1-(4-Fluorophenyl)-2-(phenylsulfonyl)ethanone

In the title compound, C14H11FO3S, the unit comprising the ethanone and 4-fluorophenyl groups is essentially planar, with an r.m.s. deviation of 0.0084 (2) Å for the ten non-H atoms, and it makes a dihedral angle of 37.31 (10)° with the phenyl ring. In the crystal, molecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R 2 2(16) graph-set motifs. The dimers are stacked along the b axis through further C—H⋯O hydrogen bonds.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 Arylsulphones are an interesting class of non-nucleoside antiviral agents. A large number of them have been also shown various interesting biological activities (Abdel-Aziz et al., 2009, 2010Silvestri et al., 2000;Stephens et al., 2001) and found application in membrane technology for nanofiltration (Grandison et al., 2002). During the course of our research on the medicinal chemistry of arylsulphones, the title compound(I) was synthesized and studied for its biological activity.
Herein the crystal structure of (I) was reported.
The title molecule has a fold structure as indicated by the dihedral angle between the 4-fluorophenyl and phenyl rings being 36.98 (12)° (Fig. 1). The ethanone unit [C1/C2/O1] lies on the same plane with the 4-fluorophenyl ring with an r.m.s. deviation of 0.0084 (2) Å for the ten non-H atoms (C1-C8/O1/F1) and the dihedral angle between the ethanone plane and the 4-fluorophenyl ring being 1.2 (2)°. The environment of S atom is a distorted tetrahedral geometry [angles around S atom are 105.67 (8)-118.24 (9)°] being surrounded by two O atoms, one C atom of the ethanone unit and one C atom of the benzene ring. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structures (Abdel-Aziz et al., 2011. In the crystal packing ( Fig. 2), the molecules are linked by pairs of weak C···H···O sulfonyl interactions (Table 1) into inversion dimers with R 2 2 (16) graph-set motifs (Bernstein et al., 1995) and these dimers are arranged into layers parallel to the ac plane and stacked along the b axis.

Experimental
The title compound was prepared according to the reported method (Xiang et al., 2007). Colorless plate-shaped single crystals suitable for an X-ray structural analysis were obtained by slow evaporation from an ethanol solution at room temperature.

Refinement
H atoms were placed in calculated positions with d(C-H) = 0.93 for aromatic and 0.97 Å for CH 2 atoms. The U iso (H) values were constrained to be 1.2U eq of the carrier atom.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009   The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.22 e Å −3 Δρ min = −0.30 e Å −3 Extinction correction: SHELXTL (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0041 (5) Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.