5-n-Butyl-4-[2-(2-ethyl-1-benzothio­phen-3-yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-en-1-yl]thio­phene-2-carbaldehyde

Yang, Z.; Fan, C.; Li, M.; Liu, W.; Liu, G.; Ng, S.W.

doi:10.1107/S1600536808036453

Volume 64
Part 12
Page o2311
December 2008

Received 23 August 2008
Accepted 6 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.046
wR = 0.151
Data-to-parameter ratio = 16.3
Details

5-n-Butyl-4-[2-(2-ethyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl]thiophene-2-carbaldehyde

Zhen Yang,^a Congbin Fan,^a ^* Min Li,^a Weijun Liu,^a Gang Liu ^a and Seik Weng Ng ^b

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: congbinfan@yahoo.com.cn

The title compound, C₂₄H₂₀F₆OS₂, exhibiting photochromic behaviour, has thienyl and benzothienyl substituents attached to the double-bond C atoms of the envelope-shaped cyclopentene ring. The mean planes of aromatic systems form dihedral angles of 43.0 (1) (thienyl) and 73.8 (1)° (benzothienyl) with the mean plane of the C-C=C-C portion of the cyclopentene ring. This conformation avoids steric hindrance between the n-butyl and ethyl substituents. The formyl substituent of the thienyl group, as well as the ethyl substituent of the benzothienyl group, are disordered [occupancies of 0.788 (17):0.212 (17) and 0.64 (5):0.36 (5), respectively].

Related literature

For the synthesis of the precursors, see: Pu et al. (2008); Ramamurthy & Venkatesan (1987); Kobatake & Irie (2004); Zheng et al. (2007). For the crystal structures of other photochromic dithienyl-substituted hexafluorocyclopentenes, see: Congbin et al. (2007); Li et al. (2008); Liu et al. (2008); Pu & Zhou (2007); Tu et al. (2008); Zhu et al. (2007).

Experimental

Crystal data

C₂₄H₂₀F₆OS₂
M_r = 502.52
Triclinic, $[P \overline 1]$
a = 10.051 (1) Å
b = 11.031 (1) Å
c = 12.019 (1) Å
= 113.126 (1)°
= 96.882 (1)°
= 103.542 (1)°
V = 1157.5 (2) Å³
Z = 2
Mo K radiation
= 0.29 mm^-1
T = 296 (2) K
0.43 × 0.43 × 0.43 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: none
10086 measured reflections
5195 independent reflections
3669 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.151
S = 1.03
5195 reflections
318 parameters
30 restraints
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.25 e Å^-3

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2080 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangxi (0620012) and the Science Fund of the Education Office of Jiangxi ([2007]279).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Congbin, F., Tianshe, Y., Qidong, T. & Gang, L. (2007). Acta Cryst. E63, o4721.
Kobatake, S. & Irie, M. (2004). Bull. Chem. Soc. Jpn, 77, 195-210.
Li, M., Pu, S.-Z., Fan, C.-B. & Le, Z.-G. (2008). Acta Cryst. E64, o517.
Liu, G., Tu, Q., Zhang, Q., Fan, C. & Yang, T. (2008). Acta Cryst. E64, o938.
Pu, S.-Z., Li, M., Fan, C.-B., Liu, G. & Shen, L. (2008). J. Mol. Struct. doi:10.1016/j.molstruc.2008.08.023.
Pu, S.-Z. & Zhou, Q.-F. (2007). Acta Cryst. E63, o927-o928.
Ramamurthy, V. & Venkatesan, K. (1987). Chem. Rev. 87, 433-481.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tu, Q., Fan, C., Liu, G., Li, M. & Ng, S. W. (2008). Acta Cryst. E64, o1007.
Westrip, S. P. (2008). publCIF. In preparation.
Zheng, C.-H., Pu, S.-Z., Xu, J.-K., Luo, M.-B., Huang, D.-C. & Shen, L. (2007). Tetrahedron, 63, 5437-5449.
Zhu, S., Rao, Y., Liu, G., Xie, Y. & Pu, S. (2007). Acta Cryst. E63, o4175.

organic compounds