2-(o-Tol-yloxy)benzoic acid.

In the crystal structure of the title compound, C(14)H(12)O(3), mol-ecules are linked via inter-molecular O-H⋯O hydrogen bonds, resulting in dimer formation. The dihedral angle between the two phenyl rings is 76.2 (2)°.

Related literature

For the synthesis, see: Glorius et al. (2009 ▶); For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12O3

M = 228.24

Triclinic,

a = 7.0900 (14) Å

b = 7.4820 (15) Å

c = 12.680 (3) Å

α = 95.34 (3)°

β = 96.36 (3)°

γ = 115.76 (3)°

V = 594.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.974, T max = 0.991

2382 measured reflections

2190 independent reflections

1437 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.178

S = 1.00

2190 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 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/S1600536811017119/vm2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017119/vm2093Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017119/vm2093Isup3.cml

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

C14H12O3	Z = 2
Mr = 228.24	F(000) = 240
Triclinic, P1	Dx = 1.275 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0900 (14) Å	Cell parameters from 25 reflections
b = 7.4820 (15) Å	θ = 9–14°
c = 12.680 (3) Å	µ = 0.09 mm−1
α = 95.34 (3)°	T = 293 K
β = 96.36 (3)°	Block, colorless
γ = 115.76 (3)°	0.30 × 0.20 × 0.10 mm
V = 594.5 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1437 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→8
Tmin = 0.974, Tmax = 0.991	l = −15→15
2382 measured reflections	3 standard reflections every 200 reflections
2190 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.094P] where P = (Fo2 + 2Fc2)/3
2190 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 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	0.4820 (3)	0.1177 (2)	0.80889 (14)	0.0712 (5)
C1	0.2152 (6)	0.0560 (7)	0.6153 (4)	0.1589 (19)
H1A	0.1796	−0.0054	0.6782	0.238*
H1B	0.1718	−0.0467	0.5539	0.238*
H1C	0.1434	0.1376	0.6043	0.238*
O2	0.0651 (3)	−0.2020 (3)	0.99961 (15)	0.0772 (6)
H2A	−0.0042	−0.1483	1.0230	0.116*
C2	0.4515 (5)	0.1851 (4)	0.6302 (2)	0.0833 (8)
O3	0.1733 (3)	0.0598 (3)	0.91609 (17)	0.0833 (6)
C3	0.5551 (8)	0.2950 (7)	0.5531 (3)	0.1137 (13)
H3A	0.4763	0.2862	0.4874	0.136*
C4	0.7687 (8)	0.4147 (6)	0.5719 (3)	0.1119 (13)
H4A	0.8334	0.4873	0.5196	0.134*
C5	0.8863 (5)	0.4283 (5)	0.6654 (3)	0.0904 (9)
H5A	1.0323	0.5095	0.6776	0.108*
C6	0.7915 (4)	0.3231 (4)	0.7426 (2)	0.0666 (7)
H6A	0.8727	0.3321	0.8075	0.080*
C7	0.5773 (4)	0.2046 (3)	0.72433 (19)	0.0570 (6)
C8	0.4571 (3)	−0.0695 (3)	0.82224 (18)	0.0533 (6)
C9	0.5732 (4)	−0.1542 (3)	0.7750 (2)	0.0654 (7)
H9A	0.6639	−0.0868	0.7289	0.078*
C10	0.5543 (5)	−0.3372 (4)	0.7963 (2)	0.0735 (7)
H10A	0.6318	−0.3935	0.7642	0.088*
C11	0.4216 (4)	−0.4382 (4)	0.8646 (2)	0.0722 (7)
H11A	0.4096	−0.5619	0.8791	0.087*
C12	0.3066 (4)	−0.3541 (3)	0.91134 (19)	0.0605 (6)
H12A	0.2185	−0.4218	0.9583	0.073*
C13	0.3188 (3)	−0.1708 (3)	0.89020 (17)	0.0497 (5)
C14	0.1800 (3)	−0.0953 (3)	0.93742 (18)	0.0522 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0866 (12)	0.0514 (9)	0.0985 (13)	0.0410 (9)	0.0489 (10)	0.0272 (9)
C1	0.102 (3)	0.141 (4)	0.193 (5)	0.043 (3)	−0.048 (3)	−0.014 (3)
O2	0.0842 (12)	0.0730 (11)	0.1051 (14)	0.0510 (10)	0.0480 (11)	0.0389 (10)
C2	0.092 (2)	0.0775 (18)	0.0812 (19)	0.0452 (16)	−0.0036 (16)	0.0006 (15)
O3	0.0924 (14)	0.0684 (11)	0.1259 (16)	0.0542 (10)	0.0591 (12)	0.0458 (11)
C3	0.174 (4)	0.131 (3)	0.064 (2)	0.099 (3)	−0.001 (2)	0.015 (2)
C4	0.161 (4)	0.127 (3)	0.093 (3)	0.089 (3)	0.065 (3)	0.053 (2)
C5	0.095 (2)	0.083 (2)	0.110 (2)	0.0428 (17)	0.0529 (19)	0.0361 (18)
C6	0.0678 (16)	0.0677 (15)	0.0724 (16)	0.0338 (13)	0.0220 (13)	0.0191 (12)
C7	0.0694 (15)	0.0468 (11)	0.0687 (15)	0.0350 (11)	0.0240 (12)	0.0141 (10)
C8	0.0582 (13)	0.0420 (11)	0.0655 (14)	0.0267 (10)	0.0141 (11)	0.0091 (10)
C9	0.0781 (16)	0.0549 (13)	0.0775 (16)	0.0382 (12)	0.0308 (13)	0.0132 (12)
C10	0.0914 (19)	0.0580 (14)	0.0921 (19)	0.0486 (14)	0.0324 (15)	0.0121 (13)
C11	0.0890 (18)	0.0517 (13)	0.0904 (19)	0.0415 (13)	0.0252 (15)	0.0169 (13)
C12	0.0660 (14)	0.0481 (12)	0.0724 (15)	0.0286 (11)	0.0168 (12)	0.0120 (11)
C13	0.0482 (11)	0.0419 (11)	0.0590 (13)	0.0213 (9)	0.0064 (10)	0.0052 (9)
C14	0.0496 (12)	0.0450 (11)	0.0649 (14)	0.0220 (9)	0.0132 (10)	0.0141 (10)

O1—C8	1.363 (2)	C5—C6	1.363 (4)
O1—C7	1.392 (3)	C5—H5A	0.9300
C1—C2	1.505 (5)	C6—C7	1.364 (3)
C1—H1A	0.9600	C6—H6A	0.9300
C1—H1B	0.9600	C8—C9	1.390 (3)
C1—H1C	0.9600	C8—C13	1.393 (3)
O2—C14	1.272 (2)	C9—C10	1.372 (3)
O2—H2A	0.8200	C9—H9A	0.9300
C2—C7	1.364 (4)	C10—C11	1.375 (4)
C2—C3	1.398 (5)	C10—H10A	0.9300
O3—C14	1.235 (2)	C11—C12	1.376 (3)
C3—C4	1.361 (5)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.390 (3)
C4—C5	1.340 (5)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.482 (3)
C8—O1—C7	119.48 (17)	C2—C7—O1	118.9 (2)
C2—C1—H1A	109.5	C6—C7—O1	118.4 (2)
C2—C1—H1B	109.5	O1—C8—C9	121.8 (2)
H1A—C1—H1B	109.5	O1—C8—C13	117.77 (18)
C2—C1—H1C	109.5	C9—C8—C13	120.32 (19)
H1A—C1—H1C	109.5	C10—C9—C8	120.0 (2)
H1B—C1—H1C	109.5	C10—C9—H9A	120.0
C14—O2—H2A	109.5	C8—C9—H9A	120.0
C7—C2—C3	116.0 (3)	C9—C10—C11	120.6 (2)
C7—C2—C1	120.1 (3)	C9—C10—H10A	119.7
C3—C2—C1	123.9 (3)	C11—C10—H10A	119.7
C4—C3—C2	121.5 (3)	C10—C11—C12	119.3 (2)
C4—C3—H3A	119.2	C10—C11—H11A	120.4
C2—C3—H3A	119.2	C12—C11—H11A	120.4
C5—C4—C3	120.4 (3)	C11—C12—C13	121.7 (2)
C5—C4—H4A	119.8	C11—C12—H12A	119.1
C3—C4—H4A	119.8	C13—C12—H12A	119.1
C4—C5—C6	119.9 (3)	C12—C13—C8	118.0 (2)
C4—C5—H5A	120.1	C12—C13—C14	118.97 (19)
C6—C5—H5A	120.1	C8—C13—C14	123.02 (18)
C5—C6—C7	119.8 (3)	O3—C14—O2	122.0 (2)
C5—C6—H6A	120.1	O3—C14—C13	122.05 (19)
C7—C6—H6A	120.1	O2—C14—C13	115.94 (18)
C2—C7—C6	122.3 (2)
C7—C2—C3—C4	−0.3 (5)	O1—C8—C9—C10	175.6 (2)
C1—C2—C3—C4	177.9 (4)	C13—C8—C9—C10	−0.9 (4)
C2—C3—C4—C5	0.7 (6)	C8—C9—C10—C11	−0.3 (4)
C3—C4—C5—C6	−0.5 (5)	C9—C10—C11—C12	0.3 (4)
C4—C5—C6—C7	−0.1 (4)	C10—C11—C12—C13	0.9 (4)
C3—C2—C7—C6	−0.3 (4)	C11—C12—C13—C8	−2.0 (4)
C1—C2—C7—C6	−178.6 (3)	C11—C12—C13—C14	175.9 (2)
C3—C2—C7—O1	172.8 (2)	O1—C8—C13—C12	−174.58 (19)
C1—C2—C7—O1	−5.5 (4)	C9—C8—C13—C12	2.0 (3)
C5—C6—C7—C2	0.5 (4)	O1—C8—C13—C14	7.6 (3)
C5—C6—C7—O1	−172.7 (2)	C9—C8—C13—C14	−175.9 (2)
C8—O1—C7—C2	94.5 (3)	C12—C13—C14—O3	−175.2 (2)
C8—O1—C7—C6	−92.1 (3)	C8—C13—C14—O3	2.6 (4)
C7—O1—C8—C9	18.4 (3)	C12—C13—C14—O2	3.5 (3)
C7—O1—C8—C13	−165.1 (2)	C8—C13—C14—O2	−178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3i	0.82	1.81	2.624 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.82	1.81	2.624 (3)	172

Symmetry code: (i) .