Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

7,8,9,10-Tetra-hydro-2-methyl-cyclo-hepta-[b]indol-6(5H)-one.

ABSTRACT: The title compound, C(14)H(15)NO, was synthesized from 2-hydroxy-methyl-enecyclo-hepta-none via a Japp-Klingemann acid-catalyzed cyclization. The seven-membered ring exhibits a slightly distorted envelope conformation. N-H?O hydrogen bonds form a centrosymmetric dimer; C-H?O hydrogen bonds and ?-? stacking inter-actions (the centers of the atoms involved in the stacking interaction are separated by 3.504?Å) give rise to another type of centrosymmetric dimer. In combination, these inter-actions create a stair-like chain of mol-ecules that inter-acts only loosely with neighboring chains via van der Waals inter-actions and weak C-H?? contacts.

SUBMITTER: Sridharan M

PROVIDER: S-EPMC2961774 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

7,8,9,10-Tetra-hydro-2-methyl-cyclo-hepta-[b]indol-6(5H)-one.

Sridharan Makuteswaran M Prasad Karnam J Rajendra KJ Ngendahimana Aimable A Zeller Matthias M

Acta crystallographica. Section E, Structure reports online 20080607 Pt 7

The title compound, C(14)H(15)NO, was synthesized from 2-hydroxy-methyl-enecyclo-hepta-none via a Japp-Klingemann acid-catalyzed cyclization. The seven-membered ring exhibits a slightly distorted envelope conformation. N-H⋯O hydrogen bonds form a centrosymmetric dimer; C-H⋯O hydrogen bonds and π-π stacking inter-actions (the centers of the atoms involved in the stacking interaction are separated by 3.504 Å) give rise to another type of centrosymmetric dimer. In combination, these inter-actions c ...[more]

PMID: 21202846

Similar Datasets

4-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title compound, C(14)H(15)NO, the seven-membered ring exhibits a slightly distorted twist-boat conformation. The pyrrole ring forms a dihedral angle of 1.44 (10)° with the fused benzene ring. N-H⋯O hydrogen bonds form a centrosymmetric dimer and weak C-H⋯π inter-actions are also found in the crystal structure.

| S-EPMC2968932 | biostudies-literature

7,8,9,10-Tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(13)H(13)NO, the dihedral angle between the benzene and pyrrole rings is 1.05?(5)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular N-H?O hydrogen bonds form centrosymmetric dimers. A C-H?? inter-action, involving the benzene ring, is also found in the structure.

| S-EPMC2960645 | biostudies-literature

2,5-Dimethyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(15)H(17)NO, the dihedral angle between the benzene and pyrrole rings is 1.45?(13)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular C-H?O hydrogen bonds are found.

| S-EPMC3009033 | biostudies-literature

2-Chloro-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(13)H(12)ClNO, the dihedral angle between the benzene and pyrrole rings is 1.38?(9)°. The cyclo-heptene ring adopts a distorted twist chair and sofa conformation. Inter-molecular N-H?O hydrogen bonds form an R(2) (2)(10) loop in the crystal packing. Further, weak C-H?O and C-H?? (involving the benzene ring) inter-actions are found in the crystal structure.

| S-EPMC3379447 | biostudies-literature

5-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(14)H(15)NO, the dihedral angle between the benzene and pyrrole rings is 1.99?(12)°. The cyclo-heptene ring adopts a slightly distorted boat conformation.

| S-EPMC3120537 | biostudies-other

2-Acetyl-3,5,5,9-tetra-methyl-6,7,8,9-tetra-hydro-5H-benzocyclo-hepten-7-one.

Project description:The title compound, C(17)H(22)O(2), was semi-synthesized from a mixture of ?-atlantone (Z) and ?-atlantone (E), which were isolated from the essential oil of the Atlas cedar (cedrus atlantica). The mol-ecule consists of fused six- and seven-membered rings. The seven-membered ring is in a screw-boat conformation.

| S-EPMC3050136 | biostudies-literature

Crystal structures of 2-benzyl-amino-4-(4-bromo-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile and 2-benzyl-amino-4-(4-chloro-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta[b]pyridine-3-carbo-nitrile.

Project description:In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-amino-pyridine ring is fused with a cyclo-heptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N-H⋯Nnitrile hydrogen bonds link the mol-ecules, forming inversion dimers with R 2 (2)(12) ring motifs. In (I), the resulting dimers are connected through C-H⋯Br hydrogen bonds, forming sheets parallel to (10-1), and π-π inter-actions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π-π inter-actions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001).

| S-EPMC4331894 | biostudies-literature

2-(4-Bromo-phen-yl)-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine.

Project description:In the title compound, C23H22BrNO, the cyclo-heptane ring adopts a chair conformation. The pyridine ring makes dihedral angles of 58.63 (15) and 8.27 (16)° with the benzene rings. The dihedral angle between the benzene rings is 56.68 (17)°. The crystal packing features C-Br⋯π inter-actions [Br⋯centroid distances= 3.813 (2) and 3.839 (2) Å; C-Br⋯centroid = 126.25 (10) and 138.31 (10)°, respectively, forming a three dimensional supramolecular architecture.

| S-EPMC3685096 | biostudies-literature

5-Methyl-1,2,3,3a-tetra-hydro-benzo[e]pyrrolo-[2,1-b][1,3]oxazepin-10(5H)-one.

Project description:The asymmetric unit of the title compound, C(13)H(15)NO(2), the main product of a photoreaction, contains two crystallographically independent mol-ecules. In both mol-ecules, the conformation of the seven-membered ring is twist sofa and that of the five-membered rings is envelope. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC3213428 | biostudies-literature

Crystal structure of 2-benzyl-amino-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile.

Project description:The title compound, C25H25N3O, comprises a 2-amino-pyridine ring fused with a cyclo-heptane ring, which adopts a chair conformation. The central pyridine ring (r.m.s. deviation = 0.013?Å) carries three substituents, viz. a benzyl-amino group, a meth-oxy-phenyl ring and a carbo-nitrile group. The N atom of the carbo-nitrile group is significantly displaced [by 0.2247?(1)?Å] from the plane of the pyridine ring, probably due to steric crowding involving the adjacent substituents. The phenyl and benzene rings are inclined to one another by 58.91?(7)° and to the pyridine ring by 76.68?(7) and 49.80?(6)°, respectively. In the crystal, inversion dimers linked by pairs of N-H?Nnitrile hydrogen bonds generate R 2 (2)(14) loops. The dimers are linked by C-H?? and slipped parallel ?-? inter-actions [centroid-centroid distance = 3.6532?(3)?Å] into a three-dimensional structure.

| S-EPMC4257429 | 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