Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure and Hirshfeld surface analysis of 2-(4-nitro-phen-yl)-2-oxoethyl picolinate.

ABSTRACT: 2-(4-Nitro-phen-yl)-2-oxoethyl picolinate, C14H10N2O5, was synthesized under mild conditions. The chemical and mol-ecular structures were confirmed by single-crystal X-ray diffraction analysis. The mol-ecules are linked by inversion into centrosymmetric dimers via weak inter-molecular C-H?O inter-actions, forming R 2 2(10) ring motifs, and further strengthened by weak ?-? inter-actions. Hirshfeld surface analyses, the d norm surfaces, electrostatic potential and two-dimensional fingerprint (FP) plots were used to verify the contributions of the different inter-molecular inter-actions within the supra-molecular structure. The shape-index surface shows that two sides of the mol-ecules are involved with the same contacts in neighbouring mol-ecules and curvedness plots show flat surface patches that are characteristic of planar stacking.

SUBMITTER: Sanjeeva Murthy TN

PROVIDER: S-EPMC6829725 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure and Hirshfeld surface analysis of 2-(4-nitro-phen-yl)-2-oxoethyl picolinate.

Sanjeeva Murthy T N TN Chidan Kumar C S CS Naveen S S Veeraiah M K MK Raghava Reddy Kakarla K Warad Ismail I

Acta crystallographica. Section E, Crystallographic communications 20191029 Pt 11

2-(4-Nitro-phen-yl)-2-oxoethyl picolinate, C14H10N2O5, was synthesized under mild conditions. The chemical and mol-ecular structures were confirmed by single-crystal X-ray diffraction analysis. The mol-ecules are linked by inversion into centrosymmetric dimers via weak inter-molecular C-H⋯O inter-actions, forming R 2 2(10) ring motifs, and further strengthened by weak π-π inter-actions. Hirshfeld surface analyses, th ...[more]

PMID: 31709105

Similar Datasets

Crystal structure and Hirshfeld surface analysis of 2-(4-nitro-phen-yl)-2-oxoethyl benzoate.

Project description:The title com-pound, C15H11NO5, is relatively planar, with the planes of the two aromatic rings being inclined to each other by 3.09 (5)°. In the crystal, mol-ecules are linked by a pair of C-H⋯O hydrogen bonds, forming inversion dimers, which enclose an R 2 2(16) ring motif. The dimers are linked by a further pair of C-H⋯O hydrogen-bonds forming ribbons enclosing R 4 4(26) ring motifs. The ribbons are linked by offset π-π inter-actions [centroid-centroid distances = 3.6754 (6)-3.7519 (6) Å] to form layers parallel to the ac plane. Through Hirshfeld surface analyses, the d norm surfaces, electrostatic potential and two-dimensional fingerprint (FP) plots were examined to verify the contributions of the different inter-molecular contacts within the supra-molecular structure. The shape-index surface shows that two sides of the mol-ecule are involved with the same contacts in neighbouring mol-ecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.

| S-EPMC6829730 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-(4-nitro-phen-yl)-2-oxoethyl 2-chloro-benzoate.

Project description:The title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56?(11)°. The central -C(=O)-C-O-C(=O)- bridge is slightly twisted, with a C-C-O-C torsion angle of 164.95?(16)°. In the crystal, mol-ecules are linked by C-H?O and C-H?Cl hydrogen bonds, forming layers parallel to the (101) plane. The layers are linked by a further C-H?O hydrogen bond, forming a three-dimensional supra-molecular structure. There are a number of offset ?-? inter-actions present between the layers [inter-centroid distances vary from 3.8264?(15) to 3.9775?(14)?Å]. Hirshfeld surface analyses, the d norm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different inter-molecular contacts within the supra-molecular structure. The shape-index surface shows that two sides of the mol-ecule are involved in the same contacts with neighbouring mol-ecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.

| S-EPMC6829745 | biostudies-literature

Crystal structure, DFT calculations and Hirshfeld surface analysis of 3-(4-methyl-phen-yl)-6-nitro-1H-indazole.

Project description:The asymmetric unit of the title compound, C14H11N3O3, consists of two independent mol-ecules having very similar conformations in which the indazole moieties are planar. The independent mol-ecules are distinguished by small differences in the rotational orientations of the nitro groups. In the crystal, N-H?O and C-H?O hydrogen bonds form zigzag chains along the b-axis direction. Additional C-H?O hydrogen bonds link the chains into layers parallel to (10). These are connected by slipped ?-stacking and C-H??(ring) inter-actions.

| S-EPMC6281119 | biostudies-literature

(E)-1-(2,6-Di-chloro-phen-yl)-2-(3-nitro-benzyl-idene)hydrazine: crystal structure and Hirshfeld surface analysis.

Project description:The stabilized conformation of the title compound, C13H9Cl2N3O2, is similar to that of the isomeric compound (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine. The 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25?(16)°. In the crystal, face-to-face ?-? stacking inter-actions along the a-axis direction occur between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. The mol-ecules are further linked by C-H?O contacts and N-H?O and C-H?Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular layers parallel to (100). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H?H (22.1%), Cl?H/H?Cl (20.5%), O?H/H?O (19.7%), C?C (11.1%) and C?H/H?C (8.3%) inter-actions.

| S-EPMC7405561 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of N,N'-bis-(2-nitro-phen-yl)glutaramide.

Project description:The asymmetric unit of the title compound, C17H16N4O6, contains two independent mol-ecules (A and B). The two benzene rings are twisted by an angle of 79.14?(7)° in mol-ecule A, whereas, in mol-ecule B, they are inclined by 19.02?(14)°. The conformations of the mol-ecules are stabilized by intra-molecular N-H?O hydrogen bonds between the amide nitro-gen atom and the O atom of the ortho-nitro substituent on the phenyl ring, enclosing an S(6) ring motif. In the amide and aliphatic segments, all the N-H, C=O and C-H bonds are anti to each other. In the crystal, the A and B mol-ecules are linked by inter-molecular amide-to-amide N-H?O hydrogen bonds, resulting in chains running along the b-axis direction. The inter-molecular inter-actions were analysed using Hirshfeld surface analysis. The two-dimensional fingerprint plots of the inter-molecular contacts indicate that the major contributions are from H?H and O?H inter-actions.

| S-EPMC6176432 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-di-chloro-phen-yl)-2-(2-nitro-benzyl-idene)hydrazine.

Project description:In the title compound, C13H9Cl2N3O2, the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16?(14)°. In the crystal, face-to-face ?-? stacking inter-actions occur along the a-axis direction between the centroids of the 2,6-di-chloro-phenyl ring and the nitro-substituted benzene ring. Furthermore, these mol-ecules show intra-molecular N-H?Cl and C-H?O contacts and are linked by inter-molecular N-H?O and C-H?Cl hydrogen bonds, forming pairs of hydrogen-bonded mol-ecular layers parallel to (20). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H?H (23.0%), O?H/H?O (20.1%), Cl?H/H?Cl (19.0%), C?C (11.2%) and H?C/C?H (8.0%) inter-actions.

| S-EPMC7405556 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

Project description:In the title compound, C14H8Cl2FN3O2, the 4-fluoro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29?(8)°. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds into chains running parallel to the c axis. The crystal packing is further stabilized by C-Cl??, C-F?? and N-O?? inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H?O/O?H (15.5%), H?H (15.3%), Cl?H/H?Cl (13.8%), C?H/H?C (9.5%) and F?H/H?F (8.2%) inter-actions.

| S-EPMC6362658 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitro-phen-yl)imino]-meth-yl}phenol.

Project description:The title compound, C15H14N2O3, was prepared by condensation of 2-hy-droxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenyl-amine in ethanol. The configuration of the C=N bond is E. An intra-molecular O-H?N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C-C-N-C torsion angle of 178.53?(13)°]. In the crystal, mol-ecules are linked by C-H?O inter-actions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (37.2%), C?H (30.7%) and O?H (24.9%) inter-actions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311?G(d,p) level is compared to the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7534237 | biostudies-literature

2-Methyl-4-(4-nitro-phen-yl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study.

Project description:The di-substituted acetyl-ene residue in the title compound, C11H11NO3, is capped at either end by di-methyl-hydroxy and 4-nitro-benzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the mol-ecular packing is the formation, via hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds, of hexa-meric clusters about a site of symmetry . The aggregates are sustained by 12-membered {⋯OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C-H⋯O(nitro) inter-actions, involving both nitro-O atoms. The aforementioned inter-actions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker inter-molecular contacts.

| S-EPMC6690440 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-methyl-3-nitro-N-[(E)-(5-nitro-thio-phen-2-yl)methyl-idene]aniline.

Project description:The title compound, C12H9N3O4S, synthesized by condensation of 5-nitro-thio-phene-2-carbaldehyde and 2-methyl-3-nitro-aniline, crystallizes in the ortho-rhom-bic space group P212121. In the mol-ecule, the aromatic benzene and thio-phene rings are twisted with respect to each other, making a dihedral angle of 23.16 (7)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds into chains extending along the c-axis direction. Weak π-π stacking inter-actions along the a-axis direction provide additional stabilization of the crystal structure. The roles of the various inter-molecular inter-actions were clarified by Hirshfeld surface analysis, which reveals that the crystal packing is dominated by O⋯H (39%) and H⋯H (21.3%) contacts. The crystal studied was refined as a two-component inversion twin.

| S-EPMC7869546 | 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