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Volume 65 
Part 5 
Pages m498-m499  
May 2009  

Received 12 March 2009
Accepted 3 April 2009
Online 8 April 2009

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Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.122
Data-to-parameter ratio = 21.8
Details
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{6,6'-Diethoxy-2,2'-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) dihydrate

Hadi Kargar,a Reza Kia,b+ Arezoo Jamshidvanda and Hoong-Kun Funb*

aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title complex, [Ni(C26H26N2O4)]·2H2O, the NiII ion, lying on a twofold crystallographic rotation axis, has a square-planar geometry, being coordinated by the N2O2 unit of the tetradentate Schiff base ligand. The asymmetric unit of the title compound comprises one-half of the complex molecule and one of the water molecules of crystallization. The water H atoms form bifurcated O-H...(O,O) hydrogen bonds with the O atoms of the phenolato and ethoxy groups with R12(5) and R12(6) ring motifs. The dihedral angle between the central benzene ring and the two outer benzene rings are 4.07 (11) and 3.99 (12)°. The dihedral angle between the two O-Ni-N coordination planes is only 0.77 (11)°. In the crystal structure, the molecules are linked together into extended chains along the c axis by intermolecular O-H...O and C-H...O interactions. An interesting feature of the crystal structure is a short intermolecular C ... C [3.355 (3) Å] contact, which is shorter than the sum of the van der Waals radii. The crystal structure may be further stabilized by intermolecular [pi]-[pi] interactions [centroid-centroid distances in the range 3.5758 (13)-3.6337 (13) Å].

Related literature

For bond-length data, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For related structures see, for example: Clark et al. (1968[Clark, G. R., Hall, D. & Waters, T. N. (1968). J. Chem. Soc. A, pp. 223-226.], 1969[Clark, G. R., Hall, D. & Waters, T. N. (1969). J. Chem. Soc. A, pp. 823-829.], 1970[Clark, G. R., Hall, D. & Waters, T. N. (1970). J. Chem. Soc. A, pp. 396-399.]). For the applications and bioactivity of Schiff base complexes see, for example: Elmali et al. (2000[Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423-424.]); Blower (1998[Blower, P. J. (1998). Transition Met. Chem. 23, 109-112.]); Granovski et al. (1993[Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1-69.]); Li & Chang, (1991[Li, C. H. & Chang, T. C. (1991). Eur. Polym. J. 27, 35-39.]); Shahrokhian et al. (2000[Shahrokhian, S., Amini, M. K., Kia, R. & Tangestaninejad, S. (2000). Anal. Chem. 72, 956-962.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • [Ni(C26H26N2O4)]·2H2O

  • Mr = 525.23

  • Orthorhombic, P b c n

  • a = 12.8706 (4) Å

  • b = 16.1130 (4) Å

  • c = 11.8546 (3) Å

  • V = 2458.45 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.83 mm-1

  • T = 294 K

  • 0.30 × 0.16 × 0.08 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2 , SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.790, Tmax = 0.935

  • 16330 measured reflections

  • 3517 independent reflections

  • 2007 reflections with I > 2[sigma]I)

  • Rint = 0.065
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.122

  • S = 1.01

  • 3517 reflections

  • 161 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Selected bond lengths (Å)

Ni1-O1 1.8447 (15)
Ni1-N1 1.8573 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W1...O1 0.82 2.50 3.087 (2) 129
O1W-H1W1...O2 0.82 2.39 3.145 (3) 152
O1W-H2W1...O1i 0.82 2.47 3.083 (3) 133
O1W-H2W1...O2i 0.82 2.41 3.121 (3) 146
C7-H7A...O1Wii 0.93 2.57 3.383 (3) 146
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [x, -y, z+{\script{1\over 2}}].

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2114 ).

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blower, P. J. (1998). Transition Met. Chem. 23, 109-112.  [CrossRef] [ChemPort]
Bruker (2005). APEX2 , SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clark, G. R., Hall, D. & Waters, T. N. (1968). J. Chem. Soc. A, pp. 223-226.
Clark, G. R., Hall, D. & Waters, T. N. (1969). J. Chem. Soc. A, pp. 823-829.
Clark, G. R., Hall, D. & Waters, T. N. (1970). J. Chem. Soc. A, pp. 396-399.
Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423-424.  [CSD] [CrossRef] [details]
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1-69.
Li, C. H. & Chang, T. C. (1991). Eur. Polym. J. 27, 35-39.  [CrossRef] [ChemPort] [ISI]
Shahrokhian, S., Amini, M. K., Kia, R. & Tangestaninejad, S. (2000). Anal. Chem. 72, 956-962.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2009). E65, m498-m499   [ doi:10.1107/S1600536809012641 ]

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