3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[1,2-b]furan

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

doi:10.1107/S1600536810048361

. 2010 Nov 27;66(Pt 12):o3302. doi: 10.1107/S1600536810048361

3-(4-Fluorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan

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

PMCID: PMC3011502 PMID: 21589581

Abstract

In the title compound, C₁₉H₁₃FO₃S, the 4-fluorophenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O, C—H⋯F and C—H⋯π interactions. The crystal structure also exhibits aromatic π–π interactions between the central benzene and the outer benzene rings of neighbouring molecules [centroid–centroid distance = 3.650 (3) Å].

Related literature

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For our previous structural studies of related 3-arylsulfonyl-2-methylnaphtho[1,2-b]furan derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₉H₁₃FO₃S
M _r = 340.35
Orthorhombic,
a = 8.1456 (3) Å
b = 18.4472 (5) Å
c = 10.3618 (4) Å
V = 1557.00 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.30 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.664, T _max = 0.746
7603 measured reflections
2719 independent reflections
2502 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.075
S = 1.05
2719 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 830 Friedel pairs
Flack parameter: 0.09 (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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048361/sj5062sup1.cif

e-66-o3302-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048361/sj5062Isup2.hkl

e-66-o3302-Isup2.hkl^{(133.5KB, hkl)}

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

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

Cg1 is the centroid of the C14–C19 4-fluorophenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3ⁱ	0.95	2.46	3.379 (2)	163
C15—H15⋯F1ⁱⁱ	0.95	2.53	3.150 (3)	123
C16—H16⋯O3ⁱⁱⁱ	0.95	2.44	3.380 (2)	170
C4—H4⋯Cg1^iv	0.95	2.75	3.625 (3)	154

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

Acknowledgments

This work was supported by the Blue-Bio Industry RIC at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan City.

supplementary crystallographic information

Comment

Many compounds containing a naphthofuran moiety show diverse pharmacological properties such as antibacterial, antitumor and anthelmintic activities (Einhorn et al., 1984, Hranjec et al., 2003, Mahadevan & Vaidya, 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 3-arylsulfonyl-2-methylnaphtho[1,2-b]furan analogues (Choi et al., 2008a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle formed by the mean plane of the naphthofuran ring and the 4-fluorophenyl ring is 68.59 (5)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···O and C–H···F hydrogen bonds; the first one between a benzene H atom and the oxygen of the O═S═O unit (Table 1; C8–H8···O3ⁱ), and the second one between the 4–fluorophenyl H atom and the oxygen of the O═S═O unit (Table 1; C16–H16···O3ⁱⁱⁱ), and the third one between the 4-fluorophenyl H atom and the fluorine (Table 1; C15–H15···F1ⁱⁱ). The crystal packing (Fig. 3) is also exhibits an intermolecular C–H..π interaction between a benzene H atom and the 4-fluorophenyl ring (Table 1; C4–H4···Cg1^iv, Cg1 is the centroid of the C14-C19 4-fluorophenyl ring). The crystal packing (Fig. 3) is further stabilized by an aromatic π–π interaction between the central benzene and the outer benzene rings of neighbouring molecules. The Cg2···Cg3^viii distance is 3.650 (3) Å (Cg2 and Cg3 are the centroids of the C2/C3/C4/C5/C10/C11 benzene ring and the C5-C10 benzene ring, respectively).

Experimental

77% 3-chloroperoxybenzoic acid (493 mg, 2.2 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2-methylnaphtho [1,2-b]furan (339 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 439-440 K; R_f = 0.55 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.