3-Ethyl-sulfanyl-2,5-diphenyl-1-benzofuran.

In the title compound, C(22)H(18)OS, the 2-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 29.18 (6)°. The dihedral angle between the 5-phenyl ring and the benzofuran plane is 20.42 (5)°. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯π inter-actions.

Related literature

For the crystal structures of similar 3-alkyl­sulfanyl-2,5-diaryl-1-benzofuran derivatives, see: Choi, et al. (2006 ▶, 2010 ▶). 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 ▶).

Experimental

Crystal data

C22H18OS

M = 330.42

Monoclinic,

a = 10.4968 (3) Å

b = 7.2025 (2) Å

c = 12.0783 (3) Å

β = 112.474 (1)°

V = 843.81 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 174 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.966

7930 measured reflections

3380 independent reflections

3229 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.06

3380 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1271 Friedel pairs

Flack parameter: 0.05 (6)

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/S1600536810028308/cs2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028308/cs2130Isup2.hkl

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

C22H18OS	F(000) = 348
Mr = 330.42	Dx = 1.300 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5754 reflections
a = 10.4968 (3) Å	θ = 2.2–27.6°
b = 7.2025 (2) Å	µ = 0.20 mm−1
c = 12.0783 (3) Å	T = 174 K
β = 112.474 (1)°	Block, colourless
V = 843.81 (4) Å3	0.24 × 0.20 × 0.18 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	3380 independent reflections
Radiation source: rotating anode	3229 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→9
Tmin = 0.954, Tmax = 0.966	l = −15→15
7930 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.1018P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3380 reflections	Δρmax = 0.20 e Å−3
218 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (6)

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
S	0.52254 (4)	0.25661 (7)	0.85171 (3)	0.03269 (11)
O	0.64105 (10)	0.32731 (17)	0.57860 (9)	0.0280 (2)
C1	0.54722 (15)	0.2879 (2)	0.71715 (13)	0.0257 (3)
C2	0.43709 (15)	0.2982 (2)	0.60132 (13)	0.0247 (3)
C3	0.29352 (15)	0.2969 (2)	0.55943 (13)	0.0252 (3)
H3	0.2485	0.2815	0.6138	0.030*
C4	0.21667 (15)	0.3182 (2)	0.43754 (13)	0.0247 (3)
C5	0.28644 (16)	0.3366 (2)	0.35838 (14)	0.0278 (3)
H5	0.2336	0.3477	0.2749	0.033*
C6	0.42891 (16)	0.3391 (3)	0.39822 (14)	0.0293 (3)
H6	0.4747	0.3519	0.3444	0.035*
C7	0.50068 (15)	0.3221 (2)	0.51984 (14)	0.0259 (3)
C8	0.66776 (15)	0.3084 (2)	0.69972 (14)	0.0266 (3)
C9	0.06340 (15)	0.3277 (2)	0.39132 (13)	0.0242 (3)
C10	−0.00910 (15)	0.2388 (3)	0.45240 (14)	0.0275 (3)
H10	0.0395	0.1659	0.5212	0.033*
C11	−0.15161 (15)	0.2563 (3)	0.41335 (15)	0.0323 (3)
H11	−0.1996	0.1959	0.4558	0.039*
C12	−0.22321 (17)	0.3606 (3)	0.31357 (17)	0.0350 (4)
H12	−0.3203	0.3741	0.2879	0.042*
C13	−0.15343 (18)	0.4461 (3)	0.25046 (16)	0.0365 (4)
H13	−0.2031	0.5160	0.1805	0.044*
C14	−0.01146 (17)	0.4299 (3)	0.28911 (15)	0.0301 (4)
H14	0.0354	0.4893	0.2454	0.036*
C15	0.81365 (15)	0.3226 (2)	0.77699 (14)	0.0274 (3)
C16	0.86570 (16)	0.2563 (3)	0.89490 (15)	0.0353 (4)
H16	0.8056	0.1992	0.9269	0.042*
C17	1.00454 (18)	0.2741 (3)	0.96477 (16)	0.0404 (4)
H17	1.0393	0.2287	1.0447	0.048*
C18	1.09330 (19)	0.3569 (3)	0.91986 (19)	0.0394 (4)
H18	1.1884	0.3690	0.9687	0.047*
C19	1.04281 (18)	0.4221 (3)	0.80334 (18)	0.0374 (4)
H19	1.1037	0.4793	0.7723	0.045*
C20	0.90512 (17)	0.4049 (2)	0.73196 (16)	0.0313 (4)
H20	0.8718	0.4491	0.6518	0.038*
C21	0.45785 (19)	0.4872 (3)	0.86615 (17)	0.0391 (4)
H21A	0.3815	0.5199	0.7900	0.047*
H21B	0.4203	0.4841	0.9299	0.047*
C22	0.5674 (2)	0.6348 (3)	0.89573 (19)	0.0489 (5)
H22A	0.6086	0.6339	0.8354	0.073*
H22B	0.6389	0.6100	0.9749	0.073*
H22C	0.5260	0.7566	0.8962	0.073*

	U11	U22	U33	U12	U13	U23
S	0.0348 (2)	0.0388 (2)	0.02657 (19)	−0.00208 (19)	0.01411 (16)	0.00605 (19)
O	0.0247 (5)	0.0343 (6)	0.0265 (5)	−0.0002 (5)	0.0113 (4)	−0.0006 (5)
C1	0.0280 (7)	0.0243 (9)	0.0257 (7)	0.0003 (6)	0.0112 (6)	0.0029 (6)
C2	0.0298 (7)	0.0220 (9)	0.0242 (7)	−0.0011 (6)	0.0124 (6)	−0.0006 (6)
C3	0.0266 (7)	0.0251 (9)	0.0268 (7)	−0.0011 (6)	0.0135 (6)	−0.0002 (6)
C4	0.0264 (7)	0.0222 (8)	0.0275 (7)	−0.0027 (6)	0.0124 (6)	−0.0017 (6)
C5	0.0306 (8)	0.0316 (9)	0.0221 (7)	−0.0020 (7)	0.0110 (6)	−0.0007 (7)
C6	0.0322 (8)	0.0334 (9)	0.0278 (8)	−0.0022 (7)	0.0175 (7)	−0.0015 (7)
C7	0.0237 (7)	0.0268 (8)	0.0288 (8)	−0.0006 (6)	0.0120 (6)	−0.0013 (7)
C8	0.0298 (7)	0.0240 (8)	0.0264 (7)	0.0028 (6)	0.0113 (6)	0.0008 (6)
C9	0.0268 (7)	0.0211 (7)	0.0244 (7)	−0.0009 (6)	0.0096 (6)	−0.0038 (6)
C10	0.0276 (7)	0.0260 (8)	0.0293 (7)	−0.0020 (7)	0.0115 (6)	−0.0007 (7)
C11	0.0306 (8)	0.0299 (8)	0.0402 (8)	−0.0039 (8)	0.0177 (7)	−0.0030 (9)
C12	0.0238 (8)	0.0355 (10)	0.0425 (10)	−0.0022 (7)	0.0090 (7)	−0.0037 (8)
C13	0.0309 (9)	0.0362 (10)	0.0352 (9)	0.0012 (7)	0.0047 (8)	0.0045 (8)
C14	0.0300 (9)	0.0293 (9)	0.0303 (8)	−0.0038 (7)	0.0107 (7)	0.0020 (7)
C15	0.0261 (7)	0.0229 (8)	0.0331 (8)	0.0021 (7)	0.0112 (7)	−0.0017 (7)
C16	0.0308 (8)	0.0367 (9)	0.0378 (8)	0.0019 (8)	0.0123 (7)	0.0029 (9)
C17	0.0362 (9)	0.0421 (12)	0.0347 (8)	0.0047 (9)	0.0046 (7)	0.0023 (9)
C18	0.0260 (8)	0.0352 (10)	0.0491 (11)	0.0029 (7)	0.0054 (8)	−0.0021 (9)
C19	0.0300 (9)	0.0327 (10)	0.0504 (11)	0.0002 (7)	0.0163 (8)	0.0014 (9)
C20	0.0284 (8)	0.0275 (9)	0.0375 (9)	0.0024 (7)	0.0119 (7)	0.0026 (7)
C21	0.0408 (10)	0.0484 (12)	0.0320 (9)	0.0039 (9)	0.0181 (8)	−0.0019 (8)
C22	0.0638 (13)	0.0459 (12)	0.0350 (10)	−0.0056 (10)	0.0168 (10)	−0.0048 (9)

S—C1	1.755 (1)	C12—C13	1.387 (3)
S—C21	1.828 (2)	C12—H12	0.9500
O—C7	1.370 (2)	C13—C14	1.386 (2)
O—C8	1.387 (2)	C13—H13	0.9500
C1—C8	1.368 (2)	C14—H14	0.9500
C1—C2	1.436 (2)	C15—C16	1.400 (2)
C2—C3	1.394 (2)	C15—C20	1.403 (2)
C2—C7	1.395 (2)	C16—C17	1.383 (2)
C3—C4	1.391 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.380 (3)
C4—C5	1.416 (2)	C17—H17	0.9500
C4—C9	1.489 (2)	C18—C19	1.383 (3)
C5—C6	1.385 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.377 (2)
C6—C7	1.376 (2)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C8—C15	1.461 (2)	C21—C22	1.505 (3)
C9—C14	1.394 (2)	C21—H21A	0.9900
C9—C10	1.401 (2)	C21—H21B	0.9900
C10—C11	1.392 (2)	C22—H22A	0.9800
C10—H10	0.9500	C22—H22B	0.9800
C11—C12	1.375 (3)	C22—H22C	0.9800
C11—H11	0.9500
C1—S—C21	99.40 (8)	C13—C12—H12	120.1
C7—O—C8	106.70 (11)	C14—C13—C12	120.22 (17)
C8—C1—C2	106.98 (13)	C14—C13—H13	119.9
C8—C1—S	128.97 (12)	C12—C13—H13	119.9
C2—C1—S	124.05 (11)	C13—C14—C9	120.83 (15)
C3—C2—C7	119.15 (14)	C13—C14—H14	119.6
C3—C2—C1	135.14 (13)	C9—C14—H14	119.6
C7—C2—C1	105.64 (13)	C16—C15—C20	118.66 (15)
C4—C3—C2	119.50 (12)	C16—C15—C8	122.16 (14)
C4—C3—H3	120.2	C20—C15—C8	119.18 (15)
C2—C3—H3	120.2	C17—C16—C15	119.99 (16)
C3—C4—C5	119.01 (13)	C17—C16—H16	120.0
C3—C4—C9	120.55 (12)	C15—C16—H16	120.0
C5—C4—C9	120.42 (14)	C18—C17—C16	120.83 (17)
C6—C5—C4	122.36 (14)	C18—C17—H17	119.6
C6—C5—H5	118.8	C16—C17—H17	119.6
C4—C5—H5	118.8	C17—C18—C19	119.55 (17)
C7—C6—C5	116.58 (13)	C17—C18—H18	120.2
C7—C6—H6	121.7	C19—C18—H18	120.2
C5—C6—H6	121.7	C20—C19—C18	120.60 (16)
O—C7—C6	126.30 (13)	C20—C19—H19	119.7
O—C7—C2	110.36 (13)	C18—C19—H19	119.7
C6—C7—C2	123.34 (14)	C19—C20—C15	120.36 (16)
C1—C8—O	110.31 (13)	C19—C20—H20	119.8
C1—C8—C15	135.63 (14)	C15—C20—H20	119.8
O—C8—C15	114.01 (12)	C22—C21—S	112.73 (14)
C14—C9—C10	118.17 (14)	C22—C21—H21A	109.0
C14—C9—C4	121.24 (13)	S—C21—H21A	109.0
C10—C9—C4	120.55 (14)	C22—C21—H21B	109.0
C11—C10—C9	120.68 (16)	S—C21—H21B	109.0
C11—C10—H10	119.7	H21A—C21—H21B	107.8
C9—C10—H10	119.7	C21—C22—H22A	109.5
C12—C11—C10	120.21 (15)	C21—C22—H22B	109.5
C12—C11—H11	119.9	H22A—C22—H22B	109.5
C10—C11—H11	119.9	C21—C22—H22C	109.5
C11—C12—C13	119.87 (15)	H22A—C22—H22C	109.5
C11—C12—H12	120.1	H22B—C22—H22C	109.5
C21—S—C1—C8	106.15 (17)	C7—O—C8—C15	−176.39 (13)
C21—S—C1—C2	−73.27 (15)	C3—C4—C9—C14	149.59 (16)
C8—C1—C2—C3	−176.13 (17)	C5—C4—C9—C14	−28.4 (2)
S—C1—C2—C3	3.4 (3)	C3—C4—C9—C10	−28.1 (2)
C8—C1—C2—C7	0.84 (18)	C5—C4—C9—C10	153.88 (17)
S—C1—C2—C7	−179.64 (12)	C14—C9—C10—C11	−1.5 (2)
C7—C2—C3—C4	0.4 (2)	C4—C9—C10—C11	176.25 (16)
C1—C2—C3—C4	177.06 (16)	C9—C10—C11—C12	0.3 (3)
C2—C3—C4—C5	1.4 (2)	C10—C11—C12—C13	1.1 (3)
C2—C3—C4—C9	−176.65 (14)	C11—C12—C13—C14	−1.3 (3)
C3—C4—C5—C6	−1.8 (3)	C12—C13—C14—C9	0.2 (3)
C9—C4—C5—C6	176.31 (15)	C10—C9—C14—C13	1.2 (3)
C4—C5—C6—C7	0.2 (3)	C4—C9—C14—C13	−176.49 (16)
C8—O—C7—C6	178.86 (16)	C1—C8—C15—C16	21.8 (3)
C8—O—C7—C2	−0.62 (18)	O—C8—C15—C16	−161.40 (16)
C5—C6—C7—O	−177.68 (15)	C1—C8—C15—C20	−158.25 (19)
C5—C6—C7—C2	1.7 (3)	O—C8—C15—C20	18.5 (2)
C3—C2—C7—O	177.43 (13)	C20—C15—C16—C17	0.5 (3)
C1—C2—C7—O	−0.13 (18)	C8—C15—C16—C17	−179.59 (17)
C3—C2—C7—C6	−2.1 (3)	C15—C16—C17—C18	0.1 (3)
C1—C2—C7—C6	−179.63 (16)	C16—C17—C18—C19	−0.3 (3)
C2—C1—C8—O	−1.26 (18)	C17—C18—C19—C20	−0.1 (3)
S—C1—C8—O	179.25 (12)	C18—C19—C20—C15	0.7 (3)
C2—C1—C8—C15	175.57 (17)	C16—C15—C20—C19	−0.9 (3)
S—C1—C8—C15	−3.9 (3)	C8—C15—C20—C19	179.21 (16)
C7—O—C8—C1	1.18 (17)	C1—S—C21—C22	−70.50 (15)

Cg1 and Cg2 are the centroids of the C9–C14 (5-phenyl) and C15–C20 (2-phenyl) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1i	0.95	2.73	3.592 (3)	152
C14—H14···Cg2ii	0.95	2.79	3.549 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 (5-phen­yl) and C15–C20 (2-phen­yl) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1i	0.95	2.73	3.592 (3)	152
C14—H14⋯Cg2ii	0.95	2.79	3.549 (3)	138

Symmetry codes: (i) ; (ii) .