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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 66| Part 8| August 2010| Page m949
https://doi.org/10.1107/S160053681002756X

Bis(acetyl­acetonato-κ2O,O′)[copper(II)nickel(II)(0.31/0.69)]: a mixed-metal complex

Muhammad Shahid,a* Mazhar Hamid,a Muhammad Mazhar,b Mohammad Azad Malikc and James Rafteryc

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cThe School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, England
*Correspondence e-mail: shahid_chme@yahoo.com

(Received 26 June 2010; accepted 12 July 2010; online 17 July 2010)

The title complex, [Cu0.31Ni0.69(C5H7O2)2], was isolated from the reaction of bis­(N,N-dimethyamino­ethanol)copper(II) with bis­(acetyl­acetonato)nickel(II), which yielded crystals with mixed sites at the central metal position; the refined copper–nickel occupancy ratio is 0.31 (4):0.69 (4). Two acetyl­acetonate ligands, related by a centre of symmetry, are coordinated to the central metal atom in a square-planar configuration while the methyne C atoms of the acetyl­acetonate ligands, ca 3.02 Å away, are orthogonal to this plane at the metal site.

Related literature

For heterobimetallic complexes of copper and nickel, see: Hamid et al. (2006[Hamid, M., Tahir, A. A., Mazhar, M., Zeller, M., Molloy, K. C. & Hunter, A. D. (2006). Inorg. Chem. 45, 10457-10466.]). For disorder in metal sites, see: Werndrup & Kessler (2001[Werndrup, P. & Kessler, V. G. (2001). J. Chem. Soc. Dalton Trans. pp. 574-579.]). For applications of mixed-metal ceramic oxides, see: Auciello & Ramesh(1996[Auciello, O. & Ramesh, R. (1996). Editors. Special Issue on Electroceramic Thin Films, Parts I and II. MRS Bull. 21 (6,7).]) and references therein. For mixed copper/nickel oxide catalysts, see: Kessler et al. (2001[Kessler, G. V., Gohil, S., Kritikos, M., Korsak, N. O., Knyazeva, E. E., Moskovskaya, F. I. & Romanovsky, V. B. (2001). Polyhedron, 20, 915-922.]). For the synthesis of Cu(dmae)2 (dmae = N,N-dimethyl­aminoethanolato), see: Johnson et al. (2001[Johnson, B. F. G., Klunduk, M. C., O'Connell, T. J. O., McIntosh, C. & Ridland, J. (2001). J. Chem. Soc. Dalton Trans. pp. 1553-1555.]). For the crystal structure of Cu(acac)2 (acac = acetyl­acetonato), see: LeBrun et al. (1986[LeBrun, P. C., Lyon, W. D. & Kuska, H. A. (1986). J. Crystallogr. Spectrosc. Res. 6, 889-893.]). For the crystal structure of Ni(acac)2·2H2O, see: Zhou et al. (2001[Zhou, X.-F., Han, A.-J., Chu, D.-B. & Huang, Z.-X. (2001). Acta Cryst. E57, m506-m508.]). For the O—Cu/Ni—O chelate bite angle in related complexes, see: Aruffo et al. (1983[Aruffo, A. A., Anderson, L. D., Lingafelter, E. C. & Schomaker, V. (1983). Acta Crtyst. C39, 201-203.]).

[Scheme 1]

Experimental

Crystal data

  • [Cu0.31Ni0.69(C5H7O2)2]

  • Mr = 258.40

  • Monoclinic, P 21 /n

  • a = 10.265 (1) Å

  • b = 4.6300 (5) Å

  • c = 11.2830 (11) Å

  • β = 92.431 (2)°

  • V = 535.76 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.87 mm−1

  • T = 100 K

  • 0.45 × 0.45 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.487, Tmax = 0.706

  • 3086 measured reflections

  • 1242 independent reflections

  • 1159 reflections with I > 2σ(I)

  • Rint = 0.013
Refinement

  • R[F2 > 2σ(F2)] = 0.022

  • wR(F2) = 0.059

  • S = 1.07

  • 1242 reflections

  • 73 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681002756X/su2192sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002756X/su2192Isup2.hkl

checkCIF report


Comment top

Heterobimetallic complexes of copper and nickel have already been reported as precursors for chemical vapor deposition of ceramic material thin films (Hamid et al., 2006). Mixed metal ceramic oxides have multiple compositions and crystal structures, which results in a diversity of properties leading to a vast variety of potential applications (Auciello et al., 1996, and references therein). For example, a mixed copper/nickel oxide catalyst was deposited on a zeolite support and was shown to have extremely high activity towards methanol oxidation (Kessler et al., 2001).

The title complex was synthesized by the reaction of Cu (dmae)2 (dmae = N,N-dimethylaminoethanolato) (Johnson et al., 2001) with Ni(acac)2.2H2O (acac = acetylacetonato) in toluene. In contrast to the formation of the oligomeric bimetallic complex (Hamid et al., 2006), the title compound crystallized out with the central position partially occupied by Cu and partially by Ni, with a refined Cu:Ni occupancy ratio of 0.31 (4):0.69 (4). A similar type of disorder in the metal site was observed previously in Ni(Ni0.25Cu0.75)2(µ3-OH)(µ-OAc)2(η1-OAc)2(µ,η2–ORN)2 (η2-RNOH)][RN–OH=(CH3)2N(CH2)(CHOH)CH3)] (Werndrup et al., 2001), where the two metal sites were occupied by 75% Cu and 25% Ni. The distribution of two metals at the central position in the title complex is random which means some of the molecules would have each of the two Cu and Ni atoms, or in other words if we consider it to be systematic, in every molecule the position will be occupied by exactly 0.31 Cu and 0.69 Ni atoms.

The molecular structure of the title complex is shown in Figure 1. The geometry of the title complex is square planer, similar to that of Cu(acac)2 (LeBrun et al., 1986) where two ligands coordinate to the metal atom in the same plane, while in the nickel(II) complex, Ni(acac)2 (Zhou et al., 2001), which crystallized with two coordinated water molecules, the metal has an octahedral coordination sphere. The metal to oxygen (O1, O2) bond distances [1.9196 (10) and 1.9225 (10) Å] are slightly longer than those in Cu(acac)2 [1.914 (4), 1.914 (4)Å] but shorter than the average value found in Ni(acac)2 [2.0147Å]. The O—Cu/Ni—O chelate bite angle is 93.72 (4)° which is comparable to that found in Cu(acac)2 [93.2 (2)°] and other complexes of this type (Aruffo et al., 1983). The chelate bite angles are of course larger than those in the octahedral nickel(II) complex mentioned above [91.65 (8)°, 89.99 (8)°].

Related literature top

For heterobimetallic complexes of copper and nickel, see: Hamid et al. (2006). For disorder in metal sites, see: Werndrup et al. (2001). For applications of mixed-metal ceramic oxides, see: Auciello et al. (1996) and references therein. For mixed copper/nickel oxide catalysts, see: Kessler et al. (2001). For the synthesis of Cu(dmae)2, see: Johnson et al. (2001). For the crystal structure of Cu(acac)2 (acac = acetylacetonato), see: LeBrun et al. (1986). For the crystal structure of Ni(acac)2.2H2O, see: Zhou et al. (2001). For the O—Cu/Ni—O chelate bite angle in related complexes, see: Aruffo et al. (1983).

Experimental top

Bis(N,N-dimethylaminoethanolatoκ2 O, N) copper(II) (0.5 g, 2.1 mmol) and bis(acetylacetonato κ2 O, O') nickel(II) (0.54 g, 2.1 mmol) were reacted in 20 ml toluene as a solvent. After stirring for two hours, the solution was cannula filtered to remove unreacted reagents. Slow evaporation of the filtrate gave block-like blue crystals, suitable for single-crystal X-ray analysis, after two weeks.

Refinement top

The H-atoms were included in calculated positions, with C—H = 0.95(CH), 0.99(CH2) & 0.98(CH3) Å, with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H-atoms and 1.2 for all other H-atoms.

The occupancy of the metal site was examined under three assumptions: All Ni gave R1(>4sig)= 0.0227, R1(all)= 0.0243; All Cu gave R1(>4sig)= 0.0236, R1(all)= 0.0252. Variable Ni:Cu ratio [which converged to 69 (4):31 (4)] gave R1(>4sig)= 0.0221, R1(all)= 0.0238. Elemental analysis of the Cu/Ni with a ICP-OES Fisons Horizon Spectrometer has: ratio Cu:Ni (31:69); Cu calulated 7.62%: found 7.86%; Ni calculated 15.68%: found 15.23%. The agreement is surprisingly good considering that Cu and Ni differ by only one electron.

Structure description top

Heterobimetallic complexes of copper and nickel have already been reported as precursors for chemical vapor deposition of ceramic material thin films (Hamid et al., 2006). Mixed metal ceramic oxides have multiple compositions and crystal structures, which results in a diversity of properties leading to a vast variety of potential applications (Auciello et al., 1996, and references therein). For example, a mixed copper/nickel oxide catalyst was deposited on a zeolite support and was shown to have extremely high activity towards methanol oxidation (Kessler et al., 2001).

The title complex was synthesized by the reaction of Cu (dmae)2 (dmae = N,N-dimethylaminoethanolato) (Johnson et al., 2001) with Ni(acac)2.2H2O (acac = acetylacetonato) in toluene. In contrast to the formation of the oligomeric bimetallic complex (Hamid et al., 2006), the title compound crystallized out with the central position partially occupied by Cu and partially by Ni, with a refined Cu:Ni occupancy ratio of 0.31 (4):0.69 (4). A similar type of disorder in the metal site was observed previously in Ni(Ni0.25Cu0.75)2(µ3-OH)(µ-OAc)2(η1-OAc)2(µ,η2–ORN)2 (η2-RNOH)][RN–OH=(CH3)2N(CH2)(CHOH)CH3)] (Werndrup et al., 2001), where the two metal sites were occupied by 75% Cu and 25% Ni. The distribution of two metals at the central position in the title complex is random which means some of the molecules would have each of the two Cu and Ni atoms, or in other words if we consider it to be systematic, in every molecule the position will be occupied by exactly 0.31 Cu and 0.69 Ni atoms.

The molecular structure of the title complex is shown in Figure 1. The geometry of the title complex is square planer, similar to that of Cu(acac)2 (LeBrun et al., 1986) where two ligands coordinate to the metal atom in the same plane, while in the nickel(II) complex, Ni(acac)2 (Zhou et al., 2001), which crystallized with two coordinated water molecules, the metal has an octahedral coordination sphere. The metal to oxygen (O1, O2) bond distances [1.9196 (10) and 1.9225 (10) Å] are slightly longer than those in Cu(acac)2 [1.914 (4), 1.914 (4)Å] but shorter than the average value found in Ni(acac)2 [2.0147Å]. The O—Cu/Ni—O chelate bite angle is 93.72 (4)° which is comparable to that found in Cu(acac)2 [93.2 (2)°] and other complexes of this type (Aruffo et al., 1983). The chelate bite angles are of course larger than those in the octahedral nickel(II) complex mentioned above [91.65 (8)°, 89.99 (8)°].

For heterobimetallic complexes of copper and nickel, see: Hamid et al. (2006). For disorder in metal sites, see: Werndrup et al. (2001). For applications of mixed-metal ceramic oxides, see: Auciello et al. (1996) and references therein. For mixed copper/nickel oxide catalysts, see: Kessler et al. (2001). For the synthesis of Cu(dmae)2, see: Johnson et al. (2001). For the crystal structure of Cu(acac)2 (acac = acetylacetonato), see: LeBrun et al. (1986). For the crystal structure of Ni(acac)2.2H2O, see: Zhou et al. (2001). For the O—Cu/Ni—O chelate bite angle in related complexes, see: Aruffo et al. (1983).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title molecule with displacement ellipsoids drawn at the 50% probability level.
Bis(acetylacetonato-κ2O,O')[copper(II)nickel(II)(0.31/0.69)] top
Crystal data top
[Cu0.31Ni0.69(C5H7O2)2]F(000) = 269
Mr = 258.40Dx = 1.602 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2222 reflections
a = 10.265 (1) Åθ = 2.6–28.2°
b = 4.6300 (5) ŵ = 1.87 mm−1
c = 11.2830 (11) ÅT = 100 K
β = 92.431 (2)°Block, blue
V = 535.76 (9) Å30.45 × 0.45 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		1242 independent reflections
Radiation source: fine-focus sealed tube1159 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
phi and ω scansθmax = 28.2°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)		h = −9→13
Tmin = 0.487, Tmax = 0.706k = −6→5
3086 measured reflectionsl = −13→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0305P)2 + 0.3448P]
where P = (Fo2 + 2Fc2)/3
1242 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Cu0.31Ni0.69(C5H7O2)2]V = 535.76 (9) Å3
Mr = 258.40Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.265 (1) ŵ = 1.87 mm−1
b = 4.6300 (5) ÅT = 100 K
c = 11.2830 (11) Å0.45 × 0.45 × 0.20 mm
β = 92.431 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1242 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)		1159 reflections with I > 2σ(I)
Tmin = 0.487, Tmax = 0.706Rint = 0.013
3086 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.07Δρmax = 0.37 e Å−3
1242 reflectionsΔρmin = −0.35 e Å−3
73 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*/UeqOcc. (<1)
C10.81881 (15)0.5644 (4)0.55275 (14)0.0207 (3)
H1A0.87980.42280.52200.031*
H1B0.85470.64310.62790.031*
H1C0.80560.72130.49520.031*
C20.69044 (14)0.4199 (3)0.57303 (13)0.0167 (3)
C30.61101 (16)0.5306 (3)0.65990 (14)0.0184 (3)
H30.64160.69410.70370.022*
C40.48909 (14)0.4159 (3)0.68655 (13)0.0170 (3)
C50.41401 (16)0.5520 (4)0.78376 (14)0.0219 (3)
H5A0.36030.71000.75080.033*
H5B0.47510.62790.84520.033*
H5C0.35780.40650.81860.033*
Ni10.50000.00000.50000.01368 (10)0.69 (4)
Cu10.50000.00000.50000.01368 (10)0.31 (4)
O10.66241 (10)0.2061 (2)0.50564 (9)0.0185 (2)
O20.43456 (10)0.2013 (2)0.63411 (9)0.0182 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0171 (7)0.0222 (7)0.0229 (7)−0.0021 (6)0.0022 (6)−0.0017 (6)
C20.0168 (7)0.0163 (7)0.0170 (7)0.0004 (6)−0.0016 (5)0.0029 (5)
C30.0196 (7)0.0186 (7)0.0172 (7)−0.0019 (6)0.0008 (5)−0.0023 (5)
C40.0192 (7)0.0167 (7)0.0151 (7)0.0016 (6)0.0008 (5)0.0013 (5)
C50.0228 (8)0.0230 (8)0.0204 (7)−0.0013 (6)0.0058 (6)−0.0039 (6)
Ni10.01363 (14)0.01262 (15)0.01500 (15)−0.00132 (9)0.00309 (9)−0.00194 (9)
Cu10.01363 (14)0.01262 (15)0.01500 (15)−0.00132 (9)0.00309 (9)−0.00194 (9)
O10.0179 (5)0.0171 (5)0.0207 (5)−0.0008 (4)0.0029 (4)−0.0019 (4)
O20.0188 (5)0.0165 (5)0.0195 (5)−0.0015 (4)0.0037 (4)−0.0015 (4)
Geometric parameters (Å, º) top
C1—C21.504 (2)C4—C51.505 (2)
C1—H1A0.9800C5—H5A0.9800
C1—H1B0.9800C5—H5B0.9800
C1—H1C0.9800C5—H5C0.9800
C2—O11.2737 (18)Ni1—O1i1.9196 (10)
C2—C31.399 (2)Ni1—O11.9196 (10)
C3—C41.404 (2)Ni1—O2i1.9225 (10)
C3—H30.9500Ni1—O21.9226 (10)
C4—O21.2737 (18)
C2—C1—H1A109.5C4—C5—H5A109.5
C2—C1—H1B109.5C4—C5—H5B109.5
H1A—C1—H1B109.5H5A—C5—H5B109.5
C2—C1—H1C109.5C4—C5—H5C109.5
H1A—C1—H1C109.5H5A—C5—H5C109.5
H1B—C1—H1C109.5H5B—C5—H5C109.5
O1—C2—C3125.43 (14)O1i—Ni1—O1179.999 (1)
O1—C2—C1115.60 (13)O1i—Ni1—O2i93.72 (4)
C3—C2—C1118.95 (14)O1—Ni1—O2i86.28 (4)
C2—C3—C4124.25 (14)O1i—Ni1—O286.28 (4)
C2—C3—H3117.9O1—Ni1—O293.72 (4)
C4—C3—H3117.9O2i—Ni1—O2180.0
O2—C4—C3125.02 (14)C2—O1—Ni1125.45 (10)
O2—C4—C5115.87 (13)C4—O2—Ni1125.62 (9)
C3—C4—C5119.10 (14)
O1—C2—C3—C41.3 (3)O2i—Ni1—O1—C2172.90 (12)
C1—C2—C3—C4179.64 (14)O2—Ni1—O1—C2−7.10 (12)
C2—C3—C4—O2−1.3 (2)C3—C4—O2—Ni1−4.3 (2)
C2—C3—C4—C5178.91 (15)C5—C4—O2—Ni1175.47 (10)
C3—C2—O1—Ni14.2 (2)O1i—Ni1—O2—C4−172.85 (12)
C1—C2—O1—Ni1−174.11 (10)O1—Ni1—O2—C47.15 (12)
O1i—Ni1—O1—C2170 (6)O2i—Ni1—O2—C498 (29)
Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula[Cu0.31Ni0.69(C5H7O2)2]
Mr258.40
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)10.265 (1), 4.6300 (5), 11.2830 (11)
β (°) 92.431 (2)
V (Å3)535.76 (9)
Z2
Radiation typeMo Kα
µ (mm−1)1.87
Crystal size (mm)0.45 × 0.45 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.487, 0.706
No. of measured, independent and
observed [I > 2σ(I)] reflections		3086, 1242, 1159
Rint0.013
(sin θ/λ)max (Å−1)0.665
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.059, 1.07
No. of reflections1242
No. of parameters73
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.35

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We thank the Higher Education Commission of Pakistan for funding.

References

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page m949
https://doi.org/10.1107/S160053681002756X
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