Literature DB >> 22220023

2-(3-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

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

Abstract

In the title compound, C(21)H(15)FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluoro-phenyl and phenyl rings are 1.76 (5) and 32.29 (5)°, respectively. In the crystal, mol-ecules are linked by a slipped π-π inter-action between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.665 (2) Å, inter-planar distance = 3.391 (2) Å and slippage = 1.390 (2) Å].

Entities:  

Year:  2011        PMID： 22220023      PMCID： PMC3247405          DOI： 10.1107/S1600536811042541

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 related structures, see: Choi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C21H15FOS M = 334.39 Triclinic, a = 4.7692 (1) Å b = 9.6442 (2) Å c = 17.4049 (3) Å α = 89.7700 (1)° β = 87.589 (1)° γ = 80.061 (1)° V = 787.82 (3) Å3 Z = 2 Mo Kα radiation μ = 0.22 mm−1 T = 296 K 0.34 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.929, T max = 0.974 13895 measured reflections 3590 independent reflections 3234 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.091 S = 1.04 3590 reflections 218 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.25 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/S1600536811042541/ff2033sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042541/ff2033Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811042541/ff2033Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H15FOSZ = 2
Mr = 334.39F(000) = 348
Triclinic, P1Dx = 1.410 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.7692 (1) ÅCell parameters from 7407 reflections
b = 9.6442 (2) Åθ = 2.3–27.5°
c = 17.4049 (3) ŵ = 0.22 mm−1
α = 89.7700 (1)°T = 296 K
β = 87.589 (1)°Block, colourless
γ = 80.061 (1)°0.34 × 0.25 × 0.12 mm
V = 787.82 (3) Å3
Bruker SMART APEXII CCD diffractometer3590 independent reflections
Radiation source: rotating anode3234 reflections with I > 2σ(I)
graphite multilayerRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.1°
φ and ω scansh = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.929, Tmax = 0.974l = −22→22
13895 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)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.091H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0451P)2 + 0.3462P] where P = (Fo2 + 2Fc2)/3
3590 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.25 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
S10.94952 (7)0.43069 (3)0.147672 (18)0.02311 (10)
F10.2102 (2)0.79398 (10)0.01953 (5)0.0391 (2)
O11.05781 (19)0.76869 (9)0.26561 (5)0.0218 (2)
C11.0423 (3)0.56199 (13)0.20611 (7)0.0196 (2)
C21.2552 (3)0.53713 (13)0.26345 (7)0.0199 (2)
C31.4383 (3)0.41893 (13)0.28916 (7)0.0198 (2)
H31.43910.33100.26740.024*
C41.6195 (3)0.43454 (13)0.34781 (7)0.0200 (2)
C51.6144 (3)0.56915 (14)0.38003 (7)0.0232 (3)
H51.73780.57870.41890.028*
C61.4325 (3)0.68749 (14)0.35590 (7)0.0238 (3)
H61.42950.77570.37770.029*
C71.2556 (3)0.66699 (13)0.29759 (7)0.0205 (2)
C80.9298 (3)0.70255 (13)0.20980 (7)0.0203 (2)
C91.8215 (3)0.31190 (13)0.37610 (7)0.0211 (3)
C101.9415 (3)0.20260 (14)0.32642 (8)0.0248 (3)
H101.89100.20550.27530.030*
C112.1353 (3)0.08960 (14)0.35218 (8)0.0308 (3)
H112.21430.01760.31840.037*
C122.2111 (4)0.08401 (15)0.42809 (9)0.0367 (4)
H122.34200.00870.44530.044*
C132.0914 (4)0.19081 (16)0.47824 (9)0.0362 (4)
H132.14060.18670.52940.043*
C141.8985 (3)0.30393 (15)0.45263 (8)0.0279 (3)
H141.81950.37530.48680.034*
C150.7126 (3)0.79758 (13)0.16924 (7)0.0212 (3)
C160.6597 (3)0.94127 (15)0.18697 (8)0.0299 (3)
H160.76100.97560.22500.036*
C170.4572 (3)1.03289 (16)0.14822 (9)0.0357 (3)
H170.42391.12810.16080.043*
C180.3041 (3)0.98512 (16)0.09120 (8)0.0315 (3)
H180.16921.04640.06480.038*
C190.3592 (3)0.84369 (15)0.07508 (8)0.0262 (3)
C200.5568 (3)0.74876 (14)0.11223 (7)0.0237 (3)
H200.58590.65360.09950.028*
C211.2261 (3)0.41386 (17)0.07312 (9)0.0352 (3)
H21A1.21590.50140.04610.053*
H21B1.20170.34100.03790.053*
H21C1.40860.39020.09560.053*
U11U22U33U12U13U23
S10.02386 (17)0.02130 (17)0.02495 (17)−0.00512 (12)−0.00487 (12)−0.00323 (12)
F10.0392 (5)0.0395 (5)0.0387 (5)−0.0029 (4)−0.0205 (4)−0.0007 (4)
O10.0230 (5)0.0190 (4)0.0229 (4)−0.0008 (3)−0.0057 (3)−0.0021 (3)
C10.0188 (6)0.0206 (6)0.0196 (6)−0.0038 (4)−0.0018 (4)−0.0009 (4)
C20.0189 (6)0.0217 (6)0.0194 (6)−0.0048 (5)−0.0001 (4)−0.0014 (5)
C30.0204 (6)0.0181 (6)0.0212 (6)−0.0042 (4)−0.0001 (4)−0.0014 (4)
C40.0204 (6)0.0192 (6)0.0204 (6)−0.0033 (5)−0.0001 (4)0.0004 (4)
C50.0248 (6)0.0236 (6)0.0214 (6)−0.0035 (5)−0.0054 (5)−0.0022 (5)
C60.0278 (7)0.0193 (6)0.0243 (6)−0.0029 (5)−0.0040 (5)−0.0048 (5)
C70.0204 (6)0.0186 (6)0.0217 (6)−0.0009 (4)−0.0021 (5)0.0003 (5)
C80.0204 (6)0.0222 (6)0.0189 (6)−0.0051 (5)−0.0018 (4)−0.0016 (5)
C90.0208 (6)0.0198 (6)0.0235 (6)−0.0053 (5)−0.0033 (5)0.0022 (5)
C100.0297 (7)0.0203 (6)0.0245 (6)−0.0038 (5)−0.0056 (5)0.0008 (5)
C110.0365 (8)0.0198 (6)0.0342 (8)0.0015 (5)−0.0069 (6)−0.0032 (5)
C120.0435 (9)0.0221 (7)0.0427 (9)0.0034 (6)−0.0199 (7)0.0010 (6)
C130.0486 (9)0.0287 (7)0.0307 (7)−0.0009 (6)−0.0183 (7)0.0010 (6)
C140.0344 (7)0.0241 (7)0.0245 (7)−0.0015 (5)−0.0061 (5)−0.0022 (5)
C150.0189 (6)0.0223 (6)0.0219 (6)−0.0024 (5)0.0002 (5)0.0012 (5)
C160.0318 (7)0.0243 (7)0.0328 (7)−0.0010 (5)−0.0093 (6)−0.0027 (5)
C170.0408 (8)0.0227 (7)0.0413 (8)0.0030 (6)−0.0113 (7)−0.0011 (6)
C180.0284 (7)0.0310 (7)0.0327 (7)0.0030 (6)−0.0067 (6)0.0060 (6)
C190.0229 (6)0.0330 (7)0.0233 (6)−0.0054 (5)−0.0049 (5)0.0007 (5)
C200.0235 (6)0.0235 (6)0.0240 (6)−0.0031 (5)−0.0023 (5)0.0000 (5)
C210.0333 (8)0.0419 (9)0.0319 (7)−0.0110 (6)0.0015 (6)−0.0137 (6)
S1—C11.7537 (13)C10—H100.9300
S1—C211.7984 (15)C11—C121.383 (2)
F1—C191.3597 (16)C11—H110.9300
O1—C71.3719 (14)C12—C131.382 (2)
O1—C81.3830 (15)C12—H120.9300
C1—C81.3698 (17)C13—C141.3854 (19)
C1—C21.4435 (17)C13—H130.9300
C2—C71.3887 (17)C14—H140.9300
C2—C31.3955 (17)C15—C201.3946 (18)
C3—C41.3897 (17)C15—C161.3984 (19)
C3—H30.9300C16—C171.387 (2)
C4—C51.4122 (18)C16—H160.9300
C4—C91.4873 (17)C17—C181.383 (2)
C5—C61.3843 (18)C17—H170.9300
C5—H50.9300C18—C191.372 (2)
C6—C71.3829 (18)C18—H180.9300
C6—H60.9300C19—C201.3758 (18)
C8—C151.4629 (17)C20—H200.9300
C9—C101.3942 (18)C21—H21A0.9600
C9—C141.3948 (18)C21—H21B0.9600
C10—C111.3879 (18)C21—H21C0.9600
C1—S1—C21101.72 (6)C10—C11—H11120.0
C7—O1—C8106.60 (9)C13—C12—C11119.73 (13)
C8—C1—C2106.46 (11)C13—C12—H12120.1
C8—C1—S1129.09 (10)C11—C12—H12120.1
C2—C1—S1124.41 (9)C12—C13—C14120.36 (13)
C7—C2—C3119.37 (11)C12—C13—H13119.8
C7—C2—C1105.75 (11)C14—C13—H13119.8
C3—C2—C1134.88 (12)C13—C14—C9120.69 (13)
C4—C3—C2119.05 (11)C13—C14—H14119.7
C4—C3—H3120.5C9—C14—H14119.7
C2—C3—H3120.5C20—C15—C16118.60 (12)
C3—C4—C5119.45 (12)C20—C15—C8121.58 (12)
C3—C4—C9120.87 (11)C16—C15—C8119.82 (12)
C5—C4—C9119.67 (11)C17—C16—C15120.44 (13)
C6—C5—C4122.43 (12)C17—C16—H16119.8
C6—C5—H5118.8C15—C16—H16119.8
C4—C5—H5118.8C18—C17—C16121.14 (14)
C7—C6—C5116.14 (12)C18—C17—H17119.4
C7—C6—H6121.9C16—C17—H17119.4
C5—C6—H6121.9C19—C18—C17117.29 (13)
O1—C7—C6125.91 (11)C19—C18—H18121.4
O1—C7—C2110.53 (11)C17—C18—H18121.4
C6—C7—C2123.56 (12)F1—C19—C18118.41 (12)
C1—C8—O1110.66 (11)F1—C19—C20117.96 (13)
C1—C8—C15135.74 (12)C18—C19—C20123.63 (13)
O1—C8—C15113.59 (11)C19—C20—C15118.90 (12)
C10—C9—C14118.30 (12)C19—C20—H20120.6
C10—C9—C4120.71 (11)C15—C20—H20120.6
C14—C9—C4120.98 (12)S1—C21—H21A109.5
C11—C10—C9120.88 (12)S1—C21—H21B109.5
C11—C10—H10119.6H21A—C21—H21B109.5
C9—C10—H10119.6S1—C21—H21C109.5
C12—C11—C10120.04 (13)H21A—C21—H21C109.5
C12—C11—H11120.0H21B—C21—H21C109.5
C21—S1—C1—C8100.68 (13)C3—C4—C9—C1032.27 (18)
C21—S1—C1—C2−81.81 (12)C5—C4—C9—C10−146.70 (13)
C8—C1—C2—C7−0.32 (13)C3—C4—C9—C14−148.48 (13)
S1—C1—C2—C7−178.30 (9)C5—C4—C9—C1432.55 (18)
C8—C1—C2—C3178.54 (13)C14—C9—C10—C11−0.8 (2)
S1—C1—C2—C30.6 (2)C4—C9—C10—C11178.47 (13)
C7—C2—C3—C4−0.78 (18)C9—C10—C11—C120.3 (2)
C1—C2—C3—C4−179.52 (13)C10—C11—C12—C130.5 (2)
C2—C3—C4—C50.00 (18)C11—C12—C13—C14−0.7 (3)
C2—C3—C4—C9−178.97 (11)C12—C13—C14—C90.1 (2)
C3—C4—C5—C60.65 (19)C10—C9—C14—C130.6 (2)
C9—C4—C5—C6179.63 (12)C4—C9—C14—C13−178.66 (14)
C4—C5—C6—C7−0.48 (19)C1—C8—C15—C202.0 (2)
C8—O1—C7—C6−179.95 (12)O1—C8—C15—C20−178.56 (11)
C8—O1—C7—C2−0.27 (13)C1—C8—C15—C16−177.34 (14)
C5—C6—C7—O1179.30 (12)O1—C8—C15—C162.05 (17)
C5—C6—C7—C2−0.4 (2)C20—C15—C16—C17−0.3 (2)
C3—C2—C7—O1−178.71 (10)C8—C15—C16—C17179.10 (13)
C1—C2—C7—O10.36 (14)C15—C16—C17—C18−0.3 (2)
C3—C2—C7—C60.99 (19)C16—C17—C18—C190.5 (2)
C1—C2—C7—C6−179.94 (12)C17—C18—C19—F1179.64 (13)
C2—C1—C8—O10.17 (14)C17—C18—C19—C20−0.1 (2)
S1—C1—C8—O1178.03 (9)F1—C19—C20—C15179.80 (11)
C2—C1—C8—C15179.58 (14)C18—C19—C20—C15−0.4 (2)
S1—C1—C8—C15−2.6 (2)C16—C15—C20—C190.63 (19)
C7—O1—C8—C10.05 (13)C8—C15—C20—C19−178.76 (12)
C7—O1—C8—C15−179.50 (10)
  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.  2-(4-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17

6.  2-(4-Chloro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-13

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.  2-(2-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-13
  1 in total

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