In the title ternary co-crystalline adduct, C7H14N4·2C6H5NO3, molecules are linked by two intermolecular O—H...N hydrogen bonds, forming a tricomponent aggregates in the asymmetric unit. The hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction. In the title adduct, the two independent nitrophenol molecules are essentially planar, with maximum deviations of 0.0157 (13) and 0.0039 (13) Å. The dihedral angles between the planes of the nitro group and the attached benzene rings are 4.04 (17) and 5.79 (17)°. In the crystal, aggregates are connected by C—H...O hydrogen bonds, forming a supramolecular dimer enclosing anR66(32) ring motif. Additional C—H...O intermolecular hydrogen-bonding interactions form a second supramolecular inversion dimer with anR22(10) motif. These units are linkedviaC—H...O and C—H...N hydrogen bonds, forming a three-dimensional network.

The asymmetric unit of the title compound, C28H42N2O5·H2O, consists of one half of the organic mol­ecule and one half-mol­ecule of water, both of which are located on a mirror plane which passes through the central C atoms and the hydroxyl group of the heterocyclic system. The hydroxyl group at the central ring is disordered over two equally occupied positions. The six-membered ring adopts a chair conformation, and the 2-hy­droxy­benzyl substituents occupy the sterically preferred equatorial positions. The aromatic rings make dihedral angles of 75.57 (9)° with the mean plane of the heterocyclic ring. The dihedral angle between the two aromatic rings is 19.18 (10)°. The mol­ecular structure features two intra­molecular phenolic O—H⋯N hydrogen bonds with graph-set motif S(6). In the crystal, mol­ecules are connected via O—H⋯O hydrogen bonds into zigzag chains running along the a-axis direction.

The components of the ternary co-crystalline adduct are linked by inter­molecular O–H⋯N hydrogen bonds.

The title chiral quaternary ammonium salt, C13H25N4+·I−, was synthesized through the Menschutkin reaction between the cage aminal (2S,7S)-1,8,10,12-tetraazatetracyclo[8.3.1.18,12.02,7]pentadecane and ethyl iodide. The quaternization occurred regioselectively on the nitrogen with major sp3 character. The crystal structure consists of anions and cations separated by normal distances. Ions are not linked through C—H...I hydrogen bonds

The title molecular salt, C11H21N4(+)·C6H4NO3(-)·C6H5NO3, (II), crystallizes with two independent three-component aggregates in the asymmetric unit. In the cations, the cyclohexane rings fused to the cage azaadamantane systems both adopt a chair conformation. In the crystal structure, the aggregates are connected by C-H···O hydrogen bonds, forming a supramolecular unit enclosing an R4(4)(24) ring motif. These units are linked via C-H···O and C-H···N hydrogen bonds, forming a three-dimensional network. Even hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction. The C-N bond distances provide structural evidence for a strong anomeric effect. The structure also displays O-H···O and N-H···O hydrogen bonding. Geometric optimization and natural bond orbital (NBO) analysis of (II) were undertaken by utilizing DFT/B3LYP with the 6-31+G(d,p) basis set. NBO second-order perturbation theory calculations indicate donor-acceptor interactions between nitrogen lone pairs and the antibonding orbital of the C-C and C-N bonds for the protonated polyamine, in agreement with the occurrence of bond-length and bond-angle changes within the aminal cage structure.