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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 [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.080
Data-to-parameter ratio = 14.4
Details
Open access

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

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-H...N hydrogen bonding is present in the crystal structure.

Related literature

For details of zwitterionic chromophores and their applications, see: Hao (2011[Hao, W.-H. (2011). PhD thesis, Carleton University, Canada.]); Hao et al. (2011[Hao, W.-H., McBride, A., McBride, S., Gao, J.-P. & Wang, Z.-Y. (2011). J. Mater. Chem. 21, 1040-1048.]). For related structures, see: Metzger & Heimer (1984[Metzger, R. M. & Heimer, N. E. (1984). Mol. Cryst. Liq. Cryst. 107, 133-149.]); Bell et al. (2002[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 et al. (1997[Cole, J. C., Cole, J. M., Cross, G. H., Farsari, M., Howard, J. A. K. & Szablewski, M. (1997). Acta Cryst. B53, 812-821.]); Szablewski et al. (1997[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 et al.(2008[Xiong, Y., Tang, H., Zhang, J., Wang, Z.-Y., Campo, J., Wenseleers, W. & Goovaerts, E. (2008). Chem. Mater. 20, 7465-7473.]). For the synthesis, see: Hao (2011[Hao, W.-H. (2011). PhD thesis, Carleton University, Canada.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C22H22FN3

  • Mr = 347.43

  • Monoclinic, P 21 /c

  • a = 10.485 (3) Å

  • b = 8.809 (2) Å

  • c = 21.313 (5) Å

  • [beta] = 100.628 (4)°

  • V = 1934.7 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.986

  • 9762 measured reflections

  • 3406 independent reflections

  • 2154 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.080

  • S = 1.01

  • 3406 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...N2i 0.93 2.61 3.535 (3) 175
C16-H16A...N1ii 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[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CSD] [CrossRef] [ChemPort]
Cole, J. C., Cole, J. M., Cross, G. H., Farsari, M., Howard, J. A. K. & Szablewski, M. (1997). Acta Cryst. B53, 812-821.  [CrossRef] [ISI] [details]
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.  [ISI] [CrossRef] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Metzger, R. M. & Heimer, N. E. (1984). Mol. Cryst. Liq. Cryst. 107, 133-149.  [CrossRef] [ChemPort]
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.  [CrossRef] [details]
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.  [CrossRef] [ChemPort] [ISI]
Xiong, Y., Tang, H., Zhang, J., Wang, Z.-Y., Campo, J., Wenseleers, W. & Goovaerts, E. (2008). Chem. Mater. 20, 7465-7473.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o82  [ doi:10.1107/S160053681105166X ]

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