2-(3-Meth­oxy­phen­oxy)benzoic acid

Zhi-Fang Zhang

doi:10.1107/S1600536811011019

. 2011 Apr 7;67(Pt 5):o1078. doi: 10.1107/S1600536811011019

2-(3-Methoxyphenoxy)benzoic acid

Zhi-Fang Zhang ^a,^*

PMCID: PMC3089338 PMID: 21754401

Abstract

In the crystal structure of the title compound, C₁₄H₁₂O₄, the molecules form classical O—H⋯O hydrogen-bonded carboxylic acid dimers. These dimers are linked by C—H⋯pi; interactions into a three-dimensional network. The benzene rings are oriented at a dihedral angle of 69.6 (3)°.

Related literature

For applications of the title compound, see: Jackson et al. (1993) ▶; Gapinski et al. (1990 ▶). For related structures, see: Shi et al. (2011 ▶); Raghunathan et al. (1982 ▶). For the synthesis of the title compound, see: Pellón et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₂O₄
M _r = 244.24
Orthorhombic,
a = 14.309 (3) Å
b = 8.5330 (17) Å
c = 19.432 (4) Å
V = 2372.6 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.970, T _max = 0.995
4273 measured reflections
2175 independent reflections
1056 reflections with I > 2σ(I)
R _int = 0.093
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.133
S = 1.00
2175 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011019/hg5013sup1.cif

e-67-o1078-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011019/hg5013Isup2.hkl

e-67-o1078-Isup2.hkl^{(107KB, hkl)}

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

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

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3ⁱ	0.82	1.82	2.633 (3)	173
C1—H1B⋯Cg1ⁱⁱ	0.96	2.89	3.784 (4)	155

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

Acknowledgments

The author gratefully acknowledges financial support from the Natural Science Foundation of the Education Department of Shaanxi Provincial Government (09JK844) and is grateful for support provided by the key industry problem plan of Yulin (gygg200807) and the special research projects of Yulin University (08YK17).

supplementary crystallographic information

Comment

The title compound, 2-(3-methoxyphenoxy)benzoic acid is an important intermediate of xanthone dicarboxylic acids (Jackson et al., 1972). Xanthone dicarboxylic acid, such as LY223982, which inhibited the binding of LTB4 to receptors on intact human neutrophils nearly as well as nonradioactive LTB4 (Gapinski et al., 1990). Knowledge of the crystal structure of such benzoicacid derivatives gives us not only information about nuclearity of the complex molecule, but is important in understanding the behaviour of these compounds with respect to the mechanisms of pharmacological activities and physiological activities. Therefore, we have synthesized the title compound, (I), and report its crystal structure here.

The molecular structure of (I) is shown in Fig. 1, and the intermolecular O—H···O hydrogen bond (Table 1) results in the formation of carboxylic acid dimers (Fig. 2.). The bond lengths are within normal ranges (Allen et al., 1987). Similar crystal structure of some compounds have been reported (Shi et al., 2011; Raghunathan et al., 1982).

In the molecule of (I), the dihedral angle of the rings(C3—C6) and (C8—C13) is 69.6 (3)°, the molecules were connected together via O—H···O intermolecular hydrogen bonds to form dimers. These dimers are linked by C—H···π and weak C—H···O interactions to give a three-dimensional network, which seems to be very effective in the stabilization of the crystal structure.

Experimental

The title compound (I) was prepared by the method of Ullmann condensation reaction reported in literature (Pellón et al., 1995). A mixture of 2-chlorobenzoic acid (6.26 g, 0.04 mol), 3-methoxyphenol (9.93 g, 0.08 mol), anhydrous K₂CO₃ (11.04 g' 0.08 mol), pyridine (1.58 g' 0.02 mol), Cu powder (0.2 g) and cuprous iodide (0.2 g) in 25 ml water was kept at reflux for two hours. The mixture was then basified with Na₂CO₃ solution and extracted with diethyl ether. The aqueous solution was acidified with HCl, the precipitated solid was filtered off and disolved in NaOH; the basic solution was filtered (charcoal) and acidified with acetic acid. The 2-(3-methoxyphenoxy)benzoic acid was crystalized from the mixture.