(Z)-1-(4-Methylphenyl)-2-(phenylsulfonyl)ethanone oxime

The molecule of the title compound, C15H15NO3S, has a twisted U-shaped conformation: the twist occurs at the central C—S(=O)2—C—C—C unit and the benzene ring makes a dihedral angle of 28.74 (7)° with the phenyl ring. The S—C—C=N torsion angle is −88.95 (13)°. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R 2 2(6) loops, and C—H⋯O hydrogen bonds connect the dimers into a three-dimensional network.

The molecule of the title compound, C 15 H 15 NO 3 S, has a twisted U-shaped conformation: the twist occurs at the central C-S( O) 2 -C-C-C unit and the benzene ring makes a dihedral angle of 28.74 (7) with the phenyl ring. The S-C-C N torsion angle is À88.95 (13) . In the crystal, inversion dimers linked by pairs of O-HÁ Á ÁN hydrogen bonds generate R 2 2 (6) loops, and C-HÁ Á ÁO hydrogen bonds connect the dimers into a three-dimensional network.

Related literature
For the biological activity of arylsulphones, see: Stephens et al. (2001); Abdel-Aziz et al. (2010). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).
The molecular structure of the title compound is shown in Fig. 1. The molecule adopts a twisted U-shaped conformation. The twist occurs at the central C6-S1-C7-C8-C9 unit and the C1-C6 benzene ring makes a dihedral angle of 28.74 (7)° with the C9-C14 phenyl ring.

Experimental
A mixture of 2-(phenylsulfonyl)-1-p-tolylethanone (0.274 g, 1 mmol), hydroxylamine hydrochloride (0.11 g, 1.5 mmol) and anhydrous sodium acetate (0.123 g, 1.5 mmol) in ethanol (50 ml) was refluxed for 1 h, then left to cool. The reaction mixture was poured into cold water and the solid product was filtered off, washed with water, dried and finally recrystallized from ethanol to afford the title compound as yellow needles.

Refinement
Atom H1O3 was located in a difference fourier map and refined freely [O3-H1O3 = 0.96 (2) Å]. The remaining H atoms were positioned geometrically [C-H = 0.93, 0.96 and 0.97 Å] and refined using a riding model with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl group.

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 with 50% probability displacement ellipsoids.  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 > σ(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.