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

In the title compound, C21H21FO2S, the cyclo-hexyl ring adopts a chair conformation. The 2-fluoro-benzene ring makes a dihedral angle of 38.68 (6)° with the mean plane [r.m.s. deviation = 0.018 (2) Å] of the benzo-furan fragment. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimers, which are further packed into stacks along the c axis by C-H⋯O hydrogen bonds. In addition, the stacked mol-ecules exhibit S⋯O contacts [3.1733 (13) Å] involving the sulfinyl groups. The F atom is disordered over two positions, with site-occupancy factors of 0.961 (3) and 0.039 (3).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008 ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C21H21FO2S

M = 356.44

Monoclinic,

a = 33.0231 (12) Å

b = 5.6347 (2) Å

c = 19.2200 (6) Å

β = 95.855 (2)°

V = 3557.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.31 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.545, T max = 0.746

29435 measured reflections

4455 independent reflections

3455 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 1.07

4455 reflections

237 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.33 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012701/tk5225sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012701/tk5225Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012701/tk5225Isup3.cml

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

C21H21FO2S	F(000) = 1504
Mr = 356.44	Dx = 1.331 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7608 reflections
a = 33.0231 (12) Å	θ = 2.4–27.9°
b = 5.6347 (2) Å	µ = 0.20 mm−1
c = 19.2200 (6) Å	T = 173 K
β = 95.855 (2)°	Block, colourless
V = 3557.7 (2) Å3	0.31 × 0.15 × 0.09 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Radiation source: rotating anode	3455 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.066
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −44→42
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −5→7
Tmin = 0.545, Tmax = 0.746	l = −25→25
29435 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.122	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0503P)2 + 2.7846P] where P = (Fo2 + 2Fc2)/3
4455 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.36 e Å−3
14 restraints	Δρmin = −0.33 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	Occ. (<1)
S1	0.206366 (12)	0.27237 (7)	0.42614 (2)	0.02355 (12)
O1	0.11688 (4)	0.5340 (3)	0.29615 (6)	0.0347 (3)
O2	0.21653 (4)	0.4453 (2)	0.48408 (6)	0.0320 (3)
C1	0.16017 (5)	0.3784 (3)	0.38215 (8)	0.0233 (3)
C2	0.12801 (5)	0.4947 (3)	0.41447 (9)	0.0251 (4)
C3	0.11880 (5)	0.5338 (3)	0.48284 (9)	0.0271 (4)
H3	0.1356	0.4687	0.5212	0.033*
C4	0.08520 (6)	0.6673 (4)	0.49437 (9)	0.0340 (4)
C5	0.06078 (7)	0.7595 (4)	0.43703 (11)	0.0494 (6)
H5	0.0377	0.8519	0.4454	0.059*
C6	0.06884 (7)	0.7218 (4)	0.36850 (11)	0.0497 (6)
H6	0.0519	0.7849	0.3300	0.060*
C7	0.10277 (5)	0.5879 (4)	0.35935 (9)	0.0330 (4)
C8	0.15236 (5)	0.4084 (3)	0.31233 (8)	0.0252 (4)
C9	0.07601 (6)	0.7166 (4)	0.56872 (10)	0.0358 (4)
H9	0.0931	0.6047	0.5996	0.043*
C10	0.03215 (7)	0.6704 (5)	0.58103 (12)	0.0508 (6)
H10A	0.0251	0.5041	0.5685	0.061*
H10B	0.0141	0.7755	0.5504	0.061*
C11	0.02494 (8)	0.7145 (5)	0.65731 (13)	0.0620 (8)
H11A	−0.0042	0.6906	0.6631	0.074*
H11B	0.0409	0.5990	0.6877	0.074*
C12	0.03733 (7)	0.9641 (5)	0.67931 (12)	0.0505 (6)
H12A	0.0194	1.0792	0.6522	0.061*
H12B	0.0338	0.9858	0.7295	0.061*
C13	0.08082 (7)	1.0129 (5)	0.66758 (11)	0.0504 (6)
H13A	0.0990	0.9109	0.6990	0.061*
H13B	0.0874	1.1804	0.6794	0.061*
C14	0.08855 (7)	0.9658 (4)	0.59173 (11)	0.0465 (5)
H14A	0.0731	1.0822	0.5609	0.056*
H14B	0.1179	0.9881	0.5868	0.056*
C15	0.17462 (5)	0.3439 (3)	0.25303 (8)	0.0263 (4)
C16A	0.19517 (6)	0.1306 (3)	0.25044 (9)	0.0301 (4)	0.961 (3)
F1A	0.19125 (4)	−0.0328 (2)	0.30066 (6)	0.0405 (4)	0.961 (3)
C16B	0.19517 (6)	0.1306 (3)	0.25044 (9)	0.0301 (4)	0.04
H16B	0.1930	0.0181	0.2867	0.036*	0.039 (3)
C17	0.21859 (6)	0.0748 (4)	0.19744 (10)	0.0370 (5)
H17	0.2329	−0.0714	0.1979	0.044*
C18	0.22086 (6)	0.2346 (4)	0.14361 (10)	0.0383 (5)
H18	0.2371	0.1992	0.1068	0.046*
C19	0.19974 (6)	0.4449 (4)	0.14305 (9)	0.0374 (5)
H19	0.2010	0.5530	0.1054	0.045*
C20A	0.17669 (6)	0.4997 (4)	0.19703 (9)	0.0317 (4)	0.961 (3)
H20A	0.1621	0.6452	0.1960	0.038*	0.961 (3)
C20B	0.17669 (6)	0.4997 (4)	0.19703 (9)	0.0317 (4)	0.04
F1B	0.1515 (6)	0.680 (3)	0.1832 (13)	0.031 (7)	0.039 (3)
C21	0.18645 (6)	0.0135 (3)	0.46404 (10)	0.0360 (4)
H21A	0.2084	−0.0696	0.4923	0.054*
H21B	0.1746	−0.0918	0.4268	0.054*
H21C	0.1654	0.0599	0.4938	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0256 (2)	0.0259 (2)	0.0196 (2)	0.00267 (16)	0.00441 (15)	0.00009 (16)
O1	0.0323 (7)	0.0526 (8)	0.0196 (6)	0.0133 (6)	0.0049 (5)	0.0022 (6)
O2	0.0346 (7)	0.0348 (7)	0.0257 (6)	0.0027 (5)	−0.0020 (5)	−0.0065 (5)
C1	0.0271 (8)	0.0246 (8)	0.0186 (8)	0.0012 (7)	0.0045 (6)	−0.0007 (6)
C2	0.0257 (8)	0.0292 (9)	0.0209 (8)	0.0016 (7)	0.0054 (6)	0.0005 (7)
C3	0.0263 (8)	0.0339 (9)	0.0215 (8)	0.0018 (7)	0.0046 (7)	0.0008 (7)
C4	0.0352 (10)	0.0427 (11)	0.0254 (9)	0.0066 (8)	0.0096 (8)	−0.0003 (8)
C5	0.0427 (12)	0.0707 (16)	0.0366 (11)	0.0285 (11)	0.0126 (9)	0.0036 (11)
C6	0.0448 (12)	0.0762 (16)	0.0283 (10)	0.0309 (11)	0.0047 (9)	0.0060 (10)
C7	0.0325 (10)	0.0469 (11)	0.0203 (9)	0.0098 (8)	0.0063 (7)	0.0005 (8)
C8	0.0259 (8)	0.0285 (9)	0.0214 (8)	0.0027 (7)	0.0033 (6)	−0.0007 (7)
C9	0.0378 (10)	0.0461 (11)	0.0253 (9)	0.0097 (9)	0.0110 (8)	−0.0015 (8)
C10	0.0497 (13)	0.0640 (15)	0.0423 (12)	−0.0144 (11)	0.0225 (10)	−0.0213 (11)
C11	0.0598 (15)	0.0855 (19)	0.0462 (13)	−0.0247 (14)	0.0324 (12)	−0.0241 (13)
C12	0.0426 (12)	0.0723 (16)	0.0386 (12)	0.0047 (11)	0.0134 (10)	−0.0210 (11)
C13	0.0461 (12)	0.0668 (16)	0.0399 (12)	−0.0060 (11)	0.0113 (10)	−0.0195 (11)
C14	0.0444 (12)	0.0585 (14)	0.0390 (12)	−0.0084 (10)	0.0163 (9)	−0.0109 (10)
C15	0.0283 (9)	0.0329 (9)	0.0180 (8)	−0.0016 (7)	0.0037 (6)	−0.0032 (7)
C16A	0.0364 (10)	0.0315 (10)	0.0227 (9)	−0.0017 (8)	0.0044 (7)	−0.0041 (7)
F1A	0.0590 (8)	0.0315 (6)	0.0326 (7)	0.0058 (5)	0.0117 (5)	0.0008 (5)
C16B	0.0364 (10)	0.0315 (10)	0.0227 (9)	−0.0017 (8)	0.0044 (7)	−0.0041 (7)
C17	0.0361 (10)	0.0422 (11)	0.0336 (10)	0.0015 (8)	0.0071 (8)	−0.0124 (9)
C18	0.0362 (10)	0.0545 (13)	0.0255 (9)	−0.0047 (9)	0.0096 (8)	−0.0142 (9)
C19	0.0396 (11)	0.0545 (13)	0.0187 (9)	−0.0068 (9)	0.0059 (8)	0.0012 (8)
C20A	0.0335 (10)	0.0391 (11)	0.0223 (9)	0.0002 (8)	0.0025 (7)	0.0007 (8)
C20B	0.0335 (10)	0.0391 (11)	0.0223 (9)	0.0002 (8)	0.0025 (7)	0.0007 (8)
F1B	0.030 (10)	0.036 (11)	0.028 (10)	−0.002 (8)	0.006 (7)	0.000 (8)
C21	0.0427 (11)	0.0311 (10)	0.0350 (10)	0.0002 (8)	0.0070 (9)	0.0103 (8)

S1—O2	1.4921 (13)	C11—C12	1.513 (3)
S1—C1	1.7708 (17)	C11—H11A	0.9900
S1—C21	1.7856 (19)	C11—H11B	0.9900
S1—O2i	3.1733 (13)	C12—C13	1.502 (3)
O1—C8	1.377 (2)	C12—H12A	0.9900
O1—C7	1.379 (2)	C12—H12B	0.9900
C1—C8	1.351 (2)	C13—C14	1.529 (3)
C1—C2	1.442 (2)	C13—H13A	0.9900
C2—C7	1.383 (2)	C13—H13B	0.9900
C2—C3	1.396 (2)	C14—H14A	0.9900
C3—C4	1.377 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—C16A	1.384 (3)
C4—C5	1.398 (3)	C15—C20A	1.396 (2)
C4—C9	1.516 (2)	C16A—F1A	1.3495 (19)
C5—C6	1.387 (3)	C16A—C17	1.377 (2)
C5—H5	0.9500	C17—C18	1.380 (3)
C6—C7	1.377 (3)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.374 (3)
C8—C15	1.464 (2)	C18—H18	0.9500
C9—C10	1.514 (3)	C19—C20A	1.383 (3)
C9—C14	1.517 (3)	C19—H19	0.9500
C9—H9	1.0000	C20A—H20A	0.9500
C10—C11	1.529 (3)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800
O2—S1—C1	104.66 (7)	C12—C11—H11B	109.5
O2—S1—C21	107.05 (9)	C10—C11—H11B	109.5
C1—S1—C21	97.77 (9)	H11A—C11—H11B	108.1
O2—S1—O2i	74.92 (6)	C13—C12—C11	111.33 (19)
C1—S1—O2i	173.96 (6)	C13—C12—H12A	109.4
C21—S1—O2i	76.76 (7)	C11—C12—H12A	109.4
C8—O1—C7	105.70 (13)	C13—C12—H12B	109.4
C8—C1—C2	107.27 (15)	C11—C12—H12B	109.4
C8—C1—S1	125.75 (13)	H12A—C12—H12B	108.0
C2—C1—S1	125.75 (12)	C12—C13—C14	111.50 (18)
C7—C2—C3	119.27 (15)	C12—C13—H13A	109.3
C7—C2—C1	104.79 (14)	C14—C13—H13A	109.3
C3—C2—C1	135.90 (16)	C12—C13—H13B	109.3
C4—C3—C2	119.62 (16)	C14—C13—H13B	109.3
C4—C3—H3	120.2	H13A—C13—H13B	108.0
C2—C3—H3	120.2	C9—C14—C13	111.81 (19)
C3—C4—C5	119.06 (17)	C9—C14—H14A	109.3
C3—C4—C9	119.58 (17)	C13—C14—H14A	109.3
C5—C4—C9	121.34 (17)	C9—C14—H14B	109.3
C6—C5—C4	122.73 (18)	C13—C14—H14B	109.3
C6—C5—H5	118.6	H14A—C14—H14B	107.9
C4—C5—H5	118.6	C16A—C15—C20A	117.12 (15)
C7—C6—C5	116.29 (19)	C16A—C15—C8	122.04 (16)
C7—C6—H6	121.9	C20A—C15—C8	120.82 (16)
C5—C6—H6	121.9	F1A—C16A—C17	118.39 (17)
C6—C7—O1	125.86 (17)	F1A—C16A—C15	118.93 (15)
C6—C7—C2	123.02 (17)	C17—C16A—C15	122.65 (17)
O1—C7—C2	111.09 (15)	C16A—C17—C18	118.91 (19)
C1—C8—O1	111.12 (14)	C16A—C17—H17	120.5
C1—C8—C15	133.03 (16)	C18—C17—H17	120.5
O1—C8—C15	115.78 (14)	C19—C18—C17	120.16 (17)
C10—C9—C4	113.72 (17)	C19—C18—H18	119.9
C10—C9—C14	110.52 (17)	C17—C18—H18	119.9
C4—C9—C14	111.67 (17)	C18—C19—C20A	120.30 (18)
C10—C9—H9	106.8	C18—C19—H19	119.8
C4—C9—H9	106.8	C20A—C19—H19	119.8
C14—C9—H9	106.8	C19—C20A—C15	120.78 (18)
C9—C10—C11	111.53 (18)	C19—C20A—H20A	119.6
C9—C10—H10A	109.3	C15—C20A—H20A	119.6
C11—C10—H10A	109.3	S1—C21—H21A	109.5
C9—C10—H10B	109.3	S1—C21—H21B	109.5
C11—C10—H10B	109.3	H21A—C21—H21B	109.5
H10A—C10—H10B	108.0	S1—C21—H21C	109.5
C12—C11—C10	110.8 (2)	H21A—C21—H21C	109.5
C12—C11—H11A	109.5	H21B—C21—H21C	109.5
C10—C11—H11A	109.5
O2—S1—C1—C8	131.23 (16)	C7—O1—C8—C15	−176.16 (16)
C21—S1—C1—C8	−118.80 (17)	C3—C4—C9—C10	−132.0 (2)
O2—S1—C1—C2	−34.53 (17)	C5—C4—C9—C10	49.6 (3)
C21—S1—C1—C2	75.45 (16)	C3—C4—C9—C14	102.1 (2)
C8—C1—C2—C7	−0.1 (2)	C5—C4—C9—C14	−76.3 (3)
S1—C1—C2—C7	167.87 (14)	C4—C9—C10—C11	178.0 (2)
C8—C1—C2—C3	−178.0 (2)	C14—C9—C10—C11	−55.5 (3)
S1—C1—C2—C3	−10.0 (3)	C9—C10—C11—C12	56.3 (3)
C7—C2—C3—C4	−1.0 (3)	C10—C11—C12—C13	−55.9 (3)
C1—C2—C3—C4	176.7 (2)	C11—C12—C13—C14	55.2 (3)
C2—C3—C4—C5	0.5 (3)	C10—C9—C14—C13	54.5 (3)
C2—C3—C4—C9	−177.98 (17)	C4—C9—C14—C13	−177.83 (17)
C3—C4—C5—C6	0.2 (4)	C12—C13—C14—C9	−54.7 (3)
C9—C4—C5—C6	178.6 (2)	C1—C8—C15—C16A	39.3 (3)
C4—C5—C6—C7	−0.3 (4)	O1—C8—C15—C16A	−143.89 (17)
C5—C6—C7—O1	−178.3 (2)	C1—C8—C15—C20A	−139.2 (2)
C5—C6—C7—C2	−0.2 (4)	O1—C8—C15—C20A	37.6 (2)
C8—O1—C7—C6	176.9 (2)	C20A—C15—C16A—F1A	−174.72 (16)
C8—O1—C7—C2	−1.4 (2)	C8—C15—C16A—F1A	6.7 (3)
C3—C2—C7—C6	0.9 (3)	C20A—C15—C16A—C17	3.3 (3)
C1—C2—C7—C6	−177.5 (2)	C8—C15—C16A—C17	−175.27 (17)
C3—C2—C7—O1	179.23 (16)	F1A—C16A—C17—C18	176.19 (17)
C1—C2—C7—O1	0.9 (2)	C15—C16A—C17—C18	−1.9 (3)
C2—C1—C8—O1	−0.8 (2)	C16A—C17—C18—C19	−0.5 (3)
S1—C1—C8—O1	−168.73 (13)	C17—C18—C19—C20A	1.2 (3)
C2—C1—C8—C15	176.11 (19)	C18—C19—C20A—C15	0.4 (3)
S1—C1—C8—C15	8.2 (3)	C16A—C15—C20A—C19	−2.5 (3)
C7—O1—C8—C1	1.3 (2)	C8—C15—C20A—C19	176.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ii	0.95	2.44	3.220 (2)	140
C21—H21A···O2i	0.98	2.57	3.265 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.95	2.44	3.220 (2)	140
C21—H21A⋯O2ii	0.98	2.57	3.265 (2)	128

Symmetry codes: (i) ; (ii) .