Issue 3, 2004
From the journal:

CrystEngComm

Co-crystalline hydrogen bonded solids based on the alcohol–carboxylic acid–alcohol supramolecular motif

Solhe F. Alshahateet,a   Kazunori Nakano,†a   Roger Bishop,*a   Donald C. Craig,a   Kenneth D. M. Harrisb  and  Marcia L. Scuddera  

* Corresponding authors

a School of Chemical Sciences, The University of New South Wales, UNSW Sydney, Australia
E-mail: r.bishop@unsw.edu.au

b Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, UK

Abstract

The helical tubuland diol 4 forms 1 ∶ 1 hydrogen bonded co-crystalline adducts with 2-propanol and propanoic acid in space group P21/c, and with benzoic acid in C2/c. In the first of these compounds, the 2-propanol molecules contribute one hydroxy group to the intermolecular ⋯O–H⋯O–H⋯O–H⋯ hydrogen bond repeat unit. The co-crystals formed with propanoic acid and benzoic acid both contain a ⋯O–H⋯O[double bond, length as m-dash]C(R)–O–H⋯O–H⋯ repeat unit with the hydrogen bonds surrounding a pseudo-threefold screw axis, and where the carboxylic acid group functions like an extended alcohol hydroxy group. Aromatic offset face–face associations also play a significant role in the crystal structure of the benzoic acid compound.

Graphical abstract: Co-crystalline hydrogen bonded solids based on the alcohol–carboxylic acid–alcohol supramolecular motif

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Article information

DOI
https://doi.org/10.1039/B313956E
Article type
Paper
Submitted
03 Nov 2003
Accepted
19 Dec 2003
First published
08 Jan 2004

CrystEngComm, 2004,6, 5-10

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Co-crystalline hydrogen bonded solids based on the alcohol–carboxylic acid–alcohol supramolecular motif

S. F. Alshahateet, K. Nakano, R. Bishop, D. C. Craig, K. D. M. Harris and M. L. Scudder, CrystEngComm, 2004, 6, 5 DOI: 10.1039/B313956E

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