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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814005157

. 2014 Mar 12;70(Pt 4):o416. doi: 10.1107/S1600536814005157

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

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

PMCID: PMC3998563 PMID: 24826129

Abstract

In the title compound, C₂₀H₁₆O₃S, the dihedral angle between the mean planes of the naphthofuran and 3-methylphenyl fragments is 88.56 (2)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked by π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.701 (2) Å] into supramolecular chains running along the a-axis direction.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2012a ▶,b ▶).

Experimental

Crystal data

C₂₀H₁₆O₃S
M _r = 336.39
Monoclinic,
a = 11.1667 (2) Å
b = 7.7400 (1) Å
c = 18.4736 (3) Å
β = 98.683 (1)°
V = 1578.38 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.51 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.697, T _max = 0.746
15253 measured reflections
3946 independent reflections
3390 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.117
S = 1.05
3946 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.52 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 for Windows (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/S1600536814005157/zq2218sup1.cif

e-70-0o416-sup1.cif^{(26.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005157/zq2218Isup2.hkl

e-70-0o416-Isup2.hkl^{(193.4KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814005157/zq2218Isup3.cml

CCDC reference: 990319

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2ⁱ	0.98	2.54	3.507 (2)	171

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

1. Comment

As a part of our continuing study of 2-methylnaphtho[2,1-b]furan derivatives containing phenylsulfonyl (Choi et al., 2008), 4-methylphenylsulfonyl (Choi et al., 2012a) and 4-bromophenylsulfonyl (Choi et al., 2012b) substituents in 1-position, we report here the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.025 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.014 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the naphthofuran ring system and the 3-methylphenyl ring is 88.56 (2)°. In the crystal structure (Fig. 2), molecules are connected via pairs of C–H···O hydrogen bonds (Table 1), forming inversion dimers. These dimers are further packed by π–π interactions between the furan rings of neighbouring molecules, with a Cg1···Cg1ⁱⁱ distance of 3.701 (2) Å and an interplanar distance of 3.503 (2) Å resulting in a slippage of 1.194 (2) Å (Cg1 is the centroid of the C1/C2/C11/O1/C12 furan ring), forming supramolecular chains running along the a-axis direction.

2. Experimental

3-Chloroperoxybenzoic acid (77%, 538 mg, 2.4 mmol) was added in small portions to a stirred solution of 2-methyl-1-(3-methylphenylsulfanyl)naphtho[2,1-b]furan (334 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, 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 72%, m.p. 424-425 K; R_f = 0.52 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.