1-(2′,4′-Difluoro­biphenyl-4-yl)ethanone

Meng-Ping Guo; Ji-Hua Deng; Qiao-Chu Zhang; Hui-Rui Guo; Lin Yuan

doi:10.1107/S1600536808028596

. 2008 Sep 13;64(Pt 10):o1923. doi: 10.1107/S1600536808028596

1-(2′,4′-Difluorobiphenyl-4-yl)ethanone

Meng-Ping Guo ^a,^*, Ji-Hua Deng ^b, Qiao-Chu Zhang ^b, Hui-Rui Guo ^a, Lin Yuan ^b

PMCID: PMC2959460 PMID: 21201131

Abstract

In the crystal structure of the title compound, C₁₄H₁₀F₂O, the dihedral angles between the benzene rings in the two crystallographically independent molecules are 46.9 (2) and 47.6 (2)°. The molecules are linked into dimers by C—H⋯F interactions and these dimers are further stacked into columns along the b axis by π–π interactions between the benzene rings [centroid–centroid distance = 3.8221 Å; the dihedral angle between the planes of these rings is 4.87 (2)°]. In addition, C—F⋯π interactions also contribute to the crystal packing (C⋯centroid distance = 3.5919 Å).

Related literature

For general background, see: William & Ruyle (1973 ▶). For related structures, see:Kuchar et al. (1997 ▶); Jegorov et al. (1995 ▶, 1997 ▶).

Experimental

Crystal data

C₁₄H₁₀F₂O
M _r = 232.22
Orthorhombic,
a = 13.092 (7) Å
b = 6.102 (3) Å
c = 27.719 (15) Å
V = 2214 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.46 × 0.32 × 0.25 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
15497 measured reflections
2576 independent reflections
2219 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.207
S = 1.13
2576 reflections
309 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks gmp, I. DOI: 10.1107/S1600536808028596/nc2113sup1.cif

e-64-o1923-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028596/nc2113Isup2.hkl

e-64-o1923-Isup2.hkl^{(126.3KB, 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
C12—H12A⋯F2ⁱ	0.93	2.46	3.369 (6)	167
C22—H22⋯F4ⁱⁱ	0.93	2.40	3.318 (6)	167

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

Table 2. C—F⋯π interactions (Å, °).

C—F⋯Cg^a	F⋯Cg	C⋯Cg	γ^b	C—F⋯Cg
C1—F1⋯Cg(C7→C12)ⁱⁱⁱ	3.8358	3.5919	27.36	69
C15—F3⋯Cg(C21→C26)^iv	3.8814	3.5966	27.14	68

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Notes: Cg ^a = centre of gravity of the six-membered ring. γ^b = angle defined by a line connecting the centre of gravity of the six-membered ring with H atom and the normal to the six-membered ring. Symmetry codes: (iii) Inline graphic ; (IV) .

Table 3. π⋯π interactions (Å, °).

π⋯π contacts	Cg⋯Cg(Å)	α^a(°)	β^b(°)	Cg⋯Plane(Å)
Cg(C1→C6)⋯Cg(C7→C12)ⁱⁱⁱ	3.8221	4.87	27.32	3.616
Cg(C15→C20)⋯Cg(C21→C26)^iv	3.8284	5.68	23.57	3.642

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Notes: α^a = angle between planes of two aromatic rings. β^b = angle between Cg⋯Cg line and normal to the plane of the first aromatic ring. Symmetry codes: (iii) Inline graphic ; (IV) .

Acknowledgments

The work was supported by the National Natural Science Foundation of China (No. 20763008) and the Key Science & Technology Plan of Yichun City (No. [2006] 56).

supplementary crystallographic information

Comment

The crystal structure of the title compound was determined as a part of a project on the synthesis of 1-(2',4'-difluorobiphenyl-4-yl)ethanone, which have excellent activity against various bacteria, antifebrile and abirritation (William et al., 1973; Kuchar et al., 1997; Jegorov, Husak et al., 1997; Jegorov, Sedmera et al., 1995). The title compound is an intermediate in this synthesis.

The asymmetric unit of (I) contains two crystallographically indepedent molecules of the same stereochemical configuration (Fig. 1). The dihedral angle between aromatic ring C1-C6 and C7-C12 amount to 46.8 (2) ° and between ring C15-C20 and C21-C26 it is 47.6 (2) ° (Fig. 1). The molecules are connected into dimers via C—H···F interactions (Table 1). There also exist π—π stacking interactions between the benzene rings of adjacent molecules. The distances of the centroids of the rings C1-C6 and C7-C12 as well as rings C15-C20 and C21-C26) amount to 3.8821 and 3.8284 /%A, respectively. In the direction of the b-axis, the molecules shows a herringbone like arrangement.

Experimental

0.1892 g (1 mmol) 1-(4-bromophenyl)ethanone, 0.2385 g (1.5 mmol) 2,4-difluorophenylboronic acid, 0.2123 g (2 mmol) Na₂CO₃ and 0.2255 g (1 mmol) Pd(OAc)₂ were dissolved in a water-acetone mixture (1:1 v/v; 50 ml). After stirring for 20 min at 308 K, the mixture were extracted using diethylether for four times. Then the resultant diethylether solution were dried over magnesium sulfate and concentrated in vacuo. Well shaped light yellow crystals suitable for X-ray structure analysis were obtained by recrystalling the crude product from ethanol.