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

In the crystal structure of the title compound, C(14)H(12)O(3), the mol-ecules form classical O-H⋯O hydrogen-bonded carb-oxy-lic acid dimers. The dihedral angle between the two rings is 80.9 (3)°.

Related literature

For related structures, see: Shi et al. (2011 ▶); Raghunathan et al. (1982 ▶); Zhang (2011 ▶). For the synthesis of the title compound, see: Pellon et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12O3

M = 228.24

Triclinic,

a = 5.193 (1) Å

b = 7.8000 (16) Å

c = 14.868 (3) Å

α = 94.28 (3)°

β = 97.50 (3)°

γ = 102.54 (3)°

V = 579.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.982, T max = 0.991

2387 measured reflections

2132 independent reflections

1132 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.116

S = 1.00

2132 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 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 datablock(s) I, global. DOI: 10.1107/S1600536811026171/hg5059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026171/hg5059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026171/hg5059Isup3.cml

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

C14H12O3	Z = 2
Mr = 228.24	F(000) = 240
Triclinic, P1	Dx = 1.308 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.193 (1) Å	Cell parameters from 25 reflections
b = 7.8000 (16) Å	θ = 9–12°
c = 14.868 (3) Å	µ = 0.09 mm−1
α = 94.28 (3)°	T = 293 K
β = 97.50 (3)°	Block, colourless
γ = 102.54 (3)°	0.20 × 0.20 × 0.10 mm
V = 579.5 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.982, Tmax = 0.991	l = −17→17
2387 measured reflections	3 standard reflections every 200 reflections
2132 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
2132 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.12 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	0.3075 (4)	0.93730 (19)	0.80140 (11)	0.0780 (6)
C1	0.1740 (8)	0.8008 (4)	0.4694 (2)	0.1111 (12)
H1A	0.3613	0.8039	0.4758	0.167*
H1B	0.1429	0.9087	0.4479	0.167*
H1C	0.0778	0.7027	0.4264	0.167*
O2	0.7293 (3)	0.95411 (19)	0.92424 (11)	0.0683 (6)
C2	0.0798 (7)	0.7808 (3)	0.56045 (19)	0.0694 (8)
O3	0.9363 (3)	1.21756 (19)	0.99325 (11)	0.0706 (6)
H3B	1.0355	1.1598	1.0172	0.106*
C3	0.2341 (6)	0.8720 (3)	0.63921 (19)	0.0660 (8)
H3A	0.3994	0.9455	0.6366	0.079*
C4	0.1428 (6)	0.8542 (3)	0.72192 (19)	0.0617 (8)
C5	−0.0968 (6)	0.7484 (3)	0.7283 (2)	0.0720 (8)
H5A	−0.1568	0.7396	0.7844	0.086*
C6	−0.2495 (6)	0.6544 (4)	0.6507 (2)	0.0856 (10)
H6A	−0.4126	0.5789	0.6539	0.103*
C7	−0.1597 (7)	0.6725 (4)	0.5675 (2)	0.0826 (10)
H7A	−0.2652	0.6092	0.5151	0.099*
C8	0.3485 (5)	1.1181 (3)	0.81945 (15)	0.0519 (7)
C9	0.1781 (5)	1.2089 (3)	0.77587 (16)	0.0640 (8)
H9A	0.0352	1.1490	0.7324	0.077*
C10	0.2199 (6)	1.3888 (3)	0.79684 (17)	0.0673 (8)
H10A	0.1049	1.4500	0.7672	0.081*
C11	0.4270 (6)	1.4776 (3)	0.86027 (17)	0.0671 (8)
H11A	0.4544	1.5992	0.8737	0.081*
C12	0.5958 (5)	1.3877 (3)	0.90456 (16)	0.0580 (7)
H12A	0.7366	1.4495	0.9482	0.070*
C13	0.5610 (5)	1.2048 (3)	0.88546 (14)	0.0459 (6)
C14	0.7462 (5)	1.1132 (3)	0.93547 (15)	0.0488 (6)

	U11	U22	U33	U12	U13	U23
O1	0.1006 (15)	0.0443 (9)	0.0743 (12)	0.0174 (10)	−0.0369 (12)	−0.0027 (9)
C1	0.168 (4)	0.092 (2)	0.081 (2)	0.049 (2)	0.014 (2)	0.0103 (19)
O2	0.0736 (13)	0.0455 (9)	0.0766 (12)	0.0160 (9)	−0.0205 (10)	−0.0042 (8)
C2	0.089 (2)	0.0538 (16)	0.0635 (19)	0.0329 (17)	−0.0149 (18)	−0.0047 (14)
O3	0.0756 (13)	0.0522 (10)	0.0735 (12)	0.0157 (10)	−0.0223 (11)	−0.0048 (9)
C3	0.070 (2)	0.0504 (15)	0.0723 (19)	0.0160 (14)	−0.0116 (17)	0.0070 (14)
C4	0.0639 (19)	0.0383 (13)	0.0723 (19)	0.0136 (13)	−0.0245 (16)	−0.0067 (13)
C5	0.070 (2)	0.0588 (16)	0.084 (2)	0.0207 (16)	0.0002 (18)	−0.0067 (15)
C6	0.066 (2)	0.0715 (19)	0.108 (3)	0.0098 (17)	−0.007 (2)	−0.014 (2)
C7	0.081 (2)	0.0577 (17)	0.095 (3)	0.0232 (18)	−0.036 (2)	−0.0216 (17)
C8	0.0642 (17)	0.0412 (12)	0.0474 (14)	0.0131 (13)	−0.0009 (13)	−0.0003 (11)
C9	0.0706 (19)	0.0557 (15)	0.0618 (17)	0.0210 (14)	−0.0129 (15)	0.0011 (13)
C10	0.081 (2)	0.0549 (16)	0.0689 (18)	0.0288 (15)	0.0007 (17)	0.0041 (14)
C11	0.083 (2)	0.0448 (14)	0.0751 (19)	0.0217 (15)	0.0086 (17)	0.0025 (14)
C12	0.0656 (18)	0.0453 (13)	0.0589 (16)	0.0100 (13)	0.0028 (14)	−0.0012 (12)
C13	0.0534 (15)	0.0438 (13)	0.0387 (13)	0.0108 (12)	0.0019 (12)	0.0040 (10)
C14	0.0523 (16)	0.0449 (13)	0.0446 (14)	0.0053 (13)	0.0035 (12)	−0.0012 (11)

O1—C8	1.380 (2)	C5—H5A	0.9300
O1—C4	1.389 (3)	C6—C7	1.384 (4)
C1—C2	1.506 (4)	C6—H6A	0.9300
C1—H1A	0.9600	C7—H7A	0.9300
C1—H1B	0.9600	C8—C9	1.377 (3)
C1—H1C	0.9600	C8—C13	1.390 (3)
O2—C14	1.222 (2)	C9—C10	1.378 (3)
C2—C7	1.365 (4)	C9—H9A	0.9300
C2—C3	1.380 (3)	C10—C11	1.357 (3)
O3—C14	1.304 (2)	C10—H10A	0.9300
O3—H3B	0.8200	C11—C12	1.371 (3)
C3—C4	1.380 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.401 (3)
C4—C5	1.355 (4)	C12—H12A	0.9300
C5—C6	1.371 (3)	C13—C14	1.476 (3)
C8—O1—C4	118.75 (17)	C2—C7—H7A	119.2
C2—C1—H1A	109.5	C6—C7—H7A	119.2
C2—C1—H1B	109.5	C9—C8—O1	121.0 (2)
H1A—C1—H1B	109.5	C9—C8—C13	121.0 (2)
C2—C1—H1C	109.5	O1—C8—C13	118.0 (2)
H1A—C1—H1C	109.5	C8—C9—C10	119.8 (2)
H1B—C1—H1C	109.5	C8—C9—H9A	120.1
C7—C2—C3	118.2 (3)	C10—C9—H9A	120.1
C7—C2—C1	121.2 (3)	C11—C10—C9	120.7 (2)
C3—C2—C1	120.7 (3)	C11—C10—H10A	119.7
C14—O3—H3B	109.5	C9—C10—H10A	119.7
C2—C3—C4	119.9 (3)	C10—C11—C12	119.9 (2)
C2—C3—H3A	120.1	C10—C11—H11A	120.1
C4—C3—H3A	120.1	C12—C11—H11A	120.1
C5—C4—C3	121.6 (3)	C11—C12—C13	121.4 (2)
C5—C4—O1	118.9 (3)	C11—C12—H12A	119.3
C3—C4—O1	119.3 (3)	C13—C12—H12A	119.3
C4—C5—C6	118.9 (3)	C8—C13—C12	117.2 (2)
C4—C5—H5A	120.5	C8—C13—C14	123.17 (19)
C6—C5—H5A	120.5	C12—C13—C14	119.6 (2)
C5—C6—C7	119.7 (3)	O2—C14—O3	121.7 (2)
C5—C6—H6A	120.2	O2—C14—C13	124.1 (2)
C7—C6—H6A	120.2	O3—C14—C13	114.12 (19)
C2—C7—C6	121.7 (3)
C7—C2—C3—C4	−0.9 (4)	C13—C8—C9—C10	0.9 (4)
C1—C2—C3—C4	179.0 (2)	C8—C9—C10—C11	−0.2 (4)
C2—C3—C4—C5	0.0 (4)	C9—C10—C11—C12	−0.4 (4)
C2—C3—C4—O1	175.7 (2)	C10—C11—C12—C13	0.4 (4)
C8—O1—C4—C5	−110.5 (3)	C9—C8—C13—C12	−0.9 (3)
C8—O1—C4—C3	73.7 (3)	O1—C8—C13—C12	−178.5 (2)
C3—C4—C5—C6	1.3 (4)	C9—C8—C13—C14	178.8 (2)
O1—C4—C5—C6	−174.5 (2)	O1—C8—C13—C14	1.2 (3)
C4—C5—C6—C7	−1.6 (4)	C11—C12—C13—C8	0.2 (4)
C3—C2—C7—C6	0.6 (4)	C11—C12—C13—C14	−179.4 (2)
C1—C2—C7—C6	−179.3 (3)	C8—C13—C14—O2	−0.6 (4)
C5—C6—C7—C2	0.7 (4)	C12—C13—C14—O2	179.0 (2)
C4—O1—C8—C9	18.2 (4)	C8—C13—C14—O3	178.6 (2)
C4—O1—C8—C13	−164.2 (2)	C12—C13—C14—O3	−1.8 (3)
O1—C8—C9—C10	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2i	0.82	1.83	2.648 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O2i	0.82	1.83	2.648 (2)	176

Symmetry code: (i) .