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Volume 69 
Part 12 
Page m663  
December 2013  

Received 7 November 2013
Accepted 8 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.076
Data-to-parameter ratio = 12.1
Details
Open access

Bis(5-hy­droxy­isophthalato-[kappa]O1)bis­[4-(pyridine-3-carboxamido-[kappa]N3)pyridinium]copper(II) tetra­hydrate

aLyman Briggs College, Department of Chemistry, Michigan State University, East Lansing, MI 48825, USA
Correspondence e-mail: laduca@msu.edu

In the title compound, [Cu(C11H10N3O)2(C8H4O5)2]·4H2O, the CuII ion, located on a crystallographic inversion center, is coordinated in a square-planar environment by two trans-O atoms belonging to two monodentate 5-hy­droxy­isophthalate (hip) dianions and two trans nicotinamide pyridyl N-donor atoms from monodentate protonated pendant N-(pyridin-4-yl)nicotinamide (4-pnaH) ligands. The protonated 4-pyridyl­amine groups engage in N-H+...O- hydrogen-bond donation to unligated hip O atoms to construct supra­molecular chain motifs parallel to [100]. Water mol­ecules of crystallization, situated between the chains, engage in O-H...O hydrogen bonding to form supra­molecular layers and the overall three-dimensional network structure.

Related literature

For the preparation of 4-pyridyl­nicotinamide, see: Gardner et al. (1954[Gardner, T. S., Wenis, E. & Lee, J. (1954). J. Org. Chem. 19, 753-757.]). For the preparation of other di­carboxyl­ate coordin­ation polymers containing 4-pyridyl­nicotinamide, see: Kumar (2009[Kumar, D. K. (2009). Inorg. Chim. Acta, 362, 1767-1771.]); Wilson et al. (2013[Wilson, J. A., Uebler, J. W. & LaDuca, R. L. (2013). CrystEngComm, 15, 5218-5225.])

[Scheme 1]

Experimental

Crystal data
  • [Cu(C11H10N3O)2(C8H4O5)2]·4H2O

  • Mr = 896.27

  • Monoclinic, P 21 /c

  • a = 16.402 (2) Å

  • b = 7.7699 (10) Å

  • c = 16.403 (2) Å

  • [beta] = 115.466 (1)°

  • V = 1887.3 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 173 K

  • 0.50 × 0.20 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.686, Tmax = 0.745

  • 15084 measured reflections

  • 3483 independent reflections

  • 3122 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.076

  • S = 1.07

  • 3483 reflections

  • 288 parameters

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...O4i 0.87 1.85 2.7164 (18) 170
O1W-H1WB...O3ii 0.87 1.92 2.775 (2) 169
O2W-H2WA...O2 0.87 1.97 2.814 (2) 163
O2W-H2WB...O2iii 0.87 1.94 2.8049 (18) 177
O5-H5...O1W 0.84 1.81 2.6384 (18) 168
N2-H2...O2Wiv 0.88 2.00 2.823 (2) 156
N3-H3...O3v 0.91 (3) 1.69 (3) 2.582 (2) 166 (2)
Symmetry codes: (i) -x, -y, -z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalMaker (Palmer, 2007[Palmer, D. (2007). CrystalMaker. CrystalMaker Software Ltd, Bicester, England.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5361 ).


Acknowledgements

We gratefully acknowledge Michigan State University for funding this work. We thank Dr A. Lifeson for helpful assistance.

References

Bruker (2006). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA.
Bruker (2012). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gardner, T. S., Wenis, E. & Lee, J. (1954). J. Org. Chem. 19, 753-757.  [CrossRef] [ChemPort]
Kumar, D. K. (2009). Inorg. Chim. Acta, 362, 1767-1771.  [Web of Science] [CSD] [CrossRef]
Palmer, D. (2007). CrystalMaker. CrystalMaker Software Ltd, Bicester, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wilson, J. A., Uebler, J. W. & LaDuca, R. L. (2013). CrystEngComm, 15, 5218-5225.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m663  [ doi:10.1107/S1600536813030675 ]

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