1-(Phenylsulfonyl)naphthalene

In the title compound, C16H12O2S, the phenyl ring is nearly perpendicular to the naphthalene system [dihedral angle = 80.3 (1)°]. The packing is consolidated by a weak C—H⋯π interaction involving neighbouring naphthalene and benzene rings. In addition, there exist two different offset π–π stacking interactions between benzene rings and between naphthalene systems of symmetry-related molecules [centroid–centroid distances = 3.876 (9) and 3.566 (4) Å, and slippage = 1.412 and 0.554 Å, respectively.


1-(Phenylsulfonyl)naphthalene
Ying Fu, Wenbo Zhu, Hongxia Hou, Yinxia He and Hulin Li Comment Phenyl sulphone derivatives are an important class of organic sulfur compounds due to their broad spectrum of biological activities in a wide range of fields such as agrochemicals (Borys et al. 2012), pharmaceuticals (Padwa et al. 1990;Block, 1992) and polymers (Mackinnon & Wang, 1998). The molecular structure is shown in Fig. 1. All bond lengths and angles are in the normal range.
In the molecule of (I), Figure 1, both the naphthalene ring and the phenyl ring adopt essentially planar conformation with a maximum deviation of 0.0032 Å for the phenyl ring and 0.0038 Å for the naphthalene ring. The phenyl ring is nearly perpendicular to the naphthalene ring with the dihedral angle 80.3 (1)°.

Experimental
For the synthesis of the title compound,see: Boroujeni (2010); Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in petroleum ether-ethyl acetate (5:1).

Refinement
All H atoms were geometrically positioned and refined using a riding model with C-H = 0.93 Å, U iso (H) = 1.2 U eq (C).

1-(Phenylsulfonyl)naphthalene
Crystal data C 16 H 12 O 2 S M r = 268.32 Triclinic, P1 Hall symbol: -P 1 a = 7.721 (7) Å b = 9.444 (9) Å c = 9.726 (9) Å α = 86.669 (8) where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.17 e Å −3 Δρ min = −0.32 e Å −3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.