4-Hy-droxy-6-methyl-pyridin-2(1H)-one.

In the crystal structure of the title compound, C6H7NO2, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules, forming a zigzag array along [001] and a layer structure parallel to the ab plane.

Related literature

For the potential of related compounds in anti-HIV treatment, see: De Clercq (2005 ▶); Dollé et al. (1995 ▶); Medina-Franco et al. (2007 ▶).

Experimental

Crystal data

C6H7NO2

M = 125.13

Monoclinic,

a = 4.7082 (5) Å

b = 12.2988 (8) Å

c = 10.0418 (7) Å

β = 91.303 (7)°

V = 581.32 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.65 × 0.20 × 0.18 mm

Data collection

Bruker P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.216, T max = 0.259

2445 measured reflections

1701 independent reflections

1269 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 97 reflections intensity decay: 9.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.160

S = 1.06

1701 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813024240/im2437sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024240/im2437Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024240/im2437Isup3.cml

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

C6H7NO2	F(000) = 264
Mr = 125.13	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 51 reflections
a = 4.7082 (5) Å	θ = 6.6–12.3°
b = 12.2988 (8) Å	µ = 0.11 mm−1
c = 10.0418 (7) Å	T = 298 K
β = 91.303 (7)°	Prismatic, colorless
V = 581.32 (8) Å3	0.65 × 0.20 × 0.18 mm
Z = 4

Bruker P4 diffractometer	1269 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 30.0°, θmin = 2.6°
2θ/ω scans	h = −1→6
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −1→17
Tmin = 0.216, Tmax = 0.259	l = −14→14
2445 measured reflections	3 standard reflections every 97 reflections
1701 independent reflections	intensity decay: 9.4%

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: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
1701 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. IR: 3296, 3094, 2891, 1640 cm^-1. 1Ĥ NMR (CDCl~3~): δ 10.99 (s, NH-1), 10.40 (s, OH), 5.59 (s, H-3), 5.34 (s, H-5) 2.07 (s, 3H, CH~3~—C-6). ^13Ĉ NMR (CDCl~3~): δ 167.6, 164.8, 145.9, 98.2, 95.7, 18.5. MS m/e (int. rel): [M]^+^ 125 (100), 97 (16).

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
O1	0.7844 (3)	0.91089 (9)	0.60053 (9)	0.0364 (3)
O2	0.2045 (2)	0.68616 (10)	0.32761 (10)	0.0396 (3)
H2B	0.2292	0.6556	0.2562	0.059*
N1	0.7786 (3)	0.93124 (10)	0.37596 (11)	0.0301 (3)
H1A	0.9049	0.9813	0.3858	0.036*
C1	0.6811 (3)	0.88072 (12)	0.48782 (12)	0.0288 (3)
C2	0.4786 (3)	0.79830 (13)	0.46911 (13)	0.0326 (3)
H2A	0.4026	0.7638	0.5426	0.039*
C3	0.3912 (3)	0.76793 (12)	0.34229 (13)	0.0303 (3)
C4	0.4958 (3)	0.82420 (12)	0.23072 (14)	0.0321 (3)
H4A	0.4353	0.8053	0.1450	0.038*
C5	0.6858 (3)	0.90624 (12)	0.25012 (13)	0.0293 (3)
C6	0.8049 (4)	0.97389 (15)	0.14088 (15)	0.0403 (4)
H6D	0.7267	0.9501	0.0567	0.060*
H6A	1.0078	0.9662	0.1411	0.060*
H6B	0.7566	1.0488	0.1548	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0491 (7)	0.0370 (6)	0.0227 (5)	−0.0064 (5)	−0.0062 (4)	0.0009 (4)
O2	0.0483 (7)	0.0407 (6)	0.0297 (5)	−0.0133 (5)	0.0024 (5)	−0.0057 (4)
N1	0.0360 (6)	0.0315 (6)	0.0227 (5)	−0.0037 (5)	−0.0032 (5)	0.0022 (4)
C1	0.0352 (7)	0.0297 (7)	0.0214 (6)	0.0034 (6)	−0.0013 (5)	0.0010 (5)
C2	0.0399 (8)	0.0340 (7)	0.0238 (6)	−0.0026 (6)	0.0015 (5)	0.0009 (5)
C3	0.0324 (7)	0.0311 (7)	0.0273 (6)	0.0002 (6)	0.0000 (5)	−0.0014 (5)
C4	0.0380 (8)	0.0357 (8)	0.0224 (6)	0.0007 (6)	−0.0021 (5)	−0.0023 (5)
C5	0.0341 (7)	0.0319 (7)	0.0218 (6)	0.0027 (6)	−0.0004 (5)	0.0016 (5)
C6	0.0534 (10)	0.0420 (9)	0.0255 (6)	−0.0049 (8)	0.0007 (6)	0.0068 (6)

O1—C1	1.2768 (16)	C2—H2A	0.9300
O2—C3	1.3418 (18)	C3—C4	1.415 (2)
O2—H2B	0.8200	C4—C5	1.359 (2)
N1—C5	1.3629 (17)	C4—H4A	0.9300
N1—C1	1.3719 (17)	C5—C6	1.496 (2)
N1—H1A	0.8600	C6—H6D	0.9600
C1—C2	1.401 (2)	C6—H6A	0.9600
C2—C3	1.3809 (19)	C6—H6B	0.9600
C3—O2—H2B	109.5	C5—C4—C3	119.30 (13)
C5—N1—C1	123.42 (13)	C5—C4—H4A	120.4
C5—N1—H1A	118.3	C3—C4—H4A	120.4
C1—N1—H1A	118.3	C4—C5—N1	119.76 (13)
O1—C1—N1	117.79 (14)	C4—C5—C6	124.34 (13)
O1—C1—C2	124.99 (13)	N1—C5—C6	115.90 (14)
N1—C1—C2	117.21 (12)	C5—C6—H6D	109.5
C3—C2—C1	120.46 (13)	C5—C6—H6A	109.5
C3—C2—H2A	119.8	H6D—C6—H6A	109.5
C1—C2—H2A	119.8	C5—C6—H6B	109.5
O2—C3—C2	119.01 (13)	H6D—C6—H6B	109.5
O2—C3—C4	121.24 (12)	H6A—C6—H6B	109.5
C2—C3—C4	119.74 (14)
C5—N1—C1—O1	179.84 (14)	O2—C3—C4—C5	−179.71 (13)
C5—N1—C1—C2	1.0 (2)	C2—C3—C4—C5	1.3 (2)
O1—C1—C2—C3	−176.62 (15)	C3—C4—C5—N1	1.8 (2)
N1—C1—C2—C3	2.2 (2)	C3—C4—C5—C6	−178.05 (15)
C1—C2—C3—O2	177.69 (13)	C1—N1—C5—C4	−3.0 (2)
C1—C2—C3—C4	−3.3 (2)	C1—N1—C5—C6	176.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	1.98	2.835 (2)	175
O2—H2B···O1ii	0.82	1.79	2.609 (2)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	1.98	2.835 (2)	175
O2—H2B⋯O1ii	0.82	1.79	2.609 (2)	180

Symmetry codes: (i) ; (ii) .