Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure and DFT study of 8-hy-droxy-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.

ABSTRACT: In the title compound, C13H15NO2, the fused non-aromatic rings of the julolidine moiety adopt envelope conformations. The hy-droxy group forms an intra-molecular hydrogen bond to the aldehyde O atom, generating an S(6) ring motif. Weak inter-molecular C-H⋯O hydrogen bonds help to stabilize the crystal structure. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state.

SUBMITTER: Faizi MSH

PROVIDER: S-EPMC5418808 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure and DFT study of 8-hy-droxy-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.

Faizi Md Serajul Haque MSH Dege Necmi N Malysheva Maria L ML

Acta crystallographica. Section E, Crystallographic communications 20170428 Pt 5

In the title compound, C13H15NO2, the fused non-aromatic rings of the julolidine moiety adopt envelope conformations. The hy-droxy group forms an intra-molecular hydrogen bond to the aldehyde O atom, generating an S(6) ring motif. Weak inter-molecular C-H⋯O hydrogen bonds help to stabilize the crystal structure. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular st ...[more]

PMID: 28529800

Similar Datasets

8-{(E)-[(4-Chloro-phen-yl)imino]-meth-yl}-1,1,7,7-tetra-methyl-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinolin-9-ol.

Project description:The title Schiff base, C23H27ClN2O adopts the phenol-imine tautomeric form, with an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. Three C atoms of the heterocyclic moiety of the hexa-hydro-pyrido-quinoline unit, as well as the two methyl groups bonded to one of these C atoms, are disordered over two set of sites, with anoccupancy ratio of 0.740 (4):0.260 (4).

| S-EPMC3685040 | biostudies-literature

Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.

Project description:In the title mol-ecule, C(14)H(15)NO(3), the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C-H⋯π inter-actions link the mol-ecules into centrosymmetric dimers, and weak inter-molecular C-H⋯O hydrogen bonds link these dimers into columns propagated along [100].

| S-EPMC2977288 | biostudies-literature

6-Hy-droxy-1,2-dihydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one.

Project description:The mol-ecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056 (1) Å]. In the crystal, strong O-H⋯O hydrogen bonds form zigzag chains along the b axis. The mol-ecules form stacks along the a axis due to π-π inter-actions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146 (7) Å.

| S-EPMC3588512 | biostudies-literature

6-Eth-oxy-carbonyl-5,7-dihy-droxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide.

Project description:In the title salt, C15H16NO4(+.)Br3(-), classical intra-molecular O-H⋯O hydrogen bonds are found, which results in the co-planarity of the ester substituents with the quinolinium residue [C-C-C-O torsion angle = 1.0 (10)°]. The bromine anions are placed on both sides of heterocyclic cation and form Br⋯N contacts of 3.674 (9) and 3.860 (9) Å, which confirms the location of positive charge on the N atom. Non-classical inter-molecular C-H⋯Br inter-actions stabilize the three-dimensional crystal structure. Moreover, anion⋯π inter-actions are noted [Br⋯ring centroid range = 3.367 (9)-3.697 (9) Å]. The partly saturated heterocycle is disordered over two sofa conformations with occupancies in the ratio 0.56 (2):0.44 (2).

| S-EPMC3588293 | biostudies-literature

10-(1,3-Benzothia-zol-2-yl)-1,1,7,7-tetra-methyl-2,3,6,7-tetra-hydro-1H,5H,11H-pyrano[3,2-g]pyrido[3,2,1-hi]quinoline.

Project description:In the title compound, C(26)H(26)N(2)O(2)S, the dihedral angle between the benzothia-zole and coumarin rings is 8.34 (7)°, indicating that the overall benzothia-zole substituent is almost coplanar with the coumarin rings. An intra-molecular S⋯O [2.813 (1) Å] contact may help to stabilize the mol-ecular conformation. In the crystal structure, π-π stacking inter-actions [centroid-centroid distances = 3.480 (2) Å] link pairs of mol-ecules.

| S-EPMC2983933 | biostudies-literature

Ethyl 4-(5-bromo-2-hy-droxy-phen-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C21H24BrNO4, the dihedral angle between the heterocyclic ring and the pendant aromatic ring is 80.20?(13)°. The hexahydroquinone [i.e. the one with the C=O group] ring adopts a sofa conformation. An intra-molecular O-H?O hydrogen bond generates an S(6) ring motif. The ethyl group is disordered over two sets of sites with a refined site occupancy ratio of 0.633?(10):0.366?(10). In the crystal, mol-ecules are linked by N-H?O inter-actions, forming chains parallel to [101]. There are no significant C-H?? or ?-? inter-actions in the crystal structure.

| S-EPMC3629593 | biostudies-literature

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives.

Project description:The Pd-catalyzed C-H bond functionalization of lilolidine was investigated. The use of a palladium-diphosphine catalyst associated to acetate bases in DMA was found to promote the regioselective arylation at α-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these α-arylated lilolidines, a second arylation at the β-position gives the access to α,β-diarylated lilolidines containing two different aryl groups. The one pot access to α,β-diarylated lilolidines with two identical aryl groups is also possible by using a larger amount of aryl bromide. The synthesis of 5,6-dihydrodibenzo[a,c]pyrido[3,2,1-jk]carbazoles from lilolidine via three successive direct arylations is also described. Therefore, this methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C-H bond functionalization steps allowing to tune their biological properties.

| S-EPMC6719733 | biostudies-literature

Crystal structure of (E)-9-({[4-(di-ethyl-amino)-phen-yl]imino}-meth-yl)-2,3,6,7-tetra-hydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol.

Project description:The title compound, C23H29N3O, was synthesized from the condensation reaction of 8-hy-droxy-julolidine-9-carbaldehyde and N,N-diethyl-p-phenyl-enedi-amine. The hy-droxy group forms a intra-molecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (14)°. One of the fused non-aromatic rings of the julolidine moiety adopts an envelope conformation and the other has a screw-boat conformation. In the crystal, mol-ecules are linked by C-H⋯π inter-actions involving the aromatic julolidine ring, forming slabs parallel to the bc plane. The tricyclic fragment of the julolidine ring and the azomethine C=N bond are disordered over two sets of sites with a refined occupancy ratio of 0.773 (3):0.227 (3).

| S-EPMC5209767 | biostudies-literature

1-(2,2-Dimeth-oxy-eth-yl)-8-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridin-5-ol.

Project description:In the title compound, C(11)H(19)N(3)O(5), the six-membered ring displays a half-chair conformation and the imidazolidine ring is essentially planar (r.m.s. deviation = 0.088 Å). An inter-molecular hydrogen bond between the hy-droxy O atom and a nitro O atom stabilizes the crystal packing.

| S-EPMC3007961 | biostudies-literature

Quinoline-2-carbaldehyde.

Project description:The title compound, C(10)H(7)NO, crystallizes with two almost planar mol-ecules (A and B) in the asymmetric unit (r.m.s. deviations = 0.018 and 0.020 Å). In the crystal, the A mol-ecules are linked by weak C-H⋯O inter-actions, thereby generating C(9) [001] chains. The B mol-ecules do not exhibit any directional bonding inter-actions.

| S-EPMC3201271 | biostudies-literature