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Issue 6, 2016
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Persistence of a self-complementary N–H⋯N tape motif in chloro-s-triazine crystals: crystal structures of simazine and atrazine herbicides and their polymorphic and inclusion behaviour

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Abstract

The bis-N-alkyl-chloro-s-triazines simazine 1 and atrazine 2 are potent and widely used commercial herbicides; however, their crystal structures have been unreported to date. This study reports the synchrotron crystal structures of 1 and 2, with the latter forming two polymorphs, as well as acting as a host structure for three haloalkane guest molecules. The molecular assembly in all of the crystal structures is an N–H⋯N hydrogen-bonded tape between hydrophobic phases formed by tightly packed alkyl side chains. The hydrogen-bonded tape is persistent across all structures in this study, and a survey of the literature and the Cambridge Structural Database (CSD) reveals the tape formation to be a persistent, highly stable motif in a range of chloro-s-triazines. The tape morphology occurs as different sub-groups that correlate to the volume of the N-substituent in a way that may permit a certain level of prediction and design for unknown crystal structures.

Graphical abstract: Persistence of a self-complementary N–H⋯N tape motif in chloro-s-triazine crystals: crystal structures of simazine and atrazine herbicides and their polymorphic and inclusion behaviour

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Publication details

The article was received on 10 Nov 2015, accepted on 31 Dec 2015 and first published on 04 Jan 2016


Article type: Paper
DOI: 10.1039/C5CE02206A
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Citation: CrystEngComm, 2016,18, 962-970
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    Persistence of a self-complementary N–H⋯N tape motif in chloro-s-triazine crystals: crystal structures of simazine and atrazine herbicides and their polymorphic and inclusion behaviour

    T. Le, M. Bhadbhade, J. Gao, J. M. Hook and C. E. Marjo, CrystEngComm, 2016, 18, 962
    DOI: 10.1039/C5CE02206A

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