Co-crystalline hydrogen bonded solids based on the alcohol–carboxylic acid–alcohol supramolecular motif
- 8 January 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in CrystEngComm
- Vol. 6 (3), 5-10
- https://doi.org/10.1039/b313956e
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⋯OC(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.Keywords
This publication has 29 references indexed in Scilit:
- Co-crystalline hydrogen bonded solids formed by helical tubuland diolsCrystEngComm, 2002
- Organic nanoporous structuresCurrent Opinion in Solid State and Materials Science, 2001
- Polymorphism inp-Hydroxybenzoic Acid: The Effect of Intermolecular Hydrogen Bonding in Controlling Proton Order versus Disorder in the Carboxylic Acid Dimer MotifAngewandte Chemie International Edition, 2000
- Formation and Structure of a New Family of Organic CocrystalsChemistry of Materials, 1994
- 2,7-Dimethyltricyclo[4.3.1.13,8]undecane-syn-2,syn-7-diol: structural analysis of the ellipsoidal clathrate and hemihydrate crystal formsJournal of the Chemical Society, Perkin Transactions 2, 1993
- The development of versions 3 and 4 of the Cambridge Structural Database SystemJournal of Chemical Information and Computer Sciences, 1991
- Mapping the molecular pathway during photoaddition of guest acetophenone and p-fluoroacetophenone to host deoxycholic acid as studied by x-ray diffraction in systems undergoing single-crystal-to-single-crystal transformationJournal of the American Chemical Society, 1987
- 2?1 Complex of desoxycholic acid and ethyl acetate: Disorder in the structure at 298 and 163 KJournal of Chemical Crystallography, 1986
- Modification of tube size and shape in a helical tubuland inclusion lattice formed by a new family of diol hosts: syntheses and crystal structuresJournal of the Chemical Society, Perkin Transactions 2, 1986
- The structure of the 2:1 complex between the bile acid deoxycholic acid and (+)-camphorActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1982