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Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy-droxy-4-methyl-anilino)-methyl-idene]-4-methyl-cyclo-hexa-2,4-dien-1-one.

ABSTRACT: The title compound, C₁₅H₁₅NO₂, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra-molecular N-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers with an R ² ₂(18) ring motif. The dimers are linked by very weak π-π inter-actions, forming layers parallel to (01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter-actions.

SUBMITTER: Kansiz S

PROVIDER: S-EPMC6658948 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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 ?-? stacking [centroid-centroid separation = 3.6131?(9)?Å] also occurs.

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Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

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Project description:The title compound, C14H12N2O4, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming dimers with an R 2 2(18) ring motif. The dimers are linked by pairs of C-H⋯O contacts with an R 2 2(10) ring motif, forming ribbons extended along the [20] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) inter-actions.

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Crystal structure and Hirshfeld surface analysis of a Schiff base: (<i>Z</i>)-6-[(5-chloro-2-meth-oxy-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dien-1-one.

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Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-5-methyl-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Project description:In the title Schiff base compound, C21H19NO3, the conformation about the C=C bond is Z. The N-H group and carbonyl O atom form an intra-molecular N-H?O hydrogen bond with an S(6) ring motif. The benz-yloxy ring and the 2-hy-droxy-5-methyl-phenyl ring are inclined to the central six-membered ring by 13.68?(9) and 9.13?(8)°, respectively, and to one another by 21.95?(9)°. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds, forming helical chains along [010].

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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?? inter-actions.

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Project description:In the title compound, C(16)H(10)Br(2)N(2)O·H(2)O, bifurcated intra-molecular N-H?(N,O) hydrogen bonding defines the essential planarity of the main mol-ecule: the dihedral angle between the quinoline and benzene rings is 7.53?(8)°. Inter-molecular O-H?O and weak C-H?O hydrogen bonds consolidate the crystal packing, which exhibits ?-? inter-actions with a distance of 3.588?(1)?Å between the centroids of the aromatic rings and short Br?Br contacts of 3.5757?(6)?Å.

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3-[1-(2-Hy-droxy-anilino)ethyl-idene]-3H-chromen-2,4-dione.

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