In the title compound, C17H15BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions.

In the title compound, C17H15BrO2S, the 4-methyl­phenyl ring makes a dihedral angle of 14.46 (5)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by pairs of Br⋯O contacts [3.151 (2) Å] into centrosymmetric dimers.

In the title compound, C16H13FO2S, the 4-methyl­phenyl ring makes a dihedral angle of 29.53 (4)° with the mean plane of the benzofuran fragment [r.m.s. deviation = 0.004 (1) Å]. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds, forming inversion dimers that stack along the a axis.

In the title compound, C17H13FO4S, the 3-fluoro­phenyl ring makes a dihedral angle of 6.14 (5)° with the mean plane [r.m.s. deviation = 0.008 (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. The crystal structure also exhibits slipped π–π inter­actions between the 3-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.769 (2) Å and slippage = 1.684 (2) Å].

In the title compound, C22H23FO3S, the cyclo­pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The 4-fluoro­phenyl ring makes a dihedral angle of 43.67 (3)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions, forming a three--dimensional network. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.883 (2) Å and slippage = 1.731 (2) Å].

In the title compound, C16H13BrO2S, the 4-methyl­phenyl ring makes a dihedral angle of 29.58 (7)° with the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzofuran fragment. In the crystal, the molecules are linked by pairs of C—H⋯O hydrogen bonds into centrosymmetric dimers.

In the title compound, C20H12BrFO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluoro­phenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯π inter­actions.

In the title compound, C16H12BrFO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].

There are two symmetry-independent mol­ecules, A and B, in the asymmetric unit of the title compound, C17H14FIO3S. The dihedral angle formed by the 4-fluoro­phenyl ring and the mean plane [r.m.s. deviation = 0.013 (2) Å in mol­ecule A and 0.016 (2) Å in mol­ecule B] of the benzofuran fragment is 57.71 (7)° in mol­ecule A and 44.95 (7)° in mol­ecule B. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and I⋯O contacts [I⋯O = 3.3646 (15) and 3.2354 (14) Å], forming a three--dimensional network.

In the title compound, C21H22O2S, the cyclo­pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The benzofuran unit is essentially planar, with a mean deviation from the least-squares plane defined by the nine constituent ring atoms of 0.008 (2) Å. In the crystal, mol­ecules are linked via pairs of C—H⋯π inter­actions, forming inversion dimers. In the ring of the 4-methyl­phenyl group, four C atoms and their attached H atoms are disordered over two sets of sites, with site-ccupancy factors of 0.899 (5) and 0.10.

In the title compound, C19H12BrFO3S, the 3-fluoro­phenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by slipped π–π inter­actions between the furan and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].

In the title compound, C17H14FIO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 14.56 (5)° with the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked via pairs of I⋯O contacts [3.038 (2) Å], forming inversion dimers. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions, with site-occupancy factors of 0.747 (3) and 0.253 (3).

In the title compound, C17H15IO3S, the 4-methyl­phenyl ring makes a dihedral angle of 76.95 (5)° with the mean plane [r.m.s. deviation = 0.019 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.671 (3) Å and slippage = 1.049 (3) Å].

In the title compound, C16H12FIO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 76.47 (6)° with the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds,forming chains along the b-axis direction, and an I⋯O contact [3.204 (2) Å]. The crystal structure also exhibits slipped π–π inter­actions between the 3-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.683 (3) Å and slippage = 1.708 (3) Å].

In the title compound, C22H24O2S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. In the methyl­sulfinyl group, the methyl group and S atom are disordered over two sets of sites, with site-occupancy factors of 0.58 (3) and 0.42 (3). In the ring of the 4-methyl­phenyl group, the four C atoms are disordered over two sets of sites, with site-occupancy factors of 0.858 (5) and 0.142 (5).

In the title compound, C17H15FO3S, the 2-fluoro­phenyl ring makes a dihedral angle of 89.12 (8)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions.

In the title compound, C18H17FO2S, the 2-fluoro­phenyl ring makes a dihedral angle of 85.45 (4)° with the mean plane [r.m.s. deviation = 0.017 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions.

In the title compound, C15H10F2O3S, the 3-fluoro­phenyl ring makes a dihedral angle of 79.51 (6)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯F and C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distances = 3.563 (3) and 3.820 (3) Å and slippages of 0.358 (3)and 1.551 (3) Å]. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.887 (3) and 0.113 (3).

In the title compound, C15H10BrFO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 85.0 (1)° with the mean plane [r.m.s. deviation = 0.008 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and a Br⋯O contact [3.200 (3) Å]. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.619 (4) Å and slippage of 1.389 (4) Å]. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.583 (5) and 0.417 (5).

In the title compound, C16H13IO2S, the 4-methyl­phenyl ring makes a dihedral angle of 88.36 (7)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and an I⋯O contact [3.103 (2) Å]. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.659 (2) Å].

In the title compound, C19H13BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho­furan ring. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits slipped π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho­furan benzene ring and the furan ring of neighbouring mol­ecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].

In the title compound, C16H13BrO3S, the 4-methyl­phenyl group makes a dihedral angle of 70.1 (1)° with the mean plane [average deviation = 0.012 (2) Å] of the benzofuran unit. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds. There are also π–π inter­actions between the furan and benzene rings of adjacent benzofuran systems [centroid–centroid distances = 3.621 (2) and 3.665 (2) Å], along with halogen–halogen inter­actions [Br⋯Br separation = 3.674 (1) Å].

In the title compound, C15H10BrClO2S, the 4-bromo­phenyl ring makes a dihedral angle of 86.85 (6)° with the mean plane [mean deviation = 0.009 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by slipped π–π inter­actions between the benzene and the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.884 (2), inter­planar distance = 3.369 (2) and slippage = 1.945 (2) Å], and between the 4-bromo­phenyl rings of adjacent mol­ecules [centroid–centroid distance = 3.882 (2), inter­planar distance = 3.552 (2) and slippage = 1.566 (2) Å]. A Br⋯Br [3.6446 (4) Å] halogen inter­action is also observed.

In the title compound, C15H10BrClO3S, the 4-bromo-substituted benzene ring forms a dihedral angle of 72.55 (6)° with the mean plane [mean deviation = 0.008 (2) Å] of the benzofuran ring system. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds into chains along [001]. There are also π–π inter­actions between the furan and benzene rings of symmetry-related benzofuran systems [centroid–centroid distances = 3.549 (3) and 3.632 (3) Å].

In the title compound, C20H19FO2S, the benzofuran fragment is essentially planar, with a largest deviation from the mean plane of 0.026 (2) Å. The benzene ring makes a dihedral angle of 30.72 (12)° with this plane. The cyclo­pentyl group adopts an envelope conformation, with the α-C atom as the flap. This atom is disordered over two sites with occupancy factors of 0.803 (16) and 0.197 (16). In the crystal, mol­ecules are linked by weak C—H⋯O, C—H⋯π and C—F⋯π [3.257 (3) Å] inter­actions.