Crystal structure of edoxaban tosylate monohydrate Form I, (C24H31ClN7O4S)(C7H7O3S)(H2O). Issue 2 (June 2021)

• Record Type: Journal Article
• Authors: Kaduk, James A.; Gindhart, Amy M.; Blanton, Thomas N.
• Is Part Of: Powder diffraction. Volume 36:Issue 2(2021)
• Page Start: 107
• Page End: 113
• Publication Date: 2021-06
• Subjects: edoxaban, -- Lixiana®, -- Rietveld refinement, -- density functional theory; Powder metallurgy -- Periodicals; Materials -- Analysis -- Periodicals; 620.1127
• DOI: 10.1017/S0885715621000117
• Languages: English
• ISSNs: 0885-7156

Abstract

Abstract : 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 21 (#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™.