Supramolecular structures of four (Z)-5-arylmethylene-2-thioxothia-zolidin-4-ones: hydrogen-bonded dimers, chains of rings and sheets

P. Delgado, J. Quiroga, J. Cobo, C. Glidewell

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    Abstract

    In each of the four title compounds, namely (Z)-5-benzylidene-2-thioxothiazolidin-4-one, C10H7NOS2, (I), which crystallizes with Z'=2 in space group P2(1)/n, (Z)-5-(4-methylbenzylidene)-2-thioxothiazolidin-4-one, C11H9NOS2, (II), (Z)-2-thioxo-5-[4-(trifluoromethyl)benzylidene]thiazolidin-4-one, C11H6F3NOS2, (III), and (Z)-5-( 4- methoxybenzylidene)-2-thioxothiazolidin-4-one, C11H9NO2S2, (IV), there is a very wide C-C-C angle (ca 130 degrees) at the methine C atom linking the two rings. Pairs of N-H center dot center dot center dot O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C-H center dot center dot center dot pi(arene) hydrogen bonds. The molecules of (II) are linked by paired N-H center dot center dot center dot O hydrogen bonds into centrosymmetric R-2(2)(8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N-H center dot center dot center dot S and C-H center dot center dot center dot O hydrogen bonds in (III), and from a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen bonds in (IV).

    Original languageEnglish
    Pages (from-to)o477-o482
    Number of pages6
    JournalActa Crystallographica Section C, Crystal Structure Communications
    Volume61
    Issue number61
    DOIs
    Publication statusPublished - 2005

    Cite this

    Supramolecular structures of four (Z)-5-arylmethylene-2-thioxothia-zolidin-4-ones: hydrogen-bonded dimers, chains of rings and sheets. / Delgado, P.; Quiroga, J.; Cobo, J.; Glidewell, C.

    In: Acta Crystallographica Section C, Crystal Structure Communications, Vol. 61, No. 61, 2005, p. o477-o482.

    Research output: Contribution to journalArticle

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    title = "Supramolecular structures of four (Z)-5-arylmethylene-2-thioxothia-zolidin-4-ones: hydrogen-bonded dimers, chains of rings and sheets",
    abstract = "In each of the four title compounds, namely (Z)-5-benzylidene-2-thioxothiazolidin-4-one, C10H7NOS2, (I), which crystallizes with Z'=2 in space group P2(1)/n, (Z)-5-(4-methylbenzylidene)-2-thioxothiazolidin-4-one, C11H9NOS2, (II), (Z)-2-thioxo-5-[4-(trifluoromethyl)benzylidene]thiazolidin-4-one, C11H6F3NOS2, (III), and (Z)-5-( 4- methoxybenzylidene)-2-thioxothiazolidin-4-one, C11H9NO2S2, (IV), there is a very wide C-C-C angle (ca 130 degrees) at the methine C atom linking the two rings. Pairs of N-H center dot center dot center dot O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C-H center dot center dot center dot pi(arene) hydrogen bonds. The molecules of (II) are linked by paired N-H center dot center dot center dot O hydrogen bonds into centrosymmetric R-2(2)(8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N-H center dot center dot center dot S and C-H center dot center dot center dot O hydrogen bonds in (III), and from a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen bonds in (IV).",
    author = "P. Delgado and J. Quiroga and J. Cobo and C. Glidewell",
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    AU - Delgado, P.

    AU - Quiroga, J.

    AU - Cobo, J.

    AU - Glidewell, C.

    PY - 2005

    Y1 - 2005

    N2 - In each of the four title compounds, namely (Z)-5-benzylidene-2-thioxothiazolidin-4-one, C10H7NOS2, (I), which crystallizes with Z'=2 in space group P2(1)/n, (Z)-5-(4-methylbenzylidene)-2-thioxothiazolidin-4-one, C11H9NOS2, (II), (Z)-2-thioxo-5-[4-(trifluoromethyl)benzylidene]thiazolidin-4-one, C11H6F3NOS2, (III), and (Z)-5-( 4- methoxybenzylidene)-2-thioxothiazolidin-4-one, C11H9NO2S2, (IV), there is a very wide C-C-C angle (ca 130 degrees) at the methine C atom linking the two rings. Pairs of N-H center dot center dot center dot O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C-H center dot center dot center dot pi(arene) hydrogen bonds. The molecules of (II) are linked by paired N-H center dot center dot center dot O hydrogen bonds into centrosymmetric R-2(2)(8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N-H center dot center dot center dot S and C-H center dot center dot center dot O hydrogen bonds in (III), and from a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen bonds in (IV).

    AB - In each of the four title compounds, namely (Z)-5-benzylidene-2-thioxothiazolidin-4-one, C10H7NOS2, (I), which crystallizes with Z'=2 in space group P2(1)/n, (Z)-5-(4-methylbenzylidene)-2-thioxothiazolidin-4-one, C11H9NOS2, (II), (Z)-2-thioxo-5-[4-(trifluoromethyl)benzylidene]thiazolidin-4-one, C11H6F3NOS2, (III), and (Z)-5-( 4- methoxybenzylidene)-2-thioxothiazolidin-4-one, C11H9NO2S2, (IV), there is a very wide C-C-C angle (ca 130 degrees) at the methine C atom linking the two rings. Pairs of N-H center dot center dot center dot O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C-H center dot center dot center dot pi(arene) hydrogen bonds. The molecules of (II) are linked by paired N-H center dot center dot center dot O hydrogen bonds into centrosymmetric R-2(2)(8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N-H center dot center dot center dot S and C-H center dot center dot center dot O hydrogen bonds in (III), and from a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen bonds in (IV).

    U2 - 10.1107/S0108270105021888

    DO - 10.1107/S0108270105021888

    M3 - Article

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    JO - Acta Crystallographica Section C, Crystal Structure Communications

    JF - Acta Crystallographica Section C, Crystal Structure Communications

    SN - 0108-2701

    IS - 61

    ER -