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

In the title compound, C(20)H(19)FO(2)S, the benzofuran fragment is essentially planar, with a largest deviation from the mean plane of 0.026 (2) Å. The benzene ring makes a dihedral angle of 30.72 (12)° with this plane. The cyclo-pentyl group adopts an envelope conformation, with the α-C atom as the flap. This atom is disordered over two sites with occupancy factors of 0.803 (16) and 0.197 (16). In the crystal, mol-ecules are linked by weak C-H⋯O, C-H⋯π and C-F⋯π [3.257 (3) Å] inter-actions.

Related literature

For the crystal structures of related compounds, see: Choi et al. (2011 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C20H19FO2S

M = 342.41

Monoclinic,

a = 6.1024 (3) Å

b = 25.3030 (11) Å

c = 10.6840 (5) Å

β = 90.231 (1)°

V = 1649.69 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.40 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.954

13224 measured reflections

2905 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.165

S = 1.02

2905 reflections

228 parameters

30 restraints

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −0.55 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/S1600536812025482/yk2058sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025482/yk2058Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025482/yk2058Isup3.cml

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

C20H19FO2S	F(000) = 720
Mr = 342.41	Dx = 1.379 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5280 reflections
a = 6.1024 (3) Å	θ = 2.5–28.2°
b = 25.3030 (11) Å	µ = 0.22 mm−1
c = 10.6840 (5) Å	T = 173 K
β = 90.231 (1)°	Block, colourless
V = 1649.69 (13) Å3	0.40 × 0.25 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2905 independent reflections
Radiation source: rotating anode	2568 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −30→30
Tmin = 0.919, Tmax = 0.954	l = −12→12
13224 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)] = 0.060	Hydrogen site location: difference Fourier map
wR(F2) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.087P)2 + 2.8614P] where P = (Fo2 + 2Fc2)/3
2905 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 1.35 e Å−3
30 restraints	Δρmin = −0.55 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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	0.49517 (11)	0.72428 (3)	0.41704 (6)	0.0274 (2)
O1	0.5749 (3)	0.56958 (7)	0.45210 (17)	0.0261 (4)
O2	0.4494 (4)	0.74049 (8)	0.28532 (19)	0.0403 (6)
F1	1.2882 (3)	0.56555 (10)	0.6805 (2)	0.0617 (6)
C1	0.3984 (4)	0.57030 (11)	0.3714 (2)	0.0245 (6)
C2	0.6189 (4)	0.62149 (11)	0.4815 (2)	0.0242 (6)
C3	0.4786 (4)	0.65466 (11)	0.4202 (2)	0.0234 (6)
C4	0.1509 (5)	0.63050 (11)	0.2681 (3)	0.0289 (6)
H4	0.1049	0.6654	0.2488	0.035*
C5	0.0407 (5)	0.58719 (12)	0.2184 (3)	0.0344 (7)
C6	0.1179 (5)	0.53590 (12)	0.2453 (3)	0.0356 (7)
H6	0.0429	0.5066	0.2096	0.043*
C7	0.2976 (5)	0.52630 (11)	0.3211 (3)	0.0306 (6)
H7	0.3486	0.4915	0.3376	0.037*
C8	0.3310 (4)	0.62182 (10)	0.3474 (2)	0.0233 (6)
C9	−0.1701 (6)	0.59386 (12)	0.1427 (3)	0.0448 (8)
H9A	−0.2944	0.5837	0.1984	0.054*	0.803 (16)
H9B	−0.2753	0.5944	0.2142	0.054*	0.197 (16)
C10A	−0.1826 (10)	0.5586 (2)	0.0271 (5)	0.0527 (19)	0.803 (16)
H10A	−0.2053	0.5212	0.0505	0.063*	0.803 (16)
H10B	−0.0476	0.5615	−0.0236	0.063*	0.803 (16)
C10B	−0.283 (3)	0.5505 (2)	0.0671 (11)	0.035 (3)	0.197 (16)
H10C	−0.3989	0.5330	0.1167	0.043*	0.197 (16)
H10D	−0.1763	0.5236	0.0390	0.043*	0.197 (16)
C11	−0.3803 (8)	0.58042 (15)	−0.0439 (5)	0.0776 (16)
H11A	−0.3541	0.5794	−0.1352	0.093*	0.803 (16)
H11B	−0.5127	0.5593	−0.0252	0.093*	0.803 (16)
H11C	−0.2866	0.5788	−0.1192	0.093*	0.197 (16)
H11D	−0.5234	0.5637	−0.0628	0.093*	0.197 (16)
C12	−0.4100 (5)	0.63712 (13)	0.0002 (3)	0.0377 (7)
H12A	−0.5526	0.6415	0.0428	0.045*
H12B	−0.4034	0.6619	−0.0713	0.045*
C13	−0.2206 (5)	0.64710 (12)	0.0912 (3)	0.0377 (7)
H13A	−0.0923	0.6620	0.0472	0.045*
H13B	−0.2649	0.6717	0.1586	0.045*
C14	0.7931 (4)	0.62945 (11)	0.5734 (2)	0.0258 (6)
C15	0.9653 (4)	0.59298 (12)	0.5813 (3)	0.0297 (6)
H15	0.9718	0.5635	0.5263	0.036*
C16	1.1247 (5)	0.60094 (13)	0.6706 (3)	0.0341 (7)
C17	1.1235 (5)	0.64302 (14)	0.7524 (3)	0.0390 (8)
H17	1.2369	0.6474	0.8126	0.047*
C18	0.9526 (5)	0.67855 (13)	0.7442 (3)	0.0380 (7)
H18	0.9485	0.7079	0.7995	0.046*
C19	0.7870 (5)	0.67197 (12)	0.6566 (3)	0.0304 (6)
H19	0.6690	0.6964	0.6530	0.036*
C20	0.2521 (5)	0.73842 (12)	0.5038 (3)	0.0339 (7)
H20A	0.2213	0.7764	0.4998	0.051*
H20B	0.2733	0.7279	0.5913	0.051*
H20C	0.1286	0.7188	0.4679	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0324 (4)	0.0216 (4)	0.0281 (4)	−0.0040 (3)	−0.0031 (3)	0.0021 (2)
O1	0.0283 (10)	0.0232 (9)	0.0266 (10)	0.0024 (7)	−0.0057 (8)	0.0012 (7)
O2	0.0606 (15)	0.0312 (11)	0.0290 (11)	−0.0028 (10)	0.0000 (10)	0.0099 (9)
F1	0.0414 (12)	0.0772 (16)	0.0665 (15)	0.0171 (11)	−0.0087 (10)	0.0048 (12)
C1	0.0263 (13)	0.0261 (14)	0.0210 (13)	0.0024 (11)	−0.0039 (10)	0.0022 (10)
C2	0.0254 (13)	0.0252 (13)	0.0219 (13)	−0.0018 (10)	0.0016 (10)	−0.0007 (10)
C3	0.0270 (13)	0.0226 (13)	0.0205 (13)	−0.0010 (10)	−0.0019 (10)	0.0010 (10)
C4	0.0356 (15)	0.0229 (14)	0.0280 (14)	0.0018 (11)	−0.0092 (12)	0.0030 (11)
C5	0.0420 (17)	0.0282 (15)	0.0330 (16)	−0.0005 (13)	−0.0125 (13)	0.0015 (12)
C6	0.0451 (18)	0.0238 (14)	0.0379 (17)	−0.0038 (12)	−0.0144 (14)	−0.0035 (12)
C7	0.0387 (16)	0.0218 (14)	0.0313 (15)	0.0026 (12)	−0.0070 (12)	0.0010 (11)
C8	0.0263 (13)	0.0225 (13)	0.0210 (13)	−0.0002 (10)	−0.0008 (10)	0.0008 (10)
C9	0.0461 (19)	0.0373 (18)	0.0509 (18)	−0.0018 (15)	−0.0180 (15)	0.0010 (14)
C10A	0.050 (3)	0.033 (2)	0.075 (3)	0.006 (2)	−0.039 (3)	−0.014 (2)
C10B	0.022 (7)	0.034 (6)	0.050 (6)	−0.006 (5)	0.009 (5)	−0.004 (4)
C11	0.084 (3)	0.041 (2)	0.107 (3)	0.016 (2)	−0.072 (3)	−0.018 (2)
C12	0.0324 (16)	0.0392 (17)	0.0416 (17)	0.0035 (13)	−0.0108 (13)	−0.0001 (14)
C13	0.0411 (17)	0.0322 (16)	0.0398 (17)	0.0042 (13)	−0.0130 (14)	−0.0041 (13)
C14	0.0231 (13)	0.0308 (14)	0.0236 (13)	−0.0023 (11)	−0.0011 (10)	0.0047 (11)
C15	0.0269 (14)	0.0348 (16)	0.0276 (14)	−0.0008 (12)	−0.0003 (11)	0.0019 (12)
C16	0.0223 (14)	0.0446 (18)	0.0354 (16)	0.0027 (12)	−0.0020 (12)	0.0099 (13)
C17	0.0310 (16)	0.055 (2)	0.0313 (16)	−0.0076 (14)	−0.0098 (12)	0.0031 (14)
C18	0.0391 (17)	0.0437 (18)	0.0311 (16)	−0.0048 (14)	−0.0067 (13)	−0.0056 (13)
C19	0.0298 (15)	0.0341 (15)	0.0274 (14)	−0.0005 (12)	−0.0022 (11)	−0.0008 (12)
C20	0.0394 (17)	0.0291 (15)	0.0332 (16)	0.0042 (13)	0.0000 (13)	−0.0008 (12)

S1—O2	1.491 (2)	C10B—C11	1.5254 (17)
S1—C3	1.765 (3)	C10B—H10C	0.9900
S1—C20	1.789 (3)	C10B—H10D	0.9900
O1—C2	1.377 (3)	C11—C12	1.521 (5)
O1—C1	1.377 (3)	C11—H11A	0.9900
F1—C16	1.345 (4)	C11—H11B	0.9900
C1—C7	1.380 (4)	C11—H11C	0.9900
C1—C8	1.390 (4)	C11—H11D	0.9900
C2—C3	1.364 (4)	C12—C13	1.528 (4)
C2—C14	1.458 (4)	C12—H12A	0.9900
C3—C8	1.449 (4)	C12—H12B	0.9900
C4—C5	1.390 (4)	C13—H13A	0.9900
C4—C8	1.402 (4)	C13—H13B	0.9900
C4—H4	0.9500	C14—C19	1.396 (4)
C5—C6	1.410 (4)	C14—C15	1.401 (4)
C5—C9	1.526 (4)	C15—C16	1.375 (4)
C6—C7	1.383 (4)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.377 (5)
C7—H7	0.9500	C17—C18	1.379 (5)
C9—C13	1.487 (4)	C17—H17	0.9500
C9—C10A	1.5249 (16)	C18—C19	1.386 (4)
C9—C10B	1.5250 (17)	C18—H18	0.9500
C9—H9A	1.0000	C19—H19	0.9500
C9—H9B	1.0000	C20—H20A	0.9800
C10A—C11	1.5254 (17)	C20—H20B	0.9800
C10A—H10A	0.9900	C20—H20C	0.9800
C10A—H10B	0.9900
O2—S1—C3	106.38 (12)	C12—C11—C10A	106.4 (3)
O2—S1—C20	106.37 (14)	C12—C11—H11A	110.5
C3—S1—C20	98.18 (13)	C10B—C11—H11A	133.6
C2—O1—C1	106.34 (19)	C10A—C11—H11A	110.5
O1—C1—C7	125.4 (2)	C12—C11—H11B	110.5
O1—C1—C8	111.0 (2)	C10B—C11—H11B	83.8
C7—C1—C8	123.6 (2)	C10A—C11—H11B	110.5
C3—C2—O1	110.9 (2)	H11A—C11—H11B	108.6
C3—C2—C14	133.8 (3)	C12—C11—H11C	111.1
O1—C2—C14	115.2 (2)	C10B—C11—H11C	112.7
C2—C3—C8	107.0 (2)	C10A—C11—H11C	86.0
C2—C3—S1	126.0 (2)	H11B—C11—H11C	128.0
C8—C3—S1	126.7 (2)	C12—C11—H11D	111.1
C5—C4—C8	119.0 (3)	C10B—C11—H11D	106.7
C5—C4—H4	120.5	C10A—C11—H11D	130.0
C8—C4—H4	120.5	H11A—C11—H11D	86.2
C4—C5—C6	119.2 (3)	H11C—C11—H11D	109.2
C4—C5—C9	121.4 (3)	C11—C12—C13	105.2 (2)
C6—C5—C9	119.3 (3)	C11—C12—H12A	110.7
C7—C6—C5	123.0 (3)	C13—C12—H12A	110.7
C7—C6—H6	118.5	C11—C12—H12B	110.7
C5—C6—H6	118.5	C13—C12—H12B	110.7
C1—C7—C6	116.0 (3)	H12A—C12—H12B	108.8
C1—C7—H7	122.0	C9—C13—C12	103.9 (2)
C6—C7—H7	122.0	C9—C13—H13A	111.0
C1—C8—C4	119.3 (2)	C12—C13—H13A	111.0
C1—C8—C3	104.8 (2)	C9—C13—H13B	111.0
C4—C8—C3	135.9 (2)	C12—C13—H13B	111.0
C13—C9—C5	118.0 (3)	H13A—C13—H13B	109.0
C13—C9—C10A	102.7 (3)	C19—C14—C15	119.4 (3)
C5—C9—C10A	113.8 (3)	C19—C14—C2	120.9 (2)
C13—C9—C10B	111.3 (3)	C15—C14—C2	119.6 (3)
C5—C9—C10B	125.4 (5)	C16—C15—C14	118.3 (3)
C13—C9—H9A	107.2	C16—C15—H15	120.9
C5—C9—H9A	107.2	C14—C15—H15	120.9
C10A—C9—H9A	107.2	F1—C16—C15	118.7 (3)
C10B—C9—H9A	77.8	F1—C16—C17	118.1 (3)
C13—C9—H9B	97.9	C15—C16—C17	123.2 (3)
C5—C9—H9B	98.0	C16—C17—C18	118.1 (3)
C10A—C9—H9B	126.7	C16—C17—H17	121.0
C10B—C9—H9B	97.2	C18—C17—H17	121.0
C9—C10A—C11	103.2 (3)	C17—C18—C19	120.9 (3)
C9—C10A—H10A	111.1	C17—C18—H18	119.5
C11—C10A—H10A	111.1	C19—C18—H18	119.5
C9—C10A—H10B	111.1	C18—C19—C14	120.1 (3)
C11—C10A—H10B	111.1	C18—C19—H19	119.9
H10A—C10A—H10B	109.1	C14—C19—H19	119.9
C9—C10B—C11	103.2 (3)	S1—C20—H20A	109.5
C9—C10B—H10C	111.1	S1—C20—H20B	109.5
C11—C10B—H10C	111.1	H20A—C20—H20B	109.5
C9—C10B—H10D	111.1	S1—C20—H20C	109.5
C11—C10B—H10D	111.1	H20A—C20—H20C	109.5
H10C—C10B—H10D	109.1	H20B—C20—H20C	109.5
C12—C11—C10B	105.9 (5)
C2—O1—C1—C7	−178.4 (3)	C4—C5—C9—C10B	169.7 (9)
C2—O1—C1—C8	0.9 (3)	C6—C5—C9—C10B	−14.5 (10)
C1—O1—C2—C3	−1.1 (3)	C13—C9—C10A—C11	−40.4 (6)
C1—O1—C2—C14	176.1 (2)	C5—C9—C10A—C11	−169.1 (4)
O1—C2—C3—C8	0.9 (3)	C10B—C9—C10A—C11	70.6 (5)
C14—C2—C3—C8	−175.6 (3)	C13—C9—C10B—C11	7.3 (14)
O1—C2—C3—S1	−172.60 (18)	C5—C9—C10B—C11	−146.2 (7)
C14—C2—C3—S1	10.9 (4)	C10A—C9—C10B—C11	−70.6 (5)
O2—S1—C3—C2	137.4 (2)	C9—C10B—C11—C12	−24.6 (13)
C20—S1—C3—C2	−112.8 (3)	C9—C10B—C11—C10A	70.6 (5)
O2—S1—C3—C8	−34.9 (3)	C9—C10A—C11—C12	22.9 (7)
C20—S1—C3—C8	74.9 (3)	C9—C10A—C11—C10B	−70.6 (5)
C8—C4—C5—C6	−2.3 (4)	C10B—C11—C12—C13	33.3 (9)
C8—C4—C5—C9	173.6 (3)	C10A—C11—C12—C13	2.6 (6)
C4—C5—C6—C7	1.1 (5)	C5—C9—C13—C12	168.4 (3)
C9—C5—C6—C7	−174.9 (3)	C10A—C9—C13—C12	42.3 (4)
O1—C1—C7—C6	177.9 (3)	C10B—C9—C13—C12	12.7 (9)
C8—C1—C7—C6	−1.3 (4)	C11—C12—C13—C9	−27.9 (4)
C5—C6—C7—C1	0.7 (5)	C3—C2—C14—C19	28.7 (5)
O1—C1—C8—C4	−179.2 (2)	O1—C2—C14—C19	−147.7 (3)
C7—C1—C8—C4	0.1 (4)	C3—C2—C14—C15	−153.4 (3)
O1—C1—C8—C3	−0.3 (3)	O1—C2—C14—C15	30.2 (3)
C7—C1—C8—C3	179.0 (3)	C19—C14—C15—C16	−0.7 (4)
C5—C4—C8—C1	1.7 (4)	C2—C14—C15—C16	−178.7 (3)
C5—C4—C8—C3	−176.7 (3)	C14—C15—C16—F1	178.7 (3)
C2—C3—C8—C1	−0.4 (3)	C14—C15—C16—C17	−0.2 (4)
S1—C3—C8—C1	173.1 (2)	F1—C16—C17—C18	−178.4 (3)
C2—C3—C8—C4	178.2 (3)	C15—C16—C17—C18	0.5 (5)
S1—C3—C8—C4	−8.3 (5)	C16—C17—C18—C19	0.2 (5)
C4—C5—C9—C13	17.8 (5)	C17—C18—C19—C14	−1.1 (5)
C6—C5—C9—C13	−166.4 (3)	C15—C14—C19—C18	1.4 (4)
C4—C5—C9—C10A	138.2 (5)	C2—C14—C19—C18	179.2 (3)
C6—C5—C9—C10A	−45.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2i	0.95	2.52	3.326 (4)	143
C20—H20B···O2i	0.98	2.47	3.279 (4)	140
C9—H9A···Cg1ii	1.00	2.76	3.626 (4)	145
C15—H15···Cg2iii	0.95	2.94	3.461 (4)	116

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C3/C8/O1 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.95	2.52	3.326 (4)	143
C20—H20B⋯O2i	0.98	2.47	3.279 (4)	140
C9—H9A⋯Cg1ii	1.00	2.76	3.626 (4)	145
C15—H15⋯Cg2iii	0.95	2.94	3.461 (4)	116

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