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

In the title compound, C(22)H(24)O(3)S, the cyclo-hexyl ring adopts a chair conformation. The 4-methyl-phenyl ring makes a dihedral angle of 80.95 (4)° with the mean plane [mean deviation = 0.011 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C22H24O3S

M = 368.47

Monoclinic,

a = 10.6806 (2) Å

b = 12.5869 (3) Å

c = 14.2736 (3) Å

β = 93.094 (1)°

V = 1916.08 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.36 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.936, T max = 0.956

19350 measured reflections

4762 independent reflections

3810 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.05

4762 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 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/S1600536812010434/fb2242sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010434/fb2242Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010434/fb2242Isup3.cml

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

C22H24O3S	F(000) = 784
Mr = 368.47	Dx = 1.277 Mg m−3
Monoclinic, P21/n	Melting point = 437–438 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.6806 (2) Å	Cell parameters from 5853 reflections
b = 12.5869 (3) Å	θ = 2.2–27.7°
c = 14.2736 (3) Å	µ = 0.19 mm−1
β = 93.094 (1)°	T = 173 K
V = 1916.08 (7) Å3	Block, colourless
Z = 4	0.36 × 0.26 × 0.24 mm

Bruker SMART APEXII CCD diffractometer	4762 independent reflections
Radiation source: rotating anode	3810 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −16→16
Tmin = 0.936, Tmax = 0.956	l = −18→19
19350 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.6267P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4762 reflections	Δρmax = 0.29 e Å−3
238 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
94 constraints	Extinction coefficient: 0.0052 (10)
Primary atom site location: structure-invariant direct methods

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	0.27825 (3)	0.22598 (3)	0.23844 (2)	0.02775 (12)
O1	0.44984 (10)	0.12891 (8)	0.47290 (7)	0.0312 (2)
O2	0.16711 (10)	0.28891 (9)	0.24653 (8)	0.0348 (3)
O3	0.27066 (12)	0.12657 (9)	0.18864 (8)	0.0392 (3)
C1	0.34066 (13)	0.20282 (11)	0.35128 (10)	0.0257 (3)
C2	0.33675 (13)	0.27597 (11)	0.42945 (10)	0.0246 (3)
C3	0.28562 (13)	0.37621 (11)	0.44468 (10)	0.0262 (3)
H3	0.2377	0.4114	0.3960	0.031*
C4	0.30579 (14)	0.42369 (12)	0.53198 (10)	0.0286 (3)
C5	0.37647 (17)	0.36927 (13)	0.60298 (11)	0.0354 (4)
H5	0.3897	0.4024	0.6625	0.042*
C6	0.42743 (16)	0.26992 (13)	0.58987 (11)	0.0349 (4)
H6	0.4746	0.2338	0.6384	0.042*
C7	0.40552 (14)	0.22645 (11)	0.50199 (10)	0.0278 (3)
C8	0.40998 (14)	0.11734 (12)	0.38090 (11)	0.0289 (3)
C9	0.25195 (15)	0.53261 (12)	0.54981 (10)	0.0293 (3)
H9	0.2209	0.5618	0.4877	0.035*
C10	0.34893 (17)	0.60968 (14)	0.59082 (18)	0.0542 (5)
H10A	0.4183	0.6159	0.5479	0.065*
H10B	0.3841	0.5818	0.6515	0.065*
C11	0.2925 (2)	0.71952 (15)	0.60601 (19)	0.0599 (6)
H11A	0.3572	0.7670	0.6354	0.072*
H11B	0.2642	0.7505	0.5447	0.072*
C12	0.1826 (2)	0.71215 (16)	0.66823 (14)	0.0532 (5)
H12A	0.2123	0.6875	0.7314	0.064*
H12B	0.1448	0.7834	0.6748	0.064*
C13	0.08508 (19)	0.63650 (15)	0.62771 (16)	0.0521 (5)
H13A	0.0491	0.6652	0.5676	0.063*
H13B	0.0164	0.6302	0.6713	0.063*
C14	0.14023 (17)	0.52678 (14)	0.61102 (15)	0.0443 (4)
H14A	0.1667	0.4943	0.6721	0.053*
H14B	0.0750	0.4807	0.5804	0.053*
C15	0.45123 (17)	0.01826 (13)	0.33566 (13)	0.0396 (4)
H15A	0.4121	−0.0430	0.3648	0.059*
H15B	0.5426	0.0121	0.3437	0.059*
H15C	0.4262	0.0202	0.2686	0.059*
C16	0.39138 (14)	0.30592 (12)	0.18739 (10)	0.0289 (3)
C17	0.38998 (15)	0.41549 (13)	0.19887 (11)	0.0335 (3)
H17	0.3265	0.4485	0.2328	0.040*
C18	0.48222 (16)	0.47598 (14)	0.16024 (12)	0.0391 (4)
H18	0.4812	0.5510	0.1678	0.047*
C19	0.57661 (16)	0.42936 (15)	0.11046 (12)	0.0397 (4)
C20	0.57578 (17)	0.31987 (16)	0.09985 (13)	0.0451 (4)
H20	0.6392	0.2869	0.0659	0.054*
C21	0.48410 (16)	0.25753 (14)	0.13786 (12)	0.0387 (4)
H21	0.4848	0.1826	0.1301	0.046*
C22	0.67779 (19)	0.49602 (19)	0.07082 (16)	0.0586 (6)
H22A	0.7388	0.5166	0.1213	0.088*
H22B	0.6405	0.5599	0.0418	0.088*
H22C	0.7201	0.4550	0.0235	0.088*

	U11	U22	U33	U12	U13	U23
S1	0.0288 (2)	0.0292 (2)	0.02484 (19)	0.00142 (14)	−0.00237 (13)	−0.00406 (13)
O1	0.0351 (6)	0.0265 (5)	0.0316 (5)	0.0055 (4)	−0.0032 (4)	0.0009 (4)
O2	0.0266 (5)	0.0437 (6)	0.0334 (6)	0.0046 (5)	−0.0036 (4)	−0.0028 (5)
O3	0.0504 (7)	0.0344 (6)	0.0324 (6)	−0.0037 (5)	−0.0025 (5)	−0.0098 (5)
C1	0.0250 (7)	0.0257 (7)	0.0263 (7)	0.0003 (5)	0.0009 (5)	−0.0021 (5)
C2	0.0245 (7)	0.0258 (7)	0.0234 (6)	−0.0020 (5)	0.0006 (5)	0.0002 (5)
C3	0.0279 (7)	0.0279 (7)	0.0228 (6)	0.0018 (5)	0.0013 (5)	0.0018 (5)
C4	0.0331 (8)	0.0264 (7)	0.0264 (7)	0.0002 (6)	0.0042 (6)	0.0008 (6)
C5	0.0490 (10)	0.0339 (8)	0.0228 (7)	0.0011 (7)	−0.0030 (6)	−0.0022 (6)
C6	0.0425 (9)	0.0354 (8)	0.0261 (7)	0.0042 (7)	−0.0058 (6)	0.0038 (6)
C7	0.0292 (7)	0.0253 (7)	0.0288 (7)	0.0016 (5)	0.0005 (6)	0.0024 (6)
C8	0.0274 (7)	0.0283 (7)	0.0310 (7)	−0.0013 (6)	0.0011 (6)	−0.0005 (6)
C9	0.0371 (8)	0.0269 (7)	0.0243 (7)	0.0029 (6)	0.0045 (6)	0.0002 (6)
C10	0.0347 (9)	0.0336 (9)	0.0952 (16)	−0.0068 (7)	0.0131 (10)	−0.0150 (10)
C11	0.0483 (11)	0.0318 (10)	0.1003 (18)	−0.0080 (8)	0.0102 (11)	−0.0207 (10)
C12	0.0756 (14)	0.0419 (10)	0.0426 (10)	0.0152 (10)	0.0083 (10)	−0.0107 (8)
C13	0.0461 (11)	0.0418 (10)	0.0712 (13)	0.0083 (8)	0.0295 (10)	0.0054 (9)
C14	0.0369 (9)	0.0333 (9)	0.0642 (12)	−0.0006 (7)	0.0166 (8)	0.0030 (8)
C15	0.0431 (9)	0.0305 (8)	0.0445 (9)	0.0099 (7)	−0.0034 (7)	−0.0066 (7)
C16	0.0304 (7)	0.0321 (8)	0.0239 (7)	0.0042 (6)	0.0000 (6)	−0.0004 (6)
C17	0.0341 (8)	0.0329 (8)	0.0334 (8)	0.0054 (6)	0.0023 (6)	−0.0033 (6)
C18	0.0410 (9)	0.0347 (9)	0.0416 (9)	−0.0014 (7)	0.0008 (7)	−0.0002 (7)
C19	0.0340 (9)	0.0502 (10)	0.0348 (8)	−0.0013 (7)	0.0007 (7)	0.0041 (7)
C20	0.0390 (9)	0.0526 (11)	0.0449 (10)	0.0085 (8)	0.0132 (8)	−0.0012 (8)
C21	0.0411 (9)	0.0350 (8)	0.0406 (9)	0.0089 (7)	0.0083 (7)	−0.0029 (7)
C22	0.0437 (11)	0.0731 (15)	0.0596 (13)	−0.0112 (10)	0.0084 (9)	0.0082 (11)

S1—O2	1.4368 (11)	C11—H11B	0.9900
S1—O3	1.4391 (11)	C12—C13	1.504 (3)
S1—C1	1.7343 (15)	C12—H12A	0.9900
S1—C16	1.7603 (16)	C12—H12B	0.9900
O1—C8	1.3663 (18)	C13—C14	1.525 (2)
O1—C7	1.3874 (17)	C13—H13A	0.9900
C1—C8	1.360 (2)	C13—H13B	0.9900
C1—C2	1.4490 (19)	C14—H14A	0.9900
C2—C7	1.385 (2)	C14—H14B	0.9900
C2—C3	1.396 (2)	C15—H15A	0.9800
C3—C4	1.388 (2)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.408 (2)	C16—C21	1.388 (2)
C4—C9	1.514 (2)	C16—C17	1.389 (2)
C5—C6	1.381 (2)	C17—C18	1.383 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.377 (2)	C18—C19	1.394 (2)
C6—H6	0.9500	C18—H18	0.9500
C8—C15	1.482 (2)	C19—C20	1.386 (3)
C9—C10	1.514 (2)	C19—C22	1.503 (3)
C9—C14	1.518 (2)	C20—C21	1.388 (2)
C9—H9	1.0000	C20—H20	0.9500
C10—C11	1.528 (3)	C21—H21	0.9500
C10—H10A	0.9900	C22—H22A	0.9800
C10—H10B	0.9900	C22—H22B	0.9800
C11—C12	1.512 (3)	C22—H22C	0.9800
C11—H11A	0.9900
O2—S1—O3	119.62 (7)	C13—C12—C11	110.87 (16)
O2—S1—C1	107.21 (7)	C13—C12—H12A	109.5
O3—S1—C1	108.73 (7)	C11—C12—H12A	109.5
O2—S1—C16	107.86 (7)	C13—C12—H12B	109.5
O3—S1—C16	108.31 (7)	C11—C12—H12B	109.5
C1—S1—C16	104.03 (7)	H12A—C12—H12B	108.1
C8—O1—C7	106.75 (11)	C12—C13—C14	111.60 (17)
C8—C1—C2	107.52 (13)	C12—C13—H13A	109.3
C8—C1—S1	126.65 (11)	C14—C13—H13A	109.3
C2—C1—S1	125.65 (11)	C12—C13—H13B	109.3
C7—C2—C3	119.11 (13)	C14—C13—H13B	109.3
C7—C2—C1	104.68 (12)	H13A—C13—H13B	108.0
C3—C2—C1	136.20 (13)	C9—C14—C13	111.61 (14)
C4—C3—C2	119.05 (13)	C9—C14—H14A	109.3
C4—C3—H3	120.5	C13—C14—H14A	109.3
C2—C3—H3	120.5	C9—C14—H14B	109.3
C3—C4—C5	119.19 (14)	C13—C14—H14B	109.3
C3—C4—C9	119.93 (13)	H14A—C14—H14B	108.0
C5—C4—C9	120.89 (13)	C8—C15—H15A	109.5
C6—C5—C4	122.88 (14)	C8—C15—H15B	109.5
C6—C5—H5	118.6	H15A—C15—H15B	109.5
C4—C5—H5	118.6	C8—C15—H15C	109.5
C7—C6—C5	115.76 (14)	H15A—C15—H15C	109.5
C7—C6—H6	122.1	H15B—C15—H15C	109.5
C5—C6—H6	122.1	C21—C16—C17	120.55 (15)
C6—C7—C2	124.01 (14)	C21—C16—S1	118.98 (12)
C6—C7—O1	125.47 (14)	C17—C16—S1	120.45 (11)
C2—C7—O1	110.51 (13)	C18—C17—C16	119.15 (15)
C1—C8—O1	110.52 (13)	C18—C17—H17	120.4
C1—C8—C15	134.40 (14)	C16—C17—H17	120.4
O1—C8—C15	115.08 (13)	C17—C18—C19	121.45 (16)
C4—C9—C10	112.78 (13)	C17—C18—H18	119.3
C4—C9—C14	111.75 (13)	C19—C18—H18	119.3
C10—C9—C14	110.55 (14)	C20—C19—C18	118.27 (16)
C4—C9—H9	107.1	C20—C19—C22	120.96 (17)
C10—C9—H9	107.1	C18—C19—C22	120.76 (18)
C14—C9—H9	107.1	C19—C20—C21	121.32 (16)
C9—C10—C11	111.57 (16)	C19—C20—H20	119.3
C9—C10—H10A	109.3	C21—C20—H20	119.3
C11—C10—H10A	109.3	C20—C21—C16	119.26 (16)
C9—C10—H10B	109.3	C20—C21—H21	120.4
C11—C10—H10B	109.3	C16—C21—H21	120.4
H10A—C10—H10B	108.0	C19—C22—H22A	109.5
C12—C11—C10	110.64 (17)	C19—C22—H22B	109.5
C12—C11—H11A	109.5	H22A—C22—H22B	109.5
C10—C11—H11A	109.5	C19—C22—H22C	109.5
C12—C11—H11B	109.5	H22A—C22—H22C	109.5
C10—C11—H11B	109.5	H22B—C22—H22C	109.5
H11A—C11—H11B	108.1
O2—S1—C1—C8	151.36 (13)	C7—O1—C8—C15	178.36 (13)
O3—S1—C1—C8	20.71 (16)	C3—C4—C9—C10	−128.70 (17)
C16—S1—C1—C8	−94.55 (14)	C5—C4—C9—C10	51.3 (2)
O2—S1—C1—C2	−34.09 (14)	C3—C4—C9—C14	106.03 (17)
O3—S1—C1—C2	−164.74 (12)	C5—C4—C9—C14	−73.9 (2)
C16—S1—C1—C2	80.00 (13)	C4—C9—C10—C11	178.75 (17)
C8—C1—C2—C7	−0.40 (16)	C14—C9—C10—C11	−55.3 (2)
S1—C1—C2—C7	−175.82 (11)	C9—C10—C11—C12	56.7 (3)
C8—C1—C2—C3	178.17 (16)	C10—C11—C12—C13	−56.5 (3)
S1—C1—C2—C3	2.8 (3)	C11—C12—C13—C14	56.0 (2)
C7—C2—C3—C4	0.4 (2)	C4—C9—C14—C13	−179.20 (16)
C1—C2—C3—C4	−178.05 (15)	C10—C9—C14—C13	54.3 (2)
C2—C3—C4—C5	−0.4 (2)	C12—C13—C14—C9	−55.1 (2)
C2—C3—C4—C9	179.60 (13)	O2—S1—C16—C21	−154.15 (13)
C3—C4—C5—C6	0.1 (3)	O3—S1—C16—C21	−23.34 (15)
C9—C4—C5—C6	−179.94 (15)	C1—S1—C16—C21	92.22 (14)
C4—C5—C6—C7	0.3 (3)	O2—S1—C16—C17	27.71 (14)
C5—C6—C7—C2	−0.4 (2)	O3—S1—C16—C17	158.52 (13)
C5—C6—C7—O1	178.60 (15)	C1—S1—C16—C17	−85.92 (14)
C3—C2—C7—C6	0.0 (2)	C21—C16—C17—C18	0.0 (2)
C1—C2—C7—C6	178.91 (15)	S1—C16—C17—C18	178.14 (13)
C3—C2—C7—O1	−179.07 (12)	C16—C17—C18—C19	−0.3 (3)
C1—C2—C7—O1	−0.20 (16)	C17—C18—C19—C20	0.4 (3)
C8—O1—C7—C6	−178.37 (15)	C17—C18—C19—C22	−178.60 (17)
C8—O1—C7—C2	0.72 (16)	C18—C19—C20—C21	−0.3 (3)
C2—C1—C8—O1	0.87 (17)	C22—C19—C20—C21	178.70 (18)
S1—C1—C8—O1	176.23 (10)	C19—C20—C21—C16	0.1 (3)
C2—C1—C8—C15	−178.30 (17)	C17—C16—C21—C20	0.1 (3)
S1—C1—C8—C15	−2.9 (3)	S1—C16—C21—C20	−178.07 (14)
C7—O1—C8—C1	−0.98 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.52	3.3888 (19)	152
C13—H13B···O2ii	0.99	2.55	3.447 (2)	151
C10—H10A···Cg1iii	0.99	2.73	3.675 (2)	159
C11—H11A···Cg2iii	0.99	2.95	3.646 (2)	128
C20—H20···Cg1iv	0.95	2.82	3.745 (2)	164
C22—H22C···Cg2iv	0.98	2.96	3.907 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene and the C1/C2/C7/O1/C8 furan rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.52	3.3888 (19)	152
C13—H13B⋯O2ii	0.99	2.55	3.447 (2)	151
C10—H10A⋯Cg1iii	0.99	2.73	3.675 (2)	159
C11—H11A⋯Cg2iii	0.99	2.95	3.646 (2)	128
C20—H20⋯Cg1iv	0.95	2.82	3.745 (2)	164
C22—H22C⋯Cg2iv	0.98	2.96	3.907 (2)	164

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