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Volume 69 
Part 7 
Pages m417-m418  
July 2013  

Received 14 June 2013
Accepted 21 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 170 K
Mean [sigma](C-C) = 0.007 Å
R = 0.062
wR = 0.153
Data-to-parameter ratio = 16.9
Details
Open access

(3-Acetyl-4-methyl-1H-pyrazol-1-ide-5-carboxylato)bis(1,10-phenanthroline)nickel(II) 3.5-hydrate

aDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kiev, Ukraine,bFaculty of Chemistry, University of Wroclaw, F. Joliot-Curie Street 14, 50-383 Wroclaw, Poland, and cDepartment of Chemistry, Kyiv National University of Construction and Architecture, Povitroflotsky Avenue 31, 03680 Kiev, Ukraine
Correspondence e-mail: tiskenderov@ukr.net

The title compound, [Ni(C7H6N2O3)(C12H8N2)2]·3.5H2O, crystallizes as a neutral mononuclear complex with 3.5 solvent water molecules. One of the water molecules lies on an inversion centre, so that its H atoms are disordered over two sites. The coordination environment of NiII has a slightly distorted octahedral geometry, which is formed by one O and five N atoms belonging to the N,O-chelating pyrazol-1-ide-5-carboxylate and two N,N'-chelating phenanthroline molecules. In the crystal, O-H...O, N-H...O and O-H...N hydrogen bonds involving the solvent water molecules and pyrazole-5-carboxylate ligands form layers parallel to the ab plane. These layers are linked further via weak [pi]-[pi] interactions between two adjacent phenanthroline molecules, with centroid-to-centroid distances in the range 3.886 (2)-4.018 (1) Å, together with C-H...[pi] contacts, forming a three-dimensional network.

Related literature

The work presented here continues studies of complexes based on pyrazolate ligands with transition metals, see: Klingele et al. (2009[Klingele, J., Dechert, S. & Meyer, F. (2009). Coord. Chem. Rev. 253, 2698-2741.]); Malinkin et al. (2009[Malinkin, S., Penkova, L., Pavlenko, V. A., Haukka, M. & Fritsky, I. O. (2009). Acta Cryst. E65, m1247-m1248.], 2012a[Malinkin, S., Penkova, L., Moroz, Y. S., Haukka, M., Maciag, A., Gumienna-Kontecka, E., Pavlova, S., Nordlander, E., Fritsky, I. O. & Pavlenko, V. A. (2012a). Eur. J. Inorg. Chem. pp. 1639-1649.],b[Malinkin, S. O., Penkova, L., Moroz, Y. S., Bon, V., Gumienna-Kontecka, E., Pekhnyo, V. I., Meyer, F. & Fritsky, I. O. (2012b). Polyhedron, 37, 77-84.],c[Malinkin, S. O., Moroz, Y. S., Penkova, L., Haukka, M., Szebesczyk, A., Gumienna-Kontecka, E., Pavlenko, V. A., Nordlander, E., Meyer, F. & Fritsky, I. O. (2012c). Inorg. Chim. Acta, 392, 322-330.]); Ng et al. (2011[Ng, G. K.-Y., Ziller, J. W. & Borovik, A. S. (2011). Inorg. Chem. 50, 7922-7924.]); Penkova et al. (2008[Penkova, L., Demeshko, S., Haukka, M., Pavlenko, V. A., Meyer, F. & Fritsky, I. O. (2008). Z. Anorg. Allg. Chem. 634, 2428-2436.], 2009[Penkova, L. V., Maciag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.]); Meyer & Pritzkow (2000[Meyer, F. & Pritzkow, H. (2000). Angew. Chem. Int. Ed. 39, 2112-2115.]); Bauer-Siebenlist et al. (2005[Bauer-Siebenlist, B., Dechert, S. & Meyer, F. (2005). Chem. Eur. J. 11, 5343-5352.]); Swiatek-Kozlowska et al. (2000[Swiatek-Kozlowska, J., Fritsky, I. O., Dobosz, A., Karaczyn, A., Dudarenko, N. M., Sliva, T. Yu., Gumienna-Kontecka, E. & Jerzykiewicz, L. (2000). J. Chem. Soc. Dalton Trans. pp. 4064-4068.]). For related structures, see: Zhong et al. (2009[Zhong, F., Ying, S., Liu, J., Duan, D., Shi, T. & Wang, Q. (2009). Chem. Res. Appl. 21, 385-391.]); Zheng et al. (2009[Zheng, Z.-B., Wu, R.-T., Li, J.-K. & Sun, Y.-F. (2009). J. Mol. Struct. 928, 78-84.]); Bouchene et al. (2013[Bouchene, R., Khadri, A., Bouacida, S., Berrah, F. & Merazig, H. (2013). Acta Cryst. E69, m309-m310.]); Fang & Wang (2010[Fang, Z. & Wang, J. (2010). Acta Cryst. E66, m1285.]); Fritsky et al. (2004[Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.], 2006[Fritsky, I. O., Kozlowski, H., Kanderal, O. M., Haukka, M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.]); Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]); Moroz et al. (2010[Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.]). For the starting material, see: Sachse et al. (2008[Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, 5, 800-806.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C7H6N2O3)(C12H8N2)2]·3.5H2O

  • Mr = 648.29

  • Triclinic, [P \overline 1]

  • a = 9.865 (3) Å

  • b = 11.659 (4) Å

  • c = 13.561 (5) Å

  • [alpha] = 91.91 (3)°

  • [beta] = 98.85 (3)°

  • [gamma] = 105.20 (4)°

  • V = 1482.8 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.71 mm-1

  • T = 170 K

  • 0.23 × 0.18 × 0.11 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: numerical (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.857, Tmax = 0.929

  • 12624 measured reflections

  • 6830 independent reflections

  • 3040 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.153

  • S = 0.85

  • 6830 reflections

  • 405 parameters

  • 13 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 1.12 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Table 1
Selected bond lengths (Å)

N1-Ni1 2.041 (4)
N3-Ni1 2.085 (4)
N4-Ni1 2.080 (4)
N5-Ni1 2.078 (3)
N6-Ni1 2.093 (4)
O2-Ni1 2.066 (3)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/N2/C2/C3/C4 pyrazole ring.

D-H...A D-H H...A D...A D-H...A
O4-H4A...O3 0.95 2.31 3.088 (6) 139
O4-H4B...N2i 0.94 2.01 2.906 (6) 157
O5-H5A...O4ii 0.86 2.02 2.875 (6) 172
O5-H5B...O1 0.90 2.00 2.787 (5) 145
O6-H6D...O5 0.87 2.05 2.895 (6) 163
O6-H6E...O2 0.88 1.98 2.827 (5) 163
O7-H7D...O3 0.89 2.16 2.964 (4) 150
O7-H7E...O4 0.89 2.02 2.821 (5) 149
C12-H12...Cg1iii 0.93 2.77 3.646 (6) 158
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5334 ).


Acknowledgements

The authors are grateful for financial support from the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program).

References

Bauer-Siebenlist, B., Dechert, S. & Meyer, F. (2005). Chem. Eur. J. 11, 5343-5352.  [PubMed] [ChemPort]
Bouchene, R., Khadri, A., Bouacida, S., Berrah, F. & Merazig, H. (2013). Acta Cryst. E69, m309-m310.  [CrossRef] [ChemPort] [IUCr Journals]
Fang, Z. & Wang, J. (2010). Acta Cryst. E66, m1285.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fritsky, I. O., Kozlowski, H., Kanderal, O. M., Haukka, M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.  [CSD] [CrossRef]
Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.  [CrossRef] [PubMed]
Klingele, J., Dechert, S. & Meyer, F. (2009). Coord. Chem. Rev. 253, 2698-2741.  [Web of Science] [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Malinkin, S. O., Moroz, Y. S., Penkova, L., Haukka, M., Szebesczyk, A., Gumienna-Kontecka, E., Pavlenko, V. A., Nordlander, E., Meyer, F. & Fritsky, I. O. (2012c). Inorg. Chim. Acta, 392, 322-330.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Malinkin, S. O., Penkova, L., Moroz, Y. S., Bon, V., Gumienna-Kontecka, E., Pekhnyo, V. I., Meyer, F. & Fritsky, I. O. (2012b). Polyhedron, 37, 77-84.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Malinkin, S., Penkova, L., Moroz, Y. S., Haukka, M., Maciag, A., Gumienna-Kontecka, E., Pavlova, S., Nordlander, E., Fritsky, I. O. & Pavlenko, V. A. (2012a). Eur. J. Inorg. Chem. pp. 1639-1649.  [Web of Science] [CSD] [CrossRef]
Malinkin, S., Penkova, L., Pavlenko, V. A., Haukka, M. & Fritsky, I. O. (2009). Acta Cryst. E65, m1247-m1248.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Meyer, F. & Pritzkow, H. (2000). Angew. Chem. Int. Ed. 39, 2112-2115.  [CrossRef] [ChemPort]
Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Ng, G. K.-Y., Ziller, J. W. & Borovik, A. S. (2011). Inorg. Chem. 50, 7922-7924.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.
Penkova, L., Demeshko, S., Haukka, M., Pavlenko, V. A., Meyer, F. & Fritsky, I. O. (2008). Z. Anorg. Allg. Chem. 634, 2428-2436.  [CSD] [CrossRef] [ChemPort]
Penkova, L. V., Maciag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, 5, 800-806.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Swiatek-Kozlowska, J., Fritsky, I. O., Dobosz, A., Karaczyn, A., Dudarenko, N. M., Sliva, T. Yu., Gumienna-Kontecka, E. & Jerzykiewicz, L. (2000). J. Chem. Soc. Dalton Trans. pp. 4064-4068.
Zheng, Z.-B., Wu, R.-T., Li, J.-K. & Sun, Y.-F. (2009). J. Mol. Struct. 928, 78-84.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zhong, F., Ying, S., Liu, J., Duan, D., Shi, T. & Wang, Q. (2009). Chem. Res. Appl. 21, 385-391.  [ChemPort]


Acta Cryst (2013). E69, m417-m418   [ doi:10.1107/S1600536813017194 ]

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