2-(3-Meth-oxy-phen-oxy)benzoic acid.

In the crystal structure of the title compound, C(14)H(12)O(4), the mol-ecules form classical O-H⋯O hydrogen-bonded carb-oxy-lic acid dimers. These dimers are linked by C-H⋯pi; inter-actions 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 = 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

Δρmax = 0.16 e Å−3

Δρmin = −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.

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

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

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

C14H12O4	F(000) = 1024
Mr = 244.24	Dx = 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

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

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(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3
2175 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .