Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Zwitterionic 1-{(E)-[(2-methyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

ABSTRACT: The title Schiff base, C18H15NO, crystallizes in its zwitterionic form and an N-H?O hydrogen bond closes an S(6) ring. The dihedral angle between the aromatic ring systems is 36.91?(10)°. Weak aromatic ?-? stacking occurs in the crystal [minimum centroid-centroid separation = 3.7771?(15)?Å].

SUBMITTER: Khelifa Baghdouche A

PROVIDER: S-EPMC4051036 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Zwitterionic 1-{(E)-[(2-methyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

Khelifa Baghdouche Ammar A Mosbah Salima S Belhocine Youghourta Y Bencharif Leïla L

Acta crystallographica. Section E, Structure reports online 20140517 Pt 6

The title Schiff base, C18H15NO, crystallizes in its zwitterionic form and an N-H⋯O hydrogen bond closes an S(6) ring. The dihedral angle between the aromatic ring systems is 36.91 (10)°. Weak aromatic π-π stacking occurs in the crystal [minimum centroid-centroid separation = 3.7771 (15) Å]. ...[more]

PMID: 24940256

Similar Datasets

Zwitterionic (E)-1-[(4-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

Project description:The title compound, C(17)H(12)N(2)O(3), was synthesized by the reaction of 2-hy-droxy-1-naphthaldehyde with 4-nitro-benzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto-amino tautomer has a fairly short intra-molecular N-H?O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The mol-ecule is essentially planar, with a dihedral angle of 1.96?(3)° between the ring systems. In the crystal, the mol-ecules are linked via inter-molecular C-H?O hydrogen bonds, forming a layer parallel to (101).

| S-EPMC3089354 | biostudies-literature

3-{(E)-[(4-Formyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

Project description:The title Schiff base compound, C(18)H(13)NO(2), is a zwitterion, with the naphthol 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 naphthyl ring system and the benzene ring is 1.73?(11)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, adjacent mol-ecules are connected by inter-molecular C-H?O hydrogen bonds, forming a supra-molecular ribbon along the b axis.

| S-EPMC3050369 | biostudies-other

(E)-1-[(2-Amino-5-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

Project description:The title Schiff base compound, C(17)H(13)N(3)O(3), crystallizes in a zwitterionic form and exists in a trans configuration about the C=N bond. The mol-ecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80?(9)°. The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88?(12)°]. Bifurcated intra-molecular N-H?N and N-H?O hydrogen bonds formed between iminium groups and amine N atoms and naphthalen-2-olate O atoms generate S(5) and S(6) ring motifs, respectively. In the crystal, neighbouring zwitterions are linked through weak C-H?O inter-actions, giving rise to screw chains along [010]. Mol-ecules in these chains are linked to those of an adjacent chains through N-H?O hydrogen bonds and weak C-H?O inter-actions, forming sheets parallel to the ac plane. O?C [2.895?(3)?Å] short contacts and ?-? inter-actions [centroid-centroid distance = 3.8249?(19)?Å] are also observed.

| S-EPMC2979134 | biostudies-literature

Zwitterionic 1-{(1<i>E</i>)-[(4-hy-droxy-phen-yl)iminio]meth-yl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis.

Project description:The title zwitterion, C17H13NO2 (systematic name: 1-{(1E)-[(4-hy-droxy-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate), features an intra-molecular charge-assisted N+-H?O- hydrogen bond. A twist in the mol-ecule is evident around the N-C(hy-droxy-benzene) bond [C-N-C-C torsion angle = 39.42?(8)°] and is reflected in the dihedral angle of 39.42?(8)° formed between the aromatic regions of the mol-ecule. In the crystal, zigzag supra-molecular chains along the a axis are formed by charge-assisted hy-droxy-O-H?O(phenoxide) hydrogen bonding. These are connected into a layer in the ab plane by charge-assisted hy-droxy-benzene-C-H?O(phenoxide) inter-actions and ?-? contacts [inter-centroid distance between naphthyl-C6 rings = 3.4905?(12)?Å]. Layers stack along the c axis with no specific inter-actions between them. The Hirshfeld surface analysis points to the significance C?H contacts between layers.

| S-EPMC5683488 | biostudies-literature

1-{[4-(4-{[(2-Oxidonaphthalen-1-yl)methyl-idene]aza-nium-yl}phen-oxy)phen-yl]iminiumylmeth-yl}naphthalen-2-olate.

Project description:The title Schiff base compound, C34H24N2O3, was prepared by a condensation reaction of bifunctional aromatic diamine (4,4'-diamino-diphenyl ether) with hy-droxy-naphtaldehyde. The asymmetric unit contains two independent mol-ecules with similar conformations. The compound contains a central oxygen bridge and two functionalized [(E)-(phenyl-iminio)meth-yl]naphthalen-2-olate units. The dihedral angles between the benzene rings linking to the central O atom are 74.64?(19) and 69.85?(18)° in the two independent mol-ecules. Intra-molecular O-H?O hydrogen bonding occurs between the protonated imino N atoms and deprotonated hy-droxy O atoms in both mol-ecules. In the crystal, weak C-H?O hydrogen bonds are observed.

| S-EPMC3629627 | biostudies-literature

1-[(2-Methyl-piperidin-1-yl)(phen-yl)meth-yl]naphthalen-2-ol.

Project description:In the title compound, C(23)H(25)NO, an intra-molecular O-H?N hydrogen bond defines the mol-ecular conformation; the naphthol mean plane and the benzene ring form a dihedral angle of 75.8?(2)°. The piperidine ring adopts a chair conformation. The crystal packing exhibits no short inter-molecular contacts.

| S-EPMC3470315 | biostudies-literature

1-{[(E)-(4-{[(2Z)-2,3-Di-hydro-1,3-thia-zol-2-yl-idene]sulfamo-yl}phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

Project description:In the title zwitterionic compound, C20H15N3O3S2, the 2-hy-droxy-naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia-zol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125?Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70?(10), 79.97?(7) and 83.14?(6)°, respectively. There is an intra-molecular S(6) motif involving the imine N-H and the naphtho-late O atom. In the crystal, inversion-related mol-ecules form dimers as a result of N-H?N and N-H?O hydrogen bonds with R 2 (2)(8) and R 1 (2)(4) motifs, respectively. Weak ?-? inter-actions between the benzene and naphthyl rings of inversion-related mol-ecules have ring centroid-centroid distances of 3.638?(2) and 4.041?(2)?Å. A C-H?? inter-action occurs between the thia-zol ring and the benzene ring of an adjacent mol-ecule.

| S-EPMC4459363 | biostudies-other

1-[(3-Methyl-piperidin-1-yl)(3-nitro-phen-yl)meth-yl]naphthalen-2-ol.

Project description:The title compound, C(23)H(24)N(2)O(3), was synthesized from naphthalen-2-ol, 3-nitro-benzaldehyde and 3-methyl-piperidine. The dihedral angles between the naphthalene system and the nitro-benzene and methyl-piperidine rings are 78.53?(13) and 64.14?(15)°, respectively. The mol-ecular conformation is stabilized by a strong intra-molecular O-H?N hydrogen bond.

| S-EPMC3011680 | biostudies-literature

(2-Hy-droxy-7-meth-oxy-naphthalen-1-yl)(4-methyl-phen-yl)methanone.

Project description:In the title compound, C(19)H(16)O(3), an intra-molecular O-H?O=C hydrogen bond is formed between the hy-droxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63?(6) and 47.99?(7)°, respectively. The dihedral angle between the latter planes is 61.39?(5)°. In the crystal, two mol-ecules are connected by pairs of inter-molecular O-H?O=C hydrogen bonds, forming centrosymmetric dimers with an R(2) (2)(4) graph-set motif. The mol-ecular packing features C-H?? interactions.

| S-EPMC3009359 | biostudies-literature

Crystal structure of 2-{(E)-[(2-hy-droxy-phen-yl)iminium-yl]meth-yl}-4-methyl-phenolate.

Project description:The title compound, C14H13NO2, exists as a zwitterion in the solid state, with the H atom of the phenol group transferred to the imine N atom. The dihedral angle between the planes of the benzene rings is 10.13?(9)°. Intra-molecular N-H?O hydrogen bond generate S(6) and S(5) loops. In the crystal, mol-ecules are connected by O-H?O hydrogen bonds, generating C(9) chains propagating in the [010] direction.

| S-EPMC4420074 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data