(Z)-1,1-Dicyano-2-(4-fluoro­phen­yl)-3-(1-hexyl­pyridin-1-ium-4-yl)prop-2-en-1-ide

Hao, W.-H.; Wang, C.; Qian, G.; Wang, Z.-Y.

doi:10.1107/S160053681105166X

Volume 68
Part 1
Page o82
January 2012

Received 18 November 2011
Accepted 30 November 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.080
Data-to-parameter ratio = 14.4
Details

(Z)-1,1-Dicyano-2-(4-fluorophenyl)-3-(1-hexylpyridin-1-ium-4-yl)prop-2-en-1-ide

Wen-Hui Hao,^a Cheng Wang,^b Gang Qian ^a and Zhi-Yuan Wang ^a ^*

^aDepartment of Chemistry, Carleton University, Ottawa, Ontario, Canada K1S 5B6, and ^bKey Laboratory of Functional Materials and Key Laboratory of Polymer Functional Materials, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: wayne_wang@carleton.ca

The title compound, C₂₂H₂₂FN₃, exists as a zwitterion with the negative charge on the dicyanomethanide group and the positive charge on the pyridinium N atom. The molecule adopts a Z conformation about the central C=C bond. The dihedral angle between the pyridinium and benzene rings is 65.65 (5)°. Weak C-HN hydrogen bonding is present in the crystal structure.

Related literature

For details of zwitterionic chromophores and their applications, see: Hao (2011); Hao et al. (2011). For related structures, see: Metzger & Heimer (1984); Bell et al. (2002); Cole et al. (1997); Szablewski et al. (1997); Xiong et al.(2008). For the synthesis, see: Hao (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₂₂H₂₂FN₃
M_r = 347.43
Monoclinic, P 2₁ /c
a = 10.485 (3) Å
b = 8.809 (2) Å
c = 21.313 (5) Å
= 100.628 (4)°
V = 1934.7 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 295 K
0.24 × 0.21 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.982, T_max = 0.986
9762 measured reflections
3406 independent reflections
2154 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.080
S = 1.01
3406 reflections
237 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3AN2ⁱ	0.93	2.61	3.535 (3)	175
C16-H16AN1ⁱⁱ	0.93	2.51	3.354 (3)	151
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: XU5392 ).

Acknowledgements

We acknowledge financial support for research from the Natural Sciences and Engineering Research Council of Canada, and NSFC grant No. 21110402016.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bell, N. A., Crouch, D. J., Simmonds, D. J., Goeta, A. E., Gelbrich, T. & Hursthouse, M. B. (2002). J. Mater. Chem. 12, 1274-1279.
Cole, J. C., Cole, J. M., Cross, G. H., Farsari, M., Howard, J. A. K. & Szablewski, M. (1997). Acta Cryst. B53, 812-821.
Hao, W.-H. (2011). PhD thesis, Carleton University, Canada.
Hao, W.-H., McBride, A., McBride, S., Gao, J.-P. & Wang, Z.-Y. (2011). J. Mater. Chem. 21, 1040-1048.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Metzger, R. M. & Heimer, N. E. (1984). Mol. Cryst. Liq. Cryst. 107, 133-149.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Szablewski, M., Thomas, P. R., Thornton, A., Bloor, D., Cross, G. H., Cole, J. M., Howard, J. A. K., Malagoli, M., Meyers, F., Bredas, J.-L., Wenseleers, W. & Goovaerts, E. (1997). J. Am. Chem. Soc. 119, 3144-3154.
Xiong, Y., Tang, H., Zhang, J., Wang, Z.-Y., Campo, J., Wenseleers, W. & Goovaerts, E. (2008). Chem. Mater. 20, 7465-7473.

organic compounds