5-Fluoro-3-(3-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)F(2)O(3)S, the 3-fluoro-phenyl ring makes a dihedral angle of 79.51 (6)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯F and C-H⋯O hydrogen bonds. The crystal structure also exhibits slipped π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distances = 3.563 (3) and 3.820 (3) Å and slippages of 0.358 (3)and 1.551 (3) Å]. In the 3-fluoro-phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.887 (3) and 0.113 (3).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C15H10F2O3S

M = 308.29

Monoclinic,

a = 7.2772 (2) Å

b = 11.0972 (3) Å

c = 16.5625 (5) Å

β = 100.698 (2)°

V = 1314.28 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.663, T max = 0.746

12792 measured reflections

3275 independent reflections

2732 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.04

3275 reflections

202 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031972/pk2432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031972/pk2432Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031972/pk2432Isup3.cml

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

C15H10F2O3S	F(000) = 632
Mr = 308.29	Dx = 1.558 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3933 reflections
a = 7.2772 (2) Å	θ = 2.2–28.2°
b = 11.0972 (3) Å	µ = 0.28 mm−1
c = 16.5625 (5) Å	T = 296 K
β = 100.698 (2)°	Block, colourless
V = 1314.28 (6) Å3	0.30 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3275 independent reflections
Radiation source: rotating anode	2732 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.663, Tmax = 0.746	l = −22→22
12792 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.3108P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3275 reflections	Δρmax = 0.36 e Å−3
202 parameters	Δρmin = −0.31 e Å−3
14 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (14)

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	Occ. (<1)
S1	0.21640 (5)	0.63440 (3)	0.70540 (2)	0.03087 (13)
F1	0.25059 (17)	0.17801 (10)	0.54399 (7)	0.0617 (3)
O1	0.25258 (16)	0.65312 (11)	0.47256 (7)	0.0437 (3)
O2	0.13169 (15)	0.52825 (10)	0.73181 (7)	0.0373 (3)
O3	0.13613 (15)	0.75027 (10)	0.71521 (7)	0.0407 (3)
C1	0.2307 (2)	0.61487 (14)	0.60279 (9)	0.0324 (3)
C2	0.24256 (19)	0.49996 (14)	0.56282 (9)	0.0323 (3)
C3	0.2414 (2)	0.37946 (15)	0.58555 (10)	0.0375 (4)
H3	0.2332	0.3559	0.6387	0.045*
C4	0.2532 (2)	0.29710 (17)	0.52459 (11)	0.0437 (4)
C5	0.2648 (2)	0.32726 (19)	0.44430 (11)	0.0491 (5)
H5	0.2715	0.2671	0.4059	0.059*
C6	0.2664 (2)	0.44598 (18)	0.42199 (10)	0.0456 (4)
H6	0.2745	0.4688	0.3687	0.055*
C7	0.2553 (2)	0.53018 (16)	0.48228 (9)	0.0369 (4)
C8	0.2376 (2)	0.70287 (16)	0.54652 (10)	0.0391 (4)
C9	0.2333 (3)	0.83607 (17)	0.54796 (12)	0.0547 (5)
H9A	0.2265	0.8632	0.6024	0.082*
H9B	0.1259	0.8644	0.5101	0.082*
H9C	0.3449	0.8671	0.5324	0.082*
C10	0.4518 (2)	0.63802 (13)	0.75603 (9)	0.0298 (3)
C11	0.5530 (2)	0.74450 (14)	0.75670 (10)	0.0375 (3)
H11	0.4957	0.8143	0.7332	0.045*
C12	0.7390 (2)	0.74468 (16)	0.79277 (11)	0.0420 (4)	0.887 (3)
H12	0.8083	0.8150	0.7925	0.050*	0.887 (3)
C12'	0.7390 (2)	0.74468 (16)	0.79277 (11)	0.0420 (4)	0.11
F2'	0.8472 (11)	0.8379 (6)	0.8099 (5)	0.042 (3)	0.113 (3)
C13	0.8244 (2)	0.64277 (16)	0.82925 (10)	0.0409 (4)
H13	0.9504	0.6434	0.8535	0.049*
C14	0.7198 (2)	0.54100 (15)	0.82885 (10)	0.0402 (4)	0.887 (3)
F2	0.80371 (19)	0.44337 (11)	0.86633 (8)	0.0619 (4)	0.887 (3)
C14'	0.7198 (2)	0.54100 (15)	0.82885 (10)	0.0402 (4)	0.11
H14'	0.7770	0.4726	0.8546	0.048*	0.113 (3)
C15	0.5338 (2)	0.53388 (14)	0.79236 (9)	0.0354 (3)
H15	0.4666	0.4626	0.7921	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0314 (2)	0.0312 (2)	0.0326 (2)	0.00158 (14)	0.01275 (15)	−0.00048 (14)
F1	0.0746 (8)	0.0435 (6)	0.0622 (7)	0.0073 (6)	−0.0001 (6)	−0.0119 (5)
O1	0.0432 (7)	0.0576 (8)	0.0303 (6)	−0.0037 (5)	0.0070 (5)	0.0065 (5)
O2	0.0380 (6)	0.0387 (6)	0.0384 (6)	−0.0052 (5)	0.0158 (5)	−0.0007 (5)
O3	0.0392 (6)	0.0379 (6)	0.0478 (7)	0.0076 (5)	0.0157 (5)	−0.0022 (5)
C1	0.0281 (7)	0.0384 (8)	0.0318 (7)	0.0015 (6)	0.0084 (6)	0.0008 (6)
C2	0.0227 (7)	0.0446 (9)	0.0293 (7)	0.0015 (6)	0.0044 (5)	−0.0022 (6)
C3	0.0337 (8)	0.0431 (9)	0.0347 (8)	0.0026 (6)	0.0040 (6)	−0.0033 (6)
C4	0.0373 (9)	0.0446 (10)	0.0459 (9)	0.0041 (7)	−0.0007 (7)	−0.0090 (7)
C5	0.0390 (9)	0.0659 (13)	0.0404 (9)	0.0022 (8)	0.0023 (7)	−0.0205 (9)
C6	0.0346 (8)	0.0720 (13)	0.0296 (8)	−0.0023 (8)	0.0046 (6)	−0.0066 (8)
C7	0.0265 (7)	0.0530 (10)	0.0306 (7)	−0.0012 (6)	0.0044 (6)	0.0004 (7)
C8	0.0342 (8)	0.0475 (10)	0.0360 (8)	0.0008 (7)	0.0072 (6)	0.0050 (7)
C9	0.0671 (13)	0.0459 (11)	0.0512 (11)	−0.0017 (9)	0.0116 (9)	0.0113 (8)
C10	0.0329 (7)	0.0301 (7)	0.0287 (7)	0.0007 (6)	0.0117 (6)	−0.0034 (5)
C11	0.0417 (8)	0.0307 (8)	0.0419 (8)	−0.0004 (6)	0.0126 (7)	0.0003 (6)
C12	0.0406 (9)	0.0416 (9)	0.0457 (9)	−0.0081 (7)	0.0131 (7)	−0.0085 (7)
C12'	0.0406 (9)	0.0416 (9)	0.0457 (9)	−0.0081 (7)	0.0131 (7)	−0.0085 (7)
F2'	0.038 (4)	0.041 (5)	0.048 (5)	−0.014 (3)	0.013 (3)	−0.005 (3)
C13	0.0344 (8)	0.0540 (10)	0.0345 (8)	0.0003 (7)	0.0072 (6)	−0.0090 (7)
C14	0.0445 (9)	0.0409 (9)	0.0348 (8)	0.0089 (7)	0.0065 (7)	0.0014 (7)
F2	0.0601 (8)	0.0469 (8)	0.0715 (9)	0.0124 (6)	−0.0070 (7)	0.0121 (6)
C14'	0.0445 (9)	0.0409 (9)	0.0348 (8)	0.0089 (7)	0.0065 (7)	0.0014 (7)
C15	0.0416 (8)	0.0303 (8)	0.0355 (8)	−0.0009 (6)	0.0103 (6)	−0.0006 (6)

S1—O3	1.4339 (11)	C6—H6	0.9300
S1—O2	1.4349 (11)	C8—C9	1.479 (2)
S1—C1	1.7354 (15)	C9—H9A	0.9600
S1—C10	1.7627 (16)	C9—H9B	0.9600
F1—C4	1.361 (2)	C9—H9C	0.9600
O1—C8	1.366 (2)	C10—C15	1.386 (2)
O1—C7	1.374 (2)	C10—C11	1.391 (2)
C1—C8	1.357 (2)	C11—C12	1.374 (2)
C1—C2	1.447 (2)	C11—H11	0.9300
C2—C3	1.390 (2)	C12—C13	1.375 (2)
C2—C7	1.395 (2)	C12—H12	0.9300
C3—C4	1.376 (2)	C13—C14	1.361 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.389 (3)	C14—F2	1.3383 (19)
C5—C6	1.369 (3)	C14—C15	1.378 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.381 (2)
O3—S1—O2	119.64 (7)	C1—C8—O1	110.14 (15)
O3—S1—C1	108.82 (7)	C1—C8—C9	134.79 (16)
O2—S1—C1	107.65 (7)	O1—C8—C9	115.07 (15)
O3—S1—C10	107.83 (7)	C8—C9—H9A	109.5
O2—S1—C10	107.96 (7)	C8—C9—H9B	109.5
C1—S1—C10	103.84 (7)	H9A—C9—H9B	109.5
C8—O1—C7	107.34 (12)	C8—C9—H9C	109.5
C8—C1—C2	107.87 (13)	H9A—C9—H9C	109.5
C8—C1—S1	126.82 (13)	H9B—C9—H9C	109.5
C2—C1—S1	125.29 (11)	C15—C10—C11	121.37 (15)
C3—C2—C7	119.67 (15)	C15—C10—S1	119.32 (12)
C3—C2—C1	136.08 (14)	C11—C10—S1	119.29 (12)
C7—C2—C1	104.24 (14)	C12—C11—C10	118.79 (15)
C4—C3—C2	115.85 (15)	C12—C11—H11	120.6
C4—C3—H3	122.1	C10—C11—H11	120.6
C2—C3—H3	122.1	C11—C12—C13	121.22 (16)
F1—C4—C3	117.79 (16)	C11—C12—H12	119.4
F1—C4—C5	117.77 (16)	C13—C12—H12	119.4
C3—C4—C5	124.43 (18)	C14—C13—C12	118.25 (16)
C6—C5—C4	119.70 (16)	C14—C13—H13	120.9
C6—C5—H5	120.2	C12—C13—H13	120.9
C4—C5—H5	120.2	F2—C14—C13	117.58 (16)
C5—C6—C7	116.84 (16)	F2—C14—C15	118.89 (16)
C5—C6—H6	121.6	C13—C14—C15	123.53 (15)
C7—C6—H6	121.6	C14—C15—C10	116.82 (15)
O1—C7—C6	126.08 (15)	C14—C15—H15	121.6
O1—C7—C2	110.41 (14)	C10—C15—H15	121.6
C6—C7—C2	123.51 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F2i	0.93	2.45	3.302 (2)	153
C15—H15···O3ii	0.93	2.47	3.3754 (19)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F2i	0.93	2.45	3.302 (2)	153
C15—H15⋯O3ii	0.93	2.47	3.3754 (19)	165

Symmetry codes: (i) ; (ii) .