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).
Crystal structures of methyl 3-phenyl-4,5-dihydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxylate and methyl 1-methyl-3-phenyl-4,5-dihydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxylate
In two benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxylates, the seven-membered oxazepane rings both have a twist-chair conformation. The dihedral angle between the phenyl ring and the benzimidazole ring system is significantly smaller in one of the compounds, viz. 73.42 (10) compared to 83.07 (17)°.
The title compounds, C19H18N2O3, (I), and C20H20N2O3, (II), differ only by a methyl substituent on the seven-membered oxazepine ring in (II). In both compounds, these rings have a twist-chair conformation. The phenyl ring makes a dihedral angle of 73.42 (10)° with the benzimidazole ring system mean plane (r.m.s. deviation = 0.015 Å) in (I) and 83.07 (7)° in (II) (r.m.s. deviation = 0.026 Å). The methyl carboxylate groups are planar to within 0.031 (2) in (I) and 0.003 (2) Å in (II). They are inclined to the phenyl and benzimidazole ring system by 33.78 (16) and 87.56 (14)°, respectively, in (I) and by 53.04 (12) and 60.22 (11)°, respectively, in (II). In the crystal of (I), molecules stack in a herringbone fashion and are linked by C—H⋯O hydrogen bonds, forming chains along . In the crystal of (II), there are no significant intermolecular interactions present.
crystal structure; oxazepine; benzimidazole; angiogenesis; natural products.
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.
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.
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].
The asymmetric unit of the title compound, C21H15Cl2N5O4, contains two independent molecules (A and B) having similar conformations. The amine (NH2) group forms an intramolecular hydrogen bond with the benzoyl group, giving an S(6) ring motif in both molecules. The central six-membered rings adopt sofa conformations and the imidazole rings are planar (r.m.s deviations = 0.0150 and 0.0166 Å). The pyridine and imidazole rings are inclined to one another by 3.54 (1) and 3.03 (1)° in molecules A and B, respectively. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains along the a axis which enclose R
2(16) ring motifs. The rings are linked by weak N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions forming sheets lying parallel to (001). A region of disordered electron density, most probably disordered solvent molecules, occupying voids of ca 753 Å3 for an electron count of 260, was treated using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.
crystal structure; spiro; imidazole; pyridine-indoline C—H⋯π interactions; hydrogen bonding
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.
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, 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, C9H10N2O, the imidazo[1,2-a]pyridine moiety is approximately planar (r.m.s. deviation = 0.024 Å). The methanol group is nearly perpendicular to its mean plane as indicated by the C—C—C—O and N—C—C—O torsion angles of 80.04 (16) and −96.30 (17)°, respectively. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming inversion dimers with an R
2(10) ring motif. The dimers are liked via C—H⋯O hydrogen bonds, enclosing R
2(10) ring motifs and forming ribbons along . The ribbons are linked via a number of π–π interactions [centroid–centroid distances vary from 3.4819 (8) to 3.7212 (8) Å], forming a three-dimensional structure.
crystal structure; imidazo[1,2-a]pyridine; hydrogen bonding; π–π interactions
In the title compound, C14H11Cl2N5O, the plane of the 1H-imidazo[4,5-c]pyridine ring system [r.m.s. deviation = 0.087 (19) Å] makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring. An intramolecular N—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, N—H⋯O hydrogen bonds link the molecules into inversion dimers. These dimers are connected by π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å].
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.
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 C21H17N5O4·C2H6OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp2 hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH2 group forms an intramolecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R
2(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent molecule which acts as both an acceptor and a donor..
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).
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 .
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.
In the title compound, C19H11N3O2SClBr, the chromene ring system and the thiazole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The molecule adopts an E configuration about the central C=N double bond. The central thiazole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The molecular structure features a short C—H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains along the b axis. π–π stacking interactions [centroid-centroid distance = 3.4813 (15) Å] are also present.
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, C22H18BrN5O4, the central six-membered ring, derived from 1,4-dihydropyridine, adopts a distorted boat conformation with a puckering amplitude of 0.197 (3) Å, the imidazole ring adopts a twisted conformation with a puckering amplitude of 0.113 (3) Å, and the oxindole moiety is planar with an r.m.s. deviation of 0.0125 Å. Two intramolecular N—H⋯O hydrogen bonds are formed, each closing an S(6) loop. In the crystal, strong N—H⋯O hydrogen bonds lead to the formation of zigzag chains along the c axis. These are consolidated in the three-dimensional crystal packing by weak N—H⋯O hydrogen bonding, as well as by C—H⋯O, C—H⋯Br and C—H⋯π interactions. A small region of electron density well removed from the main molecule was removed with the SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155] following unsuccessful attempts to model it as a plausible solvent molecule. The unit-cell characteristics do not take into account this feature of the structure.
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.