Stereochemical Assignment of Substituted 2-Aminobicyclo[3.1.0]hexane and 2-Aminobicyclo[5.1.0]octane Derivatives via Single Crystal X-ray Diffraction

Journal article

Crystals of benzyl (RS,RS,RS)-7-phenylbicyclo[5.1.0]octan-2-ylcarbamate 9 and (RS,RS,RS)-N-[3′-(4′-methylpiperazin-1′-yl)propyl]-N-{5- (4‴-cyanophenyl)bicyclo[3.1.0]hexan-2-yl}amine dihydrochloride 10•2HCl were synthesised and single crystal X-ray diffraction was used to establish unambiguously the relative configurations within these structures. Compound 9 crystallizes in the orthorhombic space group P2 1 2 1 2 1 with cell parameters of a = 6.85340(10) Å, b = 9.8732(2) Å, c = 27.5407(6) Å, V = 1863.54(6) Å3 and Z = 4. In the crystal structure adjacent molecules are linked by N-H•••O=C hydrogen bonds. Compound 10•2HCl crystallizes as the corresponding monohydrate in the monoclinic space group P2 1/n with cell parameters of a = 7.1540(17) Å, b = 39.763(12) Å, c = 8.163(3) Å, β = 91.062(7)°, V = 2321.7(11) Å3 and Z = 4. In the crystal structure adjacent molecules are linked by a series of hydrogen bonds between the ammonium groups, chloride ions and adventitious water molecules. © 2011 Springer Science+Business Media, LLC.

Authors: Christensen, K; Csatayova, K; Davies, S; Lee, J; Roberts, P

• Publication status: Published
• Journal: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
• Volume: 41
• Issue: 7
• Pages: 1007-1012
• Publication date: 2011-07-01
• DOI: 10.1007/s10870-011-0034-6
• EISSN: 1572-8854
• ISSN: 1074-1542
• Language: English
• Keywords: cis-SCH-A; Simmons-Smith; Allylic carbamate; Cyclopropane; X-ray crystal structure