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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812012603

. 2012 Mar 31;68(Pt 4):o1246. doi: 10.1107/S1600536812012603

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

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

PMCID: PMC3344175 PMID: 22606178

Abstract

In the title compound, C₁₉H₁₃BrO₂S, the 4-bromophenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphthofuran fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π interactions between the central naphthofuran benzene rings of neighbouring molecules [centroid–centroid distance = 3.483 (2) Å, interplanar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007 ▶, 2012 ▶).

Experimental

Crystal data

C₁₉H₁₃BrO₂S
M _r = 385.26
Triclinic,
a = 8.7124 (1) Å
b = 9.4857 (1) Å
c = 10.2898 (1) Å
α = 82.883 (1)°
β = 71.126 (1)°
γ = 75.672 (1)°
V = 778.74 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.78 mm⁻¹
T = 173 K
0.33 × 0.29 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.462, T _max = 0.517
14577 measured reflections
3853 independent reflections
3461 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.080
S = 1.05
3853 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.60 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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012603/sj5222sup1.cif

e-68-o1246-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012603/sj5222Isup2.hkl

e-68-o1246-Isup2.hkl^{(188.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012603/sj5222Isup3.cml

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
C19—H19⋯O2ⁱ	0.95	2.35	3.221 (2)	152

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfinyl (Choi et al., 2007) and 1-(4-methylphenylsulfinyl) (Choi et al., 2012) 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 0.024 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran fragment is 83.75 (4)°. In the crystal structure, molecules are linked via pairs of C—H···O hydrogen bonds (Fig. 2 & Table 1), forming inversion dimers. These dimers are connected by weak π–π interactions between the central naphthofuran benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.483 (2) Å and an interplanar distance of 3.416 (2) Å resulting in a slippage of 0.680 (2) Å (Fig. 2, Cg is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring).

Experimental

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 1-(4-bromophenylsulfanyl)-2-methylnaphtho [2,1-b]furan (295 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 466–467 K; R_f = 0.59 (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.