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In the title compound, C18H40NO2+·Br−, the ion pairs formed by the hydrogen-bonded bromide anions and organic cations are arranged into thick layers with the alkyl groups directed to the inside and the trimethylaminium groups and the bromide anions situated on the layer surface. The long alkyl chain in the cation adopts an all-trans conformation. In the crystal structure, molecules are connected by intermolecular O—H...Br hydrogen bonds, forming ionic pairs that are further connected into an extended chain structure via C—H...O hydrogen-bonding interactions. The crystal is chiral but nearly 90% of atoms in the unit cell are related by a pseudo-inversion center. The crystal shows racemic twinning with a 0.33:0.67 domain ratio.

The chemical name of the title compound in the paper by Sun, Li, Wang, Fu & Wang [Acta Cryst. (2009), E65, o262] is corrected and the structural diagram is updated.

In the crystal structure of the title compound, C20H39N2+·Br−·H2O, the 1-hexadecyl-3-methylimidazolium cations are stacked along the b axis, forming channels parallel to [100] which are occupied by the bromide anions and water molecules. The crystal is stabilized by O—H...Br, C—H...O and C—H...Br hydrogen-bonding interactions, generating a two-dimensional network.

In the title molecule, C18H14N2O3, O—H...N and N—H...O hydrogen bonds influence the molecular conformation; the benzene and naphthalene planes are inclined at a dihedral angle of 11.54 (5)°. In the crystal structure, intermolecular O—H...O hydrogen bonds link the molecules into chains running in the [01overline{1}] direction.

In the title molecule, C10H14N4S, the thiorea plane and benzene ring form a dihedral angle of 16.0 (3) Å. In the crystal structure, intermolecular N—H...S hydrogen bonds link the molecules into ribbons extended in the [100] direction; these incorporate inversion dimers.