Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

ABSTRACT: The title mol-ecule, C₂₀H₁₅NO₃, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di-hydro-quinoline unit. In the crystal, corrugated layers are formed by C-H⋯O hydrogen bonds and are stacked by C-H⋯π(ring) inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (26.6%) and H⋯O/O⋯H (16.3%) 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 HOMO-LUMO energy gap is 4.0319 eV.

SUBMITTER: Bouzian Y

PROVIDER: S-EPMC8340981 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

Bouzian Younos Y Chkirate Karim K Mague Joel T JT Al-Ostoot Fares Hezam FH Hammou Ahabchane Noureddine N Essassi El Mokhtar EM

Acta crystallographica. Section E, Crystallographic communications 20210723 Pt 8

The title mol-ecule, C20H15NO3, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di-hydro-quinoline unit. In the crystal, corrugated layers are formed by C-H⋯O hydrogen bonds and are stacked by C-H⋯π(ring) inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (26.6%) and H⋯O/O⋯H (16.3%) inter-actions. The optimized structure calculated us ...[more]

PMID: 34422309

Similar Datasets

Crystal structure and DFT study of benzyl 1-benzyl-2-oxo-1,2-di-hydro-quinoline-4-carboxyl-ate.

Project description:In the title quinoline derivative, C24H19NO3, the two benzyl rings are inclined to the quinoline ring mean plane by 74.09 (8) and 89.43 (7)°, and to each other by 63.97 (10)°. The carboxyl-ate group is twisted from the quinoline ring mean plane by 32.2 (2)°. There is a short intra-molecular C-H⋯O contact forming an S(6) ring motif. In the crystal, mol-ecules are linked by bifurcated C-H,H⋯O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C-H⋯π inter-actions, forming a supra-molecular three-dimensional structure.

| S-EPMC6659339 | 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 and Hirshfeld surface analysis of hexyl 1-hexyl-2-oxo-1,2-di-hydro-quinoline-4-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C22H31NO3, comprises of one mol-ecule. The mol-ecule is not planar, with the carboxyl-ate ester group inclined by 33.47 (4)° to the heterocyclic ring. Individual mol-ecules are linked by aromaticC-H⋯Ocarbon-yl hydrogen bonds into chains running parallel to [001]. Slipped π-π stacking inter-actions between quinoline moieties link these chains into layers extending parallel to (100). Hirshfeld surface analysis, two-dimensional fingerprint plots and mol-ecular electrostatic potential surfaces were used to qu-antify the inter-molecular inter-actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (72%), O⋯H/H⋯O (14.5%) and C⋯H/H⋯C (5.6%) inter-actions.

| S-EPMC7199246 | biostudies-literature

Crystal structure, Hirshfeld surface analysis, inter-action energy and energy framework calculations, as well as density functional theory (DFT) com-putation, of methyl 2-oxo-1-(prop-2-yn-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

Project description:In the title mol-ecule, C14H11NO3, the di-hydro-quinoline core deviates slightly from planarity, indicated by the dihedral angle of 1.07 (3)° between the two six-membered rings. In the crystal, layers of mol-ecules almost parallel to the bc plane are formed by C-H⋯O hydro-gen bonds. These are joined by π-π stacking inter-actions. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (36.0%), H⋯C/C⋯H (28.9%) and H⋯O/O⋯H (23.5%) inter-actions. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the dispersion energy contribution. Moreover, the mol-ecular structure optimized by density functional theory (DFT) at the B3LYP/6-311G(d,p) level is com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC10561202 | biostudies-literature

Ethyl 8-meth-oxy-4-oxo-1,4-di-hydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C13H13NO4, the asymmetric unit contains four independent mol-ecules, each exhibiting an intra-molecular N-H⋯O hydrogen bond. The ethyl group in one of the four mol-ecules is disordered, with a refined occupancy ratio of 0.295 (16):0.705 (16). A face-to-face stacking inter-action is found between the benzene rings of the quinoline units of two of the mol-ecules [centroid-centroid distance = 3.541 (2) Å], which are sandwiched by the other two mol-ecules through N-H⋯O hydrogen bonding. In the crystal, the sandwiched mol-ecules are assembled via stacking inter-actions along the b-axis direction with their translation-symmetry equivalents [centroid-centroid distance = 3.529 (2) Å], and are further linked through N-H⋯O hydrogen bonding. The other two mol-ecules are linked via stacking inter-actions with their inversion-symmetry equivalents [centroid-centroid distances = 3.512 (3) and 3.716 (4) Å] and via N-H⋯O hydrogen bonding.

| S-EPMC4051033 | biostudies-literature

Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C(18)H(14)ClNO(3), the dihydro-quinolin-2-one ring system is almost planar (r.m.s. deviation = 0.033 Å). The carboxyl-ate plane and the phenyl group are twisted away from the dihydro-quinolin-2-one ring system by 50.3 (1) and 64.9 (1)°, respectively. In the crystal structure, inversion-related mol-ecules form R(2) (2)(8) dimers via pairs of N-H⋯O hydrogen bonds.

| S-EPMC2972051 | biostudies-literature

Dimethyl 6-iodo-2-methyl-1,2-di-hydro-quinoline-2,4-di-carboxyl-ate.

Project description:In the title compound, C14H14INO4, the di-hydro-pyridine ring adopts a twist conformation. In the crystal, pairs of N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into inversion R 2 (2)(10) and R 2 (2)(18) dimers, forming infinite double chains running along the c axis.

| S-EPMC3884475 | biostudies-literature

Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C(21)H(25)NO(3), the hydro-pyridine ring that constitutes a part of the hexa-hydro-quinoline fused-ring system adopts a sofa conformation; the methine C atom deviates from the least-squares plane defined by the remaining five non-H atoms (r.m.s. deviation = 0.088?Å) by 0.454?(3)?Å. The phenyl ring is aligned at 85.5?(1)° with respect to this mean plane. In the crystal, adjacent molecules are linked via an N-H?O hydrogen bond, involving the amino group and the carbonyl O atom of the fused-ring system, forming chains running along [100]. The ethyl group is disordered over two positions in a 0.609?(6):0.391?(6) ratio.

| S-EPMC3394024 | biostudies-literature

Crystal structure of ethyl 8-chloro-4-oxo-1,4-di-hydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C12H10ClNO3, the asymmetric unit comprises two independent mol-ecules, and the dihedral angle between the least-square planes of the quinoline ring systems of these mol-ecules is 73.30 (5)°. In the crystal, N-H⋯O hydrogen bonds between the independent mol-ecules lead to supra-molecular layers parallel to (-1-10); both N-H H atoms are bifurcated.

| S-EPMC4571399 | biostudies-literature

Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.

Project description:In the title mol-ecule, C(14)H(15)NO(3), the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C-H⋯π inter-actions link the mol-ecules into centrosymmetric dimers, and weak inter-molecular C-H⋯O hydrogen bonds link these dimers into columns propagated along [100].

| S-EPMC2977288 | 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