Crystal structure of 5-hy-droxy-methyl-2-meth-oxy-phenol.

In the title compound, C8H10O3, the hy-droxy-methyl group is twisted by 74.51 (13)° from the plane of the benzene ring to which it is connected. By contrast, the benzene and meth-oxy groups are almost coplanar, making a dihedral angle of 4.0 (2)°. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For the background to alcoholic hy­droxy compounds and their applications, see: Patrick (2001 ▸); Yasohara et al. (2001 ▸); Rodríguez-Barrios & Gago (2004 ▸); Wu et al. (2008 ▸); Matteelli et al. (2010 ▸); Coimbra et al. (2010 ▸); Hans et al. (2010 ▸); Cordova et al. (2006 ▸). For the synthesis of derivatives of the title compound, see: Ashraf et al. (2014 ▸, 2015 ▸).

Experimental

Crystal data

C8H10O3

M = 154.16

Orthorhombic,

a = 15.011 (4) Å

b = 6.1354 (18) Å

c = 16.543 (5) Å

V = 1523.6 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

28952 measured reflections

1900 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.149

S = 1.07

1900 reflections

108 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901501230X/tk5370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501230X/tk5370Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501230X/tk5370Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501230X/tk5370fig1.tif

The mol­ecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S205698901501230X/tk5370fig2.tif

Part of the crystal structure of the title compound, showing the 3-D network of mol­ecules linked by inter­molecular O—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1409010

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H10O3	F(000) = 656
Mr = 154.16	Dx = 1.344 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7746 reflections
a = 15.011 (4) Å	θ = 2.5–28.2°
b = 6.1354 (18) Å	µ = 0.10 mm−1
c = 16.543 (5) Å	T = 296 K
V = 1523.6 (7) Å3	Block, brown
Z = 8	0.28 × 0.25 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 28.4°, θmin = 2.5°
φ and ω scans	h = −20→19
28952 measured reflections	k = −8→8
1900 independent reflections	l = −22→20
1530 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.6464P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1900 reflections	Δρmax = 0.38 e Å−3
108 parameters	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.56019 (17)	0.3078 (3)	0.91644 (10)	0.1025 (9)
H1	0.559 (2)	0.268 (6)	0.959 (2)	0.129 (13)*
C2	0.61335 (11)	0.1812 (3)	0.86876 (9)	0.0462 (4)
H2A	0.5895	0.0345	0.8663	0.055*
H2B	0.6727	0.1737	0.8919	0.055*
C3	0.61828 (10)	0.2752 (3)	0.78509 (9)	0.0383 (4)
C4	0.57178 (10)	0.1775 (3)	0.72196 (8)	0.0388 (4)
H4	0.5385	0.0524	0.7316	0.047*
C5	0.57476 (10)	0.2651 (3)	0.64505 (8)	0.0375 (3)
C6	0.62554 (10)	0.4516 (3)	0.62970 (9)	0.0368 (3)
C7	0.67100 (11)	0.5504 (3)	0.69227 (10)	0.0452 (4)
H7	0.7042	0.6757	0.6828	0.054*
C8	0.66682 (11)	0.4616 (3)	0.76955 (9)	0.0454 (4)
H8	0.6973	0.5292	0.8116	0.054*
O9	0.52924 (10)	0.1784 (2)	0.58164 (7)	0.0554 (4)
H9	0.498 (2)	0.060 (6)	0.5924 (18)	0.124 (12)*
O10	0.62581 (8)	0.5189 (2)	0.55089 (7)	0.0472 (3)
C11	0.67256 (15)	0.7139 (3)	0.53259 (12)	0.0588 (5)
H11A	0.6682	0.7433	0.4757	0.088*
H11B	0.7341	0.6976	0.5473	0.088*
H11C	0.647	0.8328	0.5624	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.1593 (19)	0.1051 (14)	0.0432 (8)	0.0824 (14)	0.0458 (10)	0.0312 (9)
C2	0.0512 (9)	0.0580 (10)	0.0293 (7)	0.0082 (7)	−0.0009 (6)	0.0039 (7)
C3	0.0371 (7)	0.0506 (9)	0.0272 (7)	0.0057 (6)	0.0004 (5)	0.0000 (6)
C4	0.0443 (8)	0.0425 (8)	0.0296 (7)	−0.0036 (6)	0.0043 (6)	−0.0003 (6)
C5	0.0429 (7)	0.0434 (8)	0.0263 (7)	−0.0021 (6)	0.0013 (5)	−0.0039 (6)
C6	0.0395 (7)	0.0431 (8)	0.0277 (7)	0.0011 (6)	0.0025 (5)	0.0014 (6)
C7	0.0469 (8)	0.0503 (9)	0.0384 (8)	−0.0110 (7)	−0.0005 (6)	−0.0007 (7)
C8	0.0443 (8)	0.0590 (10)	0.0327 (8)	−0.0063 (7)	−0.0063 (6)	−0.0050 (7)
O9	0.0752 (9)	0.0631 (8)	0.0279 (6)	−0.0280 (7)	−0.0037 (5)	−0.0024 (5)
O10	0.0610 (7)	0.0505 (7)	0.0302 (6)	−0.0110 (5)	0.0009 (5)	0.0060 (5)
C11	0.0761 (13)	0.0528 (11)	0.0476 (10)	−0.0137 (9)	0.0028 (9)	0.0127 (8)

O1—C2	1.365 (2)	C6—O10	1.3677 (18)
O1—H1	0.74 (4)	C6—C7	1.380 (2)
C2—C3	1.501 (2)	C7—C8	1.391 (2)
C2—H2A	0.97	C7—H7	0.93
C2—H2B	0.97	C8—H8	0.93
C3—C8	1.380 (2)	O9—H9	0.88 (4)
C3—C4	1.392 (2)	O10—C11	1.420 (2)
C4—C5	1.382 (2)	C11—H11A	0.96
C4—H4	0.93	C11—H11B	0.96
C5—O9	1.3601 (18)	C11—H11C	0.96
C5—C6	1.398 (2)
C2—O1—H1	112 (3)	O10—C6—C5	114.96 (13)
O1—C2—C3	110.07 (15)	C7—C6—C5	119.54 (14)
O1—C2—H2A	109.6	C6—C7—C8	119.66 (16)
C3—C2—H2A	109.6	C6—C7—H7	120.2
O1—C2—H2B	109.6	C8—C7—H7	120.2
C3—C2—H2B	109.6	C3—C8—C7	121.29 (14)
H2A—C2—H2B	108.2	C3—C8—H8	119.4
C8—C3—C4	118.80 (14)	C7—C8—H8	119.4
C8—C3—C2	121.06 (14)	C5—O9—H9	116 (2)
C4—C3—C2	120.12 (15)	C6—O10—C11	117.34 (13)
C5—C4—C3	120.48 (15)	O10—C11—H11A	109.5
C5—C4—H4	119.8	O10—C11—H11B	109.5
C3—C4—H4	119.8	H11A—C11—H11B	109.5
O9—C5—C4	122.81 (14)	O10—C11—H11C	109.5
O9—C5—C6	116.99 (13)	H11A—C11—H11C	109.5
C4—C5—C6	120.20 (13)	H11B—C11—H11C	109.5
O10—C6—C7	125.50 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O9i	0.74 (4)	2.11 (4)	2.773 (2)	150 (4)
O1—H1···O10i	0.74 (4)	2.54 (4)	3.152 (2)	142 (4)
O9—H9···O1ii	0.88 (4)	1.78 (4)	2.641 (2)	163 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O9i	0.74(4)	2.11(4)	2.773(2)	150(4)
O1H1O10i	0.74(4)	2.54(4)	3.152(2)	142(4)
O9H9O1ii	0.88(4)	1.78(4)	2.641(2)	163(3)

Symmetry codes: (i) ; (ii) .