The title compound, C21H18N2O2, was synthesized using a novel tandem annulation reaction between (1H-benzimidazol-2-yl)(phenyl)methanone and (E)-ethyl 4-bromobut-2-enoate under mild conditions. The dihedral angles between the mean planes of the five-membered imidazole ring and the pyridine, benzene and phenyl rings are 0.45 (6), 1.69 (1) and 70.96 (8)°, respectively. In the crystal, molecules are linked through intermolecular C—H⋯N hydrogen bonds.
The 1,4-dihydropyridine ring in the title hydrate, C17H18BrNO2·H2O, has a flattened-boat conformation, and the benzene ring is occupies a position orthogonal to this [dihedral angle: 82.19 (16)°]. In the crystal packing, supramolecular arrays mediated by N—H⋯Owater and Owater—H⋯Ocarbonyl hydrogen bonding are formed in the bc plane. A highly disordered solvent molecule is present within a molecular cavity defined by the organic and water molecules. Its contribution to the electron density was removed from the observed data in the final cycles of refinement and the formula, molecular weight and density are given without taking into account the contribution of the solvent molecule.
In the title salt, C37H51N2O10
+·Br−, the 1,4-dihydropyridine (1,4-DHP) ring adopts a slighly puckered boat conformation. The N and opposite C atoms deviate from the least-squares plane calculated through the four other ring atoms by 0.068 (5) and 0.224 (5) Å, respectively. The orientation of both C=O groups is similar (cis with respect to the double bonds of 1,4-DHP. The pyridinium ring has an axial orientation with respect to the1,4-DHP ring and is almost perpendicular to the least-squares plane of the 1,4-DHP ring, making a dihedral angle of 89.2 (3)°. The molecule has a compact shape due to the parallel orientation of the long-chain substituents. One of the butoxy groups was fond to be disordered (occupancy ratio 0.70:0.30). In the crystal, the bromide anion accepts a weak hydrogen bond from the N—H group of a neighboring 1,4-DHP ring.
2-Amino-5,7-bis(4-fluorophenyl)-1′,3′-dimethyl-7,8-dihydrospiro[pyrido[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2′,4,4′,6′(3H,1′H,3′H,5′H)-tetraone ethanol solvate
In the molecule of the title compound, C24H20F2N6O4·C2H5OH, the pyrimidine ring is oriented at dihedral angles of 42.64 (3) and 62.94 (3)° with respect to the benzene rings, while the dihedral angle between the benzene rings is 74.45 (3)°. The pyridine ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonds link the molecules into a two-dimensional network, forming R
2(8) ring motifs. π–π contacts between the pyrimidine and benzene rings [centroid–centroid distances = 3.516 (1) and 3.927 (1) Å] may further stabilize the structure.
In the title compound, C21H28N2O4, the dihydropyridine ring adopts a flattened boat conformation. The mean plane of the dihydropyridine ring and the attached benzene ring form a dihedral angle of 85.1 (1) Å. One of two ethyl fragments is disordered between two conformations in a 0.67 (4):0.33 (4) ratio. In the crystal structure, molecules related by translation along the a axis are linked into chains via intermolecular N—H⋯O hydrogen bonds.
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 ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydropyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, molecules are bridged via O—H⋯O hydrogen bonds involving the partially occupied water molecule, and this arrangement is strengthened by a pair of N—H⋯O hydrogen bonds and C—H⋯O interactions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).
The title compound, C18H19NO5, is a product of the Hantzsch reaction of p-phthalaldehyde, methyl acetoacetate, and ammonium acetate. The 1,4-dihydropyridine ring of the molecule adopts a flattened boat conformation. The benzene ring is almost perpendicular to the 1,4-dihydropyridine ring; the plane through the six C atoms of the benzene ring and the plane through the four C atoms that form the base of the boat-shaped 1,4-dihydropyridine ring (excluding the ring N atom and the opposite ring C atom) make a dihedral angle of 87.60 (3)°. Intermolecular N—H⋯O hydrogen bonds result in the formation of extended chains along the a axis.
The title compound, C15H9BrN2S, was prepared by the reaction of 1-bromo-2-(2,2-dibromovinyl)benzene with 1H-benzo[d]imidazole-2(3H)-thione. The thiazolo[3,2-a]benzimidazole fused-ring system is nearly planar, the maximum atomic deviation being 0.049 (4) Å. This mean plane is oriented at a dihedral angle of 71.55 (17)° with respect ot the bromophenyl ring. π–π stacking is observed in the crystal structure, the centroid–centroid distance between the thiazole and imidazole rings of adjacent molecules being 3.582 (2) Å.
The title molecule, C14H19NO6, was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH4HCO3. In the crystal structure, the dihydropyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong intermolecular hydrogen bonds. N—H⋯O interactions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain.
In the title compound, C19H23NO6, the 1,4-dihydropyridine ring is twisted slightly from planarity, with a maximum deviation of 0.101 (1) Å, and adopts a very flattened boat conformation. The dihedral angle formed between the plane through the four C atoms of the 1,4-dihydropyridine ring and the benzene ring is 84.67 (7)°. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.
In the title compound, C28H32N2O7, the 1,4-dihydropyridine ring adopts a flattened boat conformation. The two benzene rings are approximately perpendicular to the dihydropyridine ring, forming dihedral angles of 84.29 (9) and 82.96 (9)° with the mean plane of the 1,4-dihydropyridine unit, whereas the ester groups are only slightly twisted relative to this plane, with dihedral angles of 10.6 (1) and 9.0 (1)°.
The imidazole ring in the title compound, C27H22N8, adopts a slight envelope conformation with the C atom carrying the phenyl ring being the flap atom. The phenyl ring is almost perpendicular to the mean plane of the imidazole ring [dihedral angle = 88.90 (7)°]. The (1H-benzotriazol-1-yl)methyl groups bound to the imidazole ring are positioned on the same side of the imidazole ring. The dihedral angle between these benzotriazolyl rings is 17.71 (5)°. The crystal packing is stabilized by a C—H⋯π interaction, which connects the molecules into zigzag chains running along the b axis.
The title compound, C10H8BrCl2NO2, is a target molecule in our research on herbicide safeners. The oxazine ring has an envelope conformation, with puckering parameters close to ideal values [Q = 0.498 (3) Å, θ = 53.7 (3)° and ϕ = 253.4 (4)°]. The crystal structure is stabilized by C—H⋯O, C—H⋯Cl and C—H⋯Br interactions.
In the structure of the title compound, C17H17BrN2O, the central phenyl and imidazol-2-one rings are coplanar (dihedral angle between planes of 0.73 (11)°). The angles subtended by the substituents on the N atoms of the imidazol-2-one ring range from 109.71 (14)° to 128.53 (15) due to steric hindrance of these substituents with the phenyl H atoms. The carbonyl O and Br both make two weak C—H⋯O and C—H⋯Br interactions with two adjacent molecules, thus forming an three-dimensional array.
The title compound, C24H24N2O4·CH3CN, a disubstituted benzimidazole, crystallized as an acetonitrile monosolvate. The benzene ring of the 2-ethoxy-6-methylphenol substiuent is approximately perpendicular to the nearly planar benzimidazole ring system [maximum deviation = 0.016 (1) Å], making a dihedral angle of 84.27 (8)°. The benzene ring of the 2-ethoxyphenol substituent is inclined to the benzimidazole mean plane by 29.68 (8)°. The dihedral angle between the benzene rings is 80.36 (9)°. In the molecule, there are strong O—H⋯N and O—H⋯O hydrogen bonds. In the crystal, molecules are connected by bifurcated O—H⋯(O,O) hydrogen bonds, forming chains propagating along .
The title compound, C19H18Cl2N2O5, was synthesized by the reaction of N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide and acetic anhydride. The oxadiazole ring makes dihedral angles of 82.82 (7) and 9.92 (7)° with the 3,4-dichlorobenzene and the 3,4,5-trimethoxybenzene ring planes, respectively. The crystal structure is stabilized by intermolecular C—H⋯ O and C—H⋯ N hydrogen bonds. Intramolecular C—H⋯O and C—H⋯N hydrogen bonds are also present.
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 asymmetric unit of the title compound, C25H35NO6, contains two independent molecules. In each molecule, the 1,4-dihydropyridine ring adopts a flattened boat conformation. The dihedral angles between the 1,4-dihydropyridine and benzene rings are 87.55 (7) and 87.23 (7)°. In one of these molecules, one of the isobutyl groups is disordered over two sets of sites, with an occupancy ratio of 0.890 (2):0.110 (2). In the crystal, molecules are linked through N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds forming two-dimensional networks parallel to the ab plane. The crystal structure is further stabilized by weak C—H⋯π interactions.
The title molecule, C19H23NO4, was synthesized by the reaction of benzaldehyde, ethyl acetoacetate and NH4HCO3. The dihydropyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 88.78 (9)° with the phenyl ring. The packing is stabilized by strong intermolecular N—H⋯O and weak intermolecular C—H⋯O hydrogen bonds.
The asymmetric unit of the title compound, C20H17N3, contains two crystallographically independent molecules (A and B). In molecule A, the two benzene rings form dihedral angles of 74.12 (7) and 7.83 (7)° with the pyridine ring, while in molecule B these angles are 77.48 (7) and 21.50 (7)°. The seven-membered heterocyclic ring adopts a boat conformation in both molecules. In the crystal structure, each of the independent molecules forms a centrosymmetric R
2(8) dimer linked by paired N—H⋯N hydrogen bonds. The crystal structure is further stabilized by intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions.
In the title compound, C20H21N3O4, the 1,4-dihydropyridine ring adopts a boat conformation. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The pyrazole ring makes dihedral angles of 87.81 (7) and 45.09 (7)° with the mean plane of the 1,4-dihydropyridine ring and the phenyl ring, respectively. In the crystal, molecules are linked by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network.
In the title compound, C22H25N3O4, the dihydropyridine ring adopts a flattened boat conformation. The pyrazole ring makes a dihedral angle of 29.04 (5)° with the benzene ring. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond which generates an S(9) ring motif. In the crystal, molecules are linked via N—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. The crystal structure is further consolidated by weak C—H⋯π interactions.
In the title molecule, C19H23NO5, the dihedral angle formed by the benzene ring and the planar part of the dihydropyridine ring is 83.52 (5)°. The dihydropyridine ring adopts a flattened boat conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating chains running parallel to . The crystal structure is consolidated by C—H⋯O contacts.
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.