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Volume 68 
Part 12 
Page m1482  
December 2012  

Received 31 October 2012
Accepted 9 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.093
Data-to-parameter ratio = 18.5
Details
Open access

Bis(2-{[bis(dimethylamino)methylidene]amino-[kappa]N}benzenesulfonato-[kappa]N)copper(II)

aUniversität Paderborn, Fakultät für Naturwissenschaften, Department Chemie, Warburger Strasse 100, 33098 Paderborn, Germany
Correspondence e-mail: ulrich.floerke@upb.de

The molecular structure of the title compound, [Cu(C11H16N3O3S)2], shows the CuII atom with a distorted square-planar coordination geometry from the N2O2 donor set of the two chelating 2-{[bis(dimethylamino)methylidene]amino}benzenesulfonate ligands. The CuII atom lies 0.065 (1) Å above the N2O2 plane and the Cu-O [2 × 1.945 (2) Å] and Cu-N bond lengths [1.968 (3) and 1.962 (3) Å] lie in expected ranges. The two aromatic ring planes make a dihedral angle of 85.48 (1)°.

Related literature

For bifunctional peralkylated guanidine ligands, see: Bienemann et al. (2011[Bienemann, O., Hoffmann, A. & Herres-Pawlis, S. (2011). Rev. Inorg. Chem. 31, 83-108.]); Börner et al. (2009[Börner, J., Flörke, U., Huber, K., Döring, A., Kuckling, D. & Herres-Pawlis, S. (2009). Chem. Eur. J. 15, 2362-2376.]); Herres-Pawlis et al. (2005[Herres-Pawlis, S., Neuba, A., Seewald, O., Seshadri, T., Egold, H., Flörke, U. & Henkel, G. (2005). Eur. J. Org. Chem. pp. 4879-4890.], 2009[Herres-Pawlis, S., Verma, P., Haase, R., Kang, P., Lyons, C. T., Wasinger, E. C., Flörke, U., Henkel, G. & Stack, T. D. P. (2009). J. Am. Chem. Soc. 131, 1154-1169.]); Neuba et al. (2008[Neuba, A., Haase, R., Bernard, M., Flörke, U. & Herres-Pawlis, S. (2008). Z. Anorg. Allg. Chem. 634, 2511-2517.], 2010[Neuba, A., Herres-Pawlis, S., Seewald, O., Börner, J., Heuwing, J., Flörke, U. & Henkel, G. (2010). Z. Anorg. Allg. Chem. 636, 2641-2649.]); Pohl et al. (2000[Pohl, S., Harmjanz, M., Schneider, J., Saak, W. & Henkel, G. (2000). J. Chem. Soc. Dalton Trans. pp. 3473-3479.]); Raab et al. (2003[Raab, V., Harms, K., Sundermeyer, J., Kovacevic, B. & Maksic, Z. B. (2003). J. Org. Chem. 68, 8790-8797.]); Wittmann et al. (2001[Wittmann, H., Raab, V., Schorm, A., Plackmeyer, J. & Sundermeyer, J. (2001). Eur. J. Inorg. Chem. pp. 1937-1948.]). For guanidine-sulfur hybrids to mimic the structural and physical as well as functional characteristics of the CuII atom in cytochrome c oxidase and N2O reductase, see: Neuba et al. (2011[Neuba, A., Flörke, U., Meyer-Klaucke, W., Salomone-Stagni, M., Bill, E., Bothe, E., Höfer, P. & Henkel, G. (2011). Angew. Chem. 123, 4596-4600.], 2012[Neuba, A., Haase, R. U., Meyer-Klaucke, W., Flörke, U. & Henkel, G. (2012). Angew. Chem. 124, 1746-1750.]). For related structures with Cu(N2O2) motifs, see: Robinson et al. (2004[Robinson, R. I., Stephens, J. C., Worden, S. M., Blake, A. J., Wilson, C. & Woodward, S. (2004). Eur. J. Org. Chem. pp. 4596-4605.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C11H16N3O3S)2]

  • Mr = 604.20

  • Orthorhombic, P n a 21

  • a = 19.940 (3) Å

  • b = 12.2947 (14) Å

  • c = 10.9508 (14) Å

  • V = 2684.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.02 mm-1

  • T = 120 K

  • 0.29 × 0.23 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.757, Tmax = 0.822

  • 22901 measured reflections

  • 6315 independent reflections

  • 4939 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.093

  • S = 1.02

  • 6315 reflections

  • 342 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2953 Friedel pairs

  • Flack parameter: 0.021 (12)

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2076 ).


Acknowledgements

We thank the German Research Council (DFG) and the Federal Ministry of Education and Research (BMBF) for continuous support of our work.

References

Bienemann, O., Hoffmann, A. & Herres-Pawlis, S. (2011). Rev. Inorg. Chem. 31, 83-108.  [CrossRef]
Börner, J., Flörke, U., Huber, K., Döring, A., Kuckling, D. & Herres-Pawlis, S. (2009). Chem. Eur. J. 15, 2362-2376.  [PubMed]
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Herres-Pawlis, S., Neuba, A., Seewald, O., Seshadri, T., Egold, H., Flörke, U. & Henkel, G. (2005). Eur. J. Org. Chem. pp. 4879-4890.  [CSD] [CrossRef]
Herres-Pawlis, S., Verma, P., Haase, R., Kang, P., Lyons, C. T., Wasinger, E. C., Flörke, U., Henkel, G. & Stack, T. D. P. (2009). J. Am. Chem. Soc. 131, 1154-1169.  [ISI] [PubMed] [ChemPort]
Neuba, A., Flörke, U., Meyer-Klaucke, W., Salomone-Stagni, M., Bill, E., Bothe, E., Höfer, P. & Henkel, G. (2011). Angew. Chem. 123, 4596-4600.  [CrossRef]
Neuba, A., Haase, R., Bernard, M., Flörke, U. & Herres-Pawlis, S. (2008). Z. Anorg. Allg. Chem. 634, 2511-2517.  [CSD] [CrossRef] [ChemPort]
Neuba, A., Haase, R. U., Meyer-Klaucke, W., Flörke, U. & Henkel, G. (2012). Angew. Chem. 124, 1746-1750.  [CrossRef]
Neuba, A., Herres-Pawlis, S., Seewald, O., Börner, J., Heuwing, J., Flörke, U. & Henkel, G. (2010). Z. Anorg. Allg. Chem. 636, 2641-2649.  [CSD] [CrossRef] [ChemPort]
Pohl, S., Harmjanz, M., Schneider, J., Saak, W. & Henkel, G. (2000). J. Chem. Soc. Dalton Trans. pp. 3473-3479.  [CrossRef]
Raab, V., Harms, K., Sundermeyer, J., Kovacevic, B. & Maksic, Z. B. (2003). J. Org. Chem. 68, 8790-8797.  [CSD] [CrossRef] [PubMed] [ChemPort]
Robinson, R. I., Stephens, J. C., Worden, S. M., Blake, A. J., Wilson, C. & Woodward, S. (2004). Eur. J. Org. Chem. pp. 4596-4605.  [CSD] [CrossRef]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wittmann, H., Raab, V., Schorm, A., Plackmeyer, J. & Sundermeyer, J. (2001). Eur. J. Inorg. Chem. pp. 1937-1948.  [CrossRef]


Acta Cryst (2012). E68, m1482  [ doi:10.1107/S1600536812046387 ]

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