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

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.

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 Creators:
Böck, Denise1, Author
Beuchel, Andreas1, Author
Goddard, Richard2, Author           
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Martin-Luther-Universität Halle-Wittenberg, Institut für Pharmazie, Wolfgang-Langenbeck-Str. 4, 06120, Halle (Saale), Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: 1-(4-Methylpyridin-2-yl)thiourea; 2-Aminothiazoles; Hantzsch reaction; Hydrogen Bonding; Polymorphism; Crystal structure
 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.

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Language(s): eng - English
 Dates: 2020-06-112020-10-012021-09-01
 Publication Status: Published in print
 Pages: 11
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1007/s10870-020-00863-0
 Degree: -

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Title: Journal of Chemical Crystallography
  Abbreviation : J. Chem. Crystallogr.
Source Genre: Journal
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Publ. Info: New York : Springer Science+Business Media
Pages: - Volume / Issue: 51 (9) Sequence Number: - Start / End Page: 394 - 404 Identifier: ISSN: 1074-1542
CoNE: https://pure.mpg.de/cone/journals/resource/954925604775