2-(3-Hydroxypropyl)isoindoline-1,3-dione: competition among hydrogen-bond acceptors.
The title compound, C(11)H(11)NO(3), has two molecules in the asymmetric unit, which differ in the orientation of their side-chain OH groups, allowing them to form intermolecular O-H...O hydrogen bonds to different acceptors. In one case, the acceptor is the OH group of the other molecule, and in the other case it is an imide O=C group. This is the first example in the N-substituted phthalimide series in which independent molecules have different types of acceptor. Molecular-orbital calculations place the greatest negative charge on the OH group.
Wang
Honghao
H
School of Life and Health Sciences, Aston University, Aston Triangle, Birmingham B4 7ET, England.
Bache
Chris J
CJ
Schwalbe
Carl H
CH
D003461:Crystallography; D006860:Hydrogen Bonding; D054833:Isoindoles / Q000737:chemistry*; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*
C531933:2-(3-hydroxypropyl)isoindoline-1,3-dione; D054833:Isoindoles; D010797:Phthalimides