Three-dimensional Hydrogen-bonded Network Research Articles

Molecular dynamics models and thermodynamic characteristics of hydrogen bonds in 1,2-ethanediol

A correlation between the lifetimes of hydrogen bonds and the thermodynamic characteristics of their formation and breaking, and the experimental relaxation times of dielectric spectra and the energy characteristics of relaxation processes, is observed via molecular dynamics (MD) simulation of the rearranging of the network structure of 1,2-ethanediol. The MD torsional frequency of the transition of gauche conformer tGg′ at 224.1 cm−1 and the experimental frequency of the band maximum of torsional vibrations at 230 cm−1 in the infrared spectrum correlate with the oscillation frequency of molecules at 240 cm−1 inside clusters in the Dissado–Hill (DH) model. The MD and DH models indicate a predominantly parallel alignment of the electric dipole moments of conformers tGg′ in the three-dimensional network of hydrogen bonds of the liquid 1,2-ethanediol phase.

A dihydro-β-agarofuran sesquiterpene from Maytenus boaria.

The natural compound (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9,10-trihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, C22H30O9, (I), is a β-agarofuran sesquiterpene isolated from the seeds of Maytenus boaria as part of a study of the secondary metabolites from Chilean flora. The compound presents a central structure formed by a decalin system esterified with acetate at site 1 and furan-3-carboxylate at site 9. The chirality of the skeleton can be described as 1S,4S,5S,6R,7R,8R,9R,10S, which is consistent with that suggested by NMR studies. Unlike previously reported structures of sesquiterpenes containing a pure dihydro-β-agarofuran skeleton, (I) exhibits a three-dimensional hydrogen-bonded network.

Hydrogen bonding in protic and aprotic amide mixtures: Low-frequency Raman spectroscopy, small-angle neutron scattering, and molecular dynamics simulations

The hydrogen-bonding interactions in protic and aprotic amide solvent mixtures, i.e., formamide (FA) and N,N-dimethylformamide (DMF), were investigated via low-frequency Raman spectroscopy, small-angle neutron scattering (SANS) experiments, and molecular dynamics (MD) simulations. In a neat amide system, the low-frequency Raman spectra R(ν)s were well reproduced by the corresponding S(ν) spectra derived from the MD simulations. The observed peaks in R(ν)s at around <200cm−1 were assigned to the intermolecular interactions, particularly in terms of the hydrogen-bonding network formation and its dimensionality in the liquid state. The SANS experiments for the FA–DMF mixtures demonstrated that the FA molecules forming an extended three–dimensional hydrogen-bonding structure in the neat system interacted with DMF molecules through the hydrogen bonds in the mixtures over the whole range of solvent compositions, resulting in a homogeneous mixing state. Additionally, the R(ν) spectra for the mixtures were represented by the corresponding S(ν) spectra. From the R(ν) and S(ν) spectra of the FA–DMF mixtures, we found that (1) the Raman band at around 110cm−1 mainly originates from the libration mode of amide molecules in the chain-like hydrogen-bonded structure and (2) the higher frequency band (approximately 200cm−1) was attributed to the libration of the FA molecule restricted by the three-dimensional hydrogen-bonded network, which remained even in the DMF-rich compositions.

Crystal structure of [Co(en)3][NpO4(OH)2]·5H2O (en = ethylenediamine, H2N(CH2)2NH2)

A Np(VII) compound with [Co(en)3]3+ cations, [Co(en)3][NpO4(OH)2]·5H2O (en = ethylenediamine), was synthesized and studied by single crystal X-ray diffraction. The structure consists of [NpO4(OH)2]3– anions and [Co(en)3]3+ cations forming electrically neutral layers, between which water molecules are arranged. A three-dimensional network of hydrogen bonds involving all the constituents of the structure is formed in the crystal. The effect of hydrogen bonding on the geometric characteristics of [NpO4(OH)2]3– anions is discussed.

Crystal structure of hydrocortisone acetate, C23H32O6

The crystal structure of hydrocortisone acetate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Hydrocortisone acetate crystallizes in space groupP21(#4) witha= 8.85173(3) Å,b= 13.53859(3) Å,c= 8.86980(4) Å,β= 101.5438(3)°,V= 1041.455(6) Å3, andZ= 2. Both hydroxyl groups form hydrogen bonds to the ketone oxygen atom on the steroid ring system, resulting in a three-dimensional hydrogen bond network. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File™.

Pyridine and 3-methylpyridine solvates of the triple sulfa drug constitutent sulfamethazine.

Sulfonamides display a wide variety of pharmacological activities. Sulfamethazine [abbreviated as SMZ; systematic name 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide], one of the constitutents of the triple sulfa drugs, has wide clinical use. Pharmaceutical solvates are crystalline solids of active pharmaceutical ingredients (APIs) incorporating one or more solvent molecules in the crystal lattice, and these have received special attention, as the solvent molecule can impart characteristic physicochemical properties to APIs and solvates, therefore playing a significant role in drug development. The ability of SMZ to form solvates has been investigated. Both pyridine and 3-methylpyridine form solvates with SMZ in 1:1 molar ratios. The pyridine monosolvate, C12H14N4O2S·C5H5N, crystallizes in the orthorhombic space group Pna21, with Z = 8 and two molecules per assymetric unit, whereas the 3-methylpyridine monosolvate, C12H14N4O2S·C6H7N, crystallizes in the orthorhombic space group P212121, with Z = 4. Crystal structure analysis reveals intramolecular N-H...N hydrogen bonds between the molecules of SMZ and the pyridine solvent molecules. The solvent molecules in both structures play an active part in strong intermolecular interactions, thereby contributing significantly to the stability of both structures. Three-dimensional hydrogen-bonding networks exist in both structures involving at least one sulfonyl O atom and the amine N atom. In the pyridine solvate, there is a short π-π interaction [centroid-centroid distance = 3.926 (3) Å] involving the centroids of the pyridine rings of two solvent molecules and a weak intermolecular C-H...π interaction also contributes to the stability of the crystal packing.

Proton-Conducting Phenolate-Based Zr Metal–Organic Framework: A Joint Experimental–Modeling Investigation

The proton-conduction performances of the chemically stable porous zirconium phenolate MIL-163 MOF were characterized for the first time by complex impedance spectroscopy. Whereas this large square-shaped channel-like MOF exhibits very poor conductivity under anhydrous conditions, measurements performed at 90 °C and 95% relative humidity evidenced a superprotonic behavior with a conductivity of 2.1 × 10–3 S·cm–1, among the highest values reported so far for water-stable MOFs. This experimental investigation was further supported by Monte Carlo simulations to shed light on the effects of both the guest molecules (i.e., dimethylamine and water) and the acidic protons from the constitutive inorganic chains on the conduction properties of this porous hybrid solid. It was found that the water molecules form a three-dimensional hydrogen-bond network leading to the formation of multiple pathways that bridge the acidic Zr-bonded phenol groups of the organic linker, which act as a proton source. The dimethylamine ...

Hydrogen bonding, π-π stacking and van der Waals forces-dominated layered regions in the crystal structure of 4-amino-pyridinium hydrogen (9-phosphono-non-yl)phospho-nate.

The asymmetric unit of the title mol-ecular salt, [C5H7N2+][(HO)2OP(CH2)9PO2(OH)-], consists of one 4-amino-pyridinium cation and one hydrogen (9-phos-phono-non-yl)phospho-nate anion, both in general positions. As expected, the 4-amino-pyridinium moieties are protonated exclusively at their endocyclic nitro-gen atom due to a mesomeric stabilization by the imine form which would not be given in the corresponding double-protonated dicationic species. In the crystal, the phosphonyl (-PO3H2) and hydrogen phospho-nate (-PO3H) groups of the anions form two-dimensional O-H⋯O hydrogen-bonded networks in the ab plane built from 24-membered hydrogen-bonded ring motifs with the graph-set descriptor R66(24). These networks are pairwise linked by the anions' alkyl-ene chains. The 4-amino-pyridinium cations are stacked in parallel displaced face-to-face arrangements and connect neighboring anionic substructures via medium-strong charge-supported N-H⋯O hydrogen bonds along the c axis. The resulting three-dimensional hydrogen-bonded network shows clearly separated hydro-philic and hydro-phobic structural domains.

Synthesis, structural characterization, IR- and Raman spectroscopy, magnetic properties of new organically templated metal sulfates with 4-aminopyridinium

Crystal structures of the series of twelve 4-aminopyridinium templated metal sulfates: (C5H7N2)2[MeII(H2O)6](SO4)2 (MeII = Cu (1), Co (2), Mg (3), Zn (4), Fe (5), Mn (6a)), (C5H7N2)2[MeII(H2O)4(SO4)2]·4H2O (MeII = Mn (6b), Cd (7a)), (C5H7N2)2[MnII(H2O)4(SO4)2] (6c), (C5H7N2)2[Cd(H2O)4(SO4)2] (7b), (C5H7N2)[Al(H2O)6](SO4)2·4H2O (low (8lt) and room temperature (8rt) phases) and (C5H7N2)[FeIII(H2O)4(SO4)2] (9) were determined by single-crystal X-ray diffraction. Compounds 1-6a are isostructural, crystal structure consists of [Me(H2O)6]2+ octahedra, 4-aminopyridinium cations (4ap) and sulfate anions. Crystal packing in 1-6a series is characterized by alternating 4ap and inorganic layers. In the structure of 1 Cu2+ coordination environment is axially deformed due to Jahn-Teller effect to tetragonal bipyramidal. Compounds 6 (a, b) and 7a at ambient conditions dehydrate to produce isostructural complexes 6c and 7b, respectively. In structures of 6c, 7b and 9 sulfate anions are involved in slightly distorted octahedral metal coordination composed of six O atoms from four water molecules and two sulfate anions. Room temperature phase of 8 is characterized by disorder of 4ap around center of inversion. Continuous phase transition at ≈185 K leads to the cell doubling and ordering of 4ap. All of the structures are governed by an extensive three-dimensional hydrogen bond networks, as well as π–π interactions visualized by Hirshfeld surface analysis. Moreover, selected compounds were characterized by the IR and Raman spectroscopy and magnetic measurement studies.

Purine 3':5'-cyclic nucleotides with the nucleobase in a syn orientation: cAMP, cGMP and cIMP.

Purine 3':5'-cyclic nucleotides are very well known for their role as the secondary messengers in hormone action and cellular signal transduction. Nonetheless, their solid-state conformational details still require investigation. Five crystals containing purine 3':5'-cyclic nucleotides have been obtained and structurally characterized, namely adenosine 3':5'-cyclic phosphate dihydrate, C10H12N5O6P·2H2O or cAMP·2H2O, (I), adenosine 3':5'-cyclic phosphate 0.3-hydrate, C10H12N5O6P·0.3H2O or cAMP·0.3H2O, (II), guanosine 3':5'-cyclic phosphate pentahydrate, C10H12N5O7P·5H2O or cGMP·5H2O, (III), sodium guanosine 3':5'-cyclic phosphate tetrahydrate, Na(+)·C10H11N5O7P(-)·4H2O or Na(cGMP)·4H2O, (IV), and sodium inosine 3':5'-cyclic phosphate tetrahydrate, Na(+)·C10H10N4O7P(-)·4H2O or Na(cIMP)·4H2O, (V). Most of the cyclic nucleotide zwitterions/anions [two from four cAMP present in total in (I) and (II), cGMP in (III), cGMP(-) in (IV) and cIMP(-) in (V)] are syn conformers about the N-glycosidic bond, and this nucleobase arrangement is accompanied by Crib-H...Npur hydrogen bonds (rib = ribose and pur = purine). The base orientation is tuned by the ribose pucker. An analysis of data obtained from the Cambridge Structural Database made in the context of syn-anti conformational preferences has revealed that among the syn conformers of various purine nucleotides, cyclic nucleotides and dinucleotides predominate significantly. The interactions stabilizing the syn conformation have been indicated. The inter-nucleotide contacts in (I)-(V) have been systematized in terms of the chemical groups involved. All five structures display three-dimensional hydrogen-bonded networks.

Effect of 1-ethyl-3-methylimidazolium bromide on interfacial and aggregation behavior of mixed cationic and anionic surfactants

Aggregation behavior and interaction of sodium dodecyl sulfate (SDS), tetradecyl trimethyl ammonium bromide (TTAB) and their mixtures with an excess of anionic surfactant in the presence of imidazolium-based ionic liquid, 1-ethyl-3-methylimidazolium bromide (EMIm Br) were investigated using surface tension, electrical conductivity, dynamic light scattering (DLS), transmission electron microscopy (TEM) and cyclic voltammetry measurements. Different physicochemical properties such as critical micelle concentration (CMC), degree of counterion dissociation (αdiss), interfacial properties, the standard Gibbs energy of adsorption and the size of aggregates were determined. The effects of ionic liquid (IL) as additive on the interactions between the surfactants; TTAB, SDS and their mixtures were analyzed on the basis of regular solution theory, both for mixed monolayers at the air/liquid interface (βδ) and for mixed micelles (βM). Interaction parameter values suggested that the formation of aggregates is due to the synergistic interactions in the case of SDS/TTAB systems and becomes more affected by adding IL. It was shown that an excess of cationic surfactant and IL resulted in an increase in the nano-aggregate sizes. The synergism observed for three component systems (surfactant–water–IL) revealed the effect of attractive electrostatic interaction, formation of a three-dimensional hydrogen bond network and hydrophobic forces on mixed micelle formation.

Crystal structure of mupirocin form I, C26H44O9

The crystal structure of mupirocin Form I has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Mupirocin Form I crystallizes in space groupP21(#4) witha= 12.562 81(16),b= 5.103 63(4),c= 21.713 34(29) Å,β= 100.932(1)°,V= 1366.91(2) Å3, andZ= 2. Although the three hydroxyl groups and the carboxylic acid participate in a three-dimensional hydrogen bond network, the crystal energy appears to be dominated by van der Waals interactions. The Rietveld-refined and density functional optimized structures differ significantly. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File™.

(Acetato-κO){2-[(2-aminoethyl-κN)disulfanyl]ethanaminium}dichloridozinc(II)

In the title compound, [Zn(C4H13N2S2)(CH3COO)Cl2], the ZnIIion is in a tetrahedral coordination geometry, coordinated by one acetate, two chloride and one 2-[(2-aminoethyl)disulfanyl]ethanaminium ligand, with a Zn—O distance of 1.977 (3) Å, a Zn—N distance of 2.015 (3) Å and Zn—Cl distances of 2.2673 (18) and 2.2688 (15) Å. In the crystal, molecules are self-assembled by N—H...Cl hydrogen bonds, leading to a one-dimensional chain structure. The chains interact with each other through N—H...O, N—H...S, C—H...Cl and C—H...S hydrogen bonding, completing a three-dimensional hydrogen-bonding network structure.

Copper(II) Coordination Polymers Self-Assembled from Aminoalcohols and Pyromellitic Acid: Highly Active Precatalysts for the Mild Water-Promoted Oxidation of Alkanes.

Three novel water-soluble 2D copper(II) coordination polymers-[{Cu2(μ2-dmea)2(H2O)}2(μ4-pma)]n·4nH2O (1), [{Cu2(μ2-Hedea)2}2(μ4-pma)]n·4nH2O (2), and [{Cu(bea)(Hbea)}4(μ4-pma)]n·2nH2O (3)-were generated by an aqueous medium self-assembly method from copper(II) nitrate, pyromellitic acid (H4pma), and different aminoalcohols [N,N-dimethylethanolamine (Hdmea), N-ethyldiethanolamine (H2edea), and N-benzylethanolamine (Hbea)]. Compounds 2 and 3 represent the first coordination polymers derived from H2edea and Hbea. All the products were characterized by infrared (IR), electron paramagnetic resonance (EPR), and ultraviolet-visible light (UV-vis) spectroscopy, electrospray ionization-mass spectroscopy (ESI-MS(±)), thermogravimetric and elemental analysis, and single-crystal X-ray diffraction (XRD), which revealed that their two-dimensional (2D) metal-organic networks are composed of distinct dicopper(II) or monocopper(II) aminoalcoholate units and μ4-pyromellitate spacers. From the topological viewpoint, the underlying 2D nets of 1-3 can be classified as uninodal 4-connected layers with the sql topology. The structures of 1 and 2 are further extended by multiple intermolecular hydrogen bonds, resulting in three-dimensional (3D) hydrogen-bonded networks with rare or unique topologies. The obtained compounds also act as highly efficient precatalysts for the mild homogeneous oxidation, by aqueous H2O2 in acidic MeCN/H2O medium, of various cycloalkanes to the corresponding alcohols and ketones. Overall product yields up to 45% (based on cycloalkane) were attained and the effects of various reaction parameters were investigated, including the type of precatalyst and acid promoter, influence of water, and substrate scope. Although water usually strongly inhibits the alkane oxidations, a very pronounced promoting behavior of H2O was detected when using the precatalyst 1, resulting in a 15-fold growth of an initial reaction rate in the cyclohexane oxidation on increasing the amount of H2O from ∼4 M to 17 M in the reaction mixture, followed by a 2-fold product yield growth.

Redetermination of the crystal structure of 3,5-di-methyl-pyrazolium β-octa-molybdate tetra-hydrate.

The title compound, (C5H9N2)4[Mo8O26]·4H2O, was reported previously from a room-temperature data collection from which only the metal atoms could be refined anisotropically [FitzRoy et al. (1989 ▸). Inorg. Chim. Acta, 157, 187–194]. The current redetermination at 180 (2) K models all the non-H atoms with anisotropic displacement parameters and fully describes the supra­molecular N—H⋯O and O—H⋯O hydrogen-bonded network connecting the 3,5-di­methyl­pyrazolium cations, the water mol­ecules of crystallization and the β-octa­molybdate anion. All H atoms involved in the three-dimensional hydrogen-bonding network could be located from difference Fourier maps, with the exception of those of one disordered water mol­ecule, firstly seen in this structural report [refined over two distinct locations with site-occupancy factors of 0.65 (2) and 0.35 (2)]. The complete β-octa­molybdate anion is generated by a crystallographic inversion centre.

Synthon preference in a hydrated β-resorcylic acid structure and its cocrystal with thymine.

Multicomponent crystals or cocrystals play a significant role in crystal engineering, the main objective of which is to understand the role of intermolecular interactions and to utilize such understanding in the design of novel crystal structures. Molecules possessing carboxylic acid and amide functional groups are good candidates for forming cocrystals. β-Resorcylic acid monohydrate, C7H6O4·H2O, (I), crystallizes in the triclinic space group P-1 with one β-resorcylic acid molecule and one water molecule in the asymmetric unit. The cocrystal thymine-β-resorcylic acid-water (1/1/1), C5H6N2O2·C7H6O4·H2O, (II), crystallizes in the orthorhombic space group Pca21, with one molecule each of thymine, β-resorcylic acid and water in the asymmetric unit. All available donor and acceptor atoms in (I) and (II) are utilized for hydrogen bonding. The acid and amide functional groups are well known for the formation of self-complementary acid-acid and amide-amide homosynthons. In (I), an acid-acid homosynthon is observed, while in (II), an amide-acid heterosynthon is present. In (I), the β-resorcylic acid molecule exhibits the expected intramolecular S(6) motif between the hydroxy and carbonyl O atoms, and an intermolecular R2(2)(8) dimer motif between the carboxylic acid groups; only the former motif is observed in (II). The water solvent molecule in (I) propagates the discrete dimers into two-dimensional hydrogen-bonded sheets. In (II), thymine and β-resorcylic acid molecules do not form self-complementary amide-amide and acid-acid homosynthons; instead, a thymine-β-resorcylic acid heterosynthon is observed. With the help of the water molecule, this heterosynthon is aggregated into a three-dimensional hydrogen-bonded network. The absence of thymine base pairing in (II) might be linked to the availability of additional functional groups and the preference of the donor and acceptor hydrogen-bond combinations.

Synthesis, Crystal Structures, and Characterization of Two New Complexes Constructed From Acipimox Ligands: Two Three-Dimensional Networks Formed Via Hydrogen Bonding

Two new complexes, [Co(aci)2(H2O)2]·2H2O (1) and [Zn(aci)2(H2O)2]·2H2O (2) (aciH = 4-oxo-5-methylpyrazine-2-carboxylic acid) were obtained by the reaction of corresponding metal salts and aciH, and characterized by elemental analysis, FT-IR spectroscopy, single-crystal X-Ray diffraction, and magnetic susceptibility measurement. X-Ray analysis demonstrates that two compounds both crystallize in triclinic system, space group P-1, and contain a mononuclear complex and two lattice water molecules. The two discrete complexes are further linked into three-dimensional hydrogen-bond networks via rich hydrogen bonding interactions.

Hirshfeld surface analysis of sulfameter (polymorph III), sulfameter dioxane monosolvate and sulfameter tetrahydrofuran monosolvate, all at 296 K.

The ability of the antibacterial agent sulfameter (SMT) to form solvates is investigated. The X-ray crystal structures of sulfameter solvates have been determined to be conformational polymorphs. Both 1,4-dioxane and tetrahydrofuran form solvates with sulfameter in a 1:1 molar ratio. 4-Amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide (polymorph III), C11H12N4O3S, (1), has two molecules of sulfameter in the asymmetric unit cell. 4-Amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide 1,4-dioxane monosolvate, C11H12N4O3S·C4H8O2, (2), and 4-amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide tetrahydrofuran monosolvate, C11H12N4O3S·C4H8O, (3), crystallize in the imide form. Hirshfeld surface analyses and fingerprint analyses were performed to study the nature of the interactions and their quantitative contributions towards the crystal packing. Finally, Hirshfeld surfaces, fingerprint plots and structural overlays were employed for a comparison of the two independent molecules in the asymmetric unit of (1), and also for a comparison of (2) and (3) in the monoclinic crystal system. A three-dimensional hydrogen-bonding network exists in all three structures, involving one of the sulfone O atoms and the aniline N atom. All three structures are stabilized by strong intermolecular N-H···N interactions. The tetrahydrofuran solvent molecule also takes part in forming significant intermolecular C-H···O interactions in the crystal structure of (3), contributing to the stability of the crystal packing.

Dehydration of raffinose pentahydrate: structures of raffinose 5-, 4.433-, 4.289- and 4.127-hydrate at 93 K.

Raffinose [or O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside] pentahydrate, C18H32O16·5H2O, (I), and three lower hydrates, namely the 4.433-, (II), 4.289-, (III), and 4.127-hydrated, (IV), forms, obtained in the course of the dehydration of (I), have been studied. The unit cells in the space group P2₁2₁2₁ are of similar dimensions for all the crystals. The conformation of the raffinose molecules remains almost the same across the four crystal structures. The raffinose molecules are linked into a three-dimensional hydrogen-bonded network involving all the -OH groups, the ring and glycosidic O atoms, and the water molecules. Six water sites were identified in the structures of (II), (III) and (IV), of which W1, W4 and W6 (W = water) are partially occupied with their populations coupled. W1, W4 and one of the -OH groups of the galactose ring form an infinite hydrogen-bonding chain around a 2₁ axis parallel to the a axis (denoted chain A), and W6 and the same -OH group form a similar chain (chain A') disordered with chain A. The occupancy ratio of chain A to chain A' for N-hydrates (N is a hydration number between 4 and 5) is (N - 4):(5 - N). The transformation of chain A to chain A' as part of the dehydration process has little effect on the rest of the structure. Thus, the dehydration proceeds without significant impact on the crystal structure.

Crystal structure of new organically templated copper sulfate with 2-amino-pyridinium.

The title compound, (C5H7N2)2[Cu(H2O)6](SO4)2·4H2O [systematic name: bis(2-aminopyridinium) hexaaquacopper(II) bis(sulfate) tetrahydrate], comprises axially elongated hexa­aqua-coordinated octa­hedral CuII ions located on an inversion centre, non-coordinating sulfate anions, 2-amino­pyridinium cations and lattice water mol­ecules. The crystal structure is built of successive inorganic and organic layers extending parallel to (001) that are connected by an extensive three-dimensional hydrogen-bonded network of the type O—H⋯O and N—H⋯O, as well as π–π inter­actions [centroid–centroid distance 3.4140 (14) Å, offset 0.277 Å].