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4-[(Z)-(n-Butyl-amino)(phenyl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

ABSTRACT: The title compound, C(21)H(23)N(3)O, exists in an enamine-keto form with the amino group involved in an intra-molecular N-H⋯O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6)°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 4.81 (6) and 69.81 (5)° wth the phenyl rings. In the crystal, pairs of weak C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers.

SUBMITTER: Wang HW

PROVIDER: S-EPMC3343944 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(Z)-4-[(2-Amino-4,5-dichloro-anilino)(phenyl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:The mol-ecule of the title compound, C(23)H(18)Cl(2)N(4)O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61?(19), 76.73?(14) and 52.57?(19)° with the three benzene rings. The secondary amino group is involved in an intra-molecular N-H?O hydrogen bond. In the crystal, mol-ecules are linked by pairs of N-H?O hydrogen bonds, forming inversion dimers. An offset stacking inter-action is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid-centroid distance = 3.862?(1)?Å].

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4-{(Z)-(sec-Butyl-amino)(phen-yl)methyl-ene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the title compound, C(21)H(23)N(3)O, the dihedral angles formed by the pyrazolone ring with two phenyl rings are 10.38?(8) and 76.94?(6)°. The sec-butyl-amino group is disordered over two positions, with refined site-occupancy factors of 0.730?(4) and 0.270?(4). The compound could potentially be ligand stabilized in the solid state in a keto-enamine tautomeric form. The amine functionality is involved in an intra-molecular N-H?O hydrogen bond, while weak inter-molecular C-H?O and C-H?N hydrogen bonds participate in the formation of the crystal structure.

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(Z)-4-[(2-Amino-anilino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:The mol-ecule of the title compound, C(23)H(20)N(4)O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 10.33?(11), 65.34?(11) and 63.52?(10)° with the three benzene rings. In the crystal, the mol-ecules are linked by inter-molecular N-H?N hydrogen bonds, generating chains parallel to the b axis. The secondary amino group is involved in an intra-molecular N-H?O hydrogen bond.

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(Z)-4-[(Ethyl-amino)(furan-2-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the crystal of the title compound, C(17)H(17)N(3)O(2), the mol-ecules exist in the keto-enamine form. The pyrazole ring is oriented at 10.59?(4) and 57.98?(5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30?(11)°. An intra-molecular N-H?O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into supra-molecular chains along the b axis.

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(E)-3-Amino-4-(2-phenyl-hydrazinyl-idene)-1H-pyrazol-5(4H)-one.

Project description:The mol-ecule of the title compound, C(9)H(9)N(5)O, is essentially planar (r.m.s. deviation of all atoms = 0.02?Å) except for the NH(2) H atoms. An intra-molecular hydrazinyl-idene-carbonyl N-H?O=C hydrogen bond is present. In the crystal, mol-ecules are connected via N-H?N/O hydrogen bonds, forming thick layers parallel to (100).

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(Z)-3-Methyl-1-phenyl-4-[(p-tol-yl)(p-tolyl-amino)-methyl-idene]-1H-pyrazol-5(4H)-one.

Project description:In the title mol-ecule, C(25)H(23)N(3)O(2), the pyrazole ring forms dihedral angles of 28.56?(7), 80.35?(7) and 31.99?(7)° with the phenyl ring, the p-tolyl ring and the p-tolyl-amino ring, respectively. The N-H group attached to the exocyclic C=C bond is in a syn arrangement with respect to the C=O bond of the pyrazolone group and an intra-molecular N-H?O hydrogen bond is observed. In the crystal, weak C-H?? inter-actions link mol-ecules along [100].

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Project description:In the title compound, C(23)H(19)N(3)O(2), the dihedral angles formed by the pyrazolone ring with the three benzene rings are 30.91?(6), 60.96?(4) and 57.01?(4)°. The ligand is in the enamine-keto form and its structure is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, O-H?N hydrogen bonds link mol-ecules into chains parallel to [01-1].

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(Z)-4-{1-[(2-Hy-droxy-ethyl)-amino]-ethyl-idene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the title compound C(14)H(17)N(3)O(2), the dihedral angle between the rings is 16.68 (13)°. Although the compound crystallizes in the keto form, the possibility of keto-enamine-enol-imine tautomerism is explained by a strong intra-molecular N-H⋯O hydrogen bond.

| S-EPMC3051635 | biostudies-literature

(Z)-4-[(3-Aminona-phthalen-2-yl-amino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:The mol-ecule of the title compound, C(27)H(22)N(4)O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 12.73 (11), 65.17 (6) and 49.82 (6)°, respectively, with the two benzene rings and the naphthalene ring system. In the crystal, pairs of mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intra-molecular N-H⋯O hydrogen bond.

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4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl-idene]amino}-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C(12)H(10)N(6)S, a weak intra-molecular C-H?S hydrogen bond stabilizes the mol-ecular conformation. The pyrazole and triazole rings form a dihedral angle of 17.82?(8)°. The mol-ecule adopts an E configuration with respect to the central C=N double bond. In the crystal, inter-molecular N-H?N and N-H?S hydrogen bonds link mol-ecules into chains propagating in [20[Formula: see text]].

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