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Volume 69 
Part 11 
Pages o1628-o1629  
November 2013  

Received 20 September 2013
Accepted 23 September 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.068
wR = 0.192
Data-to-parameter ratio = 15.9
Details
Open access

(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro­phenyl­sulfon­yl)-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­oxy­iso­indole

aDepartment of Chemistry, Faculty of Arts and Sciences, Nigde University, TR-51240 Nigde, Turkey, and bOndokuz Mayis University, Arts and Sciences Faculty, Department of Physics, TR-55139 Samsun, Turkey
Correspondence e-mail: etemel@omu.edu.tr

In the title compound, C15H15ClN2O5S, the tetra­hydro­furan ring adopts an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts an envelope conformation with the chlorine-substituted C atom as the flap. In the crystal, two types of C-H...O hydrogen bonds generate R22(20) and R44(26) rings, with adjacent rings running parallel to ac plane. Further C-H...O hydrogen bonds form a C(6) chain, linking the mol­ecules in the b-axis direction.

Related literature

For chemical background to protecting groups, see: Greene & Wuts (1999[Greene, T. W. & Wuts, P. G. M. (1999). Protective Groups in Organic Synthesis, 3rd ed. New York: John Wiley & Sons, Inc.]); Romanski et al. (2012[Romanski, J., Nowak, P., Kosinski, K. & Jurczak, J. (2012). Tetrahedron Lett. 53, 5287-5289.]); Chan & White (2004[Chan, W. C. & White, P. D. (2004). In Fmoc Solid Phase Peptide Synthesis. Oxford University Press.]); Yasushi & Higuchi (2006[Yasushi, K. & Higuchi, T. (2006). FEMS Microbiol. Lett. 24, 225-229.]); Blanc & Bochet (2007[Blanc, A. & Bochet, C. G. (2007). Org. Lett. 9, 2649-2651.]); Demircan & Parsons (2002[Demircan, A. & Parsons, P. J. (2002). Heterocycl. Commun. 8, 531-536.]); Demirtas et al. (2002[Demirtas, I., Büyükkidan, B. & Elmastas, M. (2002). Turk. J. Chem. 26, 889-896.]); Katritzky et al. (2004[Katritzky, A. R., Hoffmann, S. & Suzuki, K. (2004). Arkivoc, xii, 14-22.]); Merlin et al. (1988[Merlin, P., Braekman, J. C. & Daloze, D. (1988). Tetrahedron Lett. 29, 1691-1694.]); Büyükgüngör et al. (2005[Büyükgüngör, O., Kosar, B., Demircan, A. & Turaç, E. (2005). Acta Cryst. E61, o1441-o1442.]); Kosar et al. (2006a[Kosar, B., Demircan, A., Karaarslan, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o765-o767.],b[Kosar, B., Göktürk, E., Demircan, A. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o4192-o4193.]); Karaarslan et al. (2007[Karaarslan, M., Göktürk, E. & Demircan, A. (2007). J. Chem. Res. 2, 117-120.]); Demircan et al. (2011[Demircan, A., Sahin, E., Beyazova, G., Karaaslan, M. & Hökelek, T. (2011). Acta Cryst. E67, o1085-o1086.]); Temel et al. (2011[Temel, E., Demircan, A., Arslan, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o1304-o1305.], 2012[Temel, E., Demircan, A., Beyazova, G. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1102-o1103.]). For puckering parameters, see: Cremer & Pople, (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15ClN2O5S

  • Mr = 370.80

  • Monoclinic, P 21 /c

  • a = 8.6049 (5) Å

  • b = 7.1949 (3) Å

  • c = 26.8195 (15) Å

  • [beta] = 101.186 (4)°

  • V = 1628.89 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.39 mm-1

  • T = 296 K

  • 0.48 × 0.24 × 0.02 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.894, Tmax = 0.992

  • 13941 measured reflections

  • 3449 independent reflections

  • 1564 reflections with I > 2[sigma](I)

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.192

  • S = 0.89

  • 3449 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.12 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O3i 0.93 2.46 3.205 (6) 138
C7-H7A...O2ii 0.97 2.51 3.219 (6) 129
C9-H9...O4iii 0.93 2.52 3.388 (6) 155
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z+1; (iii) x+1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6935 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the diffractometer (purchased under grant F.279 of University Research Fund) and also The Scientific & Technological Research Council of Turkey (TÜBITAK) for the financial support of this work (P·N.: 107 T831).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Blanc, A. & Bochet, C. G. (2007). Org. Lett. 9, 2649-2651.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Büyükgüngör, O., Kosar, B., Demircan, A. & Turaç, E. (2005). Acta Cryst. E61, o1441-o1442.  [CSD] [CrossRef] [IUCr Journals]
Chan, W. C. & White, P. D. (2004). In Fmoc Solid Phase Peptide Synthesis. Oxford University Press.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Demircan, A. & Parsons, P. J. (2002). Heterocycl. Commun. 8, 531-536.  [ChemPort]
Demircan, A., Sahin, E., Beyazova, G., Karaaslan, M. & Hökelek, T. (2011). Acta Cryst. E67, o1085-o1086.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Demirtas, I., Büyükkidan, B. & Elmastas, M. (2002). Turk. J. Chem. 26, 889-896.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Greene, T. W. & Wuts, P. G. M. (1999). Protective Groups in Organic Synthesis, 3rd ed. New York: John Wiley & Sons, Inc.
Karaarslan, M., Göktürk, E. & Demircan, A. (2007). J. Chem. Res. 2, 117-120.  [CrossRef]
Katritzky, A. R., Hoffmann, S. & Suzuki, K. (2004). Arkivoc, xii, 14-22.  [CrossRef]
Kosar, B., Demircan, A., Karaarslan, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o765-o767.  [CSD] [CrossRef] [IUCr Journals]
Kosar, B., Göktürk, E., Demircan, A. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o4192-o4193.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Merlin, P., Braekman, J. C. & Daloze, D. (1988). Tetrahedron Lett. 29, 1691-1694.  [CrossRef] [ChemPort] [Web of Science]
Romanski, J., Nowak, P., Kosinski, K. & Jurczak, J. (2012). Tetrahedron Lett. 53, 5287-5289.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Temel, E., Demircan, A., Arslan, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o1304-o1305.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Temel, E., Demircan, A., Beyazova, G. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1102-o1103.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Yasushi, K. & Higuchi, T. (2006). FEMS Microbiol. Lett. 24, 225-229.


Acta Cryst (2013). E69, o1628-o1629   [ doi:10.1107/S1600536813026329 ]

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