The title compound, C11H8N2O3S, is roughly planar; the dihedral angle between the planes of the thiophene and benzene rings is 8.38 (10)°. An intramolecular O—H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, molecules are linked into centrosymmetric dimers by pairs of O—H⋯O hydrogen bonds with an R
2(22) graph-set motif. Aromatic π–π stacking interactions [centroid–centroid separations = 3.653 (3) and 3.852 (3) Å] link the dimers into a three-dimensional network.
crystal structure; Schiff bases; phenol; hydrogen bonding; π–π stacking
The title molecule, C12H10N2O3S, is nonplanar with an interplanar angle of 33.44 (7)° between the benzene and thiophene rings. In the crystal there exist only weak intermolecular C—H⋯O interactions, π–π interactions between the benzene rings [centroid–centroid distance = 3.7465 (14) Å] and X—Y⋯π interactions to the thiophene and benzene rings [N⋯centroid distances = 3.718 (3) and 3.355 (3) Å, respectively]. Intermolecular C—H⋯O interactions link the molecules into chains parallel to the a axis.
In the title compound, C12H10N2O3S, the dihedral angle between the benzene and thiophene rings is 43.17 (4)°. The crystal structure is devoid of any hydrogen-bonding interactions. However, π–π interactions between the benzene and thiophene rings [distance between ring centroids = 3.6850 (11) Å] stack the molecules along the a axis. The absolute structure could not be determined as the crystal studied was a racemic twin with a BASF parameter of 0.31 (6).
In the title Schiff-base type compound, C18H13N3O5, the central furan ring makes dihedral angles of 12.80 (7) and 51.43 (4)° with the terminal benzene rings. The dihedral angle between the benzene rings is 45.43 (3)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into layers parallel to (010). In addition, there are π–π stacking interactions within the layer [centroid–centroid distance = 3.584 (1) Å] and between the layers [centroid–centroid distance 3.751 (1) Å].
The title compound, C23H16N2OS, is not planar, the phenyl ring of the benzoyl group making a dihedral of 77.61 (7)° with the benzothiophene system ring. The benzothiophene system and the remaining phenyl ring make an angle of 12.71 (13)°. The conformation around the imine functions is E for the C=N bond towards the benzothiophene system and Z for the C=N bond towards the benzoyl group. The packing of the molecules shows C—H⋯π interactions. A weak intramolecular C—H⋯N bond also occurs.
In the crystal structure of the title compound, C12H10N2O2S, the benzene and the 2-nitrothiophene rings make a dihedral angle of 7.47 (12)°. The dihedral angle between the nitro group and the attached ring is 1.9 (6)°.
The title Schiff base, C17H19IN2O, is not planar, displaying a dihedral angle of 34.9 (2)° between the two aromatic rings. The molecular conformation allows the formation of a strong intramolecular O—H⋯N hydrogen bond with graph-set motif S(6) between the hydroxy group and the imine N atom.
The title Schiff base, C19H24N2O3, exists in the crystal structure in the phenol–imine tautomeric form with an intramolecular O—H⋯N hydrogen bond. The planes of the aromatic rings form a dihedral angle of 36.8 (8)°. The crystal packing is characterized by C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distance = 3.478 (4)Å].
In the title compound, C6H6N2O3·C8H8O4, the 2-amino-4-nitrophenol (ANP) and 1-(2,4,6-trihydroxyphenyl)ethanone (THA) molecules are both nearly planar, with r.m.s. deviations of 0.0630 and 0.0313 Å, respectively. The angle between the least-squares planes of THA and ANP is 48.99 (2)°. In THA, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds lead to the formation of a three-dimensional network. There are also intermolecular π–π interactions between the benzene rings of ANP–ANP and of THA–THA molecules, with centroid–centroid distances of 3.5313 (14) and 3.8440 (16) Å, respectively. Weak C—O⋯π and N—O⋯π interactions also occur.
In the title compound, C17H15NS, the benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 61.99 (7)°. An intermolecular C—H⋯π interaction contributes to the stability of the crystal structure.
The dihedral angle between the benzene and thiophene rings in the title compound, C12H10N2O3S, is 27.94 (13)°. An intermolecular C—H⋯π interaction contributes to the stability of the crystal structure.
In the title conpound, C16H12N2O2S, the 1-benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 53.36 (6)°. The molecular conformation features a short C—H⋯N contact. There are no significant intermolecular contacts.
In the title compound, C13H12N2O2S, the dihedral angle between the benzene and thiophene rings is 36.72 (8)°. An intermolecular C—H⋯π interaction contributes to the stability of the crystal structure.
The molecule of the title compound, C23H17NO2, a Schiff base derived from 2-hydroxy-1-naphthaldehyde, crystallizes in the keto–amine tautomeric form. The dihedral angle between the aniline and hydroxybenzene rings is 77.41 (17)°, whereas the planes of the naphthaldehyde and fused aniline benzene rings are nearly coplanar, making a dihedral angle of 8.29 (15)°. Intramolecular N—H⋯O hydrogen bonding, a characteristic hydrogen bond for Schiff bases, helps to stabilize the molecular structure. Weak intermolecular C—H⋯π interactions are present in the crystal structure.
The title compound, C16H17NO, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state. The molecule is almost planar, with a dihedral angle of 4.61 (4)° between the aromatic rings. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond which generates a six membered ring.
The molecule of the title compound, C13H17N3O4, exists as a zwitterion, with the H atom of the phenol group being transferred to the imine N atom. The C=O, CAr—CAr and C—N bond lengths are in agreement with the oxocyclohexadienide–iminium zwitterionic form. A strong intramolecular N+—H⋯O hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. In the crystal, molecules are linked into centrosymmetric dimers by intermolecular N—H⋯O hydrogen bonds. In addition, C—H⋯O hydrogen bonds and very weak C—H⋯π interactions are observed.
X-ray analysis reveals that the title Schiff base compound, C17H19NO3, possesses both OH and NH tautomeric character in its molecular structure. The occupancies of the enol and keto tautomers are 0.62 (3) and 0.38 (3), respectively. The presence of the minor keto form could not be confirmed from the IR spectrum. The molecule is approximately planar, the dihedral angle between the planes of the two aromatic rings being 6.97 (8)°. The molecular structure of the major component is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates an S(6) ring motif (N—H⋯O hydrogen bond in the minor component).
The title compound, C15H11Cl2NO2, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state, being stabilized by a strong intramolecular O—H⋯N hydrogen bond. The molecule is almost planar (r.m.s. deviation for all non-H atoms = 0.049 Å), displaying a dihedral angle of 3.1 (3)° between the planes of the two aromatic rings.
The title compound, C13H10ClNO2, exists in the phenol–imine form in the crystal, and the aromatic rings are oriented at a dihedral angle of 2.82 (9)°. An intramolecular O—H⋯N hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains.
In the molecule of the title compound, C23H17N3O2, the methoxyphenyl ring is oriented at dihedral angles of 13.34 (12) and 88.83 (12)° with respect to the methylphenyl and phthalonitrile rings, respectively; the dihedral angle between methylphenyl and phthalonitrile rings is 89.67 (10)°. In the crystal structure, weak intermolecular C—H⋯N interactions link molecules into chains. A weak C—H⋯π interaction is also found..
In the title compound, C21H12ClN3O, the phenoxy ring makes dihedral angles of 51.42 (5) and 65.01 (6)°, respectively, with the chlorophenyl and phthalonitrile rings. In the crystal structure, the molecules are interlinked through weak C—H⋯N and C—H⋯π contacts, and π–π stacking interactions via crystallographic inversion centres form a three-dimensional network. The distance between the centroids of the phthalonitrile rings is 3.9104 (11)Å, with a slippage between the rings of 1.626 Å and a perpendicular distance between the rings of 3.556 Å.
There are two independent molecules in the asymmetric unit of the title compound, C15H14BrNO3, with very similar geometrical parameters. Each molecule adopts the phenol–imine tautomeric form, with strong intramolecular O—H⋯N hydrogen bonds. The two molecules are non-planar, the dihedral angles between the two aromatic rings being are 24.6 (2) and 30.30 (13)°.
The title compound, C14H11Cl2NO, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state. There are two molecules in the asymmetric unit. Head-to-tail π–π interactions [centroid-to-centroid distances of 3.682 (2), 3.708 (2), 3.904 (2) and 3.910 (2) Å] between adjacent molecules produce two symmetry-independent infinite chains running along the b axis.
The title Schiff base compound, C14H12N2O4, is in an intermediate state between NH and OH tautomers. Apart from the intramolecular O—H⋯N hydrogen bond, there are intermolecular C—H⋯O hydrogen bonds, generating centrosymmetric R
2(18) and R
The molecule of the title compound, C14H12ClNO, adopts the enol–imine tautomeric form, with an intramolecular O—H⋯N hydrogen bond. In the molecule, the two benzene rings are twisted with respect to each other by 30.6 (2)°. The crystal structure is stabilized by intermolecular C—H⋯π interactions.