| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1403713 | Journal of Molecular Structure | 2011 | 7 Pages |
A monohydrate, and three solvates of a metabolite of an antibacterial agent, sulfamerazine, N4-acetylsulfamerazine (NSMZ), were identified and characterized by nuclear magnetic resonance spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and single crystal X-ray diffraction. The solvates were obtained with the solvents: acetic acid, methanol, and 1,4-dioxane. All the crystal structures belong to the triclinic, P1¯ space group. Analysis of hydrogen bonding in the crystal structures revealed that the NSMZ molecules form a dimer via a pair of intermolecular N–H⋯N hydrogen bonds. These dimers are interconnected to each other via the solvent molecules forming extended hydrogen bonded networks. The conformations of the NSMZ in the hydrate/solvates are found to be significantly different. Thermal analysis established the stability and confirmed molar ratios of the reported hydrate/solvates, whereas crystal lattice energies and competitive crystallization experiments confirmed the stability of methanol solvate over the hydrate and other solvates.
► N4-acetylsulfamerazine (NSMZ) forms a monohydrate, and three solvates. ► Single crystal X-ray diffraction revealed different hydrogen bonded networks. ► NSMZ molecule adopts different conformations in crystal structures of solvates/hydrate. ► Computational analysis revealed the greater stability of methanol solvate. ► Competitive crystallization experiments are consistent with the computational analysis.
