5-Cyclo-pentyl-2-(4-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(20)H(19)FO(2)S, the cyclo-pentyl ring adopts an envelope conformation. The 4-fluoro-phenyl ring makes a dihedral angle of 27.10 (7)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. In the cyclo-pentyl ring, one C atom is disordered over two orientations with site-occupancy factors of 0.617 (7) and 0.383 (7).

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 structural studies of related 2-(4-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C20H19FO2S

M = 342.41

Orthorhombic,

a = 20.0254 (13) Å

b = 33.197 (2) Å

c = 10.0233 (7) Å

V = 6663.3 (8) Å3

Z = 16

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.35 × 0.26 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.961

16962 measured reflections

4136 independent reflections

3915 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.06

4136 reflections

223 parameters

96 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1949 Friedel pairs

Flack parameter: 0.15 (7)

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) I. DOI: 10.1107/S1600536811036087/gk2398sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036087/gk2398Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036087/gk2398Isup3.cml

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

C20H19FO2S	F(000) = 2880
Mr = 342.41	Dx = 1.365 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 6619 reflections
a = 20.0254 (13) Å	θ = 2.4–27.7°
b = 33.197 (2) Å	µ = 0.21 mm−1
c = 10.0233 (7) Å	T = 173 K
V = 6663.3 (8) Å3	Block, colourless
Z = 16	0.35 × 0.26 × 0.19 mm

Bruker SMART APEXII CCD diffractometer	4136 independent reflections
Radiation source: rotating anode	3915 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.4°
φ and ω scans	h = −26→23
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −44→42
Tmin = 0.930, Tmax = 0.961	l = −13→13
16962 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0576P)2 + 8.9505P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4136 reflections	Δρmax = 0.48 e Å−3
223 parameters	Δρmin = −0.37 e Å−3
96 restraints	Absolute structure: Flack (1983), 1949 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.15 (7)

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	Occ. (<1)
S1	0.28603 (2)	0.120706 (14)	0.30091 (12)	0.02721 (11)
F1	0.22523 (7)	0.07977 (4)	−0.34573 (18)	0.0441 (3)
O1	0.31307 (7)	0.21374 (4)	0.06022 (18)	0.0312 (3)
O2	0.33631 (8)	0.11882 (5)	0.4113 (2)	0.0370 (4)
C1	0.29639 (10)	0.16799 (6)	0.2227 (2)	0.0262 (4)
C2	0.32275 (10)	0.20417 (6)	0.2840 (2)	0.0290 (4)
C3	0.34184 (12)	0.21599 (7)	0.4113 (2)	0.0357 (5)
H3	0.3357	0.1984	0.4851	0.043*
C4	0.37027 (13)	0.25424 (8)	0.4294 (3)	0.0404 (5)
C5	0.37902 (12)	0.27952 (7)	0.3188 (3)	0.0396 (5)
H5	0.3988	0.3052	0.3320	0.048*
C6	0.36010 (12)	0.26866 (7)	0.1916 (3)	0.0374 (5)
H6	0.3658	0.2862	0.1175	0.045*
C7	0.33230 (11)	0.23083 (6)	0.1784 (2)	0.0305 (4)
C8	0.29208 (10)	0.17501 (6)	0.0893 (2)	0.0274 (4)
C9	0.39134 (15)	0.26922 (8)	0.5643 (3)	0.0533 (7)
H9A	0.4160	0.2951	0.5521	0.064*	0.617 (7)
H9B	0.4273	0.2883	0.5361	0.064*	0.383 (7)
C10A	0.33241 (16)	0.27685 (18)	0.6576 (2)	0.0594 (11)	0.617 (7)
H10A	0.3050	0.2997	0.6255	0.071*	0.617 (7)
H10B	0.3038	0.2526	0.6644	0.071*	0.617 (7)
C10B	0.3491 (5)	0.2980 (3)	0.64769 (16)	0.0594 (11)	0.383 (7)
H10C	0.3011	0.2945	0.6278	0.071*	0.383 (7)
H10D	0.3617	0.3263	0.6298	0.071*	0.383 (7)
C11	0.3643 (2)	0.28668 (11)	0.79210 (19)	0.0710 (10)
H11A	0.3745	0.3158	0.7992	0.085*	0.617 (7)
H11B	0.3346	0.2789	0.8667	0.085*	0.617 (7)
H11C	0.3704	0.3113	0.8466	0.085*	0.383 (7)
H11D	0.3269	0.2709	0.8301	0.085*	0.383 (7)
C12	0.42736 (18)	0.26191 (9)	0.7924 (3)	0.0585 (7)
H12A	0.4253	0.2407	0.8618	0.070*
H12B	0.4669	0.2791	0.8092	0.070*
C13	0.4306 (2)	0.24326 (13)	0.6533 (4)	0.0819 (13)
H13A	0.4775	0.2418	0.6223	0.098*
H13B	0.4118	0.2157	0.6546	0.098*
C14	0.27300 (10)	0.15066 (6)	−0.0241 (2)	0.0271 (4)
C15	0.22789 (11)	0.11913 (7)	−0.0111 (2)	0.0312 (4)
H15	0.2076	0.1141	0.0730	0.037*
C16	0.21211 (11)	0.09501 (7)	−0.1192 (2)	0.0338 (4)
H16	0.1819	0.0731	−0.1099	0.041*
C17	0.24099 (11)	0.10340 (7)	−0.2402 (2)	0.0318 (4)
C18	0.28529 (11)	0.13457 (7)	−0.2591 (2)	0.0349 (5)
H18	0.3042	0.1397	−0.3443	0.042*
C19	0.30136 (11)	0.15821 (7)	−0.1500 (2)	0.0326 (4)
H19	0.3320	0.1798	−0.1602	0.039*
C20	0.20733 (10)	0.13041 (8)	0.3791 (3)	0.0356 (5)
H20A	0.1952	0.1075	0.4359	0.053*
H20B	0.1730	0.1342	0.3105	0.053*
H20C	0.2107	0.1548	0.4337	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0302 (2)	0.0261 (2)	0.0254 (2)	0.00067 (19)	−0.00003 (18)	0.00238 (18)
F1	0.0492 (8)	0.0511 (8)	0.0321 (7)	−0.0062 (6)	−0.0020 (6)	−0.0098 (6)
O1	0.0371 (8)	0.0276 (7)	0.0290 (7)	−0.0008 (6)	0.0008 (6)	0.0027 (6)
O2	0.0312 (8)	0.0433 (9)	0.0365 (8)	0.0021 (7)	−0.0056 (6)	0.0111 (7)
C1	0.0253 (9)	0.0257 (9)	0.0277 (9)	0.0004 (7)	0.0014 (8)	0.0018 (7)
C2	0.0262 (9)	0.0265 (9)	0.0344 (10)	0.0029 (7)	0.0022 (8)	−0.0022 (7)
C3	0.0411 (12)	0.0342 (11)	0.0319 (10)	−0.0022 (9)	0.0019 (9)	−0.0036 (9)
C4	0.0419 (13)	0.0368 (11)	0.0425 (12)	−0.0004 (9)	0.0001 (10)	−0.0133 (9)
C5	0.0400 (12)	0.0279 (10)	0.0510 (14)	−0.0023 (9)	0.0008 (10)	−0.0085 (10)
C6	0.0383 (12)	0.0247 (9)	0.0492 (13)	0.0006 (8)	0.0032 (10)	0.0004 (8)
C7	0.0301 (10)	0.0277 (9)	0.0336 (10)	0.0036 (8)	0.0002 (7)	−0.0022 (8)
C8	0.0239 (9)	0.0288 (9)	0.0294 (10)	0.0018 (7)	0.0029 (7)	0.0033 (7)
C9	0.0850 (19)	0.0369 (11)	0.0381 (11)	−0.0150 (12)	0.0014 (12)	−0.0100 (10)
C10A	0.086 (2)	0.053 (3)	0.0391 (13)	0.0215 (19)	−0.0073 (13)	0.0017 (14)
C10B	0.086 (2)	0.053 (3)	0.0391 (13)	0.0215 (19)	−0.0073 (13)	0.0017 (14)
C11	0.108 (3)	0.071 (2)	0.0337 (10)	0.0304 (18)	−0.0064 (14)	−0.0035 (12)
C12	0.087 (2)	0.0503 (15)	0.0382 (13)	0.0047 (14)	−0.0166 (15)	0.0034 (12)
C13	0.086 (3)	0.096 (3)	0.064 (2)	0.046 (2)	−0.032 (2)	−0.032 (2)
C14	0.0247 (9)	0.0303 (9)	0.0261 (9)	0.0018 (7)	−0.0001 (7)	0.0017 (7)
C15	0.0275 (10)	0.0405 (11)	0.0256 (10)	−0.0026 (8)	0.0026 (8)	−0.0002 (8)
C16	0.0300 (10)	0.0366 (11)	0.0348 (11)	−0.0049 (8)	−0.0005 (8)	−0.0014 (9)
C17	0.0287 (10)	0.0396 (11)	0.0271 (10)	0.0032 (8)	−0.0026 (8)	−0.0040 (8)
C18	0.0359 (11)	0.0436 (12)	0.0253 (10)	0.0000 (9)	0.0018 (8)	0.0016 (9)
C19	0.0324 (11)	0.0368 (10)	0.0284 (9)	−0.0028 (8)	0.0031 (8)	0.0054 (8)
C20	0.0258 (10)	0.0486 (12)	0.0324 (11)	−0.0019 (9)	0.0010 (8)	0.0075 (9)

S1—O2	1.4973 (16)	C10B—C11	1.5258 (14)
S1—C1	1.767 (2)	C10B—H10C	0.9900
S1—C20	1.789 (2)	C10B—H10D	0.9900
F1—C17	1.354 (2)	C11—C12	1.507 (5)
O1—C7	1.369 (3)	C11—H11A	0.9900
O1—C8	1.384 (2)	C11—H11B	0.9900
C1—C8	1.360 (3)	C11—H11C	0.9900
C1—C2	1.449 (3)	C11—H11D	0.9900
C2—C3	1.388 (3)	C12—C13	1.527 (4)
C2—C7	1.393 (3)	C12—H12A	0.9900
C3—C4	1.403 (3)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.402 (4)	C13—H13B	0.9900
C4—C9	1.501 (4)	C14—C15	1.389 (3)
C5—C6	1.378 (4)	C14—C19	1.406 (3)
C5—H5	0.9500	C15—C16	1.384 (3)
C6—C7	1.380 (3)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.373 (3)
C8—C14	1.447 (3)	C16—H16	0.9500
C9—C13	1.469 (5)	C17—C18	1.376 (3)
C9—C10B	1.5249 (14)	C18—C19	1.384 (3)
C9—C10A	1.5272 (14)	C18—H18	0.9500
C9—H9A	1.0000	C19—H19	0.9500
C9—H9B	1.0000	C20—H20A	0.9800
C10A—C11	1.5266 (14)	C20—H20B	0.9800
C10A—H10A	0.9900	C20—H20C	0.9800
C10A—H10B	0.9900
O2—S1—C1	106.63 (9)	C12—C11—C10A	103.6 (3)
O2—S1—C20	106.03 (10)	C12—C11—H11A	111.0
C1—S1—C20	97.93 (10)	C10B—C11—H11A	82.5
C7—O1—C8	106.75 (15)	C10A—C11—H11A	111.0
C8—C1—C2	107.34 (18)	C12—C11—H11B	111.0
C8—C1—S1	125.54 (16)	C10B—C11—H11B	131.4
C2—C1—S1	126.22 (16)	C10A—C11—H11B	111.0
C3—C2—C7	118.73 (19)	H11A—C11—H11B	109.0
C3—C2—C1	136.4 (2)	C12—C11—H11C	110.2
C7—C2—C1	104.73 (18)	C10B—C11—H11C	110.2
C2—C3—C4	119.1 (2)	C10A—C11—H11C	135.7
C2—C3—H3	120.4	H11B—C11—H11C	82.8
C4—C3—H3	120.4	C12—C11—H11D	110.2
C5—C4—C3	119.3 (2)	C10B—C11—H11D	110.2
C5—C4—C9	118.6 (2)	C10A—C11—H11D	84.9
C3—C4—C9	122.0 (2)	H11A—C11—H11D	130.1
C6—C5—C4	122.7 (2)	H11C—C11—H11D	108.5
C6—C5—H5	118.6	C11—C12—C13	104.8 (2)
C4—C5—H5	118.6	C11—C12—H12A	110.8
C5—C6—C7	116.0 (2)	C13—C12—H12A	110.8
C5—C6—H6	122.0	C11—C12—H12B	110.8
C7—C6—H6	122.0	C13—C12—H12B	110.8
O1—C7—C6	125.0 (2)	H12A—C12—H12B	108.9
O1—C7—C2	110.83 (17)	C9—C13—C12	107.1 (3)
C6—C7—C2	124.1 (2)	C9—C13—H13A	110.3
C1—C8—O1	110.33 (18)	C12—C13—H13A	110.3
C1—C8—C14	133.92 (19)	C9—C13—H13B	110.3
O1—C8—C14	115.71 (17)	C12—C13—H13B	110.3
C13—C9—C4	120.2 (2)	H13A—C13—H13B	108.6
C13—C9—C10B	109.4 (2)	C15—C14—C19	118.79 (19)
C4—C9—C10B	123.1 (3)	C15—C14—C8	121.27 (18)
C13—C9—C10A	98.0 (3)	C19—C14—C8	119.93 (18)
C4—C9—C10A	112.9 (2)	C16—C15—C14	120.7 (2)
C13—C9—H9A	108.3	C16—C15—H15	119.6
C4—C9—H9A	108.3	C14—C15—H15	119.6
C10B—C9—H9A	78.6	C17—C16—C15	118.6 (2)
C10A—C9—H9A	108.3	C17—C16—H16	120.7
C13—C9—H9B	99.1	C15—C16—H16	120.7
C4—C9—H9B	99.1	F1—C17—C16	118.3 (2)
C10B—C9—H9B	99.1	F1—C17—C18	118.61 (18)
C10A—C9—H9B	128.7	C16—C17—C18	123.1 (2)
C11—C10A—C9	104.7 (2)	C17—C18—C19	117.9 (2)
C11—C10A—H10A	110.8	C17—C18—H18	121.1
C9—C10A—H10A	110.8	C19—C18—H18	121.1
C11—C10A—H10B	110.8	C18—C19—C14	120.9 (2)
C9—C10A—H10B	110.8	C18—C19—H19	119.5
H10A—C10A—H10B	108.9	C14—C19—H19	119.5
C9—C10B—C11	104.8 (2)	S1—C20—H20A	109.5
C9—C10B—H10C	110.8	S1—C20—H20B	109.5
C11—C10B—H10C	110.8	H20A—C20—H20B	109.5
C9—C10B—H10D	110.8	S1—C20—H20C	109.5
C11—C10B—H10D	110.8	H20A—C20—H20C	109.5
H10C—C10B—H10D	108.9	H20B—C20—H20C	109.5
C12—C11—C10B	107.6 (3)
O2—S1—C1—C8	141.47 (18)	C5—C4—C9—C10A	111.4 (3)
C20—S1—C1—C8	−109.11 (19)	C3—C4—C9—C10A	−68.1 (4)
O2—S1—C1—C2	−26.3 (2)	C13—C9—C10A—C11	45.6 (4)
C20—S1—C1—C2	83.13 (19)	C4—C9—C10A—C11	173.3 (3)
C8—C1—C2—C3	−176.1 (2)	C10B—C9—C10A—C11	−69.7 (3)
S1—C1—C2—C3	−6.5 (4)	C13—C9—C10B—C11	−1.6 (8)
C8—C1—C2—C7	0.1 (2)	C4—C9—C10B—C11	148.3 (4)
S1—C1—C2—C7	169.66 (15)	C10A—C9—C10B—C11	69.9 (3)
C7—C2—C3—C4	−0.2 (3)	C9—C10B—C11—C12	16.7 (8)
C1—C2—C3—C4	175.5 (2)	C9—C10B—C11—C10A	−70.0 (3)
C2—C3—C4—C5	−0.3 (4)	C9—C10A—C11—C12	−32.1 (4)
C2—C3—C4—C9	179.3 (2)	C9—C10A—C11—C10B	69.6 (3)
C3—C4—C5—C6	0.8 (4)	C10B—C11—C12—C13	−25.0 (6)
C9—C4—C5—C6	−178.8 (2)	C10A—C11—C12—C13	5.7 (4)
C4—C5—C6—C7	−0.7 (4)	C4—C9—C13—C12	−164.7 (3)
C8—O1—C7—C6	176.1 (2)	C10B—C9—C13—C12	−13.9 (6)
C8—O1—C7—C2	−1.3 (2)	C10A—C9—C13—C12	−42.3 (4)
C5—C6—C7—O1	−176.9 (2)	C11—C12—C13—C9	23.9 (4)
C5—C6—C7—C2	0.2 (3)	C1—C8—C14—C15	28.6 (3)
C3—C2—C7—O1	177.75 (19)	O1—C8—C14—C15	−154.06 (19)
C1—C2—C7—O1	0.8 (2)	C1—C8—C14—C19	−150.1 (2)
C3—C2—C7—C6	0.3 (3)	O1—C8—C14—C19	27.3 (3)
C1—C2—C7—C6	−176.7 (2)	C19—C14—C15—C16	1.3 (3)
C2—C1—C8—O1	−0.9 (2)	C8—C14—C15—C16	−177.3 (2)
S1—C1—C8—O1	−170.58 (14)	C14—C15—C16—C17	−1.2 (3)
C2—C1—C8—C14	176.6 (2)	C15—C16—C17—F1	−179.84 (19)
S1—C1—C8—C14	6.9 (3)	C15—C16—C17—C18	0.4 (4)
C7—O1—C8—C1	1.4 (2)	F1—C17—C18—C19	−179.4 (2)
C7—O1—C8—C14	−176.61 (17)	C16—C17—C18—C19	0.4 (3)
C5—C4—C9—C13	−133.7 (3)	C17—C18—C19—C14	−0.3 (3)
C3—C4—C9—C13	46.8 (4)	C15—C14—C19—C18	−0.5 (3)
C5—C4—C9—C10B	79.6 (6)	C8—C14—C19—C18	178.1 (2)
C3—C4—C9—C10B	−100.0 (6)

Cg is the centroid of the C1/C2/C7/O/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2i	0.98	2.29	3.262 (3)	169.
C16—H16···Cgi	0.95	2.53	3.365 (3)	146.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C2/C7/O/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2i	0.98	2.29	3.262 (3)	169
C16—H16⋯Cgi	0.95	2.53	3.365 (3)	146

Symmetry code: (i) .