Crystal Packing Research Articles

Synthesis, characterization and structural analysis of complexes from 2,2':6',2''-terpyridine derivatives with transition metals.

The synthesis and structural characterization of three families of coordination complexes synthesized from 4'-phenyl-2,2':6',2''-terpyridine (8, Ph-TPY), 4'-(4-chlorophenyl)-2,2':6',2''-terpyridine (9, ClPh-TPY) and 4'-(4-methoxyphenyl)-2,2':6',2''-terpyridine (10, MeOPh-TPY) ligands with the divalent metals Co2+, Fe2+, Mn2+ and Ni2+ are reported. The compounds were synthesized from a 1:2 mixture of the metal and ligand, resulting in a series of complexes with the general formula [M(R-TPY)2](ClO4)2 (where M= Co2+, Fe2+, Mn2+ and Ni2+, and R-TPY= Ph-TPY, ClPh-TPY and MeOPh-TPY). The general formula and structural and supramolecular features were determinated by single-crystal X-ray diffraction for bis(4'-phenyl-2,2':6',2''-terpyridine)nickel(II) bis(perchlorate), [Ni(C21H15N3)2](ClO4)2 or [Ni(Ph-TPY)2](ClO4)2, bis[4'-(4-methoxyphenyl)-2,2':6',2''-terpyridine]manganese(II) bis(perchlorate), [Mn(C22H17N3O)2](ClO4)2 or [Mn(MeOPh-TPY)2](ClO4)2, and bis(4'-phenyl-2,2':6',2''-terpyridine)manganese(II) bis(perchlorate), [Mn(C21H15N3)2](ClO4)2 or [Mn(Ph-TPY)2](ClO4)2. In all three cases, the complexes present distorted octahedral coordination polyhedra and the crystal packing is determined mainly by weak C-H...π interactions. All the compounds (except for the Ni derivatives, for which FT-IR, UV-Vis and thermal analysis are reported) were fully characterized by spectroscopic (FT-IR, UV-Vis and NMR spectroscopy) and thermal (TGA-DSC, thermogravimetric analysis-differential scanning calorimetry) methods.

The physical and cellular mechanism of structural color change in zebrafish

Many animals exhibit remarkable colors that are produced by the constructive interference of light reflected from arrays of intracellular guanine crystals. These animals can fine-tune their crystal-based structural colors to communicate with each other, regulate body temperature, and create camouflage. While it is known that these changes in color are caused by changes in the angle of the crystal arrays relative to incident light, the cellular machinery that drives color change is not understood. Here, using a combination of 3D focused ion beam scanning electron microscopy (FIB-SEM), micro-focused X-ray diffraction, superresolution fluorescence light microscopy, and pharmacological perturbations, we characterized the dynamics and 3D cellular reorganization of crystal arrays within zebrafish iridophores during norepinephrine (NE)-induced color change. We found that color change results from a coordinated 20° tilting of the intracellular crystals, which alters both crystal packing and the angle at which impinging light hits the crystals. Importantly, addition of the dynein inhibitor dynapyrazole-a completely blocked this NE-induced red shift by hindering crystal dynamics upon NE addition. FIB-SEM and microtubule organizing center (MTOC) mapping showed that microtubules arise from two MTOCs located near the poles of the iridophore and run parallel to, and in between, individual crystals. This suggests that dynein drives crystal angle change in response to NE by binding to the limiting membrane surrounding individual crystals and walking toward microtubule minus ends. Finally, we found that intracellular cAMP regulates the color change process. Together, our results provide mechanistic insight into the cellular machinery that drives structural color change.

Crystal structure and Hirshfeld surface analysis of dimethyl 2-oxo-4-(pyridin-2-yl)-6-(thiophen-2-yl)cyclohex-3-ene-1,3-dicarboxylate

In the title compound, C19H17NO5S, the cyclohexene ring adopts nearly an envelope conformation. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming a three-dimensional network. In addition, C—H...π interactions connect the molecules by forming layers parallel to the (010) plane. According to the Hirshfeld surface analysis, H...H (36.9%), O...H/H...O (31.0%), C...H/H...C (18.9%) and S...H/H...S (7.9%) interactions are the most significant contributors to the crystal packing.

Novel Salts of Heterocyclic Polyamines and 5-Sulfosalicylic Acid: Synthesis, Crystal Structure, and Hierarchical Supramolecular Interactions

A series of novel salts of heterocyclic polyamines with 5-sulfosalicylic acid (C4H7N4+)(C7H5O6S−)∙2(H2O) (1), (C4H6ClN4+)(C7H5O6S−)∙H2O (2), (C5H8N3+)(C7H5O6S−)∙H2O (3), (C5H7N6+)(C7H5O6S−)∙H2O (4), (C6H14N22+)(C7H4O6S2−)∙H2O (5), and (C14H19N2+)(C7H5O6S−) (6) have been successfully synthesized. Their crystal structures have been determined by single-crystal X-ray diffraction. Overall, compounds adopt a layered structure with aminium cations and 5-sulfosalicylic anions linked via water molecules. The solid-state architectures of these compounds are dominated by O(N,H)-H⋯O and N-H⋯N hydrogen bonds and stabilized by weak interconnects. C-Cl⋯π and S-O⋯π interactions, apart from π⋯π and C-H(O)⋯π, were reported. Diverse approaches were used to study the effect of substituents in the polyamines in solid-state arrangement. A Hirshfeld surface analysis, with associated 3D Hirshfeld surface maps and 2D fingerprint plots, molecular electrostatic potential, and energy frameworks were used to comprehensively investigate the nature and hierarchy of non-covalent interactions and inspect supramolecular differences. The contact enrichment ratio calculations provided deeper insight into the propensity of interconnects to influence crystal packing. The evaluation of the effects of H-bonding synthons resulting from different substituents in the polyamines on self-assemblies is also presented. In the context of crystal engineering, a specific intramolecular synthon via O-H⋯O observed in nearly all crystals can be employed in the pseudo-cyclic replacement strategy in the design of new molecules.

An Investigation of Two Cu (II)‐Based Hybrid Materials: Physico‐Chemical Characterization, Theoretical Calculation and Evaluation of The Inhibitory Activities against Key Enzymes related to Diabetes and Obesity

AbstractTwo complexes (C6H9N2)2[CuCl4] (1) and (C5H6N2Cl)2[CuCl4] (2) have been synthesized and characterized by single‐crystal X‐ray diffraction which revealed that these phases are centrosymmetric and crystallize, respectively, in monoclinic and triclinic symmetries. The thermal properties of both complexes are investigated as well as the UV‐Vis spectroscopic, photoluminescence properties, electronic paramagnetic resonance and biological activities. The crystal packing of the two compounds is guided by N−H⋅⋅⋅Cl hydrogen bonds and offset π–π stacking interactions; these interactions contribute to the overall stabilization of the structures as they connect anions and cations together into a three‐dimensional network. In addition, the optimized molecular structure was calculated by the Density Functional Theory (DFT) method using the B3LYP function with the LanL2DZ basis set. Subsequently, the thermal behavior was studied by TGA/DTA analyses. Moreover, the optical properties were studied using optical absorption UV‐visible and photoluminescence (PL) spectroscopy. The analysis of the magnetic properties is studied by electronic paramagnetic resonance (EPR). Simultaneously, compound (1) exhibits a potential inhibitory effect against the key enzymes associated with diabetes, obesity, and hyperlipidemia. It demonstrates IC50 values of 0.21 μM and 0.32 μM against α‐amylase and lipase, respectively. Consequently, it emerges as a promising candidate for the treatment of diabetes and obesity.

Synthesis and crystal structures of three organoplatinum(II) complexes bearing natural arylolefin and quinoline derivatives

Three organoplatinum(II) complexes bearing natural arylolefin and quinoline derivatives, namely, [4-methoxy-5-(2-methoxy-2-oxoethoxy)-2-(prop-2-en-1-yl)phenyl](quinolin-8-olato)platinum(II), [Pt(C13H15O4)(C9H6NO)], (I), [4-methoxy-5-(2-oxo-2-propoxyethoxy)-2-(prop-2-en-1-yl)phenyl](quinoline-2-carboxylato)platinum(II), [Pt(C15H19O4)(C10H6NO2)], (II), and chlorido[4-methoxy-5-(2-oxo-2-propoxyethoxy)-2-(prop-2-en-1-yl)phenyl](quinoline)platinum(II), [Pt(C15H19O4)Cl(C9H7N)], (III), were synthesized and structurally characterized by IR and 1H NMR spectroscopy, and by single-crystal X-ray diffraction. The results showed that the cycloplatinated arylolefin coordinates with PtII via the carbon atom of the phenyl ring and the C=Colefinic group. The deprotonated 8-hydroxyquinoline (C9H6NO) and quinoline-2-carboxylic acid (C10H6NO2) coordinate with the PtII atom via the N and O atoms in complexes (I) and (II) while the quinoline (C9H7N) coordinates via the N atom in (III). Moreover, the coordinating N atom in complexes (I)–(III) is in the cis position compared to the C=Colefinic group. The crystal packing is characterized by C—H...π, C—H...O [for (II) and (III)], C—H...Cl [for (III) and π–π [for (I)] interactions.

Comparative Analysis for the Behavior of Beryllium and Magnesium Crystals at Ultrahigh Pressures

The article presents ab initio calculation results on the structural‐phase stability of beryllium and magnesium crystals under high and ultrahigh pressures (multiterapascal regime). Magnesium is shown to undergo a number of structural transformations which markedly reduce the crystal packing factor. As for beryllium, its high‐pressure body‐centered cubic phase remains stable even under ultrahigh pressures. Changes in the electronic structure of Be and Mg crystals under compression are analyzed and some interesting effects are revealed. Specifically, a narrow bandgap appears in the electronic structure of magnesium under pressures above 2.5 TPa. For the metals of interest, pressure‐temperature diagrams are constructed and compared with available experimental and theoretical results from other investigations.

Crystal structure and Hirshfeld surface analysis of 3,3′-[ethane-1,2-diylbis(oxy)]bis(5,5-dimethylcyclohex-2-en-1-one) including an unknown solvate

The title molecule, C18H26O4, consists of two symmetrical halves related by the inversion centre at the mid-point of the central –C—C– bond. The hexene ring adopts an envelope conformation. In the crystal, the molecules are connected into dimers by C—H...O hydrogen bonds with R 2 2(8) ring motifs, forming zigzag ribbons along the b-axis direction. According to a Hirshfeld surface analysis, H...H (68.2%) and O...H/H...O (25.9%) interactions are the most significant contributors to the crystal packing. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9–18] in PLATON. The solvent contribution was not included in the reported molecular weight and density.

Unusually short H···H contacts in intramolecularly cyclized helically fused anthracenes.

The intramolecular coupling of dichloro-substituted helically fused anthracenes using the Yamamoto coupling yielded cyclized products with sterically congested molecular structures. The X-ray analysis and DFT calculations showed that the aromatic framework adopted a nonplanar structure with a twisted conformation about the newly formed single bond, which acts as a chiral axis. Interestingly, the X-ray structure obtained through the Hirshfeld atom refinement revealed short interatomic distances between the inner hydrogen atoms (1.648-1.692 Å), much shorter than the sum of their van der Waals radii. Owing to these unusually short contacts, the 1H NMR spectrum exhibited a significant deshielding (12.5 ppm) and a large nuclear Overhauser effect (44%). Additionally, the IR spectrum displayed a high-frequency shift of the C-H stretching vibration. These observations, along with the noncovalent interaction plot indicative of a characteristic steric environment, strongly support the presence of steric hindrance. Moreover, dynamic NMR measurement of the mesityl-substituted derivative yielded a barrier to helical inversion of 84 kJ mol-1. The optical properties and crystal packing of the cyclized products are also reported.

Ethynyl-substituted benzosiloxaboroles: the role of C(π)⋯B interactions in their crystal packing and use in Cu(i)-catalyzed 1,3-dipolar cycloaddition.

The synthesis and characterization of two novel 6-ethynyl-7-halogen substituted benzosiloxaboroles (Hal = F, Cl) is reported. The crystal structures of these compounds show a unique type of supramolecular assembly dictated by distinctive C(π)⋯B interactions resulting in the formation of columnar networks involving alternating ethynyl groups and boron atoms. The QTAIM, NBO and NCI analyses were performed in order to obtain a deeper quantitative insight into the nature of these interactions including energy and charge density distribution. The fluoro derivative 1c was used as a starting material in Cu-catalyzed 1,3-dipolar cycloaddition reactions with substituted benzenesulfonyl azides giving rise to benzosiloxaboroles with pendant 1-(arylsulfonyl)-1,2,3-triazole-4-yl functionalities or analogous ionic species, i.e., 1,2,3-triazolium arylsulfonates. Screening of antimicrobial activity of obtained derivatives against a wide selection of Gram-positive and Gram-negative bacteria as well as fungi strains was performed and the obtained results were compared with the data obtained previously for related benzosiloxaborole derivatives.

Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

The benzimidazole entity of the title molecule, C17H21N5O, is almost planar (r.m.s. deviation = 0.0262 Å). In the crystal, bifurcated C—H...O hydrogen bonds link individual molecules into layers extending parallel to the ac plane. Two weak C—H...π(ring) interactions may also be effective in the stabilization of the crystal structure. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H...H (57.9%), H...C/C...H (18.1%) and H...O/O...H (14.9%) interactions. Hydrogen bonding and van der Waals interactions are the most dominant forces in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization of the title compound is dominated via dispersion energy contributions. The molecular structure optimized by density functional theory (DFT) at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

A rare example of monoanionic coordination of thiourea ligands to chromium: synthesis and structure

First example of thioureato ligands with chromium(II) has been isolated and is reported here. The reaction of two equivalents of the in situ generated lithium salt of the bulky 1,3-bis(2,6-diethylphenyl)thiourea ligand (L) with [CrCl2] in tetrahydrofuran and subsequent crystallization from hexane led to the formation of the corresponding CrL2 complex. Single crystal X-ray analysis shows a centrosymmetric Cr complex with a square planar geometry in which the crystal packing of the complex is stabilized by C–H⋅⋅⋅H and C–H⋅⋅⋅S interactions. The strongest contributions (6.2%) due to S⋯H/H⋯S interactions have been further confirmed by Hirshfeld analysis that appear as dark red spots in the finger plots. The title compound, [C42H54CrN4S2], crystallized in the triclinic space group, P-1 with cell parameters: a = 9.3310(19) b = 10.987(2) c = 11.061(2) Å, α = 97.36(3) β = 107.26(3) γ = 108.88(3)°, V = 992.6(4) A3, Z = 1.

Iodo-Bridged Dicopper(I) Complex Containing a Benzothienobenzothiophene (BTBT) Unit: Structure, Characterization, and Crystal Packing Effects on Solid-State Photoluminescence

Abstract The title complex was newly synthesized by straightforward ligand substitution of a parent complex having a N2P2 set. The present complex had a deformed rhomboidal {Cu2I2} core with shortened Cu···Cu and prolonged I···I diagonals compared to those of the parent complex and formed one-dimensional channels filled with solvent molecules in crystals. The complex exhibited unusual red shift in solid-state photoluminescence assigned to halogen/metal-to-ligand charge transfer, indicating association of the unique crystal packing containing intramolecular electronic coupling between benzothienobenzothiophene moieties.

Electrospinning Nonspinnable Sols to Ceramic Fibers and Springs.

Electrospinning has been applied to produce ceramic fibers using sol gel-based spinning solutions consisting of ceramic precursors, a solvent, and a polymer to control the viscosity of the solution. However, the addition of polymers to the spinning solution makes the process more complex, increases the processing time, and results in porous mechanically weak ceramic fibers. Herein, we develop a coelectrospinning technique, where a nonspinnable sol (<10 mPa s) consisting of only the ceramic precursor(s) and solvent(s) is encapsulated inside a polymeric shell, forming core-shell precursor fibers that are further calcined into ceramic fibers with reduced porosity, decreased surface defects, uniform crystal packing, and controlled diameters. We demonstrate the versatility of this method by applying it to a series of nonspinnable sols and creating high-quality ceramic fibers containing TiO2, ZrO2, SiO2, and Al2O3. The polycrystalline TiO2 fibers possess excellent flexibility and a high Young's modulus reaching 54.3 MPa, solving the extreme brittleness problem of the previously reported TiO2 fibers. The single-component ZrO2 fibers exhibit a Young's modulus and toughness of 130.5 MPa and 11.9 KJ/m3, respectively, significantly superior to the counterparts prepared by conventional sol-gel electrospinning. We also report the creation of ceramic fibers in micro- and nanospring morphologies and examine the formation mechanisms using thermomechanical simulations. The fiber assemblies constructed by the helical fibers exhibit a density-normalized toughness of 3.5-5 times that of the straight fibers due to improved fracture strain. This work expands the selection of the electrospinning solution and enables the development of ceramic fibers with more attractive properties.

Silver(I) Octanuclear Complexes Containing N'-(4-Oxotiazolidin-2-Iliden)picolinohydrazonamide and Nitrate as Bridge Ligands. An Example of Solvatomorphism?

The versatile coordination chemistry of (2Z,N'E)-N'-(4-oxothiazolidin-2-ylidene)picolinohydrazonamide (HAmDHotaz) facilitated the synthesis of new complexes with different silver(I) salts. This paper describes the synthesis and characterization, through elemental analysis and spectroscopic techniques (when solubility permits), of a series of compounds that illustrate the coordinative and structural diversity achievable with the HAmDHotaz ligand. Five silver clusters containing the [Ag8(AmDHotaz)4]4+ nucleus were structurally analyzed by single-crystal X-ray diffraction and were found to exhibit solvomorphism. The compositions of these are [Ag8(AmDHotaz)4(NO3)3(MeOH)(H2O)](NO3)·MeOH·7.5H2O (1), {[Ag8(AmDHotaz)4(NO3)3(H2O)2](NO3)·9.5(H2O)}n (2), {[Ag8(AmDHotaz)4(NO3)3(H2O)2](NO3)·11.5(H2O)}n (2a), {[Ag8(AmDHotaz)4(NO3)2(H2O)2](NO3)(OH)·6H2O}n (3), and {[Ag8(AmDHotaz)4(NO3)2(H2O)](NO3)(OH)·4.5H2O}n (3a). Argentophilic interactions are present in each of the octanuclear structures, where Ag···Ag distances range from 2.828(2) to 2.986(1) Å. These distances are influenced by crystal packing, determined by the counterion and solvent molecules in the structure. In the solvatomorphs, solvent molecules were observed to be disordered. Various hydrogen-bonding interactions, such as N-H···O-N, O-H···O, N-H···O═C, C-H···O-N, and π-π stacking interactions, contribute to the crystal packing. The influence of these weak interactions on the crystal packing was further analyzed using DFT calculations and Bader's theory of atoms-in-molecules, with a focus on argentophilic interactions and Ag···S interactions.

Design Rules to Optimize the Intermolecular and Long-Range Packing of Organic Semiconductor Crystals

Design Rules to Optimize the Intermolecular and Long-Range Packing of Organic Semiconductor Crystals

Unveiling a Novel Solvatomorphism of Anti-inflammatory Flufenamic Acid: X-ray Structure, Quantum Chemical, and In Silico Studies.

This paper delves into the polymorphism of 2-[3-(trifluoromethyl)anilino]benzoic acid, commonly referred to as flufenamic acid (FA), a pharmaceutical agent employed in treating inflammatory conditions. The central focus of the study is on a newly unearthed solvatomorphic structure of FA in methanol (FAM), and a thorough comparison is conducted with the commercially available standard structure. Employing a comprehensive approach, including X-ray crystallography, Hirshfeld surface analysis, density functional theory (DFT), molecular docking, and molecular dynamics (MD) simulations, the research aims to unravel the structural and functional implications of solvatomorphism. The X-ray crystal structure analysis brings to light notable differences between the standard FA and solvatomorphic FAM, showcasing variations in intermolecular interactions and crystal packing. Key features such as hydrogen bonding, π···π stacking, and C-H···π interactions are identified as influential factors shaping the stability and conformation of the compounds. Hirshfeld surface analysis further quantifies the nature and contribution of intermolecular interactions, providing a comprehensive perspective on molecular stability. Density functional theory offers valuable electronic structure insights, highlighting disparities in frontier molecular orbitals between FA and FAM. Molecular docking studies against prostaglandin D2 11-ketoreductase explore potential drug interactions, unveiling distinct binding modes and hydrogen bonding patterns that shed light on how the solvatomorphic structure may impact drug-target interactions. In-depth molecular dynamics simulations over 100 ns investigate the stability of the protein-ligand complex, with root mean square deviation and root mean square fluctuation analyses revealing minimal deviations and affirming the stability of FAM within the active site of the target protein.

Synthesis and crystal structures of 5,17-dibromo-26,28-dihydroxy-25,27-dipropynyloxycalix[4]arene, 5,17-dibromo-26,28-dipropoxy-25,27-dipropynyloxycalix[4]arene and 25,27-bis(2-azidoethoxy)-5,17-dibromo-26,28-dihydroxycalix[4]arene

The calixarenes, 5,17-dibromo-26,28-dihydroxy-25,27-dipropynyloxycalix[4]arene (C34H26Br2O4, 1), 5,17-dibromo-26,28-dipropoxy-25,27-dipropynyloxycalix[4]arene (C40H38Br2O4, 2) and 25,27-bis(2-azidoethoxy)-5,17-dibromo-26,28-dihydroxycalix[4]arene (C32H28Br2N6O4, 3) possess a pinched cone molecular shape for 1 and 3, and a 1,3-alternate shape for compound 2. In calixarenes 1 and 3, the cone conformations are additionally stabilized by intramolecular O—H...O hydrogen bonds, while in calixarene 2 intramolecular Br...Br interactions consolidate the 1,3-alternate molecular conformation. The dense crystal packing of the cone dialkyne 1 is a consequence of π–π, C—H...π and C—H...O interactions. In the crystal of the diazide 3, there are large channels extending parallel to the c axis, which are filled by highly disordered CH2Cl2 solvent molecules. Their contribution to the intensity data was removed by the SQUEEZE procedure that showed an accessible void volume of 585 Å3 where there is room for 4.5 CH2Cl2 solvent molecules per unit cell. Rigid molecules of the 1,3-alternate calixarene 2 form a columnar head-to-tail packing parallel to [010] via van der Waals interactions, and the resulting columns are held together by weak C—H...π contacts.

Stabilizing Bifurcated Hydrogen Bond in 8-Aminoquinoline Appended Peptides.

The hydrogen bonding interaction between an amide N-H and the amide N of the preceding residue is prevalent in proline-containing proteins and peptides. However, the N-H···N hydrogen bonding interaction is rare in non-prolyl natural peptides due to restricted dihedral angles. Herein, we stabilize this type of interaction in 8-aminoquinoline appended non-prolyl peptides through bifurcated N···H···N hydrogen bond. The 8-aminoquinoline-incorporated model peptides 2a-i were designed, synthesized, and the crystal structures of 2a-c and 2i were solved. Analysis of crystal data reveals that the amide N-H of aminoquinoline is involved in bifurcated hydrogen bonding interaction with the nitrogen of the preceding amino acid residue and the nitrogen in quinoline. Analysis of crystal packing, Hirshfeld surface and fingerprint plots confirms that the intermolecular O···H contacts significantly contribute to stabilizing bifurcated N···H···N hydrogen bonding interaction. Furthermore, NMR experiments and CD spectroscopy were conducted to examine the preferred conformation in solution, and the data corroborate with the crystal structure conformation.

Crystal structure characterization, Hirshfeld surface analysis, and DFT calculation studies of 1-(6-amino-5-nitronaphthalen-2-yl)ethanone

The title compound, C12H10N2O3, was obtained by the deacetylation reaction of 1-(6-amino-5-nitronaphthalen-2-yl)ethanone in a concentrated sulfuric acid methanol solution. The molecule comprises a naphthalene ring system bearing an acetyl group (C-3), an amino group (C-7), and a nitro group (C-8). In the crystal, the molecules are assembled into a two-dimensional network by N...H/H...N and O...H/H...O hydrogen-bonding interactions. n–π and π–π stacking interactions are the dominant interactions in the three-dimensional crystal packing. Hirshfeld surface analysis indicates that the most important contributions are from O...H/H...O (34.9%), H...H (33.7%), and C...H/H...C (11.0%) contacts. The energies of the frontier molecular orbitals were computed using density functional theory (DFT) calculations at the B3LYP-D3BJ/def2-TZVP level of theory and the LUMO–HOMO energy gap of the molecule is 3.765 eV.