Crystal structure of 2,5-dimethyl-3-(2-methyl-phenyl-sulfin-yl)-1-benzo-furan.

In the title compound, C17H16O2S, the dihedral angle between the benzo-furan ring system [r.m.s. deviation = 0.009 (1) Å] and the 2-methyl-phenyl ring is 86.72 (4)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into columns along the b-axis direction.

Crystal structure of 5-bromo-2,4,6-trimethyl-3-[(2-methyl-phen-yl)sulfin-yl]-1-benzo-furan.

In the title compound, C18H17BrO2S, the dihedral angle between the mean planes of the benzo-furan [r.m.s. deviation = 0.025 (2) Å] and the 2-methyl-benzene rings is 87.87 (5)°. In the crystal, mol-ecules are linked into supra-molecular layers parallel to (0-11) by C-H⋯O hydrogen bonds and Br⋯Br [3.4521 (5) Å] contacts. These are connected into a three-dimensional architecture via C-H⋯π inter-actions, which link inversion-related mol-ecules into dimers, and π-π inter-actions between the benzene and furan rings [centroid-centroid distance = 3.573 (2) Å].

Crystal structure of 5-chloro-2-(2-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10ClFO2S, the dihedral angle between the mean planes of the benzo-furan ring [r.m.s. deviation = 0.007 (1) Å] and the 2-fluoro-phenyl ring is 32.53 (5)°. In the crystal, mol-ecules related by inversion are paired into dimers via two different C-H⋯O hydrogen bonds. Further, Cl⋯O halogen bonds [3.114 (1) Å], and F⋯π [F-to-furan-centroid distance = 3.109 (1) Å] and S⋯F [3.1984 (9) Å] inter-actions link these into a three-dimensional network.

Crystal structure of 2-ethyl-3-(4-fluoro-phenyl-sulfon-yl)-5,7-dimethyl-1-benzo-furan.

In the title compound, C18H17FO3S, the dihedral angle between the plane of the benzo-furan ring [r.m.s. deviation = 0.006 (1) Å] and that of the 4-fluoro-phenyl ring [r.m.s. deviation = 0.004 (1) Å] is 82.45 (4)°. In the crystal, mol-ecules are linked via three different pairs of C-H⋯O hydrogen bonds, forming chains along [001] and enclosing two R (2) 2(10) and one R (2) 2(12) ring motifs. The chains are further linked by π-π inter-actions [inter-centroid distance = 3.566 (1) Å] between the furan rings of inversion-related mol-ecules, forming a two-dimensional network lying parallel to (100).

Crystal structure of 5-chloro-3-(4-fluoro-phenyl-sulfin-yl)-2,4,6-trimethyl-1-benzo-furan.

In the title compound, C17H14ClFO2S, the dihedral angle between the mean planes of the benzo-furan ring system [maximum deviation = 0.037 (2) Å] and the 4-fluoro-benzene ring is 71.92 (5)°. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked by π-π stacking between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.7103 (10) Å]. These mol-ecules are further linked by C-S⋯π [S⋯centroid = 3.570 (1) Å] and C-H⋯O inter-actions, resulting in a three-dimensional supra-molecular network.

Crystal structure of 3-(4-bromo-phenyl-sulfon-yl)-2,5,6-trimethyl-1-benzo-furan.

In the title compound, C17H15BrO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-bromo-phenyl ring is 89.29 (6)°. In the crystal, mol-ecules are linked into a chain along the b-axis direction by C-H⋯π hydrogen bonds and C-Br⋯π [3.626 (1) Å] inter-actions.

Crystal structure of 3-(2-bromo-phenyl-sulfon-yl)-2,5,7-trimethyl-1-benzo-furan.

In the title compound, C17H15BrO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.016 (2) Å] and the 2-bromo-phenyl ring is 82.93 (6)°. In the crystal, mol-ecules are linked via pairs of C-H⋯π hydrogen bonds and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.881 (2) Å] into inversion-related dimers along the b-axis direction. These dimers are further linked by short Br⋯O [3.185 (2) Å] contacts.

Crystal structure of 5-fluoro-2-(3-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10F2O2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (1) Å] and the 3-fluoro-phenyl ring is 26.60 (5)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, and by π-π inter-actions between the benzo-furan rings of inversion-related mol-ecules [centroid(benzene)-centroid(furan) distance = 3.819 (2) Å], forming a three-dimensional network.

Crystal structure of 2-(3-fluoro-phen-yl)-5-iodo-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10FIO2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 3-fluoro-phenyl ring is 29.63 (7)°. In the crystal, mol-ecules are linked into inversion dimers along the b-axis direction by two different pairs of C-H⋯O hydrogen bonds and I⋯O [3.228 (1) Å] contacts.

Crystal structure of 2,5-dimethyl-3-(2-methyl-phenyl-sulfon-yl)-1-benzo-furan.

The title compound, C17H16O3S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the benzo-furan ring system [r.m.s. deviation of 0.013 (1) for A and 0.009 (1) Šfor B] and the 2-methyl-phenyl ring is 83.88 (5) for A and 86.94 (5)° for B. In the crystal, the B mol-ecules are linked into a chain along the b-axis direction by C-H⋯O hydrogen bonds. The A mol-ecules are connected on either side of this chain by further C-H⋯O hydrogen bonds. These chains are linked via C-H⋯π inter-actions, forming sheets parallel to (100). There are also very weak π-π inter-actions present [centroid-centroid distance = 3.925 (11) Å] involvingthe 2-methyl-phenyl rings of neighbouring A and B mol-ecules.

Crystal structure of 7-bromo-2-(3-fluoro-phen-yl)-1-(methyl-sulfin-yl)naphtho[2,1-b]furan.

In the title compound, C19H11BrFO2S, the dihedral angle between the plane of the naphtho-furan ring system [r.m.s. deviation = 0.043 (2) Å] and that of the 3-fluoro-benzene ring is 39.32 (8)°. In the crystal, mol-ecules are linked by C-H⋯O and C-Br⋯π [3.835 (1) Å] inter-actions into stacks along the c axis, forming a three-dimensional network. The F atom is disordered over two positions, with site-occupancy factors of 0.851 (3) and 0.149 (3).

Crystal structure of 5-chloro-2,7-dimethyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

In the title compound, C17H15ClO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.008 Å] and the 4-methyl-phenyl ring is 77.29 (4)°. In the crystal, mol-ecules are linked by π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.847 (2) Å] and between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.743 (2) Å]. The mol-ecules are stacked along the a-axis direction. In addition, pairs of C-H⋯O hydrogen bonds are observed between inversion-related dimers: these generate R 2 (2)(12) loops.

Crystal structure of 5-iodo-2-methyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

In the title compound, C16H13IO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-methyl-phenyl ring is 70.35 (5)°. In the crystal, mol-ecules are linked by pairs of π-π inter-actions between the furan and benzene rings, with centroid-centroid distances of 3.667 (3) and 3.701 (3) Å. The mol-ecules stack along the a-axis direction. In addition, pairs of C-H⋯O hydrogen bonds between inversion-related dimers [which generate R 2 (2)(10) loops] and a short I⋯I [3.7534 (3) Å] contact are observed.

Crystal structure of 2-ethyl-3-(4-fluoro-phenyl-sulfin-yl)-5,7-dimethyl-1-benzo-furan.

In the title compound, C18H17FO2S, the dihedral angle between the planes of the benzo-furan ring system (r.m.s. deviation = 0.004 Å) and the 4-fluoro-phenyl ring is 86.38 (6)°. The terminal C atom of the ethyl substituent is displaced by 1.444 (3) Šfrom the benzo-furan ring system to the same side of the mol-ecule as the 4-fluoro-phenyl ring. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions into inversion-related dimers. These dimers are further linked by π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.715 (3) Å] and between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.598 (3) Å]. The mol-ecules are stacked along the a-axis direction. In the sulfinyl group, the S and O atoms are disordered over two sets of sites, with site-occupancy factors of 0.797 (3) and 0.213 (3).

5-Chloro-3-(4-fluoro-phenyl-sulfon-yl)-2,7-dimethyl-1-benzo-furan.

In the title compound, C16H12ClFO3S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.007 (1) Å] and that of the 4-fluoro-phenyl ring is 76.11 (5)°. In the crystal, mol-ecules are linked into [010] chains via two different inversion-generated pairs of C-H⋯O hydrogen bonds. The crystal structure also exhibits weak π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.820 (2) Å].

Crystal structure of 5-chloro-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

In the title compound, C17H21ClO2S, the cyclo-hexyl ring adopts a chair conformation with the C-S bond in an equatorial orientation. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π hydrogen bonds and a Cl⋯π [3.594 (2) Å] contact into chains along the a-axis direction.

Crystal structure of 2,5-dimethyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C17H16O3S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.010 (1) Å] and that of the 3-methyl-phenyl ring is 79.09 (5)°. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, mol-ecules are connected into a chain along the c-axis direction by two different pairs of inversion-generated inter-actions: C-H⋯π hydrogen bonds between the methyl groups and the benzene rings of the 3-methyl-phenyl fragments and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.673 (2) Å].

Crystal structure of 5-chloro-2-(3-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10ClFO2S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.013 (1) Å] and that of the 3-fluoro-phenyl ring [r.m.s. deviation = 0.005 (1) Å] is 31.36 (5)°. In the crystal, mol-ecules are linked by two different pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

5-Bromo-3-ethyl-sulfinyl-2-(4-methyl-phen-yl)-1-benzo-furan.

In the title compound, C17H15BrO2S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.004 (3) Å] and that of the 4-methyl-phenyl ring is 0.9 (2)°. In the crystal, mol-ecules are linked by C-H⋯O, C-H⋯π and Br⋯π [3.636 (2) Å] inter-actions, and by π-π inter-actions between the 4-methyl-phenyl and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.650 (2) Å], forming a three-dimensional network.

5-Fluoro-2-(2-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

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