3-Carb-oxy-pyridinium nitrate.

In the crystal structure of the title compound, C(6)H(6)NO(2) (+)·NO(3) (-), the protonated cations are linked by N-H⋯O hydrogen bonds into chains along the b axis. The cations and anions are also linked by N-H⋯O and O-H⋯O hydrogen bonds. C-H⋯O inter-actions also occur. In the cation, the ring makes a dihedral angle of 10.1 (3)° with the carboxylate group.

Related literature

For related structures, see: Athimoolam & Rajaram (2005 ▶); Athimoolam & Natarajan (2007 ▶); Kutoglu & Scheringer (1983 ▶); Jebas et al. (2006 ▶); Slouf (2001 ▶); Ye et al. (2010 ▶). For graph-set descriptors, see: Etter (1990 ▶); Bernstein et al. (1995 ▶); Motherwell et al. (2000 ▶).

Experimental

Crystal data

C6H6NO2 +·NO3 −

M = 186.13

Triclinic,

a = 6.7530 (4) Å

b = 7.5024 (4) Å

c = 8.4439 (5) Å

α = 81.895 (2)°

β = 82.215 (1)°

γ = 66.769 (2)°

V = 387.69 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.40 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.946, T max = 0.986

15468 measured reflections

1760 independent reflections

1102 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.13

1760 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2004 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028565/lx2240sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028565/lx2240Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028565/lx2240Isup3.cml

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

C6H6NO2+·NO3−	Z = 2
Mr = 186.13	F(000) = 192
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 6.7530 (4) Å	Cell parameters from 963 reflections
b = 7.5024 (4) Å	θ = 3.3–27.5°
c = 8.4439 (5) Å	µ = 0.14 mm−1
α = 81.895 (2)°	T = 293 K
β = 82.215 (1)°	Block, colourless
γ = 66.769 (2)°	0.40 × 0.20 × 0.10 mm
V = 387.69 (4) Å3

Rigaku R-AXIS RAPID diffractometer	1760 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −9→9
Tmin = 0.946, Tmax = 0.986	l = −10→10
15468 measured 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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.025P] where P = (Fo2 + 2Fc2)/3
1760 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.2671 (2)	−0.1191 (2)	0.48174 (17)	0.0528 (4)
H1O	0.277 (4)	−0.232 (4)	0.443 (3)	0.079 (8)*
N1	0.2399 (3)	0.3328 (2)	0.7169 (2)	0.0461 (5)
H1N	0.245 (4)	0.449 (4)	0.654 (3)	0.086 (9)*
C1	0.2321 (3)	−0.1404 (3)	0.6385 (2)	0.0405 (5)
O2	0.2000 (3)	−0.2778 (2)	0.71433 (17)	0.0570 (5)
N2	0.2859 (3)	0.5132 (2)	0.2675 (2)	0.0461 (4)
C2	0.2350 (3)	0.0215 (2)	0.7207 (2)	0.0366 (4)
O3	0.2861 (3)	0.3523 (2)	0.2502 (2)	0.0723 (6)
C3	0.2385 (3)	0.1913 (3)	0.6360 (2)	0.0416 (5)
H3	0.2399	0.2079	0.5247	0.050*
O4	0.2781 (3)	0.5540 (2)	0.40863 (18)	0.0698 (5)
C4	0.2393 (3)	0.3167 (3)	0.8764 (3)	0.0483 (5)
H4	0.2410	0.4182	0.9273	0.058*
C5	0.2361 (3)	0.1507 (3)	0.9645 (2)	0.0497 (5)
H5	0.2348	0.1381	1.0758	0.060*
O5	0.2917 (3)	0.6324 (3)	0.1555 (2)	0.0817 (6)
C6	0.2350 (3)	0.0018 (3)	0.8862 (2)	0.0439 (5)
H6	0.2341	−0.1126	0.9449	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0802 (11)	0.0451 (9)	0.0395 (9)	−0.0309 (8)	0.0008 (7)	−0.0094 (6)
N1	0.0598 (11)	0.0313 (9)	0.0518 (11)	−0.0232 (8)	−0.0029 (8)	−0.0032 (7)
C1	0.0501 (11)	0.0346 (10)	0.0389 (11)	−0.0185 (9)	−0.0027 (8)	−0.0052 (8)
O2	0.0937 (12)	0.0416 (8)	0.0482 (9)	−0.0412 (8)	−0.0003 (8)	−0.0045 (7)
N2	0.0578 (11)	0.0445 (10)	0.0380 (9)	−0.0205 (8)	−0.0065 (7)	−0.0053 (7)
C2	0.0447 (10)	0.0304 (9)	0.0364 (10)	−0.0171 (8)	−0.0010 (8)	−0.0033 (7)
O3	0.1120 (14)	0.0623 (11)	0.0602 (11)	−0.0464 (10)	−0.0100 (9)	−0.0208 (8)
C3	0.0533 (12)	0.0346 (10)	0.0390 (10)	−0.0202 (9)	−0.0018 (8)	−0.0025 (8)
O4	0.1353 (15)	0.0522 (10)	0.0359 (9)	−0.0481 (10)	−0.0118 (9)	−0.0077 (7)
C4	0.0580 (13)	0.0421 (11)	0.0514 (13)	−0.0237 (10)	−0.0038 (9)	−0.0126 (9)
C5	0.0660 (14)	0.0477 (12)	0.0408 (12)	−0.0264 (11)	−0.0052 (10)	−0.0077 (9)
O5	0.1135 (15)	0.0740 (12)	0.0513 (10)	−0.0380 (11)	−0.0075 (9)	0.0208 (9)
C6	0.0585 (12)	0.0352 (10)	0.0419 (11)	−0.0230 (9)	−0.0024 (9)	−0.0031 (8)

O1—C1	1.311 (2)	N2—O4	1.261 (2)
O1—H1O	0.92 (3)	C2—C3	1.377 (2)
N1—C4	1.335 (3)	C2—C6	1.385 (3)
N1—C3	1.344 (3)	C3—H3	0.9300
N1—H1N	0.96 (3)	C4—C5	1.364 (3)
C1—O2	1.213 (2)	C4—H4	0.9300
C1—C2	1.489 (3)	C5—C6	1.379 (3)
N2—O5	1.214 (2)	C5—H5	0.9300
N2—O3	1.236 (2)	C6—H6	0.9300
C1—O1—H1O	107.7 (16)	N1—C3—C2	118.93 (18)
C4—N1—C3	123.13 (17)	N1—C3—H3	120.5
C4—N1—H1N	120.2 (16)	C2—C3—H3	120.5
C3—N1—H1N	116.7 (16)	N1—C4—C5	119.72 (18)
O2—C1—O1	124.77 (18)	N1—C4—H4	120.1
O2—C1—C2	121.11 (18)	C5—C4—H4	120.1
O1—C1—C2	114.11 (16)	C4—C5—C6	119.0 (2)
O5—N2—O3	123.04 (18)	C4—C5—H5	120.5
O5—N2—O4	119.22 (18)	C6—C5—H5	120.5
O3—N2—O4	117.74 (17)	C5—C6—C2	120.39 (18)
C3—C2—C6	118.80 (17)	C5—C6—H6	119.8
C3—C2—C1	121.64 (17)	C2—C6—H6	119.8
C6—C2—C1	119.56 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4i	0.92 (3)	1.67 (3)	2.5833 (19)	169 (2)
N1—H1N···O2ii	0.96 (3)	2.08 (3)	2.824 (2)	133 (2)
N1—H1N···O4	0.96 (3)	2.12 (3)	2.921 (2)	139 (2)
C3—H3···O3	0.93	2.45	3.330 (3)	158
C6—H6···O5iii	0.93	2.37	3.259 (2)	160
C5—H5···O3iv	0.93	2.47	3.142 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4i	0.92 (3)	1.67 (3)	2.5833 (19)	169 (2)
N1—H1N⋯O2ii	0.96 (3)	2.08 (3)	2.824 (2)	133 (2)
N1—H1N⋯O4	0.96 (3)	2.12 (3)	2.921 (2)	139 (2)
C3—H3⋯O3	0.93	2.45	3.330 (3)	158
C6—H6⋯O5iii	0.93	2.37	3.259 (2)	160
C5—H5⋯O3iv	0.93	2.47	3.142 (2)	129

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