In the title compound, C19H20O5, the pyran ring is in an envelope conformation, whereas the benzene and dihydropyran ring system is planar with an r.m.s. deviation of 0.0190 (1) Å. The hydroxy group is coplanar with the attached benzene ring [r.m.s. deviation = 0.0106 (1) Å]. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into chains along the b axis by weak C—H⋯O interactions. These chains are stacked along the a axis. C—H⋯π and weak π–π interactions [centroid–centroid distance = 3.7698 (7) Å] are also observed.
The crystal structure of the title compound, C25H18ClN5O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one with p-chloroaldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chlorophenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chlorophenyl and pyridine rings make a dihedral angle of 86.8 (2)°.
In the title compound, C24H16Cl2N2O3, the chromene ring system is almost planar, with a maximum deviation of 0.042 (1) Å. It makes dihedral angles of 3.72 (6), 73.37 (5) and 12.00 (5)° with the dihydropyrazole, benzene and phenyl rings, respectively. An intramolecular O—H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked via C—H⋯O interactions, forming an infinite chain along the a axis. The crystal packing is further stabilized by a π–π stacking interaction [centroid–centroid distance = 3.5471 (7) Å] and a Cl⋯Cl short contact [Cl⋯Cl = 3.214 (1) Å].
In the title compound, C19H19NO2, commonly called koenimbine, the pyran ring adopts a sofa conformation. The carbazole ring system is planar [r.m.s. deviation = 0.063 (1) Å]. A C(10) zigzag chain running along the b axis is formed through intermolecular C—H⋯O hydrogen bonds. The chains are linked via weak C—H⋯π and N—H⋯π interactions.
The molecule of the title compound, C17H13NO2, is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Intermolecular N—H⋯O and C—H⋯O hydrogen bonds are found in the crystal structure. C—H⋯π interactions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.
The five-membered dihydropyrazole ring in the title compound, C10H9F3N2O, is approximately planar (r.m.s. deviation 0.111 Å for all non-H atoms) and its phenyl substituent is aligned at an angle of 14.7 (2)°. Adjacent molecules are linked by N—H⋯O and O—H⋯N hydrogen bonds, generating ribbons running along the b axis of the monoclinic unit cell.
The title compound, C20H15N5O3, was synthesized by the one-pot reaction of a four-component reaction protocol in aqueous medium. The pyrano[2,3-c]pyrazole system is essentially planar, with a maximum deviation of 0.026 (2) Å. The 3-nitrophenyl and phenyl rings make dihedral angles of 81.11 (5) and 13.36 (1)°, respectively, with the mean plane of the pyrano[2,3-c]pyrazole ring. The crystal structure is stabilized by N—H⋯N hydrogen bonds, which form infinite chain propagating along the c axis and by N—H⋯O hydrogen bonds, which form infinite chains propagating along the a axis. There are also N—O⋯N—C dipole–dipole interactions along the a axis with an O⋯N distance of 3.061 (3) Å, which is shorter than that of the N—H⋯O hydrogen bond [3.196 (3) Å].
The title compound, C13H6Cl3F3N4O, was synthesized by the reaction of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile and 2-chloroacetyl chloride. The five-membered pyrazole ring makes a dihedral angle of 71.5 (3)° with the benzene ring. The –CF3 group is disordered by rotation, and the F atoms are split over two sets of sites with occupancies of 0.59 (2) and 0.41 (2). The crystal structure features weak C—H⋯O and N—H⋯N interactions involving the carbonyl and cyano groups as acceptors.
The title compound, C18H17NO2, was prepared from 1-hydroxy-7-methylcarbazole and 3,3-dimethylacrylic acid with trifluoroacetic acid as the cyclization catalyst. The molecules contain an essentially planar 6-methylindole unit. The second aromatic ring is significantly bent away from the plane of this unit, with maximum deviations of 0.171 (1) and 0.185 (1) Å for two of the C atoms. In the crystal structure, there are neither N—H⋯O hydrogen bonds nor π–π stacking between the aromatic sections of neighboring molecules. There is only one weak C—H⋯O hydrogen bond and a number of weak C—H⋯π interactions.
In the title compound, C20H14Cl2F3NO3, the trifluromethyl group is disordered over two sets of sites in a 0.784 (10):0.216 (10) ratio. The quinoline ring system is essentially planar with a maximum deviation of 0.058 (2) Å for the N atom and forms dihedral angles of 89.23 (11) and 8.13 (17)°, respectively with the mean planes of the benzene ring and the carboxylate group. In the crystal, pairs of weak C—H⋯O and C—H⋯F hydrogen bonds link molecules into centrosymmetric dimers. The crystal structure is further stabilized by weak π–π [centroid–centroid distance = 3.624 (2) Å] interactions.
In the title compound, C26H23N5O2S, an intramolecular N—H⋯O interaction generates an S(6) ring. The essentially planar S(6) and pyrazole rings [maximum deviations = −0.0270 (14) and 0.0195 (15) Å, respectively] are nearly coplanar, making a dihedral angle of 3.94 (6)°. The S(6) ring makes dihedral angles of 23.79 (6), 78.53 (6) and 67.91 (6)° with the pyrazolone ring, the pyrazole ring and the benzene ring of antipyrine, respectively. The structure exhibits a thienyl-ring flip disorder with occupancy factors in the ratio 0.82:0.18.
In the title compound, C12H2Cl2F6IN3OS, the dihedral angle between the planes of the benzene and pyrazole rings is 77.8 (2)°. In the crystal, a short I⋯N contact of 2.897 (5) Å occurs.
In the title compound, C27H27N3O5·2H2O, the dihydropyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, molecules are linked via N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C—H⋯π interactions.
The title compound, C14H12N2O2, is almost planar with an r.m.s. deviation for all non-H atoms of 0.038 Å. The observed planarity is rationalized in terms of a close intramolecular C—H⋯O interaction. Supramolecular layers, two molecules thick and with a step topology, are formed in the crystal packing via C—H⋯O contacts involving the carbonyl O atom, which accepts two such bonds, and π–π interactions between the components of the fused ring system and the phenyl ring of inversion-related molecules [centroid–centroid distances = 3.6819 (13) and 3.6759 (12) Å].
The asymmetric unit of the title compound, C8H8N2O2, comprises two independent molecules in both of which, all non-H atoms lie in a common plane (r.m.s. deviation = 0.014 and 0.017 Å). In the crystal, N—H⋯O hydrogen bonds connect the molecules into zigzag chains running along [10-1]. Weak C—H⋯O interactions connect the chains into an infinite network.
The title compound, C18H7BrCl2F3N5O2, is an L-shaped tricyclic imine. The pyrazole ring is essentially coplanar with the nitro-substituted benzene ring [dihedral angle = 3.6 (2)°] and approximately perpendicular to the trifluoromethylsubstituted ring [dihedral angle = 88.5 (2)°].
In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo[1,5-a]pyrimidine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichlorophenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluorophenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals interactions. A Cl⋯Cl interaction of 3.475 (3) Å also occurs.
The title compound, C19H10BrCl2F3N4O, is an imine with an overall Y shape. The dihedral angles between the pyrazole ring and the methoxy- and trifluoromethyl-substituted benzene ring planes are 88.4 (2) and 65.8 (2)°, respectively.
In the title molecule, C15H13ClF3N3O3, the pyrazole and benzene rings form a dihedral angle of 77.6 (3)°. In the crystal, molecules related by translation along the a axis are linked into chains via C—H⋯O hydrogen bonds. The crystal packing is stabilized further by weak π–π [centroid–centroid distance = 3.734 (6) Å] and dipole–dipole interactions [C⋯O = 3.174 (2) Å].
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 molecule, C26H20F3N3O2, the two central five-membered rings form a dihedral angle of 62.94 (8)°. The absolute configuration was determined by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y = −0.05 (11). Notable intra- and intermolecular contacts include C—H⋯O and C—H⋯π(arene) hydrogen bonds.
In the title molecule, C19H18F3N3O, the dihydropyridine and cyclohexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydropyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoromethyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link molecules into a two-dimensional network parallel to (100).
In the title molecule, C19H17F3N2O2, the fused cyclohexene and pyran rings adopt sofa and flattened boat conformations, respectively. The four essentially planar atoms of the pyran ring [maximum deviation = 0.008 (2) Å] form a dihedral angle of 88.13 (9)° with the benzene ring. The F atoms of the trifluoromethyl group were refined as disordered over three sets of sites in a 0.507 (7):0.330 (7):0.163 (3) ratio. In the crystal, molecules are connected into inversion dimers via pairs of N—H⋯N hydrogen bonds and these dimers are further linked by N—H⋯O hydrogen bonds into a two-dimensional network parallel to (100).
In the title compound, C13H11ClN2O3, the nine-membered bicycle includes an oxime group having the C=N group in an E configuration. The isoxazole ring is almost planar [r.m.s. deviation = 0.0056 Å]; the dihedral angle between the isoxazole and 4-chlorophenyl ring is 75.60 (5)°. In the crystal, intermolecular O—H⋯Nisoxazole hydrogen bonds give rise to chains running along the b axis.
In the title compound, C19H19N3OS2, the thiopyran ring adopts a twist-chair conformation and the pyrimidinone unit is essentially planar, with a mean deviation of 0.0497 Å. The thiophene ring is essentially planar with a maximum deviation of 0.024 (2) Å, while the pyrrolidine ring exhibits an envelope conformation. The pyrimidinone and thiophene rings are almost coplanar, forming a dihedral angle of 6.31 (15)°, while the dihedral angle between the mean planes of the phenyl ring and the pyrimidinone ring is 68.13 (10)°. In the crystal structure, adjacent molecules are linked by C—H⋯O hydrogen bonds, forming a two-dimensional network in the ac plane.