Acta Cryst. (2011). E67, o65 [ doi:10.1107/S1600536810051020 ]
In the title compound, C17H14ClIO2S, the 4-chlorophenyl ring makes a dihedral angle of 12.13 (5)° with the mean plane of the benzofuran ring. In the crystal, pairs of intermolecular I
O contacts [3.145 (1) Å] link the molecules into inversion dimers.
77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 2-(4-chlorophenyl)-3-ethylsulfanyl-5-iodo-7-methyl-1-benzofuran (343 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h, 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 78%, m.p. 459–460 K; R f = 0.66 (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 tetrahydofuran at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 0.99 Å for methylene, and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.
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).
![[Figure 1]](./xu5113fig1thm.gif)
| 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. |
| C17H14ClIO2S | Z = 2 |
| Mr = 444.69 | F(000) = 436 |
| Triclinic, P1 | Dx = 1.828 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.3535 (1) Å | Cell parameters from 6925 reflections |
| b = 10.4958 (2) Å | θ = 2.6–27.4° |
| c = 11.9856 (2) Å | µ = 2.28 mm−1 |
| α = 68.509 (1)° | T = 173 K |
| β = 88.317 (1)° | Block, colourless |
| γ = 70.726 (1)° | 0.26 × 0.16 × 0.13 mm |
| V = 808.07 (2) Å3 |
| Bruker SMART APEXII CCD diffractometer | 3738 independent reflections |
| Radiation source: rotating anode | 3594 reflections with I > 2σ(I) |
| graphite multilayer | Rint = 0.024 |
| Detector resolution: 10.0 pixels mm-1 | θmax = 27.6°, θmin = 1.8° |
| φ and ω scans | h = −9→9 |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −13→13 |
| Tmin = 0.583, Tmax = 0.746 | l = −15→15 |
| 14205 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.020 | Hydrogen site location: difference Fourier map |
| wR(F2) = 0.051 | H-atom parameters constrained |
| S = 1.09 | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.4245P] where P = (Fo2 + 2Fc2)/3 |
| 3738 reflections | (Δ/σ)max = 0.001 |
| 201 parameters | Δρmax = 0.45 e Å−3 |
| 0 restraints | Δρmin = −0.94 e Å−3 |
| C17H14ClIO2S | γ = 70.726 (1)° |
| Mr = 444.69 | V = 808.07 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.3535 (1) Å | Mo Kα radiation |
| b = 10.4958 (2) Å | µ = 2.28 mm−1 |
| c = 11.9856 (2) Å | T = 173 K |
| α = 68.509 (1)° | 0.26 × 0.16 × 0.13 mm |
| β = 88.317 (1)° |
| Bruker SMART APEXII CCD diffractometer | 3738 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3594 reflections with I > 2σ(I) |
| Tmin = 0.583, Tmax = 0.746 | Rint = 0.024 |
| 14205 measured reflections | θmax = 27.6° |
| R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
| wR(F2) = 0.051 | Δρmax = 0.45 e Å−3 |
| S = 1.09 | Δρmin = −0.94 e Å−3 |
| 3738 reflections | Absolute structure: ? |
| 201 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| I1 | 0.503893 (18) | 0.274401 (13) | 0.581925 (10) | 0.02859 (5) | |
| Cl1 | −0.07192 (8) | 0.84278 (7) | −0.52118 (4) | 0.03868 (12) | |
| S1 | 0.14553 (6) | 0.80350 (5) | 0.08547 (4) | 0.02301 (9) | |
| O1 | 0.30263 (18) | 0.42620 (14) | 0.04254 (11) | 0.0222 (2) | |
| O2 | 0.3030 (2) | 0.80681 (17) | 0.15921 (14) | 0.0345 (3) | |
| C1 | 0.2076 (2) | 0.62148 (19) | 0.09517 (15) | 0.0208 (3) | |
| C2 | 0.2943 (2) | 0.49373 (19) | 0.20294 (16) | 0.0210 (3) | |
| C3 | 0.3318 (3) | 0.4664 (2) | 0.32484 (16) | 0.0232 (3) | |
| H3 | 0.2922 | 0.5425 | 0.3548 | 0.028* | |
| C4 | 0.4289 (3) | 0.3238 (2) | 0.39943 (16) | 0.0235 (3) | |
| C5 | 0.4907 (3) | 0.2096 (2) | 0.35746 (17) | 0.0243 (3) | |
| H5 | 0.5592 | 0.1135 | 0.4125 | 0.029* | |
| C6 | 0.4537 (3) | 0.2344 (2) | 0.23693 (16) | 0.0226 (3) | |
| C7 | 0.3527 (2) | 0.3779 (2) | 0.16434 (15) | 0.0209 (3) | |
| C8 | 0.2147 (2) | 0.57512 (19) | 0.00175 (16) | 0.0208 (3) | |
| C9 | 0.1473 (3) | 0.6442 (2) | −0.12649 (16) | 0.0215 (3) | |
| C10 | 0.0170 (3) | 0.7870 (2) | −0.17795 (17) | 0.0254 (4) | |
| H10 | −0.0272 | 0.8422 | −0.1289 | 0.030* | |
| C11 | −0.0488 (3) | 0.8489 (2) | −0.29937 (17) | 0.0279 (4) | |
| H11 | −0.1361 | 0.9464 | −0.3339 | 0.033* | |
| C12 | 0.0141 (3) | 0.7673 (2) | −0.36959 (16) | 0.0266 (4) | |
| C13 | 0.1431 (3) | 0.6251 (2) | −0.32175 (17) | 0.0282 (4) | |
| H13 | 0.1848 | 0.5703 | −0.3714 | 0.034* | |
| C14 | 0.2101 (3) | 0.5646 (2) | −0.20065 (17) | 0.0256 (4) | |
| H14 | 0.2999 | 0.4678 | −0.1673 | 0.031* | |
| C15 | 0.5208 (3) | 0.1159 (2) | 0.18763 (18) | 0.0287 (4) | |
| H15A | 0.4093 | 0.0931 | 0.1687 | 0.043* | |
| H15B | 0.6139 | 0.0285 | 0.2478 | 0.043* | |
| H15C | 0.5829 | 0.1488 | 0.1142 | 0.043* | |
| C16 | −0.0614 (3) | 0.8112 (2) | 0.17132 (18) | 0.0297 (4) | |
| H16A | −0.0306 | 0.7209 | 0.2445 | 0.036* | |
| H16B | −0.0915 | 0.8948 | 0.1971 | 0.036* | |
| C17 | −0.2369 (3) | 0.8279 (2) | 0.0956 (2) | 0.0325 (4) | |
| H17A | −0.2731 | 0.9210 | 0.0264 | 0.049* | |
| H17B | −0.3455 | 0.8260 | 0.1448 | 0.049* | |
| H17C | −0.2048 | 0.7476 | 0.0669 | 0.049* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I1 | 0.03639 (8) | 0.02645 (8) | 0.01946 (7) | −0.01066 (6) | −0.00220 (5) | −0.00457 (5) |
| Cl1 | 0.0389 (3) | 0.0503 (3) | 0.0189 (2) | −0.0157 (2) | −0.00118 (19) | −0.0037 (2) |
| S1 | 0.0265 (2) | 0.0185 (2) | 0.0227 (2) | −0.00738 (17) | 0.00088 (17) | −0.00659 (17) |
| O1 | 0.0241 (6) | 0.0192 (6) | 0.0197 (6) | −0.0044 (5) | 0.0011 (5) | −0.0062 (5) |
| O2 | 0.0367 (8) | 0.0346 (8) | 0.0356 (8) | −0.0170 (6) | −0.0046 (6) | −0.0121 (6) |
| C1 | 0.0201 (8) | 0.0186 (8) | 0.0202 (8) | −0.0049 (6) | 0.0012 (6) | −0.0050 (7) |
| C2 | 0.0187 (8) | 0.0189 (8) | 0.0229 (8) | −0.0051 (6) | 0.0014 (6) | −0.0063 (7) |
| C3 | 0.0236 (8) | 0.0229 (9) | 0.0232 (8) | −0.0076 (7) | 0.0019 (7) | −0.0092 (7) |
| C4 | 0.0236 (8) | 0.0259 (9) | 0.0197 (8) | −0.0091 (7) | 0.0008 (6) | −0.0064 (7) |
| C5 | 0.0230 (8) | 0.0202 (9) | 0.0244 (8) | −0.0056 (7) | 0.0004 (7) | −0.0040 (7) |
| C6 | 0.0203 (8) | 0.0194 (8) | 0.0248 (8) | −0.0046 (7) | 0.0019 (7) | −0.0066 (7) |
| C7 | 0.0193 (8) | 0.0217 (9) | 0.0199 (8) | −0.0059 (7) | 0.0017 (6) | −0.0068 (7) |
| C8 | 0.0189 (8) | 0.0180 (8) | 0.0227 (8) | −0.0049 (6) | 0.0031 (6) | −0.0060 (7) |
| C9 | 0.0208 (8) | 0.0221 (9) | 0.0210 (8) | −0.0094 (7) | 0.0026 (6) | −0.0057 (7) |
| C10 | 0.0239 (9) | 0.0256 (9) | 0.0236 (9) | −0.0059 (7) | 0.0021 (7) | −0.0083 (7) |
| C11 | 0.0238 (9) | 0.0258 (10) | 0.0260 (9) | −0.0056 (7) | 0.0010 (7) | −0.0034 (8) |
| C12 | 0.0264 (9) | 0.0338 (10) | 0.0173 (8) | −0.0148 (8) | 0.0011 (7) | −0.0033 (7) |
| C13 | 0.0337 (10) | 0.0311 (10) | 0.0222 (9) | −0.0139 (8) | 0.0060 (7) | −0.0106 (8) |
| C14 | 0.0286 (9) | 0.0230 (9) | 0.0233 (9) | −0.0094 (7) | 0.0033 (7) | −0.0063 (7) |
| C15 | 0.0310 (10) | 0.0214 (9) | 0.0293 (9) | −0.0033 (7) | 0.0026 (8) | −0.0096 (8) |
| C16 | 0.0308 (10) | 0.0283 (10) | 0.0262 (9) | −0.0038 (8) | 0.0058 (8) | −0.0120 (8) |
| C17 | 0.0282 (10) | 0.0314 (11) | 0.0404 (11) | −0.0111 (8) | 0.0090 (8) | −0.0158 (9) |
| I1—C4 | 2.0995 (17) | C9—C10 | 1.397 (3) |
| I1—O2i | 3.1451 (14) | C9—C14 | 1.403 (3) |
| Cl1—C12 | 1.7351 (18) | C10—C11 | 1.384 (3) |
| S1—O2 | 1.4940 (14) | C10—H10 | 0.9500 |
| S1—C1 | 1.7709 (18) | C11—C12 | 1.378 (3) |
| S1—C16 | 1.808 (2) | C11—H11 | 0.9500 |
| O1—C7 | 1.375 (2) | C12—C13 | 1.388 (3) |
| O1—C8 | 1.375 (2) | C13—C14 | 1.383 (3) |
| C1—C8 | 1.368 (2) | C13—H13 | 0.9500 |
| C1—C2 | 1.445 (2) | C14—H14 | 0.9500 |
| C2—C7 | 1.390 (2) | C15—H15A | 0.9800 |
| C2—C3 | 1.399 (2) | C15—H15B | 0.9800 |
| C3—C4 | 1.379 (3) | C15—H15C | 0.9800 |
| C3—H3 | 0.9500 | C16—C17 | 1.524 (3) |
| C4—C5 | 1.402 (3) | C16—H16A | 0.9900 |
| C5—C6 | 1.389 (3) | C16—H16B | 0.9900 |
| C5—H5 | 0.9500 | C17—H17A | 0.9800 |
| C6—C7 | 1.385 (3) | C17—H17B | 0.9800 |
| C6—C15 | 1.502 (2) | C17—H17C | 0.9800 |
| C8—C9 | 1.458 (2) | ||
| C4—I1—O2i | 169.00 (6) | C11—C10—H10 | 119.5 |
| O2—S1—C1 | 106.72 (9) | C9—C10—H10 | 119.5 |
| O2—S1—C16 | 107.26 (9) | C12—C11—C10 | 119.13 (18) |
| C1—S1—C16 | 98.39 (9) | C12—C11—H11 | 120.4 |
| C7—O1—C8 | 106.98 (13) | C10—C11—H11 | 120.4 |
| C8—C1—C2 | 107.22 (15) | C11—C12—C13 | 121.62 (17) |
| C8—C1—S1 | 127.20 (14) | C11—C12—Cl1 | 119.41 (16) |
| C2—C1—S1 | 124.72 (13) | C13—C12—Cl1 | 118.97 (15) |
| C7—C2—C3 | 119.17 (16) | C14—C13—C12 | 118.90 (18) |
| C7—C2—C1 | 105.01 (15) | C14—C13—H13 | 120.5 |
| C3—C2—C1 | 135.80 (17) | C12—C13—H13 | 120.5 |
| C4—C3—C2 | 116.85 (16) | C13—C14—C9 | 120.86 (18) |
| C4—C3—H3 | 121.6 | C13—C14—H14 | 119.6 |
| C2—C3—H3 | 121.6 | C9—C14—H14 | 119.6 |
| C3—C4—C5 | 122.78 (16) | C6—C15—H15A | 109.5 |
| C3—C4—I1 | 119.43 (13) | C6—C15—H15B | 109.5 |
| C5—C4—I1 | 117.69 (13) | H15A—C15—H15B | 109.5 |
| C6—C5—C4 | 121.23 (17) | C6—C15—H15C | 109.5 |
| C6—C5—H5 | 119.4 | H15A—C15—H15C | 109.5 |
| C4—C5—H5 | 119.4 | H15B—C15—H15C | 109.5 |
| C7—C6—C5 | 114.88 (16) | C17—C16—S1 | 110.43 (13) |
| C7—C6—C15 | 122.11 (16) | C17—C16—H16A | 109.6 |
| C5—C6—C15 | 122.99 (17) | S1—C16—H16A | 109.6 |
| O1—C7—C6 | 124.33 (16) | C17—C16—H16B | 109.6 |
| O1—C7—C2 | 110.58 (15) | S1—C16—H16B | 109.6 |
| C6—C7—C2 | 125.05 (16) | H16A—C16—H16B | 108.1 |
| C1—C8—O1 | 110.19 (15) | C16—C17—H17A | 109.5 |
| C1—C8—C9 | 135.59 (16) | C16—C17—H17B | 109.5 |
| O1—C8—C9 | 114.19 (15) | H17A—C17—H17B | 109.5 |
| C10—C9—C14 | 118.53 (16) | C16—C17—H17C | 109.5 |
| C10—C9—C8 | 122.01 (16) | H17A—C17—H17C | 109.5 |
| C14—C9—C8 | 119.44 (16) | H17B—C17—H17C | 109.5 |
| C11—C10—C9 | 120.95 (17) | ||
| O2—S1—C1—C8 | −129.18 (16) | C3—C2—C7—C6 | −2.4 (3) |
| C16—S1—C1—C8 | 119.88 (17) | C1—C2—C7—C6 | 176.07 (17) |
| O2—S1—C1—C2 | 38.84 (17) | C2—C1—C8—O1 | −0.8 (2) |
| C16—S1—C1—C2 | −72.10 (16) | S1—C1—C8—O1 | 168.86 (12) |
| C8—C1—C2—C7 | 1.57 (19) | C2—C1—C8—C9 | 176.90 (19) |
| S1—C1—C2—C7 | −168.46 (13) | S1—C1—C8—C9 | −13.4 (3) |
| C8—C1—C2—C3 | 179.7 (2) | C7—O1—C8—C1 | −0.23 (18) |
| S1—C1—C2—C3 | 9.7 (3) | C7—O1—C8—C9 | −178.50 (14) |
| C7—C2—C3—C4 | 1.0 (2) | C1—C8—C9—C10 | −12.8 (3) |
| C1—C2—C3—C4 | −176.88 (19) | O1—C8—C9—C10 | 164.87 (16) |
| C2—C3—C4—C5 | 0.6 (3) | C1—C8—C9—C14 | 169.0 (2) |
| C2—C3—C4—I1 | 176.89 (13) | O1—C8—C9—C14 | −13.3 (2) |
| C3—C4—C5—C6 | −1.1 (3) | C14—C9—C10—C11 | −0.1 (3) |
| I1—C4—C5—C6 | −177.44 (13) | C8—C9—C10—C11 | −178.32 (17) |
| C4—C5—C6—C7 | −0.1 (3) | C9—C10—C11—C12 | 0.8 (3) |
| C4—C5—C6—C15 | 178.68 (18) | C10—C11—C12—C13 | −0.7 (3) |
| C8—O1—C7—C6 | −176.56 (17) | C10—C11—C12—Cl1 | 178.54 (15) |
| C8—O1—C7—C2 | 1.28 (18) | C11—C12—C13—C14 | −0.2 (3) |
| C5—C6—C7—O1 | 179.43 (16) | Cl1—C12—C13—C14 | −179.37 (15) |
| C15—C6—C7—O1 | 0.6 (3) | C12—C13—C14—C9 | 0.9 (3) |
| C5—C6—C7—C2 | 1.9 (3) | C10—C9—C14—C13 | −0.7 (3) |
| C15—C6—C7—C2 | −176.90 (17) | C8—C9—C14—C13 | 177.52 (17) |
| C3—C2—C7—O1 | 179.75 (15) | O2—S1—C16—C17 | 172.76 (14) |
| C1—C2—C7—O1 | −1.76 (19) | C1—S1—C16—C17 | −76.74 (16) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.
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, o770.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2960.
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.
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805.
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834.
Many compounds involving a benzofuran ring have attracted much attention owing to 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 2-(4-chlorophenyl)-3-ethylsulfinyl-5-halo-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 0.020 (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-chlorophenyl ring is 12.13 (5)°. The molecular packing is stabilized by an I···O halogen-bonding between the iodine and the oxygen of the S═O unit [I1···O2i = 3.145 (1) Å; C4—I1···O2i = 169.00 (6)°; symmetry code; - x+1, - y +1, - z +1] (Politzer et al., 2007).