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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3037.
Published online 2009 November 7. doi:  10.1107/S1600536809046339
PMCID: PMC2972074

4-(1-Naphth­yl)benzoic acid

Abstract

In the title mol­ecule, C17H12O2, the dihedral angle between the mean plane of the benzene ring and that of the naphthalene ring system is 49.09 (6)°. In the crystal structure, mol­ecules are linked to form centrosymmetric dimers via inter­molecular O—H(...)O hydrogen bonds. The hydr­oxy H atom is disordered over two sites with refined occupancies of 0.62 (3) and 0.38 (3).

Related literature

For a description of supra­molecular structures formed via hydrogen bonds, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o3037-scheme1.jpg

Experimental

Crystal data

  • C17H12O2
  • M r = 248.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3037-efi1.jpg
  • a = 3.8972 (6) Å
  • b = 40.511 (6) Å
  • c = 7.6106 (12) Å
  • β = 99.323 (3)°
  • V = 1185.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 150 K
  • 0.30 × 0.18 × 0.02 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.973, T max = 0.998
  • 4700 measured reflections
  • 2412 independent reflections
  • 1954 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.107
  • S = 1.04
  • 2412 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046339/lh2945sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046339/lh2945Isup2.hkl

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

Acknowledgments

CFRACL thanks FCT and the European Social Fund (ESF) under the third Community Support Framework (CSF) for the award of a PhD Research Grant (SRFH/BD/29394/2006). LRG thanks Fundação para o Ensino e Cultura Fernando Pessoa.

supplementary crystallographic information

Comment

In the crystal structure, molecules of the title compound form typical carboxylic acid R22(8), (Bernstein et al. 1995), dimers across inversion centers. The hydroxy H atom is disordered over two sites. Figure 1 shows a centrosymmetric dimer of the title compound.

Experimental

A solution of K2CO3(20 mmol,4 mol/eq) in 20 ml of water was added to a solution of 1-bromonaphthalene(5 mmol, 1 mol/eq), 4-carboxyphenylboronic acid (8 mmol of water, 1.6 mol/eq) and Pd(OAc)2 (2mol%) in 20 ml of water. The resultant mixture was heated at 95°C, with constant stirring, for 6 h. The final solution was allowed to cool to room temperature, acidified to pH < 5 and extracted with ethyl acetate. The organic layer was washed with aqueous 0.1MHCl, dried over anhydrous sodium sulfate and evaporated. The resulting precipitate was washed with ether yielding 0.73 g of white flakes, (yield 59%, purity 99.9%). Crystals suitable for X-ray diffraction were obtained by crystallization from a 50/50 mixture of chloroform and acetone.

Refinement

H atoms positions were calulated and refined as riding atoms with C—H(aromatic), 0.95 Å. The OH(hydroxy) was located in a difference Fourier map and identified as disordered over two sites, one H atom attached to O41 with a distance of 0.84Å and a site occupancy of 0.62 (3), the other attached to O42 with a distance of 0.88Å and a site occupancy of 0.38 (3). These atoms were refined as riding atoms. These positions were confirmed by examination of a difference map with hydroxy H atoms omitted form the structure model after the final refinement cycle (see Fig 2). The reflections 020 and 040 were omitted from the refinement since they were obscured by the beam-stop. The asymmetric unit was selected so that the centre of the dimer lies at (1/2, 1/2, 1/2).

Figures

Fig. 1.
A centrosymmetric dimer of the title compound. Atoms labelled with an 'a' are related by the symmetry operator (1 - x,1 - y,1 - z). Displacement ellipsoids are drawn at the 30% probability level. Only the major component of the disorder is shown.
Fig. 2.
A difference map with hydroxy H atoms not included in the structure model, showing a section in the plane of the disordered hydroxy H atoms and the C atom of the carboxyl group.

Crystal data

C17H12O2F(000) = 520
Mr = 248.27Dx = 1.391 Mg m3
Monoclinic, P21/cMelting point: 509 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 3.8972 (6) ÅCell parameters from 1563 reflections
b = 40.511 (6) Åθ = 6.3–26.4°
c = 7.6106 (12) ŵ = 0.09 mm1
β = 99.323 (3)°T = 150 K
V = 1185.7 (3) Å3Plate, colorless
Z = 40.30 × 0.18 × 0.02 mm

Data collection

Bruker SMART APEXII diffractometer2412 independent reflections
Radiation source: fine-focus sealed tube1954 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 8.333 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = −2→4
Absorption correction: multi-scan (SADABS; Bruker, 2003)k = −45→50
Tmin = 0.973, Tmax = 0.998l = −9→9
4700 measured 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)] = 0.044H-atom parameters constrained
wR(F2) = 0.107w = 1/[σ2(Fo2) + (0.0453P)2 + 0.4999P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2412 reflectionsΔρmax = 0.25 e Å3
174 parametersΔρmin = −0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)

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)
O410.5693 (4)0.50335 (3)0.73150 (17)0.0320 (3)
H410.48320.49230.64190.048*0.62 (3)
O420.7354 (4)0.53531 (3)0.52203 (16)0.0330 (3)
H420.65020.52020.44400.050*0.38 (3)
C11.1807 (4)0.62769 (4)1.2149 (2)0.0187 (4)
C21.3777 (4)0.61873 (4)1.3748 (2)0.0214 (4)
H21.43580.59611.39610.026*
C31.4950 (4)0.64219 (5)1.5074 (2)0.0248 (4)
H31.62960.63531.61660.030*
C41.4159 (5)0.67478 (5)1.4795 (2)0.0260 (4)
H41.50150.69051.56830.031*
C51.1179 (5)0.71913 (4)1.2917 (2)0.0266 (4)
H51.20600.73491.37970.032*
C60.9075 (5)0.72919 (4)1.1408 (2)0.0288 (4)
H60.84910.75191.12420.035*
C70.7765 (5)0.70599 (4)1.0094 (2)0.0267 (4)
H70.62810.71310.90470.032*
C80.8613 (4)0.67326 (4)1.0313 (2)0.0224 (4)
H80.76890.65790.94140.027*
C91.2078 (4)0.68535 (4)1.3196 (2)0.0216 (4)
C101.0846 (4)0.66168 (4)1.1855 (2)0.0190 (4)
C111.0745 (4)0.60175 (4)1.0782 (2)0.0180 (4)
C121.1205 (4)0.60601 (4)0.9008 (2)0.0197 (4)
H121.22560.62570.86700.024*
C131.0158 (4)0.58211 (4)0.7744 (2)0.0196 (4)
H131.04970.58540.65480.024*
C140.8601 (4)0.55312 (4)0.8215 (2)0.0192 (4)
C150.8267 (4)0.54788 (4)0.9991 (2)0.0209 (4)
H150.72940.52781.03340.025*
C160.9353 (4)0.57188 (4)1.1253 (2)0.0203 (4)
H160.91470.56801.24620.024*
C410.7169 (4)0.52934 (4)0.6815 (2)0.0215 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O410.0478 (8)0.0241 (7)0.0241 (7)−0.0120 (6)0.0064 (6)−0.0021 (5)
O420.0525 (9)0.0286 (7)0.0179 (6)−0.0113 (6)0.0056 (6)−0.0031 (5)
C10.0165 (8)0.0231 (9)0.0172 (8)−0.0026 (7)0.0047 (6)−0.0008 (6)
C20.0207 (8)0.0243 (9)0.0193 (8)0.0012 (7)0.0042 (6)0.0003 (7)
C30.0238 (9)0.0331 (10)0.0166 (8)−0.0004 (8)0.0008 (6)−0.0005 (7)
C40.0260 (9)0.0323 (10)0.0196 (9)−0.0054 (8)0.0035 (7)−0.0075 (7)
C50.0301 (10)0.0227 (9)0.0290 (9)−0.0060 (8)0.0110 (8)−0.0065 (7)
C60.0341 (10)0.0208 (9)0.0350 (10)0.0031 (8)0.0156 (8)0.0023 (8)
C70.0274 (10)0.0290 (10)0.0242 (9)0.0041 (8)0.0060 (7)0.0045 (7)
C80.0225 (9)0.0249 (9)0.0199 (8)−0.0024 (7)0.0034 (6)−0.0008 (7)
C90.0197 (9)0.0247 (9)0.0217 (8)−0.0033 (7)0.0072 (7)−0.0021 (7)
C100.0171 (8)0.0218 (9)0.0193 (8)−0.0024 (7)0.0064 (6)0.0006 (6)
C110.0147 (8)0.0198 (8)0.0189 (8)0.0030 (6)0.0014 (6)−0.0001 (6)
C120.0190 (8)0.0206 (9)0.0193 (8)−0.0013 (7)0.0023 (6)0.0025 (7)
C130.0203 (8)0.0220 (9)0.0165 (8)0.0012 (7)0.0027 (6)0.0016 (6)
C140.0186 (8)0.0194 (8)0.0189 (8)0.0019 (7)0.0011 (6)−0.0008 (6)
C150.0226 (9)0.0188 (9)0.0211 (8)0.0000 (7)0.0028 (6)0.0034 (7)
C160.0221 (9)0.0226 (9)0.0163 (8)0.0019 (7)0.0035 (6)0.0035 (6)
C410.0231 (9)0.0200 (9)0.0217 (8)0.0018 (7)0.0042 (6)0.0014 (7)

Geometric parameters (Å, °)

O41—C411.286 (2)C6—H60.9500
O41—H410.8400C7—C81.370 (2)
O42—C411.251 (2)C7—H70.9500
O42—H420.8806C8—C101.423 (2)
C1—C21.379 (2)C8—H80.9500
C1—C101.435 (2)C9—C101.426 (2)
C1—C111.489 (2)C11—C161.396 (2)
C2—C31.407 (2)C11—C121.401 (2)
C2—H20.9500C12—C131.379 (2)
C3—C41.365 (3)C12—H120.9500
C3—H30.9500C13—C141.395 (2)
C4—C91.415 (2)C13—H130.9500
C4—H40.9500C14—C151.395 (2)
C5—C61.361 (3)C14—C411.477 (2)
C5—C91.420 (2)C15—C161.384 (2)
C5—H50.9500C15—H150.9500
C6—C71.407 (3)C16—H160.9500
C41—O41—H41109.6C4—C9—C10119.45 (16)
C41—O42—H42116.4C5—C9—C10119.66 (16)
C2—C1—C10118.95 (15)C8—C10—C9117.32 (15)
C2—C1—C11118.87 (15)C8—C10—C1123.64 (15)
C10—C1—C11122.17 (14)C9—C10—C1119.00 (15)
C1—C2—C3121.67 (16)C16—C11—C12118.02 (15)
C1—C2—H2119.2C16—C11—C1120.51 (14)
C3—C2—H2119.2C12—C11—C1121.44 (14)
C4—C3—C2120.18 (16)C13—C12—C11121.06 (15)
C4—C3—H3119.9C13—C12—H12119.5
C2—C3—H3119.9C11—C12—H12119.5
C3—C4—C9120.68 (16)C12—C13—C14120.24 (15)
C3—C4—H4119.7C12—C13—H13119.9
C9—C4—H4119.7C14—C13—H13119.9
C6—C5—C9121.00 (17)C13—C14—C15119.33 (15)
C6—C5—H5119.5C13—C14—C41119.53 (14)
C9—C5—H5119.5C15—C14—C41121.06 (15)
C5—C6—C7119.97 (17)C16—C15—C14119.96 (15)
C5—C6—H6120.0C16—C15—H15120.0
C7—C6—H6120.0C14—C15—H15120.0
C8—C7—C6120.50 (17)C15—C16—C11121.24 (14)
C8—C7—H7119.8C15—C16—H16119.4
C6—C7—H7119.8C11—C16—H16119.4
C7—C8—C10121.51 (16)O42—C41—O41122.96 (15)
C7—C8—H8119.2O42—C41—C14119.94 (15)
C10—C8—H8119.2O41—C41—C14117.08 (14)
C4—C9—C5120.89 (16)
C10—C1—C2—C3−1.9 (2)C11—C1—C10—C9−177.44 (14)
C11—C1—C2—C3178.11 (14)C2—C1—C11—C1646.9 (2)
C1—C2—C3—C4−0.3 (3)C10—C1—C11—C16−133.14 (16)
C2—C3—C4—C91.7 (3)C2—C1—C11—C12−131.12 (17)
C9—C5—C6—C7−0.2 (3)C10—C1—C11—C1248.9 (2)
C5—C6—C7—C8−0.5 (3)C16—C11—C12—C133.1 (2)
C6—C7—C8—C10−0.5 (3)C1—C11—C12—C13−178.82 (15)
C3—C4—C9—C5178.49 (16)C11—C12—C13—C140.2 (2)
C3—C4—C9—C10−1.0 (2)C12—C13—C14—C15−3.0 (2)
C6—C5—C9—C4−177.62 (16)C12—C13—C14—C41173.74 (15)
C6—C5—C9—C101.9 (2)C13—C14—C15—C162.5 (2)
C7—C8—C10—C92.1 (2)C41—C14—C15—C16−174.24 (15)
C7—C8—C10—C1179.89 (15)C14—C15—C16—C110.9 (2)
C4—C9—C10—C8176.77 (15)C12—C11—C16—C15−3.7 (2)
C5—C9—C10—C8−2.7 (2)C1—C11—C16—C15178.25 (15)
C4—C9—C10—C1−1.2 (2)C13—C14—C41—O42−0.1 (2)
C5—C9—C10—C1179.34 (15)C15—C14—C41—O42176.61 (17)
C2—C1—C10—C8−175.23 (15)C13—C14—C41—O41−178.49 (15)
C11—C1—C10—C84.8 (2)C15—C14—C41—O41−1.8 (2)
C2—C1—C10—C92.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O41—H41···O42i0.841.792.6161 (18)170
O42—H42···O41i0.881.752.6161 (18)168

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2945).

References

  • Bernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Johnson, C. K. (1976). ORTEPII. Technical Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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