In the title compound, C18H17ClN2O, the quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.04 Å with a maximum deviation from the mean plane of 0.026 (4) Å for the C atom bonded to the –CH2– group. The methoxy-substituted benzene ring forms a dihedral angle of 70.22 (4)° with this ring system. The crystal structure can be described as zigzag layers in which the quinoline ring systems are parallel to (011) and molecules are connected via intermolecular N—H⋯N hydrogen bonds, forming chains along . The crystal studied was an inversion twin with a 0.86 (5):0.14 (5) domain ratio.
In three potentially anticonvulsant compounds, of which two are isoindoline derivatives and one an isoquinoline derivative, the central moiety is planar. In the crystals of all three compounds, there are C—H⋯O hydrogen bonds present linking the molecules into two-dimensional slabs for the isoindoline derivatives, and into a three-dimensional framework for the isoquinoline derivative.
The title compounds, C9H7NO3, (1), C10H7NO5, (2), and C14H9NO5, (3), are three potentially anticonvulsant compounds. Compounds (1) and (2) are isoindoline derivatives and (3) is an isoquinoline derivative. Compounds (2) and (3) crystallize with two independent molecules (A and B) in their asymmetric units. In all three cases, the isoindoline and benzoisoquinoline moieties are planar [r.m.s. deviations are 0.021 Å for (1), 0.04 and 0.018 Å for (2), and 0.033 and 0.041 Å for (3)]. The substituents attached to the N atom are almost perpendicular to the mean planes of the heterocycles, with dihedral angles of 89.7 (3)° for the N—O—Cmethyl group in (1), 71.01 (4) and 80.00 (4)° for the N—O—C(=O)O—Cmethyl groups in (2), and 75.62 (14) and 74.13 (4)° for the same groups in (3). In the crystal of (1), there are unusual intermolecular C=O⋯C contacts of 2.794 (1) and 2.873 (1) Å present in molecules A and B, respectively. There are also C—H⋯O hydrogen bonds and π–π interactions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001). In the crystal of (2), the A and B molecules are linked by C—H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π–π interactions [the most significant centroid–centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure. In the crystal of (3), the A and B molecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π–π interactions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].
crystal structure; anticonvulsant; isoindoline; isoquinoline; indoline
The title compound, C15H15NO3, adopts the enol–imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intramolecular O—H⋯N hydrogen bond. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into sheets parallel to (010). These sheets are interconnected by weak C—H⋯π interactions.
The title compound, C13H14ClNO3, crystallizes with Z′ = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent molecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two molecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two molecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent molecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π–π stacking interactions between them [centroid–centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along  are linked by a further π–π stacking interaction [centroid–centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to . However, there are no C—H⋯N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C—H⋯π hydrogen bonds; hence there are no direction-specific interactions between adjacent π-stacked chains.
crystal structure; quinolone; pseudosymmetry; twinning; π–π stacking interactions
In the title compound, C36H29ClN4O, the dihydropyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018 Å) are oriented at a dihedral angle of 71.43 (4)°. One of the quinoline rings makes a dihedral angle of 65.40 (7)° with the phenyl substituent. In the crystal, molecules are linked into chains along the b axis by intermolecular C—H⋯N hydrogen bonds. In addition, C—H⋯π and π–π [centroid–centroid distance = 3.7325 (8) Å] interactions are observed.
The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(trifluoromethyl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hydroxy H atom acts as a double proton donor in an intramolecular hydrogen bond to the 5-position methoxy O atom and in an intermolecular contact to the 2-oxo group, generating a chain along  in the crystal structure.
The asymmetric unit of the title compound, C22H26N4O2S, contains two crystallographically independent molecules (A and B). The isobutyl unit of molecule B is disordered over two orientations with refined occupancies of 0.785 (6) and 0.215 (6). In each molecule, intramolecular C—H⋯S hydrogen bonds generate S(6) ring motifs. The essentially planar 1,2,4-triazole rings [r.m.s. deviations of 0.004 (2) and 0.011 (2) Å, in A and B respectively] form dihedral angles of 85.86 (12), 8.38 (10)°, respectively, with the isobutyl-substituted phenyl ring and the 2-methoxyphenol substituent in molecule A [89.26 (13) and 2.46 (10)°, respectively, in B]. In the crystal structure, intermolecular N—H⋯N and N—H⋯S hydrogen bonds link neighbouring molecules, generating R
2(7) ring motifs. These molecules are further interconnected into extended chains along  by intermolecular O—H⋯O hydrogen bonds. The crystal structure is further stabilized by π–π [centroid-centroid distance = 3.6299 (13) Å] and C—H⋯π interactions. A short O⋯O contact of 2.781 (2) Å is also observed.
In the title hydrate, C19H15N3O3·H2O, the three aromatic groups in the quinoline derivative are close to coplanar: the central oxadiazole fragment makes dihedral angles of 15.7 (2)° with the benzene ring and 5.30 (14)° with the quinoline ring system. In the crystal, the organic molecules are connected with water molecules by pairs of O—H⋯N hydrogen bonds involving the quinoline and oxadiazole N atoms. The molecules form stacks along the a axis, neighboring molecules within each stack being related by inversion and the shortest distance between the centroids of the oxadiazole and pyridine rings being 3.500 (2) Å. Molecules from neighboring stacks are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional structure.
The title compound, C10H8O4, is one of the coumarins existing in Morinda citrifolia L (Noni). The chromenone ring system is approximately planar with a maximum deviation of 0.0208 (14) Å. The methoxy group does not deviate from this plane [C—O—C—C torsion angle = −1.5 (3)°], indicating that the whole molecule is almost planar. In the crystal packing, intermolecular O—H⋯O hydrogen bonds link the molecules into chains. These are further connected by C—H⋯O hydrogen bonds.
The title compound, C22H26O9, crystallizes with two independent molecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intramolecular O—H⋯O hydrogen bond occurs in each molecule. Intermolecular C—H⋯O hydrogen bonds stabilize the crystal structure.
In the title solvated compound, C28H19N2O4·C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C—H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C—H⋯O hydrogen bonds, C—H⋯π interactions and aromatic π–π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.
crystal structure; β-lactam ring; 1H-benzo[de]isoquinoline-1,3(2H)-dione group; disorder; azetidin-2-ones
In the title compound, the pyran and pyrone rings adopt slightly distorted half-chair and envelope conformations, respectively. In the crystal, C—H⋯O and π–π interactions connect the molecules, forming double layers that stack along the c-axis direction.
In the title compound, C30H28N2O6, the pyran ring adopts a slightly distorted half-chair conformation and the pyrone ring adopts an envelope conformation, with the C atom bearing the carboxylate group as the flap. The pyrazole ring [maximum deviation = 0.002 (2) Å] forms a dihedral angle of 13.2 (1)° with the attached benzene ring. The near-planar atoms of the pyran ring and the pyrazole ring are close to coplanar, the dihedral angles between their mean planes being 6.4 (1)°. The dihedral angle between the pyrone ring and the benzene ring of the chromene unit is 10.7 (1)°. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, C—H⋯O interactions generate supramolecular chains propagating in  and these are connected into double layers that stack along the c-axis direction by weak π–π interactions between pyrazole rings [centroid–centroid distance = 3.801 (1) Å].
crystal structure; conformation; crystal packing; chromene
In the crystal structure of (I), the molecules are linked into chains by N—H⋯O hydrogen bonds with (5) ring motifs. After the N-methylation of structure (I), no hydrogen-bonding interactions were observed for structure (II).
The title compound, C19H17N3O3S (I), was prepared by a [3 + 2]cycloaddition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methylation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzothiophene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205 (14) in (I) and 0.016 (2) Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzothiophene ring systems. The trimethoxy phenyl rings make dihedral angles with the benzothiophene rings of 38.48 (4) in (I) and 60.43 (5)° in (II). In the crystal of (I), the molecules are linked into chains by N—H⋯O hydrogen bonds with R
1(5) ring motifs. After the N-methylation of structure (I), no hydrogen-bonding interactions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzothiophene ring system [occupancy ratio 0.9363 (14):0.0637 (14)].
combretastatin A-4 analog; anti-cancer agent; triazole ring; hydrogen bonding; crystal structure
In the title compound, C33H34N6O6, the dihydrobenzimidazol-2-one ring system is essentially planar (r.m.s. deviation = 0.021 Å). The cyclohexane ring adopts a chair conformation. In the 5-(biphenyl-2-yl)-2H-tetrazole fragment, the tetrazole ring is twisted away from the attached benzene ring by 35.73 (11)° and the two benzene rings form a dihedral angle of 68.00 (9)°. An intramolecular C—H⋯O interaction is observed. In the crystal, the molecules are linked into a zigzag chain running along the b axis by intermolecular N—H⋯O hydrogen bonds.
The title compound, C26H23F3N4O, crystallizes with two symmetry-independent molecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the methoxyphenyl ring. The –CF3 group of molecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, methoxyphenyl and trifluoromethylphenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in molecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in molecule B. An intramolecular N—H⋯N hydrogen bond occurs in each molecule. In the crystal, two crystallographically independent molecules associate into a dimer via a pair of N—H⋯N hydrogen bonds, with a resulting R
2(12) ring motif and π–π stacking interactions [centroid–centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A molecules, there are intermolecular C—H⋯O hydrogen bonds between an aryl C atom of methoxyphenyl ring and a methoxy O atom of an adjacent molecule. A similar interaction is lacking in the B molecules.
The crystal packing of the title compound features O—H⋯O hydrogen bonds, which form one-dimensional chains of molecules further linked via π–π interactions.
In the title compound, C20H17NO5, the dihedral angle between the mean plane of the dihydroquinoline ring system (r.m.s. deviation = 0.003 Å) and the benzene ring is 1.83 (11)°. The almost planar conformation is a consequence of an intramolecular O—H⋯O hydrogen bond and the E configuration about the central C=C bond. In the crystal structure, O—H⋯O hydrogen bonds generate chains of molecules along the [10-1] direction. These chains are linked via π–π interactions [inter-centroid distances are in the range 3.6410 (16)–3.8663 (17) Å].
crystal structure; 4-hydroxy-1,2-dihydroquinolin-2(1H)-one; α,β-unsaturated ketones; hydrogen bonding; π–π interactions
The crystal structure of the title compound, [Mn(C14H13NO2)2(H2O)3](NO3)2, is comprised of two Schiff base 2-methoxy-6-(N-phenylcarboximidoyl)phenol (HL) ligands and three coordinated water molecules. The MnII ion lies on a twofold axis that bisects one water O atom. The coordination sphere of the five-coordinate Mn atom is completed by the two monodentate HL ligands and three coordinated water molecules binding through their O atoms, affording a distorted tetragonal–pyramidal geometry. In the phenolate ligands, the hydroxy H atom transfers to the imine N atom. This H atom is also involved in an intramolecular N—H⋯O hydrogen bond that imposes a nearly planar conformation on each ligand, with dihedral angles of 2.78 (3) and 2.43 (5)° between the aromatic rings of each ligand. In the crystal, molecules are linked by intermolecular O—H⋯O hydrogen bonds.
The title compound, C19H16N2O4, is of interest as a precursor to biologically active substituted quinolines and related compounds. The dihedral angle between the naphthalene ring system and the benzene ring is 81.9 (1)°. The crystal structure is stabilized by N—H⋯O intermolecular hydrogen bonds, linking the molecules into pairs around a center of symmetry. The crystal structure is further stabilized by intermolecular O—H⋯O hydrogen bonds, which link the molecules into chains running along a axis. An intramolecular C—H⋯O short contact is also present.
In the title resonance conformer, C15H12ClNO4, the central C–N bond [1.297 (2) Å] has considerable double-bond character and the N–O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the molecule, with both benzene rings twisted out of the central C–C–N–C plane [the dihedral angle formed between the rings = 81.99 (8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of the benzene ring to which it is connected [C—C—O—C torsion angle = −78.42 (17)°]. The most prominent intermolecular interactions involve the carboxylic acid the N+–O− residues with the O—H⋯O hydrogen bonds leading to helical supramolecular chains along the b axis. These chains are connected into layers via C–H⋯Ocarbonyl interactions and the layers are consolidated into the crystal structure by C–H⋯Cl contacts.
In the title compound, C23H17Cl2F3N4O3, the triazole ring makes dihedral angles of 50.27 (6) and 82.78 (7)° with the quinoline ring system and the dichloro-substituted benzene ring. The dihedral angle between the quinoline and dichloro-substituted benzene rings is 38.17 (4)°. In the crystal, molecules are linked via C—H⋯N, C—H⋯F and C—H⋯O hydrogen bonds into a three-dimensional network. The crystal is further consolidated by C—H⋯π contacts to the triazole ring and inversion-related π–π interactions between the benzene and pyridine rings of quinoline systems [centroid–centroid distance = 3.7037 (7) 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, C28H20Cl2N2O2, the 2-chloroquinoline and 6-chloroquinoline ring systems are twisted slightly, making a dihedral angle of 4.05 (3)°. The dihedral angle between the 2-quinoline ring system and the phenyl ring attached to it is 74.43 (5)°. In the crystal structure, a pair of intermolecular C—H⋯O hydrogen bonds connect the molecules, forming centrosymmetric dimers with R
2(16) motifs. The dimers are further consolidated by a C—H⋯π interaction and a π–π stacking interaction with a centroid–centroid distance of 3.6562 (10) Å.
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, C21H19NO6, the isoindole ring system is essentially planar [maximum deviation = 0.019 (2) Å for the N atom] and is oriented at a dihedral angle of 51.3 (1)° with respect to the benzene ring. The two methoxy groups are almost coplanar with the attached benzene ring [C—O—C—C = 3.7 (4) and 4.3 (4)°]. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(9) ring motif. In the crystal, molecules are linked through bifurcated C—H⋯(O,O) hydrogen bonds having R
2(5) ring motifs, forming chains along the b-axis direction. The crystal packing is further stabilzed by π–π interactions [centriod–centroid distance = 3.463 (1) Å].
Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-benzyloxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-14,16-dien-10-yl benzoate
In the title compound, the ring conformations of the tetracycle are twist, chair, half-chair and chair–boat forms. In the crystal, intermolecular C—H⋯O and C—H⋯π interactions link molecules to construct a three-dimensional architecture.
In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by −0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat–chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C—H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.
crystal structure; hydrogen bonds; taxane skeleton; paclitaxel; hydrogen bonding; C—H⋯π interactions