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Volume 69 
Part 4 
Page o529  
April 2013  

Received 8 February 2013
Accepted 6 March 2013
Online 13 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.088
Data-to-parameter ratio = 13.7
Details
Open access

2-Amino-4-methylpyrimidinium dihydrogen phosphate

aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and bDepartment of Chemistry, Kakatiya University, Warangal 506 009, India
Correspondence e-mail: jyothisri97@yahoo.co.in

A charge-assisted hydrogen-bonding network involving N-H...O and O-H...O hydrogen bonds stabilizes the crystal of the title salt, C5H8N3+·H2PO4-. The dihydrogen phosphate anions form one-dimensional chains along [100], via O-H...O hydrogen bonds. The 2-amino-4-methylpyrimidinium cations are linked to these chains by means of two different kinds of N-H...O hydrogen bonds. Neighbouring chains are linked via C-H...N and C-H...O hydrogen bonds forming two-dimensional slab-like networks lying parallel to (01-1).

Related literature

Intriguing anion clusters formed by the supramolecular assembly of dihydrogen phosphates have been investigated recently (see: Hossain et al., 2012[Hossain, M. A., Muhammet, I. K., Avijit, P., Musabbir, A. S. & Frank, R. F. (2012). Cryst. Growth Des. 12, 567-571.]). Methylpyrimidine derivatives are known to be synthetic precursors to many bioactive pyrimidine derivatives (see: Xue et al., 1993[Xue, S. J., Zhang, A. D. & Wang, H. T. (1993). Chem. Reagents, 15, 181-182.]). Metal complexes of pyrimidines (see: Zhu et al., 2008[Zhu, W., Liu, X. & Wang, H. (2008). Acta Opt. Sin. 28, 1155-1160.]) and their proton transfer complexes with mineral acids are reported (see: Aakeroy et al., 2003[Aakeroy, C. B., Beffert, K., Desper, J. & Elisabeth, E. (2003). Cryst. Growth Des. 3, 837-846.]). The infinite O-H...O hydrogen-bond chain present in this material is a structural feature suggestive of possible proton conducting behaviour (see: Haile et al., 2001[Haile, S. M., Boysen, D. A., Chisholm, C. R. I. & Merle, R. B. (2001). Nature, 410, 910-913.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8N3+·H2PO4-

  • Mr = 207.13

  • Triclinic, [P \overline 1]

  • a = 6.1720 (2) Å

  • b = 7.5616 (3) Å

  • c = 9.9216 (4) Å

  • [alpha] = 100.562 (3)°

  • [beta] = 99.821 (3)°

  • [gamma] = 102.279 (4)°

  • V = 434.07 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 295 K

  • 0.25 × 0.20 × 0.18 mm

Data collection
  • Oxford Xcalibur Eos (Nova) CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.928, Tmax = 0.947

  • 9718 measured reflections

  • 1717 independent reflections

  • 1546 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.088

  • S = 1.08

  • 1717 reflections

  • 125 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O4i 0.82 1.80 2.6100 (18) 168
N1-H1N...O2ii 0.86 2.14 3.000 (2) 177
O2-H2...O4iii 0.82 1.80 2.5843 (17) 161
N1-H2N...O3iv 0.86 2.01 2.845 (2) 163
N3-H3N...O3ii 0.90 (2) 1.73 (2) 2.6276 (19) 173 (2)
C4-H4...N2v 0.93 2.55 3.463 (2) 166
C5-H5B...O1vi 0.96 2.58 3.531 (3) 171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+2; (v) x+1, y, z; (vi) -x, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); 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.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: 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: DS2227 ).


Acknowledgements

SPT thanks UGC for an SRF, JS thanks UGC for research funding. SPT and SJ acknowledge Professor T. N. Guru Row for his support and XRD facility at IISc.

References

Aakeroy, C. B., Beffert, K., Desper, J. & Elisabeth, E. (2003). Cryst. Growth Des. 3, 837-846.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Haile, S. M., Boysen, D. A., Chisholm, C. R. I. & Merle, R. B. (2001). Nature, 410, 910-913.  [ISI] [CrossRef] [PubMed] [ChemPort]
Hossain, M. A., Muhammet, I. K., Avijit, P., Musabbir, A. S. & Frank, R. F. (2012). Cryst. Growth Des. 12, 567-571.  [CSD] [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Xue, S. J., Zhang, A. D. & Wang, H. T. (1993). Chem. Reagents, 15, 181-182.  [ChemPort]
Zhu, W., Liu, X. & Wang, H. (2008). Acta Opt. Sin. 28, 1155-1160.  [ChemPort]


Acta Cryst (2013). E69, o529  [ doi:10.1107/S160053681300648X ]

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