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2-[2-(1H-indol-3-yl)ethyl-iminiomethyl]-4-nitro-phenolate.

ABSTRACT: 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].

SUBMITTER: Ali HM

PROVIDER: S-EPMC2961249 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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2-[2-(1H-indol-3-yl)ethyl-iminiomethyl]-4-nitro-phenolate.

Ali Hapipah M HM Mohamed Mustafa M I MI Rizal M Razali MR Ng Seik Weng SW

Acta crystallographica. Section E, Structure reports online 20080426 Pt 5

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]. ...[more]

PMID: 21202395

Similar Datasets

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.

| S-EPMC2961161 | biostudies-literature

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

Project description: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].

| S-EPMC3200592 | biostudies-literature

2-{(E)-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vin-yl}-6-hydroxy-meth-yl-4-nitro-phenolate dihydrate.

Project description:The title merocyanine-type mol-ecule, C(21)H(22)N(2)O(5)·2H(2)O, crystallizes in a zwitterionic form and has an E configuration at the styryl C=C bond. The styryl part of the mol-ecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1)°. The 1.274 (3) Å C-O bond length in the phenolate fragment is the longest among similar mol-ecules. Hydrogen bonds between solvent water mol-ecules, two hydroxyl groups and the phenolate O atom dictate the packing arrangement of mol-ecules in the crystal and join the mol-ecules into a two-dimensional polymeric network which propagates parallel to (001). Four water mol-ecules and four hydr-oxy groups form a centrosymmetric homodromic cyclic motif of O-H⋯O hydrogen bonds. Another cyclic centrosymmetric motif is generated by four water mol-ecules and two phenolate O atoms.

| S-EPMC2977230 | biostudies-literature

Ethyl N-(3-cyano-1H-indol-2-yl)form-imidate.

Project description:In the title compound, C12H11N3O, the C=N imino bond is in an E conformation. In the crystal, adjacent mol-ecules are linked by N-H⋯Ncyano hydrogen bonds, forming a chain running along [110].

| S-EPMC3885025 | biostudies-literature

3-(2-Acetamido-eth-yl)-1H-indol-5-yl 4-nitro-phenyl carbonate.

Project description:In the title mol-ecule, C(19)H(17)N(3)O(6), the indole ring system is essentially planar (r.m.s. deviation = 0.009 Å) and forms a dihedral angle of 31.96 (9)° with the nitro-substituted benzene ring. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers which are connected by further N-H⋯O hydrogen bonds into a two-dimensional network parallel to (102).

| S-EPMC3470262 | biostudies-literature

2-[(E)-2-(4-Methyl-benzene-sulfonamido)ethyl-iminiometh-yl]-4-nitro-phenolate.

Project description:The mol-ecule of the title compound, C(16)H(17)N(3)O(5)S, crystallizes in a zwitterionic form, with a strong intra-molecular N-H⋯O hydrogen bond. The dihedral angle between the two benzene rings is 7.06 (9)°. In the crystal, mol-ecules are linked into chains along the c axis by inter-molecular N-H⋯O hydrogen bonds.

| S-EPMC2969864 | biostudies-literature

3-(1H-Imidazol-1-yl)propanaminium 2-carb-oxy-4,6-di-nitro-phenolate.

Project description:In the title salt, C6H12N3 (+)·C7H3N2O7 (-), the imidazole ring is planar, with a maximum deviation of 0.0013 (14) Å for the N attached to the propanaminium group. In the anion, a single intra-molecular O-H⋯O hydrogen bond is observed. The mean planes of the nitro groups in the anion are twisted from the benzene ring mean plane making dihedral angles of 24.7 (9) and 3.9 (6)°. In the crystal, the ammonium H atoms form N-H⋯N and N-H⋯O hydrogen bonds, resulting in an infinite chain along [111]. In addition to the classical hydrogen bonds, weak C-H⋯O and π-π [centroid-centroid distance = 3.7124 (9) Å] inter-actions are also observed, which lead to the formation a three-dimensional supramolecular structure that links the chains into layers along the bc plane.

| S-EPMC3998440 | biostudies-literature

Ethyl 2-(5-meth-oxy-2-methyl-1H-indol-3-yl)acetate.

Project description:In the title compound, C14H17NO3, the nine-membered 1H-indole ring system is essentially planar [maximum deviation = 0.019 (1) Å]. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains along [001]. These chains are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a two-dimensional network lying parallel to the ac plane.

| S-EPMC3793745 | biostudies-literature

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-nitro-benzoate.

Project description:In the title compound, C(13)H(12)N(4)O(6), the mean plane through the nitro-benzene forms a dihedral angle of 37.38 (15)° with the plane through the imidazole ring. The crystal packing is stabilized by weak inter-molecular C-H⋯O and C-H⋯N inter-actions together with π-π stacking inter-actions between nitro-benzene rings [centroid-centroid distance = 3.788 (3) Å] and between imidazole rings [centroid-centroid distance = 3.590 (2) Å].

| S-EPMC2983685 | biostudies-literature

1-{2-[(E)-2-(2-Nitro-phen-yl)ethen-yl]-1-phenyl-sulfonyl-1H-indol-3-yl}ethanone.

Project description:In the title compound, C24H18N2O5S, the S atom has a distorted tetra-hedral configuration, with bond angles varying from 105.11 (7) to 119.98 (8)°. As a result of the electron-withdrawing character of the phenyl-sulfonyl group, the N-Csp (2) bond lengths [1.414 (2) and 1.413 (2) Å] are slightly longer than the reported value of 1.355 (14) Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177 (14) Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70 (7)° with the mean plane of the indole moiety. The mol-ecular structure features intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent mol-ecules are linked via C-H⋯O hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C-H⋯π inter-actions, which form a three-dimensional structure.

| S-EPMC3884461 | biostudies-literature

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