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, C12H9ClN2S, the imidazo[2,1-b]thiazole fragment is planar (r.m.s. deviation = 0.003 Å), and the benzene ring is twisted slightly [by 5.65 (6)°] relative to this moiety. In the crystal, molecules are linked by π–π stacking interactions into columns along . The molecules within the columns are arranged alternatively by their planar rotation of 180°. Thus, in the columns, there are the two types of π–π stacking interactions, namely, (i) between two imidazo[2,1-b]thiazole fragments [interplanar distance = 3.351 (2) Å] and (ii) between an imidazo[2,1-b]thiazole fragment and the phenyl ring [interplanar distance = 3.410 (5) Å]. There are no short contacts between the columns.
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, 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.
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 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.
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.
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
In the title 1:1 co-crystal, [PtCl2(C11H14ClN3O)2]·C7H5ClO, the coordination polyhedron of the PtII atom is slightly distorted square-planar with the chloride and 2,3-dihydro-1,2,4-oxadiazole ligands mutually trans, as the Pt atom lies on an inversion center. The 4-chlorobenzaldehyde molecules are statistically disordered about an inversion centre with equal occupancies for the two positions. The PtII complex forms a three-dimensional structure through C—H⋯Cl and weaker C—H⋯O interactions with the 4-chlorobenzaldehyde molecule.
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 1:4 title co-crystal of 2-amino-4-(4-chlorophenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile, 0.2C20H14ClN3·0.8C22H14ClN3, has the atoms of the fused-ring system and those of the amino, cyano and chlorophenyl substitutents overlapped. The fused-ring system is buckled owing to the ethylene linkage in the central ring. There are two independent overlapped molecules in the asymmetric unit. In one independent molecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chlorophenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second molecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent molecules are linked by N—H⋯N hydrogen bonds into dimers.
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 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, C16H16Cl2N4, the imidazole ring mean plane makes a dihedral angle of 70.01 (1)° with the phenyl ring. The Cl atoms deviate by −0.0472 (6) and 0.0245 (8) Å from the plane of their attached benzene ring. In the crystal, molecules are linked via pairs of C—H⋯N hydrogen bonds, forming inversion dimers.
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
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, 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.
The title compound, C19H16ClO2P, was obtained by the reaction of diphenylphosphine oxide with 2-chlorobenzaldehyde. The molecule has a tetrahedral structure at the P atom. The dihedral angle between the phenyl rings attached to the P atom is 80.4 (1)°. The molecules are linked together by intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactrions. The crystal studied was an inversion twin.
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.
The asymmetric unit of the title triangulo-triruthenium compound, [Ru3(C18H12Cl3P)2(CO)10]·H2O, consists of one triangulo-triruthenium complex and one disordered water solvent molecule. Two of the 3-chlorophenyl rings are disordered over two positions with refined site occupancies of 0.671 (3)/0.329 (3) and 0.628 (3)/0.372 (3). The water molecule is disordered over two positions with refined site occupancies of 0.523 (7) and 0.477 (7). Two equatorial carbonyl groups have been substituted by the two monodentate phosphine ligands, leaving one equatorial and two axial carbonyl substituents on the two Ru atoms. The remaining Ru atom carries two equatorial and two axial terminal carbonyl ligands. In the crystal structure, molecules are linked into columns along the a axis by intermolecular C—H⋯Cl and C—H⋯O hydrogen bonds. The molecular structure is stabilized by weak intramolecular C—H⋯O hydrogen bonds.
In the title compound, C22H17N3O5, synthesized via the aza-Wittig reaction of ethyl 3-(phenyliminomethyleneamino)benzofuran-2-carboxylate, benzene isocyanate and diethyl 2-aminosuccinate, the imidazo[1,2-a]benzo[4,5]furo[2,3-d]pyrimidine ring system is essentially planar (r.m.s. deviation for all 16 non-H atoms = 0.020 Å). The phenyl ring is twisted with respect to this ring system, making a dihedral angle of 54.23 (4)°. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions.
The asymmetric unit of the title compound, C18H17ClN2O2·0.5H2O, contains two organic molecules and one solvent water molecule. In each organic molecule, the cyclohexene ring adopts an envelope conformation with the C atom connecting the two methyl groups on the flap; the 4H-pyran ring is nearly planar [maximum deviation = 0.113 (3) Å in one molecule and 0.089 (3) Å in the other molecule] and is approximately perpendicular to the chlorophenyl ring [dihedral angle = 86.43 (15)° in one molecule and 89.73 (15)° in the other molecule]. Intermolecular N—H⋯N, N—H⋯O, O—H⋯O and O—H⋯Cl hydrogen bonding is present in the crystal.