Synthesis, crystal structure determination, Hirshfeld surface and crystal void analyses, interaction energy calculations and energy frameworks of (3aRS,4RS,9aRS)-2-benzyl-3-oxo-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid
Acta Crystallographica Section E: Crystallographic Communications, vol.82, pp.722-727, 2026 (ESCI, Scopus)
- Publication Type: Article / Article
- Volume: 82
- Publication Date: 2026
- Doi Number: 10.1107/s2056989026005189
- Journal Name: Acta Crystallographica Section E: Crystallographic Communications
- Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
- Page Numbers: pp.722-727
- Keywords: benzo[f]isoindole, crystal structure, Diels-Alder reaction, IMDAV reaction, isoindole
- Hacettepe University Affiliated: Yes
Abstract
The title compound, C20H19NO3, consists of a benzyl moiety bonded to the nitrogen atom of a 1H-benzo[f]isoindole-4-carboxylic acid group. The fused pyrrole and cyclohexene rings of the isoindole group are in envelope and flattened-boat conformations, respectively. The planar benzene rings are oriented at a dihedral angle of 69.64 (3)°. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds link the molecules, enclosing R22(14) and R22(9) ring motifs, into infinite double-chains along the a-Axis direction. π-π stacking interactions and C-H⋯π(ring) interactions help to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H⋯H (52.2%), H⋯C/C⋯H (24.0%) and H⋯O/O⋯H (21.2%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 92.25 Å3 and 11.52%, showing that there is no large cavity in the crystal packing. Computational methods revealed O-H⋯O and C-H⋯O hydrogen-bonding energies of-103.8,-82.2 and-35.5 kJ mol-1. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the electrostatic energy contributions.