2-Amino-3-carb-oxy-pyrazin-1-ium dihydrogen phosphate.

In the crystal structure of the title compound, C(5)H(6)N(3)O(2) (+)·H(2)PO(4) (-), 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 inter-molecular 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 inter-molecular 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 = 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

Δρmax = 0.39 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C5H6N3O2+·H2PO4−	F(000) = 488
Mr = 237.11	Dx = 1.794 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4062 reflections
a = 8.6076 (5) Å	θ = 3.2–27.5°
b = 4.6703 (3) Å	µ = 0.33 mm−1
c = 21.9431 (13) Å	T = 150 K
β = 95.573 (2)°	Needle, colourless
V = 877.94 (9) Å3	0.45 × 0.06 × 0.04 mm
Z = 4

Bruker APEXII diffractometer	1781 reflections with I > 2σ(I)
graphite	Rint = 0.025
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −11→7
Tmin = 0.898, Tmax = 0.987	k = −6→6
7993 measured reflections	l = −28→28
2004 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.6558P] where P = (Fo2 + 2Fc2)/3
2004 reflections	(Δ/σ)max = 0.001
139 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.86142 (15)	0.8016 (3)	0.90992 (6)	0.0173 (3)
H1A	0.8733	0.8741	0.8736	0.021*
H1B	0.9191	0.8645	0.9425	0.021*
C2	0.75718 (17)	0.5988 (3)	0.91547 (6)	0.0137 (3)
N3	0.66953 (15)	0.5047 (3)	0.86483 (5)	0.0149 (3)
H3	0.6834	0.583	0.8293	0.018*
C4	0.56229 (17)	0.2967 (3)	0.86666 (7)	0.0165 (3)
H4	0.5045	0.2339	0.83	0.02*
C5	0.53675 (17)	0.1756 (3)	0.92166 (7)	0.0171 (3)
H5	0.4608	0.0288	0.923	0.02*
N6	0.61838 (15)	0.2626 (3)	0.97404 (6)	0.0166 (3)
C7	0.72487 (17)	0.4646 (3)	0.97204 (6)	0.0142 (3)
C8	0.81279 (17)	0.5559 (3)	1.03115 (7)	0.0155 (3)
O9	0.91059 (13)	0.7446 (2)	1.03400 (5)	0.0214 (3)
O10	0.77252 (13)	0.4096 (3)	1.07821 (5)	0.0212 (3)
H10	0.8219	0.4712	1.1104	0.032*
P1	0.79097 (4)	0.97152 (8)	0.740127 (16)	0.01125 (11)
O11	0.70388 (12)	0.7004 (2)	0.75265 (5)	0.0161 (2)
O12	0.66950 (12)	1.1937 (2)	0.71167 (5)	0.0162 (2)
H12	0.696	1.3588	0.7238	0.024*
O13	0.89962 (12)	0.9251 (2)	0.68787 (5)	0.0183 (2)
H13	0.9697	0.8065	0.6994	0.027*
O14	0.88101 (12)	1.0854 (2)	0.79764 (5)	0.0158 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0199 (6)	0.0194 (7)	0.0125 (6)	−0.0029 (5)	0.0013 (5)	0.0017 (5)
C2	0.0139 (7)	0.0139 (7)	0.0134 (6)	0.0041 (5)	0.0019 (5)	−0.0008 (5)
N3	0.0177 (6)	0.0157 (6)	0.0113 (6)	0.0025 (5)	0.0013 (5)	0.0010 (5)
C4	0.0150 (7)	0.0166 (7)	0.0173 (7)	0.0029 (6)	−0.0014 (6)	−0.0021 (6)
C5	0.0141 (7)	0.0177 (7)	0.0193 (7)	−0.0006 (6)	0.0015 (6)	−0.0016 (6)
N6	0.0160 (6)	0.0182 (6)	0.0158 (6)	0.0017 (5)	0.0027 (5)	0.0000 (5)
C7	0.0144 (7)	0.0160 (7)	0.0123 (6)	0.0027 (5)	0.0020 (5)	−0.0003 (5)
C8	0.0160 (7)	0.0172 (7)	0.0135 (7)	0.0028 (6)	0.0023 (5)	−0.0006 (5)
O9	0.0245 (6)	0.0223 (6)	0.0168 (5)	−0.0050 (5)	−0.0003 (4)	−0.0013 (4)
O10	0.0233 (6)	0.0296 (6)	0.0106 (5)	−0.0056 (5)	0.0011 (4)	0.0010 (4)
P1	0.01218 (19)	0.01066 (18)	0.01087 (18)	0.00067 (13)	0.00093 (13)	−0.00036 (13)
O11	0.0213 (5)	0.0112 (5)	0.0156 (5)	−0.0021 (4)	0.0010 (4)	−0.0006 (4)
O12	0.0158 (5)	0.0107 (5)	0.0212 (5)	0.0021 (4)	−0.0025 (4)	−0.0026 (4)
O13	0.0182 (5)	0.0239 (6)	0.0132 (5)	0.0094 (4)	0.0034 (4)	0.0031 (4)
O14	0.0168 (5)	0.0181 (5)	0.0121 (5)	−0.0043 (4)	0.0004 (4)	0.0003 (4)

N1—C2	1.319 (2)	N6—C7	1.319 (2)
N1—H1A	0.88	C7—C8	1.4987 (19)
N1—H1B	0.88	C8—O9	1.2161 (19)
C2—N3	1.3543 (18)	C8—O10	1.3127 (18)
C2—C7	1.442 (2)	O10—H10	0.84
N3—C4	1.343 (2)	P1—O11	1.5101 (11)
N3—H3	0.88	P1—O14	1.5120 (10)
C4—C5	1.370 (2)	P1—O12	1.5597 (11)
C4—H4	0.95	P1—O13	1.5636 (11)
C5—N6	1.3503 (19)	O12—H12	0.84
C5—H5	0.95	O13—H13	0.84
C2—N1—H1A	120	N6—C7—C2	122.16 (13)
C2—N1—H1B	120	N6—C7—C8	117.96 (13)
H1A—N1—H1B	120	C2—C7—C8	119.88 (13)
N1—C2—N3	119.16 (13)	O9—C8—O10	124.84 (14)
N1—C2—C7	125.57 (13)	O9—C8—C7	122.65 (14)
N3—C2—C7	115.26 (13)	O10—C8—C7	112.51 (13)
C4—N3—C2	122.68 (13)	C8—O10—H10	109.5
C4—N3—H3	118.7	O11—P1—O14	111.49 (6)
C2—N3—H3	118.7	O11—P1—O12	107.77 (6)
N3—C4—C5	119.62 (14)	O14—P1—O12	111.69 (6)
N3—C4—H4	120.2	O11—P1—O13	111.11 (6)
C5—C4—H4	120.2	O14—P1—O13	111.48 (6)
N6—C5—C4	120.73 (14)	O12—P1—O13	102.94 (6)
N6—C5—H5	119.6	P1—O12—H12	109.5
C4—C5—H5	119.6	P1—O13—H13	109.5
C7—N6—C5	119.53 (13)
N1—C2—N3—C4	179.23 (13)	N3—C2—C7—N6	0.6 (2)
C7—C2—N3—C4	−1.4 (2)	N1—C2—C7—C8	0.5 (2)
C2—N3—C4—C5	1.2 (2)	N3—C2—C7—C8	−178.86 (12)
N3—C4—C5—N6	−0.1 (2)	N6—C7—C8—O9	−178.37 (14)
C4—C5—N6—C7	−0.6 (2)	C2—C7—C8—O9	1.1 (2)
C5—N6—C7—C2	0.4 (2)	N6—C7—C8—O10	1.9 (2)
C5—N6—C7—C8	179.86 (13)	C2—C7—C8—O10	−178.58 (13)
N1—C2—C7—N6	179.93 (14)

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···O14iv	0.84	1.64	2.4634 (16)	164
C4—H4···O11v	0.95	2.43	3.3377 (19)	160

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⋯O14iv	0.84	1.64	2.4634 (16)	164
C4—H4⋯O11v	0.95	2.43	3.3377 (19)	160

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