4-(Hydroxy­meth­yl)phenol

Liu, W.-S.; Wei, R.-P.; Tang, X.-L.; Wang, W.-H.; Ju, Z.-H.

doi:10.1107/S1600536809022466

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1689

doi:10.1107/S1600536809022466

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4-(Hydroxymethyl)phenol

Wei-Sheng Liu,^a,^b ^* Rui-Ping Wei,^c Xiao-Liang Tang,^c Wen-Hua Wang ^c and Zheng-Hua Ju ^c

^aDepartment of Chemistry, State Key Laboratory of Applied Organic Chemistry, College of Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, ^bState Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: liuws@lzu.edu.cn

(Received 15 May 2009; accepted 12 June 2009; online 27 June 2009)

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, P n a 2₁
a = 9.524 (3) Å
b = 11.006 (4) Å
c = 5.942 (2) Å
V = 622.9 (4) Å³
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[F² > 2σ(F²)] = 0.035
wR(F²) = 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

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C2–C7 ring.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022466/hk2691sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022466/hk2691Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

For a related structure, see: Tale et al. (2003). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the C2–C7 ring.

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	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.

4-(Hydroxymethyl)phenol top

Crystal data top

C₇H₈O₂	F(000) = 264
M_r = 124.13	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0125P)² + 0.2042P] where P = (F_o² + 2F_c²)/3
1414 reflections	(Δ/σ)_max < 0.001
84 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₇H₈O₂	V = 622.9 (4) Å³
M_r = 124.13	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.524 (3) Å	µ = 0.10 mm⁻¹
b = 11.006 (4) Å	T = 298 K
c = 5.942 (2) Å	0.65 × 0.62 × 0.55 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1414 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1200 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.949	R_int = 0.036
3751 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.076	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
1414 reflections	Δρ_min = −0.17 e Å⁻³
84 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₇H₈O₂
M_r	124.13
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	9.524 (3), 11.006 (4), 5.942 (2)
V (Å³)	622.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.65 × 0.62 × 0.55

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.940, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	3751, 1414, 1200
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.076, 1.00
No. of reflections	1414
No. of parameters	84
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant Nos. 20771048 and 20621091) for financial support.

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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