Absolute configuration of (2S)-4-(4-hy-droxy-phen-yl)butan-2-ol.

The title compound, C(10)H(14)O(2), was isolated from the chloro-form extract of Taxus wallichiana Zucc. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds, forming sheets parallel to (100). There are weak inter-molecular C-H⋯π inter-actions between the sheets.

Related literature

For the isolation of the title compound, see: Fan et al. (1999 ▶). For the biological activity and medicinal uses of Taxus. wallichiana Zucc, see: Ahmed (1997 ▶); Baquar (1995 ▶); Kaul (1997 ▶); Nisar et al. (2008a ▶,b ▶; 2010 ▶); Prasain et al. (2001 ▶); Wani et al. (1971 ▶).

Experimental

Crystal data

C10H14O2

M = 166.21

Monoclinic,

a = 7.2342 (2) Å

b = 6.3815 (2) Å

c = 9.9419 (4) Å

β = 92.216 (2)°

V = 458.63 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.66 mm−1

T = 100 K

0.39 × 0.12 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.784, T max = 0.966

4954 measured reflections

1455 independent reflections

1446 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.08

1455 reflections

165 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 579 Friedel pairs

Flack parameter: −0.03 (17)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010026/lh5221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010026/lh5221Isup2.hkl

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

C10H14O2	F(000) = 180
Mr = 166.21	Dx = 1.204 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 3477 reflections
a = 7.2342 (2) Å	θ = 6.1–70.3°
b = 6.3815 (2) Å	µ = 0.66 mm−1
c = 9.9419 (4) Å	T = 100 K
β = 92.216 (2)°	Block, colorles
V = 458.63 (3) Å3	0.39 × 0.12 × 0.05 mm
Z = 2

Bruker SMART APEXII DUO CCD area-detector diffractometer	1455 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 67.5°, θmin = 6.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.784, Tmax = 0.966	k = −7→7
4954 measured reflections	l = −11→10

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.0461P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1455 reflections	Δρmax = 0.19 e Å−3
165 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 579 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (17)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.

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	0.33418 (12)	0.03888 (15)	0.11761 (9)	0.0200 (2)
O2	0.33463 (12)	0.33901 (17)	0.93717 (9)	0.0214 (2)
C1	0.22229 (17)	0.3267 (2)	0.42530 (13)	0.0191 (3)
C2	0.25737 (17)	0.2886 (2)	0.29010 (14)	0.0184 (3)
C3	0.29911 (15)	0.08712 (19)	0.24875 (13)	0.0161 (3)
C4	0.30875 (17)	−0.0757 (2)	0.34234 (14)	0.0191 (3)
C5	0.27631 (16)	−0.0347 (2)	0.47664 (13)	0.0187 (3)
C6	0.23165 (16)	0.1659 (2)	0.52052 (13)	0.0173 (3)
C7	0.19572 (19)	0.2007 (2)	0.66828 (14)	0.0222 (3)
C8	0.20129 (16)	0.4288 (2)	0.71453 (13)	0.0179 (3)
C9	0.18659 (17)	0.4510 (2)	0.86638 (13)	0.0202 (3)
C10	0.1875 (2)	0.6786 (3)	0.91038 (16)	0.0286 (4)
H1	0.192 (2)	0.463 (3)	0.4534 (16)	0.019 (4)*
H2	0.245 (2)	0.401 (3)	0.2254 (19)	0.026 (4)*
H4	0.339 (2)	−0.216 (3)	0.3145 (17)	0.024 (4)*
H5	0.281 (2)	−0.143 (3)	0.5411 (18)	0.025 (4)*
H7A	0.076 (2)	0.136 (3)	0.6896 (18)	0.027 (4)*
H7B	0.293 (3)	0.123 (3)	0.720 (2)	0.032 (5)*
H8A	0.103 (3)	0.501 (3)	0.6728 (18)	0.026 (4)*
H8B	0.322 (2)	0.494 (3)	0.6865 (15)	0.013 (4)*
H9	0.078 (2)	0.383 (3)	0.8913 (17)	0.020 (4)*
H10A	0.075 (3)	0.755 (4)	0.873 (2)	0.044 (6)*
H10B	0.304 (2)	0.749 (3)	0.8792 (17)	0.021 (4)*
H10C	0.183 (3)	0.691 (3)	1.011 (2)	0.040 (5)*
H1O1	0.319 (3)	0.151 (4)	0.062 (2)	0.043 (6)*
H1O2	0.444 (3)	0.400 (3)	0.920 (2)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0240 (4)	0.0247 (5)	0.0115 (5)	0.0004 (4)	0.0046 (3)	−0.0002 (4)
O2	0.0213 (5)	0.0303 (5)	0.0125 (5)	−0.0034 (4)	0.0007 (3)	0.0033 (4)
C1	0.0245 (6)	0.0192 (7)	0.0135 (6)	−0.0005 (5)	0.0016 (5)	−0.0021 (5)
C2	0.0220 (6)	0.0222 (8)	0.0110 (6)	−0.0008 (5)	0.0003 (5)	0.0023 (5)
C3	0.0138 (6)	0.0244 (7)	0.0101 (6)	−0.0007 (5)	0.0023 (4)	−0.0021 (5)
C4	0.0188 (6)	0.0195 (7)	0.0193 (7)	0.0006 (5)	0.0038 (4)	0.0005 (5)
C5	0.0201 (6)	0.0218 (7)	0.0142 (7)	−0.0017 (5)	0.0018 (4)	0.0029 (5)
C6	0.0180 (6)	0.0223 (7)	0.0115 (7)	−0.0027 (5)	0.0003 (5)	0.0003 (5)
C7	0.0304 (7)	0.0262 (8)	0.0102 (7)	−0.0047 (6)	0.0024 (5)	−0.0003 (5)
C8	0.0172 (6)	0.0247 (7)	0.0119 (6)	−0.0009 (5)	0.0004 (4)	0.0005 (5)
C9	0.0161 (6)	0.0325 (8)	0.0123 (7)	−0.0010 (5)	0.0024 (4)	−0.0019 (6)
C10	0.0278 (7)	0.0378 (9)	0.0201 (8)	0.0062 (7)	−0.0012 (5)	−0.0108 (6)

O1—C3	1.3728 (15)	C5—H5	0.94 (2)
O1—H1O1	0.91 (3)	C6—C7	1.5180 (17)
O2—C9	1.4473 (16)	C7—C8	1.5265 (19)
O2—H1O2	0.90 (2)	C7—H7A	0.988 (19)
C1—C6	1.3959 (19)	C7—H7B	0.99 (2)
C1—C2	1.3988 (18)	C8—C9	1.5241 (17)
C1—H1	0.943 (19)	C8—H8A	0.93 (2)
C2—C3	1.3865 (18)	C8—H8B	1.018 (15)
C2—H2	0.96 (2)	C9—C10	1.517 (2)
C3—C4	1.3948 (18)	C9—H9	0.938 (17)
C4—C5	1.390 (2)	C10—H10A	1.01 (2)
C4—H4	0.97 (2)	C10—H10B	1.013 (18)
C5—C6	1.3942 (19)	C10—H10C	1.01 (2)
C3—O1—H1O1	112.1 (15)	C8—C7—H7A	110.2 (11)
C9—O2—H1O2	109.6 (13)	C6—C7—H7B	106.5 (12)
C6—C1—C2	121.21 (12)	C8—C7—H7B	108.1 (12)
C6—C1—H1	118.9 (10)	H7A—C7—H7B	107.0 (15)
C2—C1—H1	119.9 (10)	C9—C8—C7	112.65 (11)
C3—C2—C1	119.72 (12)	C9—C8—H8A	108.3 (11)
C3—C2—H2	120.5 (11)	C7—C8—H8A	109.0 (12)
C1—C2—H2	119.7 (11)	C9—C8—H8B	109.0 (9)
O1—C3—C2	122.67 (11)	C7—C8—H8B	108.8 (9)
O1—C3—C4	117.40 (11)	H8A—C8—H8B	109.0 (14)
C2—C3—C4	119.93 (11)	O2—C9—C10	109.73 (11)
C5—C4—C3	119.64 (12)	O2—C9—C8	110.92 (10)
C5—C4—H4	119.9 (11)	C10—C9—C8	112.02 (12)
C3—C4—H4	120.4 (11)	O2—C9—H9	104.8 (11)
C4—C5—C6	121.57 (12)	C10—C9—H9	111.0 (11)
C4—C5—H5	120.8 (12)	C8—C9—H9	108.0 (10)
C6—C5—H5	117.6 (12)	C9—C10—H10A	111.3 (13)
C5—C6—C1	117.92 (12)	C9—C10—H10B	109.5 (11)
C5—C6—C7	119.18 (11)	H10A—C10—H10B	109.7 (16)
C1—C6—C7	122.90 (12)	C9—C10—H10C	111.3 (13)
C6—C7—C8	115.31 (11)	H10A—C10—H10C	105.7 (17)
C6—C7—H7A	109.3 (11)	H10B—C10—H10C	109.3 (15)
C6—C1—C2—C3	1.14 (18)	C2—C1—C6—C5	−0.29 (18)
C1—C2—C3—O1	179.72 (10)	C2—C1—C6—C7	179.64 (11)
C1—C2—C3—C4	−0.99 (17)	C5—C6—C7—C8	163.67 (11)
O1—C3—C4—C5	179.33 (10)	C1—C6—C7—C8	−16.26 (18)
C2—C3—C4—C5	0.01 (17)	C6—C7—C8—C9	−173.32 (10)
C3—C4—C5—C6	0.86 (17)	C7—C8—C9—O2	58.43 (14)
C4—C5—C6—C1	−0.71 (17)	C7—C8—C9—C10	−178.58 (11)
C4—C5—C6—C7	179.36 (11)

Cg1 is the centroid of the C1–C6 ring

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.92 (2)	1.72 (2)	2.6247 (13)	166 (2)
O2—H1O2···O1ii	0.91 (2)	1.88 (2)	2.7869 (13)	177.8 (19)
C8—H8A···Cg1iii	0.93 (2)	2.822 (15)	3.7033 (13)	158.1 (14)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.92 (2)	1.72 (2)	2.6247 (13)	166 (2)
O2—H1O2⋯O1ii	0.91 (2)	1.88 (2)	2.7869 (13)	177.8 (19)
C8—H8A⋯Cg1iii	0.93 (2)	2.822 (15)	3.7033 (13)	158.1 (14)

Symmetry codes: (i) ; (ii) ; (iii) .