[Journal logo]

Volume 69 
Part 7 
Page o1041  
July 2013  

Received 26 May 2013
Accepted 29 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.069
wR = 0.174
Data-to-parameter ratio = 13.9
Details
Open access

4-(5-{2-[5-(4-Cyanophenyl)-3-methylthiophen-2-yl]-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl}-4-methylthiophen-2-yl)benzonitrile chloroform hemisolvate

aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
Correspondence e-mail: gelhiti@ksu.edu.sa

The crystal structure of the title compound, C29H16F6N2S2·0.5CHCl3, consists of molecules with disordered perfluorocyclopentene rings [occupancy ratio 0.685 (3):0.315 (3)] and close F...F contacts (in the range 2.45-2.73 Å) between molecules. The short contacts are associated with the disorder. The dihedral angle between thiophene rings is 57.44 (8)°. The 5-(4-cyanophenyl)-3-methyl-2-thienyl groups of adjacent molecules are parallel, leading to zigzag chains of molecules along [101]. The dihedral angles between each thiophene ring and its adjacent cyanobenzene ring are 8.9 (2) and 7.15 (10)°.

Related literature

For applications of substituted thienylperfluorocyclopentenes as switches, see: Waldeck (1991[Waldeck, D. H. (1991). Chem. Rev. 91, 415-436.]); Pu et al. (2006[Pu, S., Zhang, F., Xu, J., Shen, L., Xiao, Q. & Chen, B. (2006). Mater. Lett. 60, 485-489.]); Dulic et al. (2007[Dulic, D., Kudernac, T., Puzys, A., Feringa, B. L. & Wees, B. J. (2007). Adv. Mater. 19, 2898-2902.]). For related structures, see: Irie et al. (1995[Irie, M., Sakemura, K., Okinaka, M. & Uchida, K. (1995). J. Org. Chem. 1995, 60, 8305-8309.], 2000[Irie, M., Lifka, T., Kobatake, S. & Kato, N. (2000). J. Am. Chem. Soc. 122, 4871-4876.]); Morimitsu et al. (2002[Morimitsu, K., Shibata, K., Kobatake, S. & Irie, M. (2002). J. Org. Chem. 67, 4574-4578.]); Mori et al. (2011[Mori, K., Ishibashi, Y., Mastsuda, H., Ito, S., Nagasawa, Y., Nakagawa, H., Uchida, K., Yokojima, S., Nakamura, S., Irie, M. & Miyasaka, H. (2011). J. Am. Chem. Soc. 133, 2621-2625.]).

[Scheme 1]

Experimental

Crystal data
  • C29H16F6N2S2·0.5CHCl3

  • Mr = 630.24

  • Monoclinic, C 2/c

  • a = 18.4237 (4) Å

  • b = 15.7594 (6) Å

  • c = 20.9299 (7) Å

  • [beta] = 113.280 (2)°

  • V = 5582.2 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.40 mm-1

  • T = 150 K

  • 0.40 × 0.30 × 0.30 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.857, Tmax = 0.890

  • 10636 measured reflections

  • 6329 independent reflections

  • 4168 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.174

  • S = 1.04

  • 6329 reflections

  • 455 parameters

  • 92 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; 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: ORTEP99 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2111 ).


Acknowledgements

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through research group project RGP-VPP-239.

References

Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.
Dulic, D., Kudernac, T., Puzys, A., Feringa, B. L. & Wees, B. J. (2007). Adv. Mater. 19, 2898-2902.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Irie, M., Lifka, T., Kobatake, S. & Kato, N. (2000). J. Am. Chem. Soc. 122, 4871-4876.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Irie, M., Sakemura, K., Okinaka, M. & Uchida, K. (1995). J. Org. Chem. 1995, 60, 8305-8309.
Mori, K., Ishibashi, Y., Mastsuda, H., Ito, S., Nagasawa, Y., Nakagawa, H., Uchida, K., Yokojima, S., Nakamura, S., Irie, M. & Miyasaka, H. (2011). J. Am. Chem. Soc. 133, 2621-2625.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Morimitsu, K., Shibata, K., Kobatake, S. & Irie, M. (2002). J. Org. Chem. 67, 4574-4578.  [CrossRef] [PubMed] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pu, S., Zhang, F., Xu, J., Shen, L., Xiao, Q. & Chen, B. (2006). Mater. Lett. 60, 485-489.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Waldeck, D. H. (1991). Chem. Rev. 91, 415-436.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1041  [ doi:10.1107/S1600536813014852 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.