Related Articles

In the title compound, C17H15ClN2O2, the benzene rings form dihedral angles of 89.56 (5) and 5.87 (5)° with the mean plane of the pyrazoline ring (r.m.s. deviation = 0.084 Å). The dihedral angle between the two benzene rings is 87.57 (5)°. In the crystal, mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a helical chain along the c axis. Between the chains weak C—H⋯N and C—H⋯O inter­actions are present. The crystal studied was an inversion twin with a domain ratio of 0.72 (4):0.28 (4).

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 [010]. 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, C22H24ClN3O4, intra­molecular C—H⋯O and C—H⋯N hydrogen bonds form S(9) and S(7) ring motifs, respectively. The 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The benzene ring makes a dihedral angle of 33.36 (6)° with the pyrazole ring. In the crystal, pairs of N—H⋯N hydrogen bonds link the mol­ecules into inversion dimers. The dimers are stacked in column along the a axis through N—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features C—H⋯π inter­actions involving the pyrazole ring.

In the title mol­ecule, C11H10ClN5OS, an intra­molecular N—H⋯O hydrogen forms an S(6) ring motif. The dihedral angle between the pyrazole ring and the benzene ring is 3.77 (8)°. In the crystal, mol­ecules are linked by N—H⋯S and N—H⋯O hydrogen bonds into layers parallel to the bc plane.

The title compound, C37H31ClN4O4, crystallizes with two mol­ecules (A and B) in the asymmetric unit. The pyrrole rings in both mol­ecules are connected via cis fusion, whereas one ring has a twisted conformation and the other assumes a half-chair conformation. In the crystal, the A mol­ecules form inversion dimers via a pair of C—H⋯Cl inter­actions, while the B mol­ecules form chains propagating in [10], via C—H⋯O inter­actions. In the crystal, there are also a number of C—H⋯π inter­actions present.

In the title compound, C17H15FN2O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C—H⋯O hydrogen bonds link neighbouring mol­ecules, forming an inversion dimer. The crystal structure is further consolidated by C—H⋯π inter­actions and by a π–π inter­action with a centroid–centroid distance of 3.7379 (6) Å.

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, C17H14BrFN2O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into corrugated layers parallel to the ab plane.

In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro­phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking inter­actions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].

In the title compound, C20H13ClN2O2S, the chloro­phenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of bifurcated O—H⋯O hydrogen bonds link mol­ecules into inversion dimers with R 2 2(12) graph-set motifs.

The title compound, C20H16Cl2N4O, has two mol­ecules in the asymmetric unit. The two five-membered rings form a dihedral angle of 54.2 (3)° in one mol­ecule and 56.8 (3)° in the other independent mol­ecule. The amino group of the dihydro­pyrazolone unit of one mol­ecule acts as a hydrogen-bond donor to the carbonyl group of the dihydro­pyrazolone system of the other mol­ecule. The resulting N—H⋯O hydrogen bonds generate a chain running along the c axis. The crystal selected was a pseudo-merohedral twin with a 44.9 (3)% twin component.

In the title mol­ecule, C16H13Cl2FN2OS, the dihedral angle between the thio­phene and benzene rings is 80.34 (12)°. The pyrazoline ring is in an envelope conformation, and the plane through the four coplanar atoms makes dihedral angles of 85.13 (9) and 6.89 (10)° with the thio­phene and benzene rings, respectively. The C and O atoms of the acetyl group are nearly coplanar with the attached pyrazoline ring. In the crystal structure, inversion dimers arise from pairs of inter­molecular C—H⋯O hydrogen bonds. A short inter­molecular Cl⋯S contact of 3.4250 (13) Å is also found.

The title compound, C20H18ClN3O3, is in an enamine–keto form, stabilized by two strong intra­molecular N—H⋯O hydrogen bonds. The pyrazole ring is oriented at dihedral angles of 4.13 (3) and 85.60 (3)° with respect to the aromatic rings. The dihedral angle between the aromatic rings is 81.79 (3)°. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into double chains, which are further linked by weak C—H⋯π inter­actions, forming a two-dimensional network.

In the the title compound, C27H23ClN4O2, the chloro­phenyl ring forms dihedral angles of 77.70 (9) and 86.65 (9)°, respectively, with the pyrazol-3-one and pyrazole rings. The phenyl rings attached to the pyrazole rings are twisted away from them [dihedral angles 33.80 (9) and 40.34 (10)°]. An intramolecular O—H⋯O hydrogen bond generates an S(8) ring motif. The mol­ecules are linked into chains running along the c axis by N—H⋯N hydrogen bonds, and the chains are cross-linked via C—H⋯O hydrogen bonds and C—H⋯π inter­actions involving the chloro­phenyl ring.

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, C24H26N4O2, the complete mol­ecule is generated by the application of twofold symmetry. The pyrazole ring is approximately planar [r.m.s. deviation = 0.026 Å] and the benzene ring is twisted out of this plane [dihedral angle = 21.94 (7)°]. A twist in the mol­ecule about the central C—C bond [1.566 (3) Å] is also evident [C—C—C—C torsion angle = 44.30 (14)°]. Supra­molecular layers in the bc plane are formed in the crystal packing via C—H⋯O and C—H⋯π inter­actions.

In the title compound, C16H11ClN2O2, the pyrazole ring makes dihedral angles of 11.88 (13) and 22.33 (13)° with the 3-chloro-2-hy­droxy­benzene group and phenyl rings, respectively. The phenolic hy­droxy group forms an intra­molecular O—H⋯N hydrogen bond with the imine N atom of the pyrazole unit. The formyl group is virtually coplanar with the pyrazole ring [dihedral angle = 4.5 (19)°] and acts as an acceptor in an intra­molecular C—H⋯O hydrogen bond closing seven-membered ring. In the crystal, adjacent mol­ecules are linked through C—H⋯O hydrogen bonds into infinite chains along the b axis.

The title mol­ecule, C18H18N2O2, is V-shaped with the pyrazoline moiety being inclined to the adjacent phenyl ring by an angle of 6.49 (9)°, while the 4-meth­oxy-substituted ring is inclined to the pyrazoline ring by 82.99 (9)°. In the crystal, adjacent mol­ecules are linked by C—H⋯O inter­actions, forming chains propagating in [100]. There are also C—H⋯π inter­actions involving adjacent mol­ecules and those related by an inversion center.

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 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 compound, C19H18BrFN2O, the benzene rings form dihedral angles of 5.38 (7) and 85.48 (7)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0849 Å), which approximates to an envelope conformation with the –CH2– group as the flap. The dihedral angle between the benzene rings is 82.86 (7)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the mol­ecules to form inversion dimers and together these generate chains along [011]. The crystal packing also features C—H⋯π inter­actions.

In the title compound, C16H11ClN2O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, generating R 2 1(7) and R 2 2(10) ring motifs. π–π inter­actions between the pyrazole and phenyl rings [centroid–centroid distance = 3.758 (1) Å] further stabilize the crystal structure.

In the title compound, C10H9ClN4O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chloro­benzene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(16) ring motifs. The dimers are further connected by N—H⋯N hydrogen bonds, thereby forming layers lying parallel to the bc plane.

In the title compound, C20H17ClN2O3, the dihedral angles between the pyrazole ring and the substituted and unsubstituted benzene rings are 3.64 (13) and 81.15 (17)°, respectively. Mol­ecules are connected via three pairs of weak hydrogen bonds into a centrosymmetric dimer. The crystal structure is stabilized by inter­molecular C—H⋯O and C—H⋯π inter­actions.

In the title compound, C29H27Cl2N5O2·C4H8O, the polycyclic system is composed of three parts: one central pyridine ring substituted by two functionalized pyrazoline rings. The dihedral angles between the central pyridine plane and pyrazoline planes are 5.11 (1) and 13.99 (1)°, whereas the dihedral angles between each chloro­phenyl plane and the attached pyrazoline planes are 88.65 (1) and 83.87 (1)°. Mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, forming a three-dimensional network.