5-Iodo-7-methyl-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

In the title compound, C₁₇H₁₅IO₂S, the dihedral angle between the benzofuran group (r.m.s. deviation = 0.009 Å) and the 4-methylbenzene ring is 12.69 (5)°. In the crystal, mol­ecules are linked via pairs of I...O [I...O = 3.164 (1) Å, C—I...O = 166.63 (5)°] contacts into inversion-related dimers.

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

The asymmetric unit of the title compound, C₂₂H₁₇FOS, contains two independent mol­ecules (A and B). The dihedral angles between the benzo­furan ring systems [r.m.s. deviations of 0.026 (1), 0.004 (1) and 0.003 (1) Å, respectively, for mol­ecule A, and 0.002 (1), 0.004 (1) and 0.005 (1) Å for B] and the pendant 4-fluoro­phenyl and 4-methyl­phenyl rings are 39.48 (4) and 30.86 (5)°, respectively, for mol­ecule A, and 33.34 (6) and 20.99 (8)° for B. In the crystal, mol­ecules are linked by weak C—H...F and C—H...π inter­actions, resulting in a three-dimensional network.

3-(3-Bromo­phenyl­sulfin­yl)-5-cyclo­hexyl-2-methyl-1-benzo­furan

In the title compound, C₂₁H₂₁BrO₂S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.178 (2) Å] of the benzo­furan ring system and the mean plane of the 3-bromo­phenyl ring is 86.52 (6)°. In the crystal, mol­ecules are linked by weak C—H...O and C—H...π hydrogen bonds, and by a slipped π–π inter­action between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.518 (3) Å, inter­planar distance = 3.471 (3) Å and slippage = 0.573 (3) Å], resulting in a three-dimensional network.

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

In the title compound, C₁₇H₂₁BrO₂S, the cyclo­hexyl ring adopts a chair conformation and the aryl­sulfinyl unit is positioned equatorially relative to the cyclo­hexyl group. The benzo­furan unit is essentially planar, with an r.m.s. deviation of 0.016 (2) Å. In the crystal, mol­ecules are linked by weak C—H...O, C—H...π and Br...π [3.663 (2) Å] inter­actions, resulting in a three-dimensional network. A Br...Br [3.6838 (6) Å] contact is observed. The O atom of the sulfinyl group is disordered over two orientations with an occupancy ratio of 0.863 (5):0.137 (5).

5-Bromo-2-methyl-3-(3-methyl­phenyl­sulfin­yl)-1-benzo­furan

In the title compound, C₁₆H₁₃BrO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzo­furan ring system and the 3-methyl­phenyl ring is 84.83 (4)°. In the crystal, mol­ecules are linked via pairs of Br...O [3.240 (1) Å] contacts, forming inversion dimers. These dimers are linked by C—H...π inter­actions, forming a three-dimensional network.

3-(2-Bromo­phenyl­sulfon­yl)-5-cyclo­hexyl-2-methyl-1-benzo­furan

In the title compound, C₂₁H₂₁BrO₃S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo­furan and 2-bromo­phenyl fragments is 82.47 (5)°. In the crystal, mol­ecules related by inversion are paired into dimers via C—H...π and π–π inter­actions, the latter are indicated by the short distance of 3.607 (3) Å between the centroids of the furan rings. Inter­molecular C—H...O hydrogen bonds and short Br...O [3.280 (1) Å] contacts further consolidate the crystal packing.

5-Bromo-2,4,6-trimethyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzo­furan

In the title compound, C₁₈H₁₇BrO₂S, the dihedral angle between the methyl­phenyl ring and the mean plane of the benzo­furan rung system is 87.0 (2)°. In the crystal, mol­ecules related by inversion are paired into dimers via C—H...O and C—H...π inter­actions. These dimers are further linked by C—H...O hydrogen bonds and π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.555 (5) Å], resulting in a three-dimensional supra­molecular network.

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

In the title compound, C₂₀H₁₆O₃S, the dihedral angle between the mean planes of the naphtho­furan and 3-methyl­phenyl fragments is 88.56 (2)°. In the crystal, mol­ecules are linked via pairs of C—H...O hydrogen bonds, forming inversion dimers. These dimers are linked by π–π inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.701 (2) Å] into supra­molecular chains running along the a-axis direction.

5-Bromo-2,4,6-trimethyl-3-(3-methyl­phenyl­sulfin­yl)-1-benzo­furan

In the title compound, C₁₈H₁₇BrO₂S, the dihedral angle between the mean plane of the benzo­furan ring system and the benzene ring is 68.58 (4)°. In the crystal, mol­ecules are linked via pairs of C—H...O hydrogen bonds into inversion dimers. These dimers are linked by C—H...O hydrogen bonds and π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.783 (1) Å], forming a three-dimensional network. In addition, the stacked mol­ecules exhibit inversion-related S...O contacts [3.153 (1) Å] involving the sulfinyl groups.

5-Chloro-3-ethyl­sulfinyl-7-methyl-2-(4-methyl­phen­yl)-1-benzo­furan

In the title compound, C₁₈H₁₇ClO₂S, the dihedral angle between the mean planes of the benzo­furan ring system and the methyl­phenyl ring is 14.50 (4)°. The centroid–centroid distances between the benzene and the methyl­phenyl rings are 3.827 (2) and 3.741 (2) Å, while the centroid–centroid distance between the furan and methyl­phenyl rings is 3.843 (2) Å. These distances indicate π–π inter­actions; on the other hand, the inter­planar angles between the benzene and methyl­phenyl rings, and between the furan and methyl­phenyl rings are 13.89 (4) and 15.53 (4)°, respectively. In the crystal, the mol­ecules stack along the a-axis direction.

5-Bromo-3-ethyl­sulfinyl-7-methyl-2-(4-methyl­phen­yl)-1-benzo­furan

In the title compound, C₁₈H₁₇BrO₂S, the dihedral angle between the mean planes of the benzo­furan and 4-methyl­phenyl rings is 14.54 (5)°. In the crystal, mol­ecules are linked via pairs of π–π inter­actions between the benzene and 4-methyl­phenyl rings, with centroid–centroid distances of 3.811 (3) and 3.755 (3) Å. A similar inter­action is found between the furan and 4-methyl­phenyl rings, with a centroid–centroid distance of 3.866 (3) Å between neighbouring mol­ecules. The mol­ecules are stacked along the a-axis direction. In addition, a short Br...O contact distance of 3.128 (2) Å is observed between inversion-related dimers.

5-Cyclo­hexyl-3-(2-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzo­furan

In the title compound, C₂₁H₂₁FO₃S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo­furan ring system and the fluoro­phenyl ring is 87.61 (3)°. In the crystal, mol­ecules related by inversion are linked into dimers via pairs of C—H...π inter­actions. These dimers are further linked by π–π inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.407 (2) Å and between the 2-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.742 (2) Å], resulting in a three-dimensional supra­molecular network.

5-Cyclo­pentyl-2-methyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₂₁H₂₂O₃S, the five-membered ring adopts an envelope conformation with the ipso atom deviating by 0.596 (2) Å from the plane through the rest of the ring atoms. The dihedral angle between the mean planes of the benzo­furan and m-tolyl moieties is 78.4 (1)°. In the crystal, mol­ecules related by a glide plane are linked via C—H...O hydrogen bonds into chains along the a-axis direction. These chains are in turn connected by C—H...π inter­actions into layers parallel to the ac plane.

5-Fluoro-2-methyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₁₆H₁₃FO₃S, the dihedral angle between the mean planes of the benzo­furan ring system and the 3-methyl­phenyl ring is 80.96 (4)°. In the crystal, mol­ecules are linked via pairs of π–π inter­actions between furan and benzene rings, with centroid–centroid distances of 3.758 (1) and 3.771 (1) Å. A similar inter­action is found between furan rings, with a centroid–centroid distance of 3.661 (1) Å between neighbouring mol­ecules. The mol­ecules stack along the a-axis direction. In addition, C—H...O and C—H...π hydrogen bonds are observed between inversion-related dimers.

5-Cyclo­hexyl-2-methyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₂₂H₂₄O₃S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzo­furan ring system and the benzene ring is 81.78 (4)°. In the crystal, mol­ecules are linked via pairs of C—H...π inter­actions into inversion dimers. These dimers are further linked by C—H...π inter­actions into supra­molecular chains running along the b-axis direction. In addition, C—H...O hydrogen bonds are observed between inversion-related dimers.

5-Bromo-2,7-dimethyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the mean planes of the benzo­furan and 4-methyl­phenyl rings is 76.43 (5)°. In the crystal, mol­ecules are linked via pairs of C—H...O hydrogen bonds into inversion dimers that are further linked by Br...Br [3.6517 (4) Å] contacts about inversion centers into supra­molecular sheets that lie parallel to (111).

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

In the title compound, C₁₇H₁₅FO₃S, the dihedral angle between the mean planes of the benzo­furan and 2-fluoro­phenyl rings is 87.61 (4) Å. In the crystal, mol­ecules are linked via pairs of C—H...π inter­actions into inversion-related dimers. These dimers are linked by C—H...O hydrogen bonds into supra­molecular chains running along the a-axis direction.

5-Bromo-2,7-dimethyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the mean planes of the benzo­furan and 3-methyl­phenyl rings is 77.37 (5)°. In the crystal, mol­ecules are linked via pairs of Br...O [Br...O = 3.335 (2) Å] contacts into inversion dimers. These dimers are further linked by C—H...O hydrogen bonds and π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid separation = 3.884 (3) Å] into supra­molecular chains running along the a-axis direction.

5-Chloro-2,7-dimethyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₁₇H₁₅ClO₃S, the dihedral angle between the mean planes of the benzo­furan and 3-methyl­phenyl rings is 76.99 (4)°. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds into chains along the b-axis direction. These chains are linked by π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.976 (2) Å].

5-Cyclo­pentyl-2-methyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₂₁H₂₂O₃S, the cyclo­pentyl ring adopts a twist conformation. The dihedral angle between the mean planes of the benzo­furan and 4-methyl­phenyl rings is 72.38 (6)°. In the crystal, mol­ecules are linked by C—H...O and C—H...π inter­actions, forming a three-dimensional supra­molecular network.

5-Bromo-3-ethyl­sulfinyl-2-(4-methyl­phen­yl)-1-benzo­furan

In the title compound, C₁₇H₁₅BrO₂S, the dihedral angle between the plane of the benzo­furan ring system [r.m.s. deviation = 0.004 (3) Å] and that of the 4-methyl­phenyl ring is 0.9 (2)°. In the crystal, mol­ecules are linked by C—H...O, C—H...π and Br...π [3.636 (2) Å] inter­actions, and by π–π inter­actions between the 4-methyl­phenyl and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.650 (2) Å], forming a three-dimensional network.

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

In the title compound, C₁₅H₁₀F₂O₂S, the dihedral angle between the plane of the benzo­furan ring system (r.m.s. deviation = 0.015 Å) and that of the 2-fluoro­phenyl ring is 28.53 (6)°. In the crystal, mol­ecules are linked by C—H...O and C—H...F hydrogen bonds, and by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.625 (2) Å], forming a three-dimensional network.

3-(4-Fluoro­phenyl­sulfin­yl)-2,4,5,6-tetra­methyl-1-benzo­furan

In the title compound, C₁₈H₁₇FO₂S, the dihedral angle between the plane of the benzo­furan ring system (r.m.s. deviation = 0.013 Å) and that of the 4-fluoro­phenyl ring is 74.30 (5)°. In the crystal, weak C—H...O and C—H...F hydrogen bonds link the mol­ecules into columns extending in direction [100].