(1R,3S,5R,6S)-6-Acet­oxy-8-methyl-3-(p-tolyl­sulfon­yloxy)-8-azoniabicyclo­[3.2.1]octane (2R,3R)-2,3-bis­(benzo­yloxy)-3-carboxy­propanoate

Yang, L.-M.; Xie, Y.-F.; Gu, Y.-F.; Chen, H.-Z.; Lu, Y.

doi:10.1107/S1600536809012732

Volume 65
Part 5
Page o1037
May 2009

Received 6 January 2009
Accepted 3 April 2009
Online 18 April 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.063
wR = 0.125
Data-to-parameter ratio = 14.3
Details

(1R,3S,5R,6S)-6-Acetoxy-8-methyl-3-(p-tolylsulfonyloxy)-8-azoniabicyclo[3.2.1]octane (2R,3R)-2,3-bis(benzoyloxy)-3-carboxypropanoate

Li-Min Yang,^a Yi-Fan Xie,^a Ya-Fang Gu,^a Hong-Zhuan Chen ^a and Yang Lu ^a ^*

^aDepartment of Pharmacy, Shanghai Jiao Tong University School of Medicine, South Chongqing Road 280, Shanghai 200025, People's Republic of China
Correspondence e-mail: huaxue@shsmu.edu.cn

The title compound, C₁₇H₂₄NO₅S⁺·C₁₈H₁₃O₈^-, is the key intermediate during the preparation of lesatropane [systematic name (1R,3S,5R,6S)-6-acetoxy-3-(4-methylphenylsulfonyloxy)tropane], a potential antiglaucoma agent. The tertiary N atom of the tropane ring is involved in intermolecular N-HO hydrogen bonding, and the carboxylate groups are involved in intermolecular O-HO hydrogen bonding.

Related literature

For the crystal structure of lesatropane, see: Yang et al. (2008). For its improved agonistic activity compared to its racemic counterpart, see: Zhu et al. (2008). For synthetic details, see: Yang & Wang (1998).

Experimental

Crystal data

C₁₇H₂₄NO₅S⁺·C₁₈H₁₃O₈^-
M_r = 711.72
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4153 (5) Å
b = 19.2664 (12) Å
c = 24.7388 (16) Å
V = 3534.3 (4) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 293 K
0.31 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.863, T_max = 1.000 (expected range = 0.852-0.987)
18779 measured reflections
6550 independent reflections
5135 reflections with I > 2(I)
R_int = 0.081

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.125
S = 1.06
6550 reflections
459 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), 3094 Friedel pairs
Flack parameter: 0.03 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.860 (18)	1.89 (2)	2.699 (4)	156 (3)
O4-H4O2ⁱ	0.82	1.66	2.460 (3)	164
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WW2139 ).

Acknowledgements

This work was supported by the Fund of the Science and Technology Commission of Shanghai Municipality (Key item, grant No. 06DZ19001) and the Shanghai Municipal Education Commission Fund (grant No. 06BZ009). 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, L. & Wang, H. (1998). Acta Pharm. Sin. 33, 832-835.
Yang, L.-M., Zhu, L., Niu, Y.-Y., Chen, H.-Z. & Lu, Y. (2008). Acta Cryst. E64, o2331.
Zhu, L., Yang, L.-M., Cui, Y.-Y., Zheng, P.-L., Niu, Y.-Y., Wang, H., Lu, Y., Ren, Q.-S., Wei, P.-J. & Chen, H.-Z. (2008). Acta Pharmacol. Sin. 29, 177-184.

organic compounds