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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2449.
Published online 2010 August 28. doi:  10.1107/S1600536810033581
PMCID: PMC3008065

5-Chloro-3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-1-benzofuran

Abstract

In the title compound, C16H12ClIO2S, the 4-iodo­phenyl ring is rotated out of the benzofuran plane by 9.4 (1)°. In the crystal structure, inter­molecular C—H(...)π inter­actions and short inter­molecular I(...)O contacts [3.142 (2) Å] are observed.

Related literature

For the crystal structures of related 3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-1-benzofuran derivatives, see: Choi et al. (2010a [triangle],b [triangle]). For a review on halogen bonding, see: Politzer et al. (2007 [triangle]).

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Object name is e-66-o2449-scheme1.jpg

Experimental

Crystal data

  • C16H12ClIO2S
  • M r = 430.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2449-efi7.jpg
  • a = 11.9782 (3) Å
  • b = 10.4604 (3) Å
  • c = 12.9624 (4) Å
  • β = 107.827 (1)°
  • V = 1546.16 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.38 mm−1
  • T = 173 K
  • 0.35 × 0.25 × 0.14 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.514, T max = 0.746
  • 14190 measured reflections
  • 3549 independent reflections
  • 3252 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.054
  • S = 1.67
  • 3549 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.75 e Å−3
  • Δρmin = −0.91 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033581/nc2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033581/nc2194Isup2.hkl

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

supplementary crystallographic information

Comment

As a part of our ongoing studies of the substituent effect on the solid state structures of 3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-iodophenyl ring is 9.4 (1)° (Fig. 1). In the crystal structure weak C—H···π interactions between the methylene H atom of the ethyl group and the benzene ring of an adjacent benzofuran ring is observed (Fig. 2 and Tab. 1). In addition, a short I···O contact is observed [I···O2ii = 3.142 (2)Å; C12—I···O2ii = 158.24 (7)°] which indicate a weak interaction (Politzer et al., 2007).

Experimental

3-chloroperoxybenzoic acid (77%) (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(4-iodophenyl)-1-benzofuran (373 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. The mixture was stirred for 5 h at room temperature, 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 76%, m.p. 439–440 K; Rf = 0.56 (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 acetone at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aryl, 0.97 Å for methylene, and 0.96 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms, 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.
Fig. 2.
C—H···π and I···O interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 3/2, y - 1/2, - z + 3/2; (ii) x - 1,y, ...

Crystal data

C16H12ClIO2SF(000) = 840
Mr = 430.67Dx = 1.850 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8003 reflections
a = 11.9782 (3) Åθ = 2.6–27.5°
b = 10.4604 (3) ŵ = 2.38 mm1
c = 12.9624 (4) ÅT = 173 K
β = 107.827 (1)°Block, colourless
V = 1546.16 (8) Å30.35 × 0.25 × 0.14 mm
Z = 4

Data collection

Bruker SMART APEXII CCD diffractometer3549 independent reflections
Radiation source: rotating anode3252 reflections with I > 2σ(I)
graphite multilayerRint = 0.032
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.6°
[var phi] and ω scansh = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −13→13
Tmin = 0.514, Tmax = 0.746l = −16→15
14190 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)] = 0.025Hydrogen site location: difference Fourier map
wR(F2) = 0.054H-atom parameters constrained
S = 1.67w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
3549 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = −0.91 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
I0.020729 (12)0.410793 (14)0.735141 (13)0.03083 (6)
Cl0.91427 (5)0.77704 (6)0.50411 (5)0.03458 (14)
S0.66881 (5)0.44141 (5)0.74904 (5)0.02532 (12)
O10.45082 (12)0.67491 (14)0.53906 (12)0.0240 (3)
O20.75087 (15)0.37662 (16)0.69934 (15)0.0382 (4)
C10.59438 (18)0.56061 (19)0.65608 (17)0.0217 (4)
C20.64728 (18)0.6403 (2)0.59295 (17)0.0215 (4)
C30.76078 (18)0.6605 (2)0.58850 (18)0.0243 (5)
H30.82490.61810.63490.029*
C40.77369 (19)0.74651 (19)0.51177 (18)0.0249 (5)
C50.6793 (2)0.8095 (2)0.43905 (19)0.0287 (5)
H50.69210.86470.38750.034*
C60.5667 (2)0.7897 (2)0.44369 (19)0.0293 (5)
H60.50230.83090.39650.035*
C70.55461 (18)0.7064 (2)0.52149 (17)0.0229 (4)
C80.47620 (18)0.58480 (19)0.62118 (17)0.0220 (4)
C90.37422 (17)0.5421 (2)0.65070 (17)0.0222 (4)
C100.2620 (2)0.5747 (2)0.5829 (2)0.0274 (5)
H100.25410.62100.51990.033*
C110.16345 (19)0.5382 (2)0.60939 (19)0.0290 (5)
H110.08950.56250.56540.035*
C120.17458 (18)0.4656 (2)0.70127 (18)0.0242 (5)
C130.2839 (2)0.4300 (2)0.7671 (2)0.0335 (6)
H130.29110.37970.82790.040*
C140.38293 (19)0.4693 (2)0.74239 (19)0.0320 (5)
H140.45660.44670.78800.038*
C150.7574 (2)0.5465 (2)0.8530 (2)0.0342 (6)
H15A0.82210.49840.90040.041*
H15B0.79000.61360.81920.041*
C160.6874 (3)0.6064 (2)0.9197 (2)0.0447 (7)
H16A0.62640.65890.87390.067*
H16B0.73820.65790.97600.067*
H16C0.65310.54020.95160.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I0.02630 (9)0.03230 (10)0.03857 (11)−0.00398 (6)0.01689 (7)−0.00332 (6)
Cl0.0289 (3)0.0336 (3)0.0473 (4)−0.0040 (2)0.0206 (3)−0.0008 (3)
S0.0215 (3)0.0245 (3)0.0300 (3)0.0028 (2)0.0080 (2)0.0053 (2)
O10.0194 (7)0.0275 (8)0.0247 (8)0.0010 (6)0.0061 (6)0.0032 (6)
O20.0343 (9)0.0375 (9)0.0468 (11)0.0128 (8)0.0186 (8)0.0069 (8)
C10.0218 (10)0.0211 (10)0.0218 (12)0.0017 (8)0.0058 (8)0.0008 (8)
C20.0222 (10)0.0205 (10)0.0223 (11)0.0002 (8)0.0073 (8)−0.0019 (8)
C30.0210 (10)0.0236 (11)0.0282 (12)0.0021 (9)0.0076 (9)0.0000 (9)
C40.0237 (10)0.0240 (11)0.0295 (13)−0.0030 (9)0.0120 (9)−0.0048 (9)
C50.0338 (12)0.0277 (12)0.0265 (13)−0.0031 (10)0.0121 (10)0.0036 (9)
C60.0278 (11)0.0307 (12)0.0274 (13)0.0023 (10)0.0054 (9)0.0047 (10)
C70.0202 (10)0.0246 (11)0.0235 (12)−0.0010 (8)0.0062 (9)−0.0017 (9)
C80.0228 (10)0.0217 (10)0.0205 (11)0.0003 (8)0.0052 (8)−0.0018 (8)
C90.0191 (10)0.0229 (10)0.0243 (12)−0.0004 (8)0.0061 (8)−0.0027 (9)
C100.0254 (11)0.0255 (11)0.0305 (13)0.0005 (9)0.0072 (9)0.0069 (9)
C110.0191 (10)0.0288 (11)0.0362 (14)0.0018 (9)0.0042 (9)0.0045 (10)
C120.0200 (10)0.0251 (11)0.0298 (13)−0.0021 (9)0.0110 (9)−0.0055 (9)
C130.0288 (12)0.0459 (15)0.0280 (14)0.0019 (11)0.0121 (10)0.0084 (11)
C140.0198 (11)0.0482 (15)0.0274 (13)0.0027 (10)0.0063 (9)0.0059 (11)
C150.0295 (12)0.0372 (13)0.0291 (14)−0.0065 (11)−0.0012 (10)0.0073 (10)
C160.0638 (19)0.0336 (14)0.0331 (15)−0.0055 (13)0.0093 (13)−0.0016 (11)

Geometric parameters (Å, °)

I—C122.101 (2)C6—H60.9300
I—O2i3.1422 (17)C8—C91.458 (3)
Cl—C41.746 (2)C9—C141.388 (3)
S—O21.4928 (17)C9—C101.404 (3)
S—C11.773 (2)C10—C111.380 (3)
S—C151.810 (2)C10—H100.9300
O1—C71.371 (2)C11—C121.384 (3)
O1—C81.384 (2)C11—H110.9300
C1—C81.371 (3)C12—C131.378 (3)
C1—C21.444 (3)C13—C141.382 (3)
C2—C71.392 (3)C13—H130.9300
C2—C31.394 (3)C14—H140.9300
C3—C41.385 (3)C15—C161.513 (4)
C3—H30.9300C15—H15A0.9700
C4—C51.396 (3)C15—H15B0.9700
C5—C61.384 (3)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.374 (3)C16—H16C0.9600
C12—I—O2i158.24 (7)C14—C9—C8122.93 (19)
O2—S—C1106.65 (10)C10—C9—C8118.68 (19)
O2—S—C15106.48 (11)C11—C10—C9120.4 (2)
C1—S—C1597.87 (11)C11—C10—H10119.8
C7—O1—C8107.13 (15)C9—C10—H10119.8
C8—C1—C2107.12 (18)C10—C11—C12120.1 (2)
C8—C1—S127.41 (16)C10—C11—H11120.0
C2—C1—S125.09 (16)C12—C11—H11120.0
C7—C2—C3119.10 (19)C13—C12—C11120.3 (2)
C7—C2—C1105.36 (18)C13—C12—I121.68 (17)
C3—C2—C1135.5 (2)C11—C12—I118.04 (15)
C4—C3—C2116.9 (2)C12—C13—C14119.8 (2)
C4—C3—H3121.5C12—C13—H13120.1
C2—C3—H3121.5C14—C13—H13120.1
C3—C4—C5123.1 (2)C13—C14—C9121.1 (2)
C3—C4—Cl118.77 (17)C13—C14—H14119.4
C5—C4—Cl118.11 (17)C9—C14—H14119.4
C6—C5—C4119.9 (2)C16—C15—S112.07 (18)
C6—C5—H5120.0C16—C15—H15A109.2
C4—C5—H5120.0S—C15—H15A109.2
C7—C6—C5116.7 (2)C16—C15—H15B109.2
C7—C6—H6121.6S—C15—H15B109.2
C5—C6—H6121.6H15A—C15—H15B107.9
O1—C7—C6125.38 (19)C15—C16—H16A109.5
O1—C7—C2110.43 (18)C15—C16—H16B109.5
C6—C7—C2124.19 (19)H16A—C16—H16B109.5
C1—C8—O1109.93 (18)C15—C16—H16C109.5
C1—C8—C9136.1 (2)H16A—C16—H16C109.5
O1—C8—C9113.98 (17)H16B—C16—H16C109.5
C14—C9—C10118.39 (19)
O2—S—C1—C8132.8 (2)S—C1—C8—O1−172.77 (15)
C15—S—C1—C8−117.3 (2)C2—C1—C8—C9−177.9 (2)
O2—S—C1—C2−39.1 (2)S—C1—C8—C99.1 (4)
C15—S—C1—C270.8 (2)C7—O1—C8—C10.7 (2)
C8—C1—C2—C7−1.2 (2)C7—O1—C8—C9179.31 (17)
S—C1—C2—C7172.11 (16)C1—C8—C9—C149.4 (4)
C8—C1—C2—C3−179.9 (2)O1—C8—C9—C14−168.7 (2)
S—C1—C2—C3−6.6 (4)C1—C8—C9—C10−170.0 (2)
C7—C2—C3—C40.0 (3)O1—C8—C9—C1011.9 (3)
C1—C2—C3—C4178.6 (2)C14—C9—C10—C112.0 (3)
C2—C3—C4—C5−1.6 (3)C8—C9—C10—C11−178.6 (2)
C2—C3—C4—Cl179.06 (16)C9—C10—C11—C12−2.1 (3)
C3—C4—C5—C61.8 (3)C10—C11—C12—C130.4 (3)
Cl—C4—C5—C6−178.83 (18)C10—C11—C12—I−178.92 (17)
C4—C5—C6—C7−0.4 (3)O2i—I—C12—C13−172.72 (15)
C8—O1—C7—C6177.6 (2)O2i—I—C12—C116.6 (3)
C8—O1—C7—C2−1.5 (2)C11—C12—C13—C141.4 (4)
C5—C6—C7—O1179.7 (2)I—C12—C13—C14−179.32 (18)
C5—C6—C7—C2−1.3 (3)C12—C13—C14—C9−1.5 (4)
C3—C2—C7—O1−179.39 (19)C10—C9—C14—C13−0.2 (4)
C1—C2—C7—O11.6 (2)C8—C9—C14—C13−179.6 (2)
C3—C2—C7—C61.5 (3)O2—S—C15—C16−172.90 (17)
C1—C2—C7—C6−177.5 (2)C1—S—C15—C1677.08 (19)
C2—C1—C8—O10.3 (2)

Symmetry codes: (i) x−1, y, z.

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C15—H15A···Cgii0.973.043.750 (3)131.

Symmetry codes: (ii) −x+3/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2194).

References

  • 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, o1862. [PMC free article] [PubMed]
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1985. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • 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]

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