Browse
Submit Data
Databases
API
Help

Dataset Information

8 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

1-Ethyl 2-methyl 3,4-bis-(acet-yloxy)pyrrolidine-1,2-di-carboxyl-ate: crystal structure, Hirshfeld surface analysis and computational chemistry.

ABSTRACT: The title compound, C₁₃H₁₉NO₈, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C-C bond; the C_m-C_a-C_a-C_me torsion angle is 38.26 (15)° [m = methyl-carboxyl-ate, a = acet-yloxy and me = methyl-ene]. While the N-bound ethyl-carboxyl-ate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supra-molecular double-layers are formed by weak methyl- and methyl-ene-C-H⋯O(carbon-yl) inter-actions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional inter-actions between them. The Hirshfeld surface is dominated by H⋯H (55.7%) and H⋯C/C⋯H (37.0%) contacts; H⋯H contacts are noted in the inter-double-layer region. The inter-action energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.

SUBMITTER: Dallasta Pedroso S

PROVIDER: S-EPMC7273984 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

4-Nitro-benzyl 3,4-bis-(acet-yloxy)-2-(4-meth-oxy-phen-yl)pyrrolidine-1-carboxyl-ate: crystal structure, Hirshfeld surface analysis and computational chemistry.

Project description:The title compound, C23H24N2O9, is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C-C bond bearing the adjacent acet-yloxy substituents. These are flanked on one side by a C-bound 4-meth-oxy-phen-yl group and on the other by a methyl-ene group. The almost sp 2-N atom [sum of angles = 357°] bears a 4-nitro-benzyl-oxycarbonyl substituent. In the crystal, ring-methyl-ene-C-H?O(acet-yloxy-carbon-yl) and methyl-ene-C-H?O(carbon-yl) inter-actions lead to supra-molecular layers lying parallel to (01); the layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surfaces indicates the combined importance of H?H (42.3%), H?O/O?H (37.3%) and H?C/C?H (14.9%) surface contacts. Further, the inter-action energies, largely dominated by the dispersive term, point to the stabilizing influence of H?H and O?O contacts in the inter-layer region.

| S-EPMC7336773 | biostudies-literature

Ethyl 3'-cyano-1'-methyl-2-oxo-4'-phenylspiro-[acenaphthene-1,2'-pyrrolidine]-3'-carboxyl-ate.

Project description:In the title compound, C(26)H(22)N(2)O(3), the acenaphthen-1-one ring system is nearly planar and the pyrrolidine ring adopts a distorted envelope conformation. An inter-molecular C-H?O hydrogen bond stabilizes the crystal structure.

| S-EPMC2960275 | biostudies-literature

Ethyl 3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

Project description:The non-H atoms of the title compound, C(9)H(13)NO(2), are almost coplanar (r.m.s. deviation = 0.0358?Å). Weak inter-molecular N-H?O hydrogen bonds link the mol-ecules into zigzag chains along the b axis with graph-set motif C(5). The chains are further linked into a three-dimensional network by C-H?O hydrogen bonds and C-H?? inter-actions.

| S-EPMC3008020 | biostudies-literature

Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

Project description:The mol-ecule of the title compound, C(10)H(13)NO(3), is approximately planar (maximum deviation 0.1424?Å). In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H?O hydrogen bonds, and the dimeric units are linked by non-classical C-H?O hydrogen bonds, forming a layered structure.

| S-EPMC2969404 | biostudies-literature

Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa-hydro-pyrrolo-[2',3':3,4]pyrrolo-[1,2-a]benzimidazole-2-carboxyl-ate.

Project description:The title mol-ecule, C(22)H(23)N(3)O(2), was obtained via an intra-molecular cyclo-addition of an azomethine ylide and an alkene tethered by a benzimidazole unit. The benzoimidazole unit is essentially planar, with an r.m.s. deviation of 0.0087?Å from the nine constituent atoms. It has a cis fusion of the two pyrrolidine rings as well as a cis ester appendage. The two pyrrolidine rings rings have envelope conformations. The crystal packing is stabilized by aromatic ?-? stacking of parallel benzimidazole ring systems, with a centroid-to-centroid distance of 3.518?(6)?Å. Weak inter-molecular C-H?O contacts may also play a role in the stability of the packing.

| S-EPMC3089295 | biostudies-literature

Ethyl 1''-benzyl-1'-methyl-2''-oxodi-spiro-[indeno-[1,2-b]quinoxaline-11,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate.

Project description:In the title compound, C36H30N4O3, the quinoxaline-indene system is roughly planar, with a maximum deviation from the mean plane of 0.218 Å for the C atom shared with the central pyrrolidine ring. This latter ring forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline-indene system and the indole ring, respectively. The central pyrrolidine ring has an envelope conformation with the N atom as the flap, while the pyrrolidine and five-membered rings of the indole group adopt twisted conformation and envelope (with the C atom bearing the quinoxaline-indene system as the flap) conformations, respectively. In the crystal, mol-ecules are linked via weak C-H⋯N hydrogen bonds, forming a chain running along [100].

| S-EPMC3684912 | biostudies-literature

Ethyl 2-acet-amido-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

Project description:In the title compound, C(13)H(17)NO(3)S, the dihedral angles between the thio-phene ring and the ethyl ester and acetamide groups are 5.21?(13) and 10.06?(16)°, respectively. The cyclo-hezene ring adopts a half-chair conformation. An S(6) ring is formed due to an intra-molecular N-H?O hydrogen bond. In the crystal, mol-ecules are linked by C-H?O inter-actions between the tetra-hydro-1-benzothio-phene unit and the ethyl ester group, forming C(7) chains propagating along the b-axis direction.

| S-EPMC3393310 | biostudies-literature

Ethyl 5-methyl-imidazo[1,2-a]pyridine-2-carboxyl-ate.

Project description:The title compound, C(11)H(12)N(2)O(2), was synthesized from the reaction of 6-methyl-pyridin-2-amine and ethyl 3-bromo-2-oxopropionate. In the mol-ecular structure, the six- and five-membered rings are individually almost planar with r.m.s. deviations of 0.003 and 0.002?Å, respectively. The two rings are almost coplanar, the dihedral angle between their planes being 1.4?(3)°. Inter-molecular C-H?O and C-H?N hydrogen bonds are present in the crystal structure.

| S-EPMC3007311 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of ethyl 6'-amino-2'-(chloro-meth-yl)-5'-cyano-2-oxo-1,2-di-hydro-spiro-[indoline-3,4'-pyran]-3'-carboxyl-ate.

Project description:The mol-ecular conformation of the title compound, C17H14ClN3O4, is stabilized by an intra-molecular C-H⋯O contact, forming an S(6) ring motif. In the crystal, the mol-ecules are connected by N-H⋯O hydrogen-bond pairs along the b-axis direction as dimers with R 2 2(8) and R 2 2(14) ring motifs and as ribbons formed by inter-molecular C-H⋯N hydrogen bonds. There are weak van der Waals inter-actions between the ribbons. The most important contributions to the surface contacts are from H⋯H (34.9%), O⋯H/H⋯O (19.2%), C⋯H/H⋯C (11.9%), Cl⋯H/H⋯Cl (10.7%) and N⋯H/H⋯N (10.4%) inter-actions, as concluded from a Hirshfeld surface analysis.

| S-EPMC8382051 | biostudies-literature

2,2-Diethyl 3,4-dimethyl 5-(4-cyano-phen-yl)pyrrolidine-2,2,3,4-tetra-carboxyl-ate.

Project description:The title compound, C(21)H(24)N(2)O(8), was synthesized by a 1,3-dipolar cyclo-addition reaction of dimethyl fumarate, diethyl 2-amino-malonate and 4-cyano-benzaldehyde. Both methyl ester groups display a trans configuration and the pyrrolidine ring possesses an envelope conformation, with the C atom in the 3-position as the flap. In the crystal, N-H?N hydrogen bonds and weak C-H?O inter-actions occur.

| S-EPMC3414296 | 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