5-Cyclo-hexyl-2-methyl-3-(4-methyl-phenyl-sulfin-yl)-1-benzofuran.

In the title compound, C(22)H(24)O(2)S, the cyclo-hexyl ring adopts a chair conformation. The 4-methyl-phenyl ring makes a dihedral angle of 81.60 (5)° with the mean plane [r.m.s. deviation = 0.004 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and weak π-π inter-actions between the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.545 (2) Å, inter-planar distance = 3.489 (2) Å and slippage = 0.628 (2) Å.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C22H24O2S

M = 352.47

Monoclinic,

a = 16.6086 (4) Å

b = 8.8344 (2) Å

c = 13.0330 (3) Å

β = 104.064 (1)°

V = 1854.97 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.37 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.934, T max = 0.958

16901 measured reflections

4265 independent reflections

3545 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.06

4265 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.31 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/S1600536812008409/gk2461sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008409/gk2461Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008409/gk2461Isup3.cml

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

C22H24O2S	F(000) = 752
Mr = 352.47	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6233 reflections
a = 16.6086 (4) Å	θ = 2.5–27.5°
b = 8.8344 (2) Å	µ = 0.19 mm−1
c = 13.0330 (3) Å	T = 173 K
β = 104.064 (1)°	Block, colourless
V = 1854.97 (7) Å3	0.37 × 0.25 × 0.23 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4265 independent reflections
Radiation source: rotating anode	3545 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.3°
φ and ω scans	h = −21→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→11
Tmin = 0.934, Tmax = 0.958	l = −16→16
16901 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.6552P] where P = (Fo2 + 2Fc2)/3
4265 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.31 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	0.13691 (3)	0.27171 (5)	0.44504 (3)	0.03485 (14)
O1	0.03313 (7)	0.67453 (14)	0.40263 (9)	0.0342 (3)
O2	0.15932 (9)	0.21178 (14)	0.55463 (10)	0.0447 (3)
C1	0.10429 (9)	0.45997 (18)	0.45194 (11)	0.0287 (3)
C2	0.13345 (9)	0.57018 (17)	0.53478 (11)	0.0272 (3)
C3	0.19160 (9)	0.57274 (18)	0.63229 (11)	0.0280 (3)
H3	0.2236	0.4854	0.6577	0.034*
C4	0.20187 (9)	0.70563 (18)	0.69176 (12)	0.0298 (3)
C5	0.15399 (10)	0.8332 (2)	0.65225 (14)	0.0360 (4)
H5	0.1617	0.9233	0.6932	0.043*
C6	0.09584 (10)	0.8331 (2)	0.55585 (14)	0.0369 (4)
H6	0.0639	0.9203	0.5299	0.044*
C7	0.08702 (9)	0.69938 (18)	0.49981 (12)	0.0302 (3)
C8	0.04472 (9)	0.52723 (19)	0.37593 (12)	0.0315 (3)
C9	0.26367 (10)	0.71423 (18)	0.79833 (12)	0.0323 (3)
H9	0.2620	0.8199	0.8253	0.039*
C10	0.35226 (10)	0.6834 (3)	0.79134 (14)	0.0493 (5)
H10A	0.3679	0.7570	0.7423	0.059*
H10B	0.3555	0.5806	0.7622	0.059*
C11	0.41355 (11)	0.6952 (3)	0.89943 (15)	0.0522 (5)
H11A	0.4699	0.6687	0.8924	0.063*
H11B	0.4149	0.8008	0.9251	0.063*
C12	0.38954 (12)	0.5904 (2)	0.97924 (15)	0.0497 (5)
H12A	0.3949	0.4840	0.9580	0.060*
H12B	0.4280	0.6060	1.0495	0.060*
C13	0.30210 (13)	0.6187 (3)	0.98700 (14)	0.0520 (5)
H13A	0.2985	0.7207	1.0171	0.062*
H13B	0.2870	0.5435	1.0355	0.062*
C14	0.24081 (11)	0.6080 (2)	0.87911 (13)	0.0437 (4)
H14A	0.1845	0.6334	0.8867	0.052*
H14B	0.2396	0.5026	0.8530	0.052*
C15	−0.00704 (11)	0.4748 (2)	0.27292 (12)	0.0409 (4)
H15A	0.0108	0.5256	0.2154	0.061*
H15B	−0.0654	0.4989	0.2684	0.061*
H15C	−0.0008	0.3651	0.2668	0.061*
C16	0.23179 (11)	0.31164 (18)	0.40764 (12)	0.0326 (3)
C17	0.22949 (12)	0.31441 (19)	0.30040 (12)	0.0373 (4)
H17	0.1788	0.2968	0.2493	0.045*
C18	0.30144 (13)	0.3429 (2)	0.26885 (13)	0.0431 (4)
H18	0.2997	0.3467	0.1955	0.052*
C19	0.37674 (12)	0.3662 (2)	0.34233 (15)	0.0454 (4)
C20	0.37743 (12)	0.3619 (2)	0.44926 (15)	0.0463 (4)
H20	0.4282	0.3778	0.5005	0.056*
C21	0.30568 (11)	0.3349 (2)	0.48239 (13)	0.0398 (4)
H21	0.3071	0.3323	0.5557	0.048*
C22	0.45564 (15)	0.3941 (3)	0.3071 (2)	0.0705 (7)
H22A	0.5017	0.4099	0.3693	0.106*
H22B	0.4489	0.4843	0.2620	0.106*
H22C	0.4675	0.3064	0.2672	0.106*

	U11	U22	U33	U12	U13	U23
S1	0.0461 (3)	0.0245 (2)	0.0314 (2)	−0.00455 (17)	0.00458 (16)	−0.00145 (14)
O1	0.0289 (5)	0.0360 (6)	0.0353 (6)	0.0024 (5)	0.0031 (4)	0.0061 (5)
O2	0.0633 (8)	0.0338 (7)	0.0361 (6)	0.0014 (6)	0.0104 (6)	0.0089 (5)
C1	0.0304 (7)	0.0267 (8)	0.0276 (7)	−0.0033 (6)	0.0042 (5)	0.0009 (6)
C2	0.0270 (7)	0.0236 (7)	0.0314 (7)	−0.0021 (6)	0.0080 (6)	0.0018 (6)
C3	0.0284 (7)	0.0230 (7)	0.0314 (7)	0.0005 (6)	0.0053 (6)	0.0007 (6)
C4	0.0264 (7)	0.0278 (8)	0.0347 (7)	−0.0033 (6)	0.0067 (6)	−0.0024 (6)
C5	0.0351 (8)	0.0258 (8)	0.0471 (9)	0.0009 (7)	0.0099 (7)	−0.0061 (7)
C6	0.0334 (8)	0.0275 (8)	0.0486 (9)	0.0079 (7)	0.0080 (7)	0.0026 (7)
C7	0.0255 (7)	0.0303 (8)	0.0343 (7)	0.0008 (6)	0.0064 (6)	0.0050 (6)
C8	0.0288 (7)	0.0343 (9)	0.0307 (7)	−0.0048 (6)	0.0063 (6)	0.0038 (6)
C9	0.0332 (8)	0.0261 (8)	0.0355 (8)	−0.0032 (6)	0.0047 (6)	−0.0063 (6)
C10	0.0301 (9)	0.0803 (15)	0.0372 (9)	−0.0076 (9)	0.0075 (7)	−0.0024 (9)
C11	0.0316 (9)	0.0774 (16)	0.0443 (10)	−0.0060 (9)	0.0027 (7)	−0.0053 (10)
C12	0.0531 (11)	0.0478 (12)	0.0410 (9)	0.0060 (9)	−0.0026 (8)	−0.0034 (8)
C13	0.0555 (12)	0.0668 (15)	0.0329 (9)	−0.0076 (10)	0.0092 (8)	−0.0018 (9)
C14	0.0402 (9)	0.0577 (12)	0.0342 (8)	−0.0097 (8)	0.0113 (7)	−0.0046 (8)
C15	0.0354 (8)	0.0531 (11)	0.0302 (8)	−0.0069 (8)	0.0001 (6)	0.0045 (7)
C16	0.0446 (9)	0.0230 (8)	0.0289 (7)	0.0044 (7)	0.0064 (6)	−0.0006 (6)
C17	0.0531 (10)	0.0277 (8)	0.0279 (7)	0.0052 (7)	0.0035 (7)	−0.0029 (6)
C18	0.0641 (12)	0.0358 (10)	0.0314 (8)	0.0111 (9)	0.0158 (8)	−0.0008 (7)
C19	0.0499 (10)	0.0419 (11)	0.0472 (10)	0.0136 (9)	0.0174 (8)	0.0010 (8)
C20	0.0422 (10)	0.0512 (12)	0.0418 (9)	0.0091 (9)	0.0033 (7)	0.0013 (8)
C21	0.0468 (10)	0.0422 (10)	0.0274 (7)	0.0066 (8)	0.0030 (7)	0.0011 (7)
C22	0.0610 (14)	0.088 (2)	0.0710 (15)	0.0125 (13)	0.0325 (12)	0.0018 (13)

S1—O2	1.4834 (12)	C11—H11B	0.9900
S1—C1	1.7582 (16)	C12—C13	1.501 (3)
S1—C16	1.7940 (18)	C12—H12A	0.9900
O1—C8	1.373 (2)	C12—H12B	0.9900
O1—C7	1.3792 (19)	C13—C14	1.525 (2)
C1—C8	1.355 (2)	C13—H13A	0.9900
C1—C2	1.447 (2)	C13—H13B	0.9900
C2—C7	1.391 (2)	C14—H14A	0.9900
C2—C3	1.397 (2)	C14—H14B	0.9900
C3—C4	1.394 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.403 (2)	C15—H15C	0.9800
C4—C9	1.515 (2)	C16—C21	1.384 (2)
C5—C6	1.386 (2)	C16—C17	1.389 (2)
C5—H5	0.9500	C17—C18	1.378 (3)
C6—C7	1.378 (2)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.393 (3)
C8—C15	1.482 (2)	C18—H18	0.9500
C9—C10	1.521 (2)	C19—C20	1.391 (3)
C9—C14	1.526 (2)	C19—C22	1.510 (3)
C9—H9	1.0000	C20—C21	1.383 (3)
C10—C11	1.528 (2)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900	C22—H22A	0.9800
C11—C12	1.516 (3)	C22—H22B	0.9800
C11—H11A	0.9900	C22—H22C	0.9800
O2—S1—C1	107.26 (7)	C13—C12—H12A	109.4
O2—S1—C16	107.48 (8)	C11—C12—H12A	109.4
C1—S1—C16	97.46 (7)	C13—C12—H12B	109.4
C8—O1—C7	106.50 (12)	C11—C12—H12B	109.4
C8—C1—C2	107.63 (14)	H12A—C12—H12B	108.0
C8—C1—S1	123.82 (12)	C12—C13—C14	111.56 (15)
C2—C1—S1	128.54 (11)	C12—C13—H13A	109.3
C7—C2—C3	119.37 (14)	C14—C13—H13A	109.3
C7—C2—C1	104.43 (13)	C12—C13—H13B	109.3
C3—C2—C1	136.19 (15)	C14—C13—H13B	109.3
C4—C3—C2	118.92 (14)	H13A—C13—H13B	108.0
C4—C3—H3	120.5	C13—C14—C9	112.06 (15)
C2—C3—H3	120.5	C13—C14—H14A	109.2
C3—C4—C5	119.37 (15)	C9—C14—H14A	109.2
C3—C4—C9	121.06 (14)	C13—C14—H14B	109.2
C5—C4—C9	119.57 (14)	C9—C14—H14B	109.2
C6—C5—C4	122.67 (16)	H14A—C14—H14B	107.9
C6—C5—H5	118.7	C8—C15—H15A	109.5
C4—C5—H5	118.7	C8—C15—H15B	109.5
C7—C6—C5	116.24 (15)	H15A—C15—H15B	109.5
C7—C6—H6	121.9	C8—C15—H15C	109.5
C5—C6—H6	121.9	H15A—C15—H15C	109.5
C6—C7—O1	125.79 (14)	H15B—C15—H15C	109.5
C6—C7—C2	123.42 (15)	C21—C16—C17	120.55 (16)
O1—C7—C2	110.78 (14)	C21—C16—S1	121.67 (12)
C1—C8—O1	110.65 (13)	C17—C16—S1	117.76 (13)
C1—C8—C15	133.23 (17)	C18—C17—C16	119.32 (16)
O1—C8—C15	116.11 (14)	C18—C17—H17	120.3
C4—C9—C10	112.70 (13)	C16—C17—H17	120.3
C4—C9—C14	112.02 (13)	C17—C18—C19	121.36 (16)
C10—C9—C14	109.74 (15)	C17—C18—H18	119.3
C4—C9—H9	107.4	C19—C18—H18	119.3
C10—C9—H9	107.4	C20—C19—C18	118.16 (18)
C14—C9—H9	107.4	C20—C19—C22	120.8 (2)
C9—C10—C11	111.72 (15)	C18—C19—C22	121.02 (18)
C9—C10—H10A	109.3	C21—C20—C19	121.29 (17)
C11—C10—H10A	109.3	C21—C20—H20	119.4
C9—C10—H10B	109.3	C19—C20—H20	119.4
C11—C10—H10B	109.3	C20—C21—C16	119.31 (15)
H10A—C10—H10B	107.9	C20—C21—H21	120.3
C12—C11—C10	111.32 (17)	C16—C21—H21	120.3
C12—C11—H11A	109.4	C19—C22—H22A	109.5
C10—C11—H11A	109.4	C19—C22—H22B	109.5
C12—C11—H11B	109.4	H22A—C22—H22B	109.5
C10—C11—H11B	109.4	C19—C22—H22C	109.5
H11A—C11—H11B	108.0	H22A—C22—H22C	109.5
C13—C12—C11	111.39 (17)	H22B—C22—H22C	109.5
O2—S1—C1—C8	−146.67 (14)	C7—O1—C8—C15	−179.73 (13)
C16—S1—C1—C8	102.36 (14)	C3—C4—C9—C10	60.1 (2)
O2—S1—C1—C2	33.43 (16)	C5—C4—C9—C10	−120.06 (18)
C16—S1—C1—C2	−77.54 (14)	C3—C4—C9—C14	−64.24 (19)
C8—C1—C2—C7	−0.07 (16)	C5—C4—C9—C14	115.60 (17)
S1—C1—C2—C7	179.84 (12)	C4—C9—C10—C11	179.09 (17)
C8—C1—C2—C3	179.21 (16)	C14—C9—C10—C11	−55.3 (2)
S1—C1—C2—C3	−0.9 (3)	C9—C10—C11—C12	55.9 (3)
C7—C2—C3—C4	−0.4 (2)	C10—C11—C12—C13	−55.0 (2)
C1—C2—C3—C4	−179.61 (16)	C11—C12—C13—C14	54.7 (2)
C2—C3—C4—C5	−0.2 (2)	C12—C13—C14—C9	−55.4 (2)
C2—C3—C4—C9	179.61 (13)	C4—C9—C14—C13	−178.94 (15)
C3—C4—C5—C6	0.4 (2)	C10—C9—C14—C13	55.1 (2)
C9—C4—C5—C6	−179.46 (15)	O2—S1—C16—C21	−21.67 (17)
C4—C5—C6—C7	0.1 (3)	C1—S1—C16—C21	89.13 (15)
C5—C6—C7—O1	−179.92 (14)	O2—S1—C16—C17	156.54 (13)
C5—C6—C7—C2	−0.8 (2)	C1—S1—C16—C17	−92.67 (14)
C8—O1—C7—C6	179.88 (15)	C21—C16—C17—C18	−1.0 (3)
C8—O1—C7—C2	0.67 (16)	S1—C16—C17—C18	−179.22 (13)
C3—C2—C7—C6	1.0 (2)	C16—C17—C18—C19	1.2 (3)
C1—C2—C7—C6	−179.60 (15)	C17—C18—C19—C20	−0.8 (3)
C3—C2—C7—O1	−179.80 (12)	C17—C18—C19—C22	178.7 (2)
C1—C2—C7—O1	−0.37 (16)	C18—C19—C20—C21	0.2 (3)
C2—C1—C8—O1	0.49 (17)	C22—C19—C20—C21	−179.3 (2)
S1—C1—C8—O1	−179.43 (10)	C19—C20—C21—C16	0.0 (3)
C2—C1—C8—C15	179.27 (16)	C17—C16—C21—C20	0.4 (3)
S1—C1—C8—C15	−0.6 (3)	S1—C16—C21—C20	178.54 (14)
C7—O1—C8—C1	−0.72 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2i	0.95	2.48	3.140 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2i	0.95	2.48	3.140 (2)	127

Symmetry code: (i) .