4-Hydroxy-meth-yl-2-methoxy-phenol.

The title compound, C(8)H(10)O(3), is close to planar (r.m.s. deviation = 0.042 Å) apart from the hydroxyl O atom [deviation = 1.285 (1) Å] and an intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, inter-molecular O-H⋯O links lead to chains propagating in [001].

Related literature

For a related compound used as a food additive, see: Kumar et al. (2004 ▶); Shaughnessy et al. (2001 ▶).

Experimental

Crystal data

C8H10O3

M = 154.16

Monoclinic,

a = 9.8476 (6) Å

b = 6.1721 (4) Å

c = 15.4915 (7) Å

β = 126.877 (2)°

V = 753.19 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.29 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.971, T max = 0.993

3996 measured reflections

1475 independent reflections

1249 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.05

1475 reflections

102 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043025/hb5154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043025/hb5154Isup2.hkl

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

C8H10O3	F(000) = 328
Mr = 154.16	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1768 reflections
a = 9.8476 (6) Å	θ = 2.6–27.6°
b = 6.1721 (4) Å	µ = 0.10 mm−1
c = 15.4915 (7) Å	T = 293 K
β = 126.877 (2)°	Plate, colorless
V = 753.19 (8) Å3	0.29 × 0.11 × 0.07 mm
Z = 4

Bruker SMART CCD diffractometer	1475 independent reflections
Radiation source: fine-focus sealed tube	1249 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→8
Tmin = 0.971, Tmax = 0.993	k = −7→7
3996 measured reflections	l = −17→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.2254P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1475 reflections	Δρmax = 0.24 e Å−3
102 parameters	Δρmin = −0.19 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (6)

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	0.16947 (13)	0.60312 (18)	0.16129 (8)	0.0462 (3)
H1A	0.1727	0.4901	0.1347	0.069*
O2	0.35690 (14)	0.26017 (19)	0.27618 (8)	0.0501 (3)
O3	0.16416 (15)	0.1981 (2)	0.52945 (9)	0.0621 (4)
H3B	0.0675	0.2067	0.4697	0.093*
C1	0.19570 (17)	0.5586 (2)	0.25692 (11)	0.0352 (3)
C2	0.12924 (18)	0.6933 (2)	0.29368 (12)	0.0407 (4)
H2A	0.0704	0.8173	0.2550	0.049*
C3	0.14955 (19)	0.6447 (2)	0.38857 (12)	0.0416 (4)
H3A	0.1034	0.7361	0.4125	0.050*
C4	0.23753 (17)	0.4625 (2)	0.44737 (11)	0.0383 (3)
C5	0.31075 (18)	0.3308 (2)	0.41213 (11)	0.0394 (4)
H5A	0.3734	0.2100	0.4524	0.047*
C6	0.29122 (17)	0.3781 (2)	0.31805 (11)	0.0360 (3)
C7	0.2509 (2)	0.3978 (3)	0.54583 (12)	0.0467 (4)
H7A	0.3696	0.3823	0.6065	0.056*
H7B	0.2026	0.5111	0.5632	0.056*
C8	0.4600 (2)	0.0789 (3)	0.33595 (13)	0.0491 (4)
H8A	0.4997	0.0128	0.2987	0.074*
H8B	0.3948	−0.0242	0.3435	0.074*
H8C	0.5554	0.1256	0.4061	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.0591 (7)	0.0473 (6)	0.0406 (6)	0.0118 (5)	0.0344 (5)	0.0107 (5)
O2	0.0624 (7)	0.0559 (7)	0.0461 (6)	0.0249 (5)	0.0400 (6)	0.0144 (5)
O3	0.0635 (7)	0.0802 (9)	0.0413 (6)	−0.0217 (7)	0.0308 (6)	−0.0033 (6)
C1	0.0360 (7)	0.0382 (7)	0.0338 (7)	−0.0010 (6)	0.0223 (6)	0.0021 (6)
C2	0.0446 (8)	0.0359 (8)	0.0413 (8)	0.0057 (6)	0.0256 (7)	0.0033 (6)
C3	0.0467 (8)	0.0412 (8)	0.0434 (8)	0.0016 (6)	0.0304 (7)	−0.0052 (6)
C4	0.0389 (7)	0.0440 (8)	0.0318 (7)	−0.0031 (6)	0.0212 (6)	−0.0040 (6)
C5	0.0399 (7)	0.0428 (8)	0.0339 (7)	0.0070 (6)	0.0212 (6)	0.0056 (6)
C6	0.0348 (7)	0.0403 (8)	0.0360 (7)	0.0029 (6)	0.0228 (6)	0.0008 (6)
C7	0.0542 (9)	0.0532 (10)	0.0374 (8)	−0.0009 (7)	0.0300 (7)	−0.0031 (7)
C8	0.0526 (9)	0.0500 (9)	0.0496 (9)	0.0155 (7)	0.0332 (8)	0.0079 (7)

O1—C1	1.3702 (16)	C3—H3A	0.9300
O1—H1A	0.8200	C4—C5	1.397 (2)
O2—C6	1.3683 (16)	C4—C7	1.5041 (19)
O2—C8	1.4181 (18)	C5—C6	1.3820 (19)
O3—C7	1.433 (2)	C5—H5A	0.9300
O3—H3B	0.8416	C7—H7A	0.9700
C1—C2	1.375 (2)	C7—H7B	0.9700
C1—C6	1.3977 (19)	C8—H8A	0.9600
C2—C3	1.392 (2)	C8—H8B	0.9600
C2—H2A	0.9300	C8—H8C	0.9600
C3—C4	1.378 (2)
C1—O1—H1A	109.5	C4—C5—H5A	119.6
C6—O2—C8	117.84 (11)	O2—C6—C5	125.55 (13)
C7—O3—H3B	107.5	O2—C6—C1	114.85 (12)
O1—C1—C2	119.92 (12)	C5—C6—C1	119.60 (13)
O1—C1—C6	120.39 (12)	O3—C7—C4	111.63 (12)
C2—C1—C6	119.68 (12)	O3—C7—H7A	109.3
C1—C2—C3	120.32 (13)	C4—C7—H7A	109.3
C1—C2—H2A	119.8	O3—C7—H7B	109.3
C3—C2—H2A	119.8	C4—C7—H7B	109.3
C4—C3—C2	120.58 (13)	H7A—C7—H7B	108.0
C4—C3—H3A	119.7	O2—C8—H8A	109.5
C2—C3—H3A	119.7	O2—C8—H8B	109.5
C3—C4—C5	118.93 (13)	H8A—C8—H8B	109.5
C3—C4—C7	121.65 (13)	O2—C8—H8C	109.5
C5—C4—C7	119.38 (13)	H8A—C8—H8C	109.5
C6—C5—C4	120.78 (13)	H8B—C8—H8C	109.5
C6—C5—H5A	119.6

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.31	2.6669 (16)	107
O1—H1A···O3i	0.82	1.96	2.7390 (16)	158
O3—H3B···O1ii	0.84	2.07	2.8666 (15)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	2.31	2.6669 (16)	107
O1—H1A⋯O3i	0.82	1.96	2.7390 (16)	158
O3—H3B⋯O1ii	0.84	2.07	2.8666 (15)	158

Symmetry codes: (i) ; (ii) .