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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1087.
Published online 2008 May 17. doi:  10.1107/S1600536808014220
PMCID: PMC2961561

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 [triangle]); Datta & Pati (2006 [triangle]); Zwier et al. (1996 [triangle]).

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Object name is e-64-o1087-scheme1.jpg

Experimental

Crystal data

  • C13H10O3
  • M r = 214.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1087-efi1.jpg
  • 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 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The author thanks South China Normal University for supporting this study.

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 Uiso(H) = 1.2 Ueq(C); O—H = 0.82 Å and with Uiso(H) = 1.5 Ueq(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

C13H10O3F000 = 448
Mr = 214.21Dx = 1.428 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1560 reflections
a = 8.6500 (7) Åθ = 1.4–28.0º
b = 5.5077 (5) ŵ = 0.10 mm1
c = 20.9655 (18) ÅT = 293 (2) K
β = 94.145 (3)ºPlate, colorless
V = 996.22 (15) Å30.21 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer854 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
Monochromator: graphiteθmax = 25.2º
T = 293(2) Kθmin = 2.0º
[var phi] and ω scansh = −10→10
Absorption correction: nonek = −5→6
6310 measured reflectionsl = −24→25
1800 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-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 reflectionsΔρmax = 0.18 e Å3
160 parametersΔρmin = −0.19 e Å3
24 restraintsExtinction 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 (Å2)

xyzUiso*/UeqOcc. (<1)
C11.3074 (3)0.0387 (7)0.03781 (15)0.0499 (9)
C80.7212 (3)0.1508 (6)0.15024 (14)0.0448 (8)
C90.6208 (3)0.3440 (6)0.13452 (16)0.0578 (10)
H90.64990.45970.10540.069*
C100.4806 (3)0.3688 (7)0.16071 (17)0.0593 (10)
H100.41670.49990.14930.071*
C110.4352 (3)0.2019 (7)0.20337 (15)0.0525 (9)
C120.5302 (4)0.0092 (7)0.22074 (16)0.0596 (10)
H120.5001−0.10520.25000.072*
C130.6703 (4)−0.0119 (6)0.19414 (15)0.0545 (9)
H130.7339−0.14240.20640.065*
O11.3852 (2)−0.1522 (5)0.05016 (11)0.0704 (8)
O21.3483 (2)0.2037 (5)0.00069 (12)0.0696 (8)
H21.43420.1717−0.01120.104*
O30.2936 (3)0.2362 (5)0.22900 (12)0.0720 (8)
H3A0.26720.10990.24580.108*
C21.15866 (19)0.0702 (5)0.06838 (10)0.0480 (8)0.43 (2)
C31.0867 (8)0.2959 (6)0.0682 (6)0.052 (3)0.43 (2)
H31.13270.42880.04980.063*0.43 (2)
C40.9458 (8)0.3228 (6)0.0954 (6)0.045 (2)0.43 (2)
H40.89760.47380.09520.054*0.43 (2)
C50.8770 (2)0.1241 (4)0.12279 (11)0.0441 (8)0.43 (2)
C60.9490 (7)−0.1015 (7)0.1230 (5)0.045 (3)0.43 (2)
H60.9029−0.23450.14130.054*0.43 (2)
C71.0898 (8)−0.1285 (7)0.0958 (6)0.052 (3)0.43 (2)
H71.1380−0.27950.09590.062*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)
H3'1.08450.36470.01530.063*0.57 (2)
C4'0.9160 (7)0.2818 (15)0.0734 (5)0.049 (2)0.57 (2)
H4'0.84850.40450.05880.059*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)
H6'0.9505−0.16210.17580.057*0.57 (2)
C7'1.1161 (6)−0.0845 (15)0.1155 (4)0.047 (2)0.57 (2)
H7'1.1827−0.20970.12910.056*0.57 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0396 (18)0.061 (2)0.051 (2)0.0010 (18)0.0134 (16)0.0005 (19)
C80.0388 (17)0.044 (2)0.0527 (18)−0.0001 (16)0.0113 (15)−0.0022 (17)
C90.0445 (19)0.058 (2)0.073 (2)0.0005 (18)0.0159 (17)0.011 (2)
C100.0418 (19)0.057 (2)0.081 (2)0.0079 (18)0.0170 (18)0.008 (2)
C110.0338 (17)0.062 (3)0.064 (2)−0.0032 (17)0.0160 (15)−0.0135 (19)
C120.049 (2)0.061 (3)0.071 (2)0.0015 (18)0.0214 (18)0.0075 (19)
C130.0448 (19)0.051 (2)0.069 (2)0.0088 (17)0.0183 (17)0.0053 (18)
O10.0529 (15)0.0705 (18)0.0910 (18)0.0171 (13)0.0281 (13)0.0188 (15)
O20.0460 (14)0.083 (2)0.0837 (18)0.0127 (13)0.0307 (13)0.0194 (15)
O30.0418 (13)0.090 (2)0.0882 (18)0.0033 (13)0.0308 (12)−0.0057 (16)
C20.0334 (17)0.062 (2)0.050 (2)−0.0008 (17)0.0144 (15)0.0031 (18)
C30.040 (5)0.065 (7)0.054 (5)0.002 (5)0.015 (4)0.006 (5)
C40.046 (5)0.047 (6)0.043 (5)0.005 (4)0.012 (4)0.000 (4)
C50.0367 (17)0.049 (2)0.0476 (19)−0.0041 (16)0.0129 (14)0.0004 (17)
C60.045 (5)0.052 (5)0.039 (5)−0.002 (4)0.002 (4)−0.008 (4)
C70.041 (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—O21.264 (4)C3—C41.3900
C1—O11.265 (4)C3—H30.9300
C1—C21.488 (4)C4—C51.3900
C8—C131.379 (4)C4—H40.9300
C8—C91.398 (4)C5—C61.3900
C8—C51.510 (3)C6—C71.3900
C9—C101.374 (4)C6—H60.9300
C9—H90.9300C7—H70.9300
C10—C111.360 (5)C2'—C7'1.3793
C10—H100.9300C2'—C3'1.4061
C11—C121.375 (4)C3'—C4'1.3820
C11—O31.386 (4)C3'—H3'0.9300
C12—C131.375 (4)C4'—C5'1.4147
C12—H120.9300C4'—H4'0.9300
C13—H130.9300C5'—C6'1.3903
O2—H20.8200C6'—C7'1.3923
O3—H3A0.8200C6'—H6'0.9300
C2—C31.3900C7'—H7'0.9300
C2—C71.3900
O2—C1—O1123.7 (3)C3—C4—C5120.0
O2—C1—C2118.1 (3)C3—C4—H4120.0
O1—C1—C2118.2 (3)C5—C4—H4120.0
C13—C8—C9115.4 (3)C6—C5—C4120.0
C13—C8—C5121.9 (3)C6—C5—C8119.8 (2)
C9—C8—C5122.7 (3)C4—C5—C8120.1 (2)
C10—C9—C8122.2 (3)C5—C6—C7120.0
C10—C9—H9118.9C5—C6—H6120.0
C8—C9—H9118.9C7—C6—H6120.0
C11—C10—C9120.1 (3)C6—C7—C2120.0
C11—C10—H10120.0C6—C7—H7120.0
C9—C10—H10120.0C2—C7—H7120.0
C10—C11—C12120.1 (3)C7'—C2'—C3'119.2
C10—C11—O3117.9 (3)C4'—C3'—C2'119.5
C12—C11—O3122.0 (3)C4'—C3'—H3'120.2
C11—C12—C13119.0 (3)C2'—C3'—H3'120.2
C11—C12—H12120.5C3'—C4'—C5'121.3
C13—C12—H12120.5C3'—C4'—H4'119.4
C12—C13—C8123.3 (3)C5'—C4'—H4'119.4
C12—C13—H13118.4C6'—C5'—C4'118.4
C8—C13—H13118.4C5'—C6'—C7'120.1
C3—C2—C7120.0C5'—C6'—H6'120.0
C3—C2—C1120.3 (2)C7'—C6'—H6'120.0
C7—C2—C1119.7 (2)C2'—C7'—C6'121.5
C4—C3—C2120.0C2'—C7'—H7'119.3
C4—C3—H3120.0C6'—C7'—H7'119.3
C2—C3—H3120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.822.624 (3)168
O3—H3A···O3ii0.822.203.0041 (18)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2111).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed.34, 1555–1573.
  • Bruker (2004). APEX2 and SMART Bruker AXS Inc, Madison, Wisconsin, USA.
  • Datta, A. & Pati, S. K. (2006). Chem. Soc. Rev. pp. 1305–1323. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zwier, T. S. (1996). Annu. Rev. Phys. Chem.47, 205–241.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography