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

In the title compound, C(20)H(20)O(3)S, the cyclo-pentyl ring adopts an envelope conformation. The phenyl ring makes a dihedral angle of 81.40 (6)° 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.

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 5-alkyl-2-methyl-3-phenyl­sulfonyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C20H20O3S

M = 340.42

Monoclinic,

a = 6.2999 (9) Å

b = 15.001 (2) Å

c = 17.743 (2) Å

β = 92.011 (3)°

V = 1675.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.27 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.946, T max = 0.983

15497 measured reflections

3616 independent reflections

2869 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.130

S = 1.04

3616 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.44 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 datablock(s) global, I. DOI: 10.1107/S160053681103042X/zl2391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103042X/zl2391Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103042X/zl2391Isup3.cml

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

C20H20O3S	F(000) = 720
Mr = 340.42	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3720 reflections
a = 6.2999 (9) Å	θ = 2.3–25.9°
b = 15.001 (2) Å	µ = 0.21 mm−1
c = 17.743 (2) Å	T = 173 K
β = 92.011 (3)°	Block, colourless
V = 1675.8 (4) Å3	0.27 × 0.10 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3616 independent reflections
Radiation source: rotating anode	2869 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.065
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −18→19
Tmin = 0.946, Tmax = 0.983	l = −22→22
15497 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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.8019P] where P = (Fo2 + 2Fc2)/3
3616 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.44 e Å−3
0 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
S1	0.49451 (8)	0.34441 (4)	0.69600 (3)	0.03570 (17)
O1	0.2815 (2)	0.42140 (10)	0.49705 (9)	0.0416 (4)
O2	0.7200 (2)	0.33502 (12)	0.70766 (9)	0.0469 (4)
O3	0.3805 (3)	0.40440 (11)	0.74236 (9)	0.0502 (4)
C1	0.4473 (3)	0.37248 (14)	0.60261 (12)	0.0337 (5)
C2	0.5648 (3)	0.33976 (13)	0.53954 (11)	0.0311 (4)
C3	0.7450 (3)	0.28710 (13)	0.53044 (11)	0.0304 (4)
H3	0.8255	0.2661	0.5731	0.036*
C4	0.8043 (3)	0.26593 (13)	0.45818 (11)	0.0312 (4)
C5	0.6835 (3)	0.29847 (15)	0.39625 (12)	0.0391 (5)
H5	0.7246	0.2829	0.3469	0.047*
C6	0.5081 (4)	0.35192 (16)	0.40378 (13)	0.0417 (5)
H6	0.4289	0.3742	0.3613	0.050*
C7	0.4540 (3)	0.37123 (14)	0.47631 (12)	0.0349 (5)
C8	0.2785 (3)	0.42026 (14)	0.57351 (13)	0.0380 (5)
C9	0.9944 (3)	0.20828 (14)	0.44394 (11)	0.0341 (5)
H9	1.0897	0.2426	0.4106	0.041*
C10	1.1282 (3)	0.17647 (15)	0.51169 (13)	0.0399 (5)
H10A	1.0380	0.1504	0.5506	0.048*
H10B	1.2124	0.2260	0.5343	0.048*
C11	1.2724 (4)	0.10590 (17)	0.47845 (15)	0.0503 (6)
H11A	1.3148	0.0610	0.5170	0.060*
H11B	1.4021	0.1336	0.4589	0.060*
C12	1.1391 (4)	0.06297 (18)	0.41446 (14)	0.0551 (7)
H12A	1.2193	0.0619	0.3675	0.066*
H12B	1.1012	0.0010	0.4277	0.066*
C13	0.9395 (4)	0.11989 (16)	0.40397 (13)	0.0463 (6)
H13A	0.8167	0.0908	0.4272	0.056*
H13B	0.9051	0.1299	0.3498	0.056*
C14	0.1001 (4)	0.46840 (16)	0.60728 (15)	0.0508 (6)
H14A	0.1019	0.5309	0.5914	0.076*
H14B	0.1147	0.4652	0.6624	0.076*
H14C	−0.0346	0.4410	0.5905	0.076*
C15	0.3793 (3)	0.23799 (14)	0.70462 (11)	0.0306 (4)
C16	0.4923 (4)	0.16333 (15)	0.68364 (12)	0.0397 (5)
H16	0.6306	0.1693	0.6645	0.048*
C17	0.4017 (4)	0.08023 (16)	0.69086 (13)	0.0484 (6)
H17	0.4779	0.0285	0.6769	0.058*
C18	0.2011 (4)	0.07225 (16)	0.71818 (13)	0.0475 (6)
H18	0.1400	0.0148	0.7235	0.057*
C19	0.0885 (4)	0.14626 (16)	0.73774 (13)	0.0438 (5)
H19	−0.0504	0.1399	0.7562	0.053*
C20	0.1760 (3)	0.23023 (15)	0.73080 (12)	0.0378 (5)
H20	0.0977	0.2818	0.7438	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0368 (3)	0.0405 (3)	0.0297 (3)	−0.0009 (2)	−0.0001 (2)	−0.0102 (2)
O1	0.0392 (8)	0.0379 (9)	0.0475 (10)	0.0027 (6)	−0.0034 (7)	0.0097 (7)
O2	0.0366 (8)	0.0688 (12)	0.0350 (9)	−0.0052 (7)	−0.0044 (6)	−0.0048 (8)
O3	0.0600 (10)	0.0460 (10)	0.0449 (10)	−0.0011 (8)	0.0077 (8)	−0.0213 (8)
C1	0.0347 (10)	0.0302 (10)	0.0361 (12)	−0.0023 (8)	0.0001 (9)	−0.0050 (9)
C2	0.0348 (10)	0.0296 (10)	0.0288 (11)	−0.0066 (8)	−0.0008 (8)	−0.0004 (8)
C3	0.0339 (10)	0.0318 (11)	0.0253 (10)	−0.0038 (8)	−0.0027 (8)	0.0015 (8)
C4	0.0347 (10)	0.0326 (11)	0.0262 (11)	−0.0109 (8)	0.0002 (8)	0.0023 (8)
C5	0.0450 (12)	0.0464 (13)	0.0260 (11)	−0.0102 (10)	0.0021 (9)	0.0043 (9)
C6	0.0433 (12)	0.0494 (14)	0.0318 (12)	−0.0079 (10)	−0.0067 (9)	0.0155 (10)
C7	0.0335 (10)	0.0320 (11)	0.0390 (12)	−0.0040 (8)	−0.0031 (9)	0.0077 (9)
C8	0.0380 (11)	0.0294 (11)	0.0465 (14)	−0.0032 (8)	−0.0009 (9)	−0.0003 (9)
C9	0.0387 (11)	0.0360 (11)	0.0280 (11)	−0.0076 (9)	0.0071 (9)	0.0003 (9)
C10	0.0380 (11)	0.0415 (13)	0.0402 (13)	−0.0051 (9)	−0.0004 (9)	−0.0068 (10)
C11	0.0436 (13)	0.0509 (15)	0.0569 (16)	0.0045 (11)	0.0083 (11)	−0.0020 (12)
C12	0.0709 (17)	0.0497 (15)	0.0459 (15)	0.0079 (12)	0.0178 (13)	−0.0066 (12)
C13	0.0574 (14)	0.0453 (14)	0.0360 (13)	−0.0031 (11)	−0.0001 (11)	−0.0090 (10)
C14	0.0413 (12)	0.0395 (13)	0.0715 (18)	0.0065 (10)	0.0017 (12)	−0.0011 (12)
C15	0.0343 (10)	0.0370 (11)	0.0201 (10)	0.0053 (8)	−0.0036 (8)	−0.0044 (8)
C16	0.0434 (12)	0.0450 (13)	0.0310 (12)	0.0156 (10)	0.0062 (9)	0.0021 (9)
C17	0.0731 (16)	0.0380 (13)	0.0345 (13)	0.0196 (11)	0.0065 (11)	0.0013 (10)
C18	0.0697 (16)	0.0392 (13)	0.0332 (13)	−0.0023 (11)	−0.0015 (11)	−0.0002 (10)
C19	0.0406 (12)	0.0512 (14)	0.0393 (13)	−0.0034 (10)	−0.0004 (10)	−0.0015 (10)
C20	0.0360 (11)	0.0413 (12)	0.0361 (12)	0.0076 (9)	0.0005 (9)	−0.0070 (9)

S1—O3	1.4295 (15)	C10—H10B	0.9900
S1—O2	1.4351 (16)	C11—C12	1.530 (4)
S1—C1	1.725 (2)	C11—H11A	0.9900
S1—C15	1.763 (2)	C11—H11B	0.9900
O1—C8	1.358 (3)	C12—C13	1.526 (3)
O1—C7	1.382 (3)	C12—H12A	0.9900
C1—C8	1.368 (3)	C12—H12B	0.9900
C1—C2	1.449 (3)	C13—H13A	0.9900
C2—C7	1.383 (3)	C13—H13B	0.9900
C2—C3	1.397 (3)	C14—H14A	0.9800
C3—C4	1.385 (3)	C14—H14B	0.9800
C3—H3	0.9500	C14—H14C	0.9800
C4—C5	1.402 (3)	C15—C20	1.383 (3)
C4—C9	1.506 (3)	C15—C16	1.385 (3)
C5—C6	1.376 (3)	C16—C17	1.379 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.374 (3)	C17—C18	1.374 (4)
C6—H6	0.9500	C17—H17	0.9500
C8—C14	1.481 (3)	C18—C19	1.369 (3)
C9—C10	1.520 (3)	C18—H18	0.9500
C9—C13	1.537 (3)	C19—C20	1.382 (3)
C9—H9	1.0000	C19—H19	0.9500
C10—C11	1.527 (3)	C20—H20	0.9500
C10—H10A	0.9900
O3—S1—O2	119.56 (10)	C10—C11—C12	105.06 (19)
O3—S1—C1	109.02 (10)	C10—C11—H11A	110.7
O2—S1—C1	107.38 (10)	C12—C11—H11A	110.7
O3—S1—C15	107.67 (10)	C10—C11—H11B	110.7
O2—S1—C15	107.89 (10)	C12—C11—H11B	110.7
C1—S1—C15	104.29 (10)	H11A—C11—H11B	108.8
C8—O1—C7	107.31 (16)	C13—C12—C11	106.46 (19)
C8—C1—C2	107.29 (19)	C13—C12—H12A	110.4
C8—C1—S1	126.56 (17)	C11—C12—H12A	110.4
C2—C1—S1	125.71 (16)	C13—C12—H12B	110.4
C7—C2—C3	119.22 (19)	C11—C12—H12B	110.4
C7—C2—C1	104.71 (18)	H12A—C12—H12B	108.6
C3—C2—C1	136.06 (19)	C12—C13—C9	104.8 (2)
C4—C3—C2	118.90 (19)	C12—C13—H13A	110.8
C4—C3—H3	120.5	C9—C13—H13A	110.8
C2—C3—H3	120.5	C12—C13—H13B	110.8
C3—C4—C5	119.3 (2)	C9—C13—H13B	110.8
C3—C4—C9	121.93 (18)	H13A—C13—H13B	108.9
C5—C4—C9	118.78 (18)	C8—C14—H14A	109.5
C6—C5—C4	122.9 (2)	C8—C14—H14B	109.5
C6—C5—H5	118.6	H14A—C14—H14B	109.5
C4—C5—H5	118.6	C8—C14—H14C	109.5
C7—C6—C5	116.1 (2)	H14A—C14—H14C	109.5
C7—C6—H6	121.9	H14B—C14—H14C	109.5
C5—C6—H6	121.9	C20—C15—C16	120.9 (2)
C6—C7—O1	126.0 (2)	C20—C15—S1	119.64 (16)
C6—C7—C2	123.6 (2)	C16—C15—S1	119.45 (16)
O1—C7—C2	110.42 (18)	C17—C16—C15	119.2 (2)
O1—C8—C1	110.25 (19)	C17—C16—H16	120.4
O1—C8—C14	115.8 (2)	C15—C16—H16	120.4
C1—C8—C14	133.9 (2)	C18—C17—C16	120.0 (2)
C4—C9—C10	118.02 (17)	C18—C17—H17	120.0
C4—C9—C13	113.90 (17)	C16—C17—H17	120.0
C10—C9—C13	101.75 (18)	C19—C18—C17	120.6 (2)
C4—C9—H9	107.5	C19—C18—H18	119.7
C10—C9—H9	107.5	C17—C18—H18	119.7
C13—C9—H9	107.5	C18—C19—C20	120.3 (2)
C9—C10—C11	103.48 (18)	C18—C19—H19	119.8
C9—C10—H10A	111.1	C20—C19—H19	119.8
C11—C10—H10A	111.1	C19—C20—C15	118.9 (2)
C9—C10—H10B	111.1	C19—C20—H20	120.5
C11—C10—H10B	111.1	C15—C20—H20	120.5
H10A—C10—H10B	109.0
O3—S1—C1—C8	−21.6 (2)	S1—C1—C8—O1	−173.51 (15)
O2—S1—C1—C8	−152.50 (19)	C2—C1—C8—C14	178.7 (2)
C15—S1—C1—C8	93.2 (2)	S1—C1—C8—C14	6.0 (4)
O3—S1—C1—C2	167.01 (17)	C3—C4—C9—C10	−2.7 (3)
O2—S1—C1—C2	36.1 (2)	C5—C4—C9—C10	177.77 (18)
C15—S1—C1—C2	−78.21 (19)	C3—C4—C9—C13	116.6 (2)
C8—C1—C2—C7	−0.1 (2)	C5—C4—C9—C13	−63.0 (2)
S1—C1—C2—C7	172.67 (15)	C4—C9—C10—C11	168.43 (18)
C8—C1—C2—C3	−178.6 (2)	C13—C9—C10—C11	43.0 (2)
S1—C1—C2—C3	−5.8 (3)	C9—C10—C11—C12	−32.8 (2)
C7—C2—C3—C4	−1.7 (3)	C10—C11—C12—C13	9.5 (3)
C1—C2—C3—C4	176.6 (2)	C11—C12—C13—C9	17.1 (3)
C2—C3—C4—C5	0.6 (3)	C4—C9—C13—C12	−165.15 (18)
C2—C3—C4—C9	−178.99 (17)	C10—C9—C13—C12	−37.1 (2)
C3—C4—C5—C6	0.8 (3)	O3—S1—C15—C20	19.5 (2)
C9—C4—C5—C6	−179.64 (19)	O2—S1—C15—C20	149.86 (17)
C4—C5—C6—C7	−0.9 (3)	C1—S1—C15—C20	−96.18 (18)
C5—C6—C7—O1	−178.17 (19)	O3—S1—C15—C16	−161.71 (17)
C5—C6—C7—C2	−0.3 (3)	O2—S1—C15—C16	−31.40 (19)
C8—O1—C7—C6	176.6 (2)	C1—S1—C15—C16	82.56 (18)
C8—O1—C7—C2	−1.5 (2)	C20—C15—C16—C17	−1.6 (3)
C3—C2—C7—C6	1.6 (3)	S1—C15—C16—C17	179.70 (17)
C1—C2—C7—C6	−177.2 (2)	C15—C16—C17—C18	0.4 (3)
C3—C2—C7—O1	179.78 (16)	C16—C17—C18—C19	0.7 (4)
C1—C2—C7—O1	1.0 (2)	C17—C18—C19—C20	−0.5 (4)
C7—O1—C8—C1	1.4 (2)	C18—C19—C20—C15	−0.7 (3)
C7—O1—C8—C14	−178.18 (18)	C16—C15—C20—C19	1.7 (3)
C2—C1—C8—O1	−0.8 (2)	S1—C15—C20—C19	−179.54 (17)

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3i	0.99	2.52	3.493 (3)	166.
C17—H17···O3ii	0.95	2.49	3.183 (3)	129.
C10—H10B···Cgiii	0.99	2.68	3.604 (3)	156.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O3i	0.99	2.52	3.493 (3)	166
C17—H17⋯O3ii	0.95	2.49	3.183 (3)	129
C10—H10B⋯Cgiii	0.99	2.68	3.604 (3)	156

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