Literature DB >> 21589545

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

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

Abstract

In the title compound, C(17)H(14)FIO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 18.88 (9)° with the mean plane of the benzofuran ring. In the crystal, pairs of inter-molecular I⋯O contacts [3.153 (2) Å] link the mol-ecules into inversion dimers.

Entities:  

Year:  2010        PMID： 21589545      PMCID： PMC3011574          DOI： 10.1107/S1600536810047665

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


Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For our previous structural studies of related 3-alkyl­sulfinyl-2-(4-fluoro­phen­yl)-5-iodo-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14FIO2S M = 428.24 Triclinic, a = 8.4345 (1) Å b = 9.5874 (2) Å c = 10.9324 (2) Å α = 68.643 (1)° β = 70.618 (1)° γ = 89.241 (1)° V = 770.83 (2) Å3 Z = 2 Mo Kα radiation μ = 2.23 mm−1 T = 180 K 0.23 × 0.22 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.594, T max = 0.746 13711 measured reflections 3544 independent reflections 3407 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.020 wR(F 2) = 0.055 S = 1.14 3544 reflections 201 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.93 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810047665/su2229sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047665/su2229Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H14FIO2SZ = 2
Mr = 428.24F(000) = 420
Triclinic, P1Dx = 1.845 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4345 (1) ÅCell parameters from 9898 reflections
b = 9.5874 (2) Åθ = 2.3–27.5°
c = 10.9324 (2) ŵ = 2.23 mm−1
α = 68.643 (1)°T = 180 K
β = 70.618 (1)°Block, colourless
γ = 89.241 (1)°0.23 × 0.22 × 0.12 mm
V = 770.83 (2) Å3
Bruker SMART APEXII CCD diffractometer3544 independent reflections
Radiation source: rotating anode3407 reflections with I > 2σ(I)
graphite multilayerRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.1°
φ and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.594, Tmax = 0.746l = −14→14
13711 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: difference Fourier map
wR(F2) = 0.055H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0298P)2 + 0.238P] where P = (Fo2 + 2Fc2)/3
3544 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.93 e Å−3
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.
xyzUiso*/Ueq
I10.417391 (15)0.151710 (13)1.131578 (12)0.02794 (6)
S10.35022 (6)0.16149 (5)0.56324 (5)0.02224 (10)
F10.08962 (18)0.68702 (15)0.06579 (14)0.0395 (3)
O10.27453 (17)0.55572 (14)0.60153 (14)0.0241 (3)
O20.46705 (19)0.07898 (17)0.63276 (17)0.0324 (3)
C10.3041 (2)0.3160 (2)0.61705 (19)0.0213 (3)
C20.3257 (2)0.3290 (2)0.7385 (2)0.0213 (3)
C30.3567 (2)0.2321 (2)0.8569 (2)0.0238 (4)
H30.36970.12930.87160.029*
C40.3677 (2)0.2918 (2)0.9521 (2)0.0240 (4)
C50.3511 (3)0.4434 (2)0.9322 (2)0.0279 (4)
H50.36110.48010.99950.034*
C60.3203 (3)0.5403 (2)0.8147 (2)0.0284 (4)
H60.30870.64350.79910.034*
C70.3074 (2)0.4790 (2)0.7221 (2)0.0234 (4)
C80.2727 (2)0.4542 (2)0.5392 (2)0.0216 (3)
C90.2301 (2)0.5145 (2)0.4121 (2)0.0221 (4)
C100.2428 (2)0.6710 (2)0.3413 (2)0.0253 (4)
H100.28340.73740.37390.030*
C110.1966 (3)0.7288 (2)0.2242 (2)0.0290 (4)
H110.20630.83480.17520.035*
C120.1363 (2)0.6309 (2)0.1796 (2)0.0273 (4)
C130.1226 (3)0.4763 (2)0.2458 (2)0.0278 (4)
H130.08180.41110.21200.033*
C140.1698 (3)0.4187 (2)0.3627 (2)0.0264 (4)
H140.16110.31250.41000.032*
C150.1418 (2)0.0465 (2)0.6546 (2)0.0245 (4)
H150.05420.11150.63090.029*
C160.0973 (3)−0.0158 (3)0.8118 (2)0.0350 (5)
H16A−0.0086−0.08430.85680.053*
H16B0.08330.06750.84480.053*
H16C0.1883−0.07090.83590.053*
C170.1496 (3)−0.0768 (2)0.5953 (3)0.0396 (5)
H17A0.2342−0.14220.61870.059*
H17B0.1811−0.02990.49320.059*
H17C0.0384−0.13700.63620.059*
U11U22U33U12U13U23
I10.03365 (9)0.02957 (8)0.02477 (9)0.00348 (5)−0.01555 (6)−0.01020 (6)
S10.0247 (2)0.0215 (2)0.0218 (2)0.00425 (17)−0.00912 (18)−0.00885 (17)
F10.0464 (8)0.0401 (7)0.0277 (7)0.0044 (6)−0.0213 (6)−0.0007 (5)
O10.0285 (7)0.0208 (6)0.0257 (7)0.0037 (5)−0.0134 (6)−0.0084 (5)
O20.0322 (8)0.0346 (7)0.0376 (8)0.0131 (6)−0.0195 (7)−0.0156 (7)
C10.0214 (8)0.0220 (8)0.0212 (9)0.0022 (6)−0.0080 (7)−0.0084 (7)
C20.0190 (8)0.0236 (8)0.0227 (9)0.0022 (6)−0.0069 (7)−0.0106 (7)
C30.0244 (9)0.0237 (8)0.0253 (10)0.0048 (7)−0.0106 (7)−0.0099 (7)
C40.0225 (9)0.0287 (9)0.0226 (9)0.0035 (7)−0.0109 (7)−0.0094 (8)
C50.0298 (10)0.0309 (10)0.0305 (11)0.0048 (8)−0.0139 (8)−0.0169 (8)
C60.0335 (10)0.0241 (9)0.0342 (11)0.0061 (8)−0.0163 (9)−0.0144 (8)
C70.0213 (9)0.0240 (8)0.0254 (10)0.0031 (7)−0.0103 (7)−0.0084 (7)
C80.0202 (8)0.0219 (8)0.0226 (9)0.0013 (6)−0.0074 (7)−0.0086 (7)
C90.0189 (8)0.0226 (8)0.0211 (9)0.0015 (6)−0.0056 (7)−0.0054 (7)
C100.0235 (9)0.0225 (8)0.0272 (10)0.0023 (7)−0.0080 (8)−0.0072 (8)
C110.0286 (10)0.0212 (8)0.0300 (11)0.0039 (7)−0.0095 (8)−0.0026 (8)
C120.0239 (9)0.0315 (9)0.0208 (9)0.0048 (7)−0.0093 (7)−0.0022 (8)
C130.0295 (10)0.0291 (9)0.0245 (10)0.0002 (8)−0.0110 (8)−0.0083 (8)
C140.0320 (10)0.0206 (8)0.0247 (10)0.0003 (7)−0.0126 (8)−0.0042 (7)
C150.0251 (9)0.0205 (8)0.0272 (10)0.0017 (7)−0.0118 (8)−0.0059 (7)
C160.0344 (11)0.0356 (11)0.0258 (11)−0.0043 (9)−0.0104 (9)−0.0014 (9)
C170.0460 (13)0.0288 (10)0.0476 (14)0.0008 (9)−0.0163 (11)−0.0185 (10)
I1—C42.1074 (19)C9—C141.397 (3)
I1—O2i3.1525 (15)C9—C101.402 (2)
S1—O21.4876 (15)C10—C111.381 (3)
S1—C11.7774 (18)C10—H100.9500
S1—C151.841 (2)C11—C121.374 (3)
F1—C121.351 (2)C11—H110.9500
O1—C71.373 (2)C12—C131.380 (3)
O1—C81.380 (2)C13—C141.384 (3)
C1—C81.367 (3)C13—H130.9500
C1—C21.446 (3)C14—H140.9500
C2—C31.396 (3)C15—C161.510 (3)
C2—C71.396 (2)C15—C171.532 (3)
C3—C41.385 (3)C15—H151.0000
C3—H30.9500C16—H16A0.9800
C4—C51.402 (3)C16—H16B0.9800
C5—C61.388 (3)C16—H16C0.9800
C5—H50.9500C17—H17A0.9800
C6—C71.375 (3)C17—H17B0.9800
C6—H60.9500C17—H17C0.9800
C8—C91.460 (3)
C4—I1—O2i170.73 (6)C11—C10—H10119.9
O2—S1—C1106.47 (8)C9—C10—H10119.9
O2—S1—C15107.12 (9)C12—C11—C10119.07 (18)
C1—S1—C1599.87 (9)C12—C11—H11120.5
C7—O1—C8106.69 (14)C10—C11—H11120.5
C8—C1—C2106.99 (15)F1—C12—C11119.27 (17)
C8—C1—S1126.19 (15)F1—C12—C13118.10 (18)
C2—C1—S1125.82 (13)C11—C12—C13122.63 (19)
C3—C2—C7118.97 (17)C12—C13—C14118.15 (18)
C3—C2—C1135.97 (17)C12—C13—H13120.9
C7—C2—C1105.06 (16)C14—C13—H13120.9
C4—C3—C2117.37 (17)C13—C14—C9120.93 (17)
C4—C3—H3121.3C13—C14—H14119.5
C2—C3—H3121.3C9—C14—H14119.5
C3—C4—C5122.52 (18)C16—C15—C17113.13 (17)
C3—C4—I1119.10 (14)C16—C15—S1111.52 (14)
C5—C4—I1118.36 (14)C17—C15—S1106.42 (14)
C6—C5—C4120.40 (18)C16—C15—H15108.5
C6—C5—H5119.8C17—C15—H15108.5
C4—C5—H5119.8S1—C15—H15108.5
C7—C6—C5116.43 (17)C15—C16—H16A109.5
C7—C6—H6121.8C15—C16—H16B109.5
C5—C6—H6121.8H16A—C16—H16B109.5
O1—C7—C6125.06 (16)C15—C16—H16C109.5
O1—C7—C2110.64 (16)H16A—C16—H16C109.5
C6—C7—C2124.30 (18)H16B—C16—H16C109.5
C1—C8—O1110.61 (16)C15—C17—H17A109.5
C1—C8—C9134.93 (17)C15—C17—H17B109.5
O1—C8—C9114.36 (15)H17A—C17—H17B109.5
C14—C9—C10119.02 (18)C15—C17—H17C109.5
C14—C9—C8121.04 (16)H17A—C17—H17C109.5
C10—C9—C8119.88 (17)H17B—C17—H17C109.5
C11—C10—C9120.20 (18)
O2—S1—C1—C8147.63 (17)S1—C1—C8—O1−168.30 (13)
C15—S1—C1—C8−101.09 (18)C2—C1—C8—C9−175.53 (19)
O2—S1—C1—C2−19.38 (18)S1—C1—C8—C915.5 (3)
C15—S1—C1—C291.91 (17)C7—O1—C8—C1−0.2 (2)
C8—C1—C2—C3178.6 (2)C7—O1—C8—C9176.86 (15)
S1—C1—C2—C3−12.3 (3)C1—C8—C9—C1417.1 (3)
C8—C1—C2—C7−0.9 (2)O1—C8—C9—C14−159.09 (17)
S1—C1—C2—C7168.15 (14)C1—C8—C9—C10−165.7 (2)
C7—C2—C3—C40.0 (3)O1—C8—C9—C1018.2 (2)
C1—C2—C3—C4−179.5 (2)C14—C9—C10—C11−0.2 (3)
C2—C3—C4—C5−0.8 (3)C8—C9—C10—C11−177.49 (17)
C2—C3—C4—I1−179.23 (13)C9—C10—C11—C120.8 (3)
C3—C4—C5—C60.9 (3)C10—C11—C12—F1179.47 (18)
I1—C4—C5—C6179.27 (15)C10—C11—C12—C13−1.1 (3)
C4—C5—C6—C70.0 (3)F1—C12—C13—C14−179.79 (18)
C8—O1—C7—C6179.81 (18)C11—C12—C13—C140.8 (3)
C8—O1—C7—C2−0.40 (19)C12—C13—C14—C9−0.1 (3)
C5—C6—C7—O1178.82 (18)C10—C9—C14—C13−0.2 (3)
C5—C6—C7—C2−0.9 (3)C8—C9—C14—C13177.14 (18)
C3—C2—C7—O1−178.83 (16)O2—S1—C15—C1643.28 (16)
C1—C2—C7—O10.8 (2)C1—S1—C15—C16−67.49 (15)
C3—C2—C7—C61.0 (3)O2—S1—C15—C17−80.53 (15)
C1—C2—C7—C6−179.40 (18)C1—S1—C15—C17168.70 (14)
C2—C1—C8—O10.7 (2)
  8 in total

1.  Benzofurans and another constituent from seeds of Styrax officinalis.

Authors:  Yurdanur Yayla Akgul; Huseyin Anil
Journal:  Phytochemistry       Date:  2003-08       Impact factor: 4.072

2.  A new structural alternative in benzo[b]furans for antimicrobial activity.

Authors:  M Wahab Khan; M Jahangir Alam; M A Rashid; R Chowdhury
Journal:  Bioorg Med Chem       Date:  2005-08-15       Impact factor: 3.641

3.  A short history of SHELX.

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

4.  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

5.  Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus fretessi (Moraceae).

Authors:  Nunuk H Soekamto; Sjamsul A Achmad; Emilio L Ghisalberti; Euis H Hakim; Yana M Syah
Journal:  Phytochemistry       Date:  2003-10       Impact factor: 4.072

6.  2-(4-Fluoro-phen-yl)-5-iodo-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:  2009-12-04

7.  Synthesis of potent antitumor and antiviral benzofuran derivatives.

Authors:  Shadia A Galal; Amira S Abd El-All; Mohamed M Abdallah; Hoda I El-Diwani
Journal:  Bioorg Med Chem Lett       Date:  2009-03-21       Impact factor: 2.823

8.  3-Ethyl-sulfinyl-2-(4-fluoro-phen-yl)-5-iodo-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-10
  8 in total
  1 in total

1.  2-(4-Fluoro-phen-yl)-5-iodo-3-isopropyl-sulfonyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-10-20
  1 in total

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