Bis(4-eth­oxy­phen­yl) sulfoxide

Kang Meng; Cheng Wu; Jing Cao; Ping Ma; Lihong Liu

doi:10.1107/S1600536811013213

. 2011 Apr 16;67(Pt 5):o1136. doi: 10.1107/S1600536811013213

Bis(4-ethoxyphenyl) sulfoxide

Kang Meng ^a, Cheng Wu ^a, Jing Cao ^a, Ping Ma ^a, Lihong Liu ^a,^*

PMCID: PMC3089090 PMID: 21754445

Abstract

In the title compound, C₁₆H₁₈O₃S, the dihedral angle between the benzene rings is 82.7 (2)°. The O atom of the sulfoxide group is disordered over two orientations with refined occupancy factors of 0.563 (3):0.437 (3). In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For background to Friedel–Crafts acylation, see: Edward & Sibelle (1963 ▶); DeHaan et al. (1979 ▶); Fillion & Fishlock (2005 ▶); Nishimoto et al. (2008 ▶). For the structures of related arylsulfoxides, see: Casarini et al. (2004 ▶); Noland & Kedrowski (2000 ▶).

Experimental

Crystal data

C₁₆H₁₈O₃S
M _r = 290.36
Triclinic,
a = 8.2052 (16) Å
b = 9.856 (2) Å
c = 10.196 (2) Å
α = 64.71 (3)°
β = 83.78 (3)°
γ = 82.88 (3)°
V = 738.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T _min = 0.957, T _max = 0.974
6624 measured reflections
3450 independent reflections
2590 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.095
S = 1.06
3450 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536811013213/rz2577sup1.cif

e-67-o1136-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013213/rz2577Isup2.hkl

e-67-o1136-Isup2.hkl^{(169.2KB, 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
C11—H11⋯O1ⁱ	0.93	2.51	3.3013 (18)	143

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Friedel-Crafts acylation is a potent method for building acylbenzene derivatives (Edward & Sibelle, 1963; DeHaan et al., 1979; Fillion & Fishlock, 2005; Nishimoto et al., 2008). Thiocarbonylbenzenes may be prepared by Friedel-Crafts acylation of benzene derivatives with thiocarbonyl chloride in the presence of anhydrous aluminium chloride. Thus, in order to investigate the potentiality of the method, the title compound was prepared by Friedel-Crafts acylation of phenetol, an electron-rich benzene derivative.

In the title compound (Fig. 1) the dihedral angle between the two benzene rings (C3—C8 and C9—C14) is 82.7 (2)°. The S=O bond length is shorter than those found in previously reported arylsulfoxides (Casarini et al., 2004; Noland & Kedrowski, 2000). The oxygen atom of the sulfoxide group is disordered over two orientations with site occupancies of 0.563 (3) and 0.437 (3) for the major and minor components, repectively. In the crystal structure, molecules are linkied by intermolecular C—H···O hydrogen bonds (Table 1) to form chains along the b axis.

Experimental

A round-bottomed flask was charged with 1.19 g (10 mmol) of freshly distilled thionyl chloride, 2.44 g (20 mmol) of phenetol and 20 ml of dried dichloromethane, and the mixture was stirred on an ice-water bath followed by addition of 2.67 g (20 mmol) of anhydrous aluminium chloride in a portionwise manner. The resulting mixture was stirred at room temperature overnight and poured into 200 ml of ice-water. The mixture thus formed was exacted with three 50-ml portions of dichloromethane, and the combined exacts were washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude title compound. Pure title compound was obtained by column chromatography. Crystals suitable for X-ray diffraction were obtained through slow evaporation of a ethyl acetate/petroleum ether (1:10 v/v) solution.