2-Amino-6-(hydroxy­meth­yl)pyridine

The molecule of the title compound, C₆H₈N₂O, is almost planar; the hydroxy­methyl group deviates slightly from the plane of the ring. The mol­ecules are linked into a chain running along the a-axis direction by an O—H...N hydrogen bond. N—H...O and N—H...N hydrogen bonds connect the chains, forming a mol­ecular layer parallel to the (001) plane. A C—H...π inter­action is also observed in the layer.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-Amino-6-(hydroxymethyl)pyridine

Crystal data

C6H8N2O	F(000) = 264
Mr = 124.14	Dx = 1.295 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1373 reflections
a = 6.9279 (2) Å	θ = 2.1–29.0°
b = 4.7570 (1) Å	µ = 0.09 mm^−1
c = 19.3436 (5) Å	T = 297 K
β = 92.657 (2)°	Block, colourless
V = 636.80 (3) Å^3	0.44 × 0.36 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	1699 independent reflections
Radiation source: fine-focus sealed tube	1373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm^-1	θmax = 29.0°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.961, Tmax = 0.979	l = −26→26
8090 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.0978P] where P = (Fo^2 + 2Fc^2)/3
1699 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.13559 (13)	0.2220 (2)	0.11410 (6)	0.0556 (3)
N1	0.34165 (12)	0.4952 (2)	0.08010 (5)	0.0361 (2)
N2	0.64074 (15)	0.7070 (3)	0.07044 (6)	0.0485 (3)
C1	0.47416 (15)	0.6739 (2)	0.10652 (6)	0.0363 (3)
C2	0.45329 (18)	0.8128 (3)	0.16953 (6)	0.0439 (3)
C3	0.29098 (18)	0.7615 (3)	0.20516 (6)	0.0475 (3)
C4	0.15234 (17)	0.5746 (3)	0.17874 (6)	0.0440 (3)
C5	0.18320 (14)	0.4471 (2)	0.11606 (5)	0.0353 (3)
C6	0.04437 (17)	0.2388 (3)	0.08254 (7)	0.0430 (3)
H2	0.553 (2)	0.946 (3)	0.1864 (8)	0.060 (4)*
H3	0.275 (2)	0.855 (3)	0.2490 (8)	0.055 (4)*
H4	0.041 (2)	0.533 (3)	0.2039 (8)	0.058 (4)*
H6A	0.103 (2)	0.053 (4)	0.0854 (8)	0.054 (4)*
H6B	0.028 (2)	0.292 (3)	0.0330 (9)	0.060 (4)*
H1N2	0.629 (2)	0.668 (3)	0.0258 (9)	0.058 (4)*
H2N2	0.711 (2)	0.859 (4)	0.0807 (9)	0.065 (5)*
H1O1	−0.198 (3)	0.377 (5)	0.1003 (10)	0.083 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0353 (5)	0.0545 (6)	0.0782 (7)	−0.0131 (4)	0.0130 (4)	0.0059 (5)
N1	0.0306 (4)	0.0370 (5)	0.0410 (5)	−0.0046 (4)	0.0061 (3)	−0.0018 (4)
N2	0.0355 (5)	0.0572 (7)	0.0537 (6)	−0.0159 (5)	0.0116 (4)	−0.0126 (5)
C1	0.0294 (5)	0.0376 (6)	0.0420 (5)	−0.0019 (4)	0.0032 (4)	−0.0010 (4)
C2	0.0393 (6)	0.0478 (7)	0.0444 (6)	−0.0038 (5)	−0.0001 (4)	−0.0071 (5)
C3	0.0485 (7)	0.0559 (8)	0.0384 (6)	0.0031 (6)	0.0050 (5)	−0.0058 (5)
C4	0.0381 (6)	0.0519 (7)	0.0432 (6)	0.0004 (5)	0.0126 (4)	0.0040 (5)
C5	0.0298 (5)	0.0340 (5)	0.0423 (5)	−0.0003 (4)	0.0048 (4)	0.0069 (4)
C6	0.0327 (5)	0.0404 (7)	0.0561 (7)	−0.0068 (5)	0.0055 (5)	0.0036 (5)

Geometric parameters (Å, º)

O1—C6	1.4156 (14)	C2—H2	0.984 (17)
O1—H1O1	0.89 (2)	C3—C4	1.3888 (18)
N1—C1	1.3353 (14)	C3—H3	0.968 (16)
N1—C5	1.3460 (13)	C4—C5	1.3813 (16)
N2—C1	1.3850 (14)	C4—H4	0.954 (15)
N2—H1N2	0.883 (17)	C5—C6	1.5065 (16)
N2—H2N2	0.889 (19)	C6—H6A	0.971 (16)
C1—C2	1.3997 (16)	C6—H6B	0.992 (17)
C2—C3	1.3676 (17)
C6—O1—H1O1	104.6 (12)	C4—C3—H3	120.6 (9)
C1—N1—C5	118.24 (9)	C5—C4—C3	118.14 (10)
C1—N2—H1N2	115.3 (10)	C5—C4—H4	121.2 (9)
C1—N2—H2N2	116.0 (10)	C3—C4—H4	120.6 (9)
H1N2—N2—H2N2	114.6 (15)	N1—C5—C4	122.82 (10)
N1—C1—N2	116.98 (10)	N1—C5—C6	114.15 (10)
N1—C1—C2	122.46 (10)	C4—C5—C6	123.02 (10)
N2—C1—C2	120.48 (10)	O1—C6—C5	114.14 (10)
C3—C2—C1	118.38 (11)	O1—C6—H6A	107.2 (9)
C3—C2—H2	122.1 (9)	C5—C6—H6A	108.5 (9)
C1—C2—H2	119.5 (9)	O1—C6—H6B	111.7 (10)
C2—C3—C4	119.96 (11)	C5—C6—H6B	106.8 (9)
C2—C3—H3	119.4 (9)	H6A—C6—H6B	108.3 (13)
C5—N1—C1—N2	176.38 (10)	C1—N1—C5—C4	0.07 (16)
C5—N1—C1—C2	−0.40 (17)	C1—N1—C5—C6	−178.99 (10)
N1—C1—C2—C3	0.22 (18)	C3—C4—C5—N1	0.42 (18)
N2—C1—C2—C3	−176.45 (11)	C3—C4—C5—C6	179.40 (11)
C1—C2—C3—C4	0.29 (19)	N1—C5—C6—O1	−170.27 (10)
C2—C3—C4—C5	−0.59 (19)	C4—C5—C6—O1	10.67 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N2^i	0.89 (2)	2.00 (2)	2.8837 (16)	175 (2)
N2—H2N2···O1^ii	0.889 (18)	2.113 (18)	2.9991 (16)	174.5 (15)
N2—H1N2···N1^iii	0.883 (17)	2.209 (17)	3.0745 (15)	166.5 (13)
C6—H6A···Cg1^iv	0.971 (16)	2.711 (17)	3.6257 (14)	156.8 (12)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y+1, z; (iii) −x+1, −y+1, −z; (iv) x, y−1, z.