2-(4-Methyl­phen­yl)-1-(phenyl­sulfon­yl)propan-2-ol

Bao-Jun Shi; Liang-Zhu Huang; You-Qiang Li; Chang-Mei Si; Zhen-Ting Du

doi:10.1107/S1600536811039894

. 2011 Oct 5;67(Pt 11):o2845. doi: 10.1107/S1600536811039894

2-(4-Methylphenyl)-1-(phenylsulfonyl)propan-2-ol

Bao-Jun Shi ^a, Liang-Zhu Huang ^b, You-Qiang Li ^b, Chang-Mei Si ^b, Zhen-Ting Du ^b,^*

PMCID: PMC3247583 PMID: 22219888

Abstract

The title compound, C₁₆H₁₈O₃S, features a U-shape molecular structure with a dihedral angle between the terminal benzene rings of 20.8 (1)°. An intramolecular O—H⋯O hydrogen bond helps to stabilize the molecular structure. Intermolecular classical O—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the use of organic sulfones as intermediates in organic synthesis, see: Consiglio et al. (1983 ▶); Wenkert et al. (1983 ▶); Trost (1991 ▶). For related structures, see: Gu et al. (2004 ▶); Garst et al. (2006 ▶); Ding et al., (2009 ▶); Groszek et al. (2006 ▶); Shi et al. (2011 ▶). For background to our program to synthesis new herbicide derivatives, see: Du et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₈O₃S
M _r = 290.36
Orthorhombic,
a = 15.6696 (14) Å
b = 11.7501 (11) Å
c = 15.9042 (16) Å
V = 2928.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.38 × 0.29 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.919, T _max = 0.954
13679 measured reflections
2578 independent reflections
1590 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.141
S = 1.08
2578 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536811039894/xu5336sup1.cif

e-67-o2845-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039894/xu5336Isup2.hkl

e-67-o2845-Isup2.hkl^{(126.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039894/xu5336Isup3.cml

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
O1—H1⋯O3	0.82	2.14	2.848 (3)	144
O1—H1⋯O3ⁱ	0.82	2.45	3.103 (3)	137
C15—H15⋯O2ⁱⁱ	0.93	2.48	3.403 (5)	173

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

Acknowledgments

Financial support from the Fundamental Research Funds for the Central Universities in NWSUAF (No. QN2009048) and the opening project of Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin (BRTD1004) as well as the National Natural Science Foundation of China (20802058) is greatly appreciated.

supplementary crystallographic information

Comment

Organic sulfones have been proven as good intermediates in organic synthesis (Consiglio et al., 1983; Wenkert et al., 1983; Trost 1991). As a result of our program of synthesis of new herbcide derivatives (Du et al., 2011), we obtained a intermediate compound C₁₆H₁₈O₃S (I) in the synthesis and structure are reported here. There are two benzene rings in the title compound and they exhibit face-to-face conformation. The dihedral angle between the two benzene rings is 20.8 (1)°. The molecules of I are crystalized in Pbca space group which differs from that of 2-methoxy-4-methyl-1-(1-(phenylsulfonyl)propan-2-yl)benzene (P2~1~/c, Shi et al., 2011). In the crystal structure there is an intramolecular C—H···O hydrogen-bonding interaction (Table 1) which is benefical to the stabilization of the packing, and whose symmetry code is defined as -x, -y + 1, -z + 1.

Experimental

A mixture of 2-methyl-2-(p-tolyl)oxirane (148 mg, 1 mmol) and sodium benzenesulfinate (246 mg, 1.5 mmol) in dry DMF (3 ml) was stirred over night at 80°C. When the reaction was completed, 2 ml water was added to the reaction mixture to quench reaction, then was extracted with ethyl acetate (20 ml × 3). The ethyl acetate layers were combined and washed by 20 ml water, then 15 ml saturated sodium chloride and dried over anhydrous sodium sulfate. The solution was evapourated and the residue was separated on silica gel column chromatography with a gradient of petroleum ether and ethyl acetate as eluent to yield 348 mg the title compound. The compound was then dissolved in methanol, and colorless crystals were formed on slow evaporation at room temperature over one week.