2-(3-Meth­oxy­phen­oxy)benzoic acid

Zhang, Z.-F.

doi:10.1107/S1600536811011019

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1078

doi:10.1107/S1600536811011019

Open

access

2-(3-Methoxyphenoxy)benzoic acid

Zhi-Fang Zhang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Yulin University, Yulin 719000, People's Republic of China
^*Correspondence e-mail: zhifang889@sohu.com

(Received 19 March 2011; accepted 24 March 2011; online 7 April 2011)

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, P b c a
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[F² > 2σ(F²)] = 0.062
wR(F²) = 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

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
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) (thermal ellipsoids are shown at 30% probability levels).
	Fig. 2. The structure of a dimer of (I).

2-(3-Methoxyphenoxy)benzoic acid top

Crystal data top

C₁₄H₁₂O₄	F(000) = 1024
M_r = 244.24	D_x = 1.367 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 14.309 (3) Å	θ = 9–12°
b = 8.5330 (17) Å	µ = 0.10 mm⁻¹
c = 19.432 (4) Å	T = 295 K
V = 2372.6 (8) Å³	Block, colourless
Z = 8	0.30 × 0.10 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.093
Graphite monochromator	θ_max = 25.4°, θ_min = 2.1°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.970, T_max = 0.995	l = −23→23
4273 measured reflections	3 standard reflections every 200 reflections
2175 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.039P)²] where P = (F_o² + 2F_c²)/3
2175 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

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

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
2175 reflections	Δρ_min = −0.16 e Å⁻³
163 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.60412 (16)	0.2617 (3)	0.77635 (10)	0.0641 (7)
C1	0.6361 (3)	0.4135 (4)	0.79576 (18)	0.0738 (11)
H1A	0.6239	0.4863	0.7592	0.111*
H1B	0.7021	0.4098	0.8046	0.111*
H1C	0.6040	0.4468	0.8366	0.111*
O2	0.70190 (16)	0.0652 (2)	0.99264 (12)	0.0668 (7)
C2	0.6162 (2)	0.1419 (4)	0.82240 (16)	0.0510 (8)
O3	0.88741 (15)	0.0003 (3)	0.97959 (10)	0.0654 (7)
C3	0.6528 (2)	0.1601 (4)	0.88657 (16)	0.0495 (8)
H3A	0.6720	0.2584	0.9016	0.059*
O4	0.95145 (16)	−0.0699 (3)	1.07827 (11)	0.0783 (8)
H4A	0.9992	−0.0465	1.0573	0.117*
C4	0.6614 (2)	0.0306 (4)	0.92945 (16)	0.0472 (8)
C5	0.6323 (2)	−0.1143 (4)	0.90941 (18)	0.0570 (9)
H5A	0.6371	−0.2000	0.9388	0.068*
C6	0.5953 (3)	−0.1298 (4)	0.84420 (18)	0.0660 (10)
H6A	0.5751	−0.2279	0.8296	0.079*
C7	0.5878 (2)	−0.0056 (5)	0.80078 (18)	0.0638 (10)
H7A	0.5636	−0.0193	0.7568	0.077*
C8	0.7034 (2)	−0.0465 (4)	1.04428 (17)	0.0533 (8)
C9	0.7889 (2)	−0.0922 (3)	1.06981 (15)	0.0454 (7)
C10	0.7896 (2)	−0.1884 (4)	1.12863 (16)	0.0535 (9)
H10A	0.8463	−0.2195	1.1477	0.064*
C11	0.7077 (3)	−0.2363 (4)	1.15792 (17)	0.0598 (9)
H11A	0.7090	−0.3012	1.1964	0.072*
C12	0.6238 (3)	−0.1898 (5)	1.1312 (2)	0.0666 (10)
H12A	0.5683	−0.2236	1.1512	0.080*
C13	0.6218 (2)	−0.0919 (5)	1.0743 (2)	0.0699 (10)
H13A	0.5650	−0.0575	1.0567	0.084*
C14	0.8796 (2)	−0.0495 (4)	1.03863 (15)	0.0488 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0741 (17)	0.0676 (16)	0.0506 (13)	0.0054 (14)	−0.0066 (12)	0.0027 (13)
C1	0.091 (3)	0.067 (3)	0.064 (2)	0.008 (2)	−0.008 (2)	0.010 (2)
O2	0.0799 (17)	0.0490 (13)	0.0716 (15)	−0.0051 (12)	−0.0318 (14)	0.0080 (12)
C2	0.049 (2)	0.055 (2)	0.0488 (19)	0.0094 (18)	0.0042 (15)	0.0037 (18)
O3	0.0670 (15)	0.0839 (17)	0.0452 (12)	−0.0097 (13)	−0.0051 (11)	0.0177 (14)
C3	0.046 (2)	0.0420 (19)	0.061 (2)	−0.0060 (16)	−0.0011 (16)	−0.0044 (16)
O4	0.0547 (15)	0.115 (2)	0.0654 (16)	−0.0057 (16)	−0.0086 (13)	0.0296 (15)
C4	0.0391 (18)	0.046 (2)	0.0565 (19)	0.0019 (14)	−0.0081 (16)	−0.0041 (18)
C5	0.062 (2)	0.045 (2)	0.064 (2)	0.0033 (19)	0.0009 (19)	−0.0012 (18)
C6	0.081 (3)	0.043 (2)	0.074 (2)	−0.0001 (19)	0.002 (2)	−0.014 (2)
C7	0.064 (2)	0.070 (2)	0.057 (2)	0.001 (2)	−0.0037 (17)	−0.020 (2)
C8	0.062 (2)	0.0448 (19)	0.0530 (19)	0.0070 (18)	−0.0061 (17)	0.0012 (16)
C9	0.0518 (18)	0.0384 (17)	0.0461 (16)	−0.0025 (15)	0.0024 (16)	−0.0004 (14)
C10	0.058 (2)	0.059 (2)	0.0439 (19)	0.0086 (18)	−0.0046 (18)	−0.0023 (15)
C11	0.070 (2)	0.061 (2)	0.0485 (19)	−0.002 (2)	0.0065 (19)	0.0034 (17)
C12	0.053 (2)	0.075 (3)	0.072 (3)	0.003 (2)	0.015 (2)	−0.002 (2)
C13	0.048 (2)	0.079 (3)	0.083 (3)	0.011 (2)	0.001 (2)	−0.006 (2)
C14	0.057 (2)	0.0475 (18)	0.0423 (18)	−0.0035 (17)	−0.0138 (16)	0.0029 (15)

Geometric parameters (Å, º) top

O1—C2	1.369 (3)	C5—H5A	0.9300
O1—C1	1.425 (4)	C6—C7	1.360 (5)
C1—H1A	0.9600	C6—H6A	0.9300
C1—H1B	0.9600	C7—H7A	0.9300
C1—H1C	0.9600	C8—C13	1.362 (4)
O2—C8	1.384 (3)	C8—C9	1.377 (4)
O2—C4	1.389 (3)	C9—C10	1.407 (4)
C2—C3	1.362 (4)	C9—C14	1.477 (4)
C2—C7	1.388 (4)	C10—C11	1.366 (4)
O3—C14	1.229 (3)	C10—H10A	0.9300
C3—C4	1.389 (4)	C11—C12	1.366 (4)
C3—H3A	0.9300	C11—H11A	0.9300
O4—C14	1.296 (3)	C12—C13	1.386 (5)
O4—H4A	0.8200	C12—H12A	0.9300
C4—C5	1.362 (4)	C13—H13A	0.9300
C5—C6	1.379 (4)

C2—O1—C1	117.7 (2)	C6—C7—C2	119.7 (3)
O1—C1—H1A	109.5	C6—C7—H7A	120.1
O1—C1—H1B	109.5	C2—C7—H7A	120.1
H1A—C1—H1B	109.5	C13—C8—C9	121.8 (3)
O1—C1—H1C	109.5	C13—C8—O2	119.6 (3)
H1A—C1—H1C	109.5	C9—C8—O2	118.1 (3)
H1B—C1—H1C	109.5	C8—C9—C10	117.7 (3)
C8—O2—C4	120.0 (2)	C8—C9—C14	124.2 (3)
O1—C2—C3	124.2 (3)	C10—C9—C14	118.1 (3)
O1—C2—C7	116.2 (3)	C11—C10—C9	120.5 (3)
C3—C2—C7	119.6 (3)	C11—C10—H10A	119.8
C2—C3—C4	119.5 (3)	C9—C10—H10A	119.8
C2—C3—H3A	120.2	C10—C11—C12	120.6 (3)
C4—C3—H3A	120.2	C10—C11—H11A	119.7
C14—O4—H4A	109.5	C12—C11—H11A	119.7
C5—C4—O2	125.0 (3)	C11—C12—C13	119.8 (3)
C5—C4—C3	121.5 (3)	C11—C12—H12A	120.1
O2—C4—C3	113.4 (3)	C13—C12—H12A	120.1
C4—C5—C6	117.9 (3)	C8—C13—C12	119.7 (4)
C4—C5—H5A	121.1	C8—C13—H13A	120.2
C6—C5—H5A	121.1	C12—C13—H13A	120.2
C7—C6—C5	121.7 (3)	O3—C14—O4	122.0 (3)
C7—C6—H6A	119.1	O3—C14—C9	123.2 (3)
C5—C6—H6A	119.1	O4—C14—C9	114.8 (3)

C1—O1—C2—C3	3.1 (5)	C13—C8—C9—C10	−0.1 (5)
C1—O1—C2—C7	−177.4 (3)	O2—C8—C9—C10	171.1 (3)
O1—C2—C3—C4	179.6 (3)	C13—C8—C9—C14	178.6 (3)
C7—C2—C3—C4	0.1 (5)	O2—C8—C9—C14	−10.2 (5)
C8—O2—C4—C5	−9.0 (5)	C8—C9—C10—C11	1.3 (4)
C8—O2—C4—C3	171.1 (3)	C14—C9—C10—C11	−177.5 (3)
C2—C3—C4—C5	−1.3 (5)	C9—C10—C11—C12	−1.0 (5)
C2—C3—C4—O2	178.6 (3)	C10—C11—C12—C13	−0.6 (6)
O2—C4—C5—C6	−178.6 (3)	C9—C8—C13—C12	−1.5 (5)
C3—C4—C5—C6	1.3 (5)	O2—C8—C13—C12	−172.5 (3)
C4—C5—C6—C7	−0.1 (5)	C11—C12—C13—C8	1.8 (6)
C5—C6—C7—C2	−1.1 (6)	C8—C9—C14—O3	−16.7 (5)
O1—C2—C7—C6	−178.4 (3)	C10—C9—C14—O3	162.0 (3)
C3—C2—C7—C6	1.1 (5)	C8—C9—C14—O4	163.9 (3)
C4—O2—C8—C13	−67.7 (4)	C10—C9—C14—O4	−17.4 (4)
C4—O2—C8—C9	121.0 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₄
M_r	244.24
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	14.309 (3), 8.5330 (17), 19.432 (4)
V (Å³)	2372.6 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	4273, 2175, 1056
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.133, 1.00
No. of reflections	2175
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+3/2, y+1/2, z.

Acknowledgements

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).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans.2, pp. S1–19. Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gapinski, D. M., Mallett, B. E., Froelich, L. L. & Jackson, W. T. (1990). J. Med. Chem. 33, 2798-2807. CrossRef CAS PubMed Web of Science Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Jackson, W. T., Boyd, R. J., Froelich, L. L., Gapinski, D. M., Mallett, B. E. & Sawyer, J. S. (1993). J. Med. Chem. 36, 1726–1734. CrossRef CAS PubMed Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Pellón, R. F., Carrasco, R., Milián, V.& Rodes, L. (1995). Synth. Commun. 25, 1077–1083. Google Scholar
Raghunathan, S., Chandrasekhar, K. & Pattabhi, V. (1982). Acta Cryst. B38, 2536–2538. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, L., Zhang, Q., Xiao, Q., Wu, T. & Zhu, H.-J. (2011). Acta Cryst. E67, o748. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1078

doi:10.1107/S1600536811011019

Open

access