3,4,5-Trimeth­oxy­phenol

Xiao-Chuan Jia; Jing Li; Zhi-Rui Yu; Hui Zhang; Lei Zhou

doi:10.1107/S1600536812042997

. 2012 Oct 20;68(Pt 11):o3160. doi: 10.1107/S1600536812042997

3,4,5-Trimethoxyphenol

Xiao-Chuan Jia ^a,^*, Jing Li ^a, Zhi-Rui Yu ^a, Hui Zhang ^a, Lei Zhou ^a

PMCID: PMC3515255 PMID: 23284475

Abstract

The asymmetric unit of the title compound, C₉H₁₂O₄, consists of two crystallographically independent molecules with similar conformations: essentially planar [r.m.s deviations for C₆O₄ = 0.0057 and 0.0137 Å] except for the central methoxy-methyl group [C—C—O—C torsion angles = 83.3 (2) and 83.9 (2)°]. In the crystal, O—H⋯O hydrogen bonds link the molecules, generating supramolecular chains along the b axis.The three-dimensional crystal structure is stabilized by C—H⋯O and C—H⋯π interactions.

Related literature

For background information on the energetics and anti-oxidant potential of phenolic compounds, see: Matos et al. (2008 ▶); Gong et al. (2009 ▶).

Experimental

Crystal data

C₉H₁₂O₄
M _r = 184.19
Monoclinic,
a = 15.355 (3) Å
b = 11.139 (2) Å
c = 11.546 (2) Å
β = 111.38 (3)°
V = 1839.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.990
16747 measured reflections
3257 independent reflections
2957 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.123
S = 1.05
3257 reflections
243 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(20.4KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042997/tk5160sup1.cif

e-68-o3160-sup1.cif^{(20.4KB, cif)}

Click here for additional data file.^{(159.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042997/tk5160Isup2.hkl

e-68-o3160-Isup2.hkl^{(159.8KB, hkl)}

Click here for additional data file.^{(3.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812042997/tk5160Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1–C3,C5,C7,C9 and C10–C12,C14,C16,C18 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O7ⁱ	0.82	1.93	2.7484 (18)	179
O1—H1⋯O3ⁱⁱ	0.82	1.90	2.7204 (17)	175
C6—H6A⋯O1ⁱⁱⁱ	0.96	2.57	3.256 (3)	129
C15—H15A⋯O5^iv	0.96	2.59	3.270 (3)	128
C4—H4B⋯Cg1^v	0.96	2.86	3.777 (2)	160
C17—H17B⋯Cg2^vi	0.96	2.85	3.736 (2)	154
C13—H13B⋯O1^vii	0.96	2.49	3.303 (3)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Acknowledgments

We thank the Tianjin Entry–Exit Inspection and Quarantine Bureau for financial support.

supplementary crystallographic information

Comment

The study of the energetics of phenolic compounds (Matos et al., 2008) has considerable practical interest since this class of chemical compound includes a large number of synthetic and naturally occurring antioxidants. They inhibit the oxidation of materials of both commercial and biological importance. This antioxidant function is due to the ability of phenols to trap the peroxyl radicals via the hydrogen transfer reaction (Gong et al., 2009). In order to expand this field, we now report the structure of the title compound.

The molecule of the title compound (Fig. 1), consists of two crystallographically independent molecules, A and B, with similar conformations. All O-atoms in both molecules are coplanar with the benzene rings they are attached to, and the mean r.s.m in molecules A and B are 0.0057 and 0.0137 Å, respectively.

In the crystal, it is worth mentioning that strong intermolecular O—H···O hydrogen bonds link molecules A and B to generate a one dimensional chain (Fig. 2 and Table 1) along the b axis. These are connected into a supramolecular layer in the bc plane by C—H···O and C-H···π interactions (Table 1). The layers are connected into a three-dimensional crystal structure by C—H···O hydrogen bonds (Table 2) involving the C13 and O1 atoms (Table 1).

Experimental

3,4,5-Trimethoxyphenol was obtained commercially from Aldrich Chemical Co. Single crystals suitable for X-ray diffraction were obtained by recrystallizing the prude product from its chloroform solution by slow evaporation at room temperature over a period of seven days.