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Volume 69 
Part 11 
Page o1672  
November 2013  

Received 6 September 2013
Accepted 1 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.023
wR = 0.064
Data-to-parameter ratio = 14.6
Details
Open access

(R)-(-)-Quinuclidin-3-ol

aInstitut de Chimie Moleculaire de l'Universite de Bourgogne - ICMUB, UMR CNRS 6302, Universite de Bourgogne, 9, Av. Alain Savary, 21078 Dijon Cedex, France, and bCordenPharma - Synkem, 47 rue de Longvic, 21301 Chenove, France
Correspondence e-mail: yoann.rousselin@u-bourgogne.fr

The structure of the title compound [alternatively called (R)-(-)-1-aza­bicyclo­[2.2.2]octan-3-ol], C7H13NO, at 100 K has hexa­gonal (P61) symmetry. The structure shows a twist along the C-N pseudo-threefold axis. In the crystal, mol­ecules are linked via O-H...N hydrogen bonds, forming infinite chains along the c-axis direction. The crystal studied was twinned by merohedry (twin law: 010, 100, 00-1; population: 0.925:0.075)

Related literature

The title compound is a key building block for the syntheses of muscarinic receptor ligands, including solifenacin (Naito et al., 2005[Naito, R., Yonetoku, Y., Okamoto, Y., Toyoshima, A., Ikeda, K. & Takeuchi, M. (2005). J. Med. Chem. 48, 6597-6606.]), revatropate (Alabaster, 1997[Alabaster, V. A. (1997). Life Sci. 60, 1053-1060.]) and talsaclidine (Leusch et al., 2000[Leusch, A., Tröger, W., Greischel, A. & Roth, W. (2000). Xenobiotica, 30, 797-813.]). For properties of the title compound, see: Bosak et al. (2005[Bosak, A., Primozic, I., Orsulic, M., Tomic, S. & Simeon-Rudolf, V. (2005). Croat. Chem. Acta, 78, 121-128.]); Carroll et al. (1991[Carroll, F. I., Abraham, P., Gaetano, K., Mascarella, S. W., Wohl, R. A., Lind, J. & Petzoldt, K. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 3017-3026.]); Frackenpohl & Hoffmann (2000[Frackenpohl, J. & Hoffmann, H. M. R. (2000). J. Org. Chem. 65, 3982-3996.]); Day & Motherwell (2006[Day, M. G. & Motherwell, W. D. S. (2006). Cryst. Growth Des. 6, 1985-1990.]); Malone & Armstrong (2006[Malone, K. Y. & Armstrong, E. P. (2006). Pharmacotherapy, 26, 1694-1702.]); Siczek & Lis (2008[Siczek, M. & Lis, T. (2008). Acta Cryst. E64, o842.]); Sterling et al. (1988[Sterling, G. H., Doukas, P. H., Sheldon, R. J. & O?Neill, J. J. (1988). Biochem. Pharmacol. 37, 379-384.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); For absolute configuration, see: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); The twin law was determined using TwinRotMat implemented in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C7H13NO

  • Mr = 127.18

  • Hexagonal, P 61

  • a = 6.2076 (3) Å

  • c = 29.8731 (13) Å

  • V = 996.91 (11) Å3

  • Z = 6

  • Cu K[alpha]1 radiation

  • [mu] = 0.67 mm-1

  • T = 100 K

  • 0.58 × 0.44 × 0.32 mm

Data collection
  • Bruker D8 VENTURE diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.58, Tmax = 0.74

  • 15447 measured reflections

  • 1240 independent reflections

  • 1240 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.064

  • S = 1.15

  • 1240 reflections

  • 85 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

  • Absolute structure: Parsons & Flack (2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.]).

  • Absolute structure parameter: 0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.84 2.00 2.8366 (19) 176
Symmetry code: (i) [y-1, -x+y, z-{\script{1\over 6}}].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2517 ).


Acknowledgements

We thank Ms Marie-Jose Penouilh for the NMR and ESI mass spectra.

References

Alabaster, V. A. (1997). Life Sci. 60, 1053-1060.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Bosak, A., Primozic, I., Orsulic, M., Tomic, S. & Simeon-Rudolf, V. (2005). Croat. Chem. Acta, 78, 121-128.  [ChemPort]
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carroll, F. I., Abraham, P., Gaetano, K., Mascarella, S. W., Wohl, R. A., Lind, J. & Petzoldt, K. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 3017-3026.  [CSD] [CrossRef]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Day, M. G. & Motherwell, W. D. S. (2006). Cryst. Growth Des. 6, 1985-1990.  [CSD] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Frackenpohl, J. & Hoffmann, H. M. R. (2000). J. Org. Chem. 65, 3982-3996.  [CSD] [CrossRef] [PubMed] [ChemPort]
Leusch, A., Tröger, W., Greischel, A. & Roth, W. (2000). Xenobiotica, 30, 797-813.  [CrossRef] [PubMed] [ChemPort]
Malone, K. Y. & Armstrong, E. P. (2006). Pharmacotherapy, 26, 1694-1702.  [Web of Science] [PubMed]
Naito, R., Yonetoku, Y., Okamoto, Y., Toyoshima, A., Ikeda, K. & Takeuchi, M. (2005). J. Med. Chem. 48, 6597-6606.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siczek, M. & Lis, T. (2008). Acta Cryst. E64, o842.  [CSD] [CrossRef] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sterling, G. H., Doukas, P. H., Sheldon, R. J. & O?Neill, J. J. (1988). Biochem. Pharmacol. 37, 379-384.


Acta Cryst (2013). E69, o1672  [ doi:10.1107/S1600536813026998 ]

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