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(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]phenolate.

ABSTRACT: In the title mol-ecule, C(13)H(10)N(2)O(4), the dihedral angle between the mean planes of the benzene and phenolate rings is 21.6?(4)°. The nitro O atoms are twisted slightly out of the plane of the ring to which the nitro group is attached [dihedral angle 8.4?(3)°]. The amine group forms an intra-molecular hydrogen bond with both nearby O atoms. An extended ? delocalization throughout the entire mol-ecule exists producing a zwitterionic effect in this region of the mol-ecule. The shortened C-O bond [1.2997?(15)?Å] in concert with the slightly longer C-OH bond [1.3310?(16)?Å] provide evidence for this effect. The crystal packing is influenced by strong inter-molecular O-H?O hydrogen bonding. As a result, mol-ecules are linked into an infinite zigzag chain running along the b axis. A MOPAC PM3 calculation provides support to these observations.

SUBMITTER: Hijji YM

PROVIDER: S-EPMC2968543 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]phenolate.

Hijji Yousef M YM Barare Belygona B Butcher Ray J RJ Jasinski Jerry P JP

Acta crystallographica. Section E, Structure reports online 20090211 Pt 3

In the title mol-ecule, C(13)H(10)N(2)O(4), the dihedral angle between the mean planes of the benzene and phenolate rings is 21.6 (4)°. The nitro O atoms are twisted slightly out of the plane of the ring to which the nitro group is attached [dihedral angle 8.4 (3)°]. The amine group forms an intra-molecular hydrogen bond with both nearby O atoms. An extended π delocalization throughout the entire mol-ecule exists producing a zwitterionic effect in this region of the mol-ecule. The shortened C-O ...[more]

PMID: 21582157

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(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]-4-nitro-phenolate.

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Project description:The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth-oxy group is almost coplanar [C-O-C-C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules are linked into zigzag chains along [010] by O-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

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Project description:The metal center in the structure of the title compound, [Eu(NCS)(3)(C(15)H(15)NO(2))(3)], is coordinated by three Schiff base 2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate (L) ligands and three independent thio-cyanate ions. In the crystal structure, the acidic H atom is located on the Schiff base N atom and hydrogen bonded to the phenolate O atom. The coordination environment of the Eu(III) ion is nine-coordinate by three chelating methoxy-phenolate pairs of O atoms and three N-atom terminals of the thio-cyanate ions. The compound is isostructural with the Ce(III) analogue [Liu et al. (2009 ?). Acta Cryst. E65, m650].

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