A series of 1,3,5-triaryl-2-pyrazolines 2a-g were synthesized by the reaction of 4,4 0 -disubstituted chalcone with phenyl hydrazine. All these compounds were characterized by NMR, IR and mass spectral and single crystal XRD data. All the synthesized products were screened for their in vitro antimicrobial, analgesic and antioxidant properties. The docking studies were carried out for these compounds against the active site of methionyl-tRNA synthetase (metRS). Some of the tested compounds exhibited significant antimicrobial, analgesic, DPPH scavenging activities and molecular binding.

In the asymmetric unit of the title compound, C17H14F2N2O, there are three independent mol­ecules (A, B and C) which differ slightly in the relative orientations of the two fluoro­phenyl rings. In mol­ecules A and C one of the fluoro­phenyl rings is disordered over two positions, with occupancy ratios of 0.72 (2):0.28 (2) for mol­ecule A and 0.67 (2):0.33 (2) for mol­ecule C. The dihedral angle between the two fluoro­phenyl rings in the independent mol­ecules lie in the range 70.3 (3)–84.0 (3)°. In the crystal structure, the mol­ecules are linked via inter­molecular C—H⋯O and C—H⋯F hydrogen bonds and π⋯π stacking inter­actions [centroid–centroid distance = 3.7508 (13) Å], forming a three-dimensional network.

In the title compound, C21H16F2N2, the dihedral angle between the fluoro­phenyl groups is 66.34 (8)°, and the dihedral angle between the envelope-configured pyrazole group (N/N/C/C/C) and the benzene ring is 11.50 (9)°. The dihedral angles between the benzene and the two fluoro-substituted phenyl groups are 77.7 (6) and 16.7 (5)°. Weak C—H⋯π interactions contribute to the stability of the crystal structure.

New functionalized terphenyl derivatives incorporating various heterocyclic rings are prepared by using 4,4′′-difluoro-5′-hydroxy-1,1′:3′,1′′-terphenyl-4′-carbohydrazide as a key intermediate derived from 4,4′-difluoro chalcone, a versatile synthone. All the derivatives are characterized by 1H NMR, IR, and mass spectral data. All the synthesized products are screened for their in vitro antimicrobial and antioxidant properties. The majority of the tested compounds exhibited significant antioxidant activity and some of them showed good antimicrobial activity.

In the title compound, C21H16Br2N2, the central pyrazole ring adopts an flattened envelope conformation, with the stereogenic C atom in the flap position. The deviations from planarity for this ring are relatively minor (r.m.s. deviation = 0.045 Å) and the dihedral angles formed with the N- and Cimine-bound benzene rings are 7.73 (13) and 11.00 (13)°, respectively. By contrast, the benzene ring bound at the chiral C atom is almost orthogonal to the rest of the mol­ecule; the dihedral angle formed between this ring and the pyrazole ring is 79.53 (13)°. In the crystal, the packing is stabilized by C—H⋯N and C—H⋯Br inter­actions.

The 3-cyclo­hexene units adopt envelope conformations in each of the two independent mol­ecules that comprise the asymmetric unit of the title compound, C20H16F2O3. The dihedral angles between the two fluoro­phenyl rings are 79.7 (2) and 73.7 (2)° in the two mol­ecules. In one of the mol­ecules, two C—H groups of the cyclo­hexene ring are disordered over two sets of sites in a 0.818 (13):0.182 (13) ratio, the major and minor components corresponding to the two enanti­omeric forms of the mol­ecule. Weak inter­molecular C—H⋯O inter­actions help to stabilize the crystal structure.

In the title mol­ecule, C16H12F2N2O, the pyrazole ring adopts a slight envelope conformation with the methyl­ene C atom deviating by 0.114 (3) Å from the mean plane of the other four atoms [maximum deviation = 0.021 (3) Å]. The dihedral angles between the four essentially planar atoms of the pyrazole ring and the fluoro-substituted benzene rings are 2.6 (2) and 82.2 (2)°. The dihedral angle between the two benzene rings is 83.7 (2)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.

In the title compound, C21H16F2N2, the seven-membered 1,4-diazepine ring of the benzodiazepine ring system adopts a distorted-boat conformation. The benzene ring of this system makes dihedral angles of 18.6 (2) and 78.8 (2)° with those of two fluoro­phenyl substituents. In the crystal, inversion dimers linked by two weak C—H⋯F hydrogen bonds generate R 2 2(20) ring motifs. There are also weak N—H⋯π and C—H⋯π inter­actions.