7-Bromo-1-(3-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812040470

. 2012 Sep 29;68(Pt 10):o3047. doi: 10.1107/S1600536812040470

7-Bromo-1-(3-fluorophenylsulfonyl)-2-methylnaphtho[2,1-b]furan

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

PMCID: PMC3470396 PMID: 23125809

Abstract

In the title compound, C₁₉H₁₂BrFO₃S, the 3-fluorophenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphthofuran fragment. In the crystal, molecules are linked by slipped π–π interactions between the furan and the outer benzene rings of neighbouring molecules [centroid–centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2011 ▶).

Experimental

Crystal data

C₁₉H₁₂BrFO₃S
M _r = 419.26
Triclinic,
a = 7.7141 (2) Å
b = 8.1619 (2) Å
c = 13.4046 (4) Å
α = 74.277 (2)°
β = 86.410 (2)°
γ = 89.044 (2)°
V = 810.80 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.573, T _max = 0.746
15010 measured reflections
4031 independent reflections
3483 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.075
S = 1.06
4031 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812040470/rk2381sup1.cif

e-68-o3047-sup1.cif^{(25KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040470/rk2381Isup2.hkl

e-68-o3047-Isup2.hkl^{(197.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812040470/rk2381Isup3.cml

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

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

supplementary crystallographic information

Comment

As a part of our ongoing study of 7-bromo-2-methylnaphtho[2,1-b]furan derivatives containing 1-(4-methylphenylsulfonyl) (Choi et al., 2008) and 1-(4-fluorophenylsulfonyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.009 (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 3-fluorophenyl ring is 80.85 (5)°. In the crystal structure (Fig. 2), molecules are connected by slipped π···π interactions between the furan and outer benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱ distance of 3.756 (3)Å and an interplanar distance of 3.563 (3)Å resulting in a slippage of 1.189 (3)Å (Cg1 and Cg2 are the centroids of the C1/C2/C11/O1/C12 furan ring and the C3–C8 benzene ring, respectively). Symmetry code: (i) -x+2, -y+1, -z+1.

Experimental

The 77% 3-chloroperoxybenzoic acid (336 mg, 1.5 mmol) was added in small portions to a stirred solution of 7-bromo-1-(3-fluorophenylsulfanyl)-2-methylnaphtho[2,1-b]furan (271 mg, 0.7 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10 h, 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 (benzene) to afford the title compound as a colourless solid - yield 67%, m.p. 472–473 K; Rf = 0.68 (benzene). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.