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C-H...πarene, Csp³-H...O=C and O-H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: a meta-tyrosine derivative

Gallagher, John F. and Murphy, Carol (1999) C-H...πarene, Csp³-H...O=C and O-H...O intermolecular interactions in (2R/2S)-3-(3-hydroxyphenyl)-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid: a meta-tyrosine derivative. Acta Crystallographica Section C, 55 (12). pp. 2167-2169. ISSN 0108-2701

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Abstract

The title compound, C₁₇H₁₅NO₄, a DL-meta-tyrosine derivative forms a hydrogen-bonded network in the solid state which consists of Oacid--H... Ophenyl--H...O=Cisoindole chains [O...O 2.668 (2) and 2.653 (2)Å], Csp³--H ...O=Cacid [C...O 3.225 (3)Å] and two C--H...πarene intermolecular interactions. The Carene--H...πphenyl interaction is short, C...Cg 3.542(3)Å, where Cg is the phenyl ring centroid (H...Cg 2.64 Å and C--H...Cg 165°). The interplanar angle between the five- and six-membered rings of the isoindole system is 0.95 (13)° with the carbonyl-O atom 0.096(3)Å from the C₄N ring plane. π-π stacking involving inversion symmetry-related isoindole groups occurs with RS pairs (interplanar distance of 3.43 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/S0108270199010884
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License
ID Code:299
Deposited On:12 Mar 2008 by DORAS Administrator. Last Modified 03 Feb 2009 13:04

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