Crystal packing in some flexible carboxylic acids and esters attached to a naphthalene ring?

CrystEngComm Pub Date: 2008-08-12 DOI: 10.1039/B808399A

Abstract

A structural study of four dicarboxylic acids and four esters attached to a naphthalene ring is presented. (4-Carboxymethoxy-naphthalen-2-yloxy)-acetic acid (1) has a chain structure in the lattice while (6-carboxymethoxy-naphthalen-1-yloxy)-acetic acid (2) and (7-carboxymethoxy-naphthalen-2-yloxy)-acetic acid (3) adopt a sheet-like structure through weak intermolecular interactions, C–H?O and C–H?π hydrogen bonds. (3-Carboxymethylsulfanyl-1,4-dihydroxy-naphthalen-2-ylsulfanyl)-acetic acid has two symmetrically non-equivalent molecules per unit cell. The asymmetry is caused by weak C–H?S interactions. The packing pattern of the methyl esters differs significantly from the parent carboxylic acids and the packing patterns in each case were found to be determined by the C–H?O and C–H?π interactions.

Graphical abstract: Crystal packing in some flexible carboxylic acids and esters attached to a naphthalene ring
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