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  A solid solution of ethyl and d3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate

Beuchel, A., Goddard, R., Imming, P., & Seidel, R. W. (2020). A solid solution of ethyl and d3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate. Acta Crystallographica Section E: Structure Reports Online, 76(8), 1255-1259. doi:10.1107/S2056989020008956.

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 Creators:
Beuchel, Andreas1, Author
Goddard, Richard2, Author              
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut 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: 2-aminothiazole; Hantzsch reaction; heterocycle; solid solution; hydrogen bonding; crystal structure
 Abstract: The synthesis of ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole- 5-carboxylate via the Hantzsch reaction and partial in situ transesterification during recrystallization from methanol-d4 to the d3-methyl ester, resulting in the title solid solution, ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thia- zole-5-carboxylate–d3-methyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate (0.88/0.12), 0.88C17H16N4O2S∙0.12C16D3H11N4O2S, is reported. The refined ratio of ethyl to d3-methyl ester in the crystal is 0.880 (6):0.120 (6). The pyridine ring is significantly twisted out of the plane of the approximately planar picoline thiazole ester moiety. N—H∙ ∙ ∙N hydrogen bonds between the secondary amino group and the pyridine nitrogen atom of an adjacent symmetry-related molecule link the molecules into polymeric hydrogen-bonded zigzag tapes extending by glide symmetry in the [001] direction. There is structural evidence for intramolecular N∙ ∙ ∙S chalcogen bonding and intermolecular weak C—H∙ ∙ ∙O hydrogen bonds between adjacent zigzag tapes.

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Language(s): eng - English
 Dates: 2020-06-292020-07-102020-08-01
 Publication Status: Published online
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1107/S2056989020008956
 Degree: -

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Title: Acta Crystallographica Section E: Structure Reports Online
  Other : Struct. Rep. Online
  Other : Structure Reports Online
  Abbreviation : Acta Crystallogr., Sect. E: Struct. Rep. Online
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Chester, UK : International Union of Crystallography
Pages: - Volume / Issue: 76 (8) Sequence Number: - Start / End Page: 1255 - 1259 Identifier: ISSN: 1600-5368
CoNE: https://pure.mpg.de/cone/journals/resource/954925468297