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ISSN: 2056-9890

3-(3-Fluoro­phenyl­sulfin­yl)-2,5,7-tri­methyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 7 April 2011; accepted 17 May 2011; online 20 May 2011)

In the title compound, C17H15FO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits a slipped ππ inter­action between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.719 (2) Å, inter­planar distance = 3.475 (2) Å and slippage = 1.325 Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For structural studies of related 3-(4-fluoro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o472.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o543.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15FO2S

  • Mr = 302.35

  • Triclinic, [P \overline 1]

  • a = 6.2942 (2) Å

  • b = 11.1162 (4) Å

  • c = 11.8021 (6) Å

  • α = 110.701 (3)°

  • β = 100.176 (3)°

  • γ = 103.621 (2)°

  • V = 719.39 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.29 × 0.25 × 0.21 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.951

  • 12696 measured reflections

  • 3301 independent reflections

  • 2760 reflections with I > 2σ(I)

  • Rint = 0.122

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.133

  • S = 1.07

  • 3301 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O2i 0.93 2.51 3.227 (2) 134
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Many compounds containing a benzofuran ring system exhibit interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a 3-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C13—H13···O2i). The crystal packing (Fig. 2) is further stabilized by a weak slipped ππ interaction between the furan rings of neighbouring molecules, with a Cg···Cgii distance of 3.719 (2) Å and an interplanar distance of 3.475 (2) Å resulting in a slippage of 1.325 Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

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 structural studies of related 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (342 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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 (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 75%, m.p. 434–435 K; Rf = 0.72 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.96 Å for methyl H atoms. Uiso(H) =1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A view of the C—H···O and ππ interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 2, - y + 1, - z + 2 ; (ii) - x + , - y + 1, - z + 1.]
3-(3-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top
Crystal data top
C17H15FO2SZ = 2
Mr = 302.35F(000) = 316
Triclinic, P1Dx = 1.396 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2942 (2) ÅCell parameters from 5769 reflections
b = 11.1162 (4) Åθ = 2.2–27.5°
c = 11.8021 (6) ŵ = 0.24 mm1
α = 110.701 (3)°T = 296 K
β = 100.176 (3)°Block, colourless
γ = 103.621 (2)°0.29 × 0.25 × 0.21 mm
V = 719.39 (5) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3301 independent reflections
Radiation source: rotating anode2760 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.122
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1414
Tmin = 0.935, Tmax = 0.951l = 1515
12696 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.133H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.086P]
where P = (Fo2 + 2Fc2)/3
3301 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C17H15FO2Sγ = 103.621 (2)°
Mr = 302.35V = 719.39 (5) Å3
Triclinic, P1Z = 2
a = 6.2942 (2) ÅMo Kα radiation
b = 11.1162 (4) ŵ = 0.24 mm1
c = 11.8021 (6) ÅT = 296 K
α = 110.701 (3)°0.29 × 0.25 × 0.21 mm
β = 100.176 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3301 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2760 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.951Rint = 0.122
12696 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.07Δρmax = 0.52 e Å3
3301 reflectionsΔρmin = 0.44 e Å3
193 parameters
Special details top

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) top
xyzUiso*/Ueq
S10.61779 (7)0.50213 (4)0.83763 (4)0.02605 (15)
O10.2342 (2)0.38830 (12)0.49387 (10)0.0275 (3)
O20.8652 (2)0.52089 (14)0.85568 (12)0.0361 (3)
F10.7099 (2)0.14993 (13)1.00630 (12)0.0517 (4)
C10.4798 (3)0.42715 (17)0.67501 (15)0.0249 (3)
C20.5132 (3)0.31895 (16)0.57616 (15)0.0250 (3)
C30.6547 (3)0.23900 (18)0.56868 (17)0.0303 (4)
H30.76180.25160.64060.036*
C40.6325 (3)0.14076 (18)0.45232 (18)0.0342 (4)
C50.4696 (3)0.12330 (18)0.34451 (18)0.0350 (4)
H50.45730.05610.26700.042*
C60.3262 (3)0.20148 (18)0.34811 (16)0.0307 (4)
C70.3566 (3)0.29841 (16)0.46668 (15)0.0256 (4)
C80.3133 (3)0.46537 (17)0.62103 (15)0.0253 (3)
C90.7843 (4)0.0524 (2)0.4405 (2)0.0470 (5)
H9A0.92380.09700.42900.070*
H9B0.70750.03320.36910.070*
H9C0.81770.03730.51600.070*
C100.1525 (4)0.1847 (2)0.23408 (17)0.0417 (5)
H10A0.00340.16320.24590.063*
H10B0.15680.11250.16080.063*
H10C0.18630.26780.22260.063*
C110.2019 (3)0.56740 (18)0.67277 (17)0.0324 (4)
H11A0.04900.52200.66870.049*
H11B0.19820.62050.62410.049*
H11C0.28630.62590.75910.049*
C120.5032 (3)0.35709 (16)0.86983 (14)0.0243 (3)
C130.6565 (3)0.30906 (17)0.92600 (15)0.0280 (4)
H130.81320.34780.94410.034*
C140.5646 (3)0.20107 (18)0.95355 (17)0.0326 (4)
C150.3363 (3)0.14339 (18)0.93105 (17)0.0352 (4)
H150.28140.07060.95130.042*
C160.1877 (3)0.19579 (19)0.87727 (18)0.0352 (4)
H160.03130.15830.86180.042*
C170.2699 (3)0.30294 (18)0.84667 (17)0.0309 (4)
H170.17030.33840.81100.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0285 (3)0.0248 (2)0.0201 (2)0.00624 (17)0.00117 (16)0.00820 (17)
O10.0280 (6)0.0311 (6)0.0233 (6)0.0126 (5)0.0020 (5)0.0117 (5)
O20.0248 (6)0.0437 (7)0.0335 (7)0.0014 (5)0.0012 (5)0.0196 (6)
F10.0560 (8)0.0466 (7)0.0606 (8)0.0225 (6)0.0038 (6)0.0334 (7)
C10.0251 (8)0.0269 (8)0.0228 (8)0.0100 (6)0.0033 (6)0.0111 (7)
C20.0256 (8)0.0249 (8)0.0247 (8)0.0080 (7)0.0053 (6)0.0115 (7)
C30.0283 (9)0.0320 (9)0.0349 (9)0.0141 (7)0.0078 (7)0.0163 (8)
C40.0365 (10)0.0290 (9)0.0430 (11)0.0148 (8)0.0173 (8)0.0159 (8)
C50.0454 (11)0.0257 (8)0.0300 (9)0.0093 (8)0.0147 (8)0.0067 (8)
C60.0352 (9)0.0274 (8)0.0255 (8)0.0058 (7)0.0078 (7)0.0098 (7)
C70.0267 (8)0.0248 (8)0.0250 (8)0.0091 (7)0.0059 (7)0.0104 (7)
C80.0267 (8)0.0264 (8)0.0222 (8)0.0084 (7)0.0040 (6)0.0110 (7)
C90.0534 (13)0.0413 (11)0.0591 (13)0.0285 (10)0.0272 (11)0.0216 (11)
C100.0533 (12)0.0370 (10)0.0235 (9)0.0065 (9)0.0003 (8)0.0101 (8)
C110.0341 (10)0.0335 (9)0.0336 (9)0.0173 (8)0.0086 (8)0.0148 (8)
C120.0290 (8)0.0238 (8)0.0164 (7)0.0082 (6)0.0034 (6)0.0058 (6)
C130.0275 (8)0.0291 (8)0.0241 (8)0.0100 (7)0.0031 (7)0.0088 (7)
C140.0439 (10)0.0287 (8)0.0261 (8)0.0176 (8)0.0051 (8)0.0109 (7)
C150.0465 (11)0.0263 (9)0.0292 (9)0.0071 (8)0.0104 (8)0.0104 (7)
C160.0306 (9)0.0335 (9)0.0360 (10)0.0046 (8)0.0098 (8)0.0116 (8)
C170.0270 (8)0.0339 (9)0.0292 (9)0.0107 (7)0.0038 (7)0.0116 (8)
Geometric parameters (Å, º) top
S1—O21.4876 (13)C9—H9A0.9600
S1—C11.7527 (16)C9—H9B0.9600
S1—C121.8017 (17)C9—H9C0.9600
O1—C81.3639 (19)C10—H10A0.9600
O1—C71.3851 (19)C10—H10B0.9600
F1—C141.357 (2)C10—H10C0.9600
C1—C81.360 (2)C11—H11A0.9600
C1—C21.437 (2)C11—H11B0.9600
C2—C71.389 (2)C11—H11C0.9600
C2—C31.391 (2)C12—C171.386 (2)
C3—C41.378 (3)C12—C131.386 (2)
C3—H30.9300C13—C141.377 (3)
C4—C51.407 (3)C13—H130.9300
C4—C91.513 (2)C14—C151.363 (3)
C5—C61.389 (3)C15—C161.388 (3)
C5—H50.9300C15—H150.9300
C6—C71.378 (2)C16—C171.377 (3)
C6—C101.499 (2)C16—H160.9300
C8—C111.479 (2)C17—H170.9300
O2—S1—C1108.38 (8)H9A—C9—H9C109.5
O2—S1—C12105.93 (7)H9B—C9—H9C109.5
C1—S1—C1297.25 (7)C6—C10—H10A109.5
C8—O1—C7106.64 (12)C6—C10—H10B109.5
C8—C1—C2107.69 (14)H10A—C10—H10B109.5
C8—C1—S1123.27 (13)C6—C10—H10C109.5
C2—C1—S1129.04 (12)H10A—C10—H10C109.5
C7—C2—C3119.25 (15)H10B—C10—H10C109.5
C7—C2—C1104.76 (13)C8—C11—H11A109.5
C3—C2—C1135.99 (15)C8—C11—H11B109.5
C4—C3—C2118.52 (16)H11A—C11—H11B109.5
C4—C3—H3120.7C8—C11—H11C109.5
C2—C3—H3120.7H11A—C11—H11C109.5
C3—C4—C5119.93 (16)H11B—C11—H11C109.5
C3—C4—C9119.97 (17)C17—C12—C13121.95 (16)
C5—C4—C9120.09 (18)C17—C12—S1120.18 (12)
C6—C5—C4123.21 (17)C13—C12—S1117.72 (13)
C6—C5—H5118.4C14—C13—C12116.56 (16)
C4—C5—H5118.4C14—C13—H13121.7
C7—C6—C5114.34 (16)C12—C13—H13121.7
C7—C6—C10121.75 (17)F1—C14—C15118.44 (17)
C5—C6—C10123.91 (17)F1—C14—C13118.02 (17)
C6—C7—O1124.90 (15)C15—C14—C13123.54 (16)
C6—C7—C2124.74 (15)C14—C15—C16118.45 (17)
O1—C7—C2110.36 (14)C14—C15—H15120.8
C1—C8—O1110.54 (14)C16—C15—H15120.8
C1—C8—C11133.15 (16)C17—C16—C15120.52 (17)
O1—C8—C11116.28 (13)C17—C16—H16119.7
C4—C9—H9A109.5C15—C16—H16119.7
C4—C9—H9B109.5C16—C17—C12118.94 (16)
H9A—C9—H9B109.5C16—C17—H17120.5
C4—C9—H9C109.5C12—C17—H17120.5
O2—S1—C1—C8138.58 (15)C1—C2—C7—C6178.81 (16)
C12—S1—C1—C8111.91 (16)C3—C2—C7—O1179.52 (15)
O2—S1—C1—C241.89 (18)C1—C2—C7—O10.63 (19)
C12—S1—C1—C267.61 (17)C2—C1—C8—O10.7 (2)
C8—C1—C2—C70.79 (19)S1—C1—C8—O1178.92 (12)
S1—C1—C2—C7178.79 (14)C2—C1—C8—C11178.47 (19)
C8—C1—C2—C3179.4 (2)S1—C1—C8—C111.1 (3)
S1—C1—C2—C31.0 (3)C7—O1—C8—C10.30 (19)
C7—C2—C3—C40.7 (3)C7—O1—C8—C11178.49 (15)
C1—C2—C3—C4179.12 (19)O2—S1—C12—C17172.33 (13)
C2—C3—C4—C50.1 (3)C1—S1—C12—C1760.80 (15)
C2—C3—C4—C9179.70 (17)O2—S1—C12—C1312.06 (14)
C3—C4—C5—C60.2 (3)C1—S1—C12—C13123.59 (13)
C9—C4—C5—C6179.39 (19)C17—C12—C13—C142.3 (2)
C4—C5—C6—C70.1 (3)S1—C12—C13—C14177.84 (12)
C4—C5—C6—C10179.67 (18)C12—C13—C14—F1178.73 (15)
C5—C6—C7—O1179.93 (16)C12—C13—C14—C151.5 (3)
C10—C6—C7—O10.3 (3)F1—C14—C15—C16179.91 (16)
C5—C6—C7—C20.7 (3)C13—C14—C15—C160.1 (3)
C10—C6—C7—C2179.67 (17)C14—C15—C16—C170.5 (3)
C8—O1—C7—C6179.21 (16)C15—C16—C17—C120.3 (3)
C8—O1—C7—C20.23 (19)C13—C12—C17—C161.8 (3)
C3—C2—C7—C61.0 (3)S1—C12—C17—C16177.22 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.513.227 (2)134
Symmetry code: (i) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC17H15FO2S
Mr302.35
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.2942 (2), 11.1162 (4), 11.8021 (6)
α, β, γ (°)110.701 (3), 100.176 (3), 103.621 (2)
V3)719.39 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.29 × 0.25 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.935, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
12696, 3301, 2760
Rint0.122
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.07
No. of reflections3301
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.513.227 (2)134
Symmetry code: (i) x+2, y+1, z+2.
 

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