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O-H...O, C-H...O and C-H...[pi]arene intermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid

Gallagher, John F. and Brady, Fiona (2000) O-H...O, C-H...O and C-H...[pi]arene intermolecular interactions in (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid. Acta Crystallographica Section C, 56 (5). pp. 619-622. ISSN 0108-2701

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Abstract

In the first of the title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, C₁₃H₁₅NO₃, prepared from L-norvaline, a hydrogen-bonded network is formed in the solid state through O-H...O=C, C-H...O=C and C-H...πarene intermolecular interactions, with shortest O...O, C...O and C...centroid distances of 2.582 (13), 3.231 (11) and 3.466 (3) Å, respectively. In the L-valine derivative, (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, C₁₃H₁₅NO₃, O-H...O=C and Carene-H...O=C intermolecular interactions generate a cyclic R²₂(9) motif through cooperativity, with shortest O...O and C...O distances of 2.634 (3) and 3.529 (5) Å, respectively. Methylene C-H...O=Cindole interactions complete the hydrogen bonding, with C...O distances ranging from 3.283 (4) to 3.477 (4) Å.

Item Type:Article (Published)
Refereed:Yes
Subjects:Physical Sciences > Chemistry
Physical Sciences > Crystallography
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Publisher:International Union of Crystallography
Official URL:http://dx.doi.org/10.1107/S0108270100003553
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License
ID Code:302
Deposited On:12 Mar 2008 by DORAS Administrator. Last Modified 03 Feb 2009 14:24

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