2-Hy-droxy-6-isopropyl-3-methyl-benzoic acid.

The title compound, C(11)H(14)O(3), is a multiple-substituted derivative of benzoic acid. Intra-cyclic C-C-C angles span a range of 117.16 (19)-122.32 (19)°. Apart from intra-molecular hydrogen bonds between hydroxyl and carboxyl groups, inter-molecular hydrogen bonds are present in the crystal structure, the latter ones giving rise to centrosymmetric carb-oxy-lic acid dimers.

Related literature

For the X-ray crystal structure of benzoic acid, see: Bruno & Randaccio (1980 ▶). For the crystal structure of benzoic acid applying neutron radiation, see: Wilson et al. (1996 ▶). For the crystal structure of meta-methyl­benzoic acid (without three-dimensional coordinates), see: Ellas & García-Blanco (1963 ▶). For a recent crystal structure analysis of salicylic acid, see: Munshi & Guru Row (2006 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H14O3

M = 194.22

Orthorhombic,

a = 16.8864 (17) Å

b = 6.6653 (7) Å

c = 18.238 (2) Å

V = 2052.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.51 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

10325 measured reflections

2546 independent reflections

1365 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 0.99

2546 reflections

132 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011998/bh2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011998/bh2346Isup2.hkl

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

C11H14O3	F(000) = 832
Mr = 194.22	Dx = 1.257 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1806 reflections
a = 16.8864 (17) Å	θ = 3.3–26.5°
b = 6.6653 (7) Å	µ = 0.09 mm−1
c = 18.238 (2) Å	T = 200 K
V = 2052.7 (4) Å3	Rod, colourless
Z = 8	0.51 × 0.16 × 0.08 mm

Bruker APEXII CCD diffractometer	1365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
graphite	θmax = 28.3°, θmin = 3.3°
φ and ω scans	h = −18→22
10325 measured reflections	k = −8→8
2546 independent reflections	l = −16→24

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
2546 reflections	(Δ/σ)max < 0.001
132 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.24 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
O1	0.04216 (9)	0.85849 (19)	0.42308 (8)	0.0409 (4)
H1	0.0189	0.9643	0.4358	0.061*
O2	0.03999 (9)	0.8162 (2)	0.54297 (8)	0.0357 (4)
O3	0.10701 (9)	0.5223 (2)	0.60346 (7)	0.0386 (4)
H3	0.0830	0.6324	0.6010	0.058*
C1	0.09835 (11)	0.5574 (3)	0.47072 (11)	0.0262 (4)
C2	0.12250 (11)	0.4550 (3)	0.53481 (11)	0.0297 (5)
C3	0.16463 (12)	0.2740 (3)	0.53193 (11)	0.0325 (5)
C4	0.18243 (12)	0.1994 (3)	0.46369 (12)	0.0369 (5)
H4	0.2128	0.0799	0.4601	0.044*
C5	0.15747 (12)	0.2931 (3)	0.40016 (12)	0.0364 (5)
H5	0.1703	0.2341	0.3543	0.044*
C6	0.11437 (11)	0.4699 (3)	0.40105 (11)	0.0286 (5)
C7	0.18707 (14)	0.1685 (3)	0.60150 (13)	0.0463 (6)
H71	0.2190	0.0499	0.5898	0.069*
H72	0.1390	0.1269	0.6275	0.069*
H73	0.2178	0.2595	0.6326	0.069*
C8	0.08638 (12)	0.5538 (3)	0.32753 (12)	0.0345 (5)
H8	0.0399	0.6429	0.3373	0.041*
C9	0.05933 (15)	0.3885 (4)	0.27477 (14)	0.0525 (7)
H91	0.1053	0.3094	0.2592	0.079*
H92	0.0342	0.4494	0.2318	0.079*
H93	0.0212	0.3009	0.2996	0.079*
C10	0.15119 (15)	0.6819 (4)	0.29282 (14)	0.0563 (7)
H101	0.1669	0.7880	0.3271	0.084*
H102	0.1312	0.7426	0.2475	0.084*
H103	0.1971	0.5975	0.2816	0.084*
C11	0.05805 (11)	0.7512 (3)	0.48107 (11)	0.0282 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0625 (11)	0.0252 (7)	0.0349 (9)	0.0137 (7)	0.0030 (8)	−0.0027 (7)
O2	0.0455 (9)	0.0275 (7)	0.0342 (8)	0.0079 (6)	0.0033 (7)	−0.0065 (6)
O3	0.0473 (9)	0.0373 (8)	0.0313 (9)	0.0094 (7)	0.0050 (7)	−0.0009 (7)
C1	0.0232 (9)	0.0204 (8)	0.0350 (12)	−0.0017 (7)	0.0039 (8)	−0.0037 (8)
C2	0.0287 (10)	0.0272 (10)	0.0332 (12)	−0.0025 (8)	0.0050 (9)	−0.0038 (9)
C3	0.0281 (10)	0.0278 (10)	0.0416 (13)	−0.0012 (8)	0.0038 (9)	0.0031 (9)
C4	0.0332 (11)	0.0247 (10)	0.0530 (15)	0.0069 (8)	0.0056 (10)	−0.0016 (10)
C5	0.0380 (12)	0.0321 (10)	0.0392 (13)	0.0042 (9)	0.0056 (10)	−0.0078 (10)
C6	0.0279 (10)	0.0244 (9)	0.0334 (12)	−0.0016 (8)	0.0032 (9)	−0.0043 (9)
C7	0.0473 (13)	0.0382 (11)	0.0534 (16)	0.0075 (10)	0.0047 (12)	0.0107 (11)
C8	0.0371 (11)	0.0332 (10)	0.0330 (12)	0.0053 (9)	−0.0002 (9)	−0.0070 (9)
C9	0.0639 (16)	0.0539 (15)	0.0399 (15)	0.0033 (12)	−0.0049 (12)	−0.0178 (12)
C10	0.0536 (15)	0.0668 (16)	0.0485 (16)	−0.0077 (13)	−0.0021 (12)	0.0183 (13)
C11	0.0290 (10)	0.0202 (9)	0.0355 (12)	−0.0020 (8)	0.0003 (9)	−0.0048 (8)

O1—C11	1.305 (2)	C5—H5	0.9500
O1—H1	0.8400	C6—C8	1.528 (3)
O2—C11	1.247 (2)	C7—H71	0.9800
O3—C2	1.355 (2)	C7—H72	0.9800
O3—H3	0.8400	C7—H73	0.9800
C1—C2	1.414 (3)	C8—C10	1.526 (3)
C1—C6	1.424 (3)	C8—C9	1.533 (3)
C1—C11	1.472 (3)	C8—H8	1.0000
C2—C3	1.402 (3)	C9—H91	0.9800
C3—C4	1.373 (3)	C9—H92	0.9800
C3—C7	1.499 (3)	C9—H93	0.9800
C4—C5	1.382 (3)	C10—H101	0.9800
C4—H4	0.9500	C10—H102	0.9800
C5—C6	1.385 (3)	C10—H103	0.9800
C11—O1—H1	109.5	H71—C7—H73	109.5
C2—O3—H3	109.5	H72—C7—H73	109.5
C2—C1—C6	119.03 (17)	C10—C8—C6	110.31 (18)
C2—C1—C11	116.80 (17)	C10—C8—C9	110.84 (19)
C6—C1—C11	124.16 (18)	C6—C8—C9	112.35 (18)
O3—C2—C3	114.68 (18)	C10—C8—H8	107.7
O3—C2—C1	123.25 (17)	C6—C8—H8	107.7
C3—C2—C1	122.07 (18)	C9—C8—H8	107.7
C4—C3—C2	117.16 (19)	C8—C9—H91	109.5
C4—C3—C7	122.81 (19)	C8—C9—H92	109.5
C2—C3—C7	120.02 (19)	H91—C9—H92	109.5
C3—C4—C5	121.99 (19)	C8—C9—H93	109.5
C3—C4—H4	119.0	H91—C9—H93	109.5
C5—C4—H4	119.0	H92—C9—H93	109.5
C4—C5—C6	122.32 (19)	C8—C10—H101	109.5
C4—C5—H5	118.8	C8—C10—H102	109.5
C6—C5—H5	118.8	H101—C10—H102	109.5
C5—C6—C1	117.30 (18)	C8—C10—H103	109.5
C5—C6—C8	117.62 (17)	H101—C10—H103	109.5
C1—C6—C8	125.07 (17)	H102—C10—H103	109.5
C3—C7—H71	109.5	O2—C11—O1	119.55 (17)
C3—C7—H72	109.5	O2—C11—C1	122.27 (18)
H71—C7—H72	109.5	O1—C11—C1	118.17 (17)
C3—C7—H73	109.5
C6—C1—C2—O3	−177.21 (18)	C2—C1—C6—C5	−3.8 (3)
C11—C1—C2—O3	3.1 (3)	C11—C1—C6—C5	175.81 (17)
C6—C1—C2—C3	2.7 (3)	C2—C1—C6—C8	174.92 (18)
C11—C1—C2—C3	−176.96 (17)	C11—C1—C6—C8	−5.4 (3)
O3—C2—C3—C4	−179.57 (18)	C5—C6—C8—C10	−85.4 (2)
C1—C2—C3—C4	0.5 (3)	C1—C6—C8—C10	95.8 (2)
O3—C2—C3—C7	1.5 (3)	C5—C6—C8—C9	38.8 (3)
C1—C2—C3—C7	−178.43 (18)	C1—C6—C8—C9	−140.0 (2)
C2—C3—C4—C5	−2.6 (3)	C2—C1—C11—O2	−5.6 (3)
C7—C3—C4—C5	176.35 (19)	C6—C1—C11—O2	174.72 (18)
C3—C4—C5—C6	1.3 (3)	C2—C1—C11—O1	173.29 (17)
C4—C5—C6—C1	1.9 (3)	C6—C1—C11—O1	−6.4 (3)
C4—C5—C6—C8	−176.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	1.77	2.5171 (19)	146
O1—H1···O2i	0.84	1.81	2.6475 (19)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84	1.77	2.5171 (19)	146
O1—H1⋯O2i	0.84	1.81	2.6475 (19)	174

Symmetry code: (i) .