Benzhydryl phenyl sulfone

Mahiuddin Baidya; Herbert Mayr; Peter Mayer

doi:10.1107/S1600536809050363

. 2009 Nov 28;65(Pt 12):o3224. doi: 10.1107/S1600536809050363

Benzhydryl phenyl sulfone

Mahiuddin Baidya ^a, Herbert Mayr ^a, Peter Mayer ^a,^*

PMCID: PMC2972123 PMID: 21578931

Abstract

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.

Related literature

For background to the sulfone anion, see: da Silva Corrêa et al. (1968 ▶); Mayr et al. (2001 ▶, 2008 ▶). For a related structure, see: Li et al. (2005 ▶). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). graphic file with name e-65-o3224-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₆O₂S
M _r = 308.40
Orthorhombic,
a = 16.3250 (4) Å
b = 5.7979 (1) Å
c = 16.4983 (4) Å
V = 1561.58 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 200 K
0.20 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
11675 measured reflections
3499 independent reflections
3136 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.075
S = 1.04
3499 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1646 Friedel pairs
Flack parameter: −0.03 (6)

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050363/ds2011sup1.cif

e-65-o3224-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050363/ds2011Isup2.hkl

e-65-o3224-Isup2.hkl^{(171.6KB, 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
C1—H1⋯O2ⁱ	1.00	2.46	3.449 (2)	171
C4—H4⋯O1ⁱⁱ	0.95	2.66	3.390 (2)	134
C7—H7⋯O2ⁱ	0.95	2.68	3.543 (2)	152

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

Acknowledgments

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

supplementary crystallographic information

Comment

During our studies on the ambident reactivity of the phenylsulfinate anion we used diarylcarbenium ions (Ar₂CH⁺) as reference electrophiles [Mayr et al. (2001, 2008)] and, hence, obtained the title compound from a reaction of sodium benzenesulfinate with benzhydryl chloride (Ph₂CHCl) 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 C₁¹(4) for the H1···O2 interaction, C₁¹(6) for the H7···O2 interaction, and C₁¹(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 (MgSO₄). 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)]).