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

In the title compound, C(14)H(11)FO(3)S, the unit comprising the ethanone and 4-fluoro-phenyl groups is essentially planar, with an r.m.s. deviation of 0.0084 (2) Å for the ten non-H atoms, and it makes a dihedral angle of 37.31 (10)° with the phenyl ring. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds into inversion dimers with R(2) (2)(16) graph-set motifs. The dimers are stacked along the b axis through further C-H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the chemistry of aryl­sulphones, see: Abdel-Aziz et al. (2009 ▶, 2010 ▶); Grandison et al. (2002 ▶); Silvestri et al. (2000 ▶); Stephens et al. (2001 ▶); Xiang et al. (2007 ▶). For related structures, see: Abdel-Aziz et al. (2011 ▶, 2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H11FO3S

M = 278.30

Monoclinic,

a = 13.7046 (3) Å

b = 5.3216 (1) Å

c = 20.4401 (5) Å

β = 119.612 (2)°

V = 1296.01 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.36 mm−1

T = 296 K

0.58 × 0.23 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.341, T max = 0.852

8880 measured reflections

2393 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.07

2393 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.30 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/S1600536812019666/is5133sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019666/is5133Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019666/is5133Isup3.cml

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

C14H11FO3S	F(000) = 576
Mr = 278.30	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2393 reflections
a = 13.7046 (3) Å	θ = 3.7–71.2°
b = 5.3216 (1) Å	µ = 2.36 mm−1
c = 20.4401 (5) Å	T = 296 K
β = 119.612 (2)°	Plate, colorless
V = 1296.01 (6) Å3	0.58 × 0.23 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2393 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 71.2°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.341, Tmax = 0.852	k = −5→6
8880 measured reflections	l = −24→25

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.2892P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2393 reflections	Δρmax = 0.22 e Å−3
173 parameters	Δρmin = −0.30 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: 0.0041 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.55567 (3)	0.70852 (8)	0.61500 (2)	0.04632 (18)
F1	0.96706 (13)	0.1120 (4)	0.55007 (10)	0.1107 (6)
O1	0.81880 (12)	0.9811 (3)	0.68962 (8)	0.0662 (4)
O2	0.45075 (10)	0.8367 (3)	0.58825 (8)	0.0616 (4)
O3	0.55394 (12)	0.4560 (2)	0.58997 (8)	0.0603 (4)
C1	0.63784 (15)	0.8990 (3)	0.58896 (10)	0.0492 (4)
H1A	0.6133	0.8700	0.5362	0.059*
H1B	0.6236	1.0741	0.5944	0.059*
C2	0.76418 (15)	0.8516 (4)	0.63472 (9)	0.0492 (4)
C3	0.81547 (14)	0.6528 (4)	0.61084 (9)	0.0488 (4)
C4	0.75317 (15)	0.5065 (4)	0.54707 (10)	0.0540 (4)
H4A	0.6762	0.5324	0.5178	0.065*
C5	0.80438 (17)	0.3233 (4)	0.52674 (11)	0.0630 (5)
H5A	0.7629	0.2242	0.4844	0.076*
C6	0.91764 (19)	0.2912 (5)	0.57045 (13)	0.0716 (6)
C7	0.98184 (18)	0.4289 (6)	0.63456 (13)	0.0798 (7)
H7A	1.0585	0.3991	0.6638	0.096*
C8	0.93098 (16)	0.6100 (5)	0.65444 (12)	0.0660 (6)
H8A	0.9735	0.7059	0.6974	0.079*
C9	0.62748 (14)	0.7076 (3)	0.71439 (10)	0.0470 (4)
C10	0.70719 (16)	0.5235 (4)	0.75248 (11)	0.0560 (4)
H10A	0.7222	0.4007	0.7263	0.067*
C11	0.76409 (19)	0.5262 (5)	0.83057 (12)	0.0691 (6)
H11A	0.8182	0.4049	0.8573	0.083*
C12	0.7406 (2)	0.7079 (5)	0.86849 (12)	0.0718 (6)
H12A	0.7791	0.7089	0.9208	0.086*
C13	0.6606 (2)	0.8885 (5)	0.82995 (13)	0.0733 (6)
H13A	0.6452	1.0099	0.8563	0.088*
C14	0.60266 (17)	0.8904 (4)	0.75166 (12)	0.0596 (5)
H14A	0.5485	1.0119	0.7252	0.072*

	U11	U22	U33	U12	U13	U23
S1	0.0442 (3)	0.0421 (3)	0.0460 (3)	0.00262 (16)	0.01715 (19)	−0.00338 (15)
F1	0.0781 (9)	0.1412 (15)	0.1014 (11)	0.0380 (9)	0.0356 (8)	−0.0343 (10)
O1	0.0622 (8)	0.0691 (10)	0.0584 (8)	−0.0055 (7)	0.0229 (7)	−0.0153 (7)
O2	0.0431 (6)	0.0673 (9)	0.0636 (8)	0.0067 (6)	0.0181 (6)	−0.0023 (6)
O3	0.0713 (8)	0.0437 (8)	0.0575 (8)	−0.0013 (6)	0.0253 (6)	−0.0084 (6)
C1	0.0533 (9)	0.0428 (10)	0.0480 (9)	0.0091 (7)	0.0222 (7)	0.0055 (7)
C2	0.0498 (9)	0.0508 (11)	0.0437 (9)	−0.0009 (8)	0.0207 (7)	0.0027 (7)
C3	0.0446 (8)	0.0566 (11)	0.0415 (8)	0.0032 (7)	0.0184 (7)	0.0025 (7)
C4	0.0449 (8)	0.0656 (12)	0.0445 (9)	0.0057 (8)	0.0168 (7)	−0.0008 (8)
C5	0.0577 (11)	0.0790 (15)	0.0482 (10)	0.0086 (10)	0.0229 (8)	−0.0076 (9)
C6	0.0606 (11)	0.0879 (17)	0.0655 (13)	0.0192 (11)	0.0305 (10)	−0.0078 (11)
C7	0.0468 (10)	0.109 (2)	0.0684 (13)	0.0185 (11)	0.0168 (9)	−0.0101 (13)
C8	0.0478 (10)	0.0837 (16)	0.0527 (10)	0.0038 (10)	0.0144 (8)	−0.0103 (10)
C9	0.0468 (8)	0.0465 (10)	0.0464 (9)	−0.0037 (7)	0.0221 (7)	−0.0027 (7)
C10	0.0611 (10)	0.0485 (11)	0.0540 (10)	0.0013 (8)	0.0248 (8)	0.0029 (8)
C11	0.0695 (12)	0.0637 (14)	0.0588 (12)	−0.0041 (10)	0.0200 (10)	0.0138 (10)
C12	0.0808 (15)	0.0851 (17)	0.0468 (10)	−0.0192 (12)	0.0294 (10)	−0.0010 (10)
C13	0.0826 (15)	0.0838 (17)	0.0647 (13)	−0.0155 (13)	0.0449 (12)	−0.0212 (12)
C14	0.0591 (10)	0.0609 (13)	0.0611 (11)	−0.0017 (9)	0.0314 (9)	−0.0102 (9)

S1—O2	1.4333 (13)	C6—C7	1.374 (3)
S1—O3	1.4342 (14)	C7—C8	1.364 (3)
S1—C9	1.7664 (17)	C7—H7A	0.9300
S1—C1	1.7807 (19)	C8—H8A	0.9300
F1—C6	1.349 (3)	C9—C14	1.378 (3)
O1—C2	1.210 (2)	C9—C10	1.385 (3)
C1—C2	1.528 (2)	C10—C11	1.388 (3)
C1—H1A	0.9700	C10—H10A	0.9300
C1—H1B	0.9700	C11—C12	1.374 (4)
C2—C3	1.480 (3)	C11—H11A	0.9300
C3—C4	1.391 (3)	C12—C13	1.376 (4)
C3—C8	1.399 (3)	C12—H12A	0.9300
C4—C5	1.380 (3)	C13—C14	1.391 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.366 (3)	C14—H14A	0.9300
C5—H5A	0.9300
O2—S1—O3	118.24 (9)	C5—C6—C7	122.8 (2)
O2—S1—C9	108.90 (9)	C8—C7—C6	118.70 (19)
O3—S1—C9	108.02 (8)	C8—C7—H7A	120.7
O2—S1—C1	106.18 (9)	C6—C7—H7A	120.7
O3—S1—C1	109.15 (9)	C7—C8—C3	120.62 (19)
C9—S1—C1	105.67 (8)	C7—C8—H8A	119.7
C2—C1—S1	114.57 (12)	C3—C8—H8A	119.7
C2—C1—H1A	108.6	C14—C9—C10	122.02 (18)
S1—C1—H1A	108.6	C14—C9—S1	118.98 (15)
C2—C1—H1B	108.6	C10—C9—S1	119.00 (14)
S1—C1—H1B	108.6	C9—C10—C11	118.5 (2)
H1A—C1—H1B	107.6	C9—C10—H10A	120.7
O1—C2—C3	122.41 (16)	C11—C10—H10A	120.7
O1—C2—C1	117.92 (17)	C12—C11—C10	120.1 (2)
C3—C2—C1	119.67 (15)	C12—C11—H11A	120.0
C4—C3—C8	118.88 (18)	C10—C11—H11A	120.0
C4—C3—C2	122.52 (16)	C11—C12—C13	120.8 (2)
C8—C3—C2	118.59 (17)	C11—C12—H12A	119.6
C5—C4—C3	120.65 (17)	C13—C12—H12A	119.6
C5—C4—H4A	119.7	C12—C13—C14	120.3 (2)
C3—C4—H4A	119.7	C12—C13—H13A	119.9
C6—C5—C4	118.29 (19)	C14—C13—H13A	119.9
C6—C5—H5A	120.9	C9—C14—C13	118.3 (2)
C4—C5—H5A	120.9	C9—C14—H14A	120.8
F1—C6—C5	117.9 (2)	C13—C14—H14A	120.8
F1—C6—C7	119.2 (2)
O2—S1—C1—C2	159.03 (13)	C4—C3—C8—C7	0.4 (3)
O3—S1—C1—C2	−72.49 (15)	C2—C3—C8—C7	−180.0 (2)
C9—S1—C1—C2	43.46 (15)	O2—S1—C9—C14	−23.82 (18)
S1—C1—C2—O1	−93.21 (19)	O3—S1—C9—C14	−153.41 (16)
S1—C1—C2—C3	87.07 (18)	C1—S1—C9—C14	89.87 (16)
O1—C2—C3—C4	−178.92 (19)	O2—S1—C9—C10	156.30 (15)
C1—C2—C3—C4	0.8 (3)	O3—S1—C9—C10	26.71 (18)
O1—C2—C3—C8	1.5 (3)	C1—S1—C9—C10	−90.01 (16)
C1—C2—C3—C8	−178.84 (18)	C14—C9—C10—C11	−0.6 (3)
C8—C3—C4—C5	−0.5 (3)	S1—C9—C10—C11	179.24 (15)
C2—C3—C4—C5	179.91 (18)	C9—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	−0.5 (3)	C10—C11—C12—C13	0.2 (4)
C4—C5—C6—F1	−179.9 (2)	C11—C12—C13—C14	−0.4 (4)
C4—C5—C6—C7	1.7 (4)	C10—C9—C14—C13	0.4 (3)
F1—C6—C7—C8	179.8 (3)	S1—C9—C14—C13	−179.46 (16)
C5—C6—C7—C8	−1.8 (4)	C12—C13—C14—C9	0.1 (3)
C6—C7—C8—C3	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O3i	0.97	2.23	3.183 (2)	168
C5—H5A···O2ii	0.93	2.57	3.218 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O3i	0.97	2.23	3.183 (2)	168
C5—H5A⋯O2ii	0.93	2.57	3.218 (3)	127

Symmetry codes: (i) ; (ii) .