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

Fun, H.-K.; Hemamalini, M.; Rajakannan, V.

doi:10.1107/S1600536811051646

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 21.4
Details

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

Hoong-Kun Fun,^a ^*⁺ Madhukar Hemamalini ^a and Venkatachalam Rajakannan ^b

^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-HO 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-HO hydrogen bonds, forming an R²₂(8) ring motif. The ion pairs are connected via further N-HO hydrogen bonds and a short C-HO interaction, forming layers lying parallel to the bc plane.

Related literature

For background to pyrimidine compounds, see: Glidewell et al. (2003); Panneerselvam et al. (2004). For details of maleic acid, see: James & Williams (1974); Bertolasi et al. (1980). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₄H₅ClN₃⁺·C₄H₃O₄^-
M_r = 245.62
Monoclinic, P 2₁ /c
a = 9.3974 (6) Å
b = 5.5167 (4) Å
c = 20.0654 (13) Å
= 95.264 (1)°
V = 1035.86 (12) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.860, T_max = 0.954
12808 measured reflections
3443 independent reflections
2745 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(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
_max = 0.35 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2O4ⁱ	0.881 (19)	1.810 (18)	2.6897 (14)	177.6 (19)
N3-H1N3O1ⁱⁱ	0.860 (17)	2.592 (18)	3.0814 (16)	117.2 (14)
N3-H1N3O2ⁱⁱ	0.860 (17)	2.128 (17)	2.9795 (16)	170.2 (16)
N3-H2N3O3ⁱ	0.893 (18)	1.975 (18)	2.8629 (17)	172.8 (16)
O1-H1O3O3	0.86 (3)	1.60 (3)	2.4514 (15)	179 (3)
C2-H2AO2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 2287-2291.
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.
James, M. N. G. & Williams, G. J. B. (1974). Acta Cryst. B30, 1249-1257.
Panneerselvam, P., Muthiah, P. T. & Francis, S. (2004). Acta Cryst. E60, o747-o749.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds