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

In the title compound, C21H21FO2S, the cyclo-hexyl ring adopts a chair conformation. The 3-fluoro-phenyl ring makes a dihedral angle of 83.16 (4)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo-furan ring system. In the crystal, mol-ecules are linked by pairs of C-H⋯π inter-actions into inversion dimers, which are further packed into stacks along the a-axis direction by C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C21H21FO2S

M = 356.44

Triclinic,

a = 8.9147 (1) Å

b = 10.1270 (2) Å

c = 10.5101 (2) Å

α = 90.376 (1)°

β = 110.407 (1)°

γ = 97.439 (1)°

V = 880.44 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.33 × 0.31 × 0.29 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.692, T max = 0.746

19435 measured reflections

4369 independent reflections

3897 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.04

4369 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.41 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) global, I. DOI: 10.1107/S160053681301475X/bx2442sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301475X/bx2442Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301475X/bx2442Isup3.cml

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

C21H21FO2S	Z = 2
Mr = 356.44	F(000) = 376
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Melting point = 403–404 K
a = 8.9147 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1270 (2) Å	Cell parameters from 9475 reflections
c = 10.5101 (2) Å	θ = 2.6–28.3°
α = 90.376 (1)°	µ = 0.21 mm−1
β = 110.407 (1)°	T = 173 K
γ = 97.439 (1)°	Block, colourless
V = 880.44 (3) Å3	0.33 × 0.31 × 0.29 mm

Bruker SMART APEXII CCD diffractometer	4369 independent reflections
Radiation source: rotating anode	3897 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.692, Tmax = 0.746	l = −13→14
19435 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) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0748P)2 + 0.2924P] where P = (Fo2 + 2Fc2)/3
4369 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.41 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	0.65884 (4)	0.48559 (3)	0.79845 (3)	0.02628 (11)
F1	0.84222 (15)	0.35909 (14)	0.41074 (11)	0.0615 (4)
O1	0.47089 (13)	0.17436 (11)	0.94217 (10)	0.0312 (2)
O2	0.54304 (14)	0.54929 (11)	0.68662 (11)	0.0358 (3)
C1	0.55705 (16)	0.33517 (14)	0.82691 (13)	0.0252 (3)
C2	0.44498 (15)	0.23532 (13)	0.72755 (13)	0.0235 (3)
C3	0.38240 (16)	0.21856 (13)	0.58605 (13)	0.0242 (3)
H3	0.4136	0.2834	0.5317	0.029*
C4	0.27338 (16)	0.10501 (13)	0.52593 (13)	0.0248 (3)
C5	0.22910 (18)	0.01022 (15)	0.60832 (15)	0.0307 (3)
H5	0.1549	−0.0669	0.5659	0.037*
C6	0.28993 (18)	0.02523 (16)	0.74949 (15)	0.0323 (3)
H6	0.2597	−0.0393	0.8045	0.039*
C7	0.39658 (16)	0.13922 (14)	0.80477 (13)	0.0268 (3)
C8	0.56642 (17)	0.29422 (15)	0.95219 (14)	0.0281 (3)
C9	0.20412 (16)	0.08110 (14)	0.37274 (14)	0.0264 (3)
H9	0.1189	0.0013	0.3508	0.032*
C10	0.12469 (18)	0.19886 (15)	0.30242 (14)	0.0292 (3)
H10A	0.0361	0.2136	0.3349	0.035*
H10B	0.2054	0.2804	0.3272	0.035*
C11	0.05690 (19)	0.17497 (17)	0.14790 (15)	0.0341 (3)
H11A	−0.0336	0.1006	0.1225	0.041*
H11B	0.0138	0.2558	0.1061	0.041*
C12	0.18461 (19)	0.14180 (17)	0.09251 (15)	0.0350 (3)
H12A	0.1342	0.1200	−0.0066	0.042*
H12B	0.2683	0.2205	0.1072	0.042*
C13	0.2628 (2)	0.02487 (19)	0.16166 (16)	0.0408 (4)
H13A	0.3497	0.0087	0.1277	0.049*
H13B	0.1812	−0.0561	0.1386	0.049*
C14	0.3336 (2)	0.05058 (19)	0.31578 (16)	0.0396 (4)
H14A	0.4218	0.1269	0.3393	0.048*
H14B	0.3803	−0.0288	0.3581	0.048*
C15	0.6580 (2)	0.35137 (18)	1.09261 (15)	0.0377 (4)
H15A	0.6953	0.4463	1.0897	0.057*
H15B	0.7515	0.3045	1.1339	0.057*
H15C	0.5878	0.3410	1.1468	0.057*
C16	0.79260 (16)	0.41782 (13)	0.72905 (13)	0.0248 (3)
C17	0.75975 (17)	0.41440 (15)	0.59050 (14)	0.0291 (3)
H17	0.6656	0.4446	0.5295	0.035*
C18	0.8701 (2)	0.36513 (17)	0.54482 (16)	0.0354 (3)
C19	1.0094 (2)	0.32320 (17)	0.62948 (18)	0.0398 (4)
H19	1.0829	0.2907	0.5939	0.048*
C20	1.0398 (2)	0.32951 (18)	0.76767 (18)	0.0404 (4)
H20	1.1352	0.3006	0.8281	0.049*
C21	0.93245 (18)	0.37764 (17)	0.81917 (15)	0.0344 (3)
H21	0.9542	0.3830	0.9143	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.02997 (19)	0.02451 (18)	0.02462 (17)	0.00348 (13)	0.01014 (13)	−0.00131 (12)
F1	0.0640 (7)	0.0929 (10)	0.0356 (5)	0.0216 (7)	0.0239 (5)	−0.0039 (6)
O1	0.0346 (5)	0.0388 (6)	0.0242 (5)	0.0057 (4)	0.0152 (4)	0.0056 (4)
O2	0.0386 (6)	0.0332 (6)	0.0378 (6)	0.0126 (5)	0.0136 (5)	0.0070 (4)
C1	0.0261 (6)	0.0285 (6)	0.0226 (6)	0.0049 (5)	0.0103 (5)	0.0001 (5)
C2	0.0227 (6)	0.0254 (6)	0.0248 (6)	0.0054 (5)	0.0109 (5)	0.0021 (5)
C3	0.0245 (6)	0.0247 (6)	0.0244 (6)	0.0038 (5)	0.0097 (5)	0.0029 (5)
C4	0.0230 (6)	0.0247 (6)	0.0271 (6)	0.0042 (5)	0.0091 (5)	0.0019 (5)
C5	0.0284 (7)	0.0274 (7)	0.0357 (7)	−0.0009 (5)	0.0125 (6)	0.0020 (6)
C6	0.0331 (7)	0.0321 (7)	0.0355 (7)	0.0014 (6)	0.0177 (6)	0.0089 (6)
C7	0.0269 (6)	0.0319 (7)	0.0252 (6)	0.0058 (5)	0.0132 (5)	0.0042 (5)
C8	0.0287 (6)	0.0343 (7)	0.0245 (6)	0.0079 (6)	0.0121 (5)	0.0012 (5)
C9	0.0254 (6)	0.0253 (6)	0.0261 (6)	0.0021 (5)	0.0067 (5)	−0.0004 (5)
C10	0.0319 (7)	0.0306 (7)	0.0275 (6)	0.0093 (6)	0.0118 (5)	0.0020 (5)
C11	0.0338 (7)	0.0420 (8)	0.0276 (7)	0.0119 (6)	0.0099 (6)	0.0039 (6)
C12	0.0371 (8)	0.0417 (8)	0.0284 (7)	0.0035 (6)	0.0149 (6)	−0.0027 (6)
C13	0.0418 (8)	0.0500 (10)	0.0311 (7)	0.0180 (7)	0.0095 (6)	−0.0080 (7)
C14	0.0349 (8)	0.0532 (10)	0.0305 (7)	0.0205 (7)	0.0063 (6)	−0.0063 (7)
C15	0.0426 (8)	0.0493 (9)	0.0229 (6)	0.0084 (7)	0.0130 (6)	−0.0009 (6)
C16	0.0260 (6)	0.0229 (6)	0.0255 (6)	0.0021 (5)	0.0096 (5)	0.0016 (5)
C17	0.0283 (7)	0.0322 (7)	0.0252 (6)	0.0040 (5)	0.0076 (5)	0.0013 (5)
C18	0.0383 (8)	0.0393 (8)	0.0308 (7)	0.0021 (6)	0.0162 (6)	−0.0039 (6)
C19	0.0343 (8)	0.0400 (9)	0.0499 (9)	0.0083 (7)	0.0199 (7)	−0.0028 (7)
C20	0.0310 (8)	0.0447 (9)	0.0449 (9)	0.0129 (7)	0.0098 (7)	0.0071 (7)
C21	0.0328 (7)	0.0406 (8)	0.0278 (7)	0.0089 (6)	0.0069 (6)	0.0061 (6)

S1—O2	1.4831 (11)	C11—C12	1.519 (2)
S1—C1	1.7523 (15)	C11—H11A	0.9900
S1—C16	1.7992 (14)	C11—H11B	0.9900
F1—C18	1.3424 (18)	C12—C13	1.512 (2)
O1—C8	1.3703 (18)	C12—H12A	0.9900
O1—C7	1.3842 (16)	C12—H12B	0.9900
C1—C8	1.3609 (19)	C13—C14	1.526 (2)
C1—C2	1.4520 (18)	C13—H13A	0.9900
C2—C7	1.3920 (19)	C13—H13B	0.9900
C2—C3	1.3948 (17)	C14—H14A	0.9900
C3—C4	1.3925 (19)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.406 (2)	C15—H15B	0.9800
C4—C9	1.5149 (18)	C15—H15C	0.9800
C5—C6	1.390 (2)	C16—C17	1.3809 (18)
C5—H5	0.9500	C16—C21	1.3891 (19)
C6—C7	1.377 (2)	C17—C18	1.379 (2)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.4852 (19)	C18—C19	1.373 (2)
C9—C10	1.5281 (19)	C19—C20	1.381 (2)
C9—C14	1.536 (2)	C19—H19	0.9500
C9—H9	1.0000	C20—C21	1.387 (2)
C10—C11	1.5277 (19)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900
O2—S1—C1	107.99 (7)	C10—C11—H11B	109.2
O2—S1—C16	107.08 (6)	H11A—C11—H11B	107.9
C1—S1—C16	98.41 (6)	C13—C12—C11	110.99 (13)
C8—O1—C7	106.54 (11)	C13—C12—H12A	109.4
C8—C1—C2	107.28 (12)	C11—C12—H12A	109.4
C8—C1—S1	124.17 (11)	C13—C12—H12B	109.4
C2—C1—S1	128.51 (10)	C11—C12—H12B	109.4
C7—C2—C3	119.47 (12)	H12A—C12—H12B	108.0
C7—C2—C1	104.60 (11)	C12—C13—C14	111.35 (13)
C3—C2—C1	135.92 (13)	C12—C13—H13A	109.4
C4—C3—C2	118.74 (12)	C14—C13—H13A	109.4
C4—C3—H3	120.6	C12—C13—H13B	109.4
C2—C3—H3	120.6	C14—C13—H13B	109.4
C3—C4—C5	119.68 (13)	H13A—C13—H13B	108.0
C3—C4—C9	120.75 (12)	C13—C14—C9	111.27 (12)
C5—C4—C9	119.56 (12)	C13—C14—H14A	109.4
C6—C5—C4	122.44 (13)	C9—C14—H14A	109.4
C6—C5—H5	118.8	C13—C14—H14B	109.4
C4—C5—H5	118.8	C9—C14—H14B	109.4
C7—C6—C5	116.01 (13)	H14A—C14—H14B	108.0
C7—C6—H6	122.0	C8—C15—H15A	109.5
C5—C6—H6	122.0	C8—C15—H15B	109.5
C6—C7—O1	125.68 (13)	H15A—C15—H15B	109.5
C6—C7—C2	123.65 (13)	C8—C15—H15C	109.5
O1—C7—C2	110.67 (12)	H15A—C15—H15C	109.5
C1—C8—O1	110.90 (12)	H15B—C15—H15C	109.5
C1—C8—C15	133.45 (15)	C17—C16—C21	121.91 (13)
O1—C8—C15	115.64 (13)	C17—C16—S1	119.95 (11)
C4—C9—C10	111.98 (11)	C21—C16—S1	118.02 (10)
C4—C9—C14	111.49 (11)	C18—C17—C16	116.83 (13)
C10—C9—C14	109.86 (12)	C18—C17—H17	121.6
C4—C9—H9	107.8	C16—C17—H17	121.6
C10—C9—H9	107.8	F1—C18—C19	117.70 (14)
C14—C9—H9	107.8	F1—C18—C17	118.79 (15)
C11—C10—C9	111.76 (12)	C19—C18—C17	123.50 (14)
C11—C10—H10A	109.3	C18—C19—C20	118.24 (14)
C9—C10—H10A	109.3	C18—C19—H19	120.9
C11—C10—H10B	109.3	C20—C19—H19	120.9
C9—C10—H10B	109.3	C19—C20—C21	120.67 (14)
H10A—C10—H10B	107.9	C19—C20—H20	119.7
C12—C11—C10	111.91 (12)	C21—C20—H20	119.7
C12—C11—H11A	109.2	C20—C21—C16	118.81 (14)
C10—C11—H11A	109.2	C20—C21—H21	120.6
C12—C11—H11B	109.2	C16—C21—H21	120.6
O2—S1—C1—C8	−134.55 (12)	C7—O1—C8—C15	179.79 (12)
C16—S1—C1—C8	114.34 (12)	C3—C4—C9—C10	−54.46 (17)
O2—S1—C1—C2	42.59 (13)	C5—C4—C9—C10	126.65 (14)
C16—S1—C1—C2	−68.53 (13)	C3—C4—C9—C14	69.09 (17)
C8—C1—C2—C7	−0.61 (14)	C5—C4—C9—C14	−109.80 (15)
S1—C1—C2—C7	−178.13 (10)	C4—C9—C10—C11	179.30 (12)
C8—C1—C2—C3	179.01 (14)	C14—C9—C10—C11	54.84 (16)
S1—C1—C2—C3	1.5 (2)	C9—C10—C11—C12	−54.84 (17)
C7—C2—C3—C4	−0.38 (19)	C10—C11—C12—C13	54.65 (18)
C1—C2—C3—C4	−179.96 (14)	C11—C12—C13—C14	−55.75 (19)
C2—C3—C4—C5	−0.09 (19)	C12—C13—C14—C9	57.1 (2)
C2—C3—C4—C9	−178.99 (11)	C4—C9—C14—C13	179.29 (14)
C3—C4—C5—C6	0.2 (2)	C10—C9—C14—C13	−55.97 (18)
C9—C4—C5—C6	179.11 (13)	O2—S1—C16—C17	−9.39 (14)
C4—C5—C6—C7	0.2 (2)	C1—S1—C16—C17	102.44 (12)
C5—C6—C7—O1	179.75 (13)	O2—S1—C16—C21	166.74 (12)
C5—C6—C7—C2	−0.7 (2)	C1—S1—C16—C21	−81.42 (13)
C8—O1—C7—C6	−179.98 (14)	C21—C16—C17—C18	2.0 (2)
C8—O1—C7—C2	0.40 (15)	S1—C16—C17—C18	177.96 (11)
C3—C2—C7—C6	0.8 (2)	C16—C17—C18—F1	179.49 (14)
C1—C2—C7—C6	−179.50 (13)	C16—C17—C18—C19	−1.5 (2)
C3—C2—C7—O1	−179.57 (11)	F1—C18—C19—C20	179.71 (16)
C1—C2—C7—O1	0.13 (14)	C17—C18—C19—C20	0.7 (3)
C2—C1—C8—O1	0.90 (15)	C18—C19—C20—C21	−0.3 (3)
S1—C1—C8—O1	178.55 (9)	C19—C20—C21—C16	0.8 (3)
C2—C1—C8—C15	−179.85 (15)	C17—C16—C21—C20	−1.7 (2)
S1—C1—C8—C15	−2.2 (2)	S1—C16—C21—C20	−177.77 (13)
C7—O1—C8—C1	−0.81 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cg1i	0.99	3.00	3.697 (1)	128
C14—H14B···Cg2i	0.99	2.91	3.569 (1)	125
C19—H19···Cg2ii	0.95	2.90	3.677 (1)	140

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1i	0.99	3.00	3.697 (1)	128
C14—H14B⋯Cg2i	0.99	2.91	3.569 (1)	125
C19—H19⋯Cg2ii	0.95	2.90	3.677 (1)	140

Symmetry codes: (i) ; (ii) .