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Issue 42, 2016
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Solvatomorphism in (Z)-4-fluoro-N′-(3-fluorophenyl)benzimidamide: the role of intermolecular O–H⋯F interaction

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Abstract

The synthesized compound (Z)-4-fluoro-N′-(3-fluorophenyl)benzimidamide exhibits solvatomorphism in the solid state. The anhydrous and the hydrate forms were obtained at room temperature from slow evaporation of cyclohexane and hexane solvents, respectively. Both forms crystallize in the triclinic P[1 with combining macron] with two symmetry-independent molecules in the asymmetric unit. The crystal packing of the anhydrous form is stabilized via a strong N–H⋯N chain, whereas the hydrate form is stabilized via a strong (N–H⋯N)–(N–H⋯O)–(O–H⋯N) chain. The water molecule plays an important role in the crystal packing by the formation of “extremely short” N–H⋯O and O–H⋯N hydrogen bonds, which are further supported by weak O–H⋯F–C and C–H⋯O interactions. The basic structural building motifs were structurally and energetically equivalent in both forms. PIXEL and QTAIM approaches provide quantitative insights into the nature and energetics of strong as well as weak intermolecular interactions. The NCI descriptor shows the “attractive” nature of the rarely observed O–H⋯F interaction. The thermal stabilities of the solvatomorphs were characterized via differential scanning calorimetry, hot stage microscopy, and thermogravimetric analysis. Hirshfeld surface analysis and 2D fingerprint plots of the individual molecules present in both forms differentiate the trends in crystal packing as well as the contribution from the different intermolecular interactions.

Graphical abstract: Solvatomorphism in (Z)-4-fluoro-N′-(3-fluorophenyl)benzimidamide: the role of intermolecular O–H⋯F interaction

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Publication details

The article was received on 29 Jul 2016, accepted on 15 Sep 2016 and first published on 16 Sep 2016


Article type: Paper
DOI: 10.1039/C6CE01668E
Citation: CrystEngComm, 2016,18, 8291-8300
  • Open access: Creative Commons BY-NC license
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    Solvatomorphism in (Z)-4-fluoro-N′-(3-fluorophenyl)benzimidamide: the role of intermolecular O–H⋯F interaction

    D. Dey and D. Chopra, CrystEngComm, 2016, 18, 8291
    DOI: 10.1039/C6CE01668E

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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