Pyridine Moiety Research Articles

Host-guest complexes of a cryptand based on 5H-cyclopenta[2,1-b:3,4b′]pyridine moieties: prediction of ion selectivity by quantum chemical calculations XVI

Selective alkaline and earth alkaline metal ion encapsulation by six different Lehn-type cryptands was predicted by DFT (B3LYP/LANL2DZp) computational chemistry. All cryptands contain three identical moieties connected by the aliphatic nitrogen atom, constructing a very structurally flexible system for accommodating different-sized metal cations. Inspiration for selected hosts was taken from already well-known Lehn-type Cryptand [phen.phen.phen] where one phenanthroline was substituted by 5H-cyclopenta[2,1-b:3,4b′]pyridine in which the CH2– group was replaced by a series of heteroatoms forming the selected series of investigated hosts. The ion selectivity and the ability of the hosts to adjust their structure to accommodate the metal cations successfully were based on energy and geometric criteria. Medium-size cations have been proven to be best fitted for the selected host series.

Unexpected Reduction of a Coordinated Diazapyridinophane Ligand Bound to Chromium(III) Ion Leading to Delocalization of the Unpaired Electron across Two Isolated Pyridine Units.

In the tetraazamacrocyclic ligand N,N'-dimethyl-2,11-diaza-[3.3](2,6)pyridinophane (L-N4 Me2 ), the two pyridine units are separated from each other by sp3 -hybridized triatomic bridges. Such electronically isolated pyridine moieties are considerably less prone to reductions than di- or triimines. A detailed structural, magnetic, and spectroscopic investigation of the complexes [Cr(L-N4 Me2 )(OAc)2 ] and [Cr(L-N4 Me2 )(OAc)2 ](PF6 ), in combination with theoretical calculations, reveals that the reduced complex must be described as a chromium(III) ion coordinated to the anionic radical ligand (L-N4 Me2 )⋅- rather than a low-spin chromium(II) ion bound to closed-shell ligands. Thus, it is, to the best of our knowledge, only the second example of a stable and structurally characterized metal complex containing a reduced isolated pyridine unit. The stability is attributed to the delocalization of the unpaired electron across the two pyridine units, mediated by their interaction to the metal ion.

Sterically attenuated electronic communication in cobalt complexes of meridional isoquinoline-derived ligands for applications in electrocatalysis.

The ability to synthetically tune the ligand frameworks of redox-active molecules is of critical importance to the economy of solar fuels because manipulating their redox properties can afford control over the operating potentials of sustained electrocatalytic or photoelectrocatalytic processes. The electronic and steric properties of 2,2':6',2″-terpyridine (Terpy) ligand frameworks can be tuned by functional group substitution on ligand backbones, and these correlate strongly to their Hammett parameters. The synthesis of a new series of tridentate meridional ligands of 2,4,6-trisubstituted pyridines that engineers the ability to finely tune the redox potentials of cobalt complexes to more positive potentials than that of their Terpy analogs is achieved by aryl-functionalizing at the four-position and by including isoquinoline at the two- and six-positions of pyridine (Aryl-DiQ). Their cobalt complex syntheses, their electronic properties, and their catalytic activity for carbon dioxide (CO2) reduction are reported and compared to their Terpy analogs. The cobalt derivatives generally experience a positive shift in their redox features relative to the Terpy-based analogs, covering a complementary potential range. Although those evaluated fail to produce any quantifiable products for the reduction of CO2 and suffer from long-term instability, these results suggest possible alternate strategies for stabilizing these compounds during catalysis. We speculate that lower equilibrium association constants to the cobalt center are intrinsic to these ligands, which originate from a steric interaction between protons on the pyridine and isoquinoline moieties. Nevertheless, the new Aryl-DiQ ligand framework has been engineered to selectively tune homoleptic cobalt complexes' redox potentials.

Synthesis of chalcone derivatives with methoxybenzene and pyridine moieties as potential antimalarial agents

Malaria remains an endemic disease in tropical regions, urgently needed the search for effective antimalarial agents due to resistance against existing drugs. This study investigated the potential antimalarial activity of pyridine-based chalcone derivatives against P. falciparum 3D7 and FCR3 strains. The chalcones were synthesized through a one-pot method using various pyridine carbaldehyde, resulting in yields ranging from 53.74 to 86.37%, and all products were characterized using FTIR, GC-MS, and NMR spectroscopies. Among the six chalcones tested, chalcone A [1-(2-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one] displayed the highest antimalarial activity with IC50 values of 0.48 and 0.31 μg/mL against P. falciparum 3D7 and FCR3 strains, respectively, and a resistance index of 0.65. Molecular docking studies highlighted the interaction of the carbonyl group of all chalcones with Asn108 amino acid residue in the PfDHFR-TS active site via hydrogen bonding, demonstrating their potential as the antimalarial agent. Notably, the positioning of methoxy and pyridine substituents significantly influenced the antimalarial activity of the chalcones.

A Multi-Pyridine-Anchored and -Linked Bilayer Photocathode for Water Reduction.

The development of efficient photocathodes is of critical importance for the constructions of promising tandem photo-electrochemical cells. Most known dye-sensitized photocathodes are prepared with the conventional carboxylic or phosphonic acid anchors and require the presence of other terminal linking groups to connect catalysts; they suffer from high synthetic difficulty and low adsorption stability in aqueous media. Here, a compact bilayer photocathode has been prepared by using a pyrene-based photosensitizer with multiple terminal pyridine moieties as both the anchoring and linking groups to connect a Co hydrogen-evolution catalyst to the NiO substrate. The catalyst and dye molecule are assembled in a layer-by-layer manner on NiO through the metal-pyridine coordination. This photocathode exhibits good dye adsorption stability in aqueous media. A stable cathodic photocurrent of 70 μA cm-2 was achieved, with H2 being generated at the photocathode under the visible-light irradiation. The Faraday efficiency of H2 evolution was estimated to be 9.1 %. Transient absorption spectral studies suggest that the interfacial hole transfer occurs within a few picoseconds. The integration of the organic photosensitizer with pyridine anchoring and linking groups is expected to provide a simple method for the fabrication of stable and efficient photocathodes.

Design, synthesis, in vitro, and in silico evaluations of kojic acid derivatives linked to amino pyridine moiety as potent tyrosinase inhibitors

In the present study, novel series of kojic acid derivatives conjugated to amino pyridine moiety were designed and synthesized to explore their inhibitory activity against tyrosinase. To this end, the structure of all derivatives was characterized by 1H NMR, 13C NMR, FT-IR, and elemental analysis. Next, all derivatives were evaluated against tyrosinase compared to the kojic acid as positive control and exhibited different inhibitory potencies. Furthermore, the antioxidant potential of all derivatives was determined. The kinetic analysis of the most active agent revealed that 3-hydroxy-6-(hydroxymethyl)-2-((3-nitrophenyl)(pyridin-2-ylamino)methyl)-4H-pyran-4-one (4h) binds to the enzyme in the uncompetitive mode of action. The docking analysis and molecular dynamic simulations showed considerable binding affinity and significant interactions with tyrosinase enzyme to target the melanogenesis pathway, proposing them as potent candidates to control hyperpigmentation in the future.

Construction of intramolecular donor–acceptor type carbon nitride for photocatalytic hydrogen production

High-efficiency photocatalysts based on organic polymeric semiconductor are often limited by slow charge separation kinetics and sluggish redox reaction dynamics. Herein, the donor–acceptor conjugated polymeric carbon nitride (D/A-CN) was synthesized by grafting benzene ring and pyridine moiety into the backbone of CN through a flexible pyrolysis strategy. The D/A-CN shows a high photocatalytic H2 evolution rate of 4795 µmol·h−1·g−1, which is ≈6.08 times higher than that of pristine CN (787.5 µmol·h−1·g−1). Both experimental and theoretical results confirm that the robust internal electric field is established in the D/A-CN framework due to the enhanced molecular dipole, which apply a kinetic force to facilitate the separation and mobility of photogenerated carriers. Meanwhile, the deeper conduction band potential caused by the elevated orbital energy level of D/A-CN contributes to the enhanced reduction ability of photoinduced electron. Consequently, the faster carrier transfer kinetics and the stronger thermodynamic reduction driving force synergistically lead to efficient photocatalytic H2 production of D/A-CN. This work reinforces the comprehension of the structure-performance relationship of donor–acceptor structural photocatalysts and provides an insight for enhancing the photocatalytic activity of polymeric photocatalysts at the molecular level.

Vanadium(V) Pyridine-Containing Schiff Base Catecholate Complexes are Lipophilic, Redox-Active and Selectively Cytotoxic in Glioblastoma (T98G) Cells.

Two new series of complexes with pyridine-containing Schiff bases, [VV O(SALIEP)L] and [VV O(Cl-SALIEP)L] (SALIEP=N-(salicylideneaminato)-2-(2-aminoethylpyridine; Cl-SALIEP=N-(5-chlorosalicylideneaminato)-2-(2-aminoethyl)pyridine, L=catecholato(2-) ligand) have been synthesized. Characterization by 1 H and 51 V NMR and UV-Vis spectroscopies confirmed that: 1) most complexes form two major geometric isomers in solution, and [VV O(SALIEP)(DTB)] (DTB=3,5-di-tert-butylcatecholato(2-)) forms two isomers that equilibrate in solution; and 2) tert-butyl substituents were necessary to stabilize the reduced VIV species (EPR spectroscopy and cyclic voltammetry). The pyridine moiety within the Schiff base ligands significantly changed their chemical properties with unsubstituted catecholate ligands compared with the parent HSHED (N-(salicylideneaminato)-N'-(2-hydroxyethyl)-1,2-ethanediamine) Schiff base complexes. Immediate reduction to VIV occurred for the unsubstituted-catecholato VV complexes on dissolution in DMSO. By contrast, the pyridine moiety within the Schiff base significantly improved the hydrolytic stability of [VV O(SALIEP)(DTB)] compared with [VV O(HSHED)(DTB)]. [VV O(SALIEP)(DTB)] had moderate stability in cell culture media. There was significant cellular uptake of the intact complex by T98G (human glioblastoma) cells and very good anti-proliferative activity (IC50 6.7±0.9 μM, 72 h), which was approximately five times higher than for the non-cancerous human cell line, HFF-1 (IC50 34±10 μM). This made [VV O(SALIEP)(DTB)] a potential drug candidate for the treatment of advanced gliomas by intracranial injection.

A novel pyrazole–pyridine derivative (PPD) targets specific biological pathways in the larval stages of the northern house mosquito Culex pipiens Linnaeus (Diptera: Culicidae)

BackgroundMosquitoes cause a variety of health problems in humans and pets. So, the control of mosquito larvae is one of the best ways to avoid health problems arising from diseases transmitted by these insects. There are various control mechanisms including mechanical, biological and chemical control. The latter, despite the presence of some obstacles associated with its use, is preferred because of its ability to supply rapid management results.ResultA novel laboratory-synthesized chemical compound containing pyrazole and pyridine moieties (pyrazole–pyridine derivatives, PPD) was used to control and address the biological effects on Culex pipiens mosquito second larval instar. A sublethal concentration (LC30) of PPD inhibited larval growth by about 50%. Furthermore, the developmental time of larvae into pupae and the emergence of adults from the pupal stages were increased by about 20% and 17%, respectively. The ultrastructural studies on the midgut cells revealed that treated larvae suffered dramatic degeneration in the gastric caeca and the posterior midgut cells, while the anterior midgut epithelium appeared with an abundance of lysosomal activities. Additionally, treated larvae showed fluctuated activities in the levels of the detoxifying enzymes and increased levels in total antioxidants.ConclusionsThese results clearly show that pyrazole and pyridine moieties containing compounds can be used against larval stages of C. pipiens.

Synthesis and Characterization of Some New Pyridine-Carboxamide Derivatives of Potential Biological Activities

A facile synthetic routes to access some new heterocyclic systems containing potent pharmacophoric groups such as pyrazole, pyrazolo[5,1-c]-1,2,4-triazine, 1,2,4-triazino[4,3-a]benzimidazole, and pyridine moieties linked to pyridine-carboxamide moiety are reported. Construction of the target compounds was achieved via reaction of 3-oxo-butanamides 1a,b with hydrazonoyl halides, heterocyclic diazonium salts, and malononitrile derivatives, respectively. The structures of the new products were confirmed by all possible spectral and elemental analyses. The antibacterial assessment showed that one product was moderately active against both K. pneumonia and S. aureus.

The anticancer and anti-inflammatory activity screening of pyridazinone-based analogs against human epidermoid skin cancer with detailed mechanistic analyses

3(2H)-Pyridazinone derivatives based on 4-biphenyl, naphtha-2-yl, pyridine, or piperidine moiety were synthesized and characterized using I-R and 1HNMR spectra. The activity and cytotoxicity of some synthesized compounds on the skin epidermoid cancer cell proliferation and progression were investigated. The pyridazine isomer with pyridine revealed a significant decrease in the level of nitric oxide p < 0.01 than the activity of caffeine phenecyl ester. The activity of the three active isomers recorded significant activity for their total antioxidant content that triggers their ability for the scavenging the oxygen free radicals significantly p < 0.01. Moreover, revealing the pharmaceutical activity of the isomers as anti-inflammatory agents, IL-6, IL10, and IL12 have been decreased by variable significant values. Additionally, the active isomers revealed variable actions on the skin cancer cell to induce apoptosis using annexin V-FITC/PI. Pyridine was the highest isomer to induce late apoptosis and necrosis for the skin cancer cells against the use of cisplatin. Importantly, Molecular modeling experiments including docking and dynamic simulations were done for the most active 3 analogs to explore the ligand binding and stability leading to exploring the structure-activity relationship with biological target PARP1 which showed a good binding propensity to pyridazine binding site which supports the in vitro data. In conclusion, the pyridazine moieties with piperdine, naphthayl, and pyridine have pharmacological activities against skin cancer epidermoid by triggering action in inhibition of the proliferation and progression with an up-regulated apoptotic mechanism that evades the emergence of cisplatin resistance among different cancer cells. Communicated by Ramaswamy H. Sarma

Introducing Design Strategies to Preserve N-Heterocycles Throughout the On-Surface Synthesis of Graphene Nanostructures.

Despite the impressive advances in the synthesis of atomically precise graphene nanostructures witnessed during the last decade, advancing in compositional complexity faces major challenges. The concept of introducing the desired functional groups or dopants in the molecular precursor often fails due to their lack of stability during the reaction path. Here, a study on the stability of different pyridine and pyrimidine moieties during the on-surface synthesis of graphene nanoribbons on Au(111) is presented. Combining bond-resolved scanning tunneling microscopy with X-ray photoelectron spectroscopy, the thermal evolution of the nitrogen dopants throughout the whole reaction sequence is tracked. A comparative experimental and ab initio electronic characterization confirms the presence of dopants in the final structures, revealing also that the pyridinic nitrogen leads to a significant band downshift. The results demonstrate that, by using synthetic strategies to lower the reaction temperatures, one can preserve specific N-heterocycles throughout all the reaction steps of the synthesis of graphene nanoribbons and beyond the interibbon coupling reaction that leads to nanoporousgraphene.

Investigation of novel bis-thiadiazole bearing schiff base derivatives as effective inhibitors of thymidine phosphorylase: Synthesis, in vitro bioactivity and molecular docking study

Thymidine phosphorylase (TP) is an angiogenic enzyme. It is crucial for the development, invasion and metastasis of tumors as well as angiogenesis. In our current research, we examine how structurally changing bis-thiadiazole bearing bis-schiff bases affects their ability to inhibit TP. Through the oxidative cyclization of pyridine-based bis-thiosemicarbazone with iodine, a series of fourteen analogs of bis-thiadiazole-based bis-imines with pyridine moiety were developed. Newly synthesized scaffolds were assessed in vitro for their thymidine phosphorylase inhibitory potential and showed moderate to good inhibition profile. Eleven scaffolds such as 4a-4d,4f-4 h and 4j-4 m were discovered to be more effective than standard drug at inhibiting the thymidine phosphorylase enzyme with IC50 values of 1.16 ± 1.20, 1.77 ± 1.10, 2.48 ± 1.30, 12.54 ± 1.60, 14.63 ± 1.70, 15.53 ± 1.80, 17.47 ± 1.70, 18.98 ± 1.70, 19.53 ± 1.50, 22.73 ± 2.40 and 24.87 ± 2.80 respectively, while remaining three analogs such as 4n, 4i and 4ewere found to be more potent, but they were less potent than the standard drug. All analogs underwent SAR studies based on the pattern of substitutions around the aryl part of the bis-thiadiazole skeleton. The most active analogs in the synthesized series were then molecular docking study performed to investigate their interactions of active part of enzyme. The results showed that remarkable interactions were exhibited by these analogs with the targeted enzymes active sites. Furthermore, to confirm the structure of synthesized analogs by employing spectroscopic tools such as HREI-MS and NMR.

One‐pot sequential regioselective intramolecular synthesis of furo[3,2‐c]chromen and imidazo[1,2‐a]pyridine via catalyst‐free and basic conditions

AbstractWe developed a sequential intramolecular ring‐closure‐opening‐closure pathway using a catalyst‐free and organo‐base catalyzed system for the synthesis of fused regioselective tricyclic furo[3,2‐c]chromen and bicyclic imidazo[1,2‐a]pyridine via a one‐pot three‐component reaction. The protocol involved a Knoevenagel and Michael adduct via intramolecular cyclization with 4‐hydroxycoumarin, aromatic glyoxal, and 2‐aminopyridine under heating and ambient conditions with very good yields. The merits of this methodology were studied, and new practical ways were developed to access furo[3,2‐c]chromen and imidazo[1,2‐a]pyridine moieties.

Unexpected products using Biginelli reaction: Synthesis, antimicrobial potency, docking simulation, and DFT investigations of some new amidopyridines

The Biginelli reaction of 3-oxo-N-(2-pyridyl)butanamide with thiourea (or urea) and some aromatic aldehydes afforded new chemical skeletons containing tetrahydropyrimidine, pyridine, and carboxamide pharmacophoric moieties. The expected products of this reaction were not isolated in the case of 4-nitrobenzaldehyde, pyridine-2-carbaldehyde, and thiophene-2-carbaldehyde; rather the corresponding acrylamide derivatives were obtained. Chemical structures of the newly synthesized hybrids were elucidated by FT-IR, NMR spectroscopy in addition to mass spectrometry and elemental analyses. The in-vitro antimicrobial activity showed that the products were highly active against the tested pathogens that were confirmed through molecular docking simulation with different proteins such as PDBID:3t88, 2wje, 1tgh, and 4ynt which showed a different binding affinity with attraction of amino acids of proteins. Furthermore, the optimization of different pyridine carboxamides utilized a DFT/B3LYP-6311(G) basis set to know the cyclization of butanamide 1 with thiourea and different aldehydes in the presence of electron-donating/withdrawing groups which affected of the expected products with different transition states. Moreover, the determination of the energy gap and physical descriptors of these pyridine carboxamide derivatives showed the stability of tetrahydropyrimidines 2a,b due to the presence of donating groups which enhanced the activity and stability. Determination of the ESP and MEP of compounds 2a,b confirmed a correlation with biological evaluations.

N-Heterocyclic Compounds, In silico Molecular Docking Studies, and In vitro Enzyme Inhibition Effect against Acetylcholinesterase Inhibitors.

This work contains the synthesis of seven new N-heterocyclic compounds bearing imidazole, benzimidazole, pyridine, and morpholine moieties. We aimed to synthesize N-heterocyclic compounds for a more effective drug candidate to increase the amount of acetylcholine in synapses in Alzheimer's disease. All compounds were characterized by 1H NMR, 13C NMR, FTIR and elemental analysis. Enzyme inhibition activity of all compounds against acetylcholinesterase was investigated, which is an indirect treatment for Alzheimer's. Molecular docking was applied to estimate the binding energy of these compounds to the acetylcholinesterase. All compounds were synthesized from reactions of 2 equivalents of N-heterocyclic starting material and 1 equivalent of 4,4'-bis(chloromethyl)-1,1'-biphenyl. The inhibition parameters of IC50 and Ki were calculated by the spectrophotometric method. AutoDock4 was used to define the binding pose of the compounds. Ki values were found in the range of 80.03 ± 19.64 to 5014.98 ± 1139.60 nM for AChE as an enzyme inhibition strategy, which is an important parameter for the treatment of neurodegenerative such as Alzheimer's disease. In this study, molecular docking is exerted to predict the binding energy of heterocyclic compounds (especially 2, 3, and 5) against acetylcholinesterase enzyme. Their docking binding energies are in good agreement with experimental findings. These new syntheses are drugs that can be used as AChE inhibitors in Alzheimer's disease.

Supramolecular Memristor Based on Bistable [2]Catenanes: Toward High‐Density and Non‐Volatile Memory Devices

AbstractThe ever‐increasing demand for data storage and neuromorphic computing calls for innovative, high‐density solutions, such as resistive random‐access memory (RRAM). However, the integration of resistive switching and rectification at the nanoscale remains a formidable challenge. In this study, we introduce a bistable [2]catenane‐based supramolecular junction that simultaneously functions as a resistive switch and a diode. All supramolecular junctions are highly stable and reproducible over thousands of resistive switching cycles, because the nano‐confinement of two mechanically interlocked rings can stabilize the radical states of pyridinium moieties under ambient conditions. The successful realization of supramolecular junctions in functionality with a thickness of approximately 2 nm presents a promising avenue for the development of molecule‐scale based RRAM for a better solution to high density and energy efficiency.

Supramolecular Self-Assembly of the Zwitterionic Sn(IV)-Porphyrin Complex

[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3)2TPyHP]2+ species consists of two anionic axial Sn–O–SO3 units and four peripheral pyridinium moieties, with an overall dicationic charge balanced by two hydrogen sulfate (HSO4−) counter-anions. Ionic hydrogen bonding between the oxygen atoms of axial sulfato ligands and the peripheral pyridinium groups of adjacent Sn(IV)-porphyrin cations led to the formation of a 1D channel filled with counter-anions and water molecules. The supramolecular self-assembly of 1 was further characterized using various spectroscopic techniques, including 1H NMR spectroscopy, elemental analysis, ESI-mass spectrometry, UV-vis spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, thermogravimetric analysis (TGA), and powder X-ray diffractometry. The zwitterionic [Sn(OSO3)2TPyHP]2+ complex is a structurally well-defined complementary scaffold involved in supramolecular self-assembly. This novel class of ion-assembled metalloporphyrin is a potential functional porphyrin material used in ion exchange applications.

Supramolecular Memristor Based on Bistable [2]Catenanes: Toward High-Density and Non-Volatile Memory Devices.

The ever-increasing demand for data storage and neuromorphic computing calls for innovative, high-density solutions, such as resistive random-access memory (RRAM). However, the integration of resistive switching and rectification at nanoscale remains a formidable challenge. In this study, we introduce a bistable [2]catenane-based supramolecular junction that simultaneously functions as a resistive switch and a diode. All supramolecular junctions are highly stable and reproducible over thousands of resistive switching cycles, because the nano-confinement of two mechanically interlocked rings can stabilize the radical states of pyridinium moieties under ambient conditions. The successful realization of supramolecular junctions in functionality with a thickness of approximately 2 nm presents a promising avenue for the development of molecule-scale based RRAM for a better solution of high-density and energy-efficiency.

The unusual (syn-/anti-)2 conformation of a di-meth-oxy-pyrimidyl-based tennimide.

The tennimide macrocycle, (I) (C52H40N16O16.0.167H2O), was synthesized from 2-amino-4,6-di-meth-oxy-pyrimidine and pyridine-2,6-dicarbonyl dichloride. Compound (I) represents the first tennimide incorporating pyridine rings in the macrocycle scaffold. In the macrocycle ring, the carbonyl groups at each successive dicarbon-yl(pyridine) moiety adopt the (syn/anti)2 conformation. This contrasts with all previously reported tetra-imide macrocycles, which exhibit the (syn)4 conformation. The effect is to close any potential cavity or niche by having two of the central pyridine C5N rings aligned close to each other [with closest pyridine Cg⋯Cg ring centroid separations of 3.5775 (19) Å; closest C⋯C = 3.467 (5) Å]. A partial occupancy water mol-ecule (with s.o.f. = 0.167), resides with its oxygen atom on a twofold axis at hydrogen-bonding distances to the carbonyl O atom, in a mol-ecular niche between two pyridine rings. Macrocyles of (I) have all six C=O groups and all eight meth-oxy O atoms present on the macrocycle surface. However, all twelve N atoms are effectively shielded on steric grounds from any potential inter-molecular inter-actions. The remaining two C=O O atoms inter-act with the partial occupancy water mol-ecule via two O-H⋯O=C hydrogen bonds. Macrocycles of (I) stack as one-dimensional chains along the b-axis direction with primary inter-molecular inter-actions involving weak C-H⋯O=C/OCH3/H2O contacts. Chains inter-lock weakly via meth-oxy-meth-oxy C-H⋯O inter-actions into two-dimensional sheets.