1,8-Bis(4-fluoro­phen­yl)naphthalene

Jin-Wu Feng; Qing-Chuan Han

doi:10.1107/S1600536811020563

. 2011 Jun 11;67(Pt 7):o1595. doi: 10.1107/S1600536811020563

1,8-Bis(4-fluorophenyl)naphthalene

Jin-Wu Feng ^a,^*, Qing-Chuan Han ^a

PMCID: PMC3151928 PMID: 21837003

Abstract

In the title compound, C₂₂H₁₄F₂, the two benzene rings are oriented with respect to the naphthalene ring system at 67.76 (8) and 67.50 (8)°, and the two benzene rings are twisted with respect to each other at 18.95 (10)°. Weak intermolecular C—H⋯π interactions are present in the crystal structure.

Related literature

For related structures, see: Beagley et al. (1996 ▶); Wolf & Tumambac (2003 ▶).

Experimental

Crystal data

C₂₂H₁₄F₂
M _r = 316.33
Triclinic,
a = 8.4086 (11) Å
b = 9.6252 (11) Å
c = 11.2618 (13) Å
α = 87.705 (9)°
β = 74.895 (10)°
γ = 64.111 (12)°
V = 788.81 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
5315 measured reflections
2885 independent reflections
1543 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.095
S = 0.83
2885 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020563/xu5229sup1.cif

e-67-o1595-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020563/xu5229Isup2.hkl

e-67-o1595-Isup2.hkl^{(141.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020563/xu5229Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811020563/xu5229Isup4.cml

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

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

Cg1 and Cg2 are the centroids of the C7-benzene and C14-benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1ⁱ	0.93	2.88	3.6815 (19)	146
C22—H22⋯Cg2ⁱⁱ	0.93	2.84	3.6595 (19)	148

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

1,8-diaryl naphthalenes have attracted much attention mainly because of its U-shaped face-to-face geometry. These derivatives provide a special model to study the interactions of aromatic rings not only in the ground state but also in the transition state for rotation where they adopt an approximate edge-to-face conformation. Herein, we report 1,8-bis(4-fluorophenyl) naphthalene, a member of the 1,8-diaryl naphthalene family.

The asymmetric unit of the crystal structure contains one molecule featuring U-shaped geometry (Fig 1). The bond lengths and angles are normal and similar to those in related structures (Beagley et al., 1996; Wolf & Tumambac, 2003). In the crystal structure, two phenyl rings twisting out of the naphthalene plane form dihedral angle of 18.95 (10)°. And the dihedral angles between the naphthalene and two phenyl rings are 67.76 (8)° and 67.50 (8)°.

Experimental

1,8-Dibromonaphthalene (286 mg 1 mmol), 4-fluorophenylboronic acid (286 mg, 2.2 mmol), K₂CO₃ (1.38 g, 10 mmol) and Pd(PPh₃)₄ (5 mg, 0.004 mmol) in 50 ml of degassed toluene/ethanol (10:1) were mixed and refluxed for 12 h under N₂, then filtrated. The filtrate was evaporated under reduced pressure. The crude products were purified by column chromatography (silica gel) from n-hexane as eluent to give the product in 92% yield (291 mg). Recrystallization from n-hexane/CH₂Cl₂ (5:1) gave colorless crystals.