2-Amino-3-carb­oxy­pyrazin-1-ium dihydrogen phosphate

Berrah, F.; Bouacida, S.; Roisnel, T.

doi:10.1107/S1600536811017521

Volume 67
Part 6
Pages o1409-o1410
June 2011

Received 2 May 2011
Accepted 9 May 2011
Online 14 May 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.079
Data-to-parameter ratio = 14.4
Details

2-Amino-3-carboxypyrazin-1-ium dihydrogen phosphate

Fadila Berrah,^a ^*⁺ Sofiane Bouacida ^b ⁺⁺ and Thierry Roisnel ^c

^aLaboratoire de Chimie Appliquée et Technologie des Matériaux LCATM, Université Larbi Ben M'Hidi, 04000 Oum El Bouaghi, Algeria,^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université Mentouri Constantine 25000, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
Correspondence e-mail: fadilaber@yahoo.fr

In the crystal structure of the title compound, C₅H₆N₃O₂⁺·H₂PO₄^-, the dihydrogen phosphate anions are linked through short O-HO hydrogen bonds, forming infinite double chains running parallel to the b axis. Centrosymetric N-HO hydrogen-bonded cationic dimers form bridges between these chains by means of intermolecular N-HO and O-HO hydrogen bonds, leading to a two-dimensional network parallel to (100) in which R₃³(12), R₄³(10) R₂²(8) and C(4) graph-set motifs are generated. Weak intermolecular C-HO hydrogen bonds connect these layers, forming a three-dimensional network.

Related literature

For hybrid compounds based on N-heterocycles, see: Akriche & Rzaigui (2007); Berrah et al. (2011a,b,c); Ouakkaf et al. (2011). For related dihydrogenphosphte compounds, see: Lin et al. (2009); Shao et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

C₅H₆N₃O₂⁺·H₂PO₄^-
M_r = 237.11
Monoclinic, P 2₁ /c
a = 8.6076 (5) Å
b = 4.6703 (3) Å
c = 21.9431 (13) Å
= 95.573 (2)°
V = 877.94 (9) Å³
Z = 4
Mo K radiation
= 0.33 mm^-1
T = 150 K
0.45 × 0.06 × 0.04 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.898, T_max = 0.987
7993 measured reflections
2004 independent reflections
1781 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.079
S = 1.04
2004 reflections
139 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO14	0.88	1.94	2.8171 (17)	171
N1-H1BO9	0.88	2.09	2.7275 (17)	128
N1-H1BO9ⁱ	0.88	2.37	3.0640 (19)	136
N3-H3O11	0.88	1.79	2.6690 (16)	173
O10-H10O13ⁱⁱ	0.84	1.83	2.6591 (16)	169
O12-H12O11ⁱⁱⁱ	0.84	1.72	2.5386 (14)	166
O13-H13O14^iv	0.84	1.64	2.4634 (16)	164
C4-H4O11^v	0.95	2.43	3.3377 (19)	160
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5248 ).

Acknowledgements

We are grateful to the LCATM laboratory, Université Larbi Ben M'Hidi, Oum El Bouaghi, Algeria, for financial support.

References

Akriche, S. & Rzaigui, M. (2007). Acta Cryst. E63, o3460.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Berrah, F., Ouakkaf, A., Bouacida, S. & Roisnel, T. (2011a). Acta Cryst. E67, o525-o526.
Berrah, F., Ouakkaf, A., Bouacida, S. & Roisnel, T. (2011b). Acta Cryst. E67, o677-o678.
Berrah, F., Ouakkaf, A., Bouacida, S. & Roisnel, T. (2011c). Acta Cryst. E67, o953-o954.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Lin, C.-H., Liu, N.-S. & Jian, F.-F. (2009). Acta Cryst. E65, o2639.
Ouakkaf, A., Berrah, F., Bouacida, S. & Roisnel, T. (2011). Acta Cryst. E67, o1171-o1172.
Shao, Z.-D., Jiang, X., Lan, S.-M., Di, W.-J. & Liang, Y.-X. (2010). Acta Cryst. E66, o1757-o1758.
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds