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

In the title compound, C17H13FO4S, the 3-fluoro-phenyl ring makes a dihedral angle of 6.14 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯F, C-H⋯O and C-H⋯π inter-actions, forming a three--dimensional network. The crystal structure also exhibits slipped π-π inter-actions between the 3-fluoro-phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.769 (2) Å and slippage = 1.684 (2) Å].

Related literature

For background information on and the crystal structures of related benzofuran compounds, see: Choi et al. (2010 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C17H13FO4S

M = 332.33

Monoclinic,

a = 8.8516 (2) Å

b = 21.8221 (4) Å

c = 7.7228 (2) Å

β = 102.949 (1)°

V = 1453.80 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.39 × 0.29 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.937

14376 measured reflections

3600 independent reflections

3131 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.02

3600 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.35 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044832/mw2094sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044832/mw2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044832/mw2094Isup3.cml

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

C17H13FO4S	F(000) = 688
Mr = 332.33	Dx = 1.518 Mg m−3
Monoclinic, P21/c	Melting point: 408 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8516 (2) Å	Cell parameters from 6139 reflections
b = 21.8221 (4) Å	θ = 2.9–28.2°
c = 7.7228 (2) Å	µ = 0.25 mm−1
β = 102.949 (1)°	T = 173 K
V = 1453.80 (6) Å3	Block, colourless
Z = 4	0.39 × 0.29 × 0.26 mm

Bruker SMART APEXII CCD diffractometer	3600 independent reflections
Radiation source: rotating anode	3131 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −29→27
Tmin = 0.908, Tmax = 0.937	l = −10→10
14376 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.7371P] where P = (Fo2 + 2Fc2)/3
3600 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.35 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	0.20748 (4)	0.653717 (15)	0.40724 (5)	0.02313 (11)
F1	−0.09845 (13)	0.46852 (5)	0.11643 (15)	0.0452 (3)
O1	0.44774 (12)	0.52350 (4)	0.70767 (14)	0.0247 (2)
O2	0.76433 (15)	0.73096 (6)	0.93233 (18)	0.0424 (3)
O3	0.86160 (15)	0.64201 (6)	1.07899 (18)	0.0431 (3)
O4	0.18119 (13)	0.70803 (5)	0.51487 (16)	0.0341 (3)
C1	0.33826 (16)	0.60530 (6)	0.55117 (19)	0.0215 (3)
C2	0.47112 (16)	0.62662 (6)	0.68258 (18)	0.0222 (3)
C3	0.54231 (17)	0.68385 (7)	0.7276 (2)	0.0252 (3)
H3	0.5037	0.7207	0.6683	0.030*
C4	0.67160 (18)	0.68235 (7)	0.8635 (2)	0.0271 (3)
C5	0.72968 (17)	0.62887 (7)	0.9530 (2)	0.0278 (3)
C6	0.66316 (17)	0.57266 (7)	0.9140 (2)	0.0271 (3)
H6	0.7020	0.5362	0.9755	0.033*
C7	0.53247 (16)	0.57424 (6)	0.77457 (19)	0.0229 (3)
C8	0.32896 (16)	0.54330 (6)	0.57115 (19)	0.0223 (3)
C9	0.8859 (2)	0.70603 (8)	1.0666 (2)	0.0403 (4)
H9A	0.9872	0.7137	1.0365	0.048*
H9B	0.8866	0.7259	1.1821	0.048*
C10	0.22658 (16)	0.49448 (6)	0.48447 (19)	0.0225 (3)
C11	0.10942 (17)	0.50551 (7)	0.3331 (2)	0.0257 (3)
H11	0.0948	0.5451	0.2812	0.031*
C12	0.01626 (18)	0.45741 (7)	0.2619 (2)	0.0274 (3)
C13	0.03117 (18)	0.39881 (7)	0.3285 (2)	0.0292 (3)
H13	−0.0358	0.3668	0.2743	0.035*
C14	0.14759 (19)	0.38828 (7)	0.4776 (2)	0.0314 (3)
H14	0.1613	0.3483	0.5272	0.038*
C15	0.24452 (18)	0.43523 (7)	0.5557 (2)	0.0280 (3)
H15	0.3238	0.4272	0.6583	0.034*
C16	0.33604 (19)	0.67847 (7)	0.2700 (2)	0.0306 (3)
H16A	0.2947	0.7164	0.2061	0.037*
H16B	0.4390	0.6880	0.3462	0.037*
C17	0.3535 (2)	0.62964 (10)	0.1369 (3)	0.0450 (4)
H17A	0.3961	0.5923	0.2000	0.068*
H17B	0.4237	0.6443	0.0642	0.068*
H17C	0.2519	0.6206	0.0600	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.02202 (18)	0.01839 (17)	0.02712 (19)	0.00208 (12)	0.00156 (13)	0.00075 (13)
F1	0.0445 (6)	0.0362 (5)	0.0436 (6)	−0.0053 (4)	−0.0138 (5)	−0.0012 (4)
O1	0.0256 (5)	0.0197 (5)	0.0266 (5)	0.0015 (4)	0.0013 (4)	0.0023 (4)
O2	0.0397 (7)	0.0311 (6)	0.0465 (7)	−0.0092 (5)	−0.0113 (6)	−0.0031 (5)
O3	0.0365 (7)	0.0404 (7)	0.0419 (7)	−0.0063 (5)	−0.0133 (5)	0.0026 (5)
O4	0.0370 (6)	0.0226 (5)	0.0417 (7)	0.0079 (4)	0.0069 (5)	−0.0049 (5)
C1	0.0206 (6)	0.0208 (6)	0.0233 (6)	0.0025 (5)	0.0050 (5)	0.0011 (5)
C2	0.0216 (6)	0.0227 (7)	0.0226 (7)	0.0025 (5)	0.0056 (5)	−0.0009 (5)
C3	0.0261 (7)	0.0212 (7)	0.0278 (7)	0.0020 (5)	0.0046 (6)	−0.0011 (5)
C4	0.0264 (7)	0.0257 (7)	0.0288 (7)	−0.0023 (6)	0.0051 (6)	−0.0037 (6)
C5	0.0225 (7)	0.0342 (8)	0.0248 (7)	−0.0003 (6)	0.0011 (6)	−0.0010 (6)
C6	0.0262 (7)	0.0271 (7)	0.0264 (7)	0.0040 (6)	0.0021 (6)	0.0047 (6)
C7	0.0233 (7)	0.0211 (7)	0.0241 (7)	0.0002 (5)	0.0051 (5)	0.0000 (5)
C8	0.0219 (6)	0.0220 (7)	0.0225 (7)	0.0022 (5)	0.0041 (5)	0.0007 (5)
C9	0.0382 (9)	0.0403 (9)	0.0363 (9)	−0.0093 (8)	−0.0048 (7)	−0.0005 (7)
C10	0.0241 (7)	0.0196 (6)	0.0253 (7)	0.0001 (5)	0.0086 (5)	−0.0007 (5)
C11	0.0279 (7)	0.0212 (7)	0.0278 (7)	0.0001 (5)	0.0058 (6)	−0.0005 (5)
C12	0.0271 (7)	0.0274 (7)	0.0270 (7)	0.0003 (6)	0.0045 (6)	−0.0030 (6)
C13	0.0319 (8)	0.0242 (7)	0.0333 (8)	−0.0058 (6)	0.0111 (6)	−0.0059 (6)
C14	0.0391 (9)	0.0202 (7)	0.0360 (8)	−0.0007 (6)	0.0106 (7)	0.0017 (6)
C15	0.0308 (7)	0.0236 (7)	0.0289 (7)	0.0009 (6)	0.0050 (6)	0.0031 (6)
C16	0.0310 (8)	0.0296 (8)	0.0301 (8)	−0.0033 (6)	0.0046 (6)	0.0080 (6)
C17	0.0486 (11)	0.0550 (12)	0.0347 (9)	−0.0016 (9)	0.0162 (8)	−0.0018 (8)

S1—O4	1.4954 (11)	C8—C10	1.4602 (19)
S1—C1	1.7651 (14)	C9—H9A	0.9900
S1—C16	1.8029 (16)	C9—H9B	0.9900
F1—C12	1.3568 (18)	C10—C11	1.399 (2)
O1—C7	1.3717 (17)	C10—C15	1.400 (2)
O1—C8	1.3809 (16)	C11—C12	1.372 (2)
O2—C4	1.3733 (18)	C11—H11	0.9500
O2—C9	1.424 (2)	C12—C13	1.373 (2)
O3—C5	1.3724 (18)	C13—C14	1.381 (2)
O3—C9	1.420 (2)	C13—H13	0.9500
C1—C8	1.366 (2)	C14—C15	1.385 (2)
C1—C2	1.4473 (19)	C14—H14	0.9500
C2—C7	1.3905 (19)	C15—H15	0.9500
C2—C3	1.407 (2)	C16—C17	1.513 (3)
C3—C4	1.369 (2)	C16—H16A	0.9900
C3—H3	0.9500	C16—H16B	0.9900
C4—C5	1.395 (2)	C17—H17A	0.9800
C5—C6	1.365 (2)	C17—H17B	0.9800
C6—C7	1.393 (2)	C17—H17C	0.9800
C6—H6	0.9500
O4—S1—C1	106.63 (7)	O3—C9—H9B	109.9
O4—S1—C16	106.65 (7)	O2—C9—H9B	109.9
C1—S1—C16	97.95 (7)	H9A—C9—H9B	108.3
C7—O1—C8	107.07 (10)	C11—C10—C15	118.99 (13)
C4—O2—C9	105.97 (13)	C11—C10—C8	121.69 (13)
C5—O3—C9	105.99 (13)	C15—C10—C8	119.32 (13)
C8—C1—C2	107.41 (12)	C12—C11—C10	118.03 (14)
C8—C1—S1	128.05 (11)	C12—C11—H11	121.0
C2—C1—S1	124.35 (11)	C10—C11—H11	121.0
C7—C2—C3	120.10 (13)	F1—C12—C11	117.79 (14)
C7—C2—C1	104.88 (12)	F1—C12—C13	117.90 (13)
C3—C2—C1	135.01 (13)	C11—C12—C13	124.31 (14)
C4—C3—C2	114.80 (13)	C12—C13—C14	117.26 (14)
C4—C3—H3	122.6	C12—C13—H13	121.4
C2—C3—H3	122.6	C14—C13—H13	121.4
C3—C4—O2	127.07 (14)	C13—C14—C15	120.90 (14)
C3—C4—C5	123.50 (14)	C13—C14—H14	119.5
O2—C4—C5	109.43 (13)	C15—C14—H14	119.5
C6—C5—O3	126.94 (14)	C14—C15—C10	120.50 (14)
C6—C5—C4	123.35 (14)	C14—C15—H15	119.8
O3—C5—C4	109.70 (14)	C10—C15—H15	119.8
C5—C6—C7	113.02 (13)	C17—C16—S1	111.26 (12)
C5—C6—H6	123.5	C17—C16—H16A	109.4
C7—C6—H6	123.5	S1—C16—H16A	109.4
O1—C7—C2	110.68 (12)	C17—C16—H16B	109.4
O1—C7—C6	124.09 (12)	S1—C16—H16B	109.4
C2—C7—C6	125.22 (13)	H16A—C16—H16B	108.0
C1—C8—O1	109.95 (12)	C16—C17—H17A	109.5
C1—C8—C10	135.85 (13)	C16—C17—H17B	109.5
O1—C8—C10	114.20 (12)	H17A—C17—H17B	109.5
O3—C9—O2	108.90 (13)	C16—C17—H17C	109.5
O3—C9—H9A	109.9	H17A—C17—H17C	109.5
O2—C9—H9A	109.9	H17B—C17—H17C	109.5
O4—S1—C1—C8	134.07 (14)	C1—C2—C7—C6	179.62 (14)
C16—S1—C1—C8	−115.83 (15)	C5—C6—C7—O1	178.29 (14)
O4—S1—C1—C2	−40.34 (14)	C5—C6—C7—C2	−0.7 (2)
C16—S1—C1—C2	69.76 (13)	C2—C1—C8—O1	0.08 (16)
C8—C1—C2—C7	−0.34 (16)	S1—C1—C8—O1	−175.09 (10)
S1—C1—C2—C7	175.05 (11)	C2—C1—C8—C10	−179.64 (16)
C8—C1—C2—C3	178.82 (16)	S1—C1—C8—C10	5.2 (3)
S1—C1—C2—C3	−5.8 (2)	C7—O1—C8—C1	0.22 (16)
C7—C2—C3—C4	0.3 (2)	C7—O1—C8—C10	180.00 (12)
C1—C2—C3—C4	−178.78 (16)	C5—O3—C9—O2	0.8 (2)
C2—C3—C4—O2	178.99 (15)	C4—O2—C9—O3	−1.3 (2)
C2—C3—C4—C5	−0.4 (2)	C1—C8—C10—C11	5.9 (3)
C9—O2—C4—C3	−178.18 (17)	O1—C8—C10—C11	−173.83 (13)
C9—O2—C4—C5	1.29 (19)	C1—C8—C10—C15	−173.27 (17)
C9—O3—C5—C6	178.63 (17)	O1—C8—C10—C15	7.0 (2)
C9—O3—C5—C4	−0.03 (19)	C15—C10—C11—C12	0.5 (2)
C3—C4—C5—C6	0.0 (3)	C8—C10—C11—C12	−178.70 (14)
O2—C4—C5—C6	−179.54 (15)	C10—C11—C12—F1	179.18 (13)
C3—C4—C5—O3	178.68 (15)	C10—C11—C12—C13	−0.6 (2)
O2—C4—C5—O3	−0.81 (19)	F1—C12—C13—C14	−179.45 (14)
O3—C5—C6—C7	−177.91 (15)	C11—C12—C13—C14	0.3 (2)
C4—C5—C6—C7	0.6 (2)	C12—C13—C14—C15	0.1 (2)
C8—O1—C7—C2	−0.45 (16)	C13—C14—C15—C10	−0.2 (2)
C8—O1—C7—C6	−179.59 (14)	C11—C10—C15—C14	−0.1 (2)
C3—C2—C7—O1	−178.82 (13)	C8—C10—C15—C14	179.08 (14)
C1—C2—C7—O1	0.49 (16)	O4—S1—C16—C17	−172.19 (12)
C3—C2—C7—C6	0.3 (2)	C1—S1—C16—C17	77.73 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O4i	0.99	2.45	3.314 (2)	145
C9—H9B···O2ii	0.99	2.59	3.519 (3)	156
C16—H16A···O4iii	0.99	2.29	3.2689 (19)	169
C6—H6···F1iv	0.95	2.37	3.2532 (18)	154
C17—H17B···Cg1v	0.98	2.74	3.642 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O4i	0.99	2.45	3.314 (2)	145
C9—H9B⋯O2ii	0.99	2.59	3.519 (3)	156
C16—H16A⋯O4iii	0.99	2.29	3.2689 (19)	169
C6—H6⋯F1iv	0.95	2.37	3.2532 (18)	154
C17—H17B⋯Cg1v	0.98	2.74	3.642 (3)	153

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