Supramolecular hydrogen-bonding network in 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate crystal

• Crystal of 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate was obtained.
• Hydrogen bonding motif R22(8) of 1:1 forms supramolecular complex.
• The characteristic vibrational bands of the H and D analogue are discussed.

The single crystals of 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate were grown using a solution growth technique. The compound crystallises in the centrosymmetric P21/c space group of the monoclinic system. The conformation of the 1-(diaminomethylene)thiouron-1-ium cation is not strictly planar, but twisted. Both arms of the cation are oppositely rotated by 8.5(1)° around the CN bonds involving the central N atom. The arrangement of oppositely charged components, i.e. 1-(diaminomethylene)thiouron-1-ium cations and 4-hydroxybenzenesulfonate anions in the crystal is mainly determined by ionic and hydrogen-bonding interactions forming supramolecular network. The possible hydrogen-bonding interactions between cation and anion units were analysed on the basis of molecular orbital calculations. The obtained deuterated analogue crystallises similar as H-compound in the monoclinic system (P21/c) with quite similar lattice parameters. The compound was also characterised by the FT-IR and Raman spectroscopies. The characteristic bands of the functional and skeletal groups of the protiated and deuterated analogue of 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate are discussed.

The solid-state organisation of 1-(diaminomethylene) thiouron-1-ium 4-hydroxybenzenesulfonate has been analysed with respect to cation–anion and hydrogen bonding interactions. The oppositely charged units interact via hydrogen bonds with the graph of R22(8).Figure optionsDownload as PowerPoint slide