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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2081.
Published online 2010 July 21. doi:  10.1107/S1600536810028308
PMCID: PMC3007278

3-Ethyl­sulfanyl-2,5-diphenyl-1-benzofuran

Abstract

In the title compound, C22H18OS, 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, mol­ecules are linked by weak inter­molecular C—H(...)π inter­actions.

Related literature

For the crystal structures of similar 3-alkyl­sulfanyl-2,5-diaryl-1-benzofuran derivatives, see: Choi, et al. (2006 [triangle], 2010 [triangle]). For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 [triangle]); Galal et al. (2009 [triangle]); Khan et al. (2005 [triangle]). For natural products with benzofuran rings, see: Akgul & Anil (2003 [triangle]); Soekamto et al. (2003 [triangle]).

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Object name is e-66-o2081-scheme1.jpg

Experimental

Crystal data

  • C22H18OS
  • M r = 330.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2081-efi5.jpg
  • 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 [triangle]) 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 [triangle]), 1271 Friedel pairs
  • Flack parameter: 0.05 (6)

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

The compounds containing benzofuran skeleton show interesting pharmacological properties such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) activity. These compounds occur in nature (Akgul & Anil, 2003; Soekamto et al.., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 3-alkylsulfanyl-2,5-diaryl-1-benzofuran analogues (Choi et al.., 2006, 2010), we report the crystal structure of the title compound (Fig. 1).

The title compound crystallizes in the monoclinic space group P21. The benzofuran unit is essentially planar, with a mean deviation of 0.020 (1) Å from the least-squares plane defined by the nine constituent atoms. In the molecule, the benzofuran plane makes dihedral angles of 29.18 (6) and 20.42 (5)° with the 2-phenyl ring and the 5-phenyl ring, respectively. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···π interactions; the first one between the 5-phenyl H atom and the 5-phenyl ring of an adjacent molecule, with a C10—H10···Cg1i, and the second one between the 5-phenyl H atom and the 2-phenyl ring of a neighbouring molecule, with a C14—H14···Cg2ii, respectively (Table 1, Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C15–C20 phenyl ring, respectively, for symmetry operators see Fig. 2 legend).

Experimental

Zinc chloride (300 mg, 2.2 mmol) was added to a stirred solution of 4-phenylphenol (375 mg, 2.2 mmol) and 2-chloro-2-(ethylsulfanyl)acetophenone (472 mg, 2.2 mmol) in dichloromethane (30 mL) at room temperature, and stirring was continued at the same temperature for 1hr. The reaction was quenched by the addition of water and the organic layer separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (carbon tetrachloride) to afford the title compound as a colorless solid [yield 46%, m.p. 368–369 K; Rf = 0.51 (carbon tetrachloride)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 0.95 Å for methylene and 0.99 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene, 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small circles of arbitrary radius.
Fig. 2.
C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x, y - 1/2, - z + 1; (ii) - x + 1, y + 1/2, - z + 1; (iii) - x, y + 1/2, - ...

Crystal data

C22H18OSF(000) = 348
Mr = 330.42Dx = 1.300 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5754 reflections
a = 10.4968 (3) Åθ = 2.2–27.6°
b = 7.2025 (2) ŵ = 0.20 mm1
c = 12.0783 (3) ÅT = 174 K
β = 112.474 (1)°Block, colourless
V = 843.81 (4) Å30.24 × 0.20 × 0.18 mm
Z = 2

Data collection

Bruker SMART APEXII CCD diffractometer3380 independent reflections
Radiation source: rotating anode3229 reflections with I > 2σ(I)
graphite multilayerRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 1.8°
[var phi] and ω scansh = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −8→9
Tmin = 0.954, Tmax = 0.966l = −15→15
7930 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.080w = 1/[σ2(Fo2) + (0.0418P)2 + 0.1018P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3380 reflectionsΔρmax = 0.20 e Å3
218 parametersΔρmin = −0.24 e Å3
1 restraintAbsolute structure: Flack (1983), 1271 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (6)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S0.52254 (4)0.25661 (7)0.85171 (3)0.03269 (11)
O0.64105 (10)0.32731 (17)0.57860 (9)0.0280 (2)
C10.54722 (15)0.2879 (2)0.71715 (13)0.0257 (3)
C20.43709 (15)0.2982 (2)0.60132 (13)0.0247 (3)
C30.29352 (15)0.2969 (2)0.55943 (13)0.0252 (3)
H30.24850.28150.61380.030*
C40.21667 (15)0.3182 (2)0.43754 (13)0.0247 (3)
C50.28644 (16)0.3366 (2)0.35838 (14)0.0278 (3)
H50.23360.34770.27490.033*
C60.42891 (16)0.3391 (3)0.39822 (14)0.0293 (3)
H60.47470.35190.34440.035*
C70.50068 (15)0.3221 (2)0.51984 (14)0.0259 (3)
C80.66776 (15)0.3084 (2)0.69972 (14)0.0266 (3)
C90.06340 (15)0.3277 (2)0.39132 (13)0.0242 (3)
C10−0.00910 (15)0.2388 (3)0.45240 (14)0.0275 (3)
H100.03950.16590.52120.033*
C11−0.15161 (15)0.2563 (3)0.41335 (15)0.0323 (3)
H11−0.19960.19590.45580.039*
C12−0.22321 (17)0.3606 (3)0.31357 (17)0.0350 (4)
H12−0.32030.37410.28790.042*
C13−0.15343 (18)0.4461 (3)0.25046 (16)0.0365 (4)
H13−0.20310.51600.18050.044*
C14−0.01146 (17)0.4299 (3)0.28911 (15)0.0301 (4)
H140.03540.48930.24540.036*
C150.81365 (15)0.3226 (2)0.77699 (14)0.0274 (3)
C160.86570 (16)0.2563 (3)0.89490 (15)0.0353 (4)
H160.80560.19920.92690.042*
C171.00454 (18)0.2741 (3)0.96477 (16)0.0404 (4)
H171.03930.22871.04470.048*
C181.09330 (19)0.3569 (3)0.91986 (19)0.0394 (4)
H181.18840.36900.96870.047*
C191.04281 (18)0.4221 (3)0.80334 (18)0.0374 (4)
H191.10370.47930.77230.045*
C200.90512 (17)0.4049 (2)0.73196 (16)0.0313 (4)
H200.87180.44910.65180.038*
C210.45785 (19)0.4872 (3)0.86615 (17)0.0391 (4)
H21A0.38150.51990.79000.047*
H21B0.42030.48410.92990.047*
C220.5674 (2)0.6348 (3)0.89573 (19)0.0489 (5)
H22A0.60860.63390.83540.073*
H22B0.63890.61000.97490.073*
H22C0.52600.75660.89620.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0348 (2)0.0388 (2)0.02657 (19)−0.00208 (19)0.01411 (16)0.00605 (19)
O0.0247 (5)0.0343 (6)0.0265 (5)−0.0002 (5)0.0113 (4)−0.0006 (5)
C10.0280 (7)0.0243 (9)0.0257 (7)0.0003 (6)0.0112 (6)0.0029 (6)
C20.0298 (7)0.0220 (9)0.0242 (7)−0.0011 (6)0.0124 (6)−0.0006 (6)
C30.0266 (7)0.0251 (9)0.0268 (7)−0.0011 (6)0.0135 (6)−0.0002 (6)
C40.0264 (7)0.0222 (8)0.0275 (7)−0.0027 (6)0.0124 (6)−0.0017 (6)
C50.0306 (8)0.0316 (9)0.0221 (7)−0.0020 (7)0.0110 (6)−0.0007 (7)
C60.0322 (8)0.0334 (9)0.0278 (8)−0.0022 (7)0.0175 (7)−0.0015 (7)
C70.0237 (7)0.0268 (8)0.0288 (8)−0.0006 (6)0.0120 (6)−0.0013 (7)
C80.0298 (7)0.0240 (8)0.0264 (7)0.0028 (6)0.0113 (6)0.0008 (6)
C90.0268 (7)0.0211 (7)0.0244 (7)−0.0009 (6)0.0096 (6)−0.0038 (6)
C100.0276 (7)0.0260 (8)0.0293 (7)−0.0020 (7)0.0115 (6)−0.0007 (7)
C110.0306 (8)0.0299 (8)0.0402 (8)−0.0039 (8)0.0177 (7)−0.0030 (9)
C120.0238 (8)0.0355 (10)0.0425 (10)−0.0022 (7)0.0090 (7)−0.0037 (8)
C130.0309 (9)0.0362 (10)0.0352 (9)0.0012 (7)0.0047 (8)0.0045 (8)
C140.0300 (9)0.0293 (9)0.0303 (8)−0.0038 (7)0.0107 (7)0.0020 (7)
C150.0261 (7)0.0229 (8)0.0331 (8)0.0021 (7)0.0112 (7)−0.0017 (7)
C160.0308 (8)0.0367 (9)0.0378 (8)0.0019 (8)0.0123 (7)0.0029 (9)
C170.0362 (9)0.0421 (12)0.0347 (8)0.0047 (9)0.0046 (7)0.0023 (9)
C180.0260 (8)0.0352 (10)0.0491 (11)0.0029 (7)0.0054 (8)−0.0021 (9)
C190.0300 (9)0.0327 (10)0.0504 (11)0.0002 (7)0.0163 (8)0.0014 (9)
C200.0284 (8)0.0275 (9)0.0375 (9)0.0024 (7)0.0119 (7)0.0026 (7)
C210.0408 (10)0.0484 (12)0.0320 (9)0.0039 (9)0.0181 (8)−0.0019 (8)
C220.0638 (13)0.0459 (12)0.0350 (10)−0.0056 (10)0.0168 (10)−0.0048 (9)

Geometric parameters (Å, °)

S—C11.755 (1)C12—C131.387 (3)
S—C211.828 (2)C12—H120.9500
O—C71.370 (2)C13—C141.386 (2)
O—C81.387 (2)C13—H130.9500
C1—C81.368 (2)C14—H140.9500
C1—C21.436 (2)C15—C161.400 (2)
C2—C31.394 (2)C15—C201.403 (2)
C2—C71.395 (2)C16—C171.383 (2)
C3—C41.391 (2)C16—H160.9500
C3—H30.9500C17—C181.380 (3)
C4—C51.416 (2)C17—H170.9500
C4—C91.489 (2)C18—C191.383 (3)
C5—C61.385 (2)C18—H180.9500
C5—H50.9500C19—C201.377 (2)
C6—C71.376 (2)C19—H190.9500
C6—H60.9500C20—H200.9500
C8—C151.461 (2)C21—C221.505 (3)
C9—C141.394 (2)C21—H21A0.9900
C9—C101.401 (2)C21—H21B0.9900
C10—C111.392 (2)C22—H22A0.9800
C10—H100.9500C22—H22B0.9800
C11—C121.375 (3)C22—H22C0.9800
C11—H110.9500
C1—S—C2199.40 (8)C13—C12—H12120.1
C7—O—C8106.70 (11)C14—C13—C12120.22 (17)
C8—C1—C2106.98 (13)C14—C13—H13119.9
C8—C1—S128.97 (12)C12—C13—H13119.9
C2—C1—S124.05 (11)C13—C14—C9120.83 (15)
C3—C2—C7119.15 (14)C13—C14—H14119.6
C3—C2—C1135.14 (13)C9—C14—H14119.6
C7—C2—C1105.64 (13)C16—C15—C20118.66 (15)
C4—C3—C2119.50 (12)C16—C15—C8122.16 (14)
C4—C3—H3120.2C20—C15—C8119.18 (15)
C2—C3—H3120.2C17—C16—C15119.99 (16)
C3—C4—C5119.01 (13)C17—C16—H16120.0
C3—C4—C9120.55 (12)C15—C16—H16120.0
C5—C4—C9120.42 (14)C18—C17—C16120.83 (17)
C6—C5—C4122.36 (14)C18—C17—H17119.6
C6—C5—H5118.8C16—C17—H17119.6
C4—C5—H5118.8C17—C18—C19119.55 (17)
C7—C6—C5116.58 (13)C17—C18—H18120.2
C7—C6—H6121.7C19—C18—H18120.2
C5—C6—H6121.7C20—C19—C18120.60 (16)
O—C7—C6126.30 (13)C20—C19—H19119.7
O—C7—C2110.36 (13)C18—C19—H19119.7
C6—C7—C2123.34 (14)C19—C20—C15120.36 (16)
C1—C8—O110.31 (13)C19—C20—H20119.8
C1—C8—C15135.63 (14)C15—C20—H20119.8
O—C8—C15114.01 (12)C22—C21—S112.73 (14)
C14—C9—C10118.17 (14)C22—C21—H21A109.0
C14—C9—C4121.24 (13)S—C21—H21A109.0
C10—C9—C4120.55 (14)C22—C21—H21B109.0
C11—C10—C9120.68 (16)S—C21—H21B109.0
C11—C10—H10119.7H21A—C21—H21B107.8
C9—C10—H10119.7C21—C22—H22A109.5
C12—C11—C10120.21 (15)C21—C22—H22B109.5
C12—C11—H11119.9H22A—C22—H22B109.5
C10—C11—H11119.9C21—C22—H22C109.5
C11—C12—C13119.87 (15)H22A—C22—H22C109.5
C11—C12—H12120.1H22B—C22—H22C109.5
C21—S—C1—C8106.15 (17)C7—O—C8—C15−176.39 (13)
C21—S—C1—C2−73.27 (15)C3—C4—C9—C14149.59 (16)
C8—C1—C2—C3−176.13 (17)C5—C4—C9—C14−28.4 (2)
S—C1—C2—C33.4 (3)C3—C4—C9—C10−28.1 (2)
C8—C1—C2—C70.84 (18)C5—C4—C9—C10153.88 (17)
S—C1—C2—C7−179.64 (12)C14—C9—C10—C11−1.5 (2)
C7—C2—C3—C40.4 (2)C4—C9—C10—C11176.25 (16)
C1—C2—C3—C4177.06 (16)C9—C10—C11—C120.3 (3)
C2—C3—C4—C51.4 (2)C10—C11—C12—C131.1 (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—C90.2 (3)
C9—C4—C5—C6176.31 (15)C10—C9—C14—C131.2 (3)
C4—C5—C6—C70.2 (3)C4—C9—C14—C13−176.49 (16)
C8—O—C7—C6178.86 (16)C1—C8—C15—C1621.8 (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—C21.7 (3)O—C8—C15—C2018.5 (2)
C3—C2—C7—O177.43 (13)C20—C15—C16—C170.5 (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—C180.1 (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—O179.25 (12)C18—C19—C20—C150.7 (3)
C2—C1—C8—C15175.57 (17)C16—C15—C20—C19−0.9 (3)
S—C1—C8—C15−3.9 (3)C8—C15—C20—C19179.21 (16)
C7—O—C8—C11.18 (17)C1—S—C21—C22−70.50 (15)

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···AD—HH···AD···AD—H···A
C10—H10···Cg1i0.952.733.592 (3)152
C14—H14···Cg2ii0.952.793.549 (3)138

Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2130).

References

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  • Choi, H. D., Seo, P. J., Kang, B. W., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4796–o4797.
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o336. [PMC free article] [PubMed]
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  • Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem 13, 4796–4805. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. [PubMed]

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