5-Cyclo-pentyl-3-methyl-sulfinyl-2-phenyl-1-benzofuran.

In the title compound, C(20)H(20)O(2)S, the cyclo-pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The phenyl ring makes a dihedral angle of 32.36 (9)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak C-H⋯O inter-actions. In the cyclo-pentyl ring, two adjacent C atoms are disordered over two sets of sites with site occupancy factors of 0.675 (8) and 0.325 (8).

Related literature

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 ▶). For structural studies of related 2-aryl-5-cyclo­hexyl-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C20H20O2S

M = 324.42

Monoclinic,

a = 5.9586 (7) Å

b = 25.397 (3) Å

c = 10.7804 (12) Å

β = 90.038 (2)°

V = 1631.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.34 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.934, T max = 0.976

15888 measured reflections

3749 independent reflections

2998 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.139

S = 1.06

3749 reflections

228 parameters

36 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.37 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 datablocks global, I. DOI: 10.1107/S1600536811010920/tk2730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010920/tk2730Isup2.hkl

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

C20H20O2S	F(000) = 688
Mr = 324.42	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3689 reflections
a = 5.9586 (7) Å	θ = 2.5–26.8°
b = 25.397 (3) Å	µ = 0.21 mm−1
c = 10.7804 (12) Å	T = 173 K
β = 90.038 (2)°	Block, colourless
V = 1631.4 (3) Å3	0.34 × 0.15 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3749 independent reflections
Radiation source: rotating anode	2998 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.043
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.6°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −33→32
Tmin = 0.934, Tmax = 0.976	l = −14→13
15888 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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F2) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0448P)2 + 1.8445P] where P = (Fo2 + 2Fc2)/3
3749 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.42 e Å−3
36 restraints	Δρmin = −0.37 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	Occ. (<1)
S1	−0.00822 (10)	0.27762 (2)	0.59148 (5)	0.03089 (17)
O1	−0.0724 (3)	0.43153 (6)	0.54750 (15)	0.0316 (4)
O2	0.0353 (4)	0.26204 (7)	0.72244 (17)	0.0452 (5)
C1	0.0137 (4)	0.34662 (9)	0.5858 (2)	0.0274 (5)
C2	0.1643 (4)	0.37906 (9)	0.6581 (2)	0.0291 (5)
C3	0.3432 (4)	0.37030 (9)	0.7400 (2)	0.0348 (5)
H3	0.3856	0.3354	0.7616	0.042*
C4	0.4575 (5)	0.41296 (10)	0.7891 (3)	0.0429 (6)
C5	0.3859 (5)	0.46426 (10)	0.7584 (2)	0.0429 (6)
H5	0.4628	0.4934	0.7939	0.051*
C6	0.2092 (4)	0.47403 (9)	0.6792 (2)	0.0364 (6)
H6	0.1631	0.5088	0.6592	0.044*
C7	0.1034 (4)	0.43049 (9)	0.6309 (2)	0.0300 (5)
C8	−0.1229 (4)	0.37977 (9)	0.5210 (2)	0.0294 (5)
C9A	0.6772 (5)	0.40623 (12)	0.8627 (3)	0.0267 (9)	0.675 (8)
H9A	0.8081	0.4161	0.8096	0.032*	0.675 (8)
C9B	0.5876 (14)	0.4037 (2)	0.9106 (5)	0.052 (3)	0.325 (8)
H9B	0.4761	0.4041	0.9799	0.063*	0.325 (8)
C10A	0.6756 (8)	0.44015 (19)	0.9815 (4)	0.0447 (13)	0.675 (8)
H10A	0.5346	0.4354	1.0287	0.054*	0.675 (8)
H10B	0.6956	0.4779	0.9620	0.054*	0.675 (8)
C10B	0.7683 (15)	0.4454 (4)	0.9408 (8)	0.054 (3)	0.325 (8)
H10C	0.7012	0.4797	0.9635	0.065*	0.325 (8)
H10D	0.8749	0.4502	0.8713	0.065*	0.325 (8)
C11	0.8799 (6)	0.41795 (13)	1.0536 (4)	0.0754 (12)
H11A	1.0166	0.4387	1.0354	0.091*	0.675 (8)
H11B	0.8519	0.4189	1.1441	0.091*	0.675 (8)
H11C	1.0272	0.4340	1.0732	0.091*	0.325 (8)
H11D	0.7826	0.4198	1.1279	0.091*	0.325 (8)
C12	0.9068 (5)	0.36158 (11)	1.0090 (3)	0.0431 (6)
H12A	0.8976	0.3367	1.0796	0.052*
H12B	1.0534	0.3568	0.9673	0.052*
C13	0.7140 (5)	0.35212 (10)	0.9178 (3)	0.0417 (6)
H13A	0.7567	0.3263	0.8532	0.050*	0.675 (8)
H13B	0.5779	0.3394	0.9612	0.050*	0.675 (8)
H13C	0.7728	0.3422	0.8352	0.050*	0.325 (8)
H13D	0.6146	0.3236	0.9481	0.050*	0.325 (8)
C14	−0.3000 (4)	0.37178 (9)	0.4292 (2)	0.0305 (5)
C15	−0.4765 (4)	0.40780 (10)	0.4209 (2)	0.0356 (5)
H15	−0.4818	0.4372	0.4752	0.043*
C16	−0.6434 (4)	0.40057 (12)	0.3334 (3)	0.0444 (6)
H16	−0.7626	0.4253	0.3272	0.053*
C17	−0.6375 (5)	0.35756 (13)	0.2550 (3)	0.0483 (7)
H17	−0.7534	0.3524	0.1957	0.058*
C18	−0.4623 (5)	0.32203 (12)	0.2631 (2)	0.0448 (6)
H18	−0.4584	0.2925	0.2091	0.054*
C19	−0.2934 (4)	0.32909 (10)	0.3487 (2)	0.0366 (5)
H19	−0.1724	0.3048	0.3527	0.044*
C20	0.2414 (4)	0.26247 (10)	0.5071 (2)	0.0387 (6)
H20A	0.3681	0.2819	0.5428	0.058*
H20B	0.2221	0.2727	0.4201	0.058*
H20C	0.2710	0.2246	0.5121	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.0364 (3)	0.0241 (3)	0.0322 (3)	−0.0045 (2)	−0.0029 (2)	0.0024 (2)
O1	0.0363 (9)	0.0261 (8)	0.0324 (9)	0.0025 (7)	−0.0072 (7)	0.0017 (6)
O2	0.0682 (13)	0.0342 (10)	0.0330 (10)	−0.0025 (9)	0.0011 (9)	0.0087 (8)
C1	0.0324 (12)	0.0235 (10)	0.0262 (11)	−0.0018 (8)	−0.0006 (9)	0.0013 (8)
C2	0.0358 (12)	0.0264 (11)	0.0251 (11)	−0.0014 (9)	−0.0013 (9)	0.0008 (9)
C3	0.0471 (14)	0.0244 (11)	0.0328 (12)	0.0012 (10)	−0.0112 (11)	0.0026 (9)
C4	0.0603 (17)	0.0283 (12)	0.0400 (14)	−0.0025 (11)	−0.0204 (13)	0.0010 (10)
C5	0.0616 (17)	0.0264 (12)	0.0406 (14)	−0.0038 (11)	−0.0191 (13)	−0.0029 (10)
C6	0.0496 (15)	0.0241 (11)	0.0354 (13)	0.0012 (10)	−0.0070 (11)	0.0015 (10)
C7	0.0363 (12)	0.0284 (11)	0.0254 (11)	0.0013 (9)	−0.0025 (9)	0.0008 (9)
C8	0.0314 (11)	0.0295 (12)	0.0273 (11)	−0.0011 (9)	0.0011 (9)	0.0006 (9)
C9A	0.0252 (17)	0.0292 (18)	0.0258 (18)	−0.0023 (13)	0.0028 (13)	0.0030 (13)
C9B	0.062 (6)	0.046 (5)	0.050 (5)	−0.011 (4)	−0.016 (5)	0.003 (4)
C10A	0.041 (3)	0.034 (2)	0.059 (3)	0.010 (2)	−0.026 (2)	−0.014 (2)
C10B	0.030 (5)	0.045 (5)	0.087 (7)	0.002 (4)	−0.002 (5)	−0.018 (5)
C11	0.078 (2)	0.0490 (19)	0.100 (3)	0.0152 (17)	−0.061 (2)	−0.0193 (18)
C12	0.0372 (14)	0.0417 (15)	0.0505 (16)	0.0036 (11)	−0.0111 (12)	0.0004 (12)
C13	0.0458 (15)	0.0351 (13)	0.0442 (15)	0.0034 (11)	−0.0128 (12)	−0.0053 (11)
C14	0.0296 (11)	0.0348 (12)	0.0271 (11)	−0.0022 (9)	−0.0014 (9)	0.0043 (9)
C15	0.0317 (12)	0.0386 (13)	0.0366 (13)	0.0008 (10)	0.0009 (10)	0.0031 (10)
C16	0.0315 (13)	0.0531 (17)	0.0485 (16)	0.0027 (12)	−0.0036 (11)	0.0111 (13)
C17	0.0366 (14)	0.067 (2)	0.0408 (15)	−0.0094 (13)	−0.0133 (12)	0.0061 (14)
C18	0.0473 (16)	0.0527 (17)	0.0343 (14)	−0.0065 (13)	−0.0079 (12)	−0.0051 (12)
C19	0.0366 (13)	0.0394 (14)	0.0338 (13)	−0.0003 (10)	−0.0040 (10)	−0.0007 (10)
C20	0.0446 (14)	0.0322 (13)	0.0395 (14)	0.0034 (11)	−0.0004 (11)	−0.0018 (10)

S1—O2	1.4888 (19)	C10B—H10C	0.9900
S1—C1	1.758 (2)	C10B—H10D	0.9900
S1—C20	1.786 (3)	C11—C12	1.519 (4)
O1—C8	1.379 (3)	C11—H11A	0.9900
O1—C7	1.380 (3)	C11—H11B	0.9900
C1—C8	1.363 (3)	C11—H11C	0.9900
C1—C2	1.446 (3)	C11—H11D	0.9900
C2—C7	1.387 (3)	C12—C13	1.530 (4)
C2—C3	1.402 (3)	C12—H12A	0.9900
C3—C4	1.385 (3)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.410 (4)	C13—H13B	0.9900
C4—C9B	1.539 (4)	C13—H13C	0.9900
C4—C9A	1.540 (4)	C13—H13D	0.9900
C5—C6	1.377 (4)	C14—C19	1.389 (3)
C5—H5	0.9500	C14—C15	1.397 (3)
C6—C7	1.375 (3)	C15—C16	1.382 (4)
C6—H6	0.9500	C15—H15	0.9500
C8—C14	1.461 (3)	C16—C17	1.382 (4)
C9A—C13	1.513 (4)	C16—H16	0.9500
C9A—C10A	1.544 (4)	C17—C18	1.383 (4)
C9A—H9A	1.0000	C17—H17	0.9500
C9B—C13	1.513 (4)	C18—C19	1.377 (4)
C9B—C10B	1.543 (4)	C18—H18	0.9500
C9B—H9B	1.0000	C19—H19	0.9500
C10A—C11	1.550 (2)	C20—H20A	0.9800
C10A—H10A	0.9900	C20—H20B	0.9800
C10A—H10B	0.9900	C20—H20C	0.9800
C10B—C11	1.551 (2)
O2—S1—C1	106.54 (11)	H11A—C11—H11B	108.8
O2—S1—C20	106.33 (12)	C12—C11—H11C	111.2
C1—S1—C20	97.78 (11)	C10A—C11—H11C	130.7
C8—O1—C7	106.39 (17)	C10B—C11—H11C	111.2
C8—C1—C2	107.1 (2)	H11A—C11—H11C	25.0
C8—C1—S1	126.08 (18)	H11B—C11—H11C	86.0
C2—C1—S1	126.56 (17)	C12—C11—H11D	111.2
C7—C2—C3	118.8 (2)	C10A—C11—H11D	85.9
C7—C2—C1	105.1 (2)	C10B—C11—H11D	111.2
C3—C2—C1	136.1 (2)	H11A—C11—H11D	128.2
C4—C3—C2	119.4 (2)	H11B—C11—H11D	26.2
C4—C3—H3	120.3	H11C—C11—H11D	109.1
C2—C3—H3	120.3	C11—C12—C13	105.8 (2)
C3—C4—C5	119.0 (2)	C11—C12—H12A	110.6
C3—C4—C9B	117.0 (3)	C13—C12—H12A	110.6
C5—C4—C9B	119.5 (3)	C11—C12—H12B	110.6
C3—C4—C9A	121.9 (2)	C13—C12—H12B	110.6
C5—C4—C9A	118.7 (2)	H12A—C12—H12B	108.7
C9B—C4—C9A	28.0 (3)	C9A—C13—C9B	28.5 (3)
C6—C5—C4	122.9 (2)	C9A—C13—C12	102.6 (2)
C6—C5—H5	118.6	C9B—C13—C12	105.7 (3)
C4—C5—H5	118.6	C9A—C13—H13A	111.2
C7—C6—C5	116.1 (2)	C9B—C13—H13A	131.7
C7—C6—H6	122.0	C12—C13—H13A	111.2
C5—C6—H6	122.0	C9A—C13—H13B	111.2
C6—C7—O1	125.4 (2)	C9B—C13—H13B	84.2
C6—C7—C2	123.9 (2)	C12—C13—H13B	111.2
O1—C7—C2	110.7 (2)	H13A—C13—H13B	109.2
C1—C8—O1	110.6 (2)	C9A—C13—H13C	86.0
C1—C8—C14	133.8 (2)	C9B—C13—H13C	110.6
O1—C8—C14	115.5 (2)	C12—C13—H13C	110.6
C13—C9A—C4	115.2 (2)	H13A—C13—H13C	26.7
C13—C9A—C10A	100.5 (3)	H13B—C13—H13C	129.2
C4—C9A—C10A	111.1 (2)	C9A—C13—H13D	134.9
C13—C9A—H9A	109.9	C9B—C13—H13D	110.6
C4—C9A—H9A	109.9	C12—C13—H13D	110.6
C10A—C9A—H9A	109.9	H13A—C13—H13D	84.4
C13—C9B—C4	115.2 (2)	H13B—C13—H13D	28.0
C13—C9B—C10B	103.6 (6)	H13C—C13—H13D	108.7
C4—C9B—C10B	115.2 (5)	C19—C14—C15	119.5 (2)
C13—C9B—H9B	107.5	C19—C14—C8	120.7 (2)
C4—C9B—H9B	107.5	C15—C14—C8	119.8 (2)
C10B—C9B—H9B	107.5	C16—C15—C14	119.9 (2)
C9A—C10A—C11	102.0 (3)	C16—C15—H15	120.1
C9A—C10A—H10A	111.4	C14—C15—H15	120.1
C11—C10A—H10A	111.4	C17—C16—C15	120.3 (3)
C9A—C10A—H10B	111.4	C17—C16—H16	119.9
C11—C10A—H10B	111.4	C15—C16—H16	119.9
H10A—C10A—H10B	109.2	C16—C17—C18	119.8 (3)
C9B—C10B—C11	99.0 (3)	C16—C17—H17	120.1
C9B—C10B—H10C	112.0	C18—C17—H17	120.1
C11—C10B—H10C	112.0	C19—C18—C17	120.6 (3)
C9B—C10B—H10D	112.0	C19—C18—H18	119.7
C11—C10B—H10D	112.0	C17—C18—H18	119.7
H10C—C10B—H10D	109.6	C18—C19—C14	120.0 (2)
C12—C11—C10A	105.5 (3)	C18—C19—H19	120.0
C12—C11—C10B	102.7 (5)	C14—C19—H19	120.0
C10A—C11—C10B	26.8 (3)	S1—C20—H20A	109.5
C12—C11—H11A	110.6	S1—C20—H20B	109.5
C10A—C11—H11A	110.6	H20A—C20—H20B	109.5
C10B—C11—H11A	87.6	S1—C20—H20C	109.5
C12—C11—H11B	110.6	H20A—C20—H20C	109.5
C10A—C11—H11B	110.6	H20B—C20—H20C	109.5
C10B—C11—H11B	133.6
O2—S1—C1—C8	−139.2 (2)	C5—C4—C9B—C13	−162.9 (5)
C20—S1—C1—C8	111.2 (2)	C9A—C4—C9B—C13	−66.5 (3)
O2—S1—C1—C2	34.2 (2)	C3—C4—C9B—C10B	161.8 (6)
C20—S1—C1—C2	−75.4 (2)	C5—C4—C9B—C10B	−42.3 (8)
C8—C1—C2—C7	0.5 (2)	C9A—C4—C9B—C10B	54.1 (9)
S1—C1—C2—C7	−173.96 (17)	C13—C9A—C10A—C11	45.1 (4)
C8—C1—C2—C3	−178.4 (3)	C4—C9A—C10A—C11	167.5 (3)
S1—C1—C2—C3	7.2 (4)	C13—C9B—C10B—C11	−45.0 (8)
C7—C2—C3—C4	−1.5 (4)	C4—C9B—C10B—C11	−171.7 (5)
C1—C2—C3—C4	177.2 (3)	C9A—C10A—C11—C12	−26.3 (5)
C2—C3—C4—C5	2.1 (4)	C9A—C10A—C11—C10B	61.3 (9)
C2—C3—C4—C9B	158.0 (4)	C9B—C10B—C11—C12	45.7 (7)
C2—C3—C4—C9A	−170.2 (2)	C9B—C10B—C11—C10A	−53.6 (5)
C3—C4—C5—C6	−1.4 (5)	C10A—C11—C12—C13	−2.3 (4)
C9B—C4—C5—C6	−156.7 (5)	C10B—C11—C12—C13	−29.8 (5)
C9A—C4—C5—C6	171.1 (3)	C4—C9A—C13—C9B	−66.7 (3)
C4—C5—C6—C7	0.2 (4)	C10A—C9A—C13—C9B	52.8 (5)
C5—C6—C7—O1	−178.1 (2)	C4—C9A—C13—C12	−166.4 (3)
C5—C6—C7—C2	0.3 (4)	C10A—C9A—C13—C12	−47.0 (3)
C8—O1—C7—C6	178.3 (2)	C4—C9B—C13—C9A	66.7 (3)
C8—O1—C7—C2	−0.3 (2)	C10B—C9B—C13—C9A	−60.1 (7)
C3—C2—C7—C6	0.3 (4)	C4—C9B—C13—C12	154.3 (5)
C1—C2—C7—C6	−178.8 (2)	C10B—C9B—C13—C12	27.5 (6)
C3—C2—C7—O1	179.0 (2)	C11—C12—C13—C9A	30.8 (3)
C1—C2—C7—O1	−0.1 (3)	C11—C12—C13—C9B	1.6 (5)
C2—C1—C8—O1	−0.7 (3)	C1—C8—C14—C19	−30.9 (4)
S1—C1—C8—O1	173.79 (16)	O1—C8—C14—C19	146.6 (2)
C2—C1—C8—C14	176.8 (2)	C1—C8—C14—C15	150.1 (3)
S1—C1—C8—C14	−8.7 (4)	O1—C8—C14—C15	−32.5 (3)
C7—O1—C8—C1	0.6 (2)	C19—C14—C15—C16	0.4 (4)
C7—O1—C8—C14	−177.40 (19)	C8—C14—C15—C16	179.5 (2)
C3—C4—C9A—C13	−21.6 (4)	C14—C15—C16—C17	0.6 (4)
C5—C4—C9A—C13	166.1 (3)	C15—C16—C17—C18	−0.8 (4)
C9B—C4—C9A—C13	66.6 (3)	C16—C17—C18—C19	0.0 (4)
C3—C4—C9A—C10A	−135.0 (4)	C17—C18—C19—C14	1.0 (4)
C5—C4—C9A—C10A	52.7 (4)	C15—C14—C19—C18	−1.2 (4)
C9B—C4—C9A—C10A	−46.8 (5)	C8—C14—C19—C18	179.7 (2)
C3—C4—C9B—C13	41.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2i	0.95	2.53	3.324 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.95	2.53	3.324 (3)	142

Symmetry code: (i) .