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Volume 67 
Part 3 
Pages m379-m380  
March 2011  

Received 5 February 2011
Accepted 22 February 2011
Online 26 February 2011

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 18.2
Details
Open access

Bis(8-hydroxy-2-methylquinolinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) methanol monosolvate monohydrate

Hossein Aghabozorg,a Ahmad Gholizadeh,a* Masoud Mirzaeib and Behrouz Notashc

aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran,bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
Correspondence e-mail: r3.chemist@gmail.com

The title compound, (C10H10NO)2[Cu(C7H3NO4)2]·CH3OH·H2O was prepared by the reaction of copper(II) nitrate hexahydrate, 8-hydroxy-2-methylquinoline, and pyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in an aqueous solution. The geometry of the resulting CuN2O4 coordination can be described as distorted octahedral. In the crystal, there are several intermolecular O-H...O, N-H...O and C-H...O hydrogen bonds. An intramolecular N-H...O hydrogen bond occurs in one of the cations. Considerable [pi]-[pi] stacking interactions are also observed between the aromatic rings of the cations, with centroid-centroid distances of 3.4567 (13), 3.5342 (14), 3.6941 (14) and 3.4568 (13) Å. These non-covalent interactions connect the components, forming a three-dimensional supramolecular structure.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008[Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184-227.]). For examples of proton transfer from pyridine-2,6-dicarboxylic acid (pydcH2) to different amine base ligands, see: Eshtiagh-Hosseini et al. (2010a[Eshtiagh-Hosseini, H., Yousefi, Z., Safiee, M. & Mirzaei, M. (2010a). J. Coord. Chem. 63, 3187-3197.],b[Eshtiagh-Hosseini, H., Aghabozorg, H., Mirzaei, M., Amini, M. M., Chen, Y.-G., Shokrollahi, A. & Aghaei, R. (2010b). J. Mol. Struct. 973, 180-189.],c[Eshtiagh-Hosseini, H., Alfi, N., Mirzaei, M., Fanwick, P. & Fanwick, P. E. (2010c). Acta Cryst. E66, m1450.]).

[Scheme 1]

Experimental

Crystal data

  • (C10H10NO)2[Cu(C7H3NO4)2]·CH4O·H2O

  • Mr = 764.20

  • Triclinic, [P \overline 1]

  • a = 10.116 (2) Å

  • b = 12.895 (3) Å

  • c = 14.816 (3) Å

  • [alpha] = 64.45 (3)°

  • [beta] = 76.23 (3)°

  • [gamma] = 83.74 (3)°

  • V = 1693.5 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 298 K

  • 0.5 × 0.4 × 0.3 mm
Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.714, Tmax = 0.803

  • 18924 measured reflections

  • 9061 independent reflections

  • 7185 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.109

  • S = 1.01

  • 9061 reflections

  • 498 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O9 0.83 (3) 2.37 (2) 2.692 (2) 104.3 (17)
N3-H3A...O11 0.83 (3) 1.93 (3) 2.739 (3) 164 (2)
N4-H4A...O8i 0.95 (3) 1.87 (3) 2.723 (2) 149 (2)
O9-H9A...O5 0.78 (3) 1.79 (3) 2.563 (2) 176 (3)
O10-H10A...O4 0.87 (4) 1.70 (4) 2.555 (3) 167 (3)
O11-H11A...O1i 0.83 (4) 1.88 (4) 2.706 (3) 172 (4)
O12-H12A...O7 0.82 (3) 2.14 (3) 2.895 (3) 154 (4)
O12-H12B...O2ii 0.82 (4) 2.21 (4) 2.974 (3) 156 (4)
C10-H10...O3iii 0.93 2.55 3.177 (3) 125
C15-H15C...O2i 0.96 2.55 3.480 (3) 163
C17-H17...O6iv 0.93 2.29 3.185 (3) 161
C25-H25C...O8i 0.96 2.48 3.212 (3) 133
C27-H27...O2v 0.93 2.50 3.394 (3) 162
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z+1; (v) x-1, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2078 ).

Acknowledgements

The authors thank the Faculty of Chemistry, Islamic Azad University, North Tehran Branch, for financial support.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184-227.  [ChemPort]
Eshtiagh-Hosseini, H., Aghabozorg, H., Mirzaei, M., Amini, M. M., Chen, Y.-G., Shokrollahi, A. & Aghaei, R. (2010b). J. Mol. Struct. 973, 180-189.  [ChemPort]
Eshtiagh-Hosseini, H., Alfi, N., Mirzaei, M., Fanwick, P. & Fanwick, P. E. (2010c). Acta Cryst. E66, m1450.  [CrossRef] [details]
Eshtiagh-Hosseini, H., Yousefi, Z., Safiee, M. & Mirzaei, M. (2010a). J. Coord. Chem. 63, 3187-3197.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [ISI] [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2005). X-AREA and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

Acta Cryst (2011). E67, m379-m380   [ doi:10.1107/S160053681100674X ]

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