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Volume 68 
Part 1 
Pages m47-m48  
January 2012  

Received 25 November 2011
Accepted 30 November 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.065
Data-to-parameter ratio = 13.5
Details
Open access

trans-Bis(ethylenediamine-[kappa]2N,N')bis(6-methyl-2,2,4-trioxo-3,4-dihydro-1,2[lambda]6,3-oxathiazin-3-ido-[kappa]N)copper(II)

aOndokuz Mayis University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and bOndokuz Mayis University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey
Correspondence e-mail: gunesd@omu.edu.tr

In the crystal structure of the title compound, [Cu(C4H4NO4S)2(C2H8N2)2], the Cu2+ ion resides on a centre of symmetry. The environment of Cu2+ ion is a distorted octahedron. The axial bond lengths between the CuII ion and the N atoms are considerably longer than the equatorial bond distances between the CuII ion and the N atoms of the ethylenediamine ligand as a consequence of the Jahn-Teller effect. The molecular conformation is stabilized by intramolecular N-H...O hydrogen bonds. In the crystal, molecules are connected by intermolecular N-H...O hydrogen bonds into chains running along the a axis.

Related literature

For background to acesulfame [systematic name: 6-methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide], see: Clauss & Jensen (1973[Clauss, K. & Jensen, H. (1973). Angew. Chem. Int. Ed. Engl. 12, 869-942.]); Duffy & Anderson (1998[Duffy, V. D. & Anderson, G. H. (1998). J. Am. Diet. Assoc. 98, 580-587.]); O'Brien Nabors (2001[O'Brien Nabors, L. (2001). Alternative Sweeteners, 3rd ed. New York: Marcel Dekker.]); Içbudak et al. (2006[Içbudak, H., Adiyaman, E., Çetin, N., Bulut, A. & Büyükgüngör, O. (2006). Transition Met. Chem. 31, 666-672.]) For the crystal structures of acesulfame and its metal complexes, see: Beck et al. (1985[Beck, W., Ambach, E. & Nagel, U. (1985). Chem. Ber. 118, 444-449.]); Bulut et al. (2005[Bulut, A., Içbudak, H., Sezer, G. & Kazak, C. (2005). Acta Cryst. C61, m228-m230.]); Cavicchioli et al. (2010[Cavicchioli, M., Massabni, A. C., Heinrich, T. A., Costa-Neto, C. M., Abrão, E. P., Fonseca, B. A. L., Castellano, E. E., Corbi, P. P., Lustri, W. R. & Leite, C. Q. F. (2010). J. Inorg. Biochem. 104, 533-540.]); Içbudak et al. (2005a[Içbudak, H., Bulut, A., Çetin, N. & Kazak, C. (2005a). Acta Cryst. C61, m1-m3.], 2006[Içbudak, H., Adiyaman, E., Çetin, N., Bulut, A. & Büyükgüngör, O. (2006). Transition Met. Chem. 31, 666-672.], 2007b[Içbudak, H., Uyanik, A., Bulut, A., Arici, C. & Ülkü, D. (2007b). Z. Kristallogr. 222, 432-436.]); Sahin et al. (2009[Sahin, Z. S., Içbudak, H. & Isik, S. (2009). Acta Cryst. C65, m463-m465.], 2010[Sahin, Z. S., Sevindi, F., Içbudak, H. & Isik, S. (2010). Acta Cryst. C66, m314-m318.]); Velaga et al. (2010[Velaga, S. P., Vangala, V. R., Basavoju, S. & Boström, D. (2010). Chem. Commun. 46, 3562-3564.]) and for spectroscopic, thermal analysis, magnetic susceptibility and conductivity studies on metal complexes of acesulfame, see: Beck et al. (1985[Beck, W., Ambach, E. & Nagel, U. (1985). Chem. Ber. 118, 444-449.]); Içbudak et al. (2005a[Içbudak, H., Bulut, A., Çetin, N. & Kazak, C. (2005a). Acta Cryst. C61, m1-m3.],b[Içbudak, H., Heren, Z., Uyanik, A. & Odabasoglu, M. (2005b). J. Therm. Anal. Calorim. 82, 303-306.], 2006[Içbudak, H., Adiyaman, E., Çetin, N., Bulut, A. & Büyükgüngör, O. (2006). Transition Met. Chem. 31, 666-672.], 2007a[Içbudak, H., Adiyaman, E., Uyanik, A. & Cakir, S. (2007a). Transition Met. Chem. 32, 864-869.],b[Içbudak, H., Uyanik, A., Bulut, A., Arici, C. & Ülkü, D. (2007b). Z. Kristallogr. 222, 432-436.]). For Cu2+ complexes with an octahedral coordination geometry, see: Bulut et al. (2005[Bulut, A., Içbudak, H., Sezer, G. & Kazak, C. (2005). Acta Cryst. C61, m228-m230.]); Içbudak et al. (2007b[Içbudak, H., Uyanik, A., Bulut, A., Arici, C. & Ülkü, D. (2007b). Z. Kristallogr. 222, 432-436.]); Pariya et al. (1998a[Pariya, C., Liao, F.-L., Wang, S.-L. & Chung, C.-S. (1998a). Polyhedron, 17, 547-554.],b[Pariya, C., Panneerselvan, K., Chung, C.-S. & Lu, T.-H. (1998b). Polyhedron, 17, 2555-2561.]); Sahin et al. (2010[Sahin, Z. S., Sevindi, F., Içbudak, H. & Isik, S. (2010). Acta Cryst. C66, m314-m318.]). For the Jahn-Teller effect, see: Jahn & Teller (1937[Jahn, H. A. & Teller, E. (1937). Proc. R. Soc. London Ser. A, 161, 220-235.]). For the structural flexibility owing to the electronic configuration, see: Kozlevcar et al. (2006[Kozlevcar, B., Golobic, A. & Strauch, P. (2006). Polyhedron, 25, 2824-2828.]). For the octahedral geometry of the Cu2+ ion, see: Petric et al. (1998[Petric, M., Pohleven, F., Turel, I., Segedin, P., White, A. J. P. & Williams, D. J. (1998). Polyhedron, 17, 255-260.]);

[Scheme 1]

Experimental

Crystal data
  • [Cu(C4H4NO4S)2(C2H8N2)2]

  • Mr = 508.03

  • Monoclinic, P 21 /c

  • a = 6.9853 (3) Å

  • b = 17.5355 (6) Å

  • c = 8.4092 (4) Å

  • [beta] = 93.017 (3)°

  • V = 1028.62 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.32 mm-1

  • T = 296 K

  • 0.75 × 0.47 × 0.32 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.438, Tmax = 0.678

  • 14620 measured reflections

  • 2023 independent reflections

  • 1865 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.065

  • S = 1.09

  • 2023 reflections

  • 150 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Selected bond lengths (Å)

Cu1-N1 2.7434 (15)
Cu1-N2 2.0090 (16)
Cu1-N3 2.0101 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3B...O4 0.82 (2) 2.20 (2) 2.905 (2) 143 (2)
N2-H2A...O4i 0.82 (2) 2.13 (2) 2.931 (2) 167 (2)
N2-H2B...O1ii 0.87 (2) 2.57 (2) 3.250 (2) 137 (2)
N3-H3A...O2iii 0.85 (2) 2.23 (2) 2.974 (2) 147 (2)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: WinGX (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5731 ).


Acknowledgements

The authors thank the Ondokuz Mayis University Research Fund for financial support.

References

Beck, W., Ambach, E. & Nagel, U. (1985). Chem. Ber. 118, 444-449.  [CrossRef] [ChemPort]
Bulut, A., Içbudak, H., Sezer, G. & Kazak, C. (2005). Acta Cryst. C61, m228-m230.  [CSD] [CrossRef] [details]
Cavicchioli, M., Massabni, A. C., Heinrich, T. A., Costa-Neto, C. M., Abrão, E. P., Fonseca, B. A. L., Castellano, E. E., Corbi, P. P., Lustri, W. R. & Leite, C. Q. F. (2010). J. Inorg. Biochem. 104, 533-540.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Clauss, K. & Jensen, H. (1973). Angew. Chem. Int. Ed. Engl. 12, 869-942.  [CrossRef] [ISI]
Duffy, V. D. & Anderson, G. H. (1998). J. Am. Diet. Assoc. 98, 580-587.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Içbudak, H., Adiyaman, E., Çetin, N., Bulut, A. & Büyükgüngör, O. (2006). Transition Met. Chem. 31, 666-672.
Içbudak, H., Adiyaman, E., Uyanik, A. & Cakir, S. (2007a). Transition Met. Chem. 32, 864-869.
Içbudak, H., Bulut, A., Çetin, N. & Kazak, C. (2005a). Acta Cryst. C61, m1-m3.  [CSD] [CrossRef] [details]
Içbudak, H., Heren, Z., Uyanik, A. & Odabasoglu, M. (2005b). J. Therm. Anal. Calorim. 82, 303-306.
Içbudak, H., Uyanik, A., Bulut, A., Arici, C. & Ülkü, D. (2007b). Z. Kristallogr. 222, 432-436.
Jahn, H. A. & Teller, E. (1937). Proc. R. Soc. London Ser. A, 161, 220-235.  [ChemPort]
Kozlevcar, B., Golobic, A. & Strauch, P. (2006). Polyhedron, 25, 2824-2828.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
O'Brien Nabors, L. (2001). Alternative Sweeteners, 3rd ed. New York: Marcel Dekker.
Pariya, C., Liao, F.-L., Wang, S.-L. & Chung, C.-S. (1998a). Polyhedron, 17, 547-554.  [ISI] [CrossRef] [ChemPort]
Pariya, C., Panneerselvan, K., Chung, C.-S. & Lu, T.-H. (1998b). Polyhedron, 17, 2555-2561.  [ISI] [CrossRef] [ChemPort]
Petric, M., Pohleven, F., Turel, I., Segedin, P., White, A. J. P. & Williams, D. J. (1998). Polyhedron, 17, 255-260.  [ChemPort]
Sahin, Z. S., Içbudak, H. & Isik, S. (2009). Acta Cryst. C65, m463-m465.  [CSD] [CrossRef] [details]
Sahin, Z. S., Sevindi, F., Içbudak, H. & Isik, S. (2010). Acta Cryst. C66, m314-m318.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Velaga, S. P., Vangala, V. R., Basavoju, S. & Boström, D. (2010). Chem. Commun. 46, 3562-3564.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, m47-m48   [ doi:10.1107/S1600536811051658 ]

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