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, 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].
In the title compound, C21H20ClN5·H2O, the 1H-imidazo[4,5-c]quinoline ring is approximately planar, with a maximum deviation of 0.0795 (7) Å, and it forms a dihedral angle of 7.65 (3)° with the chlorophenyl ring. In the crystal, the components are linked into chains along the a axis via intermolecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds. One of the H atoms of the water molecule is disordered over two positions with a site-occupancy ratio of 0.80 (4):0.20 (4).
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 molecule of the title compound, C12H15BrN4O2, the imidazole and pyridine rings are strictly coplanar [maximum deviation 0.006 (3) Å]. In the crystal structure, molecules are linked into chains running parallel to the a axis by intermolecular N—H⋯O hydrogen bonds. Centrosymmetrically related chains are further connected by N—H⋯N hydrogen-bonding interactions to form a two-dimensional layer structure parallel to the ab plane.
In the title compound, C18H11BrN4OS, the imidazothiadiazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothiadiazole and bromophenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, intermolecular C—H⋯N interactions result in chains of molecules along the b and c axes. Moreover, C—H⋯O interactions result in centrosymmetric head-to-head dimers with R
2(24) graph-set motifs. The molecular packing is further stabilized by π–π stacking interactions between the imidazole rings with a shortest centroid–centroid distance of 3.492 (3) Å. In addition, C—H⋯π interactions are observed in the crystal structure.
In the title molecule, C23H14N4O, the dihedral angle between the pyridine rings of the phenanthroline unit is 4.43 (8)° and the dihedral angle formed by the nine essentially planar [maximum deviation 0.0389 (16)Å] non-H atoms of the benzimidazole unit and the naphthalene ring system is 74.22 (5)°. In the crystal, molecules are linked by intermolecular N—H⋯N and O—H⋯N hydrogen bonds, forming a three-dimensional network.
The title compound, C27H18N4O·2CH4O, is a unsymmetrically substituted quinoxaline. An intramolecular O—H⋯N hydrogen bond involving the hydroxy and imino groups generates an S(6) ring motif. Intermolecular C—H⋯O and N—H⋯O hydrogen bonds form an R
1(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring molecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π–π interactions [centroid–centroid distances = 3.5234 (9)–3.7885 (10) Å]. The crystal structure is stabilized by intramolecular O—H⋯N, intermolecular O—H⋯O, N—H⋯O and C—H⋯O (× 2) hydrogen bonds and weak intermolecular C—H⋯π and π–π interactions.
In the title compound, C20H14N4, all the non-H atoms are roughly coplanar with an r.m.s. deviation of 0.0776 Å. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, forming chains along the (). The chains are connected by intermolecular C—H⋯N hydrogen bonds and π–π stacking interactions between inversion-related phenanthroline, imidazole and phenyl rings with centroid–centroid distances in the range 3.777 (1)–3.905 (1) Å.
In the title compound, C10H6F3N3, the imidazo[1,2-a]pyridine group is essentially planar with a maximum deviation of 0.021 (1) Å. The F atoms in the trifluoromethyl group and the methyl H atoms are each disordered over two sets of sites with refined site occupancies of 0.68 (1):0.32 (1). In the crystal, molecules are linked into infinite chains through two C—H⋯N interactions forming R
2(12) and R
2(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.
In the title compound, C23H20N4·1.5H2O, the mean planes of the imidazo[4,5-f][1,10]phenanthroline system and the benzene ring make a dihedral angle of 21.76 (2)°. One water O atom lies on a twofold rotation axis. The organic molecules and water molecules are linked via N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. Weak intermolecular C—H⋯N hydrogen bonds and π–π stacking interactions between inversion-related phenanthroline rings complete the three-dimensional hydrogen-bonding network in the crystal structure. The stacking distance is short at 3.513 (2) Å and the perpendicular distance between the rings is 3.355 Å. The three methyl groups are disordered over two positions, with a site-occupancy ratio of 0.875 (14):0.125 (14).
The benzyl residue in the title compound, C21H23N5·0.5H2O, is oriented at a dihedral angle of 83.8 (3)° towards the 1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine system. The piperidine ring adopts a chair conformation with the cis substituents displaying a torsion angle of −45.91 (16)°. In the crystal, molecules are accumulated as racemic dimers by two intermolecular hydrogen bonds between the pyrrolopyridine systems. Another hydrogen bond is formed between the imidazole ring and the cocrystallized water molecule, which is located on a twofold rotation axis.
The room-temperature reaction of propargyl bromide and 6-bromo-1,3-dihydroimidazo[4,5-b]pyridin-2-one in dimethylformamide yields the title compound, C12H8BrN3O, which features nitrogen-bound propynyl substituents. The imidazopyridine fused ring is almost planar (r.m.s. deviation = 0.011 Å); the propynyl chains point in opposite directions relative to the fused ring. One acetylenic H atom is hydrogen bonded to the carbonyl O atom of an inversion-related molecule, forming a dimer; adjacent dimers are linked by a second acetylene–pyridine C—H⋯N interaction, forming a layer motif.
In the title compound, C21H20N4O2, the statistically planar 1H-limidazole ring [maximum deviation = 0.003 (1) Å] makes dihedral angles of 1.33 (9) and 8.23 (7)°, respectively, with the essentially planar fused pyridine ring [maximum devation = 0.018 (1) Å] and the pendant benzene ring, which is attached to the pyridine ring by an —NH— group. An intramolecular C—H⋯N interaction, which generates an S(6) ring, helps to estalish the molecular conformation. In the crystal, the molecules are linked by N—H⋯O, C—H⋯O and O—H—N hydrogen bonds, which generate bifurcated R
2(6) and R
2(9) ring motifs, resulting in supramolecular  chains. The crystal structure also features weak π–π stacking [centroid–centroid distance = 3.5943 (9) Å] and C—H⋯π interactions.
In the title compound, C11H11N5OS, the pyrazole ring is approximately planar, with a maximum deviation of 0.010 (2) Å. The dihedral angles between the benzene ring and the pyrazole and carbothioamide groups are 5.42 (9) and 10.61 (18)°, respectively. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are connected by intermolecular N—H⋯O and C—H⋯S hydrogen bonds, forming R
2(12) ring motifs. In addition, there is a π–π stacking interaction [centroid–centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These interactions link the molecules into infinite chains along .
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.
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intramolecular C—H⋯O hydrogen bond stabilizes the molecular structure and forms an S(6) ring motif. In the crystal packing, intermolecular N—H⋯N hydrogen bonds link centrosymmetrically related molecules into dimers, generating R
2(8) ring motifs. The dimers are then linked into a three-dimensional network by intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π interactions. Further stabilization is provided by π–π interactions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
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.
The title compound, C13H16N2O4, is approximately planar (r.m.s. deviation = 0.065 Å for the 19 non-H atoms). An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif and the molecule adopts an E conformation with respect to the central C=N double bond. In the crystal, pairs of intermolecular C—H⋯O hydrogen bonds link adjacent molecules into inversion dimers. The crystal structure also features weak C—H⋯π interactions.
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, C13H9Br2N3O, the molecular skeleton, influenced by an intramolecular O—H⋯N hydrogen bond, is roughly planar, with a mean deviation of 0.033 Å. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating in . Weak intermolecular π–π interactions [centroid–centroid distances = 3.760 (3) and 3.723 (3) Å] further consolidate the packing.
In the title compound, C16H19ClN4O3, the cyclohexane ring displays a chair formation and the tetrahydropyridine ring displays an envelope conformation with the methylene C atom as the flap; the imidazolidine ring also displays an envelope conformation with a methylene C atom as the flap. In the crystal, O—H⋯N hydrogen bonds between hydroxy groups and pyridine rings link inversion-related molecules into dimers. Weak C—H⋯O hydrogen bonds further link the dimers into supramolecular chains running along the c axis.
In the title compound, C25H16BrN3O2S·CHCl3, the thiazole ring is approximately planar [maximum deviation = 0.002 (3) Å] and makes dihedral angles of 10.75 (14) and 87.75 (15)/2.80 (14)° with the pyran ring system and the two terminal phenyl rings, respectively. The solvent molecule is disordered over two sets of sites, with refined occupancies of 0.639 (7) and 0.361 (7). In the crystal, molecules are connected via pairs of weak C—H⋯O interactions, forming centrosymmetric dimers. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif.
In the title compound, C16H10N4O, both the methoxy and nitrile substituents lie in the plane defined by the benzo[g]imidazo[1,2-a]-1,8-naphthyridine ring system, resulting in a nearly planar geometry for the entire molecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044 Å). In the solid-state, the molecules form a three-dimensional polymer through intermolecular C—H⋯N and C—H⋯O hydrogen bonds. In addition, the packing mode results in stabilizing π–π stacking interactions between the asymmetric units.
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.