



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040482/wn2192sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040482/wn2192Isup2.hkl |
CCDC reference: 660319
3-Chloroperbenzoic acid (77%, 247 mg, 1.10 mmol) was added in small portions to a stirred solution of 5-iodo-2-methyl-3-phenylsulfanyl-1-benzofuran (366 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 2 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (chloroform) to afford the title compound as a colorless solid [yield 81%, m.p. 441–442 K; Rf = 0.82 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in chloroform at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The deepest hole in the residual electron density is 0.70 Å from I.
This work is related to an earlier communication on the synthesis and structure of a 5-iodo-1-benzofuran analogue, viz. 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007). Here we report the molecular and crystal structure of the title compound, 5-iodo-2-methyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.006 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C10–C15) is almost perpendicular to the plane of the benzofuran system [85.75 (7)°] and is tilted slightly towards it. The molecular packing (Fig. 2) is stabilized by a C—H···O hydrogen bond between the hydrogen of methyl group and the oxygen of the S═O unit (Table 1). The molecular packing (Fig. 2) is further stabilized by a halogen bond between the iodine atom and the oxygen of a neighbouring S═O unit, C—I···O2ii (symmetry code as in Fig. 2). The observed I···O separation of 3.165 (2) Å and the nearly linear C—I···O angle of 165.55 (7)° are typical for such halogen bonds. A search of the Cambridge Structural Database (version 5.28; Allen, 2002) revealed 39 compounds with C—I···O═S contact distances equal to or less than 3.3 Å.
For the crystal structure of an isomer of the title compound, see: Choi et al. (2007). For related literature, see: Allen (2002).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
C15H11IO2S | F(000) = 744 |
Mr = 382.20 | Dx = 1.810 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6974 reflections |
a = 12.9995 (6) Å | θ = 2.2–28.3° |
b = 11.5063 (5) Å | µ = 2.43 mm−1 |
c = 9.7556 (4) Å | T = 173 K |
β = 106.004 (1)° | Block, colourless |
V = 1402.65 (11) Å3 | 0.60 × 0.60 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3049 independent reflections |
Radiation source: fine-focus sealed tube | 2850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 2.4° |
φ and ω scans | h = −14→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −14→9 |
Tmin = 0.248, Tmax = 0.613 | l = −12→12 |
8261 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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0335P)2 + 1.54P] where P = (Fo2 + 2Fc2)/3 |
3049 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −1.04 e Å−3 |
C15H11IO2S | V = 1402.65 (11) Å3 |
Mr = 382.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9995 (6) Å | µ = 2.43 mm−1 |
b = 11.5063 (5) Å | T = 173 K |
c = 9.7556 (4) Å | 0.60 × 0.60 × 0.20 mm |
β = 106.004 (1)° |
Bruker SMART CCD area-detector diffractometer | 3049 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 2850 reflections with I > 2σ(I) |
Tmin = 0.248, Tmax = 0.613 | Rint = 0.017 |
8261 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.92 e Å−3 |
3049 reflections | Δρmin = −1.04 e Å−3 |
173 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | ||
I | 0.778381 (14) | 0.338404 (14) | 0.039433 (19) | 0.03671 (8) | |
S | 0.70023 (5) | −0.16978 (5) | −0.27520 (6) | 0.02966 (14) | |
O1 | 0.93626 (15) | −0.17067 (14) | 0.07595 (18) | 0.0302 (4) | |
O2 | 0.71346 (16) | −0.09253 (17) | −0.39233 (18) | 0.0388 (4) | |
C1 | 0.79820 (19) | −0.1358 (2) | −0.1165 (2) | 0.0263 (4) | |
C2 | 0.82329 (18) | −0.0273 (2) | −0.0382 (2) | 0.0243 (4) | |
C3 | 0.78457 (18) | 0.0870 (2) | −0.0546 (2) | 0.0262 (4) | |
H3 | 0.7272 | 0.1094 | −0.1338 | 0.031* | |
C4 | 0.8340 (2) | 0.16585 (19) | 0.0503 (3) | 0.0279 (5) | |
C5 | 0.9196 (2) | 0.1361 (2) | 0.1672 (3) | 0.0309 (5) | |
H5 | 0.9504 | 0.1933 | 0.2366 | 0.037* | |
C6 | 0.9596 (2) | 0.0242 (2) | 0.1824 (2) | 0.0314 (5) | |
H6 | 1.0187 | 0.0027 | 0.2598 | 0.038* | |
C7 | 0.90908 (18) | −0.0551 (2) | 0.0789 (2) | 0.0262 (4) | |
C8 | 0.86830 (19) | −0.2171 (2) | −0.0443 (2) | 0.0286 (5) | |
C9 | 0.8844 (2) | −0.3418 (2) | −0.0694 (3) | 0.0359 (6) | |
H9A | 0.8368 | −0.3649 | −0.1619 | 0.054* | |
H9B | 0.8680 | −0.3881 | 0.0063 | 0.054* | |
H9C | 0.9589 | −0.3549 | −0.0690 | 0.054* | |
C10 | 0.58474 (19) | −0.1178 (2) | −0.2266 (2) | 0.0292 (5) | |
C11 | 0.5264 (2) | −0.0268 (2) | −0.3007 (3) | 0.0360 (5) | |
H11 | 0.5499 | 0.0125 | −0.3723 | 0.043* | |
C12 | 0.4327 (2) | 0.0070 (3) | −0.2695 (3) | 0.0465 (7) | |
H12 | 0.3916 | 0.0696 | −0.3203 | 0.056* | |
C13 | 0.3993 (2) | −0.0497 (3) | −0.1655 (3) | 0.0503 (8) | |
H13 | 0.3352 | −0.0263 | −0.1447 | 0.060* | |
C14 | 0.4586 (3) | −0.1408 (3) | −0.0911 (3) | 0.0489 (8) | |
H14 | 0.4354 | −0.1791 | −0.0187 | 0.059* | |
C15 | 0.5521 (2) | −0.1769 (3) | −0.1217 (3) | 0.0396 (6) | |
H15 | 0.5926 | −0.2403 | −0.0721 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.03934 (12) | 0.02297 (10) | 0.04727 (12) | −0.00219 (6) | 0.01102 (8) | −0.00116 (6) |
S | 0.0380 (3) | 0.0268 (3) | 0.0238 (3) | −0.0043 (2) | 0.0080 (2) | −0.0041 (2) |
O1 | 0.0321 (9) | 0.0279 (9) | 0.0298 (8) | 0.0025 (7) | 0.0072 (7) | 0.0032 (6) |
O2 | 0.0492 (11) | 0.0429 (11) | 0.0277 (8) | −0.0024 (9) | 0.0163 (8) | 0.0026 (8) |
C1 | 0.0299 (11) | 0.0250 (11) | 0.0253 (10) | −0.0027 (9) | 0.0099 (9) | −0.0023 (9) |
C2 | 0.0258 (10) | 0.0258 (11) | 0.0227 (9) | −0.0027 (9) | 0.0090 (8) | −0.0007 (8) |
C3 | 0.0261 (11) | 0.0275 (11) | 0.0250 (10) | −0.0010 (9) | 0.0069 (8) | 0.0012 (9) |
C4 | 0.0318 (12) | 0.0231 (11) | 0.0302 (11) | −0.0041 (9) | 0.0107 (10) | 0.0005 (8) |
C5 | 0.0345 (13) | 0.0308 (12) | 0.0259 (11) | −0.0089 (10) | 0.0059 (9) | −0.0023 (9) |
C6 | 0.0310 (12) | 0.0353 (13) | 0.0249 (10) | −0.0054 (10) | 0.0025 (9) | 0.0039 (9) |
C7 | 0.0283 (11) | 0.0257 (11) | 0.0256 (10) | −0.0004 (9) | 0.0089 (9) | 0.0035 (9) |
C8 | 0.0317 (12) | 0.0284 (12) | 0.0290 (11) | −0.0007 (9) | 0.0138 (9) | −0.0002 (9) |
C9 | 0.0434 (15) | 0.0257 (13) | 0.0431 (14) | 0.0032 (10) | 0.0191 (12) | 0.0007 (10) |
C10 | 0.0310 (12) | 0.0309 (12) | 0.0238 (10) | −0.0103 (10) | 0.0043 (9) | −0.0044 (9) |
C11 | 0.0342 (13) | 0.0384 (14) | 0.0336 (12) | −0.0061 (11) | 0.0063 (10) | 0.0036 (11) |
C12 | 0.0328 (13) | 0.0528 (18) | 0.0498 (16) | 0.0000 (12) | 0.0046 (12) | 0.0023 (14) |
C13 | 0.0306 (13) | 0.073 (2) | 0.0468 (16) | −0.0076 (14) | 0.0098 (12) | −0.0052 (15) |
C14 | 0.0415 (16) | 0.071 (2) | 0.0369 (14) | −0.0201 (15) | 0.0145 (12) | −0.0015 (14) |
C15 | 0.0423 (15) | 0.0454 (16) | 0.0290 (12) | −0.0119 (12) | 0.0066 (11) | 0.0045 (11) |
I—C4 | 2.106 (2) | C6—H6 | 0.9500 |
I—O2i | 3.165 (2) | C8—C9 | 1.479 (3) |
S—O2 | 1.495 (2) | C9—H9A | 0.9800 |
S—C1 | 1.756 (2) | C9—H9B | 0.9800 |
S—C10 | 1.797 (3) | C9—H9C | 0.9800 |
O1—C8 | 1.368 (3) | C10—C11 | 1.375 (4) |
O1—C7 | 1.378 (3) | C10—C15 | 1.389 (3) |
C1—C8 | 1.360 (3) | C11—C12 | 1.390 (4) |
C1—C2 | 1.452 (3) | C11—H11 | 0.9500 |
C2—C7 | 1.396 (3) | C12—C13 | 1.374 (4) |
C2—C3 | 1.402 (3) | C12—H12 | 0.9500 |
C3—C4 | 1.386 (3) | C13—C14 | 1.382 (5) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.398 (4) | C14—C15 | 1.393 (5) |
C5—C6 | 1.381 (4) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.385 (3) | ||
C4—I—O2i | 165.55 (7) | C1—C8—C9 | 133.4 (2) |
O2—S—C1 | 109.5 (1) | O1—C8—C9 | 115.7 (2) |
O2—S—C10 | 106.5 (1) | C8—C9—H9A | 109.5 |
C1—S—C10 | 98.6 (1) | C8—C9—H9B | 109.5 |
C8—O1—C7 | 106.6 (2) | H9A—C9—H9B | 109.5 |
C8—C1—C2 | 107.3 (2) | C8—C9—H9C | 109.5 |
C8—C1—S | 121.5 (2) | H9A—C9—H9C | 109.5 |
C2—C1—S | 131.2 (2) | H9B—C9—H9C | 109.5 |
C7—C2—C3 | 119.3 (2) | C11—C10—C15 | 121.6 (3) |
C7—C2—C1 | 104.3 (2) | C11—C10—S | 119.6 (2) |
C3—C2—C1 | 136.5 (2) | C15—C10—S | 118.6 (2) |
C4—C3—C2 | 116.8 (2) | C10—C11—C12 | 119.2 (3) |
C4—C3—H3 | 121.6 | C10—C11—H11 | 120.4 |
C2—C3—H3 | 121.6 | C12—C11—H11 | 120.4 |
C3—C4—C5 | 123.0 (2) | C13—C12—C11 | 120.2 (3) |
C3—C4—I | 119.8 (2) | C13—C12—H12 | 119.9 |
C5—C4—I | 117.20 (17) | C11—C12—H12 | 119.9 |
C6—C5—C4 | 120.5 (2) | C12—C13—C14 | 120.3 (3) |
C6—C5—H5 | 119.8 | C12—C13—H13 | 119.9 |
C4—C5—H5 | 119.8 | C14—C13—H13 | 119.9 |
C5—C6—C7 | 116.6 (2) | C13—C14—C15 | 120.4 (3) |
C5—C6—H6 | 121.7 | C13—C14—H14 | 119.8 |
C7—C6—H6 | 121.7 | C15—C14—H14 | 119.8 |
O1—C7—C6 | 125.3 (2) | C10—C15—C14 | 118.3 (3) |
O1—C7—C2 | 110.8 (2) | C10—C15—H15 | 120.9 |
C6—C7—C2 | 123.8 (2) | C14—C15—H15 | 120.9 |
C1—C8—O1 | 110.9 (2) | ||
O2—S—C1—C8 | −122.3 (2) | C1—C2—C7—O1 | −0.1 (2) |
C10—S—C1—C8 | 126.7 (2) | C3—C2—C7—C6 | 0.1 (3) |
O2—S—C1—C2 | 57.2 (2) | C1—C2—C7—C6 | 179.4 (2) |
C10—S—C1—C2 | −53.8 (2) | C2—C1—C8—O1 | 0.8 (3) |
C8—C1—C2—C7 | −0.4 (2) | S—C1—C8—O1 | −179.60 (16) |
S—C1—C2—C7 | −179.97 (18) | C2—C1—C8—C9 | −179.6 (2) |
C8—C1—C2—C3 | 178.8 (2) | S—C1—C8—C9 | 0.0 (4) |
S—C1—C2—C3 | −0.8 (4) | C7—O1—C8—C1 | −0.9 (2) |
C7—C2—C3—C4 | −1.1 (3) | C7—O1—C8—C9 | 179.4 (2) |
C1—C2—C3—C4 | 179.8 (2) | O2—S—C10—C11 | 3.0 (2) |
C2—C3—C4—C5 | 0.9 (3) | C1—S—C10—C11 | 116.3 (2) |
C2—C3—C4—I | −177.91 (15) | O2—S—C10—C15 | 178.09 (19) |
O2i—I—C4—C3 | 147.5 (2) | C1—S—C10—C15 | −68.6 (2) |
O2i—I—C4—C5 | −31.4 (4) | C15—C10—C11—C12 | 0.2 (4) |
C3—C4—C5—C6 | 0.4 (4) | S—C10—C11—C12 | 175.1 (2) |
I—C4—C5—C6 | 179.26 (18) | C10—C11—C12—C13 | 0.2 (4) |
C4—C5—C6—C7 | −1.4 (3) | C11—C12—C13—C14 | 0.0 (5) |
C8—O1—C7—C6 | −178.9 (2) | C12—C13—C14—C15 | −0.7 (5) |
C8—O1—C7—C2 | 0.6 (2) | C11—C10—C15—C14 | −0.8 (4) |
C5—C6—C7—O1 | −179.3 (2) | S—C10—C15—C14 | −175.9 (2) |
C5—C6—C7—C2 | 1.2 (3) | C13—C14—C15—C10 | 1.1 (4) |
C3—C2—C7—O1 | −179.44 (19) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O2ii | 0.98 | 2.48 | 3.257 (3) | 136 |
Symmetry code: (ii) x, −y−1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H11IO2S |
Mr | 382.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 12.9995 (6), 11.5063 (5), 9.7556 (4) |
β (°) | 106.004 (1) |
V (Å3) | 1402.65 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.43 |
Crystal size (mm) | 0.60 × 0.60 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.248, 0.613 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8261, 3049, 2850 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.066, 1.05 |
No. of reflections | 3049 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.92, −1.04 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O2i | 0.98 | 2.48 | 3.257 (3) | 135.8 |
Symmetry code: (i) x, −y−1/2, z+1/2. |
This work is related to an earlier communication on the synthesis and structure of a 5-iodo-1-benzofuran analogue, viz. 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007). Here we report the molecular and crystal structure of the title compound, 5-iodo-2-methyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.006 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C10–C15) is almost perpendicular to the plane of the benzofuran system [85.75 (7)°] and is tilted slightly towards it. The molecular packing (Fig. 2) is stabilized by a C—H···O hydrogen bond between the hydrogen of methyl group and the oxygen of the S═O unit (Table 1). The molecular packing (Fig. 2) is further stabilized by a halogen bond between the iodine atom and the oxygen of a neighbouring S═O unit, C—I···O2ii (symmetry code as in Fig. 2). The observed I···O separation of 3.165 (2) Å and the nearly linear C—I···O angle of 165.55 (7)° are typical for such halogen bonds. A search of the Cambridge Structural Database (version 5.28; Allen, 2002) revealed 39 compounds with C—I···O═S contact distances equal to or less than 3.3 Å.