Redetermination of 3,5-dimethyl­phenol

Richard Betz; Cedric McCleland; Harold Marchand

doi:10.1107/S1600536811013547

. 2011 Apr 16;67(Pt 5):o1152. doi: 10.1107/S1600536811013547

Redetermination of 3,5-dimethylphenol

Richard Betz ^a,^*, Cedric McCleland ^a, Harold Marchand ^a

PMCID: PMC3089283 PMID: 21754460

Abstract

The previous structure determination [Gillier-Pandraud et al. (1972 ▶). C. R. Acad. Sci. Ser. C, 275, 1495] of the title compound, C₈H₁₀O, did not report atomic coordinates. There are two molecules in the asymmetric unit, A and B, which both show approximate non-crystallographic C _s symmetry. The intracyclic C—C—C angles cover the range 118.74 (12)–121.76 (13)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, generating [001] C ₂ ²(4) chains such that molecules A and B alternate. There is no aromatic π–π stacking in the crystal as the shortest centroid–centroid distance is greater than 4.74 Å.

Related literature

The compound has been deposited with the CSD (refcode: DMPHNL) but no three-dimensional-coordinates are available (Gillier-Pandraud et al., 1972 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₈H₁₀O
M _r = 122.16
Monoclinic,
a = 11.9807 (6) Å
b = 13.8725 (7) Å
c = 8.5378 (4) Å
β = 90.000 (2)°
V = 1419.00 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.50 × 0.41 × 0.33 mm

Data collection

Bruker APEXII CCD diffractometer
12884 measured reflections
3392 independent reflections
2998 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.143
S = 1.04
3392 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013547/hb5838sup1.cif

e-67-o1152-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013547/hb5838Isup2.hkl

e-67-o1152-Isup2.hkl^{(166.4KB, 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⋯O2ⁱ	0.84	1.91	2.7463 (13)	171
O2—H2⋯O1ⁱⁱ	0.84	1.90	2.7327 (13)	172

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

Acknowledgments

The authors thank Mrs Jenny Bell for helpful discussions.

supplementary crystallographic information

Comment

Phenol and derivatives are interesting bonding partners for a variety of transition metals and elements from the p-block of the periodic system. They can act as neutral or – upon deprotonation – as anionic monodentate ligands. Upon variation of the substituents on the aromatic system, a seemingly endless series of symmetric as well as asymmetric phenol derivatives featuring different steric pretenses and acidities of the hydroxyl-group are available. At the beginning of a larger study aimed at elucidating the coordination behaviour of various phenol-derivatives in dependence of pH-value and substitution pattern on the phenyl moiety, it seemed of interest to determine the crystal structure of the title compound to enable comparisons with metric parameters in envisioned coordination compounds. Although the structure has been deposited with the Cambridge Structural Database (Gillier-Pandraud et al., 1972), no three-dimensional-coordinates were provided.

The asymmetric unit comprises two molecules of the title compound which are nearly orientated perpendicular to each other. The least-squares planes defined by the C-atoms of the respective phenyl moieties intersect at an angle of 87.87 (4) °. Intracyclic C–C–C angles span a range of 119–122 ° with the biggest angles invariably found on the C-atoms bearing the hydroxyl group and the C-atoms in para-position to these, respectively. The H-atoms of both hydroxyl groups are approximately in plane with the aromatic systems (Fig. 1).

In the crystal structure, a set of cooperative hydrogen bonds connects the molecules to infinite chains along the crystallographic c-axis. Both molecules in the asymmetric unit participate alternately in these chains. In terms of graph-set analysis, the description of these intermolecular interactions necessitates a C²₂(4) descriptor on the binary level (Fig. 2). The closest distance between two centers of gravity was measured at 4.7437 (8) Å.

The packing of the title compound in the crystal structure is shown in Figure 3.

Experimental

The compound was obtained commercially (Fluka). Crystals suitable for the X-ray diffraction study were taken directly from the provided compound.