2-(5-Fluoro-3-isopropyl­sulfanyl-7-methyl-1-benzofuran-2-yl)acetic acid

The title compound, C14H15FO3S, was prepared by alkaline hydrolysis of ethyl 2-(5-fluoro-3-isopropyl­sulfanyl-7-methyl-1-benzofuran-2-yl)acetate. In the crystal, mol­ecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak C—H⋯O hydrogen bonds

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

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

In the title mol­ecule, C19H14O3S, the phenyl ring forms a dihedral angle of 69.13 (6)° with the plane of the naphthofuran fragment, being slightly tilted towards it. The crystal packing exhibits π–π inter­actions between the benzene rings from neighbouring mol­ecules [centroid–centroid distance = 3.616 (4) Å] and weak C—H⋯O and C—H⋯π inter­actions

2-(5-Cyclo­hexyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid

In the title compound, C17H20O3S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further stabilized by weak inter­molecular C—H⋯O hydrogen bonds. In addition, the crystal structure also exhibits aromatic π–π inter­actions between the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.505 (2) Å, inter­planar distance = 3.385 (2) Å and slippage = 0.909 (2) Å], and inter­molecular C—H⋯π inter­actions

2-(4-Fluoro­phen­yl)-1-(phenyl­sulfin­yl)­naphtho­[2,1-b]furan

In the title compound, C24H15FO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 19.43 (4)° with the mean plane of the naphtho­furan fragment. The dihedral angle between the phenyl ring and the mean plane of the naphtho­furan fragment is 85.83 (4)°. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds

2-(3-Ethyl­sulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid

The title compound, C18H16O3S, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit. The phenyl rings are rotated out of the benzofuran planes, making dihedral angles of 43.38 (7) and 56.13 (6)° in the two mol­ecules. The carboxyl groups are involved in inversion-related inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by weak non-classical inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits inter­molecular C—H⋯π inter­actions, and two aromatic π–π inter­actions between the furan rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.500 (3) and 3.605 (3) Å

Methyl 2-(5-methyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

The title compound, C13H14O4S, was prepared by oxidation of methyl 2-(5-methyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro­peroxy­benzoic acid. The O atom and methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The crystal structure is stabilized by inter­molecular aromatic π–π inter­actions between the benzene rings of neighbouring mol­ecules, with a centroid–centroid separation of 3.841 (3) Å