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Two polymorphs (A and B) of trans-1,4-diethynylcyclohex-ane-1,4-diol represent a unique example of the simultaneous occurrence of both conformational polymorphism and conformational isomorphism, while a pseudopolymorphic monohydrate is closely related.

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Molecules of the title compound, C(16)H(14)O, are chiral and crystallize in space group P-4 with Z' = 2, and with one R and one S molecule in the asymmetric unit. The conformations of the phenyl rings in the two independent molecules differ slightly. Supramolecular organization in the crystal is via tetrameric O-H. H(O) hydrogen-bonded synthons formed separately by each conformer. These tetrameric synthons stack along the c axis via C[triple-bond]C-H.O(H) hydrogen bonds. The only link between the conformer stacks is provided by weaker C(methylene)-H and C(phenyl)-H interactions with pi(arene) density.

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Structures of the title compounds are all mediated by strong cooperative arrangements of O—H...O hydrogen bonds, supported by a variety of weaker interactions which affect the type of O—H...O synthon that is formed. The tetrafluoro compound contains hexameric O—H...O synthons in a supramolecular chair conformation, together with C≡C—H...F interactions. However, the tetrachloro and tetrabromo compounds both form tetrameric O—H...O synthons. This dominant pattern is supported by halogen...halogen interactions having one C—Cl[Br]...Cl[Br] angle close to 180° and the other close to 90°, and by C≡C—H...Cl[Br] interactions.

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