2-Methyl-3-(phenyl­sulfon­yl)naphtho[1,2-b]furan

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

doi:10.1107/S1600536808000895

. 2008 Jan 16;64(Pt 2):o452. doi: 10.1107/S1600536808000895

2-Methyl-3-(phenylsulfonyl)naphtho[1,2-b]furan

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

PMCID: PMC2960217 PMID: 21201479

Abstract

In the title molecule, C₁₉H₁₄O₃S, the phenyl ring forms a dihedral angle of 69.13 (6)° with the plane of the naphthofuran fragment, being slightly tilted towards it. The crystal packing exhibits π–π interactions between the benzene rings from neighbouring molecules [centroid–centroid distance = 3.616 (4) Å] and weak C—H⋯O and C—H⋯π interactions.

Related literature

The crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been reported by Choi et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₁₄O₃S
M _r = 322.36
Orthorhombic,
a = 8.198 (4) Å
b = 18.589 (8) Å
c = 10.049 (4) Å
V = 1531.4 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8102 measured reflections
2714 independent reflections
2538 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.083
S = 1.05
2714 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1125 Friedel pairs
Flack parameter: 0.04 (7)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536808000895/cv2379sup1.cif

e-64-0o452-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000895/cv2379Isup2.hkl

e-64-0o452-Isup2.hkl^{(133.3KB, hkl)}

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

Table 1. Selected interatomic distances (Å).

Cg2 and Cg3 are the centroids of the C2–C5/C10/C11 benzene ring and the C5–C10 benzene ring, respectively.

Cg2⋯Cg3ⁱ

3.616 (4)

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Symmetry code: (i) Inline graphic .

Table 2. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1ⁱ	0.98	2.64	3.483 (3)	144
C8—H8⋯O3ⁱⁱ	0.95	2.51	3.406 (3)	157
C16—H16⋯O3ⁱⁱⁱ	0.95	2.51	3.430 (3)	164

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

supplementary crystallographic information

Comment

As part of our ongoing study of 2-methylnaphtho[1,2-b]furan derivatives, the crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been recently reported (Choi et al., 2006). Herein we present the molecular and crystal structure of the title compound, (I).

In (I) (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the thirteen constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between adjacent benzene rings. The Cg2···Cg3ⁱ distance is 3.616 (4) Å (Table 1; Cg2 and Cg3 are the centroids of the C2—C5/C10/C11 benzene ring and the C5—C10 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by CH₂—H···π interactions between the methyl group and the furan ring of the naphthofuran unit, with a C13—H13A···Cg1ⁱ separation of 2.64 Å (Fig. 2 and Table 2; Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring; symmetry code as in Fig. 2). Additionally, the weak hydrogen bonds were observed; one between the benzene H atom of naphthofuran unit and the O atom of sulfonyl group, with a C8—H8···O3ⁱⁱ, a second between the benzene H atom of phenylsulfonyl group and adjacent O atom of sulfonyl group, with a C16—H16···O3ⁱⁱⁱ (Fig. 2 and Table 2; symmetry code as in Fig. 2).

Experimental

3-Chloroperbenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 2-methyl-3-(phenylsulfanyl)naphtho[1,2-b] furan (348 mg, 1.2 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 4 h, 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 pale yellow solid [yield 84%, m.p. 412–413 K; R_f = 0.64 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in acetone at room temperature.