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The title compound, C8H9ClO, packs with two independent mol­ecules in the asymmetric unit, without significant differences in corresponding bond lengths and angles, with the ethyl group in each oriented nearly perpendicular to the aromatic ring having ring-to-side chain torsion angles of 81.14 (18) and −81.06 (19)°. In the crystal, mol­ecules form an O—H...O hydrogen-bonded chain extending along the b-axis direction, through the phenol groups in which the H atoms are disordered. These chains pack together in the solid state, giving a sheet lying parallel to (001), via an offset face-to-face π-stacking inter­action characterized by a centroid–centroid distance of 3.580 (1) Å, together with a short inter­molecular Cl...Cl contact [3.412 (1) Å].

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The title compound, C9H7FO, crystallizes with two independent mol­ecules in the asymmetric unit, in which corresponding bond lengths are the same within experimental error. The five-membered ring in each molecule is almost planar, with r.m.s. deviations of 0.016 and 0.029 Å. In the crystal, mol­ecules form sheets parallel to (1 0 0) via C—H...O and C—H...F inter­actions with F...F contacts [3.1788 (16) and 3.2490 (16) Å] between the sheets.

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In the crystal structure of the title compound, C6H5ClIN, the amino group engages in N—H...N hydrogen bonding, creating [100] chains. A Cl...I contact is observed [3.7850 (16) Å]. The parallel planes of neigbouring mol­ecules reveal highly offset π-stacking characterized by a centroid–centroid distance of 4.154 (1), a centroid-to-plane distance of 3.553 (3) and ring-offset slippage of 2.151 (6) Å.
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