3-(3-Fluoro-phenyl-sulfin-yl)-2,5,7-trimethyl-1-benzofuran.

In the title compound, C(17)H(15)FO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds. The crystal structure also exhibits a slipped π-π inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.719 (2) Å, inter-planar distance = 3.475 (2) Å and slippage = 1.325 Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 3-(4-fluoro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C17H15FO2S

M = 302.35

Triclinic,

a = 6.2942 (2) Å

b = 11.1162 (4) Å

c = 11.8021 (6) Å

α = 110.701 (3)°

β = 100.176 (3)°

γ = 103.621 (2)°

V = 719.39 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.29 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.951

12696 measured reflections

3301 independent reflections

2760 reflections with I > 2σ(I)

R int = 0.122

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.07

3301 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.44 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/S1600536811018654/ez2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018654/ez2242Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018654/ez2242Isup3.cml

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

C17H15FO2S	Z = 2
Mr = 302.35	F(000) = 316
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2942 (2) Å	Cell parameters from 5769 reflections
b = 11.1162 (4) Å	θ = 2.2–27.5°
c = 11.8021 (6) Å	µ = 0.24 mm−1
α = 110.701 (3)°	T = 296 K
β = 100.176 (3)°	Block, colourless
γ = 103.621 (2)°	0.29 × 0.25 × 0.21 mm
V = 719.39 (5) Å3

Bruker SMART APEXII CCD diffractometer	3301 independent reflections
Radiation source: rotating anode	2760 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.122
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.935, Tmax = 0.951	l = −15→15
12696 measured 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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.133	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3
3301 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.44 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
S1	0.61779 (7)	0.50213 (4)	0.83763 (4)	0.02605 (15)
O1	0.2342 (2)	0.38830 (12)	0.49387 (10)	0.0275 (3)
O2	0.8652 (2)	0.52089 (14)	0.85568 (12)	0.0361 (3)
F1	0.7099 (2)	0.14993 (13)	1.00630 (12)	0.0517 (4)
C1	0.4798 (3)	0.42715 (17)	0.67501 (15)	0.0249 (3)
C2	0.5132 (3)	0.31895 (16)	0.57616 (15)	0.0250 (3)
C3	0.6547 (3)	0.23900 (18)	0.56868 (17)	0.0303 (4)
H3	0.7618	0.2516	0.6406	0.036*
C4	0.6325 (3)	0.14076 (18)	0.45232 (18)	0.0342 (4)
C5	0.4696 (3)	0.12330 (18)	0.34451 (18)	0.0350 (4)
H5	0.4573	0.0561	0.2670	0.042*
C6	0.3262 (3)	0.20148 (18)	0.34811 (16)	0.0307 (4)
C7	0.3566 (3)	0.29841 (16)	0.46668 (15)	0.0256 (4)
C8	0.3133 (3)	0.46537 (17)	0.62103 (15)	0.0253 (3)
C9	0.7843 (4)	0.0524 (2)	0.4405 (2)	0.0470 (5)
H9A	0.9238	0.0970	0.4290	0.070*
H9B	0.7075	−0.0332	0.3691	0.070*
H9C	0.8177	0.0373	0.5160	0.070*
C10	0.1525 (4)	0.1847 (2)	0.23408 (17)	0.0417 (5)
H10A	0.0034	0.1632	0.2459	0.063*
H10B	0.1568	0.1125	0.1608	0.063*
H10C	0.1863	0.2678	0.2226	0.063*
C11	0.2019 (3)	0.56740 (18)	0.67277 (17)	0.0324 (4)
H11A	0.0490	0.5220	0.6687	0.049*
H11B	0.1982	0.6205	0.6241	0.049*
H11C	0.2863	0.6259	0.7591	0.049*
C12	0.5032 (3)	0.35709 (16)	0.86983 (14)	0.0243 (3)
C13	0.6565 (3)	0.30906 (17)	0.92600 (15)	0.0280 (4)
H13	0.8132	0.3478	0.9441	0.034*
C14	0.5646 (3)	0.20107 (18)	0.95355 (17)	0.0326 (4)
C15	0.3363 (3)	0.14339 (18)	0.93105 (17)	0.0352 (4)
H15	0.2814	0.0706	0.9513	0.042*
C16	0.1877 (3)	0.19579 (19)	0.87727 (18)	0.0352 (4)
H16	0.0313	0.1583	0.8618	0.042*
C17	0.2699 (3)	0.30294 (18)	0.84667 (17)	0.0309 (4)
H17	0.1703	0.3384	0.8110	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.0285 (3)	0.0248 (2)	0.0201 (2)	0.00624 (17)	0.00117 (16)	0.00820 (17)
O1	0.0280 (6)	0.0311 (6)	0.0233 (6)	0.0126 (5)	0.0020 (5)	0.0117 (5)
O2	0.0248 (6)	0.0437 (7)	0.0335 (7)	0.0014 (5)	−0.0012 (5)	0.0196 (6)
F1	0.0560 (8)	0.0466 (7)	0.0606 (8)	0.0225 (6)	0.0038 (6)	0.0334 (7)
C1	0.0251 (8)	0.0269 (8)	0.0228 (8)	0.0100 (6)	0.0033 (6)	0.0111 (7)
C2	0.0256 (8)	0.0249 (8)	0.0247 (8)	0.0080 (7)	0.0053 (6)	0.0115 (7)
C3	0.0283 (9)	0.0320 (9)	0.0349 (9)	0.0141 (7)	0.0078 (7)	0.0163 (8)
C4	0.0365 (10)	0.0290 (9)	0.0430 (11)	0.0148 (8)	0.0173 (8)	0.0159 (8)
C5	0.0454 (11)	0.0257 (8)	0.0300 (9)	0.0093 (8)	0.0147 (8)	0.0067 (8)
C6	0.0352 (9)	0.0274 (8)	0.0255 (8)	0.0058 (7)	0.0078 (7)	0.0098 (7)
C7	0.0267 (8)	0.0248 (8)	0.0250 (8)	0.0091 (7)	0.0059 (7)	0.0104 (7)
C8	0.0267 (8)	0.0264 (8)	0.0222 (8)	0.0084 (7)	0.0040 (6)	0.0110 (7)
C9	0.0534 (13)	0.0413 (11)	0.0591 (13)	0.0285 (10)	0.0272 (11)	0.0216 (11)
C10	0.0533 (12)	0.0370 (10)	0.0235 (9)	0.0065 (9)	0.0003 (8)	0.0101 (8)
C11	0.0341 (10)	0.0335 (9)	0.0336 (9)	0.0173 (8)	0.0086 (8)	0.0148 (8)
C12	0.0290 (8)	0.0238 (8)	0.0164 (7)	0.0082 (6)	0.0034 (6)	0.0058 (6)
C13	0.0275 (8)	0.0291 (8)	0.0241 (8)	0.0100 (7)	0.0031 (7)	0.0088 (7)
C14	0.0439 (10)	0.0287 (8)	0.0261 (8)	0.0176 (8)	0.0051 (8)	0.0109 (7)
C15	0.0465 (11)	0.0263 (9)	0.0292 (9)	0.0071 (8)	0.0104 (8)	0.0104 (7)
C16	0.0306 (9)	0.0335 (9)	0.0360 (10)	0.0046 (8)	0.0098 (8)	0.0116 (8)
C17	0.0270 (8)	0.0339 (9)	0.0292 (9)	0.0107 (7)	0.0038 (7)	0.0116 (8)

S1—O2	1.4876 (13)	C9—H9A	0.9600
S1—C1	1.7527 (16)	C9—H9B	0.9600
S1—C12	1.8017 (17)	C9—H9C	0.9600
O1—C8	1.3639 (19)	C10—H10A	0.9600
O1—C7	1.3851 (19)	C10—H10B	0.9600
F1—C14	1.357 (2)	C10—H10C	0.9600
C1—C8	1.360 (2)	C11—H11A	0.9600
C1—C2	1.437 (2)	C11—H11B	0.9600
C2—C7	1.389 (2)	C11—H11C	0.9600
C2—C3	1.391 (2)	C12—C17	1.386 (2)
C3—C4	1.378 (3)	C12—C13	1.386 (2)
C3—H3	0.9300	C13—C14	1.377 (3)
C4—C5	1.407 (3)	C13—H13	0.9300
C4—C9	1.513 (2)	C14—C15	1.363 (3)
C5—C6	1.389 (3)	C15—C16	1.388 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.378 (2)	C16—C17	1.377 (3)
C6—C10	1.499 (2)	C16—H16	0.9300
C8—C11	1.479 (2)	C17—H17	0.9300
O2—S1—C1	108.38 (8)	H9A—C9—H9C	109.5
O2—S1—C12	105.93 (7)	H9B—C9—H9C	109.5
C1—S1—C12	97.25 (7)	C6—C10—H10A	109.5
C8—O1—C7	106.64 (12)	C6—C10—H10B	109.5
C8—C1—C2	107.69 (14)	H10A—C10—H10B	109.5
C8—C1—S1	123.27 (13)	C6—C10—H10C	109.5
C2—C1—S1	129.04 (12)	H10A—C10—H10C	109.5
C7—C2—C3	119.25 (15)	H10B—C10—H10C	109.5
C7—C2—C1	104.76 (13)	C8—C11—H11A	109.5
C3—C2—C1	135.99 (15)	C8—C11—H11B	109.5
C4—C3—C2	118.52 (16)	H11A—C11—H11B	109.5
C4—C3—H3	120.7	C8—C11—H11C	109.5
C2—C3—H3	120.7	H11A—C11—H11C	109.5
C3—C4—C5	119.93 (16)	H11B—C11—H11C	109.5
C3—C4—C9	119.97 (17)	C17—C12—C13	121.95 (16)
C5—C4—C9	120.09 (18)	C17—C12—S1	120.18 (12)
C6—C5—C4	123.21 (17)	C13—C12—S1	117.72 (13)
C6—C5—H5	118.4	C14—C13—C12	116.56 (16)
C4—C5—H5	118.4	C14—C13—H13	121.7
C7—C6—C5	114.34 (16)	C12—C13—H13	121.7
C7—C6—C10	121.75 (17)	F1—C14—C15	118.44 (17)
C5—C6—C10	123.91 (17)	F1—C14—C13	118.02 (17)
C6—C7—O1	124.90 (15)	C15—C14—C13	123.54 (16)
C6—C7—C2	124.74 (15)	C14—C15—C16	118.45 (17)
O1—C7—C2	110.36 (14)	C14—C15—H15	120.8
C1—C8—O1	110.54 (14)	C16—C15—H15	120.8
C1—C8—C11	133.15 (16)	C17—C16—C15	120.52 (17)
O1—C8—C11	116.28 (13)	C17—C16—H16	119.7
C4—C9—H9A	109.5	C15—C16—H16	119.7
C4—C9—H9B	109.5	C16—C17—C12	118.94 (16)
H9A—C9—H9B	109.5	C16—C17—H17	120.5
C4—C9—H9C	109.5	C12—C17—H17	120.5
O2—S1—C1—C8	−138.58 (15)	C1—C2—C7—C6	−178.81 (16)
C12—S1—C1—C8	111.91 (16)	C3—C2—C7—O1	−179.52 (15)
O2—S1—C1—C2	41.89 (18)	C1—C2—C7—O1	0.63 (19)
C12—S1—C1—C2	−67.61 (17)	C2—C1—C8—O1	0.7 (2)
C8—C1—C2—C7	−0.79 (19)	S1—C1—C8—O1	−178.92 (12)
S1—C1—C2—C7	178.79 (14)	C2—C1—C8—C11	178.47 (19)
C8—C1—C2—C3	179.4 (2)	S1—C1—C8—C11	−1.1 (3)
S1—C1—C2—C3	−1.0 (3)	C7—O1—C8—C1	−0.30 (19)
C7—C2—C3—C4	−0.7 (3)	C7—O1—C8—C11	−178.49 (15)
C1—C2—C3—C4	179.12 (19)	O2—S1—C12—C17	−172.33 (13)
C2—C3—C4—C5	0.1 (3)	C1—S1—C12—C17	−60.80 (15)
C2—C3—C4—C9	179.70 (17)	O2—S1—C12—C13	12.06 (14)
C3—C4—C5—C6	0.2 (3)	C1—S1—C12—C13	123.59 (13)
C9—C4—C5—C6	−179.39 (19)	C17—C12—C13—C14	2.3 (2)
C4—C5—C6—C7	0.1 (3)	S1—C12—C13—C14	177.84 (12)
C4—C5—C6—C10	179.67 (18)	C12—C13—C14—F1	178.73 (15)
C5—C6—C7—O1	179.93 (16)	C12—C13—C14—C15	−1.5 (3)
C10—C6—C7—O1	0.3 (3)	F1—C14—C15—C16	179.91 (16)
C5—C6—C7—C2	−0.7 (3)	C13—C14—C15—C16	0.1 (3)
C10—C6—C7—C2	179.67 (17)	C14—C15—C16—C17	0.5 (3)
C8—O1—C7—C6	179.21 (16)	C15—C16—C17—C12	0.3 (3)
C8—O1—C7—C2	−0.23 (19)	C13—C12—C17—C16	−1.8 (3)
C3—C2—C7—C6	1.0 (3)	S1—C12—C17—C16	−177.22 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.93	2.51	3.227 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.93	2.51	3.227 (2)	134

Symmetry code: (i) .