3-(4-Fluoro-phenyl-sulfin-yl)-2,5,7-trimethyl-1-benzofuran.

In the title mol-ecule, C(17)H(15)FO(2)S, the O atom and the 4-fluoro-phenyl group of the 4-fluoro-phenyl-sulfinyl substituent lie on opposite sides of the benzofuran fragment. The mean planes of the benzofuran and 4-fluoro-phenyl fragments form a dihedral angle of 86.07 (4)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further linked via inter-molecular C-H⋯π inter-actions.

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2008 ▶). For the biological 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 ▶).

Experimental

Crystal data

C17H15FO2S

M = 302.35

Triclinic,

a = 6.2558 (2) Å

b = 11.1848 (3) Å

c = 11.9766 (5) Å

α = 110.355 (2)°

β = 99.448 (2)°

γ = 104.130 (1)°

V = 732.75 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 172 K

0.43 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.681, T max = 0.746

12781 measured reflections

3350 independent reflections

3071 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.03

3350 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 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/S160053681000293X/cv2691sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000293X/cv2691Isup2.hkl

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

C17H15FO2S	Z = 2
Mr = 302.35	F(000) = 316
Triclinic, P1	Dx = 1.370 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2558 (2) Å	Cell parameters from 9234 reflections
b = 11.1848 (3) Å	θ = 3.3–27.5°
c = 11.9766 (5) Å	µ = 0.23 mm−1
α = 110.355 (2)°	T = 172 K
β = 99.448 (2)°	Block, colourless
γ = 104.130 (1)°	0.43 × 0.28 × 0.26 mm
V = 732.75 (4) Å3

Bruker SMART APEXII CCD diffractometer	3350 independent reflections
Radiation source: Rotating Anode	3071 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.026
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 = 0.681, Tmax = 0.746	l = −15→15
12781 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.3002P] where P = (Fo2 + 2Fc2)/3
3350 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.37 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	0.61072 (6)	0.50406 (3)	0.83633 (3)	0.02837 (11)
F	0.28727 (19)	0.04833 (10)	0.97162 (10)	0.0498 (3)
O1	0.23445 (16)	0.38938 (10)	0.49810 (8)	0.0282 (2)
O2	0.86249 (18)	0.53145 (12)	0.85499 (10)	0.0409 (3)
C1	0.4760 (2)	0.42813 (13)	0.67695 (12)	0.0262 (3)
C2	0.5133 (2)	0.32114 (13)	0.58028 (12)	0.0265 (3)
C3	0.6563 (3)	0.24226 (15)	0.57323 (14)	0.0329 (3)
H3	0.7644	0.2546	0.6454	0.040*
C4	0.6370 (3)	0.14528 (15)	0.45835 (16)	0.0380 (3)
C5	0.4753 (3)	0.12862 (15)	0.35294 (15)	0.0391 (4)
H5	0.4639	0.0608	0.2755	0.047*
C6	0.3315 (3)	0.20587 (14)	0.35596 (13)	0.0337 (3)
C7	0.3589 (2)	0.30150 (13)	0.47270 (12)	0.0273 (3)
C8	0.3107 (2)	0.46565 (13)	0.62320 (11)	0.0261 (3)
C9	0.7900 (3)	0.05875 (18)	0.4476 (2)	0.0522 (5)
H9A	0.9355	0.1056	0.4379	0.078*
H9B	0.7145	−0.0271	0.3754	0.078*
H9C	0.8196	0.0416	0.5226	0.078*
C10	0.1578 (3)	0.19014 (17)	0.24463 (14)	0.0464 (4)
H10A	0.0033	0.1588	0.2532	0.070*
H10B	0.1734	0.1242	0.1698	0.070*
H10C	0.1834	0.2772	0.2382	0.070*
C11	0.1968 (3)	0.56646 (15)	0.67177 (13)	0.0337 (3)
H11A	0.0400	0.5202	0.6690	0.051*
H11B	0.1925	0.6186	0.6210	0.051*
H11C	0.2823	0.6274	0.7575	0.051*
C12	0.5089 (2)	0.35932 (13)	0.87080 (11)	0.0264 (3)
C13	0.6686 (2)	0.31841 (15)	0.92889 (12)	0.0310 (3)
H13	0.8279	0.3625	0.9454	0.037*
C14	0.5933 (3)	0.21171 (15)	0.96292 (13)	0.0350 (3)
H14	0.6994	0.1810	1.0023	0.042*
C15	0.3616 (3)	0.15211 (14)	0.93807 (13)	0.0348 (3)
C16	0.1997 (3)	0.19321 (15)	0.88255 (14)	0.0361 (3)
H16	0.0407	0.1499	0.8678	0.043*
C17	0.2753 (2)	0.29939 (15)	0.84890 (13)	0.0326 (3)
H17	0.1683	0.3309	0.8112	0.039*

	U11	U22	U33	U12	U13	U23
S	0.02613 (19)	0.03171 (19)	0.02281 (17)	0.00535 (14)	0.00233 (13)	0.01064 (13)
F	0.0627 (7)	0.0372 (5)	0.0530 (6)	0.0114 (5)	0.0166 (5)	0.0253 (4)
O1	0.0271 (5)	0.0333 (5)	0.0240 (4)	0.0108 (4)	0.0038 (4)	0.0120 (4)
O2	0.0236 (5)	0.0554 (7)	0.0374 (5)	0.0007 (5)	0.0002 (4)	0.0234 (5)
C1	0.0236 (6)	0.0306 (6)	0.0240 (6)	0.0080 (5)	0.0055 (5)	0.0117 (5)
C2	0.0237 (6)	0.0285 (6)	0.0278 (6)	0.0069 (5)	0.0080 (5)	0.0129 (5)
C3	0.0284 (7)	0.0352 (7)	0.0417 (8)	0.0131 (6)	0.0124 (6)	0.0200 (6)
C4	0.0403 (8)	0.0319 (7)	0.0522 (9)	0.0148 (6)	0.0261 (7)	0.0208 (7)
C5	0.0491 (9)	0.0294 (7)	0.0377 (7)	0.0090 (6)	0.0233 (7)	0.0098 (6)
C6	0.0389 (8)	0.0304 (7)	0.0275 (6)	0.0044 (6)	0.0116 (6)	0.0103 (5)
C7	0.0269 (7)	0.0285 (6)	0.0269 (6)	0.0073 (5)	0.0084 (5)	0.0122 (5)
C8	0.0246 (6)	0.0298 (6)	0.0241 (6)	0.0075 (5)	0.0063 (5)	0.0121 (5)
C9	0.0561 (11)	0.0433 (9)	0.0754 (13)	0.0285 (8)	0.0380 (10)	0.0278 (9)
C10	0.0601 (11)	0.0419 (8)	0.0245 (7)	0.0067 (8)	0.0047 (7)	0.0086 (6)
C11	0.0315 (7)	0.0368 (7)	0.0357 (7)	0.0160 (6)	0.0099 (6)	0.0145 (6)
C12	0.0257 (6)	0.0304 (6)	0.0210 (5)	0.0083 (5)	0.0049 (5)	0.0092 (5)
C13	0.0264 (7)	0.0374 (7)	0.0280 (6)	0.0119 (6)	0.0053 (5)	0.0118 (5)
C14	0.0393 (8)	0.0368 (7)	0.0314 (7)	0.0187 (6)	0.0065 (6)	0.0138 (6)
C15	0.0454 (9)	0.0280 (6)	0.0294 (6)	0.0100 (6)	0.0120 (6)	0.0105 (5)
C16	0.0296 (7)	0.0377 (7)	0.0359 (7)	0.0047 (6)	0.0078 (6)	0.0138 (6)
C17	0.0257 (7)	0.0396 (7)	0.0316 (7)	0.0100 (6)	0.0041 (5)	0.0154 (6)

S—O2	1.4919 (11)	C9—H9A	0.9800
S—C1	1.7521 (13)	C9—H9B	0.9800
S—C12	1.8013 (14)	C9—H9C	0.9800
F—C15	1.3591 (17)	C10—H10A	0.9800
O1—C8	1.3702 (15)	C10—H10B	0.9800
O1—C7	1.3814 (16)	C10—H10C	0.9800
C1—C8	1.3567 (19)	C11—H11A	0.9800
C1—C2	1.4450 (18)	C11—H11B	0.9800
C2—C7	1.3899 (19)	C11—H11C	0.9800
C2—C3	1.3942 (19)	C12—C13	1.3811 (19)
C3—C4	1.388 (2)	C12—C17	1.3885 (19)
C3—H3	0.9500	C13—C14	1.393 (2)
C4—C5	1.406 (2)	C13—H13	0.9500
C4—C9	1.509 (2)	C14—C15	1.372 (2)
C5—C6	1.387 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.378 (2)
C6—C7	1.3856 (19)	C16—C17	1.385 (2)
C6—C10	1.503 (2)	C16—H16	0.9500
C8—C11	1.4799 (19)	C17—H17	0.9500
O2—S—C1	108.53 (6)	H9A—C9—H9C	109.5
O2—S—C12	105.94 (6)	H9B—C9—H9C	109.5
C1—S—C12	97.96 (6)	C6—C10—H10A	109.5
C8—O1—C7	106.44 (10)	C6—C10—H10B	109.5
C8—C1—C2	107.66 (11)	H10A—C10—H10B	109.5
C8—C1—S	122.90 (10)	C6—C10—H10C	109.5
C2—C1—S	129.43 (10)	H10A—C10—H10C	109.5
C7—C2—C3	119.26 (13)	H10B—C10—H10C	109.5
C7—C2—C1	104.44 (11)	C8—C11—H11A	109.5
C3—C2—C1	136.30 (13)	C8—C11—H11B	109.5
C4—C3—C2	118.46 (14)	H11A—C11—H11B	109.5
C4—C3—H3	120.8	C8—C11—H11C	109.5
C2—C3—H3	120.8	H11A—C11—H11C	109.5
C3—C4—C5	119.76 (14)	H11B—C11—H11C	109.5
C3—C4—C9	119.71 (16)	C13—C12—C17	121.61 (13)
C5—C4—C9	120.53 (15)	C13—C12—S	118.26 (11)
C6—C5—C4	123.51 (14)	C17—C12—S	119.88 (11)
C6—C5—H5	118.2	C12—C13—C14	119.19 (13)
C4—C5—H5	118.2	C12—C13—H13	120.4
C7—C6—C5	114.30 (14)	C14—C13—H13	120.4
C7—C6—C10	121.21 (15)	C15—C14—C13	118.22 (14)
C5—C6—C10	124.49 (14)	C15—C14—H14	120.9
O1—C7—C6	124.51 (13)	C13—C14—H14	120.9
O1—C7—C2	110.78 (11)	F—C15—C14	118.43 (14)
C6—C7—C2	124.70 (13)	F—C15—C16	118.07 (14)
C1—C8—O1	110.67 (11)	C14—C15—C16	123.49 (14)
C1—C8—C11	133.59 (12)	C15—C16—C17	118.13 (14)
O1—C8—C11	115.72 (11)	C15—C16—H16	120.9
C4—C9—H9A	109.5	C17—C16—H16	120.9
C4—C9—H9B	109.5	C16—C17—C12	119.34 (14)
H9A—C9—H9B	109.5	C16—C17—H17	120.3
C4—C9—H9C	109.5	C12—C17—H17	120.3
O2—S—C1—C8	−134.93 (12)	C1—C2—C7—O1	0.50 (14)
C12—S—C1—C8	115.24 (12)	C3—C2—C7—C6	1.2 (2)
O2—S—C1—C2	44.44 (14)	C1—C2—C7—C6	−178.86 (13)
C12—S—C1—C2	−65.40 (13)	C2—C1—C8—O1	0.87 (15)
C8—C1—C2—C7	−0.82 (15)	S—C1—C8—O1	−179.65 (9)
S—C1—C2—C7	179.74 (11)	C2—C1—C8—C11	179.02 (14)
C8—C1—C2—C3	179.13 (15)	S—C1—C8—C11	−1.5 (2)
S—C1—C2—C3	−0.3 (2)	C7—O1—C8—C1	−0.55 (15)
C7—C2—C3—C4	−0.7 (2)	C7—O1—C8—C11	−179.07 (11)
C1—C2—C3—C4	179.31 (15)	O2—S—C12—C13	12.66 (12)
C2—C3—C4—C5	−0.2 (2)	C1—S—C12—C13	124.61 (11)
C2—C3—C4—C9	179.74 (13)	O2—S—C12—C17	−172.98 (11)
C3—C4—C5—C6	0.8 (2)	C1—S—C12—C17	−61.03 (12)
C9—C4—C5—C6	−179.12 (14)	C17—C12—C13—C14	2.0 (2)
C4—C5—C6—C7	−0.4 (2)	S—C12—C13—C14	176.26 (10)
C4—C5—C6—C10	179.89 (15)	C12—C13—C14—C15	−0.6 (2)
C8—O1—C7—C6	179.37 (13)	C13—C14—C15—F	−179.71 (12)
C8—O1—C7—C2	0.00 (14)	C13—C14—C15—C16	−0.8 (2)
C5—C6—C7—O1	−179.85 (12)	F—C15—C16—C17	179.68 (13)
C10—C6—C7—O1	−0.2 (2)	C14—C15—C16—C17	0.7 (2)
C5—C6—C7—C2	−0.6 (2)	C15—C16—C17—C12	0.7 (2)
C10—C6—C7—C2	179.13 (14)	C13—C12—C17—C16	−2.0 (2)
C3—C2—C7—O1	−179.46 (12)	S—C12—C17—C16	−176.20 (11)

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.50	3.194 (2)	130
C11—H11B···Cgii	0.98	2.87	3.663 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.50	3.194 (2)	130
C11—H11B⋯Cgii	0.98	2.87	3.663 (2)	139

Symmetry codes: (i) ; (ii) .