A concise preparative IMDAV strategy for the synthesis of benzo-, carbocyclo-, and thienothiopheneisoindolecarboxylic acids, which display antifungal and antibacterial activity, starting from readily available materials is proposed.

The molecular conformation of the title compound, C₂₄H₂₃NO₅·C₃H₇NO, is consolidated by intramolecular C—H...O O—H...O hydrogen bonds, forming an S(6) ring motif. In the crystal, the molecules are connected by C—H...O hydrogen bonds, forming layers parallel to the (101) plane. Furthermore, the molecules form layers parallel to the (102) plane by C—H...π interactions. Important intermolecular interactions highlighted by Hirshfeld surface analysis are H...H (54.7%), O...H/H...O (23.0%), and C...H/H...C (19.9%) contacts.

In the title compound, C₂₂H₁₉NO₅S·C₂D₆OS, the central six-membered ring has a slightly distorted boat conformation, while the fused pyrrolidine ring adopts an envelope conformation. These conformations are stabilized by O—H...O hydrogen bonds between the main compound and solvent molecules. In addition, intramolecular C—H...O hydrogen bonds in the main molecule form two S(6) rings. Molecules are connected by pairs of intermolecular C—H...O hydrogen bonds, forming dimers with a R ² ₂(8) motif. These dimers form a three-dimensional network through O—H...O, O—H...S and C—H...O hydrogen bonds with each other directly and through solvent molecules. In addition, weak π–π stacking interactions [centroid-to-centroid distances = 3.9937 (10) and 3.9936 (10) Å, slippages of 2.034 and 1.681 Å] are observed. The intermolecular contacts were quantified using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative contributions of the contacts to the crystal packing to be H...H 41.7%, O...H/H...O 27.7%, C...H/H...C 17.0%, and S...H/H...S 7.5%.

In the title compound, C₂₄H₂₁NO₃S, the cyclopentene ring adopts an envelope conformation. In the crystal, molecules are linked by C—H...π interactions, forming ribbons along the a axis. Intermolecular C—H...O hydrogen bonds connect these ribbons to each other, forming layers parallel to the (0\overline{1}1) plane. The molecular packing is strengthened by van der Waals interactions between the layers. The intermolecular contacts were quantified using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative contributions of the contacts to the crystal packing to be H...H 46.0%, C...H/H...C 21.1%, O...H/H...O 20.6% and S...H/H...S 9.0%.

The title compound, C ₂₈ H ₂₃ ClN ₂ O ₅ S, crystallizes with two independent molecules ( A and B ) in the asymmetric unit. In the central fused ring systems, the pyrrolidine rings adopt envelope conformations and the cyclohexene rings adopt distorted-half chair conformations. In molecules A and B , the least-squares mean planes of the sixteen-membered central ring systems form dihedral angles of 81.5 (1) and 84.0 (1)°, respectively, with the benzene rings attached to the sulfanyl groups, while they make dihedral angles of 18.6 (1) and 7.7 (1)°, respectively, with the chlorobenzene rings. In the crystal, O—H...O hydrogen bonds and weak C—H...O and C—H...Cl interactions link the molecules, forming a three-dimensional network. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015). Acta Cryst . C71, 9–18] in PLATON . The solvent contribution was not included in the reported molecular weight and density. A Hirshfeld surface analysis indicates that H...H (36.8% for molecule A ; 29.8% for molecule B ), O...H/H...O (22.1% for A and 27.3% for B ), C...H/H...C (22.1% for A and 20.2% for B ) and Cl...H/H...Cl (9.7% for A and 13.2% for B ) interactions are the most important contributors to the crystal packing.