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4-(2-Methyl-anilino)pent-3-en-2-one.

ABSTRACT: The title enamino ketone, C(12)H(15)NO, a derivative of 4-(phenyl-amino)-pent-3-en-2-one, presents a roughly planar [greatest displacement of an atom from the pentenone plane is 0.033 (2) Å] pentenone backbone, enhanced by an intra-molecular N-H⋯O hydrogen bond; the asymmetry in C-C distances in the group suggests the presence of unsaturated bonds. The overall geometry in the free ligand differs significantly from that in other reported compounds, in which it is coordinated to rhodium; this is reflected in the bond distances [the N⋯O distance is significantly increased (0.2 Å) upon coordination to the metal] and the dihedral angle between the benzene ring and the pentenone backbone [49.53 (5)°]. All of the methyl goups are rotationally disordered over two orientations of equal occupancy.

SUBMITTER: Venter GJ

PROVIDER: S-EPMC3006949 | biostudies-literature |

REPOSITORIES: biostudies-literature

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4-(2,3-Dimethyl-anilino)pent-3-en-2-one.

Project description:In the title compound, C(13)H(17)NO, the dihedral angle between the aryl ring and the amino-acryl-aldehyde mean plane [N-C=C-C=O; maximum deviation = 0.0144?(9)?Å] is 53.43?(4)°. There is an intra-molecular N-H?O hydrogen bond involving the amine and carbonyl groups. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming chains propagating along [001].

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(Z)-4-(2-Hy-droxy-anilino)pent-3-en-2-one.

Project description:In the title compound, C(11)H(13)NO(2), the dihedral angle between the planes defined by the 2-hy-droxy-phenyl-amino group and the pent-3-en-2-one mean plane [maximum deviations = 0.0275 (19) and 0.054 (2) Å, respectively] is 31.01 (10)°. There are intra-molecular bifurcated N-H⋯(O,O) hydrogen bonds involving the amine NH group and the adjacent carbonyl and hy-droxy O atoms. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains propagating along [100].

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(Z)-4-(2,5-Di-tert-butyl-anilino)pent-3-en-2-one.

Project description:In the crystal structure of the title ketoamine, C(19)H(29)NO, the bond lengths from the N atom through the alkene group to the ketone O atom show the presence of an extensively delocalized ?-system. The dihedral angle between the plane of the phenyl ring and that of the alkene component is 63.45?(7)° due to steric hindrance exerted by the tert-butyl groups. The mol-ecule has a Z-configured alkene function, which is facilitated by an intra-molecular N-H?O hydrogen bond between the amine and ketone groups. The mol-ecules are linked into extended chains, which run parallel to the [010] direction, by a very weak C-H?O inter-action between the methyl substituent of the alkene group and the ketone O atom of a neighbouring mol-ecule.

| S-EPMC3120447 | biostudies-literature

2,6-Dichloro-aniline-4-(2,6-dichloro-anilino)-pent-3-en-2-one (1/2).

Project description:The asymmetric unit of the title compound, C6H5Cl2N·2C11H11Cl2NO, is composed of one mol-ecule of an enamino-ketone [i.e. -(2,6-dichloro-phenyl-amino)-pent-3-en-2-one] and half a mol-ecule of 2,6-dichloro-aniline, the whole mol-ecule of the latter component being generated by twofold rotational symmetry. In this latter mol-ecule, there are two intra-molecular N-H?Cl contacts. In the enamino-ketone mol-ecule, there is an N-H?O hydrogen bond of moderate strength, and the dihedral angle between the benzene ring and penta-none fragment [C-C(-N)=C-C(=O)-C; planar within 0.005?(1)?Å] is 81.85?(7)°. In the crystal, two mol-ecules of the enamino-ketone are bridged by a mol-ecule of 2,6-dichloro-aniline via N-H?O hydrogen bonds of moderate strength. There are also ?-? inter-actions present, involving the benzene rings of inversion-related enamino-ketone mol-ecules [centroid-centroid distance = 3.724?(4)?Å].

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4-(2,6-Dibromo-4-fluoro-anilino)pent-3-en-2-one.

Project description:The title enamino-ketone, C(11)H(10)Br(2)FNO, has a roughly planar pentenone chain; the maximum displacement of an atom from the pentenone plane is 0.071?(4)?Å. The dihedral angle between the benzene ring and the pentenone unit is 77.2?(1)°. Inter-molecular C-H?Br and C-H?O inter-actions, as well as an intra-molecular N-H?O inter-action, are observed. In both methyl groups, each H atom is disordered equally over two sites.

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4-[(4-Methyl-phen-yl)amino]-pent-3-en-2-one.

Project description:The title enamino-ketone, C(12)H(15)NO, is a derivative of 4-(phenyl-amino)-pent-3-en-2-one with an approximately planar pentenone backbone, the greatest displacement from the plane being 0.042 (1) Å; the asymmetry in C-C distances in the group suggests the presence of unsaturated bonds. The dihedral angle between the benzene ring and the pentenone plane is 29.90 (4)°. In the crystal, an intra-molecular N-H⋯O inter-action and an inter-molecular C-H⋯O hydrogen bond are observed.

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Dichlorido[(Z)-4-(2,6-diisopropyl-anilino)pent-3-en-2-one]dimethyl-tin(IV).

Project description:In the crystal structure of the title compound, [Sn(CH(3))(2)Cl(2)(C(17)H(25)NO)], the Sn atom adopts a trigonal-bipyramidal geometry with the O and one Cl atom in axial positions. A weak intra-molecular N-H?O hydrogen bond occurs. The crystal structure displays weak inter-molecular C-H?Cl inter-actions.

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4-Hy-droxy-2-methyl-3,4-diphenyl-cyclo-pent-2-en-1-one.

Project description:The asymmetric unit of title compound, C(18)H(16)O(2), contains two mol-ecules with slightly different conformations. In the first mol-ecule, the two phenyl rings make dihedral angles of 84.98?(11)° and the five-membered ring makes dihedral angles of 84.80?(12) and 73.00?(12)° with the phenyl rings; the corresponding angles for the second mol-ecule are 86.74?(11), 81.20?(13) and 71.36?(12)°. O-H?O hydrogen bonds between the hy-droxy and carbonyl groups are a feature of the crystal packing, which results in chains extending parallel to [100]. Weak C-H?O and C-H?? inter-actions are also observed.

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4-(2-Chloro-phenyl-amino)-pent-3-en-2-one.

Project description:In the title compound, C(11)H(12)ClNO, intra-molecular N-H?O hydrogen bonding is present. The dihedral angle between the benzene ring and the pentenone unit is 46.52?(5)°. In the crystal, C-H?O inter-actions between hydrogen atoms of the aryl moiety and two separate oxygen atoms occur, leading to a three-dimensional network.

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(Z)-4-(2-Naphthyl-amino)-pent-3-en-2-one.

Project description:The title compound, C(15)H(15)NO, which was synthesized under solvent-free conditions by the reaction of acetoacetone and 2-naphthyl-amine, adopts a Z conformation about the C=C bond. The enamine-ketone fragment is approximately planar [maximum deviation = 0.026 (3) Å] and forms a dihedral angle of 39.78 (3)° with the naphthalene ring system. An intra-molecular N-H⋯O hydrogen bond is observed.

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