Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure and Hirshfeld surface analysis of 4-allyl-2-meth-oxy-6-nitro-phenol.

ABSTRACT: The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-meth-oxy-phenol) with a mixture of nitric acid and sulfuric acid, consists of three independent mol-ecules of similar geometry. Each mol-ecule displays an intra-molecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by inter-molecular C-H?O hydrogen bonds in addition to ?-? stacking inter-actions between the aromatic rings [centroid-centroid distances = 3.6583?(17)-4.0624?(16)?Å]. The Hirshfeld surface analysis and the two-dimensional fingerprint plots show that H?H (39.6%), O?H/H?O (37.7%), C?H/H?C (12.5%) and C?C (4%) are the most important contributors towards the crystal packing.

SUBMITTER: El Ghallab Y

PROVIDER: S-EPMC7057379 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure and Hirshfeld surface analysis of 4-allyl-2-meth-oxy-6-nitro-phenol.

El Ghallab Yassine Y Derfoufi Sanae S Ketatni El Mostafa EM Saadi Mohamed M El Ammari Lahcen L

Acta crystallographica. Section E, Crystallographic communications 20200228 Pt 3

The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-meth-oxy-phenol) with a mixture of nitric acid and sulfuric acid, consists of three independent mol-ecules of similar geometry. Each mol-ecule displays an intra-molecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by inter-molecular C-H⋯O hydrogen bonds in addit ...[more]

PMID: 32148895

Similar Datasets

2-[(1E)-({[(Benzyl-sulfan-yl)methane-thio-yl]amino}-imino)-meth-yl]-6-meth-oxy-phenol: crystal structure and Hirshfeld surface analysis.

Project description:The title di-thio-carbazate ester, C16H16N2O2S2, comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intra-molecular hy-droxy-O-H⋯N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the mol-ecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the mol-ecule, facilitating the formation of inter-molecular N-H⋯S hydrogen bonds leading to eight-membered {⋯HNCS}2 synthons in the crystal. These aggregates are connected by phenyl-C-H⋯O(hy-droxy) inter-actions into a supra-molecular layer in the bc plane; these stack with no directional inter-actions between them. An analysis of the Hirshfeld surface confirms the nature of the inter-molecular inter-actions.

| S-EPMC4910345 | biostudies-literature

Synthesis, crystal structure and spectroscopic and Hirshfeld surface analysis of 4-hy-droxy-3-meth-oxy-5-nitro-benzaldehyde.

Project description:The title compound, C8H7NO5, is planar with an r.m.s. deviation for all non-hydrogen atoms of 0.018 Å. An intra-molecular O-H⋯O hydrogen bond involving the adjacent hy-droxy and nitro groups forms an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by C-H⋯O hydrogen bonds, forming layers parallel to the bc plane. The layers are linked by a further C-H⋯O hydrogen bond, forming slabs, which are linked by C=O⋯π inter-actions, forming a three-dimensional supra-molecular structure. Hirshfeld surface analysis was used to investigate inter-molecular inter-actions in the solid state. The mol-ecule was also characterized spectroscopically and its thermal stability investigated by differential scanning calorimetry and by thermogravimetric analysis.

| S-EPMC7001823 | 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

Crystal structure, Hirshfeld surface analysis, inter-action energy and DFT studies of 4-[(4-allyl-2-meth-oxy-phen-oxy)meth-yl]-1-(4-meth-oxy-phen-yl)-1H-1,2,3-triazole.

Project description:In the title mol-ecule, C20H21N3O3, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C-HMthphn⋯OMthphn (Mthphn = meth-oxy-phen-yl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C-H⋯π(ring) inter-actions, together with π-π stacking inter-actions [centroid-to-centroid distance = 3.7318 (10) Å] between parallel phenyl rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (48.7%) and H⋯C/C⋯H (23.3%) inter-actions. Computational chemistry reveals that the C-HMthphn⋯OMthphn hydrogen bond energy is 47.1 kJ mol-1. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level, is compared with the experimentally determined mol-ecular structure. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7273996 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hy-droxy-3-meth-oxy-5-nitro-benzyl-idene)amino]-benzoate.

Project description:The title Schiff base compound, C17H16N2O6, has an E configuration with respect to the C=N bond, with a dihedral angle between the two benzene rings of 31.90 (12)°. There is an intra-molecular O-H⋯Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers enclosing an R22(4) ring motif. The dimers are linked about an inversion centre by pairs of C-H⋯O hydrogen bonds, which enclose R22(22) loops, forming chains propagating along the [10] direction. Hirshfeld surface analysis and fingerprint plots show enrichment ratios for the H⋯H, O⋯H and C⋯H contacts, indicating a high propensity of such inter-actions in the crystal. Both the nitro group and the CH3-CH2-O- group are positionally disordered.

| S-EPMC6073003 | biostudies-literature

Hirshfeld surface analysis and crystal structure of N-(2-meth-oxy-phen-yl)acetamide.

Project description:The title compound, C9H11NO2, was obtained as unexpected product from the reaction of (4-{2-benz-yloxy-5-[(E)-(3-chloro-4-methyl-phen-yl)diazen-yl]benzyl-idene}-2-phenyl-oxazol-5(4H)-one) with 2-meth-oxy-aniline in the presence of acetic acid as solvent. The amide group is not coplanar with the benzene ring, as shown by the C-N-C-O and C-N-C-C torsion angles of -2.5 (3) and 176.54 (19)°, respectively. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (53.9%), C⋯H/H⋯C (21.4%), O⋯H/H⋯O (21.4%) and N⋯H/H⋯N (1.7%) inter-actions.

| S-EPMC6658953 | biostudies-literature

Crystal structure of 3,4-di-meth-oxy-phenol.

Project description:The title compound, C8H10O3, has two planar mol-ecules in the asymmetric unit possessing mean deviations from planarity of 0.051 and 0.071 Å. In the crystal, there are two distinct infinite chains, both along [010]. The chains are formed by O-H⋯O inter-actions between the phenol and both the 3-meth-oxy and the 4-meth-oxy groups.

| S-EPMC4719955 | biostudies-literature

The crystal structure, Hirshfeld surface analysis and energy frameworks of 2-[2-(meth-oxy-carbon-yl)-3,6-bis-(meth-oxy-meth-oxy)phen-yl]acetic acid.

Project description:In the title compound, C14H18O8, (I), the meth-oxy-carbonyl [-C(=O)OCH3] and the acetic acid [-CH2C(=O)OH] groups are inclined to the benzene ring by 79.24?(11) and 76.71?(13)°, respectively, and are normal to each other with a dihedral angle of 90.00?(13)°. In the crystal, mol-ecules are linked by a pair of O-H?O hydrogen bonds forming the familiar acetic acid inversion dimer. The dimers are linked by two C-H?O hydrogen bonds and an offset ?-? inter-action [inter-centroid distance = 3.6405?(14)?Å], forming layers lying parallel to the (10) plane. The layers are linked by a third C-H?O hydrogen bond and a C-H?? inter-action to form a supra-molecular framework.

| S-EPMC7336770 | biostudies-literature

Crystal structure of 2-{[2-meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]iminomethyl}-4-nitro-phenol.

Project description:In the title compound, C15H11F3N2O4, the N=C bond of the central imine group adopts an E conformation. The dihedral angle between two benzene rings is 6.2 (2)°. There is an intra-molecular bifurcated O-H⋯(N,O) hydrogen bond with S(6) and S(9) ring motifs. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into a helical chain along the 31 screw axis parallel to c. The -CF3 group shows rotational disorder over two sites, with occupancies of 0.39 (2) and 0.61 (2).

| S-EPMC4518952 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-(2,3-di-hydro-1H-perimidin-2-yl)-6-meth-oxy-phenol.

Project description:The title compound, C18H16N2O2, consists of perimidine and meth-oxy-phenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44?(7)° with respect to the best plane of the other five atoms. In the crystal, O-HPhnl?NPrmdn and N-HPrmdn?OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the mol-ecules into infinite chains along the b-axis direction. Weak C-H?? inter-actions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (49.0%), H?C/C?H (35.8%) and H?O/O?H (12.0%) 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 O-HPhnl?NPrmdn and N-HPrmdn?OPhnl hydrogen-bond energies are 58.4 and 38.0?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-EPMC7199263 | 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