3-(4-Bromo­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812001973

. 2012 Jan 21;68(Pt 2):o481. doi: 10.1107/S1600536812001973

3-(4-Bromophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran

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

PMCID: PMC3275229 PMID: 22347085

Abstract

In the title compound, C₁₈H₁₇BrO₂S, the 4-bromophenyl ring makes a dihedral angle of 89.03 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₈H₁₇BrO₂S
M _r = 377.29
Orthorhombic,
a = 12.0900 (4) Å
b = 20.8119 (10) Å
c = 6.4865 (2) Å
V = 1632.11 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.65 mm⁻¹
T = 173 K
0.28 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.524, T _max = 0.857
8826 measured reflections
3658 independent reflections
2943 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.076
S = 0.99
3658 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▶), 1607 Friedel pairs
Flack parameter: 0.005 (8)

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/S1600536812001973/xu5447sup1.cif

e-68-0o481-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001973/xu5447Isup2.hkl

e-68-0o481-Isup2.hkl^{(179.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812001973/xu5447Isup3.cml

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

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

Cg1 and Cg2 are centroids of the C2–C7 benzene ring and the C13–C18 bromophenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.95	2.58	3.397 (3)	144
C10—H10B⋯Cg1ⁱⁱ	0.98	2.87	3.604 (3)	132
C12—H12B⋯Cg2ⁱⁱⁱ	0.98	2.84	3.671 (3)	143

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

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

Benzofuran analogues have drawn much attention owing to their valuable biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing study of 2,4,6,7-tetramethyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a) or 3-(4-chlorophenylsulfinyl) (Choi et al., 2010b) substituents, we report herein 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 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran fragment is 89.03 (6) °. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1, first entry). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions (Table 1, second & third entry, Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 4-bromophenyl ring, respectively).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (325 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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 colorless solid [yield 71%, m.p. 452–453 K; R_f = 0.46 (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.