1-(1-Benzo­furan-2-yl)ethanone O-(2,6-di­fluoro­benz­yl)oxime

Tomasz Kosmalski; Andrzej K Gzella

doi:10.1107/S1600536813034090

. 2013 Dec 24;70(Pt 1):o91. doi: 10.1107/S1600536813034090

1-(1-Benzofuran-2-yl)ethanone O-(2,6-difluorobenzyl)oxime

Tomasz Kosmalski ^a, Andrzej K Gzella ^b,^*

PMCID: PMC3914113 PMID: 24527020

Abstract

In the title compound, C₁₇H₁₃F₂NO₂, the 2,2-difluorobenzyloxy residue assumes an E configuration with respect to the benzofuran system. The benzene ring makes a dihedral angle of 61.70 (4)° with the fused ring system (r.m.s. deviation = 0.008 Å). In the crystal, molecules are connected by weak C—H⋯F hydrogen bonds into chains extending parallel to the b-axis direction.

Related literature

For background to antifungal agents, see: Benedetti & Bani (1999 ▶); Sheehan et al. (1999 ▶). For the biological activity of oximes and their ethers, see: Attia et al. (2013 ▶); De Luca (2006 ▶); Emami et al. (2004 ▶); Karakurt et al. (2001 ▶); Massolini et al. (1993 ▶); Mixich & Thiele (1985 ▶). For the synthesis of the title compound, see: Demirayak et al. (2002 ▶). graphic file with name e-70-00o91-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₃F₂NO₂
M _r = 301.28
Monoclinic,
a = 7.36652 (17) Å
b = 17.0314 (4) Å
c = 11.2047 (2) Å
β = 90.020 (2)°
V = 1405.76 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 130 K
0.35 × 0.15 × 0.12 mm

Data collection

Agilent Xcalibur Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.992, T _max = 1.000
24335 measured reflections
3548 independent reflections
2887 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.099
S = 1.03
3548 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536813034090/zs2281sup1.cif

e-70-00o91-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034090/zs2281Isup2.hkl

e-70-00o91-Isup2.hkl^{(170.5KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536813034090/zs2281Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F22ⁱ	0.93	2.54	3.3537 (16)	147

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

1. Comment

The increase in fungal infections and the gained resistance to the currently used drugs in recent years directed the studies on obtaining new antifungal drugs (Benedetti & Bani, 1999). After the discovery of oxiconazole (Sheehan et al., 1999), ether oximes became of interest and a number of oximes were synthesized and found to be active against fungi (Attia et al., 2013; De Luca, 2006; Emami et al., 2004; Karakurt et al., 2001; Massolini et al., 1993; Mixich & Thiele, 1985). The crystal structure investigation of the title compound was undertaken to confirm the E configuration of the molecule, proposed on the basis of spectroscopic data.

The molecular structure of the title compound and the atom-labelling scheme is illustrated in Fig. 1. In this compound, the nine-membered benzofuran system is planar with an r.m.s. deviation of 0.0083 Å. The 2,6-difluorobenzyloxy moiety is in the E configuration with respect to the benzofuran system [torsion angle C2—C10—N12—O13: 178.89 (9)°]. The C10—N12 bond is antiperiplanar in relation to the O13—C14 bond [torsion angle C10—N12—O13—C14: 176.13 (10)°]. A similar observation has been made for bonds N12—O13 and C14—C15 [torsion angle N12—O13—C14—C15: 170.08 (10)°]. The planar benzofuran system and the phenyl ring form a dihedral angle of 61.70 (4)°.

The molecular packing in the crystal lattice is stabilized by possible C7—H7···F22ⁱ non-classical intermolecular hydrogen bonds (Table 1) which link molecules into chains lying parallel to the b axis (Fig. 2).

2. Experimental

1-(1-Benzofuran-2-yl)ethanone O-(2,6-difluorobenzyl)oxime was synthesized from 1-(benzofuran-2-yl)ethanone oxime and 2,6-difluorobenzyl bromide, according to the literature procedure of Demirayak et al. (2002). Crystals were obtained after crystallization from ethanol.