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Volume 69 
Part 10 
Pages o1551-o1552  
October 2013  

Received 9 September 2013
Accepted 12 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.110
Data-to-parameter ratio = 15.1
Details
Open access

(3aR,6S,7aR)-7a-Chloro-2-[(4-nitrophenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

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

In the title compound, C14H13ClN2O5S, the chlorine-substituted tetrahydrofuran ring adopts a twist conformation and the other tetrahydrofuran ring an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts a twist conformation. In the crystal, C-H...O hydrogen bonds link the molecules into zigzag chains running along the b-axis direction.

Related literature

For Diels-Alder reactions, see: Winkler (1996[Winkler, J. D. (1996). Chem. Rev. 96, 167-176.]); Paulvannan (2004[Paulvannan, K. (2004). J. Org. Chem. 69, 1207-1214.]); Norton (1942[Norton, J. A. (1942). Chem. Rev. 31, 319-523.]); Fraile et al. (2001[Fraile, J. M., Garcia, J. I., Gómez, M. A., de la Hoz, A., Mayoral, J. A., Moreno, A., Prieto, P., Salvatella, L. & Vázquez, E. (2001). Eur. J. Org. Chem. pp. 2891-2899.]); Padwa et al. (2003[Padwa, A., Crawford, K. R., Rashatasakhon, P. & Rose, M. (2003). J. Org. Chem. 68, 2609-2617.]); Medimagh et al. (2008[Medimagh, R., Marque, S., Prim, D., Chatti, S. & Zarrouk, H. (2008). J. Org. Chem. 73, 2191-2198.]); Avalos et al. (2003[Avalos, M., Babiano, R., Cabello, N., Cintas, P., Hursthouse, M. B., Jiménez, J. L., Light, M. E. & Palacios, J. C. (2003). J. Org. Chem. 68, 7193-7203.]). For the thermal IMDA reaction of furan-cored compounds, see: Karaarslan & Demircan (2006[Karaarslan, M. & Demircan, A. (2006). Asian J. Chem. 18, 645-649.]); Kosar et al. (2006[Kosar, B., Demircan, A., Karaarslan, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o765-o767.], 2007[Kosar, B., Karaarslan, M., Yildiz, Y. K., Demircan, A. & Büyükgüngör, O. (2007). Acta Cryst. E63, o1169-o1170.], 2011[Kosar, B., Demircan, A., Arslan, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o994-o995.]); Arslan et al. (2008[Arslan, H., Demircan, A. & Göktürk, E. (2008). Spect. Chim. Act. Part A. A69, 105-112.]); Temel et al. (2012[Temel, E., Demircan, A., Beyazova, G. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1102-o1103.]). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13ClN2O5S

  • Mr = 356.77

  • Monoclinic, P 21 /c

  • a = 7.5193 (3) Å

  • b = 9.7278 (4) Å

  • c = 20.7616 (7) Å

  • [beta] = 93.659 (3)°

  • V = 1515.54 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 296 K

  • 0.68 × 0.63 × 0.60 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 = 0.811, Tmax = 0.850

  • 11192 measured reflections

  • 3151 independent reflections

  • 2494 reflections with I > 2[sigma](I)

  • Rint = 0.242

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.110

  • S = 1.03

  • 3151 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O4i 0.93 2.58 3.437 (3) 154
C14-H14B...O5ii 0.97 2.54 3.317 (2) 137
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6932 ).


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 (PN: 107 T831).

References

Arslan, H., Demircan, A. & Göktürk, E. (2008). Spect. Chim. Act. Part A. A69, 105-112.  [CrossRef]
Avalos, M., Babiano, R., Cabello, N., Cintas, P., Hursthouse, M. B., Jiménez, J. L., Light, M. E. & Palacios, J. C. (2003). J. Org. Chem. 68, 7193-7203.  [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [IUCr Journals]
Fraile, J. M., Garcia, J. I., Gómez, M. A., de la Hoz, A., Mayoral, J. A., Moreno, A., Prieto, P., Salvatella, L. & Vázquez, E. (2001). Eur. J. Org. Chem. pp. 2891-2899.  [CrossRef]
Karaarslan, M. & Demircan, A. (2006). Asian J. Chem. 18, 645-649.  [ChemPort]
Kosar, B., Demircan, A., Arslan, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o994-o995.  [CSD] [CrossRef] [IUCr Journals]
Kosar, B., Demircan, A., Karaarslan, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o765-o767.  [CSD] [CrossRef] [IUCr Journals]
Kosar, B., Karaarslan, M., Yildiz, Y. K., Demircan, A. & Büyükgüngör, O. (2007). Acta Cryst. E63, o1169-o1170.  [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]
Medimagh, R., Marque, S., Prim, D., Chatti, S. & Zarrouk, H. (2008). J. Org. Chem. 73, 2191-2198.  [CrossRef] [PubMed] [ChemPort]
Norton, J. A. (1942). Chem. Rev. 31, 319-523.  [CrossRef] [ChemPort]
Padwa, A., Crawford, K. R., Rashatasakhon, P. & Rose, M. (2003). J. Org. Chem. 68, 2609-2617.  [CrossRef] [PubMed] [ChemPort]
Paulvannan, K. (2004). J. Org. Chem. 69, 1207-1214.  [CSD] [CrossRef] [PubMed] [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., Beyazova, G. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1102-o1103.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Winkler, J. D. (1996). Chem. Rev. 96, 167-176.  [CrossRef] [PubMed] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1551-o1552   [ doi:10.1107/S1600536813025336 ]

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