Structural Characterization of Two Polymorphs of 
1-(4-Methylpyridin-2-yl)thiourea and Two Derived 2-Aminothiazoles

Böck, Denise; Beuchel, Andreas; Goddard, Richard; Imming, Peter; Seidel, Rüdiger W.

doi:10.1007/s10870-020-00863-0

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Structural Characterization of Two Polymorphs of 1-(4-Methylpyridin-2-yl)thiourea and Two Derived 2-Aminothiazoles

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Goddard, Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Böck, D., Beuchel, A., Goddard, R., Imming, P., & Seidel, R. W. (2021). Structural Characterization of Two Polymorphs of 1-(4-Methylpyridin-2-yl)thiourea and Two Derived 2-Aminothiazoles. Journal of Chemical Crystallography, 51(9), 394-404. doi:10.1007/s10870-020-00863-0.

Cite as: https://hdl.handle.net/21.11116/0000-0009-04A3-A

Abstract

Two polymorphic forms of 1-(4-methylpyridin-2-yl)thiourea (1) and the crystal and molecular structures of the 2-aminothiazoles N-(4-methylpyridin-2-yl)-4-(pyridin-2-yl)thiazol-2-amine (2) and N-(4-methylpyridin-2-yl)-4-(pyrazin-2-yl)thiazol-2-amine (3), derived from 1 and the respective α-bromoketone via the Hantzsch reaction, are described. Both polymorphic forms 1α (space group P2₁/c, Z = 4) and 1β (space group P2₁/n, Z = 8) crystallize in the monoclinic system but exhibit distinctly different intermolecular hydrogen bonding patterns. Compound 2 (orthorhombic, space group Pca2₁, Z = 8) forms polymeric N–H⋯N hydrogen-bonded zigzag tapes in the polar crystal structure, with a significant twisting between the thiazole and pyridine rings. In contrast, the crystal structure of 3 (monoclinic, space group P2₁/c, Z = 4) features nearly planar centrosymmetric N–H⋯N hydrogen-bonded dimers, which are laterally joined through long C–H⋯N contacts, affording a π⋯π stacked layered structure.