Research Article: 3-(4-Bromo­phenyl­sulfon­yl)-5-cyclo­hexyl-2-methyl-1-benzofuran

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Hong Dae Choi, Pil Ja Seo, Uk Lee.


In the title compound, C21H21BrO3S, the cyclo­hexyl ring adopts a chair conformation. The 4-bromo­phenyl ring makes a dihedral angle of 80.88 (6)° with the mean plane of the benzofuran fragment. An intra­molecular C—H⋯O hydrogen bond is formed between an O atom of the sulfonyl group and one H atom of the aromatic ring such that a five-membered ring is formed. The crystal packing is stabilized by an inter­molecular C—H⋯O hydrogen bond, which links the mol­ecules into chains with graph-set notation C(6) running parallel to the c axis, and π–π stacking inter­actions [centroid–centroid distance = 3.6129 (12) Å].

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For the biological 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. (2011 ▶); Seo et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).