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

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

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

The title compound, C12H11FO3S, was prepared by alkaline hydrolysis of ethyl 2–(3–ethyl­sulfan­yl–5–fluoro–1–benzofuran–2–­yl) acetate. In the crystal structure, the carboxyl groups are involved in 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 aromatic π–π inter­actions between the furan ring and the benzene ring of neighbouring benzofuran ring systems [centroid–centroid distance = 3.684 (5) Å]

5-Fluoro-2-(4-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran

In the title compound, C15H10F2O2S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-fluoro­phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 28.09 (3)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O and C—H⋯F hydrogen bonds

5-Bromo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran

In the title compound, C20H13BrO2S, the O atom and the phenyl group of the phenyl­sulfinyl substituent are located on opposite sides of the plane of the benzofuran system. The S-bound phenyl ring is almost perpendicular to this plane [80.35 (8)°]. The phenyl ring in the 2-position is twisted with respect to the benzofuran plane, making a dihedral angle of 16.0 (1)°

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

There are two mol­ecules in the asymmetric unit of the title compound, C14H16O3S. In the crystal structure, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the a axis by aromatic π–π inter­actions between the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.430 (4) Å] and by additional C—H⋯π and C—H⋯O inter­actions

3-Cyclo­hexyl­sulfonyl-5-iodo-2,7-dimethyl-1-benzofuran

In the title compound, C16H19IO3S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, pairs of inter­molecular I⋯O contacts [3.269 (2) Å] link the mol­ecules into inversion dimers. These dimers are further stabilized by a slipped π–π inter­action between the benzene and furan rings of adjacent mol­ecules [centroid–centroid distance = 3.701 (3) Å, inter­planar distance = 3.372 (3) Å and slippage = 1.525 (3) Å]

2-(4-Chloro­phen­yl)-3-ethyl­sulfinyl-5-iodo-7-methyl-1-benzofuran

In the title compound, C17H14ClIO2S, the 4-chloro­phenyl ring makes a dihedral angle of 12.13 (5)° with the mean plane of the benzofuran ring. In the crystal, pairs of inter­molecular I⋯O contacts [3.145 (1) Å] link the mol­ecules into inversion dimers

Isopropyl 2-(5-fluoro-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

In the title compound, C14H15FO4S, the O atom and the methyl group of the methyl­sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment which is essentially planar with a mean deviation of 0.008 (1) Å from its least-squares plane. The crystal structure stabilized by three different inter­molecular non-classical C—H⋯O hydrogen bonds. The crystal structure also exhibits aromatic π–π inter­actions between the benzene rings of adjacent benzofuran ring systems [centroid–centroid distance = 3.688 (2) Å

2,5,7-Trimethyl-3-phenyl­sulfinyl-1-benzo­furan

The title compound, C17H16O2S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenyl­sulfanyl-1-benzofuran with 3-chloro­peroxy­benzoic acid. The O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [88.30 (9)°] and is tilted slightly towards it. No π–π or C—H⋯π inter­actions are observed between neighbouring mol­ecules in the crystal structure because of steric hindrance induced by the three methyl groups