In the title compound, C28H19FN2O, the phenanthrene fused with an imidazole ring, constituting an essentially planar tetracyclic system [maximum deviation = 0.032 (2) Å], makes dihedral angles of 60.83 (4) and 80.55 (4)° with the fluorobenzene and methoxybenzene rings, respectively. The dihedral angle between the the methoxybenzene and fluorobenzene rings is 69.45 (6)°. In the crystal, C—H⋯O hydrogen bonds connect the molecules into infinite strands along the b axis. The crystal structure is further consolidated by C—H⋯π interactions.
In the title molecule, C28H28F2N2O2, the ethene bond exhibits an E conformation and the piperazine ring adopts a chair conformation. The amide-N atom of the piperazine ring is almost planar (bond-angle sum = 358.8°) whereas the other N atom is clearly pyramidal (bond-angle sum = 330.5°). The dihedral angle between the fluorobenzene rings is 76.36 (17)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R
In the title compound, C22H17ClFN3O2S, the pyrazole ring is approximately planar with a maximum deviation of 0.001 (4) Å and makes dihedral angles of 4.95 (19), 35.78 (18) and 54.73 (18)° with the thiazole, fluorobenzene and chlorobenzene rings, respectively. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into chains along the a axis.
In the title compound, C25H16F2N2O, the pyrazole ring is almost planar (r.m.s. deviation = 0.028 Å) and makes a dihedral angle of 5.86 (11)° with the indazole benzene ring. The dihedral angle between the pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The dihedral angles between the unsubstituted phenyl and the two fluorophenyl groups are 57.69 (10) and 18.01 (10)°. In the crystal, molecules are linked by intermolecular N—H⋯O and C—H⋯F interactions, forming infinite chains along the b axis with graph-set motif R
2(19). The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.5916 (13) and 3.6890 (13) Å] and C—H⋯π interactions.
The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent molecules with similar conformations. In the molecules, the thiazole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluorophenyl ring and chlorophenyl rings at 9.96 (18) and 70.39 (18)° in one molecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluorophenyl and chlorophenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Intermolecular C—H⋯O and C—H⋯F hydrogen bonds stabilize the three-dimensional supramolecular architecture. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.877 (3) Å] lead to a criss-cross molecular packing along the c axis.
In the title compound, C25H20FN3S, two independent molecules comprise the asymmetric unit, which differ in the relative orientation of the fluorobenzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two molecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the molecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thiazole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each molecule has a T-shape. In the crystal, molecules are connected into a three-dimensional architecture by weak C—H⋯π interactions.
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, C21H16BrFN2, the fluoro-substituted benzene ring is disordered over two orientations about the C—F bond and the C—C bond between the benzene and pyrazole groups with a site-occupancy ratio of 0.516 (8):0.484 (8). The central pyrazole ring [maximum deviation = 0.035 (3) Å] makes dihedral angles of 22.4 (2), 11.0 (2), 77.19 (16) and 7.44 (17)° with the two disorder components of the benzene ring, the bromo-substituted benzene ring and the phenyl ring, respectively. In the crystal, molecules are linked into a layer parallel to the bc plane through C—H⋯π interactions.
In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and difluorobenzene rings is 50.30 (13)°, while those between the pyrazole and fluorobenzene rings and between the difluorobenzene and fluorobenzene rings are 38.56 (13) and 53.50 (11)°, respectively. Aromatic π–π stacking interactions between adjacent difluorobenzene rings [centroid–centroid separation = 3.6082 (11) Å] link the molecules into dimers parallel to [21-2].
In the title compound, C28H22ClFN6O2, the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyanophenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chlorophenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, intermolecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds link the molecules into sheets parallel to the ac plane.
In the title compound, C28H28F2N2O2, the piperazine ring has a chair conformation with the pendant N—C bonds in equatorial orientations. The C=C double bond has an E conformation and the dihedral angle between the fluorobenzene rings is 70.8 (3)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds.
The title co-crystal, 3-(4-fluorophenyl)-1H-pyrazole–5-(4-fluorophenyl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent molecules (A, B, C and D) in the asymmetric unit exhibiting two tautomeric forms (A and D; B and C) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in molecules A, B, C and D, respectively. In the crystal, N—H⋯N hydrogen bonds link the four molecules in the asymmetric unit into a ring with an R
4(12) motif. Furthermore, weak C—H⋯F interactions link the molecules into a three-dimensional network.
crystal structure; pyrazole derivative; tautomeric forms; hydrogen bonds
The asymmetric unit of the title compound, C25H14ClFN4S, contains two independent molecules (A and B). Each molecule consists of five rings, namely chlorophenyl, fluorophenyl, 1H-pyrazole, thiazole and benzonitrile. In molecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chlorophenyl, fluorophenyl and thiazole rings. The corresponding values in molecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, molecules are linked into dimers by C—H⋯N hydrogen bonds, generating R
2(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via intermolecular weak C—H⋯N and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π interactions [with centroid–centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C—H⋯π interactions.
In the title molecule, C19H13FN2, the benzimidazole unit is close to planar [maximum deviation = 0.0342 (9) Å] and forms dihedral angles of 58.94 (3) and 51.43 (3)° with the phenyl and fluorobenzene rings, respectively; the dihedral angle between the phenyl and fluorobenzene rings is 60.17 (6)°. In the crystal, three C—H⋯F hydrogen bonds and two weak C—H⋯π interactions involving the fused benzene ring lead to a three-dimensional architecture.
The molecule of the title hydrazone derivative, C14H11FN4O4, is nearly planar, with a dihedral angle between the benzene rings of 3.71 (7)°. The central ethylidenehydrazine N—N=C—C plane makes dihedral angles of 5.32 (10) and 9.02 (10)° with the 2,4-dinitro- and 3-fluoro-substituted benzene rings, respectively. An intramolecular N—H⋯O bond generates an S(6) ring motif. In the crystal, molecules are linked by weak C—H⋯O interactions into a sheet parallel to (10-1). The molecules are further stacked along the a axis by π–π interactions with centroid–centroid distances of 3.6314 (9) and 3.7567 (10) Å. A C⋯F short contact [2.842 (3) Å] is observed. The 3-fluorophenyl group is disordered over two orientations with a site-occupancy ratio of 0.636 (3):0.364 (3).
The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluorophenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluorobenzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thioamide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intramolecular hydrogen bond with a ring N atom. In the crystal, supramolecular double layers in the bc plane are formed via N—H⋯S, N—H⋯F and C—H⋯F interactions.
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, C18H15FO4S, the fluorobenzene ring makes a dihedral angle of 4.3 (1)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations, with site-occupancy factors of 0.940 (3) and 0.060 (3).
In the title molecule, C18H17FN2, the imidazole ring is essentially planar [maximum deviation of 0.005 (1) Å and makes dihedral angles of 72.33 (8) and 18.71 (8)° with the methylphenyl and fluorophenyl rings, respectively. The dihedral angle between the two benzene rings is 75.05 (7)°. The crystal packing is stabilized by intermolecular C—H⋯N hydrogen bonds.
The title compound, C15H12FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline and crystallizes with two molecules A and B in the asymmetric unit. The two unique molecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluorobenzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in molecules A and B. The amide C—N—C(O)—C portions of the molecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluorobenzene rings in molecules A and B. The 2-fluoroacetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, intermolecular N—H⋯O hydrogen bonds augmented by weak C—H⋯π interactions link molecules into rows in a head-to-tail fashion along a. Additional weak C—H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a.
In the title molecule, C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3 (3)°]. In the crystal, molecules are linked by intermolecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.7713 (9) Å].
In the crystal structure of the title compound, C21H18ClFO3·0.5C7H8, the toluene solvent molecules occupy special positions on centres of symmetry, and consequently are disordered across this site. The cyclohexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 72.90 (7)° and their planes make dihedral angles of 30.09 (10) (chlorophenyl) and 88.13 (6)° (fluorophenyl) with the approximately planar part of the cyclohexenone ring [maximum deviation from plane through five atoms is 0.030 (2) Å, the sixth atom is 0.672 (3)Å out of this plane]. Weak intermolecular C—H⋯O and C—H⋯X (X = F, Cl) interactions join molecules into a three-dimensional structure. Also, a relatively short and directional C—Cl⋯F—C contact is observed [Cl⋯F = 3.119 (2) Å, C—Cl⋯F = 157.5 (2)° and C—F⋯Cl 108.3 (2)°]. The solvent molecules fill the voids in the crystal structure and are kept there by relatively short and directional C—H⋯π interactions.
In the title compound, C21H17ClFN3O2, the 1H-pyrazole ring makes dihedral angles of 36.73 (7), 18.73 (7) and 60.88 (8)°, respectively, with the mean planes of the chlorophenyl, 4-oxopiperidine and fluorophenyl rings. The molecular structure is stabilized by an intramolecular C—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, intermolecular C—H⋯O hydrogen bonds link molecules into chains along . In addition, intermolecular C—H⋯F hydrogen bonds with an R
1(7) ring motif connect neighbouring chains into layers parallel to the ac plane.
The asymmetric unit of the title compound, C23H23ClFN5O2, contains two crystallographically independent molecules. In one molecule, the pyrazole ring makes dihedral angles of 43.93 (7) and 35.82 (7)°, respectively, with the fluoro- and chloro-substituted benzene rings, while the corresponding angles in the other molecule are 52.26 (8) and 36.85 (7)°. The piperazine rings adopt chair conformations. In the crystal, adjacent molecules are connected via intermolecular N—H⋯O, C—H⋯F, C—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure is further stabilized by a weak π–π interaction with a centroid–centroid distance of 3.6610 (8) Å and by C—H⋯π interactions.
In the title molecule, C17H14ClFN2O, the mean plane of the pyrazoline ring makes dihedral angles of 18.19 (1) and 83.51 (4)° with the 4-chlorobenzene and 4-fluorobenzene rings, respectively. The two benzene rings make a dihedral angle of 76.11 (2)°. Weak intermolecular C—H⋯O hydrogen bonds help stabilize the crystal structure.