2-Amino-3-carb-oxy-pyrazin-1-ium nitrate monohydrate.

In crystal structure of the title compound, C(5)H(6)N(3)O(2) (+)·NO(3) (-)·H(2)O, inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds link the cations, anions and water mol-ecules into ribbons extending in [10]. Weak inter-molecular C-H⋯O hydrogen bonds further link these ribbons into sheets parallel to (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 = 220.15

Triclinic,

a = 5.1277 (4) Å

b = 7.6368 (6) Å

c = 12.1571 (10) Å

α = 97.872 (3)°

β = 100.588 (3)°

γ = 106.194 (3)°

V = 440.37 (6) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.03

1967 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.25 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., 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003126/cv5043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003126/cv5043Isup2.hkl

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

C5H6N3O2+·NO3−·H2O	Z = 2
Mr = 220.15	F(000) = 228
Triclinic, P1	Dx = 1.66 Mg m−3
a = 5.1277 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6368 (6) Å	Cell parameters from 2815 reflections
c = 12.1571 (10) Å	θ = 2.8–27.5°
α = 97.872 (3)°	µ = 0.15 mm−1
β = 100.588 (3)°	T = 150 K
γ = 106.194 (3)°	Prism, yellow
V = 440.37 (6) Å3	0.58 × 0.49 × 0.42 mm

Bruker APEXII diffractometer	1693 reflections with I > 2σ(I)
graphite	Rint = 0.028
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→6
Tmin = 0.773, Tmax = 0.938	k = −9→9
5333 measured reflections	l = −15→15
1967 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.1681P] where P = (Fo2 + 2Fc2)/3
1967 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.3536 (3)	0.81463 (18)	0.56444 (11)	0.0213 (3)
C2	0.5373 (3)	0.93343 (17)	0.67594 (11)	0.0196 (3)
C3	0.5053 (3)	1.11068 (18)	0.71720 (11)	0.0206 (3)
C4	0.8826 (3)	1.14836 (19)	0.87398 (11)	0.0243 (3)
H4A	1.0058	1.2218	0.9434	0.029*
C5	0.9034 (3)	0.97938 (19)	0.83049 (11)	0.0239 (3)
H5	1.0420	0.9354	0.8702	0.029*
N1	0.4633 (3)	1.60420 (16)	0.88650 (10)	0.0226 (3)
N2	0.3198 (3)	1.18108 (16)	0.66687 (11)	0.0270 (3)
H2A	0.3137	1.2905	0.6980	0.032*
H2B	0.2019	1.1188	0.6021	0.032*
N3	0.6850 (2)	1.20958 (15)	0.81712 (10)	0.0228 (3)
H3	0.6719	1.3181	0.8460	0.027*
N4	0.7294 (2)	0.87393 (15)	0.73168 (9)	0.0219 (3)
O1	0.3992 (2)	0.65591 (14)	0.54062 (9)	0.0303 (3)
H1	0.3004	0.5977	0.4759	0.045*
O2	0.1873 (2)	0.86840 (14)	0.50431 (9)	0.0288 (3)
O3	0.4414 (2)	1.75010 (14)	0.93506 (9)	0.0326 (3)
O4	0.6850 (2)	1.56230 (14)	0.91237 (9)	0.0279 (3)
O5	0.2640 (2)	1.49165 (15)	0.80957 (9)	0.0337 (3)
O1W	0.8473 (3)	0.53972 (18)	0.65527 (11)	0.0490 (4)
H1W	0.979 (6)	0.543 (4)	0.704 (3)	0.074*
H2W	0.793 (6)	0.637 (4)	0.671 (2)	0.074*

	U11	U22	U33	U12	U13	U23
C1	0.0231 (6)	0.0211 (6)	0.0170 (6)	0.0071 (5)	0.0009 (5)	0.0001 (5)
C2	0.0215 (6)	0.0196 (6)	0.0156 (6)	0.0051 (5)	0.0021 (5)	0.0017 (5)
C3	0.0209 (6)	0.0205 (6)	0.0174 (6)	0.0035 (5)	0.0043 (5)	−0.0001 (5)
C4	0.0246 (7)	0.0254 (7)	0.0157 (6)	0.0011 (5)	0.0002 (5)	0.0009 (5)
C5	0.0236 (7)	0.0255 (7)	0.0178 (6)	0.0050 (5)	−0.0014 (5)	0.0029 (5)
N1	0.0265 (6)	0.0208 (5)	0.0185 (6)	0.0066 (5)	0.0036 (5)	0.0014 (4)
N2	0.0284 (6)	0.0234 (6)	0.0255 (6)	0.0119 (5)	−0.0023 (5)	−0.0038 (5)
N3	0.0253 (6)	0.0195 (5)	0.0189 (6)	0.0049 (5)	0.0017 (5)	−0.0029 (4)
N4	0.0242 (6)	0.0212 (5)	0.0173 (6)	0.0055 (5)	0.0011 (4)	0.0023 (4)
O1	0.0380 (6)	0.0252 (5)	0.0214 (5)	0.0159 (4)	−0.0088 (4)	−0.0075 (4)
O2	0.0300 (5)	0.0276 (5)	0.0243 (5)	0.0135 (4)	−0.0071 (4)	−0.0016 (4)
O3	0.0406 (6)	0.0231 (5)	0.0337 (6)	0.0116 (5)	0.0108 (5)	−0.0023 (4)
O4	0.0256 (5)	0.0275 (5)	0.0250 (5)	0.0093 (4)	−0.0031 (4)	−0.0030 (4)
O1W	0.0619 (9)	0.0472 (7)	0.0308 (6)	0.0396 (7)	−0.0220 (6)	−0.0188 (5)
O5	0.0284 (6)	0.0316 (6)	0.0316 (6)	0.0109 (4)	−0.0085 (4)	−0.0070 (4)

C1—O2	1.2162 (17)	C5—H5	0.9500
C1—O1	1.3017 (16)	N1—O3	1.2314 (14)
C1—C2	1.5050 (18)	N1—O4	1.2621 (15)
C2—N4	1.3132 (17)	N1—O5	1.2635 (15)
C2—C3	1.4420 (17)	N2—H2A	0.8800
C3—N2	1.3150 (18)	N2—H2B	0.8800
C3—N3	1.3580 (17)	N3—H3	0.8800
C4—N3	1.3488 (18)	O1—H1	0.8400
C4—C5	1.3663 (19)	O1W—H1W	0.81 (3)
C4—H4A	0.9500	O1W—H2W	0.88 (3)
C5—N4	1.3520 (17)
O2—C1—O1	125.51 (12)	C4—C5—H5	119.6
O2—C1—C2	121.65 (11)	O3—N1—O4	121.00 (12)
O1—C1—C2	112.82 (12)	O3—N1—O5	120.97 (12)
N4—C2—C3	121.68 (12)	O4—N1—O5	118.02 (11)
N4—C2—C1	118.46 (11)	C3—N2—H2A	120.0
C3—C2—C1	119.83 (12)	C3—N2—H2B	120.0
N2—C3—N3	118.84 (12)	H2A—N2—H2B	120.0
N2—C3—C2	125.70 (12)	C4—N3—C3	122.72 (11)
N3—C3—C2	115.46 (12)	C4—N3—H3	118.6
N3—C4—C5	119.16 (12)	C3—N3—H3	118.6
N3—C4—H4A	120.4	C2—N4—C5	120.09 (11)
C5—C4—H4A	120.4	C1—O1—H1	109.5
N4—C5—C4	120.89 (13)	H1W—O1W—H2W	110 (3)
N4—C5—H5	119.6
O2—C1—C2—N4	−174.02 (13)	N3—C4—C5—N4	0.1 (2)
O1—C1—C2—N4	4.43 (18)	C5—C4—N3—C3	−0.5 (2)
O2—C1—C2—C3	4.1 (2)	N2—C3—N3—C4	−179.55 (13)
O1—C1—C2—C3	−177.47 (12)	C2—C3—N3—C4	0.68 (19)
N4—C2—C3—N2	179.80 (13)	C3—C2—N4—C5	0.1 (2)
C1—C2—C3—N2	1.8 (2)	C1—C2—N4—C5	178.13 (12)
N4—C2—C3—N3	−0.45 (19)	C4—C5—N4—C2	0.1 (2)
C1—C2—C3—N3	−178.48 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wi	0.84	1.69	2.5233 (17)	168
O1W—H1W···O5ii	0.80 (3)	1.93 (3)	2.7152 (18)	167 (3)
O1W—H2W···O1	0.88 (3)	2.39 (3)	2.8825 (19)	116 (2)
O1W—H2W···N4	0.88 (3)	1.99 (3)	2.8566 (18)	170 (2)
N2—H2A···O5	0.88	2.01	2.8549 (17)	161
N2—H2B···O2	0.88	2.08	2.7163 (17)	128
N2—H2B···O2iii	0.88	2.20	2.9125 (18)	137
N3—H3···O4	0.88	1.91	2.7825 (16)	174
C4—H4A···O4iv	0.95	2.24	3.1818 (17)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1Wi	0.84	1.69	2.5233 (17)	168
O1W—H1W⋯O5ii	0.80 (3)	1.93 (3)	2.7152 (18)	167 (3)
O1W—H2W⋯O1	0.88 (3)	2.39 (3)	2.8825 (19)	116 (2)
O1W—H2W⋯N4	0.88 (3)	1.99 (3)	2.8566 (18)	170 (2)
N2—H2A⋯O5	0.88	2.01	2.8549 (17)	161
N2—H2B⋯O2	0.88	2.08	2.7163 (17)	128
N2—H2B⋯O2iii	0.88	2.20	2.9125 (18)	137
N3—H3⋯O4	0.88	1.91	2.7825 (16)	174
C4—H4A⋯O4iv	0.95	2.24	3.1818 (17)	169

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