1,8-Bis(4-fluoro­phen­yl)naphthalene

Feng, J.-W.; Han, Q.-C.

doi:10.1107/S1600536811020563

organic compounds

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Volume 67| Part 7| July 2011| Page o1595

doi:10.1107/S1600536811020563

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1,8-Bis(4-fluorophenyl)naphthalene

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

^aDepartment of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China
^*Correspondence e-mail: jinwu_feng@163.com

(Received 27 May 2011; accepted 29 May 2011; online 11 June 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020563/xu5229sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811020563/xu5229Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811020563/xu5229Isup4.cml

checkCIF report

Comment top

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)°.

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed down the a axis.

1,8-Bis(4-fluorophenyl)naphthalene top

Crystal data top

C₂₂H₁₄F₂	Z = 2
M_r = 316.33	F(000) = 328
Triclinic, P1	D_x = 1.332 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4086 (11) Å	Cell parameters from 1771 reflections
b = 9.6252 (11) Å	θ = 3.6–29.2°
c = 11.2618 (13) Å	µ = 0.09 mm⁻¹
α = 87.705 (9)°	T = 293 K
β = 74.895 (10)°	Block, colorless
γ = 64.111 (12)°	0.20 × 0.20 × 0.16 mm
V = 788.81 (16) Å³

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.3°, θ_min = 3.6°
Detector resolution: 10.3592 pixels mm^-1	h = −10→7
ω scans	k = −11→11
5315 measured reflections	l = −13→13
2885 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
2885 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₂H₁₄F₂	γ = 64.111 (12)°
M_r = 316.33	V = 788.81 (16) Å³
Triclinic, P1	Z = 2
a = 8.4086 (11) Å	Mo Kα radiation
b = 9.6252 (11) Å	µ = 0.09 mm⁻¹
c = 11.2618 (13) Å	T = 293 K
α = 87.705 (9)°	0.20 × 0.20 × 0.16 mm
β = 74.895 (10)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 0.83	Δρ_max = 0.14 e Å⁻³
2885 reflections	Δρ_min = −0.14 e Å⁻³
217 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
F1	0.37936 (19)	0.21582 (15)	0.99923 (10)	0.1062 (5)
F2	0.78304 (18)	0.38981 (15)	0.97949 (10)	0.0976 (4)
C1	0.4395 (3)	0.2123 (3)	0.87403 (17)	0.0661 (6)
C2	0.3265 (3)	0.3170 (2)	0.81271 (19)	0.0677 (6)
H2	0.2094	0.3895	0.8549	0.081*
C3	0.3897 (2)	0.3131 (2)	0.68655 (17)	0.0572 (5)
H3	0.3129	0.3828	0.6432	0.069*
C4	0.5657 (2)	0.20736 (19)	0.62257 (15)	0.0446 (4)
C5	0.6740 (2)	0.10154 (19)	0.69004 (15)	0.0499 (5)
H5	0.7910	0.0276	0.6492	0.060*
C6	0.6115 (3)	0.1040 (2)	0.81600 (17)	0.0608 (5)
H6	0.6852	0.0332	0.8605	0.073*
C7	0.6285 (2)	0.20390 (18)	0.48640 (15)	0.0437 (4)
C8	0.5392 (2)	0.16090 (19)	0.42018 (17)	0.0552 (5)
H8	0.4422	0.1405	0.4634	0.066*
C9	0.5858 (3)	0.1461 (2)	0.29184 (18)	0.0635 (5)
H9	0.5219	0.1156	0.2509	0.076*
C10	0.7243 (3)	0.1765 (2)	0.22772 (17)	0.0604 (5)
H10	0.7570	0.1653	0.1419	0.072*
C11	0.8212 (2)	0.22514 (18)	0.28818 (15)	0.0487 (5)
C12	0.7750 (2)	0.24087 (17)	0.41961 (14)	0.0409 (4)
C13	0.8780 (2)	0.29298 (18)	0.47501 (14)	0.0423 (4)
C14	1.0158 (2)	0.32195 (19)	0.39941 (15)	0.0526 (5)
H14	1.0830	0.3540	0.4358	0.063*
C15	1.0593 (3)	0.3056 (2)	0.27130 (17)	0.0588 (5)
H15	1.1533	0.3267	0.2236	0.071*
C16	0.9638 (3)	0.2587 (2)	0.21706 (16)	0.0582 (5)
H16	0.9921	0.2482	0.1314	0.070*
C17	0.8487 (2)	0.31863 (18)	0.60942 (14)	0.0427 (4)
C18	0.9840 (2)	0.2255 (2)	0.66502 (16)	0.0546 (5)
H18	1.0912	0.1458	0.6175	0.066*
C19	0.9624 (3)	0.2488 (2)	0.78916 (18)	0.0626 (5)
H19	1.0528	0.1852	0.8262	0.075*
C20	0.8053 (3)	0.3675 (2)	0.85619 (16)	0.0600 (5)
C21	0.6700 (3)	0.4637 (2)	0.80646 (16)	0.0553 (5)
H21	0.5646	0.5439	0.8551	0.066*
C22	0.6922 (2)	0.44001 (18)	0.68275 (15)	0.0465 (4)
H22	0.6013	0.5060	0.6471	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1273 (12)	0.1060 (11)	0.0602 (8)	−0.0503 (9)	0.0131 (7)	0.0029 (7)
F2	0.1270 (12)	0.1024 (10)	0.0591 (8)	−0.0398 (9)	−0.0378 (7)	0.0068 (7)
C1	0.0790 (16)	0.0652 (15)	0.0519 (12)	−0.0405 (14)	0.0016 (12)	0.0036 (11)
C2	0.0498 (13)	0.0642 (14)	0.0749 (15)	−0.0241 (12)	0.0053 (11)	−0.0058 (11)
C3	0.0432 (12)	0.0519 (12)	0.0719 (13)	−0.0182 (10)	−0.0131 (10)	0.0039 (9)
C4	0.0410 (11)	0.0397 (10)	0.0558 (11)	−0.0217 (9)	−0.0111 (9)	0.0068 (9)
C5	0.0503 (11)	0.0371 (10)	0.0570 (12)	−0.0177 (9)	−0.0094 (9)	0.0070 (9)
C6	0.0715 (15)	0.0505 (12)	0.0578 (12)	−0.0269 (12)	−0.0145 (11)	0.0139 (10)
C7	0.0404 (10)	0.0303 (9)	0.0581 (11)	−0.0118 (8)	−0.0174 (8)	0.0092 (8)
C8	0.0550 (12)	0.0449 (11)	0.0720 (13)	−0.0234 (10)	−0.0261 (10)	0.0143 (9)
C9	0.0759 (15)	0.0502 (12)	0.0771 (14)	−0.0291 (12)	−0.0390 (12)	0.0076 (10)
C10	0.0740 (14)	0.0464 (12)	0.0569 (12)	−0.0189 (11)	−0.0253 (11)	0.0049 (9)
C11	0.0523 (12)	0.0334 (10)	0.0520 (11)	−0.0107 (9)	−0.0160 (9)	0.0064 (8)
C12	0.0399 (10)	0.0284 (9)	0.0472 (10)	−0.0073 (8)	−0.0143 (8)	0.0054 (7)
C13	0.0374 (10)	0.0312 (9)	0.0508 (10)	−0.0096 (8)	−0.0098 (8)	0.0045 (8)
C14	0.0479 (11)	0.0458 (11)	0.0600 (12)	−0.0201 (9)	−0.0092 (9)	0.0044 (9)
C15	0.0517 (12)	0.0512 (12)	0.0629 (13)	−0.0212 (10)	−0.0020 (10)	0.0090 (9)
C16	0.0573 (13)	0.0484 (12)	0.0509 (11)	−0.0125 (10)	−0.0058 (10)	0.0073 (9)
C17	0.0418 (11)	0.0370 (10)	0.0528 (11)	−0.0202 (9)	−0.0139 (9)	0.0058 (8)
C18	0.0427 (11)	0.0488 (12)	0.0661 (13)	−0.0144 (9)	−0.0145 (9)	0.0015 (9)
C19	0.0625 (14)	0.0600 (13)	0.0706 (14)	−0.0233 (12)	−0.0340 (11)	0.0129 (11)
C20	0.0782 (16)	0.0618 (14)	0.0466 (12)	−0.0331 (13)	−0.0236 (11)	0.0076 (10)
C21	0.0617 (13)	0.0444 (11)	0.0527 (12)	−0.0189 (10)	−0.0114 (10)	−0.0011 (9)
C22	0.0473 (11)	0.0341 (10)	0.0550 (11)	−0.0145 (9)	−0.0154 (9)	0.0060 (8)

Geometric parameters (Å, º) top

F1—C1	1.3646 (19)	C11—C16	1.414 (2)
F2—C20	1.3648 (19)	C11—C12	1.425 (2)
C1—C2	1.358 (3)	C12—C13	1.441 (2)
C1—C6	1.361 (3)	C13—C14	1.376 (2)
C2—C3	1.377 (2)	C13—C17	1.482 (2)
C2—H2	0.9300	C14—C15	1.390 (2)
C3—C4	1.390 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.348 (2)
C4—C5	1.390 (2)	C15—H15	0.9300
C4—C7	1.483 (2)	C16—H16	0.9300
C5—C6	1.375 (2)	C17—C18	1.388 (2)
C5—H5	0.9300	C17—C22	1.395 (2)
C6—H6	0.9300	C18—C19	1.377 (2)
C7—C8	1.371 (2)	C18—H18	0.9300
C7—C12	1.445 (2)	C19—C20	1.361 (3)
C8—C9	1.391 (2)	C19—H19	0.9300
C8—H8	0.9300	C20—C21	1.355 (3)
C9—C10	1.344 (2)	C21—C22	1.371 (2)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.412 (2)	C22—H22	0.9300
C10—H10	0.9300

C2—C1—C6	122.77 (18)	C11—C12—C13	117.21 (14)
C2—C1—F1	119.0 (2)	C11—C12—C7	117.47 (15)
C6—C1—F1	118.2 (2)	C13—C12—C7	125.33 (14)
C1—C2—C3	118.37 (19)	C14—C13—C12	118.86 (15)
C1—C2—H2	120.8	C14—C13—C17	115.85 (15)
C3—C2—H2	120.8	C12—C13—C17	125.28 (14)
C2—C3—C4	121.43 (18)	C13—C14—C15	123.13 (17)
C2—C3—H3	119.3	C13—C14—H14	118.4
C4—C3—H3	119.3	C15—C14—H14	118.4
C5—C4—C3	117.57 (16)	C16—C15—C14	119.22 (17)
C5—C4—C7	122.12 (15)	C16—C15—H15	120.4
C3—C4—C7	120.21 (16)	C14—C15—H15	120.4
C6—C5—C4	121.32 (17)	C15—C16—C11	121.14 (17)
C6—C5—H5	119.3	C15—C16—H16	119.4
C4—C5—H5	119.3	C11—C16—H16	119.4
C1—C6—C5	118.50 (18)	C18—C17—C22	117.78 (15)
C1—C6—H6	120.8	C18—C17—C13	119.94 (15)
C5—C6—H6	120.8	C22—C17—C13	122.19 (15)
C8—C7—C12	118.37 (15)	C19—C18—C17	121.23 (17)
C8—C7—C4	116.25 (15)	C19—C18—H18	119.4
C12—C7—C4	125.38 (14)	C17—C18—H18	119.4
C7—C8—C9	123.50 (17)	C20—C19—C18	118.20 (18)
C7—C8—H8	118.2	C20—C19—H19	120.9
C9—C8—H8	118.2	C18—C19—H19	120.9
C10—C9—C8	119.15 (18)	C21—C20—C19	123.14 (17)
C10—C9—H9	120.4	C21—C20—F2	118.63 (18)
C8—C9—H9	120.4	C19—C20—F2	118.23 (18)
C9—C10—C11	121.25 (17)	C20—C21—C22	118.43 (17)
C9—C10—H10	119.4	C20—C21—H21	120.8
C11—C10—H10	119.4	C22—C21—H21	120.8
C10—C11—C16	119.35 (17)	C21—C22—C17	121.20 (16)
C10—C11—C12	120.23 (16)	C21—C22—H22	119.4
C16—C11—C12	120.43 (16)	C17—C22—H22	119.4

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄F₂
M_r	316.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4086 (11), 9.6252 (11), 11.2618 (13)
α, β, γ (°)	87.705 (9), 74.895 (10), 64.111 (12)
V (Å³)	788.81 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5315, 2885, 1543
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.095, 0.83
No. of reflections	2885
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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	2.8763	3.6815 (19)	146
C22—H22···Cg2ⁱⁱ	0.93	2.8364	3.6595 (19)	148

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

References

Beagley, B., Edge, N. C., Jaiboon, N., James, J. J., McAuliffe, C. A., Thorp, M. S., Watkinson, M., Whiting, A. & Wright, D. C. (1996). Tetrahedron, 30, 10193–10204. CrossRef Google Scholar
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wolf, C. & Tumambac, G. E. (2003). J. Phys. Chem. A, 105, 815–817. CrossRef Google Scholar

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doi:10.1107/S1600536811020563

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