3-Hy-droxy-pyridinium-2-carboxylate.

Comparable to many amino acids, the title compound, C(6)H(5)NO(3), is a substitution product of picolinic acid. The mol-ecule shows approximate non-crystallographic C(s) symmetry. Like many amino acids, the mol-ecule is present in its zwitterionic state. Intra- as well as inter-molecular hydrogen bonds are observed, the latter connecting the mol-ecules into zigzag chains along the crystallographic b axis. An inter-molecular C-C distance of only 3.368 (2) Å exclusively involving carbon atoms of aromatic rings (centroid-centroid separation = 3.803 Å) is indicative of π-π inter-actions connecting the mol-ecules into stacks along the crystallographic a axis.

Related literature

For the use of chelate ligands as opposed to monodentate ligands, see: Gade (1998 ▶). For the crystal structures of two mercury coordination compounds applying the title compound as a mono-, as well as a bidentate, ligand, see: Popović et al. (2007 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H5NO3

M = 139.11

Monoclinic,

a = 3.8034 (1) Å

b = 6.8144 (2) Å

c = 11.1807 (4) Å

β = 95.102 (1)°

V = 288.63 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 200 K

0.56 × 0.50 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

2659 measured reflections

768 independent reflections

758 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.07

768 reflections

96 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027462/ez2254sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811027462/ez2254Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027462/ez2254Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811027462/ez2254Isup4.cml

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

C6H5NO3	F(000) = 144
Mr = 139.11	Dx = 1.601 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2465 reflections
a = 3.8034 (1) Å	θ = 3.0–28.3°
b = 6.8144 (2) Å	µ = 0.13 mm−1
c = 11.1807 (4) Å	T = 200 K
β = 95.102 (1)°	Block, colourless
V = 288.63 (2) Å3	0.56 × 0.50 × 0.22 mm
Z = 2

Bruker APEXII CCD diffractometer	758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −5→3
2659 measured reflections	k = −9→9
768 independent reflections	l = −14→14

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.0435P] where P = (Fo2 + 2Fc2)/3
768 reflections	(Δ/σ)max < 0.001
96 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (588 pairs) have been merged and the item was removed from the CIF.

	x	y	z	Uiso*/Ueq
O1	−0.0877 (3)	0.8750 (2)	0.28327 (12)	0.0355 (3)
O2	−0.0543 (4)	0.7074 (2)	0.45701 (11)	0.0357 (3)
O3	0.1674 (4)	0.7340 (2)	0.10355 (11)	0.0350 (3)
H3	0.0796	0.8189	0.1465	0.053*
N1	0.2583 (3)	0.4001 (2)	0.35230 (10)	0.0207 (3)
H71	0.188 (7)	0.386 (5)	0.437 (2)	0.051 (7)*
C1	−0.0040 (4)	0.7302 (2)	0.35008 (14)	0.0242 (3)
C2	0.1756 (4)	0.5650 (2)	0.28933 (12)	0.0191 (3)
C3	0.2518 (4)	0.5751 (2)	0.16925 (12)	0.0226 (3)
C4	0.4148 (4)	0.4133 (3)	0.11965 (12)	0.0270 (4)
H4	0.4699	0.4169	0.0385	0.032*
C5	0.4942 (4)	0.2504 (3)	0.18837 (14)	0.0274 (3)
H5	0.6056	0.1411	0.1549	0.033*
C6	0.4120 (4)	0.2445 (3)	0.30745 (14)	0.0254 (3)
H6	0.4648	0.1315	0.3556	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0439 (7)	0.0223 (6)	0.0408 (7)	0.0096 (6)	0.0061 (5)	0.0009 (5)
O2	0.0495 (7)	0.0310 (7)	0.0287 (5)	0.0057 (6)	0.0149 (5)	−0.0076 (5)
O3	0.0464 (7)	0.0322 (7)	0.0274 (6)	0.0076 (6)	0.0081 (5)	0.0125 (6)
N1	0.0247 (6)	0.0195 (6)	0.0182 (5)	−0.0026 (5)	0.0037 (4)	0.0009 (5)
C1	0.0254 (7)	0.0189 (7)	0.0288 (7)	0.0011 (6)	0.0046 (5)	−0.0054 (6)
C2	0.0206 (6)	0.0175 (6)	0.0196 (6)	−0.0010 (5)	0.0034 (4)	−0.0007 (6)
C3	0.0240 (6)	0.0236 (8)	0.0202 (6)	−0.0008 (6)	0.0021 (5)	0.0034 (6)
C4	0.0272 (7)	0.0352 (9)	0.0194 (6)	0.0013 (7)	0.0061 (5)	−0.0038 (7)
C5	0.0278 (7)	0.0261 (8)	0.0285 (7)	0.0035 (7)	0.0045 (5)	−0.0087 (7)
C6	0.0282 (7)	0.0196 (7)	0.0281 (7)	0.0007 (6)	0.0012 (5)	0.0014 (6)

O1—C1	1.261 (2)	C2—C3	1.4002 (17)
O2—C1	1.237 (2)	C3—C4	1.403 (2)
O3—C3	1.332 (2)	C4—C5	1.369 (3)
O3—H3	0.8400	C4—H4	0.9500
N1—C6	1.330 (2)	C5—C6	1.395 (2)
N1—C2	1.348 (2)	C5—H5	0.9500
N1—H71	1.01 (2)	C6—H6	0.9500
C1—C2	1.510 (2)
?···?	?
C3—O3—H3	109.5	O3—C3—C4	120.95 (13)
C6—N1—C2	123.88 (12)	C2—C3—C4	118.48 (14)
C6—N1—H71	115.9 (19)	C5—C4—C3	119.92 (12)
C2—N1—H71	120.1 (19)	C5—C4—H4	120.0
O2—C1—O1	128.19 (15)	C3—C4—H4	120.0
O2—C1—C2	117.13 (15)	C4—C5—C6	120.15 (15)
O1—C1—C2	114.68 (13)	C4—C5—H5	119.9
N1—C2—C3	118.89 (12)	C6—C5—H5	119.9
N1—C2—C1	118.73 (12)	N1—C6—C5	118.68 (15)
C3—C2—C1	122.36 (13)	N1—C6—H6	120.7
O3—C3—C2	120.57 (13)	C5—C6—H6	120.7
C6—N1—C2—C3	0.5 (2)	N1—C2—C3—C4	−0.6 (2)
C6—N1—C2—C1	179.01 (13)	C1—C2—C3—C4	−179.10 (14)
O2—C1—C2—N1	2.6 (2)	O3—C3—C4—C5	−179.02 (14)
O1—C1—C2—N1	−176.69 (13)	C2—C3—C4—C5	0.2 (2)
O2—C1—C2—C3	−178.94 (14)	C3—C4—C5—C6	0.3 (2)
O1—C1—C2—C3	1.8 (2)	C2—N1—C6—C5	0.1 (2)
N1—C2—C3—O3	178.64 (14)	C4—C5—C6—N1	−0.5 (2)
C1—C2—C3—O3	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.84	1.75	2.4997 (17)	148.
N1—H71···O2i	1.01 (2)	1.80 (3)	2.6767 (17)	143 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.84	1.75	2.4997 (17)	148
N1—H71⋯O2i	1.01 (2)	1.80 (3)	2.6767 (17)	143 (3)

Symmetry code: (i) .