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Volume 69 
Part 5 
Page o689  
May 2013  

Received 19 February 2013
Accepted 29 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in solvent or counterion
R = 0.053
wR = 0.163
Data-to-parameter ratio = 12.6
Details
Open access

2-[3-(Pyridin-1-ium-2-yl)-1H-pyrazol-1-yl]-6-[3-(pyridin-2-yl)-1H-pyrazol-1-yl]pyridinium sulfate methanol monosolvate

aSchool of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
Correspondence e-mail: mhshu@sjtu.edu.cn

The title solvated salt, C21H17N72+·SO42-·CH3OH, was obtained when we attempted to prepare the complex of ferrous sulfate and 2,6-bis[3-(pyridin-2-yl)-1H-pyrazol-1-yl]pyridine in methanol. The dihedral angles between adjacent pyridine and pyrazole rings range from 3.8 (1) to 13.4 (1)°. An intramolecular N-H...N hydrogen bond occurs. In the crystal, N-H...O and O-H...N hydrogen bonds between solvent methanol molecules and the cations generate zigzag chains along [110].

Related literature

For general background to the chemistry of oligapyridine ligands, see: Constable et al. (1988[Constable, E. C., Drew, M. G. B., Forsyth, G. & Ward, M. D. (1988). J. Chem. Soc. Chem. Commun. pp. 1450-1451.], 1992[Constable, E. C. (1992). Tetrahedron, 48, 10013-10059.], 1997[Constable, E. C., Heitzler, F., Neuburger, M. & Zehnder, M. (1997). J. Am. Chem. Soc. 119, 5606-5617.]); Fu, Li et al. (1996[Fu, Y., Li, Q., Zhou, Z., Wang, D., Wak, T. C. W., Hu, H. & Tang, W. (1996). Chem. Commun. pp. 1549-1550.]); Fu, Sun et al. (1996[Fu, Y., Sun, J., Li, Q., Chen, Y., Dai, W., Wang, D., Mak, T. C. W., Tang, W. & Hu, H. (1996). J. Chem. Soc. Dalton Trans. pp. 2309-2313.]). For the synthesis of the ligand, see: Jameson & Goldsby (1990[Jameson, D. L. & Goldsby, K. A. (1990). J. Org. Chem., 55, 4992-4994.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17N72+·SO42-·CH4O

  • Mr = 495.52

  • Triclinic, [P \overline 1]

  • a = 9.2575 (5) Å

  • b = 12.1707 (7) Å

  • c = 12.1991 (7) Å

  • [alpha] = 112.786 (6)°

  • [beta] = 100.997 (5)°

  • [gamma] = 106.363 (5)°

  • V = 1143.90 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 293 K

  • 0.26 × 0.23 × 0.20 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.952, Tmax = 0.963

  • 7326 measured reflections

  • 4192 independent reflections

  • 2629 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.163

  • S = 1.01

  • 4192 reflections

  • 334 parameters

  • 21 restraints

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N7-H7...N6 0.86 (1) 2.35 (1) 2.713 (10) 106 (1)
O5-H5...N1 0.86 (3) 1.97 (3) 2.79 (3) 159 (4)
N7-H7...O5i 0.86 (1) 1.88 (1) 2.690 (10) 156 (1)
Symmetry code: (i) x+1, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Ata Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Ata Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Ata Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2223 ).


Acknowledgements

The authors acknowledge financial support by the Natural Science Foundation of China (grant No. 21271129).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Constable, E. C. (1992). Tetrahedron, 48, 10013-10059.  [CrossRef] [ChemPort] [ISI]
Constable, E. C., Drew, M. G. B., Forsyth, G. & Ward, M. D. (1988). J. Chem. Soc. Chem. Commun. pp. 1450-1451.  [CrossRef] [ISI]
Constable, E. C., Heitzler, F., Neuburger, M. & Zehnder, M. (1997). J. Am. Chem. Soc. 119, 5606-5617.  [CrossRef] [ChemPort] [ISI]
Fu, Y., Li, Q., Zhou, Z., Wang, D., Wak, T. C. W., Hu, H. & Tang, W. (1996). Chem. Commun. pp. 1549-1550.  [CrossRef]
Fu, Y., Sun, J., Li, Q., Chen, Y., Dai, W., Wang, D., Mak, T. C. W., Tang, W. & Hu, H. (1996). J. Chem. Soc. Dalton Trans. pp. 2309-2313.  [CrossRef]
Jameson, D. L. & Goldsby, K. A. (1990). J. Org. Chem., 55, 4992-4994.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Ata Cryst. A64, 112-122.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o689  [ doi:10.1107/S1600536813008647 ]

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