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(E)-1-[(2,4,6-Tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.

ABSTRACT: The title azo mol-ecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intra-molecular O-H?N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80?(16)°. In the crystal, mol-ecules are stacked in columns along the a axis by ?-? inter-actions [centroid-centroid distances = 3.815?(3) and 3.990?(3)?Å].

SUBMITTER: Chetioui S

PROVIDER: S-EPMC3793751 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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(E)-1-[(2,4,6-Tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.

Chetioui Souheyla S Boudraa Issam I Bouacida Sofiane S Bouchoul Abdelkader A Bouaoud Salah Eddine SE

Acta crystallographica. Section E, Structure reports online 20130713 Pt 8

The title azo mol-ecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, mol-ecules are stacked in columns along the a axis by π-π inter-actions [centroid-centroid distances = 3.815 (3) and 3.990 (3) Å]. ...[more]

PMID: 24109338

Similar Datasets

Crystal structure of 5-[2-(2,4,6-tri-bromo-phen-yl)diazen-yl]tropolone.

Project description:The title compound {systematic name: 2-hy-droxy-5-[2-(2,4,6-tri-bromo-phen-yl)diazen-1-yl]cyclo-hepta-2,4,6-trien-1-one}, C13H7Br3N2O2, is essentially planar, with an r.m.s. deviation of 0.054?Å. The mol-ecular structure is fixed in the azo tautomer by intra-molecular C-H?N inter-actions, with O-H?O hydrogen bonds creating linked dimers. Charge-transfer inter-actions are observed, with the segregated stacks linked by Br?Br inter-actions.

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Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.

Project description:In the copper(II) complex, bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naph-thalen-2-olato}copper(II), [Cu(C16H8Br3N2O)2], (I), the metal cation is coord-inated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intra-molecular Cu⋯Br inter-action [3.134 (2) Å], while in the other ligand, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}nickel(II), [Ni(C16H8Br3N2O)2], (II), and bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}palladium(II), [Pd(C16H8Br3N2O)2], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tri-bromo-benzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), mol-ecules are linked by C-H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (011). In the crystals of (II) and (III), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9-18]. The formula mass and unit-cell characteristics of the disordered solvent mol-ecules were not taken into account during refinement.

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Crystal structure, characterization and Hirshfeld analysis of bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}copper(II) dimethyl sulfoxide monosolvate.

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