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

In the title compound, C22H24O3S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzo-furan ring system and the benzene ring is 81.78 (4)°. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions into inversion dimers. These dimers are further linked by C-H⋯π inter-actions into supra-molecular chains running along the b-axis direction. In addition, C-H⋯O hydrogen bonds are observed between inversion-related dimers.

Related literature

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

Experimental

Crystal data

C22H24O3S

M = 368.47

Triclinic,

a = 8.9729 (1) Å

b = 10.3462 (1) Å

c = 11.0978 (2) Å

α = 91.027 (1)°

β = 112.142 (1)°

γ = 96.920 (1)°

V = 945.09 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.45 × 0.24 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.704, T max = 0.746

17505 measured reflections

4676 independent reflections

3862 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

4676 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.36 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/S1600536814006448/kj2238sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006448/kj2238Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006448/kj2238Isup3.cml

CCDC reference: 993236

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

C22H24O3S	Z = 2
Mr = 368.47	F(000) = 392
Triclinic, P1	Dx = 1.295 Mg m−3
Hall symbol: -P 1	Melting point = 428–429 K
a = 8.9729 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3462 (1) Å	Cell parameters from 6413 reflections
c = 11.0978 (2) Å	θ = 2.5–28.0°
α = 91.027 (1)°	µ = 0.19 mm−1
β = 112.142 (1)°	T = 173 K
γ = 96.920 (1)°	Block, colourless
V = 945.09 (2) Å3	0.45 × 0.24 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	4676 independent reflections
Radiation source: rotating anode	3862 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.027
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 = 0.704, Tmax = 0.746	l = −14→14
17505 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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.3454P] where P = (Fo2 + 2Fc2)/3
4676 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.36 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	0.35800 (4)	0.03292 (4)	0.20843 (3)	0.02902 (11)
O1	0.55693 (14)	0.33589 (12)	0.08723 (11)	0.0373 (3)
O2	0.46948 (14)	−0.02883 (11)	0.31363 (10)	0.0359 (3)
O3	0.27359 (15)	−0.03917 (11)	0.08444 (11)	0.0405 (3)
C1	0.46417 (18)	0.17522 (15)	0.18450 (14)	0.0290 (3)
C2	0.57504 (17)	0.26991 (14)	0.28633 (14)	0.0275 (3)
C3	0.63168 (17)	0.28333 (14)	0.42235 (14)	0.0279 (3)
H3	0.5980	0.2181	0.4694	0.033*
C4	0.73853 (18)	0.39425 (15)	0.48773 (15)	0.0299 (3)
C5	0.78770 (19)	0.48851 (16)	0.41575 (16)	0.0369 (4)
H5	0.8608	0.5636	0.4613	0.044*
C6	0.7337 (2)	0.47625 (17)	0.28097 (17)	0.0389 (4)
H6	0.7682	0.5404	0.2333	0.047*
C7	0.62752 (19)	0.36615 (16)	0.22028 (15)	0.0327 (3)
C8	0.45740 (19)	0.22001 (16)	0.06823 (15)	0.0338 (3)
C9	0.79994 (18)	0.41730 (15)	0.63454 (14)	0.0310 (3)
H9	0.8961	0.4868	0.6611	0.037*
C10	0.8576 (2)	0.29841 (18)	0.70674 (16)	0.0426 (4)
H10A	0.9431	0.2692	0.6810	0.051*
H10B	0.7657	0.2266	0.6813	0.051*
C15	0.3672 (2)	0.1726 (2)	−0.07082 (16)	0.0449 (4)
H15A	0.3005	0.0889	−0.0758	0.067*
H15B	0.4446	0.1613	−0.1119	0.067*
H15C	0.2970	0.2365	−0.1163	0.067*
C16	0.21417 (17)	0.08713 (14)	0.26325 (14)	0.0274 (3)
C17	0.24711 (17)	0.09527 (14)	0.39576 (14)	0.0283 (3)
H17	0.3450	0.0700	0.4555	0.034*
C18	0.13676 (19)	0.14042 (15)	0.44124 (15)	0.0325 (3)
C19	−0.0052 (2)	0.17699 (17)	0.35005 (17)	0.0391 (4)
H19	−0.0811	0.2095	0.3795	0.047*
C20	−0.0379 (2)	0.16714 (18)	0.21828 (17)	0.0410 (4)
H20	−0.1362	0.1918	0.1584	0.049*
C21	0.07095 (19)	0.12176 (16)	0.17273 (15)	0.0350 (3)
H21	0.0488	0.1143	0.0820	0.042*
C22	0.1720 (2)	0.1479 (2)	0.58506 (17)	0.0450 (4)
H22A	0.2309	0.0759	0.6250	0.068*
H22B	0.0696	0.1414	0.5986	0.068*
H22C	0.2385	0.2312	0.6253	0.068*
C11	0.9247 (2)	0.32679 (18)	0.85430 (16)	0.0436 (4)
H11A	0.9557	0.2458	0.8976	0.052*
H11B	1.0235	0.3921	0.8810	0.052*
C12	0.8014 (2)	0.3777 (2)	0.89752 (17)	0.0467 (4)
H12A	0.8507	0.4010	0.9926	0.056*
H12B	0.7080	0.3085	0.8802	0.056*
C13	0.7425 (3)	0.4959 (2)	0.82666 (19)	0.0627 (6)
H13A	0.8335	0.5684	0.8525	0.075*
H13B	0.6564	0.5237	0.8526	0.075*
C14	0.6753 (3)	0.4684 (2)	0.67829 (18)	0.0586 (6)
H14A	0.5764	0.4032	0.6511	0.070*
H14B	0.6447	0.5497	0.6355	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.0321 (2)	0.03056 (19)	0.02058 (18)	0.00720 (14)	0.00497 (14)	−0.00076 (13)
O1	0.0391 (6)	0.0488 (7)	0.0271 (6)	0.0072 (5)	0.0157 (5)	0.0078 (5)
O2	0.0390 (6)	0.0375 (6)	0.0295 (6)	0.0160 (5)	0.0080 (5)	0.0054 (5)
O3	0.0492 (7)	0.0387 (6)	0.0258 (6)	0.0042 (5)	0.0066 (5)	−0.0077 (5)
C1	0.0287 (7)	0.0357 (8)	0.0227 (7)	0.0086 (6)	0.0087 (5)	0.0006 (6)
C2	0.0241 (7)	0.0332 (7)	0.0260 (7)	0.0070 (5)	0.0095 (5)	0.0027 (6)
C3	0.0259 (7)	0.0322 (7)	0.0246 (7)	0.0044 (5)	0.0083 (5)	0.0033 (5)
C4	0.0254 (7)	0.0331 (8)	0.0289 (7)	0.0050 (6)	0.0074 (6)	0.0027 (6)
C5	0.0314 (8)	0.0361 (8)	0.0381 (9)	−0.0001 (6)	0.0089 (7)	0.0053 (7)
C6	0.0347 (8)	0.0439 (9)	0.0384 (9)	0.0020 (7)	0.0149 (7)	0.0118 (7)
C7	0.0303 (7)	0.0429 (9)	0.0272 (7)	0.0091 (6)	0.0122 (6)	0.0061 (6)
C8	0.0337 (8)	0.0441 (9)	0.0258 (7)	0.0117 (6)	0.0120 (6)	0.0033 (6)
C9	0.0284 (7)	0.0308 (7)	0.0273 (7)	0.0016 (6)	0.0041 (6)	0.0009 (6)
C10	0.0561 (11)	0.0430 (9)	0.0298 (8)	0.0213 (8)	0.0131 (7)	0.0036 (7)
C15	0.0536 (11)	0.0588 (11)	0.0218 (8)	0.0124 (9)	0.0124 (7)	0.0017 (7)
C16	0.0266 (7)	0.0273 (7)	0.0239 (7)	0.0032 (5)	0.0050 (5)	0.0015 (5)
C17	0.0262 (7)	0.0303 (7)	0.0244 (7)	0.0047 (5)	0.0048 (5)	0.0029 (5)
C18	0.0318 (7)	0.0344 (8)	0.0309 (8)	0.0044 (6)	0.0113 (6)	0.0032 (6)
C19	0.0307 (8)	0.0446 (9)	0.0430 (9)	0.0101 (7)	0.0136 (7)	0.0039 (7)
C20	0.0290 (8)	0.0465 (9)	0.0396 (9)	0.0112 (7)	0.0024 (7)	0.0063 (7)
C21	0.0321 (8)	0.0404 (8)	0.0248 (7)	0.0066 (6)	0.0016 (6)	0.0048 (6)
C22	0.0495 (10)	0.0573 (11)	0.0353 (9)	0.0183 (8)	0.0207 (8)	0.0068 (8)
C11	0.0551 (11)	0.0439 (10)	0.0288 (8)	0.0162 (8)	0.0098 (7)	0.0054 (7)
C12	0.0441 (10)	0.0616 (12)	0.0310 (9)	−0.0035 (8)	0.0141 (7)	−0.0066 (8)
C13	0.0647 (13)	0.0845 (16)	0.0359 (10)	0.0439 (12)	0.0064 (9)	−0.0132 (10)
C14	0.0554 (12)	0.0823 (15)	0.0344 (9)	0.0429 (11)	0.0035 (8)	−0.0074 (9)

S1—O3	1.4370 (11)	C15—H15C	0.9800
S1—O2	1.4396 (11)	C16—C17	1.385 (2)
S1—C1	1.7356 (16)	C16—C21	1.393 (2)
S1—C16	1.7619 (16)	C17—C18	1.390 (2)
O1—C8	1.368 (2)	C17—H17	0.9500
O1—C7	1.3821 (18)	C18—C19	1.396 (2)
C1—C8	1.361 (2)	C18—C22	1.504 (2)
C1—C2	1.451 (2)	C19—C20	1.378 (2)
C2—C7	1.387 (2)	C19—H19	0.9500
C2—C3	1.398 (2)	C20—C21	1.380 (3)
C3—C4	1.394 (2)	C20—H20	0.9500
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.405 (2)	C22—H22A	0.9800
C4—C9	1.514 (2)	C22—H22B	0.9800
C5—C6	1.386 (2)	C22—H22C	0.9800
C5—H5	0.9500	C11—C12	1.504 (3)
C6—C7	1.373 (2)	C11—H11A	0.9900
C6—H6	0.9500	C11—H11B	0.9900
C8—C15	1.488 (2)	C12—C13	1.507 (3)
C9—C10	1.516 (2)	C12—H12A	0.9900
C9—C14	1.519 (2)	C12—H12B	0.9900
C9—H9	1.0000	C13—C14	1.533 (3)
C10—C11	1.526 (2)	C13—H13A	0.9900
C10—H10A	0.9900	C13—H13B	0.9900
C10—H10B	0.9900	C14—H14A	0.9900
C15—H15A	0.9800	C14—H14B	0.9900
C15—H15B	0.9800
O3—S1—O2	119.03 (7)	C17—C16—C21	121.58 (15)
O3—S1—C1	108.30 (7)	C17—C16—S1	119.06 (11)
O2—S1—C1	107.58 (7)	C21—C16—S1	119.36 (12)
O3—S1—C16	108.82 (7)	C16—C17—C18	119.96 (13)
O2—S1—C16	107.73 (7)	C16—C17—H17	120.0
C1—S1—C16	104.43 (7)	C18—C17—H17	120.0
C8—O1—C7	106.82 (12)	C17—C18—C19	118.09 (15)
C8—C1—C2	107.39 (14)	C17—C18—C22	119.86 (14)
C8—C1—S1	126.89 (12)	C19—C18—C22	122.05 (15)
C2—C1—S1	125.71 (11)	C20—C19—C18	121.58 (16)
C7—C2—C3	119.35 (14)	C20—C19—H19	119.2
C7—C2—C1	104.61 (13)	C18—C19—H19	119.2
C3—C2—C1	136.03 (14)	C19—C20—C21	120.49 (15)
C4—C3—C2	118.79 (14)	C19—C20—H20	119.8
C4—C3—H3	120.6	C21—C20—H20	119.8
C2—C3—H3	120.6	C20—C21—C16	118.29 (15)
C3—C4—C5	119.38 (14)	C20—C21—H21	120.9
C3—C4—C9	121.55 (14)	C16—C21—H21	120.9
C5—C4—C9	119.06 (14)	C18—C22—H22A	109.5
C6—C5—C4	122.58 (15)	C18—C22—H22B	109.5
C6—C5—H5	118.7	H22A—C22—H22B	109.5
C4—C5—H5	118.7	C18—C22—H22C	109.5
C7—C6—C5	116.20 (15)	H22A—C22—H22C	109.5
C7—C6—H6	121.9	H22B—C22—H22C	109.5
C5—C6—H6	121.9	C12—C11—C10	111.21 (15)
C6—C7—O1	125.67 (15)	C12—C11—H11A	109.4
C6—C7—C2	123.70 (15)	C10—C11—H11A	109.4
O1—C7—C2	110.63 (14)	C12—C11—H11B	109.4
C1—C8—O1	110.55 (14)	C10—C11—H11B	109.4
C1—C8—C15	134.82 (16)	H11A—C11—H11B	108.0
O1—C8—C15	114.63 (14)	C11—C12—C13	111.00 (16)
C4—C9—C10	113.42 (13)	C11—C12—H12A	109.4
C4—C9—C14	112.13 (13)	C13—C12—H12A	109.4
C10—C9—C14	110.10 (15)	C11—C12—H12B	109.4
C4—C9—H9	106.9	C13—C12—H12B	109.4
C10—C9—H9	106.9	H12A—C12—H12B	108.0
C14—C9—H9	106.9	C12—C13—C14	111.88 (17)
C9—C10—C11	111.95 (14)	C12—C13—H13A	109.2
C9—C10—H10A	109.2	C14—C13—H13A	109.2
C11—C10—H10A	109.2	C12—C13—H13B	109.2
C9—C10—H10B	109.2	C14—C13—H13B	109.2
C11—C10—H10B	109.2	H13A—C13—H13B	107.9
H10A—C10—H10B	107.9	C9—C14—C13	111.20 (15)
C8—C15—H15A	109.5	C9—C14—H14A	109.4
C8—C15—H15B	109.5	C13—C14—H14A	109.4
H15A—C15—H15B	109.5	C9—C14—H14B	109.4
C8—C15—H15C	109.5	C13—C14—H14B	109.4
H15A—C15—H15C	109.5	H14A—C14—H14B	108.0
H15B—C15—H15C	109.5
O3—S1—C1—C8	6.42 (17)	C7—O1—C8—C15	178.75 (14)
O2—S1—C1—C8	136.29 (14)	C3—C4—C9—C10	46.6 (2)
C16—S1—C1—C8	−109.42 (15)	C5—C4—C9—C10	−134.85 (16)
O3—S1—C1—C2	−174.83 (12)	C3—C4—C9—C14	−78.8 (2)
O2—S1—C1—C2	−44.96 (15)	C5—C4—C9—C14	99.67 (19)
C16—S1—C1—C2	69.33 (14)	C4—C9—C10—C11	177.73 (14)
C8—C1—C2—C7	−0.28 (16)	C14—C9—C10—C11	−55.7 (2)
S1—C1—C2—C7	−179.24 (12)	O3—S1—C16—C17	146.24 (12)
C8—C1—C2—C3	178.68 (17)	O2—S1—C16—C17	15.91 (14)
S1—C1—C2—C3	−0.3 (3)	C1—S1—C16—C17	−98.28 (13)
C7—C2—C3—C4	0.6 (2)	O3—S1—C16—C21	−34.28 (14)
C1—C2—C3—C4	−178.23 (16)	O2—S1—C16—C21	−164.62 (12)
C2—C3—C4—C5	−0.7 (2)	C1—S1—C16—C21	81.19 (13)
C2—C3—C4—C9	177.82 (13)	C21—C16—C17—C18	−0.8 (2)
C3—C4—C5—C6	0.2 (2)	S1—C16—C17—C18	178.65 (11)
C9—C4—C5—C6	−178.34 (15)	C16—C17—C18—C19	−0.3 (2)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—C22	179.37 (15)
C5—C6—C7—O1	178.77 (15)	C17—C18—C19—C20	1.1 (3)
C5—C6—C7—C2	−0.4 (2)	C22—C18—C19—C20	−178.58 (17)
C8—O1—C7—C6	−178.71 (16)	C18—C19—C20—C21	−0.8 (3)
C8—O1—C7—C2	0.58 (17)	C19—C20—C21—C16	−0.3 (3)
C3—C2—C7—C6	0.0 (2)	C17—C16—C21—C20	1.1 (2)
C1—C2—C7—C6	179.13 (15)	S1—C16—C21—C20	−178.35 (12)
C3—C2—C7—O1	−179.35 (13)	C9—C10—C11—C12	56.2 (2)
C1—C2—C7—O1	−0.18 (17)	C10—C11—C12—C13	−55.2 (2)
C2—C1—C8—O1	0.66 (17)	C11—C12—C13—C14	55.2 (2)
S1—C1—C8—O1	179.60 (11)	C4—C9—C14—C13	−177.83 (18)
C2—C1—C8—C15	−178.72 (18)	C10—C9—C14—C13	54.9 (2)
S1—C1—C8—C15	0.2 (3)	C12—C13—C14—C9	−55.4 (3)
C7—O1—C8—C1	−0.77 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2i	0.95	2.55	3.415 (2)	151
C13—H13B···Cg1ii	0.99	2.83	3.670 (2)	143
C19—H19···Cg2iii	0.95	2.85	3.705 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2i	0.95	2.55	3.415 (2)	151
C13—H13B⋯Cg1ii	0.99	2.83	3.670 (2)	143
C19—H19⋯Cg2iii	0.95	2.85	3.705 (2)	150

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