 17, SK-812 31 Bratislava, Slovak Republic,cInstitute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and dInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
Correspondence e-mail: viktor.vrabel@stuba.sk

The absolute configuration of the title compound, C14H13NOS, was assigned from the synthesis and confirmed by the structure determination. There are two independent mol­ecules in the asymmetric unit. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviations from the mean planes being 0.569 (3) and 0.561 (3) Å for the indolizine bridgehead C atoms of the two mol­ecules. The benzothieno ring attached to the indolizine ring system is planar to within 0.015 (3) Å in both mol­ecules. In the crystal, weak C-H...O and C-H...[pi] inter­actions lead to the formation of a three-dimensional framework structure.

Related literature

For background to indolizine derivatives, see: Gubin et al. (1992[Gubin, J., Lucchetti, J., Mahaux, J., Nisato, D., Rosseels, G., Clinet, M., Polster, P. & Chatelain, P. (1992). J. Med. Chem. 35, 981-988.]); Gupta et al. (2003[Gupta, S. P., Mathur, A. N., Nagappa, A. N., Kumar, D. & Kumaran, S. (2003). Eur. J. Med. Chem. 38, 867-873.]); Liu et al. (2007[Liu, Y., Song, Z. & Yan, B. (2007). Org. Lett. 9, 409-412.]); 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.]); Molyneux & James (1982[Molyneux, R. J. & James, L. F. (1982). Science, 216, 190-191.]); Nash et al. (1988[Nash, R. J., Fellows, L. E., Dring, J. V., Stirton, C. H., Carter, D., Hegarty, M. P. & Bell, E. A. (1988). Phytochemistry, 27, 1403-1406.]); Pearson & Guo (2001[Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.]); Ruprecht et al. (1989[Ruprecht, R. M., Mullaney, S., Andersen, J. & Bronson, R. (1989). J. Acquir. Immune Defic. Syndr. 2, 149-157.]); Smith et al. (2007[Smith, C. R., Bunnelle, E. M., Rhodes, A. J. & Sarpong, R. (2007). Org. Lett. 9, 1169-1171.]); Teklu et al. (2005[Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1362.]). For the synthesis, see: Safár et al. (2009[Safár, P., Zuziová, J., Marchalín, S., Tóthová, E., Prónayová, N., Svorc, L., Vrábel, V. & Daich, A. (2009). Tetrahedron Asymmetry, pp. 626-634.]). For a related structure, see: Vrábel et al. (2012[Vrábel, V., Svorc, L., Marchalín, S. & Safár, P. (2012). Acta Cryst. E68, o3327-o3328.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NOS

  • Mr = 243.31

  • Monoclinic, P 21

  • a = 9.3327 (8) Å

  • b = 12.4575 (7) Å

  • c = 10.3103 (7) Å

  • [beta] = 105.469 (8)°

  • V = 1155.27 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.15 mm

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

  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, , England.]) Tmin = 0.942, Tmax = 0.969

  • 17520 measured reflections

  • 4061 independent reflections

  • 2918 reflections with I > 2[sigma](I)

  • Rint = 0.093

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.065

  • S = 0.94

  • 4061 reflections

  • 307 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1923 Friedel pairs

  • Absolute structure parameter: -0.07 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg14 are the centroids of the C8-C13 and C22-C27 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C20-H20B...O2i 0.97 2.48 3.307 (4) 144
C3-H3B...Cg14 0.97 2.59 3.502 (3) 157
C17-H17A...Cg4 0.97 2.92 3.800 (4) 151
C29-H29B...Cg4ii 0.97 2.90 3.706 (3) 142
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+2]; (ii) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, , England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, , 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2001[Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2390 ).


Acknowledgements

The authors thank the Grant Agency of the Ministry of Education of the Slovak Republic, (grant Nos. 1/0429/11 and 1/0679/11) and the Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer. This work was supported by the Slovak Research and Development Agency under contract Nos. APVV-0797-11 and APVV-0204-10, and the Structural Funds, Inter­reg IIIA. This contribution is also the result of the project `Research Center for Industrial Synthesis of Drugs, ITMS 26240220061' supported by the Research & Development Operational Programme funded by the ERDF.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1362.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gubin, J., Lucchetti, J., Mahaux, J., Nisato, D., Rosseels, G., Clinet, M., Polster, P. & Chatelain, P. (1992). J. Med. Chem. 35, 981-988.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Gupta, S. P., Mathur, A. N., Nagappa, A. N., Kumar, D. & Kumaran, S. (2003). Eur. J. Med. Chem. 38, 867-873.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Liu, Y., Song, Z. & Yan, B. (2007). Org. Lett. 9, 409-412.  [Web of Science] [CSD] [CrossRef] [PubMed] [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]
Molyneux, R. J. & James, L. F. (1982). Science, 216, 190-191.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Nash, R. J., Fellows, L. E., Dring, J. V., Stirton, C. H., Carter, D., Hegarty, M. P. & Bell, E. A. (1988). Phytochemistry, 27, 1403-1406.  [CrossRef] [ChemPort] [Web of Science]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, , England.
Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.  [Web of Science] [CrossRef] [ChemPort]
Ruprecht, R. M., Mullaney, S., Andersen, J. & Bronson, R. (1989). J. Acquir. Immune Defic. Syndr. 2, 149-157.  [ChemPort] [PubMed]
Safár, P., Zuziová, J., Marchalín, S., Tóthová, E., Prónayová, N., Svorc, L., Vrábel, V. & Daich, A. (2009). Tetrahedron Asymmetry, pp. 626-634.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, C. R., Bunnelle, E. M., Rhodes, A. J. & Sarpong, R. (2007). Org. Lett. 9, 1169-1171.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.  [CrossRef] [PubMed] [ChemPort]
Vrábel, V., Svorc, L., Marchalín, S. & Safár, P. (2012). Acta Cryst. E68, o3327-o3328.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1819-o1820   [ doi:10.1107/S1600536813031693 ]

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