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1-{(E)-[(2-Fluoro-5-nitro-phen-yl)imino]-meth-yl}naphthalen-2-ol.

ABSTRACT: The title mol-ecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond forming an S(6) ring motif. The H atom of the intra-molecular hydrogen bond was found to be disordered over two sites and thus both the hy-droxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hy-droxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hy-droxy form. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to (101). π-π stacking inter-actions [centroid-centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.

SUBMITTER: Kennedy AR

PROVIDER: S-EPMC3684934 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-1-[(3-Iodo-phen-yl)imino-meth-yl]naphthalen-2-ol.

Project description:In the title mol-ecule, C(17)H(12)INO, the dihedral angle between the naphthaldeyde plane and the 3-iodo-aniline plane is20.07?(13)°. It exists in the solid state as an enol-imine tautomer with a strong intra-molecular O-H?N hydrogen bond.

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(E)-1-[(2-Chloro-4-nitro-phenyl-imino)-meth-yl]naphthalen-2-ol.

Project description:In the title compound, C(17)H(11)ClN(2)O(3), an intra-molecular O-H⋯N hydrogen bond influences the mol-ecular conformation; the naphthol system and the substituted benzene ring form a dihedral angle of 3.5 (1)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains in the [010] direction The crystal packing exhibits π-π inter-actions between the aromatic rings from the neighbouring mol-ecules, with a centroid-centroid distance of 3.566 (7) Å.

| S-EPMC3151923 | biostudies-literature

1-{(E)-[4-Bromo-2-(trifluoro-meth-oxy)phen-yl]imino-meth-yl}naphthalen-2-ol.

Project description:The title compound, C18H11BrF3NO2, crystallizes in the phenol-imine tautomeric form, with a strong intra-molecular O-H?N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 28.54?(10)°.

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1-[(3-Methyl-piperidin-1-yl)(3-nitro-phen-yl)meth-yl]naphthalen-2-ol.

Project description:The title compound, C(23)H(24)N(2)O(3), was synthesized from naphthalen-2-ol, 3-nitro-benzaldehyde and 3-methyl-piperidine. The dihedral angles between the naphthalene system and the nitro-benzene and methyl-piperidine rings are 78.53?(13) and 64.14?(15)°, respectively. The mol-ecular conformation is stabilized by a strong intra-molecular O-H?N hydrogen bond.

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Crystal structure of (E)-1-{[(3,5-di-methyl-phen-yl)imino]-meth-yl}naphthalen-2-ol.

Project description:The title compound, C19H17NO, has an E conformation about the N=C bond. The mol-ecule is relatively planar, with the benzene ring and naphthalene ring plane being inclined to one another by 4.28 (10)°. There is an intra-molecular O-H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains propagating along [100]. Within the chains there are π-π inter-actions involving the benzene ring and the naphthalene ring system of an adjacent mol-ecule [inter-centroid distance = 3.6405 (14) Å].

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Crystal structure of 1-{(E)-[(3,4-di-chloro-phen-yl)imino]-meth-yl}naphthalen-2-ol.

Project description:In the title compound, C17H11Cl2NO, the dihedral angle between the planes of the naphthalene ring system and the benzene ring is 28.88 (11)°. The main twist in the mol-ecule occurs about the N-Cb (b = benzene ring) bond, as indicated by the C=N-Cb-Cb torsion angle of 31.0 (4)°. An intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of very weak C-H⋯O inter-actions generate R 2 (2)(16) loops.

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1-[(Dimethyl-amino)(phen-yl)meth-yl]naphthalen-2-ol.

Project description:In the title compound, C(19)H(19)NO, the dihedral angle between the naphthyl ring system and the phenyl ring is 79.83?(6)°. An intra-molecular O-H?N hydrogen bond, together with van der Waals inter-actions, stabilizes the mol-ecular conformation.

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1-[(Butyl-amino)(phen-yl)meth-yl]naphthalen-2-ol.

Project description:In the title compound, C(21)H(23)NO, obtained via a one-pot synthesis, an intra-molecular O-H?N hydrogen bond stabilizes the mol-ecular conformation. The dihedral angle between the fused ring system and the phenyl ring is 78.27?(5)°. The crystal packing is characterized by helical chains of mol-ecules linked by C-H?O hydrogen bonds.

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(E)-1-[(3-Bromo-phen-yl)imino-meth-yl]naphthalen-2-ol.

Project description:The title compound, C(17)H(12)BrNO, exists in an enol-imine form and the mol-ecular structure features an intra-molecular O-H?N hydrogen bond. The dihedral angle between the benzene ring and the naphthalene ring system is 17.27?(15)°.

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1-[(4-Bromo-phen-yl)(morpholin-4-yl)meth-yl]naphthalen-2-ol.

Project description:The title compound, C(21)H(20)BrNO(2), was obtained from a condensation reaction of 4-bromo-benzaldehyde, 2-naphthol and morpholine. The mol-ecular conformation is stabilized by an intra-molecular O-H?N hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72?(8)°. In addition to the intra-molecular hydrogen bond, the O-H groups of centrosymmetrically related mol-ecules form short inter-molecular H?O contacts of 2.59?Å. These mol-ecules are also linked by pairs of C-H?O inter-actions, generating an R(2) (2)(14) motif.

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