5-Cyclo-hexyl-2-(4-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 classic chair conformation. The 4-fluoro-phenyl ring makes a dihedral angle of 31.05 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

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 2-(4-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan derivatives, see: Choi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C21H21FO2S

M = 356.44

Orthorhombic,

a = 16.4070 (6) Å

b = 11.3751 (4) Å

c = 18.7490 (7) Å

V = 3499.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.26 × 0.17 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.972

17170 measured reflections

4007 independent reflections

3190 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 0.93

4007 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.44 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/S1600536811002297/fl2333sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002297/fl2333Isup2.hkl

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

C21H21FO2S	F(000) = 1504
Mr = 356.44	Dx = 1.353 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4239 reflections
a = 16.4070 (6) Å	θ = 2.2–27.3°
b = 11.3751 (4) Å	µ = 0.21 mm−1
c = 18.7490 (7) Å	T = 173 K
V = 3499.1 (2) Å3	Block, colourless
Z = 8	0.26 × 0.17 × 0.14 mm

Bruker SMART APEXII CCD diffractometer	4007 independent reflections
Radiation source: rotating anode	3190 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −21→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.949, Tmax = 0.972	l = −24→23
17170 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) = 0.112	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0621P)2 + 1.9145P] where P = (Fo2 + 2Fc2)/3
4007 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.44 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	0.22808 (2)	0.03255 (4)	0.46770 (2)	0.02460 (12)
F1	0.19074 (7)	−0.29503 (10)	0.76480 (6)	0.0432 (3)
O1	0.42443 (7)	0.03716 (10)	0.59102 (6)	0.0241 (3)
O2	0.20712 (7)	0.14989 (11)	0.43665 (7)	0.0324 (3)
C1	0.32425 (9)	0.04757 (14)	0.50865 (8)	0.0215 (3)
C2	0.38848 (9)	0.12710 (14)	0.48685 (8)	0.0215 (3)
C3	0.39949 (9)	0.20728 (14)	0.43111 (8)	0.0220 (3)
H3	0.3591	0.2159	0.3952	0.026*
C4	0.47040 (9)	0.27410 (15)	0.42914 (8)	0.0231 (3)
C5	0.52971 (9)	0.25870 (15)	0.48281 (8)	0.0256 (3)
H5	0.5784	0.3037	0.4805	0.031*
C6	0.51959 (10)	0.18048 (16)	0.53860 (8)	0.0259 (4)
H6	0.5598	0.1711	0.5746	0.031*
C7	0.44797 (9)	0.11676 (15)	0.53917 (8)	0.0227 (3)
C8	0.34835 (10)	−0.00304 (15)	0.57127 (8)	0.0227 (3)
C9	0.30871 (10)	−0.08261 (14)	0.62133 (8)	0.0231 (3)
C10	0.32514 (10)	−0.07323 (15)	0.69434 (8)	0.0246 (3)
H10	0.3633	−0.0165	0.7106	0.030*
C11	0.28651 (10)	−0.14560 (15)	0.74306 (8)	0.0272 (4)
H11	0.2980	−0.1402	0.7926	0.033*
C12	0.23105 (11)	−0.22544 (15)	0.71749 (9)	0.0286 (4)
C13	0.21323 (11)	−0.23782 (16)	0.64647 (9)	0.0310 (4)
H13	0.1742	−0.2940	0.6310	0.037*
C14	0.25320 (11)	−0.16691 (15)	0.59778 (8)	0.0292 (4)
H14	0.2428	−0.1757	0.5482	0.035*
C15	0.48353 (9)	0.35926 (14)	0.36836 (8)	0.0229 (3)
H15	0.4301	0.3682	0.3433	0.028*
C16	0.51036 (12)	0.48237 (16)	0.39185 (9)	0.0314 (4)
H16A	0.4695	0.5153	0.4252	0.038*
H16B	0.5631	0.4770	0.4173	0.038*
C17	0.51939 (12)	0.56396 (17)	0.32774 (10)	0.0364 (4)
H17A	0.4654	0.5758	0.3053	0.044*
H17B	0.5395	0.6415	0.3440	0.044*
C18	0.57831 (12)	0.51361 (19)	0.27288 (11)	0.0406 (5)
H18A	0.6338	0.5108	0.2936	0.049*
H18B	0.5799	0.5658	0.2306	0.049*
C19	0.55313 (12)	0.39042 (18)	0.24985 (9)	0.0370 (4)
H19A	0.5007	0.3944	0.2238	0.044*
H19B	0.5947	0.3579	0.2171	0.044*
C20	0.54405 (11)	0.30958 (16)	0.31408 (9)	0.0293 (4)
H20A	0.5978	0.2992	0.3372	0.035*
H20B	0.5250	0.2314	0.2979	0.035*
C21	0.26034 (12)	−0.05707 (17)	0.39440 (9)	0.0338 (4)
H21A	0.2153	−0.0659	0.3605	0.051*
H21B	0.2766	−0.1347	0.4121	0.051*
H21C	0.3067	−0.0197	0.3705	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0214 (2)	0.0258 (2)	0.0266 (2)	−0.00355 (16)	−0.00049 (14)	0.00255 (16)
F1	0.0587 (7)	0.0383 (7)	0.0326 (6)	−0.0129 (6)	0.0100 (5)	0.0092 (5)
O1	0.0261 (6)	0.0242 (6)	0.0221 (5)	−0.0022 (5)	−0.0018 (4)	0.0027 (4)
O2	0.0283 (6)	0.0280 (7)	0.0411 (7)	0.0044 (5)	−0.0038 (5)	0.0052 (6)
C1	0.0241 (7)	0.0195 (8)	0.0208 (7)	−0.0006 (6)	0.0002 (6)	−0.0027 (6)
C2	0.0212 (7)	0.0208 (8)	0.0224 (7)	−0.0001 (6)	0.0002 (5)	−0.0035 (6)
C3	0.0219 (7)	0.0239 (8)	0.0201 (7)	−0.0008 (6)	−0.0009 (5)	−0.0011 (6)
C4	0.0238 (7)	0.0227 (9)	0.0228 (7)	0.0008 (6)	0.0020 (6)	−0.0006 (6)
C5	0.0217 (7)	0.0276 (9)	0.0273 (8)	−0.0034 (7)	−0.0006 (6)	−0.0013 (7)
C6	0.0233 (7)	0.0297 (9)	0.0248 (8)	−0.0004 (7)	−0.0039 (6)	−0.0010 (7)
C7	0.0253 (7)	0.0221 (8)	0.0207 (7)	0.0020 (7)	0.0005 (6)	−0.0002 (6)
C8	0.0248 (7)	0.0203 (8)	0.0230 (7)	−0.0005 (6)	−0.0006 (6)	−0.0019 (6)
C9	0.0277 (8)	0.0183 (8)	0.0232 (7)	0.0011 (6)	0.0011 (6)	0.0007 (6)
C10	0.0280 (8)	0.0222 (9)	0.0237 (7)	0.0009 (7)	−0.0020 (6)	−0.0004 (6)
C11	0.0343 (9)	0.0264 (9)	0.0209 (7)	0.0055 (7)	0.0007 (6)	0.0013 (7)
C12	0.0374 (9)	0.0218 (9)	0.0265 (8)	0.0018 (7)	0.0082 (6)	0.0049 (7)
C13	0.0408 (9)	0.0224 (9)	0.0299 (9)	−0.0071 (8)	−0.0003 (7)	−0.0013 (7)
C14	0.0415 (9)	0.0244 (9)	0.0218 (7)	−0.0028 (8)	−0.0013 (7)	−0.0008 (7)
C15	0.0224 (7)	0.0226 (8)	0.0238 (7)	−0.0018 (6)	0.0006 (6)	0.0018 (6)
C16	0.0389 (9)	0.0244 (9)	0.0309 (9)	−0.0017 (8)	0.0008 (7)	−0.0033 (7)
C17	0.0420 (10)	0.0249 (10)	0.0423 (10)	−0.0038 (8)	−0.0001 (8)	0.0046 (8)
C18	0.0394 (10)	0.0375 (11)	0.0449 (11)	−0.0041 (9)	0.0089 (8)	0.0146 (9)
C19	0.0437 (10)	0.0384 (11)	0.0291 (8)	0.0045 (9)	0.0095 (7)	0.0057 (8)
C20	0.0340 (9)	0.0264 (9)	0.0277 (8)	0.0014 (7)	0.0050 (6)	−0.0009 (7)
C21	0.0443 (10)	0.0270 (9)	0.0302 (8)	−0.0018 (8)	−0.0083 (7)	−0.0053 (7)

S1—O2	1.4959 (13)	C12—C13	1.371 (2)
S1—C1	1.7633 (16)	C13—C14	1.384 (2)
S1—C21	1.7910 (18)	C13—H13	0.9500
F1—C12	1.3607 (18)	C14—H14	0.9500
O1—C8	1.3800 (19)	C15—C20	1.530 (2)
O1—C7	1.3836 (19)	C15—C16	1.533 (2)
C1—C8	1.366 (2)	C15—H15	1.0000
C1—C2	1.448 (2)	C16—C17	1.526 (2)
C2—C7	1.389 (2)	C16—H16A	0.9900
C2—C3	1.399 (2)	C16—H16B	0.9900
C3—C4	1.390 (2)	C17—C18	1.523 (3)
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.411 (2)	C17—H17B	0.9900
C4—C15	1.511 (2)	C18—C19	1.523 (3)
C5—C6	1.383 (2)	C18—H18A	0.9900
C5—H5	0.9500	C18—H18B	0.9900
C6—C7	1.381 (2)	C19—C20	1.522 (2)
C6—H6	0.9500	C19—H19A	0.9900
C8—C9	1.457 (2)	C19—H19B	0.9900
C9—C14	1.394 (2)	C20—H20A	0.9900
C9—C10	1.399 (2)	C20—H20B	0.9900
C10—C11	1.383 (2)	C21—H21A	0.9800
C10—H10	0.9500	C21—H21B	0.9800
C11—C12	1.372 (2)	C21—H21C	0.9800
C11—H11	0.9500
O2—S1—C1	106.78 (7)	C13—C14—H14	119.9
O2—S1—C21	106.10 (8)	C9—C14—H14	119.9
C1—S1—C21	97.17 (8)	C4—C15—C20	110.95 (13)
C8—O1—C7	106.31 (11)	C4—C15—C16	114.25 (13)
C8—C1—C2	107.21 (13)	C20—C15—C16	110.01 (14)
C8—C1—S1	126.32 (12)	C4—C15—H15	107.1
C2—C1—S1	126.07 (12)	C20—C15—H15	107.1
C7—C2—C3	119.46 (14)	C16—C15—H15	107.1
C7—C2—C1	105.02 (14)	C17—C16—C15	110.99 (14)
C3—C2—C1	135.46 (14)	C17—C16—H16A	109.4
C4—C3—C2	119.00 (14)	C15—C16—H16A	109.4
C4—C3—H3	120.5	C17—C16—H16B	109.4
C2—C3—H3	120.5	C15—C16—H16B	109.4
C3—C4—C5	119.36 (15)	H16A—C16—H16B	108.0
C3—C4—C15	119.36 (13)	C18—C17—C16	111.38 (15)
C5—C4—C15	121.26 (14)	C18—C17—H17A	109.4
C6—C5—C4	122.44 (15)	C16—C17—H17A	109.4
C6—C5—H5	118.8	C18—C17—H17B	109.4
C4—C5—H5	118.8	C16—C17—H17B	109.4
C7—C6—C5	116.47 (14)	H17A—C17—H17B	108.0
C7—C6—H6	121.8	C17—C18—C19	111.44 (15)
C5—C6—H6	121.8	C17—C18—H18A	109.3
C6—C7—O1	125.93 (14)	C19—C18—H18A	109.3
C6—C7—C2	123.25 (15)	C17—C18—H18B	109.3
O1—C7—C2	110.81 (13)	C19—C18—H18B	109.3
C1—C8—O1	110.65 (13)	H18A—C18—H18B	108.0
C1—C8—C9	133.35 (14)	C20—C19—C18	110.97 (15)
O1—C8—C9	115.89 (13)	C20—C19—H19A	109.4
C14—C9—C10	119.18 (15)	C18—C19—H19A	109.4
C14—C9—C8	121.00 (14)	C20—C19—H19B	109.4
C10—C9—C8	119.81 (14)	C18—C19—H19B	109.4
C11—C10—C9	120.83 (15)	H19A—C19—H19B	108.0
C11—C10—H10	119.6	C19—C20—C15	111.52 (14)
C9—C10—H10	119.6	C19—C20—H20A	109.3
C12—C11—C10	117.84 (14)	C15—C20—H20A	109.3
C12—C11—H11	121.1	C19—C20—H20B	109.3
C10—C11—H11	121.1	C15—C20—H20B	109.3
F1—C12—C13	118.01 (16)	H20A—C20—H20B	108.0
F1—C12—C11	118.67 (14)	S1—C21—H21A	109.5
C13—C12—C11	123.31 (15)	S1—C21—H21B	109.5
C12—C13—C14	118.66 (16)	H21A—C21—H21B	109.5
C12—C13—H13	120.7	S1—C21—H21C	109.5
C14—C13—H13	120.7	H21A—C21—H21C	109.5
C13—C14—C9	120.15 (15)	H21B—C21—H21C	109.5
O2—S1—C1—C8	141.75 (14)	C7—O1—C8—C9	−175.83 (13)
C21—S1—C1—C8	−108.99 (15)	C1—C8—C9—C14	32.7 (3)
O2—S1—C1—C2	−30.00 (15)	O1—C8—C9—C14	−151.68 (15)
C21—S1—C1—C2	79.26 (15)	C1—C8—C9—C10	−146.03 (18)
C8—C1—C2—C7	0.58 (17)	O1—C8—C9—C10	29.6 (2)
S1—C1—C2—C7	173.63 (12)	C14—C9—C10—C11	−0.6 (2)
C8—C1—C2—C3	−176.33 (17)	C8—C9—C10—C11	178.17 (15)
S1—C1—C2—C3	−3.3 (3)	C9—C10—C11—C12	−0.8 (2)
C7—C2—C3—C4	0.6 (2)	C10—C11—C12—F1	−178.13 (15)
C1—C2—C3—C4	177.17 (17)	C10—C11—C12—C13	1.0 (3)
C2—C3—C4—C5	0.6 (2)	F1—C12—C13—C14	179.42 (16)
C2—C3—C4—C15	178.85 (14)	C11—C12—C13—C14	0.3 (3)
C3—C4—C5—C6	−1.1 (2)	C12—C13—C14—C9	−1.8 (3)
C15—C4—C5—C6	−179.33 (15)	C10—C9—C14—C13	1.9 (3)
C4—C5—C6—C7	0.4 (2)	C8—C9—C14—C13	−176.85 (16)
C5—C6—C7—O1	−177.69 (15)	C3—C4—C15—C20	−103.02 (17)
C5—C6—C7—C2	0.9 (2)	C5—C4—C15—C20	75.18 (19)
C8—O1—C7—C6	178.41 (16)	C3—C4—C15—C16	131.93 (16)
C8—O1—C7—C2	−0.35 (17)	C5—C4—C15—C16	−49.9 (2)
C3—C2—C7—C6	−1.4 (2)	C4—C15—C16—C17	−178.01 (14)
C1—C2—C7—C6	−178.94 (15)	C20—C15—C16—C17	56.44 (19)
C3—C2—C7—O1	177.37 (13)	C15—C16—C17—C18	−56.0 (2)
C1—C2—C7—O1	−0.14 (17)	C16—C17—C18—C19	55.1 (2)
C2—C1—C8—O1	−0.83 (18)	C17—C18—C19—C20	−54.9 (2)
S1—C1—C8—O1	−173.86 (11)	C18—C19—C20—C15	56.2 (2)
C2—C1—C8—C9	174.93 (17)	C4—C15—C20—C19	175.80 (14)
S1—C1—C8—C9	1.9 (3)	C16—C15—C20—C19	−56.79 (18)
C7—O1—C8—C1	0.74 (17)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C9–C14 4-fluorophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2i	0.98	2.51	3.468 (2)	166
C13—H13···Cg1i	0.95	2.55	3.427 (2)	153
C20—H20A···Cg2ii	0.99	2.73	3.537 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C9–C14 4-fluoro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯O2i	0.98	2.51	3.468 (2)	166
C13—H13⋯Cg1i	0.95	2.55	3.427 (2)	153
C20—H20A⋯Cg2ii	0.99	2.73	3.537 (2)	140

Symmetry codes: (i) ; (ii) .