3-(4-Bromo-phenyl-sulfin-yl)-5-cyclo-hexyl-2-methyl-1-benzofuran.

In the title compound, C(21)H(21)BrO(2)S, the cyclohexyl ring adopts a chair conformation. The 4-bromo-phenyl ring makes a dihedral angle of 81.62 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits a slipped π-π inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distances = 3.540 (3) Å, inter-planar distance = 3.481 (3) Å and slippage = 0.644 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C21H21BrO2S

M = 417.35

Monoclinic,

a = 16.7340 (4) Å

b = 8.8290 (2) Å

c = 13.0178 (3) Å

β = 105.197 (1)°

V = 1856.05 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.34 mm−1

T = 173 K

0.25 × 0.23 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.561, T max = 0.746

17836 measured reflections

4653 independent reflections

3467 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.04

4653 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.61 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 datablock(s) global, I. DOI: 10.1107/S1600536811054158/ff2048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054158/ff2048Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054158/ff2048Isup3.cml

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

C21H21BrO2S	F(000) = 856
Mr = 417.35	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6823 reflections
a = 16.7340 (4) Å	θ = 2.5–25.9°
b = 8.8290 (2) Å	µ = 2.34 mm−1
c = 13.0178 (3) Å	T = 173 K
β = 105.197 (1)°	Block, colourless
V = 1856.05 (7) Å3	0.25 × 0.23 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4653 independent reflections
Radiation source: rotating anode	3467 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.3°
φ and ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→11
Tmin = 0.561, Tmax = 0.746	l = −17→15
17836 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.7692P] where P = (Fo2 + 2Fc2)/3
4653 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.61 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
Br1	0.468766 (17)	0.59993 (4)	0.30483 (2)	0.06137 (12)
S1	0.13569 (3)	0.72783 (5)	0.44840 (4)	0.03017 (13)
O1	0.03213 (8)	0.32472 (16)	0.40283 (11)	0.0312 (3)
O2	0.15901 (10)	0.78663 (16)	0.55882 (12)	0.0384 (4)
C1	0.10321 (12)	0.5392 (2)	0.45372 (15)	0.0259 (4)
C2	0.13294 (12)	0.4289 (2)	0.53755 (16)	0.0246 (4)
C3	0.19099 (12)	0.4260 (2)	0.63618 (16)	0.0253 (4)
H3	0.2228	0.5135	0.6625	0.030*
C4	0.20162 (12)	0.2931 (2)	0.69560 (16)	0.0267 (4)
C5	0.15359 (13)	0.1661 (2)	0.65496 (18)	0.0328 (5)
H5	0.1613	0.0759	0.6962	0.039*
C6	0.09542 (13)	0.1663 (2)	0.55754 (18)	0.0335 (5)
H6	0.0635	0.0790	0.5309	0.040*
C7	0.08631 (12)	0.2995 (2)	0.50145 (16)	0.0279 (4)
C8	0.04359 (12)	0.4725 (2)	0.37654 (16)	0.0285 (4)
C9	0.26423 (12)	0.2852 (2)	0.80359 (16)	0.0287 (4)
H9	0.2630	0.1795	0.8308	0.034*
C10	0.35211 (13)	0.3162 (3)	0.79681 (18)	0.0404 (5)
H10A	0.3547	0.4182	0.7663	0.048*
H10B	0.3675	0.2412	0.7487	0.048*
C11	0.41427 (14)	0.3071 (3)	0.90723 (19)	0.0435 (6)
H11A	0.4164	0.2018	0.9340	0.052*
H11B	0.4702	0.3341	0.9008	0.052*
C12	0.39071 (16)	0.4119 (3)	0.9856 (2)	0.0460 (6)
H12A	0.3950	0.5181	0.9633	0.055*
H12B	0.4298	0.3982	1.0566	0.055*
C13	0.30362 (16)	0.3820 (3)	0.99321 (19)	0.0480 (6)
H13A	0.2887	0.4573	1.0414	0.058*
H13B	0.3009	0.2801	1.0238	0.058*
C14	0.24169 (15)	0.3912 (3)	0.88407 (19)	0.0409 (5)
H14A	0.1859	0.3648	0.8911	0.049*
H14B	0.2397	0.4966	0.8575	0.049*
C15	−0.00823 (13)	0.5249 (3)	0.27284 (17)	0.0374 (5)
H15A	−0.0039	0.6352	0.2681	0.056*
H15B	−0.0660	0.4967	0.2660	0.056*
H15C	0.0108	0.4774	0.2154	0.056*
C16	0.22978 (13)	0.6877 (2)	0.41199 (15)	0.0275 (4)
C17	0.22676 (14)	0.6868 (2)	0.30470 (16)	0.0320 (5)
H17	0.1759	0.7059	0.2532	0.038*
C18	0.29773 (15)	0.6579 (2)	0.27262 (17)	0.0358 (5)
H18	0.2960	0.6548	0.1991	0.043*
C19	0.37075 (15)	0.6337 (3)	0.34865 (19)	0.0374 (5)
C20	0.37513 (14)	0.6356 (3)	0.45633 (19)	0.0388 (5)
H20	0.4263	0.6186	0.5076	0.047*
C21	0.30379 (13)	0.6628 (2)	0.48822 (17)	0.0337 (5)
H21	0.3055	0.6644	0.5617	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.04820 (18)	0.0874 (2)	0.0565 (2)	−0.00961 (14)	0.02786 (14)	−0.00300 (14)
S1	0.0388 (3)	0.0241 (2)	0.0259 (3)	0.0038 (2)	0.0053 (2)	0.0013 (2)
O1	0.0262 (7)	0.0341 (8)	0.0312 (8)	−0.0033 (6)	0.0036 (6)	−0.0058 (6)
O2	0.0513 (9)	0.0334 (8)	0.0294 (8)	−0.0014 (7)	0.0086 (7)	−0.0065 (6)
C1	0.0268 (10)	0.0256 (10)	0.0244 (10)	0.0022 (8)	0.0050 (8)	−0.0019 (8)
C2	0.0238 (9)	0.0232 (9)	0.0277 (10)	0.0023 (7)	0.0083 (8)	−0.0011 (8)
C3	0.0250 (10)	0.0229 (9)	0.0278 (10)	−0.0009 (7)	0.0068 (8)	−0.0013 (8)
C4	0.0245 (9)	0.0268 (10)	0.0295 (11)	0.0028 (8)	0.0079 (8)	0.0023 (8)
C5	0.0322 (11)	0.0257 (10)	0.0412 (13)	0.0000 (8)	0.0110 (9)	0.0056 (9)
C6	0.0292 (11)	0.0263 (10)	0.0445 (13)	−0.0068 (8)	0.0089 (9)	−0.0030 (9)
C7	0.0215 (9)	0.0319 (11)	0.0302 (11)	−0.0005 (8)	0.0065 (8)	−0.0048 (8)
C8	0.0260 (10)	0.0318 (10)	0.0286 (11)	0.0031 (8)	0.0085 (8)	−0.0037 (8)
C9	0.0278 (10)	0.0243 (10)	0.0323 (11)	0.0014 (8)	0.0051 (8)	0.0069 (8)
C10	0.0278 (11)	0.0626 (15)	0.0306 (12)	0.0051 (10)	0.0074 (9)	0.0004 (11)
C11	0.0280 (11)	0.0610 (16)	0.0385 (13)	0.0035 (11)	0.0034 (10)	0.0069 (11)
C12	0.0514 (15)	0.0446 (14)	0.0345 (13)	−0.0050 (11)	−0.0023 (11)	0.0016 (10)
C13	0.0556 (16)	0.0619 (16)	0.0264 (12)	0.0096 (12)	0.0105 (11)	0.0013 (11)
C14	0.0390 (13)	0.0524 (14)	0.0341 (13)	0.0105 (10)	0.0145 (10)	0.0074 (10)
C15	0.0310 (11)	0.0516 (14)	0.0268 (11)	0.0063 (10)	0.0022 (9)	−0.0037 (10)
C16	0.0378 (11)	0.0208 (9)	0.0232 (10)	−0.0040 (8)	0.0067 (9)	0.0006 (7)
C17	0.0428 (12)	0.0264 (10)	0.0238 (10)	−0.0037 (9)	0.0033 (9)	0.0026 (8)
C18	0.0509 (14)	0.0330 (11)	0.0247 (11)	−0.0086 (10)	0.0120 (10)	0.0007 (9)
C19	0.0391 (12)	0.0377 (12)	0.0382 (13)	−0.0088 (10)	0.0151 (10)	−0.0013 (10)
C20	0.0341 (12)	0.0480 (13)	0.0311 (12)	−0.0070 (10)	0.0026 (9)	−0.0006 (10)
C21	0.0403 (12)	0.0374 (11)	0.0212 (10)	−0.0064 (9)	0.0040 (9)	−0.0003 (9)

Br1—C19	1.896 (2)	C11—C12	1.505 (4)
S1—O2	1.4812 (15)	C11—H11A	0.9900
S1—C1	1.759 (2)	C11—H11B	0.9900
S1—C16	1.795 (2)	C12—C13	1.510 (4)
O1—C8	1.375 (3)	C12—H12A	0.9900
O1—C7	1.382 (2)	C12—H12B	0.9900
C1—C8	1.351 (3)	C13—C14	1.525 (3)
C1—C2	1.450 (3)	C13—H13A	0.9900
C2—C3	1.392 (3)	C13—H13B	0.9900
C2—C7	1.394 (3)	C14—H14A	0.9900
C3—C4	1.391 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.400 (3)	C15—H15B	0.9800
C4—C9	1.519 (3)	C15—H15C	0.9800
C5—C6	1.382 (3)	C16—C17	1.384 (3)
C5—H5	0.9500	C16—C21	1.386 (3)
C6—C7	1.372 (3)	C17—C18	1.382 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.475 (3)	C18—C19	1.373 (3)
C9—C10	1.521 (3)	C18—H18	0.9500
C9—C14	1.524 (3)	C19—C20	1.384 (3)
C9—H9	1.0000	C20—C21	1.384 (3)
C10—C11	1.540 (3)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900
O2—S1—C1	107.40 (9)	C10—C11—H11B	109.3
O2—S1—C16	107.42 (9)	H11A—C11—H11B	108.0
C1—S1—C16	97.18 (9)	C11—C12—C13	111.4 (2)
C8—O1—C7	106.49 (15)	C11—C12—H12A	109.3
C8—C1—C2	107.95 (17)	C13—C12—H12A	109.3
C8—C1—S1	123.96 (16)	C11—C12—H12B	109.3
C2—C1—S1	128.09 (15)	C13—C12—H12B	109.3
C3—C2—C7	119.31 (18)	H12A—C12—H12B	108.0
C3—C2—C1	136.49 (18)	C12—C13—C14	111.2 (2)
C7—C2—C1	104.20 (17)	C12—C13—H13A	109.4
C4—C3—C2	119.01 (18)	C14—C13—H13A	109.4
C4—C3—H3	120.5	C12—C13—H13B	109.4
C2—C3—H3	120.5	C14—C13—H13B	109.4
C3—C4—C5	119.23 (18)	H13A—C13—H13B	108.0
C3—C4—C9	120.69 (17)	C9—C14—C13	112.17 (19)
C5—C4—C9	120.08 (17)	C9—C14—H14A	109.2
C6—C5—C4	122.86 (19)	C13—C14—H14A	109.2
C6—C5—H5	118.6	C9—C14—H14B	109.2
C4—C5—H5	118.6	C13—C14—H14B	109.2
C7—C6—C5	116.29 (19)	H14A—C14—H14B	107.9
C7—C6—H6	121.9	C8—C15—H15A	109.5
C5—C6—H6	121.9	C8—C15—H15B	109.5
C6—C7—O1	125.95 (18)	H15A—C15—H15B	109.5
C6—C7—C2	123.30 (19)	C8—C15—H15C	109.5
O1—C7—C2	110.74 (17)	H15A—C15—H15C	109.5
C1—C8—O1	110.62 (17)	H15B—C15—H15C	109.5
C1—C8—C15	133.38 (19)	C17—C16—C21	120.7 (2)
O1—C8—C15	115.99 (17)	C17—C16—S1	117.72 (16)
C4—C9—C10	112.38 (17)	C21—C16—S1	121.55 (16)
C4—C9—C14	111.90 (17)	C18—C17—C16	119.9 (2)
C10—C9—C14	110.29 (18)	C18—C17—H17	120.0
C4—C9—H9	107.3	C16—C17—H17	120.0
C10—C9—H9	107.3	C19—C18—C17	118.9 (2)
C14—C9—H9	107.3	C19—C18—H18	120.5
C9—C10—C11	111.30 (18)	C17—C18—H18	120.5
C9—C10—H10A	109.4	C18—C19—C20	121.9 (2)
C11—C10—H10A	109.4	C18—C19—Br1	118.97 (18)
C9—C10—H10B	109.4	C20—C19—Br1	119.09 (18)
C11—C10—H10B	109.4	C21—C20—C19	119.0 (2)
H10A—C10—H10B	108.0	C21—C20—H20	120.5
C12—C11—C10	111.59 (19)	C19—C20—H20	120.5
C12—C11—H11A	109.3	C20—C21—C16	119.5 (2)
C10—C11—H11A	109.3	C20—C21—H21	120.3
C12—C11—H11B	109.3	C16—C21—H21	120.3
O2—S1—C1—C8	146.84 (17)	C7—O1—C8—C15	179.75 (17)
C16—S1—C1—C8	−102.33 (18)	C3—C4—C9—C10	−60.3 (2)
O2—S1—C1—C2	−32.9 (2)	C5—C4—C9—C10	119.9 (2)
C16—S1—C1—C2	77.98 (19)	C3—C4—C9—C14	64.4 (2)
C8—C1—C2—C3	−178.9 (2)	C5—C4—C9—C14	−115.3 (2)
S1—C1—C2—C3	0.8 (4)	C4—C9—C10—C11	−179.87 (18)
C8—C1—C2—C7	0.1 (2)	C14—C9—C10—C11	54.5 (3)
S1—C1—C2—C7	179.79 (15)	C9—C10—C11—C12	−55.4 (3)
C7—C2—C3—C4	0.8 (3)	C10—C11—C12—C13	55.4 (3)
C1—C2—C3—C4	179.7 (2)	C11—C12—C13—C14	−55.1 (3)
C2—C3—C4—C5	−0.2 (3)	C4—C9—C14—C13	179.11 (19)
C2—C3—C4—C9	−179.96 (17)	C10—C9—C14—C13	−55.0 (3)
C3—C4—C5—C6	0.0 (3)	C12—C13—C14—C9	55.4 (3)
C9—C4—C5—C6	179.74 (19)	O2—S1—C16—C17	−156.18 (15)
C4—C5—C6—C7	−0.3 (3)	C1—S1—C16—C17	92.99 (16)
C5—C6—C7—O1	179.92 (18)	O2—S1—C16—C21	21.95 (19)
C5—C6—C7—C2	0.9 (3)	C1—S1—C16—C21	−88.88 (18)
C8—O1—C7—C6	−179.9 (2)	C21—C16—C17—C18	1.2 (3)
C8—O1—C7—C2	−0.8 (2)	S1—C16—C17—C18	179.39 (15)
C3—C2—C7—C6	−1.2 (3)	C16—C17—C18—C19	−1.4 (3)
C1—C2—C7—C6	179.60 (19)	C17—C18—C19—C20	0.8 (3)
C3—C2—C7—O1	179.69 (17)	C17—C18—C19—Br1	−178.19 (15)
C1—C2—C7—O1	0.5 (2)	C18—C19—C20—C21	−0.1 (3)
C2—C1—C8—O1	−0.6 (2)	Br1—C19—C20—C21	178.94 (17)
S1—C1—C8—O1	179.68 (13)	C19—C20—C21—C16	−0.1 (3)
C2—C1—C8—C15	−179.2 (2)	C17—C16—C21—C20	−0.5 (3)
S1—C1—C8—C15	1.1 (3)	S1—C16—C21—C20	−178.55 (17)
C7—O1—C8—C1	0.9 (2)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2i	0.95	2.47	3.112 (3)	125.
C15—H15B···Cg2ii	0.98	3.06	3.532 (3)	111.

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
C17—H17⋯O2i	0.95	2.47	3.112 (3)	125
C15—H15B⋯Cg2ii	0.98	3.06	3.532 (3)	111

Symmetry codes: (i) ; (ii) .