Literature DB >> 21202411

5-Iodo-2,7-dimethyl-3-phenyl-sulfonyl-1-benzofuran.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.   

Abstract

The title compound, C(16)H(13)IO(3)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules, and between the benzene rings of neighbouring mol-ecules; the centroid-centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the crystal structure exhibits inter- and intra-molecular C-H⋯O inter-actions, and an I⋯O halogen bond with an I⋯O distance of 3.282 (2) Å and a nearly linear C-I⋯O angle of 165.69 (8)°.

Entities:  

Year:  2008        PMID： 21202411      PMCID： PMC2961136          DOI： 10.1107/S1600536808011240

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the crystal structures of similar 3-phenyl­sulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H13IO3S M = 412.22 Monoclinic, a = 8.1165 (5) Å b = 14.0295 (9) Å c = 13.2470 (8) Å β = 90.320 (1)° V = 1508.42 (16) Å3 Z = 4 Mo Kα radiation μ = 2.27 mm−1 T = 173 (2) K 0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.579, T max = 0.641 9110 measured reflections 3285 independent reflections 3069 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026 wR(F 2) = 0.074 S = 0.99 3285 reflections 193 parameters H-atom parameters constrained Δρmax = 1.13 e Å−3 Δρmin = −1.01 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011240/zl2112sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011240/zl2112Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13IO3SF000 = 808
Mr = 412.22Dx = 1.815 Mg m−3
Monoclinic, P21/nMelting point = 431–432 K
Hall symbol: -P_2ynMo Kα radiation λ = 0.71073 Å
a = 8.1165 (5) ÅCell parameters from 6912 reflections
b = 14.0295 (9) Åθ = 2.9–28.3º
c = 13.2470 (8) ŵ = 2.27 mm−1
β = 90.320 (1)ºT = 173 (2) K
V = 1508.42 (16) Å3Block, colorless
Z = 40.40 × 0.20 × 0.20 mm
Bruker SMART CCD diffractometer3285 independent reflections
Radiation source: fine-focus sealed tube3069 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
Detector resolution: 10.0 pixels mm-1θmax = 27.0º
T = 173(2) Kθmin = 2.9º
φ and ω scansh = −10→7
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)k = −17→16
Tmin = 0.579, Tmax = 0.641l = −16→16
9110 measured reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027  w = 1/[σ2(Fo2) + (0.0428P)2 + 1.8205P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max = 0.001
S = 0.99Δρmax = 1.13 e Å−3
3285 reflectionsΔρmin = −1.01 e Å−3
193 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0204 (8)
Secondary atom site location: difference Fourier map
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.
xyzUiso*/Ueq
I0.01644 (2)0.271298 (12)0.412327 (13)0.03036 (10)
S0.31859 (7)0.47908 (4)0.80435 (4)0.02106 (14)
O10.3994 (2)0.62669 (12)0.55765 (13)0.0216 (3)
O20.2767 (3)0.38039 (13)0.79316 (14)0.0304 (4)
O30.4628 (2)0.50442 (16)0.86163 (15)0.0343 (4)
C10.3367 (3)0.52624 (17)0.68298 (18)0.0196 (5)
C20.2699 (3)0.48622 (17)0.59100 (18)0.0192 (5)
C30.1833 (3)0.40340 (17)0.56413 (18)0.0216 (5)
H30.15300.35700.61280.026*
C40.1444 (3)0.39292 (18)0.46308 (19)0.0236 (5)
C50.1860 (3)0.46045 (18)0.39014 (19)0.0240 (5)
H50.15490.44970.32180.029*
C60.2718 (3)0.54330 (18)0.41501 (18)0.0224 (5)
C70.3120 (3)0.55133 (17)0.51657 (18)0.0204 (5)
C80.4119 (3)0.60993 (18)0.65900 (18)0.0216 (5)
C90.1490 (3)0.53904 (18)0.85741 (18)0.0240 (5)
C100.1754 (4)0.6275 (2)0.9019 (2)0.0381 (7)
H100.28250.65480.90330.046*
C110.0447 (5)0.6749 (3)0.9437 (3)0.0508 (9)
H110.06100.73550.97410.061*
C12−0.1097 (5)0.6348 (3)0.9418 (2)0.0497 (10)
H12−0.19960.66820.97070.060*
C13−0.1359 (4)0.5464 (3)0.8984 (2)0.0456 (9)
H13−0.24320.51930.89780.055*
C14−0.0047 (3)0.4970 (2)0.85537 (19)0.0311 (6)
H14−0.02070.43610.82550.037*
C150.3140 (4)0.6191 (2)0.3392 (2)0.0308 (6)
H15A0.23940.67350.34740.046*
H15B0.30210.59330.27080.046*
H15C0.42790.64010.35000.046*
C160.4982 (3)0.6852 (2)0.7172 (2)0.0284 (5)
H16A0.60320.70010.68460.043*
H16B0.51890.66260.78610.043*
H16C0.42950.74260.71930.043*
U11U22U33U12U13U23
I0.02777 (13)0.02830 (13)0.03502 (14)−0.00635 (6)0.00123 (8)−0.00964 (7)
S0.0220 (3)0.0220 (3)0.0192 (3)0.0029 (2)0.0004 (2)0.0016 (2)
O10.0229 (8)0.0197 (8)0.0224 (8)−0.0016 (7)0.0032 (7)0.0006 (7)
O20.0432 (12)0.0204 (9)0.0275 (9)0.0044 (8)0.0045 (8)0.0035 (7)
O30.0264 (10)0.0488 (12)0.0277 (9)−0.0001 (9)−0.0064 (8)0.0021 (9)
C10.0192 (11)0.0205 (11)0.0190 (11)0.0006 (9)0.0015 (9)−0.0001 (9)
C20.0169 (10)0.0208 (11)0.0200 (11)0.0020 (9)0.0024 (8)−0.0003 (9)
C30.0208 (11)0.0198 (11)0.0243 (11)−0.0006 (9)0.0030 (9)−0.0005 (9)
C40.0196 (11)0.0228 (12)0.0285 (12)0.0002 (9)0.0019 (9)−0.0051 (10)
C50.0243 (12)0.0274 (12)0.0203 (11)0.0035 (10)−0.0015 (9)−0.0028 (10)
C60.0222 (12)0.0232 (12)0.0219 (11)0.0054 (9)0.0025 (9)0.0018 (10)
C70.0178 (11)0.0185 (11)0.0250 (11)0.0004 (8)0.0027 (9)−0.0012 (9)
C80.0212 (11)0.0213 (11)0.0222 (11)0.0010 (9)0.0028 (9)−0.0005 (9)
C90.0296 (13)0.0250 (12)0.0174 (10)0.0053 (10)0.0046 (10)0.0042 (9)
C100.0479 (18)0.0284 (14)0.0383 (15)−0.0016 (13)0.0175 (14)−0.0031 (12)
C110.073 (3)0.0323 (16)0.0474 (19)0.0140 (16)0.0297 (18)0.0001 (14)
C120.058 (2)0.059 (2)0.0323 (16)0.0347 (18)0.0188 (15)0.0125 (15)
C130.0245 (14)0.085 (3)0.0269 (14)0.0115 (15)0.0020 (11)0.0152 (16)
C140.0261 (13)0.0458 (16)0.0214 (12)0.0018 (12)−0.0038 (10)0.0030 (11)
C150.0378 (15)0.0302 (14)0.0245 (12)0.0014 (11)0.0019 (11)0.0068 (11)
C160.0288 (13)0.0264 (13)0.0299 (13)−0.0052 (11)0.0018 (10)−0.0049 (11)
I—O2i3.282 (2)C8—C161.481 (3)
I—C42.106 (3)C9—C141.380 (4)
S—O21.433 (2)C9—C101.390 (4)
S—O31.436 (2)C10—C111.371 (4)
S—C11.746 (2)C10—H100.9500
S—C91.762 (3)C11—C121.374 (6)
O1—C81.366 (3)C11—H110.9500
O1—C71.383 (3)C12—C131.383 (6)
C1—C81.362 (3)C12—H120.9500
C1—C21.444 (3)C13—C141.395 (4)
C2—C71.388 (3)C13—H130.9500
C2—C31.403 (3)C14—H140.9500
C3—C41.381 (3)C15—H15A0.9800
C3—H30.9500C15—H15B0.9800
C4—C51.396 (4)C15—H15C0.9800
C5—C61.394 (4)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.387 (3)C16—H16C0.9800
C6—C151.504 (3)
C4—I—O2i165.69 (8)O1—C8—C16114.9 (2)
O2—S—O3119.1 (1)C14—C9—C10121.8 (3)
O2—S—C1107.0 (1)C14—C9—S119.7 (2)
O3—S—C1108.7 (1)C10—C9—S118.5 (2)
O2—S—C9108.5 (1)C11—C10—C9119.1 (3)
O3—S—C9107.9 (1)C11—C10—H10120.4
C1—S—C9104.9 (1)C9—C10—H10120.4
C8—O1—C7106.9 (2)C10—C11—C12120.1 (3)
C8—C1—C2107.7 (2)C10—C11—H11120.0
C8—C1—S125.6 (2)C12—C11—H11120.0
C2—C1—S126.6 (2)C11—C12—C13120.9 (3)
C7—C2—C3119.3 (2)C11—C12—H12119.6
C7—C2—C1104.5 (2)C13—C12—H12119.6
C3—C2—C1136.1 (2)C12—C13—C14119.9 (3)
C4—C3—C2116.5 (2)C12—C13—H13120.0
C4—C3—H3121.8C14—C13—H13120.0
C2—C3—H3121.8C9—C14—C13118.2 (3)
C3—C4—C5122.9 (2)C9—C14—H14120.9
C3—C4—I120.4 (2)C13—C14—H14120.9
C5—C4—I116.7 (2)C6—C15—H15A109.5
C6—C5—C4121.7 (2)C6—C15—H15B109.5
C6—C5—H5119.2H15A—C15—H15B109.5
C4—C5—H5119.2C6—C15—H15C109.5
C7—C6—C5114.3 (2)H15A—C15—H15C109.5
C7—C6—C15122.5 (2)H15B—C15—H15C109.5
C5—C6—C15123.2 (2)C8—C16—H16A109.5
O1—C7—C2110.6 (2)C8—C16—H16B109.5
O1—C7—C6124.1 (2)H16A—C16—H16B109.5
C2—C7—C6125.3 (2)C8—C16—H16C109.5
C1—C8—O1110.3 (2)H16A—C16—H16C109.5
C1—C8—C16134.8 (2)H16B—C16—H16C109.5
O2—S—C1—C8−163.4 (2)C5—C6—C7—O1178.8 (2)
O3—S—C1—C8−33.6 (3)C15—C6—C7—O1−2.7 (4)
C9—S—C1—C881.5 (2)C5—C6—C7—C2−1.7 (4)
O2—S—C1—C219.2 (2)C15—C6—C7—C2176.8 (2)
O3—S—C1—C2149.0 (2)C2—C1—C8—O1−0.4 (3)
C9—S—C1—C2−95.8 (2)S—C1—C8—O1−178.2 (2)
C8—C1—C2—C70.1 (3)C2—C1—C8—C16178.1 (3)
S—C1—C2—C7177.8 (2)S—C1—C8—C160.3 (4)
C8—C1—C2—C3178.8 (3)C7—O1—C8—C10.5 (3)
S—C1—C2—C3−3.4 (4)C7—O1—C8—C16−178.3 (2)
C7—C2—C3—C4−0.4 (3)O2—S—C9—C14−17.4 (2)
C1—C2—C3—C4−179.1 (3)O3—S—C9—C14−147.6 (2)
C2—C3—C4—C5−0.7 (4)C1—S—C9—C1496.7 (2)
C2—C3—C4—I179.5 (2)O2—S—C9—C10161.6 (2)
C3—C4—C5—C60.7 (4)O3—S—C9—C1031.4 (2)
I—C4—C5—C6−179.5 (2)C1—S—C9—C10−84.4 (2)
C4—C5—C6—C70.5 (4)C14—C9—C10—C11−0.9 (5)
C4—C5—C6—C15−178.0 (2)S—C9—C10—C11−179.8 (3)
C8—O1—C7—C2−0.5 (3)C9—C10—C11—C120.3 (5)
C8—O1—C7—C6179.0 (2)C10—C11—C12—C130.3 (5)
C3—C2—C7—O1−178.7 (2)C11—C12—C13—C14−0.3 (5)
C1—C2—C7—O10.3 (3)C10—C9—C14—C130.8 (4)
C3—C2—C7—C61.7 (4)S—C9—C14—C13179.8 (2)
C1—C2—C7—C6−179.3 (2)C12—C13—C14—C9−0.3 (4)
D—H···AD—HH···AD···AD—H···A
C11—H11···O1ii0.952.593.382 (4)141
C13—H13···O3iii0.952.443.342 (4)159
C14—H14···O20.952.582.931 (4)103
C16—H16B···O30.982.483.191 (4)129
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11⋯O1i0.952.593.382 (4)141
C13—H13⋯O3ii0.952.443.342 (4)159
C14—H14⋯O20.952.582.931 (4)103
C16—H16B⋯O30.982.483.191 (4)129

Symmetry codes: (i) ; (ii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  An overview of halogen bonding.

Authors:  Peter Politzer; Pat Lane; Monica C Concha; Yuguang Ma; Jane S Murray
Journal:  J Mol Model       Date:  2006-09-30       Impact factor: 1.810

3.  2,5,7-Trimethyl-3-phenyl-sulfonyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-02

4.  5-Bromo-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-02
  4 in total
  4 in total

1.  5-Fluoro-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-09

2.  5-Fluoro-3-(4-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-03

3.  3-(4-Fluoro-phenyl-sulfon-yl)-5-iodo-2,7-dimethyl-1-benzofuran.

Authors:  Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-10

4.  5-Iodo-2,7-dimethyl-3-(4-methyl-phenyl-sulfon-yl)-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-08
  4 in total

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