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.ORCID: 0000-0003-4130-4556 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
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.