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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1813.
Published online 2010 June 26. doi:  10.1107/S1600536810023834
PMCID: PMC3006839

3-(4-Fluoro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzofuran

Abstract

In the title compound, C17H15FO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.67 (5)° with the benzofuran plane. In the crystal, mol­ecules are linked by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

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]). For the crystal structures of related 2,5-dimethyl-3-phenyl­sulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a [triangle],b [triangle]).

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Object name is e-66-o1813-scheme1.jpg

Experimental

Crystal data

  • C17H15FO3S
  • M r = 318.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1813-efi1.jpg
  • a = 8.2851 (2) Å
  • b = 9.3762 (2) Å
  • c = 11.2241 (3) Å
  • α = 70.441 (1)°
  • β = 71.177 (1)°
  • γ = 69.407 (1)°
  • V = 748.07 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 173 K
  • 0.23 × 0.21 × 0.19 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.948, T max = 0.957
  • 13476 measured reflections
  • 3449 independent reflections
  • 3097 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.105
  • S = 1.04
  • 3449 reflections
  • 202 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.38 e Å−3

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/S1600536810023834/ds2040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023834/ds2040Isup2.hkl

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

supplementary crystallographic information

Comment

Compounds containing a benzofuran moiety show potent pharmacological properties such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) activities. These compounds widely 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 2,5-dimethyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al.., 2008a, b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 72.67 (5)° with the benzofuran plane. The crystal packing (Fig. 2) is stabilized by three intermolecular C—H···O hydrogen bonds; the first one between the methyl H atom and the oxygen of the O═S═O unit, with a C10—H10B···O2i, the second one between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with a C13—H13···O2ii, and the third one between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with a C17—H17···O3iii, respectively (Table 1).

Experimental

77% 3-Chloroperoxybenzoic acid (538 mg, 2.4 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,5,7-trimethy-1-benzofuran (343 mg, 1.2 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (silica gel, hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 414-415 K; Rf = 0.41 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in diisopropyl ether at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms, Uiso(H) = 1.2 Ueq(C) for aryl and 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 spheres of arbitrary radius.
Fig. 2.
C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 2, - z + 1; (iii) - x + 1, - y + 2, - z.]

Crystal data

C17H15FO3SZ = 2
Mr = 318.35F(000) = 332
Triclinic, P1Dx = 1.413 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.2851 (2) ÅCell parameters from 7810 reflections
b = 9.3762 (2) Åθ = 2.4–27.5°
c = 11.2241 (3) ŵ = 0.24 mm1
α = 70.441 (1)°T = 173 K
β = 71.177 (1)°Block, colourless
γ = 69.407 (1)°0.23 × 0.21 × 0.19 mm
V = 748.07 (3) Å3

Data collection

Bruker SMART APEXII CCD diffractometer3449 independent reflections
Radiation source: rotating anode3097 reflections with I > 2σ(I)
graphite multilayerRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 2.0°
[var phi] and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.948, Tmax = 0.957l = −14→14
13476 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.105H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0536P)2 + 0.3586P] where P = (Fo2 + 2Fc2)/3
3449 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.38 e Å3

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
S0.48710 (5)0.89687 (4)0.29416 (3)0.02449 (12)
F0.98555 (17)1.27225 (14)−0.00227 (13)0.0583 (3)
O10.75715 (15)0.45344 (12)0.32852 (11)0.0300 (2)
O20.39991 (14)0.94794 (13)0.41216 (10)0.0304 (2)
O30.38323 (15)0.91207 (14)0.20728 (11)0.0328 (3)
C10.60789 (19)0.70192 (17)0.33737 (14)0.0254 (3)
C20.67369 (19)0.62533 (16)0.45489 (14)0.0242 (3)
C30.6664 (2)0.66868 (17)0.56438 (14)0.0271 (3)
H30.60380.77180.57500.033*
C40.7533 (2)0.55674 (19)0.65748 (15)0.0299 (3)
C50.8449 (2)0.40466 (18)0.63998 (15)0.0315 (3)
H50.90440.33090.70460.038*
C60.8531 (2)0.35680 (17)0.53365 (15)0.0292 (3)
C70.76463 (19)0.47267 (17)0.44329 (14)0.0262 (3)
C80.6618 (2)0.59417 (18)0.26597 (15)0.0278 (3)
C90.7515 (3)0.5984 (2)0.77707 (17)0.0415 (4)
H9A0.70240.71230.76670.062*
H9B0.87280.56660.78830.062*
H9C0.67820.54340.85370.062*
C100.9501 (2)0.19388 (19)0.51553 (18)0.0373 (4)
H10A1.06030.19670.44850.056*
H10B0.87530.15510.48860.056*
H10C0.97790.12360.59770.056*
C110.6407 (3)0.5985 (2)0.13829 (17)0.0382 (4)
H11A0.75760.57740.07860.057*
H11B0.56790.70270.10220.057*
H11C0.58290.51830.14980.057*
C120.64455 (19)1.00421 (17)0.20516 (14)0.0251 (3)
C130.7224 (2)1.05360 (19)0.27106 (15)0.0309 (3)
H130.69591.02570.36340.037*
C140.8396 (2)1.1442 (2)0.20033 (18)0.0381 (4)
H140.89571.17870.24290.046*
C150.8722 (2)1.1827 (2)0.06712 (18)0.0386 (4)
C160.7969 (2)1.1347 (2)−0.00004 (17)0.0400 (4)
H160.82331.1638−0.09240.048*
C170.6816 (2)1.0430 (2)0.07044 (15)0.0333 (3)
H170.62831.00680.02700.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.02610 (19)0.02512 (19)0.02153 (19)−0.00398 (14)−0.00822 (13)−0.00554 (13)
F0.0579 (7)0.0490 (7)0.0633 (8)−0.0316 (6)−0.0054 (6)0.0012 (6)
O10.0343 (6)0.0252 (5)0.0327 (6)−0.0066 (4)−0.0092 (5)−0.0100 (4)
O20.0309 (6)0.0314 (6)0.0254 (5)−0.0035 (4)−0.0054 (4)−0.0092 (4)
O30.0340 (6)0.0364 (6)0.0301 (6)−0.0077 (5)−0.0148 (5)−0.0058 (5)
C10.0276 (7)0.0249 (7)0.0237 (7)−0.0065 (6)−0.0074 (6)−0.0056 (5)
C20.0247 (7)0.0234 (7)0.0237 (7)−0.0078 (5)−0.0057 (5)−0.0034 (5)
C30.0296 (7)0.0255 (7)0.0252 (7)−0.0068 (6)−0.0066 (6)−0.0055 (6)
C40.0329 (8)0.0324 (8)0.0235 (7)−0.0116 (6)−0.0075 (6)−0.0022 (6)
C50.0325 (8)0.0285 (8)0.0289 (8)−0.0109 (6)−0.0100 (6)0.0040 (6)
C60.0277 (7)0.0221 (7)0.0346 (8)−0.0089 (6)−0.0072 (6)−0.0011 (6)
C70.0269 (7)0.0246 (7)0.0278 (7)−0.0097 (6)−0.0052 (6)−0.0057 (6)
C80.0292 (7)0.0273 (7)0.0286 (7)−0.0079 (6)−0.0078 (6)−0.0080 (6)
C90.0522 (11)0.0445 (10)0.0285 (8)−0.0108 (8)−0.0172 (8)−0.0051 (7)
C100.0373 (9)0.0231 (7)0.0476 (10)−0.0058 (6)−0.0124 (7)−0.0041 (7)
C110.0475 (10)0.0396 (9)0.0335 (9)−0.0092 (8)−0.0130 (7)−0.0157 (7)
C120.0280 (7)0.0223 (7)0.0228 (7)−0.0032 (5)−0.0076 (5)−0.0050 (5)
C130.0356 (8)0.0306 (8)0.0267 (7)−0.0066 (6)−0.0091 (6)−0.0084 (6)
C140.0407 (9)0.0346 (9)0.0448 (10)−0.0121 (7)−0.0116 (8)−0.0137 (7)
C150.0380 (9)0.0279 (8)0.0437 (10)−0.0123 (7)−0.0055 (7)−0.0015 (7)
C160.0442 (10)0.0428 (10)0.0263 (8)−0.0140 (8)−0.0071 (7)0.0010 (7)
C170.0381 (8)0.0368 (8)0.0248 (7)−0.0100 (7)−0.0109 (6)−0.0042 (6)

Geometric parameters (Å, °)

S—O21.4384 (11)C9—H9A0.9800
S—O31.4402 (11)C9—H9B0.9800
S—C11.7351 (15)C9—H9C0.9800
S—C121.7669 (15)C10—H10A0.9800
F—C151.3561 (19)C10—H10B0.9800
O1—C81.3647 (19)C10—H10C0.9800
O1—C71.3823 (18)C11—H11A0.9800
C1—C81.362 (2)C11—H11B0.9800
C1—C21.452 (2)C11—H11C0.9800
C2—C71.392 (2)C12—C171.387 (2)
C2—C31.396 (2)C12—C131.388 (2)
C3—C41.390 (2)C13—C141.387 (2)
C3—H30.9500C13—H130.9500
C4—C51.406 (2)C14—C151.373 (3)
C4—C91.513 (2)C14—H140.9500
C5—C61.384 (2)C15—C161.374 (3)
C5—H50.9500C16—C171.383 (2)
C6—C71.389 (2)C16—H160.9500
C6—C101.503 (2)C17—H170.9500
C8—C111.484 (2)
O2—S—O3119.38 (7)C4—C9—H9C109.5
O2—S—C1107.27 (7)H9A—C9—H9C109.5
O3—S—C1109.18 (7)H9B—C9—H9C109.5
O2—S—C12107.00 (7)C6—C10—H10A109.5
O3—S—C12107.22 (7)C6—C10—H10B109.5
C1—S—C12106.04 (7)H10A—C10—H10B109.5
C8—O1—C7107.03 (11)C6—C10—H10C109.5
C8—C1—C2107.63 (13)H10A—C10—H10C109.5
C8—C1—S126.31 (12)H10B—C10—H10C109.5
C2—C1—S126.04 (11)C8—C11—H11A109.5
C7—C2—C3119.44 (13)C8—C11—H11B109.5
C7—C2—C1104.30 (13)H11A—C11—H11B109.5
C3—C2—C1136.26 (14)C8—C11—H11C109.5
C4—C3—C2118.13 (14)H11A—C11—H11C109.5
C4—C3—H3120.9H11B—C11—H11C109.5
C2—C3—H3120.9C17—C12—C13121.50 (15)
C3—C4—C5120.01 (14)C17—C12—S118.94 (12)
C3—C4—C9120.21 (15)C13—C12—S119.50 (11)
C5—C4—C9119.77 (15)C14—C13—C12119.12 (15)
C6—C5—C4123.49 (14)C14—C13—H13120.4
C6—C5—H5118.3C12—C13—H13120.4
C4—C5—H5118.3C15—C14—C13118.22 (16)
C5—C6—C7114.38 (14)C15—C14—H14120.9
C5—C6—C10123.44 (15)C13—C14—H14120.9
C7—C6—C10122.18 (15)F—C15—C14118.37 (16)
O1—C7—C6124.84 (14)F—C15—C16118.03 (16)
O1—C7—C2110.61 (13)C14—C15—C16123.59 (16)
C6—C7—C2124.53 (14)C15—C16—C17118.18 (16)
C1—C8—O1110.43 (13)C15—C16—H16120.9
C1—C8—C11134.21 (15)C17—C16—H16120.9
O1—C8—C11115.35 (13)C16—C17—C12119.37 (15)
C4—C9—H9A109.5C16—C17—H17120.3
C4—C9—H9B109.5C12—C17—H17120.3
H9A—C9—H9B109.5
O2—S—C1—C8157.19 (13)C1—C2—C7—O1−0.13 (16)
O3—S—C1—C826.50 (16)C3—C2—C7—C6−0.8 (2)
C12—S—C1—C8−88.73 (15)C1—C2—C7—C6178.84 (14)
O2—S—C1—C2−24.51 (15)C2—C1—C8—O10.16 (17)
O3—S—C1—C2−155.21 (12)S—C1—C8—O1178.72 (10)
C12—S—C1—C289.57 (13)C2—C1—C8—C11−179.06 (17)
C8—C1—C2—C7−0.02 (16)S—C1—C8—C11−0.5 (3)
S—C1—C2—C7−178.58 (11)C7—O1—C8—C1−0.25 (16)
C8—C1—C2—C3179.48 (16)C7—O1—C8—C11179.14 (13)
S—C1—C2—C30.9 (3)O2—S—C12—C17−147.39 (12)
C7—C2—C3—C40.8 (2)O3—S—C12—C17−18.20 (14)
C1—C2—C3—C4−178.62 (15)C1—S—C12—C1798.35 (13)
C2—C3—C4—C5−0.1 (2)O2—S—C12—C1329.85 (14)
C2—C3—C4—C9179.17 (14)O3—S—C12—C13159.04 (12)
C3—C4—C5—C6−0.8 (2)C1—S—C12—C13−84.41 (13)
C9—C4—C5—C6179.94 (15)C17—C12—C13—C140.2 (2)
C4—C5—C6—C70.9 (2)S—C12—C13—C14−176.95 (12)
C4—C5—C6—C10−179.56 (15)C12—C13—C14—C150.7 (2)
C8—O1—C7—C6−178.73 (14)C13—C14—C15—F179.52 (15)
C8—O1—C7—C20.24 (16)C13—C14—C15—C16−0.9 (3)
C5—C6—C7—O1178.75 (13)F—C15—C16—C17179.80 (16)
C10—C6—C7—O1−0.8 (2)C14—C15—C16—C170.2 (3)
C5—C6—C7—C2−0.1 (2)C15—C16—C17—C120.7 (3)
C10—C6—C7—C2−179.66 (14)C13—C12—C17—C16−0.9 (2)
C3—C2—C7—O1−179.73 (12)S—C12—C17—C16176.28 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10B···O2i0.982.563.363 (2)139
C13—H13···O2ii0.952.453.365 (2)160
C17—H17···O3iii0.952.503.198 (2)130

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2040).

References

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  • Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226.
  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2009). APEX2 SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o794. [PMC free article] [PubMed]
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o850. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett 19, 2420–2428. [PubMed]
  • 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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