1-(4-Methyl-phen-yl)-2-(phenyl-sulfon-yl)ethanone.

In the title compound, C(15)H(14)O(3)S, the benzene and phenyl rings make a dihedral angle of 33.56 (16)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into a layer parallel to the ab plane.

Related literature

For background to the chemistry of sulfones, see: Xiang et al. (2007 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶). For a related structure, see: Abdel-Aziz et al. (2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14O3S

M = 274.32

Orthorhombic,

a = 11.5555 (12) Å

b = 10.1981 (11) Å

c = 22.843 (2) Å

V = 2692.0 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.15 mm−1

T = 296 K

0.55 × 0.12 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.386, T max = 0.919

10168 measured reflections

2487 independent reflections

1446 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 0.89

2487 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200966X/is5087sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200966X/is5087Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200966X/is5087Isup3.cml

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

C15H14O3S	F(000) = 1152
Mr = 274.32	Dx = 1.354 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 484 reflections
a = 11.5555 (12) Å	θ = 3.9–33.7°
b = 10.1981 (11) Å	µ = 2.15 mm−1
c = 22.843 (2) Å	T = 296 K
V = 2692.0 (5) Å3	Needle, colourless
Z = 8	0.55 × 0.12 × 0.04 mm

Bruker SMART APEXII CCD area-detector diffractometer	2487 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
φ and ω scans	θmax = 70.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→14
Tmin = 0.386, Tmax = 0.919	k = −9→11
10168 measured reflections	l = −27→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0623P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max < 0.001
2487 reflections	Δρmax = 0.19 e Å−3
174 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00131 (15)

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
S1	0.69612 (6)	0.25970 (7)	0.35841 (3)	0.0496 (2)
O1	0.67330 (18)	0.12398 (18)	0.34807 (10)	0.0602 (6)
O2	0.60372 (18)	0.3428 (2)	0.37858 (10)	0.0666 (6)
O3	0.94161 (18)	0.2723 (2)	0.27397 (11)	0.0727 (7)
C1	0.8099 (2)	0.2698 (3)	0.40947 (13)	0.0498 (7)
C2	0.8117 (3)	0.3717 (3)	0.44912 (14)	0.0652 (9)
H2A	0.7562	0.4377	0.4476	0.078*
C3	0.8977 (3)	0.3739 (4)	0.49129 (15)	0.0791 (11)
H3A	0.8998	0.4410	0.5188	0.095*
C4	0.9795 (4)	0.2774 (4)	0.49242 (17)	0.0835 (12)
H4A	1.0372	0.2799	0.5208	0.100*
C5	0.9782 (3)	0.1777 (4)	0.45296 (17)	0.0797 (11)
H5A	1.0354	0.1135	0.4542	0.096*
C6	0.8919 (3)	0.1715 (3)	0.41090 (14)	0.0636 (8)
H6A	0.8894	0.1026	0.3842	0.076*
C7	0.7484 (3)	0.3314 (3)	0.29256 (12)	0.0513 (7)
H7A	0.6841	0.3433	0.2658	0.062*
H7B	0.7799	0.4174	0.3013	0.062*
C8	0.8414 (2)	0.2493 (3)	0.26254 (12)	0.0503 (7)
C9	0.8077 (2)	0.1467 (3)	0.22005 (12)	0.0459 (6)
C10	0.6939 (2)	0.1183 (3)	0.20632 (13)	0.0520 (7)
H10A	0.6344	0.1646	0.2243	0.062*
C11	0.6681 (3)	0.0219 (3)	0.16615 (13)	0.0575 (8)
H11A	0.5910	0.0031	0.1580	0.069*
C12	0.7533 (3)	−0.0470 (3)	0.13781 (13)	0.0559 (7)
C13	0.8667 (3)	−0.0200 (3)	0.15236 (14)	0.0576 (8)
H13A	0.9258	−0.0669	0.1344	0.069*
C14	0.8942 (2)	0.0743 (3)	0.19262 (13)	0.0549 (7)
H14A	0.9714	0.0902	0.2017	0.066*
C15	0.7230 (3)	−0.1491 (3)	0.09252 (15)	0.0753 (10)
H15B	0.6483	−0.1854	0.1012	0.113*
H15C	0.7799	−0.2176	0.0931	0.113*
H15A	0.7214	−0.1093	0.0545	0.113*

	U11	U22	U33	U12	U13	U23
S1	0.0458 (4)	0.0490 (4)	0.0540 (4)	−0.0012 (3)	0.0010 (3)	−0.0013 (3)
O1	0.0659 (14)	0.0448 (12)	0.0700 (14)	−0.0143 (9)	−0.0041 (11)	−0.0014 (10)
O2	0.0541 (13)	0.0746 (16)	0.0710 (15)	0.0124 (10)	0.0071 (11)	−0.0079 (11)
O3	0.0480 (13)	0.0813 (17)	0.0887 (17)	−0.0041 (11)	−0.0105 (12)	−0.0201 (13)
C1	0.0506 (17)	0.0480 (17)	0.0509 (15)	−0.0049 (13)	0.0002 (13)	0.0035 (12)
C2	0.078 (2)	0.057 (2)	0.0599 (19)	−0.0065 (16)	−0.0027 (18)	−0.0040 (15)
C3	0.093 (3)	0.084 (3)	0.061 (2)	−0.024 (2)	−0.007 (2)	−0.0066 (19)
C4	0.074 (3)	0.114 (4)	0.062 (2)	−0.018 (2)	−0.0189 (19)	0.023 (2)
C5	0.067 (2)	0.094 (3)	0.078 (3)	0.006 (2)	−0.007 (2)	0.018 (2)
C6	0.0573 (19)	0.065 (2)	0.068 (2)	0.0057 (15)	−0.0047 (17)	0.0045 (16)
C7	0.0611 (18)	0.0432 (17)	0.0495 (16)	0.0030 (13)	−0.0005 (14)	0.0020 (12)
C8	0.0482 (17)	0.0517 (17)	0.0508 (16)	0.0008 (13)	−0.0023 (13)	0.0039 (13)
C9	0.0421 (15)	0.0466 (16)	0.0491 (15)	0.0022 (11)	0.0002 (13)	0.0034 (12)
C10	0.0408 (15)	0.0613 (18)	0.0540 (17)	0.0053 (13)	0.0030 (14)	0.0020 (13)
C11	0.0465 (18)	0.066 (2)	0.0599 (18)	−0.0071 (14)	−0.0064 (15)	0.0013 (15)
C12	0.0628 (19)	0.0579 (18)	0.0471 (15)	−0.0022 (14)	−0.0031 (16)	0.0031 (14)
C13	0.0544 (19)	0.0594 (19)	0.0590 (18)	0.0086 (13)	0.0040 (16)	−0.0045 (15)
C14	0.0412 (16)	0.0636 (19)	0.0599 (18)	0.0035 (13)	−0.0013 (14)	−0.0034 (14)
C15	0.093 (3)	0.071 (2)	0.061 (2)	−0.0040 (18)	−0.0110 (19)	−0.0085 (17)

S1—O1	1.4287 (19)	C7—H7A	0.9700
S1—O2	1.439 (2)	C7—H7B	0.9700
S1—C1	1.760 (3)	C8—C9	1.480 (4)
S1—C7	1.778 (3)	C9—C10	1.382 (4)
O3—C8	1.210 (3)	C9—C14	1.391 (4)
C1—C2	1.379 (4)	C10—C11	1.377 (4)
C1—C6	1.380 (4)	C10—H10A	0.9300
C2—C3	1.385 (4)	C11—C12	1.373 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.364 (5)	C12—C13	1.379 (4)
C3—H3A	0.9300	C12—C15	1.509 (4)
C4—C5	1.359 (5)	C13—C14	1.368 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.386 (5)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15B	0.9600
C6—H6A	0.9300	C15—H15C	0.9600
C7—C8	1.525 (4)	C15—H15A	0.9600
O1—S1—O2	119.10 (13)	H7A—C7—H7B	107.7
O1—S1—C1	107.69 (13)	O3—C8—C9	122.0 (3)
O2—S1—C1	107.92 (14)	O3—C8—C7	118.1 (3)
O1—S1—C7	108.74 (14)	C9—C8—C7	119.9 (2)
O2—S1—C7	106.32 (14)	C10—C9—C14	118.0 (3)
C1—S1—C7	106.42 (14)	C10—C9—C8	123.2 (3)
C2—C1—C6	121.4 (3)	C14—C9—C8	118.8 (3)
C2—C1—S1	119.4 (2)	C11—C10—C9	120.4 (3)
C6—C1—S1	119.1 (2)	C11—C10—H10A	119.8
C1—C2—C3	118.7 (3)	C9—C10—H10A	119.8
C1—C2—H2A	120.7	C12—C11—C10	121.6 (3)
C3—C2—H2A	120.7	C12—C11—H11A	119.2
C4—C3—C2	119.9 (4)	C10—C11—H11A	119.2
C4—C3—H3A	120.0	C11—C12—C13	117.7 (3)
C2—C3—H3A	120.0	C11—C12—C15	120.7 (3)
C5—C4—C3	121.3 (4)	C13—C12—C15	121.6 (3)
C5—C4—H4A	119.3	C14—C13—C12	121.5 (3)
C3—C4—H4A	119.3	C14—C13—H13A	119.2
C4—C5—C6	120.1 (4)	C12—C13—H13A	119.2
C4—C5—H5A	120.0	C13—C14—C9	120.6 (3)
C6—C5—H5A	120.0	C13—C14—H14A	119.7
C1—C6—C5	118.5 (3)	C9—C14—H14A	119.7
C1—C6—H6A	120.7	C12—C15—H15B	109.5
C5—C6—H6A	120.7	C12—C15—H15C	109.5
C8—C7—S1	113.21 (19)	H15B—C15—H15C	109.5
C8—C7—H7A	108.9	C12—C15—H15A	109.5
S1—C7—H7A	108.9	H15B—C15—H15A	109.5
C8—C7—H7B	108.9	H15C—C15—H15A	109.5
S1—C7—H7B	108.9
O1—S1—C1—C2	−146.6 (2)	S1—C7—C8—O3	−92.6 (3)
O2—S1—C1—C2	−16.8 (3)	S1—C7—C8—C9	88.4 (3)
C7—S1—C1—C2	97.0 (3)	O3—C8—C9—C10	179.8 (3)
O1—S1—C1—C6	30.0 (3)	C7—C8—C9—C10	−1.2 (4)
O2—S1—C1—C6	159.8 (2)	O3—C8—C9—C14	0.2 (4)
C7—S1—C1—C6	−86.4 (3)	C7—C8—C9—C14	179.1 (3)
C6—C1—C2—C3	−0.4 (5)	C14—C9—C10—C11	−0.6 (4)
S1—C1—C2—C3	176.1 (2)	C8—C9—C10—C11	179.7 (3)
C1—C2—C3—C4	1.0 (5)	C9—C10—C11—C12	−1.2 (5)
C2—C3—C4—C5	−0.4 (6)	C10—C11—C12—C13	2.3 (5)
C3—C4—C5—C6	−0.8 (6)	C10—C11—C12—C15	−178.0 (3)
C2—C1—C6—C5	−0.8 (5)	C11—C12—C13—C14	−1.5 (5)
S1—C1—C6—C5	−177.3 (3)	C15—C12—C13—C14	178.7 (3)
C4—C5—C6—C1	1.4 (5)	C12—C13—C14—C9	−0.3 (5)
O1—S1—C7—C8	−46.2 (3)	C10—C9—C14—C13	1.4 (4)
O2—S1—C7—C8	−175.5 (2)	C8—C9—C14—C13	−178.9 (3)
C1—S1—C7—C8	69.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1i	0.97	2.42	3.366 (3)	164
C10—H10A···O3ii	0.93	2.48	3.342 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.97	2.42	3.366 (3)	164
C10—H10A⋯O3ii	0.93	2.48	3.342 (4)	154

Symmetry codes: (i) ; (ii) .