3-Cyclo-hexyl-sulfonyl-5-fluoro-2-methyl-1-benzofuran.

In the title compound, C(15)H(17)FO(3)S, the cyclo-hexyl ring adopts a classic chair conformation and the aryl-sulfonyl unit is positioned equatorial relative to the cyclo-hexyl group. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the pharmacological 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 structural studies of related 3-aryl­sulfonyl-5-fluoro-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C15H17FO3S

M = 296.35

Monoclinic,

a = 5.5830 (4) Å

b = 26.879 (2) Å

c = 9.1092 (7) Å

β = 93.762 (1)°

V = 1364.04 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.23 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.654, T max = 0.746

12713 measured reflections

3141 independent reflections

2682 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.05

3141 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.38 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/S1600536811008580/jj2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008580/jj2079Isup2.hkl

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

C15H17FO3S	F(000) = 624
Mr = 296.35	Dx = 1.443 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4637 reflections
a = 5.5830 (4) Å	θ = 2.4–27.5°
b = 26.879 (2) Å	µ = 0.25 mm−1
c = 9.1092 (7) Å	T = 173 K
β = 93.762 (1)°	Block, colourless
V = 1364.04 (18) Å3	0.23 × 0.16 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3141 independent reflections
Radiation source: rotating anode	2682 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −34→34
Tmin = 0.654, Tmax = 0.746	l = −11→11
12713 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.046P)2 + 0.8694P] where P = (Fo2 + 2Fc2)/3
3141 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.38 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	0.43863 (7)	0.591832 (16)	0.47491 (4)	0.02169 (13)
F1	1.0284 (2)	0.65629 (5)	0.01106 (14)	0.0425 (3)
O1	0.2604 (2)	0.53800 (5)	0.08250 (13)	0.0277 (3)
O2	0.3535 (2)	0.55223 (5)	0.56384 (14)	0.0301 (3)
O3	0.6834 (2)	0.60843 (5)	0.50319 (14)	0.0305 (3)
C1	0.4053 (3)	0.57456 (6)	0.29077 (18)	0.0223 (3)
C2	0.5493 (3)	0.59124 (6)	0.17416 (18)	0.0229 (3)
C3	0.7474 (3)	0.62235 (7)	0.1628 (2)	0.0265 (4)
H3	0.8195	0.6395	0.2457	0.032*
C4	0.8324 (3)	0.62684 (7)	0.0254 (2)	0.0304 (4)
C5	0.7336 (4)	0.60331 (8)	−0.0995 (2)	0.0335 (4)
H5	0.8002	0.6083	−0.1917	0.040*
C6	0.5370 (4)	0.57253 (7)	−0.0889 (2)	0.0310 (4)
H6	0.4646	0.5558	−0.1723	0.037*
C7	0.4519 (3)	0.56741 (6)	0.04852 (19)	0.0256 (4)
C8	0.2371 (3)	0.54272 (6)	0.23030 (19)	0.0249 (4)
C9	0.0458 (4)	0.51238 (7)	0.2908 (2)	0.0324 (4)
H9A	0.1155	0.4817	0.3334	0.049*
H9B	−0.0752	0.5040	0.2119	0.049*
H9C	−0.0296	0.5313	0.3673	0.049*
C10	0.2431 (3)	0.64368 (6)	0.49108 (18)	0.0217 (3)
H10	0.0757	0.6320	0.4648	0.026*
C11	0.2542 (4)	0.66111 (7)	0.6511 (2)	0.0288 (4)
H11A	0.2134	0.6332	0.7157	0.035*
H11B	0.4190	0.6723	0.6813	0.035*
C12	0.0778 (4)	0.70386 (7)	0.6677 (2)	0.0356 (5)
H12A	−0.0881	0.6916	0.6464	0.043*
H12B	0.0916	0.7160	0.7705	0.043*
C13	0.1256 (4)	0.74662 (8)	0.5641 (2)	0.0397 (5)
H13A	0.0023	0.7727	0.5732	0.048*
H13B	0.2844	0.7614	0.5924	0.048*
C14	0.1207 (4)	0.72886 (7)	0.4055 (2)	0.0349 (4)
H14A	0.1623	0.7569	0.3415	0.042*
H14B	−0.0436	0.7177	0.3739	0.042*
C15	0.2966 (3)	0.68617 (7)	0.3869 (2)	0.0291 (4)
H15A	0.2820	0.6741	0.2840	0.035*
H15B	0.4630	0.6981	0.4086	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.0208 (2)	0.0277 (2)	0.0166 (2)	−0.00039 (16)	0.00182 (15)	−0.00055 (15)
F1	0.0383 (7)	0.0517 (8)	0.0391 (7)	−0.0079 (6)	0.0143 (6)	0.0069 (6)
O1	0.0329 (7)	0.0283 (7)	0.0215 (6)	−0.0016 (5)	−0.0005 (5)	−0.0035 (5)
O2	0.0399 (7)	0.0296 (7)	0.0212 (6)	−0.0001 (6)	0.0053 (6)	0.0035 (5)
O3	0.0188 (6)	0.0474 (8)	0.0251 (6)	−0.0011 (6)	0.0000 (5)	−0.0050 (6)
C1	0.0234 (8)	0.0253 (8)	0.0183 (8)	0.0014 (7)	0.0018 (7)	−0.0005 (6)
C2	0.0253 (8)	0.0250 (8)	0.0184 (8)	0.0054 (7)	0.0022 (7)	0.0008 (6)
C3	0.0268 (9)	0.0295 (9)	0.0232 (9)	0.0016 (7)	0.0022 (7)	0.0010 (7)
C4	0.0297 (9)	0.0318 (10)	0.0307 (10)	0.0031 (8)	0.0085 (8)	0.0061 (7)
C5	0.0421 (11)	0.0375 (10)	0.0218 (9)	0.0089 (9)	0.0096 (8)	0.0041 (8)
C6	0.0421 (11)	0.0324 (10)	0.0184 (8)	0.0081 (8)	0.0013 (8)	−0.0012 (7)
C7	0.0296 (9)	0.0244 (8)	0.0228 (9)	0.0044 (7)	0.0009 (7)	0.0003 (7)
C8	0.0280 (9)	0.0246 (8)	0.0219 (8)	0.0031 (7)	0.0017 (7)	−0.0012 (6)
C9	0.0324 (10)	0.0323 (10)	0.0326 (10)	−0.0060 (8)	0.0036 (8)	−0.0016 (8)
C10	0.0187 (7)	0.0258 (8)	0.0208 (8)	−0.0012 (7)	0.0036 (6)	−0.0013 (6)
C11	0.0336 (10)	0.0318 (9)	0.0215 (8)	0.0018 (8)	0.0056 (7)	−0.0019 (7)
C12	0.0421 (11)	0.0352 (10)	0.0307 (10)	0.0035 (9)	0.0102 (9)	−0.0065 (8)
C13	0.0495 (13)	0.0268 (10)	0.0433 (12)	0.0015 (9)	0.0070 (10)	−0.0050 (8)
C14	0.0401 (11)	0.0285 (9)	0.0366 (11)	0.0019 (8)	0.0058 (9)	0.0055 (8)
C15	0.0312 (9)	0.0311 (9)	0.0257 (9)	−0.0013 (8)	0.0068 (8)	0.0036 (7)

S1—O2	1.4373 (13)	C9—H9B	0.9800
S1—O3	1.4444 (13)	C9—H9C	0.9800
S1—C1	1.7386 (17)	C10—C15	1.527 (2)
S1—C10	1.7824 (17)	C10—C11	1.529 (2)
F1—C4	1.364 (2)	C10—H10	1.0000
O1—C8	1.367 (2)	C11—C12	1.527 (3)
O1—C7	1.381 (2)	C11—H11A	0.9900
C1—C8	1.360 (2)	C11—H11B	0.9900
C1—C2	1.445 (2)	C12—C13	1.521 (3)
C2—C7	1.391 (2)	C12—H12A	0.9900
C2—C3	1.396 (2)	C12—H12B	0.9900
C3—C4	1.373 (3)	C13—C14	1.521 (3)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.384 (3)	C13—H13B	0.9900
C5—C6	1.383 (3)	C14—C15	1.527 (3)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.375 (2)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C8—C9	1.479 (3)	C15—H15B	0.9900
C9—H9A	0.9800
O2—S1—O3	118.18 (8)	C15—C10—C11	111.49 (15)
O2—S1—C1	109.13 (8)	C15—C10—S1	112.80 (12)
O3—S1—C1	107.13 (8)	C11—C10—S1	109.37 (12)
O2—S1—C10	107.78 (8)	C15—C10—H10	107.7
O3—S1—C10	108.73 (8)	C11—C10—H10	107.7
C1—S1—C10	105.14 (8)	S1—C10—H10	107.7
C8—O1—C7	107.02 (13)	C12—C11—C10	109.78 (15)
C8—C1—C2	107.46 (15)	C12—C11—H11A	109.7
C8—C1—S1	125.88 (13)	C10—C11—H11A	109.7
C2—C1—S1	126.66 (13)	C12—C11—H11B	109.7
C7—C2—C3	118.95 (16)	C10—C11—H11B	109.7
C7—C2—C1	104.82 (15)	H11A—C11—H11B	108.2
C3—C2—C1	136.22 (17)	C13—C12—C11	111.51 (16)
C4—C3—C2	116.29 (17)	C13—C12—H12A	109.3
C4—C3—H3	121.9	C11—C12—H12A	109.3
C2—C3—H3	121.9	C13—C12—H12B	109.3
F1—C4—C3	117.75 (18)	C11—C12—H12B	109.3
F1—C4—C5	117.76 (17)	H12A—C12—H12B	108.0
C3—C4—C5	124.49 (18)	C14—C13—C12	111.04 (16)
C6—C5—C4	119.45 (17)	C14—C13—H13A	109.4
C6—C5—H5	120.3	C12—C13—H13A	109.4
C4—C5—H5	120.3	C14—C13—H13B	109.4
C7—C6—C5	116.54 (18)	C12—C13—H13B	109.4
C7—C6—H6	121.7	H13A—C13—H13B	108.0
C5—C6—H6	121.7	C13—C14—C15	111.70 (17)
C6—C7—O1	125.48 (17)	C13—C14—H14A	109.3
C6—C7—C2	124.28 (18)	C15—C14—H14A	109.3
O1—C7—C2	110.23 (15)	C13—C14—H14B	109.3
C1—C8—O1	110.46 (15)	C15—C14—H14B	109.3
C1—C8—C9	133.81 (17)	H14A—C14—H14B	107.9
O1—C8—C9	115.71 (16)	C10—C15—C14	109.86 (15)
C8—C9—H9A	109.5	C10—C15—H15A	109.7
C8—C9—H9B	109.5	C14—C15—H15A	109.7
H9A—C9—H9B	109.5	C10—C15—H15B	109.7
C8—C9—H9C	109.5	C14—C15—H15B	109.7
H9A—C9—H9C	109.5	H15A—C15—H15B	108.2
H9B—C9—H9C	109.5
O2—S1—C1—C8	28.15 (18)	C3—C2—C7—O1	179.22 (15)
O3—S1—C1—C8	157.20 (16)	C1—C2—C7—O1	0.18 (19)
C10—S1—C1—C8	−87.23 (17)	C2—C1—C8—O1	−0.6 (2)
O2—S1—C1—C2	−151.98 (15)	S1—C1—C8—O1	179.25 (12)
O3—S1—C1—C2	−22.93 (18)	C2—C1—C8—C9	177.52 (19)
C10—S1—C1—C2	92.64 (16)	S1—C1—C8—C9	−2.6 (3)
C8—C1—C2—C7	0.27 (19)	C7—O1—C8—C1	0.75 (19)
S1—C1—C2—C7	−179.62 (13)	C7—O1—C8—C9	−177.78 (15)
C8—C1—C2—C3	−178.5 (2)	O2—S1—C10—C15	−173.03 (13)
S1—C1—C2—C3	1.6 (3)	O3—S1—C10—C15	57.74 (15)
C7—C2—C3—C4	−0.2 (3)	C1—S1—C10—C15	−56.72 (14)
C1—C2—C3—C4	178.45 (19)	O2—S1—C10—C11	62.29 (14)
C2—C3—C4—F1	−178.89 (16)	O3—S1—C10—C11	−66.94 (13)
C2—C3—C4—C5	0.7 (3)	C1—S1—C10—C11	178.61 (12)
F1—C4—C5—C6	178.99 (17)	C15—C10—C11—C12	57.4 (2)
C3—C4—C5—C6	−0.6 (3)	S1—C10—C11—C12	−177.14 (13)
C4—C5—C6—C7	0.0 (3)	C10—C11—C12—C13	−56.3 (2)
C5—C6—C7—O1	−179.06 (17)	C11—C12—C13—C14	55.6 (2)
C5—C6—C7—C2	0.5 (3)	C12—C13—C14—C15	−55.5 (2)
C8—O1—C7—C6	179.06 (17)	C11—C10—C15—C14	−57.2 (2)
C8—O1—C7—C2	−0.56 (19)	S1—C10—C15—C14	179.30 (13)
C3—C2—C7—C6	−0.4 (3)	C13—C14—C15—C10	55.9 (2)
C1—C2—C7—C6	−179.45 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.44	3.306 (2)	151
C10—H10···O3ii	1.00	2.33	3.274 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.44	3.306 (2)	151
C10—H10⋯O3ii	1.00	2.33	3.274 (2)	157

Symmetry codes: (i) ; (ii) .