Crystal structure of 3,4-di­meth­oxy­phenol

Heather A Mills-Robles; Vasumathi Desikan; James A Golen; David R Manke

doi:10.1107/S2056989015022860

. 2015 Dec 6;71(Pt 12):o1019. doi: 10.1107/S2056989015022860

Crystal structure of 3,4-dimethoxyphenol

Heather A Mills-Robles ^a, Vasumathi Desikan ^a, James A Golen ^b, David R Manke ^b,^*

PMCID: PMC4719955 PMID: 26870474

Abstract

The title compound, C₈H₁₀O₃, has two planar molecules in the asymmetric unit possessing mean deviations from planarity of 0.051 and 0.071 Å. In the crystal, there are two distinct infinite chains, both along [010]. The chains are formed by O—H⋯O interactions between the phenol and both the 3-methoxy and the 4-methoxy groups.

Keywords: crystal structure, hydrogen bonding, phenols

Related literature

For the crystal structure of the related 4-[(2,3-dimethylbut-3-en-2-yl)oxy]-3-methoxyphenol, see: Yamamoto et al. (2014 ▸). For the crystal structure of 3,4,5-trimethoxyphenol, see: Jia et al. (2012 ▸). For background and crystal structures solved during the study, see: McDonald et al. (2015 ▸); Nguyen et al. (2015 ▸). graphic file with name e-71-o1019-scheme1.jpg

Experimental

Crystal data

C₈H₁₀O₃
M _r = 154.16
Orthorhombic,
a = 8.7477 (4) Å
b = 13.8218 (7) Å
c = 26.6422 (13) Å
V = 3221.3 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.5 × 0.4 × 0.4 mm

Data collection

Bruker Venture D8 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.700, T _max = 0.746
29914 measured reflections
3996 independent reflections
3360 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.116
S = 1.04
3996 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸) and olex2.refine (Bourhis et al., 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022860/ff2145sup1.cif

e-71-o1019-sup1.cif^{(937.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022860/ff2145Isup2.hkl

e-71-o1019-Isup2.hkl^{(318.9KB, hkl)}

Click here for additional data file.^{(3.3KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015022860/ff2145Isup3.cml

Click here for additional data file.^{(1MB, tif)}

. DOI: 10.1107/S2056989015022860/ff2145fig1.tif

Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Click here for additional data file.^{(2.8MB, tif)}

. DOI: 10.1107/S2056989015022860/ff2145fig2.tif

Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

CCDC reference: 1439495

Additional supporting information: 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	0.86 (1)	2.25 (1)	2.9663 (12)	141 (2)
O1—H1⋯O3ⁱ	0.86 (1)	2.13 (1)	2.8834 (13)	145 (2)
O4—H4⋯O5ⁱ	0.86 (1)	2.15 (2)	2.8384 (13)	137 (2)
O4—H4⋯O6ⁱ	0.86 (1)	2.37 (1)	3.1107 (14)	145 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We greatly acknowledge support from the National Science Foundation (CHE-1429086).

supplementary crystallographic information

S1. Comment

In a continuing collaborative study of the solid state structure of aromatic alcohols between UMass Dartmouth and Massasoit Community College (McDonald et al., 2015; Nguyen et al., 2015), we report herein the structure of 3,4-dimethoxyphenol. A similar 3,4-dialkoxyphenol complex has been structurally characterized (Yamamoto et al., 2014) and demonstrates tip-to-tail hydrogen bonding with the 4-alkoxy group. The structure of the trisubstituted 3,4,5-trimethoxyphenol demonstrates a similar interaction, with just the 4-methoxy group involved in hydrogen bonding (Jia et al., 2012). In contrast, the title compound exhibits hydrogen bonding chains with interactions involving the methoxy groups at both the 3 and 4 positions.

The molecular structure of the title compound is shown in Figure 1. There are two molecules in the asymmetric unit, with non-hydrogen atoms possessing mean deviations from the plane of 0.051 Å and 0.071 Å. There are two distinct hydrogen bonding chains which both propagate along [010]. One is formed by O1–H1···O2 and O1–H1···O3 interactions, and the other by O4–H4···O5 and O4–H4···O6 interactions. The packing of the title compound indicating hydrogen bonding is shown in Figure 2.

S2. Experimental

A commercial sample (Aldrich) was used for crystallization. Single crystals suitable for X-ray diffraction studies were grown by slow evaporation of a methylene chloride solution.

S3. Refinement

All non-hydrogen atoms were refined anisotropically (Olex2) by full matrix least squares on F². Hydrogen atoms H1 and H4 were found from a Fourier difference map, and refined with a fixed distance of 0.86 (0.005) Å and isotropic displacement parameters of 1.50 times U_eq of the parent O atoms. The remaining hydrogen atoms were placed in calculated positions and then refined with a riding model with C–H lengths of 0.95 Å (sp²) and 0.98 Å (sp³) with isotropic displacement parameters set to 1.20 (sp²) and 1.50 (sp³) times U_eq of the parent C atom.