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Volume 69 
Part 7 
Page o1027  
July 2013  

Received 13 May 2013
Accepted 25 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
H completeness 98%
Disorder in solvent or counterion
R = 0.049
wR = 0.156
Data-to-parameter ratio = 16.2
Details
Open access

Theobrominium perchlorate dibenzo-18-crown-6 3.25-hydrate

aInstitut für Anorganische Chemie, Universität zu Köln, Greinstrasse 6, D-50939 Köln, Germany
Correspondence e-mail: gerd.meyer@uni-koeln.de

The co-crystal, C7H9N4O2+·ClO4-·C20H24O6·3.25H2O, consists of theobrominium (3,7-dimethyl-2,6-dioxo-1H-purin-9-ium) cations, perchlorate anions and dibenzo-18-crown-6 and water molecules. The crown ether is in a bent conformation, in which the planes of the aromatic rings subtend an angle of 63.7 (1)°. Intermolecular O-H...O hydrogen bonding between the water molecules and the O atoms of the cyclic ether delimit an empty space reminiscent of a hollow cage. The water molecules are additionally linked to the cations by N-H...O hydrogen bonding. One of the positions of the water molecules is occupied only fractionally (25%) and is located outside this framework.

Related literature

For applications of crown ethers, see: Lehn (1995[Lehn, J.-M. (1995). In Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH Verlagsgesellschaft mbH.]). For host-guest chemistry of dibenzo-18-crown-6 with nitrogen bases, see: Lämsä et al. (1998[Lämsä, M., Huuskonen, J., Rissanen, K. & Pursiainen, J. (1998). Chem. Eur. J. 4, 84-92.]). For the crystal structure of dibenzo-18-crown-6, see: Lima et al. (2008[Lima, G. M. de, Wardell, J. L. & Harrison, W. T. A. (2008). Acta Cryst. E64, o2001.]).

[Scheme 1]

Experimental

Crystal data
  • C7H9N4O2+·ClO4-·C20H24O6·3.23H2O

  • Mr = 699.58

  • Orthorhombic, P 21 21 21

  • a = 11.9292 (3) Å

  • b = 15.2505 (5) Å

  • c = 18.1222 (5) Å

  • V = 3296.90 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 293 K

  • 0.5 × 0.5 × 0.3 mm

Data collection
  • Stoe & Cie IPDS II diffractometer

  • Absorption correction: numerical [X-RED (Stoe & Cie, 2001[Stoe & Cie (2001). X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]) and X-SHAPE (Stoe & Cie, 1999[Stoe & Cie (1999). X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.])] Tmin = 0.991, Tmax = 0.997

  • 51074 measured reflections

  • 7018 independent reflections

  • 5299 reflections with I > 4[sigma](I)

  • Rint = 0.084

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

  • wR(F2) = 0.156

  • S = 1.04

  • 7017 reflections

  • 434 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3092 Friedel pairs

  • Flack parameter: 0.02 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N9-H9...O3W 0.86 1.74 2.594 (4) 172
O1W-H1O1...O12 0.82 2.17 2.941 (3) 158
O2W-H1O2...O16 0.82 2.41 3.156 (3) 152
O2W-H1O2...O11 0.82 2.48 3.182 (3) 145
O2W-H2O2...O14 0.82 2.31 3.124 (3) 175
O3W-H1O3...O1W 0.82 1.99 2.802 (3) 172
O3W-H2O3...O15 0.82 1.98 2.769 (3) 161
N1-H1...O1Wi 0.86 2.01 2.871 (3) 174
O1W-H2O1...O2Wii 0.82 1.93 2.747 (3) 175
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Crystal Impact, 2012[Crystal Impact (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2312 ).


Acknowledgements

VK is grateful to the Studienstiftung des Deutschen Volkes for a PhD scholarship.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Crystal Impact (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Lämsä, M., Huuskonen, J., Rissanen, K. & Pursiainen, J. (1998). Chem. Eur. J. 4, 84-92.
Lehn, J.-M. (1995). In Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH Verlagsgesellschaft mbH.
Lima, G. M. de, Wardell, J. L. & Harrison, W. T. A. (2008). Acta Cryst. E64, o2001.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (1999). X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.
Stoe & Cie (2001). X-RED. Stoe & Cie GmbH, Darmstadt, Germany.
Stoe & Cie (2002). X-AREA. Stoe & Cie GmbH, Darmstadt, Germany.


Acta Cryst (2013). E69, o1027  [ doi:10.1107/S1600536813014463 ]

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