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Volume 68 
Part 1 
Pages m31-m32  
January 2012  

Received 20 November 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.039
wR = 0.081
Data-to-parameter ratio = 12.5
Details
Open access

2,9-Dimethyl-1,10-phenanthrolin-1-ium (6-carboxy-4-hydroxypyridine-2-carboxylato-[kappa]3O2,N,O6)(4-hydroxypyridine-2,6-dicarboxylato-[kappa]3O2,N,O6)zincate(II) 2.35-hydrate: a proton-transfer compound

aFaculty of Science, Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Iran,bInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland, and cIran Compiling Encyclopedia Foundation, Tajrish, Tehran, Iran
Correspondence e-mail: zderik@yahoo.com

In the title compound, (C14H13N2)[Zn(C7H3NO5)(C7H4NO5)]·2.35H2O, the ZnII atom is coordinated by two N atoms and four O atoms from the carboxylate groups of the 4-hydroxypyridine-2,6-dicarboxylate and 6-carboxy-4-hydroxypyridine-2-carboxylate ligands, forming a distored octahedral geometry. In the anion, the two pyridine rings are inclined to one another by 87.75 (13)°. Two types of robust O-H...O hydrogen bond synthons, viz. R22(16) and R66(42), link the anions to form a two-dimensional network parallel to the bc plane. Furthermore, O-H...O, N-H...O, N-H...N and weak C-H...O hydrogen bonds connect the two dimensional networks, forming a three-dimensional structure. In the crystal, there are also C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distances of 3.5554 (18) and 3.7681 (18) Å], and C=O...[pi] interactions [O...centroid distance = 3.117 (2) Å] present. One of the three crystal water molecules shows an occupancy of 0.35.

Related literature

For related structures, see: Aghabozorg et al. (2007a[Aghabozorg, H., Ghadermazi, M., Soleimannejad, J. & Sheshmani, S. (2007a). Acta Cryst. E63, m1917-m1918.],b[Aghabozorg, H., Manteghi, F., Ghadermazi, M., Mohammad Panah, F. & Sheshmani, S. (2007b). J. Tech. Educ. 1, 57-78.],c[Aghabozorg, H., Sadrkhanlou, E., Soleimannejad, J. & Adams, H. (2007c). Acta Cryst. E63, m1760.], 2008a[Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008a). J. Iran. Chem. Soc. 5, 184-227.],b[Aghabozorg, H., Motyeian, E., Attar Gharamaleki, J., Soleimannejad, J., Ghadermazi, M. & Spey Sharon, E. (2008b). Acta Cryst. E64, m144-m145.],c[Aghabozorg, H., Motyeian, E., Soleimannejad, J., Ghadermazi, M. & Attar Gharamaleki, J. (2008c). Acta Cryst. E64, m252-m253.]); Derakhshandeh et al. (2010[Derakhshandeh, M., Derikvand, Z., Nemati, A. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, m1084-m1085.]); Moghimi et al. (2005a[Moghimi, A., Aghabozorg, H., Sheshmani, S. & Soleimannejad, J. (2005a). Anal. Sci. 21, x71-x72.],b[Moghimi, A., Aghabozorg, H., Soleimannejad, J. & Ramezanipour, F. (2005b). Acta Cryst. E61, o442-o444.]).

[Scheme 1]

Experimental

Crystal data
  • (C14H13N2)[Zn(C7H3NO5)(C7H4NO5)]·2.35H2O

  • Mr = 680.19

  • Monoclinic, P 21 /c

  • a = 11.0687 (18) Å

  • b = 9.7888 (14) Å

  • c = 25.776 (4) Å

  • [beta] = 94.160 (19)°

  • V = 2785.4 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.96 mm-1

  • T = 223 K

  • 0.38 × 0.15 × 0.15 mm

Data collection
  • Stoe IPDS diffractometer

  • Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) Tmin = 0.972, Tmax = 1.000

  • 20517 measured reflections

  • 5464 independent reflections

  • 3242 reflections with I > 2[sigma](I)

  • Rint = 0.079

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.081

  • S = 0.82

  • 5464 reflections

  • 437 parameters

  • 12 restraints

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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1-C5 ring.

D-H...A D-H H...A D...A D-H...A
N3-H3...N4 0.87 2.37 2.721 (3) 105
N3-H3...O1W 0.87 2.01 2.848 (4) 161
O5-H5...O2W 0.83 1.76 2.570 (4) 166
O7-H7...O2i 0.83 1.66 2.402 (3) 147
O10-H10...O3ii 0.83 1.75 2.562 (3) 166
O1W-H1WA...O9iii 0.83 (3) 2.02 (4) 2.833 (4) 169 (4)
O1W-H1WB...O4iv 0.84 (4) 2.18 (4) 2.960 (4) 156 (3)
O2W-H2WA...O8v 0.82 (4) 1.98 (4) 2.738 (4) 155 (4)
O2W-H2WB...O4vi 0.81 (2) 2.25 (3) 3.046 (4) 171 (4)
O3W-H3WA...O4 0.83 (2) 1.75 (5) 2.530 (7) 157 (13)
O3W-H3WB...O2Wv 0.82 (2) 2.21 (4) 2.750 (9) 123 (3)
C27-H27C...O3vii 0.97 2.58 3.504 (4) 160
C22-H22...Cg1viii 0.94 2.76 3.634 (4) 155
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+2, -z; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+1, -z; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vii) x+1, y, z; (viii) x, y-1, z.

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000[Stoe & Cie (2000). EXPOSE, CELL and INTEGRATE in IPDS-I. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, PLATON and 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: LH5386 ).


Acknowledgements

HSE thanks the XRD Application Lab. of the CSEM, Neuchâtel, for access to the X-ray diffraction equipment.

References

Aghabozorg, H., Ghadermazi, M., Soleimannejad, J. & Sheshmani, S. (2007a). Acta Cryst. E63, m1917-m1918.  [CSD] [CrossRef] [details]
Aghabozorg, H., Manteghi, F., Ghadermazi, M., Mohammad Panah, F. & Sheshmani, S. (2007b). J. Tech. Educ. 1, 57-78.
Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008a). J. Iran. Chem. Soc. 5, 184-227.  [ChemPort]
Aghabozorg, H., Motyeian, E., Attar Gharamaleki, J., Soleimannejad, J., Ghadermazi, M. & Spey Sharon, E. (2008b). Acta Cryst. E64, m144-m145.  [CSD] [CrossRef] [details]
Aghabozorg, H., Motyeian, E., Soleimannejad, J., Ghadermazi, M. & Attar Gharamaleki, J. (2008c). Acta Cryst. E64, m252-m253.  [CSD] [CrossRef] [details]
Aghabozorg, H., Sadrkhanlou, E., Soleimannejad, J. & Adams, H. (2007c). Acta Cryst. E63, m1760.  [CSD] [CrossRef] [details]
Derakhshandeh, M., Derikvand, Z., Nemati, A. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, m1084-m1085.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Moghimi, A., Aghabozorg, H., Sheshmani, S. & Soleimannejad, J. (2005a). Anal. Sci. 21, x71-x72.  [ChemPort]
Moghimi, A., Aghabozorg, H., Soleimannejad, J. & Ramezanipour, F. (2005b). Acta Cryst. E61, o442-o444.  [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 (2000). EXPOSE, CELL and INTEGRATE in IPDS-I. Stoe & Cie GmbH, Darmstadt, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, m31-m32   [ doi:10.1107/S1600536811052445 ]

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