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

In the title compound, C21H21FO2S, the cyclo-hexyl ring adopts a chair conformation. The 2-fluoro-phenyl ring makes a dihedral angle of 88.47 (4)° with the mean plane [r.m.s. deviation = 0.013 (1) Å] of the benzo-furan fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions, forming chains propagating along [100]. The crystal structure also exhibits slipped π-π inter-actions between the furan rings of neighboring mol-ecules [centroid-to-centroid distance = 3.397 (2) Å, inter-planar distance = 3.346 (2) Å and slippage = 0.586 (2) Å].

Related literature

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

Experimental

Crystal data

C21H21FO2S

M = 356.44

Triclinic,

a = 9.0667 (2) Å

b = 10.3647 (2) Å

c = 10.6838 (2) Å

α = 105.395 (1)°

β = 93.418 (1)°

γ = 110.839 (1)°

V = 891.33 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.30 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.681, T max = 0.746

16785 measured reflections

4455 independent reflections

3495 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.04

4455 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.30 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, 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/S1600536813011902/zl2547sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011902/zl2547Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011902/zl2547Isup3.cml

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

C21H21FO2S	Z = 2
Mr = 356.44	F(000) = 376
Triclinic, P1	Dx = 1.328 Mg m−3
Hall symbol: -P 1	Melting point = 424–425 K
a = 9.0667 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3647 (2) Å	Cell parameters from 5827 reflections
c = 10.6838 (2) Å	θ = 2.5–28.3°
α = 105.395 (1)°	µ = 0.20 mm−1
β = 93.418 (1)°	T = 173 K
γ = 110.839 (1)°	Block, colourless
V = 891.33 (3) Å3	0.30 × 0.22 × 0.21 mm

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Radiation source: rotating anode	3495 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.681, Tmax = 0.746	l = −14→14
16785 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2597P] where P = (Fo2 + 2Fc2)/3
4455 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.30 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	0.76058 (5)	1.09181 (4)	0.70859 (4)	0.03217 (12)
O1	1.03485 (12)	0.87847 (12)	0.60101 (10)	0.0301 (2)
O2	0.67934 (15)	1.12362 (13)	0.60291 (12)	0.0422 (3)
F1	0.79828 (12)	0.97950 (14)	0.92911 (10)	0.0507 (3)
C1	0.84436 (18)	0.96774 (16)	0.63603 (14)	0.0264 (3)
C2	0.77490 (17)	0.83447 (15)	0.52735 (14)	0.0251 (3)
C3	0.62620 (18)	0.75355 (16)	0.44660 (15)	0.0278 (3)
H3	0.5406	0.7860	0.4560	0.033*
C4	0.60561 (19)	0.62411 (16)	0.35184 (16)	0.0306 (3)
C5	0.7353 (2)	0.58063 (18)	0.33814 (17)	0.0364 (4)
H5	0.7198	0.4925	0.2726	0.044*
C6	0.8845 (2)	0.66036 (18)	0.41581 (17)	0.0351 (4)
H6	0.9717	0.6304	0.4045	0.042*
C7	0.89918 (18)	0.78535 (16)	0.51019 (15)	0.0273 (3)
C8	0.99753 (18)	0.98799 (16)	0.67553 (15)	0.0282 (3)
C9	0.4458 (2)	0.52941 (17)	0.26325 (17)	0.0362 (4)
H9	0.4510	0.4334	0.2193	0.043*
C10	0.4120 (2)	0.5904 (2)	0.15474 (17)	0.0394 (4)
H10A	0.4059	0.6858	0.1949	0.047*
H10B	0.5012	0.6055	0.1039	0.047*
C11	0.2557 (2)	0.4885 (2)	0.06208 (19)	0.0517 (5)
H11A	0.2343	0.5336	−0.0041	0.062*
H11B	0.2662	0.3970	0.0147	0.062*
C12	0.1165 (2)	0.4548 (2)	0.1352 (2)	0.0489 (5)
H12A	0.0959	0.5439	0.1717	0.059*
H12B	0.0194	0.3816	0.0730	0.059*
C13	0.1483 (2)	0.3982 (2)	0.2457 (2)	0.0567 (6)
H13A	0.1532	0.3019	0.2083	0.068*
H13B	0.0590	0.3860	0.2963	0.068*
C14	0.3054 (2)	0.5009 (2)	0.3382 (2)	0.0516 (5)
H14A	0.2964	0.5940	0.3829	0.062*
H14B	0.3254	0.4580	0.4067	0.062*
C15	1.1253 (2)	1.09951 (19)	0.78339 (17)	0.0372 (4)
H15A	1.0949	1.1821	0.8190	0.056*
H15B	1.2256	1.1323	0.7493	0.056*
H15C	1.1401	1.0581	0.8533	0.056*
C16	0.60472 (19)	0.97077 (17)	0.76771 (15)	0.0303 (3)
C17	0.6418 (2)	0.93040 (19)	0.87463 (16)	0.0347 (4)
C18	0.5274 (2)	0.8447 (2)	0.92798 (18)	0.0406 (4)
H18	0.5560	0.8180	1.0014	0.049*
C19	0.3692 (2)	0.79842 (19)	0.87168 (19)	0.0416 (4)
H19	0.2872	0.7398	0.9074	0.050*
C20	0.3288 (2)	0.83647 (19)	0.76392 (19)	0.0427 (4)
H20	0.2194	0.8025	0.7254	0.051*
C21	0.4458 (2)	0.92345 (18)	0.71169 (17)	0.0364 (4)
H21	0.4175	0.9504	0.6383	0.044*

	U11	U22	U33	U12	U13	U23
S1	0.0368 (2)	0.0274 (2)	0.0298 (2)	0.01355 (17)	0.00040 (16)	0.00423 (16)
O1	0.0240 (5)	0.0359 (6)	0.0295 (6)	0.0102 (5)	0.0022 (4)	0.0111 (5)
O2	0.0506 (7)	0.0417 (7)	0.0430 (7)	0.0253 (6)	0.0040 (6)	0.0176 (6)
F1	0.0376 (6)	0.0818 (8)	0.0353 (6)	0.0238 (6)	−0.0011 (5)	0.0229 (6)
C1	0.0276 (7)	0.0260 (7)	0.0232 (7)	0.0083 (6)	0.0021 (6)	0.0069 (6)
C2	0.0277 (7)	0.0251 (7)	0.0236 (7)	0.0093 (6)	0.0038 (6)	0.0103 (6)
C3	0.0269 (7)	0.0264 (7)	0.0289 (8)	0.0086 (6)	0.0019 (6)	0.0095 (6)
C4	0.0321 (8)	0.0245 (7)	0.0309 (8)	0.0073 (6)	0.0003 (6)	0.0079 (6)
C5	0.0426 (10)	0.0276 (8)	0.0342 (9)	0.0141 (7)	0.0030 (7)	0.0019 (7)
C6	0.0348 (9)	0.0368 (9)	0.0368 (9)	0.0183 (7)	0.0077 (7)	0.0099 (7)
C7	0.0255 (7)	0.0300 (7)	0.0257 (7)	0.0084 (6)	0.0027 (6)	0.0113 (6)
C8	0.0293 (8)	0.0299 (8)	0.0250 (8)	0.0085 (6)	0.0033 (6)	0.0121 (6)
C9	0.0364 (9)	0.0224 (7)	0.0396 (9)	0.0068 (7)	−0.0048 (7)	0.0019 (7)
C10	0.0337 (9)	0.0483 (10)	0.0296 (9)	0.0080 (8)	0.0040 (7)	0.0126 (8)
C11	0.0410 (11)	0.0669 (13)	0.0342 (10)	0.0092 (10)	−0.0038 (8)	0.0129 (9)
C12	0.0332 (9)	0.0543 (12)	0.0502 (11)	0.0084 (9)	−0.0025 (8)	0.0155 (9)
C13	0.0379 (10)	0.0543 (12)	0.0627 (13)	−0.0061 (9)	−0.0035 (9)	0.0294 (11)
C14	0.0390 (10)	0.0554 (12)	0.0464 (11)	−0.0057 (9)	−0.0023 (8)	0.0284 (10)
C15	0.0306 (8)	0.0394 (9)	0.0329 (9)	0.0057 (7)	−0.0051 (7)	0.0105 (7)
C16	0.0345 (8)	0.0312 (8)	0.0251 (8)	0.0169 (7)	0.0036 (6)	0.0032 (6)
C17	0.0350 (9)	0.0408 (9)	0.0278 (8)	0.0187 (7)	0.0014 (7)	0.0050 (7)
C18	0.0502 (11)	0.0438 (10)	0.0353 (9)	0.0257 (9)	0.0104 (8)	0.0128 (8)
C19	0.0426 (10)	0.0317 (9)	0.0494 (11)	0.0152 (8)	0.0149 (8)	0.0083 (8)
C20	0.0329 (9)	0.0373 (9)	0.0525 (11)	0.0149 (8)	−0.0001 (8)	0.0048 (8)
C21	0.0369 (9)	0.0364 (9)	0.0349 (9)	0.0186 (7)	−0.0021 (7)	0.0053 (7)

S1—O2	1.4823 (12)	C11—C12	1.508 (3)
S1—C1	1.7516 (15)	C11—H11A	0.9900
S1—C16	1.7988 (17)	C11—H11B	0.9900
O1—C8	1.3647 (19)	C12—C13	1.506 (3)
O1—C7	1.3790 (18)	C12—H12A	0.9900
F1—C17	1.3569 (19)	C12—H12B	0.9900
C1—C8	1.351 (2)	C13—C14	1.527 (3)
C1—C2	1.447 (2)	C13—H13A	0.9900
C2—C3	1.392 (2)	C13—H13B	0.9900
C2—C7	1.395 (2)	C14—H14A	0.9900
C3—C4	1.392 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.403 (2)	C15—H15B	0.9800
C4—C9	1.513 (2)	C15—H15C	0.9800
C5—C6	1.381 (2)	C16—C17	1.379 (2)
C5—H5	0.9500	C16—C21	1.383 (2)
C6—C7	1.371 (2)	C17—C18	1.368 (3)
C6—H6	0.9500	C18—C19	1.380 (3)
C8—C15	1.479 (2)	C18—H18	0.9500
C9—C10	1.524 (2)	C19—C20	1.382 (3)
C9—C14	1.527 (3)	C19—H19	0.9500
C9—H9	1.0000	C20—C21	1.381 (3)
C10—C11	1.522 (2)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900
O2—S1—C1	108.76 (7)	C10—C11—H11B	109.3
O2—S1—C16	106.28 (8)	H11A—C11—H11B	107.9
C1—S1—C16	97.18 (7)	C13—C12—C11	111.76 (17)
C8—O1—C7	106.55 (11)	C13—C12—H12A	109.3
C8—C1—C2	107.67 (13)	C11—C12—H12A	109.3
C8—C1—S1	122.41 (12)	C13—C12—H12B	109.3
C2—C1—S1	129.89 (11)	C11—C12—H12B	109.3
C3—C2—C7	119.50 (14)	H12A—C12—H12B	107.9
C3—C2—C1	136.36 (14)	C12—C13—C14	111.52 (15)
C7—C2—C1	104.13 (13)	C12—C13—H13A	109.3
C2—C3—C4	118.59 (14)	C14—C13—H13A	109.3
C2—C3—H3	120.7	C12—C13—H13B	109.3
C4—C3—H3	120.7	C14—C13—H13B	109.3
C3—C4—C5	119.45 (15)	H13A—C13—H13B	108.0
C3—C4—C9	121.17 (14)	C9—C14—C13	111.25 (17)
C5—C4—C9	119.38 (14)	C9—C14—H14A	109.4
C6—C5—C4	122.89 (15)	C13—C14—H14A	109.4
C6—C5—H5	118.6	C9—C14—H14B	109.4
C4—C5—H5	118.6	C13—C14—H14B	109.4
C7—C6—C5	116.01 (15)	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	125.80 (14)	H15A—C15—H15B	109.5
C6—C7—C2	123.52 (15)	C8—C15—H15C	109.5
O1—C7—C2	110.68 (13)	H15A—C15—H15C	109.5
C1—C8—O1	110.97 (13)	H15B—C15—H15C	109.5
C1—C8—C15	132.96 (15)	C17—C16—C21	119.06 (16)
O1—C8—C15	116.03 (13)	C17—C16—S1	120.14 (13)
C4—C9—C10	112.40 (13)	C21—C16—S1	120.71 (13)
C4—C9—C14	113.24 (14)	F1—C17—C18	119.26 (15)
C10—C9—C14	109.31 (14)	F1—C17—C16	118.10 (15)
C4—C9—H9	107.2	C18—C17—C16	122.63 (16)
C10—C9—H9	107.2	C17—C18—C19	117.89 (17)
C14—C9—H9	107.2	C17—C18—H18	121.1
C11—C10—C9	111.29 (15)	C19—C18—H18	121.1
C11—C10—H10A	109.4	C18—C19—C20	120.65 (17)
C9—C10—H10A	109.4	C18—C19—H19	119.7
C11—C10—H10B	109.4	C20—C19—H19	119.7
C9—C10—H10B	109.4	C21—C20—C19	120.64 (17)
H10A—C10—H10B	108.0	C21—C20—H20	119.7
C12—C11—C10	111.80 (16)	C19—C20—H20	119.7
C12—C11—H11A	109.3	C20—C21—C16	119.12 (16)
C10—C11—H11A	109.3	C20—C21—H21	120.4
C12—C11—H11B	109.3	C16—C21—H21	120.4
O2—S1—C1—C8	131.20 (13)	C7—O1—C8—C15	178.13 (12)
C16—S1—C1—C8	−118.85 (14)	C3—C4—C9—C10	75.69 (19)
O2—S1—C1—C2	−46.74 (16)	C5—C4—C9—C10	−104.29 (18)
C16—S1—C1—C2	63.21 (15)	C3—C4—C9—C14	−48.8 (2)
C8—C1—C2—C3	178.69 (16)	C5—C4—C9—C14	131.23 (17)
S1—C1—C2—C3	−3.1 (3)	C4—C9—C10—C11	176.45 (15)
C8—C1—C2—C7	−0.48 (16)	C14—C9—C10—C11	−56.9 (2)
S1—C1—C2—C7	177.70 (12)	C9—C10—C11—C12	55.9 (2)
C7—C2—C3—C4	0.9 (2)	C10—C11—C12—C13	−53.9 (2)
C1—C2—C3—C4	−178.16 (16)	C11—C12—C13—C14	53.8 (3)
C2—C3—C4—C5	−1.5 (2)	C4—C9—C14—C13	−176.82 (15)
C2—C3—C4—C9	178.51 (14)	C10—C9—C14—C13	57.0 (2)
C3—C4—C5—C6	0.5 (3)	C12—C13—C14—C9	−56.0 (2)
C9—C4—C5—C6	−179.48 (15)	O2—S1—C16—C17	−174.67 (12)
C4—C5—C6—C7	1.0 (2)	C1—S1—C16—C17	73.34 (14)
C5—C6—C7—O1	177.69 (14)	O2—S1—C16—C21	1.70 (15)
C5—C6—C7—C2	−1.7 (2)	C1—S1—C16—C21	−110.29 (14)
C8—O1—C7—C6	−179.97 (15)	C21—C16—C17—F1	−179.18 (14)
C8—O1—C7—C2	−0.55 (15)	S1—C16—C17—F1	−2.8 (2)
C3—C2—C7—C6	0.7 (2)	C21—C16—C17—C18	0.1 (2)
C1—C2—C7—C6	−179.93 (14)	S1—C16—C17—C18	176.54 (13)
C3—C2—C7—O1	−178.71 (12)	F1—C17—C18—C19	178.98 (15)
C1—C2—C7—O1	0.63 (16)	C16—C17—C18—C19	−0.3 (3)
C2—C1—C8—O1	0.17 (17)	C17—C18—C19—C20	0.7 (3)
S1—C1—C8—O1	−178.18 (10)	C18—C19—C20—C21	−1.0 (3)
C2—C1—C8—C15	−177.26 (15)	C19—C20—C21—C16	0.8 (3)
S1—C1—C8—C15	4.4 (2)	C17—C16—C21—C20	−0.3 (2)
C7—O1—C8—C1	0.23 (16)	S1—C16—C21—C20	−176.75 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.60	3.5024 (19)	160
C20—H20···O1ii	0.95	2.53	3.316 (2)	140
C21—H21···O2i	0.95	2.49	3.332 (2)	148
C14—H14B···Cg2iii	0.99	2.69	3.618 (2)	156
C15—H15B···Cg2iv	0.98	2.85	3.422 (2)	118

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.60	3.5024 (19)	160
C20—H20⋯O1ii	0.95	2.53	3.316 (2)	140
C21—H21⋯O2i	0.95	2.49	3.332 (2)	148
C14—H14B⋯Cg2iii	0.99	2.69	3.618 (2)	156
C15—H15B⋯Cg2iv	0.98	2.85	3.422 (2)	118

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