Benzhydryl phenyl sulfone

In the title compound, C19H16O2S, the sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group, making a dihedral angle of 12.53 (10)°, and forms a dihedral angle of 41.25 (9)° with the other phenyl ring. In the crystal, weak C—H⋯O interactions form a two-dimensional network propagating along the bc plane.

In the title compound, C 19 H 16 O 2 S, the sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group, making a dihedral angle of 12.53 (10) , and forms a dihedral angle of 41.25 (9) with the other phenyl ring. In the crystal, weak C-HÁ Á ÁO interactions form a two-dimensional network propagating along the bc plane.

Comment
During our studies on the ambident reactivity of the phenylsulfinate anion we used diarylcarbenium ions (Ar 2 CH + ) as reference electrophiles [Mayr et al. (2001[Mayr et al. ( , 2008] and, hence, obtained the title compound from a reaction of sodium benzenesulfinate with benzhydryl chloride (Ph 2 CHCl) in dimethyl sulfoxide.
The asymmetric unit of the title compound contains one complete molecule, which is shown in Figure 1. The sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group with an dihedral angle of 12.53 (10)°. The other one forms a dihedral angle of 41.25 (9)° with the phenyl group bound to the sulfur atom.
Three weak C-H···O interactions are found (Table 1) which lead to the formation of a two-dimensional network that propagates along the bc plane (Fig. 2). Contacts of this type have been described for a structure of a related sulfone [Li et al. (2005)]. In terms of graph-set analysis [Bernstein et al. (1995), Etter et al. (1990], the descriptors on the unitary level are C 1 1 (4) for the H1···O2 interaction, C 1 1 (6) for the H7···O2 interaction, and C 1 1 (7) for the H4···O1 interaction.

Experimental
Benzhydryl Phenyl Sulfone was obtained by heating a mixture of sodium benzenesulfinate (0.21 g, 1.3 mmol) and benzhydryl chloride (0.26 g, 1.3 mmol) in DMSO at 70 °C. After completion of the reaction (4 h), the reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic phase was washed several times with water and dried (MgSO 4 ). A viscous oil was obtained after evaporation of the solvent under reduced pressure that solidified on standing. After column chromatography (silica gel, isohexane/EtOAc = 9/1), benzhydryl phenyl sulfone was isolated as colorless solid (0.33 g, 82%). A small amount of the title compound was dissolved in ethyl acetate. The solvent was allowed to evaporate slowly at room temperature. After 2 days crystals had formed that were suitable for X-ray analysis. mp 189°C (186-187 °C [da Silva Corrêa et al. (1968)]).

Refinement
All H atoms were found in difference maps. C-bonded H atoms were positioned geometrically (C-H = 1.00 Å for aliphatic, 0.95 Å for aromatic H) and treated as riding on their parent atoms [U iso (H) = 1.2U eq (C)].
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.  as those based on F, and R-factors based on all data will be even larger.