Literature DB >> 22259594

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

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

Abstract

In the title compound, C(16)H(12)FIO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, and by an I⋯I contact [3.7764 (3) Å]. The crystal structure also exhibits a weak C-I⋯π [3.901 (3) Å] inter-action and a slipped π-π inter-action between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.845 (3), inter-planar distance = 3.555 (3) and slippage = 1.465 (3) Å].

Entities:  

Year:  2011        PMID： 22259594      PMCID： PMC3254446          DOI： 10.1107/S1600536811052792

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


Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For related structures, see: Choi et al. (2008 ▶, 2011 ▶).

Experimental

Crystal data

C16H12FIO3S M = 430.22 Triclinic, a = 7.5839 (2) Å b = 10.2443 (3) Å c = 10.4651 (3) Å α = 79.424 (1)° β = 75.652 (1)° γ = 80.361 (1)° V = 767.94 (4) Å3 Z = 2 Mo Kα radiation μ = 2.24 mm−1 T = 173 K 0.32 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.534, T max = 0.689 13962 measured reflections 3785 independent reflections 3585 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.022 wR(F 2) = 0.057 S = 1.08 3785 reflections 201 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.72 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 datablock(s) global, I. DOI: 10.1107/S1600536811052792/bh2405sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052792/bh2405Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811052792/bh2405Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H12FIO3SZ = 2
Mr = 430.22F(000) = 420
Triclinic, P1Dx = 1.861 Mg m−3
Hall symbol: -P 1Melting point: 430 K
a = 7.5839 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2443 (3) ÅCell parameters from 9929 reflections
c = 10.4651 (3) Åθ = 2.7–28.3°
α = 79.424 (1)°µ = 2.24 mm−1
β = 75.652 (1)°T = 173 K
γ = 80.361 (1)°Block, colourless
V = 767.94 (4) Å30.32 × 0.30 × 0.18 mm
Bruker SMART APEXII CCD diffractometer3785 independent reflections
Radiation source: rotating anode3585 reflections with I > 2σ(I)
graphite multilayerRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
φ and ω scansh = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −13→13
Tmin = 0.534, Tmax = 0.689l = −13→13
13962 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)] = 0.022Hydrogen site location: difference Fourier map
wR(F2) = 0.057H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.028P)2 + 0.3904P] where P = (Fo2 + 2Fc2)/3
3785 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
0 constraints
xyzUiso*/Ueq
I10.458085 (17)0.514608 (14)0.182660 (11)0.03682 (6)
S10.09268 (6)0.13784 (4)0.70600 (4)0.02423 (9)
F10.7392 (2)−0.17671 (16)0.86383 (18)0.0602 (4)
O10.07637 (18)0.50285 (12)0.77645 (12)0.0243 (2)
O20.1076 (2)0.12200 (14)0.56993 (14)0.0337 (3)
O3−0.06489 (19)0.09921 (14)0.80627 (15)0.0332 (3)
C10.1071 (2)0.30519 (17)0.70547 (17)0.0227 (3)
C20.1812 (2)0.39985 (16)0.59204 (17)0.0219 (3)
C30.2651 (2)0.39515 (18)0.45767 (17)0.0242 (3)
H30.28280.31540.41950.029*
C40.3210 (2)0.51397 (19)0.38343 (17)0.0259 (3)
C50.2946 (3)0.63304 (18)0.43641 (19)0.0281 (4)
H50.33450.71140.38020.034*
C60.2110 (3)0.63949 (17)0.56963 (19)0.0261 (3)
C70.1583 (2)0.51938 (17)0.64268 (17)0.0226 (3)
C80.0489 (2)0.37130 (17)0.81325 (18)0.0242 (3)
C90.1834 (3)0.76435 (19)0.6319 (2)0.0358 (4)
H9A0.27860.75970.68170.054*
H9B0.06230.77230.69280.054*
H9C0.19140.84250.56200.054*
C10−0.0272 (3)0.3303 (2)0.95636 (18)0.0326 (4)
H10A−0.05230.23730.97120.049*
H10B−0.14140.38850.98530.049*
H10C0.06160.33791.00770.049*
C110.2897 (2)0.04748 (16)0.75598 (17)0.0239 (3)
C120.2733 (3)−0.02336 (19)0.88349 (19)0.0318 (4)
H120.1580−0.01910.94530.038*
C130.4256 (3)−0.1004 (2)0.9203 (2)0.0391 (5)
H130.4169−0.15141.00670.047*
C140.5908 (3)−0.1011 (2)0.8280 (2)0.0380 (4)
C150.6120 (3)−0.0298 (2)0.7025 (2)0.0368 (4)
H150.7288−0.03180.64250.044*
C160.4587 (3)0.0453 (2)0.66519 (19)0.0304 (4)
H160.46860.09510.57830.037*
U11U22U33U12U13U23
I10.03090 (8)0.05323 (10)0.02085 (7)−0.00336 (6)−0.00149 (5)0.00069 (5)
S10.0273 (2)0.02141 (18)0.0241 (2)−0.00622 (16)−0.00472 (16)−0.00224 (15)
F10.0409 (8)0.0588 (9)0.0736 (11)0.0116 (7)−0.0215 (7)0.0040 (8)
O10.0276 (6)0.0228 (6)0.0215 (6)−0.0025 (5)−0.0034 (5)−0.0042 (4)
O20.0468 (8)0.0291 (7)0.0292 (7)−0.0055 (6)−0.0134 (6)−0.0071 (5)
O30.0276 (7)0.0322 (7)0.0373 (8)−0.0115 (5)−0.0017 (6)0.0002 (6)
C10.0243 (8)0.0213 (7)0.0219 (8)−0.0038 (6)−0.0043 (6)−0.0018 (6)
C20.0204 (8)0.0220 (7)0.0225 (8)−0.0020 (6)−0.0046 (6)−0.0024 (6)
C30.0237 (8)0.0260 (8)0.0221 (8)−0.0020 (6)−0.0043 (6)−0.0032 (6)
C40.0227 (8)0.0328 (9)0.0199 (8)−0.0028 (7)−0.0035 (6)−0.0002 (7)
C50.0273 (9)0.0271 (8)0.0282 (9)−0.0061 (7)−0.0073 (7)0.0043 (7)
C60.0264 (9)0.0223 (8)0.0299 (9)−0.0037 (6)−0.0080 (7)−0.0016 (7)
C70.0215 (8)0.0235 (8)0.0220 (8)−0.0017 (6)−0.0040 (6)−0.0033 (6)
C80.0238 (8)0.0247 (8)0.0239 (8)−0.0036 (6)−0.0054 (6)−0.0026 (6)
C90.0468 (12)0.0237 (8)0.0384 (11)−0.0065 (8)−0.0107 (9)−0.0050 (8)
C100.0386 (11)0.0356 (10)0.0208 (8)−0.0062 (8)−0.0015 (7)−0.0028 (7)
C110.0271 (9)0.0191 (7)0.0240 (8)−0.0036 (6)−0.0033 (6)−0.0026 (6)
C120.0320 (10)0.0310 (9)0.0272 (9)−0.0056 (7)−0.0011 (7)0.0026 (7)
C130.0424 (12)0.0353 (10)0.0342 (10)−0.0031 (9)−0.0099 (9)0.0088 (8)
C140.0342 (11)0.0324 (10)0.0470 (12)0.0029 (8)−0.0133 (9)−0.0057 (9)
C150.0282 (10)0.0413 (11)0.0382 (11)−0.0025 (8)−0.0010 (8)−0.0100 (9)
C160.0308 (10)0.0329 (9)0.0252 (8)−0.0066 (7)−0.0006 (7)−0.0037 (7)
I1—C42.1000 (17)C6—C91.501 (3)
I1—I1i3.7764 (3)C8—C101.475 (2)
S1—O21.4372 (14)C9—H9A0.9800
S1—O31.4388 (14)C9—H9B0.9800
S1—C11.7349 (17)C9—H9C0.9800
S1—C111.7633 (19)C10—H10A0.9800
F1—C141.348 (3)C10—H10B0.9800
O1—C81.368 (2)C10—H10C0.9800
O1—C71.375 (2)C11—C121.384 (3)
C1—C81.364 (2)C11—C161.393 (2)
C1—C21.447 (2)C12—C131.382 (3)
C2—C71.390 (2)C12—H120.9500
C2—C31.398 (2)C13—C141.379 (3)
C3—C41.388 (2)C13—H130.9500
C3—H30.9500C14—C151.367 (3)
C4—C51.395 (3)C15—C161.382 (3)
C5—C61.390 (3)C15—H150.9500
C5—H50.9500C16—H160.9500
C6—C71.388 (2)
C4—I1—I1i159.65 (5)O1—C8—C10115.71 (15)
O2—S1—O3119.47 (9)C6—C9—H9A109.5
O2—S1—C1106.66 (8)C6—C9—H9B109.5
O3—S1—C1108.80 (8)H9A—C9—H9B109.5
O2—S1—C11107.68 (9)C6—C9—H9C109.5
O3—S1—C11107.59 (9)H9A—C9—H9C109.5
C1—S1—C11105.89 (8)H9B—C9—H9C109.5
C8—O1—C7107.10 (13)C8—C10—H10A109.5
C8—C1—C2107.64 (15)C8—C10—H10B109.5
C8—C1—S1125.62 (13)H10A—C10—H10B109.5
C2—C1—S1126.74 (13)C8—C10—H10C109.5
C7—C2—C3119.58 (16)H10A—C10—H10C109.5
C7—C2—C1104.40 (14)H10B—C10—H10C109.5
C3—C2—C1136.01 (16)C12—C11—C16120.97 (18)
C4—C3—C2116.04 (16)C12—C11—S1119.54 (14)
C4—C3—H3122.0C16—C11—S1119.47 (14)
C2—C3—H3122.0C13—C12—C11119.60 (18)
C3—C4—C5123.23 (16)C13—C12—H12120.2
C3—C4—I1118.75 (13)C11—C12—H12120.2
C5—C4—I1118.01 (13)C14—C13—C12118.06 (19)
C6—C5—C4121.44 (16)C14—C13—H13121.0
C6—C5—H5119.3C12—C13—H13121.0
C4—C5—H5119.3F1—C14—C15118.3 (2)
C7—C6—C5114.51 (16)F1—C14—C13118.0 (2)
C7—C6—C9122.07 (17)C15—C14—C13123.6 (2)
C5—C6—C9123.40 (17)C14—C15—C16118.16 (19)
O1—C7—C6124.09 (15)C14—C15—H15120.9
O1—C7—C2110.72 (14)C16—C15—H15120.9
C6—C7—C2125.19 (16)C15—C16—C11119.55 (19)
C1—C8—O1110.13 (15)C15—C16—H16120.2
C1—C8—C10134.10 (16)C11—C16—H16120.2
O2—S1—C1—C8160.36 (16)C3—C2—C7—O1−178.98 (15)
O3—S1—C1—C830.24 (19)C1—C2—C7—O1−0.15 (19)
C11—S1—C1—C8−85.14 (18)C3—C2—C7—C60.7 (3)
O2—S1—C1—C2−19.34 (19)C1—C2—C7—C6179.55 (17)
O3—S1—C1—C2−149.46 (16)C2—C1—C8—O11.5 (2)
C11—S1—C1—C295.16 (17)S1—C1—C8—O1−178.27 (13)
C8—C1—C2—C7−0.8 (2)C2—C1—C8—C10−175.6 (2)
S1—C1—C2—C7178.95 (14)S1—C1—C8—C104.7 (3)
C8—C1—C2—C3177.7 (2)C7—O1—C8—C1−1.56 (19)
S1—C1—C2—C3−2.5 (3)C7—O1—C8—C10176.10 (16)
C7—C2—C3—C40.2 (3)O2—S1—C11—C12−140.80 (15)
C1—C2—C3—C4−178.18 (19)O3—S1—C11—C12−10.81 (17)
C2—C3—C4—C5−0.9 (3)C1—S1—C11—C12105.39 (16)
C2—C3—C4—I1177.53 (12)O2—S1—C11—C1637.34 (17)
I1i—I1—C4—C363.4 (2)O3—S1—C11—C16167.33 (14)
I1i—I1—C4—C5−118.06 (16)C1—S1—C11—C16−76.46 (16)
C3—C4—C5—C60.8 (3)C16—C11—C12—C13−1.8 (3)
I1—C4—C5—C6−177.66 (14)S1—C11—C12—C13176.32 (16)
C4—C5—C6—C70.1 (3)C11—C12—C13—C141.4 (3)
C4—C5—C6—C9178.53 (19)C12—C13—C14—F1−179.7 (2)
C8—O1—C7—C6−178.67 (17)C12—C13—C14—C150.1 (4)
C8—O1—C7—C21.04 (19)F1—C14—C15—C16178.6 (2)
C5—C6—C7—O1178.82 (16)C13—C14—C15—C16−1.2 (3)
C9—C6—C7—O10.4 (3)C14—C15—C16—C110.8 (3)
C5—C6—C7—C2−0.8 (3)C12—C11—C16—C150.7 (3)
C9—C6—C7—C2−179.31 (18)S1—C11—C16—C15−177.42 (15)
D—H···AD—HH···AD···AD—H···A
C12—H12···O3ii0.952.543.253 (2)132.
C15—H15···O2iii0.952.523.294 (3)139.
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C12—H12⋯O3i0.952.543.253 (2)132
C15—H15⋯O2ii0.952.523.294 (3)139

Symmetry codes: (i) ; (ii) .

  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.  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

5.  5-Iodo-2,7-dimethyl-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:  2008-04-30

6.  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

7.  Antibacterial and antifungal activity of cicerfuran and related 2-arylbenzofurans and stilbenes.

Authors:  Shazia N Aslam; Philip C Stevenson; Tetsuo Kokubun; David R Hall
Journal:  Microbiol Res       Date:  2007-04-05       Impact factor: 5.415

8.  3-(4-Fluoro-phenyl-sulfin-yl)-5-iodo-2,7-dimethyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13
  8 in total
  1 in total

1.  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
  1 in total

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