5-Cyclo-hexyl-3-(4-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

In the title compound, C(21)H(21)FO(3)S, the cyclo-hexyl ring adopts a chair conformation. The 4-fluoro-phenyl ring makes a dihedral angle of 77.71 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through inter-molecular C-H⋯O hydrogen bonds and aromatic π-π inter-actions between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.578 (2) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For our previous structural studies of related 3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzo­furan derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C21H21FO3S

M = 372.44

Triclinic,

a = 9.2014 (3) Å

b = 10.2563 (4) Å

c = 11.1105 (4) Å

α = 80.564 (2)°

β = 66.317 (2)°

γ = 71.825 (2)°

V = 911.41 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.33 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.640, T max = 0.746

15715 measured reflections

3967 independent reflections

3395 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.03

3967 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.39 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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006593/kp2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006593/kp2311Isup2.hkl

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

C21H21FO3S	Z = 2
Mr = 372.44	F(000) = 392
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2014 (3) Å	Cell parameters from 6718 reflections
b = 10.2563 (4) Å	θ = 2.5–27.5°
c = 11.1105 (4) Å	µ = 0.21 mm−1
α = 80.564 (2)°	T = 173 K
β = 66.317 (2)°	Block, colourless
γ = 71.825 (2)°	0.33 × 0.23 × 0.17 mm
V = 911.41 (6) Å3

Bruker SMART APEXII CCD diffractometer	3967 independent reflections
Radiation source: rotating anode	3395 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→13
Tmin = 0.640, Tmax = 0.746	l = −14→14
15715 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.3006P] where P = (Fo2 + 2Fc2)/3
3967 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.39 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	0.17745 (5)	0.50397 (4)	0.70139 (3)	0.03247 (12)
F1	0.60299 (14)	0.09412 (12)	0.93389 (12)	0.0614 (3)
O1	−0.07799 (13)	0.32075 (11)	0.61095 (11)	0.0385 (3)
O2	0.28066 (15)	0.57220 (12)	0.59295 (11)	0.0417 (3)
O3	0.04350 (14)	0.58296 (11)	0.80566 (11)	0.0418 (3)
C1	0.09922 (18)	0.40980 (15)	0.63832 (14)	0.0309 (3)
C2	0.19131 (19)	0.32218 (15)	0.52695 (14)	0.0313 (3)
C3	0.35461 (19)	0.28136 (15)	0.44039 (14)	0.0330 (3)
H3	0.4340	0.3158	0.4458	0.040*
C4	0.3973 (2)	0.18808 (16)	0.34550 (14)	0.0358 (3)
C5	0.2739 (2)	0.14063 (17)	0.33786 (16)	0.0414 (4)
H5	0.3033	0.0796	0.2734	0.050*
C6	0.1113 (2)	0.18053 (18)	0.42166 (17)	0.0425 (4)
H6	0.0307	0.1485	0.4152	0.051*
C7	0.0751 (2)	0.27039 (16)	0.51537 (15)	0.0351 (3)
C8	−0.06007 (19)	0.40433 (15)	0.68512 (15)	0.0345 (3)
C9	−0.2136 (2)	0.46764 (19)	0.79404 (17)	0.0441 (4)
H9A	−0.1905	0.5242	0.8411	0.066*
H9B	−0.2558	0.3968	0.8528	0.066*
H9C	−0.2941	0.5229	0.7588	0.066*
C10	0.5742 (2)	0.13649 (16)	0.25294 (15)	0.0388 (4)
H10	0.5752	0.0787	0.1905	0.047*
C11	0.6477 (2)	0.25270 (16)	0.17308 (15)	0.0379 (4)
H11A	0.5823	0.3044	0.1221	0.046*
H11B	0.6428	0.3146	0.2327	0.046*
C12	0.8261 (2)	0.19855 (17)	0.08055 (16)	0.0410 (4)
H12A	0.8295	0.1467	0.0135	0.049*
H12B	0.8707	0.2754	0.0371	0.049*
C13	0.9320 (2)	0.10759 (18)	0.15317 (18)	0.0467 (4)
H13A	0.9408	0.1624	0.2120	0.056*
H13B	1.0420	0.0693	0.0903	0.056*
C14	0.8602 (2)	−0.00825 (19)	0.23200 (19)	0.0583 (6)
H14A	0.9268	−0.0608	0.2818	0.070*
H14B	0.8633	−0.0693	0.1724	0.070*
C15	0.6827 (3)	0.0469 (2)	0.32611 (18)	0.0578 (6)
H15A	0.6810	0.1006	0.3911	0.069*
H15B	0.6385	−0.0295	0.3720	0.069*
C16	0.30614 (19)	0.38018 (15)	0.77139 (14)	0.0317 (3)
C17	0.2384 (2)	0.33178 (17)	0.90047 (15)	0.0383 (4)
H17	0.1261	0.3643	0.9490	0.046*
C18	0.3384 (2)	0.23538 (19)	0.95594 (17)	0.0451 (4)
H18	0.2956	0.2023	1.0423	0.054*
C19	0.5031 (2)	0.18935 (18)	0.88040 (18)	0.0418 (4)
C20	0.5731 (2)	0.23555 (18)	0.75333 (18)	0.0425 (4)
H20	0.6853	0.2018	0.7054	0.051*
C21	0.47341 (19)	0.33341 (17)	0.69787 (16)	0.0380 (4)
H21	0.5179	0.3676	0.6121	0.046*

	U11	U22	U33	U12	U13	U23
S1	0.0357 (2)	0.0309 (2)	0.0242 (2)	−0.00993 (15)	−0.00282 (15)	−0.00406 (14)
F1	0.0580 (7)	0.0651 (7)	0.0675 (8)	−0.0096 (6)	−0.0381 (6)	0.0045 (6)
O1	0.0357 (6)	0.0430 (6)	0.0352 (6)	−0.0116 (5)	−0.0113 (5)	−0.0005 (5)
O2	0.0492 (7)	0.0392 (6)	0.0311 (6)	−0.0191 (5)	−0.0055 (5)	0.0024 (5)
O3	0.0423 (7)	0.0381 (6)	0.0338 (6)	−0.0055 (5)	−0.0030 (5)	−0.0123 (5)
C1	0.0320 (7)	0.0300 (7)	0.0244 (7)	−0.0058 (6)	−0.0061 (6)	−0.0017 (6)
C2	0.0383 (8)	0.0287 (7)	0.0234 (7)	−0.0077 (6)	−0.0100 (6)	0.0011 (6)
C3	0.0385 (8)	0.0319 (7)	0.0246 (7)	−0.0094 (6)	−0.0076 (6)	−0.0024 (6)
C4	0.0465 (9)	0.0311 (7)	0.0239 (7)	−0.0096 (7)	−0.0082 (6)	−0.0008 (6)
C5	0.0599 (11)	0.0370 (8)	0.0280 (8)	−0.0156 (8)	−0.0140 (7)	−0.0041 (7)
C6	0.0528 (10)	0.0434 (9)	0.0378 (9)	−0.0184 (8)	−0.0193 (8)	−0.0024 (7)
C7	0.0389 (8)	0.0353 (8)	0.0293 (8)	−0.0097 (6)	−0.0125 (6)	0.0020 (6)
C8	0.0371 (8)	0.0316 (7)	0.0293 (8)	−0.0065 (6)	−0.0103 (6)	0.0018 (6)
C9	0.0323 (8)	0.0485 (10)	0.0398 (9)	−0.0063 (7)	−0.0046 (7)	−0.0040 (7)
C10	0.0493 (9)	0.0333 (8)	0.0253 (7)	−0.0097 (7)	−0.0042 (7)	−0.0074 (6)
C11	0.0438 (9)	0.0334 (8)	0.0310 (8)	−0.0074 (7)	−0.0116 (7)	0.0008 (6)
C12	0.0445 (9)	0.0400 (9)	0.0321 (8)	−0.0111 (7)	−0.0086 (7)	−0.0006 (7)
C13	0.0452 (10)	0.0423 (9)	0.0433 (10)	0.0000 (8)	−0.0129 (8)	−0.0103 (8)
C14	0.0573 (12)	0.0407 (10)	0.0444 (11)	0.0086 (8)	−0.0046 (9)	0.0026 (8)
C15	0.0613 (12)	0.0428 (10)	0.0350 (9)	0.0066 (9)	−0.0022 (8)	0.0068 (8)
C16	0.0339 (8)	0.0348 (8)	0.0248 (7)	−0.0130 (6)	−0.0051 (6)	−0.0051 (6)
C17	0.0347 (8)	0.0483 (9)	0.0248 (7)	−0.0129 (7)	−0.0022 (6)	−0.0037 (7)
C18	0.0496 (10)	0.0547 (10)	0.0290 (8)	−0.0177 (8)	−0.0120 (7)	0.0031 (7)
C19	0.0451 (9)	0.0420 (9)	0.0468 (10)	−0.0128 (7)	−0.0247 (8)	−0.0027 (7)
C20	0.0301 (8)	0.0481 (10)	0.0458 (10)	−0.0118 (7)	−0.0071 (7)	−0.0090 (8)
C21	0.0351 (8)	0.0440 (9)	0.0293 (8)	−0.0160 (7)	−0.0014 (6)	−0.0041 (7)

S1—O3	1.4336 (11)	C10—H10	0.9800
S1—O2	1.4360 (11)	C11—C12	1.524 (2)
S1—C1	1.7329 (16)	C11—H11A	0.9700
S1—C16	1.7599 (16)	C11—H11B	0.9700
F1—C19	1.3567 (19)	C12—C13	1.512 (2)
O1—C8	1.3675 (19)	C12—H12A	0.9700
O1—C7	1.3793 (19)	C12—H12B	0.9700
C1—C8	1.361 (2)	C13—C14	1.516 (3)
C1—C2	1.451 (2)	C13—H13A	0.9700
C2—C7	1.389 (2)	C13—H13B	0.9700
C2—C3	1.392 (2)	C14—C15	1.525 (2)
C3—C4	1.395 (2)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.403 (2)	C15—H15A	0.9700
C4—C10	1.511 (2)	C15—H15B	0.9700
C5—C6	1.378 (2)	C16—C21	1.387 (2)
C5—H5	0.9300	C16—C17	1.390 (2)
C6—C7	1.374 (2)	C17—C18	1.376 (2)
C6—H6	0.9300	C17—H17	0.9300
C8—C9	1.481 (2)	C18—C19	1.373 (2)
C9—H9A	0.9600	C18—H18	0.9300
C9—H9B	0.9600	C19—C20	1.369 (2)
C9—H9C	0.9600	C20—C21	1.381 (2)
C10—C15	1.529 (3)	C20—H20	0.9300
C10—C11	1.530 (2)	C21—H21	0.9300
O3—S1—O2	119.61 (7)	C12—C11—H11B	109.2
O3—S1—C1	108.35 (7)	C10—C11—H11B	109.2
O2—S1—C1	107.95 (7)	H11A—C11—H11B	107.9
O3—S1—C16	107.80 (7)	C13—C12—C11	111.76 (13)
O2—S1—C16	107.38 (7)	C13—C12—H12A	109.3
C1—S1—C16	104.78 (7)	C11—C12—H12A	109.3
C8—O1—C7	107.23 (12)	C13—C12—H12B	109.3
C8—C1—C2	107.66 (14)	C11—C12—H12B	109.3
C8—C1—S1	125.98 (12)	H12A—C12—H12B	107.9
C2—C1—S1	126.35 (12)	C12—C13—C14	111.51 (16)
C7—C2—C3	119.17 (14)	C12—C13—H13A	109.3
C7—C2—C1	104.49 (13)	C14—C13—H13A	109.3
C3—C2—C1	136.33 (15)	C12—C13—H13B	109.3
C2—C3—C4	118.99 (15)	C14—C13—H13B	109.3
C2—C3—H3	120.5	H13A—C13—H13B	108.0
C4—C3—H3	120.5	C13—C14—C15	111.21 (15)
C3—C4—C5	119.14 (15)	C13—C14—H14A	109.4
C3—C4—C10	120.85 (15)	C15—C14—H14A	109.4
C5—C4—C10	120.00 (14)	C13—C14—H14B	109.4
C6—C5—C4	122.90 (15)	C15—C14—H14B	109.4
C6—C5—H5	118.5	H14A—C14—H14B	108.0
C4—C5—H5	118.5	C14—C15—C10	111.44 (14)
C7—C6—C5	116.07 (16)	C14—C15—H15A	109.3
C7—C6—H6	122.0	C10—C15—H15A	109.3
C5—C6—H6	122.0	C14—C15—H15B	109.3
C6—C7—O1	125.83 (15)	C10—C15—H15B	109.3
C6—C7—C2	123.71 (15)	H15A—C15—H15B	108.0
O1—C7—C2	110.46 (13)	C21—C16—C17	121.00 (15)
C1—C8—O1	110.16 (13)	C21—C16—S1	119.73 (12)
C1—C8—C9	135.13 (15)	C17—C16—S1	119.26 (12)
O1—C8—C9	114.70 (14)	C18—C17—C16	119.55 (15)
C8—C9—H9A	109.5	C18—C17—H17	120.2
C8—C9—H9B	109.5	C16—C17—H17	120.2
H9A—C9—H9B	109.5	C19—C18—C17	118.27 (15)
C8—C9—H9C	109.5	C19—C18—H18	120.9
H9A—C9—H9C	109.5	C17—C18—H18	120.9
H9B—C9—H9C	109.5	F1—C19—C20	117.78 (16)
C4—C10—C15	111.52 (13)	F1—C19—C18	118.83 (16)
C4—C10—C11	112.73 (13)	C20—C19—C18	123.39 (16)
C15—C10—C11	110.17 (15)	C19—C20—C21	118.49 (15)
C4—C10—H10	107.4	C19—C20—H20	120.8
C15—C10—H10	107.4	C21—C20—H20	120.8
C11—C10—H10	107.4	C20—C21—C16	119.29 (15)
C12—C11—C10	111.90 (13)	C20—C21—H21	120.4
C12—C11—H11A	109.2	C16—C21—H21	120.4
C10—C11—H11A	109.2
O3—S1—C1—C8	−4.02 (16)	C7—O1—C8—C9	−179.75 (13)
O2—S1—C1—C8	−134.92 (14)	C3—C4—C10—C15	67.17 (19)
C16—S1—C1—C8	110.87 (14)	C5—C4—C10—C15	−111.92 (18)
O3—S1—C1—C2	176.35 (12)	C3—C4—C10—C11	−57.37 (19)
O2—S1—C1—C2	45.45 (15)	C5—C4—C10—C11	123.54 (16)
C16—S1—C1—C2	−68.77 (14)	C4—C10—C11—C12	179.92 (14)
C8—C1—C2—C7	0.40 (16)	C15—C10—C11—C12	54.64 (18)
S1—C1—C2—C7	−179.91 (11)	C10—C11—C12—C13	−54.48 (19)
C8—C1—C2—C3	−178.10 (16)	C11—C12—C13—C14	54.41 (19)
S1—C1—C2—C3	1.6 (3)	C12—C13—C14—C15	−55.3 (2)
C7—C2—C3—C4	−0.8 (2)	C13—C14—C15—C10	56.3 (2)
C1—C2—C3—C4	177.49 (15)	C4—C10—C15—C14	178.45 (16)
C2—C3—C4—C5	1.5 (2)	C11—C10—C15—C14	−55.6 (2)
C2—C3—C4—C10	−177.55 (13)	O3—S1—C16—C21	−150.86 (13)
C3—C4—C5—C6	−1.0 (2)	O2—S1—C16—C21	−20.74 (15)
C10—C4—C5—C6	178.11 (15)	C1—S1—C16—C21	93.88 (13)
C4—C5—C6—C7	−0.3 (2)	O3—S1—C16—C17	28.49 (15)
C5—C6—C7—O1	−178.25 (14)	O2—S1—C16—C17	158.60 (13)
C5—C6—C7—C2	1.0 (2)	C1—S1—C16—C17	−86.78 (14)
C8—O1—C7—C6	178.84 (15)	C21—C16—C17—C18	−0.4 (2)
C8—O1—C7—C2	−0.53 (16)	S1—C16—C17—C18	−179.76 (13)
C3—C2—C7—C6	−0.5 (2)	C16—C17—C18—C19	−0.5 (3)
C1—C2—C7—C6	−179.30 (15)	C17—C18—C19—F1	−179.88 (15)
C3—C2—C7—O1	178.90 (12)	C17—C18—C19—C20	0.8 (3)
C1—C2—C7—O1	0.08 (16)	F1—C19—C20—C21	−179.41 (14)
C2—C1—C8—O1	−0.74 (17)	C18—C19—C20—C21	0.0 (3)
S1—C1—C8—O1	179.56 (10)	C19—C20—C21—C16	−0.9 (2)
C2—C1—C8—C9	179.96 (16)	C17—C16—C21—C20	1.1 (2)
S1—C1—C8—C9	0.3 (3)	S1—C16—C21—C20	−179.53 (12)
C7—O1—C8—C1	0.79 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O3i	0.93	2.59	3.2970 (19)	133
C20—H20···O1ii	0.93	2.60	3.285 (2)	131
C21—H21···O2iii	0.93	2.42	3.3114 (19)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O3i	0.93	2.59	3.2970 (19)	133
C20—H20⋯O1ii	0.93	2.60	3.285 (2)	131
C21—H21⋯O2iii	0.93	2.42	3.3114 (19)	160

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