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(E)-2-Hydr-oxy-6-[(4-propyl-phenyl)-iminiometh-yl]phenolate.

ABSTRACT: The title compound, C(16)H(17)NO(2), crystallizes with three crystallographically independent zwitterionic mol-ecules in the asymmetric unit which differ significantly in the orientations of the propyl side chains. The dihedral angles between the two benzene rings in the three mol-ecules are 6.17?(7), 6.75?(7) and 23.67?(7)°, respectively. In each independent mol-ecule, an intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, each independent mol-ecule exists as part of an O-H?O hydrogen-bonded centrosymmetric R(2) (2)(10) dimer.

SUBMITTER: Yaz?c? S

PROVIDER: S-EPMC2980080 | biostudies-other | 2009

REPOSITORIES: biostudies-other

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(E)-2-Hydr-oxy-6-[(4-propyl-phenyl)-iminiometh-yl]phenolate.

Yazıcı Serap S Albayrak Ciğdem C Gümrükçüoğlu Ismail I Senel Ismet I Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20091209 Pt 1

The title compound, C(16)H(17)NO(2), crystallizes with three crystallographically independent zwitterionic mol-ecules in the asymmetric unit which differ significantly in the orientations of the propyl side chains. The dihedral angles between the two benzene rings in the three mol-ecules are 6.17 (7), 6.75 (7) and 23.67 (7)°, respectively. In each independent mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, each independent mol-ecule exists as part ...[more]

PMID: 21580188

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

Project description: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.

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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.

| S-EPMC2968345 | biostudies-other

2-[(E)-(3-Carb-oxy-4-hy-droxy-phen-yl)iminiometh-yl]-4-chloro-phenolate.

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Project description:The title compound, C(18)H(20)N(2)O(3), adopts a cis conformation with respect to the C=N double bond. The crystal structure is stabilized by intra-molecular N-H⋯O and inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC2915260 | biostudies-literature

(E)-4-Bromo-2-[(2-hydroxy-phen-yl)iminiometh-yl]phenolate.

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

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.

| S-EPMC2971951 | biostudies-literature

(E)-2-[(2-Hydroxy-ethyl)iminiometh-yl]-6-methoxy-phenolate.

Project description:The title Schiff base compound, C(10)H(13)NO(3), obtained by the reaction of 2-hydr-oxy-3-methoxy-benzaldehyde and 2-amino-ethanol in methanol solution, crystallizes in a zwitterionic form, in which the mol-ecule adopts a trans configuration about the central C=N bond. An intra-molecular N-H?O hydrogen bond occurs. In the crystal structure, mol-ecules are linked into chains by inter-molecular O-H?O hydrogen bonding.

| S-EPMC2968608 | biostudies-literature

(E)-4-Hy-droxy-2-[(2-hy-droxy-phen-yl)iminiometh-yl]phenolate.

Project description:The title compound, C(13)H(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol-ecule is almost planar, the dihedral angle between the two benzene rings being 4.32?(8)°. The two hy-droxy substit-uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053?(2) and 0.0052?(2)?Å]. An intra-molecular N-H?O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol-ecules are linked through O-H?O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O-H?O hydrogen bonds in an anti-parallel manner. ?-? inter-actions are also observed, with centroid-centroid distances of 3.7115?(19) and 3.743?(2)?Å.

| S-EPMC3006709 | biostudies-literature

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