2-Amino-3-carb­oxy­pyrazin-1-ium nitrate monohydrate

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

doi:10.1107/S1600536811003126

Volume 67
Part 2
Pages o525-o526
February 2011

Received 18 January 2011
Accepted 24 January 2011
Online 29 January 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 13.8
Details

2-Amino-3-carboxypyrazin-1-ium nitrate monohydrate

Fadila Berrah,^a,^b ^* Amira Ouakkaf,^a Sofiane Bouacida ^b,^c and Thierry Roisnel ^d

^aLaboratoire de Chimie Appliquée et Technologie des Matériaux, Université Larbi Ben M'Hidi, 04000 Oum El Bouaghi, Algeria,^bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, 04000 Oum El Bouaghi, Algeria,^cUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université Mentouri Constantine 25000, Algeria, and ^dCentre 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 crystal structure of the title compound, C₅H₆N₃O₂⁺·NO₃^-·H₂O, intermolecular N-HO, O-HN and O-HO hydrogen bonds link the cations, anions and water molecules into ribbons extending in [ $[\overline{1}]$ 10]. Weak intermolecular C-HO hydrogen bonds further link these ribbons into sheets parallel to ( $[\overline{1}]$ $[\overline{1}]$ 3).

Related literature

For similar compounds, see: Berrah et al. (2005a,b); Bouacida et al. (2005, 2009); Dobson & Gerkin (1996). For hydrogen-bond graph-set motifs, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₅H₆N₃O₂⁺·NO₃^-·H₂O
M_r = 220.15
Triclinic, $[P \overline 1]$
a = 5.1277 (4) Å
b = 7.6368 (6) Å
c = 12.1571 (10) Å
= 97.872 (3)°
= 100.588 (3)°
= 106.194 (3)°
V = 440.37 (6) Å³
Z = 2
Mo K radiation
= 0.15 mm^-1
T = 150 K
0.58 × 0.49 × 0.42 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.773, T_max = 0.938
5333 measured reflections
1967 independent reflections
1693 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
1967 reflections
143 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1Wⁱ	0.84	1.69	2.5233 (17)	168
O1W-H1WO5ⁱⁱ	0.80 (3)	1.93 (3)	2.7152 (18)	167 (3)
O1W-H2WO1	0.88 (3)	2.39 (3)	2.8825 (19)	116 (2)
O1W-H2WN4	0.88 (3)	1.99 (3)	2.8566 (18)	170 (2)
N2-H2AO5	0.88	2.01	2.8549 (17)	161
N2-H2BO2	0.88	2.08	2.7163 (17)	128
N2-H2BO2ⁱⁱⁱ	0.88	2.20	2.9125 (18)	137
N3-H3O4	0.88	1.91	2.7825 (16)	174
C4-H4AO4^iv	0.95	2.24	3.1818 (17)	169
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y-1, z; (iii) -x, -y+2, -z+1; (iv) -x+2, -y+3, -z+2.

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); 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: CV5043 ).

Acknowledgements

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Berrah, F., Benali-Cherif, N. & Lamraoui, H. (2005a). Acta Cryst. E61, o1517-o1519.
Berrah, F., Lamraoui, H. & Benali-Cherif, N. (2005b). Acta Cryst. E61, o210-o212.
Bouacida, S., Belhouas, R., Kechout, H., Merazig, H. & Bénard-Rocherullé, P. (2009). Acta Cryst. E65, o628-o629.
Bouacida, S., Merazig, H., Beghidja, A. & Beghidja, C. (2005). Acta Cryst. E61, m1153-m1155.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
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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.
Dobson, A. J. & Gerkin, R. E. (1996). Acta Cryst. C52, 1512-1514.
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.
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds