3-(4-Fluoro-phenyl-sulfin-yl)-2,4,6,7-tetra-methyl-1-benzofuran.

In the title compound, C(18)H(17)FO(2)S, the 4-fluoro-phenyl ring is almost perpendicular to the benzofuran fragment [88.07 (5)°]. The crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The mol-ecules form pseudo-helices along the a axis.

Related literature

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

C18H17FO2S

M = 316.38

Orthorhombic,

a = 12.0034 (5) Å

b = 19.7455 (7) Å

c = 6.4918 (3) Å

V = 1538.64 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 169 K

0.18 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.644, T max = 0.746

8107 measured reflections

2280 independent reflections

2175 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.06

2280 reflections

204 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 366 Friedel pairs

Flack parameter: 0.01 (12)

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 I. DOI: 10.1107/S1600536810005702/gw2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005702/gw2077Isup2.hkl

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

C18H17FO2S	F(000) = 664
Mr = 316.38	Dx = 1.366 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4518 reflections
a = 12.0034 (5) Å	θ = 2.7–27.4°
b = 19.7455 (7) Å	µ = 0.23 mm−1
c = 6.4918 (3) Å	T = 169 K
V = 1538.64 (11) Å3	Block, colourless
Z = 4	0.18 × 0.17 × 0.16 mm

Bruker SMART APEXII CCD diffractometer	2280 independent reflections
Radiation source: Rotating Anode	2175 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −13→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −25→25
Tmin = 0.644, Tmax = 0.746	l = −4→8
8107 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1527P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2280 reflections	Δρmax = 0.25 e Å−3
204 parameters	Δρmin = −0.28 e Å−3
1 restraint	Absolute structure: Flack (1983), 366 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (12)

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	0.38790 (4)	0.25971 (2)	0.83129 (12)	0.02606 (12)
F	0.48409 (13)	0.07177 (8)	0.1553 (3)	0.0599 (5)
O1	0.66099 (10)	0.36300 (7)	0.9163 (2)	0.0258 (3)
O2	0.28018 (11)	0.29365 (7)	0.7817 (3)	0.0352 (4)
C1	0.49909 (14)	0.31749 (9)	0.8113 (3)	0.0235 (4)
C2	0.52977 (15)	0.36899 (9)	0.6611 (3)	0.0232 (4)
C3	0.48697 (16)	0.39560 (10)	0.4772 (3)	0.0273 (4)
C4	0.54918 (17)	0.44634 (9)	0.3828 (3)	0.0307 (4)
H4	0.5214	0.4655	0.2587	0.037*
C5	0.65120 (17)	0.47098 (9)	0.4609 (4)	0.0306 (4)
C6	0.69347 (16)	0.44561 (9)	0.6454 (4)	0.0265 (4)
C7	0.62992 (15)	0.39505 (9)	0.7356 (3)	0.0241 (4)
C8	0.57968 (16)	0.31611 (9)	0.9575 (3)	0.0246 (4)
C9	0.38031 (17)	0.37126 (12)	0.3799 (3)	0.0315 (5)
H9A	0.3537	0.4051	0.2812	0.047*
H9B	0.3239	0.3644	0.4871	0.047*
H9C	0.3939	0.3284	0.3081	0.047*
C10	0.71324 (19)	0.52419 (10)	0.3411 (5)	0.0419 (5)
H10A	0.7075	0.5678	0.4126	0.063*
H10B	0.6809	0.5282	0.2031	0.063*
H10C	0.7918	0.5112	0.3297	0.063*
C11	0.80130 (18)	0.46820 (11)	0.7418 (4)	0.0362 (5)
H11A	0.8622	0.4395	0.6920	0.054*
H11B	0.7959	0.4643	0.8920	0.054*
H11C	0.8160	0.5154	0.7043	0.054*
C12	0.59977 (17)	0.27324 (11)	1.1404 (4)	0.0297 (4)
H12A	0.5354	0.2436	1.1630	0.045*
H12B	0.6109	0.3021	1.2615	0.045*
H12C	0.6664	0.2455	1.1179	0.045*
C13	0.42124 (15)	0.20619 (9)	0.6169 (3)	0.0248 (4)
C14	0.33994 (16)	0.19268 (9)	0.4725 (4)	0.0274 (4)
H14	0.2697	0.2146	0.4812	0.033*
C15	0.36070 (16)	0.14697 (9)	0.3142 (4)	0.0311 (4)
H15	0.3059	0.1375	0.2127	0.037*
C16	0.46320 (18)	0.11590 (10)	0.3093 (4)	0.0370 (5)
C17	0.54509 (18)	0.12796 (11)	0.4537 (4)	0.0387 (5)
H17	0.6145	0.1050	0.4460	0.046*
C18	0.52465 (16)	0.17380 (10)	0.6092 (4)	0.0309 (4)
H18	0.5800	0.1832	0.7097	0.037*

	U11	U22	U33	U12	U13	U23
S	0.0189 (2)	0.0315 (2)	0.0278 (2)	−0.00380 (16)	0.0001 (2)	0.0014 (2)
F	0.0513 (8)	0.0624 (9)	0.0659 (11)	0.0177 (7)	−0.0131 (9)	−0.0339 (9)
O1	0.0215 (7)	0.0287 (6)	0.0273 (7)	−0.0043 (5)	−0.0026 (6)	0.0005 (6)
O2	0.0195 (7)	0.0421 (8)	0.0440 (10)	0.0022 (6)	0.0003 (6)	−0.0035 (7)
C1	0.0197 (8)	0.0252 (8)	0.0255 (9)	−0.0019 (6)	0.0007 (8)	−0.0010 (8)
C2	0.0212 (8)	0.0233 (8)	0.0252 (9)	0.0028 (7)	0.0013 (7)	−0.0002 (8)
C3	0.0268 (9)	0.0274 (9)	0.0276 (10)	0.0066 (7)	−0.0018 (8)	−0.0002 (8)
C4	0.0328 (10)	0.0297 (9)	0.0294 (11)	0.0072 (8)	0.0002 (8)	0.0044 (8)
C5	0.0326 (10)	0.0221 (8)	0.0372 (11)	0.0048 (8)	0.0075 (10)	0.0043 (9)
C6	0.0257 (9)	0.0216 (8)	0.0322 (10)	0.0009 (7)	0.0042 (9)	−0.0023 (8)
C7	0.0223 (9)	0.0241 (8)	0.0258 (9)	0.0019 (6)	0.0010 (8)	−0.0015 (8)
C8	0.0211 (9)	0.0263 (9)	0.0263 (9)	−0.0023 (7)	0.0005 (8)	−0.0026 (7)
C9	0.0289 (10)	0.0375 (10)	0.0282 (12)	0.0049 (8)	−0.0065 (8)	0.0007 (8)
C10	0.0422 (11)	0.0345 (10)	0.0490 (13)	0.0003 (9)	0.0082 (13)	0.0131 (12)
C11	0.0327 (11)	0.0328 (10)	0.0431 (12)	−0.0084 (8)	0.0013 (10)	−0.0025 (10)
C12	0.0259 (10)	0.0351 (10)	0.0279 (10)	−0.0026 (8)	−0.0022 (9)	0.0053 (8)
C13	0.0205 (9)	0.0235 (8)	0.0303 (9)	−0.0031 (7)	−0.0028 (8)	0.0019 (8)
C14	0.0212 (9)	0.0268 (8)	0.0342 (10)	−0.0014 (7)	−0.0054 (8)	0.0023 (8)
C15	0.0275 (9)	0.0294 (9)	0.0364 (12)	−0.0023 (7)	−0.0083 (10)	−0.0017 (10)
C16	0.0374 (11)	0.0314 (9)	0.0421 (13)	0.0042 (8)	−0.0050 (11)	−0.0079 (10)
C17	0.0277 (11)	0.0358 (11)	0.0525 (14)	0.0074 (8)	−0.0074 (11)	−0.0071 (11)
C18	0.0228 (9)	0.0297 (9)	0.0403 (11)	0.0010 (8)	−0.0071 (9)	0.0002 (9)

S—O2	1.4915 (14)	C9—H9C	0.9800
S—C1	1.7606 (18)	C10—H10A	0.9800
S—C13	1.793 (2)	C10—H10B	0.9800
F—C16	1.350 (3)	C10—H10C	0.9800
O1—C8	1.372 (2)	C11—H11A	0.9800
O1—C7	1.384 (2)	C11—H11B	0.9800
C1—C8	1.356 (3)	C11—H11C	0.9800
C1—C2	1.456 (3)	C12—H12A	0.9800
C2—C7	1.394 (3)	C12—H12B	0.9800
C2—C3	1.402 (3)	C12—H12C	0.9800
C3—C4	1.392 (3)	C13—C14	1.379 (3)
C3—C9	1.506 (3)	C13—C18	1.397 (3)
C4—C5	1.412 (3)	C14—C15	1.390 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.394 (3)	C15—C16	1.375 (3)
C5—C10	1.504 (3)	C15—H15	0.9500
C6—C7	1.386 (3)	C16—C17	1.379 (3)
C6—C11	1.505 (3)	C17—C18	1.378 (3)
C8—C12	1.478 (3)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800
O2—S—C1	110.49 (9)	C5—C10—H10B	109.5
O2—S—C13	106.91 (10)	H10A—C10—H10B	109.5
C1—S—C13	98.95 (9)	C5—C10—H10C	109.5
C8—O1—C7	106.41 (15)	H10A—C10—H10C	109.5
C8—C1—C2	107.61 (16)	H10B—C10—H10C	109.5
C8—C1—S	118.44 (15)	C6—C11—H11A	109.5
C2—C1—S	133.91 (15)	C6—C11—H11B	109.5
C7—C2—C3	118.25 (18)	H11A—C11—H11B	109.5
C7—C2—C1	104.08 (16)	C6—C11—H11C	109.5
C3—C2—C1	137.67 (18)	H11A—C11—H11C	109.5
C4—C3—C2	116.62 (18)	H11B—C11—H11C	109.5
C4—C3—C9	120.07 (19)	C8—C12—H12A	109.5
C2—C3—C9	123.30 (18)	C8—C12—H12B	109.5
C3—C4—C5	123.73 (19)	H12A—C12—H12B	109.5
C3—C4—H4	118.1	C8—C12—H12C	109.5
C5—C4—H4	118.1	H12A—C12—H12C	109.5
C6—C5—C4	120.03 (18)	H12B—C12—H12C	109.5
C6—C5—C10	121.0 (2)	C14—C13—C18	121.06 (19)
C4—C5—C10	119.0 (2)	C14—C13—S	118.92 (15)
C7—C6—C5	114.95 (18)	C18—C13—S	119.72 (16)
C7—C6—C11	120.7 (2)	C13—C14—C15	120.07 (18)
C5—C6—C11	124.32 (19)	C13—C14—H14	120.0
O1—C7—C6	122.64 (18)	C15—C14—H14	120.0
O1—C7—C2	110.96 (16)	C16—C15—C14	117.8 (2)
C6—C7—C2	126.40 (19)	C16—C15—H15	121.1
C1—C8—O1	110.94 (17)	C14—C15—H15	121.1
C1—C8—C12	133.67 (17)	F—C16—C15	118.1 (2)
O1—C8—C12	115.30 (17)	F—C16—C17	118.86 (19)
C3—C9—H9A	109.5	C15—C16—C17	123.0 (2)
C3—C9—H9B	109.5	C18—C17—C16	118.98 (19)
H9A—C9—H9B	109.5	C18—C17—H17	120.5
C3—C9—H9C	109.5	C16—C17—H17	120.5
H9A—C9—H9C	109.5	C17—C18—C13	119.01 (19)
H9B—C9—H9C	109.5	C17—C18—H18	120.5
C5—C10—H10A	109.5	C13—C18—H18	120.5
O2—S—C1—C8	137.99 (16)	C11—C6—C7—C2	−179.11 (19)
C13—S—C1—C8	−110.10 (17)	C3—C2—C7—O1	−179.38 (16)
O2—S—C1—C2	−44.4 (2)	C1—C2—C7—O1	0.3 (2)
C13—S—C1—C2	67.5 (2)	C3—C2—C7—C6	−0.1 (3)
C8—C1—C2—C7	−0.4 (2)	C1—C2—C7—C6	179.60 (18)
S—C1—C2—C7	−178.16 (16)	C2—C1—C8—O1	0.3 (2)
C8—C1—C2—C3	179.2 (2)	S—C1—C8—O1	178.51 (13)
S—C1—C2—C3	1.4 (4)	C2—C1—C8—C12	−176.0 (2)
C7—C2—C3—C4	0.3 (3)	S—C1—C8—C12	2.2 (3)
C1—C2—C3—C4	−179.3 (2)	C7—O1—C8—C1	−0.1 (2)
C7—C2—C3—C9	179.36 (18)	C7—O1—C8—C12	176.90 (17)
C1—C2—C3—C9	−0.2 (4)	O2—S—C13—C14	−13.62 (19)
C2—C3—C4—C5	0.6 (3)	C1—S—C13—C14	−128.35 (17)
C9—C3—C4—C5	−178.50 (19)	O2—S—C13—C18	172.58 (16)
C3—C4—C5—C6	−1.7 (3)	C1—S—C13—C18	57.85 (18)
C3—C4—C5—C10	177.73 (19)	C18—C13—C14—C15	−1.0 (3)
C4—C5—C6—C7	1.7 (3)	S—C13—C14—C15	−174.70 (16)
C10—C5—C6—C7	−177.71 (18)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C11	179.86 (19)	C14—C15—C16—F	−179.6 (2)
C10—C5—C6—C11	0.4 (3)	C14—C15—C16—C17	0.2 (4)
C8—O1—C7—C6	−179.43 (18)	F—C16—C17—C18	179.0 (2)
C8—O1—C7—C2	−0.12 (19)	C15—C16—C17—C18	−0.8 (4)
C5—C6—C7—O1	178.31 (17)	C16—C17—C18—C13	0.6 (4)
C11—C6—C7—O1	0.1 (3)	C14—C13—C18—C17	0.3 (3)
C5—C6—C7—C2	−0.9 (3)	S—C13—C18—C17	173.99 (18)

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.95	2.59	3.529 (3)	169
C18—H18···O2ii	0.95	2.49	3.328 (2)	147
C11—H11A···Cgii	0.98	2.66	3.553 (3)	152
C12—H12A···Cgiii	0.98	2.78	3.590 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.95	2.59	3.529 (3)	169
C18—H18⋯O2ii	0.95	2.49	3.328 (2)	147
C11—H11A⋯Cgii	0.98	2.66	3.553 (3)	152
C12—H12A⋯Cgiii	0.98	2.78	3.590 (3)	141

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