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  In situ cryocrystallization and solid-state structures of furfural and some derivatives

Seidel, R. W., Goddard, R., Nöthling, N., & Lehmann, C. W. (2019). In situ cryocrystallization and solid-state structures of furfural and some derivatives. CrystEngComm, 21(21), 3295-3303. doi:10.1039/c9ce00435a.

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Seidel, Rüdiger W.1, Author
Goddard, Richard2, Author              
Nöthling, Nils2, Author              
Lehmann, Christian W.2, Author              
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Straße 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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 Abstract: The crystal and molecular structures of the bio-based platform chemical furfural (1) and its derivatives furfurylamine (2), 2-furonitrile (3) and 2-methylfuran (4), which are all liquid at ambient temperature, have been determined by in situ cryocrystallography. Compound 1 crystallizes with three molecules in the asymmetric unit (Z′ = 3), which all adopt the syn conformation. Compound 2 crystallizes with two crystallographically distinct molecules in gauche and anti conformers, which are linked by N–H⋯N and N–H⋯O hydrogen bonds. The crystal structure of 3 is characterized by C–H⋯N interactions between C4 of the furan ring and the nitrile group. Compound 4 was found to crystallize in the non-centrosymmetric space group P42bc with a polar c axis. The molecular structures are compared with results from spectroscopic studies in the literature. Compounds 1–4 show a difference of ca. 14° between the external C–C–C and C–C–O angles to the substituent carbon atom in 2-position of the furan ring. Using this criterion as an indicator for the assignment of the oxygen atom in 2-substituted furan derivatives, a number of crystal structures in the Cambridge Structural Database (CSD) are called into question.

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Language(s): eng - English
 Dates: 2019-03-232019-05-012019-06-07
 Publication Status: Published online
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/c9ce00435a
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Title: CrystEngComm
  Other : CrystEngComm
Source Genre: Journal
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Publ. Info: London : Royal Society of Chemistry
Pages: - Volume / Issue: 21 (21) Sequence Number: - Start / End Page: 3295 - 3303 Identifier: ISSN: 1466-8033
CoNE: https://pure.mpg.de/cone/journals/resource/954928434986