2-(2,5-Dimethyl­phen­oxy)ethanol

Miho Ukai; Tsunehisa Okuno

doi:10.1107/S1600536813005187

. 2013 Feb 28;69(Pt 3):o456. doi: 10.1107/S1600536813005187

2-(2,5-Dimethylphenoxy)ethanol

Miho Ukai ^a, Tsunehisa Okuno ^a,^*

PMCID: PMC3588424 PMID: 23476623

Abstract

There are two independent molecules in the asymmetric unit of the title phenoxyethanol derivative, C₁₀H₁₄O₂, Each molecule has an approximately planar structure except for the hydroxy groups (r.m.s. deviations = 0.0281 and 0.0144 Å). The ethylenedioxy groups have a gauche conformation. In the crystal, the molecules form O—H⋯O hydrogen-bonded chains along the a axis.

Related literature

For related structures of phenoxyethanol derivatives, see: Sanyal & Lahti (2006 ▶); Sierra & Lahti (2004 ▶).

Experimental

Crystal data

C₁₀H₁₄O₂
M _r = 166.22
Orthorhombic,
a = 8.274 (3) Å
b = 13.745 (4) Å
c = 17.113 (5) Å
V = 1946.2 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.10 × 0.09 × 0.09 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T _min = 0.989, T _max = 0.993
16794 measured reflections
2661 independent reflections
2440 reflections with F ² > 2σ(F ²)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.121
S = 1.09
2660 reflections
223 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare, et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(34.8KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005187/nk2198sup1.cif

e-69-0o456-sup1.cif^{(34.8KB, cif)}

Click here for additional data file.^{(130.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005187/nk2198Isup2.hkl

e-69-0o456-Isup2.hkl^{(130.7KB, hkl)}

Click here for additional data file.^{(3.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005187/nk2198Isup3.cml

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
O2—H2⋯O4ⁱ	0.84	1.82	2.623 (3)	159
O4—H4⋯O2ⁱⁱ	0.84	1.80	2.626 (3)	167

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

supplementary crystallographic information

Comment

The title compound, C₁₀H₁₄O₂, is a phenoxyethanol derivative whose structures are often observed in phenyleneethynylene derivatives (Sanyal & Lahti, 2006) or phynylenevinylene derivatives (Sierra & Lahti, 2004). Introduction of ethylenedioxy groups was aiming for control of intermolecular interacrions and/or for improvement of solubility to common organic solvents.

The molecular structure of the title compound is shown in Fig. 1. There are two crystallographically independent molecules (A and B) in the unit cell. Both molecules have a planar structure (the C1—C10/O1 plane: r.m.s. deviation = 0.0281 Å, the C11—C20/O3 plane: r.m.s. deviation = 0.0144 Å) except for the hydroxyl groups. The significant difference between A and B is recognized at the torsion angles of ethylenedioxy groups which have a gauche conformation.

In the crystal, the molecules form one-dimensional O—H···O hydrogen-bonds (Fig. 2), where the intermolecular distances of O2···O4ⁱ and O2···O4ⁱⁱ are 2.623 (3) Å and 2.626 (3) Å, respectively [Symmetry codes: (i) -x + 1, -y + 1, z + 1/2; (ii) -x + 1/2, y + 1/2, z + 1/2.].

Experimental

The title compound was commercially purchased. Single crystals with sufficient quality were prepared by sublimation at room temperature.