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

In the title compound, C₁₇H₁₅BrO₂S, the 4-methyl­benzene ring makes a dihedral angle of 89.01 (7)° with the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked into supra­molecular layers that stack along [001] by weak C—H...O, C—H...π and C—S...π [3.364 (2) Å] inter­actions.

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

In the title compound, C₂₁H₁₅FOS, the dihedral angles between the mean plane [r.m.s. deviation = 0.041 (1) Å] of the benzo­furan fragment and the pendant 2-fluoro­phenyl and phenyl rings are 46.09 (3) and 24.34 (5)°, respectively. In the crystal, mol­ecules are linked by weak C—H...π inter­actions, forming a three-dimensional network.

3-(4-Bromo­phenyl­sulfin­yl)-5-chloro-2,7-dimethyl-1-benzo­furan

In the title compound, C₁₆H₁₂BrClO₂S, the 4-bromo­phenyl ring makes a dihedral angle of 88.84 (5)° with the mean plane [r.m.s. deviation = 0.009 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H...O and C—S...π [3.386 (2) Å] inter­actions, forming a chain perpendicular to the bc plane.

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

In the title compound, C₁₅H₁₀BrFO₂S, the 2-fluoro­phenyl ring makes a dihedral angle of 32.28 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds and Br...O contacts [3.0917 (13) Å], forming a three-dimensional network.

2,5-Dimethyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

In the title compound, C₁₇H₁₆O₃S, the dihedral angle between the 4-methyl­phenyl ring and the mean plane [r.m.s. deviation = 0.011 (1) Å] of the benzo­furan ring system is 71.47 (5)°. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds, and by slipped π–π inter­actions between the benzo­furan ring systems of neighbouring mol­ecules [centroid–centroid distances = 3.638 (2) and 3.766 (2) Å, inter­planar distances = 3.564 (2) and 3.454 (2) Å, and slippages = 0.730 (2) and 1.501 (2) Å], forming a three-dimensional network.

2-(4-Fluoro­phen­yl)-5-iodo-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

In the title compound, C₂₁H₁₄FIO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzo­furan fragment and the pendant 4-fluoro­phenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal, mol­ecules are linked by pairs of C—H...I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H...O hydrogen bonds. In addition, the stacked mol­ecules exhibit inversion-related S...O contacts [2.9627 (14) Å] involving the sulfinyl groups.

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

In the title compound, C₁₇H₁₅FO₂S, the benzo­furan ring system, being essentially planar, with an r.m.s. deviation from the least-squares plane of 0.009 (2) Å, makes a dihedral angle of 79.02 (5)° with the plane of the 2-fluoro­phenyl group. In the crystal, mol­ecules are linked by pairs of weak C—H...O hydrogen bonds into centrosymmetric dimers.

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

In the title compound, C₂₁H₂₁FO₂S, the cyclo­hexyl ring adopts a chair conformation. The 2-fluoro­benzene ring makes a dihedral angle of 38.68 (6)° with the mean plane [r.m.s. deviation = 0.018 (2) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by pairs of C—H...O hydrogen bonds into dimers, which are further packed into stacks along the c axis by C—H...O hydrogen bonds. In addition, the stacked mol­ecules exhibit S...O contacts [3.1733 (13) Å] involving the sulfinyl groups. The F atom is disordered over two positions, with site-occupancy factors of 0.961 (3) and 0.039 (3).

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

In the title compound, C₂₁H₂₁FO₂S, the cyclo­hexyl ring adopts a chair conformation. The 2-fluoro­phenyl ring makes a dihedral angle of 88.47 (4)° with the mean plane [r.m.s. deviation = 0.013 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H...O and C—H...π inter­actions, forming chains propagating along [100]. The crystal structure also exhibits slipped π–π inter­actions between the furan rings of neighboring mol­ecules [centroid-to-centroid distance = 3.397 (2) Å, inter­planar distance = 3.346 (2) Å and slippage = 0.586 (2) Å].

5-Chloro-2-(4-fluoro­phen­yl)-7-methyl-3-methyl­sulfinyl-1-benzo­furan

In the title compound, C₁₆H₁₂ClFO₂S, the 4-fluoro­phenyl ring makes a dihedral angle of 16.43 (4)° with the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by pairs of Cl...O contacts [3.1839 (12) Å] into inversion dimers, which are further packed into stacks along the b axis by weak C—H...O hydrogen bonds.

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

In the title compound, C₁₇H₁₅FO₂S, the 2-fluoro­phenyl ring makes a dihedral angle of 87.53 (5)° with the mean plane [r.m.s. deviation = 0.013 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H...F, C—H...O and C—H...π inter­actions, forming a three-dimensional network.

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

In the title compound, C₂₁H₂₁FO₂S, the cyclo­hexyl ring adopts a chair conformation. The 3-fluoro­phenyl ring makes a dihedral angle of 83.16 (4)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo­furan ring system. In the crystal, mol­ecules are linked by pairs of C—H...π inter­actions into inversion dimers, which are further packed into stacks along the a-axis direction by C—H...π inter­actions.

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

The title compound, C₁₆H₁₃ClO₃S, crystallized with two independent mol­ecules in the asymmetric unit. The 4-methyl­phenyl rings make dihedral angles of 75.15 (4)° and 72.18 (4)° with the planes of the benzo­furan ring systems in the two mol­ecules. In the crystal, mol­ecules are linked by weak C—H...O and C—H...π inter­actions, forming a three-dimensional network.

3-Ethyl­sulfinyl-2-(3-fluoro­phen­yl)-5-phenyl-1-benzo­furan

In the title compound, C₂₂H₁₇FO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo­furan ring system and the pendant 3-fluoro­phenyl and phenyl rings are 23.92 (5) and 32.44 (5)°, respectively. In the crystal, mol­ecules are linked by two weak C—H...O(sulfin­yl) hydrogen bonds and a C—H...π inter­action, forming a sheet, which lies in the ab plane. A π–π inter­action between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.976 (2) Å] links the mol­ecules into inversion dimers and connects adjacent sheets, resulting in a three-dimensional network.

5-Bromo-2-(4-fluoro­phen­yl)-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

In the title compound, C₂₁H₁₄BrFO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo­furan ring system and the pendant 4-fluoro­phenyl and phenyl rings are 1.50 (8) and 81.47 (6)°, respectively. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds into supra­molecular chains running along the a-axis direction. A short S...O contact [2.9623 (13) Å] involving the sulfinyl groups is observed between inversion-related chains.

7-Bromo-2-(4-methyl­phen­yl)-1-(methyl­sulfin­yl)naphtho­[2,1-b]furan

In the title compound, C₂₀H₁₅BrO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030 (2) Å] of the naphtho­furan ring system and the 4-methyl­phenyl ring is 38.49 (9)°. In the crystal, mol­ecules are linked by C—H...π and C—Br...π [3.871 (2) Å] inter­actions into stacks along the b-axis direction. These stacks are further linked by weak C—H...O hydrogen bonds, forming a three-dimensional network.

5-Fluoro-2-(4-fluoro­phen­yl)-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

In the title compound, C₂₁H₁₄F₂O₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzo­furan ring system and the pendant 4-fluoro­phenyl and phenyl rings are 5.93 (9) and 80.23 (5)°, respectively. In the crystal, mol­ecules are linked by weak C—H...O and C—H...π inter­actions, forming a three-dimensional network.

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

In the title compound, C₁₇H₁₅BrO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.003 (2) Å] of the benzo­furan ring system and the mean plane [r.m.s. deviation = 0.006 (2) Å] of the 4-bromo­phenyl ring is 83.09 (7)°. In the crystal, weak C—H...π inter­actions are observed.

5-Chloro-3-ethyl­sulfinyl-2-(3-fluoro­phen­yl)-1-benzo­furan

The asymmetric unit of the title compound, C₁₆H₁₂ClFO₂S, contains two independent mol­ecules in which the benzo­furan ring systems are essentially planar, with r.m.s. deviations of 0.007 (1) and 0.013 (1) Å. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds into chains extending along the b axis. These chains are further packed into stacks along the c -axis by S...O contacts [3.1898 (11) and 3.1361 (11) Å] involving the sulfinyl groups. In both 3-fluoro­phenyl rings, the F atom is disordered over two positions, with site-occupancy factors of 0.921 (2) and 0.079 (2).

5-Chloro-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

In the title compound, C₁₆H₁₃ClO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.004 (2) Å] of the benzo­furan ring system and the 4-methyl­phenyl ring is 29.25 (8)°. In the crystal, inversion dimers linked by pairs of weak C—H...O interactions generate R₂²(14) loops.

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

In the title compound, C₁₇H₁₅BrO₂S, both the benzo­furan and 2-bromo­phenyl rings are virtually planar, with r.m.s. deviations of 0.009 (2) and 0.006 (2) Å, respectively. The dihedral angle between these mean planes is 89.31 (7)°. 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. In addition, C—S...π inter­actions, with an S-to-ring-centroid distance of 3.50 (2) Å, are observed between inversion-related dimers.

3-(4-Chloro­phenyl­sulfin­yl)-2,4,7-tri­meth­yl-1-benzo­furan

In the title compound, C₁₇H₁₅ClO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.020 (2) Å] of the benzo­furan ring system and the mean plane [r.m.s. deviation = 0.011 (1) Å] of the 4-chloro­phenyl ring is 72.68 (6)°. In the crystal, mol­ecules are linked via pairs of C—H...π inter­actions into inversion dimers. These dimers are further packed by C—H...O hydrogen bonds into supra­molecular chains running along the a-axis direction. In addition, the crystal structure also exhibits π–π inter­actions between the 4-chloro­phenyl rings of adjacent mol­ecules [centroid–centroid distance = 4.094 (3) Å, inter­planar distance = 3.648 (3) Å and slippage = 1.656 (3) Å].

5-Cyclo­hexyl-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzo­furan

The asymmetric unit of the title compound, C₂₆H₂₃FO₂S, contains two independent mol­ecules (A and B), in both of which the cyclo­hexyl ring adopts a chair conformation. The benzo­furan ring systems, the 4-fluoro­phenyl and phenyl rings are essentially planar, with r.m.s. deviations of 0.008 (1), 0.002 (1) and 0.003 (1) Å, respectively, for mol­ecule A, and 0.016 (1), 0.004 (1) and 0.002 (1) Å, respectively, for mol­ecule B. The dihedral angles between the benzo­furan ring system and the pendant 4-fluoro­phenyl and phenyl rings are 12.3 (7) and 85.42 (4)°, respectively, for mol­ecule A, and 39.67 (6) and 72.17 (4)°, respectively, for mol­ecule B. In the crystal, mol­ecules are linked by weak C—H...O and C—H...π inter­actions, resulting in a three-dimensional network.

5-Cyclo­hexyl-3-ethyl­sulfinyl-2-(3-fluoro­phen­yl)-1-benzo­furan

In the title compound, C₂₂H₂₃FO₂S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzo­furan ring system and the mean plane [r.m.s. deviation = 0.009 (2) Å] of the 3-fluoro­phenyl ring is 24.80 (4)°. In the crystal, mol­ecules are connected by C—H...O hydrogen bonds, forming chains along [10-1]. These chains are linked via C—H...F hydrogen bonds, forming a three-dimensional structure. There are also inter­planar inter­actions present involving the furan ring of the benzo­furan ring system and the 3-fluoro­phenyl ring [centroid–centroid distance = 3.728 (2) Å].