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

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ISSN: 2056-9890

trans-Di­methano­lbis(1,1,1-tri­fluoro-5,5-di­methyl­hexane-2,4-dionato)zinc(II)

aYoungstown State University, Department of Chemistry, 1 University Plaza, Youngstown, OH 44555, USA
*Correspondence e-mail: bdleskiw@ysu.edu

(Received 13 November 2008; accepted 14 November 2008; online 10 December 2008)

The title compound, [Zn(C8H10F3O2)2(CH4O)2], is a dimethanol coordinated zinc complex with the acetyl acetonate derivative 1,1,1-trifluoro-5,5-dimethyl­hexane-2,4-dionate. The bis­-β-diketonate complex, which is isostructural with its Co analogue, is located on a crystallographic inversion center. The complex is octa­hedral with basically no distortion, and the methanol mol­ecules are in trans positions with respect to one another. The planes of the β-diketonate and the ZnO4 unit are tilted by 18.64 (10)° against each other. O—H⋯O hydrogen bonds between the methanol hydroxyl groups and neighboring diketonate O atoms create chains running along [100].

Related literature

For information regarding the synthesis of various metal β-diketonates refer to Watson & Lin (1966[Watson, W. H. & Lin, C. (1966). Inorg. Chem. 5, 1074-1077.]). For mass spectrometry related articles see Lerach & Leskiw (2008[Lerach, O. J. & Leskiw, B. D. (2008). Rapid Commun. Mass Spectrom. 4139-4146.]) and Schildcrout (1976[Schildcrout, S. M. (1976). J. Phys. Chem. 80, 2834-2838.]). For a variety of applications and properties of metal β-diketonate complexes refer to Burtoloso (2005[Burtoloso, A. (2005). Synlett, 18, 2859.]), Katok et al. (2006[Katok, K. V., Tertykh, V. A., Brichka, S. Y. & Prikhod, G. P. (2006). J. Therm. Anal. Calorim. 86, 109-114.]) and Condorelli et al. (2007[Condorelli, G. G., Motta, A., Bedoya, C., Di Mauro, G. P. & Smecca, E. (2007). Inorg. Chim. Acta, 360, 170-178.]). Lerach et al. (2007[Lerach, J. O., Zeller, M. & Leskiw, B. D. (2007). Acta Cryst. E63, m2639.]) report the structure of the Co analogue of the title compound.

[Scheme 1]

Experimental

Crystal data
  • [Zn(C8H10F3O2)2(CH4O)2]

  • Mr = 519.79

  • Triclinic, [P \overline 1]

  • a = 5.470 (2) Å

  • b = 8.755 (3) Å

  • c = 12.031 (4) Å

  • α = 78.785 (5)°

  • β = 80.542 (5)°

  • γ = 88.083 (5)°

  • V = 557.5 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.18 mm−1

  • T = 100 (2) K

  • 0.55 × 0.26 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (APEX2; Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.603, Tmax = 0.943

  • 5584 measured reflections

  • 2736 independent reflections

  • 2103 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.114

  • S = 1.04

  • 2736 reflections

  • 149 parameters

  • 1 restraint

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

  • Δρmax = 0.85 e Å−3

  • Δρmin = −0.97 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3A⋯O1i 0.82 (2) 2.06 (2) 2.869 (3) 168 (4)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; 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.

Supporting information


Comment top

β-Diketonates and especially metal β-diketonate complexes have been widely studied for both their instrinsic properties as well as a variety of scientific and technolgical applications. Especially interesting applications include, but are not limited to, catalysis (Burtoloso, 2005), carbon-nanotube structures (Katok et al., 2006), or the deposition of metallic or ceramic thin films (Condorelli et al., 2007). In our own laboratory we are investigating gas phase reactions of a series of metal acetylacetonate (acac) complexes. Through mass spectrometric analysis, several acetylacetonate and substituted acetyl acetonate species were observed to undergo various reactions including ligand exchange and association (Schildcrout, 1976; Lerach & Leskiw, 2008). In this context fluorinated metal-β-diketonates are especially interesting because of their increased volality, thermal stability, and also their ease of preparation.

The title compound, [Zn(C8H10F3O2)2(CH3OH)2], which is isostructural with its Co analogue (Lerach et al., 2007) is a dimethanol coordinate of a zinc complex with the ligand 1,1,1-trifluoro-5,5-dimethylhexane-2,4-dionate, an acetyl acetonate derivative with each a tert-butyl and a trifluoromethyl substituent. A thermal ellipsoid plot of the molecule is shown in Fig. 1. The bis-β-diketonate complex is located on a crystallographic inversion center with the two methanol molecules in trans position to each other. The coordination environment of the central zinc cation is octahedral with only a very slight distortion: angles around the Zn atom deviate from 90° by 0.36 (8)° or less, and Zn—O distances are 2.054 (2) and 2.040 (2) Å for the zinc β-diketonate bonds and 2.161 (2) Å towards the methanol molecules. The mean planes of the diketonate ligands, defined by the atoms O1, O2 and C1 to C5, and that of the ZnO4 unit are tilted against each other by an angle of 18.64 (10)°, which is virtually identical to the vaule of 17.41 (7)° observed in the structure of the Co analogue of the title compound.

Packing of the molecules within the structure is assisted by hydrogen bonds between the methanol hydroxyl groups and diketonate oxygen atoms of neighboring molecules (Table 1). The O—H···O interactions create hydrogen bonded chains that stretch along the a-axis of the structure.

Related literature top

For information regarding the synthesis of various metal β-diketonates refer to Watson & Lin (1966). For mass spectrometry related articles see Lerach & Leskiw (2008) and Schildcrout (1976). For a variety of applications and properties of metal β-diketonate complexes refer to Burtoloso (2005), Katok et al. (2006) and Condorelli et al. (2007). Lerach et al. (2007) report the structure of the Co analogue of the title compound.

Experimental top

The synthesis of the title compound was adapted from Watson & Lin (1966). 0.80 ml (5.0 mmol) of the ligand were added to a stirring solution of 0.22 g of ZnCl2 (1.6 m mol) and 50 ml of de-inoized water. Diluted 1:1 (v/v) NH4OH was added dropwise to the mixture until no more visible precipitate formed. The solution was stirred for another hour at room temperature, and the precipitate was isolated by vacuum filtration. The desired product was re-crystallized by overnight evaporation of a concentrated methanolic solution.

Refinement top

The hydroxyl H atom was located in a difference density Fourier map and the O—H distance was restrained to 0.84 (2) Å. All other H atoms were placed in calculated positions with C—H distances of 0.98 (methyl) and 0.95 Å (CH). The methyl and hydroxyl H's were refined with an isotropic displacement parameter Uiso of 1.5 times Ueq of the adjacent carbon or oxygen atom, and the C—H hydrogen atom with Uiso = 1.2 Ueq(C). Methyl hydrogen atoms were allowed to rotate to best fit the experimental electron density.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: APEX2 (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP representation of the asymmetric unit of the title compound (50% probability displacement ellipsoids). H atoms are shown as circles of arbitrary radii.
trans-Dimethanolbis(1,1,1-trifluoro-5,5-dimethylhexane- 2,4-dionato)zinc(II) top
Crystal data top
[Zn(C8H10F3O2)2(CH4O)2]Z = 1
Mr = 519.79F(000) = 268
Triclinic, P1Dx = 1.548 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.470 (2) ÅCell parameters from 1117 reflections
b = 8.755 (3) Åθ = 2.4–29.6°
c = 12.031 (4) ŵ = 1.18 mm1
α = 78.785 (5)°T = 100 K
β = 80.542 (5)°Plate, colourless
γ = 88.083 (5)°0.55 × 0.26 × 0.05 mm
V = 557.5 (3) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
2736 independent reflections
Radiation source: fine-focus sealed tube2103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.8°
ω scansh = 77
Absorption correction: multi-scan
(APEX2; Bruker, 2008)
k = 1111
Tmin = 0.603, Tmax = 0.943l = 1516
5584 measured reflections
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)] = 0.052Hydrogen site location: difference Fourier map
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1141P]
where P = (Fo2 + 2Fc2)/3
2736 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.85 e Å3
1 restraintΔρmin = 0.97 e Å3
Crystal data top
[Zn(C8H10F3O2)2(CH4O)2]γ = 88.083 (5)°
Mr = 519.79V = 557.5 (3) Å3
Triclinic, P1Z = 1
a = 5.470 (2) ÅMo Kα radiation
b = 8.755 (3) ŵ = 1.18 mm1
c = 12.031 (4) ÅT = 100 K
α = 78.785 (5)°0.55 × 0.26 × 0.05 mm
β = 80.542 (5)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2736 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2008)
2103 reflections with I > 2σ(I)
Tmin = 0.603, Tmax = 0.943Rint = 0.044
5584 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.85 e Å3
2736 reflectionsΔρmin = 0.97 e Å3
149 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
C11.1698 (6)1.2211 (4)0.7642 (3)0.0245 (7)
C21.0749 (5)1.0950 (3)0.7105 (3)0.0196 (6)
C30.9063 (5)0.9904 (3)0.7791 (3)0.0211 (6)
H30.85531.00230.85630.025*
C40.8021 (5)0.8648 (3)0.7425 (3)0.0199 (6)
C50.6476 (5)0.7405 (3)0.8316 (3)0.0200 (6)
C60.4765 (6)0.8131 (4)0.9221 (3)0.0266 (7)
H6A0.36700.88950.88400.040*
H6B0.57680.86470.96430.040*
H6C0.37640.73120.97580.040*
C70.8326 (6)0.6306 (4)0.8926 (3)0.0265 (7)
H7A0.74100.55120.95210.040*
H7B0.93540.69100.92780.040*
H7C0.93890.58010.83640.040*
C80.4976 (6)0.6471 (4)0.7721 (3)0.0298 (8)
H8A0.39990.56810.82970.045*
H8B0.61030.59610.71840.045*
H8C0.38610.71710.73000.045*
C90.7190 (6)1.3221 (4)0.5071 (3)0.0290 (7)
H9A0.71251.34800.58320.044*
H9B0.58541.37680.47020.044*
H9C0.87931.35420.45990.044*
F11.4150 (3)1.2087 (2)0.76434 (17)0.0350 (5)
F21.0662 (4)1.2202 (2)0.87310 (16)0.0385 (5)
F31.1312 (4)1.3633 (2)0.70461 (18)0.0384 (5)
O11.1718 (4)1.1047 (2)0.60505 (17)0.0214 (5)
O20.8347 (4)0.8468 (2)0.64018 (18)0.0223 (5)
O30.6892 (4)1.1570 (2)0.51870 (19)0.0252 (5)
H3A0.547 (4)1.129 (4)0.548 (3)0.038*
Zn11.00001.00000.50000.01973 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0202 (15)0.0285 (17)0.0260 (17)0.0026 (13)0.0032 (13)0.0083 (13)
C20.0129 (13)0.0233 (15)0.0249 (16)0.0025 (11)0.0068 (11)0.0075 (12)
C30.0172 (14)0.0256 (16)0.0212 (15)0.0002 (12)0.0031 (12)0.0067 (12)
C40.0109 (13)0.0223 (15)0.0257 (16)0.0043 (11)0.0019 (11)0.0040 (12)
C50.0163 (14)0.0205 (15)0.0227 (16)0.0004 (11)0.0018 (12)0.0039 (12)
C60.0196 (15)0.0272 (16)0.0301 (17)0.0004 (13)0.0005 (13)0.0024 (14)
C70.0196 (15)0.0253 (16)0.0323 (18)0.0009 (12)0.0015 (13)0.0020 (14)
C80.0251 (16)0.0338 (18)0.0301 (18)0.0146 (14)0.0014 (14)0.0048 (14)
C90.0271 (17)0.0235 (16)0.0370 (19)0.0037 (13)0.0037 (14)0.0088 (14)
F10.0192 (9)0.0440 (12)0.0478 (13)0.0032 (8)0.0100 (9)0.0191 (10)
F20.0398 (12)0.0472 (13)0.0315 (11)0.0171 (10)0.0070 (9)0.0227 (10)
F30.0513 (13)0.0216 (10)0.0473 (13)0.0004 (9)0.0196 (10)0.0093 (9)
O10.0172 (10)0.0255 (11)0.0222 (11)0.0015 (8)0.0026 (8)0.0067 (9)
O20.0211 (10)0.0221 (11)0.0241 (11)0.0026 (8)0.0028 (9)0.0059 (9)
O30.0148 (10)0.0226 (11)0.0374 (13)0.0007 (9)0.0000 (9)0.0076 (10)
Zn10.0150 (3)0.0215 (3)0.0228 (3)0.00167 (19)0.00203 (19)0.0050 (2)
Geometric parameters (Å, º) top
C1—F21.338 (4)C7—H7B0.9800
C1—F31.339 (4)C7—H7C0.9800
C1—F11.342 (3)C8—H8A0.9800
C1—C21.526 (4)C8—H8B0.9800
C2—O11.280 (3)C8—H8C0.9800
C2—C31.372 (4)C9—O31.438 (4)
C3—C41.428 (4)C9—H9A0.9800
C3—H30.9500C9—H9B0.9800
C4—O21.254 (4)C9—H9C0.9800
C4—C51.536 (4)O1—Zn12.054 (2)
C5—C81.523 (4)O2—Zn12.040 (2)
C5—C61.536 (4)O3—Zn12.161 (2)
C5—C71.547 (4)O3—H3A0.824 (18)
C6—H6A0.9800Zn1—O2i2.040 (2)
C6—H6B0.9800Zn1—O1i2.054 (2)
C6—H6C0.9800Zn1—O3i2.161 (2)
C7—H7A0.9800
F2—C1—F3106.6 (3)C5—C8—H8A109.5
F2—C1—F1106.0 (3)C5—C8—H8B109.5
F3—C1—F1106.3 (2)H8A—C8—H8B109.5
F2—C1—C2114.7 (2)C5—C8—H8C109.5
F3—C1—C2111.1 (3)H8A—C8—H8C109.5
F1—C1—C2111.6 (2)H8B—C8—H8C109.5
O1—C2—C3130.0 (3)O3—C9—H9A109.5
O1—C2—C1112.4 (2)O3—C9—H9B109.5
C3—C2—C1117.7 (3)H9A—C9—H9B109.5
C2—C3—C4124.6 (3)O3—C9—H9C109.5
C2—C3—H3117.7H9A—C9—H9C109.5
C4—C3—H3117.7H9B—C9—H9C109.5
O2—C4—C3123.5 (3)C2—O1—Zn1119.7 (2)
O2—C4—C5116.9 (3)C4—O2—Zn1126.7 (2)
C3—C4—C5119.6 (3)C9—O3—Zn1122.6 (2)
C8—C5—C4110.1 (2)C9—O3—H3A112 (3)
C8—C5—C6110.5 (2)Zn1—O3—H3A124 (3)
C4—C5—C6111.6 (2)O2i—Zn1—O2180.0
C8—C5—C7109.1 (3)O2i—Zn1—O1i89.64 (8)
C4—C5—C7106.9 (2)O2—Zn1—O1i90.36 (8)
C6—C5—C7108.5 (3)O2i—Zn1—O190.36 (8)
C5—C6—H6A109.5O2—Zn1—O189.64 (8)
C5—C6—H6B109.5O1i—Zn1—O1180.00 (11)
H6A—C6—H6B109.5O2i—Zn1—O389.95 (8)
C5—C6—H6C109.5O2—Zn1—O390.05 (8)
H6A—C6—H6C109.5O1i—Zn1—O389.97 (8)
H6B—C6—H6C109.5O1—Zn1—O390.03 (8)
C5—C7—H7A109.5O2i—Zn1—O3i90.05 (8)
C5—C7—H7B109.5O2—Zn1—O3i89.95 (8)
H7A—C7—H7B109.5O1i—Zn1—O3i90.03 (8)
C5—C7—H7C109.5O1—Zn1—O3i89.97 (9)
H7A—C7—H7C109.5O3—Zn1—O3i179.999 (1)
H7B—C7—H7C109.5
F2—C1—C2—O1177.3 (2)C3—C2—O1—Zn120.4 (4)
F3—C1—C2—O156.2 (3)C1—C2—O1—Zn1160.1 (2)
F1—C1—C2—O162.2 (3)C3—C4—O2—Zn18.4 (4)
F2—C1—C2—C33.2 (4)C5—C4—O2—Zn1173.6 (2)
F3—C1—C2—C3124.2 (3)C4—O2—Zn1—O1i159.3 (2)
F1—C1—C2—C3117.3 (3)C4—O2—Zn1—O120.7 (2)
O1—C2—C3—C40.2 (5)C4—O2—Zn1—O369.4 (2)
C1—C2—C3—C4179.2 (3)C4—O2—Zn1—O3i110.6 (2)
C2—C3—C4—O27.7 (5)C2—O1—Zn1—O2i155.1 (2)
C2—C3—C4—C5170.3 (3)C2—O1—Zn1—O224.9 (2)
O2—C4—C5—C817.8 (4)C2—O1—Zn1—O365.1 (2)
C3—C4—C5—C8164.0 (3)C2—O1—Zn1—O3i114.9 (2)
O2—C4—C5—C6141.0 (3)C9—O3—Zn1—O2i43.4 (2)
C3—C4—C5—C640.8 (4)C9—O3—Zn1—O2136.6 (2)
O2—C4—C5—C7100.5 (3)C9—O3—Zn1—O1i133.0 (2)
C3—C4—C5—C777.6 (3)C9—O3—Zn1—O147.0 (2)
Symmetry code: (i) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1ii0.82 (2)2.06 (2)2.869 (3)168 (4)
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formula[Zn(C8H10F3O2)2(CH4O)2]
Mr519.79
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.470 (2), 8.755 (3), 12.031 (4)
α, β, γ (°)78.785 (5), 80.542 (5), 88.083 (5)
V3)557.5 (3)
Z1
Radiation typeMo Kα
µ (mm1)1.18
Crystal size (mm)0.55 × 0.26 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(APEX2; Bruker, 2008)
Tmin, Tmax0.603, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
5584, 2736, 2103
Rint0.044
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.114, 1.04
No. of reflections2736
No. of parameters149
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.85, 0.97

Computer programs: APEX2 (Bruker, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.82 (2)2.06 (2)2.869 (3)168 (4)
Symmetry code: (i) x1, y, z.
 

Acknowledgements

GOH would like to thank Mr Jordan Lerach for his fundamental contributions in the initial stages of this new research project and his continued help and assistance. The diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU.

References

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