Literature DB >> 21754073

2,5-Bis(4-fluoro-phen-yl)-2-methyl-sulfanyl-1-benzofuran.

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

Abstract

The crystal studied of the title compound, C(21)H(14)F(2)OS, was an inversion twin with a 0.67 (8):0.33 (8) domain ratio. The 4-fluoro-phenyl ring in the 2-position makes a dihedral angle of 25.14 (6)° with the mean plane of the benzofuran fragment, and the dihedral angle between 4-fluoro-phenyl ring in the 5-position and the mean plane of the benzofuran fragment is 28.50 (7)°. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯F and C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID： 21754073      PMCID： PMC3099888          DOI： 10.1107/S1600536811007458

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 structural studies of related 3-alkyl­sulfanyl-2-(4-fluoro­phen­yl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C21H14F2OS M = 352.38 Monoclinic, a = 10.7673 (7) Å b = 7.2986 (5) Å c = 11.5145 (8) Å β = 116.124 (1)° V = 812.44 (10) Å3 Z = 2 Mo Kα radiation μ = 0.23 mm−1 T = 173 K 0.32 × 0.29 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.972 7891 measured reflections 3710 independent reflections 3501 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.101 S = 1.06 3710 reflections 228 parameters 1 restraint H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.21 e Å−3 Absolute structure: Flack (1983 ▶), 1700 Friedel pairs Flack parameter: 0.33 (8) 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/S1600536811007458/sj5110sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007458/sj5110Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H14F2OSF(000) = 364
Mr = 352.38Dx = 1.440 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3532 reflections
a = 10.7673 (7) Åθ = 2.2–27.1°
b = 7.2986 (5) ŵ = 0.23 mm−1
c = 11.5145 (8) ÅT = 173 K
β = 116.124 (1)°Block, colourless
V = 812.44 (10) Å30.32 × 0.29 × 0.13 mm
Z = 2
Bruker SMART APEXII CCD diffractometer3710 independent reflections
Radiation source: rotating anode3501 reflections with I > 2σ(I)
graphite multilayerRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.0°
φ and ω scansh = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −9→9
Tmin = 0.930, Tmax = 0.972l = −14→14
7891 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.101w = 1/[σ2(Fo2) + (0.056P)2 + 0.1486P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3710 reflectionsΔρmax = 0.33 e Å−3
228 parametersΔρmin = −0.21 e Å−3
1 restraintAbsolute structure: Flack (1983), 1700 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.33 (8)
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
S10.43705 (5)0.35582 (9)0.12177 (4)0.03705 (15)
F11.36155 (13)0.4416 (2)0.73988 (15)0.0491 (4)
F2−0.24680 (12)0.4131 (2)−0.00514 (13)0.0463 (3)
O10.36309 (13)0.4157 (2)0.42787 (12)0.0294 (3)
C10.43510 (19)0.3862 (3)0.27194 (17)0.0269 (4)
C20.55585 (18)0.3959 (3)0.39519 (16)0.0253 (4)
C30.69845 (18)0.3930 (3)0.43512 (17)0.0260 (4)
H30.73460.37900.37380.031*
C40.78673 (18)0.4111 (3)0.56623 (17)0.0243 (4)
C50.7295 (2)0.4268 (3)0.65587 (18)0.0280 (4)
H50.79050.43630.74540.034*
C60.5895 (2)0.4287 (3)0.61797 (18)0.0303 (4)
H60.55230.43950.67880.036*
C70.5052 (2)0.4142 (3)0.48647 (18)0.0277 (4)
C80.32360 (19)0.3989 (3)0.29668 (17)0.0273 (4)
C90.93978 (18)0.4152 (3)0.61213 (16)0.0243 (4)
C101.0238 (2)0.5099 (3)0.72483 (19)0.0290 (4)
H100.98260.56930.77260.035*
C111.1652 (2)0.5193 (3)0.7686 (2)0.0344 (5)
H111.22140.58460.84530.041*
C121.2229 (2)0.4318 (3)0.6983 (2)0.0320 (4)
C131.1449 (2)0.3356 (3)0.58707 (19)0.0334 (4)
H131.18730.27640.54020.040*
C141.0033 (2)0.3270 (3)0.54499 (19)0.0297 (4)
H140.94820.25980.46890.036*
C150.17419 (19)0.4016 (3)0.21639 (17)0.0261 (4)
C160.1142 (2)0.3192 (3)0.09396 (18)0.0298 (4)
H160.17140.26100.06150.036*
C17−0.0278 (2)0.3218 (3)0.01996 (18)0.0315 (4)
H17−0.06880.2643−0.06240.038*
C18−0.1079 (2)0.4093 (3)0.06815 (19)0.0313 (4)
C19−0.0530 (2)0.4919 (3)0.1888 (2)0.0328 (4)
H19−0.11120.55060.22000.039*
C200.0880 (2)0.4865 (3)0.26212 (19)0.0293 (4)
H200.12750.54150.34540.035*
C210.5127 (3)0.5682 (4)0.1057 (3)0.0520 (7)
H21A0.45390.67050.10610.078*
H21B0.52060.56830.02410.078*
H21C0.60480.58170.17810.078*
U11U22U33U12U13U23
S10.0418 (3)0.0475 (3)0.0259 (2)−0.0051 (2)0.0186 (2)−0.0059 (2)
F10.0243 (6)0.0571 (9)0.0646 (9)0.0009 (6)0.0185 (6)−0.0050 (7)
F20.0245 (6)0.0532 (9)0.0509 (7)0.0006 (6)0.0073 (5)0.0010 (6)
O10.0258 (6)0.0405 (8)0.0231 (6)−0.0011 (6)0.0119 (5)−0.0019 (6)
C10.0279 (9)0.0307 (10)0.0228 (8)−0.0028 (8)0.0118 (7)−0.0028 (7)
C20.0295 (9)0.0258 (10)0.0219 (8)−0.0014 (7)0.0125 (7)−0.0011 (7)
C30.0281 (9)0.0286 (10)0.0256 (8)−0.0024 (8)0.0157 (7)−0.0011 (8)
C40.0269 (9)0.0207 (8)0.0265 (8)0.0014 (7)0.0128 (7)0.0010 (7)
C50.0266 (9)0.0317 (10)0.0228 (8)0.0013 (8)0.0083 (7)0.0001 (8)
C60.0327 (10)0.0372 (11)0.0253 (9)0.0010 (8)0.0165 (8)−0.0004 (8)
C70.0249 (8)0.0317 (10)0.0275 (9)−0.0012 (8)0.0124 (7)−0.0004 (8)
C80.0303 (9)0.0282 (10)0.0233 (8)−0.0024 (8)0.0116 (7)−0.0004 (7)
C90.0250 (9)0.0217 (8)0.0259 (8)0.0020 (7)0.0109 (7)0.0054 (7)
C100.0286 (10)0.0316 (10)0.0290 (9)0.0029 (8)0.0146 (8)−0.0024 (8)
C110.0298 (10)0.0362 (11)0.0321 (10)0.0004 (9)0.0091 (8)−0.0049 (9)
C120.0240 (9)0.0319 (10)0.0417 (11)0.0032 (8)0.0159 (8)0.0035 (9)
C130.0366 (10)0.0317 (10)0.0397 (10)0.0057 (9)0.0240 (9)−0.0010 (9)
C140.0326 (10)0.0265 (10)0.0309 (9)0.0016 (8)0.0147 (8)−0.0019 (8)
C150.0268 (9)0.0246 (9)0.0263 (8)−0.0022 (8)0.0112 (7)0.0016 (7)
C160.0318 (10)0.0287 (10)0.0285 (9)−0.0017 (8)0.0128 (8)−0.0009 (8)
C170.0346 (11)0.0302 (11)0.0238 (9)−0.0029 (8)0.0075 (8)−0.0007 (8)
C180.0249 (9)0.0289 (10)0.0337 (9)−0.0012 (8)0.0071 (8)0.0059 (8)
C190.0316 (11)0.0305 (10)0.0397 (11)0.0022 (8)0.0188 (9)0.0003 (9)
C200.0341 (11)0.0259 (9)0.0262 (9)−0.0020 (8)0.0117 (8)−0.0017 (7)
C210.0554 (16)0.0591 (17)0.0478 (14)−0.0053 (12)0.0286 (13)0.0144 (12)
S1—C11.7527 (18)C10—C111.379 (3)
S1—C211.798 (3)C10—H100.9500
F1—C121.354 (2)C11—C121.375 (3)
F2—C181.355 (2)C11—H110.9500
O1—C71.374 (2)C12—C131.375 (3)
O1—C81.383 (2)C13—C141.384 (3)
C1—C81.354 (3)C13—H130.9500
C1—C21.444 (2)C14—H140.9500
C2—C71.387 (2)C15—C201.398 (3)
C2—C31.396 (2)C15—C161.402 (3)
C3—C41.392 (2)C16—C171.384 (3)
C3—H30.9500C16—H160.9500
C4—C51.420 (3)C17—C181.372 (3)
C4—C91.493 (2)C17—H170.9500
C5—C61.373 (3)C18—C191.385 (3)
C5—H50.9500C19—C201.375 (3)
C6—C71.385 (3)C19—H190.9500
C6—H60.9500C20—H200.9500
C8—C151.461 (3)C21—H21A0.9800
C9—C141.395 (3)C21—H21B0.9800
C9—C101.395 (3)C21—H21C0.9800
C1—S1—C21101.24 (12)C10—C11—H11120.9
C7—O1—C8106.02 (14)F1—C12—C13118.83 (18)
C8—C1—C2106.74 (15)F1—C12—C11118.70 (19)
C8—C1—S1127.83 (14)C13—C12—C11122.47 (18)
C2—C1—S1125.39 (14)C12—C13—C14118.42 (18)
C7—C2—C3119.62 (16)C12—C13—H13120.8
C7—C2—C1105.38 (15)C14—C13—H13120.8
C3—C2—C1134.99 (16)C13—C14—C9121.27 (18)
C4—C3—C2118.87 (16)C13—C14—H14119.4
C4—C3—H3120.6C9—C14—H14119.4
C2—C3—H3120.6C20—C15—C16118.72 (17)
C3—C4—C5119.24 (17)C20—C15—C8119.79 (17)
C3—C4—C9120.40 (16)C16—C15—C8121.49 (17)
C5—C4—C9120.36 (16)C17—C16—C15120.55 (18)
C6—C5—C4122.47 (17)C17—C16—H16119.7
C6—C5—H5118.8C15—C16—H16119.7
C4—C5—H5118.8C18—C17—C16118.58 (18)
C5—C6—C7116.47 (17)C18—C17—H17120.7
C5—C6—H6121.8C16—C17—H17120.7
C7—C6—H6121.8F2—C18—C17118.40 (18)
O1—C7—C6126.02 (17)F2—C18—C19118.85 (19)
O1—C7—C2110.67 (15)C17—C18—C19122.75 (18)
C6—C7—C2123.31 (17)C20—C19—C18118.17 (19)
C1—C8—O1111.18 (15)C20—C19—H19120.9
C1—C8—C15134.39 (17)C18—C19—H19120.9
O1—C8—C15114.42 (15)C19—C20—C15121.21 (18)
C14—C9—C10117.96 (17)C19—C20—H20119.4
C14—C9—C4121.93 (16)C15—C20—H20119.4
C10—C9—C4120.11 (16)S1—C21—H21A109.5
C11—C10—C9121.60 (18)S1—C21—H21B109.5
C11—C10—H10119.2H21A—C21—H21B109.5
C9—C10—H10119.2S1—C21—H21C109.5
C12—C11—C10118.28 (19)H21A—C21—H21C109.5
C12—C11—H11120.9H21B—C21—H21C109.5
C21—S1—C1—C8115.0 (2)C5—C4—C9—C14152.2 (2)
C21—S1—C1—C2−67.4 (2)C3—C4—C9—C10151.49 (19)
C8—C1—C2—C70.0 (2)C5—C4—C9—C10−28.1 (3)
S1—C1—C2—C7−178.03 (16)C14—C9—C10—C110.9 (3)
C8—C1—C2—C3−179.1 (2)C4—C9—C10—C11−178.74 (19)
S1—C1—C2—C32.9 (3)C9—C10—C11—C12−0.2 (3)
C7—C2—C3—C4−0.8 (3)C10—C11—C12—F1179.42 (19)
C1—C2—C3—C4178.1 (2)C10—C11—C12—C13−0.2 (3)
C2—C3—C4—C51.7 (3)F1—C12—C13—C14−179.68 (18)
C2—C3—C4—C9−177.88 (18)C11—C12—C13—C14−0.1 (3)
C3—C4—C5—C6−1.4 (3)C12—C13—C14—C90.8 (3)
C9—C4—C5—C6178.20 (19)C10—C9—C14—C13−1.2 (3)
C4—C5—C6—C70.1 (3)C4—C9—C14—C13178.46 (18)
C8—O1—C7—C6179.7 (2)C1—C8—C15—C20−154.5 (2)
C8—O1—C7—C2−0.3 (2)O1—C8—C15—C2024.2 (3)
C5—C6—C7—O1−179.09 (19)C1—C8—C15—C1626.1 (3)
C5—C6—C7—C20.9 (3)O1—C8—C15—C16−155.20 (18)
C3—C2—C7—O1179.44 (16)C20—C15—C16—C17−0.1 (3)
C1—C2—C7—O10.2 (2)C8—C15—C16—C17179.37 (17)
C3—C2—C7—C6−0.5 (3)C15—C16—C17—C181.1 (3)
C1—C2—C7—C6−179.78 (19)C16—C17—C18—F2179.39 (17)
C2—C1—C8—O1−0.1 (2)C16—C17—C18—C19−1.3 (3)
S1—C1—C8—O1177.79 (15)F2—C18—C19—C20179.82 (18)
C2—C1—C8—C15178.6 (2)C17—C18—C19—C200.6 (3)
S1—C1—C8—C15−3.5 (4)C18—C19—C20—C150.5 (3)
C7—O1—C8—C10.3 (2)C16—C15—C20—C19−0.8 (3)
C7—O1—C8—C15−178.75 (16)C8—C15—C20—C19179.82 (18)
C3—C4—C9—C14−28.1 (3)
Cg is the centroid of the C15–C20 4-fluorophenyl ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···F1i0.952.453.322 (2)153
C10—H10···Cgii0.952.673.441 (2)139
C17—H17···Cgiii0.952.863.557 (2)131
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15–C20 4-fluoro­phenyl ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C6—H6⋯F1i0.952.453.322 (2)153
C10—H10⋯Cgii0.952.673.441 (2)139
C17—H17⋯Cgiii0.952.863.557 (2)131

Symmetry codes: (i) ; (ii) ; (iii) .

  7 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.  3-Ethyl-sulfanyl-2-(4-fluoro-phen-yl)-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:  2010-01-13

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
  7 in total
  1 in total

1.  5-(4-Fluoro-phen-yl)-2-(4-methyl-phen-yl)-3-methyl-sulfanyl-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-08
  1 in total

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