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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.

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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].

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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.

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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].

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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.

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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.
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