2-Amino-pyridin-3-ol.

The molecule of the title pyridine derivative, C(5)H(6)N(2)O, shows approximate C(s) symmetry. Intra-cyclic angles cover the range 118.34 (10)-123.11 (10)°. In the crystal, O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds connect the mol-ecules into double layers perpendicular to the a axis. The shortest centroid-centroid distance between two π-systems is 3.8887 (7) Å.

Related literature

For the crystal structure of 2,3-diamino­pyridine, see: Betz et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For general information about the chelate effect in coordination chemistry, see: Gade (1998 ▶).

Experimental

Crystal data

C5H6N2O

M = 110.12

Monoclinic,

a = 12.5310 (6) Å

b = 3.8887 (2) Å

c = 11.6042 (5) Å

β = 113.139 (2)°

V = 519.98 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.29 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

4820 measured reflections

1289 independent reflections

1008 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.117

S = 1.13

1289 reflections

81 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.22 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: ORTEP-3 (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/S1600536811034775/bh2372sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811034775/bh2372Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034775/bh2372Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811034775/bh2372Isup4.cml

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

C5H6N2O	F(000) = 232
Mr = 110.12	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2447 reflections
a = 12.5310 (6) Å	θ = 3.5–28.1°
b = 3.8887 (2) Å	µ = 0.10 mm−1
c = 11.6042 (5) Å	T = 200 K
β = 113.139 (2)°	Block, brown
V = 519.98 (4) Å3	0.29 × 0.25 × 0.13 mm
Z = 4

Bruker APEXII CCD diffractometer	1008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −15→16
4820 measured reflections	k = −5→3
1289 independent reflections	l = −15→15

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) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.0455P] where P = (Fo2 + 2Fc2)/3
1289 reflections	(Δ/σ)max < 0.001
81 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.22 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
O1	0.36008 (7)	0.7180 (3)	0.48635 (7)	0.0334 (3)
H1	0.3249	0.7262	0.5328	0.050*
N1	0.26183 (8)	0.7983 (3)	0.15240 (8)	0.0262 (3)
N2	0.43131 (8)	0.5713 (3)	0.30122 (10)	0.0290 (3)
H71	0.4673 (14)	0.495 (4)	0.3773 (16)	0.037 (4)*
H72	0.4404 (14)	0.444 (5)	0.2414 (17)	0.051 (5)*
C1	0.32537 (9)	0.7224 (3)	0.27173 (10)	0.0223 (3)
C2	0.28799 (9)	0.8073 (3)	0.36913 (10)	0.0233 (3)
C3	0.18289 (10)	0.9681 (3)	0.33747 (11)	0.0273 (3)
H3	0.1558	1.0290	0.4006	0.033*
C4	0.11580 (10)	1.0419 (3)	0.21157 (11)	0.0302 (3)
H4	0.0424	1.1509	0.1877	0.036*
C5	0.15829 (10)	0.9537 (3)	0.12361 (10)	0.0300 (3)
H5	0.1127	1.0043	0.0382	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0280 (5)	0.0579 (6)	0.0161 (4)	0.0062 (4)	0.0109 (4)	0.0035 (4)
N1	0.0277 (5)	0.0355 (6)	0.0170 (5)	−0.0017 (4)	0.0103 (4)	0.0006 (4)
N2	0.0275 (5)	0.0420 (7)	0.0207 (5)	0.0060 (4)	0.0129 (4)	0.0020 (4)
C1	0.0237 (6)	0.0271 (6)	0.0182 (5)	−0.0031 (4)	0.0106 (4)	−0.0002 (4)
C2	0.0246 (6)	0.0300 (6)	0.0167 (5)	−0.0025 (4)	0.0096 (4)	−0.0004 (4)
C3	0.0284 (6)	0.0337 (7)	0.0235 (6)	−0.0001 (5)	0.0143 (5)	−0.0026 (5)
C4	0.0251 (6)	0.0360 (7)	0.0297 (6)	0.0045 (5)	0.0109 (5)	0.0028 (5)
C5	0.0280 (6)	0.0399 (7)	0.0197 (5)	0.0003 (5)	0.0069 (4)	0.0047 (5)

O1—C2	1.3496 (13)	C1—C2	1.4219 (14)
O1—H1	0.8200	C2—C3	1.3712 (16)
N1—C1	1.3312 (14)	C3—C4	1.3994 (16)
N1—C5	1.3490 (15)	C3—H3	0.9500
N2—C1	1.3667 (14)	C4—C5	1.3675 (16)
N2—H71	0.870 (17)	C4—H4	0.9500
N2—H72	0.895 (18)	C5—H5	0.9500
C2—O1—H1	109.5	C3—C2—C1	118.34 (10)
C1—N1—C5	118.74 (9)	C2—C3—C4	119.53 (10)
C1—N2—H71	117.7 (9)	C2—C3—H3	120.2
C1—N2—H72	116.8 (11)	C4—C3—H3	120.2
H71—N2—H72	115.2 (15)	C5—C4—C3	118.52 (11)
N1—C1—N2	118.74 (9)	C5—C4—H4	120.7
N1—C1—C2	121.74 (10)	C3—C4—H4	120.7
N2—C1—C2	119.46 (10)	N1—C5—C4	123.11 (10)
O1—C2—C3	125.40 (9)	N1—C5—H5	118.4
O1—C2—C1	116.25 (10)	C4—C5—H5	118.4
C5—N1—C1—N2	−178.69 (10)	O1—C2—C3—C4	−179.09 (11)
C5—N1—C1—C2	−1.36 (18)	C1—C2—C3—C4	0.32 (18)
N1—C1—C2—O1	−179.79 (10)	C2—C3—C4—C5	−0.72 (19)
N2—C1—C2—O1	−2.49 (17)	C1—N1—C5—C4	0.94 (19)
N1—C1—C2—C3	0.74 (18)	C3—C4—C5—N1	0.1 (2)
N2—C1—C2—C3	178.05 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.85	2.6639 (12)	172.
N2—H71···O1ii	0.870 (17)	2.276 (17)	3.0184 (13)	143.2 (12)
N2—H72···N2iii	0.895 (18)	2.358 (17)	3.1249 (15)	143.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.85	2.6639 (12)	172
N2—H71⋯O1ii	0.870 (17)	2.276 (17)	3.0184 (13)	143.2 (12)
N2—H72⋯N2iii	0.895 (18)	2.358 (17)	3.1249 (15)	143.8 (15)

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