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Hydrogen-bond networks in the mono- and diprotonated cyclic diamine [9]aneN2S

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Abstract

The hydrogen-bond networks in the mono- and diprotonated cyclic diamine, 1-thia-4,7-diazacyclononane, [9]aneN2S, have been examined. Crystals of the monoprotonated, form [9]aneN2S ⋅ HCl, contain a ribbon-like network of alternating strong and weak intermolecular N\(---\)H ⋅⋅⋅ Cl hydrogen bonds and weak intramolecular N\(---\)H ⋅⋅⋅ N hydrogen bonds. Crystal data for [9]aneN2S ⋅ HCl: monoclinic, a = 6.6640(6) Å, b = 10.3493(9) Å, c = 6.9807(6) Å, β = 108.847(1)°, V = 455.63(7) Å3, space group P21, Z = 2. In the di-protonated form, [9]aneN2S ⋅ 2HBr, the ribbon-like network comprises strong intermolecular and weak intramolecular N\(---\)H ⋅⋅⋅ Br hydrogen bonds. Crystal data for [9]aneN2S ⋅ 2HBr: orthorhombic, a = 12.5918(13) Å, b = 8.0753(9) Å, c = 10.6856(11) Å, V = 1086.5(2) Å3, space group Pnma, Z = 4. The chloride anions of [9]aneN2S ⋅ HCl align in interlocking columns in the a- and c-direction whereas the bromide anions in [9]aneN2S ⋅ 2HBr occupy channels in the b-direction.

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Authors and Affiliations

  1. Department of Chemistry, University of Louisville, Louisville, Kentucky, 40292

    Craig A. Grapperhaus, Ming Li, Erica R. Gibson & Mark S. Mashuta

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  1. Craig A. Grapperhaus
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  2. Ming Li
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  3. Erica R. Gibson
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  4. Mark S. Mashuta
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Correspondence to Craig A. Grapperhaus.

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Grapperhaus, C.A., Li, M., Gibson, E.R. et al. Hydrogen-bond networks in the mono- and diprotonated cyclic diamine [9]aneN2S. Journal of Chemical Crystallography 34, 5–11 (2004). https://doi.org/10.1023/B:JOCC.0000014681.88460.f4

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