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.

In the title compound, C₂₀H₁₈N₂S, the asymmetric unit comprises two similar molecules (A and B). In molecule A, the central thiophene ring makes dihedral angles of 89.96 (12) and 57.39 (13)° with the 1H-pyrrole rings, which are bent at 83.22 (14)° relative to each other, and makes an angle of 85.98 (11)° with the phenyl ring. In molecule B, the corresponding dihedral angles are 89.49 (13), 54.64 (12)°, 83.62 (14)° and 85.67 (11)°, respectively. In the crystal, molecular pairs are bonded to each other by N—H...N interactions. N—H...π and C—H...π interactions further connect the molecules, forming a three-dimensional network. A Hirshfeld surface analysis indicates that H...H (57.1% for molecule A; 57.3% for molecule B), C...H/H...C (30.7% for molecules A and B) and S...H/H...S (6.2% for molecule A; 6.4% for molecule B) interactions are the most important contributors to the crystal packing.

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%.

A concise preparative IMDAV strategy for the synthesis of benzo- and carbocyclofuroisoindole carboxylic acids starting from readily available materials was proposed.

In the title compound, C ₁₇ H ₁₁ NO ₃ S, the thieno[2,3- f ]isoindole ring system and the phenyl ring are oriented at a dihedral angle of 20.57 (13)°. The strong intramolecular O—H...O hydrogen bond partly ensures the coplanarity of the carboxyl group and the ring system. In crystal, the molecules are linked through C—H...O hydrogen bonds, enclosing R ² ₂ (14) ring motifs, into a three-dimensional architecture. π–π interactions between parallel five-membered and phenyl rings [centroid-to-centroid distances of 3.564 (3) and 3.591 (3) Å] further contribute to the cohesion of the crystal structure. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (35.5%), H...O/O...H (21.3%), C...C (14.1%) and H...C/C...H (12.8%) interactions.