Consistent supramolecular motif of C(7) O - H⋯O hydrogen-bonded chains and different local symmetries in three isoindole-4-carboxylic acid derivatives

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Alekseeva K. A., Gurbanov A. V., Tsiulina E. N., Golubenkova A. S., AKKURT M., Manahelohe G. M.

Acta Crystallographica Section E: Crystallographic Communications, cilt.82, ss.40-46, 2026 (ESCI, Scopus)

• Yayın Türü: Makale / Tam Makale
• Cilt numarası: 82
• Basım Tarihi: 2026
• Doi Numarası: 10.1107/s2056989025010709
• Dergi Adı: Acta Crystallographica Section E: Crystallographic Communications
• Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
• Sayfa Sayıları: ss.40-46
• Anahtar Kelimeler: crystal structure, Hirshfeld surface analysis, hydrogen bonds, zigzag chains
• Erciyes Üniversitesi Adresli: Evet

Özet

The syntheses and structures of (3aRS,4RS,9aSR)-3-oxo-2-(2-phenylethyl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid, C21H21NO3 (I), (3aRS,4RS,9aSR)-3-oxo-2-(propan-2-yl)-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid, C16H19NO3 (II) and (4RS)-3-oxo-2-phenyl-2,3,4,9-tetrahydro-1H-benzo[f]isoindole-4-carboxylic acid, C19H15NO3 (III), are described. Compound (I) crystallizes with two molecules in the asymmetric unit. In the extended structures of (I), (II) and (III) the molecules are linked by Oc - H⋯Oi (c = carboxylic acid, i = indole) hydrogen bonds, forming a common C(7) zigzag chain motif propagating along the [010] direction, despite the different local symmetries. These chains are connected by weak C - H⋯O and C - H⋯π interactions, forming a three-dimensional network in each case. A Hirshfeld surface analysis was undertaken to investigate and quantify the intermolecular interactions, which are dominated by H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts in each case.