Abstract
In the title compound, C7H14N4·2C6H5ClO, which crystallized with two crystallographically independent 4-chloro-phenol mol-ecules and one 1,3,6,8-tetra-aza-tri-cyclo-[4.3.1.13,8]undecane (TATU) mol-ecule in the asymmetric unit, the independent components are linked by two O-H⋯N hydrogen bonds. The hydrogen-bond acceptor sites are two non-equivalent N atoms from the aminal cage structure, and the tricyclic system distorts by changing the C-N bond lengths. In the crystal, these hydrogen-bonded aggregates are linked into chains along the c axis by C-H⋯N hydrogen bonds. The crystal structure also features C-H⋯π contacts.
Highlights
C7H14N4Á2C6H5ClO, which crystallized with two crystallographically independent 4-chlorophenol molecules and one 1,3,6,8tetraazatricyclo[4.3.1.13,8]undecane (TATU) molecule in the asymmetric unit, the independent components are linked by two O—HÁ Á ÁN hydrogen bonds
Following our previous work on phenol–amine adducts based on cyclic aminal cages with phenol derivatives (Rivera et al, 2015a,b,c), we report the synthesis and crystal structure of the title 1:2 complex assembled through hydrogen-bonding interactions between the aminal cage, 1,3,6,8-tetraazatricyclo [4.3.1.13,8]undecane (TATU), with 4-chlorophenol under solvent-free conditions at low temperature
In the structure found for the three-component aggregates observed here, both types of nitrogen atom mentioned above are involved in hydrogen bonding with N1 and N3 acting as hydrogen-bond acceptors
Summary
Following our previous work on phenol–amine adducts based on cyclic aminal cages with phenol derivatives (Rivera et al, 2015a,b,c), we report the synthesis and crystal structure of the title 1:2 complex assembled through hydrogen-bonding interactions between the aminal cage, 1,3,6,8-tetraazatricyclo [4.3.1.13,8]undecane (TATU), with 4-chlorophenol under solvent-free conditions at low temperature. TATU, a small tricyclic aminal cage, is an interesting option for studying hydrogen-bonding situations as it has four nitrogen atoms as potential hydrogen-bond acceptors. These N atoms have two different environments, N1 and N2 from the ethylene fragment (NCH2CH2N) and N3 and N4 from the 1,1-gem-diaminic units. These present two discrete options for hydrogen bonding to the aminal cage. Studies on phenol complexes with tertiary amines in the solid state show that the proton transfer depends on the. The reaction to produce the cocrystal occurs efficiently in the solid state by grinding a mixture of finely powdered TATU and 4-chlorophenol at room temperature; there are no by-products, and the work-up procedure is easy
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
