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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3261.
Published online 2010 November 20. doi:  10.1107/S1600536810047665
PMCID: PMC3011574

2-(4-Fluoro­phen­yl)-5-iodo-3-isopropyl­sulfinyl-1-benzofuran

Abstract

In the title compound, C17H14FIO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 18.88 (9)° with the mean plane of the benzofuran ring. In the crystal, pairs of inter­molecular I(...)O contacts [3.153 (2) Å] link the mol­ecules into inversion dimers.

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 our previous structural studies of related 3-alkyl­sulfinyl-2-(4-fluoro­phen­yl)-5-iodo-1-benzofuran derivatives, see: Choi et al. (2010a [triangle],b [triangle]). For a review of halogen bonding, see: Politzer et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3261-scheme1.jpg

Experimental

Crystal data

  • C17H14FIO2S
  • M r = 428.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3261-efi1.jpg
  • a = 8.4345 (1) Å
  • b = 9.5874 (2) Å
  • c = 10.9324 (2) Å
  • α = 68.643 (1)°
  • β = 70.618 (1)°
  • γ = 89.241 (1)°
  • V = 770.83 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.23 mm−1
  • T = 180 K
  • 0.23 × 0.22 × 0.12 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.594, T max = 0.746
  • 13711 measured reflections
  • 3544 independent reflections
  • 3407 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.020
  • wR(F 2) = 0.055
  • S = 1.14
  • 3544 reflections
  • 201 parameters
  • H-atom parameters constrained
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.93 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047665/su2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047665/su2229Isup2.hkl

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

Acknowledgments

This work was supported by Blue-Bio Industry RIC at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan City.

supplementary crystallographic information

Comment

Many compounds involving a benzofuran ring have received much attention in view of their potent pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 3-alkylsulfinyl-2-(4-fluorophenyl)-5-iodo-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran ring and the 4-fluorophenyl ring is 18.88 (9)°. The molecular packing is stabilized by an I···O halogen-bonding between the iodine and the oxygen of the S═O unit [I1···O2i = 3.153 (2) Å; C4—I1···O2i = 170.73 (6)°; (i) - x + 1, - y, - z + 2 ] (Politzer et al., 2007).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-isopropylsulfanyl-1-benzofuran (371 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 430–431 K. Rf = 0.65 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow 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, 1.00 Å for methine, and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methine, 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.

Crystal data

C17H14FIO2SZ = 2
Mr = 428.24F(000) = 420
Triclinic, P1Dx = 1.845 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4345 (1) ÅCell parameters from 9898 reflections
b = 9.5874 (2) Åθ = 2.3–27.5°
c = 10.9324 (2) ŵ = 2.23 mm1
α = 68.643 (1)°T = 180 K
β = 70.618 (1)°Block, colourless
γ = 89.241 (1)°0.23 × 0.22 × 0.12 mm
V = 770.83 (2) Å3

Data collection

Bruker SMART APEXII CCD diffractometer3544 independent reflections
Radiation source: rotating anode3407 reflections with I > 2σ(I)
graphite multilayerRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.1°
[var phi] and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.594, Tmax = 0.746l = −14→14
13711 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)] = 0.020Hydrogen site location: difference Fourier map
wR(F2) = 0.055H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0298P)2 + 0.238P] where P = (Fo2 + 2Fc2)/3
3544 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = −0.93 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
I10.417391 (15)0.151710 (13)1.131578 (12)0.02794 (6)
S10.35022 (6)0.16149 (5)0.56324 (5)0.02224 (10)
F10.08962 (18)0.68702 (15)0.06579 (14)0.0395 (3)
O10.27453 (17)0.55572 (14)0.60153 (14)0.0241 (3)
O20.46705 (19)0.07898 (17)0.63276 (17)0.0324 (3)
C10.3041 (2)0.3160 (2)0.61705 (19)0.0213 (3)
C20.3257 (2)0.3290 (2)0.7385 (2)0.0213 (3)
C30.3567 (2)0.2321 (2)0.8569 (2)0.0238 (4)
H30.36970.12930.87160.029*
C40.3677 (2)0.2918 (2)0.9521 (2)0.0240 (4)
C50.3511 (3)0.4434 (2)0.9322 (2)0.0279 (4)
H50.36110.48010.99950.034*
C60.3203 (3)0.5403 (2)0.8147 (2)0.0284 (4)
H60.30870.64350.79910.034*
C70.3074 (2)0.4790 (2)0.7221 (2)0.0234 (4)
C80.2727 (2)0.4542 (2)0.5392 (2)0.0216 (3)
C90.2301 (2)0.5145 (2)0.4121 (2)0.0221 (4)
C100.2428 (2)0.6710 (2)0.3413 (2)0.0253 (4)
H100.28340.73740.37390.030*
C110.1966 (3)0.7288 (2)0.2242 (2)0.0290 (4)
H110.20630.83480.17520.035*
C120.1363 (2)0.6309 (2)0.1796 (2)0.0273 (4)
C130.1226 (3)0.4763 (2)0.2458 (2)0.0278 (4)
H130.08180.41110.21200.033*
C140.1698 (3)0.4187 (2)0.3627 (2)0.0264 (4)
H140.16110.31250.41000.032*
C150.1418 (2)0.0465 (2)0.6546 (2)0.0245 (4)
H150.05420.11150.63090.029*
C160.0973 (3)−0.0158 (3)0.8118 (2)0.0350 (5)
H16A−0.0086−0.08430.85680.053*
H16B0.08330.06750.84480.053*
H16C0.1883−0.07090.83590.053*
C170.1496 (3)−0.0768 (2)0.5953 (3)0.0396 (5)
H17A0.2342−0.14220.61870.059*
H17B0.1811−0.02990.49320.059*
H17C0.0384−0.13700.63620.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.03365 (9)0.02957 (8)0.02477 (9)0.00348 (5)−0.01555 (6)−0.01020 (6)
S10.0247 (2)0.0215 (2)0.0218 (2)0.00425 (17)−0.00912 (18)−0.00885 (17)
F10.0464 (8)0.0401 (7)0.0277 (7)0.0044 (6)−0.0213 (6)−0.0007 (5)
O10.0285 (7)0.0208 (6)0.0257 (7)0.0037 (5)−0.0134 (6)−0.0084 (5)
O20.0322 (8)0.0346 (7)0.0376 (8)0.0131 (6)−0.0195 (7)−0.0156 (7)
C10.0214 (8)0.0220 (8)0.0212 (9)0.0022 (6)−0.0080 (7)−0.0084 (7)
C20.0190 (8)0.0236 (8)0.0227 (9)0.0022 (6)−0.0069 (7)−0.0106 (7)
C30.0244 (9)0.0237 (8)0.0253 (10)0.0048 (7)−0.0106 (7)−0.0099 (7)
C40.0225 (9)0.0287 (9)0.0226 (9)0.0035 (7)−0.0109 (7)−0.0094 (8)
C50.0298 (10)0.0309 (10)0.0305 (11)0.0048 (8)−0.0139 (8)−0.0169 (8)
C60.0335 (10)0.0241 (9)0.0342 (11)0.0061 (8)−0.0163 (9)−0.0144 (8)
C70.0213 (9)0.0240 (8)0.0254 (10)0.0031 (7)−0.0103 (7)−0.0084 (7)
C80.0202 (8)0.0219 (8)0.0226 (9)0.0013 (6)−0.0074 (7)−0.0086 (7)
C90.0189 (8)0.0226 (8)0.0211 (9)0.0015 (6)−0.0056 (7)−0.0054 (7)
C100.0235 (9)0.0225 (8)0.0272 (10)0.0023 (7)−0.0080 (8)−0.0072 (8)
C110.0286 (10)0.0212 (8)0.0300 (11)0.0039 (7)−0.0095 (8)−0.0026 (8)
C120.0239 (9)0.0315 (9)0.0208 (9)0.0048 (7)−0.0093 (7)−0.0022 (8)
C130.0295 (10)0.0291 (9)0.0245 (10)0.0002 (8)−0.0110 (8)−0.0083 (8)
C140.0320 (10)0.0206 (8)0.0247 (10)0.0003 (7)−0.0126 (8)−0.0042 (7)
C150.0251 (9)0.0205 (8)0.0272 (10)0.0017 (7)−0.0118 (8)−0.0059 (7)
C160.0344 (11)0.0356 (11)0.0258 (11)−0.0043 (9)−0.0104 (9)−0.0014 (9)
C170.0460 (13)0.0288 (10)0.0476 (14)0.0008 (9)−0.0163 (11)−0.0185 (10)

Geometric parameters (Å, °)

I1—C42.1074 (19)C9—C141.397 (3)
I1—O2i3.1525 (15)C9—C101.402 (2)
S1—O21.4876 (15)C10—C111.381 (3)
S1—C11.7774 (18)C10—H100.9500
S1—C151.841 (2)C11—C121.374 (3)
F1—C121.351 (2)C11—H110.9500
O1—C71.373 (2)C12—C131.380 (3)
O1—C81.380 (2)C13—C141.384 (3)
C1—C81.367 (3)C13—H130.9500
C1—C21.446 (3)C14—H140.9500
C2—C31.396 (3)C15—C161.510 (3)
C2—C71.396 (2)C15—C171.532 (3)
C3—C41.385 (3)C15—H151.0000
C3—H30.9500C16—H16A0.9800
C4—C51.402 (3)C16—H16B0.9800
C5—C61.388 (3)C16—H16C0.9800
C5—H50.9500C17—H17A0.9800
C6—C71.375 (3)C17—H17B0.9800
C6—H60.9500C17—H17C0.9800
C8—C91.460 (3)
C4—I1—O2i170.73 (6)C11—C10—H10119.9
O2—S1—C1106.47 (8)C9—C10—H10119.9
O2—S1—C15107.12 (9)C12—C11—C10119.07 (18)
C1—S1—C1599.87 (9)C12—C11—H11120.5
C7—O1—C8106.69 (14)C10—C11—H11120.5
C8—C1—C2106.99 (15)F1—C12—C11119.27 (17)
C8—C1—S1126.19 (15)F1—C12—C13118.10 (18)
C2—C1—S1125.82 (13)C11—C12—C13122.63 (19)
C3—C2—C7118.97 (17)C12—C13—C14118.15 (18)
C3—C2—C1135.97 (17)C12—C13—H13120.9
C7—C2—C1105.06 (16)C14—C13—H13120.9
C4—C3—C2117.37 (17)C13—C14—C9120.93 (17)
C4—C3—H3121.3C13—C14—H14119.5
C2—C3—H3121.3C9—C14—H14119.5
C3—C4—C5122.52 (18)C16—C15—C17113.13 (17)
C3—C4—I1119.10 (14)C16—C15—S1111.52 (14)
C5—C4—I1118.36 (14)C17—C15—S1106.42 (14)
C6—C5—C4120.40 (18)C16—C15—H15108.5
C6—C5—H5119.8C17—C15—H15108.5
C4—C5—H5119.8S1—C15—H15108.5
C7—C6—C5116.43 (17)C15—C16—H16A109.5
C7—C6—H6121.8C15—C16—H16B109.5
C5—C6—H6121.8H16A—C16—H16B109.5
O1—C7—C6125.06 (16)C15—C16—H16C109.5
O1—C7—C2110.64 (16)H16A—C16—H16C109.5
C6—C7—C2124.30 (18)H16B—C16—H16C109.5
C1—C8—O1110.61 (16)C15—C17—H17A109.5
C1—C8—C9134.93 (17)C15—C17—H17B109.5
O1—C8—C9114.36 (15)H17A—C17—H17B109.5
C14—C9—C10119.02 (18)C15—C17—H17C109.5
C14—C9—C8121.04 (16)H17A—C17—H17C109.5
C10—C9—C8119.88 (17)H17B—C17—H17C109.5
C11—C10—C9120.20 (18)
O2—S1—C1—C8147.63 (17)S1—C1—C8—O1−168.30 (13)
C15—S1—C1—C8−101.09 (18)C2—C1—C8—C9−175.53 (19)
O2—S1—C1—C2−19.38 (18)S1—C1—C8—C915.5 (3)
C15—S1—C1—C291.91 (17)C7—O1—C8—C1−0.2 (2)
C8—C1—C2—C3178.6 (2)C7—O1—C8—C9176.86 (15)
S1—C1—C2—C3−12.3 (3)C1—C8—C9—C1417.1 (3)
C8—C1—C2—C7−0.9 (2)O1—C8—C9—C14−159.09 (17)
S1—C1—C2—C7168.15 (14)C1—C8—C9—C10−165.7 (2)
C7—C2—C3—C40.0 (3)O1—C8—C9—C1018.2 (2)
C1—C2—C3—C4−179.5 (2)C14—C9—C10—C11−0.2 (3)
C2—C3—C4—C5−0.8 (3)C8—C9—C10—C11−177.49 (17)
C2—C3—C4—I1−179.23 (13)C9—C10—C11—C120.8 (3)
C3—C4—C5—C60.9 (3)C10—C11—C12—F1179.47 (18)
I1—C4—C5—C6179.27 (15)C10—C11—C12—C13−1.1 (3)
C4—C5—C6—C70.0 (3)F1—C12—C13—C14−179.79 (18)
C8—O1—C7—C6179.81 (18)C11—C12—C13—C140.8 (3)
C8—O1—C7—C2−0.40 (19)C12—C13—C14—C9−0.1 (3)
C5—C6—C7—O1178.82 (18)C10—C9—C14—C13−0.2 (3)
C5—C6—C7—C2−0.9 (3)C8—C9—C14—C13177.14 (18)
C3—C2—C7—O1−178.83 (16)O2—S1—C15—C1643.28 (16)
C1—C2—C7—O10.8 (2)C1—S1—C15—C16−67.49 (15)
C3—C2—C7—C61.0 (3)O2—S1—C15—C17−80.53 (15)
C1—C2—C7—C6−179.40 (18)C1—S1—C15—C17168.70 (14)
C2—C1—C8—O10.7 (2)

Symmetry codes: (i) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2229).

References

  • Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. [PubMed]
  • 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. (2010a). Acta Cryst. E66, o44. [PMC free article] [PubMed]
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1043. [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]
  • Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model 13, 305–311. [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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