3-Fluoro-4-nitro­phenyl 4-methyl­benzene­sulfonate

Wei Ang; You-Fu Luo; Yong Deng

doi:10.1107/S1600536811005903

. 2011 Mar 2;67(Pt 4):o750. doi: 10.1107/S1600536811005903

3-Fluoro-4-nitrophenyl 4-methylbenzenesulfonate

Wei Ang ^a, You-Fu Luo ^b, Yong Deng ^a,^*

PMCID: PMC3099963 PMID: 21754047

Abstract

In the title compound, C₁₃H₁₀FNO₅S, the dihedral angle between the benzene rings is 47.63 (14)°. In the crystal, π–π stacking occurs between nearly parallel benzene rings of adjacent molecules, the centroid–centroid distance being 3.7806 (16) Å. Weak intermolecular C—H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

For related compounds and their biological activity, see: Cho et al. (2003) ▶; Marson et al. (2007 ▶).

Experimental

Crystal data

C₁₃H₁₀FNO₅S
M _r = 311.28
Orthorhombic,
a = 14.2596 (5) Å
b = 11.4800 (3) Å
c = 8.3602 (2) Å
V = 1368.57 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T _min = 0.979, T _max = 1.0
10802 measured reflections
2251 independent reflections
1855 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.083
S = 1.05
2251 reflections
191 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 752 Friedel pairs
Flack parameter: −0.06 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005903/xu5126sup1.cif

e-67-0o750-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005903/xu5126Isup2.hkl

e-67-0o750-Isup2.hkl^{(110.7KB, 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
C6—H6⋯O2ⁱ	0.93	2.55	3.224 (4)	129

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

Aryloxyalkanoic acid hydroxyamides are potent inhibitors of histone deacetylase (Marson et al., 2007; Cho et al., 2003). 3-Fluoro-4-nitrophenyl 4-methylbenzenesulfonate is one of the key intermediates to synthesize the aryloxyalkanoic acid hydroxyamides derivatives. We report here its crystal structure. In the title compound (Fig. 1), the dihedral angle between the 3-fluoro-4-nitrophenyl ring and the 4-methylbenzene ring is 47.63 (14)°. In the crystal, intermolecular π-π stacking [centroid–centroid distance = 3.7806 (16) Å] stabilizes the structure (Fig. 2). Weak C—H···O hydrogen bonding is present in the crystal structure (Table 1).

Experimental

To the 3-fluoro-4-nitrophenol (19.10 mmol) in chloroform (20 ml) at 273 K were added pyridine (3.70 ml, 45.84 mmol) dropwise over a period of 20 min and p-toluenesulfonyl chloride (22.92 mmol) in small portions. This reaction mixture was stirred at room temperature for 12 h and diluted with dichloromethane and then 10% aqueous HCl. The separated organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl; dried over NaSO4; and concentrated in vacuo. The crude 3-fluoro-4-nitrophenyl 4-methylbenzenesulfonate were purified by recrystallization. Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of ethanol.