Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059259/sj2426sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059259/sj2426Isup2.hkl |
CCDC reference: 673017
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.028
- wR factor = 0.066
- Data-to-parameter ratio = 21.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact I .. O2 .. 3.14 Ang.
Author Response: : Explained in "Comment" as halogen bond. |
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 40 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.20 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the crystal structures of similar 5-iodobenzofuran compounds, see: Choi et al. (2007a,b). For a review of halogen bonding, see: Politzer et al. (2007). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).
3-Chloroperbenzoic acid (77%, 247 mg, 1.1 mmol) was added in small portions to a stirred solution of 5-iodo-2-methyl-3-methylsulfanyl-1-benzofuran (304 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After stirring 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 (ethyl acetate) to afford the title compound as a colorless solid [yield 80%, m.p. 420–421 K; Rf = 0.44 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in acetone at room temperature.
All H atoms were geometrically located in ideal positions and refined using a riding model, with C—H=0.93 Å for aromatic H atoms and 0.96 Å for methyl H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and 1.5Ueq(C) for methyl H atoms. The highest peak in the difference map is 0.85 Å from I.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 1997).
C10H9IO2S | Z = 2 |
Mr = 320.13 | F(000) = 308 |
Triclinic, P1 | Dx = 1.938 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1521 (4) Å | Cell parameters from 8333 reflections |
b = 8.2671 (4) Å | θ = 2.5–28.3° |
c = 8.6870 (4) Å | µ = 3.08 mm−1 |
α = 104.585 (2)° | T = 298 K |
β = 99.920 (2)° | Block, silver |
γ = 97.620 (2)° | 0.41 × 0.35 × 0.20 mm |
V = 548.52 (5) Å3 |
Bruker SMART CCD diffractometer | 2695 independent reflections |
Radiation source: fine-focus sealed tube | 2448 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.4°, θmin = 2.5° |
ϕ and ω scans | h = −10→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | k = −11→10 |
Tmin = 0.301, Tmax = 0.538 | l = −11→11 |
10576 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0241P)2 + 0.6885P] where P = (Fo2 + 2Fc2)/3 |
2695 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 1.31 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
C10H9IO2S | γ = 97.620 (2)° |
Mr = 320.13 | V = 548.52 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1521 (4) Å | Mo Kα radiation |
b = 8.2671 (4) Å | µ = 3.08 mm−1 |
c = 8.6870 (4) Å | T = 298 K |
α = 104.585 (2)° | 0.41 × 0.35 × 0.20 mm |
β = 99.920 (2)° |
Bruker SMART CCD diffractometer | 2695 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 2448 reflections with I > 2σ(I) |
Tmin = 0.301, Tmax = 0.538 | Rint = 0.017 |
10576 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.31 e Å−3 |
2695 reflections | Δρmin = −0.73 e Å−3 |
128 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 | 0.14093 (3) | 0.58796 (3) | 0.80417 (3) | 0.06018 (9) | |
S | 0.19880 (9) | 0.03223 (9) | 0.15991 (8) | 0.04263 (16) | |
O1 | 0.6390 (2) | 0.1957 (3) | 0.4697 (2) | 0.0459 (4) | |
O2 | 0.1218 (3) | 0.1740 (3) | 0.1195 (3) | 0.0624 (6) | |
C1 | 0.3697 (3) | 0.1256 (3) | 0.3272 (3) | 0.0384 (5) | |
C2 | 0.3747 (3) | 0.2544 (3) | 0.4761 (3) | 0.0376 (5) | |
C3 | 0.2573 (4) | 0.3385 (4) | 0.5464 (3) | 0.0410 (6) | |
H3 | 0.1439 | 0.3164 | 0.4936 | 0.049* | |
C4 | 0.3155 (4) | 0.4566 (4) | 0.6980 (3) | 0.0442 (6) | |
C5 | 0.4861 (4) | 0.4939 (4) | 0.7772 (4) | 0.0515 (7) | |
H5 | 0.5209 | 0.5748 | 0.8781 | 0.062* | |
C6 | 0.6037 (4) | 0.4119 (4) | 0.7075 (4) | 0.0501 (7) | |
H6 | 0.7177 | 0.4363 | 0.7587 | 0.060* | |
C7 | 0.5440 (4) | 0.2926 (4) | 0.5589 (3) | 0.0419 (6) | |
C8 | 0.5284 (4) | 0.0956 (4) | 0.3289 (3) | 0.0414 (6) | |
C9 | 0.6034 (4) | −0.0215 (4) | 0.2141 (4) | 0.0519 (7) | |
H9A | 0.5166 | −0.0860 | 0.1213 | 0.078* | |
H9B | 0.6530 | −0.0975 | 0.2673 | 0.078* | |
H9C | 0.6892 | 0.0430 | 0.1792 | 0.078* | |
C10 | 0.0620 (4) | −0.0694 (5) | 0.2611 (4) | 0.0599 (8) | |
H10A | −0.0414 | −0.1285 | 0.1850 | 0.090* | |
H10B | 0.0369 | 0.0146 | 0.3481 | 0.090* | |
H10C | 0.1168 | −0.1490 | 0.3047 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.06932 (16) | 0.04801 (13) | 0.05745 (14) | 0.00644 (10) | 0.02787 (11) | −0.00282 (9) |
S | 0.0476 (4) | 0.0447 (4) | 0.0317 (3) | 0.0149 (3) | 0.0052 (3) | 0.0028 (3) |
O1 | 0.0366 (10) | 0.0573 (12) | 0.0465 (11) | 0.0108 (9) | 0.0089 (8) | 0.0184 (9) |
O2 | 0.0724 (16) | 0.0553 (13) | 0.0499 (12) | 0.0221 (11) | −0.0116 (11) | 0.0088 (10) |
C1 | 0.0401 (13) | 0.0418 (13) | 0.0339 (12) | 0.0108 (11) | 0.0071 (10) | 0.0105 (10) |
C2 | 0.0393 (13) | 0.0415 (13) | 0.0327 (12) | 0.0074 (10) | 0.0059 (10) | 0.0128 (10) |
C3 | 0.0410 (14) | 0.0423 (14) | 0.0371 (13) | 0.0074 (11) | 0.0071 (11) | 0.0079 (11) |
C4 | 0.0534 (16) | 0.0392 (13) | 0.0380 (13) | 0.0051 (12) | 0.0140 (12) | 0.0066 (11) |
C5 | 0.0615 (19) | 0.0483 (16) | 0.0355 (14) | −0.0054 (14) | 0.0058 (13) | 0.0063 (12) |
C6 | 0.0434 (15) | 0.0576 (18) | 0.0424 (15) | −0.0034 (13) | 0.0010 (12) | 0.0138 (13) |
C7 | 0.0391 (14) | 0.0480 (15) | 0.0406 (14) | 0.0052 (11) | 0.0088 (11) | 0.0171 (12) |
C8 | 0.0447 (15) | 0.0448 (14) | 0.0406 (14) | 0.0122 (11) | 0.0124 (11) | 0.0182 (12) |
C9 | 0.0546 (18) | 0.0551 (17) | 0.0577 (18) | 0.0214 (14) | 0.0259 (14) | 0.0216 (15) |
C10 | 0.0468 (17) | 0.073 (2) | 0.0527 (18) | 0.0012 (16) | 0.0032 (14) | 0.0161 (17) |
I—O2i | 3.139 (2) | C3—H3 | 0.9300 |
I—C4 | 2.100 (3) | C4—C5 | 1.397 (4) |
S—O2 | 1.489 (2) | C5—C6 | 1.382 (5) |
S—O2ii | 3.190 (2) | C5—H5 | 0.9300 |
S—C1 | 1.761 (3) | C6—C7 | 1.375 (4) |
S—C10 | 1.784 (4) | C6—H6 | 0.9300 |
O1—C7 | 1.379 (4) | C8—C9 | 1.478 (4) |
O1—C8 | 1.380 (4) | C9—H9A | 0.9600 |
O2—Sii | 3.190 (2) | C9—H9B | 0.9600 |
C1—C2 | 1.444 (4) | C9—H9C | 0.9600 |
C1—C8 | 1.347 (4) | C10—H10A | 0.9600 |
C2—C3 | 1.392 (4) | C10—H10B | 0.9600 |
C2—C7 | 1.396 (4) | C10—H10C | 0.9600 |
C3—C4 | 1.388 (4) | ||
O2—S—C1 | 106.65 (13) | C7—C6—H6 | 121.6 |
O2—S—C10 | 107.45 (17) | C5—C6—H6 | 121.6 |
C1—S—C10 | 98.26 (14) | C6—C7—O1 | 126.2 (3) |
C4—I—O2i | 164.13 (9) | C6—C7—C2 | 123.6 (3) |
C7—O1—C8 | 106.4 (2) | O1—C7—C2 | 110.3 (2) |
C8—C1—C2 | 107.5 (2) | C1—C8—O1 | 111.0 (2) |
C8—C1—S | 123.4 (2) | C1—C8—C9 | 133.2 (3) |
C2—C1—S | 128.9 (2) | O1—C8—C9 | 115.8 (3) |
C3—C2—C7 | 119.3 (3) | C8—C9—H9A | 109.5 |
C3—C2—C1 | 135.8 (3) | C8—C9—H9B | 109.5 |
C7—C2—C1 | 104.9 (2) | H9A—C9—H9B | 109.5 |
C4—C3—C2 | 117.6 (3) | C8—C9—H9C | 109.5 |
C4—C3—H3 | 121.2 | H9A—C9—H9C | 109.5 |
C2—C3—H3 | 121.2 | H9B—C9—H9C | 109.5 |
C3—C4—C5 | 121.9 (3) | S—C10—H10A | 109.5 |
C3—C4—I | 118.2 (2) | S—C10—H10B | 109.5 |
C5—C4—I | 119.9 (2) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 120.8 (3) | S—C10—H10C | 109.5 |
C6—C5—H5 | 119.6 | H10A—C10—H10C | 109.5 |
C4—C5—H5 | 119.6 | H10B—C10—H10C | 109.5 |
C7—C6—C5 | 116.8 (3) | ||
O2—S—C1—C8 | −126.7 (3) | C5—C6—C7—O1 | −179.3 (3) |
C10—S—C1—C8 | 122.2 (3) | C5—C6—C7—C2 | 1.4 (4) |
O2—S—C1—C2 | 47.1 (3) | C8—O1—C7—C6 | −179.3 (3) |
C10—S—C1—C2 | −64.0 (3) | C8—O1—C7—C2 | 0.1 (3) |
C8—C1—C2—C3 | −179.8 (3) | C3—C2—C7—C6 | −0.9 (4) |
S—C1—C2—C3 | 5.6 (5) | C1—C2—C7—C6 | 179.4 (3) |
C8—C1—C2—C7 | −0.1 (3) | C3—C2—C7—O1 | 179.7 (2) |
S—C1—C2—C7 | −174.7 (2) | C1—C2—C7—O1 | 0.0 (3) |
C7—C2—C3—C4 | −0.6 (4) | C2—C1—C8—O1 | 0.2 (3) |
C1—C2—C3—C4 | 179.1 (3) | S—C1—C8—O1 | 175.18 (19) |
C2—C3—C4—C5 | 1.4 (4) | C2—C1—C8—C9 | 179.2 (3) |
C2—C3—C4—I | 178.9 (2) | S—C1—C8—C9 | −5.8 (5) |
C3—C4—C5—C6 | −0.9 (5) | C7—O1—C8—C1 | −0.2 (3) |
I—C4—C5—C6 | −178.4 (2) | C7—O1—C8—C9 | −179.4 (2) |
C4—C5—C6—C7 | −0.5 (5) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···Cgiii | 0.96 | 2.72 | 3.527 (3) | 142 |
Symmetry code: (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H9IO2S |
Mr | 320.13 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.1521 (4), 8.2671 (4), 8.6870 (4) |
α, β, γ (°) | 104.585 (2), 99.920 (2), 97.620 (2) |
V (Å3) | 548.52 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.08 |
Crystal size (mm) | 0.41 × 0.35 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.301, 0.538 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10576, 2695, 2448 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.066, 1.08 |
No. of reflections | 2695 |
No. of parameters | 128 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.31, −0.73 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···Cgi | 0.96 | 2.72 | 3.527 (3) | 141.9 |
Symmetry code: (i) −x+1, −y, −z+1. |
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As part of our ongoing studies of the synthesis and structure of 5-iodo-1-benzofuran derivatives, we have recently described the crystal structures of 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-iodo-2-methyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007b). Herein we report the crystal and molecular structure of the title compound, 5-iodo-2-methyl-3-methylsulfinyl-1-benzofuran (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by CH2—H···π interactions between the hydrogen of 2-methyl group and a benzene ring of benzofuran unit, with a C9—H9B···Cg separation of 2.72 Å (Fig. 2 & Table 1) (Cg is the centroid of C2—C7 benzene ring, symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by a I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with a I···O2ii distance of 3.139 (2) Å (symmetry code as Fig. 2). In addition, the crystal packing exhibits a sulfinyl-sulfinyl interaction interpreted as similar to a type-II carbonyl-carbonyl interaction (Allen et al., 1998), with S···O2iii and O2···Siii distances of 3.190 (2) Å (symmetry code as Fig. 2).