OW Hydrogen Bonds Research Articles

Conformations and non-covalent interactions of cyclohexyl isothiocyanate and its water complex

The conformational equilibria of cyclohexyl isothiocyanate and its complex with water were studied by microwave spectroscopy combined with theoretical calculations. For the bare cyclohexyl isothiocyanate, the rotational spectra of the two conformers, namely a-trans and e-trans, were measured and analyzed. Additional mono-substituted isotopologues of two 13C and one 34S of a-trans and e-trans were also measured, which result in an accurate structural determination of the two conformers. For the binary complex with water, the rotational spectra were measured for the monohydrates of both a-trans and e-trans conformers. Water isotopologues were also detected for the monohydrates. All the measured rotational spectra show 14N quadrupole coupling hyperfine structures. Water molecule prefers linking to the isothiocyanate group through a OwH⋯S hydrogen bond and forming two CH⋯Ow hydrogen bonds with the oxygen atom of water acting as a proton acceptor. The non-covalent bonding features of the monohydrates were revealed by natural bond orbital analysis and symmetry-adapted perturbation theory analysis.

Molecular structures of two copper complexes with the pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction.

The crystal structures of bis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-ium-4-yl)-1,4-dihydroquinoline-3-carboxylato]copper(II) sulfate heptahydrate, [Cu(C16H18FN3O3)2]SO4·7H2O or [Cu(nor)2]SO4·7H2O (nor is norfloxacin), and bis{1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimide}dinitratocopper(II), [Cu(NO3)2(C8H13N3O4S)2] or [Cu(NO3)2(tnz)2] (tnz is tinidazole), were solved by X-ray diffraction. Both complexes crystallize in the space group P21/c, with Z= 4 (for nor) and Z= 2 (for ntz) molecules per unit cell. In [Cu(nor)2]SO4·7H2O, the CuII ion is at the centre of a square-planar environment, trans coordinated to two independent norfloxacin molecules in the zwitterionic form acting as bidentate ligands through one of the carboxyl (cbx) and the carbonyl (cb) O atoms. The solid is further stabilized by an extensive network of N-H...O(sulfate), N-H...O(cbx), N-H...OW, OW-H...O(sulfate) and OW-H...OW hydrogen bonds. The [Cu(NO3)2(tnz)2] complex is centrosymmetric, with the CuII ion in a square planar environment, coordinated to a tinidazole molecule acting as a monodentate ligand through its imidazole N atom and to one nitrate O atom. The vibrational FT-IR absorption spectra and thermal behaviour of the complexes were also studied and are briefly discussed based on the crystal structures.

Energetic Ordering of Hydrogen Bond Strengths in Methanol-Water Clusters: Insights via Molecular Tailoring Approach.

In this work, we examine the strength of various types of individual hydrogen bond (HB) in mixed methanol-water Mn Wm , (n+m=2 to 7) clusters, with an aim to understand the relative order of their strength, using our recently proposed molecular tailoring-based approach (MTA). Among all the types of HB, it is observed that the OM -H…OW HBs are the strongest (6.9 to 12.4 kcal mol-1 ). The next ones are OM -H…OM HBs (6.5 to 11.6 kcal mol-1 ). The OW -H…OW (0.2 to 10.9 kcal mol-1 ) and OW -H…OM HBs (0.3 to 10.3 kcal mol-1 ) are the weakest ones. This energetic ordering of HBs is seen to be different from the respective HB energies in the dimer i. e., OM -H…OM (5.0 to 6.0 kcal mol-1 )>OW -H…OM (1.5 to 6.0 kcal mol-1 )>OM -H…OW (3.8 to 5.6 kcal mol-1 )>OW -H…OW (1.2 to 5.0 kcal mol-1 ). The plausible reason for the difference in the HB energy ordering may be attributed to the increase or decrease in HB strengths due to the formation of cooperative or anti-cooperative HB networks. For instance, the cooperativity contribution towards the different types of HB follows: OM -H…OW (2.4 to 8.6 kcal mol-1 )>OM -H…OM (1.3 to 6.3 kcal mol-1 )>OW -H…OW (-1.0 to 6.5 kcal mol-1 )>OW -H…OM (-1.2 to 5.3 kcal mol-1 ). This ordering of cooperativity contribution is similar to the HB energy ordering obtained by the MTA-based method. It is emphasized here that, the interplay between the cooperative and anti-cooperative contributions are indispensable for the correct energetic ordering of these HBs.

Crystal structures of anhydrous and hydrated ceftibuten.

Ceftibuten, C15H14N4O6S2, with the systematic name (6R,7R)-7-{[(Z)-2-(2-amino-1,3-thia-zol-4-yl)-4-carb-oxy-but-2-eno-yl]amino}-8-oxo-5-thia-1-aza-bicyclo-[4.2.0]oct-2-ene-2-carb-oxy-lic acid, is a third generation, orally administered cephalosporin anti-biotic with broad anti-microbial activity and stability against extended spectrum β-lactamases. Ceftibuten can exist in various hydration states and to better understand the location of the water mol-ecules of crystallization and their effect on the structure, the crystal structures of anhydrous (I) and hydrated (II) ceftibuten were determined and both occur as zwitterions with proton transfer from the carboxyl-ate group adjacent to the β-lactam ring to the N atom of the thia-zole ring. The β-lactam ring in (I) is almost planar but the equivalent grouping in (II) is slightly buckled. In the extended structure of (I), O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. In (II), O-H⋯Oc, N-H⋯Oc, O-H⋯Ow, N-H⋯Ow and Ow-H⋯Ow (c = ceftibuten, w = water) hydrogen bonds link the components into a three-dimensional network. A large void space is present within the anhydrous crystal structure that can accommodate between two and three mol-ecules of water.

Conformations and structures of 1,4-pentadien-3-ol and its water complex characterized by rotational spectroscopy

The 1,4-pentadien-3-ol and its monohydrate have been characterized by microwave spectroscopy in combination with theoretical computations. Experiments and ab initio calculations revealed that the 1,4-pentadien-3-ol monomer prefers a configuration with one vinyl being syn to the hydroxyl oxygen and the hydroxyl hydrogen toward the skew arranged vinyl, which therefore makes possible simultaneous CH···O and OH···π interactions. The observed monohydrate corresponds to the global minimum predicted theoretically, which is stabilized through a primary OH···Ow hydrogen bond together with a much weaker OwH···π hydrogen bond. The NCI analyses, NBO calculation and SAPT method were applied to further elucidate the characteristics of hydrogen bonds in the 1,4-pentadien-3-ol···water complex.

Crystal structure of [{[Ni(C10H24N4)][Ni(CN)4]}·2H2O] n , a one-dimensional coordination polymer formed from the [Ni(cyclam)]2+ cation and the [Ni(CN)4]2- anion.

The asymmetric unit of the title compound, catena-poly[[[(1,4,8,11-tetra-aza-cyclo-tetra-decane-κ4 N 1,N 4,N 8,N 11)nickel(II)]-μ-cyanido-κ2 N:C-[bis-(cyanido-κC)nickel(II)]-μ-cyanido-κ2 C:N] dihydrate], {[Ni2(CN)4(C10H24N4)]·2H2O] n or [{[Ni(C10H24N4)][Ni(CN)4]}·2H2O] n , consists of a pair of crystallographically non-equivalent macrocyclic cations and anions. The nickel(II) ions (all with site symmetry ) are coordinated by the four secondary N atoms of the macrocyclic ligands, which adopt the most energetically stable trans-III conformation, and the mutually trans N atoms of the tetra-cyano-nickelate anion in a slightly tetra-gonally distorted NiN6 octa-hedral coordination geometry. The [Ni(CN)4)]2- anion exhibits a bridging function, resulting in the formation of parallel polymeric chains running along the [10] direction. The water mol-ecules of crystallization play a pivotal role in the three-dimensional supra-molecular organization of the crystal. Acting as acceptors, they form N-H⋯Ow (w = water) hydrogen bonds with the secondary amino groups of the macrocycles, forming layers oriented parallel to the (001) plane. At the same time, as donors, they inter-act with the non-coordinated cyano groups of the anion via Ow-H⋯Nc (c = cyanide) hydrogen bonds, giving two-dimensional layers oriented parallel to the (100) plane and thus generating a three-dimensional network.

Synthesis, crystal structure, vibrational study, optical properties and thermal behavior of a new hybrid material bis(3-amino-4-phenyl-1H-pyrazolium) tetrachloridocobaltate (II) monohydrate

The title organic–inorganic hybrid compound, (C9H10N3)2[CoCl4]·H2O, was synthesized by slow evaporation at room temperature. Single-crystal X-ray diffraction analysis indicates that the asymmetric unit in this compound consists of one tetrahedral geometry [CoCl4]2-, two protonated organic cations (C9H10N3)+ and one water molecule of crystallization. In the crystal structure, the inorganic layers are built from tetrachloridocobaltate anions [CoCl4]2- and free water molecules, linked together by Ow—H…Cl hydrogen bonds and halogen···halogen interactions. The organic cations are intercalated between the mineral layers via N–H⋯Cl hydrogen bonds and form chains through cycle stacking interactions. The atomic arrangement can be described as an alternation of organic and inorganic layers along the c-axis. Crystal cohesion is achieved through N–H⋯Cl, Ow—H…Cl, N–H … Ow hydrogen bonds between organic cations, inorganic anions and the water molecules building up a three-dimensional network. The vibrational properties were investigated experimentally by means of IR spectroscopy. The powder X-ray diffraction was used to confirm the phase purity. Also, The UV–visible and the photoluminescence (PL) properties of the compound were investigated at room temperature in the solid state. The crystal morphology was carried out using Bravais–Friedel–Donnay–Harker (BFDH) model. Electronic properties such as HOMO and LUMO energies were also obtained. Thermal behavior was characterized by thermogravimetric and differential scanning calorimetry TG-DSC.

Two novel mixed-ligand Ni(II) and Co(II) complexes with 1,10-phenanthroline: Synthesis, structural characterization, and thermal stability

Two nickel(II) and cobalt(II) complexes with phenanthroline, [Ni(Phen)(H2O)3Br]Br (1) and [Co(Phen)2(H2O)2](Hba)2·2H2O (2), Phen = 1,10-phenanthroline and Hba− = barbiturate anion, were synthesized and characterized by powder XRD, TGA and FT-IR. Their structures were determined by single crystal X-ray diffraction techniques. The Ni2+ ion is coordinated by two N atoms of Phen molecule, Br− ion and three H2O molecules forming an octahedron. Uncoordinated and coordinated Br− ions are connected with water molecules by OH⋯Br intermolecular hydrogen bonds with the formation of a 2D plane network which is extended into a 3D network by π−π stacking interactions. The [Co(Phen)2(H2O)2]2+ cation contains a six-coordinated cobalt atom chelated by two Phen ligands and two aqua ligands in the cis arrangement. NH⋯O, OH⋯O and CH⋯O intermolecular hydrogen bonds form a 3D net. NH⋯O hydrogen bonds form the infinite chains of Hba–. In addition, coordinated Phen molecules and lattice water molecules are linked via CH⋯OW hydrogen bonds to form infinite zigzag chains. These different chains are connected by OWH⋯O hydrogen bonds. π−π interaction plays an important role in the stabilization of structures 1–2. FT-IR, TGA, the diffuse reflectance, and UV–Vis spectra were also used to characterize these compounds.

Sulfur Hydrogen Bonding in Isolated Monohydrates: Furfuryl Mercaptan versus Furfuryl Alcohol.

The hydrogen bonds involving sulfur in the furfuryl mercaptan monohydrate are compared with the interactions originating from the hydroxyl group in furfuryl alcohol. The dimers with water were created in a supersonic jet expansion and characterized using microwave spectroscopy and supporting molecular orbital calculations. In furfuryl alcohol-water, a single isomer is observed, in which the water molecule forms an insertion complex with two simultaneous hydrogen bonds to the alcohol (O-H⋅⋅⋅Ow ) and the ring oxygen (Ow -H⋅⋅⋅Or ). When the alcohol is replaced by a thiol group in furfuryl mercaptan-water, two isomers are observed, with the thiol group preferentially behaving as proton donor to water. The first isomer is topologically equivalent to the alcohol analog but the stronger hydrogen bond is now established by water and the ring oxygen, assisted by a thiol S-H⋅⋅⋅Ow hydrogen bond. In the second isomer the sulfur group accepts a proton from water, forming a Ow -H⋅⋅⋅S hydrogen bond. Binding energies for the mercaptan-water dimer are predicted around 12 kJ mol-1 weaker than in the alcohol hydrate (B3LYP-D3(BJ)). The non-covalent interactions in the furfuryl dimers are dominantly electrostatic according to a SAPT(0) energy decomposition, but with increasing dispersion components in the mercaptan dimers, which are larger for the isomer with the weaker Ow -H⋅⋅⋅S interaction.

Enhancement of Intermolecular Magnetic Exchange through Halogen···Halogen Interactions in Bisadeninium Rhenium(IV) Salts

Two novel ReIV salts of general formula [H2ade]2[ReIVX6]X2·4H2O [H2ade2+ = 9H-adenine-1,7-diium; X = Cl(1) and Br(2)] have been synthesized and magnetostructurally characterized. 1 and 2 are isostructural salts that crystallize in the orthorhombic system with space group Fdd2. Both compounds are made up of discrete mononuclear [ReIVX6]2– and X– anions and doubly protonated adenine cations. The six-coordinate rhenium(IV) ion is bonded to six halide ligands [X = Cl (1) and Br (2)] in an octahedral geometry. Short intermolecular ReIV–X···X–ReIV interactions, as well as ReIV–X···H–N(H2ade) and ReIV–X···H–Ow hydrogen bonds, are present in the crystal lattice of 1 and 2. Magnetic susceptibility measurements on polycrystalline samples of 1 and 2 in the temperature range 2.0–300 K show the occurrence of significant intermolecular antiferromagnetic interactions in both compounds, resulting in the observation of maxima in χM at ca. 6.0 (1) and 12.0 K (2). The larger spin delocalization from the ReIV ion onto the pe...

Synthesis, structural and vibrational investigation for Tetrakis(2,6-diethylanilinium) decabromodibismuthate(III) hexahydrate [C10H16N]4Bi2Br10·6H2O

The new organic–inorganic compound, Tetrakis(2,6-diethylanilinium) decabromodibismuthate(III) hexahydrate, has been synthesized and characterized by single-crystal X-ray diffraction at room temperature. It crystallizes in the monoclinic system (P21/c space group). The structure consists of discrete dinuclear [Bi2Br10]4− anions, [C10H16N]+ cations and water molecules. The organic part consists of two organic cations which orient their two amine groups to the neighboring anions. The inorganic entity is made up by [Bi2Br10]4− dimers composed of two equivalent irregular octahedra sharing one edge. The water molecules are sandwiched between the [Bi2Br10]4−anions and the neighboring [C10H16N]+ cations. The crystal packing is governed by N(O)–H⋯Br and N–H⋯OW hydrogen bonds and π−π interactions to built a three dimensional network. The nature of the inorganic polyhedra distortion, which can be attributed to the stereo-activity of the Bi(III) lone electron pair, has been studied. The infrared and NMR spectra were calculated by Density Functional Theory (DFT) using the B3LYP method with the 6–311++G** basis set. A good consistency was found between the calculated and experimental data. The vibrational absorption bands were identified by infrared spectroscopy.

Crystal structure of (E)-N'-(5-bromo-2-hy-droxy-benzyl-idene)nicotinohydrazide monohydrate.

In the title compound, C13H10BrN3O2·H2O, the conformation about the azomethine double bond is E. The mol-ecule exists in the amido form with a C=O bond length of 1.229 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The whole mol-ecule is almost planar, with an r.m.s. deviation of 0.021 Å for all non-H atoms, and the dihedral angle between the planes of the pyridine and benzene rings is 0.74 (12)°. In the crystal, the water mol-ecule of crystallization links the organic mol-ecules via Ow-H⋯O, Ow-H⋯N and N-H⋯Ow hydrogen bonds and short C-H⋯Ow contacts, forming sheets lying parallel to (100). Within the sheets there is a weak π-π inter-action involving the pyridine and benzene rings [centroid-to-centroid distance = 3.8473 (15) Å]. The sheets are linked via C-H⋯Br inter-actions, forming a three-dimensional network.

Synthesis and Physico-Chemical Studies of a New Noncentrosymmetric Bis[N-(2-hydroxyethyl)piperazine-1,4-diium] Tetrakis(hydrogen oxalate) Trihydrate: [C6H16N2O]2(HC2O4)4·3H2O

The new noncentrosymmetric oxalate with the general formula [C6H16N2O]2(HC2O4)4·3H2O, has been synthesized and single crystals were grown from aqueous solution by slow evaporation technique. Single crystal X-ray diffraction study on grown crystal reveals that they belong to triclinic system with space group P1. The unit cell dimensions are: a = 5.688(2) A, b = 8.315(2) A, c = 16.634(3) A, α = 96.63(2)°, β = 99.81(3)°, γ = 110.01(2)° with V = 715.4(3) A3 and Z = 1. The structure has been solved using a direct method and refined to a reliability R factor of 0.052. The structure is built up from anionic chains parallel to the a-axis. These chains are interconnected by the organic cations and water molecules via hydrogen bonds so as to build a three dimensional arrangement. FT-IR spectrum confirms the presence of the functional groups in the synthesized material. The 13C CP-MAS NMR spectrum is in agreement with the X-ray structure. UV–Vis spectrum indicates that the crystal is transparent in UV and visible region with a lower cutoff wavelength of 212 nm. The DSC curve indicates that the crystal is thermally stable up to 330 K. The molecular structure of bis(N-(2-hydroxyethyl)piperazine-1,4-diium) Tetrakis(hydrogen oxalate) Trihydrate is formed by N-(2-hydroxyethyl)piperazine-1,4-diium cations, oxalate anions and water molecules held together by means of N–H⋯O, C–H⋯O, O–H⋯OW and OW–H⋯OW(O) hydrogen bonds to form three-dimensional network.

Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid.

Three salts, namely 2-amino-4,6-dimethylpyrimidin-1-ium thiobarbiturate trihydrate (I), 2-amino-4,6-dimethoxypyrimidin-1-ium thiobarbiturate dihydrate (II) and 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidin-1-ium thiobarbiturate (III), were synthesized and characterized by IR and X-ray diffraction techniques. The primary interaction between the acid and base happens via N-H...O hydrogen bonds in (II) and (III), and via water-mediated N-H...OW and OW-HW...S in (I). The water molecules present in compound (I) form a (H2O)12 water cluster via water-water interactions. In all three compounds (I)-(III), thiobarbiturate anions form self-complementary pairs with a robust R2(2)(8) motif via a pair of N-H...O/N-H...S hydrogen bonds. They mimic the nucleobase base pairs by utilizing the same groups (thymine/uracil uses N3-H and C4=O8 groups during the formation of Watson-Crick and Hoogsteen base pairs with adenine). Compound (I) forms a water-mediated base pair through N-H...OW hydrogen bonds and forms an R4(2)(12) motif. The formation of N-H...S hydrogen bonds, water-mediated base pairs and water-water interactions in these crystal systems offers scope for these systems to be considered as a model in the study of hydration of nucleobases and water-mediated nucleobase base pairs in macromolecules.

Tetraquinolinium ditelluro(VI)octavanadate(V) octahydrate

In the title compound, (C9H8N)4[Te2V8O28]·8H2O, the com­plete heteropolyanion is generated by a crystallographic inversion centre. One of the two quniolinium ions forms an N—H⋯Op (p = polyoxidometallate) hydrogen bond and the other an N—H⋯Ow (w = water) hydrogen bond. The water mol­ecules further link the components by O—H⋯Op and O—H⋯Ow hydrogen bonds. A number of C—H⋯O inter­actions and aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.541 (7) Å] are also observed. Together, these generate a three-dimensional network.

Theoretical study of the cooperativity in substituted dimethyl ethers complexed with two water molecules. Red or blue shifts of the ν(CH) vibrations?

The cooperative interactions in CH3OCH3, CH3OCH2F, CH3OCHF2, CH2FOCHF2 and CHF2OCHF2 complexed with two H2O molecules are investigated using the B3LYP method with the 6-311++G(d,p) level. The calculations include the optimized geometries, the cooperative energies along with a natural bond orbital (NBO analysis). Cyclic complexes characterized by OwHw…O and CH…Ow hydrogen bonds are formed. The pairwise or two body interaction energies are computed. The results show that the OwHw…O interaction energies increase with the proton affinity of the O atom of the ethers and that the CH…Ow interaction energies increase with increasing acidity of the CH bond. This is in agreement with the intermolecular distances. The cooperative energy represents 15–20% of the total energy. When nF=2–4, blue shifts are predicted for the ν(CH) vibration for the 1–1 complexes but red shifts are predicted for the 1–2 complexes. The variation of the CH distances is explained by a competition between the variation of the intramolecular hyperconjugation energies and the intermolecular hyperconjugation energies. The charge transfer between the ether and water molecules is analyzed. When the negative charge on one H2O molecule decreases, the positive charge on the other H2O molecule increases, indicating a nice reciprocal effect.

Bis(2-amino-benzothia-zol-3-ium) bis-(7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxyl-ato-κ(3)O(2),O(3),O(7))zincate hexa-hydrate.

In the title hydrated mol­ecular salt, (C7H7N2S)2[Zn(C8H8O5)2]·6H2O, which is isotypic with its MnII, CoII and NiII analogues, the Zn2+ ion lies on a crystallographic inversion centre and a distorted ZnO6 octa­hedral coordination geometry arises from the two doubly deprotonated O,O′,O′′-tridentate ligands. In the crystal, the components are linked by N—H⋯Oa, N—H⋯Ow, Ow—H⋯Oa and Ow—H⋯Ow hydrogen bonds (w = water and a = anion).

The three-dimensional intermolecular network formedviawater molecules intrans-bis(nitrito-κN)tetrakis(pyridine-κN)ruthenium(II) dihydrate

The molecular geometry of the tetragonal crystal structure of the title compound, [Ru(NO(2))(2)(C(5)H(5)N)(4)]·2H(2)O, differs from that previously determined by powder diffraction [Schaniel et al. (2010). Phys. Chem. Chem. Phys. 12, 6171-6178]. In the [Ru(NO(2))(C(5)H(5)N)(4)] molecule, the Ru atom lies at the intersection of three twofold axes (Wyckoff position 8b). It is coordinated by four N atoms of the pyridine rings, as well as by two N atoms of N-nitrite groups. The last two N atoms are located on a twofold axis (Wyckoff position 16f). The O atoms of the water molecules are situated on a twofold axis (Wyckoff position 16e). Short intermolecular contacts are observed in the crystal structure, viz. N-O···OW and N-O···H-OW contacts between nitrite and water, and weak C-H···OW hydrogen bonds between pyridine and water. Thus, the intercalated water molecules act as bridges connecting the trans-[Ru(NO(2))(2)(py)(4)] molecules into a three-dimensional network.

Studies on the structures and interactions of glutathione in aqueous solution by molecular dynamics simulations and NMR spectroscopy

All-atom molecular simulations and temperature-dependent NMR have been used to investigate the conformations and hydrogen bonds of glutathione (GSH) in aqueous solution. The simulations start from three different initial conformations. The properties are characterized by intramolecular distances, radius of gyration, root-mean-square deviation, and solvent-accessible surface. GSH is highly flexible in aqueous solutions in the simulations. Moreover, conformations can covert between “extended” and “folded” states. Interestingly, the two different hydrogen atoms in cysteine (H N2) and glycin (H N3) show different capabilities in forming N H⋯OW hydrogen bonds. The temperature-dependent NMR results of the different amide hydrogen atoms also show agreements with the MD simulations. Competing formation of GSH hydrogen-bonding interactions in aqueous solutions leads to hydrogen-bonding networks and the distribution of conformations. These changes will affect the activity of GSH under physiological conditions.

1,4-Bis(5-methyl-1H-1,2,4-triazol-3-yl)benzene tetrahydrate

In the title compound, C12H12N6·4H2O, the two triazole rings adopt a cis configuration with a crystallographic twofold axis passing through the central benzene group. The benzene and triazole rings are almost coplanar with a dihedral angle of 5.5 (1)°. In the crystal, water mol­ecules are joined together by OW—H⋯OW hydrogen bonds to form a one-dimensional zigzag chain. These water chains are further connected to the organic mol­ecule, forming a three-dimensional network by inter­molecular OW—H⋯N and N—H⋯OW hydrogen bonds. Moreover, π–π stacking inter­actions between triazole rings [centroid–centroid distances = 3.667 (1)–3.731 (1) Å] are observed. One of the water mol­ecules shows one of the H atoms to be disordered over two positions.