Crystal structure of the 1,3,6,8-tetra-aza-tri-cyclo[4.3.1.1(3,8)]undecane (TATU)-4-nitro-phenol (1/2) adduct: the role of anomeric effect in the formation of a second hydrogen-bond inter-action.

ABSTRACT: In the title ternary co-crystalline adduct, C7H14N4·2C6H5NO3, mol-ecules are linked by two inter-molecular 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 nitro-phenol mol-ecules 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 supra-molecular dimer enclosing an R 6 (6)(32) ring motif. Additional C-H?O inter-molecular hydrogen-bonding inter-actions form a second supra-molecular inversion dimer with an R 2 (2)(10) motif. These units are linked via C-H?O and C-H?N hydrogen bonds, forming a three-dimensional network.

SUBMITTER: Rivera A 

PROVIDER: S-EPMC4645038 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature