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

In the title compound, C(21)H(22)O(2)S, the cyclo-hexyl ring adopts a chair conformation. The phenyl ring makes a dihedral angle of 84.80 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds.

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-aryl­sulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C21H22O2S

M = 338.45

Triclinic,

a = 8.8532 (2) Å

b = 10.2011 (2) Å

c = 10.4752 (3) Å

α = 90.734 (1)°

β = 111.568 (1)°

γ = 97.127 (1)°

V = 871.25 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.650, T max = 0.746

15560 measured reflections

4012 independent reflections

3481 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.07

4012 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.26 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/S1600536811013705/zl2365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013705/zl2365Isup2.hkl

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

C21H22O2S	Z = 2
Mr = 338.45	F(000) = 360
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8532 (2) Å	Cell parameters from 6502 reflections
b = 10.2011 (2) Å	θ = 2.6–27.5°
c = 10.4752 (3) Å	µ = 0.20 mm−1
α = 90.734 (1)°	T = 173 K
β = 111.568 (1)°	Block, colourless
γ = 97.127 (1)°	0.35 × 0.25 × 0.16 mm
V = 871.25 (4) Å3

Bruker SMART APEXII CCD diffractometer	4012 independent reflections
Radiation source: rotating anode	3481 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.650, Tmax = 0.746	l = −13→13
15560 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.2372P] where P = (Fo2 + 2Fc2)/3
4012 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.26 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	0.33404 (4)	0.01587 (3)	0.18991 (3)	0.02947 (11)
O1	0.52084 (12)	0.32470 (10)	0.04883 (10)	0.0334 (2)
O2	0.45627 (13)	−0.04998 (10)	0.29798 (11)	0.0388 (3)
C1	0.43524 (16)	0.16549 (13)	0.16271 (14)	0.0279 (3)
C2	0.55010 (16)	0.26393 (13)	0.26444 (14)	0.0264 (3)
C3	0.61465 (16)	0.28037 (13)	0.40727 (14)	0.0265 (3)
H3	0.5837	0.2160	0.4611	0.032*
C4	0.72549 (16)	0.39299 (13)	0.46990 (14)	0.0273 (3)
C5	0.76898 (17)	0.48649 (14)	0.38824 (15)	0.0328 (3)
H5	0.8443	0.5631	0.4321	0.039*
C6	0.70636 (18)	0.47162 (15)	0.24594 (16)	0.0347 (3)
H6	0.7366	0.5356	0.1914	0.042*
C7	0.59801 (17)	0.35912 (14)	0.18809 (14)	0.0291 (3)
C8	0.42408 (17)	0.20589 (14)	0.03698 (14)	0.0310 (3)
C9	0.79606 (17)	0.41638 (13)	0.62465 (14)	0.0284 (3)
H9	0.8821	0.4958	0.6485	0.034*
C10	0.6659 (2)	0.44576 (18)	0.68066 (16)	0.0416 (4)
H10A	0.6177	0.5245	0.6381	0.050*
H10B	0.5769	0.3698	0.6551	0.050*
C11	0.7379 (2)	0.47091 (17)	0.83653 (16)	0.0423 (4)
H11A	0.8200	0.5516	0.8617	0.051*
H11B	0.6496	0.4863	0.8694	0.051*
C12	0.81830 (19)	0.35505 (15)	0.90597 (15)	0.0368 (3)
H12A	0.7339	0.2767	0.8892	0.044*
H12B	0.8697	0.3763	1.0065	0.044*
C13	0.94782 (19)	0.32296 (16)	0.85200 (15)	0.0364 (3)
H13A	0.9925	0.2429	0.8941	0.044*
H13B	1.0391	0.3972	0.8792	0.044*
C14	0.87798 (18)	0.29943 (14)	0.69594 (14)	0.0315 (3)
H14A	0.7965	0.2184	0.6695	0.038*
H14B	0.9674	0.2850	0.6642	0.038*
C15	0.3295 (2)	0.14926 (17)	−0.10566 (15)	0.0405 (4)
H15A	0.2767	0.0596	−0.1031	0.061*
H15B	0.4039	0.1459	−0.1552	0.061*
H15C	0.2456	0.2049	−0.1528	0.061*
C16	0.20788 (16)	0.08189 (12)	0.26836 (14)	0.0268 (3)
C17	0.06675 (19)	0.12795 (16)	0.18436 (16)	0.0387 (3)
H17	0.0404	0.1284	0.0879	0.046*
C18	−0.0358 (2)	0.17341 (18)	0.2422 (2)	0.0471 (4)
H18	−0.1330	0.2058	0.1854	0.057*
C19	0.0022 (2)	0.17188 (18)	0.3815 (2)	0.0483 (4)
H19	−0.0685	0.2035	0.4209	0.058*
C20	0.1428 (2)	0.12449 (18)	0.46414 (17)	0.0462 (4)
H20	0.1686	0.1236	0.5605	0.055*
C21	0.24659 (19)	0.07815 (15)	0.40774 (15)	0.0344 (3)
H21	0.3428	0.0444	0.4644	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0328 (2)	0.02712 (18)	0.02898 (19)	0.00368 (13)	0.01233 (15)	−0.00168 (13)
O1	0.0350 (5)	0.0415 (6)	0.0285 (5)	0.0062 (4)	0.0171 (4)	0.0062 (4)
O2	0.0405 (6)	0.0351 (5)	0.0433 (6)	0.0142 (5)	0.0154 (5)	0.0074 (5)
C1	0.0279 (7)	0.0319 (7)	0.0263 (6)	0.0064 (5)	0.0123 (5)	0.0004 (5)
C2	0.0245 (6)	0.0276 (6)	0.0300 (7)	0.0064 (5)	0.0126 (5)	0.0031 (5)
C3	0.0264 (6)	0.0267 (6)	0.0279 (7)	0.0047 (5)	0.0114 (5)	0.0039 (5)
C4	0.0238 (6)	0.0269 (6)	0.0314 (7)	0.0062 (5)	0.0097 (5)	0.0031 (5)
C5	0.0287 (7)	0.0294 (7)	0.0402 (8)	0.0010 (5)	0.0133 (6)	0.0041 (6)
C6	0.0337 (7)	0.0353 (7)	0.0395 (8)	0.0030 (6)	0.0189 (6)	0.0108 (6)
C7	0.0276 (7)	0.0355 (7)	0.0284 (7)	0.0076 (5)	0.0142 (6)	0.0055 (5)
C8	0.0304 (7)	0.0377 (7)	0.0295 (7)	0.0091 (6)	0.0152 (6)	0.0016 (6)
C9	0.0261 (6)	0.0260 (6)	0.0300 (7)	0.0015 (5)	0.0076 (5)	−0.0001 (5)
C10	0.0355 (8)	0.0534 (9)	0.0348 (8)	0.0191 (7)	0.0080 (7)	−0.0060 (7)
C11	0.0402 (9)	0.0513 (9)	0.0352 (8)	0.0160 (7)	0.0111 (7)	−0.0082 (7)
C12	0.0377 (8)	0.0427 (8)	0.0318 (7)	0.0024 (6)	0.0162 (6)	−0.0022 (6)
C13	0.0371 (8)	0.0437 (8)	0.0305 (7)	0.0133 (7)	0.0127 (6)	0.0059 (6)
C14	0.0343 (7)	0.0335 (7)	0.0301 (7)	0.0099 (6)	0.0143 (6)	0.0040 (5)
C15	0.0449 (9)	0.0518 (9)	0.0279 (7)	0.0110 (7)	0.0159 (7)	−0.0011 (6)
C16	0.0288 (7)	0.0236 (6)	0.0288 (7)	0.0018 (5)	0.0122 (6)	0.0021 (5)
C17	0.0371 (8)	0.0458 (9)	0.0342 (8)	0.0116 (7)	0.0122 (7)	0.0108 (6)
C18	0.0377 (9)	0.0493 (9)	0.0593 (11)	0.0173 (7)	0.0199 (8)	0.0125 (8)
C19	0.0471 (10)	0.0476 (9)	0.0611 (11)	0.0077 (8)	0.0326 (9)	−0.0047 (8)
C20	0.0530 (10)	0.0547 (10)	0.0352 (8)	0.0020 (8)	0.0234 (8)	−0.0054 (7)
C21	0.0338 (7)	0.0393 (8)	0.0282 (7)	0.0028 (6)	0.0099 (6)	0.0009 (6)

S1—O2	1.4843 (11)	C11—H11A	0.9900
S1—C1	1.7529 (14)	C11—H11B	0.9900
S1—C16	1.7955 (14)	C12—C13	1.519 (2)
O1—C8	1.3706 (17)	C12—H12A	0.9900
O1—C7	1.3829 (17)	C12—H12B	0.9900
C1—C8	1.3574 (19)	C13—C14	1.5239 (19)
C1—C2	1.4494 (18)	C13—H13A	0.9900
C2—C7	1.3891 (19)	C13—H13B	0.9900
C2—C3	1.3908 (18)	C14—H14A	0.9900
C3—C4	1.3931 (18)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.4006 (19)	C15—H15B	0.9800
C4—C9	1.5112 (19)	C15—H15C	0.9800
C5—C6	1.385 (2)	C16—C21	1.374 (2)
C5—H5	0.9500	C16—C17	1.380 (2)
C6—C7	1.373 (2)	C17—C18	1.382 (2)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.485 (2)	C18—C19	1.372 (3)
C9—C10	1.530 (2)	C18—H18	0.9500
C9—C14	1.5317 (19)	C19—C20	1.379 (3)
C9—H9	1.0000	C19—H19	0.9500
C10—C11	1.524 (2)	C20—C21	1.385 (2)
C10—H10A	0.9900	C20—H20	0.9500
C10—H10B	0.9900	C21—H21	0.9500
C11—C12	1.511 (2)
O2—S1—C1	107.74 (6)	C10—C11—H11B	109.4
O2—S1—C16	106.99 (6)	H11A—C11—H11B	108.0
C1—S1—C16	98.62 (6)	C11—C12—C13	111.07 (13)
C8—O1—C7	106.49 (10)	C11—C12—H12A	109.4
C8—C1—C2	107.37 (12)	C13—C12—H12A	109.4
C8—C1—S1	124.25 (11)	C11—C12—H12B	109.4
C2—C1—S1	128.29 (10)	C13—C12—H12B	109.4
C7—C2—C3	119.49 (12)	H12A—C12—H12B	108.0
C7—C2—C1	104.63 (12)	C12—C13—C14	111.68 (12)
C3—C2—C1	135.87 (12)	C12—C13—H13A	109.3
C2—C3—C4	118.76 (12)	C14—C13—H13A	109.3
C2—C3—H3	120.6	C12—C13—H13B	109.3
C4—C3—H3	120.6	C14—C13—H13B	109.3
C3—C4—C5	119.53 (13)	H13A—C13—H13B	107.9
C3—C4—C9	120.59 (12)	C13—C14—C9	111.88 (12)
C5—C4—C9	119.87 (12)	C13—C14—H14A	109.2
C6—C5—C4	122.53 (13)	C9—C14—H14A	109.2
C6—C5—H5	118.7	C13—C14—H14B	109.2
C4—C5—H5	118.7	C9—C14—H14B	109.2
C7—C6—C5	116.21 (13)	H14A—C14—H14B	107.9
C7—C6—H6	121.9	C8—C15—H15A	109.5
C5—C6—H6	121.9	C8—C15—H15B	109.5
C6—C7—O1	125.85 (12)	H15A—C15—H15B	109.5
C6—C7—C2	123.48 (13)	C8—C15—H15C	109.5
O1—C7—C2	110.67 (12)	H15A—C15—H15C	109.5
C1—C8—O1	110.83 (12)	H15B—C15—H15C	109.5
C1—C8—C15	133.47 (14)	C21—C16—C17	121.28 (13)
O1—C8—C15	115.70 (12)	C21—C16—S1	120.21 (11)
C4—C9—C10	111.77 (11)	C17—C16—S1	118.37 (11)
C4—C9—C14	112.05 (11)	C16—C17—C18	119.21 (15)
C10—C9—C14	109.62 (12)	C16—C17—H17	120.4
C4—C9—H9	107.7	C18—C17—H17	120.4
C10—C9—H9	107.7	C19—C18—C17	120.21 (16)
C14—C9—H9	107.7	C19—C18—H18	119.9
C11—C10—C9	111.62 (13)	C17—C18—H18	119.9
C11—C10—H10A	109.3	C18—C19—C20	120.03 (15)
C9—C10—H10A	109.3	C18—C19—H19	120.0
C11—C10—H10B	109.3	C20—C19—H19	120.0
C9—C10—H10B	109.3	C19—C20—C21	120.49 (16)
H10A—C10—H10B	108.0	C19—C20—H20	119.8
C12—C11—C10	111.23 (13)	C21—C20—H20	119.8
C12—C11—H11A	109.4	C16—C21—C20	118.77 (15)
C10—C11—H11A	109.4	C16—C21—H21	120.6
C12—C11—H11B	109.4	C20—C21—H21	120.6
O2—S1—C1—C8	131.22 (12)	C7—O1—C8—C1	1.01 (15)
C16—S1—C1—C8	−117.76 (13)	C7—O1—C8—C15	−179.63 (12)
O2—S1—C1—C2	−45.06 (13)	C3—C4—C9—C10	−68.63 (16)
C16—S1—C1—C2	65.96 (13)	C5—C4—C9—C10	110.04 (15)
C8—C1—C2—C7	0.77 (15)	C3—C4—C9—C14	54.86 (16)
S1—C1—C2—C7	177.55 (11)	C5—C4—C9—C14	−126.47 (14)
C8—C1—C2—C3	−179.30 (15)	C4—C9—C10—C11	−179.32 (13)
S1—C1—C2—C3	−2.5 (2)	C14—C9—C10—C11	55.83 (17)
C7—C2—C3—C4	0.36 (19)	C9—C10—C11—C12	−56.99 (19)
C1—C2—C3—C4	−179.57 (14)	C10—C11—C12—C13	55.67 (18)
C2—C3—C4—C5	0.07 (19)	C11—C12—C13—C14	−54.82 (17)
C2—C3—C4—C9	178.73 (11)	C12—C13—C14—C9	55.03 (17)
C3—C4—C5—C6	−0.3 (2)	C4—C9—C14—C13	−179.56 (12)
C9—C4—C5—C6	−178.94 (13)	C10—C9—C14—C13	−54.87 (16)
C4—C5—C6—C7	0.0 (2)	O2—S1—C16—C21	6.99 (13)
C5—C6—C7—O1	179.83 (12)	C1—S1—C16—C21	−104.63 (12)
C5—C6—C7—C2	0.4 (2)	O2—S1—C16—C17	−168.86 (11)
C8—O1—C7—C6	−179.94 (14)	C1—S1—C16—C17	79.52 (12)
C8—O1—C7—C2	−0.49 (15)	C21—C16—C17—C18	1.2 (2)
C3—C2—C7—C6	−0.6 (2)	S1—C16—C17—C18	177.02 (13)
C1—C2—C7—C6	179.30 (13)	C16—C17—C18—C19	−0.4 (3)
C3—C2—C7—O1	179.89 (11)	C17—C18—C19—C20	−0.2 (3)
C1—C2—C7—O1	−0.16 (14)	C18—C19—C20—C21	0.0 (3)
C2—C1—C8—O1	−1.12 (15)	C17—C16—C21—C20	−1.4 (2)
S1—C1—C8—O1	−178.06 (9)	S1—C16—C21—C20	−177.15 (12)
C2—C1—C8—C15	179.67 (15)	C19—C20—C21—C16	0.8 (2)
S1—C1—C8—C15	2.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2i	0.98	2.52	3.4516 (19)	159
C21—H21···O2ii	0.95	2.47	3.2793 (18)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2i	0.98	2.52	3.4516 (19)	159
C21—H21⋯O2ii	0.95	2.47	3.2793 (18)	144

Symmetry codes: (i) ; (ii) .