Crystal structure of the co-crystalline adduct 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8]dodecane (TATD)–4-iodophenol (1/2): supramolecular assembly mediated by halogen and hydrogen bonding

Abstract

The asymmetric unit of the title co-crystalline adduct, 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD)–4-iodophenol (1/2), C8H16N4·2C6H5IO, comprises a half molecule of the aminal cage polyamine plus a 4-iodophenol molecule. A twofold rotation axis generates the other half of the adduct. The components are linked by two intermolecular O—H...N hydrogen bonds. The adducts are further linked into a three-dimensional framework structure by a combination of N...I halogen bonds and weak non-conventional C—H...O and C—H...I hydrogen bonds.

First hydrogen-bonded adduct of sterically hindered 2-tert-butyl-4-methylphenol (TBMP) with 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) via coupling of classical hydrogen bonds and C—H...π non-covalent interactions

“…Co-crystals of tetraazatricyclo[4.4.1.1 3,8 ]dodecane have already been reported, i.e. with 3-nitrophenol (Rivera et al, 2019), 4-iodophenol (Rivera et al, 2017a), 4-chloro-3,5-dimethylphenol (Rivera et al, 2015a), hydroquinone (Rivera et al, 2007), and 4-bromophenol (Rivera et al, 2015b) (refcodes: HOXGUZ, JELVII, QUFROA, WEXQIA, XULKOG).…”

Mechanochemical synthesis and X-ray structural characterization of three 3-nitrophenol cocrystals with three aminal cage azaadamantanes: the role of the stereoelectronic effect on intermolecular hydrogen-bonding patterns

“…4-chlorophenol (Rivera et al, 2015a(Rivera et al, , 2016a, and the 2:1 adducts of TATD (3) with 4-bromophenol and 4-iodophenol (Rivera et al, 2015b(Rivera et al, , 2017b, crystal analysis shows that in (2a) and (3a), the 3-NP molecules are hydrogen bonded to N atoms of the same N-CH 2 -CH 2 -N moiety, which is the key structural parameter from the X-ray diffraction studies. However, although the molecular constitutions of compounds (2) and (3) differ only in the presence of one additional ethylene bridge in the tricyclic structure of (3), they nonetheless exhibit some marked differences in their conformations: in particular, the N-C-C-N torsion angles are À9.3 (5) (N1-C1-C2-N2) and 9.3 (4) (N3-C7-C8-N4) in cocrystal (3a), while the corresponding value of the N1-C2-C2-N1 torsion angle is 0.0 (2) , which indicates that the 42m symmetry of (3) is not maintained in the cage structure (Rivera et al, 2014;Murray-Rust, 1974).…”