5-Cyclo-hexyl-2-methyl-3-(3-methyl-phenyl-sulfin-yl)-1-benzo-furan.

In the title compound, C22H24O2S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo-furan and 3-methyl-phenyl moieties is 86.48 (4)°. In the crystal, mol-ecules are connected along the a-axis direction by two different inversion-generated pairs of C-H⋯π and C-H⋯O inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012 ▶, 2013 ▶, 2014 ▶).

Experimental

Crystal data

C22H24O2S

M = 352.47

Triclinic,

a = 8.8562 (2) Å

b = 10.3095 (2) Å

c = 11.1248 (2) Å

α = 91.147 (1)°

β = 113.425 (1)°

γ = 98.036 (1)°

V = 919.66 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.40 × 0.39 × 0.32 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.685, T max = 0.746

16991 measured reflections

4585 independent reflections

3954 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.03

4585 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.29 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814011192/ld2128sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011192/ld2128Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011192/ld2128Isup3.cml

CCDC reference: 1003285

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H24O2S	Z = 2
Mr = 352.47	F(000) = 376
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Melting point = 391–390 K
a = 8.8562 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3095 (2) Å	Cell parameters from 6026 reflections
c = 11.1248 (2) Å	θ = 2.5–28.3°
α = 91.147 (1)°	µ = 0.19 mm−1
β = 113.425 (1)°	T = 173 K
γ = 98.036 (1)°	Block, colourless
V = 919.66 (3) Å3	0.40 × 0.39 × 0.32 mm

Bruker SMART APEXII CCD diffractometer	4585 independent reflections
Radiation source: rotating anode	3954 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.685, Tmax = 0.746	l = −14→13
16991 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: difference Fourier map
wR(F2) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.3576P] where P = (Fo2 + 2Fc2)/3
4585 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.29 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	0.33525 (4)	0.01712 (3)	0.19341 (3)	0.02995 (11)
O1	0.54828 (13)	0.32465 (11)	0.08241 (10)	0.0345 (2)
O2	0.45096 (14)	−0.04957 (11)	0.30068 (11)	0.0386 (3)
C1	0.44786 (17)	0.16556 (14)	0.17900 (13)	0.0282 (3)
C2	0.56092 (16)	0.26407 (14)	0.28182 (13)	0.0263 (3)
C3	0.61829 (17)	0.28088 (14)	0.41837 (13)	0.0263 (3)
H3	0.5820	0.2165	0.4651	0.032*
C4	0.72974 (17)	0.39386 (14)	0.48490 (13)	0.0271 (3)
C5	0.78181 (18)	0.48692 (15)	0.41363 (15)	0.0323 (3)
H5	0.8576	0.5637	0.4601	0.039*
C6	0.72745 (19)	0.47179 (16)	0.27813 (15)	0.0342 (3)
H6	0.7640	0.5356	0.2309	0.041*
C7	0.61774 (18)	0.35936 (15)	0.21611 (14)	0.0292 (3)
C8	0.44668 (19)	0.20622 (16)	0.06342 (14)	0.0322 (3)
C9	0.79399 (18)	0.41763 (14)	0.63272 (14)	0.0285 (3)
H9	0.8804	0.4985	0.6605	0.034*
C10	0.8773 (2)	0.30491 (15)	0.70293 (14)	0.0328 (3)
H10A	0.7954	0.2227	0.6746	0.039*
H10B	0.9700	0.2930	0.6775	0.039*
C11	0.9449 (2)	0.33006 (17)	0.85189 (15)	0.0391 (4)
H11A	0.9915	0.2524	0.8934	0.047*
H11B	1.0363	0.4062	0.8814	0.047*
C12	0.8107 (2)	0.35721 (17)	0.89605 (16)	0.0405 (4)
H12A	0.8607	0.3800	0.9922	0.049*
H12B	0.7264	0.2770	0.8770	0.049*
C13	0.7266 (2)	0.4689 (2)	0.82687 (16)	0.0478 (5)
H13A	0.8081	0.5513	0.8543	0.057*
H13B	0.6346	0.4806	0.8532	0.057*
C14	0.6574 (2)	0.4421 (2)	0.67754 (16)	0.0469 (5)
H14A	0.6076	0.5184	0.6353	0.056*
H14B	0.5683	0.3644	0.6492	0.056*
C15	0.3574 (2)	0.15033 (19)	−0.07522 (15)	0.0434 (4)
H15A	0.3011	0.0608	−0.0778	0.065*
H15B	0.4375	0.1483	−0.1155	0.065*
H15C	0.2746	0.2050	−0.1239	0.065*
C16	0.20315 (17)	0.08466 (13)	0.25708 (14)	0.0271 (3)
C17	0.23952 (17)	0.08488 (13)	0.38974 (13)	0.0267 (3)
H17	0.3339	0.0498	0.4467	0.032*
C18	0.13706 (18)	0.13682 (14)	0.43984 (14)	0.0293 (3)
C19	−0.00153 (19)	0.18503 (15)	0.35310 (16)	0.0349 (3)
H19	−0.0723	0.2208	0.3858	0.042*
C20	−0.03811 (19)	0.18184 (17)	0.21998 (16)	0.0384 (4)
H20	−0.1339	0.2147	0.1623	0.046*
C21	0.06364 (19)	0.13129 (15)	0.17043 (15)	0.0341 (3)
H21	0.0387	0.1285	0.0790	0.041*
C22	0.1782 (2)	0.14006 (17)	0.58434 (16)	0.0389 (4)
H22A	0.2439	0.2255	0.6271	0.058*
H22B	0.2428	0.0701	0.6221	0.058*
H22C	0.0748	0.1268	0.5983	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.03221 (19)	0.02785 (18)	0.02855 (18)	0.00229 (14)	0.01213 (14)	−0.00417 (13)
O1	0.0349 (6)	0.0442 (6)	0.0278 (5)	0.0052 (5)	0.0166 (4)	0.0054 (4)
O2	0.0401 (6)	0.0350 (6)	0.0432 (6)	0.0124 (5)	0.0173 (5)	0.0045 (5)
C1	0.0270 (7)	0.0325 (7)	0.0256 (6)	0.0044 (6)	0.0116 (5)	−0.0018 (5)
C2	0.0231 (6)	0.0286 (7)	0.0288 (7)	0.0053 (5)	0.0120 (5)	0.0013 (5)
C3	0.0256 (6)	0.0271 (7)	0.0265 (6)	0.0036 (5)	0.0111 (5)	0.0024 (5)
C4	0.0238 (6)	0.0272 (7)	0.0292 (7)	0.0063 (5)	0.0088 (5)	0.0027 (5)
C5	0.0259 (7)	0.0298 (7)	0.0367 (8)	0.0012 (6)	0.0091 (6)	0.0033 (6)
C6	0.0302 (7)	0.0355 (8)	0.0388 (8)	0.0025 (6)	0.0165 (6)	0.0102 (6)
C7	0.0270 (7)	0.0362 (8)	0.0269 (7)	0.0065 (6)	0.0132 (5)	0.0042 (6)
C8	0.0308 (7)	0.0399 (8)	0.0281 (7)	0.0066 (6)	0.0141 (6)	−0.0005 (6)
C9	0.0269 (7)	0.0255 (7)	0.0281 (7)	0.0027 (5)	0.0065 (5)	0.0002 (5)
C10	0.0379 (8)	0.0329 (7)	0.0302 (7)	0.0124 (6)	0.0141 (6)	0.0043 (6)
C11	0.0440 (9)	0.0431 (9)	0.0306 (8)	0.0173 (7)	0.0120 (7)	0.0083 (7)
C12	0.0454 (9)	0.0449 (9)	0.0312 (8)	0.0022 (7)	0.0175 (7)	−0.0031 (7)
C13	0.0471 (10)	0.0627 (12)	0.0334 (8)	0.0247 (9)	0.0115 (7)	−0.0078 (8)
C14	0.0398 (9)	0.0667 (12)	0.0322 (8)	0.0278 (9)	0.0066 (7)	−0.0065 (8)
C15	0.0473 (9)	0.0584 (11)	0.0259 (7)	0.0072 (8)	0.0168 (7)	−0.0021 (7)
C16	0.0263 (7)	0.0242 (6)	0.0287 (7)	0.0003 (5)	0.0102 (5)	−0.0003 (5)
C17	0.0248 (6)	0.0257 (6)	0.0278 (7)	0.0037 (5)	0.0089 (5)	0.0025 (5)
C18	0.0301 (7)	0.0272 (7)	0.0317 (7)	0.0031 (6)	0.0140 (6)	0.0031 (5)
C19	0.0298 (7)	0.0345 (8)	0.0431 (8)	0.0083 (6)	0.0165 (6)	0.0047 (6)
C20	0.0287 (7)	0.0424 (9)	0.0399 (8)	0.0109 (7)	0.0076 (6)	0.0100 (7)
C21	0.0319 (7)	0.0374 (8)	0.0281 (7)	0.0044 (6)	0.0073 (6)	0.0054 (6)
C22	0.0431 (9)	0.0451 (9)	0.0350 (8)	0.0130 (7)	0.0204 (7)	0.0049 (7)

S1—O2	1.4847 (11)	C11—H11B	0.9900
S1—C1	1.7528 (15)	C12—C13	1.513 (2)
S1—C16	1.7950 (14)	C12—H12A	0.9900
O1—C8	1.3698 (19)	C12—H12B	0.9900
O1—C7	1.3815 (17)	C13—C14	1.529 (2)
C1—C8	1.357 (2)	C13—H13A	0.9900
C1—C2	1.4494 (19)	C13—H13B	0.9900
C2—C7	1.391 (2)	C14—H14A	0.9900
C2—C3	1.3953 (19)	C14—H14B	0.9900
C3—C4	1.3935 (19)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.400 (2)	C15—H15C	0.9800
C4—C9	1.5129 (19)	C16—C17	1.3797 (19)
C5—C6	1.386 (2)	C16—C21	1.387 (2)
C5—H5	0.9500	C17—C18	1.395 (2)
C6—C7	1.373 (2)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.390 (2)
C8—C15	1.484 (2)	C18—C22	1.499 (2)
C9—C10	1.5241 (19)	C19—C20	1.383 (2)
C9—C14	1.529 (2)	C19—H19	0.9500
C9—H9	1.0000	C20—C21	1.379 (2)
C10—C11	1.524 (2)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900	C22—H22A	0.9800
C11—C12	1.511 (2)	C22—H22B	0.9800
C11—H11A	0.9900	C22—H22C	0.9800
O2—S1—C1	107.71 (7)	C11—C12—H12A	109.4
O2—S1—C16	107.13 (7)	C13—C12—H12A	109.4
C1—S1—C16	97.97 (6)	C11—C12—H12B	109.4
C8—O1—C7	106.36 (11)	C13—C12—H12B	109.4
C8—C1—C2	107.14 (13)	H12A—C12—H12B	108.0
C8—C1—S1	124.02 (12)	C12—C13—C14	111.37 (14)
C2—C1—S1	128.81 (11)	C12—C13—H13A	109.4
C7—C2—C3	119.30 (13)	C14—C13—H13A	109.4
C7—C2—C1	104.68 (12)	C12—C13—H13B	109.4
C3—C2—C1	136.02 (13)	C14—C13—H13B	109.4
C4—C3—C2	118.83 (13)	H13A—C13—H13B	108.0
C4—C3—H3	120.6	C13—C14—C9	111.25 (13)
C2—C3—H3	120.6	C13—C14—H14A	109.4
C3—C4—C5	119.41 (13)	C9—C14—H14A	109.4
C3—C4—C9	120.91 (13)	C13—C14—H14B	109.4
C5—C4—C9	119.67 (13)	C9—C14—H14B	109.4
C6—C5—C4	122.75 (14)	H14A—C14—H14B	108.0
C6—C5—H5	118.6	C8—C15—H15A	109.5
C4—C5—H5	118.6	C8—C15—H15B	109.5
C7—C6—C5	116.14 (14)	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	125.75 (13)	H15B—C15—H15C	109.5
C6—C7—C2	123.57 (13)	C17—C16—C21	121.73 (13)
O1—C7—C2	110.68 (13)	C17—C16—S1	119.36 (10)
C1—C8—O1	111.14 (13)	C21—C16—S1	118.88 (11)
C1—C8—C15	133.36 (16)	C16—C17—C18	119.67 (13)
O1—C8—C15	115.49 (14)	C16—C17—H17	120.2
C4—C9—C10	111.95 (12)	C18—C17—H17	120.2
C4—C9—C14	112.42 (12)	C19—C18—C17	118.50 (13)
C10—C9—C14	109.64 (13)	C19—C18—C22	121.62 (13)
C4—C9—H9	107.5	C17—C18—C22	119.88 (13)
C10—C9—H9	107.5	C20—C19—C18	121.14 (14)
C14—C9—H9	107.5	C20—C19—H19	119.4
C11—C10—C9	111.93 (12)	C18—C19—H19	119.4
C11—C10—H10A	109.2	C21—C20—C19	120.42 (14)
C9—C10—H10A	109.2	C21—C20—H20	119.8
C11—C10—H10B	109.2	C19—C20—H20	119.8
C9—C10—H10B	109.2	C20—C21—C16	118.51 (14)
H10A—C10—H10B	107.9	C20—C21—H21	120.7
C12—C11—C10	111.65 (13)	C16—C21—H21	120.7
C12—C11—H11A	109.3	C18—C22—H22A	109.5
C10—C11—H11A	109.3	C18—C22—H22B	109.5
C12—C11—H11B	109.3	H22A—C22—H22B	109.5
C10—C11—H11B	109.3	C18—C22—H22C	109.5
H11A—C11—H11B	108.0	H22A—C22—H22C	109.5
C11—C12—C13	111.11 (14)	H22B—C22—H22C	109.5
O2—S1—C1—C8	131.33 (13)	C7—O1—C8—C15	179.61 (13)
C16—S1—C1—C8	−117.76 (13)	C3—C4—C9—C10	56.24 (17)
O2—S1—C1—C2	−46.28 (14)	C5—C4—C9—C10	−124.23 (14)
C16—S1—C1—C2	64.63 (13)	C3—C4—C9—C14	−67.70 (18)
C8—C1—C2—C7	0.82 (15)	C5—C4—C9—C14	111.83 (16)
S1—C1—C2—C7	178.75 (11)	C4—C9—C10—C11	178.94 (13)
C8—C1—C2—C3	−179.08 (15)	C14—C9—C10—C11	−55.57 (17)
S1—C1—C2—C3	−1.2 (2)	C9—C10—C11—C12	55.45 (19)
C7—C2—C3—C4	0.74 (19)	C10—C11—C12—C13	−54.59 (19)
C1—C2—C3—C4	−179.36 (14)	C11—C12—C13—C14	55.3 (2)
C2—C3—C4—C5	−0.31 (19)	C12—C13—C14—C9	−56.6 (2)
C2—C3—C4—C9	179.22 (12)	C4—C9—C14—C13	−178.73 (14)
C3—C4—C5—C6	−0.2 (2)	C10—C9—C14—C13	56.05 (19)
C9—C4—C5—C6	−179.71 (13)	O2—S1—C16—C17	9.59 (13)
C4—C5—C6—C7	0.2 (2)	C1—S1—C16—C17	−101.79 (12)
C5—C6—C7—O1	−179.97 (13)	O2—S1—C16—C21	−168.25 (12)
C5—C6—C7—C2	0.3 (2)	C1—S1—C16—C21	80.37 (13)
C8—O1—C7—C6	−179.85 (14)	C21—C16—C17—C18	−2.0 (2)
C8—O1—C7—C2	−0.05 (15)	S1—C16—C17—C18	−179.79 (11)
C3—C2—C7—C6	−0.7 (2)	C16—C17—C18—C19	1.1 (2)
C1—C2—C7—C6	179.33 (13)	C16—C17—C18—C22	−178.62 (13)
C3—C2—C7—O1	179.45 (11)	C17—C18—C19—C20	0.1 (2)
C1—C2—C7—O1	−0.47 (15)	C22—C18—C19—C20	179.84 (15)
C2—C1—C8—O1	−0.90 (16)	C18—C19—C20—C21	−0.5 (3)
S1—C1—C8—O1	−178.95 (10)	C19—C20—C21—C16	−0.3 (2)
C2—C1—C8—C15	−179.66 (16)	C17—C16—C21—C20	1.6 (2)
S1—C1—C8—C15	2.3 (3)	S1—C16—C21—C20	179.37 (12)
C7—O1—C8—C1	0.61 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O2i	0.98	2.54	3.295 (2)	134
C14—H14A···Cg1ii	0.99	2.91	3.607 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯O2i	0.98	2.54	3.295 (2)	134
C14—H14A⋯Cg1ii	0.99	2.91	3.607 (2)	128

Symmetry codes: (i) ; (ii) .