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Volume 69 
Part 4 
Page o487  
April 2013  

Received 1 February 2013
Accepted 27 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.114
Data-to-parameter ratio = 17.4
Details
Open access

3-Methyl-2-vinylpyridinium phosphate

aDepartment of Inorganic Chemistry, University of Madras, Chennai 600 025, India, and bDepartment of Physics, Presidency College, Chennai 600 005, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title salt, C8H10N+·H2PO4-, the cation is essentially planar (r.m.s. deviation = 0.063 Å). In the crystal, the phosphate anions form inversion R22(8) dimers via pairs of O-H...O hydrogen bonds. These dimers are further linked by pairs of O-H...O hydrogen bonds, also enclosing R22(8) loops, forming chains running along [001]. The cations are bonded to the anions via N-H...O hydrogen bonds and C-H...O contacts.

Related literature

For the biological activity of 4-aminopyridine, see: Judge & Bever (2006[Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224-259.]); Schwid et al. (1997[Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.]); Strupp et al. (2004[Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623-1625.]). For related structures, see: Anderson et al. (2005[Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.]); Fun et al. (2009[Fun, H.-K., John, J., Jebas, S. R. & Balasubramanian, T. (2009). Acta Cryst. E65, o765-o766.]); Sabari et al. (2012[Sabari, V., Kalaiselvi, G., Balasubramanian, S. & Aravindhan, S. (2012). Acta Cryst. E68, o2937.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N+·H2PO4-

  • Mr = 217.16

  • Monoclinic, P 21 /c

  • a = 7.7089 (6) Å

  • b = 16.3668 (13) Å

  • c = 8.0649 (6) Å

  • [beta] = 109.689 (4)°

  • V = 958.06 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]) Tmin = 0.922, Tmax = 0.947

  • 8970 measured reflections

  • 2362 independent reflections

  • 2052 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.114

  • S = 1.08

  • 2362 reflections

  • 136 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.86 1.83 2.6558 (18) 160
O3-H3A...O1i 0.89 (1) 1.72 (1) 2.5995 (18) 173 (3)
O4-H4A...O2ii 0.89 (1) 1.72 (1) 2.6002 (17) 170 (3)
C1-H1A...O1iii 0.93 2.48 3.172 (2) 131
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6887 ).


Acknowledgements

SA and VS thank the UGC, India, for financial support. The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.  [CSD] [CrossRef] [details]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., John, J., Jebas, S. R. & Balasubramanian, T. (2009). Acta Cryst. E65, o765-o766.  [CSD] [CrossRef] [details]
Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224-259.  [CrossRef] [PubMed] [ChemPort]
Sabari, V., Kalaiselvi, G., Balasubramanian, S. & Aravindhan, S. (2012). Acta Cryst. E68, o2937.  [CSD] [CrossRef] [details]
Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623-1625.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o487  [ doi:10.1107/S160053681300576X ]

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