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

In the title compound, C21H21FO3S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo-furan ring system and the fluoro-phenyl ring is 87.61 (3)°. In the crystal, mol-ecules related by inversion are linked into dimers via pairs of C-H⋯π inter-actions. These dimers are further linked by π-π inter-actions between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.407 (2) Å and between the 2-fluoro-phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.742 (2) Å], resulting in a three-dimensional supra-molecular network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012 ▶, 2014 ▶).

Experimental

Crystal data

C21H21FO3S

M = 372.44

Triclinic,

a = 9.0481 (2) Å

b = 10.5301 (2) Å

c = 10.6312 (2) Å

α = 106.025 (1)°

β = 92.561 (1)°

γ = 110.852 (1)°

V = 898.19 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.32 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.683, T max = 0.746

16579 measured reflections

4423 independent reflections

3920 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.04

4423 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.37 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) I. DOI: 10.1107/S1600536814005960/zs2290sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005960/zs2290Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005960/zs2290Isup3.cml

CCDC reference: 992238

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H21FO3S	Z = 2
Mr = 372.44	F(000) = 392
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Melting point = 437–438 K
a = 9.0481 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5301 (2) Å	Cell parameters from 3275 reflections
c = 10.6312 (2) Å	θ = 2.6–28.0°
α = 106.025 (1)°	µ = 0.21 mm−1
β = 92.561 (1)°	T = 173 K
γ = 110.852 (1)°	Block, colourless
V = 898.19 (3) Å3	0.32 × 0.18 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	4423 independent reflections
Radiation source: rotating anode	3920 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→12
Tmin = 0.683, Tmax = 0.746	l = −14→13
16579 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.3871P] where P = (Fo2 + 2Fc2)/3
4423 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.37 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	0.23801 (4)	0.57051 (4)	0.70681 (3)	0.02569 (11)
F1	0.28674 (11)	0.45682 (12)	0.92462 (9)	0.0410 (2)
O1	0.53546 (11)	0.38158 (11)	0.59971 (10)	0.0263 (2)
O2	0.15677 (13)	0.59421 (12)	0.60205 (11)	0.0343 (2)
O3	0.34140 (14)	0.69153 (11)	0.81440 (11)	0.0354 (3)
C1	0.34106 (16)	0.46540 (14)	0.63767 (13)	0.0233 (3)
C2	0.27505 (16)	0.33440 (14)	0.52683 (13)	0.0225 (3)
C3	0.12613 (16)	0.25272 (14)	0.44701 (14)	0.0254 (3)
H3	0.0394	0.2835	0.4575	0.030*
C4	0.10766 (17)	0.12480 (15)	0.35152 (14)	0.0276 (3)
C5	0.23950 (19)	0.08429 (16)	0.33530 (15)	0.0318 (3)
H5	0.2257	−0.0022	0.2686	0.038*
C6	0.38875 (18)	0.16516 (16)	0.41251 (15)	0.0309 (3)
H6	0.4774	0.1373	0.4000	0.037*
C7	0.40081 (16)	0.28817 (15)	0.50839 (14)	0.0248 (3)
C8	0.49546 (16)	0.48773 (15)	0.67799 (13)	0.0247 (3)
C9	−0.05240 (18)	0.02861 (15)	0.26472 (16)	0.0320 (3)
H9	−0.0466	−0.0665	0.2220	0.038*
C10	−0.08901 (18)	0.08408 (18)	0.15404 (15)	0.0346 (3)
H10A	−0.0001	0.0985	0.1017	0.042*
H10B	−0.0975	0.1777	0.1930	0.042*
C11	−0.2454 (2)	−0.0209 (2)	0.06288 (17)	0.0457 (4)
H11A	−0.2689	0.0201	−0.0052	0.055*
H11B	−0.2325	−0.1110	0.0167	0.055*
C12	−0.38452 (19)	−0.05379 (19)	0.13816 (18)	0.0398 (4)
H12A	−0.4088	0.0329	0.1722	0.048*
H12B	−0.4803	−0.1295	0.0771	0.048*
C13	−0.3493 (2)	−0.1026 (2)	0.2526 (2)	0.0520 (5)
H13A	−0.3422	−0.1974	0.2178	0.062*
H13B	−0.4383	−0.1133	0.3047	0.062*
C14	−0.1923 (2)	0.0033 (2)	0.34305 (19)	0.0509 (5)
H14A	−0.1703	−0.0346	0.4141	0.061*
H14B	−0.2030	0.0954	0.3852	0.061*
C15	0.62304 (18)	0.59702 (17)	0.78620 (15)	0.0318 (3)
H15A	0.5870	0.6729	0.8309	0.048*
H15B	0.7197	0.6380	0.7494	0.048*
H15C	0.6469	0.5526	0.8501	0.048*
C16	0.08913 (16)	0.45768 (15)	0.77301 (14)	0.0255 (3)
C17	−0.07163 (18)	0.41291 (16)	0.72256 (15)	0.0315 (3)
H17	−0.1022	0.4380	0.6491	0.038*
C18	−0.18705 (19)	0.33113 (17)	0.78072 (18)	0.0376 (4)
H18	−0.2973	0.3007	0.7473	0.045*
C19	−0.1428 (2)	0.29361 (17)	0.88695 (17)	0.0374 (4)
H19	−0.2231	0.2390	0.9268	0.045*
C20	0.0174 (2)	0.33479 (17)	0.93587 (16)	0.0342 (3)
H20	0.0482	0.3075	1.0077	0.041*
C21	0.13039 (17)	0.41607 (16)	0.87779 (14)	0.0293 (3)

	U11	U22	U33	U12	U13	U23
S1	0.02763 (18)	0.02397 (18)	0.02401 (18)	0.01045 (14)	0.00101 (13)	0.00503 (13)
F1	0.0303 (5)	0.0630 (6)	0.0340 (5)	0.0184 (5)	0.0005 (4)	0.0216 (5)
O1	0.0215 (5)	0.0309 (5)	0.0253 (5)	0.0089 (4)	0.0023 (4)	0.0084 (4)
O2	0.0394 (6)	0.0362 (6)	0.0336 (6)	0.0197 (5)	0.0025 (5)	0.0142 (5)
O3	0.0368 (6)	0.0255 (5)	0.0337 (6)	0.0086 (4)	−0.0001 (5)	−0.0009 (4)
C1	0.0234 (6)	0.0234 (6)	0.0205 (6)	0.0065 (5)	0.0022 (5)	0.0065 (5)
C2	0.0239 (6)	0.0223 (6)	0.0205 (6)	0.0071 (5)	0.0038 (5)	0.0079 (5)
C3	0.0231 (6)	0.0238 (6)	0.0273 (7)	0.0070 (5)	0.0009 (5)	0.0082 (5)
C4	0.0290 (7)	0.0223 (6)	0.0272 (7)	0.0056 (5)	−0.0003 (5)	0.0077 (5)
C5	0.0374 (8)	0.0248 (7)	0.0292 (7)	0.0118 (6)	0.0033 (6)	0.0031 (6)
C6	0.0302 (7)	0.0318 (7)	0.0327 (8)	0.0150 (6)	0.0070 (6)	0.0086 (6)
C7	0.0219 (6)	0.0273 (7)	0.0238 (6)	0.0065 (5)	0.0034 (5)	0.0100 (5)
C8	0.0251 (6)	0.0263 (6)	0.0221 (6)	0.0075 (5)	0.0033 (5)	0.0100 (5)
C9	0.0326 (7)	0.0203 (6)	0.0352 (8)	0.0059 (6)	−0.0056 (6)	0.0040 (6)
C10	0.0299 (7)	0.0409 (8)	0.0268 (7)	0.0060 (6)	0.0033 (6)	0.0112 (6)
C11	0.0358 (9)	0.0595 (11)	0.0302 (8)	0.0076 (8)	−0.0027 (7)	0.0117 (8)
C12	0.0289 (8)	0.0385 (9)	0.0431 (9)	0.0060 (7)	−0.0025 (7)	0.0096 (7)
C13	0.0365 (9)	0.0476 (10)	0.0545 (11)	−0.0088 (8)	−0.0055 (8)	0.0247 (9)
C14	0.0373 (9)	0.0574 (11)	0.0387 (9)	−0.0108 (8)	−0.0028 (7)	0.0252 (9)
C15	0.0266 (7)	0.0334 (8)	0.0284 (7)	0.0063 (6)	−0.0041 (6)	0.0074 (6)
C16	0.0262 (7)	0.0264 (6)	0.0226 (6)	0.0117 (5)	0.0032 (5)	0.0039 (5)
C17	0.0289 (7)	0.0324 (7)	0.0306 (7)	0.0136 (6)	−0.0001 (6)	0.0043 (6)
C18	0.0265 (7)	0.0330 (8)	0.0466 (9)	0.0093 (6)	0.0032 (7)	0.0055 (7)
C19	0.0366 (8)	0.0283 (7)	0.0439 (9)	0.0107 (6)	0.0135 (7)	0.0076 (7)
C20	0.0406 (8)	0.0345 (8)	0.0306 (8)	0.0172 (7)	0.0098 (6)	0.0108 (6)
C21	0.0279 (7)	0.0337 (7)	0.0252 (7)	0.0138 (6)	0.0017 (5)	0.0054 (6)

S1—O2	1.4331 (11)	C10—H10B	0.9900
S1—O3	1.4347 (11)	C11—C12	1.509 (2)
S1—C1	1.7267 (14)	C11—H11A	0.9900
S1—C16	1.7688 (15)	C11—H11B	0.9900
F1—C21	1.3492 (17)	C12—C13	1.508 (3)
O1—C8	1.3690 (17)	C12—H12A	0.9900
O1—C7	1.3814 (16)	C12—H12B	0.9900
C1—C8	1.3593 (19)	C13—C14	1.531 (2)
C1—C2	1.4495 (18)	C13—H13A	0.9900
C2—C7	1.3900 (19)	C13—H13B	0.9900
C2—C3	1.3948 (18)	C14—H14A	0.9900
C3—C4	1.3938 (19)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.405 (2)	C15—H15B	0.9800
C4—C9	1.5149 (19)	C15—H15C	0.9800
C5—C6	1.385 (2)	C16—C21	1.386 (2)
C5—H5	0.9500	C16—C17	1.389 (2)
C6—C7	1.374 (2)	C17—C18	1.388 (2)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.4781 (19)	C18—C19	1.382 (2)
C9—C10	1.523 (2)	C18—H18	0.9500
C9—C14	1.531 (2)	C19—C20	1.386 (2)
C9—H9	1.0000	C19—H19	0.9500
C10—C11	1.528 (2)	C20—C21	1.373 (2)
C10—H10A	0.9900	C20—H20	0.9500
O2—S1—O3	118.98 (7)	C12—C11—H11B	109.2
O2—S1—C1	108.44 (7)	C10—C11—H11B	109.2
O3—S1—C1	109.88 (7)	H11A—C11—H11B	107.9
O2—S1—C16	106.95 (7)	C13—C12—C11	111.81 (15)
O3—S1—C16	108.27 (7)	C13—C12—H12A	109.3
C1—S1—C16	103.14 (6)	C11—C12—H12A	109.3
C8—O1—C7	107.02 (10)	C13—C12—H12B	109.3
C8—C1—C2	107.83 (12)	C11—C12—H12B	109.3
C8—C1—S1	126.81 (11)	H12A—C12—H12B	107.9
C2—C1—S1	125.35 (10)	C12—C13—C14	111.71 (14)
C7—C2—C3	119.77 (13)	C12—C13—H13A	109.3
C7—C2—C1	104.36 (12)	C14—C13—H13A	109.3
C3—C2—C1	135.83 (13)	C12—C13—H13B	109.3
C4—C3—C2	118.38 (13)	C14—C13—H13B	109.3
C4—C3—H3	120.8	H13A—C13—H13B	107.9
C2—C3—H3	120.8	C13—C14—C9	111.01 (16)
C3—C4—C5	119.56 (13)	C13—C14—H14A	109.4
C3—C4—C9	121.05 (13)	C9—C14—H14A	109.4
C5—C4—C9	119.40 (13)	C13—C14—H14B	109.4
C6—C5—C4	122.76 (14)	C9—C14—H14B	109.4
C6—C5—H5	118.6	H14A—C14—H14B	108.0
C4—C5—H5	118.6	C8—C15—H15A	109.5
C7—C6—C5	115.93 (14)	C8—C15—H15B	109.5
C7—C6—H6	122.0	H15A—C15—H15B	109.5
C5—C6—H6	122.0	C8—C15—H15C	109.5
C6—C7—O1	125.87 (13)	H15A—C15—H15C	109.5
C6—C7—C2	123.55 (13)	H15B—C15—H15C	109.5
O1—C7—C2	110.57 (12)	C21—C16—C17	119.12 (14)
C1—C8—O1	110.21 (12)	C21—C16—S1	120.80 (11)
C1—C8—C15	134.27 (13)	C17—C16—S1	120.05 (11)
O1—C8—C15	115.50 (12)	C18—C17—C16	119.21 (15)
C4—C9—C10	112.58 (12)	C18—C17—H17	120.4
C4—C9—C14	113.05 (13)	C16—C17—H17	120.4
C10—C9—C14	109.00 (14)	C19—C18—C17	120.51 (15)
C4—C9—H9	107.3	C19—C18—H18	119.7
C10—C9—H9	107.3	C17—C18—H18	119.7
C14—C9—H9	107.3	C18—C19—C20	120.68 (15)
C9—C10—C11	111.03 (13)	C18—C19—H19	119.7
C9—C10—H10A	109.4	C20—C19—H19	119.7
C11—C10—H10A	109.4	C21—C20—C19	118.24 (15)
C9—C10—H10B	109.4	C21—C20—H20	120.9
C11—C10—H10B	109.4	C19—C20—H20	120.9
H10A—C10—H10B	108.0	F1—C21—C20	118.76 (14)
C12—C11—C10	112.06 (14)	F1—C21—C16	119.04 (13)
C12—C11—H11A	109.2	C20—C21—C16	122.20 (14)
C10—C11—H11A	109.2
O2—S1—C1—C8	133.20 (13)	C7—O1—C8—C15	177.95 (11)
O3—S1—C1—C8	1.62 (15)	C3—C4—C9—C10	76.96 (18)
C16—S1—C1—C8	−113.64 (13)	C5—C4—C9—C10	−103.00 (16)
O2—S1—C1—C2	−48.36 (13)	C3—C4—C9—C14	−47.1 (2)
O3—S1—C1—C2	−179.93 (11)	C5—C4—C9—C14	132.94 (16)
C16—S1—C1—C2	64.81 (12)	C4—C9—C10—C11	175.95 (14)
C8—C1—C2—C7	−0.63 (14)	C14—C9—C10—C11	−57.79 (18)
S1—C1—C2—C7	−179.32 (10)	C9—C10—C11—C12	56.0 (2)
C8—C1—C2—C3	177.13 (15)	C10—C11—C12—C13	−53.0 (2)
S1—C1—C2—C3	−1.6 (2)	C11—C12—C13—C14	53.1 (2)
C7—C2—C3—C4	0.93 (19)	C12—C13—C14—C9	−56.2 (2)
C1—C2—C3—C4	−176.57 (14)	C4—C9—C14—C13	−176.00 (15)
C2—C3—C4—C5	−2.1 (2)	C10—C9—C14—C13	58.0 (2)
C2—C3—C4—C9	177.92 (13)	O2—S1—C16—C21	−179.39 (11)
C3—C4—C5—C6	1.3 (2)	O3—S1—C16—C21	−50.05 (13)
C9—C4—C5—C6	−178.75 (14)	C1—S1—C16—C21	66.36 (13)
C4—C5—C6—C7	0.8 (2)	O2—S1—C16—C17	−1.21 (14)
C5—C6—C7—O1	177.24 (13)	O3—S1—C16—C17	128.13 (12)
C5—C6—C7—C2	−2.0 (2)	C1—S1—C16—C17	−115.46 (12)
C8—O1—C7—C6	−178.82 (13)	C21—C16—C17—C18	1.8 (2)
C8—O1—C7—C2	0.53 (14)	S1—C16—C17—C18	−176.37 (11)
C3—C2—C7—C6	1.2 (2)	C16—C17—C18—C19	−0.5 (2)
C1—C2—C7—C6	179.43 (13)	C17—C18—C19—C20	−1.1 (2)
C3—C2—C7—O1	−178.14 (11)	C18—C19—C20—C21	1.3 (2)
C1—C2—C7—O1	0.06 (14)	C19—C20—C21—F1	179.99 (13)
C2—C1—C8—O1	0.99 (15)	C19—C20—C21—C16	0.1 (2)
S1—C1—C8—O1	179.66 (9)	C17—C16—C21—F1	178.43 (13)
C2—C1—C8—C15	−177.62 (14)	S1—C16—C21—F1	−3.38 (19)
S1—C1—C8—C15	1.0 (2)	C17—C16—C21—C20	−1.7 (2)
C7—O1—C8—C1	−0.95 (15)	S1—C16—C21—C20	176.52 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg2i	0.99	2.73	3.644 (2)	154
C15—H15B···Cg2ii	0.98	2.80	3.454 (2)	125

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
C14—H14A⋯Cg2i	0.99	2.73	3.644 (2)	154
C15—H15B⋯Cg2ii	0.98	2.80	3.454 (2)	125

Symmetry codes: (i) ; (ii) .