In the title compound, C17H10F6N4O2S, an intramolecular N—H⋯N hydrogen bonds forms an S(5) ring whereas N—H⋯O and C—H⋯S interactions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the molecules are dimerized due to N—H⋯O interactions. π–π interactions are present between the benzene rings [centroid–centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoromethyl)phenyl ring [centroids–centroid distance = 3.7827 (16) Å]. One of the trifluoromethoxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoromethyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).
The crystal structure of the title compound, C16H11F3N4O2S, is stabilized in the form of polymeric chains by N—H⋯O interactions. In the molecular structure, two S(5) ring motifs are formed by intramolecular N—H⋯N and N—H⋯O hydrogen bonding and two S(6) rings are present due to N—H⋯O and C—H⋯S interactions. π–π interactions are present with distances of 3.2735 (17), 3.563 (2) and 3.664 (4)/3.688 (3) Å between the centroids of the heterocyclic rings, between the centroids of the heterocyclic ring and trifluoromethoxy-substituted phenyl ring, and between the centroids of the trifluoromethoxy-substituted phenyl rings, respectively. The trifluoromethoxyphenyl group is disordered over two sites with an occupancy ratio of 0.642 (10):0.358 (10).
In the title compound, C17H15F3N4O2, the dihedral angle between the trifluoromethoxy-substituted benzene ring and the pyrimidinone ring is 45.1 (5)°, while that between the fused benzene ring and the pyrimidinone ring is 0.67 (1)°. Part of one of the benzene rings and its trifluoromethoxy substituent are disordered over two positions of approximately equal occupancy (0.51:0.49). Intermolecular N—H⋯O and N—H⋯N hydrogen bonds contribute to the stability of the crystal structure. A weak intramolecular C—H⋯F contact is also found. In addition, π–π stacking interactions, with centroid–centroid distances in the range 3.673 (6)–3.780 (8) Å, and weak C—H⋯π interactions are also observed.
The title compound crystallized with two independent molecules in the asymmetric unit. In the crystal, they are linked to one another, forming chains enclosing (10) and (12) ring motifs.
The title compound, C22H17NO4, crystallizes with two independent molecules (A and B) in the asymmetric unit. Each molecule exists as an E isomer with C—C=C—C torsion angles of −175.69 (17) and −178.41 (17)° in A and B, respectively. In molecule A, the planes of the terminal benzene rings are twisted by an angle of 26.67 (10)°, while the biphenyl unit is non-planar, the dihedral angle between the rings being 30.81 (10)°. The dihedral angle between the nitrophenyl ring and the inner phenyl ring is 6.50 (9)°. The corresponding values in molecule B are 60.61 (9), 31.07 (8) and 31.05 (9)°. In the crystal, molecules are arranged in a head-to-head manner, with the 3-nitrophenyl groups nearly parallel to one another. The A and B molecules are linked to one another via C—H⋯O hydrogen bonds, forming chains lying parallel to (-320) and enclosing R
2(10) and R
2(12) ring motifs. The methoxy group in both molecules is positionally disordered with a refined occupancy ratio of 0.979 (4):0.021 (4) for molecule A and 0.55 (4):0.45 (4) for molecule B.
crystal structure; chalcones; C—H⋯O hydrogen bonding; main-residue disorder
The asymmetric unit of the title compound, C16H12ClF3N2O3S·H2O, contains two crystallographically independent organic molecules and two water molecules. The organic species are linked by an intermolecular O—H⋯O hydrogen bond, while the water molecules are connected to them through intermolecular O—H⋯N hydrogen bonds. The thiophene and phenyl rings are oriented at dihedral angles of 62.35 (4) in the first independent molecule and 60.74 (5)° in the second, while the pyrimidine rings adopt twisted conformations in both molecules. Intramolecular N—H⋯F interactions result in the formation of two five-membered rings having envelope conformations. In the crystal structure, further intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into chains.
The asymmetric unit of the title compound, C17H12ClF3N4O2S, contains two molecules, which differ in their planarity and hydrogen bonding. In one molecule, the 2-oxoindolin (C8/N/O A), thiosemicarbazide (N3/C/S B) and 5-chloro-2-methylphenyl (C7/Cl C) units are planar with r.m.s. deviations of 0.0110, 0.0173 and 0.0259 Å, respectively. The dihedral angles A/B, B/C and A/C are 1.74 (15), 40.70 (13) and 41.00 (11)°, respectively. In the other molecule the deviations are 0.0455, 0.0007 and 0.0143 Å, respectively, and the dihedral angles are 5.01 (14), 4.53 (16) and 3.38 (13)°, respectively. In both molecules, intramolecular N—H⋯N and N—H⋯O hydrogen bonds form S(5) and S(6) ring motifs, respectively and C—H⋯S interactions occur. In one of the molecules, an intramolecular C—H⋯F interaction is also present. In the crystal, the molecules are linked by N—H⋯O, C—H⋯F, C—H⋯O and N—H⋯S hydrogen bonding, forming a polymeric network.
The asymmetric unit of the crystal structure of the title compound, C23H19F3N2O, contains two independent molecules. In the two molecules the planar benzimidazole ring systems are oriented with respect to the phenyl/trifluoromethylbenzene rings at dihedral angles of 9.62 (6)/78.63 (7) and 2.53 (8)/83.83 (9)°. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules into R
2(6) dimers. The molecules are elongated along  and stacked along the b axis.
In the title compound, C14H9F3N2O, the best planes of the benzimidazole group and benzene ring form a dihedral angle of 26.68 (3)°. In the crystal, N—H⋯N hydrogen bonds link the molecules into infinite chains parallel to the c axis. Stacking interactions between the benzimidazole groups [centroid–centroid distance = 3.594 (5) Å] assemble the molecules into layers parallel to (100). The trifluoromethyl group is disordered over three sets of sites with site-occupancy factors of 0.787 (4), 0.107 (7) and 0.106 (7).
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 title compound, C26H21F6NO5, the dihedral angle between the cyclopropane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phenoxybenzyl group is 82.7 (1)°. In the crystal structure, weak intermolecular C—H⋯π interactions and C—H⋯F hydrogen bonds contribute to the stabilization of the packing.
The title compound, C15H11F3INO2, adopts the enol–imine tautomeric form. The molecule displays an E conformation with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 12.4 (2)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates an S(6) ring motif. The trifluoromethoxyphenyl group is disordered over two sites with an occupancy ratio of 0.621 (6):0.379 (6). The crystal structure features C—H⋯π interactions.
In the title compound, C18H12F3NO2, the planes of the benzene ring and the naphthalene system form a dihedral angle of 47.21 (3)°. The hydroxy group is involved in an intramolecular O—H⋯N hydrogen bond. In the crystal, weak C—H⋯O and C—H⋯F interactions link the molecules related by translations along the c and a axes, respectively, into sheets.
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
The title compound, C14H9ClF3NO2, crystallizes in a phenol–imine tautomeric form, with a strong intramolecular O—H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 47.62 (9)°. In the crystal, molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds, and weak C—H⋯π interactions involving both benzene rings are also observed.
In the title compound, C16H11F3N2O2, the carboxamide group connecting the two aromatic rings is in a syn-periplanar configuration; the molecule is non-planar; the dihedral angle between the two aromatic rings is 13.95 (18)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds.
The title compound [systematic name: 5-(trifluoromethoxy)-1H-indole-2,3-dione], C9H4F3NO3, crystallized with two molecules in the asymmetric unit. Intermolecular N—H⋯O hydrogen bonds link the molecules to form layers parallel to the ab plane. In addition, π–π stacking interactions are observed with a centroid–centroid distance of 3.721 (1) Å. The near planarity of the two isatin ring systems is illustrated by by the maximum deviations of 0.023 (1) and 0.025 (1) Å for the N atom in each case.
In the title solvate, C24H24N2O4·CH3NO2, the benzene ring of the 2-ethoxy-6-methylphenol substituent is approximately perpendicular to the nearly planar benzimidazole ring [maximum deviation = 0.021 (2) Å], making a dihedral angle of 84.32 (7)°. The benzene ring of the 2-ethoxyphenol group is somewhat inclined to the benzimidazole ring plane by 28.03 (5)°. The dihedral angle between the benzene rings is 82.20 (9)°. The compound reveals strong intramolecular O—H⋯N and O—H⋯O hydrogen bonds, forming six- and five-membered rings, respectively. In the crystal, molecules are connected by bifurcated O—H⋯(O,O) hydrogen bonds, forming chains along the b axis.
In the title compound, C25H17ClF3N3O2S, the five-membered 1,3-thiazolidine ring adopts a twist conformation. The three F atoms of the CF3 group are disordered over two sets of sites with refined occupancies of 0.542 (18) and 0.458 (18). In the nine-membered 1H-indoline ring system, the 1H-pyrrole ring forms a dihedral angle of 4.7 (2)° with the benzene ring, while it is twisted at an angle of 46.5 (2)° with respect to the attached phenyl ring. The dihedral angle between the phenyl and trifluoromethyl-substituted benzene rings is 56.0 (2)°. In the crystal, N—H⋯O hydrogen bonds connect the molecules into a three-dimensional network. In addition, weak C—H⋯O hydrogen bonds and weak C—H⋯π interactions are observed.
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.
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.
rac-Benzyl 3-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate was separated by chiral chromatography, and one of the enantiomers ([α]22
D = +10°) was hydrogenated in the presence of Pd/C in methanol, producing octahydro-3H-pyrrolo[3,4-c]pyridin-3-one. The latter was reacted with (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride [(R)-(−)-Mosher acid chloride], giving rise to the title compound, C17H19F3N2O3·H2O. The present structure established the absolute configuration of the pyrrolopiperidine fragment based on the known configuration of the (R)-Mosher acid chloride. The piperidine ring has a somewhat distorted chair conformation and is cis-fused with the five-membered envelope-shaped ring; the plane of the exocyclic amide bond is approximately orthogonal to the plane of the phenyl ring, making a dihedral angle of 82.31 (3)°. The water molecule acts as an acceptor to the proton of the amino group in an N—H⋯O interaction, and as a double proton donor in O—H⋯O hydrogen bonds, generating infinite bands along the a axis.
The title molecule, C17H14F3NO4, consists of two nearly planar fragments, viz. the 2-benzyloxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-methoxyprop2-enoic (r.m.s. deviation 0.004 Å) units, which form a dihedral angle of 84.19 (7)°. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules into dimers that are further connected by C—H⋯O and C—H⋯F interactions into (001) layers. In addition, π–π stacking interactions are observed within a layer between the pyridine and benzene rings [centroid–centroid distance = 3.768 (2) Å]. The F atoms of the trifluoromethyl group are disordered over two sets of sites in a 0.53 (4):0.47 (4) ratio.
The title compound, C18H11BrF3NO2, crystallizes in the phenol–imine tautomeric form, with a strong intramolecular O—H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 28.54 (10)°.
The title compound, C14H9F4NO2, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state. The H atom is located on the hydroxy O atom rather than on the N atom. This H atom is involved in a strong intramolecular O—H⋯N hydrogen bond. The molecule is almost planar, the angle between the benzene rings being 2.14 (13)°.
In the title compound, C23H20NO2
−, the acridine ring system is oriented at a dihedral angle of 23.1 (1)° with respect to the benzene ring and the carboxyl group is twisted at an angle of 74.1 (1)° relative to the acridine skeleton. In the crystal, adjacent cations are linked through C—H⋯π interactions and neighboring cations and anions via weak C—H⋯O hydrogen bonds. The mean planes of adjacent acridine units are either parallel or inclined at angles of 15.0 (1), 26.9 (1) and 48.1 (1)° in the crystal structure.