{3-Methyl-2-[(1-oxido-2-naphth­yl)methyl­idene­amino-κ2O,N]butano­ato-κO}(1H-pyrazole-κN2)nickel(II)

Peng, Q.-L.; Zhao, G.-Q.; Chen, L.-H.; Xue, L.-W.

doi:10.1107/S1600536810032472

Volume 66
Part 9
Pages m1127-m1128
September 2010

Received 11 July 2010
Accepted 12 August 2010
Online 18 August 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.008 Å
R = 0.044
wR = 0.108
Data-to-parameter ratio = 13.5
Details

{3-Methyl-2-[(1-oxido-2-naphthyl)methylideneamino-²O,N]butanoato-O}(1H-pyrazole-N²)nickel(II)

Qin-Long Peng,^a ^* Gan-Qing Zhao,^a Li-Hua Chen ^a and Ling-Wei Xue ^a

^aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
Correspondence e-mail: jecky_2002@163.com

In either of the two independent molecules within the asymmetric unit of the title compound, [Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)], the Ni^II atom is coordinated by the two N atoms and two O atoms in a distorted square-planar geometry. The crystal packing is stabilized by strong and weak intermolecular C-HO hydrogen bonds, as well as weak centroid-centroid [pi] -stacking interactions [centroid-centroid separation = 3.526 (3) Å].

Related literature

For complexes of Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, see: Li et al. (2010); Vergopoulos et al. (1993); Usman et al. (2003). For related structures, see: Basu Baul et al. (2007); Ebel & Rehder (2003); Maniukiewicz & Bukowska-Strzyzewska (2001); Xue et al. (2009); Qiu et al. (2008). For the synthesis, see: Plesch et al. (1997).

Experimental

Crystal data

[Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)]
M_r = 396.08
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.5089 (11) Å
b = 16.6194 (16) Å
c = 18.9934 (19) Å
V = 3632.9 (6) Å³
Z = 8
Mo K radiation
= 1.09 mm^-1
T = 296 K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.735, T_max = 0.772
18967 measured reflections
6400 independent reflections
4910 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.108
S = 1.02
6400 reflections
473 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.36 e Å^-3
Absolute structure: Flack (1983), 2792 Friedel pairs
Flack parameter: -0.015 (16)

Table 1
Selected geometric parameters (Å, °)

Ni1-O1	1.805 (3)
Ni1-N1	1.833 (3)
Ni1-O2	1.852 (3)
Ni1-N2	1.900 (3)

O1-Ni1-N1	94.55 (15)
O1-Ni1-O2	176.92 (16)
N1-Ni1-O2	86.20 (15)
O1-Ni1-N2	89.98 (16)
N1-Ni1-N2	173.95 (16)
O2-Ni1-N2	89.49 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O2ⁱ	0.93	2.59	3.476 (6)	159
C14-H14O6ⁱⁱ	0.98	2.42	3.318 (6)	153
C18-H18O6ⁱⁱⁱ	0.93	1.87	2.798 (5)	178
C37-H37O3^iv	0.93	1.85	2.756 (5)	163
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Table 3
Weak Cg-Cg intermolecular interactions of (I) (Å)

Distance	Cg1-Cg10	Cg3-Cg9	Cg4-Cg7	Cg4-Cg9
Centroid-centroid distance	3.940 (3)	3.709 (2)	3.526 (3)	3.932 (3)
Notes: CgI-CgJ = centroid-centroid distance between planes I and J (Å); Cg1: Ni1/O2/C13/C12/N1; Cg3: Ni1/O1/C1/C10/C11/N1; Cg4: C1/C2/C3/C4/C9/C10; Cg7: Ni2/O5/C32/C31/N4; Cg9: Ni2/O4/C20/C29/C30/N4; Cg10: C20/C21/C22/C23/C28/C29.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2044 ).

Acknowledgements

This research was supported by the National Sciences Foundation of China (grant No. 20877036) and the Top-Class Foundation of Pingdingshan University (grant Nos. 2008012 and 2009001).

References

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Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ebel, M. & Rehder, D. (2003). Inorg. Chim. Acta, 356, 210-214.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Usman, A., Fun, H.-K., Basu Baul, T. S. & Paul, P. C. (2003). Acta Cryst. E59, m438-m440.
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Xue, L.-W., Li, X.-W., Zhao, G.-Q. & Peng, Q.-L. (2009). Acta Cryst. E65, m1237.

metal-organic compounds

{3-Methyl-2-[(1-oxido-2-naphthyl)methylideneamino-2O,N]butanoato-O}(1H-pyrazole-N2)nickel(II)