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In the title compound, C6H4BrF3N4O2, the oxadiazole ring is essentially planar with a maximum deviation of 0.003 (2) Å. In the crystal, molecular pairs are connected by N—H...N hydrogen bonds, forming dimers with an R22(8) motif. The dimers are linked into layers parallel to the (10\overline{4}) plane by N—H...O hydrogen bonds. In addition, C—O...π and C—Br...π interactions connect the molecules, forming a three-dimensional network. The F atoms of the trifluoromethyl group are disordered over two sites in a 0.515 (6): 0.485 (6) ratio. The intermolecular interactions in the crystal structure were investigated and quantified using Hirshfeld surface analysis.

The overall molecular configuration of the title compound, C12H16N6OS2·C3H7NO, is stabilized in the solid state by intramolecular C—H...N, C—H...O, N—H...N and N—H...O interactions, forming S(5) ring motifs. In the crystal, molecules are linked to each other and solvent dimethylformamide molecules by N—H...S, N—H...O, C—H...O and C—H...S hydrogen bonds, forming a three dimensional network. The phenyl ring of the title compound is disordered over two sites with an occupancy ratio of 0.57 (4):0.43 (4). A Hirshfeld surface analysis was performed to quantify the contributions of the different intermolecular interactions, indicating that the most important contributions to the crystal packing are from H...H (38.7%), S...H / H...S (24.0%), C...H / H...C (18.5%) and N...H / H...N (9.8%) interactions.

In the title salt, C15H12FN2O+·Cl−·H2O, the imidazo[1,2-a]pyridin-1-ium ring system of the cation is almostly planar [maximum deviaition = −0.047 (2) Å for the ring C atom with the attached arene ring] and forms a dihedral angle of 61.81 (6)° with the plane of the fluorophenyl ring. In the crystal, water molecules form an R24(8) motif parallel to the (100) plane by bonding with the chloride ions via O—H...Cl hydrogen bonds. The cations are connected along the b axis via N—H...O hydrogen bonds involving the O atoms of water molecules, and C—H...O, C—H...Cl and π–π interactions [centroid-to-centroid distance = 3.6195 (8) Å] form layers parallel to the (100) plane. Furthermore, these layers are connected via π–π interactions [centroid-to-centroid distance = 3.8051 (9) Å] that further consolidate the crystal structure.

The bicyclic imidazo[1,2-a]pyridine core in the molecule of the title compound, C10H7F3N2O, is planar within 0.004 (1) Å. In the crystal, the molecules are linked by pairs of C—H...N and C—H...O hydrogen bonds, forming strips. These strips are connected by the F...F contacts into layers, which are further joined by π–π stacking interactions. The Hirshfeld surface analysis and fingerprint plots reveal that molecular packing is governed by F...H/H...F (31.6%), H...H (16.8%), C...H/H...C (13.8%) and O...H/H...O (8.5%) contacts.