1-(4-Bromo­phenyl­sulfin­yl)-2-methyl­naphtho­[2,1-b]furan

In the title compound, C19H13BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho­furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.483 (2) Å, inter­planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å]

5-Cyclo­hexyl-2-methyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzofuran

In the title compound, C22H24O2S, the cyclo­hexyl ring adopts a chair conformation. The 4-methyl­phenyl ring makes a dihedral angle of 81.60 (5)° with the mean plane [r.m.s. deviation = 0.004 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and weak π–π inter­actions between the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.545 (2) Å, inter­planar distance = 3.489 (2) Å and slippage = 0.628 (2) Å

2-Methyl-1-(4-methyl­phenyl­sulfinyl)naphtho­[2,1-b]furan

In the title compound, C20H16O2S, the 4-methyl­phenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and by a slipped π–π inter­action between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid-to-centroid distance = 3.671 (2) Å, inter­planar distance = 3.349 (2) Å and slippage = 1.503 (2)°]

3-(4-Bromo­phenyl­sulfin­yl)-2,5,7-trimethyl-1-benzofuran

In the title compound, C17H15BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 87.78 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, and by weak inter­molecular C—S⋯π [3.399 (2) Å] and C—Br⋯π [3.797 (2) and 3.757 (2) Å] inter­actions

3-(3-Chloro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

In the title compound, C17H15ClO2S, the 3-chloro­phenyl ring makes a dihedral angle of 71.46 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and a slipped π–π inter­action between the 3-chloro­phenyl rings of adjacent mol­ecules [centroid–centroid distance = 3.630 (2) Å, inter­planar distance = 3.375 (2) Å and slippage = 1.337 (2) Å]

2-(3-Fluoro­phen­yl)-5-iodo-7-methyl-3-methyl­sulfinyl-1-benzofuran

In the title compound, C16H12FIO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 34.93 (7)° with the mean plane [r.m.s. deviation = 0.019 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked via pairs of I⋯O contacts [3.088 (2) Å] into inversion dimers. These dimers are connected by weak C—H⋯O hydrogen bonds

3-(3-Chloro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzofuran

In the title compound, C17H15ClO3S, the 3-chloro­phenyl ring makes a dihedral angle of 77.76 (6)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions

5-Cyclo­hexyl-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran

In the title compound, C21H21FO2S, the cyclo­hexyl ring adopts a chair conformation. The 3-fluoro­phenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds