Ammonium 2-amino-pyrazine-3-carboxyl-ate.

The title compound NH(4) (+)·C(5)H(4)N(3)O(2) (-) crystallizes with two formula units in the asymmetric unit. In each anion, the carboxyl-ate is deprotonated and the planar amino group [angle sums of 359 (3) and 355 (3)° at N] remains protonated. In the crystal, the cations and anions are bridged by N-H⋯O and N-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structure of the free acid, see: Dobson & Gerkin (1996 ▶); Ptasiewicz-Bak & Leciejewicz (1997 ▶). For the metal complex with nickel, see: Ptasiewicz-Bak & Leciejewicz (1999 ▶). For the coordination chemistry of 2-pyrazine­carb­oxy­lic acid, see: Ptasiewicz-Bak et al. (1995 ▶); Ellsworth & zur Loye (2008 ▶). In the present study a half-normal probability plot (Abrahams & Keve, 1971 ▶), a quaternion fit (Mackay, 1984 ▶) and rigid-body analysis (Schomaker & Trueblood, 1998 ▶) have been used.

Experimental

Crystal data

NH4 +·C5H4N3O2 −

M = 156.15

Orthorhombic,

a = 12.5066 (6) Å

b = 3.8833 (2) Å

c = 27.9659 (14) Å

V = 1358.22 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.40 × 0.19 × 0.09 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.70, T max = 0.75

16898 measured reflections

1580 independent reflections

1540 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.072

S = 1.05

1580 reflections

247 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: manual editing of SHELXL cif file.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010865/zl2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010865/zl2357Isup2.hkl

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

NH4+·C5H4N3O2−	F(000) = 656
Mr = 156.15	Dx = 1.527 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9416 reflections
a = 12.5066 (6) Å	θ = 2.9–27.5°
b = 3.8833 (2) Å	µ = 0.12 mm−1
c = 27.9659 (14) Å	T = 150 K
V = 1358.22 (12) Å3	Plate, colourless
Z = 8	0.40 × 0.19 × 0.09 mm

Bruker Kappa APEXII diffractometer	1580 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −16→15
Tmin = 0.70, Tmax = 0.75	k = −4→5
16898 measured reflections	l = −36→36

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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.1369P] where P = (Fo2 + 2Fc2)/3
1580 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.16 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
O11	0.42965 (10)	0.7629 (3)	0.54691 (4)	0.0224 (3)
O21	0.30439 (11)	0.9858 (4)	0.59468 (5)	0.0238 (3)
N11	0.55372 (12)	0.5954 (4)	0.62042 (5)	0.0188 (3)
N21	0.50221 (12)	0.7550 (4)	0.71454 (5)	0.0200 (3)
N31	0.34689 (13)	1.0186 (4)	0.69017 (5)	0.0224 (3)
H31A	0.338 (2)	1.088 (7)	0.7212 (11)	0.031 (6)*
H31B	0.304 (2)	1.100 (7)	0.6670 (10)	0.032 (7)*
C11	0.61962 (15)	0.5125 (5)	0.65636 (6)	0.0211 (3)
H11	0.6854	0.3996	0.6498	0.025*
C21	0.59216 (14)	0.5908 (5)	0.70302 (6)	0.0209 (3)
H21	0.6395	0.5246	0.7279	0.025*
C31	0.43627 (13)	0.8473 (4)	0.67848 (6)	0.0164 (3)
C41	0.46320 (13)	0.7604 (4)	0.63013 (6)	0.0156 (3)
C51	0.39253 (13)	0.8432 (4)	0.58752 (6)	0.0174 (3)
O12	0.14633 (10)	0.3689 (4)	0.46142 (4)	0.0245 (3)
O22	0.02147 (11)	0.5588 (4)	0.41050 (5)	0.0281 (3)
N12	0.26120 (11)	0.1003 (4)	0.39032 (5)	0.0188 (3)
N22	0.21177 (12)	0.2151 (4)	0.29449 (5)	0.0207 (3)
N32	0.05731 (12)	0.4997 (4)	0.31616 (6)	0.0232 (3)
H32A	0.0512 (19)	0.574 (6)	0.2864 (10)	0.026 (6)*
H32B	0.020 (2)	0.611 (7)	0.3371 (10)	0.035 (7)*
C12	0.32517 (14)	−0.0150 (5)	0.35539 (7)	0.0211 (3)
H12	0.3883	−0.1386	0.3632	0.025*
C22	0.29979 (14)	0.0451 (5)	0.30788 (7)	0.0216 (4)
H22	0.3469	−0.0379	0.2838	0.026*
C32	0.14642 (13)	0.3310 (4)	0.32951 (6)	0.0175 (3)
C42	0.17362 (13)	0.2711 (4)	0.37884 (5)	0.0163 (3)
C52	0.10825 (13)	0.4099 (4)	0.42027 (6)	0.0189 (3)
N3	0.12272 (12)	0.8079 (4)	0.53838 (5)	0.0201 (3)
H3A	0.133 (2)	0.702 (7)	0.5094 (11)	0.032 (6)*
H3B	0.189 (2)	0.888 (7)	0.5486 (10)	0.032 (6)*
H3C	0.086 (2)	0.660 (7)	0.5602 (11)	0.037 (6)*
H3D	0.079 (2)	0.986 (7)	0.5356 (9)	0.034 (7)*
N4	0.37274 (14)	0.2716 (5)	0.47857 (6)	0.0249 (3)
H4A	0.312 (3)	0.249 (7)	0.4640 (11)	0.043 (8)*
H4B	0.380 (2)	0.443 (10)	0.5025 (14)	0.057 (9)*
H4C	0.388 (2)	0.102 (8)	0.4961 (12)	0.043 (8)*
H4D	0.420 (2)	0.315 (7)	0.4564 (10)	0.032 (6)*

	U11	U22	U33	U12	U13	U23
O11	0.0230 (6)	0.0326 (7)	0.0115 (5)	−0.0014 (5)	−0.0003 (4)	0.0001 (5)
O21	0.0174 (6)	0.0355 (7)	0.0184 (6)	0.0022 (5)	−0.0026 (4)	−0.0009 (5)
N11	0.0193 (7)	0.0201 (7)	0.0169 (7)	0.0002 (5)	0.0015 (5)	0.0005 (5)
N21	0.0234 (7)	0.0226 (7)	0.0140 (6)	−0.0029 (6)	−0.0012 (6)	0.0007 (5)
N31	0.0204 (7)	0.0308 (8)	0.0160 (7)	0.0036 (6)	−0.0001 (5)	−0.0042 (6)
C11	0.0186 (8)	0.0222 (8)	0.0225 (8)	0.0031 (6)	−0.0017 (6)	0.0005 (6)
C21	0.0224 (8)	0.0214 (8)	0.0189 (8)	−0.0019 (6)	−0.0049 (6)	0.0019 (7)
C31	0.0190 (8)	0.0168 (7)	0.0133 (7)	−0.0055 (6)	−0.0001 (5)	0.0000 (6)
C41	0.0158 (7)	0.0179 (7)	0.0131 (7)	−0.0029 (6)	0.0006 (6)	0.0006 (5)
C51	0.0178 (8)	0.0201 (7)	0.0145 (7)	−0.0060 (6)	−0.0006 (5)	0.0014 (6)
O12	0.0280 (6)	0.0322 (7)	0.0133 (5)	0.0041 (5)	0.0000 (5)	−0.0021 (5)
O22	0.0226 (6)	0.0423 (8)	0.0193 (6)	0.0091 (6)	0.0021 (5)	−0.0012 (6)
N12	0.0183 (6)	0.0220 (7)	0.0162 (6)	−0.0019 (5)	−0.0004 (5)	−0.0018 (5)
N22	0.0234 (7)	0.0237 (7)	0.0151 (6)	−0.0040 (6)	0.0019 (5)	−0.0016 (5)
N32	0.0227 (7)	0.0325 (8)	0.0144 (7)	0.0024 (6)	−0.0005 (6)	0.0043 (6)
C12	0.0190 (8)	0.0224 (9)	0.0220 (8)	0.0008 (6)	0.0014 (6)	−0.0026 (7)
C22	0.0228 (8)	0.0217 (8)	0.0203 (8)	−0.0029 (6)	0.0055 (6)	−0.0050 (6)
C32	0.0187 (8)	0.0192 (7)	0.0146 (7)	−0.0054 (6)	−0.0004 (6)	−0.0004 (6)
C42	0.0176 (7)	0.0187 (8)	0.0126 (7)	−0.0032 (6)	0.0006 (6)	−0.0012 (6)
C52	0.0198 (8)	0.0211 (8)	0.0158 (7)	−0.0014 (6)	0.0025 (6)	−0.0017 (6)
N3	0.0196 (7)	0.0230 (7)	0.0178 (7)	−0.0004 (6)	−0.0007 (5)	−0.0002 (6)
N4	0.0227 (7)	0.0348 (9)	0.0174 (7)	−0.0044 (6)	−0.0042 (6)	0.0037 (7)

O11—C51	1.266 (2)	N22—C22	1.337 (2)
O21—C51	1.250 (2)	N22—C32	1.353 (2)
N11—C41	1.329 (2)	N32—C32	1.346 (2)
N11—C11	1.339 (2)	N32—H32A	0.88 (3)
N21—C21	1.333 (2)	N32—H32B	0.86 (3)
N21—C31	1.351 (2)	C12—C22	1.386 (3)
N31—C31	1.341 (2)	C12—H12	0.9500
N31—H31A	0.92 (3)	C22—H22	0.9500
N31—H31B	0.90 (3)	C32—C42	1.440 (2)
C11—C21	1.383 (2)	C42—C52	1.517 (2)
C11—H11	0.9500	N3—H3A	0.92 (3)
C21—H21	0.9500	N3—H3B	0.93 (3)
C31—C41	1.434 (2)	N3—H3C	0.96 (3)
C41—C51	1.518 (2)	N3—H3D	0.89 (3)
O12—C52	1.256 (2)	N4—H4A	0.86 (3)
O22—C52	1.260 (2)	N4—H4B	0.95 (4)
N12—C42	1.320 (2)	N4—H4C	0.84 (3)
N12—C12	1.340 (2)	N4—H4D	0.87 (3)
C41—N11—C11	119.14 (15)	N12—C12—H12	119.8
C21—N21—C31	117.49 (15)	C22—C12—H12	119.8
C31—N31—H31A	118.4 (17)	N22—C22—C12	122.70 (16)
C31—N31—H31B	119.6 (17)	N22—C22—H22	118.7
H31A—N31—H31B	121 (2)	C12—C22—H22	118.7
N11—C11—C21	120.16 (16)	N32—C32—N22	117.48 (15)
N11—C11—H11	119.9	N32—C32—C42	122.70 (16)
C21—C11—H11	119.9	N22—C32—C42	119.81 (15)
N21—C21—C11	122.88 (16)	N12—C42—C32	120.68 (15)
N21—C21—H21	118.6	N12—C42—C52	116.10 (14)
C11—C21—H21	118.6	C32—C42—C52	123.17 (15)
N31—C31—N21	117.27 (15)	O12—C52—O22	125.71 (15)
N31—C31—C41	122.85 (15)	O12—C52—C42	116.79 (14)
N21—C31—C41	119.88 (15)	O22—C52—C42	117.50 (15)
N11—C41—C31	120.42 (15)	H3A—N3—H3B	107 (2)
N11—C41—C51	115.96 (14)	H3A—N3—H3C	111 (2)
C31—C41—C51	123.62 (14)	H3B—N3—H3C	116 (2)
O21—C51—O11	125.19 (15)	H3A—N3—H3D	111 (2)
O21—C51—C41	118.80 (14)	H3B—N3—H3D	108 (2)
O11—C51—C41	116.01 (14)	H3C—N3—H3D	103 (2)
C42—N12—C12	119.08 (15)	H4A—N4—H4B	119 (3)
C22—N22—C32	117.32 (15)	H4A—N4—H4C	113 (3)
C32—N32—H32A	119.4 (16)	H4B—N4—H4C	97 (3)
C32—N32—H32B	119.9 (18)	H4A—N4—H4D	106 (3)
H32A—N32—H32B	116 (2)	H4B—N4—H4D	107 (3)
N12—C12—C22	120.40 (16)	H4C—N4—H4D	114 (3)
C41—N11—C11—C21	1.6 (3)	C42—N12—C12—C22	0.1 (2)
C31—N21—C21—C11	−0.2 (3)	C32—N22—C22—C12	0.2 (3)
N11—C11—C21—N21	−1.4 (3)	N12—C12—C22—N22	−0.5 (3)
C21—N21—C31—N31	−178.70 (15)	C22—N22—C32—N32	−179.47 (15)
C21—N21—C31—C41	1.5 (2)	C22—N22—C32—C42	0.5 (2)
C11—N11—C41—C31	−0.2 (2)	C12—N12—C42—C32	0.5 (2)
C11—N11—C41—C51	−179.62 (15)	C12—N12—C42—C52	−176.88 (15)
N31—C31—C41—N11	178.87 (16)	N32—C32—C42—N12	179.09 (15)
N21—C31—C41—N11	−1.3 (2)	N22—C32—C42—N12	−0.8 (2)
N31—C31—C41—C51	−1.8 (2)	N32—C32—C42—C52	−3.7 (2)
N21—C31—C41—C51	178.00 (15)	N22—C32—C42—C52	176.38 (14)
N11—C41—C51—O21	177.16 (15)	N12—C42—C52—O12	4.3 (2)
C31—C41—C51—O21	−2.2 (2)	C32—C42—C52—O12	−173.05 (16)
N11—C41—C51—O11	−3.6 (2)	N12—C42—C52—O22	−176.49 (15)
C31—C41—C51—O11	177.04 (15)	C32—C42—C52—O22	6.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N31—H31A···N22i	0.92 (3)	2.20 (3)	3.103 (2)	169 (2)
N31—H31B···O21	0.90 (3)	2.07 (3)	2.726 (2)	129 (2)
N32—H32A···N21ii	0.88 (3)	2.23 (3)	3.100 (2)	168 (2)
N32—H32B···O22	0.86 (3)	2.06 (3)	2.686 (2)	129 (2)
N3—H3B···O21	0.93 (3)	1.97 (3)	2.849 (2)	157 (2)
N3—H3C···O11iii	0.96 (3)	2.58 (3)	3.287 (2)	131 (2)
N3—H3C···N11iii	0.96 (3)	2.00 (3)	2.909 (2)	159 (2)
N3—H3D···O11iv	0.89 (3)	2.13 (3)	2.944 (2)	152 (2)
N4—H4A···O12	0.86 (3)	2.13 (3)	2.897 (2)	148 (3)
N4—H4A···N12	0.86 (3)	2.23 (3)	2.912 (2)	135 (3)
N4—H4B···O11	0.95 (4)	1.86 (4)	2.793 (2)	166 (3)
N4—H4C···O11v	0.84 (3)	2.01 (4)	2.839 (2)	170 (3)
N4—H4D···O22vi	0.87 (3)	1.87 (3)	2.742 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N31—H31A⋯N22i	0.92 (3)	2.20 (3)	3.103 (2)	169 (2)
N31—H31B⋯O21	0.90 (3)	2.07 (3)	2.726 (2)	129 (2)
N32—H32A⋯N21ii	0.88 (3)	2.23 (3)	3.100 (2)	168 (2)
N32—H32B⋯O22	0.86 (3)	2.06 (3)	2.686 (2)	129 (2)
N3—H3B⋯O21	0.93 (3)	1.97 (3)	2.849 (2)	157 (2)
N3—H3C⋯O11iii	0.96 (3)	2.58 (3)	3.287 (2)	131 (2)
N3—H3C⋯N11iii	0.96 (3)	2.00 (3)	2.909 (2)	159 (2)
N3—H3D⋯O11iv	0.89 (3)	2.13 (3)	2.944 (2)	152 (2)
N4—H4A⋯O12	0.86 (3)	2.13 (3)	2.897 (2)	148 (3)
N4—H4A⋯N12	0.86 (3)	2.23 (3)	2.912 (2)	135 (3)
N4—H4B⋯O11	0.95 (4)	1.86 (4)	2.793 (2)	166 (3)
N4—H4C⋯O11v	0.84 (3)	2.01 (4)	2.839 (2)	170 (3)
N4—H4D⋯O22vi	0.87 (3)	1.87 (3)	2.742 (2)	176 (3)

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