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Volume 68 
Part 12 
Page o3437  
December 2012  

Received 29 October 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.167
Data-to-parameter ratio = 18.1
Details
Open access

2,5-Dihexylthiophene 1,1-dioxide

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: nagagold@gmail.com

In the title molecule, C16H28O2S, the two n-hexyl groups are in all-trans conformations. Their C atoms are situated close to the plane of the thiophene ring with a maximum deviation of 0.718 (6) Å for one of the terminal methyl groups. In the crystal, a short C-H...O contact is observed between thiophene 1,1-dioxide groups.

Related literature

For the preparation of the title compound, see: Barbarella et al. (1998[Barbarella, G., Favaretto, L., Sotgiu, G., Zambianchi, M., Antolini, L., Pudova, O. & Bongini, A. (1998). J. Org. Chem. 63, 5497-5506.]). For a review on thiophene-1,1-dioxide derivatives and their applications, see: Nakayama et al. (1999[Nakayama, J. & Sugihara, Y. (1999). Top. Curr. Chem. 205, 131-195.]). For the biological activity of sulfone compounds, see: Naesens et al. (2006[Naesens, L., Stephens, C. E., Andrei, G., Loregian, A., De Bolle, L., Snoeck, R., Sowell, J. W. & De Clercq, E. (2006). Antivir. Res. 72, 60-67.]); Kim et al. (2008[Kim, S. H., Tran, M. T., Ruebsam, F., Xiang, A. X., Ayida, B., McGuire, H., Ellis, D., Blazel, J., Tran, C. V., Murphy, D. E., Webber, S. E., Zhou, Y., Shah, A. M., Tsan, M., Showalter, R. E., Patel, R., Gobbi, A., LeBrun, L. A., Bartkowski, D. M., Nolan, T. G., Norris, D. A., Sergeeva, M. V., Kirkovsky, L., Zhao, Q., Han, Q. & Kissinger, C. R. (2008). Bioorg. Med. Chem. Lett. 18, 4181-4185.]); Sagardoy et al. (2010[Sagardoy, A. A., Gil, M. J., Villar, R., Viñas, M., Arrazola, A., Encío, I. & Martinez-Merino, V. (2010). Bioorg. Med. Chem. 18, 5701-5707.]).

[Scheme 1]

Experimental

Crystal data
  • C16H28O2S

  • Mr = 284.44

  • Monoclinic, P 21 /n

  • a = 5.8249 (11) Å

  • b = 11.248 (2) Å

  • c = 27.207 (6) Å

  • [beta] = 91.770 (8)°

  • V = 1781.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 1.00 × 0.30 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA.]) Tmin = 0.841, Tmax = 0.982

  • 18944 measured reflections

  • 3149 independent reflections

  • 2207 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.167

  • S = 1.07

  • 3149 reflections

  • 174 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.93 2.54 3.186 (3) 126
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2532 ).


Acknowledgements

The University of the Free State and Sasol Ltd are gratefully acknowledged for the financial support. Special thanks to Professor Andreas Roodt.

References

Barbarella, G., Favaretto, L., Sotgiu, G., Zambianchi, M., Antolini, L., Pudova, O. & Bongini, A. (1998). J. Org. Chem. 63, 5497-5506.  [CSD] [CrossRef] [ChemPort]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kim, S. H., Tran, M. T., Ruebsam, F., Xiang, A. X., Ayida, B., McGuire, H., Ellis, D., Blazel, J., Tran, C. V., Murphy, D. E., Webber, S. E., Zhou, Y., Shah, A. M., Tsan, M., Showalter, R. E., Patel, R., Gobbi, A., LeBrun, L. A., Bartkowski, D. M., Nolan, T. G., Norris, D. A., Sergeeva, M. V., Kirkovsky, L., Zhao, Q., Han, Q. & Kissinger, C. R. (2008). Bioorg. Med. Chem. Lett. 18, 4181-4185.  [CrossRef] [PubMed] [ChemPort]
Naesens, L., Stephens, C. E., Andrei, G., Loregian, A., De Bolle, L., Snoeck, R., Sowell, J. W. & De Clercq, E. (2006). Antivir. Res. 72, 60-67.  [CrossRef] [PubMed] [ChemPort]
Nakayama, J. & Sugihara, Y. (1999). Top. Curr. Chem. 205, 131-195.  [CrossRef] [ChemPort]
Sagardoy, A. A., Gil, M. J., Villar, R., Viñas, M., Arrazola, A., Encío, I. & Martinez-Merino, V. (2010). Bioorg. Med. Chem. 18, 5701-5707.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3437  [ doi:10.1107/S1600536812046867 ]

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