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Volume 64 
Part 8 
Page o1653  
August 2008  

Received 26 May 2008
Accepted 25 July 2008
Online 31 July 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.154
Data-to-parameter ratio = 6.7
Details
Open access

(R)-(+)-3-Hydroxy-2-methoxycarbonyl-8-methyl-8-azoniabicyclo[3.2.1]octane L-bitartrate

aCollege of Materials Science and Chemical Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China, and bZhejiang Huayi Pharmaceutical Company, Yiwu, Zhejiang 322000, People's Republic of China
Correspondence e-mail: grzheng@zju.edu.cn

(RS)-(±)-2-Methoxycarbonyl-3-tropinone is an important intermediate for the preparation of cocaine and its derivatives. The molecule in the title compound, C10H16NO3+·C4H5O6-, is present as the enol tautomer. The six-membered ring adopts a half boat conformation, and the five-membered ring a slightly distorted envelope conformation. There are intra- and intermolecular hydrogen bonds involving the hydroxyl, carboxyl groups and quaternary ammonium groups.

Related literature

For related literature, see: Findlay (1957[Findlay, S. P. (1957). J. Org. Chem. 22, 1385-1394.]); Meltzer et al. (1994[Meltzer, P. C., Liang, A. Y. & Madras, B. K. (1994). J. Med. Chem. 37, 2001-2010.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16NO3+·C4H5O6-

  • Mr = 347.32

  • Monoclinic, P 21

  • a = 6.5030 (10) Å

  • b = 15.914 (3) Å

  • c = 7.6626 (12) Å

  • [beta] = 96.497 (3)°

  • V = 787.9 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 (2) K

  • 0.50 × 0.49 × 0.37 mm

Data collection
  • SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.936, Tmax = 0.961

  • 4145 measured reflections

  • 1522 independent reflections

  • 1460 reflections with I > 2[sigma](I)

  • Rint = 0.082

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.154

  • S = 1.05

  • 1522 reflections

  • 226 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2 0.82 1.89 2.600 (4) 145
O7-H7...O9 0.82 2.06 2.562 (4) 120
N1-H1...O8i 0.954 (19) 1.82 (2) 2.724 (4) 158 (4)
O6-H6A...O2ii 0.82 2.58 3.182 (4) 132
O5-H5...O9i 0.82 1.72 2.535 (4) 172
Symmetry codes: (i) x, y, z+1; (ii) [-x, y-{\script{1\over 2}}, -z+1].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2093 ).


Acknowledgements

We thank the Shanghai Institute of Organic Chemistry for the X-ray data collection and analysis.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Findlay, S. P. (1957). J. Org. Chem. 22, 1385-1394.  [CrossRef] [ChemPort]
Meltzer, P. C., Liang, A. Y. & Madras, B. K. (1994). J. Med. Chem. 37, 2001-2010.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2008). publCIF. In preparation.


Acta Cryst (2008). E64, o1653  [ doi:10.1107/S1600536808023532 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.