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1.  4,4′-Dimethyl-2,2′-{[2,3,3a,4,5,6,7,7a-octa­hydro-1H-benzimidazole-1,3-di­yl]bis­(methyl­ene)}diphenol 
The asymmetric unit of the title compound, C23H30N2O2, contains one half-mol­ecule, with a twofold axis splitting the mol­ecule in two identical halves. The structure of the racemic mixture has been reported previously [Rivera et al. (2009 ▶) J. Chem. Crystallogr. 39, 827–830] but the enanti­omer reported here crystallized in the ortho­rhom­bic space group P21212 (Z = 2), whereas the racemate occurs in the triclinic space group P-1 (Z = 2). The observed mol­ecular conformation is stabilized by two intra­molecular O—H⋯N hydrogen bonds, which generate rings with graph-set motif S(6). In the crystal, mol­ecules are linked via non-classical C—H⋯O inter­actions, which stack the mol­ecules along the b axis.
doi:10.1107/S1600536813015237
PMCID: PMC3772489  PMID: 24046632
2.  (2S,7S)-10-Ethyl-1,8,10,12-tetra­aza­tetra­cyclo­[8.3.1.18,12.02,7]penta­decan-10-ium iodide 
The title chiral quaternary ammonium salt, C13H25N4 +·I−, was synthesized through the Menschutkin reaction between the cage aminal (2S,7S)-1,8,10,12-tetra­aza­tetra­cyclo­[8.3.1.18,12.02,7]penta­decane and ethyl iodide. The quaternization occurred regioselectively on the nitrogen with major sp3 character. The crystal structure consists of anions and cations separated by normal distances. Ions are not linked through C—H⋯I hydrogen bonds.
doi:10.1107/S1600536812040159
PMCID: PMC3470393  PMID: 23125806

Results 1-2 (2)