Literature DB >> 23476295

3-(4-Bromo-phenyl-sulfon-yl)-5-ethyl-2-methyl-1-benzofuran.

Hong Dae Choi1, Pil Ja Seo, Uk Lee.   

Abstract

In the title compound, C17H15BrO3S, the 4-bromo-phenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 23476295      PMCID： PMC3589059          DOI： 10.1107/S1600536812048313

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 the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C17H15BrO3S M = 379.26 Tetragonal, a = 10.2785 (3) Å c = 15.2899 (6) Å V = 1615.34 (9) Å3 Z = 4 Mo Kα radiation μ = 2.68 mm−1 T = 173 K 0.31 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.450, T max = 0.746 8518 measured reflections 3085 independent reflections 2558 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.067 S = 1.03 3085 reflections 201 parameters 1 restraint H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.29 e Å−3 Absolute structure: Flack (1983 ▶), 1000 Friedel pairs Flack parameter: 0.001 (7) 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048313/rn2111sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048313/rn2111Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812048313/rn2111Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H15BrO3SDx = 1.559 Mg m−3
Mr = 379.26Melting point = 404–405 K
Tetragonal, P43Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4cwCell parameters from 2851 reflections
a = 10.2785 (3) Åθ = 2.4–23.1°
c = 15.2899 (6) ŵ = 2.68 mm−1
V = 1615.34 (9) Å3T = 173 K
Z = 4Block, colourless
F(000) = 7680.31 × 0.17 × 0.15 mm
Bruker SMART APEXII CCD diffractometer3085 independent reflections
Radiation source: rotating anode2558 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.035
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
φ and ω scansh = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −13→12
Tmin = 0.450, Tmax = 0.746l = −20→13
8518 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.067w = 1/[σ2(Fo2) + (0.0094P)2 + 0.1451P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3085 reflectionsΔρmax = 0.35 e Å−3
201 parametersΔρmin = −0.29 e Å−3
1 restraintAbsolute structure: Flack (1983), 1000 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.001 (7)
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
Br10.83341 (3)0.52123 (5)0.64403 (3)0.06379 (15)
S10.22891 (7)0.40370 (7)0.69506 (5)0.02917 (17)
O10.1117 (2)0.2989 (2)0.46167 (13)0.0331 (5)
O20.2142 (2)0.2825 (2)0.73957 (15)0.0401 (6)
O30.1697 (2)0.5188 (2)0.73023 (15)0.0372 (5)
C120.3955 (3)0.4357 (3)0.68213 (18)0.0248 (6)
C20.1292 (3)0.4919 (3)0.5329 (2)0.0250 (6)
C170.4835 (3)0.3333 (3)0.6829 (2)0.0357 (7)
H170.45460.24640.69120.043*
C130.4374 (3)0.5626 (3)0.6707 (2)0.0346 (8)
H130.37630.63190.67050.042*
C160.6140 (3)0.3604 (3)0.6713 (2)0.0394 (8)
H160.67570.29160.67120.047*
C150.6542 (3)0.4857 (4)0.66010 (19)0.0390 (8)
C60.0458 (3)0.4963 (3)0.3844 (2)0.0370 (7)
H60.02230.45250.33200.044*
C70.0933 (3)0.4311 (3)0.4558 (2)0.0287 (7)
C50.0339 (3)0.6299 (3)0.3931 (3)0.0382 (7)
H50.00080.67870.34520.046*
C30.1165 (3)0.6262 (3)0.5399 (2)0.0299 (7)
H30.14030.66960.59230.036*
C80.1590 (3)0.2747 (3)0.5441 (2)0.0295 (7)
C90.0514 (4)0.8410 (3)0.4760 (3)0.0454 (9)
H9A0.08460.87050.53350.054*
H9B0.10460.88320.43010.054*
C140.5674 (3)0.5881 (3)0.6595 (2)0.0392 (8)
H140.59710.67480.65150.047*
C40.0687 (3)0.6956 (3)0.4694 (2)0.0359 (8)
C10.1709 (3)0.3870 (3)0.58850 (19)0.0275 (7)
C110.1847 (3)0.1373 (3)0.5637 (2)0.0399 (8)
H11A0.24690.10250.52120.060*
H11B0.10330.08800.56030.060*
H11C0.22100.12970.62280.060*
C10−0.0874 (4)0.8851 (4)0.4663 (3)0.0598 (11)
H10A−0.12020.85950.40860.090*
H10B−0.09170.97990.47210.090*
H10C−0.14090.84460.51190.090*
U11U22U33U12U13U23
Br10.02640 (18)0.1092 (4)0.0558 (2)−0.00760 (19)0.00298 (19)−0.0095 (3)
S10.0271 (4)0.0358 (4)0.0246 (3)−0.0022 (3)0.0028 (3)−0.0006 (4)
O10.0342 (12)0.0308 (12)0.0344 (12)−0.0039 (9)−0.0097 (10)−0.0053 (10)
O20.0447 (14)0.0415 (14)0.0340 (12)−0.0079 (10)0.0037 (11)0.0077 (11)
O30.0330 (13)0.0478 (14)0.0308 (12)0.0037 (10)0.0048 (10)−0.0083 (11)
C120.0189 (14)0.0371 (17)0.0183 (13)−0.0009 (12)0.0012 (12)−0.0052 (13)
C20.0176 (14)0.0285 (16)0.0288 (16)−0.0047 (12)0.0025 (13)−0.0043 (13)
C170.0399 (19)0.0355 (18)0.0316 (16)0.0026 (13)0.0022 (15)0.0029 (15)
C130.0315 (17)0.0337 (18)0.0387 (19)0.0036 (13)0.0008 (14)−0.0074 (14)
C160.0329 (18)0.052 (2)0.0330 (18)0.0134 (15)−0.0038 (14)−0.0043 (16)
C150.0219 (15)0.071 (3)0.0243 (17)−0.0017 (15)0.0011 (14)−0.0056 (17)
C60.0384 (18)0.0387 (17)0.0338 (17)−0.0044 (14)−0.0098 (16)−0.0033 (16)
C70.0233 (15)0.0279 (16)0.0348 (17)−0.0020 (12)−0.0040 (13)−0.0018 (14)
C50.0345 (18)0.0388 (18)0.0414 (17)−0.0023 (14)−0.0121 (17)0.006 (2)
C30.0296 (17)0.0273 (17)0.0329 (17)−0.0052 (13)−0.0018 (14)−0.0028 (14)
C80.0272 (17)0.0302 (17)0.0312 (17)−0.0024 (13)−0.0016 (14)0.0012 (14)
C90.058 (2)0.0264 (18)0.052 (2)−0.0003 (16)−0.0081 (19)0.0021 (16)
C140.0355 (18)0.0398 (19)0.042 (2)−0.0093 (14)0.0031 (16)−0.0073 (16)
C40.0341 (18)0.0313 (18)0.0423 (19)−0.0045 (13)−0.0024 (15)−0.0010 (15)
C10.0221 (16)0.0302 (17)0.0302 (16)−0.0048 (12)0.0000 (13)0.0004 (14)
C110.043 (2)0.0305 (18)0.047 (2)−0.0022 (15)−0.0034 (17)−0.0018 (16)
C100.072 (3)0.034 (2)0.074 (3)0.0137 (18)−0.004 (2)0.000 (2)
Br1—C151.894 (3)C6—C51.384 (4)
S1—O21.427 (2)C6—H60.9500
S1—O31.435 (2)C5—C41.395 (5)
S1—C11.743 (3)C5—H50.9500
S1—C121.754 (3)C3—C41.382 (4)
O1—C81.374 (4)C3—H30.9500
O1—C71.376 (3)C8—C11.345 (4)
C12—C131.385 (4)C8—C111.467 (4)
C12—C171.388 (4)C9—C101.505 (5)
C2—C71.384 (4)C9—C41.509 (4)
C2—C31.391 (4)C9—H9A0.9900
C2—C11.438 (4)C9—H9B0.9900
C17—C161.381 (4)C14—H140.9500
C17—H170.9500C11—H11A0.9800
C13—C141.372 (4)C11—H11B0.9800
C13—H130.9500C11—H11C0.9800
C16—C151.364 (5)C10—H10A0.9800
C16—H160.9500C10—H10B0.9800
C15—C141.381 (5)C10—H10C0.9800
C6—C71.371 (4)
O2—S1—O3119.73 (14)C4—C3—C2119.0 (3)
O2—S1—C1108.87 (14)C4—C3—H3120.5
O3—S1—C1106.63 (14)C2—C3—H3120.5
O2—S1—C12108.70 (14)C1—C8—O1109.9 (3)
O3—S1—C12107.56 (13)C1—C8—C11134.9 (3)
C1—S1—C12104.29 (13)O1—C8—C11115.2 (3)
C8—O1—C7106.7 (2)C10—C9—C4113.8 (3)
C13—C12—C17120.8 (3)C10—C9—H9A108.8
C13—C12—S1119.7 (2)C4—C9—H9A108.8
C17—C12—S1119.6 (2)C10—C9—H9B108.8
C7—C2—C3119.2 (3)C4—C9—H9B108.8
C7—C2—C1104.2 (2)H9A—C9—H9B107.7
C3—C2—C1136.6 (3)C13—C14—C15118.9 (3)
C16—C17—C12118.7 (3)C13—C14—H14120.6
C16—C17—H17120.7C15—C14—H14120.6
C12—C17—H17120.7C3—C4—C5119.6 (3)
C14—C13—C12120.0 (3)C3—C4—C9120.1 (3)
C14—C13—H13120.0C5—C4—C9120.3 (3)
C12—C13—H13120.0C8—C1—C2108.5 (3)
C15—C16—C17120.1 (3)C8—C1—S1126.0 (2)
C15—C16—H16120.0C2—C1—S1125.5 (2)
C17—C16—H16120.0C8—C11—H11A109.5
C16—C15—C14121.7 (3)C8—C11—H11B109.5
C16—C15—Br1119.6 (3)H11A—C11—H11B109.5
C14—C15—Br1118.7 (3)C8—C11—H11C109.5
C7—C6—C5116.1 (3)H11A—C11—H11C109.5
C7—C6—H6122.0H11B—C11—H11C109.5
C5—C6—H6122.0C9—C10—H10A109.5
C6—C7—O1125.7 (3)C9—C10—H10B109.5
C6—C7—C2123.6 (3)H10A—C10—H10B109.5
O1—C7—C2110.7 (3)C9—C10—H10C109.5
C6—C5—C4122.5 (3)H10A—C10—H10C109.5
C6—C5—H5118.7H10B—C10—H10C109.5
C4—C5—H5118.7
O2—S1—C12—C13−156.8 (2)C7—O1—C8—C11179.7 (3)
O3—S1—C12—C13−25.8 (3)C12—C13—C14—C15−0.1 (5)
C1—S1—C12—C1387.2 (3)C16—C15—C14—C130.1 (5)
O2—S1—C12—C1723.7 (3)Br1—C15—C14—C13179.6 (2)
O3—S1—C12—C17154.7 (2)C2—C3—C4—C50.2 (5)
C1—S1—C12—C17−92.3 (3)C2—C3—C4—C9178.8 (3)
C13—C12—C17—C16−0.5 (4)C6—C5—C4—C3−0.3 (5)
S1—C12—C17—C16179.1 (2)C6—C5—C4—C9−178.8 (3)
C17—C12—C13—C140.3 (4)C10—C9—C4—C3−117.6 (4)
S1—C12—C13—C14−179.3 (3)C10—C9—C4—C560.9 (5)
C12—C17—C16—C150.5 (5)O1—C8—C1—C20.1 (3)
C17—C16—C15—C14−0.3 (5)C11—C8—C1—C2180.0 (3)
C17—C16—C15—Br1−179.8 (2)O1—C8—C1—S1−179.2 (2)
C5—C6—C7—O1179.4 (3)C11—C8—C1—S10.7 (5)
C5—C6—C7—C2−0.4 (5)C7—C2—C1—C80.2 (3)
C8—O1—C7—C6−179.2 (3)C3—C2—C1—C8178.9 (3)
C8—O1—C7—C20.6 (3)C7—C2—C1—S1179.5 (2)
C3—C2—C7—C60.4 (5)C3—C2—C1—S1−1.8 (5)
C1—C2—C7—C6179.3 (3)O2—S1—C1—C8−22.4 (3)
C3—C2—C7—O1−179.4 (3)O3—S1—C1—C8−152.8 (3)
C1—C2—C7—O1−0.5 (3)C12—S1—C1—C893.5 (3)
C7—C6—C5—C40.4 (5)O2—S1—C1—C2158.4 (2)
C7—C2—C3—C4−0.2 (4)O3—S1—C1—C228.0 (3)
C1—C2—C3—C4−178.8 (3)C12—S1—C1—C2−85.7 (3)
C7—O1—C8—C1−0.4 (3)
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.952.533.238 (4)131
C11—H11A···O3ii0.982.583.321 (4)132
C14—H14···Cgiii0.952.703.495 (4)142
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C6—H6⋯O3i 0.952.533.238 (4)131
C11—H11A⋯O3ii 0.982.583.321 (4)132
C14—H14⋯Cg iii 0.952.703.495 (4)142

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

  6 in total

1.  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

2.  A short history of SHELX.

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

3.  5-Ethyl-3-(4-Fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-18

4.  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

5.  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

6.  5-Ethyl-3-(3-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-29
  6 in total

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