Literature DB >> 22199974

2-(4-Fluoro-phen-yl)-3-isopropyl-sulfinyl-5,6-methyl-enedi-oxy-1-benzofuran.

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

Abstract

In the title compound, C(18)H(15)FO(4)S, the fluoro-benzene ring makes a dihedral angle of 4.3 (1)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations, with site-occupancy factors of 0.940 (3) and 0.060 (3).

Entities:  

Year:  2011        PMID： 22199974      PMCID： PMC3239126          DOI： 10.1107/S1600536811051178

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. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C18H15FO4S M = 346.36 Triclinic, a = 6.2519 (1) Å b = 9.6773 (2) Å c = 12.9267 (2) Å α = 90.122 (1)° β = 94.726 (1)° γ = 101.920 (1)° V = 762.47 (2) Å3 Z = 2 Mo Kα radiation μ = 0.24 mm−1 T = 173 K 0.45 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.898, T max = 0.967 13552 measured reflections 3488 independent reflections 3171 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.101 S = 1.06 3488 reflections 229 parameters 4 restraints H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.40 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/S1600536811051178/fj2487sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051178/fj2487Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811051178/fj2487Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H15FO4SZ = 2
Mr = 346.36F(000) = 360
Triclinic, P1Dx = 1.509 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2519 (1) ÅCell parameters from 7633 reflections
b = 9.6773 (2) Åθ = 2.6–27.5°
c = 12.9267 (2) ŵ = 0.24 mm−1
α = 90.122 (1)°T = 173 K
β = 94.726 (1)°Block, colourless
γ = 101.920 (1)°0.45 × 0.21 × 0.14 mm
V = 762.47 (2) Å3
Bruker SMART APEXII CCD diffractometer3488 independent reflections
Radiation source: rotating anode3171 reflections with I > 2σ(I)
graphite multilayerRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.6°
φ and ω scansh = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.898, Tmax = 0.967l = −15→16
13552 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.101H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0457P)2 + 0.4198P] where P = (Fo2 + 2Fc2)/3
3488 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.56 e Å−3
4 restraintsΔρmin = −0.40 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*/UeqOcc. (<1)
S10.15386 (6)0.36031 (4)0.14314 (3)0.02733 (12)
F1−0.43070 (18)0.35212 (13)0.57633 (8)0.0438 (3)
O10.31016 (17)0.12210 (11)0.37742 (8)0.0264 (2)
O20.8622 (2)−0.09128 (13)0.23234 (10)0.0377 (3)
O30.8308 (2)0.03336 (14)0.08091 (10)0.0415 (3)
O4A0.2282 (2)0.32964 (14)0.04204 (9)0.0358 (4)0.940 (3)
O4B−0.0806 (7)0.3600 (18)0.1198 (15)0.030 (4)0.060 (3)
C10.2601 (2)0.25039 (15)0.23544 (11)0.0241 (3)
C20.4209 (2)0.16817 (15)0.21565 (12)0.0245 (3)
C30.5457 (3)0.15352 (16)0.13162 (12)0.0282 (3)
H30.53350.20300.06870.034*
C40.6853 (3)0.06270 (17)0.14767 (13)0.0289 (3)
C50.9256 (3)−0.07578 (18)0.12790 (14)0.0343 (4)
H5A1.0874−0.05060.12850.041*
H5B0.8725−0.16560.08820.041*
C60.7051 (3)−0.01235 (16)0.23908 (13)0.0279 (3)
C70.5854 (3)−0.00188 (16)0.32195 (12)0.0278 (3)
H70.5975−0.05300.38410.033*
C80.4441 (2)0.09170 (15)0.30558 (12)0.0248 (3)
C90.1973 (2)0.21924 (15)0.33327 (12)0.0247 (3)
C100.0418 (2)0.26129 (16)0.39856 (12)0.0249 (3)
C110.0148 (3)0.20327 (18)0.49683 (13)0.0308 (3)
H110.10530.14090.52220.037*
C12−0.1410 (3)0.23498 (19)0.55767 (13)0.0343 (4)
H12−0.15840.19540.62440.041*
C13−0.2699 (3)0.32515 (18)0.51912 (13)0.0309 (3)
C14−0.2463 (3)0.38780 (18)0.42458 (13)0.0311 (3)
H14−0.33540.45180.40100.037*
C15−0.0895 (3)0.35560 (17)0.36425 (12)0.0294 (3)
H15−0.07090.39820.29860.035*
C160.3187 (3)0.53086 (16)0.19013 (13)0.0289 (3)
H160.30110.54100.26580.035*
C170.2245 (4)0.6446 (2)0.1325 (2)0.0562 (6)
H17A0.30620.73800.15720.084*
H17B0.06970.63460.14520.084*
H17C0.23690.63460.05790.084*
C180.5593 (3)0.54184 (19)0.17658 (15)0.0365 (4)
H18A0.58140.54240.10240.055*
H18B0.60820.46080.20870.055*
H18C0.64430.62940.20990.055*
U11U22U33U12U13U23
S10.0300 (2)0.0256 (2)0.0255 (2)0.00633 (14)−0.00408 (14)0.00327 (14)
F10.0410 (6)0.0612 (7)0.0347 (6)0.0199 (5)0.0117 (4)−0.0051 (5)
O10.0268 (5)0.0275 (5)0.0268 (5)0.0092 (4)0.0047 (4)0.0070 (4)
O20.0415 (7)0.0373 (7)0.0412 (7)0.0215 (5)0.0103 (5)0.0049 (5)
O30.0502 (8)0.0434 (7)0.0398 (7)0.0246 (6)0.0185 (6)0.0069 (5)
O4A0.0480 (8)0.0365 (7)0.0234 (6)0.0108 (6)0.0003 (5)0.0014 (5)
O4B0.031 (3)0.022 (9)0.037 (10)0.006 (7)−0.004 (4)0.018 (7)
C10.0246 (7)0.0230 (7)0.0245 (7)0.0049 (5)0.0009 (5)0.0031 (5)
C20.0245 (7)0.0216 (7)0.0266 (7)0.0035 (5)0.0011 (6)0.0024 (5)
C30.0311 (8)0.0276 (7)0.0270 (8)0.0072 (6)0.0051 (6)0.0033 (6)
C40.0299 (8)0.0261 (7)0.0308 (8)0.0049 (6)0.0063 (6)−0.0013 (6)
C50.0355 (9)0.0305 (8)0.0390 (9)0.0108 (7)0.0053 (7)−0.0041 (7)
C60.0271 (7)0.0216 (7)0.0354 (8)0.0064 (6)0.0013 (6)−0.0002 (6)
C70.0281 (8)0.0250 (7)0.0309 (8)0.0073 (6)0.0022 (6)0.0053 (6)
C80.0234 (7)0.0234 (7)0.0272 (7)0.0038 (5)0.0033 (6)0.0020 (6)
C90.0233 (7)0.0227 (7)0.0277 (7)0.0050 (5)−0.0003 (6)0.0045 (6)
C100.0224 (7)0.0245 (7)0.0268 (7)0.0028 (5)0.0018 (5)0.0016 (6)
C110.0322 (8)0.0335 (8)0.0285 (8)0.0106 (6)0.0027 (6)0.0053 (6)
C120.0388 (9)0.0406 (9)0.0247 (8)0.0093 (7)0.0060 (7)0.0051 (7)
C130.0273 (8)0.0370 (8)0.0285 (8)0.0063 (6)0.0045 (6)−0.0073 (6)
C140.0284 (8)0.0341 (8)0.0325 (8)0.0110 (6)0.0005 (6)−0.0001 (6)
C150.0284 (8)0.0329 (8)0.0284 (8)0.0091 (6)0.0037 (6)0.0057 (6)
C160.0341 (8)0.0233 (7)0.0292 (8)0.0061 (6)0.0008 (6)0.0002 (6)
C170.0508 (12)0.0306 (9)0.0863 (17)0.0127 (8)−0.0105 (11)0.0137 (10)
C180.0325 (9)0.0340 (9)0.0409 (9)0.0021 (7)0.0025 (7)0.0068 (7)
S1—O4B1.4716 (17)C7—H70.9500
S1—O4A1.4724 (13)C9—C101.456 (2)
S1—C11.7783 (15)C10—C151.398 (2)
S1—C161.8290 (16)C10—C111.399 (2)
F1—C131.3623 (18)C11—C121.382 (2)
O1—C81.3707 (18)C11—H110.9500
O1—C91.3847 (17)C12—C131.373 (2)
O2—C61.3712 (19)C12—H120.9500
O2—C51.437 (2)C13—C141.371 (2)
O3—C41.3740 (19)C14—C151.384 (2)
O3—C51.428 (2)C14—H140.9500
C1—C91.371 (2)C15—H150.9500
C1—C21.443 (2)C16—C181.510 (2)
C2—C81.393 (2)C16—C171.521 (2)
C2—C31.412 (2)C16—H161.0000
C3—C41.366 (2)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C61.398 (2)C17—H17C0.9800
C5—H5A0.9900C18—H18A0.9800
C5—H5B0.9900C18—H18B0.9800
C6—C71.371 (2)C18—H18C0.9800
C7—C81.395 (2)
O4B—S1—O4A104.0 (8)O1—C9—C10114.53 (13)
O4B—S1—C1124.7 (6)C15—C10—C11118.20 (15)
O4A—S1—C1107.07 (7)C15—C10—C9121.63 (14)
O4B—S1—C16114.1 (7)C11—C10—C9120.13 (14)
O4A—S1—C16107.44 (8)C12—C11—C10121.20 (15)
C1—S1—C1698.56 (7)C12—C11—H11119.4
C8—O1—C9107.04 (11)C10—C11—H11119.4
C6—O2—C5105.72 (13)C13—C12—C11118.27 (15)
C4—O3—C5106.07 (13)C13—C12—H12120.9
C9—C1—C2107.40 (13)C11—C12—H12120.9
C9—C1—S1127.89 (12)F1—C13—C14118.35 (15)
C2—C1—S1124.56 (11)F1—C13—C12118.79 (15)
C8—C2—C3120.03 (14)C14—C13—C12122.85 (15)
C8—C2—C1105.09 (13)C13—C14—C15118.45 (15)
C3—C2—C1134.88 (14)C13—C14—H14120.8
C4—C3—C2114.84 (14)C15—C14—H14120.8
C4—C3—H3122.6C14—C15—C10120.98 (15)
C2—C3—H3122.6C14—C15—H15119.5
C3—C4—O3126.86 (15)C10—C15—H15119.5
C3—C4—C6123.73 (15)C18—C16—C17112.60 (15)
O3—C4—C6109.37 (14)C18—C16—S1111.75 (12)
O3—C5—O2107.97 (13)C17—C16—S1107.09 (12)
O3—C5—H5A110.1C18—C16—H16108.4
O2—C5—H5A110.1C17—C16—H16108.4
O3—C5—H5B110.1S1—C16—H16108.4
O2—C5—H5B110.1C16—C17—H17A109.5
H5A—C5—H5B108.4C16—C17—H17B109.5
O2—C6—C7127.12 (15)H17A—C17—H17B109.5
O2—C6—C4109.74 (14)C16—C17—H17C109.5
C7—C6—C4123.13 (14)H17A—C17—H17C109.5
C6—C7—C8113.00 (14)H17B—C17—H17C109.5
C6—C7—H7123.5C16—C18—H18A109.5
C8—C7—H7123.5C16—C18—H18B109.5
O1—C8—C2110.64 (13)H18A—C18—H18B109.5
O1—C8—C7124.08 (13)C16—C18—H18C109.5
C2—C8—C7125.27 (14)H18A—C18—H18C109.5
C1—C9—O1109.82 (13)H18B—C18—H18C109.5
C1—C9—C10135.63 (14)
O4B—S1—C1—C9−43.3 (10)C3—C2—C8—C70.3 (2)
O4A—S1—C1—C9−164.61 (14)C1—C2—C8—C7−179.36 (14)
C16—S1—C1—C984.09 (15)C6—C7—C8—O1−178.87 (13)
O4B—S1—C1—C2131.6 (10)C6—C7—C8—C20.3 (2)
O4A—S1—C1—C210.31 (15)C2—C1—C9—O10.33 (16)
C16—S1—C1—C2−100.99 (13)S1—C1—C9—O1175.95 (10)
C9—C1—C2—C8−0.13 (16)C2—C1—C9—C10−178.34 (16)
S1—C1—C2—C8−175.93 (11)S1—C1—C9—C10−2.7 (3)
C9—C1—C2—C3−179.69 (16)C8—O1—C9—C1−0.41 (16)
S1—C1—C2—C34.5 (3)C8—O1—C9—C10178.57 (12)
C8—C2—C3—C4−0.7 (2)C1—C9—C10—C150.4 (3)
C1—C2—C3—C4178.84 (16)O1—C9—C10—C15−178.21 (13)
C2—C3—C4—O3−177.24 (15)C1—C9—C10—C11178.06 (17)
C2—C3—C4—C60.6 (2)O1—C9—C10—C11−0.6 (2)
C5—O3—C4—C3−175.24 (16)C15—C10—C11—C121.7 (2)
C5—O3—C4—C66.70 (18)C9—C10—C11—C12−176.06 (15)
C4—O3—C5—O2−10.48 (18)C10—C11—C12—C130.1 (3)
C6—O2—C5—O310.29 (17)C11—C12—C13—F1177.04 (15)
C5—O2—C6—C7175.46 (16)C11—C12—C13—C14−1.9 (3)
C5—O2—C6—C4−6.21 (17)F1—C13—C14—C15−177.15 (14)
C3—C4—C6—O2−178.41 (15)C12—C13—C14—C151.8 (3)
O3—C4—C6—O2−0.28 (18)C13—C14—C15—C100.1 (2)
C3—C4—C6—C70.0 (3)C11—C10—C15—C14−1.8 (2)
O3—C4—C6—C7178.12 (14)C9—C10—C15—C14175.91 (14)
O2—C6—C7—C8177.70 (14)O4B—S1—C16—C18−159.6 (8)
C4—C6—C7—C8−0.4 (2)O4A—S1—C16—C18−44.95 (14)
C9—O1—C8—C20.32 (16)C1—S1—C16—C1866.05 (13)
C9—O1—C8—C7179.57 (14)O4B—S1—C16—C17−35.9 (8)
C3—C2—C8—O1179.52 (13)O4A—S1—C16—C1778.81 (15)
C1—C2—C8—O1−0.12 (16)C1—S1—C16—C17−170.20 (14)
D—H···AD—HH···AD···AD—H···A
C5—H5B···O4Ai0.992.273.231 (2)163
C18—H18A···O4Aii0.982.493.354 (2)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5—H5B⋯O4Ai0.992.273.231 (2)163
C18—H18A⋯O4Aii0.982.493.354 (2)147

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.  3-Ethyl-sulfinyl-2-(4-fluoro-phen-yl)-5,6-methyl-enedi-oxy-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

6.  2-(4-Fluoro-phen-yl)-5,6-methyl-enedi-oxy-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:  2010-02-13

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.  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 in total
  1 in total

1.  3-Ethyl-sulfinyl-2-(3-fluoro-phen-yl)-5,6-methyl-enedi-oxy-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-14
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.