5-Cyclo-hexyl-3-cyclo-hexyl-sulfonyl-2-methyl-1-benzofuran.

In the title compound, C(21)H(28)O(3)S, the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. Both cyclo-hexane rings adopt chair conformations.

Related literature

For the pharmacological 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-methyl­sufinyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C21H28O3S

M = 360.49

Triclinic,

a = 6.8819 (2) Å

b = 10.7244 (3) Å

c = 13.3533 (4) Å

α = 77.132 (2)°

β = 83.165 (2)°

γ = 87.597 (2)°

V = 953.83 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.969

17113 measured reflections

4397 independent reflections

3140 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.06

4397 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.32 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536811007872/nk2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007872/nk2090Isup2.hkl

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

C21H28O3S	Z = 2
Mr = 360.49	F(000) = 388
Triclinic, P1	Dx = 1.255 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8819 (2) Å	Cell parameters from 6431 reflections
b = 10.7244 (3) Å	θ = 2.6–27.5°
c = 13.3533 (4) Å	µ = 0.19 mm−1
α = 77.132 (2)°	T = 298 K
β = 83.165 (2)°	Block, colourless
γ = 87.597 (2)°	0.20 × 0.17 × 0.17 mm
V = 953.83 (5) Å3

Bruker SMART APEXII CCD diffractometer	4397 independent reflections
Radiation source: rotating anode	3140 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.6°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.963, Tmax = 0.969	l = −17→17
17113 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.1575P] where P = (Fo2 + 2Fc2)/3
4397 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.32 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	0.52844 (7)	0.02769 (5)	0.68510 (4)	0.05492 (17)
O1	0.24896 (19)	0.06179 (12)	0.95160 (10)	0.0577 (3)
O2	0.4736 (2)	−0.10029 (13)	0.68671 (12)	0.0741 (4)
O3	0.73307 (19)	0.05695 (15)	0.67114 (12)	0.0711 (4)
C1	0.4324 (2)	0.06712 (16)	0.80074 (14)	0.0471 (4)
C2	0.5173 (2)	0.15467 (16)	0.85153 (13)	0.0464 (4)
C3	0.6739 (3)	0.23846 (17)	0.82839 (14)	0.0495 (4)
H3	0.7569	0.2446	0.7673	0.059*
C4	0.7042 (3)	0.31244 (17)	0.89796 (14)	0.0519 (4)
C5	0.5794 (3)	0.2984 (2)	0.99068 (15)	0.0620 (5)
H5	0.6019	0.3475	1.0373	0.074*
C6	0.4256 (3)	0.2156 (2)	1.01573 (15)	0.0628 (5)
H6	0.3448	0.2070	1.0778	0.075*
C7	0.3978 (3)	0.14608 (17)	0.94388 (14)	0.0516 (4)
C8	0.2723 (3)	0.01559 (17)	0.86374 (15)	0.0524 (4)
C9	0.8639 (3)	0.41041 (18)	0.87500 (15)	0.0553 (5)
H9	0.8911	0.4251	0.9418	0.066*
C10	0.7991 (3)	0.53748 (19)	0.8132 (2)	0.0713 (6)
H10A	0.6801	0.5662	0.8487	0.086*
H10B	0.7702	0.5272	0.7462	0.086*
C11	0.9558 (3)	0.6382 (2)	0.7982 (2)	0.0843 (7)
H11A	0.9130	0.7165	0.7540	0.101*
H11B	0.9718	0.6566	0.8646	0.101*
C12	1.1487 (3)	0.5964 (2)	0.75125 (19)	0.0759 (6)
H12A	1.1385	0.5911	0.6805	0.091*
H12B	1.2466	0.6594	0.7500	0.091*
C13	1.2116 (3)	0.4695 (2)	0.8108 (3)	0.0896 (8)
H13A	1.2398	0.4778	0.8785	0.108*
H13B	1.3307	0.4413	0.7752	0.108*
C14	1.0539 (3)	0.3696 (2)	0.8236 (3)	0.0909 (9)
H14A	1.0340	0.3558	0.7562	0.109*
H14B	1.0975	0.2892	0.8646	0.109*
C15	0.1213 (3)	−0.0750 (2)	0.85573 (18)	0.0670 (6)
H15A	0.0979	−0.1363	0.9201	0.100*
H15B	0.1659	−0.1187	0.8016	0.100*
H15C	0.0021	−0.0288	0.8402	0.100*
C16	0.4147 (3)	0.13219 (19)	0.58508 (15)	0.0563 (5)
H16	0.4792	0.1166	0.5194	0.068*
C17	0.4450 (4)	0.2720 (2)	0.5837 (2)	0.0849 (7)
H17A	0.5839	0.2895	0.5741	0.102*
H17B	0.3902	0.2906	0.6492	0.102*
C18	0.3455 (6)	0.3575 (3)	0.4957 (3)	0.1165 (12)
H18A	0.3574	0.4463	0.4988	0.140*
H18B	0.4119	0.3462	0.4300	0.140*
C19	0.1343 (5)	0.3274 (3)	0.5015 (2)	0.1029 (9)
H19A	0.0784	0.3813	0.4431	0.124*
H19B	0.0652	0.3460	0.5643	0.124*
C20	0.1080 (4)	0.1899 (3)	0.5006 (2)	0.0874 (8)
H20A	0.1686	0.1729	0.4355	0.105*
H20B	−0.0305	0.1724	0.5064	0.105*
C21	0.1990 (3)	0.1027 (2)	0.58921 (18)	0.0741 (6)
H21A	0.1858	0.0142	0.5852	0.089*
H21B	0.1303	0.1140	0.6544	0.089*

	U11	U22	U33	U12	U13	U23
S1	0.0445 (3)	0.0590 (3)	0.0664 (3)	−0.00717 (19)	0.0051 (2)	−0.0295 (2)
O1	0.0555 (8)	0.0588 (8)	0.0563 (8)	−0.0121 (6)	0.0084 (6)	−0.0129 (6)
O2	0.0773 (10)	0.0585 (8)	0.0948 (11)	−0.0075 (7)	0.0032 (8)	−0.0399 (8)
O3	0.0423 (7)	0.0937 (11)	0.0834 (10)	−0.0075 (7)	0.0080 (7)	−0.0388 (8)
C1	0.0429 (9)	0.0460 (9)	0.0532 (10)	−0.0072 (7)	0.0013 (7)	−0.0146 (7)
C2	0.0449 (9)	0.0464 (9)	0.0482 (10)	−0.0030 (7)	−0.0029 (7)	−0.0118 (7)
C3	0.0474 (9)	0.0535 (10)	0.0489 (10)	−0.0065 (8)	−0.0039 (8)	−0.0141 (8)
C4	0.0538 (10)	0.0533 (10)	0.0513 (11)	−0.0043 (8)	−0.0124 (8)	−0.0130 (8)
C5	0.0721 (13)	0.0672 (12)	0.0534 (11)	−0.0031 (10)	−0.0104 (10)	−0.0253 (9)
C6	0.0672 (13)	0.0720 (13)	0.0501 (11)	−0.0050 (10)	0.0028 (9)	−0.0197 (9)
C7	0.0511 (10)	0.0531 (10)	0.0495 (10)	−0.0044 (8)	−0.0009 (8)	−0.0106 (8)
C8	0.0511 (10)	0.0488 (9)	0.0561 (11)	−0.0067 (8)	0.0005 (8)	−0.0115 (8)
C9	0.0615 (11)	0.0590 (11)	0.0520 (11)	−0.0098 (9)	−0.0159 (9)	−0.0196 (9)
C10	0.0525 (12)	0.0555 (11)	0.1044 (18)	−0.0008 (9)	−0.0057 (11)	−0.0160 (11)
C11	0.0698 (15)	0.0536 (12)	0.126 (2)	−0.0079 (11)	−0.0088 (14)	−0.0119 (12)
C12	0.0646 (13)	0.0882 (16)	0.0786 (15)	−0.0252 (12)	−0.0015 (11)	−0.0255 (12)
C13	0.0465 (12)	0.0799 (16)	0.156 (3)	−0.0051 (11)	−0.0167 (14)	−0.0507 (16)
C14	0.0462 (12)	0.0634 (13)	0.173 (3)	0.0006 (10)	−0.0215 (14)	−0.0417 (15)
C15	0.0567 (12)	0.0609 (12)	0.0811 (15)	−0.0215 (9)	0.0072 (10)	−0.0147 (10)
C16	0.0526 (10)	0.0691 (12)	0.0516 (11)	−0.0153 (9)	0.0048 (8)	−0.0257 (9)
C17	0.1043 (19)	0.0656 (14)	0.0884 (18)	−0.0248 (13)	−0.0321 (15)	−0.0093 (12)
C18	0.159 (3)	0.0811 (18)	0.108 (2)	−0.0358 (19)	−0.062 (2)	0.0120 (16)
C19	0.120 (3)	0.116 (2)	0.0763 (18)	0.0200 (19)	−0.0360 (17)	−0.0212 (16)
C20	0.0658 (14)	0.125 (2)	0.0737 (16)	−0.0128 (14)	−0.0137 (12)	−0.0223 (15)
C21	0.0550 (12)	0.0915 (16)	0.0764 (15)	−0.0170 (11)	−0.0042 (11)	−0.0182 (12)

S1—O2	1.4336 (14)	C12—C13	1.491 (4)
S1—O3	1.4370 (14)	C12—H12A	0.9700
S1—C1	1.7393 (17)	C12—H12B	0.9700
S1—C16	1.778 (2)	C13—C14	1.525 (3)
O1—C8	1.362 (2)	C13—H13A	0.9700
O1—C7	1.374 (2)	C13—H13B	0.9700
C1—C8	1.360 (2)	C14—H14A	0.9700
C1—C2	1.452 (2)	C14—H14B	0.9700
C2—C7	1.385 (2)	C15—H15A	0.9600
C2—C3	1.394 (2)	C15—H15B	0.9600
C3—C4	1.387 (2)	C15—H15C	0.9600
C3—H3	0.9300	C16—C17	1.518 (3)
C4—C5	1.403 (3)	C16—C21	1.523 (3)
C4—C9	1.510 (2)	C16—H16	0.9800
C5—C6	1.372 (3)	C17—C18	1.532 (4)
C5—H5	0.9300	C17—H17A	0.9700
C6—C7	1.374 (3)	C17—H17B	0.9700
C6—H6	0.9300	C18—C19	1.491 (4)
C8—C15	1.481 (3)	C18—H18A	0.9700
C9—C14	1.498 (3)	C18—H18B	0.9700
C9—C10	1.507 (3)	C19—C20	1.496 (4)
C9—H9	0.9800	C19—H19A	0.9700
C10—C11	1.523 (3)	C19—H19B	0.9700
C10—H10A	0.9700	C20—C21	1.517 (3)
C10—H10B	0.9700	C20—H20A	0.9700
C11—C12	1.495 (3)	C20—H20B	0.9700
C11—H11A	0.9700	C21—H21A	0.9700
C11—H11B	0.9700	C21—H21B	0.9700
O2—S1—O3	118.46 (9)	C12—C13—C14	111.4 (2)
O2—S1—C1	108.89 (9)	C12—C13—H13A	109.3
O3—S1—C1	106.41 (8)	C14—C13—H13A	109.3
O2—S1—C16	107.65 (9)	C12—C13—H13B	109.3
O3—S1—C16	108.06 (9)	C14—C13—H13B	109.3
C1—S1—C16	106.83 (9)	H13A—C13—H13B	108.0
C8—O1—C7	107.00 (13)	C9—C14—C13	111.67 (19)
C8—C1—C2	107.30 (15)	C9—C14—H14A	109.3
C8—C1—S1	126.59 (14)	C13—C14—H14A	109.3
C2—C1—S1	125.98 (13)	C9—C14—H14B	109.3
C7—C2—C3	119.25 (16)	C13—C14—H14B	109.3
C7—C2—C1	104.34 (15)	H14A—C14—H14B	107.9
C3—C2—C1	136.40 (16)	C8—C15—H15A	109.5
C4—C3—C2	118.98 (17)	C8—C15—H15B	109.5
C4—C3—H3	120.5	H15A—C15—H15B	109.5
C2—C3—H3	120.5	C8—C15—H15C	109.5
C3—C4—C5	119.08 (18)	H15A—C15—H15C	109.5
C3—C4—C9	121.70 (17)	H15B—C15—H15C	109.5
C5—C4—C9	119.20 (16)	C17—C16—C21	111.8 (2)
C6—C5—C4	123.02 (18)	C17—C16—S1	112.23 (14)
C6—C5—H5	118.5	C21—C16—S1	111.96 (14)
C4—C5—H5	118.5	C17—C16—H16	106.8
C5—C6—C7	116.15 (18)	C21—C16—H16	106.8
C5—C6—H6	121.9	S1—C16—H16	106.8
C7—C6—H6	121.9	C16—C17—C18	109.98 (19)
C6—C7—O1	125.66 (17)	C16—C17—H17A	109.7
C6—C7—C2	123.50 (18)	C18—C17—H17A	109.7
O1—C7—C2	110.83 (15)	C16—C17—H17B	109.7
C1—C8—O1	110.53 (16)	C18—C17—H17B	109.7
C1—C8—C15	134.11 (18)	H17A—C17—H17B	108.2
O1—C8—C15	115.35 (16)	C19—C18—C17	112.1 (2)
C14—C9—C10	109.39 (18)	C19—C18—H18A	109.2
C14—C9—C4	115.03 (16)	C17—C18—H18A	109.2
C10—C9—C4	112.23 (16)	C19—C18—H18B	109.2
C14—C9—H9	106.5	C17—C18—H18B	109.2
C10—C9—H9	106.5	H18A—C18—H18B	107.9
C4—C9—H9	106.5	C18—C19—C20	111.2 (3)
C9—C10—C11	111.57 (18)	C18—C19—H19A	109.4
C9—C10—H10A	109.3	C20—C19—H19A	109.4
C11—C10—H10A	109.3	C18—C19—H19B	109.4
C9—C10—H10B	109.3	C20—C19—H19B	109.4
C11—C10—H10B	109.3	H19A—C19—H19B	108.0
H10A—C10—H10B	108.0	C19—C20—C21	110.9 (2)
C12—C11—C10	112.5 (2)	C19—C20—H20A	109.5
C12—C11—H11A	109.1	C21—C20—H20A	109.5
C10—C11—H11A	109.1	C19—C20—H20B	109.5
C12—C11—H11B	109.1	C21—C20—H20B	109.5
C10—C11—H11B	109.1	H20A—C20—H20B	108.1
H11A—C11—H11B	107.8	C20—C21—C16	110.72 (18)
C13—C12—C11	111.2 (2)	C20—C21—H21A	109.5
C13—C12—H12A	109.4	C16—C21—H21A	109.5
C11—C12—H12A	109.4	C20—C21—H21B	109.5
C13—C12—H12B	109.4	C16—C21—H21B	109.5
C11—C12—H12B	109.4	H21A—C21—H21B	108.1
H12A—C12—H12B	108.0
O2—S1—C1—C8	−25.2 (2)	C7—O1—C8—C1	0.5 (2)
O3—S1—C1—C8	−153.94 (17)	C7—O1—C8—C15	−178.31 (16)
C16—S1—C1—C8	90.80 (18)	C3—C4—C9—C14	−40.4 (3)
O2—S1—C1—C2	149.95 (16)	C5—C4—C9—C14	141.5 (2)
O3—S1—C1—C2	21.20 (18)	C3—C4—C9—C10	85.5 (2)
C16—S1—C1—C2	−94.06 (17)	C5—C4—C9—C10	−92.6 (2)
C8—C1—C2—C7	0.7 (2)	C14—C9—C10—C11	−55.7 (3)
S1—C1—C2—C7	−175.17 (14)	C4—C9—C10—C11	175.38 (19)
C8—C1—C2—C3	−177.6 (2)	C9—C10—C11—C12	54.6 (3)
S1—C1—C2—C3	6.4 (3)	C10—C11—C12—C13	−53.1 (3)
C7—C2—C3—C4	−0.9 (3)	C11—C12—C13—C14	53.8 (3)
C1—C2—C3—C4	177.26 (19)	C10—C9—C14—C13	57.1 (3)
C2—C3—C4—C5	1.6 (3)	C4—C9—C14—C13	−175.5 (2)
C2—C3—C4—C9	−176.48 (16)	C12—C13—C14—C9	−57.0 (3)
C3—C4—C5—C6	−0.9 (3)	O2—S1—C16—C17	173.88 (16)
C9—C4—C5—C6	177.21 (19)	O3—S1—C16—C17	−57.08 (18)
C4—C5—C6—C7	−0.5 (3)	C1—S1—C16—C17	57.06 (17)
C5—C6—C7—O1	−177.38 (18)	O2—S1—C16—C21	47.25 (17)
C5—C6—C7—C2	1.2 (3)	O3—S1—C16—C21	176.29 (14)
C8—O1—C7—C6	178.74 (19)	C1—S1—C16—C21	−69.57 (16)
C8—O1—C7—C2	0.0 (2)	C21—C16—C17—C18	−53.7 (3)
C3—C2—C7—C6	−0.5 (3)	S1—C16—C17—C18	179.6 (2)
C1—C2—C7—C6	−179.22 (19)	C16—C17—C18—C19	54.7 (4)
C3—C2—C7—O1	178.26 (15)	C17—C18—C19—C20	−57.0 (3)
C1—C2—C7—O1	−0.5 (2)	C18—C19—C20—C21	57.5 (3)
C2—C1—C8—O1	−0.8 (2)	C19—C20—C21—C16	−56.4 (3)
S1—C1—C8—O1	175.11 (13)	C17—C16—C21—C20	55.3 (2)
C2—C1—C8—C15	177.7 (2)	S1—C16—C21—C20	−177.83 (17)
S1—C1—C8—C15	−6.4 (3)

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
C14—H14B···Cgi	0.97	2.80	3.649 (3)	147

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
C14—H14B⋯Cgi	0.97	2.80	3.649 (3)	147

Symmetry code: (i) .