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Volume 69 
Part 10 
Page o1503  
October 2013  

Received 16 August 2013
Accepted 29 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.172
Data-to-parameter ratio = 12.4
Details
Open access

1-(3-Carboxylatophenyl)-4,4'-bipyridin-1-ium dihydrate

aKey Lab for Fuel Cell Technology of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, People's Republic of China
Correspondence e-mail: zyfu@scut.edu.cn

In the crystal structure of the title compound, C17H12N2O2·2H2O, the carboxylate group is linked via O-H...O hydrogen bonds to two water molecules. The crystal packing is best described as parallel layers (viewed along the a axis) of viologen and water molecules associated via O-H...O hydrogen bonds and [pi]-[pi] interactions, with a centroid-centroid separation of 3.8276 (9) Å.

Related literature

For background to the applications of viologen complexes, see: Strutt et al. (2012[Strutt, N. L., Zhang, H. C., Giesener, M. A., Leia, J. & Stoddart, J. F. (2012). Chem. Commun. 48, 1647-1649.]). For related structures, see: Coe et al. (1998[Coe, B. J., Harris, J. A., Harrington, L. J., Jeffery, J. C., Rees, R. H., Houbrechts, S. & Persoons, A. (1998). Inorg. Chem. 37, 3391-3399.]); Leblanc et al. (2010[Leblanc, N., Bi, W. H., Mercier, N., Auban-Senzier, P. & Pasquier, C. (2010). Inorg. Chem. 49, 5824-5833.]); Xu et al. (2007[Xu, G., Guo, G. C., Wang, M. S. & Zhang, Z. G. (2007). Angew. Chem. Int. Ed. 46, 3249-3251.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12N2O2·2H2O

  • Mr = 312.32

  • Triclinic, [P \overline 1]

  • a = 7.8700 (16) Å

  • b = 10.090 (2) Å

  • c = 10.250 (2) Å

  • [alpha] = 81.36 (3)°

  • [beta] = 73.13 (3)°

  • [gamma] = 74.64 (3)°

  • V = 748.7 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.13 × 0.12 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.993

  • 6136 measured reflections

  • 2741 independent reflections

  • 2120 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.172

  • S = 1.18

  • 2741 reflections

  • 221 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H3...O1 0.89 (3) 1.84 (2) 2.703 (2) 164 (1)
O3-H1...O2 0.91 (2) 1.94 (2) 2.843 (3) 174 (1)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2640 ).


Acknowledgements

The authors thank the Project on Integration of Industry, Education and Research of Guangdong Province (2012B091100430), the Fundamental Research Funds for the Central Universities (2012ZD0038), the National Undergraduate Research Program and the SRP program for financial support.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Coe, B. J., Harris, J. A., Harrington, L. J., Jeffery, J. C., Rees, R. H., Houbrechts, S. & Persoons, A. (1998). Inorg. Chem. 37, 3391-3399.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Leblanc, N., Bi, W. H., Mercier, N., Auban-Senzier, P. & Pasquier, C. (2010). Inorg. Chem. 49, 5824-5833.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Strutt, N. L., Zhang, H. C., Giesener, M. A., Leia, J. & Stoddart, J. F. (2012). Chem. Commun. 48, 1647-1649.  [CrossRef] [ChemPort]
Xu, G., Guo, G. C., Wang, M. S. & Zhang, Z. G. (2007). Angew. Chem. Int. Ed. 46, 3249-3251.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1503  [ doi:10.1107/S1600536813024197 ]

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