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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 [sigma](C-C) = 0.006 Å
R = 0.063
wR = 0.125
Data-to-parameter ratio = 14.3
Details
Open access

(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

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-H...O hydrogen bonding, and the carboxylate groups are involved in intermolecular O-H...O hydrogen bonding.

Related literature

For the crystal structure of lesatropane, see: Yang et al. (2008[Yang, L.-M., Zhu, L., Niu, Y.-Y., Chen, H.-Z. & Lu, Y. (2008). Acta Cryst. E64, o2331.]). For its improved agonistic activity compared to its racemic counterpart, see: Zhu et al. (2008[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.]). For synthetic details, see: Yang & Wang (1998[Yang, L. & Wang, H. (1998). Acta Pharm. Sin. 33, 832-835.]).

[Scheme 1]

Experimental

Crystal data
  • C17H24NO5S+·C18H13O8-

  • Mr = 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[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.863, Tmax = 1.000 (expected range = 0.852-0.987)

  • 18779 measured reflections

  • 6550 independent reflections

  • 5135 reflections with I > 2[sigma](I)

  • Rint = 0.081

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3094 Friedel pairs

  • Flack parameter: 0.03 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.860 (18) 1.89 (2) 2.699 (4) 156 (3)
O4-H4...O2i 0.82 1.66 2.460 (3) 164
Symmetry code: (i) x-1, y, z.

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: 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [details]
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yang, L. & Wang, H. (1998). Acta Pharm. Sin. 33, 832-835.  [ChemPort]
Yang, L.-M., Zhu, L., Niu, Y.-Y., Chen, H.-Z. & Lu, Y. (2008). Acta Cryst. E64, o2331.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed]


Acta Cryst (2009). E65, o1037  [ doi:10.1107/S1600536809012732 ]

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