Crystal structure of edoxaban tosylate monohydrate Form I, (C ₂₄ H ₃₁ ClN ₇ O ₄ S)(C ₇ H ₇ O ₃ S)(H ₂ O)

The crystal structure of edoxaban tosylate monohydrate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Edoxaban tosylate monohydrate crystallizes in space group P 2 ₁ (#4) with a = 7.55097(2), b = 7.09010(2), c = 32.80420(21) Å, β = 96.6720(3)°, V = 1744.348(6) Å ³ , and Z = 2. The crystal structure consists of alternating layers of edoxaban cations and tosylate anions along the c -axis. The water molecules lie near the sulfonate end of the tosylate anions. The solid-state conformation of the edoxaban cation is determined by intermolecular interactions. The protonated nitrogen atom forms a strong N–H⋯O hydrogen bond to one of the tosylate oxygens. Only one of the water molecule hydrogens acts as a donor in an O–H⋯O hydrogen bond. The tosylate oxygens act as acceptors in a number of C–H⋯O hydrogen bonds. The powder pattern has been submitted to ICDD ^® for inclusion in the Powder Diffraction File™.