Issue 92, 2003
From the journal:

CrystEngComm

Molecular self-assembly: 4-formylcoumarins as versatile skeletons for complementary multipoint association via weak (C–H⋯O, C–H⋯F and C–X⋯O[double bond, length half m-dash]C) interactions

J. Narasimha Moorthy,*a   P. Venkatakrishnana  and  Ashutosh S. Singha  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology, Kanpur, India
E-mail: moorthy@iitk.ac.in
Fax: 91-512-2597436 and 91-512-2597000
Tel: 91-512-2597438

Abstract

The substituted 4-formylcoumarins feature remarkable skeletons for molecular edge-to-edge self-assembly via complementary multipoint weak C–H⋯O, C–H⋯F and C–X⋯O[double bond, length half m-dash]C interactions, as revealed by the X-ray crystal structure analyses of 1–6. It is shown that the formylcoumarins 1–6 can exploit as many as 6–10 weak interactions despite being structurally so simple. The edge-to-edge association via6 complementary hydrogen bonds in 1, 2, and 4 leads to 1-dimensional molecular arrays (tapes/strands), which get interconnected by C–H⋯O/C–X⋯O[double bond, length half m-dash]C noncovalent hydrogen/halogen bonds to form 2-dimensional sheets. The substitution of a hydrogen by fluoro group as in 5 and 6 leads to a dramatic change in the crystal packing, thereby implying the preponderant influence of C–H⋯F interactions over C–H⋯O interactions in at least the cases studied herein.

Graphical abstract: Molecular self-assembly: 4-formylcoumarins as versatile skeletons for complementary multipoint association via weak (C–H⋯O, C–H⋯F and C–X⋯O [[double bond, length half m-dash]] C) interactions

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Article information

DOI
https://doi.org/10.1039/B315065H
Article type
Paper
Submitted
20 Nov 2003
Accepted
20 Nov 2003
First published
16 Dec 2003

CrystEngComm, 2003,5, 507-513

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Molecular self-assembly: 4-formylcoumarins as versatile skeletons for complementary multipoint association via weak (C–H⋯O, C–H⋯F and C–X⋯O[double bond, length half m-dash]C) interactions

J. N. Moorthy, P. Venkatakrishnan and A. S. Singh, CrystEngComm, 2003, 5, 507 DOI: 10.1039/B315065H

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