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Synthesis and Crystal Structure of a Pyrithione Derivative: Bis {2-[(1

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Synthesis and Crystal Structure of a Pyrithione Derivative: Bis {2-[(1 molbank Short Note Synthesis and Crystal Structure of A Pyrithione Derivative: Bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5- dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-) 1, 1, 2 Łukasz Balewski *, Franciszek S ˛aczewski y and Maria Gdaniec 1 Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gda´nsk, 80-416 Gda´nsk,Poland 2 Faculty of Chemistry, A. Mickiewicz University, 61-614 Pozna´n,Poland; [email protected] * Correspondence: [email protected]; Tel.: +48-58-349-1952; Fax: +48-58-349-1654 Deceased 18 October 2018. y Received: 31 May 2019; Accepted: 20 June 2019; Published: 25 June 2019 Abstract: The pyrithione derivative, bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H- imidazol-3-ium} tetrachlorocuprate(2-) (1a) has been obtained by the reaction of one equivalent of 2-[(4,5-dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide hydrochloride with one and a half equivalents of copper (II) chloride dihydrate in methanol in a very good yield. The structure of this product was confirmed by X-ray crystallography, infrared spectroscopy, and elemental analysis. Keywords: pyrithione derivative; imidazoline derivative; tetrachlorocuprate(2-); X-ray crystallography 1. Introduction Coordination chemistry of pyrithione (N-hydroxypyridine-2(1H)-thione (Hmpo)), its heavy metal salts, and complexes have been widely investigated. Hmpo constitutes a universal O, S-donor ligand [1–4]. The infrared spectra of Hmpo indicates that the compound exists predominantly in its tautomeric thione form [5,6]. Recent UV spectra of pyrithione have shown that tautomeric equilibrium depends on the solvent used. Thione form dominates in polar and protic solvents, whereas 2-mercaptopyridine N-oxide exists in non-polar solvents [7]. Strong bactericidal and fungicidal properties of pyrithione have been well demonstrated [8]. Pyrithione acts as a proton conductor and inhibits the membrane transport processes in fungi. However, it was found that fungi can detoxify this agent at low concentration [9]. A zinc complex of N-hydroxypyridine-2(1H)-thione (zinc pyrithione) is widely used in dandruff shampoos for treating dandruff and seborrhoeic dermatitis [10]. Moreover, it was demonstrated that zinc pyrithione exhibits also antibacterial properties. Zinc pyrithione is a good example of an antibiofilm agent, which improves the antibacterial activity of silver sulfadiazine ointment [11]. Copper pyrithione has been recently considered in supplanting zinc pyrithione in view of its low toxicity [12]. Pyrithione derivative, 2-[(4,5-dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide, as a free base [CAS Registry Number 90764-93-5] [13–15] and its water-soluble acid addition salts, hydrobromide [CAS Registry Number 6937-05-9] [13–16] and hydrochloride [CAS Registry Number 62377-10-0] [17], are regarded as useful chemical agents that control microbial growth. They possess both fungistatic and bacteriostatic effects and may serve as preservatives. 2. Results and Discussion The title compound: bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-) (1a) was synthesized by slow evaporation of methanolic solution of the Molbank 2019, 2019, M1067; doi:10.3390/M1067 www.mdpi.com/journal/molbank Molbank 2019, 2019, x 2 of 5 The title compound: bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} Molbank 2019, 2019, M1067 2 of 5 tetrachlorocuprate(2-) (1a) was synthesized by slow evaporation of methanolic solution of the 2-[(4,5- dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide hydrochloride (1) with excess of copper (II) chloride 2-[(4,5-dihydro-1dihydrate. H-imidazol-2-yl)thio]pyridine 1-oxide hydrochloride (1) with excess of copper (II) chlorideFor dihydrate.the preparation of 2-[(4,5-dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide (as free base or acid Foraddition the preparation salt), 2-bromopyridine of 2-[(4,5-dihydro-1 1-oxideH-imidazol-2-yl)thio]pyridine was reacted with an imidazolidine 1-oxide (as free-2-thione base or in acid a additionhalogenated salt), hydrocarbon 2-bromopyridine solvent 1-oxide (chloroform) was reacted or in with ethanol an imidazolidine-2-thione. According to the literature in a halogenated’s data, the hydrocarbonmixture require solventd heating (chloroform) for 12 hours or in ethanol.to give acid According addition to thesalt literature’s (hydrobromide) data, the. The mixture free base required may heatingbe obtained for 12 in hdioxane to give by acid treatment addition with salt (hydrobromide).an equivalent of dimethylaniline The free base may [13,14]. be obtained in dioxane by treatmentGenerally, with 2- an[(4,5 equivalent-dihydro- of1H dimethylaniline-imidazol-2-yl)thio]pyridine [13,14]. 1-oxide hydrochloride (1) [CAS RegistryGenerally, Number 2-[(4,5-dihydro-1 62377-10-0] canH-imidazol-2-yl)thio]pyridine be synthesized as a result of 1-oxide the nu hydrochloridecleophilic attack (1) [CAS of the Registry sulfur Numberatom of 62377-10-0]2-mercaptopyridine can be synthesized 1-oxide on as aC2 result carbon of the of nucleophilic 2-chloro-4,5 attack-dihydro of the-1H- sulfurimidazole atom (2 of- 2-mercaptopyridinechloroimidazoline). 1-oxideThe reaction on C2 was carbon carried of 2-chloro-4,5-dihydro-1 out in dichloromethaneH-imidazole at room (2-chloroimidazoline). temperature in high Theyield reaction and the was product carried 1 outprecipitated in dichloromethane after mixing at roomthe reactants. temperature This in method high yield provides and the a product certain 1advantage precipitated over after traditional mixing thethermal reactants. heating. This The method reaction provides completes a certain within advantage a significantly over traditional shorter thermaltime. In the heating. next step The, brown reaction single completes crystals of within the bis{2 a significantly-[(1-oxidopyridin shorter-2-yl)sulfanyl] time. In the-4,5 next-dihydro step,- brown1H-imidazol single-3 crystals-ium} tetrachlorocuprate(2 of the bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1-) (1a) suitable for X-ray diffraction analysisH-imidazol-3-ium} were obtained tetrachlorocuprate(2-)by slow evaporation ( 1aof) suitablemethanolic for X-ray solution diffraction, containing analysis the were 2 obtained-[(4,5-dihydro by slow-1H evaporation-imidazol-2- ofyl)thio]pyridine methanolic solution,1-oxide hydrochloride containing the (1) 2-[(4,5-dihydro-1and copper (II) chlorideH-imidazol-2-yl)thio]pyridine dihydrate at room temperature 1-oxide hydrochloride(Scheme 1). (1) and copper (II) chloride dihydrate at room temperature (Scheme1). Scheme 1. Synthesis of the 2-[(4,5-dihydro-12-[(4,5-dihydro-1H--imidazol-2-yl)thio]pyridineimidazol-2-yl)thio]pyridine 1 1-oxide-oxide hydrochloride ( 1) H 1a and bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1-imidazol-3-ium}H-imidazol-3-ium} tetrachlorocuprate(2-) tetrachlorocuprate(2 ( ).-) (1a). The crystal structure of the bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-) (1a) is shown in Figure1a (see also supplementary crystallographic data). The The crystal structure of the bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3- asymmetric unit of 1a consists of the organic cation and one half of the C symmetric [CuCl ]2 anion. ium} tetrachlorocuprate(2-) (1a) is shown in Figure 1a (see also supplementary2 crystallographic4 − data). In the 2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium cation, the two rings attached The asymmetric unit of 1a consists of the organic cation and one half of the C2 symmetric [CuCl4]2− to the S atom are nearly perpendicular with the dihedral angles between the imidazoline and pyridine anion. In the 2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium cation, the two rings best planes of 87.1 and the pyridine N-oxide group is oriented anti-relative to the imidazolinium attached to the S atom◦ are nearly perpendicular with the dihedral angles between the imidazoline ring. The conformation adopted by the cation results in a large deviation from 120 of the endocyclic and pyridine best planes of 87.1° and the pyridine N-oxide group is oriented anti◦ -relative to the bond angles at the pyridine C2 atom, [N1-C2-S7 111.01(11) and C3-C2-S7 129.23(11) ], and in short imidazolinium ring. The conformation adopted by the cation◦ results in a large deviation◦ from 120° of intramolecular contact H3 C8 of 2.51 Å. The most probable reason for these angular deviations is the endocyclic bond angles··· at the pyridine C2 atom, [N1-C2-S7 111.01(11)° and C3-C2-S7 129.23(11)°], repulsive interactions between H3 and C8. The cations are connected by a pair of N-H O hydrogen and in short intramoleculari contact H3···C8i of 2.51 Å. Thei most probable reason for ···these angular bonds [N9 O1 2.7714(16) Å, H9 O1 1.91 Å, <N9-H9 O1 166◦; symmetry code i: x+1/2, y+3/2, deviations ···is repulsive interactions··· between H3 and C8.··· The cations2- are connected −by+ a pair− of N- z] into centrosymmetric dimersi that, in turn, interacti with [CuCl4] anionsi via N-H Cl− bonds −H···O hydrogeni bonds [N9···O1 2.7714(16)i Å, H9···O1 1.91 Å, <N9-H9···O1 166°; symmetry··· code i: [N12 Cl1 3.2622(12) Å, <N12-H12 Cl1 156◦; symmetry code i: x, y+1, z], forming chains extended −x+1/2,··· −y+3/2, −z] into centrosymmetric··· dimers that, in turn, interact with [CuCl4]2- anions via N- along [1 0 1] (Figure1b). In addition, there is a short contact C2-S7 Cl2i [S2 Cl2i 3. 3279(5) Å, < H+···Cl− bonds [N12···Cl1i 3.2622(12) Å , <N12-H12··· Cl1i 156°; symmetry··· code··· i: x, y+1, z], forming C2-S7 Cl2i 169.60(5) symmetry code i: x, y+1, z] pointing to a weak chalcogen bonding between chains··· extended along◦ [1 0 1] (Figure 1b).− In− addition− , there is a short contact C2-S7··· Cl2i [S2··· Cl2i cations and anions from adjacent chains.
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