4-Ethyl­phenol

Richard Betz; Peter Klüfers; Peter Mayer

doi:10.1107/S1600536809005108

. 2009 Feb 18;65(Pt 3):o544. doi: 10.1107/S1600536809005108

4-Ethylphenol

Richard Betz ^a, Peter Klüfers ^a,^*, Peter Mayer ^a

PMCID: PMC2968585 PMID: 21582203

Abstract

The title compound, C₈H₁₀O, crystallizes with three molecules in the asymmetric unit. O—H⋯O hydrogen bonds form cooperative chains connecting the molecules along [100]. On the unitary graph level, this pattern is assigned a DDD descriptor. The ternary descriptor is C ₃ ³(6).

Related literature

For the crystal structure of a co-crystallizate of the title compound and a copper complex, see: Butcher et al. (1995 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C₈H₁₀O
M _r = 122.16
Orthorhombic,
a = 5.9318 (19) Å
b = 16.514 (3) Å
c = 22.574 (9) Å
V = 2211.2 (12) Å³
Z = 12
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.47 × 0.32 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T _min = 0.977, T _max = 0.987
9193 measured reflections
2594 independent reflections
1457 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.085
S = 0.91
2594 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005108/jh2071sup1.cif

e-65-0o544-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005108/jh2071Isup2.hkl

e-65-0o544-Isup2.hkl^{(127.4KB, hkl)}

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⋯O3ⁱ	0.84	1.84	2.662 (2)	166
O2—H2⋯O1ⁱⁱ	0.84	1.81	2.642 (2)	171
O3—H3⋯O2ⁱⁱⁱ	0.84	1.84	2.664 (2)	165

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

Acknowledgments

The authors thank Professor Klapötke for generous allocation of measurement time on the diffractometer.

supplementary crystallographic information

Comment

In a program focused on the influence of bonding to pentavalent central atoms on the geometry of aromatic alcohols, the crystal structure of para-ethylphenol was determined.

There are three molecules in the asymmetric unit which do not show non-crystallographic symmetry (Fig. 1 and Fig. 2). The hydrogen atoms on the hydroxy groups reside in the planes of the respective aromatic moiety whereas the alkyl chains are oriented approximately perpendicular to them. The least-squares planes defined by the aromatic moieties and the atoms of the hydroxy group and their respective aromatic carrier atom enclose angles roughly between 1° and 16°. The least-squares planes defined by the aromatic moieties and the C atoms of the alkyl chain and their respective aromatic carrier atom intersect at angles roughly between 77° and 80°.

The hyxdroxy groups furnish the formation of cooperative chains of hydrogen bonds along [1 0 0] (Fig. 3). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), this pattern can be ascribed a DDD descriptor on the unitary level. The ternary descriptor of these chains is C₃³(6). The molecules are packed in a pseudo-trigonal mode with the hydrophilic part of the molecules residing in the center of these entities (Fig. 4).

The molecular packing of the title compound is shown in Figure 5.

Experimental

The compound was obtained commercially (Aldrich) and used for diffraction studies as received.