4-(Hydroxy­meth­yl)phenol

Abstract

In the mol­ecule of the title compound, C₇H₈O₂, the phenol O and hydroxy­methyl C atoms lie in the ring plane [deviations of −0.015 (3) and and 0.013 (3) Å, respectively]. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link mol­ecules into a network. A weak C—H⋯π inter­action is also found.

Related literature

For a related structure, see: Tale et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

• C₇H₈O₂

• M _r = 124.13

• Orthorhombic,

• a = 9.524 (3) Å

• b = 11.006 (4) Å

• c = 5.942 (2) Å

• V = 622.9 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 298 K

• 0.65 × 0.62 × 0.55 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.940, T _max = 0.949

• 3751 measured reflections

• 1414 independent reflections

• 1200 reflections with I > 2σ(I)

• R _int = 0.036

Refinement

• R[F ² > 2σ(F ²)] = 0.035

• wR(F ²) = 0.076

• S = 1.00

• 1414 reflections

• 84 parameters

• 1 restraint

• H-atom parameters constrained

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.86	2.668 (3)	169
O2—H2⋯O1ii	0.82	2.01	2.817 (3)	167
C1—H1B⋯Cg1iii	0.97	2.77	3.694 (3)	159

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C2–C7 ring.

supplementary crystallographic information

Comment

The reduction of carboxylic acids to alcohols is a key synthetic transformation in organic chemistry. There are several ways to bring about this transformation. It is conventionally carried out using sodium borohydride as a reducing agent. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar. Atoms O1, O2 and C1 are -0.015 (3), 1.279 (3) and 0.013 (3) Å away from the ring plane, respectively.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into a network, in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Experimental

The title compound was prepared by reducing corresponding carboxylic acid using sodium borohydride in THF solution according to a literatue method (Tale et al., 2003). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Refinement

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms. The absolute structure could not be determined reliably, and 605 Friedel pairs were averaged before the last cycle of refinement.

Figures

Fig. 1.

The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C7H8O2	F(000) = 264
Mr = 124.13	Dx = 1.324 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1897 reflections
a = 9.524 (3) Å	θ = 2.8–27.9°
b = 11.006 (4) Å	µ = 0.10 mm−1
c = 5.942 (2) Å	T = 298 K
V = 622.9 (4) Å3	Block, colorless
Z = 4	0.65 × 0.62 × 0.55 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1414 independent reflections
Radiation source: fine-focus sealed tube	1200 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.8°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→8
Tmin = 0.940, Tmax = 0.949	k = −14→14
3751 measured reflections	l = −7→7

Refinement

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0125P)2 + 0.2042P] where P = (Fo2 + 2Fc2)/3
1414 reflections	(Δ/σ)max < 0.001
84 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.16 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	0.65915 (14)	0.47478 (11)	0.5585 (2)	0.0477 (3)
H1	0.6206	0.5344	0.5036	0.072*
O2	0.99603 (14)	0.15137 (10)	−0.1224 (3)	0.0470 (3)
H2	1.0542	0.1183	−0.2037	0.071*
C1	1.05125 (18)	0.26412 (15)	−0.0417 (3)	0.0422 (4)
H1A	1.0696	0.3180	−0.1675	0.051*
H1B	1.1391	0.2500	0.0366	0.051*
C2	0.94754 (17)	0.32168 (14)	0.1149 (3)	0.0351 (4)
C3	0.87551 (17)	0.42678 (14)	0.0552 (3)	0.0367 (4)
H3	0.8929	0.4626	−0.0838	0.044*
C4	0.77818 (18)	0.47925 (15)	0.1993 (3)	0.0356 (4)
H4	0.7304	0.5492	0.1563	0.043*
C5	0.75251 (16)	0.42727 (13)	0.4065 (3)	0.0349 (4)
C6	0.82324 (18)	0.32200 (15)	0.4694 (3)	0.0406 (4)
H6	0.8058	0.2864	0.6086	0.049*
C7	0.91947 (18)	0.27084 (15)	0.3239 (3)	0.0411 (4)
H7	0.9666	0.2006	0.3668	0.049*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0571 (8)	0.0424 (7)	0.0437 (8)	0.0143 (6)	0.0121 (7)	0.0079 (6)
O2	0.0487 (7)	0.0391 (6)	0.0532 (8)	−0.0069 (6)	0.0148 (6)	−0.0085 (6)
C1	0.0361 (9)	0.0379 (8)	0.0526 (11)	−0.0041 (7)	0.0067 (8)	−0.0032 (9)
C2	0.0326 (8)	0.0322 (8)	0.0404 (10)	−0.0045 (7)	−0.0004 (7)	−0.0027 (7)
C3	0.0432 (9)	0.0326 (8)	0.0345 (9)	−0.0051 (7)	0.0014 (8)	0.0037 (8)
C4	0.0412 (9)	0.0277 (7)	0.0381 (10)	0.0003 (7)	−0.0028 (8)	0.0030 (7)
C5	0.0365 (8)	0.0308 (7)	0.0374 (9)	0.0000 (6)	−0.0008 (7)	−0.0008 (7)
C6	0.0475 (10)	0.0382 (9)	0.0362 (9)	0.0035 (8)	0.0012 (8)	0.0088 (7)
C7	0.0425 (9)	0.0353 (8)	0.0454 (10)	0.0079 (7)	−0.0023 (8)	0.0035 (8)

Geometric parameters (Å, °)

O1—H1	0.8200	C3—H3	0.9300
O2—H2	0.8200	C4—C5	1.380 (2)
C1—O2	1.430 (2)	C4—H4	0.9300
C1—C2	1.498 (2)	C5—O1	1.371 (2)
C1—H1A	0.9700	C5—C6	1.391 (2)
C1—H1B	0.9700	C6—C7	1.380 (3)
C2—C7	1.388 (3)	C6—H6	0.9300
C2—C3	1.391 (2)	C7—H7	0.9300
C3—C4	1.388 (2)
C5—O1—H1	109.5	C2—C3—H3	119.4
C1—O2—H2	109.5	C5—C4—C3	119.76 (15)
O2—C1—C2	109.44 (13)	C5—C4—H4	120.1
O2—C1—H1A	109.8	C3—C4—H4	120.1
C2—C1—H1A	109.8	O1—C5—C4	123.00 (14)
O2—C1—H1B	109.8	O1—C5—C6	117.03 (16)
C2—C1—H1B	109.8	C4—C5—C6	119.96 (16)
H1A—C1—H1B	108.2	C7—C6—C5	119.52 (17)
C7—C2—C3	117.92 (16)	C7—C6—H6	120.2
C7—C2—C1	120.83 (15)	C5—C6—H6	120.2
C3—C2—C1	121.25 (16)	C6—C7—C2	121.61 (16)
C4—C3—C2	121.22 (17)	C6—C7—H7	119.2
C4—C3—H3	119.4	C2—C7—H7	119.2
O2—C1—C2—C7	68.9 (2)	C3—C4—C5—C6	−0.6 (2)
O2—C1—C2—C3	−110.49 (18)	O1—C5—C6—C7	−179.38 (16)
C7—C2—C3—C4	−0.2 (2)	C4—C5—C6—C7	0.4 (3)
C1—C2—C3—C4	179.21 (16)	C5—C6—C7—C2	−0.2 (3)
C2—C3—C4—C5	0.5 (2)	C3—C2—C7—C6	0.1 (3)
C3—C4—C5—O1	179.21 (15)	C1—C2—C7—C6	−179.37 (16)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.86	2.668 (3)	169
O2—H2···O1ii	0.82	2.01	2.817 (3)	167
C1—H1B···Cg1iii	0.97	2.77	3.694 (3)	159

Symmetry codes: (i) −x+3/2, y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1; (iii) −x+1/2, y+1/2, z+1/2.