Journal of Chemical Crystallography

, Volume 41, Issue 7, pp 1007–1012 | Cite as

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

  • Kirsten E. Christensen
  • Kristína Csatayová
  • Stephen G. Davies
  • James A. Lee
  • Paul M. Roberts
  • Amber L. Thompson
  • James E. Thomson
Original Paper

Abstract

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 P212121 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 P21/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.

Graphical Abstract

The structures of benzyl (RS,RS,RS)-7-phenylbicyclo[5.1.0]octan-2-ylcarbamate and (RS,RS,RS)-N-[3′-(4″-methylpiperazin-1″-yl)propyl]-N-{5-(4′′′-cyanophenyl)bicyclo[3.1.0]hexan-2-yl}amine dihydrochloride have been analysed by single crystal X-ray diffraction.

Keywords

Simmons–Smith Cyclopropane Allylic carbamate X-ray crystal structure cis-SCH-A 

References

  1. 1.
    Aciro C, Claridge TDW, Davies SG, Roberts PM, Russell AJ, Thomson JE (2008) Org Biomol Chem 6:3751CrossRefGoogle Scholar
  2. 2.
    Aciro C, Davies SG, Roberts PM, Russell AJ, Smith AD, Thomson JE (2008) Org Biomol Chem 6:3762CrossRefGoogle Scholar
  3. 3.
    Bond CW, Cresswell AJ, Davies SG, Fletcher AM, Kurosawa W, Lee JA, Roberts PM, Russell AJ, Smith AD, Thomson JE (2009) J Org Chem 74:6735CrossRefGoogle Scholar
  4. 4.
    Bagal SK, Davies SG, Lee JA, Roberts PM, Russell AJ, Scott PM, Thomson JE (2010) Org Lett 12:136CrossRefGoogle Scholar
  5. 5.
    Davies SG, Ling KB, Roberts PM, Russell AJ, Thomson JE, Woods PA (2010) Tetrahedron 66:6806CrossRefGoogle Scholar
  6. 6.
    Davies SG, Fletcher AM, Kurosawa W, Lee JA, Poce G, Roberts PM, Thomson JE, Williamson DM (2010) J Org Chem 75:7745Google Scholar
  7. 7.
    Bagal SK, Davies SG, Lee JA, Roberts PM, Scott PM, Thomson JE (2010) J Org Chem 75:8133Google Scholar
  8. 8.
    Davies SG, Ling KB, Roberts PM, Russell AJ, Thomson JE (2007) Chem Commun 39:4029CrossRefGoogle Scholar
  9. 9.
    Csatayová K, Davies SG, Lee JA, Ling KB, Roberts PM, Russell AJ, Thomson JE (2010) Org Lett 12:3152CrossRefGoogle Scholar
  10. 10.
    Csatayová K, Davies SG, Lee JA, Ling KB, Roberts PM, Russell AJ, Thomson JE (2010) Tetrahedron 66:8420Google Scholar
  11. 11.
    The relative configuration within syn-5 was unambiguously established by single crystal X-ray analysis. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 779449Google Scholar
  12. 12.
    McBriar MD, Guzik H, Xu R, Paruchova J, Li S, Palani A, Clader JW, Greenlee WJ, Hawes BE, Kowalski TJ, O’Neill K, Spar B, Weig B (2005) J Med Chem 48:2274CrossRefGoogle Scholar
  13. 13.
    Hodgson DM, Humphreys PG, Miles SM, Brierley CAJ, Ward JG (2007) J Org Chem 72:10009CrossRefGoogle Scholar
  14. 14.
    Cosier J, Glazer AM (1986) J Appl Crystallogr 19:105CrossRefGoogle Scholar
  15. 15.
    Otwinowski Z, Minor W (1997) Methods Enzymol. Academic Press, New York, pp 307–326Google Scholar
  16. 16.
    Rigaku Americas and Rigaku Corporation (2009) CrystalClear (Version 2.0). Rigaku Americas, 9009 TX, USA, pp 77381–5209Google Scholar
  17. 17.
    Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla MC, Polidori G, Camalli M (1994) J Appl Crystallogr 27:435Google Scholar
  18. 18.
    Palatinus L, Chapuis G (1997) J Appl Crystallogr 40:786CrossRefGoogle Scholar
  19. 19.
    Betteridge PW, Carruthers JR, Cooper RI, Prout CK, Watkin DJ (2003) J Appl Crystallogr 36:1487CrossRefGoogle Scholar
  20. 20.
    Cooper RI, Thompson AL, Watkin DJ (2010) J Appl Cryst 43:1100Google Scholar
  21. 21.
    Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 733888Google Scholar
  22. 22.
    Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 783810Google Scholar
  23. 23.
    Leong MK, Mastryukov VS, Boggs JE (1998) J Mol Struct 445:149CrossRefGoogle Scholar
  24. 24.
    Abraham RJ, Castellazzi I, Sancassan F, Smith TAD (1999) J Chem Soc Perkin Trans 2:99Google Scholar
  25. 25.
    Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed 34:1555CrossRefGoogle Scholar
  26. 26.
    Flack HD (1983) Acta Cryst A39:876Google Scholar
  27. 27.
    Flack HD, Bernardinelli G (2000) J Appl Cryst 33:1143CrossRefGoogle Scholar
  28. 28.
    Hooft RWW, Straver LH, Spek AL (2008) J Appl Cryst 41:96CrossRefGoogle Scholar
  29. 29.
    Thompson AL, Watkin DJ (2009) Tetrahedron: Asymmetry 20:712CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Kirsten E. Christensen
    • 1
  • Kristína Csatayová
    • 2
  • Stephen G. Davies
    • 2
  • James A. Lee
    • 2
  • Paul M. Roberts
    • 2
  • Amber L. Thompson
    • 2
  • James E. Thomson
    • 2
  1. 1.Harwell Science and Innovation CampusDiamond Light SourceChiltonUK
  2. 2.Department of Chemistry, Chemistry Research LaboratoryUniversity of OxfordOxfordUK

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