4-(1-Naphth­yl)benzoic acid

Carlos F R A C Lima; Ligia R Gomes; Luís M N B F Santos; John Nicolson Low

doi:10.1107/S1600536809046339

. 2009 Nov 7;65(Pt 12):o3037. doi: 10.1107/S1600536809046339

4-(1-Naphthyl)benzoic acid

Carlos F R A C Lima ^a, Ligia R Gomes ^b, Luís M N B F Santos ^a, John Nicolson Low ^c,^*

PMCID: PMC2972074 PMID: 21578772

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 ▶). graphic file with name e-65-o3037-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₂O₂
M _r = 248.27
Monoclinic,
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 ▶) 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
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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.

Supplementary Material

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

e-65-o3037-sup1.cif^{(17.9KB, cif)}

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

e-65-o3037-Isup2.hkl^{(118.5KB, hkl)}

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
O41—H41⋯O42ⁱ	0.84	1.79	2.6161 (18)	170
O42—H42⋯O41ⁱ	0.88	1.75	2.6161 (18)	168

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Symmetry code: (i) Inline graphic .

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.