4′-Hydroxy­biphenyl-4-carboxylic acid

Abstract

The title compound, C₁₃H₁₀O₃, has potential oxygen donor and acceptor sites. Inter­molecular hydrogen bonding between neighboring carboxyl­ate groups leads to the formation of hydrogen-bonded dimers [graph-set motif R ₂ ²(8)]. A second hydrogen-bonding inter­action between the hydr­oxy groups generates a chain and extends the structure into a lamellar layer. One of the benzene rings is disordered over two positions with an occupancy ratio of 0.57 (2):0.43 (2).

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Datta & Pati (2006 ▶); Zwier et al. (1996 ▶).

Experimental

Crystal data

• C₁₃H₁₀O₃

• M _r = 214.21

• Monoclinic,

• a = 8.6500 (7) Å

• b = 5.5077 (5) Å

• c = 20.9655 (18) Å

• β = 94.145 (3)°

• V = 996.22 (15) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 293 (2) K

• 0.21 × 0.20 × 0.16 mm

Data collection

• Bruker APEXII area-detector diffractometer

• Absorption correction: none

• 6310 measured reflections

• 1800 independent reflections

• 854 reflections with I > 2σ(I)

• R _int = 0.063

Refinement

• R[F ² > 2σ(F ²)] = 0.058

• wR(F ²) = 0.183

• S = 1.01

• 1800 reflections

• 160 parameters

• 24 restraints

• H-atom parameters constrained

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.82	2.624 (3)	168
O3—H3A⋯O3ii	0.82	2.20	3.0041 (18)	168

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

Hydrogen-bonding interactions between ligands are specific and directional. When present in metal complexes they usually do not rely on the properties of the metal ions, but they play an important role in the overall structures and functions of the complexes and the way in which they pack in the solid state (Zwier et al., 1996; Datta & Pati, 2006). In this context we report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The C—O and C—C bond distances show no remarkable features. The title molecular structure acts as both a hydrogen bonding donor and acceptor, forming dimers with neighboring molecules through O—H···O hydrogen bonding with a R²₂(8) graph set motif (Bernstein et al., 1995). A second hydrogen bonding interaction by the hydroxyl groups forms a chain and extends the structure into a lamellar layer (Table 1, Fig. 2).

Experimental

4-Hydroxyl-biphenyl-4'-carboxylic acid was dissolved in a hot ethanol-water solution (1:1; v/v) with stirring. Colorless single crystals suitable for X-ray diffraction were obtained at room temperature by slow evaporation of the solvent over a period of several days.

Refinement

In the initial refinement with disorder not taken into account one of phenyl rings showed significantly elongated thermal ellipsoids indicating disorder, the dihedral angle between two phenyl rings is 5.66 (2) /%A, and the adjacent distances of C-H···C-H interactions in the biphenylene are 2.044 (1) and 2.077 (1) /%A, respectively, thus leading to a static repulsion between two phenyl rings,and the phenyl ring was thus refined as being disordered over two positions. The occupancy ratio refined to 0.57 (2) to 0.43 (2). The adps of the disordered atoms were restrained to be close to isotropic and those of equivalent atoms were set to be identical. Carbon-bound, hydroxyl and carboxylate group H atoms were placed at calculated positions and were treated as riding on their parent C or O atoms with C—H = 0.93 Å, with U_iso(H) = 1.2 U_eq(C); O—H = 0.82 Å and with U_iso(H) = 1.5 U_eq(O).

Figures

Fig. 1.

The structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.

Fig. 2.

A layer view of (I).

Crystal data

C13H10O3	F000 = 448
Mr = 214.21	Dx = 1.428 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1560 reflections
a = 8.6500 (7) Å	θ = 1.4–28.0º
b = 5.5077 (5) Å	µ = 0.10 mm−1
c = 20.9655 (18) Å	T = 293 (2) K
β = 94.145 (3)º	Plate, colorless
V = 996.22 (15) Å3	0.21 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	854 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Monochromator: graphite	θmax = 25.2º
T = 293(2) K	θmin = 2.0º
φ and ω scans	h = −10→10
Absorption correction: none	k = −5→6
6310 measured reflections	l = −24→25
1800 independent reflections

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.183	w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1800 reflections	Δρmax = 0.18 e Å−3
160 parameters	Δρmin = −0.19 e Å−3
24 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.3074 (3)	0.0387 (7)	0.03781 (15)	0.0499 (9)
C8	0.7212 (3)	0.1508 (6)	0.15024 (14)	0.0448 (8)
C9	0.6208 (3)	0.3440 (6)	0.13452 (16)	0.0578 (10)
H9	0.6499	0.4597	0.1054	0.069*
C10	0.4806 (3)	0.3688 (7)	0.16071 (17)	0.0593 (10)
H10	0.4167	0.4999	0.1493	0.071*
C11	0.4352 (3)	0.2019 (7)	0.20337 (15)	0.0525 (9)
C12	0.5302 (4)	0.0092 (7)	0.22074 (16)	0.0596 (10)
H12	0.5001	−0.1052	0.2500	0.072*
C13	0.6703 (4)	−0.0119 (6)	0.19414 (15)	0.0545 (9)
H13	0.7339	−0.1424	0.2064	0.065*
O1	1.3852 (2)	−0.1522 (5)	0.05016 (11)	0.0704 (8)
O2	1.3483 (2)	0.2037 (5)	0.00069 (12)	0.0696 (8)
H2	1.4342	0.1717	−0.0112	0.104*
O3	0.2936 (3)	0.2362 (5)	0.22900 (12)	0.0720 (8)
H3A	0.2672	0.1099	0.2458	0.108*
C2	1.15866 (19)	0.0702 (5)	0.06838 (10)	0.0480 (8)	0.43 (2)
C3	1.0867 (8)	0.2959 (6)	0.0682 (6)	0.052 (3)	0.43 (2)
H3	1.1327	0.4288	0.0498	0.063*	0.43 (2)
C4	0.9458 (8)	0.3228 (6)	0.0954 (6)	0.045 (2)	0.43 (2)
H4	0.8976	0.4738	0.0952	0.054*	0.43 (2)
C5	0.8770 (2)	0.1241 (4)	0.12279 (11)	0.0441 (8)	0.43 (2)
C6	0.9490 (7)	−0.1015 (7)	0.1230 (5)	0.045 (3)	0.43 (2)
H6	0.9029	−0.2345	0.1413	0.054*	0.43 (2)
C7	1.0898 (8)	−0.1285 (7)	0.0958 (6)	0.052 (3)	0.43 (2)
H7	1.1380	−0.2795	0.0959	0.062*	0.43 (2)
C2'	1.15879 (19)	0.0709 (5)	0.06822 (10)	0.0480 (8)	0.57 (2)
C3'	1.0571 (7)	0.2579 (15)	0.0469 (5)	0.052 (2)	0.57 (2)
H3'	1.0845	0.3647	0.0153	0.063*	0.57 (2)
C4'	0.9160 (7)	0.2818 (15)	0.0734 (5)	0.049 (2)	0.57 (2)
H4'	0.8485	0.4045	0.0588	0.059*	0.57 (2)
C5'	0.8725 (2)	0.1234 (5)	0.12205 (11)	0.0441 (8)	0.57 (2)
C6'	0.9755 (6)	−0.0581 (16)	0.1431 (4)	0.048 (2)	0.57 (2)
H6'	0.9505	−0.1621	0.1758	0.057*	0.57 (2)
C7'	1.1161 (6)	−0.0845 (15)	0.1155 (4)	0.047 (2)	0.57 (2)
H7'	1.1827	−0.2097	0.1291	0.056*	0.57 (2)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0396 (18)	0.061 (2)	0.051 (2)	0.0010 (18)	0.0134 (16)	0.0005 (19)
C8	0.0388 (17)	0.044 (2)	0.0527 (18)	−0.0001 (16)	0.0113 (15)	−0.0022 (17)
C9	0.0445 (19)	0.058 (2)	0.073 (2)	0.0005 (18)	0.0159 (17)	0.011 (2)
C10	0.0418 (19)	0.057 (2)	0.081 (2)	0.0079 (18)	0.0170 (18)	0.008 (2)
C11	0.0338 (17)	0.062 (3)	0.064 (2)	−0.0032 (17)	0.0160 (15)	−0.0135 (19)
C12	0.049 (2)	0.061 (3)	0.071 (2)	0.0015 (18)	0.0214 (18)	0.0075 (19)
C13	0.0448 (19)	0.051 (2)	0.069 (2)	0.0088 (17)	0.0183 (17)	0.0053 (18)
O1	0.0529 (15)	0.0705 (18)	0.0910 (18)	0.0171 (13)	0.0281 (13)	0.0188 (15)
O2	0.0460 (14)	0.083 (2)	0.0837 (18)	0.0127 (13)	0.0307 (13)	0.0194 (15)
O3	0.0418 (13)	0.090 (2)	0.0882 (18)	0.0033 (13)	0.0308 (12)	−0.0057 (16)
C2	0.0334 (17)	0.062 (2)	0.050 (2)	−0.0008 (17)	0.0144 (15)	0.0031 (18)
C3	0.040 (5)	0.065 (7)	0.054 (5)	0.002 (5)	0.015 (4)	0.006 (5)
C4	0.046 (5)	0.047 (6)	0.043 (5)	0.005 (4)	0.012 (4)	0.000 (4)
C5	0.0367 (17)	0.049 (2)	0.0476 (19)	−0.0041 (16)	0.0129 (14)	0.0004 (17)
C6	0.045 (5)	0.052 (5)	0.039 (5)	−0.002 (4)	0.002 (4)	−0.008 (4)
C7	0.041 (5)	0.061 (7)	0.052 (5)	0.003 (4)	0.001 (4)	−0.001 (5)
C2'	0.0334 (17)	0.062 (2)	0.050 (2)	−0.0008 (17)	0.0144 (15)	0.0031 (18)
C3'	0.044 (4)	0.057 (5)	0.058 (4)	0.004 (3)	0.014 (4)	0.008 (4)
C4'	0.042 (4)	0.049 (4)	0.057 (4)	0.012 (3)	0.014 (3)	0.000 (4)
C5'	0.0367 (17)	0.049 (2)	0.0476 (19)	−0.0041 (16)	0.0129 (14)	0.0004 (17)
C6'	0.036 (4)	0.068 (5)	0.039 (4)	0.007 (3)	0.010 (3)	0.009 (4)
C7'	0.029 (3)	0.063 (5)	0.049 (4)	0.011 (3)	0.005 (3)	0.007 (4)

Geometric parameters (Å, °)

C1—O2	1.264 (4)	C3—C4	1.3900
C1—O1	1.265 (4)	C3—H3	0.9300
C1—C2	1.488 (4)	C4—C5	1.3900
C8—C13	1.379 (4)	C4—H4	0.9300
C8—C9	1.398 (4)	C5—C6	1.3900
C8—C5	1.510 (3)	C6—C7	1.3900
C9—C10	1.374 (4)	C6—H6	0.9300
C9—H9	0.9300	C7—H7	0.9300
C10—C11	1.360 (5)	C2'—C7'	1.3793
C10—H10	0.9300	C2'—C3'	1.4061
C11—C12	1.375 (4)	C3'—C4'	1.3820
C11—O3	1.386 (4)	C3'—H3'	0.9300
C12—C13	1.375 (4)	C4'—C5'	1.4147
C12—H12	0.9300	C4'—H4'	0.9300
C13—H13	0.9300	C5'—C6'	1.3903
O2—H2	0.8200	C6'—C7'	1.3923
O3—H3A	0.8200	C6'—H6'	0.9300
C2—C3	1.3900	C7'—H7'	0.9300
C2—C7	1.3900
O2—C1—O1	123.7 (3)	C3—C4—C5	120.0
O2—C1—C2	118.1 (3)	C3—C4—H4	120.0
O1—C1—C2	118.2 (3)	C5—C4—H4	120.0
C13—C8—C9	115.4 (3)	C6—C5—C4	120.0
C13—C8—C5	121.9 (3)	C6—C5—C8	119.8 (2)
C9—C8—C5	122.7 (3)	C4—C5—C8	120.1 (2)
C10—C9—C8	122.2 (3)	C5—C6—C7	120.0
C10—C9—H9	118.9	C5—C6—H6	120.0
C8—C9—H9	118.9	C7—C6—H6	120.0
C11—C10—C9	120.1 (3)	C6—C7—C2	120.0
C11—C10—H10	120.0	C6—C7—H7	120.0
C9—C10—H10	120.0	C2—C7—H7	120.0
C10—C11—C12	120.1 (3)	C7'—C2'—C3'	119.2
C10—C11—O3	117.9 (3)	C4'—C3'—C2'	119.5
C12—C11—O3	122.0 (3)	C4'—C3'—H3'	120.2
C11—C12—C13	119.0 (3)	C2'—C3'—H3'	120.2
C11—C12—H12	120.5	C3'—C4'—C5'	121.3
C13—C12—H12	120.5	C3'—C4'—H4'	119.4
C12—C13—C8	123.3 (3)	C5'—C4'—H4'	119.4
C12—C13—H13	118.4	C6'—C5'—C4'	118.4
C8—C13—H13	118.4	C5'—C6'—C7'	120.1
C3—C2—C7	120.0	C5'—C6'—H6'	120.0
C3—C2—C1	120.3 (2)	C7'—C6'—H6'	120.0
C7—C2—C1	119.7 (2)	C2'—C7'—C6'	121.5
C4—C3—C2	120.0	C2'—C7'—H7'	119.3
C4—C3—H3	120.0	C6'—C7'—H7'	119.3
C2—C3—H3	120.0

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.82	2.624 (3)	168
O3—H3A···O3ii	0.82	2.20	3.0041 (18)	168

Symmetry codes: (i) −x+3, −y, −z; (ii) −x+1/2, y−1/2, −z+1/2.