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

In the title compound, C(18)H(24)O(3)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, mol-ecules are linked through weak non-classical 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. (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 3-aryl­sulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C18H24O3S

M = 320.44

Monoclinic,

a = 5.7117 (1) Å

b = 23.5045 (4) Å

c = 12.7980 (2) Å

β = 102.080 (1)°

V = 1680.09 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.26 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.957

15706 measured reflections

3870 independent reflections

3124 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.05

3870 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.49 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/S1600536811007215/rk2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007215/rk2267Isup2.hkl

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

C18H24O3S	F(000) = 688
Mr = 320.44	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Melting point = 467–468 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7117 (1) Å	Cell parameters from 7210 reflections
b = 23.5045 (4) Å	θ = 2.4–27.3°
c = 12.7980 (2) Å	µ = 0.20 mm−1
β = 102.080 (1)°	T = 173 K
V = 1680.09 (5) Å3	Block, colourless
Z = 4	0.26 × 0.25 × 0.22 mm

Bruker SMART APEXII CCD diffractometer	3870 independent reflections
Radiation source: rotating anode	3124 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→30
Tmin = 0.949, Tmax = 0.957	l = −16→16
15706 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.3753P] where P = (Fo2 + 2Fc2)/3
3870 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.49 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 > 2σ(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	0.79640 (7)	0.253935 (16)	0.35223 (3)	0.02755 (13)
O1	0.8519 (2)	0.14326 (5)	0.58586 (9)	0.0413 (3)
O2	1.0380 (2)	0.27516 (5)	0.37375 (10)	0.0411 (3)
O3	0.6959 (2)	0.23391 (5)	0.24608 (9)	0.0377 (3)
C1	0.7751 (3)	0.19902 (6)	0.44030 (12)	0.0296 (3)
C2	0.5856 (3)	0.15696 (6)	0.42805 (12)	0.0304 (3)
C3	0.3829 (3)	0.14321 (7)	0.35150 (13)	0.0327 (4)
H3	0.3395	0.1653	0.2883	0.039*
C4	0.2436 (3)	0.09669 (7)	0.36817 (14)	0.0367 (4)
C5	0.3105 (4)	0.06562 (7)	0.46338 (15)	0.0444 (5)
H5	0.2137	0.0343	0.4750	0.053*
C6	0.5089 (4)	0.07834 (7)	0.54037 (15)	0.0448 (5)
H6	0.5514	0.0567	0.6042	0.054*
C7	0.6431 (3)	0.12389 (7)	0.52048 (13)	0.0366 (4)
C8	0.9275 (3)	0.18916 (7)	0.53575 (13)	0.0353 (4)
C9	0.0319 (3)	0.07963 (8)	0.28150 (16)	0.0457 (5)
H9	−0.0566	0.1152	0.2548	0.055*
C10	−0.1454 (4)	0.03966 (8)	0.31629 (19)	0.0565 (6)
H10A	−0.0694	0.0026	0.3349	0.085*
H10B	−0.2851	0.0349	0.2577	0.085*
H10C	−0.1964	0.0556	0.3787	0.085*
C11	0.1175 (4)	0.05314 (12)	0.18821 (17)	0.0678 (7)
H11A	0.2218	0.0800	0.1612	0.102*
H11B	−0.0208	0.0440	0.1312	0.102*
H11C	0.2068	0.0182	0.2119	0.102*
C12	1.1480 (3)	0.21675 (9)	0.59454 (15)	0.0477 (5)
H12A	1.2862	0.1926	0.5913	0.072*
H12B	1.1371	0.2222	0.6693	0.072*
H12C	1.1672	0.2538	0.5621	0.072*
C13	0.6056 (3)	0.30757 (6)	0.38532 (12)	0.0258 (3)
H13	0.4401	0.2915	0.3746	0.031*
C14	0.6805 (3)	0.32676 (7)	0.50149 (12)	0.0368 (4)
H14A	0.6821	0.2937	0.5496	0.044*
H14B	0.8441	0.3430	0.5144	0.044*
C15	0.5051 (4)	0.37148 (8)	0.52512 (15)	0.0466 (5)
H15A	0.3454	0.3539	0.5191	0.056*
H15B	0.5590	0.3852	0.5994	0.056*
C16	0.4846 (4)	0.42147 (8)	0.44964 (18)	0.0556 (5)
H16A	0.6385	0.4423	0.4624	0.067*
H16B	0.3596	0.4478	0.4637	0.067*
C17	0.4210 (4)	0.40189 (8)	0.33352 (16)	0.0510 (5)
H17A	0.2583	0.3852	0.3185	0.061*
H17B	0.4198	0.4351	0.2859	0.061*
C18	0.5991 (3)	0.35795 (7)	0.30975 (13)	0.0369 (4)
H18A	0.7604	0.3752	0.3195	0.044*
H18B	0.5505	0.3449	0.2348	0.044*

	U11	U22	U33	U12	U13	U23
S1	0.0263 (2)	0.0315 (2)	0.0264 (2)	−0.00097 (14)	0.00923 (16)	−0.00148 (14)
O1	0.0547 (8)	0.0371 (7)	0.0309 (6)	0.0125 (6)	0.0067 (6)	0.0045 (5)
O2	0.0258 (6)	0.0519 (7)	0.0481 (7)	−0.0035 (5)	0.0136 (5)	−0.0003 (6)
O3	0.0509 (8)	0.0380 (6)	0.0257 (6)	−0.0039 (5)	0.0114 (5)	−0.0038 (5)
C1	0.0311 (8)	0.0296 (8)	0.0290 (8)	0.0061 (6)	0.0079 (7)	−0.0002 (6)
C2	0.0386 (9)	0.0239 (8)	0.0316 (8)	0.0059 (6)	0.0137 (7)	0.0014 (6)
C3	0.0381 (9)	0.0259 (8)	0.0353 (8)	0.0028 (6)	0.0106 (7)	0.0048 (6)
C4	0.0419 (10)	0.0261 (8)	0.0460 (10)	0.0020 (7)	0.0177 (8)	0.0024 (7)
C5	0.0652 (13)	0.0259 (9)	0.0494 (11)	−0.0007 (8)	0.0286 (10)	0.0042 (7)
C6	0.0719 (14)	0.0298 (9)	0.0365 (9)	0.0080 (9)	0.0203 (9)	0.0076 (7)
C7	0.0531 (11)	0.0282 (8)	0.0302 (8)	0.0114 (7)	0.0129 (8)	0.0014 (7)
C8	0.0383 (9)	0.0369 (9)	0.0321 (8)	0.0119 (7)	0.0104 (7)	−0.0006 (7)
C9	0.0407 (10)	0.0320 (9)	0.0653 (13)	−0.0056 (8)	0.0131 (9)	0.0057 (8)
C10	0.0537 (12)	0.0407 (11)	0.0843 (16)	−0.0120 (9)	0.0353 (11)	−0.0130 (11)
C11	0.0508 (13)	0.1066 (19)	0.0474 (12)	−0.0300 (13)	0.0135 (10)	−0.0090 (12)
C12	0.0380 (10)	0.0636 (13)	0.0375 (10)	0.0114 (9)	−0.0010 (8)	−0.0016 (9)
C13	0.0226 (7)	0.0271 (7)	0.0280 (8)	−0.0010 (6)	0.0058 (6)	0.0000 (6)
C14	0.0450 (10)	0.0387 (9)	0.0271 (8)	0.0071 (7)	0.0084 (7)	−0.0029 (7)
C15	0.0551 (12)	0.0444 (11)	0.0426 (10)	0.0081 (9)	0.0151 (9)	−0.0105 (8)
C16	0.0661 (14)	0.0319 (10)	0.0688 (14)	0.0063 (9)	0.0139 (11)	−0.0103 (9)
C17	0.0616 (13)	0.0346 (10)	0.0542 (12)	0.0126 (9)	0.0067 (10)	0.0081 (8)
C18	0.0459 (10)	0.0318 (9)	0.0316 (8)	−0.0020 (7)	0.0051 (7)	0.0048 (7)

S1—O3	1.4389 (12)	C10—H10C	0.9800
S1—O2	1.4389 (12)	C11—H11A	0.9800
S1—C1	1.7345 (16)	C11—H11B	0.9800
S1—C13	1.7747 (15)	C11—H11C	0.9800
O1—C8	1.370 (2)	C12—H12A	0.9800
O1—C7	1.383 (2)	C12—H12B	0.9800
C1—C8	1.363 (2)	C12—H12C	0.9800
C1—C2	1.450 (2)	C13—C18	1.524 (2)
C2—C3	1.389 (2)	C13—C14	1.527 (2)
C2—C7	1.396 (2)	C13—H13	1.0000
C3—C4	1.395 (2)	C14—C15	1.526 (2)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.403 (2)	C14—H14B	0.9900
C4—C9	1.514 (3)	C15—C16	1.510 (3)
C5—C6	1.370 (3)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.371 (3)	C16—C17	1.525 (3)
C6—H6	0.9500	C16—H16A	0.9900
C8—C12	1.475 (3)	C16—H16B	0.9900
C9—C10	1.515 (2)	C17—C18	1.524 (3)
C9—C11	1.515 (3)	C17—H17A	0.9900
C9—H9	1.0000	C17—H17B	0.9900
C10—H10A	0.9800	C18—H18A	0.9900
C10—H10B	0.9800	C18—H18B	0.9900
O3—S1—O2	118.13 (7)	C9—C11—H11C	109.5
O3—S1—C1	107.55 (7)	H11A—C11—H11C	109.5
O2—S1—C1	109.19 (8)	H11B—C11—H11C	109.5
O3—S1—C13	108.30 (7)	C8—C12—H12A	109.5
O2—S1—C13	108.69 (7)	C8—C12—H12B	109.5
C1—S1—C13	104.09 (7)	H12A—C12—H12B	109.5
C8—O1—C7	107.01 (12)	C8—C12—H12C	109.5
C8—C1—C2	107.65 (14)	H12A—C12—H12C	109.5
C8—C1—S1	126.16 (13)	H12B—C12—H12C	109.5
C2—C1—S1	126.13 (12)	C18—C13—C14	110.67 (13)
C3—C2—C7	118.78 (15)	C18—C13—S1	109.58 (11)
C3—C2—C1	136.71 (15)	C14—C13—S1	112.41 (11)
C7—C2—C1	104.49 (15)	C18—C13—H13	108.0
C2—C3—C4	119.51 (15)	C14—C13—H13	108.0
C2—C3—H3	120.2	S1—C13—H13	108.0
C4—C3—H3	120.2	C15—C14—C13	109.55 (14)
C3—C4—C5	118.71 (16)	C15—C14—H14A	109.8
C3—C4—C9	119.30 (15)	C13—C14—H14A	109.8
C5—C4—C9	121.93 (16)	C15—C14—H14B	109.8
C6—C5—C4	123.01 (17)	C13—C14—H14B	109.8
C6—C5—H5	118.5	H14A—C14—H14B	108.2
C4—C5—H5	118.5	C16—C15—C14	112.06 (16)
C5—C6—C7	116.56 (16)	C16—C15—H15A	109.2
C5—C6—H6	121.7	C14—C15—H15A	109.2
C7—C6—H6	121.7	C16—C15—H15B	109.2
C6—C7—O1	126.13 (15)	C14—C15—H15B	109.2
C6—C7—C2	123.41 (17)	H15A—C15—H15B	107.9
O1—C7—C2	110.46 (15)	C15—C16—C17	111.05 (15)
C1—C8—O1	110.38 (15)	C15—C16—H16A	109.4
C1—C8—C12	134.37 (17)	C17—C16—H16A	109.4
O1—C8—C12	115.25 (15)	C15—C16—H16B	109.4
C4—C9—C10	115.43 (17)	C17—C16—H16B	109.4
C4—C9—C11	110.26 (16)	H16A—C16—H16B	108.0
C10—C9—C11	108.82 (16)	C18—C17—C16	111.48 (15)
C4—C9—H9	107.3	C18—C17—H17A	109.3
C10—C9—H9	107.3	C16—C17—H17A	109.3
C11—C9—H9	107.3	C18—C17—H17B	109.3
C9—C10—H10A	109.5	C16—C17—H17B	109.3
C9—C10—H10B	109.5	H17A—C17—H17B	108.0
H10A—C10—H10B	109.5	C17—C18—C13	109.17 (14)
C9—C10—H10C	109.5	C17—C18—H18A	109.8
H10A—C10—H10C	109.5	C13—C18—H18A	109.8
H10B—C10—H10C	109.5	C17—C18—H18B	109.8
C9—C11—H11A	109.5	C13—C18—H18B	109.8
C9—C11—H11B	109.5	H18A—C18—H18B	108.3
H11A—C11—H11B	109.5
O3—S1—C1—C8	149.94 (14)	C2—C1—C8—O1	0.67 (18)
O2—S1—C1—C8	20.63 (17)	S1—C1—C8—O1	177.99 (11)
C13—S1—C1—C8	−95.29 (15)	C2—C1—C8—C12	−178.92 (18)
O3—S1—C1—C2	−33.21 (15)	S1—C1—C8—C12	−1.6 (3)
O2—S1—C1—C2	−162.53 (13)	C7—O1—C8—C1	−0.73 (17)
C13—S1—C1—C2	81.56 (14)	C7—O1—C8—C12	178.94 (14)
C8—C1—C2—C3	−179.01 (18)	C3—C4—C9—C10	−164.47 (16)
S1—C1—C2—C3	3.7 (3)	C5—C4—C9—C10	18.3 (2)
C8—C1—C2—C7	−0.33 (17)	C3—C4—C9—C11	71.7 (2)
S1—C1—C2—C7	−177.66 (12)	C5—C4—C9—C11	−105.5 (2)
C7—C2—C3—C4	−0.6 (2)	O3—S1—C13—C18	−63.30 (12)
C1—C2—C3—C4	177.97 (17)	O2—S1—C13—C18	66.20 (12)
C2—C3—C4—C5	1.2 (2)	C1—S1—C13—C18	−177.53 (11)
C2—C3—C4—C9	−176.17 (15)	O3—S1—C13—C14	173.20 (11)
C3—C4—C5—C6	−1.0 (3)	O2—S1—C13—C14	−57.30 (13)
C9—C4—C5—C6	176.28 (18)	C1—S1—C13—C14	58.97 (13)
C4—C5—C6—C7	0.1 (3)	C18—C13—C14—C15	58.75 (18)
C5—C6—C7—O1	−178.51 (16)	S1—C13—C14—C15	−178.37 (12)
C5—C6—C7—C2	0.5 (3)	C13—C14—C15—C16	−56.1 (2)
C8—O1—C7—C6	179.64 (16)	C14—C15—C16—C17	54.4 (2)
C8—O1—C7—C2	0.51 (17)	C15—C16—C17—C18	−55.1 (2)
C3—C2—C7—C6	−0.3 (2)	C16—C17—C18—C13	57.4 (2)
C1—C2—C7—C6	−179.27 (16)	C14—C13—C18—C17	−59.57 (18)
C3—C2—C7—O1	178.86 (14)	S1—C13—C18—C17	175.92 (12)
C1—C2—C7—O1	−0.11 (17)

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	1.00	2.33	3.3030 (19)	165
C14—H14A···O3ii	0.99	2.58	3.424 (2)	143
C10—H10C···Cgi	0.98	2.71	3.548 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	1.00	2.33	3.3030 (19)	165
C14—H14A⋯O3ii	0.99	2.58	3.424 (2)	143
C10—H10C⋯Cgi	0.98	2.71	3.548 (2)	144

Symmetry codes: (i) ; (ii) .