Synthesis, Spectroscopic Properties and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazoniatricyclo(16.4.0.07,12)docosane Tetrachloride Tetrahydrate

Single crystals of 3,14-dimethyl-2,6,13,17-tetraazoniatricyclo(16.4.0.07,12)docosane tetrachloridetetrahydrate compound, [C20H44N4]Cl4·4H2O (1), were obtained by a novel synthetic route andcharacterized by elemental analysis and X-ray diffraction. The synthesized compound crystallized inthe monoclinic space group P21/n with two molecules of compound 1 in the unit cell [a = 7.5548(3) Å,b = 23.1838(8) Å, c = 8.3101(4) Å; β = 103.390(3)º]. The asymmetric unit contains half acentrosymmetric macrocyclic cation, two chloride anions and two water molecules. The organic[C20H44N4]4+ fragment of 1 adopts an exodentate [3,4,3,4]-D conformation. The C–C and N–C bondlengths of the macrocyclic tetracation range 1.525(3)-1.540(3) Å and 1.505(3)-1.519(3) Å, respectively.A three-dimensional hydrogen bonding network provides crystal cohesion through O–H···Cl, N–H···Cland N–H···O interactions between organic cations, chloride anions and water molecules. The functionalgroups present in the crystal were studied by Fourier-transform infrared spectroscopy and Ramanspectroscopy. The Hirshfeld surface analysis and 2D fingerprint plots revealed that the crystal packingin 1 is dominated by H···H, Cl···H/H···Cl and O···H/H···O contacts.