4'-Hydroxy-biphenyl-4-carboxylic acid.

The title compound, C(13)H(10)O(3), has potential oxygen donor and acceptor sites. Inter-molecular hydrogen bonding between neighboring carboxyl-ate groups leads to the formation of hydrogen-bonded dimers [graph-set motif R(2) (2)(8)]. A second hydrogen-bonding inter-action between the hydr-oxy 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 = 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) Å3

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

Δρmax = 0.18 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014220/zl2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014220/zl2111Isup2.hkl

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

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

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 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

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.

	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)

	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)

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

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

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) .