2-(4-Bromo­phen­yl)-5,7-dimethyl-3-methyl­sulfanyl-1-benzofuran

The title compound, C17H15BrOS, was prepared by the Lewis acid-catalysed reaction of 2,4-dimethyl­phenol with 4′-bromo-2-chloro-2-(methyl­sulfan­yl)acetophenone. The 4-bromo­phenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 8.4 (1)°. The crystal structure is stabilized by a CH2—H⋯π inter­action between the 5-methyl group and the benzene ring of the benzofuran system

5-Bromo-2,4,6-trimethyl-3-methyl­sulfinyl-1-benzofuran

In the title compound, C12H13BrO2S, there are two symmetry-independent mol­ecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The methyl­sulfinyl group in mol­ecule B is disordered over two positions with site-occupancy factors fixed at 0.6 and 0.4. The crystal structure is stabilized by C—H⋯O hydrogen bonds and inter­molecular C—H⋯π inter­actions. In addition, the crystal structure exhibits C—Br⋯π inter­actions, with C—Br⋯Cg1 = 3.646 (8) Å where Cg1 is the centroid of the furan ring

3-(4-Chloro­phenyl­sulfon­yl)-2-methyl­naphtho[1,2-b]furan

The title compound, C19H13ClO3S, was prepared by the oxidation of 3-(4-chloro­phenyl­sulfan­yl)-2-methyl­naphtho[1,2-b]furan with 3-chloro­peroxy­benzoic acid. The 4-chloro­phenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π inter­actions between a methyl H atom and the furan ring of an adjacent mol­ecule. In addition, the crystal structure exhibits inter­molecular C—H⋯O inter­actions

3-(4-Bromo­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

In the title compound, C18H17BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 89.03 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions

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

In the title compound, C17H15BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 87.12 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions

3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[1,2-b]furan

In the title compound, C19H13FO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.650 (3) Å]

2-(4-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzofuran

In the title compound, C21H15FOS, the 4-fluoro­phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 24.3 (1)°. The dihedral angle between the phenyl ring and the benzofuran plane is 28.3 (1)°. The crystal structure may be stabilized by two very weak aromatic π–π inter­actions between the furan and the benzene rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.909 (4) and 4.028 (4) Å

5-Fluoro-2-methyl-3-phenyl­sulfonyl-1-benzofuran

There are two symmetry-independent mol­ecules, A and B, in the asymmetric unit of the title compound, C15H11FO3S. The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. In the crystal structure, the two independent mol­ecules are related by a pseudo-inversion center. The dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 80.2 (1)° in mol­ecule A and 80.7 (1)° in mol­ecule B. In the crystal structure, the A and B mol­ecules are linked by aromatic π–π inter­actions between the furan and benzene rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.671 (7) and 3.715 (7) Å. In addition, the crystal structure also exhibits two weak non-classical inter­molecular C—H⋯O hydrogen bonds

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

2,5-Bis(4-fluoro­phen­yl)-2-methyl­sulfanyl-1-benzofuran

The crystal studied of the title compound, C21H14F2OS, was an inversion twin with a 0.67 (8):0.33 (8) domain ratio. The 4-fluoro­phenyl ring in the 2-position makes a dihedral angle of 25.14 (6)° with the mean plane of the benzofuran fragment, and the dihedral angle between 4-fluoro­phenyl ring in the 5-position and the mean plane of the benzofuran fragment is 28.50 (7)°. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯F and C—H⋯π inter­actions