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

ABSTRACT: 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.

SUBMITTER: Ozek A

PROVIDER: S-EPMC2970131 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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

Ozek Arzu A Albayrak Ciğdem C Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20090815 Pt 9

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 π-π contact between the benzene rings [centroid-centroid distance = 3.6623 (10) Å] further stabilizes the structure. ...[more]

PMID: 21577562

Similar Datasets

(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.

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

Project description: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.

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(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.

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

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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.

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2-Chloro-12-phenyl-6,7,8,9,10,11-hexa-hydro-cyclo-octa-[b]quinoline.

Project description:In the mol-ecule of the title compound, C(21)H(20)ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak π-π inter-actions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.

| S-EPMC2961081 | biostudies-literature

Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives.

Project description:A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC50 values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.

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Crystal structures of 2,3,8,9,14,15-hexa-methyl-5,6,11,12,17,18-hexa-aza-tri-naphthyl-ene and 2,3,8,9,14,15-hexa-phenyl-5,6,11,12,17,18-hexa-za-tri-naphthyl-ene di-chloro-methane disolvate.

Project description:The crystal structures of two substituted HATN (hexa-aza-tri-naphthyl-ene) derivatives, namely 2,3,8,9,14,15-hexa-methyl- and 2,3,8,9,14,15-hexa-phenyl-5,6,11,12,17,18- hexa-zatri-naphthyl-ene (HATNMe6 and HATNPh6), are reported. Whereas the structure of the methyl-substituted derivative (HATNMe6) contains no solvent mol-ecules (C30H24N6), the hexa-phenyl-substituted structure (HATNPh6) contains two mol-ecules of di-chloro-methane (C60H36N6·2CH2Cl2). This class of planar bridging ligands is known for its electron-deficient systems and its ability to form π-π stacking inter-actions. Indeed, in both crystal structures strong π-π stacking inter-actions are observed, but with different packing features. The di-chloro-methane mol-ecules in the crystal structure of HATNPh6 are situated in the voids and are involved in C-H⋯N contacts to the nitro-gen atoms of the pyrazine units.

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N-Phenyl-cyclo-hexa-necarboxamide.

Project description:In the title compound, C(13)H(17)NO, the cyclo-hexane ring adopts a chair conformation and the amide C(=O)-N moiety is almost coplanar with the phenyl ring [C-N-C-O = 4.1?(2)°]. In the crystal, mol-ecules are linked to form a C(4) infinite [001] chain via N-H?O hydrogen bonds, unlike the cyclic motif seen in related structures.

| S-EPMC3009346 | biostudies-literature

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