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

In the title compound, C(21)H(21)FO(2)S, the cyclo-hexyl ring adopts a chair conformation. The 3-fluoro-phenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C21H21FO2S

M = 356.44

Orthorhombic,

a = 12.7767 (10) Å

b = 13.0764 (10) Å

c = 10.7711 (8) Å

V = 1799.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.961

17893 measured reflections

4503 independent reflections

4036 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.096

S = 1.03

4503 reflections

227 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 2131 Friedel pairs

Flack parameter: −0.07 (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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008343/bh2416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008343/bh2416Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008343/bh2416Isup3.cml

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

C21H21FO2S	Dx = 1.316 Mg m−3
Mr = 356.44	Melting point: 443 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4473 reflections
a = 12.7767 (10) Å	θ = 2.5–28.1°
b = 13.0764 (10) Å	µ = 0.20 mm−1
c = 10.7711 (8) Å	T = 173 K
V = 1799.6 (2) Å3	Block, colourless
Z = 4	0.34 × 0.24 × 0.20 mm
F(000) = 752

Bruker SMART APEXII CCD diffractometer	4503 independent reflections
Radiation source: rotating anode	4036 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.058
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.2°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −17→16
Tmin = 0.935, Tmax = 0.961	l = −14→14
17893 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.2167P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4503 reflections	Δρmax = 0.33 e Å−3
227 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 2131 Friedel pairs
0 constraints	Flack parameter: −0.07 (7)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
S1	0.56575 (3)	0.02701 (3)	0.35040 (5)	0.02691 (11)
F1	0.77633 (15)	0.11534 (12)	−0.03264 (18)	0.0792 (6)
O1	0.46206 (10)	0.30803 (10)	0.29361 (13)	0.0277 (3)
O2	0.56405 (11)	−0.00184 (12)	0.48474 (14)	0.0390 (4)
C1	0.49571 (12)	0.14257 (13)	0.33717 (18)	0.0234 (3)
C2	0.40393 (13)	0.17197 (14)	0.40656 (17)	0.0231 (3)
C3	0.33673 (13)	0.12486 (14)	0.49109 (16)	0.0254 (4)
H3	0.3475	0.0555	0.5143	0.031*
C4	0.25446 (14)	0.17975 (15)	0.54083 (17)	0.0257 (4)
C5	0.24014 (14)	0.28249 (15)	0.5060 (2)	0.0296 (4)
H5	0.1833	0.3196	0.5408	0.036*
C6	0.30589 (14)	0.33145 (15)	0.42275 (19)	0.0287 (4)
H6	0.2957	0.4009	0.3997	0.034*
C7	0.38672 (13)	0.27399 (14)	0.37531 (16)	0.0260 (4)
C8	0.52756 (14)	0.22666 (14)	0.27291 (16)	0.0256 (4)
C9	0.17818 (14)	0.12816 (16)	0.62864 (17)	0.0287 (4)
H9	0.2064	0.0585	0.6469	0.034*
C10	0.16664 (19)	0.1834 (2)	0.7521 (2)	0.0443 (5)
H10A	0.1439	0.2547	0.7367	0.053*
H10B	0.2354	0.1858	0.7943	0.053*
C11	0.08727 (19)	0.1306 (2)	0.8365 (2)	0.0554 (7)
H11A	0.1153	0.0634	0.8625	0.067*
H11B	0.0767	0.1725	0.9121	0.067*
C12	−0.01698 (19)	0.1153 (2)	0.7722 (3)	0.0573 (8)
H12A	−0.0642	0.0761	0.8273	0.069*
H12B	−0.0495	0.1827	0.7564	0.069*
C13	−0.00474 (18)	0.0591 (2)	0.6512 (3)	0.0494 (6)
H13A	−0.0736	0.0540	0.6095	0.059*
H13B	0.0206	−0.0112	0.6676	0.059*
C14	0.07219 (16)	0.1139 (2)	0.5661 (2)	0.0405 (5)
H14A	0.0434	0.1816	0.5431	0.049*
H14B	0.0813	0.0737	0.4890	0.049*
C15	0.61838 (13)	0.24653 (16)	0.19341 (17)	0.0269 (4)
C16	0.65392 (17)	0.17134 (18)	0.1135 (2)	0.0389 (5)
H16	0.6172	0.1086	0.1051	0.047*
C17	0.74380 (18)	0.18950 (19)	0.0462 (2)	0.0457 (6)
C18	0.79812 (17)	0.27964 (19)	0.0536 (2)	0.0421 (5)
H18	0.8604	0.2896	0.0069	0.051*
C19	0.76030 (16)	0.35559 (19)	0.1303 (2)	0.0376 (5)
H19	0.7957	0.4194	0.1349	0.045*
C20	0.67083 (14)	0.33938 (16)	0.20081 (19)	0.0306 (4)
H20	0.6455	0.3917	0.2541	0.037*
C21	0.47422 (18)	−0.05631 (16)	0.2771 (2)	0.0378 (5)
H21A	0.5009	−0.1266	0.2794	0.057*
H21B	0.4644	−0.0352	0.1905	0.057*
H21C	0.4071	−0.0530	0.3209	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.02477 (19)	0.0252 (2)	0.0307 (2)	0.00363 (16)	0.00124 (19)	0.0016 (2)
F1	0.0930 (12)	0.0564 (10)	0.0883 (13)	0.0007 (9)	0.0641 (10)	−0.0086 (9)
O1	0.0257 (6)	0.0243 (7)	0.0332 (7)	−0.0006 (5)	0.0024 (5)	0.0051 (6)
O2	0.0457 (9)	0.0377 (8)	0.0335 (8)	0.0094 (7)	−0.0076 (7)	0.0065 (7)
C1	0.0219 (7)	0.0237 (8)	0.0246 (9)	−0.0008 (6)	0.0011 (7)	0.0004 (8)
C2	0.0207 (7)	0.0243 (9)	0.0243 (8)	0.0011 (7)	−0.0022 (6)	0.0010 (7)
C3	0.0255 (8)	0.0236 (9)	0.0272 (9)	0.0014 (7)	0.0001 (7)	0.0023 (7)
C4	0.0246 (9)	0.0267 (10)	0.0256 (9)	0.0020 (7)	0.0008 (7)	0.0007 (7)
C5	0.0248 (9)	0.0291 (10)	0.0350 (10)	0.0042 (7)	0.0020 (7)	−0.0021 (8)
C6	0.0279 (9)	0.0232 (9)	0.0352 (10)	0.0026 (7)	−0.0013 (8)	0.0013 (8)
C7	0.0219 (8)	0.0262 (9)	0.0301 (10)	−0.0030 (7)	−0.0022 (7)	0.0023 (7)
C8	0.0244 (8)	0.0264 (10)	0.0260 (9)	0.0005 (7)	−0.0019 (7)	0.0011 (7)
C9	0.0284 (9)	0.0306 (10)	0.0271 (9)	0.0055 (7)	0.0042 (7)	0.0033 (8)
C10	0.0440 (12)	0.0575 (15)	0.0315 (11)	−0.0056 (11)	0.0084 (9)	−0.0057 (10)
C11	0.0643 (15)	0.0647 (17)	0.0373 (13)	−0.0022 (12)	0.0242 (12)	−0.0026 (13)
C12	0.0434 (13)	0.0520 (15)	0.077 (2)	0.0069 (12)	0.0309 (13)	0.0186 (14)
C13	0.0353 (11)	0.0559 (16)	0.0571 (15)	−0.0109 (11)	0.0033 (10)	0.0208 (12)
C14	0.0383 (12)	0.0457 (14)	0.0376 (11)	−0.0115 (10)	−0.0014 (9)	0.0124 (10)
C15	0.0250 (8)	0.0297 (10)	0.0261 (9)	0.0002 (7)	0.0008 (7)	0.0066 (7)
C16	0.0445 (12)	0.0335 (12)	0.0387 (12)	−0.0035 (9)	0.0140 (9)	0.0040 (9)
C17	0.0474 (13)	0.0440 (14)	0.0457 (13)	0.0073 (11)	0.0228 (11)	0.0087 (11)
C18	0.0297 (10)	0.0564 (15)	0.0402 (12)	0.0000 (10)	0.0101 (9)	0.0163 (11)
C19	0.0295 (10)	0.0448 (13)	0.0386 (11)	−0.0125 (9)	−0.0027 (9)	0.0095 (10)
C20	0.0289 (9)	0.0315 (11)	0.0312 (10)	−0.0024 (8)	−0.0044 (8)	0.0049 (8)
C21	0.0447 (12)	0.0281 (10)	0.0406 (12)	−0.0025 (9)	−0.0070 (9)	−0.0039 (9)

S1—O2	1.4954 (15)	C11—C12	1.515 (4)
S1—C1	1.7620 (17)	C11—H11A	0.9900
S1—C21	1.783 (2)	C11—H11B	0.9900
F1—C17	1.355 (3)	C12—C13	1.505 (4)
O1—C8	1.372 (2)	C12—H12A	0.9900
O1—C7	1.378 (2)	C12—H12B	0.9900
C1—C8	1.361 (3)	C13—C14	1.523 (3)
C1—C2	1.443 (2)	C13—H13A	0.9900
C2—C7	1.393 (3)	C13—H13B	0.9900
C2—C3	1.395 (2)	C14—H14A	0.9900
C3—C4	1.381 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—C16	1.383 (3)
C4—C5	1.407 (3)	C15—C20	1.389 (3)
C4—C9	1.516 (3)	C16—C17	1.378 (3)
C5—C6	1.385 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.370 (3)
C6—C7	1.376 (3)	C18—C19	1.379 (3)
C6—H6	0.9500	C18—H18	0.9500
C8—C15	1.465 (2)	C19—C20	1.389 (3)
C9—C10	1.520 (3)	C19—H19	0.9500
C9—C14	1.524 (3)	C20—H20	0.9500
C9—H9	1.0000	C21—H21A	0.9800
C10—C11	1.527 (3)	C21—H21B	0.9800
C10—H10A	0.9900	C21—H21C	0.9800
C10—H10B	0.9900
O2—S1—C1	106.69 (9)	C10—C11—H11B	109.3
O2—S1—C21	105.37 (10)	H11A—C11—H11B	107.9
C1—S1—C21	98.93 (9)	C13—C12—C11	111.69 (19)
C8—O1—C7	106.23 (14)	C13—C12—H12A	109.3
C8—C1—C2	106.92 (15)	C11—C12—H12A	109.3
C8—C1—S1	125.59 (13)	C13—C12—H12B	109.3
C2—C1—S1	126.83 (13)	C11—C12—H12B	109.3
C7—C2—C3	118.91 (16)	H12A—C12—H12B	107.9
C7—C2—C1	104.97 (15)	C12—C13—C14	111.0 (2)
C3—C2—C1	136.11 (17)	C12—C13—H13A	109.4
C4—C3—C2	119.48 (17)	C14—C13—H13A	109.4
C4—C3—H3	120.3	C12—C13—H13B	109.4
C2—C3—H3	120.3	C14—C13—H13B	109.4
C3—C4—C5	119.46 (17)	H13A—C13—H13B	108.0
C3—C4—C9	120.00 (17)	C13—C14—C9	111.42 (18)
C5—C4—C9	120.51 (16)	C13—C14—H14A	109.3
C6—C5—C4	122.35 (17)	C9—C14—H14A	109.3
C6—C5—H5	118.8	C13—C14—H14B	109.3
C4—C5—H5	118.8	C9—C14—H14B	109.3
C7—C6—C5	116.31 (17)	H14A—C14—H14B	108.0
C7—C6—H6	121.8	C16—C15—C20	119.90 (18)
C5—C6—H6	121.8	C16—C15—C8	119.84 (18)
C6—C7—O1	125.82 (17)	C20—C15—C8	120.22 (18)
C6—C7—C2	123.48 (17)	C17—C16—C15	118.6 (2)
O1—C7—C2	110.69 (15)	C17—C16—H16	120.7
C1—C8—O1	111.19 (15)	C15—C16—H16	120.7
C1—C8—C15	132.60 (17)	F1—C17—C18	119.79 (19)
O1—C8—C15	116.14 (16)	F1—C17—C16	117.5 (2)
C4—C9—C10	113.34 (18)	C18—C17—C16	122.7 (2)
C4—C9—C14	110.48 (16)	C17—C18—C19	118.5 (2)
C10—C9—C14	111.02 (18)	C17—C18—H18	120.8
C4—C9—H9	107.2	C19—C18—H18	120.8
C10—C9—H9	107.2	C18—C19—C20	120.4 (2)
C14—C9—H9	107.2	C18—C19—H19	119.8
C9—C10—C11	111.7 (2)	C20—C19—H19	119.8
C9—C10—H10A	109.3	C19—C20—C15	119.9 (2)
C11—C10—H10A	109.3	C19—C20—H20	120.0
C9—C10—H10B	109.3	C15—C20—H20	120.0
C11—C10—H10B	109.3	S1—C21—H21A	109.5
H10A—C10—H10B	107.9	S1—C21—H21B	109.5
C12—C11—C10	111.8 (2)	H21A—C21—H21B	109.5
C12—C11—H11A	109.3	S1—C21—H21C	109.5
C10—C11—H11A	109.3	H21A—C21—H21C	109.5
C12—C11—H11B	109.3	H21B—C21—H21C	109.5
O2—S1—C1—C8	133.15 (16)	C7—O1—C8—C15	−176.61 (15)
C21—S1—C1—C8	−117.75 (17)	C3—C4—C9—C10	125.5 (2)
O2—S1—C1—C2	−36.29 (18)	C5—C4—C9—C10	−56.7 (2)
C21—S1—C1—C2	72.81 (18)	C3—C4—C9—C14	−109.2 (2)
C8—C1—C2—C7	1.11 (19)	C5—C4—C9—C14	68.6 (2)
S1—C1—C2—C7	172.15 (13)	C4—C9—C10—C11	178.61 (19)
C8—C1—C2—C3	−177.8 (2)	C14—C9—C10—C11	53.6 (3)
S1—C1—C2—C3	−6.8 (3)	C9—C10—C11—C12	−53.3 (3)
C7—C2—C3—C4	0.6 (3)	C10—C11—C12—C13	54.5 (3)
C1—C2—C3—C4	179.4 (2)	C11—C12—C13—C14	−55.9 (3)
C2—C3—C4—C5	−0.4 (3)	C12—C13—C14—C9	56.4 (3)
C2—C3—C4—C9	177.44 (16)	C4—C9—C14—C13	178.2 (2)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	−55.2 (3)
C9—C4—C5—C6	−177.75 (18)	C1—C8—C15—C16	39.0 (3)
C4—C5—C6—C7	0.0 (3)	O1—C8—C15—C16	−144.42 (19)
C5—C6—C7—O1	−178.59 (17)	C1—C8—C15—C20	−139.0 (2)
C5—C6—C7—C2	0.2 (3)	O1—C8—C15—C20	37.6 (2)
C8—O1—C7—C6	178.97 (17)	C20—C15—C16—C17	2.5 (3)
C8—O1—C7—C2	0.04 (19)	C8—C15—C16—C17	−175.5 (2)
C3—C2—C7—C6	−0.5 (3)	C15—C16—C17—F1	−179.1 (2)
C1—C2—C7—C6	−179.67 (17)	C15—C16—C17—C18	−1.3 (4)
C3—C2—C7—O1	178.43 (15)	F1—C17—C18—C19	176.9 (2)
C1—C2—C7—O1	−0.7 (2)	C16—C17—C18—C19	−0.9 (4)
C2—C1—C8—O1	−1.1 (2)	C17—C18—C19—C20	1.8 (3)
S1—C1—C8—O1	−172.33 (13)	C18—C19—C20—C15	−0.6 (3)
C2—C1—C8—C15	175.59 (19)	C16—C15—C20—C19	−1.6 (3)
S1—C1—C8—C15	4.4 (3)	C8—C15—C20—C19	176.39 (18)
C7—O1—C8—C1	0.71 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2i	0.98	2.30	3.276 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯O2i	0.98	2.30	3.276 (3)	176

Symmetry code: (i) .