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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 61| Part 10| October 2005| Pages m2033-m2035
doi:10.1107/S1600536805028965

Bis[1-(2,6-di­methyl­anilino)propane-1,2-dione dioximato]nickel(II)

CROSSMARK_Color_square_no_text.svg
Hümeyra Batı,a Ayşin Zülfikaroğlu,a Murat Taş,a Omer Andaca and William T. A. Harrisonb*

aDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Kurupelit Samsun, Turkey, and bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: oandac@omu.edu.tr

(Received 8 September 2005; accepted 13 September 2005; online 17 September 2005)

The structure of the title complex consists of isolated [Ni(C11H14N3O2)2] units. The Ni atom is coordinated by four oxime N atoms in distorted square-planar geometry and lies on an inversion centre. The structure is stabilized by strong intra­molecular N—H⋯O and O—H⋯O hydrogen bonds and a possible N—H⋯π inter­molecular inter­action.

Comment

This work is part of our ongoing research on the synthesis and characterization of new vic-dioximes and their transition metal complexes (Zülfikaroglu et al., 2003[Zülfikaroglu, A., Taş, M., Batı, H. & Batı, B. (2003). Synth. React. Inorg. Met.-Org. Chem. 33, 625-638.]). Metal complexes of various glyoximate ligands have long been of importance in analytical chemistry and medicine (Chakravorty, 1974[Chakravorty, A. (1974). Coord. Chem. Rev. 13, 1-46.]; Michael et al., 2000[Michael, J. P., Anthony, W. A. & Raymond, J. B. (2000). Inorg. Chim. Acta, 300-302, 992-1003.]).

[Scheme 1]

In the title compound, (I)[link], alternately named bis­[N-(2,6-dimethyl­phen­yl)amino­methyl­glyoximato-N,N′]nickel(II) (Fig. 1[link]), the Ni atom, which lies on a site of [{\overline 1}] symmetry, is coordinated by four oxime N atoms arising from two bident­ate ligand mol­ecules. The local coordination of the NiN4 chromophore is distorted square planar (D2h symmetry). The Ni—N and O1⋯O2i distances (Tables 1[link] and 2[link]; symmetry code as in these tables) are similar to the distances found in the related complexes bis­[N-(2,6-dimethyl­phen­yl)amino­glyoximato-N,N′]nickel(II) (Ülkü et al., 1996[Ülkü, D., Ercan, F., Macit, M. & Gulce, A. (1996). Acta Cryst. C52, 2680-2682.]), bis­[N-(4-methyl­phen­yl)amino­glyoximato-N,N′]­nickel(II) (Isik et al., 2000[Isik, S., Ozturk, S., Erdonmez, A., Macit, M. & Fun, H.-K. (2000). Anal. Sci. 16, 559-560.]), bis­[N-(2,6-dimethyl­phen­yl)­amino­phenyl­glyoximato-κ2N,N′]nickel(II) dimethyl sulfoxide solvate (Batı et al., 2004[Batı, H., Zülfikaroglu, A., Taş, M., Çalışkan, N., Soylu, S., Andac, O. & Büyükgüngör, O. (2004). Acta Cryst. E60, m1334-m1336.]) and bis­[N-(4-methoxy­phen­yl)­amino­methyl­glyoximato]­nickel(II) (Batı et al., 2005[Batı, H., Daĝ, C., Soylu, M. S., Taş, M., Çalışkan, N. & Büyükgüngör, O. (2005). Acta Cryst. E61, m1866-m1868.]). In these, one Ni—N bond is significantly longer than the other (by between 0.02 and 0.05 Å). This difference can possibly be attributed to the different groups attached to oxime atoms C9 and C10.

The different N—O bond lengths reflect the chemically distinct O atoms. The oxime group has an E configuration with planar O1—N2—C9—C10. The oxime OH group is adjacent to the bridging amine group in all complexes, and in (I)[link] accepts an intra­ligand N—H⋯O bond. The benzene and five-membered chelate (NiC2N2) rings in (I)[link] are essentially planar, with r.m.s. deviations of only 0.0045 and 0.0159 Å.

Comparision of the bond lengths of the oxime group with those of the free ligand (Hökelek et al., 2001[Hökelek, T., Zülfikaroglu, A. & Batı, H. (2001). Acta Cryst. E57, o1247-o1249.]) reveals that, upon complex formation, the N2—O1, N3—O2 and C9—C10 distances are shortened by 0.040, 0.078 and 0.018 Å, respectively, whereas the C9—N2 and C10—N3 distances are increased by 0.013 and 0.028 Å, respectively.

The intra­molecular inter-ligand O⋯O separations in these compounds are all similar, lying between 2.462 (3) and 2.547 (3) Å. Such short O⋯O separations are often associated with symmetrical O⋯H⋯O hydrogen bonds (Chakravorty, 1974[Chakravorty, A. (1974). Coord. Chem. Rev. 13, 1-46.]). In (I)[link], one of the O-bound acidic H atoms is lost from each ligand during complex formation and the remaining O-bound H atom participates in a very strong intra­molecular hydrogen bond to the adjacent O atom (Table 2[link]). The H atom was clearly visible in a difference map and, like the other complexes noted above, the O—H⋯O bond is not symmetrical.

An analysis of the intermol­ecular contacts in (I)[link] with PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) revealed a possible weak N—H⋯π(−x, 1 − y, 2 − z) inter­action between the amine H atom and an adjacent benzene ring (atoms C1–C6) with an H⋯π distance of 2.965 (16) Å.

[Figure 1]
Figure 1
View of (I)[link] showing 40% probability displacement ellipsoids (arbitrary spheres for the H atoms) and hydrogen bonds as dashed lines. [Symmetry code: (i) 1 − x, 1 − y, 1 − z.]

Experimental

1-(2,6-Dimethyl­phenyl­amino)propane-1,2-dione dioxime (L) was prepared according to the method of Hökelek et al. (2001[Hökelek, T., Zülfikaroglu, A. & Batı, H. (2001). Acta Cryst. E57, o1247-o1249.]). A solution of NiCl2·6H2O (0.48 g. 2 mmol) in ethanol–water (1:1) was added dropwise to a solution of L (0.882 g. 4 mmol) in ethanol (20 ml). A 1% solution of KOH in water was then dripped slowly into the mixture until the pH reached 5.5. The resulting precipitate was removed by suction filtration, washed and dried in vacuo. Recrystallization from a chloro­form–ethanol mixture (2:1) gave orange rod crystals of (I)[link].

Crystal data

  • [Ni(C11H14N3O2)2]

  • Mr = 499.21

  • Monoclinic, P 21 /c

  • a = 8.1081 (4) Å

  • b = 16.0311 (8) Å

  • c = 8.9223 (4) Å

  • β = 94.202 (1)°

  • V = 1156.62 (10) Å3

  • Z = 2

  • Dx = 1.433 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 4650 reflections

  • θ = 2.5–32.0°

  • μ = 0.88 mm−1

  • T = 293 (2) K

  • Rod, orange

  • 0.49 × 0.30 × 0.24 mm
Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer

  • ω scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS, SHELXS97 and SHELXL97. University of Göttingen, Germany.])Tmin = 0.736, Tmax = 0.810

  • 11778 measured reflections

  • 4184 independent reflections

  • 2988 reflections with I > 2σ(I)

  • Rint = 0.021

  • θmax = 32.5°

  • h = −12 → 11

  • k = −24 → 16

  • l = −13 → 13
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.093

  • S = 0.98

  • 4184 reflections

  • 159 parameters

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

  • w = 1/[σ2(Fo2) + (0.0541P)2] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

Ni1—N2 1.8397 (11)
Ni1—N3 1.8779 (11)
N2—Ni1—N3i 97.62 (5)
N2—Ni1—N3 82.38 (5)
Symmetry code: (i) 1-x, 1-y, 1-z.

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯O2i 0.86 (1) 1.65 (1) 2.4972 (14) 171 (2)
N1—H1N⋯O1 0.82 (1) 2.20 (2) 2.6361 (16) 113 (1)
Symmetry code: (i) 1-x, 1-y, 1-z.

The O- and N-bound H atoms were found in difference maps and were refined with distance restraints [O—H = 0.84 (2) Å and N—H = 0.86 (2) Å] and with Uiso(H) = 1.2Ueq(carrier). C-bound H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2 Ueq(carrier) or Uiso(H) = 1.5Ueq(methyl carrier). The –CH3 groups were rotated to fit the electron density.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS, SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS, SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536805028965/ng6197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536805028965/ng6197Isup2.hkl


Comment top

This work is part of our ongoing research on the synthesis and characterization of new vic dioximes and their transition metal complexes (Zülfikaroglu et al., 2003). Metal complexes of various glyoximate ligands have long been of importance in analytical chemistry and medicine (Chakravorty, 1974; Michael et al., 2000). In the title compound, (I), alternately named bis[N-(2,6-dimethylphenyl)aminomethylglyoximato-N,N']nickel(II) (Fig. 1), the Ni atom that lies on a site of −1 symmetry, is coordinated by four oxime N atoms arising from two bidentate ligand molecules. The local coordination of the NiN4 chromophore is distorted square planar (D2h symmetry). The Ni—N and O1···O2i distances (Tables 1 and 2) are similar to the distances found in the related complexes bis[N-(2,6-dimethylphenyl)aminoglyoximato-N,N']nickel(II) (Ulku et al., 1996), bis[N-(4-methylphenyl) aminoglyoximato-N,N ']nickel(II) (Isik et al., 2000), bis[N-(2,6-dimethylphenyl)aminophenylglyoximato-κ2N,N']nickel(II) dimethyl sulfoxide solvate (Batı et al., 2004) and bis[N-(4-methoxyphenyl)aminomethylglyoximato]nickel(II) (Batı et al., 2005). In these, one Ni—N bond is significantly longer than the other (by between 0.02 and 0.05 Å). This difference can possibly be attributed to the different groups attached to oxime atoms C9 and C10. The intramolecular, inter-ligand, O···O separations in these compounds are all similar, lying between 2.462 (3) and 2.547 (3) Å. Such short O···O separations are often associated with symmetrical O···H···O hydrogen bonds (Chakravorty, 1974). In (I), one of the O-bound acidic H atoms is lost from each ligand during complex formation and the remaining O-bound H atom participates in a very strong intramolecular hydrogen bond to the adjacent O atom (Table 2). The H atom was clearly visible in a difference map and, like the other complexes noted above, the O—H···O bond is not symmetrical. The different N—O bond lengths reflect the chemically distinct O atoms. The oxime group has an E configuration with planar O1—N2—C9—C10. The oxime –OH group is adjacent to the bridging amine group in all complexes, and in (I) accepts an intraligand N—H···O bond. The phenyl and five-membered chelate (NiC2N2) rings in (I) are almost planar, with r.m.s deviations of 0.0045 and 0.0159 Å only.

Comparision of the bond lengths of the oxime group with those of the free ligand (Hökelek et al., 2001) reveals that, upon complex formation, the N2—O1, N3—O3 and C9—C10 distances are shortened by 0.040, 0.078 and 0.018 Å, whereas the C9—N2 and C10—N3 distances are increased by 0.013 and 0.028 Å.

An analysis of the inter-molecular contacts in (I) with PLATON (Spek, 2003) reveals a possible weak N—H···π(−x, 1 − y, 2 − z) interaction between the amine H atom and an adjacent phenyl ring (atoms C1–C6) with an H···π distance of 2.965 (16) Å.

Experimental top

1-(2,6-Dimethylphenylamino)propane-1,2-dione dioxime (L) was prepared according to the method of Hökelek et al. (2001). A solution of NiCl2·6H2O (0.48 g. 2 mmol) in ethanol–water (1:1) was added dropwise to a solution of L (0.882 g. 4 mmol) in ethanol (20 ml). Then, a 1% solution of KOH in water was dripped slowly into the mixture until the pH reached 5.5. The resulting precipitate was removed by suction filtration, washed and dried in vacuo. Recrystallization from a chloroform–ethanol mixture (2:1) gave orange rod crystals of (I).

Refinement top

The O– and N-bound H atoms were found in difference maps and were refined with distance restraints [O—H = 0.84 (2) Å and N—H = 0.86 (2) Å] and with Uiso(H) = 1.2Ueq(carrier) to yield the final values given in Table 2. C-bound H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2 Ueq(carrier) or Uiso(H) = 1.5 Ueq(methyl carrier). The –CH3 groups were rotated to fit the electron density.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of (I) showing 40% probability displacement ellipsoids (arbitrary spheres for the H atoms) and hydrogen bonds as dashed lines. [Symmetry code: (i) 1 − x, 1 − y, 1 − z.]
Bis[1-(2,6-dimethylanilino)propane-1,2-dione dioximato]nickel(II) top
Crystal data top
[Ni(C11H14N3O2)2]F(000) = 524
Mr = 499.21Dx = 1.433 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4650 reflections
a = 8.1081 (4) Åθ = 2.5–32.0°
b = 16.0311 (8) ŵ = 0.88 mm−1
c = 8.9223 (4) ÅT = 293 K
β = 94.202 (1)°Rod, orange
V = 1156.62 (10) Å30.49 × 0.30 × 0.24 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4184 independent reflections
Radiation source: fine-focus sealed tube2988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 32.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		h = −12→11
Tmin = 0.736, Tmax = 0.810k = −24→16
11778 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: none
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difmap (O-H and N-H) and geom (C-H)
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0541P)2]
where P = (Fo2 + 2Fc2)/3
4184 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
[Ni(C11H14N3O2)2]V = 1156.62 (10) Å3
Mr = 499.21Z = 2
Monoclinic, P21/cMo Kα radiation
a = 8.1081 (4) ŵ = 0.88 mm−1
b = 16.0311 (8) ÅT = 293 K
c = 8.9223 (4) Å0.49 × 0.30 × 0.24 mm
β = 94.202 (1)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		4184 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		2988 reflections with I > 2σ(I)
Tmin = 0.736, Tmax = 0.810Rint = 0.021
11778 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.45 e Å−3
4184 reflectionsΔρmin = −0.16 e Å−3
159 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.03193 (8)
O10.31671 (14)0.39481 (6)0.69080 (12)0.0479 (2)
H1O0.361 (2)0.3665 (12)0.6227 (19)0.082 (7)*
O20.55255 (14)0.67355 (6)0.52231 (12)0.0491 (2)
N10.23048 (16)0.52210 (8)0.85500 (15)0.0444 (3)
H1N0.221 (2)0.4716 (9)0.8697 (19)0.047 (5)*
N20.37428 (14)0.47315 (8)0.65657 (13)0.0379 (2)
N30.47882 (13)0.60817 (7)0.57706 (13)0.0373 (2)
C10.11259 (16)0.58122 (9)0.90465 (15)0.0391 (3)
C2−0.01565 (17)0.60907 (10)0.80574 (16)0.0460 (3)
C3−0.13125 (19)0.66334 (11)0.86028 (19)0.0550 (4)
H3−0.21690.68370.79550.066*
C4−0.1203 (2)0.68714 (11)1.0086 (2)0.0582 (4)
H4−0.19940.72261.04410.070*
C50.0076 (2)0.65839 (11)1.10458 (18)0.0532 (4)
H50.01390.67501.20470.064*
C60.12720 (17)0.60536 (10)1.05560 (16)0.0439 (3)
C70.2701 (2)0.57673 (12)1.15995 (18)0.0615 (4)
H7A0.25580.59651.25970.092*
H7B0.37140.59851.12640.092*
H7C0.27440.51691.16030.092*
C8−0.0333 (2)0.58167 (14)0.64311 (18)0.0672 (5)
H8A0.04500.61130.58740.101*
H8B−0.14340.59350.60150.101*
H8C−0.01260.52280.63720.101*
C90.32550 (16)0.53464 (9)0.73794 (15)0.0369 (3)
C100.39180 (16)0.61579 (9)0.69449 (15)0.0388 (3)
C110.3760 (2)0.69658 (10)0.7739 (2)0.0606 (4)
H11A0.45600.73530.74090.091*
H11B0.39490.68800.88030.091*
H11C0.26680.71860.75180.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02994 (11)0.03035 (12)0.03578 (12)0.00224 (8)0.00434 (8)−0.00006 (9)
O10.0569 (6)0.0344 (5)0.0547 (6)−0.0031 (4)0.0195 (5)0.0013 (5)
O20.0568 (6)0.0315 (5)0.0612 (6)−0.0033 (4)0.0193 (5)0.0003 (4)
N10.0461 (7)0.0403 (6)0.0486 (7)0.0048 (5)0.0165 (5)0.0007 (5)
N20.0381 (6)0.0334 (5)0.0430 (6)0.0003 (4)0.0084 (5)0.0007 (5)
N30.0346 (5)0.0328 (5)0.0449 (6)0.0009 (4)0.0057 (4)0.0001 (5)
C10.0359 (6)0.0413 (7)0.0412 (7)0.0013 (5)0.0099 (5)−0.0026 (5)
C20.0387 (7)0.0566 (9)0.0431 (7)0.0007 (6)0.0058 (6)−0.0020 (7)
C30.0413 (8)0.0607 (10)0.0635 (10)0.0099 (7)0.0064 (7)0.0075 (8)
C40.0522 (9)0.0548 (10)0.0701 (11)0.0102 (7)0.0230 (8)−0.0050 (8)
C50.0601 (10)0.0541 (9)0.0475 (8)−0.0007 (7)0.0181 (7)−0.0102 (7)
C60.0450 (7)0.0467 (8)0.0406 (7)−0.0027 (6)0.0068 (6)−0.0020 (6)
C70.0633 (10)0.0719 (12)0.0477 (9)0.0029 (9)−0.0061 (7)0.0019 (8)
C80.0576 (10)0.0985 (16)0.0443 (8)0.0030 (10)−0.0039 (7)−0.0096 (9)
C90.0317 (6)0.0387 (7)0.0406 (6)0.0035 (5)0.0045 (5)−0.0020 (6)
C100.0364 (6)0.0353 (6)0.0451 (7)0.0020 (5)0.0058 (5)−0.0054 (5)
C110.0628 (10)0.0439 (9)0.0786 (11)−0.0061 (7)0.0292 (8)−0.0192 (8)
Geometric parameters (Å, º) top
Ni1—N2i1.8397 (11)C3—H30.9300
Ni1—N21.8397 (11)C4—C51.375 (2)
Ni1—N3i1.8779 (11)C4—H40.9300
Ni1—N31.8779 (11)C5—C61.384 (2)
O1—N21.3817 (15)C5—H50.9300
O1—H1O0.858 (9)C6—C71.504 (2)
O2—N31.3181 (14)C7—H7A0.9600
N1—C91.3575 (18)C7—H7B0.9600
N1—C11.4389 (17)C7—H7C0.9600
N1—H1N0.824 (14)C8—H8A0.9600
N2—C91.3028 (19)C8—H8B0.9600
N3—C101.3111 (17)C8—H8C0.9600
C1—C21.387 (2)C9—C101.470 (2)
C1—C61.3979 (19)C10—C111.486 (2)
C2—C31.392 (2)C11—H11A0.9600
C2—C81.513 (2)C11—H11B0.9600
C3—C41.374 (2)C11—H11C0.9600
N2i—Ni1—N2180.0C4—C5—H5119.2
N2i—Ni1—N3i82.38 (5)C6—C5—H5119.2
N2—Ni1—N3i97.62 (5)C5—C6—C1117.53 (14)
N2i—Ni1—N397.62 (5)C5—C6—C7121.19 (14)
N2—Ni1—N382.38 (5)C1—C6—C7121.26 (13)
N3i—Ni1—N3180.0C6—C7—H7A109.5
N2—O1—H1O99.1 (15)C6—C7—H7B109.5
C9—N1—C1124.51 (13)H7A—C7—H7B109.5
C9—N1—H1N109.3 (12)C6—C7—H7C109.5
C1—N1—H1N121.9 (12)H7A—C7—H7C109.5
C9—N2—O1116.31 (12)H7B—C7—H7C109.5
C9—N2—Ni1116.99 (11)C2—C8—H8A109.5
O1—N2—Ni1126.55 (9)C2—C8—H8B109.5
C10—N3—O2120.48 (11)H8A—C8—H8B109.5
C10—N3—Ni1116.60 (9)C2—C8—H8C109.5
O2—N3—Ni1122.85 (8)H8A—C8—H8C109.5
C2—C1—C6122.03 (13)H8B—C8—H8C109.5
C2—C1—N1120.00 (13)N2—C9—N1121.96 (14)
C6—C1—N1117.88 (13)N2—C9—C10113.00 (12)
C1—C2—C3118.10 (14)N1—C9—C10124.96 (13)
C1—C2—C8122.03 (14)N3—C10—C9110.90 (12)
C3—C2—C8119.87 (15)N3—C10—C11122.18 (13)
C4—C3—C2120.84 (16)C9—C10—C11126.81 (12)
C4—C3—H3119.6C10—C11—H11A109.5
C2—C3—H3119.6C10—C11—H11B109.5
C3—C4—C5119.93 (14)H11A—C11—H11B109.5
C3—C4—H4120.0C10—C11—H11C109.5
C5—C4—H4120.0H11A—C11—H11C109.5
C4—C5—C6121.55 (15)H11B—C11—H11C109.5
N3i—Ni1—N2—C9−177.23 (10)C4—C5—C6—C7177.73 (16)
N3—Ni1—N2—C92.77 (10)C2—C1—C6—C50.3 (2)
N3i—Ni1—N2—O1−1.92 (12)N1—C1—C6—C5−176.24 (14)
N3—Ni1—N2—O1178.08 (12)C2—C1—C6—C7−178.00 (15)
N2i—Ni1—N3—C10179.36 (10)N1—C1—C6—C75.4 (2)
N2—Ni1—N3—C10−0.64 (10)O1—N2—C9—N13.3 (2)
N2i—Ni1—N3—O2−3.65 (12)Ni1—N2—C9—N1179.15 (10)
N2—Ni1—N3—O2176.35 (12)O1—N2—C9—C10−179.93 (11)
C9—N1—C1—C257.9 (2)Ni1—N2—C9—C10−4.13 (15)
C9—N1—C1—C6−125.45 (16)C1—N1—C9—N2−150.05 (14)
C6—C1—C2—C30.6 (2)C1—N1—C9—C1033.6 (2)
N1—C1—C2—C3177.13 (14)O2—N3—C10—C9−178.35 (11)
C6—C1—C2—C8−178.83 (15)Ni1—N3—C10—C9−1.29 (15)
N1—C1—C2—C8−2.3 (2)O2—N3—C10—C11−1.9 (2)
C1—C2—C3—C4−1.4 (2)Ni1—N3—C10—C11175.16 (12)
C8—C2—C3—C4178.11 (16)N2—C9—C10—N33.42 (17)
C2—C3—C4—C51.1 (3)N1—C9—C10—N3−179.97 (13)
C3—C4—C5—C6−0.1 (3)N2—C9—C10—C11−172.82 (14)
C4—C5—C6—C1−0.6 (2)N1—C9—C10—C113.8 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.86 (1)1.65 (1)2.4972 (14)171 (2)
N1—H1N···O10.82 (1)2.20 (2)2.6361 (16)113 (1)
Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Ni(C11H14N3O2)2]
Mr499.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.1081 (4), 16.0311 (8), 8.9223 (4)
β (°) 94.202 (1)
V (Å3)1156.62 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.88
Crystal size (mm)0.49 × 0.30 × 0.24
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.736, 0.810
No. of measured, independent and
observed [I > 2σ(I)] reflections		11778, 4184, 2988
Rint0.021
(sin θ/λ)max (Å−1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.093, 0.98
No. of reflections4184
No. of parameters159
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.16

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
Ni1—N21.8397 (11)Ni1—N31.8779 (11)
N2—Ni1—N3i97.62 (5)N2—Ni1—N382.38 (5)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.858 (9)1.647 (10)2.4972 (14)171 (2)
N1—H1N···O10.824 (14)2.200 (17)2.6361 (16)113.2 (14)
Symmetry code: (i) −x+1, −y+1, −z+1.
 

Acknowledgements

The authors thank Ondokuz Mayıs University for financial support.

References

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ISSN: 2056-9890
Volume 61| Part 10| October 2005| Pages m2033-m2035
doi:10.1107/S1600536805028965
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