The title molecule, C₁₆H₁₀BrNO₂, is essentially planar (r.m.s. deviation = 0.004 Å). In the crystal, molecules are linked by C—H...O and C—H...Br hydrogen bonds, forming ribbons along the b-axis direction. Furthermore, π-π interactions cause the molecules to form ribbons along the [1 0 \overline{10}] and [1 0 10] directions [centroid-to-centroid distances = 3.703 (3), 3.734 (3), 3.703 (3), and 3.734 (3) Å]. According to a Hirshfeld surface analysis, H...H (33.8%), O...H/H...O (15.1%), C...H/H...C (14.6%), Br...H/H...Br (13.8%), and C...C (11.9%) interactions are the main contributors to the crystal packing.

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 crystal structure of the title compound, C ₁₉ H ₁₇ NO ₃ , C—H...O hydrogen bonds connect molecular pairs to produce dimers with an R ² ₂ (16) ring motif. Additionally, C—H...π interactions form ribbons along the [101] direction. Van der Waals interactions between the ribbons help to consolidate the molecular packing. Hirshfeld surface analysis shows that H...H (45.5%), C...H/H...C (30.4%), and O...H/H...O (19.3%) interactions are the main contributors to the crystal packing.

In the title compound, C ₂₀ H ₁₅ BF ₂ N ₂ S, the twelve-membered ring system is essentially planar (r.m.s. deviation = 0.001 Å). The dihedral angles between the average plane of this ring and the thiophene and phenyl rings are 58.69 (4) and 61.41 (4)°, respectively. In the crystal, C—H...F interactions generate R ² ₂ (10) and three types of R ² ₃ (21) ring motifs around a molecule, resulting in layers parallel to the (101) plane. The molecules further form layers parallel to the (10 1 ) plane through C—H...π interactions. According to a Hirshfeld surface analysis, H...H (41.5%), C...H/H...C (23.5%) and F...H/H...F (18.2%) interactions are the most significant contributors to the crystal packing.