Literature DB >> 21202580

2-(4-Iodo-phen-yl)-5-methyl-3-methyl-sulfinyl-1-benzofuran.

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

Abstract

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5-methyl-3-methyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The mol-ecular packing is stabilized by C-H⋯π inter-actions between H atoms on the 4-iodo-phenyl ring and the benzofuran rings, and by an I⋯O halogen bond of 3.252 (2) Å with a nearly linear C-I⋯O angle of 163.06 (8)°. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [3.209 (2) Å] involving the sulfinyl groups.

Entities:  

Year:  2008        PMID： 21202580      PMCID： PMC2961388          DOI： 10.1107/S1600536808013706

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


Related literature

For the crystal structures of similar 2-aryl-5-methyl-3-methyl­sulfinyl-1-benzofuran compounds, see: Choi et al. (2007a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2007c ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C16H13IO2S M = 396.22 Monoclinic, a = 9.258 (2) Å b = 15.939 (3) Å c = 10.299 (2) Å β = 103.471 (3)° V = 1477.9 (5) Å3 Z = 4 Mo Kα radiation μ = 2.31 mm−1 T = 173 (2) K 0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.443, T max = 0.508 8743 measured reflections 3227 independent reflections 2934 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.026 wR(F 2) = 0.065 S = 1.15 3227 reflections 183 parameters H-atom parameters constrained Δρmax = 0.54 e Å−3 Δρmin = −0.94 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 I, global. DOI: 10.1107/S1600536808013706/sj2496sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013706/sj2496Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13IO2SF000 = 776
Mr = 396.22Dx = 1.781 Mg m−3
Monoclinic, P21/nMelting point = 472–473 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 9.258 (2) ÅCell parameters from 6653 reflections
b = 15.939 (3) Åθ = 2.4–28.2º
c = 10.299 (2) ŵ = 2.31 mm−1
β = 103.471 (3)ºT = 173 (2) K
V = 1477.9 (5) Å3Block, colorless
Z = 40.40 × 0.30 × 0.30 mm
Bruker SMART CCD diffractometer3227 independent reflections
Radiation source: fine-focus sealed tube2934 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 27.0º
T = 173(2) Kθmin = 2.4º
φ and ω scansh = −11→6
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)k = −20→20
Tmin = 0.443, Tmax = 0.508l = −11→13
8743 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.065  w = 1/[σ2(Fo2) + (0.0226P)2 + 1.1637P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
3227 reflectionsΔρmax = 0.54 e Å−3
183 parametersΔρmin = −0.94 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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
I−0.134684 (19)0.613119 (11)−0.281817 (17)0.03372 (7)
S0.51165 (7)0.54138 (4)0.32703 (6)0.02482 (13)
O10.61196 (19)0.66982 (11)0.02820 (17)0.0251 (4)
O20.5977 (2)0.57384 (14)0.45895 (18)0.0389 (5)
C10.5913 (3)0.59181 (15)0.2070 (2)0.0220 (5)
C20.7456 (3)0.61452 (15)0.2246 (2)0.0231 (5)
C30.8760 (3)0.60093 (15)0.3218 (3)0.0262 (5)
H30.87460.56870.39910.031*
C41.0087 (3)0.63528 (17)0.3040 (3)0.0309 (6)
C51.0091 (3)0.68158 (17)0.1884 (3)0.0329 (6)
H51.10060.70380.17710.039*
C60.8810 (3)0.69632 (16)0.0895 (3)0.0308 (6)
H60.88240.72770.01140.037*
C70.7515 (3)0.66243 (15)0.1120 (2)0.0249 (5)
C80.5155 (3)0.62626 (14)0.0892 (2)0.0228 (5)
C90.3610 (3)0.62508 (15)0.0136 (2)0.0217 (5)
C100.3001 (3)0.69536 (16)−0.0607 (3)0.0270 (5)
H100.35720.7453−0.05640.032*
C110.1575 (3)0.69273 (16)−0.1403 (3)0.0284 (5)
H110.11620.7410−0.18930.034*
C120.0746 (3)0.61946 (15)−0.1483 (2)0.0235 (5)
C130.1323 (3)0.54923 (15)−0.0743 (2)0.0230 (5)
H130.07460.4995−0.07970.028*
C140.2744 (3)0.55201 (15)0.0075 (2)0.0218 (5)
H140.31340.50440.05950.026*
C151.1498 (3)0.62338 (19)0.4100 (3)0.0417 (7)
H15A1.13450.64250.49620.063*
H15B1.22980.65610.38670.063*
H15C1.17690.56380.41600.063*
C160.5769 (3)0.43689 (17)0.3073 (3)0.0317 (6)
H16A0.68330.43860.30960.048*
H16B0.52270.41390.22160.048*
H16C0.56040.40130.38010.048*
U11U22U33U12U13U23
I0.02443 (11)0.04004 (12)0.03256 (11)−0.00188 (7)−0.00175 (7)0.00229 (7)
S0.0250 (3)0.0303 (3)0.0206 (3)−0.0021 (2)0.0083 (2)−0.0031 (2)
O10.0205 (8)0.0272 (9)0.0277 (9)−0.0025 (7)0.0057 (7)0.0030 (7)
O20.0418 (12)0.0538 (13)0.0214 (9)−0.0143 (10)0.0082 (8)−0.0077 (9)
C10.0224 (12)0.0229 (11)0.0215 (11)−0.0001 (9)0.0066 (9)−0.0038 (9)
C20.0239 (13)0.0225 (11)0.0233 (11)0.0009 (9)0.0062 (10)−0.0069 (9)
C30.0251 (13)0.0251 (12)0.0274 (12)0.0031 (9)0.0039 (10)−0.0077 (9)
C40.0231 (13)0.0290 (13)0.0382 (14)0.0037 (10)0.0024 (11)−0.0142 (11)
C50.0209 (13)0.0293 (13)0.0497 (16)−0.0028 (10)0.0108 (11)−0.0095 (12)
C60.0257 (13)0.0281 (13)0.0413 (15)−0.0005 (10)0.0133 (11)−0.0007 (11)
C70.0212 (12)0.0227 (12)0.0313 (12)−0.0002 (9)0.0067 (10)−0.0042 (10)
C80.0217 (12)0.0216 (11)0.0259 (12)−0.0013 (9)0.0076 (10)−0.0025 (9)
C90.0208 (12)0.0245 (12)0.0203 (11)−0.0006 (9)0.0055 (9)−0.0019 (9)
C100.0252 (13)0.0236 (12)0.0319 (13)−0.0040 (10)0.0062 (10)0.0030 (10)
C110.0286 (13)0.0250 (12)0.0308 (13)0.0012 (10)0.0051 (11)0.0068 (10)
C120.0190 (11)0.0295 (13)0.0221 (11)0.0002 (9)0.0046 (9)−0.0014 (9)
C130.0252 (12)0.0211 (11)0.0245 (11)−0.0034 (9)0.0095 (10)−0.0024 (9)
C140.0247 (12)0.0209 (11)0.0202 (11)0.0007 (9)0.0062 (9)0.0014 (9)
C150.0240 (14)0.0445 (17)0.0514 (18)0.0020 (12)−0.0017 (13)−0.0162 (14)
C160.0351 (15)0.0325 (14)0.0296 (13)0.0038 (11)0.0116 (11)0.0046 (11)
I—O2i3.252 (2)C6—H60.9500
I—C122.101 (3)C8—C91.461 (3)
S—O21.4981 (19)C9—C101.399 (3)
S—O2ii3.209 (2)C9—C141.407 (3)
S—C11.773 (2)C10—C111.383 (4)
S—C161.799 (3)C10—H100.9500
O1—C71.381 (3)C11—C121.389 (3)
O1—C81.391 (3)C11—H110.9500
C1—C81.367 (3)C12—C131.389 (3)
C1—C21.444 (3)C13—C141.388 (3)
C2—C31.394 (4)C13—H130.9500
C2—C71.400 (3)C14—H140.9500
C3—C41.395 (4)C15—H15A0.9800
C3—H30.9500C15—H15B0.9800
C4—C51.402 (4)C15—H15C0.9800
C4—C151.507 (4)C16—H16A0.9800
C5—C61.391 (4)C16—H16B0.9800
C5—H50.9500C16—H16C0.9800
C6—C71.383 (4)
C12—I—O2i163.06 (8)C10—C9—C8120.1 (2)
O2—S—C1104.84 (12)C14—C9—C8120.7 (2)
O2—S—C16107.47 (13)C11—C10—C9120.5 (2)
C1—S—C1697.80 (12)C11—C10—H10119.8
C7—O1—C8106.30 (18)C9—C10—H10119.8
C8—C1—C2107.4 (2)C10—C11—C12119.9 (2)
C8—C1—S126.1 (2)C10—C11—H11120.1
C2—C1—S125.89 (18)C12—C11—H11120.1
C3—C2—C7119.1 (2)C13—C12—C11120.6 (2)
C3—C2—C1135.8 (2)C13—C12—I119.88 (18)
C7—C2—C1105.1 (2)C11—C12—I119.44 (18)
C2—C3—C4119.1 (2)C14—C13—C12119.7 (2)
C2—C3—H3120.5C14—C13—H13120.1
C4—C3—H3120.5C12—C13—H13120.1
C3—C4—C5119.7 (2)C13—C14—C9120.2 (2)
C3—C4—C15119.8 (3)C13—C14—H14119.9
C5—C4—C15120.6 (3)C9—C14—H14119.9
C6—C5—C4122.7 (2)C4—C15—H15A109.5
C6—C5—H5118.7C4—C15—H15B109.5
C4—C5—H5118.7H15A—C15—H15B109.5
C7—C6—C5115.9 (3)C4—C15—H15C109.5
C7—C6—H6122.1H15A—C15—H15C109.5
C5—C6—H6122.1H15B—C15—H15C109.5
O1—C7—C6125.7 (2)S—C16—H16A109.5
O1—C7—C2110.7 (2)S—C16—H16B109.5
C6—C7—C2123.6 (2)H16A—C16—H16B109.5
C1—C8—O1110.5 (2)S—C16—H16C109.5
C1—C8—C9134.8 (2)H16A—C16—H16C109.5
O1—C8—C9114.6 (2)H16B—C16—H16C109.5
C10—C9—C14119.1 (2)
O2—S—C1—C8−136.9 (2)C1—C2—C7—C6−179.6 (2)
C16—S—C1—C8112.7 (2)C2—C1—C8—O10.4 (3)
O2—S—C1—C233.6 (2)S—C1—C8—O1172.33 (17)
C16—S—C1—C2−76.9 (2)C2—C1—C8—C9178.0 (3)
C8—C1—C2—C3178.7 (3)S—C1—C8—C9−10.1 (4)
S—C1—C2—C36.8 (4)C7—O1—C8—C1−0.5 (3)
C8—C1—C2—C7−0.2 (3)C7—O1—C8—C9−178.63 (19)
S—C1—C2—C7−172.09 (18)C1—C8—C9—C10146.5 (3)
C7—C2—C3—C4−0.1 (3)O1—C8—C9—C10−36.0 (3)
C1—C2—C3—C4−178.9 (3)C1—C8—C9—C14−37.5 (4)
C2—C3—C4—C5−0.9 (4)O1—C8—C9—C14140.0 (2)
C2—C3—C4—C15178.2 (2)C14—C9—C10—C11−0.8 (4)
C3—C4—C5—C61.0 (4)C8—C9—C10—C11175.3 (2)
C15—C4—C5—C6−178.1 (2)C9—C10—C11—C12−1.0 (4)
C4—C5—C6—C70.1 (4)C10—C11—C12—C131.7 (4)
C8—O1—C7—C6179.8 (2)C10—C11—C12—I−174.85 (19)
C8—O1—C7—C20.4 (2)C11—C12—C13—C14−0.6 (4)
C5—C6—C7—O1179.4 (2)I—C12—C13—C14175.94 (17)
C5—C6—C7—C2−1.2 (4)C12—C13—C14—C9−1.2 (3)
C3—C2—C7—O1−179.3 (2)C10—C9—C14—C131.9 (3)
C1—C2—C7—O1−0.2 (3)C8—C9—C14—C13−174.2 (2)
C3—C2—C7—C61.3 (4)
D—H···AD—HH···AD···AD—H···A
C10—H10···Cg1iii0.953.013.617 (4)125
C11—H11···Cg2iii0.952.773.643 (4)148
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10⋯Cg1i0.953.013.617 (4)125
C11—H11⋯Cg2i0.952.773.643 (4)148

Symmetry code: (i) . Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the O1/C8/C1/C2/C7 furan ring, respectively.

  2 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
  2 in total
  6 in total

1.  5-Chloro-7-methyl-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-04

2.  5-Cyclo-hexyl-2-(2-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-05-15

3.  2-(4-Fluoro-phen-yl)-5-iodo-7-methyl-3-phenyl-sulfinyl-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-05-04

4.  5-Fluoro-2-(4-iodo-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-08

5.  5-Bromo-2-(4-fluoro-phen-yl)-7-methyl-3-phenyl-sulfinyl-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-22

6.  5-Chloro-3-ethyl-sulfinyl-2-(3-fluoro-phen-yl)-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-06
  6 in total

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