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Crystal structure and Hirshfeld surface analysis of (<i>Z</i>)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid

Okan Simsek, Muharrem Dincer, Necmi Dege, Eiad Saif, Ibrahim Yilmaz, Alaaddin Cukurovali

2022Acta Crystallographica Section E Crystallographic Communications17 citationsDOIOpen Access PDF

Abstract

The title cyclobutyl compound, C 18 H 18 N 2 O 3 S, was synthesized by the interaction of 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine and maleic anhydride, and crystallizes in the orthorhombic space group P 2 1 2 1 2 1 with Z ′ = 1. The molecular geometry is partially stabilized by an intramolecular N—H...O hydrogen bond forming an S 1 1 (7) ring motif. The molecule is non-planar with a dihedral angle of 88.29 (11)° between the thiazole and benzene rings. In the crystal, the molecules are linked by O—H...N hydrogen bonds, forming supramolecular ribbons with C 1 1 (9) chain motifs. To further analyze the intermolecular interactions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H...H (43%), C...H (18%), O...H (17%) and N...H (6%), interactions.

Topics & Concepts

Dihedral angleChemistryCrystallographyHydrogen bondCrystal structureRing (chemistry)Surface (topology)BenzeneGroup (periodic table)Crystal (programming language)Maleic acidChain (unit)Surface structureMolecular geometrySpace (punctuation)HydrogenCrystal structures of chemical compoundsSynthesis of heterocyclic compoundsChemical Synthesis and Analysis
Crystal structure and Hirshfeld surface analysis of (<i>Z</i>)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid | Litcius