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Volume 68 
Part 1 
Page o43  
January 2012  

Received 22 November 2011
Accepted 30 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.050
wR = 0.150
Data-to-parameter ratio = 13.2
Details
Open access

2',6'-Bis(4-carboxyphenyl)-4,4'-bipyridin-1-ium nitrate 0.25-hydrate

aDepartment of Ophthalmology, The Second Hospital of Jilin University, Changchun 130041, People's Republic of China, and bDepartment of Orthopedics, The China-Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China
Correspondence e-mail: doctorzang@163.com

In the title compound, C24H17N2O4+·NO3-·0.25H2O, the central pyridine ring of the 2',6'-bis(4-carboxyphenyl)-4,4'-bipyridin-1-ium cation is almost coplanar with one benzene ring [dihedral angle = 1.03 (5)°], while it makes dihedral angles of 9.59 (5)° with the other benzene ring and 13.66 (6)° with the pyridinium ring. In the crystal, N-H...O and O-H...O hydrogen bonds link the cations and nitrate anions into a sheet in the (302) plane. The crystal structure also exhibits [pi]-[pi] interactions between the central pyridine ring and the benzene rings of neighboring molecules [centroid-centroid distance = 3.6756 (13) Å].

Related literature

For the properties and applications of molecular-ionic crystals, see: Katrusiak & Szafranski (2006[Katrusiak, A. & Szafranski, M. (2006). J. Am. Chem. Soc. 128, 15775-15785.]); Liao et al. (2008[Liao, C. Y., Chan, K. T., Chiu, P. L., Chen, C. Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.]); Wang (2010[Wang, B. (2010). Acta Cryst. E66, o1473.]).

[Scheme 1]

Experimental

Crystal data
  • C24H17N2O4+·NO3-·0.25H2O

  • Mr = 463.91

  • Monoclinic, P 21 /c

  • a = 13.6978 (11) Å

  • b = 16.0688 (12) Å

  • c = 9.6354 (8) Å

  • [beta] = 92.696 (1)°

  • V = 2118.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.25 × 0.21 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.978

  • 11529 measured reflections

  • 4158 independent reflections

  • 2605 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.150

  • S = 1.04

  • 4158 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O5i 0.86 1.84 2.697 (2) 171
O2-H2A...O3ii 0.82 1.93 2.728 (2) 163
O4-H4...O5 0.82 1.78 2.598 (2) 173
O1W-H1A...O1Wiii 0.92 2.14 2.963 (18) 149
O1W-H1B...O1iv 0.90 2.22 3.059 (8) 154
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP in SHELXTL and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5723 ).


Acknowledgements

The authors thank Jilin University for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Katrusiak, A. & Szafranski, M. (2006). J. Am. Chem. Soc. 128, 15775-15785.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Liao, C. Y., Chan, K. T., Chiu, P. L., Chen, C. Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.  [ISI] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, B. (2010). Acta Cryst. E66, o1473.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o43  [ doi:10.1107/S1600536811051506 ]

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