Exploring weak intermolecular interactions in two bis-1,3,4-oxadiazoles derivatives: A combined X-ray diffraction, Hirshfeld surface analysis and theoretical studies

Role of fluorine-fluorine and weak intermolecular interactions in the supramolecular network of a new trifluoromethyl-1,5-benzodiazepine: Crystal structure, Hirshfeld surface analysis and theoretical study

Synthesis, characterization, crystal structures, Hirshfeld surface analysis and DFT computational studies of new Schiff Bases derived from Phenylhydrazine

A single crystal X-ray diffraction analysis was performed on two positional isomers (m-tolyl and p-tolyl) of acrylonitrile derivatives, namely, (Z)-3-(4-(pyridin-2-yl) phenyl)-2-(m-tolyl) acrylonitrile (1) and (Z)-3-(4-(pyridin-2-yl)phenyl)-2-(p-tolyl) acrylonitrile (2). Compound 1 crystallized in the monoclinic P21/n space group with two crystallographically independent molecules. Compound 2 also possesses two crystallographically independent molecules and crystallized in the triclinic P-1 space group. The Hirshfeld surface analysis revealed that, in both isomers, intermolecular H⋅⋅⋅H/C/N contacts contribute significantly to the crystal packing. More than 40% of the contribution arises from intermolecular C-H⋅⋅⋅C(π) contacts. In both compounds, the relative contribution of these contacts is comparable, indicating that the positional isomeric effects are marginal. The structures in which these isomers are arranged in the solid state are very similar, and the lattice energies are also comparable between the isomers. The Coulomb-London-Pauli-PIXEL (CLP-PIXEL) energy analysis identified the energetically significant dimers. The strength of the intra- and intermolecular interactions was evaluated using the quantum theory of atoms in molecules approach. The UV-Vis absorbance in three different solvents (chloroform, ethanol, and ethyl acetate) for isomers 1 and 2 are very similar. This result is in good agreement with the time-dependent density-functional theory (TD-DFT) calculations.

Hydantoin-D,L-valine: Synthesis, characterization, and non-covalent interaction analysis from crystallographic studies, DFTB calculations, and Hirshfeld surface analysis

Co-crystals of polynuclear aromatic hydrocarbons and 9H-carbazole with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone acceptor: Varieties in crystal packing, Hirshfeld surface analysis and quantum-chemical studies

Synthesis, Hirshfeld surface analysis, DFT calculations, photoluminescence, spectroscopic and second order non linear optical studies on ammonium hydrogensquarate squaric acid monohydrate crystal

An organic-inorganic hybrid compound bis(benzamidinium)tetrachlorocobaltate(II) monohydrate, (C7H9N2)2[CoCl4]·H2O, was synthesized by slow evaporation at room temperature and characterized by powder and single-crystal X-ray diffraction (XRD), IR, UV-vis spectroscopies, and Hirshfeld surface analysis. Single-crystal X-ray diffraction analysis indicates that the structure consists of a succession of mixed layers formed by organic cations, inorganic anions and water molecules parallel to the (ab) plane and propagate according to the c-axis. The structure is stabilized by N-H···Cl, N-H···O, O-H···Cl hydrogen bonds, Cl···Cl and π-π interactions. The powder XRD analysis confirms the phase purity of the crystalline sample, while the composition of our phase was verified by semi-quantitative analysis EDX. The DFT calculations were performed using the B3LYP functional and 6-311 + G(2d,2p) basis set for H, C, N, Cl and LANL2DZ for Co. Comprehensive experimental and theoretical structural studies on the compound were carried out through IR and UV-visible spectroscopies. The thermal stability of the three-dimensional (3-D) network of this compound was also discussed. The in vitro antibacterial activity of the compound against different bacterial strains was evaluated. Hirshfeld surface analysis was used to show surface contours and 2-D fingerprint plots have been used to analyze intermolecular interactions.

Synthesis, Characterization, Crystal Structure, Hirshfeld surface analysis and DFT studies of novel compounds based on the methoxynaphthalene ring

Structural elucidation, Hirshfeld surface analysis and quantum mechanical study of para-nitro benzylidene methyl arjunolate

2D hydrogen bonded organic framework (2D-HOF) in benzodioxane-coupled-pyridine as a charge carrier: Synthesis, structural, quantum computational investigation

Different phosphoric triamide [HN]3-nP(O)[N]n (n = 1, 2) skeletons lead to identical non-covalent interactions assemblies: X-ray crystallography investigation, Hirshfeld surface analysis and molecular docking study against SARS-CoV-2

Exploration of supramolecular interactions, Hirshfeld surface, FMO, molecular electrostatic potential (MEP) analyses of pyrazole based Zn(II) complex

Two new phosphoric triamides, N-(2-chloro-5-fluorobenzoyl)-N′,N"-bis(morpholin-4-yl)-phosphoric triamide, (2-Cl,5-F-C6H3C(O)NH)P(O)(NC4H8O)2, 1, and N,N′-dibenzyl-N"-(2-chloro-5-fluorobenzoyl)-N,N′-diethylphosphoric triamide, (2-Cl,5-F-C6H3C(O)NH)P(O)(N(C2H5)(CH2C6H5))2, 2, were synthesized and characterized by 1H-, 13C-, 31P-, 19F-NMR and IR spectroscopies and single-crystal X-ray diffraction analysis. Different orientations of P(O) versus NH, anti in 1 and syn in 2, lead to different hydrogen bond patterns, mediated by N–H⋯O, as a linear arrangement forming a C(4) motif and a dimeric aggregate with an $$R_{2}^{2}\left( 8 \right)$$ ring motif, respectively. The crystal packing of both compounds present a three-dimensional supramolecular assembly, made by the cooperation from weak intermolecular interactions, C–H⋯O and C–H⋯π, for 1 and 2, and π⋯π for 2. Hirshfeld surface analysis demonstrates that the H⋯H contacts are decisive for both structures with contribution portions of 39.1% for 1 and 49.6% for 2. The O⋯H/H⋯O (1: 24.4% and 2: 9.6%) contacts are the characteristic intermolecular interactions, showing a pair of sharp spikes; while C⋯H/H⋯C contacts (1: 11.3% and 2: 21.7%), associated to the π⋯H/H⋯π interactions, can be illustrated as wings in the corresponding fingerprint plots. The C⋯C contacts are revealed for 2 (1.6%), associated to π⋯π interaction observed in the X-ray analysis. Two phosphoric triamides with the same [C(O)NH]P(O)[N(C)(C)]2 skeleton but with different molecular assemblies were investigated by the analysis of Hirshfeld surfaces and fingerprint plots.

Synthesis, crystal structure elucidation and interactions in 1,2,4,5-tetraazaspiro[5.5]undecane-3-thione:Hirshfeld surface analysis, 2d fingerprint plots and 3D energy framework calculations

The crystallographic study of 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) reveals that the compound crystallizes in the centrosymmetric space group $$P2_{1}/c$$ . In the solid state, the structure of the title compound exhibits two strong intramolecular $$\hbox {O}{-}\hbox {H}\cdots \hbox { O}$$ hydrogen bonding interactions. Further, molecules of the title compound are self-assembled by weak intermolecular $$\hbox {C}{-}\hbox {H}\cdots \hbox {O}, \pi \cdots \pi $$ and $$\hbox {H}\cdots \hbox { H}$$ and $$\hbox {C}{-}\hbox {H}\cdots \hbox { Br}$$ contacts. Various intermolecular interaction that exist in the crystal structure and their energetics are quantified using PIXEL, DFT and QTAIM analyses. Six different motifs are identified from the PIXEL calculation. Lattice energy calculation suggests that the dispersion energy has the highest contribution for the crystal formation. The relative contributions of various intermolecular contacts in the title compound and its closely related analogs are evaluated using Hirshfeld surface analysis and the decomposed fingerprint plots. The common packing features exist between the title compound and its related analogs are identified. The quantitative molecular electrostatic potential surface diagram depicts the potential binding sites which are in good agreement with the crystal structure of the title compound. The structures of title compound in gas and solvent phases are compared with the experimental structure and reveals that they are superimposed very well. The vibrational modes of the monomer and four most stabilized dimers are characterized using both the experimental and DFT calculations. The UV-Vis spectrum is calculated using time dependent-DFT (TD-DFT) method and compared with experimental spectrum. The results indicate that the calculated energy of absorbance and oscillator strength correlate well with the experimental data. SYNOPSIS. Synthesis and crystal structure analysis of 2,2’-((4-bromophenyl)methylene) bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) are reported. Molecules of this compound are self-assembled by intermolecular $$\hbox {C}{-}\hbox {H}\cdots \hbox {O}$$ , $$\pi \cdots \pi $$ and $$\hbox {H}\cdots \hbox { H}$$ and $$\hbox {C}{-}\hbox {H}\cdots \hbox { Br}$$ interactions. The relative contributions of various intermolecular interactions in the bromo derivative and its closely related analogs are quantified using theoretical approaches.