Work

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

Year: 2025

Type: article

Abstract: The syntheses and structures of (3a RS ,4 RS ,9a SR )-3-oxo-2-(2-phenylethyl)-2,3,3a,4,9,9a-hexahydro-1 H -benzo[ f ]isoindole-4-carboxylic acid, C 21 H 21 NO 3 (I), (3a RS ,4 RS ,9a SR )-3-oxo-2-(propan-2-yl)-2,3,3a,4,9,9a-hexahydro-1 H -benzo[ f ]isoindole-4-carboxylic acid, C 16 H 19 NO 3 (II) and (4 RS )-3-oxo-2-phenyl-2,3,4,9-tetrahydro-1 H -benzo[ f ]isoindole-4-carboxylic acid, C 19 H 15 NO 3 (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 O c —H...O i (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.

Source: Acta Crystallographica Section E Crystallographic Communications

DOI: 10.1107/s2056989025010709

Authors: Kseniia A. Alekseeva, Atash V. Gurbanov, Ekaterina N. Tsiulina, Alexandra S. Golubenkova, Mehmet Akkurt, Gizachew Mulugeta Manahelohe

Institutions: Peoples' Friendship University of Russia, Baku State University, Erciyes University, University of Gondar

Language: English

Topic: Crystal structures of chemical compounds

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $500

Funder: RUDN University