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6-[(5-tert-Butyl-2-hydroxy-anilino)methyl-ene]cyclo-hexa-2,4-dienone.

ABSTRACT: In the title compound, C(17)H(19)NO(2), the dihedral angle between the two aromatic rings is 26.02 (5)°. One phenol O atom is deprotonated and the N atom of the azomethine unit carries the H atom, forming an intra-molecular hydrogen bond. The packing is stabilized by an O-H⋯O hydrogen bond.

SUBMITTER: Bohme U

PROVIDER: S-EPMC2914976 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(Z)-6-[(5-Chloro-2-hydroxy-anilino)-methyl-ene]-4-methoxy-cyclo-hexa-2,4-dienone 0.25-hydrate.

Project description:The title compound, C(14)H(12)ClNO(3)·0.25H(2)O, exists in the keto-amine form, and the aromatic rings are oriented at a dihedral angle of 7.24 (7)°. Bifurcated intra-molecular N-H⋯(O,O) hydrogen bonds result in the formation of planar six- and five-membered rings. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains. π-π contacts between benzene rings [centroid-centroid distance = 3.5065 (9) Å] may further stabilize the structure. There also exists a weak C-H⋯π inter-action.

| S-EPMC2977782 | biostudies-literature

6-[(2,4-Di-methyl-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dienone.

Project description:In the title compound, C15H15NO2, the dihedral angle between the aromatic rings is 5.86 (6)°, and an intra-molecular N-H⋯O hydrogen bond generates an S(6) motif, which helps to stabilize the enamine-keto tautomer. An intra-molecular O-H⋯O hydrogen bond also occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A C-H⋯O inter-action links the dimers into [010] chains and aromatic π-π stacking [centroid-centroid separation = 3.6131 (9) Å] also occurs.

| S-EPMC3685031 | biostudies-literature

(Z)-6-{2-[(E)-2,4-Dihydroxy-benzyl-ideneamino]phenyl-amino-methyl-ene}-3-hydroxy-cyclo-hexa-2,4-dienone toluene solvate.

Project description:The bis-Schiff base title compound, C(20)H(16)N(2)O(4)·C(7)H(8), crystallized as a toluene solvate. In the solid state, it is present as its prototropic tautomer formed by transfer of one of the ortho-hydroxyl H atoms. The proton transfer is accompanied by a shift of electron pairs, as is evident from the observed C-O and C-N bond distances of 1.305?(2) and 1.315?(2)?Å, which are largely consistent with C=O and C-N distances. The actual mol-ecule present in the solid state is thus the charge-neutral ?-keto amine, with a small contribution of its zwitterionic valence tautomer via partial delocalization of electron pairs along the N-C-C-C-O atom chain. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 51.99?(8) and 12.95?(9)°. Intra-molecular O-H?N and N-H?O hydrogen bonds generate S(6) ring motifs, whereas intra-molecular N-H?N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O-H?O hydrogen bonds and weak C-H?O inter-actions link the mol-ecules into one-dimensional zigzag chains along the b axis; these chains are further stacked by O-H?O and weak C-H?O inter-actions along the c axis, forming two-dimensional extended networks parallel to the bc plane. In addition, the crystal structure is further stabilized by weak C-H?? and ?-? inter-actions.

| S-EPMC2960708 | biostudies-literature

(Z)-6-[(5-Chloro-2-hydroxy-phenyl)-aminomethyl-ene]-2-ethoxy-cyclo-hexa-2,4-dienone.

Project description:The title compound, C(15)H(14)ClNO(3), exists as the keto-amine form in the crystal and two intra-molecular N-H?O hydrogen bonds are observed. The aromatic rings are oriented at a dihedral angle of 5.85?(8)°. In the crystal structure, inter-molecular O-H?O and C-H?O hydrogen bonds link the mol-ecules into chains. A ?-? contact between the benzene rings [centroid-centroid distance = 3.6623?(10)?Å] further stabilizes the structure.

| S-EPMC2970131 | biostudies-literature

3-Diethyl-amino-6-[(Z)-(4-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dienone.

Project description:In the mol-ecule of the title compound, C(17)H(20)N(2)O(2), the aromatic rings are oriented at a dihedral angle of 6.23 (22)°. Intra-molecular N-H⋯O hydrogen bonding involving the amine H atom and the carbonyl O atom affects the conformation of the mol-ecule. One of the ethyl arms is disordered over two conformations, with occupancies of 0.59 (2) and 0.41 (2). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions.

| S-EPMC3011427 | biostudies-literature

tert-Butyl 6-methyl-2-oxo-4-[4-(trifluoro-meth-oxy)anilino]cyclo-hex-3-ene-1-carboxyl-ate.

Project description:In the title compound, C(19)H(22)F(3)NO(4), the dihedral angle between the benzene ring and the conjugated part of the enaminone ring is 42.5?(1)°. The ester substituent makes a dihedral angle of 81.3?(2)° with this latter moiety. The crystal structure is held together by strong N-H?O and weak C-H?O inter-molecular inter-actions. The enaminone ring is disordered over two orientations with relative occupancies of 0.794?(4) and 0.206?(4).

| S-EPMC3011753 | biostudies-literature

6-(2-Hydroxy-anilinomethyl-ene)-4-nitro-cyclo-hexa-2,4-dien-1-one.

Project description:The molecule of the title compound, C(13)H(10)N(2)O(4), is nearly planar with a dihedral angle between the two aromatic rings of 2.24 (9)°. The NH group forms an intramolecular hydrogen bond with the carbonyl O atom. The mol-ecules form dimers about inversion centers in the crystal structure via inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC2915241 | biostudies-literature

2-[(4-tert-Butyl-anilino)(phen-yl)meth-yl]cyclo-hexa-none.

Project description:In the mol-ecule of the title compound, C(23)H(29)NO, the cyclo-hexa-none ring has been distorted from the standard chair conformation by the ketone group such that part of the ring is almost flat. The remaining [(4-tert-butyl-anilino)(phen-yl)meth-yl] portion of the mol-ecule is in an equatorial position on the cyclo-hexa-none ring. The dihedral angle between the two benzene rings is 81.52?(8)°. In the crystal packing, mol-ecules are linked by N-H?O hydrogen bonds into infinite one-dimensional chains along the a axis and these chains are stacked down the c axis. The crystal structure is further stabilized by weak C-H?O and C-H?? inter-actions.

| S-EPMC2968565 | biostudies-other

tert-Butyl 4-(4-chloro-anilino)-6-methyl-2-oxocyclo-hex-3-ene-carboxyl-ate.

Project description:In the title compound, C(18)H(22)ClNO(3), the dihedral angle between the benzene ring and the conjugated part of the enaminone ring is 55.19?(9)°. The ester substituent makes a dihedral angle of 81.0?(2)° with this latter moiety. The crystal structure features N-H?O and weak C-H?O inter-molecular inter-actions.

| S-EPMC3050184 | biostudies-literature

2,4-Di-tert-butyl-6-[1-(3,5-di-tert-butyl-2-hydroxy-phen-yl)eth-yl]phenyl 4-methyl-benzene-sulfonate.

Project description:The title compound, C(37)H(52)O(4)S, was obtained by the reaction of 6,6'-(ethane-1,1-di-yl)bis-(2,4-di-tert-butyl-phenol) and 4-methyl-benzene-1-sulfonyl chloride. The mol-ecular conformation is stabilized by an intra-molecular O-H?O hydrogen bond. Two of the tert-butyl groups are disordered over two sets of sites with occupancies 0.530?(15)/0.470?(15) and 0.615?(11)/0.385?(11).

| S-EPMC2968069 | biostudies-literature

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