3-Cyclo-hexyl-sulfonyl-2,5-dimethyl-1-benzofuran.

In the title compound, C(16)H(20)O(3)S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfonyl unit is in the equatorial position. In the crystal, mol-ecules are linked through 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 3-cyclo­hexyl­sulfonyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C16H20O3S

M = 292.38

Monoclinic,

a = 5.6854 (3) Å

b = 21.2391 (13) Å

c = 12.3944 (7) Å

β = 99.295 (3)°

V = 1477.01 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.643, T max = 0.746

13128 measured reflections

3228 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.05

3228 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.34 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/S160053681101498X/gk2370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101498X/gk2370Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101498X/gk2370Isup3.cml

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

C16H20O3S	F(000) = 624
Mr = 292.38	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4533 reflections
a = 5.6854 (3) Å	θ = 2.5–27.0°
b = 21.2391 (13) Å	µ = 0.22 mm−1
c = 12.3944 (7) Å	T = 173 K
β = 99.295 (3)°	Block, colourless
V = 1477.01 (15) Å3	0.30 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3228 independent reflections
Radiation source: rotating anode	2477 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→27
Tmin = 0.643, Tmax = 0.746	l = −15→15
13128 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.5178P] where P = (Fo2 + 2Fc2)/3
3228 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.34 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	0.53749 (8)	0.23293 (2)	0.54070 (4)	0.02970 (14)
O1	0.5649 (2)	0.36998 (6)	0.75483 (10)	0.0354 (3)
O2	0.7773 (2)	0.21003 (7)	0.56894 (12)	0.0420 (4)
O3	0.4559 (2)	0.25126 (6)	0.42912 (10)	0.0388 (3)
C1	0.5009 (3)	0.29734 (8)	0.62295 (14)	0.0296 (4)
C2	0.3075 (3)	0.34199 (8)	0.60232 (14)	0.0284 (4)
C3	0.1036 (3)	0.34955 (8)	0.52479 (14)	0.0309 (4)
H3	0.0678	0.3204	0.4663	0.037*
C4	−0.0470 (3)	0.39994 (9)	0.53367 (15)	0.0335 (4)
C5	0.0095 (4)	0.44219 (9)	0.62117 (16)	0.0388 (5)
H5	−0.0956	0.4763	0.6272	0.047*
C6	0.2113 (4)	0.43607 (9)	0.69861 (16)	0.0392 (5)
H6	0.2484	0.4652	0.7571	0.047*
C7	0.3561 (3)	0.38557 (8)	0.68658 (14)	0.0315 (4)
C8	0.6487 (3)	0.31577 (9)	0.71474 (14)	0.0332 (4)
C9	−0.2687 (4)	0.40917 (10)	0.45077 (17)	0.0420 (5)
H9A	−0.2263	0.4284	0.3846	0.063*
H9B	−0.3793	0.4368	0.4813	0.063*
H9C	−0.3449	0.3683	0.4324	0.063*
C10	0.8718 (3)	0.29097 (11)	0.77813 (16)	0.0409 (5)
H10A	0.9014	0.2485	0.7525	0.061*
H10B	0.8573	0.2894	0.8558	0.061*
H10C	1.0048	0.3186	0.7682	0.061*
C11	0.3393 (3)	0.17417 (8)	0.57532 (14)	0.0282 (4)
H11	0.1729	0.1907	0.5573	0.034*
C12	0.3871 (4)	0.15762 (10)	0.69641 (15)	0.0384 (5)
H12A	0.5537	0.1430	0.7169	0.046*
H12B	0.3656	0.1955	0.7404	0.046*
C13	0.2166 (4)	0.10610 (10)	0.72029 (17)	0.0467 (5)
H13A	0.2528	0.0944	0.7985	0.056*
H13B	0.0510	0.1222	0.7054	0.056*
C14	0.2374 (5)	0.04836 (11)	0.65068 (19)	0.0546 (6)
H14A	0.1200	0.0164	0.6655	0.066*
H14B	0.3986	0.0300	0.6704	0.066*
C15	0.1933 (5)	0.06485 (11)	0.52957 (18)	0.0535 (6)
H15A	0.0263	0.0789	0.5082	0.064*
H15B	0.2170	0.0269	0.4863	0.064*
C16	0.3609 (4)	0.11667 (9)	0.50391 (16)	0.0404 (5)
H16A	0.3208	0.1286	0.4259	0.049*
H16B	0.5271	0.1011	0.5172	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0324 (3)	0.0304 (2)	−0.00048 (19)	0.01150 (18)	0.00121 (18)
O1	0.0377 (7)	0.0379 (8)	0.0304 (7)	−0.0085 (6)	0.0050 (6)	−0.0033 (5)
O2	0.0263 (7)	0.0467 (8)	0.0558 (9)	0.0009 (6)	0.0144 (6)	−0.0012 (7)
O3	0.0541 (9)	0.0373 (8)	0.0276 (7)	0.0000 (6)	0.0145 (6)	0.0025 (5)
C1	0.0302 (10)	0.0312 (10)	0.0289 (9)	−0.0056 (8)	0.0097 (7)	0.0009 (7)
C2	0.0311 (9)	0.0276 (9)	0.0286 (9)	−0.0069 (7)	0.0109 (7)	0.0012 (7)
C3	0.0369 (10)	0.0282 (10)	0.0287 (9)	−0.0060 (8)	0.0085 (8)	−0.0001 (7)
C4	0.0364 (10)	0.0280 (10)	0.0370 (10)	−0.0040 (8)	0.0085 (8)	0.0052 (8)
C5	0.0471 (12)	0.0272 (10)	0.0444 (11)	0.0009 (9)	0.0143 (9)	0.0018 (8)
C6	0.0519 (13)	0.0297 (11)	0.0374 (10)	−0.0061 (9)	0.0110 (9)	−0.0067 (8)
C7	0.0349 (10)	0.0320 (10)	0.0284 (9)	−0.0089 (8)	0.0075 (8)	−0.0001 (7)
C8	0.0332 (10)	0.0365 (11)	0.0319 (9)	−0.0077 (8)	0.0116 (8)	0.0033 (8)
C9	0.0413 (12)	0.0382 (12)	0.0458 (12)	0.0000 (9)	0.0047 (9)	0.0088 (9)
C10	0.0300 (10)	0.0582 (13)	0.0337 (10)	−0.0063 (9)	0.0025 (8)	0.0045 (9)
C11	0.0238 (9)	0.0324 (10)	0.0288 (9)	−0.0015 (7)	0.0052 (7)	0.0025 (7)
C12	0.0437 (11)	0.0430 (12)	0.0286 (9)	−0.0096 (9)	0.0064 (8)	0.0049 (8)
C13	0.0515 (13)	0.0547 (14)	0.0339 (10)	−0.0153 (11)	0.0072 (9)	0.0109 (9)
C14	0.0652 (15)	0.0415 (13)	0.0568 (14)	−0.0163 (11)	0.0088 (12)	0.0121 (10)
C15	0.0713 (16)	0.0432 (13)	0.0471 (12)	−0.0193 (11)	0.0131 (11)	−0.0048 (10)
C16	0.0516 (13)	0.0355 (11)	0.0362 (10)	−0.0057 (9)	0.0133 (9)	−0.0034 (8)

S1—O2	1.4368 (13)	C9—H9C	0.9800
S1—O3	1.4395 (13)	C10—H10A	0.9800
S1—C1	1.7385 (18)	C10—H10B	0.9800
S1—C11	1.7797 (17)	C10—H10C	0.9800
O1—C8	1.369 (2)	C11—C12	1.523 (2)
O1—C7	1.382 (2)	C11—C16	1.525 (3)
C1—C8	1.358 (3)	C11—H11	1.0000
C1—C2	1.443 (3)	C12—C13	1.522 (3)
C2—C7	1.390 (2)	C12—H12A	0.9900
C2—C3	1.391 (3)	C12—H12B	0.9900
C3—C4	1.386 (3)	C13—C14	1.515 (3)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.404 (3)	C13—H13B	0.9900
C4—C9	1.505 (3)	C14—C15	1.522 (3)
C5—C6	1.378 (3)	C14—H14A	0.9900
C5—H5	0.9500	C14—H14B	0.9900
C6—C7	1.375 (3)	C15—C16	1.522 (3)
C6—H6	0.9500	C15—H15A	0.9900
C8—C10	1.477 (3)	C15—H15B	0.9900
C9—H9A	0.9800	C16—H16A	0.9900
C9—H9B	0.9800	C16—H16B	0.9900
O2—S1—O3	118.14 (8)	C8—C10—H10C	109.5
O2—S1—C1	108.80 (9)	H10A—C10—H10C	109.5
O3—S1—C1	107.46 (8)	H10B—C10—H10C	109.5
O2—S1—C11	108.47 (8)	C12—C11—C16	111.65 (16)
O3—S1—C11	107.62 (8)	C12—C11—S1	112.35 (12)
C1—S1—C11	105.67 (8)	C16—C11—S1	107.96 (12)
C8—O1—C7	107.10 (14)	C12—C11—H11	108.2
C8—C1—C2	108.03 (16)	C16—C11—H11	108.2
C8—C1—S1	126.98 (15)	S1—C11—H11	108.2
C2—C1—S1	124.96 (13)	C13—C12—C11	109.85 (16)
C7—C2—C3	118.99 (17)	C13—C12—H12A	109.7
C7—C2—C1	104.56 (16)	C11—C12—H12A	109.7
C3—C2—C1	136.45 (16)	C13—C12—H12B	109.7
C4—C3—C2	119.42 (17)	C11—C12—H12B	109.7
C4—C3—H3	120.3	H12A—C12—H12B	108.2
C2—C3—H3	120.3	C14—C13—C12	111.12 (17)
C3—C4—C5	119.18 (18)	C14—C13—H13A	109.4
C3—C4—C9	120.43 (17)	C12—C13—H13A	109.4
C5—C4—C9	120.39 (18)	C14—C13—H13B	109.4
C6—C5—C4	122.59 (18)	C12—C13—H13B	109.4
C6—C5—H5	118.7	H13A—C13—H13B	108.0
C4—C5—H5	118.7	C13—C14—C15	111.09 (18)
C7—C6—C5	116.34 (18)	C13—C14—H14A	109.4
C7—C6—H6	121.8	C15—C14—H14A	109.4
C5—C6—H6	121.8	C13—C14—H14B	109.4
C6—C7—O1	126.21 (16)	C15—C14—H14B	109.4
C6—C7—C2	123.48 (18)	H14A—C14—H14B	108.0
O1—C7—C2	110.31 (16)	C14—C15—C16	111.32 (18)
C1—C8—O1	110.00 (16)	C14—C15—H15A	109.4
C1—C8—C10	134.80 (19)	C16—C15—H15A	109.4
O1—C8—C10	115.20 (16)	C14—C15—H15B	109.4
C4—C9—H9A	109.5	C16—C15—H15B	109.4
C4—C9—H9B	109.5	H15A—C15—H15B	108.0
H9A—C9—H9B	109.5	C15—C16—C11	110.25 (16)
C4—C9—H9C	109.5	C15—C16—H16A	109.6
H9A—C9—H9C	109.5	C11—C16—H16A	109.6
H9B—C9—H9C	109.5	C15—C16—H16B	109.6
C8—C10—H10A	109.5	C11—C16—H16B	109.6
C8—C10—H10B	109.5	H16A—C16—H16B	108.1
H10A—C10—H10B	109.5
O2—S1—C1—C8	−13.71 (19)	C3—C2—C7—O1	179.92 (14)
O3—S1—C1—C8	−142.70 (16)	C1—C2—C7—O1	0.39 (18)
C11—S1—C1—C8	102.59 (17)	C2—C1—C8—O1	−0.52 (19)
O2—S1—C1—C2	164.31 (14)	S1—C1—C8—O1	177.76 (12)
O3—S1—C1—C2	35.31 (17)	C2—C1—C8—C10	179.59 (19)
C11—S1—C1—C2	−79.39 (16)	S1—C1—C8—C10	−2.1 (3)
C8—C1—C2—C7	0.08 (18)	C7—O1—C8—C1	0.76 (19)
S1—C1—C2—C7	−178.25 (13)	C7—O1—C8—C10	−179.33 (15)
C8—C1—C2—C3	−179.33 (19)	O2—S1—C11—C12	59.13 (15)
S1—C1—C2—C3	2.3 (3)	O3—S1—C11—C12	−171.99 (13)
C7—C2—C3—C4	−0.5 (2)	C1—S1—C11—C12	−57.40 (15)
C1—C2—C3—C4	178.88 (18)	O2—S1—C11—C16	−64.43 (15)
C2—C3—C4—C5	−0.2 (3)	O3—S1—C11—C16	64.46 (14)
C2—C3—C4—C9	179.96 (16)	C1—S1—C11—C16	179.05 (13)
C3—C4—C5—C6	0.7 (3)	C16—C11—C12—C13	−57.1 (2)
C9—C4—C5—C6	−179.43 (18)	S1—C11—C12—C13	−178.58 (14)
C4—C5—C6—C7	−0.6 (3)	C11—C12—C13—C14	56.9 (2)
C5—C6—C7—O1	−179.30 (16)	C12—C13—C14—C15	−56.7 (2)
C5—C6—C7—C2	−0.2 (3)	C13—C14—C15—C16	55.8 (3)
C8—O1—C7—C6	178.52 (17)	C14—C15—C16—C11	−55.3 (3)
C8—O1—C7—C2	−0.71 (18)	C12—C11—C16—C15	56.4 (2)
C3—C2—C7—C6	0.7 (3)	S1—C11—C16—C15	−179.62 (15)
C1—C2—C7—C6	−178.87 (17)

Cg is the centroid of the C2–C7 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	1.00	2.31	3.273 (2)	161
C12—H12B···O3ii	0.99	2.57	3.443 (2)	146
C10—H10C···Cgiii	0.99	2.75	3.556 (2)	140

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
C11—H11⋯O2i	1.00	2.31	3.273 (2)	161
C12—H12B⋯O3ii	0.99	2.57	3.443 (2)	146
C10—H10C⋯Cgiii	0.99	2.75	3.556 (2)	140

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