A new polymorph of the title compound, C8H8BrNO, has been determined at 173 K in the space group P21/c. The previous room-temperature structure was reported to crystallize in the orthorhombic space group Pna21 [Andreetti et al. (1968 ▶). Acta Cryst. B24, 1195–1198]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds forming chains along . Weak C—H⋯π interactions are also present.
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, C28H19BrF2O2, the C=C double bond is E-configured. In the crystal, C—H⋯O and C—H⋯F contacts connect molecules into planes perpendicular to the c axis. The shortest centroid–centroid distance between two aromatic systems is 3.6745 (12) Å between one of the para-fluorophenyl rings and its symmetry-generated equivalent.
In the title pyrimidine derivative, C12H16N2OS, the tetrahydropyrimidine ring adopts an envelope conformation with the C atom of the methylene –CH2– group as the flap. In the crystal, N—H⋯O and N—H⋯S hydrogen bonds connect molecules into undulating sheets perpendicular to the a axis.
In the title compound, C21H15F2N3O2, a pyrazole derivative bearing three aromatic substituents, the central five-membered heterocyclic ring makes dihedral angles of 1.77 (14), 3.68 (13) and 72.15 (14)° with the three benzene rings. In the crystal, C—H⋯O and C—H⋯F interactions connect the molecules into double layers parallel to the bc plane.
The asymmetric unit of the title compound, C19H16N2O3, contains two independent molecules in which the dihedral angles between the naphthalene ring system and the benzene ring are 10.0 (1) and 35.3 (1)°. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional framework parallel to (001). Weak C—H⋯O and C—H⋯N hydrogen bonds complete a three-dimensional network.
The asymmetric unit of the title compound, C27H16F2N2O4, consists of two crystallographically independent molecules (A and B). In molecule B, the isoindoline-1,3-dione ring system is disordered over two set of sites with a site-occupancy ratio of 0.658 (12):0.342 (12). In molecule A, the fluoro-substituted benzene rings make dihedral angles of 18.36 (8) and 46.37 (8)° with the central benzene ring, whereas the corresponding angles are 40.90 (8) and 52.89 (9)° in molecule B. The isoindoline ring system in molecule A and the major and minor components of the disordered isoindoline ring system in molecule B make dihedral angles of 58.50 (4), 54.13 (16) and 70.01 (28) °, respectively, with their attached benzene rings, linked through the amide group. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring in each molecule. In the crystal, molecules are linked by N—H⋯O, C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. The crystal studied was a non-merohedral twin with a refined twin component ratio of 0.9316 (8):0.0684 (8).
In the title compound, C35H32N4O4, the pyrazole ring forms a dihedral angle of 15.04 (8)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.95 (8) and 1.86 (7)° with its adjacent methoxy-substituted benzene rings, whereas the equivalent angles are 80.24 (9) and 11.55 (9)° for the pyrazole ring and its adjacent benzene rings. The crystal packing features π–π interactions, the centroid–centroid distance between the pyrimidine and methoxyphenyl rings being 3.604 (1) Å. The pyrazole ring is nearly planar, with a maximum deviation of 0.020 (3) Å for the –CH2– carbon.
In the title compound, C29H22F2O2S, the central benzene ring makes dihedral angles of 45.83 (7), 38.90 (7) and 55.50 (7)° with the two fluoro-substituted benzene rings and the methylsulfanyl-substituted benzene ring, respectively. In the crystal, C—H⋯O contacts connect the molecules into layers lying perpendicular to the c axis. In addition, π–π stacking interactions between one of the fluorophenyl groups [centroid–centroid distances = 3.681 (1) and 3.818 (1) Å] are observed.
In the title compound, C28H19F3O2, the central benzene ring forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)° with the fluorobenzene rings. In the crystal, intermolecular C—H⋯O and C—H⋯F hydrogen bonds link the molecules, forming an undulating two-dimensional network parallel to the bc plane. C—H⋯π interactions further consolidate the crystal packing.
In the title compound, C29H19F2NO2, the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyanobenzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluorobenzene rings. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds link the molecules into sheets lying parallel to the ab plane. The crystal packing also features C—H⋯π interactions involving the central benzene ring.
In the crystal structure of the title compound, C15H9F2NO, the complete molecule is generated by a crystallographic twofold rotation axis and the O and N atoms of the central isoxazole ring are statistically disordered with equal site occupancies. The terminal benzene rings form a dihedral angle of 24.23 (3)° with the isoxazole ring. The dihedral angle between the benzene rings is 47.39 (2)°. No significant intermolecular interactions are observed.
In the title solvate, C47H37N3O3·C4H8O, the cyclohexane ring adopts a chair conformation and the plane through its near coplanar atoms forms dihedral angles of 82.58 (7), 89.27 (7), 60.30 (8), 54.54 (7) and 72.03 (7)°, respectively, with the three pyridine rings and the two attached benzene rings. The rings of the biphenyl units are twisted from each other, making dihedral angles of 35.27 (7) and 45.41 (7)°. All the rings are in equatorial orientations in the cyclohexane ring, except for the C=O-bonded pyridine ring in position 1, which is axial. Intramolecular O—H⋯N and C—H⋯O hydrogen bonds form one S(5) and three S(6) ring motifs. In the crystal, molecules are linked via C—H⋯O hydrogen bonds into a chain along the c axis. The crystal structure also features weak C—H⋯π interactions and aromatic π–π stacking [centroid–centroid distances = 3.5856 (10) and 3.7090 (9) Å].
The title compound, C28H19ClF2O2, is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C—H⋯Cl and C—H⋯O contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å.
In the title compound, C28H18F4O2, the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluorobenzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluorobenzene rings is 87.81 (6)°. The methoxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C—O—Car—Car [−0.06 (15)°] and C—C—Car—Car [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C—H⋯π interactions.
In the title compound, C28H19BrF2O2, the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into infinite chains along . Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.683 (2) Å] also occur and short intermolecular F⋯F contacts [2.833 (4) Å] are observed.
In the title compound, C18H17ClN2O2, the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, molecules are linked via bifurcated (C,C)–H⋯O hydrogen bonds into chains along . The crystal structure is further consolidated by C—H⋯π interactions.
In the title compound, C20H21ClN2O2, the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, molecules are linked by C—H⋯Cl and C—H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C—H⋯π interactions.
In the title compound, C31H20F4N4, the pyrazole ring adopts an envelope conformation and forms a dihedral angle of 9.91 (6)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.23 (6) and 2.16 (5)° with its adjacent fluoro-substituted benzene rings, whereas these angles are 88.22 (6) and 9.66 (6)° for the pyrazole ring and its adjacent benzene rings. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into ribbons along [01-1]. The crystal packing is further stabilized by C—H⋯π and by π–π interactions, with centroid–centroid distances of 3.7428 (7) and 3.7630 (6) Å.
In the title compound, C20H16F2O2, the cyclohex-2-en-1-one ring adopts a distorted envelope conformation and the dihedral angles between its six-atom mean plane and the fluorophenyl rings are 38.9(8) and 82.3(1)°. The two fluorophenyl rings are oriented at an angle of 77.3 (3)°. The long hydroxy O—H bond length of 1.22 (3) and the H⋯O distance of 1.28 (3) Å, together with a longer than expected C=O bond length [1.290 (2) Å] in the hydroxy(en-1-one) group, indicate sharing of the H atom as O⋯H⋯O between the two O atoms and the influence of electron delocalization. Weak C—H⋯O intermolecular interactions form an infinite two-dimensional network in (011).
In the title compound, C28H24F2N2O6S, the whole molecule is disordered over two sites with refined occupancies of 0.778 (3) and 0.222 (3). The central benzene ring makes dihedral angles of 56.0 (4), 34.5 (4) and 70.9 (4)°, respectively, with the two terminal benzene rings and the 1,3,4-oxadiazole ring in the major component of the disordered molecule. The corresponding angles in the minor component are 59.7 (16), 25.6 (13) and 75.5 (14)°. In the crystal, molecules are linked via C—H⋯F, C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds into a three-dimensional network. In addition, C—H⋯π interactions are observed.
In the title compound, C21H19F2NO2, the cyclohexa-1,3-diene ring is in a distorted envelope conformation. The dihedral angles between the mean planes of the diene moiety and the two fluorophenyl rings are 42.8 (2) and 75.0 (5)°. The two fluorophenyl rings are inclined to one another by 87.0 (3)°. In the crystal, intramolecular N—H⋯O hydrogen bonds and weak N—H⋯O and N—H⋯F intermolecular interactions are observed forming an infinite two-dimensional network along .
The title compound, C32H18F4N4S2, is a disulfide symmetrically substituted with two diaza-meta-terphenyl groups. In the crystal, the molecule adopts a twisted conformation with a C—S—S—C torsion angle of −91.82 (7)°. One of the 4,6-(4-fluorophenyl)pyrimidine groups is virtually planar, with dihedral angles between the pyrimidine and benzene groups of 4.00 (8) and 5.44 (8)°, wheares the other is non-planar with analogues dihedral angles of 18.69 (8) and 26.60 (8)°. The planar 4,6-(4-fluorophenyl)pyrimidine groups are involved in π–π stacking interactions via their 4-fluorophenyl groups [centroid–centroid distances of 3.8556 (11) and 3.9284 (11) Å] that assemble the molecules into columns extended along the a axis. In addition, the structure is stabilized by C—F⋯π [F⋯centroid = 3.4017 (16) Å], C—H⋯F and C—H⋯π interactions.
In the title compound, C22H18F2O3, the two fluoro-substituted rings form dihedral angles of 25.89 (15) and 55.00 (12)° with the central benzene ring. The ethoxy group in the molecule is disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). In the crystal, molecules are linked by C—H⋯O hydrogen bonds into chains along the a axis. The crystal packing is further stabilized by C—H⋯π and π—π interactions, with centroid–centroid distances of 3.8605 (15) Å.
In the title compound, C21H16F2O2, the central benzene ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted rings. The dihedral angle between the two terminal fluoro-subsituted rings is 68.34 (8)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by weak C—H⋯π interactions.