Two isomeric butadiene-N-(acetoxy­phenyl)maleimide Diels-Alder adducts: supramolecular structure directed by C-H⋯X (X = O and π) hydrogen bonds and perpendicular dipole carbonyl-carbonyl inter­actions

The mol­ecular and supramolecular structures of 2‐(1,3‐dioxo‐2,3,3a,4,7,7a‐hexa­hydro‐1H‐isoindol‐2‐yl)phenyl acetate, C16‐H15NO4, (I), and its para isomer, 4‐(1,3‐dioxo‐2,3,3a,4,7,7a‐hexa­hydro‐1H‐isoindol‐2‐yl)phenyl acetate, (II), are reported. The torsion angle between the succinimide and benzen...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2006-03, Vol.62 (3), p.o125-o128
Main Authors: Trujillo-Ferrara, Jose G., Santillán-Baca, Rosa Luisa, Farfán-García, Norberto, Padilla-Martínez, Itzia I., García-Báez, Efrén V.
Format: Article
Language:English
Subjects:
Chemical compounds
Molecular structure
Organic chemicals
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Summary:The mol­ecular and supramolecular structures of 2‐(1,3‐dioxo‐2,3,3a,4,7,7a‐hexa­hydro‐1H‐isoindol‐2‐yl)phenyl acetate, C16‐H15NO4, (I), and its para isomer, 4‐(1,3‐dioxo‐2,3,3a,4,7,7a‐hexa­hydro‐1H‐isoindol‐2‐yl)phenyl acetate, (II), are reported. The torsion angle between the succinimide and benzene rings depends on the position of the acet­oxy substitution [89.7 (1) and 61.9 (1)° for (I) and (II), respectively]. The twist of the acet­oxy group relative to the mean plane of the benzene ring is almost independent of the acet­oxy position [66.0 (1) and 70.0 (1)°]. Packing inter­actions for both compounds include soft C—H⋯X (X = O and Ph) inter­actions, forming chains of centrosymmetric dimers and inter­linked chains for (I) and (II), respectively. In addition, three perpendicular dipole C=O⋯C=O inter­actions contribute to the supramolecular structure of (II).
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270106002186