5-Fluoro-3-methyl-sulfinyl-2-phenyl-1-benzofuran.

In the title compound, C(15)H(11)FO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 2-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 32.1 (2)°. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.690 (5) Å]. In addition, the crystal structure exhibits inter-molecular C-H⋯O and C-H⋯F inter-actions.

Related literature

For the crystal structures of similar 5-halo-3-methyl­sulfinyl-2-phenyl-1-benzofuran derivatives, see: Choi et al. (2007a ▶,b ▶). For the biological and pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Ward (1997 ▶).

Experimental

Crystal data

C15H11FO2S

M = 274.30

Monoclinic,

a = 8.507 (4) Å

b = 16.655 (7) Å

c = 9.553 (4) Å

β = 113.732 (5)°

V = 1239.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 273 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8954 measured reflections

2251 independent reflections

1478 reflections with I > 2σ(I)

R int = 0.133

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.157

S = 1.07

2251 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536809028189/er2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028189/er2071Isup2.hkl

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

C15H11FO2S	F(000) = 568
Mr = 274.30	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2317 reflections
a = 8.507 (4) Å	θ = 2.5–26.7°
b = 16.655 (7) Å	µ = 0.27 mm−1
c = 9.553 (4) Å	T = 273 K
β = 113.732 (5)°	Block, colourless
V = 1239.1 (9) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	1478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.133
graphite	θmax = 25.5°, θmin = 2.5°
Detector resolution: 10.0 pixels mm-1	h = −10→10
φ and ω scans	k = −20→20
8954 measured reflections	l = −11→11
2251 independent reflections

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)] = 0.061	Hydrogen site location: difference Fourier map
wR(F2) = 0.157	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0649P)2 + 1.1956P] where P = (Fo2 + 2Fc2)/3
2251 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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
S	0.68313 (13)	0.69115 (6)	0.59163 (12)	0.0254 (3)
F	1.1429 (3)	0.43327 (15)	0.9193 (3)	0.0410 (7)
O1	0.6667 (3)	0.49692 (15)	0.3511 (3)	0.0239 (6)
O2	0.8646 (4)	0.71756 (17)	0.6700 (4)	0.0382 (8)
C1	0.6897 (5)	0.5933 (2)	0.5247 (4)	0.0195 (8)
C2	0.8108 (5)	0.5306 (2)	0.6026 (4)	0.0212 (8)
C3	0.9321 (5)	0.5180 (2)	0.7509 (5)	0.0255 (9)
H3	0.9490	0.5548	0.8289	0.031*
C4	1.0255 (5)	0.4483 (3)	0.7757 (5)	0.0280 (9)
C5	1.0078 (5)	0.3919 (2)	0.6625 (5)	0.0292 (10)
H5	1.0754	0.3458	0.6864	0.035*
C6	0.8909 (5)	0.4045 (2)	0.5168 (5)	0.0275 (9)
H6	0.8777	0.3682	0.4388	0.033*
C7	0.7926 (5)	0.4737 (2)	0.4896 (4)	0.0224 (8)
C8	0.6087 (5)	0.5703 (2)	0.3762 (4)	0.0207 (8)
C9	0.4741 (5)	0.6076 (2)	0.2420 (4)	0.0209 (8)
C10	0.4709 (5)	0.5957 (3)	0.0963 (5)	0.0303 (10)
H10	0.5542	0.5640	0.0838	0.036*
C11	0.3445 (6)	0.6311 (3)	−0.0293 (5)	0.0371 (11)
H11	0.3438	0.6236	−0.1260	0.044*
C12	0.2182 (5)	0.6779 (3)	−0.0119 (5)	0.0339 (10)
H12	0.1329	0.7016	−0.0966	0.041*
C13	0.2205 (5)	0.6887 (2)	0.1312 (5)	0.0269 (9)
H13	0.1353	0.7196	0.1428	0.032*
C14	0.3464 (5)	0.6547 (2)	0.2579 (5)	0.0238 (9)
H14	0.3467	0.6631	0.3542	0.029*
C15	0.6122 (6)	0.6672 (3)	0.7391 (5)	0.0403 (12)
H15A	0.6921	0.6308	0.8104	0.060*
H15B	0.5009	0.6426	0.6947	0.060*
H15C	0.6055	0.7155	0.7914	0.060*

	U11	U22	U33	U12	U13	U23
S	0.0240 (5)	0.0220 (5)	0.0278 (6)	−0.0001 (4)	0.0079 (4)	−0.0029 (4)
F	0.0295 (14)	0.0525 (17)	0.0367 (15)	0.0104 (11)	0.0086 (12)	0.0157 (12)
O1	0.0211 (14)	0.0263 (15)	0.0259 (15)	0.0005 (11)	0.0112 (12)	−0.0010 (11)
O2	0.0293 (17)	0.0332 (17)	0.048 (2)	−0.0098 (13)	0.0108 (15)	−0.0085 (14)
C1	0.0155 (18)	0.0189 (19)	0.023 (2)	0.0004 (14)	0.0071 (16)	0.0009 (15)
C2	0.0142 (19)	0.026 (2)	0.026 (2)	−0.0018 (15)	0.0110 (17)	0.0027 (15)
C3	0.020 (2)	0.031 (2)	0.027 (2)	−0.0018 (16)	0.0115 (18)	0.0017 (16)
C4	0.016 (2)	0.040 (2)	0.028 (2)	0.0038 (17)	0.0091 (18)	0.0123 (18)
C5	0.027 (2)	0.031 (2)	0.039 (3)	0.0073 (17)	0.022 (2)	0.0095 (18)
C6	0.028 (2)	0.025 (2)	0.036 (2)	0.0015 (17)	0.0193 (19)	−0.0002 (17)
C7	0.020 (2)	0.026 (2)	0.026 (2)	−0.0025 (15)	0.0139 (18)	0.0039 (16)
C8	0.021 (2)	0.0170 (19)	0.028 (2)	0.0004 (15)	0.0135 (17)	0.0001 (15)
C9	0.0177 (19)	0.023 (2)	0.022 (2)	−0.0030 (15)	0.0075 (16)	0.0018 (15)
C10	0.026 (2)	0.040 (2)	0.026 (2)	0.0028 (18)	0.0120 (19)	−0.0037 (18)
C11	0.035 (3)	0.053 (3)	0.025 (2)	0.000 (2)	0.014 (2)	0.000 (2)
C12	0.026 (2)	0.037 (3)	0.034 (3)	−0.0002 (18)	0.007 (2)	0.0096 (18)
C13	0.016 (2)	0.032 (2)	0.034 (2)	0.0027 (16)	0.0114 (18)	0.0044 (18)
C14	0.017 (2)	0.029 (2)	0.026 (2)	−0.0027 (16)	0.0107 (18)	−0.0009 (16)
C15	0.047 (3)	0.043 (3)	0.044 (3)	0.003 (2)	0.033 (2)	−0.008 (2)

S—O2	1.486 (3)	C6—H6	0.9300
S—C1	1.760 (4)	C8—C9	1.470 (5)
S—C15	1.786 (5)	C9—C10	1.395 (5)
F—C4	1.357 (4)	C9—C14	1.397 (5)
O1—C8	1.375 (4)	C10—C11	1.380 (6)
O1—C7	1.381 (5)	C10—H10	0.9300
C1—C8	1.358 (5)	C11—C12	1.390 (6)
C1—C2	1.446 (5)	C11—H11	0.9300
C2—C3	1.392 (5)	C12—C13	1.372 (6)
C2—C7	1.398 (5)	C12—H12	0.9300
C3—C4	1.373 (6)	C13—C14	1.374 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.393 (6)	C14—H14	0.9300
C5—C6	1.363 (6)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.385 (5)	C15—H15C	0.9600
O2—S—C1	106.19 (17)	C1—C8—C9	133.0 (3)
O2—S—C15	106.3 (2)	O1—C8—C9	115.6 (3)
C1—S—C15	98.6 (2)	C10—C9—C14	119.0 (4)
C8—O1—C7	106.0 (3)	C10—C9—C8	120.4 (3)
C8—C1—C2	106.9 (3)	C14—C9—C8	120.6 (3)
C8—C1—S	124.3 (3)	C11—C10—C9	120.2 (4)
C2—C1—S	127.0 (3)	C11—C10—H10	119.9
C3—C2—C7	119.4 (4)	C9—C10—H10	119.9
C3—C2—C1	135.7 (4)	C10—C11—C12	120.3 (4)
C7—C2—C1	104.9 (3)	C10—C11—H11	119.8
C4—C3—C2	116.3 (4)	C12—C11—H11	119.8
C4—C3—H3	121.9	C13—C12—C11	119.4 (4)
C2—C3—H3	121.9	C13—C12—H12	120.3
F—C4—C3	118.0 (4)	C11—C12—H12	120.3
F—C4—C5	117.8 (4)	C12—C13—C14	121.1 (4)
C3—C4—C5	124.2 (4)	C12—C13—H13	119.5
C6—C5—C4	119.7 (4)	C14—C13—H13	119.5
C6—C5—H5	120.2	C13—C14—C9	120.0 (4)
C4—C5—H5	120.2	C13—C14—H14	120.0
C5—C6—C7	117.2 (4)	C9—C14—H14	120.0
C5—C6—H6	121.4	S—C15—H15A	109.5
C7—C6—H6	121.4	S—C15—H15B	109.5
O1—C7—C6	126.1 (4)	H15A—C15—H15B	109.5
O1—C7—C2	110.6 (3)	S—C15—H15C	109.5
C6—C7—C2	123.3 (4)	H15A—C15—H15C	109.5
C1—C8—O1	111.5 (3)	H15B—C15—H15C	109.5
O2—S—C1—C8	−123.7 (3)	C3—C2—C7—C6	−0.5 (6)
C15—S—C1—C8	126.4 (4)	C1—C2—C7—C6	177.9 (3)
O2—S—C1—C2	39.2 (4)	C2—C1—C8—O1	0.4 (4)
C15—S—C1—C2	−70.7 (4)	S—C1—C8—O1	166.2 (3)
C8—C1—C2—C3	178.7 (4)	C2—C1—C8—C9	179.9 (4)
S—C1—C2—C3	13.4 (6)	S—C1—C8—C9	−14.3 (6)
C8—C1—C2—C7	0.6 (4)	C7—O1—C8—C1	−1.3 (4)
S—C1—C2—C7	−164.6 (3)	C7—O1—C8—C9	179.1 (3)
C7—C2—C3—C4	−0.8 (5)	C1—C8—C9—C10	147.8 (4)
C1—C2—C3—C4	−178.6 (4)	O1—C8—C9—C10	−32.7 (5)
C2—C3—C4—F	−178.9 (3)	C1—C8—C9—C14	−32.9 (6)
C2—C3—C4—C5	1.3 (6)	O1—C8—C9—C14	146.6 (3)
F—C4—C5—C6	179.8 (3)	C14—C9—C10—C11	0.8 (6)
C3—C4—C5—C6	−0.4 (6)	C8—C9—C10—C11	−179.8 (4)
C4—C5—C6—C7	−1.0 (6)	C9—C10—C11—C12	−0.8 (7)
C8—O1—C7—C6	−177.6 (4)	C10—C11—C12—C13	0.1 (7)
C8—O1—C7—C2	1.7 (4)	C11—C12—C13—C14	0.6 (6)
C5—C6—C7—O1	−179.3 (3)	C12—C13—C14—C9	−0.6 (6)
C5—C6—C7—C2	1.4 (6)	C10—C9—C14—C13	−0.1 (6)
C3—C2—C7—O1	−179.9 (3)	C8—C9—C14—C13	−179.5 (3)
C1—C2—C7—O1	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.48	3.282 (5)	145
C12—H12···O2ii	0.93	2.48	3.371 (5)	160
C13—H13···O2iii	0.93	2.64	3.555 (5)	170
C15—H15B···O1iv	0.96	2.67	3.493 (6)	144
C15—H15A···Fv	0.96	2.62	3.509 (6)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.48	3.282 (5)	145
C12—H12⋯O2ii	0.93	2.48	3.371 (5)	160
C13—H13⋯O2iii	0.93	2.64	3.555 (5)	170
C15—H15B⋯O1iv	0.96	2.67	3.493 (6)	144
C15—H15A⋯Fv	0.96	2.62	3.509 (6)	155

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