2-Amino-3-carb-oxy-pyridinium nitrate.

In the crystal structure of the title compound, C(6)H(7)N(2)O(2) (+)·NO(3) (-), the cations are linked via C-H⋯O hydrogen bonds, forming infinite chains running along the b axis. These chains are further linked through N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds to the nitrate anions, forming well-separated infinite planar layers parallel to (001).

Related literature

For hybrid compounds based on nicotinic acid, see: Athimoolam et al. (2005 ▶); Athimoolam & Rajaram (2005a ▶,b ▶); Chen (2009 ▶); Slouf (2001 ▶); Ye et al. (2010 ▶). For hybrid compounds based on amino-nicotinic acid derivatives, see: Akriche & Rzaigui (2007 ▶); Berrah et al. (2011a ▶); Giantsidis & Turnbull (2000 ▶). For related nitrate compounds, see: Berrah et al. (2011b ▶); Jebas et al. (2006 ▶).

Experimental

Crystal data

C6H7N2O2 +·NO3 −

M = 201.15

Tetragonal,

a = 16.122 (2) Å

c = 12.446 (3) Å

V = 3235.0 (11) Å3

Z = 16

Mo Kα radiation

μ = 0.15 mm−1

T = 150 K

0.39 × 0.07 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.476, T max = 0.993

5438 measured reflections

1509 independent reflections

921 reflections with I > 2σ(I)

R int = 0.112

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.158

S = 0.97

1509 reflections

128 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811027978/lx2193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027978/lx2193Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027978/lx2193Isup3.cml

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

C6H7N2O2+·NO3−	Dx = 1.652 Mg m−3
Mr = 201.15	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41cd	Cell parameters from 491 reflections
Hall symbol: I 4bw -2c	θ = 3.3–20.3°
a = 16.122 (2) Å	µ = 0.15 mm−1
c = 12.446 (3) Å	T = 150 K
V = 3235.0 (11) Å3	Needle, colourless
Z = 16	0.39 × 0.07 × 0.05 mm
F(000) = 1664

Bruker APEXII diffractometer	921 reflections with I > 2σ(I)
graphite	Rint = 0.112
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −16→20
Tmin = 0.476, Tmax = 0.993	k = −13→20
5438 measured reflections	l = −16→10
1509 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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F2) = 0.158	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
1509 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.28 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	0.1754 (3)	0.1137 (3)	0.0309 (6)	0.0288 (11)
C2	0.1875 (3)	0.0223 (2)	0.0276 (6)	0.0229 (10)
C3	0.1218 (3)	−0.0300 (3)	0.0259 (6)	0.0295 (12)
H3	0.0686	−0.0078	0.0264	0.035*
C4	0.1311 (3)	−0.1174 (3)	0.0233 (7)	0.0309 (11)
H4	0.0854	−0.1526	0.0215	0.037*
C5	0.2092 (3)	−0.1469 (3)	0.0235 (7)	0.0302 (12)
H5	0.2179	−0.2039	0.0221	0.036*
C6	0.2702 (2)	−0.0099 (3)	0.0279 (10)	0.0234 (10)
N1	0.1623 (2)	−0.0149 (2)	0.2777 (8)	0.0247 (8)
N2	0.2755 (2)	−0.0950 (2)	0.0256 (5)	0.0269 (9)
H2	0.3242	−0.1168	0.0256	0.032*
N3	0.3388 (2)	0.0327 (2)	0.0312 (5)	0.0308 (10)
H3A	0.3858	0.0075	0.032	0.037*
H3B	0.3371	0.086	0.0326	0.037*
O1	0.20156 (19)	0.05016 (19)	0.2755 (4)	0.0313 (8)
O2	0.08451 (16)	−0.01536 (18)	0.2757 (5)	0.0293 (8)
O3	0.19907 (18)	−0.08530 (18)	0.2798 (5)	0.0309 (8)
O5	0.09671 (19)	0.13575 (18)	0.0242 (4)	0.0342 (9)
H51	0.0932	0.1865	0.0259	0.051*
O4	0.2318 (2)	0.1628 (2)	0.0360 (4)	0.0355 (10)

	U11	U22	U33	U12	U13	U23
C1	0.035 (3)	0.017 (2)	0.035 (3)	−0.002 (2)	−0.001 (4)	−0.004 (3)
C2	0.020 (2)	0.021 (3)	0.028 (2)	0.0022 (16)	0.001 (3)	0.002 (4)
C3	0.025 (3)	0.021 (2)	0.042 (3)	−0.0068 (19)	0.000 (4)	0.003 (3)
C4	0.042 (3)	0.016 (3)	0.035 (3)	−0.001 (2)	−0.003 (5)	0.000 (3)
C5	0.040 (3)	0.014 (2)	0.036 (3)	−0.014 (2)	−0.004 (4)	−0.001 (4)
C6	0.022 (2)	0.026 (3)	0.022 (2)	−0.0025 (18)	−0.006 (5)	0.003 (3)
N1	0.0198 (18)	0.020 (2)	0.0341 (18)	−0.0058 (16)	0.006 (4)	−0.001 (4)
N2	0.024 (2)	0.022 (2)	0.035 (2)	0.0103 (15)	−0.005 (3)	−0.002 (3)
N3	0.0137 (19)	0.029 (2)	0.050 (2)	−0.0035 (15)	0.003 (3)	0.002 (3)
O1	0.0253 (18)	0.0256 (17)	0.043 (2)	−0.0062 (15)	0.000 (3)	−0.006 (3)
O2	0.0124 (15)	0.0231 (18)	0.052 (2)	0.0030 (13)	0.004 (3)	0.004 (3)
O3	0.0130 (16)	0.0233 (17)	0.056 (2)	0.0049 (13)	−0.002 (3)	−0.007 (3)
O5	0.0233 (17)	0.0205 (19)	0.059 (2)	0.0042 (14)	0.004 (3)	0.000 (3)
O4	0.0253 (19)	0.0212 (18)	0.060 (3)	0.0027 (15)	−0.003 (3)	−0.005 (3)

C1—O4	1.207 (6)	C5—H5	0.93
C1—O5	1.319 (6)	C6—N3	1.303 (5)
C1—C2	1.487 (6)	C6—N2	1.375 (6)
C2—C3	1.354 (6)	N1—O1	1.225 (4)
C2—C6	1.431 (5)	N1—O2	1.255 (4)
C3—C4	1.417 (6)	N1—O3	1.281 (4)
C3—H3	0.93	N2—H2	0.86
C4—C5	1.347 (8)	N3—H3A	0.86
C4—H4	0.93	N3—H3B	0.86
C5—N2	1.359 (6)	O5—H51	0.82
O4—C1—O5	123.4 (4)	N2—C5—H5	119.4
O4—C1—C2	123.5 (4)	N3—C6—N2	118.2 (4)
O5—C1—C2	113.0 (4)	N3—C6—C2	126.9 (5)
C3—C2—C6	120.2 (4)	N2—C6—C2	114.8 (4)
C3—C2—C1	121.0 (4)	O1—N1—O2	121.4 (4)
C6—C2—C1	118.8 (4)	O1—N1—O3	121.4 (3)
C2—C3—C4	122.5 (4)	O2—N1—O3	117.2 (3)
C2—C3—H3	118.8	C5—N2—C6	124.5 (4)
C4—C3—H3	118.8	C5—N2—H2	117.8
C5—C4—C3	116.8 (4)	C6—N2—H2	117.8
C5—C4—H4	121.6	C6—N3—H3A	120
C3—C4—H4	121.6	C6—N3—H3B	120
C4—C5—N2	121.2 (4)	H3A—N3—H3B	120
C4—C5—H5	119.4	C1—O5—H51	109.5
O4—C1—C2—C3	177.5 (7)	C3—C2—C6—N3	−178.8 (9)
O5—C1—C2—C3	−4.4 (11)	C1—C2—C6—N3	0.4 (17)
O4—C1—C2—C6	−1.6 (13)	C3—C2—C6—N2	0.3 (14)
O5—C1—C2—C6	176.4 (9)	C1—C2—C6—N2	179.5 (7)
C6—C2—C3—C4	−0.6 (12)	C4—C5—N2—C6	0.0 (14)
C1—C2—C3—C4	−179.7 (7)	N3—C6—N2—C5	179.1 (8)
C2—C3—C4—C5	0.5 (11)	C2—C6—N2—C5	−0.1 (15)
C3—C4—C5—N2	−0.3 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.86	1.97	2.803 (4)	162
N3—H3A···O2i	0.86	2.18	3.017 (4)	165
N3—H3A···O2ii	0.86	2.43	2.967 (4)	121
N3—H3B···O4	0.86	2.10	2.716 (5)	128
O5—H51···O3iii	0.82	1.85	2.670 (4)	180
C4—H4···O1iv	0.93	2.42	3.197 (6)	141
C5—H5···O4v	0.93	2.30	3.216 (6)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	1.97	2.803 (4)	162
N3—H3A⋯O2i	0.86	2.18	3.017 (4)	165
N3—H3A⋯O2ii	0.86	2.43	2.967 (4)	121
N3—H3B⋯O4	0.86	2.10	2.716 (5)	128
O5—H51⋯O3iii	0.82	1.85	2.670 (4)	180
C4—H4⋯O1iv	0.93	2.42	3.197 (6)	141
C5—H5⋯O4v	0.93	2.30	3.216 (6)	167

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