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

Fadila Berrah; Sofiane Bouacida; Thierry Roisnel

doi:10.1107/S1600536811017521

. 2011 May 14;67(Pt 6):o1409–o1410. doi: 10.1107/S1600536811017521

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

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

PMCID: PMC3120607 PMID: 21754792

Abstract

In the crystal structure of the title compound, C₅H₆N₃O₂ ⁺·H₂PO₄ ⁻, the dihydrogen phosphate anions are linked through short O—H⋯O hydrogen bonds, forming infinite double chains running parallel to the b axis. Centrosymetric N—H⋯O hydrogen-bonded cationic dimers form bridges between these chains by means of intermolecular N—H⋯O and O—H⋯O hydrogen bonds, leading to a two-dimensional network parallel to (100) in which R ₃ ³(12), R ₄ ³(10) R ₂ ²(8) and C(4) graph-set motifs are generated. Weak intermolecular C—H⋯O 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,
a = 8.6076 (5) Å
b = 4.6703 (3) Å
c = 21.9431 (13) Å
β = 95.573 (2)°
V = 877.94 (9) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.079
S = 1.04
2004 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017521/lh5248sup1.cif

e-67-o1409-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017521/lh5248Isup2.hkl

e-67-o1409-Isup2.hkl^{(96.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017521/lh5248Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O14	0.88	1.94	2.8171 (17)	171
N1—H1B⋯O9	0.88	2.09	2.7275 (17)	128
N1—H1B⋯O9ⁱ	0.88	2.37	3.0640 (19)	136
N3—H3⋯O11	0.88	1.79	2.6690 (16)	173
O10—H10⋯O13ⁱⁱ	0.84	1.83	2.6591 (16)	169
O12—H12⋯O11ⁱⁱⁱ	0.84	1.72	2.5386 (14)	166
O13—H13⋯O14^iv	0.84	1.64	2.4634 (16)	164
C4—H4⋯O11^v	0.95	2.43	3.3377 (19)	160

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our search for new hybrids based on protonated N-heterocyclic compounds and inorganic acids we have prepared the title compound. Our recent investigation in this field has revealed the ability of N-heterocyclic derivatives to generate original networks stabilized by hydrogen bonds and has shown how anion substitution may influence the hydrogen-bonding patterns (Berrah et al., 2011a,b,c; Ouakkaf et al., 2011).

The asymmetric unit of the title conpound compound contains one 2-amino-3-carboxypyrazin-1-ium cation and one dihydrogen phosphate anion (Fig. 1). Both entities display geometry similar to that reported in related compounds (Akriche & Rzaigui 2007; Berrah et al., 2011b; Shao et al., 2010). dihydrogen phosphate anions linked through strong O—H···O hydrogen bonds (Table 1), form double infinite chains running parallel to the b axis (Fig. 2). Similar chains were previously observed in related compounds (Akriche & Rzaigui 2007; Lin et al., 2009). 2-Amino-3-carboxypyrazin-1-ium centrosymetric dimers form bridges between these chains by means of N—H···O and O—H···O hydrogen bonds (Fig. 3) leading to a two-dimensional network (Fig. 4) where R³₃(12), R³₄(10), R²₂(8) and C(4) graph-set motifs are generated (Fig. 2 and Fig. 3)(Etter et al., 1990; Bernstein et al., 1995). Further stabilization is provided by intermolecular C—H···O contacts.

Experimental

The title compound was synthesized by reacting 3-amino-pyrazine-2-carboxylic acid with phosphoricic acid in a solution of equal volume of H₂O and CH₃OH. Slow evaporation leads to well crystallized colourless needles.