In the title compound, C27H22N2O4, the two indole ring systems are approximately perpendicular to each other, with a dihedral angle of 84.5 (5)° between their planes; the benzene ring is twisted with respect to the two indole ring systems at angles of 78.5 (5) and 86.5 (3)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, weak C—H⋯O and C—H⋯N hydrogen bonds, and C—H⋯π interactions into a three-dimensional supramolecular architecture.
In the title compound, C27H20O2, the phenyl ring is oriented with respect to the naphthalene ring systems at 57.87 (6) and 85.12 (6)°. The two naphthalene ring systems make a dihedral angle of 70.10 (4)°. In the molecule, the hydroxy groups are involved in a strong intramolecular O—H⋯O hydrogen bond. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds occur. A weak C—H⋯π interaction is also observed in the crystal.
In the crystal, the molecules of the title compound, C15H10BrNO, are connected into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds. The dihedral angle between the planes of indole ring system and benzene ring is 50.13 (5)°. The indole plane is significantly less twisted from the plane of the central C—C(=O)—C bridge than the benzene plane [dihedral angles = 15.51 (3) and 40.13 (7)°, respectively]. The bond angles within the benzene ring show an approximately additive effect of the influence of both substituents.
In the title compound, C29H23ClN4O4, the quinazoline-indole system and the indolin-2-one system are each essentially planar, with maximum deviations from their mean planes of 0.150 (2) and 0.072 (2) Å, respectively. The central pyrrolidine ring adopts a twisted conformation on the C—C bond involving the spiro C atoms. Its mean plane forms dihedral angles of 83.37 (9) and 86.56 (8)°, respectively, with the indole rings of the indolin-2-one and quinazoline-indole systems. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked via C—H⋯O hydrogen bonds, forming chains propagating along .
In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C—C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thiophene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules, forming inversion dimers with an R
2(8) ring motif. The dimers are linked by further N—H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100).
The title compound, C28H28N2O, was prepared by condensation of 1,2-bimethylindole and 4-methoxybenzaldehyde. In the molecular structure, the plane of the non-fused benzene ring is twisted with respect to the planes of the two indole ring systems, exhibiting dihedral angles of 72.04 (7) and 72.24 (7)°, while the planes of the two indole ring systems are oriented at a dihedral angle of 87.05 (5)°. Neither hydrogen bonding nor π–π stacking is observed in the crystal structure.
In the title compound, C20H21N2O5PS, the indole ring is essentially planar, with a maximum deviation of −0.0083 (18) Å. The methyl C atom of the methylphosphonate group and the S atom lie 0.104 (2) and −0.2158 (6) Å, respectively, from the indole mean plane. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 82.30 (8)°. The ethyl side chains are disordered over two sets of sites, with occupancy factors of 0.737 (5)/0.263 (5) and 0.529 (11)/0.471 (11). In the crystal, molecules are linked into centrosymmetric dimers via C—H⋯O hydrogen bonds, resulting in an R
2(18) graph-set motif. The crystal structure is further stabilized by C—H⋯π interactions.
In the title compound, C17H19N5O5, obtained from the condensation reaction of 4-diethylamino-2-hydroxybenzaldehyde and 2,4-dinitrophenylhydrazine, the two benzene rings are twisted by a dihedral angle of 1.75 (12)°. The nitro groups are slightly twisted with the respect to the benzene ring to which they are attached, making dihedral angles of 8.20 (15) and 5.78 (15)°. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, molecules are linked by pairs of intermolecular N—H⋯O hydrogen bonds, forming dimers through R
2(12) rings. These dimers are further linked by C—H⋯O and C—H⋯π and weak slipped π–π interactions [centroid–centroid distance = 3.743 (2)Å]. One of the ethyl groups is disordered over two positions, with occupancy factors in the ratio 0.72:0.28.
In the title molecule, C27H32O2, the aromatic rings are in a propeller configuration. In the crystal, molecules are linked through O—H⋯O hydrogen bonds forming a two-dimensional network which develops parallel to (010). Futhermore, weak C—H⋯π interactions involving the two substituted rings build up a three-dimensional network.
In the title compound, C17H24NO2
+·Br−·H2O, the pentyl group chain in the cation extends nearly perpendicular [N—C—C—C = −64.4 (3)°] to the mean plane of the indole ring with the carboxyl end group twisted such that the dihedral angle between the mean planes of the indole and carboxy groups measures 43.2 (4)°. Both ions in the salt form intermolecular hydrogen bonds (O—H⋯Br and O—H⋯O) with the water molecule. As a result of the Br⋯H—O—H⋯Br interactions, a zigzag chain is formed in the c-axis direction. The crystal packing is influenced by the collective action of the O—H⋯O and O—H⋯Br intermolecular interactions as well as π–π stacking intermolecular interactions between adjacent benzyl rings of the indole group [centroid–centroid distance = 3.721 (13) Å] and intermolecular C—H⋯π interactions between a methyl hydrogen and the benzyl ring of the indole group. The O—H⋯Br interactions form a distorted tetrahedral array about the central Br atom. A MOPAC AM1 calculation provides support to these observations.
The title compound, C23H25BrN2O3, crystallizes with two independent molecules in the asymmetric unit (Z′ = 2) which differ in the twist of the 5-bromo-1H-indole ring with respect to the plane of the 4-methyl-1,4,5,6,7,8-hexahydroquinoline ring [dihedral angles of 78.55 (9) and 89.70 (8)° in molecules A and B, respectively]. The indole ring is planar in both molecules [maximum deviations = 0.021 (3) and −0.020 (3) Å for the N atom] while the cyclohexene ring has adopts a sofa conformation. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers with R
2(6) ring motifs. These dimers are connected by N—H⋯O hydrogen bonds, generating chains along . A C—H⋯O contact occurs between the independent molecules.
In the title compound, C30H22N2O7S2, the configuration about the propene C=C bond is E. The indole unit is essentially planar, with a maximum deviation of 0.031 (3) Å. The dihedral angle between the planes of the phenyl rings of the two phenylsulfonyl groups is 80.95 (19)°. The central prop-2-ene-1-one group is oriented at a dihedral angle of 44.26 (11)° with respect to the nitrophenyl ring and at 39.24 (8)° with respect to the indole unit. The S atoms are in a distorted tetrahedral configuration. In the crystal, molecules are linked into centrosymmetric dimers via pairs of C—H⋯O hydrogen bonds with an R
2(24) graph-set motif. The crystal structure is stabilized by further C—H⋯O interactions. Short intramolecular C—H⋯O contacts result in several S(6) rings.
In the title compound, C36H30N4O3, the quinoxaline–indene system is roughly planar, with a maximum deviation from the mean plane of 0.218 Å for the C atom shared with the central pyrrolidine ring. This latter ring forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline–indene system and the indole ring, respectively. The central pyrrolidine ring has an envelope conformation with the N atom as the flap, while the pyrrolidine and five-membered rings of the indole group adopt twisted conformation and envelope (with the C atom bearing the quinoxaline–indene system as the flap) conformations, respectively. In the crystal, molecules are linked via weak C—H⋯N hydrogen bonds, forming a chain running along .
In the title compound, C28H22O6, the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methylphenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetrasubstituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methylphenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.
The title compound, C23H18N2O4S2, contains a pyrrolo group fused onto the plane of an indole ring with phenylsulfonyl and p-toluenesulfonyl groups bonded to the indole and pyrrolo rings. The angles between the mean planes of the pyrrolo-indole ring and the phenylsulfonyl and p-toluenesulfonyl rings are 73.7 (6) and 80.6 (0)°, respectively. The dihedral angle between the mean planes of the two benzene rings is 78.7 (4)°. In the crystal, both classical N—H⋯O and non-classical C—H⋯O intermolecular hydrogen-bonding interactions are observed, as well as weak π–π interactions [centroid–centroid distances = 3.6258 (8) and 3.9298 (8) Å], which contribute to the stability of the packing.
In the title molecule, C24H17N3, the didhedral angles formed by the mean planes of the indole ring systems and the benzene ring are 86.44 (7) and 86.96 (7)°. The dihedral angle between the two indole ring systems is 72.08 (6)°. In the crystal, intermolecular bifurcated (N—H)2⋯N hydrogen bonds link molecules into sheets lying parallel to (010).
In the title compound, C17H15N3O6S, which crystallized with highly disordered methanol and/or water solvent molecules, the dihedral angle between the the indole and benzene ring systems is 5.3 (2)°, which allows for the formation of intramolecular π–π stacking interactions [centroid–centroid separations = 3.641 (3) and 3.694 (3) Å] and an approximate overall U-shape for the molecule. In the crystal, dimers linked by pairs of Ns—H⋯Oc (s = sulfonamide and c = carboxylate) hydrogen bonds generate R
2(10) loops, whereas Ni—H⋯π (i = indole) interactions lead to chains propagating in  or . Together, these lead to a three-dimensional network in which the solvent voids are present as intersecting (two-dimensional) systems of  and  channels. The title compound was found to contain a heavily disordered solvent molecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155], which revealed 877.8 Å3 of solvent-accessible volume per unit cell and 126 electron-units of scattering density or 109.7 Å3 (16 electron units) per organic molecule.. This was not included in the calculations of overall formula weight, density and absorption coefficient.
The title compound, C25H19NO was synthesized by a Pd-catalysed intramolecular Diels–Alders reaction. The dihedral angle between the two benzene rings is 82.33 (5)° and the dihedral angles between the hydronaphtho[2,3-c]furan plane and the two benzene rings are 89.50 (3) and 77.64 (2)°. The O atom is displaced by 0.5929 (3) Å from the hydronaphtho[2,3-c]furan plane.
In the title compound, C20H19NO4S, the indole ring system is planar [r.m.s. deviation = 0.023 (2) Å]. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 86.75 (7)°]. The ester group is almost planar (r.m.s. deviation = 0.030 Å) and is oriented at an angle of 62.53 (5)° with respect to the indole ring system. Molecules are linked into a two-dimensional network parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds.
In the title compound, C20H19NO5, the dihedral angle between the mean plane of the pyran ring (which has a half-chair conformation) and the benzene ring of the chromeno ring system is 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system and the isoxazole ring is 21.78 (6)°, while the isoxazole ring forms a dihedral angle of 72.60 (8)° with the attached phenyl ring. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R
2(10) ring motif. These dimers are linked via C—H⋯N hydrogen bonds, forming chains along .
In the crystal structure of the title compound, C9H8O3, essentially planar molecules [the carboxyl group makes a dihedral angle of 4.53 (7)° with the plane of the ring, while the acid group forms a dihedral angle of 3.45 (8)° to the ring] aggregate by centrosymmetric hydrogen-bond pairing of ordered carboxyl groups. This yields dimers which have two orientations in a unit cell, creating a herringbone pattern. In addition, two close C—H⋯O intermolecular contacts exist: one is between a methyl H atom and the ketone of a symmetry-related molecule and the other involves a benzene H atom and the carboxyl group O atom of another molecule. The crystal studied was a non-merohedral twin with twin law [100, 00, 0] and a domain ratio of 0.8104(14): 0.1896(14).
The asymmetric unit of the title compound, C11H12N2O4, contains two crystallographically independent molecules with similar geometries. Both molecules contain an intramolecular N—H⋯O hydrogen bond. The dihedral angles between the benzene ring and the mean plane of the cyclobutane ring are 38.29 (7) and 57.04 (8)° in the two molecules, and the nitro group is twisted slightly away from the plane of the benzene ring [dihedral angles = 9.15 (12) and 9.55 (12)° in the two molecules]. In the crystal, the independent molecules are linked into dimers by O—H⋯O hydrogen bonds between their carboxyl groups, and C—H⋯O and C—H⋯π interactions are formed between dimers.
In the title compound, C21H24N2O2, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxylate group and the benzimidazole ring system is 6.87 (5)°. A weak intramolecular C—H⋯π interaction may have some influence on the conformation of the molecule. In the crystal structure, molecules are linked into infinite chains along the b axis by weak intermolecular C—H⋯O hydrogen bonds.
In the title compound, C20H18N2O3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimethoxyphenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). Molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N—H⋯O intermolecular hydrogen bonds, which form an R
2(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.
The title compound C20H20O4S, is polymorphic. In the tetragonal form, the molecule lies on a crystallographic twofold axis, while the monoclinic form has only approximate C
2 molecular symmetry. The greatest excursion from C
2 symmetry is in the orientation of the two phenyl rings; at 100 K, one of the rings is rotated −37.2 (3)° and the other by 46.9 (3)° from their symmetric (tetragonal) positions. There are only minor differences in the three-ring nucleus; the best molecular fit of the tetragonal and monoclinic forms, both at 100 K and excluding phenyl rings and H atoms, shows an r.m.s. deviation of 0.066 Å. Both forms have the same absolute configuration.