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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2609.
Published online 2009 October 3. doi:  10.1107/S1600536809039324
PMCID: PMC2971280

5-Bromo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran

Abstract

In the title compound, C20H13BrO2S, the O atom and the phenyl group of the phenyl­sulfinyl substituent are located on opposite sides of the plane of the benzofuran system. The S-bound phenyl ring is almost perpendicular to this plane [80.35 (8)°]. The phenyl ring in the 2-position is twisted with respect to the benzofuran plane, making a dihedral angle of 16.0 (1)°.

Related literature

For the crystal structures of similar 5-halo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a [triangle],b [triangle]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 [triangle]); Twyman & Allsop (1999 [triangle]). For natural products involving a benzofuran ring system, see: Akgul & Anil (2003 [triangle]); Reuss & König (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2609-scheme1.jpg

Experimental

Crystal data

  • C20H13BrO2S
  • M r = 397.27
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2609-efi1.jpg
  • a = 8.2670 (1) Å
  • b = 9.5233 (2) Å
  • c = 11.8663 (2) Å
  • α = 72.187 (1)°
  • β = 80.772 (1)°
  • γ = 69.526 (1)°
  • V = 831.76 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.61 mm−1
  • T = 293 K
  • 0.35 × 0.22 × 0.11 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.462, T max = 0.763
  • 13542 measured reflections
  • 3275 independent reflections
  • 2716 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.095
  • S = 1.05
  • 3275 reflections
  • 217 parameters
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039324/dn2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039324/dn2491Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Molecules containing benzofuran moiety have received much attenttion in the field of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999), and these compounds are ubiquitous in nature (Akgul & Anil, 2003; Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b), we present the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.010 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the plane of the benzofuran unit and the plane of 2-phenyl ring is 16.0 (1)°. The phenyl ring (C15-C20) is almost perpendicular to the plane of the benzofuran unit [80.35 (8)°].

Experimental

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-2-phenyl-3-phenylsulfanyl-1-benzofuran (343 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2 : 1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 417-418 K; Rf = 0.56 (hexane-ethyl acetate, 2 : 1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement

All H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å and Uiso(H) = 1.2Ueq(C)

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radii.

Crystal data

C20H13BrO2SZ = 2
Mr = 397.27F(000) = 400
Triclinic, P1Dx = 1.586 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2670 (1) ÅCell parameters from 5885 reflections
b = 9.5233 (2) Åθ = 2.4–26.0°
c = 11.8663 (2) ŵ = 2.61 mm1
α = 72.187 (1)°T = 293 K
β = 80.772 (1)°Block, colorless
γ = 69.526 (1)°0.35 × 0.22 × 0.11 mm
V = 831.76 (2) Å3

Data collection

Bruker SMART CCD diffractometer3275 independent reflections
Radiation source: fine-focus sealed tube2716 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 26.0°, θmin = 1.8°
[var phi] and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)k = −11→11
Tmin = 0.462, Tmax = 0.763l = −14→14
13542 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.095H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3341P] where P = (Fo2 + 2Fc2)/3
3275 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.59 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br1.01046 (4)0.24078 (4)0.38069 (3)0.07875 (15)
S0.60607 (8)0.10785 (7)0.86253 (6)0.05063 (17)
O10.5011 (2)0.56165 (18)0.71087 (15)0.0552 (4)
O20.7801 (2)0.0093 (2)0.8283 (2)0.0760 (6)
C10.5823 (3)0.3012 (2)0.7751 (2)0.0453 (5)
C20.6714 (3)0.3415 (3)0.6609 (2)0.0470 (5)
C30.7888 (3)0.2607 (3)0.5871 (2)0.0516 (6)
H30.82690.15250.60700.062*
C40.8466 (3)0.3472 (3)0.4831 (2)0.0566 (6)
C50.7910 (4)0.5094 (3)0.4506 (3)0.0655 (7)
H50.83380.56320.37960.079*
C60.6738 (4)0.5895 (3)0.5225 (3)0.0645 (7)
H60.63430.69780.50170.077*
C70.6166 (3)0.5035 (3)0.6272 (2)0.0518 (6)
C80.4830 (3)0.4365 (3)0.8020 (2)0.0486 (5)
C90.3645 (3)0.4760 (3)0.9012 (2)0.0505 (6)
C100.3612 (4)0.3686 (3)1.0094 (3)0.0660 (7)
H100.43650.26721.02070.079*
C110.2474 (4)0.4101 (4)1.1009 (3)0.0750 (8)
H110.24690.33631.17350.090*
C120.1352 (4)0.5581 (4)1.0866 (3)0.0768 (9)
H120.05810.58501.14870.092*
C130.1375 (5)0.6667 (4)0.9799 (3)0.0868 (10)
H130.06220.76800.96960.104*
C140.2507 (4)0.6265 (3)0.8877 (3)0.0732 (8)
H140.25110.70110.81560.088*
C150.4515 (3)0.0742 (2)0.7931 (2)0.0455 (5)
C160.5017 (4)0.0001 (3)0.7038 (3)0.0647 (7)
H160.6170−0.03070.67620.078*
C170.3767 (6)−0.0275 (4)0.6558 (3)0.0833 (10)
H170.4082−0.07780.59590.100*
C180.2085 (5)0.0188 (4)0.6965 (4)0.0836 (10)
H180.12540.00150.66290.100*
C190.1600 (4)0.0901 (4)0.7856 (4)0.0791 (10)
H190.04450.12000.81290.095*
C200.2804 (3)0.1180 (3)0.8351 (3)0.0592 (6)
H200.24740.16590.89640.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br0.0790 (2)0.0939 (3)0.0630 (2)−0.03538 (18)0.01864 (16)−0.02325 (17)
S0.0434 (3)0.0442 (3)0.0520 (4)−0.0148 (2)−0.0066 (3)0.0070 (2)
O10.0669 (11)0.0419 (8)0.0506 (10)−0.0212 (8)−0.0008 (8)−0.0010 (7)
O20.0417 (10)0.0554 (10)0.1019 (16)−0.0060 (8)−0.0054 (10)0.0088 (10)
C10.0446 (12)0.0424 (11)0.0450 (13)−0.0191 (9)−0.0066 (10)0.0017 (9)
C20.0452 (12)0.0475 (12)0.0462 (13)−0.0220 (10)−0.0059 (10)0.0002 (10)
C30.0468 (13)0.0515 (13)0.0524 (14)−0.0201 (10)−0.0030 (11)−0.0034 (11)
C40.0540 (14)0.0659 (15)0.0496 (15)−0.0267 (12)0.0013 (11)−0.0085 (12)
C50.0774 (19)0.0670 (17)0.0487 (15)−0.0372 (15)0.0034 (13)0.0020 (13)
C60.0787 (19)0.0507 (14)0.0568 (16)−0.0289 (13)−0.0025 (14)0.0045 (12)
C70.0548 (14)0.0484 (12)0.0489 (14)−0.0222 (11)−0.0026 (11)−0.0022 (10)
C80.0516 (13)0.0473 (12)0.0438 (13)−0.0214 (10)−0.0071 (10)0.0008 (10)
C90.0501 (13)0.0527 (13)0.0490 (14)−0.0208 (11)−0.0042 (11)−0.0085 (11)
C100.0787 (19)0.0550 (15)0.0548 (16)−0.0188 (13)0.0048 (14)−0.0090 (12)
C110.088 (2)0.0731 (19)0.0537 (17)−0.0271 (17)0.0110 (15)−0.0100 (14)
C120.0691 (19)0.088 (2)0.070 (2)−0.0255 (17)0.0152 (15)−0.0269 (17)
C130.077 (2)0.0691 (19)0.089 (3)−0.0030 (16)0.0095 (18)−0.0164 (18)
C140.0709 (19)0.0611 (16)0.0660 (19)−0.0098 (14)0.0026 (15)−0.0036 (14)
C150.0445 (12)0.0335 (10)0.0491 (13)−0.0121 (9)−0.0008 (10)0.0006 (9)
C160.0687 (17)0.0482 (13)0.0679 (18)−0.0157 (12)0.0089 (14)−0.0125 (12)
C170.127 (3)0.0537 (16)0.078 (2)−0.0311 (19)−0.018 (2)−0.0209 (15)
C180.090 (3)0.0569 (17)0.112 (3)−0.0276 (17)−0.037 (2)−0.0142 (18)
C190.0525 (17)0.0681 (18)0.116 (3)−0.0219 (14)−0.0125 (17)−0.0174 (19)
C200.0474 (14)0.0579 (14)0.0708 (18)−0.0168 (11)0.0004 (12)−0.0174 (13)

Geometric parameters (Å, °)

Br—C41.899 (3)C10—C111.377 (4)
S—O21.489 (2)C10—H100.9300
S—C11.775 (2)C11—C121.366 (5)
S—C151.789 (2)C11—H110.9300
O1—C71.366 (3)C12—C131.371 (5)
O1—C81.377 (3)C12—H120.9300
C1—C81.365 (4)C13—C141.377 (5)
C1—C21.444 (3)C13—H130.9300
C2—C31.385 (4)C14—H140.9300
C2—C71.391 (3)C15—C161.379 (4)
C3—C41.376 (3)C15—C201.383 (3)
C3—H30.9300C16—C171.390 (5)
C4—C51.393 (4)C16—H160.9300
C5—C61.366 (4)C17—C181.359 (5)
C5—H50.9300C17—H170.9300
C6—C71.378 (4)C18—C191.361 (5)
C6—H60.9300C18—H180.9300
C8—C91.459 (4)C19—C201.370 (4)
C9—C101.379 (4)C19—H190.9300
C9—C141.389 (4)C20—H200.9300
O2—S—C1106.63 (11)C11—C10—H10119.7
O2—S—C15106.87 (13)C9—C10—H10119.7
C1—S—C1597.41 (10)C12—C11—C10120.9 (3)
C7—O1—C8107.23 (18)C12—C11—H11119.6
C8—C1—C2107.74 (19)C10—C11—H11119.6
C8—C1—S127.74 (19)C11—C12—C13119.3 (3)
C2—C1—S124.50 (18)C11—C12—H12120.3
C3—C2—C7119.5 (2)C13—C12—H12120.3
C3—C2—C1136.0 (2)C12—C13—C14120.3 (3)
C7—C2—C1104.5 (2)C12—C13—H13119.9
C4—C3—C2117.2 (2)C14—C13—H13119.9
C4—C3—H3121.4C13—C14—C9120.8 (3)
C2—C3—H3121.4C13—C14—H14119.6
C3—C4—C5122.7 (3)C9—C14—H14119.6
C3—C4—Br118.6 (2)C16—C15—C20120.5 (3)
C5—C4—Br118.8 (2)C16—C15—S121.3 (2)
C6—C5—C4120.3 (2)C20—C15—S118.1 (2)
C6—C5—H5119.9C15—C16—C17118.8 (3)
C4—C5—H5119.9C15—C16—H16120.6
C5—C6—C7117.3 (2)C17—C16—H16120.6
C5—C6—H6121.4C18—C17—C16120.1 (3)
C7—C6—H6121.4C18—C17—H17120.0
O1—C7—C6126.1 (2)C16—C17—H17120.0
O1—C7—C2110.8 (2)C17—C18—C19120.9 (3)
C6—C7—C2123.0 (3)C17—C18—H18119.5
C1—C8—O1109.7 (2)C19—C18—H18119.5
C1—C8—C9135.1 (2)C18—C19—C20120.3 (3)
O1—C8—C9115.3 (2)C18—C19—H19119.8
C10—C9—C14118.1 (3)C20—C19—H19119.8
C10—C9—C8122.2 (2)C19—C20—C15119.3 (3)
C14—C9—C8119.6 (2)C19—C20—H20120.3
C11—C10—C9120.6 (3)C15—C20—H20120.3
O2—S—C1—C8−152.9 (2)C7—O1—C8—C1−1.4 (3)
C15—S—C1—C896.9 (2)C7—O1—C8—C9179.5 (2)
O2—S—C1—C225.7 (2)C1—C8—C9—C1016.4 (5)
C15—S—C1—C2−84.4 (2)O1—C8—C9—C10−164.9 (2)
C8—C1—C2—C3179.1 (3)C1—C8—C9—C14−163.9 (3)
S—C1—C2—C30.2 (4)O1—C8—C9—C1414.8 (4)
C8—C1—C2—C70.1 (3)C14—C9—C10—C110.3 (5)
S—C1—C2—C7−178.80 (18)C8—C9—C10—C11−180.0 (3)
C7—C2—C3—C40.5 (4)C9—C10—C11—C120.1 (5)
C1—C2—C3—C4−178.4 (3)C10—C11—C12—C13−0.6 (6)
C2—C3—C4—C5−0.4 (4)C11—C12—C13—C140.6 (6)
C2—C3—C4—Br179.02 (18)C12—C13—C14—C9−0.1 (6)
C3—C4—C5—C6−0.3 (4)C10—C9—C14—C13−0.3 (5)
Br—C4—C5—C6−179.7 (2)C8—C9—C14—C13179.9 (3)
C4—C5—C6—C70.8 (4)O2—S—C15—C16−14.1 (2)
C8—O1—C7—C6−178.7 (3)C1—S—C15—C1695.8 (2)
C8—O1—C7—C21.5 (3)O2—S—C15—C20162.89 (18)
C5—C6—C7—O1179.6 (3)C1—S—C15—C20−87.2 (2)
C5—C6—C7—C2−0.7 (4)C20—C15—C16—C170.9 (4)
C3—C2—C7—O1179.8 (2)S—C15—C16—C17177.9 (2)
C1—C2—C7—O1−1.0 (3)C15—C16—C17—C180.3 (4)
C3—C2—C7—C60.0 (4)C16—C17—C18—C19−1.2 (5)
C1—C2—C7—C6179.2 (3)C17—C18—C19—C200.7 (5)
C2—C1—C8—O10.9 (3)C18—C19—C20—C150.5 (5)
S—C1—C8—O1179.67 (17)C16—C15—C20—C19−1.3 (4)
C2—C1—C8—C9179.6 (3)S—C15—C20—C19−178.4 (2)
S—C1—C8—C9−1.6 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2491).

References

  • Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. [PubMed]
  • Bruker (2001). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o1809. [PMC free article] [PubMed]
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1958. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J 340, 283–289. [PubMed]
  • Reuss, S. H. & König, W. A. (2004). Phytochemistry, 65, 3113–3118. [PubMed]
  • Sheldrick, G. M. (2000). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett 40, 9383–9384.

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