5-Fluoro-3-(4-fluoro-phenyl-sulfin-yl)-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)F(2)O(2)S, the S=O and the 4-fluoro-phenyl groups are located on opposite sides of the plane of benzofuran ring system, and the 4-fluoro-phenyl ring is nearly perpendicular to the benzofuran plane with a dihedral angle of 89.93 (4)°. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonding and C-H⋯π inter-actions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran deriv­atives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C15H10F2O2S

M = 292.29

Orthorhombic,

a = 14.9369 (4) Å

b = 10.6284 (3) Å

c = 16.1532 (4) Å

V = 2564.41 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 174 K

0.40 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.898, T max = 0.927

22576 measured reflections

2962 independent reflections

2578 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.091

S = 1.08

2962 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.32 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 datablocks global, I. DOI: 10.1107/S1600536810021823/xu2777sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021823/xu2777Isup2.hkl

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

C15H10F2O2S	F(000) = 1200
Mr = 292.29	Dx = 1.514 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9962 reflections
a = 14.9369 (4) Å	θ = 2.4–27.6°
b = 10.6284 (3) Å	µ = 0.27 mm−1
c = 16.1532 (4) Å	T = 174 K
V = 2564.41 (12) Å3	Block, colourless
Z = 8	0.40 × 0.32 × 0.28 mm

Bruker SMART APEXII CCD diffractometer	2962 independent reflections
Radiation source: rotating anode	2578 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.4°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→11
Tmin = 0.898, Tmax = 0.927	l = −18→21
22576 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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.984P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2962 reflections	Δρmax = 0.29 e Å−3
183 parameters	Δρmin = −0.32 e Å−3
0 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: 0.0035 (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	0.66618 (2)	0.39412 (3)	0.07071 (2)	0.02868 (12)
F1	0.74089 (8)	0.39246 (10)	0.42659 (5)	0.0468 (3)
F2	0.43716 (7)	0.81769 (9)	0.16672 (7)	0.0533 (3)
O1	0.59409 (7)	0.09156 (9)	0.19275 (6)	0.0308 (2)
O2	0.76049 (7)	0.43398 (11)	0.08603 (7)	0.0371 (3)
C1	0.63924 (9)	0.27918 (12)	0.14445 (8)	0.0257 (3)
C2	0.65824 (8)	0.27675 (12)	0.23194 (8)	0.0244 (3)
C3	0.69806 (9)	0.35842 (13)	0.28866 (9)	0.0287 (3)
H3	0.7198	0.4390	0.2730	0.034*
C4	0.70389 (10)	0.31507 (14)	0.36869 (9)	0.0317 (3)
C5	0.67501 (10)	0.19769 (15)	0.39509 (9)	0.0334 (3)
H5	0.6817	0.1735	0.4514	0.040*
C6	0.63635 (10)	0.11614 (13)	0.33859 (9)	0.0318 (3)
H6	0.6159	0.0350	0.3544	0.038*
C7	0.62909 (8)	0.15881 (12)	0.25823 (8)	0.0265 (3)
C8	0.60257 (9)	0.16619 (13)	0.12435 (9)	0.0287 (3)
C9	0.57225 (10)	0.11157 (15)	0.04501 (10)	0.0379 (4)
H9A	0.5068	0.1058	0.0448	0.057*
H9B	0.5979	0.0273	0.0384	0.057*
H9C	0.5919	0.1654	−0.0008	0.057*
C10	0.59618 (9)	0.51953 (13)	0.10727 (8)	0.0275 (3)
C11	0.50426 (10)	0.50221 (15)	0.11532 (10)	0.0354 (3)
H11	0.4786	0.4215	0.1066	0.043*
C12	0.45059 (10)	0.60330 (15)	0.13609 (11)	0.0401 (4)
H12	0.3877	0.5934	0.1423	0.048*
C13	0.49058 (11)	0.71859 (14)	0.14756 (10)	0.0364 (3)
C14	0.58090 (11)	0.73846 (14)	0.13999 (10)	0.0391 (4)
H14	0.6061	0.8195	0.1488	0.047*
C15	0.63445 (10)	0.63648 (14)	0.11909 (9)	0.0342 (3)
H15	0.6972	0.6471	0.1129	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.03005 (19)	0.0329 (2)	0.02308 (18)	0.00313 (13)	−0.00015 (12)	0.00211 (12)
F1	0.0588 (6)	0.0527 (6)	0.0289 (5)	−0.0174 (5)	−0.0098 (4)	−0.0059 (4)
F2	0.0614 (6)	0.0369 (5)	0.0617 (7)	0.0204 (5)	0.0077 (5)	0.0049 (5)
O1	0.0328 (5)	0.0259 (5)	0.0338 (5)	−0.0047 (4)	−0.0004 (4)	−0.0046 (4)
O2	0.0271 (5)	0.0422 (6)	0.0421 (6)	0.0011 (4)	0.0044 (4)	0.0098 (5)
C1	0.0250 (6)	0.0265 (6)	0.0257 (6)	0.0018 (5)	−0.0009 (5)	−0.0013 (5)
C2	0.0227 (6)	0.0250 (6)	0.0256 (6)	0.0021 (5)	0.0002 (5)	−0.0009 (5)
C3	0.0305 (7)	0.0261 (6)	0.0294 (7)	−0.0034 (5)	−0.0007 (5)	−0.0014 (5)
C4	0.0312 (7)	0.0363 (7)	0.0275 (7)	−0.0027 (6)	−0.0048 (5)	−0.0038 (6)
C5	0.0342 (7)	0.0388 (8)	0.0273 (7)	0.0008 (6)	−0.0016 (6)	0.0063 (6)
C6	0.0331 (7)	0.0272 (7)	0.0352 (8)	−0.0009 (5)	0.0024 (6)	0.0053 (6)
C7	0.0248 (6)	0.0244 (6)	0.0302 (7)	0.0002 (5)	−0.0003 (5)	−0.0031 (5)
C8	0.0256 (6)	0.0302 (7)	0.0302 (7)	0.0024 (5)	−0.0005 (5)	−0.0039 (5)
C9	0.0349 (8)	0.0414 (8)	0.0373 (8)	−0.0003 (6)	−0.0064 (6)	−0.0134 (6)
C10	0.0292 (6)	0.0289 (7)	0.0244 (6)	0.0016 (5)	−0.0027 (5)	0.0035 (5)
C11	0.0285 (6)	0.0306 (7)	0.0471 (9)	−0.0018 (6)	−0.0034 (6)	0.0011 (6)
C12	0.0295 (7)	0.0414 (9)	0.0493 (10)	0.0042 (6)	−0.0001 (7)	0.0055 (7)
C13	0.0435 (8)	0.0303 (7)	0.0352 (8)	0.0101 (6)	0.0008 (6)	0.0064 (6)
C14	0.0477 (9)	0.0267 (7)	0.0429 (9)	−0.0032 (6)	0.0018 (7)	0.0028 (6)
C15	0.0318 (7)	0.0334 (7)	0.0374 (8)	−0.0051 (6)	0.0005 (6)	0.0041 (6)

S1—O2	1.492 (1)	C6—C7	1.379 (2)
S1—C1	1.753 (1)	C6—H6	0.9500
S1—C10	1.794 (1)	C8—C9	1.478 (2)
F1—C4	1.363 (2)	C9—H9A	0.9800
F2—C13	1.357 (2)	C9—H9B	0.9800
O1—C8	1.366 (2)	C9—H9C	0.9800
O1—C7	1.379 (2)	C10—C15	1.381 (2)
C1—C8	1.359 (2)	C10—C11	1.391 (2)
C1—C2	1.442 (2)	C11—C12	1.382 (2)
C2—C7	1.393 (2)	C11—H11	0.9500
C2—C3	1.395 (2)	C12—C13	1.376 (2)
C3—C4	1.375 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.371 (2)
C4—C5	1.387 (2)	C14—C15	1.389 (2)
C5—C6	1.385 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
O2—S1—C1	107.57 (6)	C1—C8—C9	132.66 (14)
O2—S1—C10	106.55 (7)	O1—C8—C9	116.41 (13)
C1—S1—C10	99.22 (6)	C8—C9—H9A	109.5
C8—O1—C7	106.51 (10)	C8—C9—H9B	109.5
C8—C1—C2	107.32 (12)	H9A—C9—H9B	109.5
C8—C1—S1	123.09 (10)	C8—C9—H9C	109.5
C2—C1—S1	129.30 (10)	H9A—C9—H9C	109.5
C7—C2—C3	119.53 (12)	H9B—C9—H9C	109.5
C7—C2—C1	104.67 (11)	C15—C10—C11	120.97 (13)
C3—C2—C1	135.77 (13)	C15—C10—S1	118.22 (11)
C4—C3—C2	115.84 (13)	C11—C10—S1	120.50 (11)
C4—C3—H3	122.1	C12—C11—C10	119.48 (14)
C2—C3—H3	122.1	C12—C11—H11	120.3
F1—C4—C3	117.95 (13)	C10—C11—H11	120.3
F1—C4—C5	117.26 (13)	C13—C12—C11	118.25 (14)
C3—C4—C5	124.79 (13)	C13—C12—H12	120.9
C6—C5—C4	119.34 (13)	C11—C12—H12	120.9
C6—C5—H5	120.3	F2—C13—C14	118.64 (14)
C4—C5—H5	120.3	F2—C13—C12	117.82 (14)
C7—C6—C5	116.56 (13)	C14—C13—C12	123.53 (14)
C7—C6—H6	121.7	C13—C14—C15	117.92 (14)
C5—C6—H6	121.7	C13—C14—H14	121.0
C6—C7—O1	125.52 (12)	C15—C14—H14	121.0
C6—C7—C2	123.92 (13)	C10—C15—C14	119.84 (14)
O1—C7—C2	110.55 (12)	C10—C15—H15	120.1
C1—C8—O1	110.93 (12)	C14—C15—H15	120.1
O2—S1—C1—C8	−129.33 (12)	C1—C2—C7—O1	−0.14 (14)
C10—S1—C1—C8	119.93 (12)	C2—C1—C8—O1	1.61 (15)
O2—S1—C1—C2	43.56 (14)	S1—C1—C8—O1	175.85 (9)
C10—S1—C1—C2	−67.18 (13)	C2—C1—C8—C9	−177.80 (14)
C8—C1—C2—C7	−0.87 (14)	S1—C1—C8—C9	−3.6 (2)
S1—C1—C2—C7	−174.64 (10)	C7—O1—C8—C1	−1.69 (15)
C8—C1—C2—C3	176.94 (15)	C7—O1—C8—C9	177.83 (12)
S1—C1—C2—C3	3.2 (2)	O2—S1—C10—C15	17.87 (13)
C7—C2—C3—C4	−1.17 (19)	C1—S1—C10—C15	129.42 (12)
C1—C2—C3—C4	−178.74 (14)	O2—S1—C10—C11	−168.52 (11)
C2—C3—C4—F1	−178.89 (12)	C1—S1—C10—C11	−56.97 (13)
C2—C3—C4—C5	1.3 (2)	C15—C10—C11—C12	−0.5 (2)
F1—C4—C5—C6	179.52 (13)	S1—C10—C11—C12	−173.95 (12)
C3—C4—C5—C6	−0.7 (2)	C10—C11—C12—C13	0.4 (2)
C4—C5—C6—C7	−0.1 (2)	C11—C12—C13—F2	179.03 (14)
C5—C6—C7—O1	178.89 (12)	C11—C12—C13—C14	−0.4 (3)
C5—C6—C7—C2	0.2 (2)	F2—C13—C14—C15	−179.02 (14)
C8—O1—C7—C6	−177.78 (13)	C12—C13—C14—C15	0.4 (2)
C8—O1—C7—C2	1.10 (14)	C11—C10—C15—C14	0.5 (2)
C3—C2—C7—C6	0.5 (2)	S1—C10—C15—C14	174.11 (12)
C1—C2—C7—C6	178.75 (13)	C13—C14—C15—C10	−0.5 (2)
C3—C2—C7—O1	−178.39 (11)

Cg is the centroid of the furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2i	0.98	2.45	3.200 (2)	133
C14—H14···O2ii	0.95	2.55	3.270 (2)	133
C15—H15···Cgii	0.95	2.98	3.828 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2i	0.98	2.45	3.200 (2)	133
C14—H14⋯O2ii	0.95	2.55	3.270 (2)	133
C15—H15⋯Cgii	0.95	2.98	3.828 (2)	149

Symmetry codes: (i) ; (ii) .