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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1641.
Published online 2009 June 20. doi:  10.1107/S1600536809023101
PMCID: PMC2969341

2-Phenyl-3-(phenyl­sulfin­yl)naphtho[1,2-b]furan

Abstract

In the title compound, C24H16O2S, the O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [81.54 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 18.2 (1)°.

Related literature

For the crystal structures of similar naphtho[1,2-b]furan derivatives, see: Choi et al. (2008a [triangle],b [triangle]). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 [triangle]); Piloto et al. (2005 [triangle]).

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Object name is e-65-o1641-scheme1.jpg

Experimental

Crystal data

  • C24H16O2S
  • M r = 368.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1641-efi1.jpg
  • a = 10.123 (1) Å
  • b = 14.109 (2) Å
  • c = 12.410 (2) Å
  • β = 99.743 (2)°
  • V = 1746.9 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 173 K
  • 0.20 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 10523 measured reflections
  • 3804 independent reflections
  • 2555 reflections with I > 2σ(I)
  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.137
  • S = 1.05
  • 3804 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.41 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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023101/hg2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023101/hg2520Isup2.hkl

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

supplementary crystallographic information

Comment

The naphthofuran compounds have attracted widespread interest in view of their biological and pharmacological activities (Goel & Dixit, 2004; Piloto et al., 2005). This work is related to our communications on the synthesis and structures of naphtho[1,2-b]furan analogues, viz. 2-methyl-3-(phenylsulfonyl)naphtho[1,2-b]furan (Choi et al., 2008a) and 3-(4-chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan (Choi et al., 2008b). We report the crystal structure of the title compound (I), 2-phenyl-3-(phenylsulfinyl)naphtho[1,2-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.023 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle in (I) formed by the plane of the naphthofuran ring and the plane of 2-phenyl ring is 18.2 (1)°, and the phenyl ring (C19-C24) with 81.54 (5)° lies toward the naphthofuran plane.

Experimental

The 77% 3-chloroperoxybenzoic acid (77%, 179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-phenyl-3-(phenylsulfanyl)naphtho[1,2-b]furan (282 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, 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 80%, m.p. 472-473 K; Rf = 0.52 (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 positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aromatic H atoms and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.

Crystal data

C24H16O2SF(000) = 768
Mr = 368.44Dx = 1.401 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2794 reflections
a = 10.123 (1) Åθ = 2.4–28.0°
b = 14.109 (2) ŵ = 0.20 mm1
c = 12.410 (2) ÅT = 173 K
β = 99.743 (2)°Block, colorless
V = 1746.9 (4) Å30.20 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
graphiteθmax = 27.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm-1h = −12→12
[var phi] and ω scansk = −18→17
10523 measured reflectionsl = −15→10
3804 independent 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)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.137H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0554P)2 + 0.5717P] where P = (Fo2 + 2Fc2)/3
3804 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.41 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
S0.28091 (6)0.00804 (5)0.16729 (5)0.02695 (19)
O10.40566 (16)0.15573 (12)0.43697 (13)0.0242 (4)
O20.20908 (19)0.07138 (13)0.08044 (15)0.0371 (5)
C10.3042 (2)0.07384 (17)0.2906 (2)0.0237 (5)
C20.2072 (2)0.13705 (17)0.3244 (2)0.0245 (5)
C30.0698 (2)0.15748 (18)0.2865 (2)0.0287 (6)
H30.02060.12440.22610.034*
C40.0109 (2)0.22564 (19)0.3393 (2)0.0296 (6)
H4−0.08100.23960.31460.035*
C50.0812 (2)0.27738 (18)0.4303 (2)0.0257 (6)
C60.0202 (3)0.34960 (19)0.4835 (2)0.0306 (6)
H6−0.07200.36360.46000.037*
C70.0913 (3)0.39968 (19)0.5680 (2)0.0331 (6)
H70.04810.44800.60250.040*
C80.2281 (3)0.38060 (19)0.6046 (2)0.0322 (6)
H80.27680.41630.66310.039*
C90.2907 (3)0.31082 (18)0.5560 (2)0.0287 (6)
H90.38290.29800.58120.034*
C190.1603 (2)−0.07478 (17)0.2024 (2)0.0247 (5)
C100.2198 (2)0.25777 (17)0.4690 (2)0.0234 (5)
C110.2748 (2)0.18564 (17)0.4126 (2)0.0236 (5)
C120.4218 (2)0.08750 (17)0.3604 (2)0.0238 (5)
C130.5573 (2)0.04856 (18)0.3710 (2)0.0245 (6)
C140.5820 (3)−0.03834 (18)0.3242 (2)0.0291 (6)
H140.5092−0.07410.28610.035*
C150.7112 (3)−0.07276 (19)0.3326 (2)0.0335 (6)
H150.7268−0.13180.30010.040*
C160.8175 (3)−0.0217 (2)0.3881 (2)0.0359 (7)
H160.9064−0.04490.39270.043*
C170.7944 (3)0.0634 (2)0.4371 (2)0.0372 (7)
H170.86730.09760.47730.045*
C180.6658 (3)0.0989 (2)0.4279 (2)0.0311 (6)
H180.65120.15800.46050.037*
C200.0331 (3)−0.07786 (19)0.1411 (2)0.0308 (6)
H200.0073−0.03360.08370.037*
C21−0.0565 (3)−0.1460 (2)0.1641 (2)0.0349 (7)
H21−0.1441−0.14860.12220.042*
C22−0.0190 (3)−0.21003 (19)0.2474 (2)0.0351 (7)
H22−0.0813−0.25600.26360.042*
C230.1093 (3)−0.20754 (19)0.3078 (2)0.0318 (6)
H230.1350−0.25210.36490.038*
C240.1998 (3)−0.14042 (18)0.2852 (2)0.0290 (6)
H240.2882−0.13900.32570.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0311 (3)0.0275 (4)0.0222 (3)−0.0035 (3)0.0044 (3)−0.0006 (3)
O10.0217 (8)0.0279 (10)0.0219 (9)0.0022 (7)0.0003 (7)−0.0001 (7)
O20.0493 (12)0.0350 (11)0.0250 (10)−0.0060 (9)0.0006 (9)0.0065 (8)
C10.0273 (13)0.0217 (13)0.0215 (13)−0.0017 (10)0.0021 (10)0.0016 (10)
C20.0269 (13)0.0220 (13)0.0238 (13)−0.0018 (10)0.0025 (11)0.0047 (11)
C30.0259 (13)0.0286 (14)0.0291 (14)−0.0024 (11)−0.0027 (11)0.0000 (12)
C40.0203 (12)0.0316 (15)0.0350 (15)0.0024 (11)−0.0007 (11)0.0048 (12)
C50.0274 (13)0.0259 (14)0.0242 (13)0.0018 (11)0.0056 (11)0.0062 (11)
C60.0280 (13)0.0300 (15)0.0350 (16)0.0059 (11)0.0087 (12)0.0084 (12)
C70.0413 (15)0.0288 (15)0.0320 (15)0.0071 (12)0.0144 (13)0.0011 (12)
C80.0397 (15)0.0289 (15)0.0278 (14)0.0013 (12)0.0056 (12)−0.0007 (12)
C90.0290 (13)0.0302 (15)0.0264 (14)0.0015 (11)0.0038 (11)0.0019 (11)
C190.0303 (13)0.0212 (13)0.0233 (13)−0.0026 (11)0.0061 (11)−0.0048 (10)
C100.0253 (13)0.0239 (13)0.0216 (13)−0.0006 (10)0.0053 (10)0.0046 (10)
C110.0221 (12)0.0231 (13)0.0246 (13)0.0001 (10)0.0011 (10)0.0048 (10)
C120.0299 (13)0.0209 (13)0.0210 (13)−0.0023 (11)0.0056 (10)0.0008 (10)
C130.0254 (12)0.0293 (14)0.0188 (12)0.0019 (10)0.0032 (10)0.0054 (11)
C140.0288 (13)0.0268 (14)0.0313 (15)−0.0017 (11)0.0041 (12)0.0022 (12)
C150.0359 (15)0.0286 (15)0.0365 (16)0.0080 (12)0.0077 (13)0.0038 (13)
C160.0273 (14)0.0436 (17)0.0366 (16)0.0120 (13)0.0048 (12)0.0081 (14)
C170.0300 (14)0.0487 (19)0.0302 (15)0.0029 (13)−0.0024 (12)−0.0006 (13)
C180.0313 (14)0.0335 (16)0.0266 (14)0.0035 (12)−0.0006 (11)−0.0020 (12)
C200.0333 (14)0.0303 (15)0.0277 (14)0.0002 (12)0.0017 (12)−0.0001 (12)
C210.0285 (14)0.0397 (17)0.0363 (16)−0.0065 (12)0.0048 (12)−0.0060 (13)
C220.0410 (16)0.0260 (15)0.0417 (17)−0.0080 (12)0.0167 (14)−0.0075 (13)
C230.0446 (16)0.0229 (14)0.0294 (15)0.0025 (12)0.0103 (13)0.0031 (11)
C240.0317 (14)0.0298 (14)0.0243 (13)−0.0015 (11)0.0011 (11)−0.0007 (11)

Geometric parameters (Å, °)

S—O21.4912 (19)C19—C241.390 (3)
S—C11.771 (3)C10—C111.403 (3)
S—C191.796 (3)C12—C131.463 (3)
O1—C111.375 (3)C13—C181.395 (3)
O1—C121.381 (3)C13—C141.397 (4)
C1—C121.363 (3)C14—C151.383 (4)
C1—C21.440 (3)C14—H140.9500
C2—C111.372 (3)C15—C161.378 (4)
C2—C31.420 (3)C15—H150.9500
C3—C41.356 (4)C16—C171.384 (4)
C3—H30.9500C16—H160.9500
C4—C51.429 (4)C17—C181.381 (4)
C4—H40.9500C17—H170.9500
C5—C61.412 (4)C18—H180.9500
C5—C101.431 (3)C20—C211.384 (4)
C6—C71.365 (4)C20—H200.9500
C6—H60.9500C21—C221.377 (4)
C7—C81.408 (4)C21—H210.9500
C7—H70.9500C22—C231.386 (4)
C8—C91.365 (4)C22—H220.9500
C8—H80.9500C23—C241.379 (4)
C9—C101.407 (3)C23—H230.9500
C9—H90.9500C24—H240.9500
C19—C201.381 (3)
O2—S—C1106.72 (11)C2—C11—C10125.0 (2)
O2—S—C19107.27 (11)O1—C11—C10124.2 (2)
C1—S—C1997.33 (11)C1—C12—O1110.1 (2)
C11—O1—C12106.53 (18)C1—C12—C13135.2 (2)
C12—C1—C2107.0 (2)O1—C12—C13114.7 (2)
C12—C1—S126.7 (2)C18—C13—C14118.4 (2)
C2—C1—S125.37 (18)C18—C13—C12120.0 (2)
C11—C2—C3119.4 (2)C14—C13—C12121.5 (2)
C11—C2—C1105.6 (2)C15—C14—C13120.7 (2)
C3—C2—C1135.0 (2)C15—C14—H14119.7
C4—C3—C2118.0 (2)C13—C14—H14119.7
C4—C3—H3121.0C16—C15—C14120.2 (3)
C2—C3—H3121.0C16—C15—H15119.9
C3—C4—C5122.9 (2)C14—C15—H15119.9
C3—C4—H4118.6C15—C16—C17119.8 (2)
C5—C4—H4118.6C15—C16—H16120.1
C6—C5—C4122.7 (2)C17—C16—H16120.1
C6—C5—C10117.6 (2)C18—C17—C16120.3 (3)
C4—C5—C10119.7 (2)C18—C17—H17119.8
C7—C6—C5121.1 (2)C16—C17—H17119.8
C7—C6—H6119.4C17—C18—C13120.5 (3)
C5—C6—H6119.4C17—C18—H18119.7
C6—C7—C8120.7 (3)C13—C18—H18119.7
C6—C7—H7119.6C19—C20—C21119.4 (3)
C8—C7—H7119.6C19—C20—H20120.3
C9—C8—C7120.0 (3)C21—C20—H20120.3
C9—C8—H8120.0C22—C21—C20120.2 (3)
C7—C8—H8120.0C22—C21—H21119.9
C8—C9—C10120.5 (2)C20—C21—H21119.9
C8—C9—H9119.8C21—C22—C23120.2 (3)
C10—C9—H9119.8C21—C22—H22119.9
C20—C19—C24120.7 (2)C23—C22—H22119.9
C20—C19—S119.7 (2)C24—C23—C22120.1 (3)
C24—C19—S119.35 (19)C24—C23—H23120.0
C11—C10—C9125.1 (2)C22—C23—H23120.0
C11—C10—C5115.0 (2)C23—C24—C19119.3 (2)
C9—C10—C5120.0 (2)C23—C24—H24120.3
C2—C11—O1110.7 (2)C19—C24—H24120.3
O2—S—C1—C12−127.7 (2)C12—O1—C11—C21.2 (3)
C19—S—C1—C12121.7 (2)C12—O1—C11—C10−177.3 (2)
O2—S—C1—C239.8 (2)C9—C10—C11—C2−176.7 (2)
C19—S—C1—C2−70.8 (2)C5—C10—C11—C21.9 (4)
C12—C1—C2—C110.7 (3)C9—C10—C11—O11.6 (4)
S—C1—C2—C11−168.88 (19)C5—C10—C11—O1−179.8 (2)
C12—C1—C2—C3179.5 (3)C2—C1—C12—O10.0 (3)
S—C1—C2—C310.0 (4)S—C1—C12—O1169.41 (17)
C11—C2—C3—C40.6 (4)C2—C1—C12—C13−178.7 (3)
C1—C2—C3—C4−178.1 (3)S—C1—C12—C13−9.4 (4)
C2—C3—C4—C50.2 (4)C11—O1—C12—C1−0.7 (3)
C3—C4—C5—C6178.7 (2)C11—O1—C12—C13178.3 (2)
C3—C4—C5—C100.0 (4)C1—C12—C13—C18158.3 (3)
C4—C5—C6—C7−177.9 (2)O1—C12—C13—C18−20.4 (3)
C10—C5—C6—C70.8 (4)C1—C12—C13—C14−20.9 (4)
C5—C6—C7—C80.0 (4)O1—C12—C13—C14160.3 (2)
C6—C7—C8—C9−0.5 (4)C18—C13—C14—C15−1.0 (4)
C7—C8—C9—C100.3 (4)C12—C13—C14—C15178.3 (2)
O2—S—C19—C207.9 (2)C13—C14—C15—C160.3 (4)
C1—S—C19—C20118.0 (2)C14—C15—C16—C171.2 (4)
O2—S—C19—C24−177.6 (2)C15—C16—C17—C18−2.0 (4)
C1—S—C19—C24−67.5 (2)C16—C17—C18—C131.3 (4)
C8—C9—C10—C11179.1 (2)C14—C13—C18—C170.2 (4)
C8—C9—C10—C50.5 (4)C12—C13—C18—C17−179.1 (2)
C6—C5—C10—C11−179.7 (2)C24—C19—C20—C211.3 (4)
C4—C5—C10—C11−1.0 (3)S—C19—C20—C21175.7 (2)
C6—C5—C10—C9−1.0 (4)C19—C20—C21—C220.1 (4)
C4—C5—C10—C9177.7 (2)C20—C21—C22—C23−1.0 (4)
C3—C2—C11—O1179.8 (2)C21—C22—C23—C240.5 (4)
C1—C2—C11—O1−1.2 (3)C22—C23—C24—C190.9 (4)
C3—C2—C11—C10−1.8 (4)C20—C19—C24—C23−1.8 (4)
C1—C2—C11—C10177.3 (2)S—C19—C24—C23−176.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2520).

References

  • Bruker (2001). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o452. [PMC free article] [PubMed]
  • Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o837. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Goel, A. & Dixit, M. (2004). Tetrahedron Lett 45, 8819–8821.
  • Piloto, A. M., Costa, S. P. G. & Goncalves, M. S. T. (2005). Tetrahedron Lett 46, 4757–4760.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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