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Volume 69 
Part 9 
Page m485  
September 2013  

Received 26 June 2013
Accepted 1 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.129
Data-to-parameter ratio = 47.0
Details
Open access

1-(2,3-Dimethylphenyl)piperazine-1,4-diium tetrachloridocuprate(II)

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
Correspondence e-mail: sonia.abid@fsb.rnu.tn

In the title salt, (C12H20N2)[CuCl4], the CuII atom occupies a general position in a flattened tetrahedral environment by Cl ligands, characterized by Cl-Cu-Cl angles of 134.04 (3) and 137.18 (4)°. The six-membered piperazinediium ring adopts a chair conformation. The organic cation and inorganic anion interact through N-H...Cl and C-H...Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to the properties of tetrahalidocuprate(II) compounds, see: Solomon et al. (1992[Solomon, E. I., Baldwin, M. J. & Lowery, M. D. (1992). Chem. Rev. 92, 521-542.]); Kim et al. (2001[Kim, Y. J., Kim, S. O., Kim, Y. I. & Choi, S. N. (2001). Inorg. Chem. 40, 4481-4484.]); Panja et al. (2005[Panja, A., Goswami, S., Shaikh, N., Roy, P., Manassero, M., Butcher, R. J. & Banerjee, P. (2005). Polyhedron, 24, 2921-2932.]); Lee et al. (2004[Lee, Y. K., Park, S. M., Kang, S. K., Kim, Y. I. & Choi, S. N. (2004). Bull. Korean Chem. Soc. 25, 823-828.]); Turnbull et al. (2005[Turnbull, M. M., Landee, C. P. & Wells, B. M. (2005). Coord. Chem. Rev. 249, 2567-2576.]); Shapiro et al. (2007[Shapiro, A., Landee, C. P., Turnbull, M. M., Jornet, J., Deumal, M., Novoa, J. J., Robb, M. A. & Lewis, W. (2007). J. Am. Chem. Soc. 129, 952-959.]). For general background to the geometry of the tetrahalidocuprate(II) species, see: Halvorson et al. (1990[Halvorson, K. E., Patterson, C. & Willett, R. D. (1990). Acta Cryst. B46, 508-519.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H20N2)[CuCl4]

  • Mr = 397.64

  • Triclinic, [P \overline 1]

  • a = 7.1986 (15) Å

  • b = 7.7611 (11) Å

  • c = 15.635 (4) Å

  • [alpha] = 77.035 (16)°

  • [beta] = 79.311 (19)°

  • [gamma] = 81.845 (14)°

  • V = 831.9 (3) Å3

  • Z = 2

  • Ag K[alpha] radiation

  • [lambda] = 0.56087 Å

  • [mu] = 1.01 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Nonius MACH-3 diffractometer

  • Absorption correction: part of the refinement model ([Delta]F) (Walker & Stuart, 1983[Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.]) Tmin = 0.786, Tmax = 0.863

  • 9228 measured reflections

  • 8079 independent reflections

  • 4600 reflections with I > 2[sigma](I)

  • Rint = 0.020

  • 2 standard reflections every 120 min intensity decay: 7%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.129

  • S = 1.00

  • 8079 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.68 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...Cl3i 0.91 2.48 3.1610 (18) 132
N2-H2A...Cl2ii 0.90 2.35 3.144 (2) 147
N2-H2B...Cl1iii 0.90 2.30 3.152 (2) 159
N2-H2B...Cl2iii 0.90 2.80 3.271 (2) 114
C2-H2D...Cl1i 0.97 2.74 3.666 (3) 159
C3-H3B...Cl1iv 0.97 2.78 3.585 (2) 141
C4-H4B...Cl4ii 0.97 2.66 3.616 (2) 168
C6-H6...Cl4ii 0.93 2.71 3.572 (2) 154
C12-H12C...Cl3i 0.96 2.71 3.568 (3) 149
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x+1, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: RU2053 ).


Acknowledgements

This work was supported by the Tunisian Ministry of HEScR.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Halvorson, K. E., Patterson, C. & Willett, R. D. (1990). Acta Cryst. B46, 508-519.  [CSD] [CrossRef] [details]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Kim, Y. J., Kim, S. O., Kim, Y. I. & Choi, S. N. (2001). Inorg. Chem. 40, 4481-4484.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Lee, Y. K., Park, S. M., Kang, S. K., Kim, Y. I. & Choi, S. N. (2004). Bull. Korean Chem. Soc. 25, 823-828.  [ChemPort]
Panja, A., Goswami, S., Shaikh, N., Roy, P., Manassero, M., Butcher, R. J. & Banerjee, P. (2005). Polyhedron, 24, 2921-2932.  [ISI] [CSD] [CrossRef] [ChemPort]
Shapiro, A., Landee, C. P., Turnbull, M. M., Jornet, J., Deumal, M., Novoa, J. J., Robb, M. A. & Lewis, W. (2007). J. Am. Chem. Soc. 129, 952-959.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Solomon, E. I., Baldwin, M. J. & Lowery, M. D. (1992). Chem. Rev. 92, 521-542.  [CrossRef] [ChemPort] [ISI]
Turnbull, M. M., Landee, C. P. & Wells, B. M. (2005). Coord. Chem. Rev. 249, 2567-2576.  [ISI] [CrossRef] [ChemPort]
Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.  [CrossRef] [details]


Acta Cryst (2013). E69, m485  [ doi:10.1107/S1600536813021454 ]

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