Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure, Hirshfeld surface analysis and DFT study of 1-ethyl-3-phenyl-1,2-di-hydro-quinoxalin-2-one.

ABSTRACT: In the title mol-ecule, C₁₆H₁₄N₂O, the di-hydro-quinoxaline moiety is not planar as there is a dihedral angle of 4.51?(5)° between the constituent rings. In the crystal, C-H?O hydrogen bonds form helical chains about the crystallographic 2₁ screw axis in the b-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (51.7%), H?C/C?H (26%) and H?O/O?H (8.5%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311?G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 3.8918?eV.

SUBMITTER: Al Ati G

PROVIDER: S-EPMC7784057 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure, Hirshfeld surface analysis and DFT study of 1-ethyl-3-phenyl-1,2-di-hydro-quinoxalin-2-one.

Al Ati Gamal G Chkirate Karim K Mashrai Ashraf A Mague Joel T JT Ramli Youssef Y Achour Redouane R Essassi El Mokhtar EM

Acta crystallographica. Section E, Crystallographic communications 20210101 Pt 1

In the title mol-ecule, C16H14N2O, the di-hydro-quinoxaline moiety is not planar as there is a dihedral angle of 4.51 (5)° between the constituent rings. In the crystal, C-H⋯O hydrogen bonds form helical chains about the crystallographic 21 screw axis in the b-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (51.7%), H⋯C/C⋯H (26%) and H⋯O/O⋯H (8.5%) inter-actions. The ...[more]

PMID: 33520276

Similar Datasets

Crystal structure and Hirshfeld surface analysis of ethyl 2-(7-chloro-3-methyl-2-oxo-1,2-di-hydro-quinoxalin-1-yl)acetate.

Project description:The quinoxaline moiety in the title mol-ecule, C13H13ClN2O3, is almost planar (r.m.s. deviation of the fitted atoms = 0.033 Å). In the crystal, C-H⋯O hydrogen bonds plus slipped π-stacking and C-H⋯π(ring) inter-actions generate chains of mol-ecules extending along the b-axis direction. The chains are connected by additional C-H⋯O hydrogen bonds. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.6%), H⋯O/O⋯H (22.7%) and H⋯Cl/Cl⋯H (13.1%) inter-actions.

| S-EPMC10993606 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetra-hydro-quinoxalin-1-yl)ethyl acetate.

Project description:In the title mol-ecule, C18H16N2O3, the di-hydro-quinoxaline moiety, with the exception of the N atom is essentially planar with the inner part of the methyl-propano-ate group (CH2-CH2-O) nearly perpendicular to it. In the crystal, inversion dimers formed by C-H⋯O hydrogen bonds are connected into oblique stacks by π-stacking and C-H⋯π(ring) inter-actions.

| S-EPMC8183448 | biostudies-literature

Crystal structure of ethyl 2-{4-[(2-oxo-3-phenyl-1,2-di-hydro-quinoxalin-1-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

Project description:The quinoxaline portion of the title mol-ecule, C21H19N5O3, is not quite planar as indicated by a dihedral angle of 3.38 (7)° between the constituent rings. The mol-ecule is 'U-shaped', which is consolidated by an intra-molecular anti-parallel carbonyl electrostatic inter-action with C··O distances of 2.8905 (16) and 3.0221 (15) Å, in the crystal forms corrugated layers through C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π(ring) and π-stacking inter-actions.

| S-EPMC9635411 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di-hydro-quinoxalin-1-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

Project description:The mol-ecule of the title compound, C16H17N5O3, is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di-hydro-qinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 (5)° with respect to the pendant triazole ring. In the crystal, a combination of inter-molecular C-H⋯O and C-H⋯N hydrogen bonds together with slipped π-stacking [centroid-centroid distance = 3.7772 (12) Å] and C-H⋯π (ring) inter-actions lead to the formation of chains extending along the c-axis direction. Additional C-H⋯O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary π-stacking [centroid-centroid distance = 3.5444 (12) Å] inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.5%), H⋯O/O⋯H (18.8%), H⋯N/N⋯H (17.0%) and H⋯C/C⋯H (10.4%) inter-actions.

| S-EPMC6218907 | biostudies-literature

Crystal structure of 2-oxo-1,2-di-phenyl-ethyl diiso-propyl-carbamate.

Project description:The title compound, C21H25NO3, crystallized as a racemic twin in the Sohnke space group P21. In the mol-ecular structure of the title compound, both enanti-omers show a highly similar conformation with the urethane function and the benzoyl group showing an almost perpendicular arrangement [the dihedral angle is 72.46 (8)° in the S-enanti-omer and 76.21 (8)° in the R-enanti-omer]. In the crystal structure, mol-ecules of both enanti-omers show infinite helical arrangements parallel to the b axis formed by weak C-H⋯O hydrogen bonds between the phenyl ring of the benzoyl group and the carbamate carbonyl group. In case of the R-enanti-omer, this helix is additionally stabilized by a bifurcated hydrogen bond between the carbonyl function of the benzoyl group towards both phenyl groups of the mol-ecule.

| S-EPMC8587984 | biostudies-literature

Crystal structure of (5R)-5-[(1S)-1,2-di-hydroxy-eth-yl]-4-meth-oxy-3-phenyl-2,5-di-hydro-furan-2-one.

Project description:In the title compound, C13H14O5, the furan ring is essentially planar [maximum deviation = 0.031?(3)?Å] with a stereogenic center (R) at the sp (3) hybridized C atom. The C atom bearing the dihy-droxy ethyl group is S. The absolute configuration is based on the precursor in the synthesis. The two O-H groups are in an anti conformation with respect to each other. The mean plane of the furan-one group is twisted by 8.2?(4)° from that of the phenyl ring. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds involving furan-one C=O groups and symmetry-related hy-droxy groups, forming a two-dimensional network parallel to (001). Weak C-H?O hydrogen bonds are observed within the two-dimensional network.

| S-EPMC4257168 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbamo-yl]-2-oxo-1,2-di-hydro-quinolin-1-yl}acetate.

Project description:The title com-pound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetra-hydro-2-oxo-quinolin-1-yl)acetate and 4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbomoyl] units, where the oxo-quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C-HOxqn?OEthx and C-HPh-yl?OCarbx (Oxqn = oxoquinolin, Ethx = eth-oxy, Phyl = phenyl and Carbx = carboxyl-ate) weak hydrogen bonds link the mol-ecules into a three-dimensional network sturucture. A ?-? inter-action between the constituent rings of the oxo-quinoline unit, with a centroid-centroid distance of 3.675?(1)?Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821?(8):0.179?(8) and 0.651?(18):0.349?(18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (53.9%), H?O/O?H (28.5%) and H?C/C?H (11.8%) inter-actions. Weak inter-molecular hydrogen-bond inter-actions and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO mol-ecular orbital behaviour was elucidated to determine the energy gap.

| S-EPMC6829727 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-chloro-ethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

Project description:The title compound, C15H12ClNO3, consists of a 1,2-di-hydro-quinoline-4-carb-oxyl-ate unit with 2-chloro-ethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the mol-ecules form zigzag stacks along the a-axis direction through slightly offset ?-stacking inter-actions between inversion-related quinoline moieties which are tied together by inter-molecular C-HPrpn-yl?OCarbx and C-HChlethy?OCarbx (Prpnyl = propynyl, Carbx = carboxyl-ate and Chlethy = chloro-eth-yl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (29.9%), H?O/O?H (21.4%), H?C/C? H (19.4%), H?Cl/Cl?H (16.3%) and C?C (8.6%) 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, the C-HPrpn-yl?OCarbx and C-HChlethy?OCarbx hydrogen bond energies are 67.1 and 61.7?kJ?mol-1, respectively. 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-EPMC6775731 | biostudies-literature

Crystal structure of 2-amino-1,3-di-bromo-6-oxo-5,6-di-hydro-pyrido[1,2-a]quinoxalin-11-ium bromide monohydrate.

Project description:In the title hydrated salt, C12H8Br2N3O(+)·Br(-)·H2O, which was synthesized by the reaction of the pyridine derivative Schiff base N (1),N (4)-bis-(pyridine-2-yl-methyl-ene)benzene-1,4-di-amine with bromine, the asymmetric unit contains a 2-amino-1,3-di-bromo-6-oxo-5,6-di-hydro-pyrido[1,2-a]quinoxalin-11-ium cation, with a protonated pyridine moiety, a bromide anion and a water mol-ecule of solvation. The cation is non-planar with the di-bromo-substituted benzene ring, forming dihedral angles of 24.3?(4) and 11.5?(4)° with the fused pyridine and pyrazine ring moieties, respectively. In the crystal, the cations are linked through a centrosymmetric hydrogen-bonded cyclic R 4 (2)(8) Br2(H2O)2 unit by N-H?Br, N-H?O and O-H?Br hydrogen bonds, forming one-dimensional ribbons extending along b, with the planes of the cations lying parallel to (100).

| S-EPMC4645018 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenyl-quinoxalin-2-one.

Project description:In the title mol-ecule, C23H28N2O, the phenyl ring is inclined to the quinoxaline ring system at a dihedral angle of 20.40 (9)°. In the crystal, C-H⋯O inter-actions between neighbouring mol-ecules form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (70.6%), H⋯C/C⋯H (15.5%) and H⋯O/O⋯H (4.6%) inter-actions. The optimized structure calculated using density functional theory at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied mol-ecular orbital (HOMO) and lowest unoccupied mol-ecular orbital (LUMO) energy gap is 3.8904 eV. Part of the n-nonyl chain attached to one of the nitro-gen atoms of the quinoxaline ring system shows disorder and was refined with a double conformation with occupancies of 0.604 (11) and 0.396 (11).

| S-EPMC8491532 | 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