5-Cyclo-hexyl-3-ethyl-sulfinyl-2-(3-fluoro-phen-yl)-1-benzo-furan.

In the title compound, C22H23FO2S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzo-furan ring system and the mean plane [r.m.s. deviation = 0.009 (2) Å] of the 3-fluoro-phenyl ring is 24.80 (4)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming chains along [10-1]. These chains are linked via C-H⋯F hydrogen bonds, forming a three-dimensional structure. There are also inter-planar inter-actions present involving the furan ring of the benzo-furan ring system and the 3-fluoro-phenyl ring [centroid-centroid distance = 3.728 (2) Å].

Related literature

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

Experimental

Crystal data

C22H23FO2S

M = 370.46

Monoclinic,

a = 15.1363 (5) Å

b = 15.9252 (6) Å

c = 10.6440 (6) Å

β = 133.053 (1)°

V = 1874.83 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.40 × 0.29 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.634, T max = 0.746

8392 measured reflections

3085 independent reflections

2842 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.074

S = 1.04

3085 reflections

237 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1045 (51%) Friedel pairs

Absolute structure parameter: 0.05 (7)

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/S1600536813023180/su2636sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023180/su2636Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023180/su2636Isup3.cml

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

C22H23FO2S	F(000) = 784
Mr = 370.46	Dx = 1.312 Mg m−3
Monoclinic, Cc	Melting point = 417–418 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.1363 (5) Å	Cell parameters from 3291 reflections
b = 15.9252 (6) Å	θ = 2.2–27.2°
c = 10.6440 (6) Å	µ = 0.20 mm−1
β = 133.053 (1)°	T = 173 K
V = 1874.83 (14) Å3	Block, colourless
Z = 4	0.40 × 0.29 × 0.19 mm

Bruker SMART APEXII CCD diffractometer	3085 independent reflections
Radiation source: rotating anode	2842 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.2°
φ and ω scans	h = −17→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→20
Tmin = 0.634, Tmax = 0.746	l = −12→13
8392 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0331P)2 + 0.634P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3085 reflections	Δρmax = 0.17 e Å−3
237 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 1045 (51%) Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (7)

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	0.58145 (5)	0.71011 (3)	0.55769 (7)	0.02664 (12)
F1	0.83575 (15)	0.34959 (9)	1.0261 (2)	0.0578 (4)
O1	0.60897 (13)	0.48023 (8)	0.44611 (19)	0.0295 (3)
O2	0.45182 (14)	0.73581 (10)	0.4371 (2)	0.0398 (4)
C1	0.58675 (18)	0.61762 (12)	0.4704 (3)	0.0256 (4)
C2	0.50850 (19)	0.59876 (12)	0.2895 (3)	0.0264 (4)
C3	0.42931 (19)	0.64416 (13)	0.1364 (3)	0.0272 (4)
H3	0.4163	0.7023	0.1383	0.033*
C4	0.36966 (19)	0.60334 (14)	−0.0189 (3)	0.0312 (5)
C5	0.3890 (2)	0.51695 (14)	−0.0187 (3)	0.0333 (5)
H5	0.3476	0.4894	−0.1254	0.040*
C6	0.4665 (2)	0.47071 (14)	0.1317 (3)	0.0318 (5)
H6	0.4784	0.4122	0.1306	0.038*
C7	0.52538 (18)	0.51362 (13)	0.2826 (3)	0.0280 (5)
C8	0.64494 (19)	0.54532 (13)	0.5576 (3)	0.0276 (4)
C9	0.2871 (2)	0.65312 (15)	−0.1847 (3)	0.0336 (5)
H9	0.2812	0.7112	−0.1553	0.040*
C10	0.1585 (2)	0.61773 (18)	−0.3167 (3)	0.0428 (6)
H10A	0.1236	0.6148	−0.2651	0.051*
H10B	0.1611	0.5601	−0.3488	0.051*
C11	0.0782 (2)	0.6728 (2)	−0.4780 (3)	0.0504 (7)
H11A	−0.0030	0.6471	−0.5636	0.061*
H11B	0.0688	0.7288	−0.4477	0.061*
C12	0.1316 (2)	0.68312 (19)	−0.5568 (3)	0.0516 (7)
H12A	0.0810	0.7227	−0.6548	0.062*
H12B	0.1305	0.6282	−0.6015	0.062*
C13	0.2609 (2)	0.71598 (18)	−0.4262 (3)	0.0489 (7)
H13A	0.2610	0.7741	−0.3931	0.059*
H13B	0.2952	0.7172	−0.4788	0.059*
C14	0.3392 (2)	0.66032 (16)	−0.2663 (3)	0.0399 (6)
H14A	0.3452	0.6036	−0.2981	0.048*
H14B	0.4218	0.6841	−0.1814	0.048*
C15	0.73455 (18)	0.52553 (13)	0.7407 (3)	0.0284 (4)
C16	0.8090 (2)	0.58784 (14)	0.8612 (3)	0.0367 (5)
H16	0.8054	0.6430	0.8240	0.044*
C17	0.8882 (2)	0.57015 (16)	1.0350 (3)	0.0449 (6)
H17	0.9367	0.6138	1.1160	0.054*
C18	0.8980 (2)	0.49001 (16)	1.0925 (3)	0.0430 (6)
H18	0.9524	0.4775	1.2118	0.052*
C19	0.8258 (2)	0.42899 (14)	0.9703 (3)	0.0388 (6)
C20	0.7442 (2)	0.44338 (14)	0.7971 (3)	0.0335 (5)
H20	0.6957	0.3992	0.7174	0.040*
C21	0.6568 (2)	0.78020 (13)	0.5232 (3)	0.0344 (5)
H21A	0.7411	0.7613	0.5918	0.041*
H21B	0.6149	0.7796	0.4003	0.041*
C22	0.6564 (3)	0.86840 (15)	0.5760 (4)	0.0450 (6)
H22A	0.6982	0.8687	0.6977	0.067*
H22B	0.5728	0.8873	0.5062	0.067*
H22C	0.6981	0.9063	0.5581	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0314 (3)	0.0225 (2)	0.0276 (2)	−0.0004 (2)	0.0208 (2)	−0.0017 (2)
F1	0.0739 (11)	0.0365 (8)	0.0653 (10)	0.0167 (7)	0.0484 (10)	0.0247 (7)
O1	0.0322 (8)	0.0221 (7)	0.0342 (8)	−0.0004 (6)	0.0227 (7)	−0.0020 (6)
O2	0.0349 (9)	0.0331 (8)	0.0494 (10)	0.0030 (7)	0.0280 (9)	−0.0051 (7)
C1	0.0253 (10)	0.0232 (10)	0.0292 (10)	−0.0023 (8)	0.0190 (9)	−0.0019 (8)
C2	0.0274 (11)	0.0246 (10)	0.0329 (11)	−0.0038 (8)	0.0229 (10)	−0.0056 (9)
C3	0.0276 (11)	0.0244 (11)	0.0286 (11)	−0.0008 (8)	0.0188 (9)	−0.0029 (8)
C4	0.0282 (11)	0.0370 (12)	0.0308 (11)	−0.0022 (9)	0.0210 (10)	−0.0052 (9)
C5	0.0356 (13)	0.0347 (12)	0.0362 (13)	−0.0107 (10)	0.0271 (11)	−0.0141 (10)
C6	0.0369 (12)	0.0269 (11)	0.0434 (13)	−0.0050 (9)	0.0320 (11)	−0.0086 (10)
C7	0.0275 (11)	0.0254 (10)	0.0363 (12)	−0.0016 (8)	0.0238 (10)	−0.0012 (9)
C8	0.0268 (11)	0.0244 (10)	0.0339 (11)	−0.0031 (8)	0.0216 (10)	−0.0020 (9)
C9	0.0346 (12)	0.0344 (12)	0.0278 (11)	−0.0030 (9)	0.0197 (10)	−0.0071 (9)
C10	0.0324 (13)	0.0575 (16)	0.0352 (13)	−0.0044 (11)	0.0218 (11)	−0.0027 (11)
C11	0.0326 (13)	0.0697 (18)	0.0335 (15)	0.0013 (13)	0.0165 (12)	0.0023 (12)
C12	0.0475 (16)	0.0666 (18)	0.0285 (13)	−0.0011 (13)	0.0213 (13)	−0.0014 (13)
C13	0.0506 (16)	0.0627 (18)	0.0363 (14)	−0.0076 (13)	0.0308 (13)	−0.0033 (12)
C14	0.0368 (14)	0.0499 (14)	0.0327 (12)	−0.0079 (11)	0.0236 (11)	−0.0043 (11)
C15	0.0251 (11)	0.0269 (11)	0.0344 (12)	0.0033 (8)	0.0208 (10)	0.0044 (9)
C16	0.0297 (12)	0.0310 (12)	0.0370 (12)	−0.0006 (10)	0.0178 (11)	0.0060 (10)
C17	0.0337 (13)	0.0430 (14)	0.0369 (14)	−0.0021 (10)	0.0159 (12)	−0.0002 (11)
C18	0.0364 (14)	0.0501 (15)	0.0340 (13)	0.0107 (11)	0.0207 (12)	0.0121 (11)
C19	0.0394 (14)	0.0333 (13)	0.0502 (15)	0.0150 (10)	0.0331 (13)	0.0181 (11)
C20	0.0358 (13)	0.0259 (11)	0.0430 (13)	0.0042 (9)	0.0285 (12)	0.0030 (9)
C21	0.0406 (13)	0.0272 (11)	0.0447 (13)	−0.0064 (9)	0.0328 (12)	−0.0050 (10)
C22	0.0591 (17)	0.0266 (12)	0.0598 (16)	−0.0072 (11)	0.0447 (15)	−0.0078 (11)

S1—O2	1.4920 (16)	C11—H11A	0.9900
S1—C1	1.772 (2)	C11—H11B	0.9900
S1—C21	1.804 (2)	C12—C13	1.524 (4)
F1—C19	1.361 (3)	C12—H12A	0.9900
O1—C8	1.377 (2)	C12—H12B	0.9900
O1—C7	1.381 (3)	C13—C14	1.527 (4)
C1—C8	1.359 (3)	C13—H13A	0.9900
C1—C2	1.445 (3)	C13—H13B	0.9900
C2—C7	1.391 (3)	C14—H14A	0.9900
C2—C3	1.396 (3)	C14—H14B	0.9900
C3—C4	1.390 (3)	C15—C16	1.388 (3)
C3—H3	0.9500	C15—C20	1.405 (3)
C4—C5	1.406 (3)	C16—C17	1.382 (3)
C4—C9	1.514 (3)	C16—H16	0.9500
C5—C6	1.385 (3)	C17—C18	1.379 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.373 (3)	C18—C19	1.375 (4)
C6—H6	0.9500	C18—H18	0.9500
C8—C15	1.459 (3)	C19—C20	1.367 (3)
C9—C14	1.526 (3)	C20—H20	0.9500
C9—C10	1.531 (3)	C21—C22	1.514 (3)
C9—H9	1.0000	C21—H21A	0.9900
C10—C11	1.531 (4)	C21—H21B	0.9900
C10—H10A	0.9900	C22—H22A	0.9800
C10—H10B	0.9900	C22—H22B	0.9800
C11—C12	1.519 (4)	C22—H22C	0.9800
O2—S1—C1	106.30 (10)	C11—C12—H12A	109.3
O2—S1—C21	107.36 (11)	C13—C12—H12A	109.3
C1—S1—C21	98.42 (10)	C11—C12—H12B	109.3
C8—O1—C7	106.23 (15)	C13—C12—H12B	109.3
C8—C1—C2	107.06 (18)	H12A—C12—H12B	107.9
C8—C1—S1	125.93 (17)	C12—C13—C14	110.7 (2)
C2—C1—S1	125.60 (16)	C12—C13—H13A	109.5
C7—C2—C3	119.02 (19)	C14—C13—H13A	109.5
C7—C2—C1	105.08 (18)	C12—C13—H13B	109.5
C3—C2—C1	135.88 (18)	C14—C13—H13B	109.5
C4—C3—C2	119.28 (19)	H13A—C13—H13B	108.1
C4—C3—H3	120.4	C9—C14—C13	111.6 (2)
C2—C3—H3	120.4	C9—C14—H14A	109.3
C3—C4—C5	119.4 (2)	C13—C14—H14A	109.3
C3—C4—C9	119.34 (19)	C9—C14—H14B	109.3
C5—C4—C9	121.28 (19)	C13—C14—H14B	109.3
C6—C5—C4	122.20 (19)	H14A—C14—H14B	108.0
C6—C5—H5	118.9	C16—C15—C20	119.3 (2)
C4—C5—H5	118.9	C16—C15—C8	120.53 (19)
C7—C6—C5	116.7 (2)	C20—C15—C8	120.2 (2)
C7—C6—H6	121.7	C17—C16—C15	120.4 (2)
C5—C6—H6	121.7	C17—C16—H16	119.8
C6—C7—O1	125.95 (18)	C15—C16—H16	119.8
C6—C7—C2	123.4 (2)	C18—C17—C16	121.0 (2)
O1—C7—C2	110.60 (17)	C18—C17—H17	119.5
C1—C8—O1	111.02 (19)	C16—C17—H17	119.5
C1—C8—C15	132.3 (2)	C19—C18—C17	117.3 (2)
O1—C8—C15	116.66 (18)	C19—C18—H18	121.3
C4—C9—C14	111.50 (19)	C17—C18—H18	121.3
C4—C9—C10	113.44 (19)	F1—C19—C20	118.3 (2)
C14—C9—C10	109.39 (18)	F1—C19—C18	117.6 (2)
C4—C9—H9	107.4	C20—C19—C18	124.1 (2)
C14—C9—H9	107.4	C19—C20—C15	117.8 (2)
C10—C9—H9	107.4	C19—C20—H20	121.1
C9—C10—C11	110.9 (2)	C15—C20—H20	121.1
C9—C10—H10A	109.5	C22—C21—S1	109.59 (16)
C11—C10—H10A	109.5	C22—C21—H21A	109.8
C9—C10—H10B	109.5	S1—C21—H21A	109.8
C11—C10—H10B	109.5	C22—C21—H21B	109.8
H10A—C10—H10B	108.0	S1—C21—H21B	109.8
C12—C11—C10	111.5 (2)	H21A—C21—H21B	108.2
C12—C11—H11A	109.3	C21—C22—H22A	109.5
C10—C11—H11A	109.3	C21—C22—H22B	109.5
C12—C11—H11B	109.3	H22A—C22—H22B	109.5
C10—C11—H11B	109.3	C21—C22—H22C	109.5
H11A—C11—H11B	108.0	H22A—C22—H22C	109.5
C11—C12—C13	111.7 (2)	H22B—C22—H22C	109.5
O2—S1—C1—C8	−131.38 (19)	C3—C4—C9—C14	111.2 (2)
C21—S1—C1—C8	117.7 (2)	C5—C4—C9—C14	−67.5 (3)
O2—S1—C1—C2	33.2 (2)	C3—C4—C9—C10	−124.7 (2)
C21—S1—C1—C2	−77.72 (19)	C5—C4—C9—C10	56.6 (3)
C8—C1—C2—C7	0.9 (2)	C4—C9—C10—C11	177.6 (2)
S1—C1—C2—C7	−166.14 (15)	C14—C9—C10—C11	−57.3 (3)
C8—C1—C2—C3	−177.8 (2)	C9—C10—C11—C12	56.1 (3)
S1—C1—C2—C3	15.2 (4)	C10—C11—C12—C13	−54.4 (3)
C7—C2—C3—C4	−0.2 (3)	C11—C12—C13—C14	54.2 (3)
C1—C2—C3—C4	178.4 (2)	C4—C9—C14—C13	−175.7 (2)
C2—C3—C4—C5	0.8 (3)	C10—C9—C14—C13	58.0 (3)
C2—C3—C4—C9	−177.90 (19)	C12—C13—C14—C9	−56.6 (3)
C3—C4—C5—C6	−0.4 (3)	C1—C8—C15—C16	−24.8 (4)
C9—C4—C5—C6	178.3 (2)	O1—C8—C15—C16	155.5 (2)
C4—C5—C6—C7	−0.8 (3)	C1—C8—C15—C20	153.6 (2)
C5—C6—C7—O1	−177.80 (19)	O1—C8—C15—C20	−26.1 (3)
C5—C6—C7—C2	1.5 (3)	C20—C15—C16—C17	−2.7 (3)
C8—O1—C7—C6	179.5 (2)	C8—C15—C16—C17	175.7 (2)
C8—O1—C7—C2	0.2 (2)	C15—C16—C17—C18	2.1 (4)
C3—C2—C7—C6	−1.0 (3)	C16—C17—C18—C19	−0.1 (4)
C1—C2—C7—C6	179.99 (19)	C17—C18—C19—F1	179.4 (2)
C3—C2—C7—O1	178.33 (18)	C17—C18—C19—C20	−1.2 (4)
C1—C2—C7—O1	−0.6 (2)	F1—C19—C20—C15	179.94 (19)
C2—C1—C8—O1	−0.8 (2)	C18—C19—C20—C15	0.6 (3)
S1—C1—C8—O1	166.15 (14)	C16—C15—C20—C19	1.4 (3)
C2—C1—C8—C15	179.5 (2)	C8—C15—C20—C19	−177.0 (2)
S1—C1—C8—C15	−13.5 (4)	O2—S1—C21—C22	65.6 (2)
C7—O1—C8—C1	0.4 (2)	C1—S1—C21—C22	175.71 (18)
C7—O1—C8—C15	−179.85 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2i	0.95	2.54	3.291 (3)	136
C3—H3···F1ii	0.95	2.54	3.438 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2i	0.95	2.54	3.291 (3)	136
C3—H3⋯F1ii	0.95	2.54	3.438 (3)	159

Symmetry codes: (i) ; (ii) .