Abstract:The title compound, C15H11N3O3·2H2O, crystallizes with terpyridine dioxide molecules positioned on mirror planes in the space group Pnma. Catemeric assemblages of terpyridine molecules [C—H⋯−O—+N = 3.386 (4) Å] are linked by bridging water molecules [C—H⋯O = 3.288 (4) and 3.386 (4) Å; O—H⋯−O—+N = 2.837 (3) and 2.878 (4) Å], giving stacks of two‐dimensional undulating motifs.
“…Colourless, X-ray quality crystals of 3 were obtained by slow evaporation of a CHCl 3 / MeOH solution of the crude product in the presence of excess of 1,3-diaminopropane. The IR and 1 H and 13 C NMR spectroscopic data agreed with those reported. 3,5 FAB-MS 698.0 [M + H] + (calc.…”
Section: Experimental Generalsupporting
confidence: 87%
“…Commercially available chemicals were reagent grade and were used without further purification. 1 H and 13 C NMR spectra were recorded at room temperature on a Bruker Avance DRX 500 MHz spectrometer; chemical shifts are relative to residual solvent peaks with TMS d ¼ 0 ppm. Infrared spectra were recorded on a Shimadzu FTIR-8400S spectrophotometer with solid samples on a Golden Gate diamond ATR accessory.…”
Section: Experimental Generalmentioning
confidence: 99%
“…Of these, most exhibit single water molecules or dimers, either in discrete pockets in the structure or hydrogen bonded to donor atoms in the ligand. [12][13][14][15][16][17][18] In one case, {H 2 O} 3 units interconnect ligands to produce hydrogen bonded chains. 14 Protonated tpy ligands are prone to being involved in hydrogen bonded assemblies, examples including chloride-water chains, 19 and methylsulfate-water aggregates.…”
“…Colourless, X-ray quality crystals of 3 were obtained by slow evaporation of a CHCl 3 / MeOH solution of the crude product in the presence of excess of 1,3-diaminopropane. The IR and 1 H and 13 C NMR spectroscopic data agreed with those reported. 3,5 FAB-MS 698.0 [M + H] + (calc.…”
Section: Experimental Generalsupporting
confidence: 87%
“…Commercially available chemicals were reagent grade and were used without further purification. 1 H and 13 C NMR spectra were recorded at room temperature on a Bruker Avance DRX 500 MHz spectrometer; chemical shifts are relative to residual solvent peaks with TMS d ¼ 0 ppm. Infrared spectra were recorded on a Shimadzu FTIR-8400S spectrophotometer with solid samples on a Golden Gate diamond ATR accessory.…”
Section: Experimental Generalmentioning
confidence: 99%
“…Of these, most exhibit single water molecules or dimers, either in discrete pockets in the structure or hydrogen bonded to donor atoms in the ligand. [12][13][14][15][16][17][18] In one case, {H 2 O} 3 units interconnect ligands to produce hydrogen bonded chains. 14 Protonated tpy ligands are prone to being involved in hydrogen bonded assemblies, examples including chloride-water chains, 19 and methylsulfate-water aggregates.…”
“…We have prepared the title compound as a continuing effort to understand the intermolecular contact preferences of the N-oxide group in molecular crystals [1][2][3][4]. 2,2':6',2"-Terpyridine l,l"-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5].…”
Source of materialWe have prepared the title compound as a continuing effort to understand the intermolecular contact preferences of the N-oxide group in molecular crystals [1][2][3][4]. 2,2¢:6¢,2²-Terpyridine 1,1²-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5].
Source of materialWe have prepared the title compound as a continuing effort to understand the intermolecular contact preferences of the N-oxide group in molecular crystals [1][2][3][4]. 2,2¢:6¢,2²-Terpyridine 1,1²-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5]. Dimethyldioxirane (17.71 ml, 0.08 M) in acetone was stirred with terpyridine (150.4 mg, 0.6447 mol, Aldrich 98 %) in acetone (2 ml, Fisher reagent grade) for 5 d at 300 K. Filtration of the mixture provided terpyridine dioxide as a colorless solid (92.2 %, 157.6 mg; m.p. 502 507 K, cf. 505 506 K [6]). The title cocrystals were obtained by slow evaporation of a 1:1 mixture using the previously prepared 2,2¢:6¢,2²-terpyridine 1,1²-dioxide and commercially available 1,2,4,5-tetracyanobenzene in methylene chloride solution at room temperature. The oxidizing agent, dimethyldioxirane, was prepared by reacting potassium peroxomonosulfate (0.0390 mol) and NaHCO3 (0.138 mol) in acetone (38.4 ml) and water (50 ml) [7]. Vigorous stirring of the mixture at 263 K followed by distillation (40 100 Torr) at ambient temperature resulted in 0.06 0.08 M dimethyldioxirane as verified by titration against thioanisole.
Experimental detailsThe aryl hydrogen atoms were located in a difference density map and refined isotropically. The CH distances were normalized to 1.08 Å for subsequent investigation of CH···O interactions.
DiscussionThe crystal structure of this 1:1 bimolecular compound contains tetracyanobenzene (TCNB) and terpyridinedioxide (TPDO) molecules positioned on inversion and two-fold rotation symmetry elements, respectively. Inspection of molecular conformation reveals the expected planar TCNB with TPDO skewed due to the pyridyl-N-oxide-pyridyl geometry (ÐN10C9C8N1 = 145.7(1)°). The crystal structure is stabilized by an assortment of nonbonded contacts that link adjacent TCNB and TPDO building blocks. Each TCNB moiety forms C2AH···O15 N10
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