5-Bromo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(20)H(13)BrO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl 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)°].

5-Fluoro-2-(4-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(15)H(10)F(2)O(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-fluoro-phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 28.09 (3)°.

5-(4-Bromo-phen-yl)-2-(3,4-methyl-ene-dioxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran.

The title compound, C(22)H(15)BrO(3)S, crystallizes with four mol-ecules in the asymmetric unit. The 4-bromo-phenyl rings are rotated out of the benzofuran planes, with dihedral angles for the four mol-ecules of 20.8 (2), 17.

Methyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran-2-yl]acetate.

In the title compound, C(18)H(16)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52 (6)°. The methyl group of the methyl-sulfanyl substituent is almost perpendicular to the plane of the benzofuran fragment [100.

2-(4-Bromo-phen-yl)-5,6-methyl-enedi-oxy-3-phenyl-sulfinyl-1-benzofuran benzene solvate.

In the title compound, C(21)H(13)BrO(4)S·C(6)H(6), the O atom and the phenyl group of the phenyl-sulfinyl substituent are located on opposite sides of the mean plane of the 5,6-methyl-enedioxy-benzofuran fragment; the phenyl ring is almost perpendicular to this plane [83.66 (6)°]. The 4-bromo-phenyl ring is rotated slightly out of the 5,6-methyl-enedioxy-benzo-furan plane, making a dihedral angle of 2.

Isopropyl 2-(5-fluoro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(14)H(15)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl 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 inter-molecular non-classical C-H⋯O hydrogen bonds.

2-(3-Ethyl-sulfanyl-5-fluoro-1-benzofuran-2-yl)acetic acid.

The title compound, C(12)H(11)FO(3)S, was prepared by alkaline hydrolysis of ethyl 2-(3-ethyl-sulfan-yl-5-fluoro-1-benzofuran-2--yl) acetate. In the crystal structure, the carboxyl groups are involved in inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by aromatic π-π inter-actions between the furan ring and the benzene ring of neighbouring benzofuran ring systems [centroid-centroid distance = 3.

5-Bromo-2,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(11)H(11)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by non-classical inter-molecular C-H⋯O hydrogen bonding, and by inter-molecular C-Br⋯π inter-actions, with C-Br⋯Cg = 3.629 Å (Cg is the centroid of the benzene ring).

5-(4-Bromo-phen-yl)-2-methyl-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(16)H(13)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 4-bromo-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 39.23 (8)°.

2-(5-Methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetic acid.

In the title compound, C(12)H(12)O(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment. In the crystal structure, inter-molecular C-H⋯O and O-H⋯O hydrogen-bonding inter-actions are found. The structure also exhibits aromatic π-π inter-actions between the furan and benzene rings [centroid-centroid distance = 3.

Isopropyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran-2-yl]acetate.

In the title compound, C(20)H(20)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the plane of the benzofuran unit by 32.87 (8)°. The S-C(meth-yl) bond is almost perpendicular to the plane of the benzofuran fragment [77.

2-(3-Ethyl-sulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid.

The title compound, C(18)H(16)O(3)S, crystallizes with two symmetry-independent mol-ecules in the asymmetric unit. The phenyl rings are rotated out of the benzofuran planes, making dihedral angles of 43.38 (7) and 56.

5-Fluoro-2-(4-iodo-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(15)H(10)FIO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-iodo-phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 39.4 (1)°.

Methyl 2-(5-fluoro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(12)H(11)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment [O-S-C-C and C-S-C-C torsion angles = 126.70 (13) and -123.55 (13)°, respectively].

2-(4-Bromo-phen-yl)-5-fluoro-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(15)H(10)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-bromo-phenyl ring is rotated out of the benzofuran plane [dihedral angle = 38.98 (8)°], while the structure is stabilized by an inter-molecular C-H⋯O hydrogen bond and a Br⋯O halogen bond [3.

Isopropyl 2-(5-chloro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(14)H(15)ClO(4)S, the S atom has a distorted trigonal-pyramidal coordination. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the benzofuran ring system. The crystal structure is stabilized by intermolecular aromatic π-π interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 4.

Propyl 2-(5-iodo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(14)H(15)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions between an H atom of the propyl methyl-ene group closest to the carboxyl-ate O atom and the benzene ring of a neighbouring mol-ecule, and between an H atom of the outer propyl methyl-ene group and the furan ring of a neighbouring mol-ecule, respectively. Additionally, the crystal structure exhibits inter-molecular C-H⋯O hydrogen bonds.

Isopropyl 2-(5-iodo-7-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title mol-ecule, C(15)H(17)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal structure, inter-molecular I⋯O [2.994 (3) Å] halogen bonding links the mol-ecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by inter-molecular sulfin-yl-sulfinyl inter-actions [S⋯O 3.

Methyl 2-(5-bromo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

The title compound, C(12)H(11)BrO(4)S, was synthesized by the oxidation of methyl 2-(5-bromo-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by C-H⋯π inter-actions, involving a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

Isopropyl 2-(5-iodo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(14)H(15)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by C-H⋯π inter-actions between a methyl H atom and the benzene ring of an adjacent mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

Isopropyl 2-(5-bromo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title compound, C(14)H(15)BrO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by C-H⋯π inter-actions between a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

Isopropyl 2-(4,6-dimethyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Mol-ecules of title compound, C(16)H(20)O(4)S, which was synthesized by the oxidation of isopropyl 2-(4,6-dimethyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate, inter-act through C-H⋯π inter-actions between a methyl-ene H atom and the aromatic carbon ring of the benzofuran ring system, and by C-H⋯O hydrogen bonds. Adjacent stacked mol-ecules exhibit a carbon-yl-carbonyl inter-action [3.295 (2) Å].

Methyl 2-(5-chloro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

The title compound, C(12)H(11)ClO(4)S, was prepared by the oxidation of methyl 2-(5-chloro-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.

5-Bromo-2,4,6-trimethyl-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(12)H(13)BrO(2)S, there are two symmetry-independent mol-ecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.

Isopropyl 2-(5-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

The title compound, C(15)H(18)O(4)S, was prepared by the oxidation of isopropyl 2-(5-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The crystal structure is stabilized by inter-molecular π-π inter-actions between the benzene rings; the centroid-centroid distance between the adjacent benzene rings (symmetry code: ) is 3.713 (2) Å.