Two isomeric butadiene-N-(acetoxyphenyl)maleimide Diels-Alder adducts: supramolecular structure directed by C-H...X (X = O and pi) 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 benzene rings depends on the position of the acetoxy substitution [89.7 (1) and 61.9 (1) degrees 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) degrees ]. 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).
Trujillo-Ferrara
Jose G
JG
Sección de Graduados y Departamento de Bioquímica, Escuela Superior de Medicina, Instituto Politécnico Nacional, México DF 11340, Mexico.
Santillán-Baca
Rosa Luisa
RL
Farfán-García
Norberto
N
Padilla-Martínez
Itzia I
II
García-Báez
Efrén V
EV
D002070:Butadienes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D002070:Butadienes; D008301:Maleimides; C515689:butadiene-N-(acetoxyphenyl)maleimide