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(E)-2-{[1-Carb-oxy-2-(1H-indol-3-yl)ethyl-iminio]meth-yl}-6-hy-droxy-phenolate.

ABSTRACT: In the zwitterionic title compound, C(18)H(16)N(2)O(4), the dihedral angle between the planes of the benzene and indole rings is 26.38?(10)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through N-H?O, O-H?O and C-H?O hydrogen bonds into infinite chains propagating in [010].

SUBMITTER: Ba-Salamah SA

PROVIDER: S-EPMC3200592 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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(E)-2-{[1-Carb-oxy-2-(1H-indol-3-yl)ethyl-iminio]meth-yl}-6-hy-droxy-phenolate.

Ba-Salamah Salah Ahmed SA Eltayeb Naser Eltaher NE Teoh Siang Guan SG Lo Kong Mun KM

Acta crystallographica. Section E, Structure reports online 20110827 Pt 9

In the zwitterionic title compound, C(18)H(16)N(2)O(4), the dihedral angle between the planes of the benzene and indole rings is 26.38 (10)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into infinite chains propagating in [010]. ...[more]

PMID: 22058986

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Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyl-iminio]eth-yl}phenolate-κO)zinc(II)-2-{1-[2-(1H-indol-3-yl)ethyl-iminio]eth-yl}phenolate (1/2).

Project description:In the mononuclear complex mol-ecule of the title compond, [ZnCl(2)(C(18)H(18)N(2)O)(2)]·2C(18)H(18)N(2)O, the Zn atom, which lies on a twofold rotation axis, is coordinated by phenolate O atoms in a tetra-hedral coordination geometry. The coordinated Schiff base uses its indole NH donor site to form a hydrogen bond to the negatively charged phenolate O atom of the uncoordinated zwitterionic Schiff base. There is an intra-molecular N-H⋯O hydrogen bond in the coordinated and uncoordinated Schiff bases. The indole NH site of the uncoordinated Schiff base does not engage in a hydrogen-bond inter-action. The CH(2)-CH(2) group in the uncoordinated Schiff base is disordered equally over two positions.

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Project description:The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C-O(-) bond [1.296 (2) Å] is shorter than a normal Csp(2)-O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The mol-ecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, strong O-H⋯O hydrogen bonds link the mol-ecules into double-stranded chains along the b-axis direction. Within the chains there are π-π interactions involving the benzene rings of adjacent molecules [centroid-centroid distance = 3.669 (1) Å]. The chains are linked via C-H⋯O hydrogen bonds, forming R(2) (1)(6), R(2) (1)(7) and R(2) (2)(10) ring motifs.

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Project description:The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihy-droxy-benzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethyl-pyrimidin-2-amine group. Intra-molecular O-H⋯O and N-H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from mol-ecules joined end-to-end by N-H⋯O and O-H⋯N hydrogen bonds; these feature R(2) (3)(6) loops. The polymeric chains are linked by C-H⋯O inter-actions and there are π-π inter-actions between the pyrimidine rings with a centroid-centroid distance of 3.446 (2) Å.

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Project description:The title Schiff base, C(17)H(15)N(3)O(3), exists in the zwitterionic form with the phenol H atom transferred to the imine group. Adjacent zwitterions are linked into a linear chain running along the a axis by an indole-hydr-oxy N-H⋯O hydrogen bond [3.100 (2) Å].

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Project description:Each of the two independent mol-ecules of the title comound, C(14)H(20)N(2)O(3), exists in the zwitterionic form as the imino N atoms are protonated. The =N-H unit forms an intra-molecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N-H⋯O bond, the latter resulting in inversion dimers.

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2-{[2-(Piperazin-4-ium-1-yl)ethyl-iminio]meth-yl}phenolate 0.06-chloride 0.94-perchlorate.

Project description:The structure of the title salt, C(13)H(20)N(3)O(+)·0.94ClO(4) (-)·0.06Cl(-), contains a zwitterionic Schiff base with a net positive charge and a perchlorate anion having substitutional disorder with Cl. In the cation, the azomethine N atom is protonated and donates hydrogen bonds to the phenolate O atom and to the tertiary N atom of the piperazine ring. In the crystal, two Schiff base mol-ecules are linked about a center of inversion by a pair of N-H?O hydrogen bonds. The resulting dimers are N-H?O and C-H?O hydrogen bonded to the perchlorate anions, forming a three-dimensional structure. The network is further consolidated by C-H?? inter-actions.

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(E)-4-Hy-droxy-2-{[(2-phenyl-eth-yl)iminium-yl]meth-yl}phenolate.

Project description:The title Schiff base compound, C(15)H(15)NO(2), crystallized as the iminium-phenolate zwitterion. The H atom is localized on the imine N atom, forming a strong intra-molecular hydrogen bond with the phenolate O atom, and giving rise to an S(6) ring motif. The mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating along [010]. There are also C-H⋯O inter-actions present.

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Project description:The title Schiff base compound, C(14)H(10)ClNO(4), has been synthesized by the reaction of 5-amino-2-hy-droxy-benzoic acid and 5-chloro-2-hy-droxy-benzaldehyde. The mol-ecule is a zwitterion in the crystal, with the phenolic hy-droxy group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C=N double bond. The dihedral angle between the two benzene rings is 3.83 (7)°. Intra-molecular N-H⋯O and O-H⋯O hydrogen bonding generates S(6) ring motifs. In the crystal, mol-ecules are connected by inter-molecular O-H⋯O and C-H⋯Cl hydrogen bonds, forming a supra-molecular chain.

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A new polymorph of 1-({[1,3-dihy-droxy-2-(hy-droxy-meth-yl)propan-2-yl]iminio}meth-yl)naphthalen-2-olate.

Project description:The title compound, C15H17NO4, containing two mol-ecules in the asymmetric unit is a polymorph of the crystal structure published by Martínez et al. [(2011). Eur. J. Org. Chem. pp. 3137-3145] which at 120 K is monoclinic with one mol-ecule in the asymmetric unit. Both mol-ecules in the title compound are in the trans form. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds connect mol-ecules, forming a two-dimensional network parallel to (001).

| S-EPMC4555412 | biostudies-literature

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