5-Cyclo-hexyl-2-(4-fluoro-phen-yl)-3-isopropyl-sulfonyl-1-benzofuran.

In the title compound, C(23)H(25)FO(2)S, the cyclo-hexyl ring adopts a chair conformation. The 4-fluoro-phenyl ring makes a dihedral angle of 50.74 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by inter-molecular C-H⋯π inter-actions.

Related literature

For the biological 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 2-aryl-5-cyclo­hexyl-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C23H25FO3S

M = 400.49

Monoclinic,

a = 16.2065 (3) Å

b = 8.4993 (2) Å

c = 15.4031 (3) Å

β = 110.411 (1)°

V = 1988.47 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 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 = 0.935, T max = 0.969

34421 measured reflections

4536 independent reflections

3857 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.05

4536 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.43 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/S160053681101097X/ez2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101097X/ez2240Isup2.hkl

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

C23H25FO3S	F(000) = 848
Mr = 400.49	Dx = 1.338 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9904 reflections
a = 16.2065 (3) Å	θ = 2.7–27.5°
b = 8.4993 (2) Å	µ = 0.19 mm−1
c = 15.4031 (3) Å	T = 173 K
β = 110.411 (1)°	Block, colourless
V = 1988.47 (7) Å3	0.35 × 0.25 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4536 independent reflections
Radiation source: rotating anode	3857 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.040
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.3°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→10
Tmin = 0.935, Tmax = 0.969	l = −19→19
34421 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.8589P] where P = (Fo2 + 2Fc2)/3
4536 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.43 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	0.19580 (2)	0.56351 (4)	0.11644 (2)	0.02585 (12)
F1	−0.06671 (7)	0.55451 (15)	0.39156 (8)	0.0526 (3)
O1	0.30601 (7)	0.43713 (13)	0.37816 (7)	0.0286 (2)
O2	0.12420 (7)	0.65463 (14)	0.12504 (8)	0.0355 (3)
O3	0.25519 (7)	0.63717 (14)	0.07757 (8)	0.0337 (3)
C1	0.26010 (9)	0.49468 (18)	0.22631 (10)	0.0250 (3)
C2	0.35310 (10)	0.45605 (17)	0.25534 (10)	0.0254 (3)
C3	0.41687 (10)	0.44682 (18)	0.21347 (10)	0.0271 (3)
H3	0.4025	0.4723	0.1498	0.032*
C4	0.50184 (10)	0.39963 (18)	0.26662 (11)	0.0288 (3)
C5	0.52195 (10)	0.3651 (2)	0.36117 (11)	0.0336 (4)
H5	0.5802	0.3333	0.3967	0.040*
C6	0.46071 (10)	0.3755 (2)	0.40410 (11)	0.0330 (3)
H6	0.4751	0.3522	0.4680	0.040*
C7	0.37701 (10)	0.42184 (18)	0.34923 (10)	0.0269 (3)
C8	0.23549 (10)	0.48094 (18)	0.30212 (10)	0.0262 (3)
C9	0.57531 (10)	0.38349 (19)	0.22780 (11)	0.0311 (3)
H9	0.6053	0.2810	0.2506	0.037*
C10	0.54480 (11)	0.3797 (3)	0.12306 (12)	0.0440 (4)
H10A	0.5145	0.4796	0.0978	0.053*
H10B	0.5022	0.2927	0.0996	0.053*
C11	0.62254 (12)	0.3564 (3)	0.08978 (14)	0.0464 (5)
H11A	0.6502	0.2530	0.1113	0.056*
H11B	0.6010	0.3567	0.0212	0.056*
C12	0.69027 (13)	0.4850 (3)	0.12594 (15)	0.0476 (5)
H12A	0.6644	0.5871	0.0989	0.057*
H12B	0.7413	0.4637	0.1064	0.057*
C13	0.72119 (13)	0.4951 (3)	0.23060 (16)	0.0555 (5)
H13A	0.7613	0.5862	0.2518	0.067*
H13B	0.7546	0.3988	0.2576	0.067*
C14	0.64422 (12)	0.5131 (2)	0.26502 (13)	0.0426 (4)
H14A	0.6161	0.6168	0.2454	0.051*
H14B	0.6666	0.5100	0.3336	0.051*
C15	0.15393 (10)	0.50362 (18)	0.32210 (10)	0.0274 (3)
C16	0.07583 (11)	0.4297 (2)	0.26997 (11)	0.0357 (4)
H16	0.0737	0.3676	0.2180	0.043*
C17	0.00085 (11)	0.4459 (2)	0.29324 (12)	0.0400 (4)
H17	−0.0527	0.3954	0.2580	0.048*
C18	0.00630 (11)	0.5370 (2)	0.36879 (12)	0.0360 (4)
C19	0.08251 (12)	0.6103 (2)	0.42288 (12)	0.0367 (4)
H19	0.0841	0.6712	0.4752	0.044*
C20	0.15689 (11)	0.5932 (2)	0.39912 (11)	0.0320 (3)
H20	0.2103	0.6428	0.4355	0.038*
C21	0.14993 (10)	0.3924 (2)	0.04907 (11)	0.0321 (3)
H21	0.1114	0.3382	0.0783	0.039*
C22	0.09234 (11)	0.4450 (2)	−0.04767 (11)	0.0408 (4)
H22A	0.1294	0.4911	−0.0795	0.061*
H22B	0.0499	0.5237	−0.0429	0.061*
H22C	0.0606	0.3541	−0.0828	0.061*
C23	0.22097 (13)	0.2779 (2)	0.04729 (13)	0.0449 (4)
H23A	0.1936	0.1838	0.0123	0.067*
H23B	0.2565	0.2482	0.1108	0.067*
H23C	0.2588	0.3278	0.0176	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.02457 (19)	0.0289 (2)	0.02323 (19)	0.00035 (14)	0.00727 (14)	0.00259 (14)
F1	0.0401 (6)	0.0691 (8)	0.0599 (7)	0.0072 (5)	0.0317 (5)	−0.0005 (6)
O1	0.0284 (5)	0.0351 (6)	0.0225 (5)	0.0022 (4)	0.0092 (4)	0.0014 (4)
O2	0.0306 (6)	0.0400 (6)	0.0352 (6)	0.0087 (5)	0.0105 (5)	0.0045 (5)
O3	0.0323 (6)	0.0383 (6)	0.0308 (6)	−0.0037 (5)	0.0114 (5)	0.0073 (5)
C1	0.0246 (7)	0.0265 (7)	0.0239 (7)	−0.0002 (6)	0.0083 (5)	−0.0001 (6)
C2	0.0259 (7)	0.0245 (7)	0.0237 (7)	−0.0011 (5)	0.0060 (6)	−0.0024 (6)
C3	0.0274 (7)	0.0289 (7)	0.0245 (7)	−0.0022 (6)	0.0085 (6)	−0.0026 (6)
C4	0.0254 (7)	0.0289 (7)	0.0309 (8)	−0.0024 (6)	0.0085 (6)	−0.0040 (6)
C5	0.0262 (7)	0.0378 (9)	0.0314 (8)	0.0009 (6)	0.0035 (6)	−0.0015 (7)
C6	0.0328 (8)	0.0373 (9)	0.0246 (7)	0.0018 (7)	0.0047 (6)	0.0008 (6)
C7	0.0276 (7)	0.0278 (7)	0.0259 (7)	−0.0010 (6)	0.0099 (6)	−0.0027 (6)
C8	0.0276 (7)	0.0255 (7)	0.0243 (7)	−0.0002 (6)	0.0075 (6)	−0.0010 (6)
C9	0.0269 (7)	0.0274 (8)	0.0387 (8)	0.0003 (6)	0.0109 (6)	0.0009 (7)
C10	0.0317 (8)	0.0627 (12)	0.0408 (9)	−0.0071 (8)	0.0168 (7)	−0.0154 (9)
C11	0.0415 (10)	0.0555 (12)	0.0514 (11)	−0.0043 (9)	0.0278 (8)	−0.0123 (9)
C12	0.0436 (10)	0.0474 (11)	0.0614 (12)	−0.0017 (8)	0.0304 (9)	0.0042 (10)
C13	0.0354 (10)	0.0700 (14)	0.0628 (13)	−0.0184 (10)	0.0193 (9)	−0.0085 (11)
C14	0.0360 (9)	0.0482 (10)	0.0440 (10)	−0.0148 (8)	0.0143 (8)	−0.0112 (8)
C15	0.0305 (7)	0.0289 (7)	0.0246 (7)	0.0011 (6)	0.0122 (6)	0.0019 (6)
C16	0.0345 (8)	0.0464 (10)	0.0280 (8)	−0.0034 (7)	0.0132 (7)	−0.0063 (7)
C17	0.0307 (8)	0.0544 (11)	0.0346 (9)	−0.0046 (8)	0.0110 (7)	−0.0023 (8)
C18	0.0333 (8)	0.0422 (9)	0.0387 (9)	0.0074 (7)	0.0204 (7)	0.0064 (7)
C19	0.0444 (9)	0.0350 (9)	0.0370 (9)	0.0030 (7)	0.0223 (7)	−0.0034 (7)
C20	0.0343 (8)	0.0330 (8)	0.0304 (8)	−0.0023 (7)	0.0135 (6)	−0.0033 (7)
C21	0.0332 (8)	0.0369 (8)	0.0255 (7)	−0.0078 (7)	0.0094 (6)	−0.0034 (7)
C22	0.0298 (8)	0.0606 (12)	0.0275 (8)	−0.0037 (8)	0.0044 (6)	−0.0036 (8)
C23	0.0535 (11)	0.0387 (10)	0.0366 (9)	0.0040 (8)	0.0084 (8)	−0.0087 (8)

S1—O2	1.4391 (11)	C11—H11B	0.9900
S1—O3	1.4417 (11)	C12—C13	1.515 (3)
S1—C1	1.7498 (15)	C12—H12A	0.9900
S1—C21	1.7910 (16)	C12—H12B	0.9900
F1—C18	1.3545 (18)	C13—C14	1.524 (3)
O1—C8	1.3722 (17)	C13—H13A	0.9900
O1—C7	1.3774 (17)	C13—H13B	0.9900
C1—C8	1.364 (2)	C14—H14A	0.9900
C1—C2	1.452 (2)	C14—H14B	0.9900
C2—C7	1.391 (2)	C15—C16	1.390 (2)
C2—C3	1.398 (2)	C15—C20	1.396 (2)
C3—C4	1.393 (2)	C16—C17	1.388 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.408 (2)	C17—C18	1.375 (3)
C4—C9	1.513 (2)	C17—H17	0.9500
C5—C6	1.374 (2)	C18—C19	1.375 (3)
C5—H5	0.9500	C19—C20	1.384 (2)
C6—C7	1.382 (2)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C8—C15	1.471 (2)	C21—C23	1.515 (2)
C9—C10	1.514 (2)	C21—C22	1.524 (2)
C9—C14	1.531 (2)	C21—H21	1.0000
C9—H9	1.0000	C22—H22A	0.9800
C10—C11	1.530 (2)	C22—H22B	0.9800
C10—H10A	0.9900	C22—H22C	0.9800
C10—H10B	0.9900	C23—H23A	0.9800
C11—C12	1.511 (3)	C23—H23B	0.9800
C11—H11A	0.9900	C23—H23C	0.9800
O2—S1—O3	118.75 (7)	C11—C12—H12B	109.4
O2—S1—C1	108.56 (7)	C13—C12—H12B	109.4
O3—S1—C1	106.75 (7)	H12A—C12—H12B	108.0
O2—S1—C21	107.78 (7)	C12—C13—C14	111.65 (17)
O3—S1—C21	108.32 (7)	C12—C13—H13A	109.3
C1—S1—C21	106.00 (7)	C14—C13—H13A	109.3
C8—O1—C7	106.89 (11)	C12—C13—H13B	109.3
C8—C1—C2	107.39 (13)	C14—C13—H13B	109.3
C8—C1—S1	127.10 (12)	H13A—C13—H13B	108.0
C2—C1—S1	125.27 (11)	C13—C14—C9	112.12 (16)
C7—C2—C3	119.02 (13)	C13—C14—H14A	109.2
C7—C2—C1	104.49 (13)	C9—C14—H14A	109.2
C3—C2—C1	136.49 (14)	C13—C14—H14B	109.2
C4—C3—C2	118.89 (14)	C9—C14—H14B	109.2
C4—C3—H3	120.6	H14A—C14—H14B	107.9
C2—C3—H3	120.6	C16—C15—C20	119.46 (14)
C3—C4—C5	119.52 (14)	C16—C15—C8	121.58 (14)
C3—C4—C9	123.13 (14)	C20—C15—C8	118.82 (14)
C5—C4—C9	117.35 (14)	C17—C16—C15	120.57 (15)
C6—C5—C4	122.60 (14)	C17—C16—H16	119.7
C6—C5—H5	118.7	C15—C16—H16	119.7
C4—C5—H5	118.7	C18—C17—C16	118.08 (16)
C5—C6—C7	116.35 (14)	C18—C17—H17	121.0
C5—C6—H6	121.8	C16—C17—H17	121.0
C7—C6—H6	121.8	F1—C18—C17	118.50 (16)
O1—C7—C6	125.56 (14)	F1—C18—C19	118.33 (15)
O1—C7—C2	110.82 (13)	C17—C18—C19	123.17 (16)
C6—C7—C2	123.60 (14)	C18—C19—C20	118.24 (15)
C1—C8—O1	110.41 (13)	C18—C19—H19	120.9
C1—C8—C15	136.08 (14)	C20—C19—H19	120.9
O1—C8—C15	113.50 (12)	C19—C20—C15	120.46 (15)
C4—C9—C10	114.42 (13)	C19—C20—H20	119.8
C4—C9—C14	111.02 (14)	C15—C20—H20	119.8
C10—C9—C14	109.81 (15)	C23—C21—C22	112.41 (14)
C4—C9—H9	107.1	C23—C21—S1	111.55 (11)
C10—C9—H9	107.1	C22—C21—S1	108.49 (12)
C14—C9—H9	107.1	C23—C21—H21	108.1
C9—C10—C11	111.03 (15)	C22—C21—H21	108.1
C9—C10—H10A	109.4	S1—C21—H21	108.1
C11—C10—H10A	109.4	C21—C22—H22A	109.5
C9—C10—H10B	109.4	C21—C22—H22B	109.5
C11—C10—H10B	109.4	H22A—C22—H22B	109.5
H10A—C10—H10B	108.0	C21—C22—H22C	109.5
C12—C11—C10	111.13 (16)	H22A—C22—H22C	109.5
C12—C11—H11A	109.4	H22B—C22—H22C	109.5
C10—C11—H11A	109.4	C21—C23—H23A	109.5
C12—C11—H11B	109.4	C21—C23—H23B	109.5
C10—C11—H11B	109.4	H23A—C23—H23B	109.5
H11A—C11—H11B	108.0	C21—C23—H23C	109.5
C11—C12—C13	111.19 (16)	H23A—C23—H23C	109.5
C11—C12—H12A	109.4	H23B—C23—H23C	109.5
C13—C12—H12A	109.4
O2—S1—C1—C8	20.02 (16)	C5—C4—C9—C10	164.58 (16)
O3—S1—C1—C8	149.13 (14)	C3—C4—C9—C14	109.38 (17)
C21—S1—C1—C8	−95.53 (15)	C5—C4—C9—C14	−70.45 (19)
O2—S1—C1—C2	−153.56 (13)	C4—C9—C10—C11	−177.68 (15)
O3—S1—C1—C2	−24.45 (15)	C14—C9—C10—C11	56.7 (2)
C21—S1—C1—C2	90.89 (14)	C9—C10—C11—C12	−57.9 (2)
C8—C1—C2—C7	−0.18 (17)	C10—C11—C12—C13	55.8 (2)
S1—C1—C2—C7	174.46 (11)	C11—C12—C13—C14	−53.9 (2)
C8—C1—C2—C3	179.77 (17)	C12—C13—C14—C9	54.0 (2)
S1—C1—C2—C3	−5.6 (3)	C4—C9—C14—C13	177.30 (16)
C7—C2—C3—C4	1.7 (2)	C10—C9—C14—C13	−55.2 (2)
C1—C2—C3—C4	−178.29 (16)	C1—C8—C15—C16	53.2 (3)
C2—C3—C4—C5	−1.1 (2)	O1—C8—C15—C16	−128.01 (16)
C2—C3—C4—C9	179.09 (14)	C1—C8—C15—C20	−131.11 (19)
C3—C4—C5—C6	0.1 (3)	O1—C8—C15—C20	47.7 (2)
C9—C4—C5—C6	179.98 (15)	C20—C15—C16—C17	0.8 (3)
C4—C5—C6—C7	0.2 (3)	C8—C15—C16—C17	176.42 (16)
C8—O1—C7—C6	−178.35 (15)	C15—C16—C17—C18	0.2 (3)
C8—O1—C7—C2	0.27 (17)	C16—C17—C18—F1	179.46 (16)
C5—C6—C7—O1	178.87 (15)	C16—C17—C18—C19	−1.1 (3)
C5—C6—C7—C2	0.4 (2)	F1—C18—C19—C20	−179.56 (15)
C3—C2—C7—O1	179.99 (13)	C17—C18—C19—C20	1.0 (3)
C1—C2—C7—O1	−0.06 (17)	C18—C19—C20—C15	0.0 (3)
C3—C2—C7—C6	−1.4 (2)	C16—C15—C20—C19	−0.9 (2)
C1—C2—C7—C6	178.59 (15)	C8—C15—C20—C19	−176.63 (15)
C2—C1—C8—O1	0.36 (17)	O2—S1—C21—C23	−172.18 (12)
S1—C1—C8—O1	−174.15 (11)	O3—S1—C21—C23	58.15 (14)
C2—C1—C8—C15	179.15 (17)	C1—S1—C21—C23	−56.11 (14)
S1—C1—C8—C15	4.6 (3)	O2—S1—C21—C22	63.47 (12)
C7—O1—C8—C1	−0.39 (17)	O3—S1—C21—C22	−66.20 (12)
C7—O1—C8—C15	−179.48 (12)	C1—S1—C21—C22	179.55 (11)
C3—C4—C9—C10	−15.6 (2)

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

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cgi	0.99	2.68	3.667 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cgi	0.99	2.68	3.667 (2)	172

Symmetry code: (i) .