2-(Biphenyl-4-yl-oxy)acetic acid.

In the title compound, C(14)H(12)O(3), the phenyl and benzene rings make a dihedral angle of 47.51 (4)°. In the crystal, mol-ecules are dimerized by double O-H⋯O hydrogen bonds, forming centrosymmetric R(2) (2)(8) ring motifs. The dimers are inter-linked by C-H⋯π inter-actions into zigzag layers.

Related literature

For biological studies of biphenyl compounds, see: Kamoda et al. (2006 ▶); Kumar et al. (2008 ▶); Malamas et al. (2000 ▶). For related structures, see: Ali et al. (2008 ▶); Cao (2009 ▶); Margraf et al. (2009 ▶); Li et al. (2009 ▶); Charbonneau & Delugeard (1977 ▶); Brett et al. (1999 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C14H12O3

M = 228.24

Monoclinic,

a = 5.9118 (1) Å

b = 28.5786 (3) Å

c = 6.9017 (1) Å

β = 109.631 (2)°

V = 1098.27 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 293 K

0.43 × 0.42 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.727, T max = 0.742

11989 measured reflections

2306 independent reflections

2223 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.139

S = 1.12

2306 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S1600536811002777/bh2330sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002777/bh2330Isup2.hkl

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

C14H12O3	F(000) = 480
Mr = 228.24	Dx = 1.380 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 11208 reflections
a = 5.9118 (1) Å	θ = 4.6–76.4°
b = 28.5786 (3) Å	µ = 0.79 mm−1
c = 6.9017 (1) Å	T = 293 K
β = 109.631 (2)°	Plate, colourless
V = 1098.27 (3) Å3	0.43 × 0.42 × 0.40 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2306 independent reflections
Radiation source: fine-focus sealed tube	2223 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 77.0°, θmin = 6.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.727, Tmax = 0.742	k = −36→35
11989 measured reflections	l = −7→8

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0818P)2 + 0.2839P] where P = (Fo2 + 2Fc2)/3
2306 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
O3	0.54080 (16)	0.06250 (3)	0.05489 (14)	0.0328 (3)
O2	0.39398 (17)	0.02975 (3)	−0.32997 (15)	0.0364 (3)
O1	0.76170 (18)	0.00213 (4)	−0.29161 (15)	0.0380 (3)
H1	0.6955	−0.0065	−0.4105	0.057*
C8	0.4590 (2)	0.11281 (5)	0.2933 (2)	0.0321 (3)
H8	0.2999	0.1139	0.2069	0.039*
C3	0.6254 (2)	0.08550 (4)	0.24154 (19)	0.0303 (3)
C7	0.5320 (2)	0.13840 (4)	0.4743 (2)	0.0321 (3)
H7	0.4203	0.1565	0.5085	0.039*
C6	0.7706 (2)	0.13749 (4)	0.6066 (2)	0.0302 (3)
C5	0.9320 (2)	0.10893 (5)	0.5536 (2)	0.0335 (3)
H5	1.0905	0.1073	0.6411	0.040*
C2	0.7191 (2)	0.04138 (5)	−0.0118 (2)	0.0328 (3)
H2A	0.7931	0.0156	0.0790	0.039*
H2B	0.8430	0.0641	−0.0063	0.039*
C9	0.8549 (2)	0.16649 (4)	0.7961 (2)	0.0309 (3)
C1	0.6092 (2)	0.02357 (4)	−0.2277 (2)	0.0314 (3)
C4	0.8611 (2)	0.08296 (5)	0.3732 (2)	0.0342 (3)
H4	0.9711	0.0640	0.3408	0.041*
C11	1.1469 (3)	0.22017 (5)	1.0158 (2)	0.0403 (3)
H11	1.2858	0.2379	1.0417	0.048*
C10	1.0651 (2)	0.19293 (5)	0.8395 (2)	0.0351 (3)
H10	1.1512	0.1923	0.7489	0.042*
C13	0.8131 (3)	0.19494 (5)	1.1128 (2)	0.0379 (3)
H13	0.7290	0.1954	1.2051	0.045*
C14	0.7289 (2)	0.16808 (5)	0.9348 (2)	0.0335 (3)
H14	0.5876	0.1510	0.9079	0.040*
C12	1.0218 (3)	0.22096 (5)	1.1534 (2)	0.0399 (3)
H12	1.0777	0.2389	1.2725	0.048*

	U11	U22	U33	U12	U13	U23
O3	0.0336 (5)	0.0349 (5)	0.0283 (5)	0.0004 (4)	0.0085 (4)	−0.0068 (4)
O2	0.0357 (5)	0.0383 (5)	0.0318 (5)	0.0054 (4)	0.0067 (4)	−0.0019 (4)
O1	0.0385 (5)	0.0448 (6)	0.0299 (5)	0.0059 (4)	0.0104 (4)	−0.0061 (4)
C8	0.0306 (6)	0.0336 (6)	0.0309 (7)	−0.0010 (5)	0.0084 (5)	−0.0019 (5)
C3	0.0363 (7)	0.0274 (6)	0.0267 (6)	−0.0019 (5)	0.0100 (5)	−0.0024 (4)
C7	0.0333 (6)	0.0314 (6)	0.0325 (7)	0.0011 (5)	0.0120 (5)	−0.0018 (5)
C6	0.0344 (6)	0.0268 (6)	0.0295 (6)	−0.0010 (5)	0.0106 (5)	−0.0005 (5)
C5	0.0325 (6)	0.0337 (6)	0.0317 (7)	0.0014 (5)	0.0074 (5)	−0.0034 (5)
C2	0.0341 (6)	0.0342 (6)	0.0294 (6)	0.0013 (5)	0.0097 (5)	−0.0043 (5)
C9	0.0351 (6)	0.0264 (6)	0.0296 (6)	0.0024 (5)	0.0089 (5)	−0.0004 (5)
C1	0.0367 (7)	0.0285 (6)	0.0287 (6)	0.0017 (5)	0.0106 (5)	0.0011 (5)
C4	0.0355 (7)	0.0324 (6)	0.0339 (7)	0.0041 (5)	0.0107 (5)	−0.0030 (5)
C11	0.0404 (7)	0.0360 (7)	0.0398 (8)	−0.0042 (6)	0.0072 (6)	−0.0056 (6)
C10	0.0358 (7)	0.0335 (6)	0.0350 (7)	−0.0006 (5)	0.0107 (6)	−0.0021 (5)
C13	0.0517 (8)	0.0333 (7)	0.0293 (7)	0.0033 (6)	0.0146 (6)	0.0000 (5)
C14	0.0398 (7)	0.0293 (6)	0.0318 (7)	−0.0004 (5)	0.0123 (5)	−0.0004 (5)
C12	0.0515 (8)	0.0326 (7)	0.0301 (7)	0.0004 (6)	0.0064 (6)	−0.0055 (5)

O3—C3	1.3816 (15)	C2—C1	1.5002 (17)
O3—C2	1.4190 (16)	C2—H2A	0.9700
O2—C1	1.2427 (16)	C2—H2B	0.9700
O1—C1	1.2848 (16)	C9—C14	1.3971 (18)
O1—H1	0.8200	C9—C10	1.3982 (19)
C8—C7	1.3852 (18)	C4—H4	0.9300
C8—C3	1.3933 (18)	C11—C12	1.386 (2)
C8—H8	0.9300	C11—C10	1.3873 (19)
C3—C4	1.3862 (19)	C11—H11	0.9300
C7—C6	1.3996 (19)	C10—H10	0.9300
C7—H7	0.9300	C13—C12	1.386 (2)
C6—C5	1.3946 (18)	C13—C14	1.3914 (19)
C6—C9	1.4858 (17)	C13—H13	0.9300
C5—C4	1.3880 (18)	C14—H14	0.9300
C5—H5	0.9300	C12—H12	0.9300
C3—O3—C2	115.42 (10)	C14—C9—C6	121.53 (12)
C1—O1—H1	109.5	C10—C9—C6	120.07 (12)
C7—C8—C3	119.62 (12)	O2—C1—O1	125.12 (12)
C7—C8—H8	120.2	O2—C1—C2	122.36 (12)
C3—C8—H8	120.2	O1—C1—C2	112.52 (11)
O3—C3—C4	123.75 (12)	C3—C4—C5	119.61 (12)
O3—C3—C8	116.11 (11)	C3—C4—H4	120.2
C4—C3—C8	120.14 (12)	C5—C4—H4	120.2
C8—C7—C6	121.25 (12)	C12—C11—C10	120.08 (14)
C8—C7—H7	119.4	C12—C11—H11	120.0
C6—C7—H7	119.4	C10—C11—H11	120.0
C5—C6—C7	117.92 (12)	C11—C10—C9	120.93 (13)
C5—C6—C9	120.04 (12)	C11—C10—H10	119.5
C7—C6—C9	122.03 (11)	C9—C10—H10	119.5
C4—C5—C6	121.42 (12)	C12—C13—C14	120.31 (13)
C4—C5—H5	119.3	C12—C13—H13	119.8
C6—C5—H5	119.3	C14—C13—H13	119.8
O3—C2—C1	110.21 (11)	C13—C14—C9	120.52 (13)
O3—C2—H2A	109.6	C13—C14—H14	119.7
C1—C2—H2A	109.6	C9—C14—H14	119.7
O3—C2—H2B	109.6	C11—C12—C13	119.75 (13)
C1—C2—H2B	109.6	C11—C12—H12	120.1
H2A—C2—H2B	108.1	C13—C12—H12	120.1
C14—C9—C10	118.40 (12)
C2—O3—C3—C4	−9.49 (18)	O3—C2—C1—O2	3.58 (18)
C2—O3—C3—C8	169.80 (11)	O3—C2—C1—O1	−176.89 (11)
C7—C8—C3—O3	−177.55 (11)	O3—C3—C4—C5	177.22 (11)
C7—C8—C3—C4	1.77 (19)	C8—C3—C4—C5	−2.0 (2)
C3—C8—C7—C6	0.2 (2)	C6—C5—C4—C3	0.4 (2)
C8—C7—C6—C5	−1.8 (2)	C12—C11—C10—C9	0.9 (2)
C8—C7—C6—C9	176.93 (12)	C14—C9—C10—C11	−0.1 (2)
C7—C6—C5—C4	1.5 (2)	C6—C9—C10—C11	−179.91 (12)
C9—C6—C5—C4	−177.23 (12)	C12—C13—C14—C9	0.8 (2)
C3—O3—C2—C1	−172.07 (10)	C10—C9—C14—C13	−0.80 (19)
C5—C6—C9—C14	−133.31 (14)	C6—C9—C14—C13	179.04 (12)
C7—C6—C9—C14	48.02 (18)	C10—C11—C12—C13	−0.8 (2)
C5—C6—C9—C10	46.52 (18)	C14—C13—C12—C11	0.0 (2)
C7—C6—C9—C10	−132.15 (14)

Cg is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.81	2.6235 (13)	169
C12—H12···Cgii	0.93	2.86	3.6392 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.81	2.6235 (13)	169
C12—H12⋯Cgii	0.93	2.86	3.6392 (16)	142

Symmetry codes: (i) ; (ii) .