2-Methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan

Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536808007046

. 2008 Mar 20;64(Pt 4):o727. doi: 10.1107/S1600536808007046

2-Methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan

Hong Dae Choi ^a, Pil Ja Seo ^a, Byeng Wha Son ^b, Uk Lee ^b,^*

PMCID: PMC2961025 PMID: 21202117

Abstract

The title compound, C₁₉H₁₄O₃S, was prepared by the oxidation of 2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.850 (2) Å] and weak C—H⋯π interactions. In addition, there are also intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methylnaphtho[2,1-b]furan compounds, see: Choi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C₁₉H₁₄O₃S
M _r = 322.36
Monoclinic,
a = 10.7175 (4) Å
b = 7.7972 (3) Å
c = 18.0488 (7) Å
β = 97.797 (1)°
V = 1494.33 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8784 measured reflections
3222 independent reflections
2785 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 1.05
3222 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007046/fb2090sup1.cif

e-64-0o727-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007046/fb2090Isup2.hkl

e-64-0o727-Isup2.hkl^{(158.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2	0.95	2.35	3.190 (2)	147
C18—H18⋯O2	0.95	2.46	2.869 (2)	106
C19—H19B⋯O3	0.98	2.55	2.926 (2)	103
C19—H19C⋯Cg3ⁱ	0.98	3.03	3.735 (3)	130
C16—H16⋯Cg3ⁱⁱ	0.95	2.88	3.761 (3)	155

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Symmetry codes: (i) Inline graphic ; (ii) . Cg3 is the centroid of the benzene ring of the naphthofuran unit.

supplementary crystallographic information

Comment

As a part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan derivatives, the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007) have already been described. Herein we report the molecular and the crystal structure of the title compound, 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation equal to 0.040 Å from the least-squares plane defined by thirteen constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the furan and the benzene rings from the adjacent naphthofuran fragments. The Cg1···Cg2ⁱ distance is 3.850 (2) Å (Cg1 and Cg2 are the centroids of the O1/C12/C1/C2/C11 furan and the C2/C3/C8/C9/C10/C11 benzene rings, respectively, the symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by the C—H···π interactions; in both cases the benzene ring of the naphthofuran unit (Cg3) is involved. There are also intramolecular C—H···O interactions present in the structure.

Experimental

3-Chloroperoxybenzoic acid (77%, 471 mg, 2.10 mmol) was added in small portions to a stirred solution of 2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (290 mg, 1.0 mmol) in dichloromethane (20 ml) at 273 K. After having been stirred for 4 h at room temperature, the mixture was washed with saturated sodium hydrogencarbonate 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 colourless solid [yield 84%, m.p. 431–432 K; R_f = 0.63 (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 acetone at room temperature. The average crystal size was approximately 1.0 × 1.0 × 0.5 mm. The crystals are colourless and soluble in polar solvents.