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The title compound, C12H13ClN2O2, crystallizes with two independent but very similar mol­ecules (A and B) in the asymmetric unit. The pyrazole ring in each mol­ecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B mol­ecules are linked via a pair of O—H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C—H⋯O inter­actions to form –A–B–A–B– chains propagating along the c-axis direction.

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 pyrazoline derivative, C14H12ClN3S2, the thiophene ring is disordered over two orientations with a refined site-occupancy ratio of 0.832 (4):0.168 (4). The pyrazoline ring adopts an envelope conformation with the C atom linking the thiophene ring at the flap. The dihedral angles between the benzene ring and the major and minor components of the thiophene ring are 88.6 (3) and 85.6 (15)°, respectively while the dihedral angle between the disorder components of the ring is 3.1 (16)°. The mean plane of the pyrazoline ring makes dihedral angles of 11.86 (13), 80.1 (3) and 83.0 (15)°, respectively, with the benzene ring, and the major and minor components of the thiophene ring. An intra­molecular N(amide)—H⋯N(pyrazoline) hydrogen bond generates an S(5) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯S and N(amide)—H⋯S inter­actions into a tape along [10]. C—H⋯π inter­actions are also observed.

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, C17H14Cl2N2O, the dihedral angles between the pyrazole ring and the mean planes of the benzene and chloro-substituted benzene rings are 75.97 (1) and 16.63 (1)° respectively. In the crystal, two weak C—H⋯O inter­molecular hydrogen bonds and π–π stacking inter­actions [centroid–centroid distances = 3.774 (4) and 3.716 (7) Å] are observed.

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.

In the title mol­ecule, C15H11Br2ClO2, an S(6) ring motif is formed via an intra­molecular O—H⋯O hydrogen bond. The dihedral angle formed between the chloro- and hy­droxy-substituted benzene rings is 34.10 (15)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis.

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, 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.

In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chloro­benzene and hy­droxy­benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy­droxy­phenyl ring and 11.5 (1)° with the chloro­phenyl ring. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].

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 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 dihydro­pyrimidine ring of the title compound, C13H15ClN2S, adopts an envelope conformation with five almost coplanar atoms (r.m.s. deviation = 0.054 Å) and the C atom bearing the two methyl substituents deviating from this plane by 0.441 (2) Å. The best plane through the five almost coplanar atoms forms a dihedral angle of 89.56 (5)° with the benzene ring. The crystal packing is characterized by centrosymmetric dimers connected by pairs of N—H⋯S hydrogen bonds.

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, C16H14ClN3O2, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H⋯π inter­actions are observed.

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 compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro­benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra­molecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supra­molecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.

In the title compound, C11H12N2O2, the dihydro­pyrazole and benzene rings are oriented at a dihedral angle of 68.35 (5)°. The dihydro­pyrazole ring is planar, with a mean deviation from the mean plane of 0.0409 Å. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen bonds.

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.

In the title compound, C19H17ClN2O2, the pyrazole ring is almost planar with a maximum deviation of 0.009 (3) Å and makes a dihedral angle of 8.96 (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and meth­oxy-substituted benzene rings are 50.95 (8) and 13.24 (9)°, respectively. An inter­molecular C—H⋯N hydrogen bond links the mol­ecules into infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π inter­actions.

In the title compound, C24H24N2O4, the pendant benzene and naphthalene ring systems make dihedral angles of 87.9 (3) and 19.2 (3)°, respectively, with the central pyrazoline ring. In the crystal structure, weak C—H⋯O inter­actions help to establish the packing.

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.

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, C14H12ClN3O2·H2O, the benzene ring and the pyridine rings are oriented at a dihedral angle of 57.73 (12)° and an intra­molecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, the water mol­ecule forms O—H⋯O and O—H⋯N hydrogen bonds to the organic mol­ecule, leading to chains containing R 4 4(16) loops. In addition, weak aromatic π–π stacking inter­actions between the centroids of pyridine rings [at distance of 3.864 (2) and 4.013 (2) Å] and C—H⋯π inter­actions occur.

The title compound, C29H27Cl2N5O2, contains a central pyridine ring and two functionalized pyrazoline rings. The pyridine ring and the two attached pyrazoline rings are nearly coplanar, whereas the terminal chloro­phenyl rings are nearly perpendicular to the attached pyrazoline rings [dihedral angles = 86.78 (1) and 77.70 (1)°]. Mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonding.