Hirshfeld surface analysis of sulfameter (polymorph III), sulfameter dioxane monosolvate and sulfameter tetrahydrofuran monosolvate, all at 296 K. Issue 11 (13th October 2015)

• Record Type: Journal Article
• Authors: Tailor, Sanjay M.; Patel, Urmila H.
• Is Part Of: Acta crystallographica. Volume 71:Issue 11(2015:Nov.)
• Page Start: 944
• Page End: 953
• Publication Date: 2015-10-13
• Subjects: Hirshfeld analysis -- fingerprint plots -- crystal structure -- hydrogen bonding -- active pharmaceutical ingredients -- drug development -- sulfonamides -- conformational polymorphism -- sulfameter -- crystal structure prediction; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229615017520
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The ability of the antibacterial agent sulfameter (SMT) to form solvates is investigated. The X‐ray crystal structures of sulfameter solvates have been determined to be conformational polymorphs. Both 1, 4‐dioxane and tetrahydrofuran form solvates with sulfameter in a 1:1 molar ratio. 4‐Amino‐ N ‐(5‐methoxypyrimidin‐2‐yl)benzenesulfonamide (polymorph III), C11 H12 N4 O3 S, (1), has two molecules of sulfameter in the asymmetric unit cell. 4‐Amino‐ N ‐(5‐methoxypyrimidin‐2‐yl)benzenesulfonamide 1, 4‐dioxane monosolvate, C11 H12 N4 O3 S·C4 H8 O2, (2), and 4‐amino‐ N ‐(5‐methoxypyrimidin‐2‐yl)benzenesulfonamide tetrahydrofuran monosolvate, C11 H12 N4 O3 S·C4 H8 O, (3), crystallize in the imide form. Hirshfeld surface analyses and fingerprint analyses were performed to study the nature of the interactions and their quantitative contributions towards the crystal packing. Finally, Hirshfeld surfaces, fingerprint plots and structural overlays were employed for a comparison of the two independent molecules in the asymmetric unit of (1), and also for a comparison of (2) and (3) in the monoclinic crystal system. A three‐dimensional hydrogen‐bonding network exists in all three structures, involving one of the sulfone O atoms and the aniline N atom. All three structures are stabilized by strong intermolecular N—H...N interactions. The tetrahydrofuran solvent molecule also takes part in forming significant intermolecular C—H...O interactions in the crystal structure of (3), contributing to the stability of the crystal packing.