1-Cyclo­hexyl­sulfinyl-2-methyl­naphtho­[2,1-b]furan

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

doi:10.1107/S1600536811010981

. 2011 Mar 31;67(Pt 4):o1002. doi: 10.1107/S1600536811010981

1-Cyclohexylsulfinyl-2-methylnaphtho[2,1-b]furan

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

PMCID: PMC3100045 PMID: 21754023

Abstract

In the title compound, C₁₉H₂₀O₂S, the cyclohexyl ring adopts a chair conformation and the arylsulfinyl unit is positioned equatorial relative to the cyclohexyl group. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.923 (3) and 0.077 (3).

Related literature

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For structural studies of related 2-methylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C₁₉H₂₀O₂S
M _r = 312.41
Monoclinic,
a = 5.8424 (1) Å
b = 19.5900 (3) Å
c = 13.4314 (2) Å
β = 92.649 (1)°
V = 1535.62 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.42 × 0.34 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.916, T _max = 0.946
14260 measured reflections
3527 independent reflections
3026 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.104
S = 1.06
3527 reflections
210 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.49 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 datablocks global, I. DOI: 10.1107/S1600536811010981/fl2340sup1.cif

e-67-o1002-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010981/fl2340Isup2.hkl

e-67-o1002-Isup2.hkl^{(173KB, 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
C13—H13B⋯O2Bⁱ	0.98	2.12	2.848 (6)	130
C14—H14⋯O2Aⁱⁱ	1.00	2.38	3.2947 (19)	152

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

supplementary crystallographic information

Comment

Many compounds containing a naphthofuran ring have attracted much attention owing to their potent 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 2-methylnaphtho[2,1-b]furan analogues (Choi et al., 2006, 2007), 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 0.014 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The cyclohexyl ring is in the chair form and arylsulfinyl moiety is positioned equatorial relative to the cyclohexyl group. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement, of 0.923 (3) (part A) and 0.077 (3) (part B). The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and and one of the disordered sulfinyl oxygen atoms(Table 1; C13—H13B···O2Bⁱ), and the second one between a cyclohexyl H atom and the other disordered sulfinyl oxygen (Table 1; C14—H14···O2Aⁱⁱ).

Experimental

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 1-cyclohexylsulfanyl-2-methylnaphtho[2,1-b] furan (355 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with a 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 74%, m.p. 429–430 K; R_f = 0.61 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation frroomm acetone at room temperature