Crystal structure of 5-chloro-3-cyclo­hexyl­sulfinyl-2,4,6-trimethyl-1-benzo­furan

Hong Dae Choi; Uk Lee

doi:10.1107/S1600536814019217

. 2014 Aug 30;70(Pt 9):o1067–o1068. doi: 10.1107/S1600536814019217

Crystal structure of 5-chloro-3-cyclohexylsulfinyl-2,4,6-trimethyl-1-benzofuran

Hong Dae Choi ^a, Uk Lee ^b,^*

PMCID: PMC4186066 PMID: 25309229

Abstract

In the title compound, C₁₇H₂₁ClO₂S, the cyclohexyl ring adopts a chair conformation with the C—S bond in an equatorial orientation. In the crystal, molecules are linked by C—H⋯O and C—H⋯π hydrogen bonds and a Cl⋯π [3.594 (2) Å] contact into chains along the a-axis direction.

Keywords: crystal structure, benzofuran, cyclohexyl, C—H⋯O hydrogen bonds, C—H⋯π interactions

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Howlett et al. (1999 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₂₁ClO₂S
M _r = 324.85
Triclinic,
a = 5.8612 (1) Å
b = 11.6832 (2) Å
c = 12.6432 (2) Å
α = 65.292 (1)°
β = 85.902 (1)°
γ = 83.229 (1)°
V = 780.79 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 K
0.31 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.892, T _max = 0.917
13925 measured reflections
3588 independent reflections
3221 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.102
S = 1.03
3588 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.37 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/S1600536814019217/hb7277sup1.cif

e-70-o1067-sup1.cif^{(420.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019217/hb7277Isup2.hkl

e-70-o1067-Isup2.hkl^{(175.9KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814019217/hb7277Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S1600536814019217/hb7277fig1.tif

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(1.6MB, tif)}

x y z x y z . DOI: 10.1107/S1600536814019217/hb7277fig2.tif

A view of the C—H⋯O, C—H⋯π and C—Cl⋯π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x − 1, y, z; (ii) x + 1, y, z.]

CCDC reference: 1021106

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

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

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2ⁱ	0.98	2.53	3.438 (2)	154
C12—H12⋯O2ⁱ	1.00	2.39	3.3072 (19)	152
C11—H11b⋯Cg2ⁱ	0.98	2.83	3.533 (2)	129

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Symmetry code: (i) Inline graphic .

Acknowledgments

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

supplementary crystallographic information

S1. Comment

Benzofuran compounds show significant pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Khan et al. , 2005), and inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These many benzofurans occur in a great number of natural products (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 5-chloro-3-cyclohexylsulfinyl-1-benzofuran derivatives containing methyl substituent in 2-position (Choi et al., 2011), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form and the arylsulfinyl moiety is positioned equatorially relative to the cyclohexyl group. In the crystal structure (Fig. 2), molecules are linked by C—H···O and C—H···π hydrogen bonds (Table 1, Cg2 is the centroid of the C2–C7 benzene ring). The molecules are stacked along the a-axis. A Cl···π contact between the chlorine atom and the furan ring of an adjacent molecule, with Cl1···Cg1ⁱ [3.594 (2) Å] (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring) is observed, compared to the van der Waals' separation of 3.55Å for these species.

S2. Experimental

The starting material 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran (278 mg, 0.9 mmol) in dichloromethane (20 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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 77% (250 mg); m.p. 449–450 K; R_f = 0.61 (hexane–ethyl acetate, 2:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound (26 mg) in ethyl acetate (10 ml) at room temperature.