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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.

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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.

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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].

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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.
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