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Volume 69 
Part 11 
Page o1620  
November 2013  

Received 2 October 2013
Accepted 3 October 2013
Online 9 October 2013

Key indicators
Single-crystal Synchrotron study
T = 95 K
Mean [sigma](C-C) = 0.001 Å
R = 0.029
wR = 0.079
Data-to-parameter ratio = 20.6
Details
Open access

3,14-Diethyl-2,13-di­aza-6,17-diazonia­tri­cyclo­[16.4.0.07,12]docosane dichloride tetra­hydrate from synchrotron radiation

aPohang Accelerator Laboratory, POSTECH, Pohang 790-784, Republic of Korea,bDepartment of Chemistry, Shah Jalal University of Science and Technology, Sylhet, Bangladesh, and cDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea
Correspondence e-mail: jhchoi@andong.ac.kr

The asymmetric unit of title hydrated salt, C22H46N42+·2Cl-·4H2O, comprises half a centrosymmetric dication, one Cl- anion and two water mol­ecules of crystallization. The structure determination reveals that protonation has occurred at diagonally opposite amine N atoms, and that the dication features intra­molecular N-H...N hydrogen bonds. In the crystal, a three-dimensional artchitecture is formed by O-H...Cl/N and N-H...Cl/O hydrogen bonds.

Related literature

For background to the coordination chemistry of tetra­aza­macrocycles, see: Choi et al. (2010[Choi, J.-H., Clegg, W. & Nichol, G. S. (2010). Z. Anorg. Allg. Chem. 636, 1612-1616.]); De Clercq (2010[De Clercq, E. (2010). J. Med. Chem. 53, 1438-1450.]). For the synthesis of the precursor macrocycle, see: Lim et al. (2006[Lim, J. H., Kang, J. S., Kim, H. C., Koh, E. K. & Hong, C. S. (2006). Inorg. Chem. 45, 7821-7827.]). For related structures, see: Choi et al. (2006[Choi, J.-H., Clegg, W., Harrington, R. W., Yoon, H.-M. & Hong, Y. P. (2006). Acta Cryst. E62, o644-o646.], 2011[Choi, J.-H., Subhan, M. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2173-o2174.]).

[Scheme 1]

Experimental

Crystal data
  • C22H46N42+·2Cl-·4H2O

  • Mr = 509.59

  • Monoclinic, C 2/c

  • a = 22.122 (4) Å

  • b = 13.616 (3) Å

  • c = 10.565 (2) Å

  • [beta] = 115.23 (3)°

  • V = 2878.5 (10) Å3

  • Z = 4

  • Synchrotron radiation

  • [lambda] = 0.72000 Å

  • [mu] = 0.27 mm-1

  • T = 95 K

  • 0.31 × 0.28 × 0.25 mm

Data collection
  • ADSC Q210 CCD area-detector diffractometer

  • Absorption correction: empirical (using intensity measurements) (HKL-3000 SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.922, Tmax = 0.937

  • 13046 measured reflections

  • 3663 independent reflections

  • 3446 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.079

  • S = 1.05

  • 3663 reflections

  • 178 parameters

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

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...Cl1 0.909 (13) 2.182 (14) 3.0900 (9) 177.3 (12)
N1-H2N1...N2i 0.907 (13) 2.200 (13) 2.9348 (11) 137.6 (10)
N2-H1N2...O1Wii 0.887 (13) 2.262 (13) 3.1242 (12) 164.1 (11)
O1W-H1O1...Cl1 0.833 (19) 2.400 (19) 3.2329 (14) 178.6 (17)
O1W-H2O1...Cl1iii 0.820 (18) 2.335 (18) 3.1479 (10) 171.1 (15)
O2W-H1O2...O1Wiv 0.84 (2) 2.06 (2) 2.9021 (15) 178.1 (18)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983[Arvai, A. J. & Nielsen, C. (1983). ADSC Quantum-210 ADX. Area Detector System Corporation, Poway, CA, USA.]); cell refinement: HKL3000sm (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL3000sm; program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013; molecular graphics: DIAMOND (Brandenburg, 2007[Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5261 ).


Acknowledgements

The experiment at the PLS-II 2D-SMC beamline was supported in part by MEST and POSTECH.

References

Arvai, A. J. & Nielsen, C. (1983). ADSC Quantum-210 ADX. Area Detector System Corporation, Poway, CA, USA.
Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Choi, J.-H., Clegg, W., Harrington, R. W., Yoon, H.-M. & Hong, Y. P. (2006). Acta Cryst. E62, o644-o646.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Choi, J.-H., Clegg, W. & Nichol, G. S. (2010). Z. Anorg. Allg. Chem. 636, 1612-1616.  [CSD] [CrossRef] [ChemPort]
Choi, J.-H., Subhan, M. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2173-o2174.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
De Clercq, E. (2010). J. Med. Chem. 53, 1438-1450.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lim, J. H., Kang, J. S., Kim, H. C., Koh, E. K. & Hong, C. S. (2006). Inorg. Chem. 45, 7821-7827.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1620  [ doi:10.1107/S1600536813027232 ]

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