(E)-5-(4-Methyl-benzyl-idene)-1-phenyl-4,5,6,7-tetra-hydro-1H-indazol-4-one
C Selva Meenatchi1, S Athimoolam2, J Suresh1
1Department of Physics, The Madura College, Madurai 625 011, India.
Iucrdata
|November 7, 2022
Summary
This study details the molecular structure and crystal packing of a novel organic compound. Key findings reveal specific dihedral angles and significant intermolecular interactions, including C-H⋯O bonds, influencing crystal stability.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional structure and intermolecular forces of organic molecules is crucial for predicting their physical and chemical properties.
- The title compound, C21H18N2O, presents an interesting scaffold for investigating conformational preferences and crystal packing.
Purpose of the Study:
- To elucidate the molecular structure, including conformational analysis, of the title compound (C21H18N2O).
- To investigate the intermolecular interactions present in the crystal lattice.
- To analyze the contribution of various interactions to the overall crystal stability using Hirshfeld surface analysis.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise three-dimensional structure.
- Conformational analysis was performed by measuring dihedral angles between key ring systems.
- Hirshfeld surface analysis was utilized to quantify and visualize intermolecular interactions.
Main Results:
- The non-aromatic six-membered ring adopts a distorted envelope conformation.
- Significant dihedral angles were observed: 75.3° between phenyl and 4-tolyl rings, 41.9° and 65.5° between the 1,2-diazole ring and the phenyl and 4-tolyl rings, respectively.
- Hirshfeld surface analysis revealed dominant H⋯H (51.7%) and C⋯H/H⋯C (29.2%) contacts, with a notable contribution from C-H⋯O interactions (8.6%).
Conclusions:
- The title compound exhibits a specific, non-planar conformation in the solid state.
- Intermolecular interactions, particularly C-H⋯O, H⋯H, and C⋯H/H⋯C contacts, play a vital role in stabilizing the crystal structure.
- Hirshfeld surface analysis provides valuable insights into the nature and strength of these stabilizing interactions.
More Related Videos
Related Concept Videos
01:34NMR Spectroscopy of Benzene Derivatives
8.7K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.7K
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
8.2K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
8.2K
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
4.1K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.1K
01:23Nomenclature of Aromatic Compounds with a Single Substituent
8.5K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.5K
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
2.3K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.3K
01:19Diazonium Group Substitution: –OH and –H
2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K