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Volume 69 
Part 2 
Pages m73-m74  
February 2013  

Received 15 November 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.029
wR = 0.068
Data-to-parameter ratio = 16.4
Details
Open access

Di-[mu]-chlorido-bis[(2,2'-bipyridine-5,5'-dicarboxylic acid-[kappa]2N,N')chloridocopper(II)] dimethylformamide tetrasolvate

ainGAP Centre for Research Based Innovation, Department of Chemistry, University of Oslo, 0315 Oslo, Norway
Correspondence e-mail: sigurdoi@kjemi.uio.no

In the title compound, [Cu2Cl4(C12H8N2O4)2]·4C3H7NO, which contains a chloride-bridged centrosymmetric CuII dimer, the CuII atom is in a distorted square-pyramidal 4 + 1 coordination geometry defined by the N atoms of the chelating 2,2'-bipyridine ligand, a terminal chloride and two bridging chloride ligands. Of the two independent dimethylformamide molecules, one is hydrogen bonded to a single -COOH group, while one links two adjacent -COOH groups via a strong accepted O-H...O and a weak donated C(O)-H...O hydrogen bond. Two of these last molecules and the two -COOH groups form a centrosymmetric hydrogen-bonded ring in which the CH=O and the -COOH groups by disorder adopt two alternate orientations in a 0.44:0.56 ratio. These hydrogen bonds link the CuII complex molecules and the dimethylformamide solvent molecules into infinite chains along [-111]. Slipped [pi]-[pi] stacking interactions between two centrosymmetric pyridine rings (centroid-centroid distance = 3.63 Å) contribute to the coherence of the structure along [0-11].

Related literature

For related structures with similar coordination geometry around the copper atoms, see: Goddard et al. (1990[Goddard, R., Hemalatha, B. & Rajasekharan, M. V. (1990). Acta Cryst. C46, 33-35.]); Tynan et al. (2005[Tynan, E., Jensen, P., Lees, A. C., Moubaraki, B., Murray, K. S. & Kruger, P. E. (2005). CrystEngComm, 7, 90-95.]); Han et al. (2008[Han, K.-F., Wu, H.-Y., Wang, Z.-M. & Guo, H.-Y. (2008). Acta Cryst. E64, m1607-m1608.]); Liu et al. (2009[Liu, Y.-F., Rong, D.-F., Xia, H.-T. & Wang, D.-Q. (2009). Acta Cryst. E65, m1492.]); Qi et al. (2009[Qi, Z.-P., Wang, A.-D., Zhang, H. & Wang, X.-X. (2009). Acta Cryst. E65, m1507-m1508.]). For other related structures of chloro bipyridine copper complexes, see: Wang et al. (2004[Wang, Y.-Q., Bi, W.-H., Li, X. & Cao, R. (2004). Acta Cryst. E60, m876-m877.]); Zhao et al. (2010[Zhao, J., Shi, D., Cheng, H., Chen, L., Ma, P. & Niu, J. (2010). Inorg. Chem. Commun. 13, 822-827.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu2Cl4(C12H8N2O4)2]·4C3H7NO

  • Mr = 1049.66

  • Triclinic, [P \overline 1]

  • a = 8.917 (5) Å

  • b = 11.030 (6) Å

  • c = 12.179 (7) Å

  • [alpha] = 83.171 (6)°

  • [beta] = 73.903 (6)°

  • [gamma] = 68.332 (6)°

  • V = 1069.4 (11) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 1.32 mm-1

  • T = 100 K

  • 0.20 × 0.15 × 0.02 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.789, Tmax = 0.974

  • 9231 measured reflections

  • 4824 independent reflections

  • 3969 reflections with I > 2[sigma](I)

  • Rint = 0.021

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

  • wR(F2) = 0.068

  • S = 1.02

  • 4824 reflections

  • 295 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Selected bond lengths (Å)

N1-Cu1 2.0337 (18)
N2-Cu1 2.0361 (17)
Cl1-Cu1 2.2525 (10)
Cl2-Cu1i 2.2804 (10)
Cl2-Cu1 2.7183 (12)
Symmetry code: (i) -x+2, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O6Bii 0.82 1.72 2.515 (3) 161
O1-H1...O6Aiii 0.82 1.75 2.536 (4) 161
O3-H3...O5 0.82 1.72 2.541 (2) 177
C21A-H21A...O2iv 0.93 2.71 3.591 (3) 158
C21B-H21B...O1iii 0.93 2.72 3.603 (3) 159
Symmetry codes: (ii) x+1, y-1, z-1; (iii) -x+1, -y+1, -z+1; (iv) x-1, y+1, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Materials Studio (Accelrys, 2010[Accelrys (2010). Materials Studio. Accelrys Inc., San Diego, California, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2049 ).


Acknowledgements

This work is part of the inGAP and CLIMIT, which receive financial support from the Norwegian Research Council under contract Nos. 174893 and 215735, respectively.

References

Accelrys (2010). Materials Studio. Accelrys Inc., San Diego, California, USA.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Goddard, R., Hemalatha, B. & Rajasekharan, M. V. (1990). Acta Cryst. C46, 33-35.  [CrossRef] [details]
Han, K.-F., Wu, H.-Y., Wang, Z.-M. & Guo, H.-Y. (2008). Acta Cryst. E64, m1607-m1608.  [CrossRef] [details]
Liu, Y.-F., Rong, D.-F., Xia, H.-T. & Wang, D.-Q. (2009). Acta Cryst. E65, m1492.  [CrossRef] [details]
Qi, Z.-P., Wang, A.-D., Zhang, H. & Wang, X.-X. (2009). Acta Cryst. E65, m1507-m1508.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tynan, E., Jensen, P., Lees, A. C., Moubaraki, B., Murray, K. S. & Kruger, P. E. (2005). CrystEngComm, 7, 90-95.  [ISI] [CSD] [CrossRef] [ChemPort]
Wang, Y.-Q., Bi, W.-H., Li, X. & Cao, R. (2004). Acta Cryst. E60, m876-m877.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhao, J., Shi, D., Cheng, H., Chen, L., Ma, P. & Niu, J. (2010). Inorg. Chem. Commun. 13, 822-827.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m73-m74   [ doi:10.1107/S1600536812051422 ]

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