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Issue 36, 2017
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Quantitative investigation of C–H⋯π and other intermolecular interactions in a series of crystalline N-(substituted phenyl)-2-naphthamide derivatives

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Abstract

In this study, we have investigated the nature and characteristics of different intermolecular interactions present in a series of seven N-(substituted phenyl)-2-naphthamides. The seven structures comprise 2-naphthyl ring systems linked by amide bridges to N-bound phenyl 1, or substituted benzene rings 3–7, or in the case of 2, a cyclohexane ring. A common feature of the crystal packing for all but the o-nitro derivative 7 is the presence of a strong intermolecular N–H⋯O interaction. In the case of 7, the possibility of such an interaction is obviated by the formation of an intramolecular N–H⋯O hydrogen bond. An additional feature of the crystal packing for 1–6 is the significant roles that C–H⋯π contacts play in generating three-dimensional networks. In contrast for 7, the intramolecular N–H⋯O hydrogen bond precludes the formation of molecular chains but the planar nature of this molecule allows significant π⋯π stacking interactions to stabilize the packing.

Graphical abstract: Quantitative investigation of C–H⋯π and other intermolecular interactions in a series of crystalline N-(substituted phenyl)-2-naphthamide derivatives

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Publication details

The article was received on 18 Jul 2017, accepted on 07 Aug 2017 and first published on 08 Aug 2017


Article type: Paper
DOI: 10.1039/C7CE01310H
Citation: CrystEngComm, 2017,19, 5473-5491
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    Quantitative investigation of C–H⋯π and other intermolecular interactions in a series of crystalline N-(substituted phenyl)-2-naphthamide derivatives

    R. Shukla, A. Saeed, J. Simpson and D. Chopra, CrystEngComm, 2017, 19, 5473
    DOI: 10.1039/C7CE01310H

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