Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2-Hy-droxy-5-[(E)-(1H-indol-3-yl-methyl-idene)aza-nium-yl]benzoate.

ABSTRACT: The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-amino-salicylic acid and 1H-indole-3-carbaldehyde. The whole mol-ecule is roughly planar: the 4-hy-droxy-anilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77?(11)°, whereas, the carboxyl-ate group makes a dihedral angle of 3.34?(45)° with the parent 4-hy-droxy-anilinic group. S(6) ring motifs are formed due to intra-molecular O-H?O hydrogen bonding. In the crystal, inter-molecular N-H?O and C-H?O hydrogen bonds build up pseudo-rings with R(1) (2)(4), R(2) (1)(7) and R(2) (2)(14) ring motifs. These pseudo-dimers are further linked by N-H?O hydrogen bonds into a chain extending along [101]. C-H?? inter-actions also occur, along with offset ?-? inter-actions between the anilinic phenyl and the heterocyclic five-membered rings with a centroid-centroid distance of 3.5716?(19)?Å.

SUBMITTER: Tahir MN

PROVIDER: S-EPMC3011759 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2-Hy-droxy-5-[(E)-(1H-indol-3-yl-methyl-idene)aza-nium-yl]benzoate.

Tahir M Nawaz MN Shad Hazoor Ahmad HA

Acta crystallographica. Section E, Structure reports online 20101127 Pt 12

The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-amino-salicylic acid and 1H-indole-3-carbaldehyde. The whole mol-ecule is roughly planar: the 4-hy-droxy-anilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77 (11)°, whereas, the carboxyl-ate group makes a dihedral angle of 3.34 (45)° with the parent 4-hy-droxy-anilinic group. S(6) ring motifs are formed due to intra-molecular O-H⋯O ...[more]

PMID: 21589591

Similar Datasets

2-[(2-Hy-droxy-4-meth-oxy-benzyl-idene)aza-nium-yl]benzoate monohydrate.

Project description:In the title compound, C(15)H(13)NO(4)·H(2)O, the Schiff base exists in a zwitterionic form and a bifurcated intra-molecular N-H⋯(O,O) hydrogen bond generates two S(6) rings. The dihedral angle between the two benzene rings is 25.8 (2)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC3006953 | biostudies-literature

Crystal structure of (E)-2-[(4-hy-droxy-benzyl-idene)aza-nium-yl]benzoate.

Project description:The title Schiff base, C14H11NO3, crystallizes as a zwitterion (i.e. proton transfer from the carb-oxy-lic acid group to the imine N atom). The dihedral angle between the aromatic rings is 19.59 (6)° and an intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (4)(24) loops. The dimers are linked by C-H⋯O inter-actions, generating (211) sheets.

| S-EPMC4186171 | biostudies-literature

2-Hy-droxy-5-{[(E)-4-meth-oxy-benzyl-idene]aza-nium-yl}benzoate.

Project description:In the title zwitterion, C(15)H(13)NO(4), obtained from the condensation of 5-amino-salicylic acid and 4-meth-oxy-benz-alde-hyde, the 4-hydoxyanilinic group of the 5-amino-salicylic acid moiety and the 4-meth-oxy-benzaldehyde moiety are twisted with respect to one another, making a dihedral angle of 10.37 (7)°. The carboxyl-ate group makes a dihedral angle of 5.7 (2)° with the parent 4-hydoxyanilinic group. An intra-molecular O-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, inter-molecular C-H⋯O and N-H⋯O hydrogen bonds with R(2) (1)(7) ring motifs link the mol-ecules into infinite chains extending along the c axis. The occurence of slipped π-π stacking between symmetry-related aromatic rings reinforces the packing.

| S-EPMC2983260 | biostudies-literature

(1-Hy-droxy-ethyl-idene)(meth-yl)aza-nium bromide-N-methyl-acetamide (1/1).

Project description:The asymmetric unit of the organic hybrid salt, C(3)H(8)NO(+)·Br(-)·C(3)H(7)NO, comprises an N-methyl-acetamide cation, a N-methyl-acetamide mol-ecule and a bromide anion. The amide species are linked head-to-head through a short O⋯H⋯O hydrogen bond, giving a monocation, which is extended by N-H⋯Br hydrogen bonds into chains along the b-axis direction.

| S-EPMC3344601 | biostudies-literature

1-sec-Butyl-3-[hy-droxy(1-methyl-1H-indol-3-yl)methyl-idene]pyrrolidine-2,4-dione.

Project description:In the title compound, C(18)H(20)N(2)O(3), the dihedral angle between the indole ring system (r.m.s. deviation = 0.018 Å) and the hy-droxy-methyl-enepyrrolidine-2,4-dione plane (r.m.s. deviation = 0.036 Å) is 9.87 (7)°. The keto and enol groups are involved in an intra-molecular O-H⋯O hydrogen bond. An intra-molecular C-H⋯O inter-action also occurs. The sec-butyl group is disordered over two orientations corresponding to an approximate 180° rotation about the N-C bond, with occupancies of 0.670 (6) and 0.330 (6). In the crystal, mol-ecules are linked into chains along the c axis by C-H⋯O hydrogen bonds.

| S-EPMC3008104 | biostudies-literature

Crystal structures of the 1:1 salts of 2-amino-4-nitro-benzoate with each of (2-hy-droxy-eth-yl)di-methyl-aza-nium, tert-but-yl(2-hy-droxy-eth-yl)aza-nium and 1,3-dihy-droxy-2-(hy-droxy-meth-yl)propan-2-aminium.

Project description:The crystal and mol-ecular structures of the title mol-ecular salts, C4H12NO+·C7H5N2O4 -, (I), C6H16NO+·C7H5N2O4 -, (II), and C4H12NO3 +·C7H5N2O4 -, (III), are described. The common feature of these salts is the presence of the 2-amino-4-nitro-benzoate anion, which exhibit non-chemically significant variations in the conformational relationships between the carboxyl-ate and nitro groups, and between these and the benzene rings they are connected to. The number of ammonium-N-H H atoms in the cations increases from one to three in (I) to (III), respectively, and this variation significantly influences the supra-molecular aggregation patterns in the respective crystals. Thus, a linear supra-molecular chain along [100] sustained by charge-assisted tertiary-ammonium-N-H?O(carboxyl-ate), hy-droxy-O-H?O(carboxyl-ate) and amino-N-H?O(carboxyl-ate) hydrogen-bonds is apparent in the crystal of (I). Chains are connected into a three-dimensional architecture by methyl-C-H?O(hy-droxy) and ?-? inter-actions, the latter between benzene rings [inter-centroid separation = 3.5796?(10)?Å]. In the crystal of (II), a supra-molecular tube propagating along [901] arises as a result of charge-assisted secondary-ammonium-N-H?O(carboxyl-ate) and hy-droxy-O-H?O(carboxyl-ate) hydrogen-bonding. These are connected by methyl-ene- and methyl-C-H?O(nitro) and ?-? stacking between benzene rings [inter-centroid separation = 3.5226?(10)?Å]. Finally, double-layers parallel to (100) sustained by charge-assisted ammonium-N-H?O(carboxyl-ate), ammonium-N-H?O(hy-droxy) and hy-droxy-O-H?O(carboxyl-ate) hydrogen-bonds are apparent in the crystal of (III). These are connected in a three-dimensional architecture by amine-N-H?O(nitro) hydrogen-bonds.

| S-EPMC6281114 | biostudies-literature

(S)-2-[(2-Hy-droxy-benz-yl)aza-nium-yl]-4-(methyl-sulfan-yl)butano-ate.

Project description:The zwitterionic title compound, C(12)H(17)NO(3)S, is a reduced Schiff base derived from (S)-N-(2-hy-droxy-benzyl-idene)methio-nine. An intra-molecular inter-action between the N-H and carboxyl-ate groups forms a roughly planar (r.m.s. deviation = 0.1405?Å) five-membered ring containing the H(N), N, C?, C(carboxyl-ate) and O atoms in a penta-gonal conformation. In the crystal, a supra-molecular triangle-shaped motif is generated by mol-ecules held together by O-H?O and N-H?O hydrogen bonds.

| S-EPMC3120446 | biostudies-literature

(R)-(3-Carb-oxy-2-hy-droxy-prop-yl)tri-methyl-aza-nium chloride.

Project description:In the title salt (common name l-carnitine hydro-chloride), C(7)H(16)NO(3) (+)·Cl(-), the organic cation features a carb-oxy-lic part (-CO(2)H) having unambigous single- and double-bonds [1.336 (2), 1.211 (2) Å]. There is a large N-C-C bond angle [115.9 (1)°] for the C atom connected to the bulky trimethyl-amino substituent. In the crystal, the acid H atom forms a hydrogen bond to the chloride anion, whereas the hydroxyl H atom forms a longer hydrogen bond to the anion, generating a helical chain running along [001].

| S-EPMC3344540 | biostudies-literature

(E)-2-[(2,4-Dihy-droxy-benzyl-idene)aza-nium-yl]-3-(1H-indol-3-yl)propano-ate monohydrate.

Project description:In the zwitterionic title compound, C(18)H(16)N(2)O(4)·H(2)O, the dihedral angle between the planes of the benzene and indole rings is 39.20?(8)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, inter-molecular hy-droxy and water O-H?O(carboxyl-ate) and N(+)-H?O(carboxyl-ate) and indole N-H?O(water) hydrogen bonds give a three-dimensional structure.

| S-EPMC3213555 | biostudies-other

[(5-Bromo-1H-indol-3-yl)meth-yl]dimethyl-aza-nium nitrate.

Project description:In the title compound, C(11)H(14)BrN(2) (+)·NO(3) (-), inter-molecular N-H?O and N-H?N hydrogen bonds link the proton-ated 5-bromo-gramine cation and the nitrate anions. Further N-H?O hydrogen bonds link the cation-anion pairs into a chain running parallel to [100]. C-H?O hydrogen bonds link the chains, forming a layer parallel to (001).

| S-EPMC3152118 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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