Software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015b) for (1), (3), (4), (6), (10), (11), (12), (13) SHELXL2014 (Sheldrick, 2015b) for (2), (5), (7), (8), (9).Virtually Music in El Cajon, CA, is in business of 7929 - Bands, Orchestras, Actors, and Other Entertainers and Entertainment Groups as well as 711130 - Musical Groups and Artists.
For all structures, molecular graphics: Mercury (Macrae et al., 2008). For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Additionally, some anion–π and lone-pair π secondary interactions are identified in almost all of the crystal structures. The crystal structures are determined mainly by Coulombic interactions and hydrogen bonds, and the latter form is determined by different networks.
The cation is quite rigid and all 19 cytisinium fragments in the studied series have very similar conformations. This third form may therefore be regarded as a 3+ species, or sesqui-cation, and is observed solely in the salts with bromide, iodide or triiodide (heavier halogen) anions. Three forms of the cytisinium cation were identified, namely the monocation, which is always protonated at the N atom, the dication, which utilizes both protonation sites, and the third form, which contains two cytisine moieties connected by very short and linear O H O hydrogen bonds, with an O O distance of approximately 2.4 Å. the N atom of the piperidine ring and the carbonyl O atom of the pyridone ring. Cytisine has two potential protonation sites, i.e. I −, cytisinediium (6-oxidaniumylidene-7,11-diazatricyclotrideca-2,4-dien-11-ium) bis(perchlorate), C 11H 16N 2O 2+♲ClO 4 −, and cytisinediium dichloride trihydrate, C 11H 16N 2O 2+♲Cl −♳H 2O.I 3 −♲I −, hydrogen dicytisinium bis(triiodide) iodide, C 22H 31N 4O 2 3+♲I 3 −.H 2O, hydrogen dicytisinium tribromide, C 22H 31N 4O 2 3+♳Br −, hydrogen dicytisinium triiodide, C 22H 31N 4O 2 3+♳I −, hydrogen dicytisinium triiodide diiodide, C 22H 31N 4O 2 3+.
H 2O, cytisinium nitrate monohydrate, C 11H 15N 2O +.H 2O, cytisinium iodide monohydrate, C 11H 15N 2O +.