1-(3-Meth-oxy-phen-yl)-2-(phenyl-sulfon-yl)ethan-1-one.

In the title compound, C(15)H(14)O(4)S, the dihedral angle between the benzene and phenyl rings is 88.74 (10)°. In the crystal, mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distances = 3.6092 (13)-3.8651 (13) Å].

Related literature

For the biological activity of sulfone compounds, see: Dawood et al. (2010 ▶); Suryakiran et al. (2007 ▶); Siddiq et al. (2005 ▶); Lai et al. (2005 ▶). For related structures, see: Yousuf et al. (2012 ▶); Billing et al. (2006 ▶); Pei et al. (2005 ▶); Gu et al. (2004 ▶).

Experimental

Crystal data

C15H14O4S

M = 290.32

Triclinic,

a = 7.1290 (6) Å

b = 9.6101 (8) Å

c = 10.6999 (9) Å

α = 101.787 (2)°

β = 102.550 (2)°

γ = 95.879 (2)°

V = 692.13 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.30 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.931, T max = 0.983

7866 measured reflections

2577 independent reflections

2135 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.108

S = 1.06

2577 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032795/rz2794sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032795/rz2794Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032795/rz2794Isup3.cml

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

C15H14O4S	Z = 2
Mr = 290.32	F(000) = 304
Triclinic, P1	Dx = 1.393 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1290 (6) Å	Cell parameters from 2142 reflections
b = 9.6101 (8) Å	θ = 2.2–24.2°
c = 10.6999 (9) Å	µ = 0.24 mm−1
α = 101.787 (2)°	T = 298 K
β = 102.550 (2)°	Plate, colourless
γ = 95.879 (2)°	0.30 × 0.12 × 0.07 mm
V = 692.13 (10) Å3

Bruker SMART APEX CCD area-detector diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2135 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.931, Tmax = 0.983	k = −11→11
7866 measured reflections	l = −12→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.113P] where P = (Fo2 + 2Fc2)/3
2577 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 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
S1	0.22994 (8)	0.83326 (5)	0.47049 (5)	0.04481 (19)
O1	0.4151 (2)	0.78524 (16)	0.49651 (15)	0.0599 (4)
O2	0.1737 (2)	0.91873 (16)	0.57906 (14)	0.0597 (4)
O3	0.2985 (3)	0.75030 (17)	0.20387 (17)	0.0726 (5)
O4	0.2706 (3)	1.33137 (17)	0.10446 (16)	0.0669 (5)
C1	−0.1457 (3)	0.7024 (2)	0.3856 (2)	0.0519 (5)
H1B	−0.1776	0.7931	0.4136	0.062*
C2	−0.2891 (3)	0.5848 (3)	0.3324 (2)	0.0608 (6)
H2B	−0.4189	0.5960	0.3243	0.073*
C3	−0.2412 (4)	0.4505 (3)	0.2909 (2)	0.0600 (6)
H3A	−0.3387	0.3714	0.2556	0.072*
C4	−0.0507 (4)	0.4333 (2)	0.3017 (2)	0.0579 (6)
H4A	−0.0194	0.3424	0.2736	0.069*
C5	0.0956 (3)	0.5502 (2)	0.3541 (2)	0.0489 (5)
H5A	0.2251	0.5388	0.3605	0.059*
C6	0.0467 (3)	0.6838 (2)	0.39682 (18)	0.0411 (5)
C7	0.2252 (3)	0.9421 (2)	0.35511 (19)	0.0432 (5)
H7A	0.0977	0.9713	0.3363	0.052*
H7B	0.3193	1.0286	0.3958	0.052*
C8	0.2679 (3)	0.8732 (2)	0.2256 (2)	0.0462 (5)
C9	0.2659 (3)	0.9613 (2)	0.12651 (19)	0.0411 (5)
C10	0.2567 (3)	0.8914 (2)	−0.0027 (2)	0.0469 (5)
H10A	0.2537	0.7923	−0.0250	0.056*
C11	0.2523 (3)	0.9691 (3)	−0.0966 (2)	0.0520 (6)
H11A	0.2465	0.9222	−0.1828	0.062*
C12	0.2562 (3)	1.1161 (3)	−0.0658 (2)	0.0506 (5)
H12A	0.2527	1.1676	−0.1308	0.061*
C13	0.2653 (3)	1.1867 (2)	0.0624 (2)	0.0462 (5)
C14	0.2706 (3)	1.1092 (2)	0.1588 (2)	0.0444 (5)
H14A	0.2773	1.1564	0.2450	0.053*
C15	0.2437 (5)	1.4133 (3)	0.0078 (3)	0.0859 (9)
H15A	0.2509	1.5127	0.0498	0.129*
H15B	0.1186	1.3794	−0.0523	0.129*
H15C	0.3434	1.4033	−0.0395	0.129*

	U11	U22	U33	U12	U13	U23
S1	0.0551 (3)	0.0411 (3)	0.0331 (3)	0.0025 (2)	0.0064 (2)	0.0042 (2)
O1	0.0535 (9)	0.0548 (10)	0.0617 (10)	0.0037 (7)	−0.0026 (7)	0.0119 (8)
O2	0.0897 (12)	0.0524 (9)	0.0327 (8)	0.0070 (8)	0.0155 (8)	0.0016 (7)
O3	0.1229 (16)	0.0439 (10)	0.0609 (11)	0.0186 (10)	0.0449 (10)	0.0079 (8)
O4	0.0959 (13)	0.0517 (10)	0.0565 (10)	0.0158 (9)	0.0211 (9)	0.0156 (8)
C1	0.0570 (14)	0.0500 (13)	0.0490 (13)	0.0111 (11)	0.0152 (10)	0.0088 (10)
C2	0.0487 (13)	0.0663 (16)	0.0661 (16)	0.0063 (12)	0.0135 (11)	0.0141 (13)
C3	0.0601 (15)	0.0551 (14)	0.0585 (15)	−0.0078 (11)	0.0097 (12)	0.0125 (11)
C4	0.0695 (16)	0.0400 (12)	0.0620 (15)	0.0043 (11)	0.0178 (12)	0.0071 (11)
C5	0.0520 (12)	0.0441 (12)	0.0503 (13)	0.0053 (10)	0.0160 (10)	0.0077 (10)
C6	0.0506 (12)	0.0410 (11)	0.0317 (10)	0.0041 (9)	0.0116 (9)	0.0084 (8)
C7	0.0530 (12)	0.0370 (11)	0.0372 (11)	0.0017 (9)	0.0128 (9)	0.0041 (9)
C8	0.0522 (12)	0.0428 (12)	0.0421 (12)	0.0022 (10)	0.0175 (10)	0.0029 (9)
C9	0.0354 (10)	0.0471 (12)	0.0380 (11)	0.0028 (9)	0.0109 (8)	0.0035 (9)
C10	0.0464 (12)	0.0487 (12)	0.0402 (11)	0.0018 (10)	0.0117 (9)	0.0000 (9)
C11	0.0475 (12)	0.0672 (16)	0.0345 (11)	0.0034 (11)	0.0083 (9)	0.0011 (10)
C12	0.0452 (12)	0.0674 (15)	0.0403 (12)	0.0072 (11)	0.0094 (9)	0.0167 (11)
C13	0.0437 (11)	0.0486 (13)	0.0464 (12)	0.0070 (9)	0.0121 (9)	0.0102 (10)
C14	0.0462 (11)	0.0493 (12)	0.0371 (11)	0.0070 (9)	0.0143 (9)	0.0045 (9)
C15	0.127 (3)	0.0563 (17)	0.0755 (19)	0.0147 (17)	0.0154 (17)	0.0275 (14)

S1—O1	1.4317 (16)	C7—C8	1.517 (3)
S1—O2	1.4371 (15)	C7—H7A	0.9700
S1—C6	1.760 (2)	C7—H7B	0.9700
S1—C7	1.771 (2)	C8—C9	1.485 (3)
O3—C8	1.208 (2)	C9—C14	1.388 (3)
O4—C13	1.365 (3)	C9—C10	1.393 (3)
O4—C15	1.415 (3)	C10—C11	1.366 (3)
C1—C2	1.376 (3)	C10—H10A	0.9300
C1—C6	1.384 (3)	C11—C12	1.379 (3)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.379 (3)	C12—C13	1.385 (3)
C2—H2B	0.9300	C12—H12A	0.9300
C3—C4	1.368 (3)	C13—C14	1.386 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.383 (3)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.379 (3)	C15—H15C	0.9600
C5—H5A	0.9300
O1—S1—O2	117.84 (10)	S1—C7—H7B	108.3
O1—S1—C6	109.38 (10)	H7A—C7—H7B	107.4
O2—S1—C6	108.11 (10)	O3—C8—C9	121.74 (19)
O1—S1—C7	109.20 (10)	O3—C8—C7	120.8 (2)
O2—S1—C7	104.93 (9)	C9—C8—C7	117.46 (18)
C6—S1—C7	106.79 (9)	C14—C9—C10	119.73 (19)
C13—O4—C15	117.60 (19)	C14—C9—C8	122.06 (18)
C2—C1—C6	119.1 (2)	C10—C9—C8	118.21 (18)
C2—C1—H1B	120.5	C11—C10—C9	119.7 (2)
C6—C1—H1B	120.5	C11—C10—H10A	120.2
C1—C2—C3	120.3 (2)	C9—C10—H10A	120.2
C1—C2—H2B	119.9	C10—C11—C12	121.1 (2)
C3—C2—H2B	119.9	C10—C11—H11A	119.5
C4—C3—C2	120.2 (2)	C12—C11—H11A	119.5
C4—C3—H3A	119.9	C11—C12—C13	119.7 (2)
C2—C3—H3A	119.9	C11—C12—H12A	120.2
C3—C4—C5	120.4 (2)	C13—C12—H12A	120.2
C3—C4—H4A	119.8	O4—C13—C12	124.9 (2)
C5—C4—H4A	119.8	O4—C13—C14	115.31 (19)
C6—C5—C4	119.0 (2)	C12—C13—C14	119.8 (2)
C6—C5—H5A	120.5	C13—C14—C9	119.98 (19)
C4—C5—H5A	120.5	C13—C14—H14A	120.0
C5—C6—C1	121.0 (2)	C9—C14—H14A	120.0
C5—C6—S1	120.11 (16)	O4—C15—H15A	109.5
C1—C6—S1	118.89 (16)	O4—C15—H15B	109.5
C8—C7—S1	115.89 (15)	H15A—C15—H15B	109.5
C8—C7—H7A	108.3	O4—C15—H15C	109.5
S1—C7—H7A	108.3	H15A—C15—H15C	109.5
C8—C7—H7B	108.3	H15B—C15—H15C	109.5
C6—C1—C2—C3	0.0 (3)	S1—C7—C8—C9	−179.81 (14)
C1—C2—C3—C4	−0.4 (4)	O3—C8—C9—C14	−166.6 (2)
C2—C3—C4—C5	0.0 (4)	C7—C8—C9—C14	14.8 (3)
C3—C4—C5—C6	0.8 (3)	O3—C8—C9—C10	14.1 (3)
C4—C5—C6—C1	−1.2 (3)	C7—C8—C9—C10	−164.46 (18)
C4—C5—C6—S1	177.26 (16)	C14—C9—C10—C11	−0.1 (3)
C2—C1—C6—C5	0.8 (3)	C8—C9—C10—C11	179.21 (18)
C2—C1—C6—S1	−177.68 (17)	C9—C10—C11—C12	−0.2 (3)
O1—S1—C6—C5	−10.3 (2)	C10—C11—C12—C13	0.2 (3)
O2—S1—C6—C5	−139.83 (17)	C15—O4—C13—C12	7.2 (3)
C7—S1—C6—C5	107.72 (18)	C15—O4—C13—C14	−173.1 (2)
O1—S1—C6—C1	168.16 (16)	C11—C12—C13—O4	179.8 (2)
O2—S1—C6—C1	38.66 (18)	C11—C12—C13—C14	0.0 (3)
C7—S1—C6—C1	−73.79 (18)	O4—C13—C14—C9	179.97 (18)
O1—S1—C7—C8	56.31 (17)	C12—C13—C14—C9	−0.3 (3)
O2—S1—C7—C8	−176.48 (15)	C10—C9—C14—C13	0.3 (3)
C6—S1—C7—C8	−61.87 (17)	C8—C9—C14—C13	−178.97 (18)
S1—C7—C8—O3	1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.97	2.54	3.411 (3)	149
C7—H7B···O1ii	0.97	2.37	3.334 (3)	171
C11—H11A···O2iii	0.93	2.48	3.317 (3)	150
C15—H15A···O3iv	0.96	2.47	3.413 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.97	2.54	3.411 (3)	149
C7—H7B⋯O1ii	0.97	2.37	3.334 (3)	171
C11—H11A⋯O2iii	0.93	2.48	3.317 (3)	150
C15—H15A⋯O3iv	0.96	2.47	3.413 (3)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .