1,2-Bis[5-(2,2′-dicyano­vinyl)-2-n-pentyl-3-thien­yl]-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-ene: a new photochromic diaryl­ethene compound

Li, M.; Pu, S.-Z.; Fan, C.-B.; Le, Z.-G.

doi:10.1107/S160053680800202X

Volume 64
Part 2
Page o517
February 2008

Received 24 December 2007
Accepted 19 January 2008
Online 25 January 2008

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.050
wR = 0.143
Data-to-parameter ratio = 15.2
Details

1,2-Bis[5-(2,2'-dicyanovinyl)-2-n-pentyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene: a new photochromic diarylethene compound

Min Li,^a,^b Shou-Zhi Pu,^b ^* Cong-Bin Fan ^b and Zhang-Gao Le ^a

^aKey Laboratory of Nuclear Resources and Environment of the Ministry of Education, East China Institute of Technology, Fuzhou 344000, People's Republic of China, and ^bJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China
Correspondence e-mail: pushouzhi@tsinghua.org.cn

The title compound, C₃₁H₂₆F₆N₄S₂, is a new photochromic dithienylethene with dicyanovinyl subsitituents. In the crystal structure, the molecule adopts a photoactive antiparallel conformation, with two n-pentyl groups located on opposite sides of the cyclopentene ring. The cyclopentene ring assumes an envelope conformation. The distance between the two reactive C atoms on the thiophene rings is 3.834 (7) Å. One of the n-pentyl groups is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Related literature

For general background, see: Gilat et al. (1993, 1995); Irie (2000); Pu et al. (2003, 2005); Tian & Yang (2004); Yamaguchi & Irie (2006); Zheng et al. (2007). For related structures, see: Kobatake et al. (2004); Woodward & Hoffmann (1970).

Experimental

Crystal data

C₃₁H₂₆F₆N₄S₂
M_r = 632.68
Triclinic, $[P \overline 1]$
a = 9.2500 (12) Å
b = 12.3670 (16) Å
c = 15.596 (2) Å
= 67.730 (2)°
= 85.482 (2)°
= 72.804 (2)°
V = 1576.1 (4) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 291 (2) K
0.29 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.932, T_max = 0.963
12153 measured reflections
5828 independent reflections
3782 reflections with I > 2sI)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.142
S = 1.03
5828 reflections
384 parameters
14 restraints
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.26 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2397 ).

Acknowledgements

This work was financially supported by the fund of the Key Laboratory of Nuclear Resources and Environment, East China Institute of Technology, Ministry of Education, China (No. 060607).

References

Bruker (1997). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Gilat, S. L., Kawai, S. H. & Lehn, J.-M. (1993). J. Chem. Soc. Chem. Commun., pp. 1685-1716.
Gilat, S. L., Kawai, S. H. & Lehn, J.-M. (1995). Chem. Eur. J. pp. 275-284.
Irie, M. (2000). Chem. Rev. 100, 1685-1716.
Kobatake, S., Kuma, S. & Irie, M. (2004). Bull. Chem. Soc. Jpn, 77, 945-951.
Pu, S.-Z., Yang, T.-S., Wang, R.-J. & Xu, J.-K. (2005). Acta Cryst. E61, o4077-o4079.
Pu, S.-Z., Zhang, F.-S., Fan, S., Wang, R.-J., Zhou, X.-H. & Chan, S.-K. (2003). Tetrahedron Lett. 44, 1011-1015.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, H. & Yang, S.-J. (2004). Chem. Soc. Rev. 33, 85-97.
Woodward, R. B. & Hoffmann, R. (1970). The Conservation of Orbital Symmetry, pp. 98-100. Weinheim: Verlag Chemie GmbH.
Yamaguchi, T. & Irie, M. (2006). Bull. Chem. Soc. Jpn, 79, 951-1100.
Zheng, C.-H., Pu, S.-Z., Le, Z.-G., Luo, M.-B. & Huang, D.-C. (2007). Acta Cryst. E63, o2578.

organic compounds