Weak Bonds Research Articles

Weakly Hydrated Solute of Mixed Hydrophobic-Hydrophilic Nature.

Infrared (IR) spectroscopy is a commonly used and invaluable tool in studies of solvation phenomena in aqueous solutions. Concurrently, density functional theory calculations and ab initio molecular dynamics simulations deliver the solvation shell picture at the molecular detail level. The mentioned techniques allowed us to gain insights into the structure and energy of the hydrogen bonding network of water molecules around methylsulfonylmethane (MSM). In the hydration sphere of MSM, there are two types of populations of water molecules: a significant share of water molecules weakly bonded to the sulfone group and a smaller share of water molecules strongly bonded to each other around the methyl groups of MSM. The very weak hydrogen bond of water molecules with the hydrophilic group causes the extended network of water hydrogen bonds to be not "anchored" on the sulfone group, and consequently, the MSM hydration shell is labile.

Shear Bond Strength of Orthodontic Brackets Bonded with Thermo-Cured Glass-Based Materials-An In Vitro Study.

The results of orthodontic therapy largely depend, among other factors, on the preparation of the tooth enamel itself and the choice of material used to bond orthodontic brackets. The aim of this in vitro study was to determine the shear bond strength (SBS) and adhesive remnant index (ARI) score of thermo-cured glass-ionomers on different pretreated enamel, in comparison with the commonly used composite cement. Three commercially available nano-ionomer or highly viscous glass-ionomer cements (EQUIA Forte® Fil, EQUIA Fil, Ketac Universal) and two types of compo-sites (Heliosit Orthodontic, ConTec Go!) were investigated in this study. The research involved two hundred human premolars. The teeth were cleaned and polished, then randomly divided into five groups according to the enamel preparation method and the type of material. The enamel was treated in three different ways: polyacrylic acid, phosphoric acid, 5% NaOCl + etching with phosphoric acid, and a control group without treatment. Glass-ionomer cement was thermo-cured with heat from a polymerization unit during setting. Statistical analysis was performed using a Chi-square test and one-way ANOVA for independent samples. Spearman's Rho correlation coefficient was used to examine the relationship. Regardless of the material type, the results indicated that the weakest bond between the bracket and tooth enamel was found in samples without enamel pretreatment. The majority of the materials stayed on the brackets in samples without enamel preparation, according to ARI scores. The study's findings demonstrated that the strength of the adhesion between the bracket and enamel is greatly influenced by enamel etching and glass-ionomer thermo-curing. Clinical investigations would be required to validate the outcomes.

De novo DNA-based catch bonds.

All primary chemical interactions weaken under mechanical stress, which imposes fundamental mechanical limits on the materials constructed from them. Biological materials combine plasticity with strength, for which nature has evolved a unique solution-catch bonds, supramolecular interactions that strengthen under tension. Biological catch bonds use force-gated conformational switches to convert weak bonds into strong ones. So far, catch bonds remain exclusive to nature, leaving their potential as mechanoadaptive elements in synthetic systems untapped. Here we report the design and realization of artificial catch bonds. Starting from a minimal set of thermodynamic design requirements, we created a molecular motif capable of catch bonding. It consists of a DNA duplex featuring a cryptic domain that unfolds under tension to strengthen the interaction. We show that these catch bonds recreate force-enhanced rolling adhesion, a hallmark feature of biological catch bonds in bacteria and leukocytes. This Article introduces catch bonds into the synthetic domain, and could lead to the creation of artificial catch-bonded materials.

First-principles study of Stone–Wales defects in monolayer and Bernal-stacked hexagonal boron nitride

Recently, Stone–Wales (SW) defects gradually attracted people’s research interest because of their unique properties. The theoretical research indicated that the SW defect in hexagonal boron nitride (h-BN) can lead to new defect levels in bandgap, making h-BN apply in ultraviolet emitters. However, the SW defect is always observed in graphene and rarely observed in h-BN in the experiments. Here, we confirmed the SW defects are not easily formed in h-BN under thermodynamic conditions by first-principles calculations. Specifically, the monolayer h-BN with SW defect (h-BN-SW) has the weak bond strength, dynamic stability and high-temperature thermal stability, facilitating the healing of SW defects under high-temperature conditions and the role of hydrogen. Additionally, we found the SW defect in AB stacked h-BN (AB-h-BN) have good mechanical stability, dynamic stability and thermodynamic stability than h-BN-SW, especially for AB-h-BN-2SW (2SW defects formed in upper and lower layer of AB-h-BN, respectively), which can meet the requirements for its application in electronic devices. Even under thermodynamic conditions, the formation of SW defects is extremely challenging. Electron beam irradiation technology provides a window for the generation of SW defects in h-BN. This offers opportunities for the introduction and control of SW defects, while also creating potential for their application in electronic devices. Moreover, we found that the absorption peak broadens, and a new absorption peak appears with the generation of SW defects, which is mainly induced by the decrease of bandgap and the generation of defect levels. Our research can provide theoretical guidance at atomic scale for designing and applying h-BN with SW defect in the experiments.

Exploring the molecular characteristics of organic matter in low-rank coals using GC×GC/TOF-MS plus data mining

In-depth understanding the form of organic matter in low-rank coals contributes to the clean and efficient utilization of coals. Two low-rank coals were successively dissolved with cyclohexane, acetone and methanol at 300 °C, respectively. Six thermal dissolution (TD) extracts were comparatively analyzed using comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry (GC×GC/TOF-MS). Cyclohexane tends to extract low-polar compounds inherent in coal, such as aliphatic hydrocarbons, arenes and phenols. Acetone can extract monocyclic aromatic hydrocarbons containing alkyl side chains. Meanwhile, acetone can form N-H⋯O hydrogen bonds with nitrogen-containing organic compounds (NCOCs), facilitating the extraction of a greater quantity of NCOCs. Methanol breaks the ArCH2OArR structural unit within coal molecules and forms the dominant alkyl-substituted phenol. It was revealed that sequentially TD at 300 °C using different solvents only breaks intermolecular forces and weak covalent bonds. Additionally, a series of isomers of tricyclic aromatic hydrocarbons and alkylphenols were authenticated by GC×GC/TOF-MS. Principal component analysis and hierarchical clustering analysis were applied to mine effective molecular information from the extensive MS data. The statistical results indicate that solvent had a significant impact on the structure and composition of the TD extracts, more so than the variations in coal species. Thus, the conjunction of GC×GC/TOF-MS and chemometrics provided methodological guidance for an enhanced comprehension of the molecular structure of coals.

Effect of Rare Earth Ion Substitution on Phase Decomposition of Apatite Structure.

The paper describes an investigation of phase decomposition of apatite lattice doped with rare earth ions (cerium, samarium, and holmium) at temperatures ranging from 25-1200 °C. The rare-earth ion-doped apatite minerals were synthesized using the sol-gel method. In situ high-temperature powder X-ray diffraction (XRD) was used to observe the phase changes and the lattice parameters were analyzed to ascertain the crystallographic transformations. The expansion coefficient of the compounds was determined, and it was found that the c-axis was the most expandable due to relatively weak chemical bonds along the c-crystallographic axis. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) were used to examine the decomposition properties of the materials. Due to rare earth ion doping, the produced materials had slightly variable decomposition behaviour. The cerium and samarium ions were present in multiple oxidation states (Ce3+, Ce4+, Sm3+, Sm2+), whereas only Ho3+ ions were observed. Rare earth ion substitution affects tri-calcium phosphate proportion during decomposition by regulating concentrations of vacancies. X-ray photoelectron spectroscopy (XPS) analysis indicated that cerium and samarium ion-doped apatite yielded only 25 % tricalcium phosphate during decomposition. This finding advances our understanding of apatite structures, with implications for various high-temperature processes like calcination, sintering, hydrothermal processing, and plasma spraying.

Experimental investigation of styrene destruction by DBD plasma and its conversion pathways

AbstractThis work was devoted to the investigation of the contribution of various species in plasma to styrene decomposition. Different background gases (air, argon, nitrogen, and oxygen) and plasma reactor (in‐plasma, post‐plasma, and post‐plasma with buffer tube) were employed in this experiment. The results showed that degradation and polymerization of styrene occur simultaneously in the plasma treatment process. In the discharge zone, the bombardment of electrons and energetic particles on styrene and its degradation intermediates played a role in breaking its weak bond energy and promoting their conversion. The short‐lived reactive species with high oxidation potential in plasma were the prerequisite for complete degradation of styrene, due to its ability of breaking bonds with large bond energies, such as benzene ring. Away from the discharge zone, long‐lived reactive oxygen species further oxidized and degraded styrene, and its intermediates outside the discharge zone, promoting their mineralization.

Study on the effect of hydrogen bonding network structure in amphoteric surfactant solution on the wettability of coal dust

The interaction between coal, surfactant, and water molecules is a vital surface chemistry problem. The mechanism by which the type of hydrogen bonding network structure (HBNS) between H2O and surfactant molecules in solution wets the coal dust is unclear. In this study, the results of wetting tests and Raman spectroscopy were used to evaluate the wettability of Cocamidopropyl betaine (CAB) with Dodecyldimethyl betaine (BS-12) solutions at different concentrations as well as the type of HBNS inside the solution as a percentage. The analysis revealed that CAB had better wettability on bituminous coal compared with BS-12. In addition, the composition of HBNS in solution changes with increasing concentration, with the proportion of strong hydrogen bonds increasing and the proportion of weak hydrogen bonds decreasing. Molecular dynamics and quantum chemistry results are mutually validated with experiments. The hydrogen bonding coordination number (CN) of water molecules at different concentrations (CNCAB/H2O < CNBS-12/H2O), and the hydrogen bonding interaction energy between water molecules and active agent molecules were investigated. It was finally indicated that CAB binds water molecules in higher numbers and strength than BS-12. This provides a new way to determine the wettability of surfactants.

Effect of functional groups on the adsorption of urea on activated carbon

The recovery of urea, present in the urine of mammals, has the potential of converting a current wastewater pollutant into an energy source due to its high hydrogen content, in alignment with the waste-to-energy principles. Carbon-based materials enable this approach due to their relatively high urea adsorption capacities. This work reveals that the adsorption of urea from aqueous solutions on activated carbon is a combination of weak van der Waals interactions such hydrogen bonds with the aromatic structure of the pristine carbon surface and also with carboxyl groups on the functionalised carbon, showing no appreciable interaction with hydroxyl or lactone groups. The selective introduction and quantification of different oxygen functional groups on activated carbon reveals their independent effect on the urea adsorption capacity, bringing an end to previous discrepancies in the literature. It also demonstrates that the optimisation of carbon materials must balance the increase of carboxyl groups and the decrease of the surface area associated to functionalisation treatments, providing guidance for future developments of carbon-based materials for circular economy applications.

T-shaped CH···π and antiparallel π···π interactions of metronidazole benzoate and phenyl supporting paddle-wheel manganese(II) and zinc(II) carboxylate complexes: Structural, spectroscopic, and theoretical studies

The interaction and mixing of MnCl2·4H2O with 4-methylbenzoic acid (pMeBz) (1) or ZnSO4·7H2O with phenoxylacetic acid (HPOA) (2) in alkaline alcoholic solution at room temperature, in the presence of metronidazole benzoate afforded novel paddle-wheel complexes. The complexes have been characterized by single crystal Xray diffraction (SCXRD) and spectroscopic techniques (FT-IR, NIR-Vis-UV). Both complexes exhibit weak hydrogen bonds and π···π interactions, which impact the isolated molecule arrangement for optimal packing. The crystal packing of these complexes is dependent on π···π interactions. In the manganese complex, parallel and T-shaped benzene···imidazole stacking dominates, while the zinc complex utilizes antiparallel π···π interactions involving the metronidazole benzoate. A π-hole interaction, π(CC)···π*(CO), with a π(CC)···π*(CC) transfer primarily drives the benzoate dimers formation. An additional antiparallel imidazole···imidazole dimer contributes to this crystal assembly. These findings highlight these metal complexes' interplay of electronic structure, electrostatics, and noncovalent interactions. The insights gained from this study can pave the way for designing functional materials with targeted properties by tailoring ligands to exploit specific interactions.

Dual dynamic H-bonds crosslink side chains support a robust polysiloxane elastomer and its self-repairing and recycling properties

Owning excellent mechanical properties and mild repair conditions simultaneously has always been a paradox in the field of self-healing polysiloxane elastomer research. In this work, a robust polysiloxane elastomer with autonomic self-repairing at r. t. and recyclable properties was firstly designed and synthesized. The double strong H-bonds ensure the strength of the elastomer, while the urea bond with relatively weak bond energy also acts as a sacrifice bond to dissipate energy and further bolster the mechanical properties. Meanwhile the double dynamic bonds located in the side chain with stronger molecular activity ability help to get good self-healing performance. Additionally, the material that can be recycled by crushing/remolding and dissolving/remolding methods without compromising their mechanical robustness and self-repairing properties is environmentally friendly.

Aqueous Electrolyte With Weak Hydrogen Bonds for Four-Electron Zinc-Iodine Battery Operates in a Wide Temperature Range.

In the pursuit of high-performance energy storage systems, four-electron zinc-iodine aqueous batteries (4eZIBs) with successive I-/I2/I+ redox couples are appealing for their potential to deliver high energy density and resource abundance. However, susceptibility of positive valence I+ to hydrolysis and instability of Zn plating/stripping in conventional aqueous electrolyte pose significant challenges. In response, polyethylene glycol (PEG 200) is introduced as co-solvent in 2 m ZnCl2 aqueous solution to design a wide temperature electrolyte. Through a comprehensive investigation combining spectroscopic characterizations and theoretical simulations, it is elucidated that PEG disrupts the intrinsic strong H-bonds of water by global weak PEG-H2O interaction, which strengthens the O─H covalent bond of water and intensifies the coordination with Zn2+. This synergistic effect substantially reduces water activity to restrain the I+ hydrolysis, facilitating I-/I2/I+ redox kinetics, mitigating I3 - formation and smoothening Zn deposition. The 4eZIBs in the optimized hybrid electrolyte not only deliver superior cyclability with a low fading rate of 0.0009% per cycle over 20000 cycles and a close-to-unit coulombic efficiency but also exhibit stable performance in a wide temperature range from 40°C to -40°C. This study offers valuable insights into the rational design of electrolytes for 4eZIBs.

Hydrogen‐Bond‐Enhanced Photoreforming of Biomass Furans over a Urea‐Incorporated Cu(II) Porphyrin Framework

AbstractSolar‐driven upgrading of biomass‐derived 5‐hydroxylmethylfurfural (HMF) to 2,5‐furandicarboxylic acid (FDCA) holds great promise for sustainable production of bio‐plastics and resins. However, the process is limited by poor selectivity and sluggish kinetics due to the vertical coordination of HMF at relatively strong metal sites. Here, we purposely developed a Cu(II) porphyrin framework featuring side‐chain incorporated urea linkages, denoted as TBUPP−Cu MOF, to render HMF a weak hydrogen bond at the urea site and flat adsorption via π–π stacking with the benzene moiety. The unique configuration promotes the approaching of −CHO of HMF to the photoexcited porphyrin ring towards kinetically and thermodynamically favourable intermediate formation and subsequent desorption. The charge localisation and orbital energy alignment enable the selective activation of O2 over the porphyrin to generate ⋅O2− and 1O2 instead of highly oxidative H2O2 and ⋅OH via spin‐flip electron transfer, which drive the ambient oxidation of proximal −CHO. The effective utilisation of redox species and circumvented over‐oxidation facilitate a FDCA selectivity of &gt;90 % with a high turnover number of 193 molHMF molCu−1. The facile purification of high‐purity FDCA and zero‐waste recycling of intermediates and durable catalyst feature TBUPP−Cu MOF a promising photo‐oxidation platform towards net‐zero biorefining and organic transformations.

Hydrogen-Bond-Enhanced Photoreforming of Biomass Furans over aUrea-Incorporated Cu(II) Porphyrin Framework.

Solar-driven upgrading of biomass-derived 5-hydroxylmethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) holds great promise for sustainable production of bio-plastics and resins. However, the process is limited by poor selectivity and sluggish kinetics due to the vertical coordination of HMF at relatively strong metal sites. Here, we purposely developed a Cu(II) porphyrin framework featuring side-chain incorporated urea linkages, denoted as TBUPP-Cu MOF, to render HMF a weak hydrogen bond at the urea site and flat adsorption via π-π stacking with the benzyl moiety. The unique configuration promotes the approaching of -CHO of HMF to the photoexcited porphyrin ring towards kinetically and thermodynamically favourable intermediate formation and subsequent desorption. The charge localization and orbital energy alignment enable the selective activation of O2 over the porphyrin to generate ·O2- and 1O2 instead of highly oxidative H2O2 and ·OH via spin-flip electron transfer, which drive the ambient oxidation of proximal -CHO. The effective utilisation of redox species and circumvented over-oxidation facilitate a FDCA selectivity of >90% with a high turnover number of 193 molHMF molCu-1. The facile purification of high-purity FDCA and zero-waste recycling of intermediates and durable catalyst feature TBUPP-Cu MOF a promising photo-oxidation platform towards net-zero biorefining and organic transformations.

Unusually high thermal conductivity in suspended monolayer MoSi2N4

Two-dimensional semiconductors with high thermal conductivity and charge carrier mobility are of great importance for next-generation electronic and optoelectronic devices. However, constrained by the long-held Slack’s criteria, the reported two-dimensional semiconductors such as monolayers of MoS2, WS2, MoSe2, WSe2 and black phosphorus suffer from much lower thermal conductivity than silicon (~142 W·m–1·K–1) because of the complex crystal structure, large average atomic mass and relatively weak chemical bonds. Despite the more complex crystal structure, the recently emerging monolayer MoSi2N4 semiconductor has been predicted to have high thermal conductivity and charge carrier mobility simultaneously. In this work, using a noncontact optothermal Raman technique, we experimentally measure a high thermal conductivity of ~173 W·m–1·K–1 at room temperature for suspended monolayer MoSi2N4 grown by chemical vapor deposition. First-principles calculations reveal that such unusually high thermal conductivity benefits from the high Debye temperature and small Grüneisen parameter of MoSi2N4, both of which are strongly dependent on the high Young’s modulus induced by the outmost Si-N bilayers. Our study not only establishes monolayer MoSi2N4 as a benchmark 2D semiconductor for next-generation electronic and optoelectronic devices, but also provides an insight into the design of 2D materials for efficient heat conduction.

1D-Coordination Polymer of Copper(I) thiocyanate complex with metronidazole: Synthesis, crystal structure, Hirshfeld surface analysis, PXRD, Spectroscopic properties, MEP, QTAIM, π(CN)···tetrel interaction, RDG, and thermal analysis

Within 24 h of slow evaporation of the solution containing CuCl2·2H2O, metronidazole, and NH4SCN, a red-like crystalline Cu(I) complex titled [Cu(SCN)(mnz)]n (1), [where mnz = metronidazole; SCN = thiocyanate], was synthesized. The presence of SCN− during the synthesis induces reduction of the Cu(II) to Cu(I) giving rise to novel 1D coordination polymer. The compound was characterized by single crystal X-ray diffraction, powdered X-ray diffraction, spectroscopic proprieties, and Hirshfeld surface analysis. [Cu(SCN)(mnz)]n crystallizes in the monoclinic space group P21/c. The complex possesses a 1D layer structure constructed by linking the staircase-like [CuSCN]n chains. Intermolecular interactions in the crystals investigation via Hirshfeld surface analysis reveals the major contribution is from O···H/H···O interaction (22.9 %), which is due to the presence of hydrogen bonds of the O − H···O type. The thermal properties were investigated using DTA-TGA and DSC. The study comprises the interpretation of non-covalent interactions through Quantum Theory of Atoms in Molecules (QTAIM), Natural Bond Orbital (NBO) analyses, and Reduced Density Gradient (RDG). The results show the role of interactions between SCN− and mnz through multiple connections involving the oxygen, nitrogen, and sulfur lone pairs and π-bonds for constructing the unit cell. The non-covalent arrangements include very weak hydrogen bonds that cooperatively stabilize the crystal. Along with SCN− bridging copper atoms, growth in the ab plane is favored by an uncommon π···π interaction between SCN− and the imidazole ring of mnz. In this interaction, the π(SN) and π(CN) orbitals perturb the imidazole π(CN) orbital with energies of 0.36 and 0.22 kcal/mol, respectively. In the c direction, a hydrogen bond between the hydroxyl group and CH- fragment from different mnz molecules assists structure stabilization. It is accompanied by a rarely observed π(CN)···tetrel interaction, wherein SCN− donates π-electron density to the antibonding σ(CH) orbital of the methyl carbon.

Ultralow thermal conductivity and high thermoelectric performance induced by dimensionality reduction in chain-like compounds X2PtSe2 (X=K, rb)

Balancing low lattice thermal conductivity (κL) with a high power factor is a major challenge in the research of thermoelectric (TE) materials. In this paper, we report on a class of chain-like compounds, X2PtSe2(X = K, Rb), characterized by strong lattice anharmonicity, weak bonds, and low phonon group velocities. Using first-principles calculations in conjunction with self-consistent phonon theory and the Boltzmann transport equation, we systematically investigate the thermal and electrical transport properties of X2PtSe2(X = K, Rb). At room temperature, the κL of K2PtSe2 and Rb2PtSe2 in the direction perpendicular to the Pt–Se chains is only 0.15 and 0.10 Wm−1K−1, respectively. Additionally, due to the low-dimensional nature of the Pt–Se chains, these compounds exhibit a ‘pudding-mold type’ band structure, contributing to a TE power factor. At 300K, under n-type doping, K2PtSe2 and Rb2PtSe2 achieve TE figures of merit (ZT) values of 1.66 and 1.67, respectively, in the direction perpendicular to the Pt–Se chains. At 500K, the ZT value of Rb2PtSe2 approaches 4, far surpassing traditional TE materials. These results indicate that the chain-like compounds X2PtSe2(X = K, Rb) exhibit excellent TE performance, achieving energy conversion efficiencies comparable to commercial transducer devices.

Novel Li2−2xK2xPbP2O7 glass system: Synthesis, thermal, structural and dielectric properties

Novel Li2−2xK2xPbP2O7 system (x = 0, 0.2, 0.4, 0.6, 0.8, and 1 mol%) was synthesized through the conventional melt-quenching method. The amorphous and crystalline characteristics of the resulting compounds were investigated using X-ray diffraction (XRD) and differential scanning calorimetry (DSC). The study assessed the effect of potassium doping on thermal parameters, including glass transition temperature (Tg), crystallization temperature (Tc), and overall thermal stability. The findings reveal that the stability does not consistently follow a single pattern with K2O doping. Notably, the Li1.6K0.4PbP2O7 glass exhibits the greatest stability. The addition of K2O led to a reduction of the density and an increase in the molar volume of the system. These observations align with FTIR results, which reveal that introducing additional potassium ions results in longer bond lengths and weaker bonds. The spectroscopic study was supported by Raman spectroscopy. Post-annealing XRD analysis revealed the presence of distinct crystalline phases that differed according to the K2O content The structure of the various phosphate groups in the synthesized materials after annealing was also analyzed using Fourier Transform Infrared (FTIR) spectroscopy. Moreover, dielectric studies were conducted over a range of frequencies, and the presence of the relaxation phenomenon as well as the influence of potassium content on dielectric features have been evidenced.

The crystal structures and Hirshfeld surface analysis of three new bromo-substituted 3-methyl-1-(phenylsulfonyl)-1H-indole derivatives

Three new 1H-indole derivatives, namely, 2-(bromomethyl)-3-methyl-1-(phenylsulfonyl)-1H-indole, C16H14BrNO2S, (I), 2-[(E)-2-(2-bromo-5-methoxyphenyl)ethenyl]-3-methyl-1-(phenylsulfonyl)-1H-indole, C24H20BrNO3S, (II), and 2-[(E)-2-(2-bromophenyl)ethenyl]-3-methyl-1-(phenylsulfonyl)-1H-indole, C23H18BrNO2S, (III), exhibit nearly orthogonal orientations of their indole ring systems and sulfonyl-bound phenyl rings. Such conformations are favourable for intermolecular bonding involving sets of slipped π–π interactions between the indole systems and mutual C—H...π hydrogen bonds, with the generation of two-dimensional monoperiodic patterns. The latter are found in all three structures, in the form of supramolecular columns with every pair of successive molecules related by inversion. The crystal packing of the compounds is additionally stabilized by weaker slipped π–π interactions between the outer phenyl rings (in II and III) and by weak C—H...O, C—H...Br and C—H...π hydrogen bonds. The structural significance of the different kinds of interactions agree with the results of a Hirshfeld surface analysis and the calculated interaction energies. In particular, the largest interaction energies (up to −60.8 kJ mol−1) are associated with pairing of antiparallel indole systems, while the energetics of weak hydrogen bonds and phenyl π–π interactions are comparable and account for 13–34 kJ mol−1.

Ethyl 2-[(2-oxo-2H-chromen-6-yl)oxy]acetate

Ethyl 2-[(2-oxo-2H-chromen-6-yl)oxy]acetate, C13H12O5, a member of the pharmacologically important class of coumarins, crystallizes in the monoclinic C2/c space group in the form of sheets, within which molecules are related by inversion centers and 21 axes. Multiple C—H...O weak hydrogen-bonding interactions reinforce this pattern. The planes of these sheets are oriented in the approximate direction of the ac face diagonal. Intersheet interactions are a combination of coumarin system π–π stacking and additional C—H...O weak hydrogen bonds between ethyl acetoxy groups.