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

In the title compound, C(17)H(15)FO(3)S, the 3-fluoro-phenyl ring makes a dihedral angle of 73.39 (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 and benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.743 (2) Å, inter-planar distance = 3.543 (2) Å and slippage = 1.207 (2) Å].

Related literature

For the pharmacological 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 the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C17H15FO3S

M = 318.35

Triclinic,

a = 7.3603 (1) Å

b = 10.3121 (2) Å

c = 11.0590 (2) Å

α = 111.753 (1)°

β = 92.864 (1)°

γ = 101.623 (1)°

V = 756.42 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.21 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.953, T max = 0.959

13459 measured reflections

3468 independent reflections

3111 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.04

3468 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.42 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/S1600536811048525/tk5019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048525/tk5019Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048525/tk5019Isup3.cml

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

C17H15FO3S	Z = 2
Mr = 318.35	F(000) = 332
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3603 (1) Å	Cell parameters from 7569 reflections
b = 10.3121 (2) Å	θ = 2.9–27.5°
c = 11.0590 (2) Å	µ = 0.23 mm−1
α = 111.753 (1)°	T = 173 K
β = 92.864 (1)°	Block, colourless
γ = 101.623 (1)°	0.21 × 0.20 × 0.18 mm
V = 756.42 (2) Å3

Bruker SMART APEXII CCD diffractometer	3468 independent reflections
Radiation source: rotating anode	3111 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.953, Tmax = 0.959	l = −14→14
13459 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) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.3468P] where P = (Fo2 + 2Fc2)/3
3468 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.42 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	0.51024 (4)	0.55990 (3)	0.27097 (3)	0.02048 (10)
F1	0.98547 (15)	0.34469 (13)	−0.00478 (10)	0.0483 (3)
O1	0.73981 (14)	0.96817 (11)	0.36726 (10)	0.0264 (2)
O2	0.41075 (14)	0.52113 (11)	0.36588 (10)	0.0255 (2)
O3	0.41181 (15)	0.52758 (12)	0.14377 (10)	0.0286 (2)
C1	0.61238 (19)	0.74265 (14)	0.34366 (13)	0.0212 (3)
C2	0.65279 (19)	0.82907 (14)	0.48360 (13)	0.0215 (3)
C3	0.6301 (2)	0.80574 (16)	0.59909 (14)	0.0256 (3)
H3	0.5802	0.7121	0.5963	0.031*
C4	0.6823 (2)	0.92315 (17)	0.71796 (15)	0.0307 (3)
C5	0.7596 (2)	1.06062 (17)	0.72026 (15)	0.0314 (3)
H5	0.7951	1.1389	0.8031	0.038*
C6	0.7865 (2)	1.08763 (15)	0.60761 (16)	0.0277 (3)
C7	0.72972 (19)	0.96719 (15)	0.49131 (14)	0.0237 (3)
C8	0.6676 (2)	0.83088 (15)	0.27950 (14)	0.0246 (3)
C9	0.6531 (3)	0.9053 (2)	0.84564 (17)	0.0472 (5)
H9A	0.5433	0.9401	0.8779	0.071*
H9B	0.7640	0.9607	0.9109	0.071*
H9C	0.6332	0.8034	0.8310	0.071*
C10	0.8689 (2)	1.23324 (16)	0.60873 (18)	0.0362 (4)
H10A	0.9853	1.2318	0.5695	0.054*
H10B	0.8955	1.3042	0.6995	0.054*
H10C	0.7798	1.2590	0.5579	0.054*
C11	0.6663 (3)	0.80980 (19)	0.13943 (16)	0.0353 (4)
H11A	0.6324	0.7067	0.0844	0.053*
H11B	0.7910	0.8525	0.1257	0.053*
H11C	0.5747	0.8562	0.1156	0.053*
C12	0.69861 (19)	0.47456 (14)	0.24581 (13)	0.0212 (3)
C13	0.7727 (2)	0.44175 (16)	0.34553 (15)	0.0279 (3)
H13	0.7234	0.4647	0.4267	0.033*
C14	0.9203 (2)	0.37478 (19)	0.32442 (18)	0.0364 (4)
H14	0.9728	0.3513	0.3916	0.044*
C15	0.9921 (2)	0.34180 (18)	0.20595 (18)	0.0371 (4)
H15	1.0931	0.2956	0.1912	0.045*
C16	0.9148 (2)	0.37706 (17)	0.11057 (15)	0.0323 (3)
C17	0.7679 (2)	0.44305 (16)	0.12597 (14)	0.0265 (3)
H17	0.7163	0.4660	0.0582	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.02052 (17)	0.02127 (17)	0.01861 (17)	0.00476 (12)	0.00231 (12)	0.00675 (13)
F1	0.0390 (6)	0.0602 (7)	0.0312 (5)	0.0154 (5)	0.0133 (4)	−0.0012 (5)
O1	0.0280 (5)	0.0234 (5)	0.0305 (5)	0.0062 (4)	0.0071 (4)	0.0132 (4)
O2	0.0254 (5)	0.0253 (5)	0.0263 (5)	0.0054 (4)	0.0083 (4)	0.0105 (4)
O3	0.0276 (5)	0.0333 (6)	0.0225 (5)	0.0072 (4)	−0.0016 (4)	0.0088 (4)
C1	0.0224 (6)	0.0212 (6)	0.0211 (6)	0.0070 (5)	0.0040 (5)	0.0082 (5)
C2	0.0199 (6)	0.0214 (6)	0.0233 (7)	0.0074 (5)	0.0030 (5)	0.0075 (5)
C3	0.0311 (7)	0.0235 (7)	0.0232 (7)	0.0088 (6)	0.0043 (6)	0.0089 (6)
C4	0.0373 (8)	0.0306 (8)	0.0239 (7)	0.0141 (6)	0.0031 (6)	0.0072 (6)
C5	0.0328 (8)	0.0263 (7)	0.0276 (7)	0.0100 (6)	−0.0015 (6)	0.0011 (6)
C6	0.0216 (7)	0.0214 (7)	0.0355 (8)	0.0060 (5)	0.0012 (6)	0.0059 (6)
C7	0.0215 (7)	0.0234 (7)	0.0275 (7)	0.0074 (5)	0.0042 (5)	0.0101 (6)
C8	0.0249 (7)	0.0252 (7)	0.0265 (7)	0.0089 (6)	0.0054 (6)	0.0114 (6)
C9	0.0783 (14)	0.0416 (10)	0.0234 (8)	0.0234 (10)	0.0089 (8)	0.0094 (7)
C10	0.0287 (8)	0.0220 (7)	0.0509 (10)	0.0028 (6)	0.0031 (7)	0.0084 (7)
C11	0.0464 (10)	0.0374 (9)	0.0293 (8)	0.0127 (7)	0.0115 (7)	0.0190 (7)
C12	0.0200 (6)	0.0190 (6)	0.0210 (6)	0.0029 (5)	0.0022 (5)	0.0047 (5)
C13	0.0271 (7)	0.0314 (7)	0.0268 (7)	0.0066 (6)	0.0045 (6)	0.0133 (6)
C14	0.0308 (8)	0.0410 (9)	0.0430 (9)	0.0128 (7)	0.0014 (7)	0.0209 (8)
C15	0.0266 (8)	0.0329 (8)	0.0458 (10)	0.0119 (6)	0.0031 (7)	0.0061 (7)
C16	0.0261 (7)	0.0310 (8)	0.0265 (7)	0.0044 (6)	0.0055 (6)	−0.0027 (6)
C17	0.0260 (7)	0.0278 (7)	0.0194 (6)	0.0039 (6)	0.0019 (5)	0.0038 (6)

S1—O2	1.4380 (10)	C9—H9A	0.9800
S1—O3	1.4380 (10)	C9—H9B	0.9800
S1—C1	1.7345 (14)	C9—H9C	0.9800
S1—C12	1.7672 (14)	C10—H10A	0.9800
F1—C16	1.3526 (18)	C10—H10B	0.9800
O1—C8	1.3622 (18)	C10—H10C	0.9800
O1—C7	1.3813 (17)	C11—H11A	0.9800
C1—C8	1.3619 (19)	C11—H11B	0.9800
C1—C2	1.4500 (19)	C11—H11C	0.9800
C2—C7	1.3917 (19)	C12—C13	1.385 (2)
C2—C3	1.3965 (19)	C12—C17	1.3920 (19)
C3—C4	1.387 (2)	C13—C14	1.386 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.407 (2)	C14—C15	1.387 (2)
C4—C9	1.510 (2)	C14—H14	0.9500
C5—C6	1.389 (2)	C15—C16	1.370 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.387 (2)	C16—C17	1.375 (2)
C6—C10	1.497 (2)	C17—H17	0.9500
C8—C11	1.482 (2)
O2—S1—O3	119.31 (6)	C4—C9—H9C	109.5
O2—S1—C1	107.39 (6)	H9A—C9—H9C	109.5
O3—S1—C1	109.06 (7)	H9B—C9—H9C	109.5
O2—S1—C12	107.29 (6)	C6—C10—H10A	109.5
O3—S1—C12	107.42 (6)	C6—C10—H10B	109.5
C1—S1—C12	105.55 (6)	H10A—C10—H10B	109.5
C8—O1—C7	107.03 (11)	C6—C10—H10C	109.5
C8—C1—C2	107.76 (12)	H10A—C10—H10C	109.5
C8—C1—S1	126.11 (11)	H10B—C10—H10C	109.5
C2—C1—S1	126.13 (10)	C8—C11—H11A	109.5
C7—C2—C3	119.43 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.13 (12)	H11A—C11—H11B	109.5
C3—C2—C1	136.43 (13)	C8—C11—H11C	109.5
C4—C3—C2	118.13 (14)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C13—C12—C17	122.22 (13)
C3—C4—C5	120.14 (14)	C13—C12—S1	119.21 (11)
C3—C4—C9	120.40 (15)	C17—C12—S1	118.57 (11)
C5—C4—C9	119.45 (14)	C12—C13—C14	118.59 (14)
C6—C5—C4	123.35 (14)	C12—C13—H13	120.7
C6—C5—H5	118.3	C14—C13—H13	120.7
C4—C5—H5	118.3	C13—C14—C15	120.51 (15)
C7—C6—C5	114.29 (14)	C13—C14—H14	119.7
C7—C6—C10	121.84 (15)	C15—C14—H14	119.7
C5—C6—C10	123.87 (14)	C16—C15—C14	118.77 (15)
O1—C7—C6	124.66 (13)	C16—C15—H15	120.6
O1—C7—C2	110.69 (12)	C14—C15—H15	120.6
C6—C7—C2	124.65 (14)	F1—C16—C15	118.52 (14)
C1—C8—O1	110.39 (12)	F1—C16—C17	118.28 (15)
C1—C8—C11	134.46 (14)	C15—C16—C17	123.20 (15)
O1—C8—C11	115.15 (13)	C16—C17—C12	116.71 (14)
C4—C9—H9A	109.5	C16—C17—H17	121.6
C4—C9—H9B	109.5	C12—C17—H17	121.6
H9A—C9—H9B	109.5
O2—S1—C1—C8	−158.08 (13)	C1—C2—C7—O1	−0.78 (15)
O3—S1—C1—C8	−27.46 (15)	C3—C2—C7—C6	−0.4 (2)
C12—S1—C1—C8	87.68 (14)	C1—C2—C7—C6	178.54 (14)
O2—S1—C1—C2	21.36 (14)	C2—C1—C8—O1	−0.35 (16)
O3—S1—C1—C2	151.98 (12)	S1—C1—C8—O1	179.17 (10)
C12—S1—C1—C2	−92.88 (13)	C2—C1—C8—C11	179.45 (16)
C8—C1—C2—C7	0.68 (15)	S1—C1—C8—C11	−1.0 (3)
S1—C1—C2—C7	−178.84 (10)	C7—O1—C8—C1	−0.13 (16)
C8—C1—C2—C3	179.38 (16)	C7—O1—C8—C11	−179.98 (12)
S1—C1—C2—C3	−0.1 (2)	O2—S1—C12—C13	−26.71 (13)
C7—C2—C3—C4	1.3 (2)	O3—S1—C12—C13	−156.14 (11)
C1—C2—C3—C4	−177.26 (15)	C1—S1—C12—C13	87.59 (12)
C2—C3—C4—C5	−1.3 (2)	O2—S1—C12—C17	153.52 (11)
C2—C3—C4—C9	177.35 (15)	O3—S1—C12—C17	24.09 (13)
C3—C4—C5—C6	0.5 (2)	C1—S1—C12—C17	−92.18 (12)
C9—C4—C5—C6	−178.17 (16)	C17—C12—C13—C14	−0.3 (2)
C4—C5—C6—C7	0.3 (2)	S1—C12—C13—C14	179.97 (12)
C4—C5—C6—C10	−179.86 (15)	C12—C13—C14—C15	0.1 (2)
C8—O1—C7—C6	−178.73 (14)	C13—C14—C15—C16	0.2 (3)
C8—O1—C7—C2	0.60 (15)	C14—C15—C16—F1	179.97 (15)
C5—C6—C7—O1	178.85 (13)	C14—C15—C16—C17	−0.4 (3)
C10—C6—C7—O1	−1.0 (2)	F1—C16—C17—C12	179.90 (13)
C5—C6—C7—C2	−0.4 (2)	C15—C16—C17—C12	0.3 (2)
C10—C6—C7—C2	179.80 (13)	C13—C12—C17—C16	0.0 (2)
C3—C2—C7—O1	−179.75 (12)	S1—C12—C17—C16	179.81 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.60	3.4890 (18)	156
C13—H13···O2i	0.95	2.51	3.4482 (18)	170
C17—H17···O3ii	0.95	2.41	3.3432 (18)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.60	3.4890 (18)	156
C13—H13⋯O2i	0.95	2.51	3.4482 (18)	170
C17—H17⋯O3ii	0.95	2.41	3.3432 (18)	168

Symmetry codes: (i) ; (ii) .