2-(Biphenyl-4-yl­oxy)acetic acid

Wang, E.-J.; Chen, G.-Y.

doi:10.1107/S1600536811002777

organic compounds

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Volume 67| Part 2| February 2011| Page o521

doi:10.1107/S1600536811002777

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2-(Biphenyl-4-yloxy)acetic acid

En-Ju Wang ^a ^* and Guang-Ying Chen ^a

^aHainan Provincial Key Laboratory of Tropical Pharmaceutical Herb Chemistry, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
^*Correspondence e-mail: enjuwang@163.com

(Received 4 December 2010; accepted 20 January 2011; online 29 January 2011)

In the title compound, C₁₄H₁₂O₃, the phenyl and benzene rings make a dihedral angle of 47.51 (4)°. In the crystal, molecules are dimerized by double O—H⋯O hydrogen bonds, forming centrosymmetric R₂²(8) ring motifs. The dimers are interlinked by C—H⋯π interactions 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_r = 228.24
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.12
2306 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x+1, -y, -z-1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002777/bh2330sup1.cif

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

checkCIF report

Comment top

Biphenyl moieties have been found to act as pharmacophores in many biological studies such as antimycobacterial testing (Kamoda et al., 2006). Several derivatives of biphenyl-4-yloxy acetic acid are reported to be potential drugs with anti-inflammatory activity, analgesic activity and lower ulcerogenic potential (Kumar et al., 2008). A series of benzofuran/benzothiophene biphenyl oxo-acetic acids act as potent inhibitors of protein tyrosine phosphatase 1B with good oral antihyperglycemic activity (Malamas et al., 2000). In this paper we report the crystal structure of the title compound, (I).

In the crystal of the title compound (Fig. 1), two carboxyl groups form a pair of hydrogen bonds in cyclic R₂²(8) arrangement (Etter, 1990). The pairs of hydrogen bonds link the molecules into inversion dimers. The dimers are arranged in a herringbone pattern with an angle of 66.15 (1)°. The adjacent dimers are linked via C—H···π interactions with the H···π distance of 2.86 Å (Fig. 2). Some crystal structures containing biphenyl moiety have been reported. The two benzene rings are usually nearly coplanar for the biphenyl compounds without 2-substituents (Ali et al., 2008; Cao, 2009; Margraf et al., 2009; Li et al., 2009; Charbonneau & Delugeard, 1977). But the title compound displays a twisted conformation with a dihedral angle of 47.51 (4)° between the phenyl and benzene planes. Planar conformations will be adopted by biphenyl compounds in the ground states. It is the crystal packing forces that produce the planar conformations for the biphenyl compounds (Brett et al., 1999).

Related literature top

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 top

The crystals of (biphenyl-4-yloxy)acetic acid were unexpectedly obtained in the preparation of (biphenyl-4-yloxy)acetic acid-β-cyclodextrin inclusion complex. The experiment scheme is as follows: An ethanol solution of (biphenyl-4-yloxy)acetic acid (1 mmol, 5 ml) was added dropwise to an aqueous solution of β-cyclodextrin (1 mmol, 50 ml) and stirred at 50 °C for 6 h. The resulting solution was filtered and then stored at 40 °C. Colorless crystals suitable for the single X-ray diffraction were obtained after one week.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular configuration and atom numbering scheme for the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I). Hydrogen bonds are shown as dashed lines.

2-(Biphenyl-4-yloxy)acetic acid top

Crystal data top

C₁₄H₁₂O₃	F(000) = 480
M_r = 228.24	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0818P)² + 0.2839P] where P = (F_o² + 2F_c²)/3
2306 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

Crystal data top

C₁₄H₁₂O₃	V = 1098.27 (3) Å³
M_r = 228.24	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.9118 (1) Å	µ = 0.79 mm⁻¹
b = 28.5786 (3) Å	T = 293 K
c = 6.9017 (1) Å	0.43 × 0.42 × 0.40 mm
β = 109.631 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2306 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2223 reflections with I > 2σ(I)
T_min = 0.727, T_max = 0.742	R_int = 0.028
11989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.12	Δρ_max = 0.21 e Å⁻³
2306 reflections	Δρ_min = −0.23 e Å⁻³
155 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z−1; (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₃
M_r	228.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.9118 (1), 28.5786 (3), 6.9017 (1)
β (°)	109.631 (2)
V (Å³)	1098.27 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.43 × 0.42 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.727, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	11989, 2306, 2223
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.139, 1.12
No. of reflections	2306
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z−1; (ii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We are grateful for financial support from the Natural Science Foundation of Hainan Province (No. 808145)

References

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