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Volume 69 
Part 6 
Page o870  
June 2013  

Received 26 March 2013
Accepted 2 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.125
Data-to-parameter ratio = 13.2
Details
Open access

Bis(2,3-dimethoxy-10-oxostrychnidinium) phthalate nonahydrate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist., Chennai 603 203, Tamil Nadu, India
Correspondence e-mail: phdguna@gmail.com, phdguna@gmail.com

The asymmetric unit of the title compound 2C23H27N2O4+·C8H4O42-·9H2O, contains a cation, an anionon a twofold axis and four and half molecules of water, one of which is located on the twofold axis. In the cation, both fused pyrrolidine rings exhibit twisted conformations, while the piperidine rings adopt screw-boat and boat conformations. In the crystal, the components are linked by N-H...O and O-H...O hydrogen bonds. The brucinium cations form typical undulating head-to-tail ribbon structuresalong the a-axis direction, which associate with the carboxy phthalate and the water molecules.

Related literature

For general background to brucine derivatives, see: Smith et al. (2006[Smith, G., Wermuth, U. D., Young, D. J. & White, J. M. (2006). Acta Cryst. E62, o1553-o1555.]) and for related structures, see: Smith et al. (2005[Smith, G., Wermuth, U. D., Healy, P. C., Young, D. J. & White, J. M. (2005). Acta Cryst. E61, o2646-o2648.], 2006[Smith, G., Wermuth, U. D., Young, D. J. & White, J. M. (2006). Acta Cryst. E62, o1553-o1555.]).

[Scheme 1]

Experimental

Crystal data
  • 2C23H27N2O4+·C8H4O42-·9H2O

  • Mr = 1117.19

  • Monoclinic, C 2

  • a = 13.939 (5) Å

  • b = 12.370 (5) Å

  • c = 15.321 (5) Å

  • [beta] = 90.646 (5)°

  • V = 2641.6 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 295 K

  • 0.35 × 0.30 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.963, Tmax = 0.979

  • 12452 measured reflections

  • 5094 independent reflections

  • 3854 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.125

  • S = 1.05

  • 5094 reflections

  • 385 parameters

  • 16 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 8565 Friedel pairs

  • Flack parameter: 0 (0)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O5i 0.91 1.79 2.665 (4) 159
O7-H7A...O3 0.82 (1) 1.98 (2) 2.776 (3) 165 (7)
O7-H7B...O5ii 0.82 (1) 2.10 (4) 2.836 (4) 149 (7)
O9-H9A...O6iii 0.82 (1) 1.98 (2) 2.775 (5) 164 (6)
O8-H8B...O7 0.82 (1) 1.99 (2) 2.794 (5) 165 (6)
O8-H8A...O9 0.82 (1) 1.97 (3) 2.753 (5) 158 (7)
O9-H9B...O11iv 0.82 (1) 2.01 (1) 2.824 (6) 176 (8)
O10-H10C...O6v 0.82 (1) 2.29 (3) 3.066 (5) 159 (9)
O10-H10D...O8vi 0.82 (1) 1.99 (3) 2.767 (5) 158 (8)
O11-H11A...O10 0.82 (1) 2.12 (2) 2.808 (4) 142 (3)
Symmetry codes: (i) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) -x+1, y-1, -z+1; (iii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z+1]; (iv) x, y-1, z; (v) -x+1, y, -z+1; (vi) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2399 ).


References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Smith, G., Wermuth, U. D., Healy, P. C., Young, D. J. & White, J. M. (2005). Acta Cryst. E61, o2646-o2648.  [CSD] [CrossRef] [ChemPort] [details]
Smith, G., Wermuth, U. D., Young, D. J. & White, J. M. (2006). Acta Cryst. E62, o1553-o1555.  [CSD] [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o870  [ doi:10.1107/S160053681301204X ]

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