3-Ethyl-sulfinyl-2-(4-fluoro-phen-yl)-5,6-methyl-enedi-oxy-1-benzofuran.

In the title compound, C(17)H(13)FO(4)S, the 4-fluoro-phenyl ring makes a dihedral angle of 4.92 (4)° with the plane of the 5,6-methyl-enedi-oxy-1-benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯F hydrogen bonds.

Related literature

For the crystal structures of similar 2-aryl-5,6-methyl­enedi­oxy-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2010 ▶). 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 ▶).

Experimental

Crystal data

C17H13FO4S

M = 332.33

Triclinic,

a = 7.1081 (9) Å

b = 9.631 (1) Å

c = 10.708 (1) Å

α = 93.201 (2)°

β = 95.510 (2)°

γ = 105.423 (2)°

V = 700.85 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.40 × 0.36 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.610, T max = 0.746

6872 measured reflections

3194 independent reflections

2955 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.03

3194 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.34 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/S160053681001617X/fl2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001617X/fl2302Isup2.hkl

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

C17H13FO4S	Z = 2
Mr = 332.33	F(000) = 344
Triclinic, P1	Dx = 1.575 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1081 (9) Å	Cell parameters from 4697 reflections
b = 9.631 (1) Å	θ = 2.2–27.5°
c = 10.708 (1) Å	µ = 0.26 mm−1
α = 93.201 (2)°	T = 173 K
β = 95.510 (2)°	Block, colourless
γ = 105.423 (2)°	0.40 × 0.36 × 0.28 mm
V = 700.85 (13) Å3

Bruker SMART APEXII CCD diffractometer	3194 independent reflections
Radiation source: rotating anode	2955 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.021
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
Tmin = 0.610, Tmax = 0.746	l = −13→13
6872 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.3499P] where P = (Fo2 + 2Fc2)/3
3194 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.35 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	0.03741 (5)	0.18237 (3)	0.61999 (3)	0.02096 (11)
F	0.26284 (17)	0.20685 (12)	0.00053 (8)	0.0408 (3)
O1	0.28566 (14)	0.56937 (10)	0.50825 (8)	0.0191 (2)
O2	0.19966 (18)	0.67938 (11)	0.99731 (9)	0.0294 (2)
O3	0.33831 (17)	0.87862 (11)	0.89214 (10)	0.0291 (2)
O4	−0.10317 (16)	0.18196 (12)	0.71512 (11)	0.0311 (3)
C1	0.14785 (19)	0.36484 (14)	0.59545 (12)	0.0173 (3)
C2	0.18385 (19)	0.48389 (14)	0.69123 (12)	0.0174 (3)
C3	0.15149 (19)	0.49635 (14)	0.81894 (12)	0.0192 (3)
H3	0.0949	0.4172	0.8618	0.023*
C4	0.2106 (2)	0.63511 (15)	0.87430 (12)	0.0204 (3)
C5	0.2704 (3)	0.83253 (17)	1.00884 (14)	0.0312 (3)
H5A	0.3770	0.8637	1.0766	0.037*
H5B	0.1660	0.8749	1.0281	0.037*
C6	0.2941 (2)	0.75576 (15)	0.81127 (13)	0.0209 (3)
C7	0.3259 (2)	0.74755 (14)	0.68725 (13)	0.0209 (3)
H7	0.3804	0.8277	0.6449	0.025*
C8	0.26789 (19)	0.60610 (14)	0.63121 (12)	0.0176 (3)
C9	0.21082 (19)	0.42130 (14)	0.48737 (12)	0.0176 (3)
C10	0.22097 (19)	0.36334 (15)	0.35978 (12)	0.0189 (3)
C11	0.1684 (2)	0.21477 (15)	0.32548 (13)	0.0234 (3)
H11	0.1246	0.1505	0.3849	0.028*
C12	0.1803 (2)	0.16148 (17)	0.20450 (14)	0.0273 (3)
H12	0.1437	0.0626	0.1817	0.033*
C13	0.2479 (2)	0.25910 (18)	0.11899 (13)	0.0265 (3)
C14	0.3012 (2)	0.40604 (17)	0.14766 (13)	0.0266 (3)
H14	0.3462	0.4690	0.0875	0.032*
C15	0.2863 (2)	0.45824 (15)	0.26865 (13)	0.0225 (3)
H15	0.3201	0.5575	0.2896	0.027*
C16	0.2528 (2)	0.14580 (16)	0.70193 (13)	0.0248 (3)
H16A	0.3120	0.2226	0.7678	0.030*
H16B	0.2129	0.0560	0.7414	0.030*
C17	0.4039 (2)	0.13464 (17)	0.61352 (15)	0.0276 (3)
H17A	0.3473	0.0563	0.5501	0.041*
H17B	0.5163	0.1173	0.6604	0.041*
H17C	0.4435	0.2233	0.5741	0.041*

	U11	U22	U33	U12	U13	U23
S	0.02154 (18)	0.01632 (17)	0.02366 (18)	0.00116 (13)	0.00638 (13)	0.00332 (12)
F	0.0605 (7)	0.0474 (6)	0.0187 (4)	0.0201 (5)	0.0118 (4)	−0.0023 (4)
O1	0.0233 (5)	0.0164 (5)	0.0176 (4)	0.0042 (4)	0.0053 (4)	0.0030 (3)
O2	0.0455 (7)	0.0222 (5)	0.0197 (5)	0.0063 (5)	0.0095 (4)	−0.0014 (4)
O3	0.0437 (6)	0.0185 (5)	0.0237 (5)	0.0060 (4)	0.0059 (4)	−0.0024 (4)
O4	0.0287 (6)	0.0290 (6)	0.0365 (6)	0.0040 (4)	0.0162 (5)	0.0079 (5)
C1	0.0169 (6)	0.0165 (6)	0.0184 (6)	0.0038 (5)	0.0036 (5)	0.0018 (5)
C2	0.0157 (6)	0.0171 (6)	0.0194 (6)	0.0043 (5)	0.0028 (5)	0.0021 (5)
C3	0.0202 (6)	0.0189 (6)	0.0186 (6)	0.0039 (5)	0.0046 (5)	0.0036 (5)
C4	0.0212 (6)	0.0232 (7)	0.0178 (6)	0.0072 (5)	0.0043 (5)	0.0017 (5)
C5	0.0412 (9)	0.0237 (7)	0.0253 (7)	0.0030 (6)	0.0080 (6)	−0.0045 (6)
C6	0.0220 (6)	0.0171 (6)	0.0233 (7)	0.0060 (5)	0.0015 (5)	−0.0008 (5)
C7	0.0237 (7)	0.0164 (6)	0.0229 (6)	0.0048 (5)	0.0044 (5)	0.0041 (5)
C8	0.0179 (6)	0.0192 (6)	0.0168 (6)	0.0058 (5)	0.0037 (5)	0.0029 (5)
C9	0.0179 (6)	0.0153 (6)	0.0199 (6)	0.0046 (5)	0.0027 (5)	0.0021 (5)
C10	0.0168 (6)	0.0227 (7)	0.0176 (6)	0.0060 (5)	0.0022 (5)	0.0020 (5)
C11	0.0266 (7)	0.0234 (7)	0.0198 (6)	0.0048 (6)	0.0063 (5)	0.0020 (5)
C12	0.0313 (8)	0.0259 (7)	0.0238 (7)	0.0068 (6)	0.0046 (6)	−0.0028 (6)
C13	0.0290 (7)	0.0376 (8)	0.0158 (6)	0.0139 (6)	0.0048 (5)	−0.0004 (6)
C14	0.0287 (7)	0.0349 (8)	0.0196 (7)	0.0120 (6)	0.0062 (5)	0.0090 (6)
C15	0.0240 (7)	0.0231 (7)	0.0211 (6)	0.0070 (5)	0.0039 (5)	0.0042 (5)
C16	0.0295 (7)	0.0231 (7)	0.0242 (7)	0.0093 (6)	0.0055 (6)	0.0078 (5)
C17	0.0261 (7)	0.0252 (7)	0.0339 (8)	0.0092 (6)	0.0072 (6)	0.0050 (6)

S—O4	1.493 (1)	C7—C8	1.396 (2)
S—C1	1.770 (1)	C7—H7	0.9300
S—C16	1.817 (2)	C9—C10	1.462 (2)
F—C13	1.363 (2)	C10—C11	1.397 (2)
O1—C8	1.371 (2)	C10—C15	1.401 (2)
O1—C9	1.380 (2)	C11—C12	1.385 (2)
O2—C4	1.378 (2)	C11—H11	0.9300
O2—C5	1.420 (2)	C12—C13	1.376 (2)
O3—C6	1.373 (2)	C12—H12	0.9300
O3—C5	1.434 (2)	C13—C14	1.373 (2)
C1—C9	1.370 (2)	C14—C15	1.387 (2)
C1—C2	1.447 (2)	C14—H14	0.9300
C2—C8	1.393 (2)	C15—H15	0.9300
C2—C3	1.412 (2)	C16—C17	1.519 (2)
C3—C4	1.371 (2)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C6	1.399 (2)	C17—H17A	0.9600
C5—H5A	0.9700	C17—H17B	0.9600
C5—H5B	0.9700	C17—H17C	0.9600
C6—C7	1.370 (2)
O4—S—C1	107.47 (6)	C1—C9—O1	109.89 (11)
O4—S—C16	106.53 (7)	C1—C9—C10	135.89 (12)
C1—S—C16	97.30 (7)	O1—C9—C10	114.21 (11)
C8—O1—C9	107.08 (10)	C11—C10—C15	118.46 (12)
C4—O2—C5	106.39 (11)	C11—C10—C9	121.86 (12)
C6—O3—C5	105.79 (11)	C15—C10—C9	119.68 (12)
C9—C1—C2	107.48 (11)	C12—C11—C10	121.19 (13)
C9—C1—S	128.49 (10)	C12—C11—H11	119.4
C2—C1—S	124.02 (10)	C10—C11—H11	119.4
C8—C2—C3	120.58 (12)	C13—C12—C11	118.09 (14)
C8—C2—C1	104.70 (11)	C13—C12—H12	121.0
C3—C2—C1	134.72 (12)	C11—C12—H12	121.0
C4—C3—C2	114.24 (12)	F—C13—C14	118.71 (13)
C4—C3—H3	122.9	F—C13—C12	118.20 (14)
C2—C3—H3	122.9	C14—C13—C12	123.09 (13)
C3—C4—O2	127.02 (13)	C13—C14—C15	118.31 (14)
C3—C4—C6	123.81 (13)	C13—C14—H14	120.8
O2—C4—C6	109.17 (12)	C15—C14—H14	120.8
O2—C5—O3	108.58 (11)	C14—C15—C10	120.84 (13)
O2—C5—H5A	110.0	C14—C15—H15	119.6
O3—C5—H5A	110.0	C10—C15—H15	119.6
O2—C5—H5B	110.0	C17—C16—S	111.94 (10)
O3—C5—H5B	110.0	C17—C16—H16A	109.2
H5A—C5—H5B	108.4	S—C16—H16A	109.2
C7—C6—O3	126.72 (13)	C17—C16—H16B	109.2
C7—C6—C4	123.41 (13)	S—C16—H16B	109.2
O3—C6—C4	109.87 (12)	H16A—C16—H16B	107.9
C6—C7—C8	112.81 (12)	C16—C17—H17A	109.5
C6—C7—H7	123.6	C16—C17—H17B	109.5
C8—C7—H7	123.6	H17A—C17—H17B	109.5
O1—C8—C2	110.85 (11)	C16—C17—H17C	109.5
O1—C8—C7	124.01 (12)	H17A—C17—H17C	109.5
C2—C8—C7	125.15 (12)	H17B—C17—H17C	109.5
O4—S—C1—C9	−147.47 (12)	C1—C2—C8—O1	−0.34 (14)
C16—S—C1—C9	102.60 (13)	C3—C2—C8—C7	−0.3 (2)
O4—S—C1—C2	31.24 (13)	C1—C2—C8—C7	179.35 (13)
C16—S—C1—C2	−78.69 (12)	C6—C7—C8—O1	−179.57 (12)
C9—C1—C2—C8	0.08 (14)	C6—C7—C8—C2	0.8 (2)
S—C1—C2—C8	−178.86 (10)	C2—C1—C9—O1	0.20 (15)
C9—C1—C2—C3	179.64 (14)	S—C1—C9—O1	179.08 (9)
S—C1—C2—C3	0.7 (2)	C2—C1—C9—C10	178.68 (14)
C8—C2—C3—C4	−0.45 (19)	S—C1—C9—C10	−2.4 (2)
C1—C2—C3—C4	−179.95 (14)	C8—O1—C9—C1	−0.41 (14)
C2—C3—C4—O2	−179.10 (13)	C8—O1—C9—C10	−179.25 (10)
C2—C3—C4—C6	0.7 (2)	C1—C9—C10—C11	−4.3 (2)
C5—O2—C4—C3	−177.56 (14)	O1—C9—C10—C11	174.11 (12)
C5—O2—C4—C6	2.65 (16)	C1—C9—C10—C15	176.13 (15)
C4—O2—C5—O3	−4.39 (17)	O1—C9—C10—C15	−5.45 (17)
C6—O3—C5—O2	4.45 (17)	C15—C10—C11—C12	0.1 (2)
C5—O3—C6—C7	177.68 (14)	C9—C10—C11—C12	−179.47 (13)
C5—O3—C6—C4	−2.82 (16)	C10—C11—C12—C13	0.8 (2)
C3—C4—C6—C7	−0.1 (2)	C11—C12—C13—F	178.92 (13)
O2—C4—C6—C7	179.65 (13)	C11—C12—C13—C14	−0.9 (2)
C3—C4—C6—O3	−179.66 (13)	F—C13—C14—C15	−179.73 (13)
O2—C4—C6—O3	0.13 (16)	C12—C13—C14—C15	0.1 (2)
O3—C6—C7—C8	178.87 (13)	C13—C14—C15—C10	0.9 (2)
C4—C6—C7—C8	−0.6 (2)	C11—C10—C15—C14	−0.9 (2)
C9—O1—C8—C2	0.47 (14)	C9—C10—C15—C14	178.64 (13)
C9—O1—C8—C7	−179.23 (12)	O4—S—C16—C17	176.72 (10)
C3—C2—C8—O1	−179.97 (11)	C1—S—C16—C17	−72.56 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O4i	0.93	2.62	3.380 (2)	140
C16—H16A···Fii	0.97	2.56	3.2090 (17)	125
C17—H17B···O4iii	0.96	2.61	3.469 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O4i	0.93	2.62	3.380 (2)	140
C16—H16A⋯Fii	0.97	2.56	3.2090 (17)	125
C17—H17B⋯O4iii	0.96	2.61	3.469 (2)	149

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