1-(Phenyl-sulfon-yl)naphthalene.

In the title compound, C(16)H(12)O(2)S, 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 inter-action involving neighbouring naphthalene and benzene rings. In addition, there exist two different offset π-π stacking inter-actions between benzene rings and between naphthalene systems of symmetry-related mol-ecules [centroid-centroid distances = 3.876 (9) and 3.566 (4) Å, and slippage = 1.412 and 0.554 Å, respectively.

Related literature

For recent reports on the synthesis of aryl­sulfones, see: Boroujeni (2010 ▶); Bahrami et al. (2008 ▶). For their application, see: Borys et al. (2012 ▶); Padwa et al. (1990 ▶); Block (1992 ▶); Mackinnon & Wang (1998 ▶). For single-crystal structures of sulfones, see: Chawdhury & Hargreaves (1971 ▶); Bacon & Curry (1960 ▶); Sime & Abrahams (1960 ▶); Jeyaraman & Velmurugan (1997 ▶).

Experimental

Crystal data

C16H12O2S

M = 268.32

Triclinic,

a = 7.721 (7) Å

b = 9.444 (9) Å

c = 9.726 (9) Å

α = 86.669 (8)°

β = 74.690 (8)°

γ = 69.995 (7)°

V = 642.4 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.25 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.941, T max = 0.955

4623 measured reflections

2345 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.05

2345 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030929/lr2072sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030929/lr2072Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030929/lr2072Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812030929/lr2072Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H12O2S	Z = 2
Mr = 268.32	F(000) = 280
Triclinic, P1	Dx = 1.387 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.721 (7) Å	Cell parameters from 2200 reflections
b = 9.444 (9) Å	θ = 2.2–27.4°
c = 9.726 (9) Å	µ = 0.25 mm−1
α = 86.669 (8)°	T = 296 K
β = 74.690 (8)°	Block, colourless
γ = 69.995 (7)°	0.25 × 0.23 × 0.19 mm
V = 642.4 (10) Å3

Bruker APEXII CCD diffractometer	2345 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→8
Tmin = 0.941, Tmax = 0.955	k = −11→10
4623 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.1481P] where P = (Fo2 + 2Fc2)/3
2345 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.2011 (2)	0.34105 (19)	0.13095 (18)	0.0371 (4)
C2	0.2381 (3)	0.2563 (2)	0.0103 (2)	0.0471 (5)
H2	0.2356	0.1584	0.0184	0.056*
C3	0.2797 (3)	0.3150 (2)	−0.1249 (2)	0.0552 (5)
H3	0.3031	0.2566	−0.2059	0.066*
C4	0.2859 (3)	0.4559 (2)	−0.1378 (2)	0.0542 (5)
H4	0.3140	0.4938	−0.2282	0.065*
C5	0.2506 (3)	0.5470 (2)	−0.0172 (2)	0.0448 (5)
C6	0.2557 (3)	0.6953 (3)	−0.0325 (3)	0.0622 (6)
H6	0.2860	0.7320	−0.1233	0.075*
C7	0.2173 (4)	0.7842 (3)	0.0828 (3)	0.0703 (7)
H7	0.2213	0.8815	0.0712	0.084*
C8	0.1712 (3)	0.7305 (2)	0.2201 (3)	0.0583 (6)
H8	0.1450	0.7929	0.2989	0.070*
C9	0.1642 (3)	0.5888 (2)	0.2401 (2)	0.0460 (5)
H9	0.1324	0.5557	0.3322	0.055*
C10	0.2049 (2)	0.49129 (19)	0.12201 (19)	0.0373 (4)
C11	0.3619 (3)	0.21084 (19)	0.35340 (18)	0.0392 (4)
C12	0.5126 (3)	0.0821 (2)	0.2971 (2)	0.0502 (5)
H12	0.5019	0.0197	0.2316	0.060*
C13	0.6790 (3)	0.0470 (3)	0.3391 (3)	0.0609 (6)
H13	0.7810	−0.0398	0.3021	0.073*
C14	0.6953 (3)	0.1394 (3)	0.4350 (2)	0.0579 (6)
H14	0.8086	0.1158	0.4619	0.070*
C15	0.5448 (3)	0.2663 (3)	0.4913 (2)	0.0577 (5)
H15	0.5562	0.3282	0.5569	0.069*
C16	0.3766 (3)	0.3030 (2)	0.4514 (2)	0.0494 (5)
H16	0.2743	0.3889	0.4901	0.059*
O1	−0.00281 (18)	0.35703 (15)	0.39697 (14)	0.0523 (4)
O2	0.1356 (2)	0.11219 (15)	0.26565 (15)	0.0560 (4)
S1	0.15229 (6)	0.25301 (5)	0.29564 (5)	0.04155 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0317 (9)	0.0348 (9)	0.0422 (9)	−0.0083 (7)	−0.0084 (8)	−0.0034 (7)
C2	0.0484 (11)	0.0388 (10)	0.0508 (11)	−0.0095 (9)	−0.0128 (9)	−0.0070 (8)
C3	0.0608 (14)	0.0552 (13)	0.0421 (11)	−0.0088 (11)	−0.0126 (10)	−0.0109 (9)
C4	0.0538 (13)	0.0589 (13)	0.0405 (10)	−0.0100 (10)	−0.0093 (9)	0.0048 (9)
C5	0.0397 (10)	0.0430 (11)	0.0499 (11)	−0.0113 (8)	−0.0131 (9)	0.0061 (8)
C6	0.0703 (15)	0.0524 (13)	0.0690 (14)	−0.0276 (12)	−0.0209 (12)	0.0187 (11)
C7	0.0824 (17)	0.0420 (12)	0.0986 (19)	−0.0296 (12)	−0.0348 (15)	0.0123 (13)
C8	0.0635 (14)	0.0398 (11)	0.0764 (15)	−0.0139 (10)	−0.0290 (12)	−0.0083 (10)
C9	0.0474 (11)	0.0402 (11)	0.0519 (11)	−0.0119 (9)	−0.0180 (9)	−0.0044 (8)
C10	0.0301 (9)	0.0369 (10)	0.0445 (10)	−0.0088 (7)	−0.0120 (8)	−0.0007 (8)
C11	0.0402 (10)	0.0362 (10)	0.0388 (9)	−0.0140 (8)	−0.0061 (8)	0.0073 (8)
C12	0.0511 (12)	0.0403 (11)	0.0538 (12)	−0.0113 (9)	−0.0102 (10)	−0.0001 (9)
C13	0.0443 (12)	0.0537 (13)	0.0706 (14)	−0.0041 (10)	−0.0094 (11)	0.0084 (11)
C14	0.0475 (12)	0.0718 (15)	0.0585 (13)	−0.0240 (11)	−0.0187 (10)	0.0170 (11)
C15	0.0602 (14)	0.0688 (15)	0.0506 (12)	−0.0265 (12)	−0.0191 (11)	0.0026 (10)
C16	0.0504 (12)	0.0475 (11)	0.0454 (11)	−0.0125 (9)	−0.0093 (9)	−0.0014 (9)
O1	0.0391 (8)	0.0590 (9)	0.0487 (8)	−0.0127 (6)	0.0016 (6)	−0.0058 (6)
O2	0.0611 (9)	0.0454 (8)	0.0689 (9)	−0.0308 (7)	−0.0122 (7)	0.0019 (7)
S1	0.0389 (3)	0.0396 (3)	0.0451 (3)	−0.0161 (2)	−0.0051 (2)	0.00010 (19)

C1—C2	1.369 (3)	C9—C10	1.415 (3)
C1—C10	1.426 (3)	C9—H9	0.9300
C1—S1	1.772 (2)	C11—C16	1.378 (3)
C2—C3	1.397 (3)	C11—C12	1.380 (3)
C2—H2	0.9300	C11—S1	1.763 (2)
C3—C4	1.345 (3)	C12—C13	1.377 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.407 (3)	C13—C14	1.370 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.413 (3)	C14—C15	1.369 (3)
C5—C10	1.423 (3)	C14—H14	0.9300
C6—C7	1.347 (3)	C15—C16	1.378 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.400 (3)	C16—H16	0.9300
C7—H7	0.9300	O1—S1	1.4335 (15)
C8—C9	1.358 (3)	O2—S1	1.4328 (18)
C8—H8	0.9300
C2—C1—C10	120.89 (17)	C9—C10—C5	117.97 (18)
C2—C1—S1	116.45 (16)	C9—C10—C1	125.12 (17)
C10—C1—S1	122.66 (13)	C5—C10—C1	116.90 (16)
C1—C2—C3	120.9 (2)	C16—C11—C12	120.55 (19)
C1—C2—H2	119.6	C16—C11—S1	121.51 (15)
C3—C2—H2	119.6	C12—C11—S1	117.94 (15)
C4—C3—C2	120.03 (19)	C13—C12—C11	119.3 (2)
C4—C3—H3	120.0	C13—C12—H12	120.4
C2—C3—H3	120.0	C11—C12—H12	120.4
C3—C4—C5	121.27 (19)	C14—C13—C12	120.4 (2)
C3—C4—H4	119.4	C14—C13—H13	119.8
C5—C4—H4	119.4	C12—C13—H13	119.8
C4—C5—C6	120.6 (2)	C15—C14—C13	120.1 (2)
C4—C5—C10	120.02 (19)	C15—C14—H14	120.0
C6—C5—C10	119.37 (19)	C13—C14—H14	120.0
C7—C6—C5	120.8 (2)	C14—C15—C16	120.5 (2)
C7—C6—H6	119.6	C14—C15—H15	119.8
C5—C6—H6	119.6	C16—C15—H15	119.8
C6—C7—C8	120.2 (2)	C11—C16—C15	119.24 (19)
C6—C7—H7	119.9	C11—C16—H16	120.4
C8—C7—H7	119.9	C15—C16—H16	120.4
C9—C8—C7	121.1 (2)	O2—S1—O1	118.25 (10)
C9—C8—H8	119.4	O2—S1—C11	107.09 (9)
C7—C8—H8	119.4	O1—S1—C11	108.84 (10)
C8—C9—C10	120.5 (2)	O2—S1—C1	107.42 (10)
C8—C9—H9	119.7	O1—S1—C1	109.94 (10)
C10—C9—H9	119.7	C11—S1—C1	104.41 (9)
C10—C1—C2—C3	−0.4 (3)	C16—C11—C12—C13	−0.5 (3)
S1—C1—C2—C3	−179.51 (15)	S1—C11—C12—C13	179.31 (15)
C1—C2—C3—C4	0.8 (3)	C11—C12—C13—C14	−0.4 (3)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—C15	0.9 (3)
C3—C4—C5—C6	−179.36 (19)	C13—C14—C15—C16	−0.5 (3)
C3—C4—C5—C10	−0.8 (3)	C12—C11—C16—C15	0.9 (3)
C4—C5—C6—C7	178.3 (2)	S1—C11—C16—C15	−178.94 (14)
C10—C5—C6—C7	−0.2 (3)	C14—C15—C16—C11	−0.4 (3)
C5—C6—C7—C8	−0.1 (4)	C16—C11—S1—O2	−148.12 (15)
C6—C7—C8—C9	0.0 (4)	C12—C11—S1—O2	32.06 (17)
C7—C8—C9—C10	0.5 (3)	C16—C11—S1—O1	−19.20 (18)
C8—C9—C10—C5	−0.8 (3)	C12—C11—S1—O1	160.98 (14)
C8—C9—C10—C1	−179.78 (18)	C16—C11—S1—C1	98.16 (17)
C4—C5—C10—C9	−177.90 (17)	C12—C11—S1—C1	−81.66 (17)
C6—C5—C10—C9	0.7 (3)	C2—C1—S1—O2	−8.25 (17)
C4—C5—C10—C1	1.2 (3)	C10—C1—S1—O2	172.61 (14)
C6—C5—C10—C1	179.75 (17)	C2—C1—S1—O1	−138.16 (15)
C2—C1—C10—C9	178.39 (18)	C10—C1—S1—O1	42.70 (17)
S1—C1—C10—C9	−2.5 (2)	C2—C1—S1—C11	105.24 (15)
C2—C1—C10—C5	−0.6 (3)	C10—C1—S1—C11	−73.90 (15)
S1—C1—C10—C5	178.48 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgi	0.93	2.90	3.806 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg i	0.93	2.90	3.806 (5)	166

Symmetry code: (i) .