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Volume 68 
Part 1 
Page o108  
January 2012  

Received 30 November 2011
Accepted 30 November 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 21.4
Details
Open access

2-Amino-5-chloropyrimidin-1-ium hydrogen maleate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bBiomedical Structural Biology, School of Biological Sciences, Nanyang Technological University, Singapore 138673
Correspondence e-mail: hkfun@usm.my

In the title salt, C4H5ClN3+·C4H3O4-, the 2-amino-5-chloropyrimidinium cation is protonated at one of its pyrimidine N atoms. In the roughly planar (r.m.s. deviation = 0.026 Å) hydrogen malate anion, an intramolecular O-H...O hydrogen bond generates an S(7) ring. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxylate O atoms of the anion via a pair of N-H...O hydrogen bonds, forming an R22(8) ring motif. The ion pairs are connected via further N-H...O hydrogen bonds and a short C-H...O interaction, forming layers lying parallel to the bc plane.

Related literature

For background to pyrimidine compounds, see: Glidewell et al. (2003[Glidewell, C., Low, J. N., Melguizo, M. & Quesada, A. (2003). Acta Cryst. C59, o9-o13.]); Panneerselvam et al. (2004[Panneerselvam, P., Muthiah, P. T. & Francis, S. (2004). Acta Cryst. E60, o747-o749.]). For details of maleic acid, see: James & Williams (1974[James, M. N. G. & Williams, G. J. B. (1974). Acta Cryst. B30, 1249-1257.]); Bertolasi et al. (1980[Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 2287-2291.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C4H5ClN3+·C4H3O4-

  • Mr = 245.62

  • Monoclinic, P 21 /c

  • a = 9.3974 (6) Å

  • b = 5.5167 (4) Å

  • c = 20.0654 (13) Å

  • [beta] = 95.264 (1)°

  • V = 1035.86 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 296 K

  • 0.42 × 0.36 × 0.13 mm

Data collection
  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.860, Tmax = 0.954

  • 12808 measured reflections

  • 3443 independent reflections

  • 2745 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.109

  • S = 1.04

  • 3443 reflections

  • 161 parameters

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O4i 0.881 (19) 1.810 (18) 2.6897 (14) 177.6 (19)
N3-H1N3...O1ii 0.860 (17) 2.592 (18) 3.0814 (16) 117.2 (14)
N3-H1N3...O2ii 0.860 (17) 2.128 (17) 2.9795 (16) 170.2 (16)
N3-H2N3...O3i 0.893 (18) 1.975 (18) 2.8629 (17) 172.8 (16)
O1-H1O3...O3 0.86 (3) 1.60 (3) 2.4514 (15) 179 (3)
C2-H2A...O2iii 0.93 2.39 3.3117 (17) 173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: SHELXTL; software used to prepare material for publication: SHELXTL 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: HB6543 ).


Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 2287-2291.  [CrossRef] [details] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Glidewell, C., Low, J. N., Melguizo, M. & Quesada, A. (2003). Acta Cryst. C59, o9-o13.  [CSD] [CrossRef] [details]
James, M. N. G. & Williams, G. J. B. (1974). Acta Cryst. B30, 1249-1257.  [CrossRef] [ChemPort] [details] [ISI]
Panneerselvam, P., Muthiah, P. T. & Francis, S. (2004). Acta Cryst. E60, o747-o749.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o108  [ doi:10.1107/S1600536811051646 ]

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