Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(11aS)-7-Bromo-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-3,11-dione.

ABSTRACT: The title compound, C(12)H(11)BrN(2)O(2), was prepared by an intra-cyclization reaction of (S)-1-(5-bromo-2-nitro-benz-yl)-5-oxopyrrolidine-2-carb-oxy-lic acid methyl ester in the presence of EtOH/Fe. The five-membered pyrrolidinone ring adopts an approximate envelope conformation, while the seven-membered diazepanone ring displays a twisted boat conformation. Inter-molecular classical N-H?O hydrogen bonds and weak C-H?O inter-actions help to stabilize the crystal structure.

SUBMITTER: Ma C

PROVIDER: S-EPMC3254472 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(11aS)-7-Bromo-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-3,11-dione.

Ma Chao C Wang Zhen-Zhong ZZ Pan Li L Tian Yu Y Xiao Wei W

Acta crystallographica. Section E, Structure reports online 20111214 Pt 1

The title compound, C(12)H(11)BrN(2)O(2), was prepared by an intra-cyclization reaction of (S)-1-(5-bromo-2-nitro-benz-yl)-5-oxopyrrolidine-2-carb-oxy-lic acid methyl ester in the presence of EtOH/Fe. The five-membered pyrrolidinone ring adopts an approximate envelope conformation, while the seven-membered diazepanone ring displays a twisted boat conformation. Inter-molecular classical N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions help to stabilize the crystal structure. ...[more]

PMID: 22259413

Similar Datasets

(11aS)-8-Hydr-oxy-7-meth-oxy-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-3,11-dione.

Project description:The title chiral compound, C(13)H(14)N(2)O(4), was prepared by an intra-cyclization reaction of methyl (S)-1-(4-hydr-oxy-5-meth-oxy-2-nitro-benz-yl)-5-oxopyrrolidine-2-carboxyl-ate in the presence of ethanol and iron. The five-membered substituted pyrrole ring adopts an approximate envelope conformation, while the seven-membered substituted diazepine ring displays a twist-boat conformation. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonding helps to stabilize the crystal structure.

| S-EPMC2915322 | biostudies-literature

2-Hy-droxy-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dione.

Project description:The seven-membered ring of the title compound, C(12)H(12)N(2)O(3), which is fused with the phenyl-ene ring, adopts a boat-shaped conformation (with the methine C atom as the prow and the phenyl-ene C atoms as the stern); the H atom on the methine linkage exists in an axial position. The five-membered ring that is fused with the seven-membered ring adopts an envelope conformation (with the C atom bearing the hy-droxy substituent representing the flap) [the deviation from the plane defined by the other four atoms is 0.200?(7)?Å in one mol-ecule and 0.627?(5)?Å in the other]. The two independent mol-ecules are disposed about a pseudo center of inversion and are connected by a pair of N-H?O hydrogen bonds. Adjacent dimers are linked by a pair of O-H?O hydrogen bonds, generating a chain running along the b axis.

| S-EPMC3212299 | biostudies-literature

7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione.

Project description:The title compound, C(18)H(15)ClN(2)O(2), is a potential human immunodeficiency virus type-1 (HIV-1) non-nucleoside reverse transcriptase inhibitor. The pyrrolidine ring adopts an envelope and the diazepine ring a boat conformation. In the crystal structure, two isomers (R and S) form centrosymmetric dimers via N-H?O hydrogen bonds.

| S-EPMC2960833 | biostudies-other

2-Hydr-oxy-10-phenacyl-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione.

Project description:The title compound, C(20)H(18)N(2)O(4), consists of a benzodiazepinedione system fused to a pyrrole system. The seven-membered ring adopts a boat-shaped conformation (with the methine C atom as the prow); the five-membered ring adopts an enveloped-shaped conformation (with the hydr-oxy-bearing C atom as the flap). In the crystal, the hydr-oxy group is hydrogen bonded to the carbonyl O atom of an adjacent mol-ecule, generating a zigzag chain.

| S-EPMC2983756 | biostudies-literature

Pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dithione.

Project description:The seven-membered fused-ring in the title compound, C(12)H(12)N(2)S(2), adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). This methine C atom and the tertiary N atom also belong to a five-membered ring, which has an envelope conformation. In the crystal structure, mol-ecules are linked about a center of inversion by pairs of N-H⋯S hydrogen bonds.

| S-EPMC3006926 | biostudies-literature

10-Allyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione.

Project description:The compound, C(15)H(16)N(2)O(2), features a pyrroline ring fused with a seven-membered diazepine ring; the latter system adopts a boat conformation (with the methine C atom as the prow and the two C atoms of the aromatic ring as the stern). A CH(2)-CH(2) segment of the pyrroline ring is disordered over two positions in a 1:1 ratio.

| S-EPMC2970423 | biostudies-literature

6-Nitro-2,3-dihydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione.

Project description:In the two mol-ecules of the asymmetric unit of the title compound, C(12)H(11)N(3)O(4), the seven-membered diazepine ring adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). The five-membered pyrrole ring, which has an envelope conformation, makes dihedral angles of 60.47?(10) and 54.69?(9)° with the benzene ring of the benzodiazepine unit in the two mol-ecules. In the crystal, inter-molecular N-H?O hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distance = 3.8023?(7)-3.8946?(7)?Å] lead to the formation of a three-dimensional framework.

| S-EPMC3213458 | biostudies-literature

2-Hydr-oxy-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione monohydrate.

Project description:The title compound, C(15)H(14)N(2)O(3)·H(2)O, consists of a benzodiazepinedione system fused to a pyrrole system. The seven-membered ring adopts a boat-shaped conformation (with the methine C atom as the prow); the five-membered ring adopts an enveloped-shaped conformation (with the hydr-oxy-bearing C atom as the flap). In the crystal, adjacent mol-ecules are linked by O-H⋯O hydrogen bonds into sheets parallel to (102). In addition, C(acetyl-inic)-H⋯O hydrogen bonds occur.

| S-EPMC2983934 | biostudies-literature

Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1,3-dicarboxyl-ate.

Project description:In the title compound, C(26)H(31)NO(6)S, the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered thia-zine ring is in a distorted chair conformation. The crystal packing is stabilized through an inter-molecular C-H⋯O inter-action, generating inversion-related R(2) (2)(10) ring motifs.

| S-EPMC3200855 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of (S)-10-propargyl-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dione.

Project description:The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair and boat conformations, respectively. The absolute configuration was assigned on the the basis of l-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C-HBnz⋯ODiazp and C-HProprg⋯ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = proparg-yl) hydrogen bonds link the mol-ecules into two-dimensional networks parallel to the bc plane, enclosing R 4 4(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (49.8%), H⋯C/C⋯H (25.7%) and H⋯O/O⋯H (20.1%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-H⋯O hydrogen-bond energies are 38.8 (for C-HBnz⋯ODiazp) and 27.1 (for C-HProprg⋯ODiazp) kJ mol-1. 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. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7133028 | 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