The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å].
In the imidazo[2,1-b][1,3]thiazole group of the title compound, C21H17ClN4O2S, the dihedral angle between the thiazole and imidazole rings is 1.9 (2)°. The mean plane of this group makes dihedral angles of 5.5 (2) and 39.9 (2)° with the benzene rings of the chlorophenyl and methoxyphenyl groups, respectively. The dihedral angle between these two benzene rings is 34.4 (2)°. In the crystal, molecules are connected to each other by intermolecular N—H⋯O hydrogen bonds along the b axis, generating a C(4) chain. Weak C—H⋯π interactions also occur.
In the title compound, C18H11ClN4OS, the benzisoxazole and imidazothiadiazole rings are inclined at an angle of 23.81 (7)° with respect to each other. The imidazothiadiazole and chlorophenyl rings make a dihedral angle of 27.34 (3)°. In the crystal, intermolecular C—H⋯N interactions generate a chain along the c axis and C—H⋯O interactions form centrosymmetric dimers resulting in an R
2(26) graph-set motif. Moreover, the C—H⋯N and S⋯N [3.206 (4) Å] interactions links the molecules into R(7) ring motifs. The packing is further stabilized by π–π stacking interactions between the thiadiazole rings with a shortest centroid–centroid distance of 3.497 (3) Å. In addition, C—H⋯π interactions are observed in the crystal structure
In the title compound, C14H14ClN3S, the imidazo[2,1-b][1,3,4]thiadiazole system is essentially planar, with a maximum deviation of 0.006 (2) Å. The dihedral angle between the imidazo[2,1-b][1,3,4]thiadiazole and chlorophenyl rings is 5.07 (8)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak π–π [centroid–centroid distance = 3.5697 (11) Å] and C—H⋯π interactions.
The asymmetric unit of the title compound, C22H16ClN3O5, consists of two crystallographically independent molecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and were refined using a split model. In the crystal structure, the molecules are connected via weak intra- and intermolecular C—H⋯O interactions are present. The ethyl group in one molecule is disordered over two positions, with site occupancy factors 0.55 and 0.45; in the other molecule only the methyl group is disordered over two positions, with site occupancy factors 0.6 and 0.4.
In the title compound, C15H17N3O, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.036 (1) Å. The C—N—C—C torsion angles formed between this ring system and the isobutyl unit are −99.77 (16) and 79.71 (17)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into chains along the c axis.
In the title compound, C25H15FN4·H2O, the fused ring system is essentially planar [maximum deviation of 0.0822 (14) Å]. The imidazole ring makes dihedral angles of 76.83 (7) and 32.22 (7)° with the phenyl group attached to nitrogen and the fluorobenzene group to carbon, respectively. The dihedral angle between the two phenyl rings is 72.13 (7)°. Intermolecular O—H⋯N, O—H⋯F, C—H⋯F, C—H⋯O and C—H⋯N hydrogen bonds are found in the crystal structure.
In the title compound, C24H21ClN4O2S, the two adjacent spiro junctions link an almost planar (r.m.s. deviation = 0.017 Å) 2-oxindole ring, a hexahydro-1H-pyrrolizine ring and a tetrahydroimidazo[2,1-b]thiazole ring. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur, generating an R
The asymmetric unit of the title compound, C16H11FN2OS, comprises two independent molecules in which the benzothiazole rings are essentially planar, with maximum deviations of 0.038 (2) and 0.045 (3) Å. The central benzothiazole ring makes dihedral angles of 4.87 (13) and 0.64 (12)° and 4.04 (12) and 3.67 (12)° with the two terminal phenyl rings in the two independent molecules. In the crystal, molecules are connected via weak intermolecular C—H⋯O hydrogen bonds forming supramolecular chains along the c axis.
In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thiadiazole rings is 6.0 (9)°. In the crystal, molecules are assembled by the formation of centrosymmetric dimers by π-stacking of the thiadiazole and benzene rings of neighboring molecules [centroid–centroid distance = 3.6938 (11) Å] along .
The asymmetric unit of the title compound, C14H9ClN2O, contains two molecules with dihedral angles of 33.52 (11) and 34.58 (11)° between their benzene rings and imidazole ring systems. In the crystal, C—H⋯N and C—H⋯O interactions are observed. The crystal examined was found to be a racemic twin.
In the molecule of the title compound, C15H11ClN2O2, the nine-membered heterobicycle is approximately planar [largest deviation from least-squares plane = 0.012 (2) Å] and forms a dihedral angle of 51.14 (8)° with the plane of the 4-chlorophenyl group. There is a non-classical intramolecular hydrogen bond between the pyridine α-H atom and the O atom of the benzoyl group. The crystal structure is stabilized by weak C—H⋯O and C—H⋯Cl interactions involving the ‘olate’ O atom and the Cl atom attached to the benzoyl group as acceptors.
In the title compound, C17H11BrFN3S, the imidazothiadiazole and bromophenyl rings are individually almost planar, with maximum deviations of 0.0215 (4) and 0.0044 (4) Å, respectively, and are inclined at an angle of 27.34 (3)° with respect to each other. The dihedral angle between the mean planes of the fluorobenzyl and imidazothiadiazole rings is 79.54 (3)°. The crystal structure is stabilized by intermolecular C—H⋯N interactions resulting in chains of molecules along the b axis.
In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, molecules are linked into a zigzag chain along the a axis by intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions are also present.
In the title compound, C14H17N5, the 1H-imidazo[4,5-c]quinoline ring system is essentially planar, with a maximum deviation of 0.0325 (7) Å. In the crystal, a pair of intermolecular N—H⋯N hydrogen bonds link neighbouring molecules, forming an inversion dimer and generate an R
2(10) ring motif. These dimers are further connected into a chain along the b axis via intermolecular C—H⋯N hydrogen bonds, resulting in an R
2(14) ring motif.
The organic molecule in the title hydrate, C17H14ClN3O·H2O, has a small but significant twist from planarity, as seen in the dihedral angle of 12.10 (17)° between the quinoline and benzene rings. The conformation about the C=N bond is E. Chains along the b axis are formed in the crystal structure aided by water–quinoline O—H⋯N (× 2) and hydrazone–water N—H⋯O hydrogen bonds. Layers of these chains stack along the a axis via C—H⋯π and π–π interactions [ring centroid–ring centroid distance = 3.674 (2) Å]. C—H⋯O interactions are also present.
In the title compound, C28H21ClN2O3, the quinoline ring system is essentially planar with a maximum deviation of 0.0436 (17) Å. The isoxazole and cyclohexane rings adopt envelope conformations. The isoxazole ring is almost orthogonal to both the quinoline ring system and the cyclohexane ring, making dihedral angles of 85.75 (8) and 81.46 (9) °, respectively. The O atom deviates signifigantly from the six-membered carbocyclic ring by 0.3947 (16) Å. In the crystal, molecules are linked into inversion dimers via pairs of C—H⋯O interactions, resulting in R
2(24) ring motifs.
In the title compound, C17H13ClN2O2·H2O, the dihedral angle between the quinoline ring system and the benzene ring is 13.0 (1)°. An intramolecular N—H⋯O hydrogen bond may influence the molecular conformation. In the crystal structure, acetamide molecules are linked to water molecules via intermolecular O—H⋯ N and N—H⋯O hydrogen bonds and in turn linked into chains along  via O—H⋯O hydrogen bonds.
In the title compound, C13H7ClN4, the imidazopyridazine ring system is essentially planar [maximum deviation 0.015 (1) Å]. It is inclined to the benzene ring of the benzonitrile group by 11.31 (2)°. In the crystal, molecules are linked via C—H⋯Cl and C—H⋯N interactions.
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, 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, C22H19ClN4Se2, the mean plane of the non-fused selenadiazole ring forms dihedral angles of 54.20 (16)° and 70.48 (11)°, respectively, with the essentially planar [maximum deviations of 0.025 (5) and 0.009 (2) Å, respectively] methylphenyl and chlorophenyl substituents. The tetrahydro-1,2,3-benzoselenadiazole group is disordered over two sets of sites with a refined occupancy ratio of 0.802 (5):0.198 (5). In the crystal, weak intermolecular C—H⋯N interactions are observed.
In the title compound, C16H20N4, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.0719 (15) Å. An intramolecular C—H⋯N hydrogen bond contributes to the stabilization of the molecule, forming an S(6) ring motif. In the crystal, the molecules are stacked along the b axis through weak aromatic π–π interactions between benzene and imidazole and benzene and pyridine rings [centroid–centroid distances = 3.6055 (10) and 3.5342 (10) Å, respectively].
The title compound, C22H18ClN3S, was synthesized by the reaction of 4-chlorobenzaldehyde, tetrahydrothiopyran-4-one and 3-methyl-1-phenyl-1H-pyrazol-5-amine in acetic acid without a catalyst. The pyridine and pyrazole rings are almost coplanar, the dihedral angle between their mean planes being 2.50 (1)°. The thiopyran ring exhibits an envelope conformation. The crystal packing is stabilized by intermolecular C—H⋯Cl hydrogen bonds and by C—H⋯π and π–π interactions [centroid–centroid distances of 3.825 (2) Å between pyridine rings and 3.557 (2) Å between pyrazole and pyridine rings.
In the title compound, C14H15N3S, the imidazo[2,1-b][1,3,4]thiadiazole fused-ring system is close to planar, with a maximum deviation of 0.042 (1) Å, and the dihedral angle between it and the phenyl ring is 24.21 (6)°. The isobutyl group is disordered over two sets of sites in a 0.899 (9):0.101 (9) ratio. In the crystal, weak aromatic π–π stacking interactions involving the imidazole and thiadiazole rings with a centroid–centroid distance of 3.8067 (7) Å occur.