Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa-hydro-quinoline-3-carbonitrile.

ABSTRACT: The six-membered N-heterocyclic ring of title compound, C(17)H(17)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The nitro-gen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432?(6)?Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011?Å); its benzene substituent is aligned at 84.7?(1)° to the latter plane. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, two mol-ecules are linked about a center of inversion by pairs of N-H?O hydrogen bonds, generating dimers. An ethyl-ene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3?(1)% minor component.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3201290 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa-hydro-quinoline-3-carbonitrile.

Asiri Abdullah M AM Al-Youbi Abdulrahman O AO Faidallah Hassan M HM Badahdah Khadija O KO Ng Seik Weng SW

Acta crystallographica. Section E, Structure reports online 20110914 Pt 10

The six-membered N-heterocyclic ring of title compound, C(17)H(17)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The nitro-gen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1)° to the latter plane. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, two mol-ecules are linked about a center o ...[more]

PMID: 22064694

Similar Datasets

4-(4-Bromo-phen-yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa-hydro-quinoline-3-carbonitrile.

Project description:In the title compound, C(17)H(17)BrN(2)O, the N-containing ring adopts an envelope conformation with the C atom carrying the phenyl ring displaced by -0.531?(9)?Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.0099?Å). The benzene ring is almost orthogonal to the ring to which it is attached, the C(CN)-C-C(Ph)-C(Ph) torsion angle being -101.3?(7)°. The cyclo-hexene ring is disordered over two conformations in a statistical ratio. The most prominent inter-actions in the crystal are pairs of N-H?O hydrogen bonds between inversion-related mol-ecules. The resulting dimers are linked into a three-dimensional architecture by C-H?N, C-H?Br and C-H?? inter-actions.

| S-EPMC3414305 | biostudies-literature

4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

Project description:The six-membered N-heterocyclic ring of the title compound, C(17)H(15)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The approximately planar nitro-gen-bearing ring (r.m.s. deviation 0.019?Å) is aromatic, and the N atom shows a trigonal-planar coordination; its benzene substituent is aligned at 77.1?(1) °. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, inversion-related mol-ecules are linked by pairs of N-H?O hydrogen bonds, generating dimers.

| S-EPMC3201532 | biostudies-literature

8-Methyl-2-oxo-4-(thio-phen-2-yl)-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

Project description:In the title compound, C(15)H(14)N(2)OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011?Å) and the cyclo-hexene ring has a twisted half-boat conformation with the methyl-ene C atom adjacent to the methine C atom deviating by 0.592?(7)?Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108?Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649?(4):0.351?(4) ratio, and forms dihedral angles of 51.4?(3) (major component) and 54.2?(3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol-ecules associate via an eight-membered {?HNCO}(2) synthon and these are linked into a linear supra-molecular chain along the a axis by weak ?-? inter-actions that occur between centrosymmetrically related pyridinone rings [centroid-centroid distance = 3.889?(2)?Å].

| S-EPMC3394069 | biostudies-literature

Ethyl 4-(4-chloro-phen-yl)-2-methyl-5-oxo-5,6,7,8-tetra-hydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C19H18ClNO3, the non-aromatic part of the fused ring system adopts an envelope conformation with the central methyl-ene C atom as the flap. The dihedral angle between the pyridine and benzene rings is 56.98?(3)°. In the crystal, mol-ecules are linked into double layers parallel to (100) by a network of weak C-H?O inter-actions.

| S-EPMC3770395 | biostudies-literature

2-Oxo-4-(thio-phen-2-yl)-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(18)H(12)N(2)OS, the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 16.0?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 59.5?(2)° (for the major disordered thienyl component) in order to avoid crowding the cyanide substituent. In the crystal, two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer. The thienyl ring is disordered over two sites in a 72.7?(2):27.3 ratio.

| S-EPMC3200622 | biostudies-literature

4-(4-Bromo-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(20)H(13)BrN(2)O, the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 17.7?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 82.3?(1)° in order to avoid crowding the cyanide substituent. Two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer.

| S-EPMC3200630 | biostudies-literature

4-(4-Fluoro-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(20)H(13)FN(2)O, the fluoro-phenyl ring is oriented at a dihedral angle of 72.76?(3)° with respect to the fused benzene ring. In the crystal structure, inter-molecular N-H?O, C-H?O and C-H?F inter-actions link the mol-ecules into chains. ?-? contacts between the quinoline and benzene rings [centroid-centroid distance = 3.918?(3)?Å] may further stabilize the structure. A weak C-H?? inter-action is also present. The O atom and two of the CH(2) groups of the quinoline ring system are disordered over two positions. The O atom was refined with occupancies of 0.489?(17) and 0.511?(17), while C and H atoms were refined with occupancies of 0.435?(13) and 0.565?(13).

| S-EPMC2969758 | biostudies-literature

2-Amino-4-(4-chloro-phen-yl)-5-oxo-5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile.

Project description:In the title moleclue, C(16)H(13)ClN(2)O(2), the cyclo-hexene ring is in a sofa conformation. The pyran ring is essentialy planar [maximum deviation = 0.038?(2)?Å] and forms a dihedral angle of 89.68?(10)° with the benzene ring. In the crystal, mol-ecules are linked by pairs of N-H?N hydrogen bonds, forming inversion dimers with R(2) (2)(12) ring motifs. These dimers are further linked by N-H?O hydrogen bonds into chains along [110]. Weak C-H?O hydrogen bonds are also present.

| S-EPMC3344539 | biostudies-literature

Crystal structure of 2-amino-4-(4-chloro-phen-yl)-1-(4-methyl-phen-yl)-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carbo-nitrile.

Project description:In the title compound, C23H20ClN3O, each of the cyclo-hexene and 1,4-di-hydro-pyridine rings of the 1,4,5,6,7,8-hexa-hydro-quinoline ring system adopts a twisted-boat conformation. The dihedral angle between the two benzene rings is 11.52 (7)°. In the crystal, mol-ecules are linked through a pair of amino-nitrile N-H⋯N hydrogen bonds, forming inversion dimers. These assemble into a three-dimensional network via C-H⋯O and C-H⋯π inter-actions.

| S-EPMC4719917 | biostudies-literature

2-Oxo-4-phenyl-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(20)H(14)N(2)O, the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 19.7?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 62.9?(1)° in order to avoid crowding the cyanide substituent. In the crystal, two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer.

| S-EPMC3200766 | 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