3-(2-Fluoro-phenyl-sulfin-yl)-2,4,5,6-tetra-methyl-1-benzofuran.

In the title compound, C(18)H(17)FO(2)S, the 2-fluoro-phenyl ring makes a dihedral angle of 85.45 (4)° with the mean plane [r.m.s. deviation = 0.017 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Seo et al. (2011a ▶,b ▶).

Experimental

Crystal data

C18H17FO2S

M = 316.38

Monoclinic,

a = 14.6851 (4) Å

b = 6.0786 (2) Å

c = 17.1647 (4) Å

β = 102.223 (1)°

V = 1497.47 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.33 × 0.30 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.593, T max = 0.746

24418 measured reflections

3264 independent reflections

2803 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.08

3264 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.40 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/S1600536812035714/lr2079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035714/lr2079Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035714/lr2079Isup3.cml

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

C18H17FO2S	F(000) = 664
Mr = 316.38	Dx = 1.403 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7371 reflections
a = 14.6851 (4) Å	θ = 2.4–28.3°
b = 6.0786 (2) Å	µ = 0.23 mm−1
c = 17.1647 (4) Å	T = 173 K
β = 102.223 (1)°	Block, colourless
V = 1497.47 (7) Å3	0.33 × 0.30 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3264 independent reflections
Radiation source: rotating anode	2803 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.043
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.4°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −7→7
Tmin = 0.593, Tmax = 0.746	l = −21→21
24418 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 = 1.08	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.658P] where P = (Fo2 + 2Fc2)/3
3264 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.40 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	0.21698 (3)	0.16904 (7)	0.41644 (2)	0.03042 (13)
F1	0.03896 (7)	0.32249 (18)	0.45203 (6)	0.0416 (3)
O1	0.23316 (7)	0.20829 (17)	0.64475 (6)	0.0281 (3)
O2	0.29956 (9)	0.1670 (2)	0.37937 (7)	0.0404 (3)
C1	0.24718 (11)	0.2438 (2)	0.51761 (9)	0.0252 (3)
C2	0.29950 (10)	0.4245 (2)	0.56249 (9)	0.0220 (3)
C3	0.35600 (10)	0.5993 (2)	0.54765 (9)	0.0227 (3)
C4	0.39264 (10)	0.7410 (2)	0.61115 (9)	0.0237 (3)
C5	0.37560 (10)	0.7064 (2)	0.68833 (9)	0.0243 (3)
C6	0.32286 (10)	0.5281 (3)	0.70348 (9)	0.0254 (3)
H6	0.3123	0.5001	0.7553	0.030*
C7	0.28666 (10)	0.3939 (2)	0.63998 (9)	0.0233 (3)
C8	0.21110 (10)	0.1214 (2)	0.56972 (10)	0.0272 (3)
C9	0.37842 (12)	0.6310 (3)	0.46666 (9)	0.0300 (3)
H9A	0.3410	0.7522	0.4390	0.045*
H9B	0.3641	0.4956	0.4355	0.045*
H9C	0.4447	0.6657	0.4729	0.045*
C10	0.45310 (11)	0.9320 (3)	0.59733 (10)	0.0322 (4)
H10A	0.5185	0.8857	0.6083	0.048*
H10B	0.4455	1.0536	0.6329	0.048*
H10C	0.4346	0.9807	0.5418	0.048*
C11	0.41622 (11)	0.8586 (3)	0.75636 (10)	0.0317 (4)
H11A	0.4009	0.8035	0.8057	0.048*
H11B	0.3900	1.0063	0.7450	0.048*
H11C	0.4841	0.8648	0.7626	0.048*
C12	0.15203 (12)	−0.0779 (3)	0.56170 (12)	0.0372 (4)
H12A	0.1433	−0.1347	0.5072	0.056*
H12B	0.0913	−0.0408	0.5733	0.056*
H12C	0.1824	−0.1902	0.5993	0.056*
C13	0.15085 (11)	0.4095 (3)	0.37763 (9)	0.0272 (3)
C14	0.06721 (11)	0.4548 (3)	0.39837 (9)	0.0295 (3)
C15	0.01129 (12)	0.6277 (3)	0.36623 (10)	0.0364 (4)
H15	−0.0459	0.6556	0.3818	0.044*
C16	0.04042 (13)	0.7601 (3)	0.31056 (11)	0.0398 (4)
H16	0.0033	0.8814	0.2880	0.048*
C17	0.12312 (13)	0.7163 (3)	0.28783 (10)	0.0390 (4)
H17	0.1426	0.8078	0.2495	0.047*
C18	0.17811 (12)	0.5402 (3)	0.32034 (10)	0.0338 (4)
H18	0.2343	0.5089	0.3035	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0325 (2)	0.0273 (2)	0.0304 (2)	0.00289 (16)	0.00422 (17)	−0.00763 (15)
F1	0.0326 (6)	0.0485 (6)	0.0465 (6)	−0.0011 (4)	0.0151 (5)	0.0097 (5)
O1	0.0284 (6)	0.0253 (5)	0.0309 (6)	−0.0028 (4)	0.0073 (5)	0.0056 (4)
O2	0.0386 (7)	0.0465 (7)	0.0376 (7)	0.0107 (6)	0.0114 (6)	−0.0102 (6)
C1	0.0249 (8)	0.0223 (7)	0.0276 (8)	0.0023 (6)	0.0036 (6)	−0.0011 (6)
C2	0.0214 (7)	0.0218 (7)	0.0227 (7)	0.0033 (6)	0.0044 (6)	0.0013 (5)
C3	0.0209 (7)	0.0236 (7)	0.0243 (8)	0.0028 (6)	0.0063 (6)	0.0027 (5)
C4	0.0204 (7)	0.0238 (7)	0.0274 (8)	0.0018 (6)	0.0062 (6)	0.0027 (6)
C5	0.0210 (7)	0.0271 (7)	0.0241 (8)	0.0033 (6)	0.0032 (6)	0.0005 (6)
C6	0.0253 (7)	0.0305 (8)	0.0210 (7)	0.0036 (6)	0.0065 (6)	0.0045 (6)
C7	0.0202 (7)	0.0225 (7)	0.0278 (8)	0.0000 (6)	0.0065 (6)	0.0057 (6)
C8	0.0234 (8)	0.0234 (7)	0.0332 (8)	0.0010 (6)	0.0024 (6)	0.0012 (6)
C9	0.0331 (9)	0.0327 (8)	0.0258 (8)	−0.0011 (7)	0.0099 (7)	0.0024 (6)
C10	0.0307 (8)	0.0312 (8)	0.0356 (9)	−0.0071 (7)	0.0089 (7)	−0.0005 (7)
C11	0.0329 (9)	0.0338 (9)	0.0276 (8)	−0.0007 (7)	0.0042 (7)	−0.0039 (7)
C12	0.0355 (9)	0.0257 (8)	0.0497 (11)	−0.0055 (7)	0.0075 (8)	0.0027 (7)
C13	0.0264 (8)	0.0301 (8)	0.0233 (8)	−0.0002 (6)	0.0012 (6)	−0.0055 (6)
C14	0.0274 (8)	0.0339 (8)	0.0265 (8)	−0.0031 (6)	0.0042 (6)	−0.0028 (6)
C15	0.0307 (9)	0.0419 (9)	0.0354 (9)	0.0064 (7)	0.0039 (7)	−0.0050 (7)
C16	0.0438 (11)	0.0342 (9)	0.0359 (9)	0.0043 (8)	−0.0037 (8)	−0.0001 (7)
C17	0.0448 (11)	0.0409 (10)	0.0283 (9)	−0.0078 (8)	0.0008 (8)	0.0046 (7)
C18	0.0298 (9)	0.0446 (10)	0.0263 (8)	−0.0036 (7)	0.0041 (7)	−0.0024 (7)

S1—O2	1.4839 (13)	C9—H9C	0.9800
S1—C1	1.7587 (16)	C10—H10A	0.9800
S1—C13	1.8028 (16)	C10—H10B	0.9800
F1—C14	1.3524 (19)	C10—H10C	0.9800
O1—C8	1.3660 (19)	C11—H11A	0.9800
O1—C7	1.3869 (17)	C11—H11B	0.9800
C1—C8	1.355 (2)	C11—H11C	0.9800
C1—C2	1.463 (2)	C12—H12A	0.9800
C2—C7	1.395 (2)	C12—H12B	0.9800
C2—C3	1.404 (2)	C12—H12C	0.9800
C3—C4	1.404 (2)	C13—C14	1.377 (2)
C3—C9	1.507 (2)	C13—C18	1.387 (2)
C4—C5	1.415 (2)	C14—C15	1.375 (2)
C4—C10	1.511 (2)	C15—C16	1.384 (3)
C5—C6	1.389 (2)	C15—H15	0.9500
C5—C11	1.510 (2)	C16—C17	1.378 (3)
C6—C7	1.375 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.386 (3)
C8—C12	1.479 (2)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800
O2—S1—C1	111.56 (7)	C4—C10—H10B	109.5
O2—S1—C13	105.88 (8)	H10A—C10—H10B	109.5
C1—S1—C13	99.13 (7)	C4—C10—H10C	109.5
C8—O1—C7	106.45 (12)	H10A—C10—H10C	109.5
C8—C1—C2	107.46 (13)	H10B—C10—H10C	109.5
C8—C1—S1	117.25 (12)	C5—C11—H11A	109.5
C2—C1—S1	135.13 (12)	C5—C11—H11B	109.5
C7—C2—C3	118.58 (13)	H11A—C11—H11B	109.5
C7—C2—C1	103.89 (13)	C5—C11—H11C	109.5
C3—C2—C1	137.49 (14)	H11A—C11—H11C	109.5
C4—C3—C2	117.87 (13)	H11B—C11—H11C	109.5
C4—C3—C9	120.99 (13)	C8—C12—H12A	109.5
C2—C3—C9	121.13 (14)	C8—C12—H12B	109.5
C3—C4—C5	121.39 (14)	H12A—C12—H12B	109.5
C3—C4—C10	119.42 (14)	C8—C12—H12C	109.5
C5—C4—C10	119.18 (14)	H12A—C12—H12C	109.5
C6—C5—C4	120.50 (14)	H12B—C12—H12C	109.5
C6—C5—C11	118.57 (14)	C14—C13—C18	118.43 (15)
C4—C5—C11	120.91 (14)	C14—C13—S1	120.45 (13)
C7—C6—C5	116.88 (14)	C18—C13—S1	120.81 (13)
C7—C6—H6	121.6	F1—C14—C15	118.99 (15)
C5—C6—H6	121.6	F1—C14—C13	118.43 (14)
C6—C7—O1	124.37 (13)	C15—C14—C13	122.58 (16)
C6—C7—C2	124.69 (14)	C14—C15—C16	118.40 (17)
O1—C7—C2	110.94 (13)	C14—C15—H15	120.8
C1—C8—O1	111.23 (13)	C16—C15—H15	120.8
C1—C8—C12	133.80 (16)	C17—C16—C15	120.20 (17)
O1—C8—C12	114.94 (14)	C17—C16—H16	119.9
C3—C9—H9A	109.5	C15—C16—H16	119.9
C3—C9—H9B	109.5	C16—C17—C18	120.57 (17)
H9A—C9—H9B	109.5	C16—C17—H17	119.7
C3—C9—H9C	109.5	C18—C17—H17	119.7
H9A—C9—H9C	109.5	C17—C18—C13	119.79 (16)
H9B—C9—H9C	109.5	C17—C18—H18	120.1
C4—C10—H10A	109.5	C13—C18—H18	120.1
O2—S1—C1—C8	−134.50 (13)	C3—C2—C7—C6	2.4 (2)
C13—S1—C1—C8	114.31 (13)	C1—C2—C7—C6	−179.26 (14)
O2—S1—C1—C2	50.87 (17)	C3—C2—C7—O1	−176.94 (12)
C13—S1—C1—C2	−60.32 (17)	C1—C2—C7—O1	1.35 (16)
C8—C1—C2—C7	−1.67 (16)	C2—C1—C8—O1	1.44 (17)
S1—C1—C2—C7	173.33 (13)	S1—C1—C8—O1	−174.59 (10)
C8—C1—C2—C3	176.11 (17)	C2—C1—C8—C12	179.33 (16)
S1—C1—C2—C3	−8.9 (3)	S1—C1—C8—C12	3.3 (2)
C7—C2—C3—C4	−3.3 (2)	C7—O1—C8—C1	−0.60 (17)
C1—C2—C3—C4	179.19 (16)	C7—O1—C8—C12	−178.92 (13)
C7—C2—C3—C9	175.39 (14)	O2—S1—C13—C14	177.56 (12)
C1—C2—C3—C9	−2.1 (3)	C1—S1—C13—C14	−66.81 (14)
C2—C3—C4—C5	1.7 (2)	O2—S1—C13—C18	4.09 (15)
C9—C3—C4—C5	−176.96 (14)	C1—S1—C13—C18	119.73 (13)
C2—C3—C4—C10	−179.50 (13)	C18—C13—C14—F1	177.57 (14)
C9—C3—C4—C10	1.8 (2)	S1—C13—C14—F1	3.9 (2)
C3—C4—C5—C6	0.9 (2)	C18—C13—C14—C15	−1.9 (2)
C10—C4—C5—C6	−177.87 (14)	S1—C13—C14—C15	−175.52 (13)
C3—C4—C5—C11	179.36 (13)	F1—C14—C15—C16	−179.13 (15)
C10—C4—C5—C11	0.6 (2)	C13—C14—C15—C16	0.3 (3)
C4—C5—C6—C7	−1.8 (2)	C14—C15—C16—C17	0.7 (3)
C11—C5—C6—C7	179.67 (13)	C15—C16—C17—C18	−0.1 (3)
C5—C6—C7—O1	179.48 (13)	C16—C17—C18—C13	−1.5 (3)
C5—C6—C7—C2	0.2 (2)	C14—C13—C18—C17	2.4 (2)
C8—O1—C7—C6	−179.93 (14)	S1—C13—C18—C17	176.04 (13)
C8—O1—C7—C2	−0.54 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.40	3.3279 (19)	165
C12—H12C···Cg1ii	0.98	2.69	3.486 (2)	138
C16—H16···Cg2iii	0.95	2.70	3.553 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 2-fluoro­phenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.40	3.3279 (19)	165
C12—H12C⋯Cg1ii	0.98	2.69	3.486 (2)	138
C16—H16⋯Cg2iii	0.95	2.70	3.553 (2)	149

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