Study of host–guest interactions in benzodiazacoronands by means of solid state NMR spectroscopy, X-ray diffraction and quantum mechanical computations

In this work we present solid state data for five host–guest complexes formed by N-(4,19-dioxo-2,8,15,21-tetraoxa-5,18-diazatricyclohexacosa-1(25),9(14),10,12,22(26),23-hexaen-26-yl)-benzamide (1) belonging to the group of benzodiazacoronands, achiral compounds for which chiral crystals were found (J. Kalisiak and J. Jurczak, Cryst. Growth Des., 2006, 6, 20). The X-ray structure was resolved for four of them. It was found that 1 crystallizes in P21/c, P and P21/n achiral space groups. Differentiation of molecular packing and the presence of guest molecules within the crystal lattice were analyzed with solid state NMR. An attempt was made to correlate changes in 13C δii and 15N δii chemical shift tensor values, obtained from analysis of spinning sidebands of 1D and 2D (2D PASS) NMR spectra, with changes in the strength of hydrogen bonding. Quantum mechanical DFT GIAO calculations of NMR shielding parameters carried out on structures with coordinates taken from XRD were employed for signals assignment and verification of structural constraints.