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

Yu, J.-B.; Chen, S.-W.; Zheng, G.-R.; Dai, L.-Y.

doi:10.1107/S1600536808023532

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 (C-C) = 0.005 Å
R = 0.065
wR = 0.154
Data-to-parameter ratio = 6.7
Details

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

Jian-Bing Yu,^a Shuang-Wei Chen,^b Guo-Rong Zheng ^b and Li-Yan Dai ^a ^*

^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); Meltzer et al. (1994).

Experimental

Crystal data

C₁₀H₁₆NO₃⁺·C₄H₅O₆^-
M_r = 347.32
Monoclinic, P 2₁
a = 6.5030 (10) Å
b = 15.914 (3) Å
c = 7.6626 (12) Å
= 96.497 (3)°
V = 787.9 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.936, T_max = 0.961
4145 measured reflections
1522 independent reflections
1460 reflections with I > 2(I)
R_int = 0.082

Refinement

R[F² > 2(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
_max = 0.38 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2	0.82	1.89	2.600 (4)	145
O7-H7O9	0.82	2.06	2.562 (4)	120
N1-H1O8ⁱ	0.954 (19)	1.82 (2)	2.724 (4)	158 (4)
O6-H6AO2ⁱⁱ	0.82	2.58	3.182 (4)	132
O5-H5O9ⁱ	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008).

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.
Meltzer, P. C., Liang, A. Y. & Madras, B. K. (1994). J. Med. Chem. 37, 2001-2010.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds