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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-other | 2008

REPOSITORIES: biostudies-other

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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-?O)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].

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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

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 ?-? [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?? 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 ?-? 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?? inter-actions, which form a three-dimensional structure.

| S-EPMC3884461 | biostudies-literature

Ethyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate.

Project description:In the title compound, C(8)H(11)N(3)O(4), the dihedral angle between the imidazole ring and the ethyl acetate plane is 103.1?(8)°. The crystal packing is stabilized by weak inter-molecular C-H?O and C-H?N hydrogen bonds.

| S-EPMC2983319 | biostudies-literature

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