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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.

Project description:The title mol-ecule, C(13)H(9)N(3)O(6), consists of a 2-hydr-oxy-5-nitro-phenyl-iminio group and a 4-nitro-phenolate group bonded to a methyl-ene C atom with both of the planar six-membered rings nearly in the plane of the mol-ecule [dihedral angle = 1.3?(4)°]. Each of the nitro O atoms is twisted slightly out of the plane of the mol-ecule. The amine group forms an intra-molecular hydrogen bond with both nearby O atoms, each of which has partial occupancy of attached H atoms [0.36?(3) and 0.64?(3)]. An extended ?-delocalization throughout the entire mol-ecule exists producing a zwitterionic effect in this region of the mol-ecule. The shortened phenolate C-O bond [1.2749?(19)°], in concert with the slightly longer phenol C-O bond [1.3316?(19)?Å], provides evidence for this effect. The crystal packing is influenced by extensive strong inter-molecular O-H?O hydrogen bonding between the depicted phenolate and hydr-oxy O atoms and their respective H atoms within the ?-delocalized region of the mol-ecule. As a result, mol-ecules are linked into an infinite polymeric chain diagonally along the [110] plane of the unit cell in an alternate inverted pattern. A MOPAC AM1 calculation provides support for these observations.

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Dimethyl [hydr-oxy(2-nitro-phen-yl)meth-yl]phospho-nate.

Project description:In the title compound, C(9)H(12)NO(6)P, intra-molecular C-H?O hydrogen bonds form five- and six-membered rings. In the crystal, inversion dimers lined by pairs of C-H?O hydrogen bonds occur with ring motifs R(2) (2)(10). The O atom of the hydr-oxy group behaves as an accepter and the benzene ring as donor. Adjacent dimers are connected through O-H?O links.

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Project description:The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29?(9)°. An intra-molecular N-H?O hydrogen bond formed between the iminium NH(+) and the phenolate O(-) atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O-H?O hydrogen bonds into chains along [101] and these chains are further connected through C-H?Br inter-actions into a two-dimensional network perpendicular to (101). C?C [3.572?(3)-3.592?(3)?Å] and C?Br [3.5633?(19)-3.7339?(18)?Å] short contacts are observed. The crystal studied was a twin with twin law 00, 00, 001 with a domain ratio of 0.09919?(2):0.90081?(2).

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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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Project description:The crystal structure of title compound, [Yb(NO(3))(3)(C(15)H(15)NO(2))(2)]·H(2)O, contains two Schiff base 2-[(4-methyl-phen-yl)imino-meth-yl]-6-methoxy-phenol (HL) ligands, three independent nitrate ions that chelate to the ytterbium(III) ion in an O,O'-bidentate manner and an uncoordinated water mol-ecule. The coordination number of the Yb(III) ion is eight. The HL ligands chelate with a strong Yb-O(phenolate) bond and a weak Yb-O(meth-oxy) contact. The latter augments the coordination polyhedron to give a YbO(10) bicapped square antiprism. Classical inter-molecular O-H?O and N-H?O hydrogen bonds as well as weak C-H?O contacts contribute to the stability of the structure.

| S-EPMC2971141 | biostudies-literature

Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO,O'}tris-(thio-cyanato-κN)lanthanum(III).

Project description:In the title compound, [La(NCS)(3)(C(15)H(15)NO(2))(3)], the metal centre is nine-coordinated by six O atoms from three zwitterionic Schiff base 2-meth-oxy-6-[(4-methyl-phen-yl)iminio-meth-yl]phenolate (L) ligands and three terminal N atoms of the thio-cyanate ions in a monocapped square-anti-prismatic environment. The L ligands chelate the La(III) ion with strong La-O(deprotonated phenolic) bonds [2.435 (3)-2.464 (3) Å] and significantly longer La-O(meth-oxy) bonds [2.801 (3)-2.831 (3) Å]. The La-N bond lengths range from 2.541 (4) to 2.605 (4) Å.

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