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

The structure of the title compound, C(14)H(12)O(2), displays the expected inter-molecular hydrogen bonding of the carb-oxy-lic acid groups, forming dimers. The dihedral angle between the two aromatic rings is 27.01 (7)°.

Related literature

The title compound is a potent non-steroidal anti-inflammatory agent, used to treat muscle inflammation and arthritis. For single-crystal structures of inclusion complexes between felbinac and both hepta­kis-(2,3,6-tri-O-meth­yl)-β-cyclo­dextrin and β-cyclo­dextrin, see: Harata et al. (1992 ▶) and Wang et al. (2009 ▶), respectively. For single crystal structures of different complexes of felbinac with tryptamine and 1,2-diphenyl­ethyl­enediamine (different solvates), see: Koshima et al. (1998 ▶) and Imai et al. (2007 ▶), respectively.

Experimental

Crystal data

C14H12O2

M = 212.25

Orthorhombic,

a = 46.248 (19) Å

b = 6.465 (3) Å

c = 7.470 (3) Å

V = 2233.4 (16) Å3

Z = 8

Cu Kα radiation

μ = 0.64 mm−1

T = 150 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku RAPID II diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 ▶) T min = 0.803, T max = 0.881

8644 measured reflections

1952 independent reflections

1539 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.08

1952 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and local programs.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035828/vm2040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035828/vm2040Isup2.hkl

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

C14H12O2	F(000) = 896
Mr = 212.25	Dx = 1.262 Mg m−3
Orthorhombic, Pbcn	Cu - Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2n 2ab	Cell parameters from 8644 reflections
a = 46.248 (19) Å	θ = 6–66°
b = 6.465 (3) Å	µ = 0.64 mm−1
c = 7.470 (3) Å	T = 150 K
V = 2233.4 (16) Å3	Chunk, colourless
Z = 8	0.20 × 0.20 × 0.20 mm

Rigaku RAPID II diffractometer	1539 reflections with I > 2σ(I)
confocal optics	Rint = 0.037
ω scans	θmax = 66.5°, θmin = 6.6°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)	h = −53→54
Tmin = 0.803, Tmax = 0.881	k = −7→7
8644 measured reflections	l = −8→8
1952 independent reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0731P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.038	(Δ/σ)max = 0.001
wR(F2) = 0.107	Δρmax = 0.21 e Å−3
S = 1.08	Δρmin = −0.12 e Å−3
1952 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008)
150 parameters	Extinction coefficient: 0.92E-02
0 restraints

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. Outlier data were removed using a local program based on the method of Prince and Nicholson.Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R_factor_obs 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	0.465961 (19)	0.26139 (14)	0.29970 (13)	0.0659 (3)
O2	0.50183 (2)	0.25189 (14)	0.49623 (15)	0.0673 (3)
C11	0.36381 (3)	0.24813 (16)	0.46896 (16)	0.0459 (3)
C12	0.38092 (3)	0.07334 (19)	0.44073 (17)	0.0537 (3)
C13	0.40981 (3)	0.0723 (2)	0.48829 (18)	0.0580 (4)
C14	0.42282 (3)	0.24426 (18)	0.56461 (17)	0.0519 (4)
C15	0.40583 (3)	0.4174 (2)	0.59492 (18)	0.0571 (4)
C16	0.37693 (3)	0.41946 (19)	0.54734 (17)	0.0549 (4)
C17	0.45452 (3)	0.24152 (19)	0.61233 (19)	0.0606 (4)
C18	0.47426 (3)	0.25310 (17)	0.45355 (19)	0.0513 (4)
C21	0.33265 (3)	0.25021 (16)	0.41626 (16)	0.0462 (3)
C22	0.31270 (2)	0.37583 (18)	0.50399 (17)	0.0543 (4)
C23	0.28391 (3)	0.3774 (2)	0.45408 (18)	0.0591 (4)
C24	0.27427 (3)	0.25357 (19)	0.3176 (2)	0.0594 (4)
C25	0.29358 (3)	0.1274 (2)	0.2301 (2)	0.0628 (4)
C26	0.32239 (3)	0.1263 (2)	0.27863 (18)	0.0566 (4)
H2	0.5133 (4)	0.258 (2)	0.386 (3)	0.105 (7)*
H12	0.3726	−0.0465	0.3881	0.064*
H13	0.4210	−0.0489	0.4683	0.070*
H15	0.4141	0.5363	0.6491	0.069*
H16	0.3658	0.5404	0.5686	0.066*
H22	0.3190	0.4617	0.5996	0.065*
H23	0.2707	0.4652	0.5149	0.071*
H24	0.2545	0.2549	0.2839	0.071*
H25	0.2871	0.0405	0.1357	0.075*
H26	0.3355	0.0388	0.2164	0.068*
H17A	0.4587	0.3598	0.6925	0.073*
H17B	0.4588	0.1130	0.6794	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.0465 (6)	0.0959 (8)	0.0552 (6)	−0.0007 (4)	−0.0058 (4)	0.0046 (5)
O2	0.0459 (6)	0.0945 (9)	0.0617 (6)	0.0005 (4)	−0.0098 (5)	−0.0014 (5)
C11	0.0472 (7)	0.0521 (8)	0.0384 (7)	−0.0008 (5)	0.0040 (5)	−0.0001 (5)
C12	0.0536 (8)	0.0521 (7)	0.0555 (8)	−0.0006 (6)	0.0023 (6)	−0.0078 (6)
C13	0.0545 (8)	0.0584 (8)	0.0611 (9)	0.0074 (6)	0.0030 (6)	−0.0049 (7)
C14	0.0499 (8)	0.0642 (9)	0.0416 (7)	−0.0003 (5)	0.0006 (5)	0.0029 (6)
C15	0.0571 (8)	0.0584 (8)	0.0559 (8)	−0.0041 (6)	−0.0027 (6)	−0.0090 (7)
C16	0.0529 (8)	0.0530 (7)	0.0587 (8)	0.0032 (6)	−0.0010 (6)	−0.0090 (6)
C17	0.0550 (9)	0.0761 (10)	0.0508 (8)	0.0019 (6)	−0.0054 (6)	−0.0001 (7)
C18	0.0469 (7)	0.0527 (8)	0.0543 (8)	0.0006 (5)	−0.0104 (6)	−0.0015 (6)
C21	0.0485 (8)	0.0490 (7)	0.0411 (7)	−0.0024 (5)	0.0041 (5)	0.0017 (5)
C22	0.0539 (8)	0.0611 (9)	0.0479 (7)	0.0028 (6)	0.0003 (6)	−0.0072 (6)
C23	0.0518 (8)	0.0678 (9)	0.0576 (9)	0.0068 (6)	0.0047 (6)	−0.0003 (7)
C24	0.0487 (8)	0.0666 (9)	0.0628 (9)	−0.0047 (6)	−0.0040 (6)	0.0066 (7)
C25	0.0585 (9)	0.0688 (10)	0.0612 (9)	−0.0073 (6)	−0.0072 (6)	−0.0109 (7)
C26	0.0551 (8)	0.0603 (9)	0.0544 (8)	−0.0010 (6)	0.0025 (6)	−0.0103 (6)

O1—C18	1.2128 (17)	C17—C18	1.499 (2)
O2—C18	1.3144 (15)	C17—H17A	0.9900
O2—H2	0.98 (2)	C17—H17B	0.9900
C11—C16	1.3921 (16)	C21—C26	1.3869 (17)
C11—C12	1.3957 (16)	C21—C22	1.3930 (16)
C11—C21	1.4937 (18)	C22—C23	1.3827 (16)
C12—C13	1.3822 (16)	C22—H22	0.9500
C12—H12	0.9500	C23—C24	1.3710 (18)
C13—C14	1.3870 (17)	C23—H23	0.9500
C13—H13	0.9500	C24—C25	1.3749 (18)
C14—C15	1.3865 (16)	C24—H24	0.9500
C14—C17	1.5088 (18)	C25—C26	1.3811 (16)
C15—C16	1.3830 (16)	C25—H25	0.9500
C15—H15	0.9500	C26—H26	0.9500
C16—H16	0.9500
C18—O2—H2	108.7 (11)	C14—C17—H17B	108.80
C16—C11—C12	117.42 (12)	H17A—C17—H17B	107.70
C16—C11—C21	121.62 (10)	O1—C18—O2	122.48 (13)
C12—C11—C21	120.97 (11)	O1—C18—C17	124.01 (12)
C13—C12—C11	120.89 (12)	O2—C18—C17	113.50 (13)
C13—C12—H12	119.60	C26—C21—C22	117.31 (12)
C11—C12—H12	119.60	C26—C21—C11	121.35 (10)
C12—C13—C14	121.41 (11)	C22—C21—C11	121.34 (11)
C12—C13—H13	119.30	C23—C22—C21	121.02 (12)
C14—C13—H13	119.30	C23—C22—H22	119.50
C15—C14—C13	117.92 (12)	C21—C22—H22	119.50
C15—C14—C17	121.45 (11)	C24—C23—C22	120.62 (12)
C13—C14—C17	120.63 (11)	C24—C23—H23	119.70
C16—C15—C14	120.90 (12)	C22—C23—H23	119.70
C16—C15—H15	119.50	C23—C24—C25	119.27 (13)
C14—C15—H15	119.50	C23—C24—H24	120.40
C15—C16—C11	121.46 (11)	C25—C24—H24	120.40
C15—C16—H16	119.30	C24—C25—C26	120.31 (13)
C11—C16—H16	119.30	C24—C25—H25	119.80
C18—C17—C14	113.85 (12)	C26—C25—H25	119.80
C18—C17—H17A	108.80	C25—C26—C21	121.47 (12)
C14—C17—H17A	108.80	C25—C26—H26	119.30
C18—C17—H17B	108.80	C21—C26—H26	119.30
C16—C11—C12—C13	−0.35 (19)	C14—C17—C18—O2	179.61 (9)
C21—C11—C12—C13	179.48 (11)	C16—C11—C21—C26	152.94 (12)
C11—C12—C13—C14	−0.3 (2)	C12—C11—C21—C26	−26.89 (17)
C12—C13—C14—C15	1.1 (2)	C16—C11—C21—C22	−27.41 (17)
C12—C13—C14—C17	−178.81 (12)	C12—C11—C21—C22	152.77 (12)
C13—C14—C15—C16	−1.2 (2)	C26—C21—C22—C23	−0.55 (17)
C17—C14—C15—C16	178.71 (12)	C11—C21—C22—C23	179.79 (11)
C14—C15—C16—C11	0.5 (2)	C21—C22—C23—C24	0.58 (19)
C12—C11—C16—C15	0.25 (19)	C22—C23—C24—C25	−0.14 (19)
C21—C11—C16—C15	−179.59 (11)	C23—C24—C25—C26	−0.3 (2)
C15—C14—C17—C18	−106.63 (14)	C24—C25—C26—C21	0.3 (2)
C13—C14—C17—C18	73.25 (15)	C22—C21—C26—C25	0.09 (18)
C14—C17—C18—O1	−0.88 (18)	C11—C21—C26—C25	179.76 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.98 (2)	1.69 (2)	2.6663 (16)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.98 (2)	1.69 (2)	2.6663 (16)	178 (2)

Symmetry code: (i) .