2-Hydroxy­methyl-4-methyl­phenol

The title compound, C₈H₁₀O₂, packs into a three-dimensional network via inter­molecular O—H...O hydrogen-bonding inter­actions; a 12-membered ring is produced by hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.045
• wR factor = 0.126
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker 2000); cell refinement: SAINT (Bruker 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Hydroxymethyl-4-methylphenol

Crystal data

C8H10O2	F(000) = 296
Mr = 138.16	Dx = 1.241 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1038 reflections
a = 16.322 (3) Å	θ = 2.5–26.1°
b = 5.4697 (9) Å	µ = 0.09 mm^−1
c = 8.4504 (14) Å	T = 291 K
β = 101.447 (3)°	Block, colourless
V = 739.4 (2) Å^3	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1590 independent reflections
Radiation source: fine-focus sealed tube	996 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→20
Tmin = 0.985, Tmax = 0.994	k = −6→6
4132 measured reflections	l = −10→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0673P)^2] where P = (Fo^2 + 2Fc^2)/3
1590 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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 > 2σ(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
C1	0.31812 (10)	0.6033 (3)	0.98760 (17)	0.0435 (4)
C2	0.32328 (10)	0.3942 (3)	1.08462 (18)	0.0440 (4)
C3	0.25128 (11)	0.2813 (3)	1.1091 (2)	0.0553 (5)
H3	0.2548	0.1420	1.1732	0.066*
C4	0.17416 (11)	0.3739 (3)	1.0390 (2)	0.0613 (5)
H4	0.1262	0.2953	1.0564	0.074*
C5	0.16625 (11)	0.5814 (3)	0.9430 (2)	0.0581 (5)
C6	0.23935 (10)	0.6912 (3)	0.91914 (19)	0.0527 (4)
H6	0.2354	0.8299	0.8544	0.063*
C7	0.39506 (10)	0.7260 (3)	0.95579 (18)	0.0479 (4)
H7A	0.3809	0.8858	0.9085	0.057*
H7B	0.4349	0.7477	1.0564	0.057*
C8	0.08172 (12)	0.6875 (4)	0.8659 (3)	0.0922 (7)
H8A	0.0401	0.6302	0.9228	0.138*
H8B	0.0673	0.6366	0.7551	0.138*
H8C	0.0843	0.8627	0.8710	0.138*
O1	0.40109 (7)	0.3096 (2)	1.15262 (15)	0.0551 (4)
O2	0.43120 (8)	0.5782 (2)	0.84744 (12)	0.0526 (4)
H1	0.3968 (14)	0.191 (4)	1.210 (3)	0.104 (9)*
H2	0.4836 (14)	0.611 (4)	0.861 (2)	0.081 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0531 (9)	0.0401 (8)	0.0379 (8)	0.0006 (7)	0.0105 (7)	−0.0045 (7)
C2	0.0497 (9)	0.0415 (8)	0.0419 (8)	0.0005 (7)	0.0119 (7)	−0.0014 (7)
C3	0.0613 (11)	0.0493 (10)	0.0575 (10)	−0.0038 (8)	0.0167 (8)	0.0068 (8)
C4	0.0516 (11)	0.0662 (11)	0.0680 (12)	−0.0074 (9)	0.0160 (9)	−0.0023 (10)
C5	0.0518 (10)	0.0652 (11)	0.0557 (10)	0.0037 (8)	0.0068 (8)	−0.0027 (9)
C6	0.0631 (11)	0.0508 (9)	0.0435 (9)	0.0073 (8)	0.0089 (8)	0.0024 (7)
C7	0.0608 (11)	0.0406 (8)	0.0429 (9)	−0.0014 (7)	0.0114 (8)	0.0021 (7)
C8	0.0615 (13)	0.1151 (18)	0.0950 (17)	0.0096 (12)	0.0031 (12)	0.0129 (14)
O1	0.0508 (7)	0.0521 (7)	0.0628 (8)	0.0030 (6)	0.0126 (6)	0.0165 (6)
O2	0.0505 (8)	0.0640 (8)	0.0450 (7)	−0.0097 (6)	0.0133 (5)	−0.0103 (5)

Geometric parameters (Å, º)

C1—C6	1.387 (2)	C5—C8	1.519 (2)
C1—C2	1.400 (2)	C6—H6	0.9300
C1—C7	1.494 (2)	C7—O2	1.4331 (18)
C2—O1	1.3665 (18)	C7—H7A	0.9700
C2—C3	1.379 (2)	C7—H7B	0.9700
C3—C4	1.377 (2)	C8—H8A	0.9600
C3—H3	0.9300	C8—H8B	0.9600
C4—C5	1.386 (2)	C8—H8C	0.9600
C4—H4	0.9300	O1—H1	0.82 (2)
C5—C6	1.386 (2)	O2—H2	0.86 (2)
C6—C1—C2	118.07 (15)	C5—C6—H6	118.6
C6—C1—C7	120.79 (14)	C1—C6—H6	118.6
C2—C1—C7	121.13 (14)	O2—C7—C1	109.21 (12)
O1—C2—C3	122.26 (14)	O2—C7—H7A	109.8
O1—C2—C1	117.76 (14)	C1—C7—H7A	109.8
C3—C2—C1	119.98 (15)	O2—C7—H7B	109.8
C4—C3—C2	120.27 (16)	C1—C7—H7B	109.8
C4—C3—H3	119.9	H7A—C7—H7B	108.3
C2—C3—H3	119.9	C5—C8—H8A	109.5
C3—C4—C5	121.61 (16)	C5—C8—H8B	109.5
C3—C4—H4	119.2	H8A—C8—H8B	109.5
C5—C4—H4	119.2	C5—C8—H8C	109.5
C6—C5—C4	117.20 (16)	H8A—C8—H8C	109.5
C6—C5—C8	120.47 (18)	H8B—C8—H8C	109.5
C4—C5—C8	122.34 (17)	C2—O1—H1	109.6 (15)
C5—C6—C1	122.87 (16)	C7—O2—H2	108.9 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82 (2)	1.89 (2)	2.670 (2)	158 (2)
O2—H2···O1^ii	0.86 (2)	1.96 (2)	2.805 (2)	169 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2.