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Acta Cryst. (2009). E65, m1681    [ doi:10.1107/S1600536809049812 ]

Tris(methyl 3-oxobutanoato-[kappa]2O,O')aluminium(III)

G. M. Neelgund, S. A. Shivashankar, T. Narasimhamurthy and S. W. Ng

Abstract top

In the title compound, [Al(C5H7O3)3], three acac-type ligands (methyl 3-oxobutanoate anions) chelate to the aluminium(III) cation in a slightly distorted AlO6 octahedral coordination geometry. Electron delocalization occurs within the chelating rings.

Related literature top

For the crystal structure of tris(acetylacetonato)aluminium, see: von Chrzanowski et al. (2007).

Experimental top

Aluminium isopropoxide (10 mmol, 2.04 g) was dissolved in toluene (25 ml) under a nitrogen atmosphere. Methyl acetoacetate (30 mmol, 3.2 ml) was added. The mixture turned yellow. The solution was stirred for 6 h. The solvent was removed by fractional distillation under vacuum to yield the product, which was purified by repeated recrystallization from cyclohexane.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The final difference Fourier map had a peak in the vicinity of the C13 and C14 atoms.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Al(C5H7O3)3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Tris(methyl 3-oxobutanoato-κ2O,O')aluminium(III) top
Crystal data top
[Al(C5H7O3)3]Z = 2
Mr = 372.30F(000) = 392
Triclinic, P1Dx = 1.350 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.476 (1) ÅCell parameters from 712 reflections
b = 9.986 (2) Åθ = 2.5–25.9°
c = 14.368 (2) ŵ = 0.15 mm−1
α = 90.478 (2)°T = 293 K
β = 92.229 (2)°Block, yellow
γ = 99.337 (2)°0.5 × 0.4 × 0.2 mm
V = 916.1 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer		3207 independent reflections
Radiation source: fine-focus sealed tube2304 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)		h = −7→7
Tmin = 0.927, Tmax = 0.970k = −11→11
8801 measured reflectionsl = −17→17
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0907P)2 + 1.477P]
where P = (Fo2 + 2Fc2)/3
3207 reflections(Δ/σ)max = 0.001
232 parametersΔρmax = 1.26 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
[Al(C5H7O3)3]γ = 99.337 (2)°
Mr = 372.30V = 916.1 (2) Å3
Triclinic, P1Z = 2
a = 6.476 (1) ÅMo Kα radiation
b = 9.986 (2) ŵ = 0.15 mm−1
c = 14.368 (2) ÅT = 293 K
α = 90.478 (2)°0.5 × 0.4 × 0.2 mm
β = 92.229 (2)°
Data collection top
Bruker SMART APEX
diffractometer		3207 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)		2304 reflections with I > 2σ(I)
Tmin = 0.927, Tmax = 0.970Rint = 0.041
8801 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.189Δρmax = 1.26 e Å−3
S = 1.02Δρmin = −0.28 e Å−3
3207 reflectionsAbsolute structure: ?
232 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Al10.61876 (18)0.34609 (11)0.25756 (8)0.0287 (3)
O10.8373 (4)0.4902 (2)0.29494 (17)0.0298 (6)
O21.0420 (4)0.6906 (3)0.2872 (2)0.0407 (7)
O30.4846 (4)0.4644 (3)0.18716 (19)0.0348 (7)
O40.7671 (4)0.2253 (2)0.32512 (17)0.0279 (6)
O50.8034 (4)0.0612 (3)0.42532 (19)0.0388 (7)
O60.4689 (4)0.3726 (2)0.36122 (18)0.0317 (6)
O70.7870 (4)0.3167 (3)0.15592 (17)0.0342 (7)
O80.9151 (5)0.1916 (3)0.0516 (2)0.0472 (8)
O90.4156 (4)0.1989 (3)0.21949 (19)0.0375 (7)
C11.1890 (6)0.6352 (5)0.3464 (3)0.0419 (10)
H1A1.31370.70110.35600.063*
H1B1.22350.55510.31760.063*
H1C1.12830.61250.40520.063*
C20.8676 (6)0.6084 (4)0.2614 (3)0.0302 (9)
C30.7318 (7)0.6615 (4)0.1987 (3)0.0364 (10)
H30.76740.75090.17990.044*
C40.5509 (6)0.5875 (4)0.1646 (3)0.0324 (9)
C50.4062 (7)0.6453 (4)0.0957 (3)0.0418 (11)
H5A0.26920.63770.12030.063*
H5B0.39780.59570.03780.063*
H5C0.46020.73910.08540.063*
C60.9613 (7)0.0242 (5)0.3656 (3)0.0423 (10)
H6A1.0342−0.04000.39680.063*
H6B1.05900.10390.35180.063*
H6C0.8953−0.01570.30880.063*
C70.7055 (6)0.1615 (4)0.3967 (3)0.0280 (8)
C90.4357 (6)0.2936 (4)0.4312 (3)0.0317 (9)
C80.5413 (6)0.1888 (4)0.4513 (3)0.0336 (9)
H80.50380.13450.50210.040*
C100.2692 (7)0.3274 (4)0.4948 (3)0.0433 (11)
H10A0.14540.33720.45830.065*
H10B0.32050.41090.52790.065*
H10C0.23640.25570.53850.065*
C111.0873 (7)0.2966 (5)0.0492 (3)0.0464 (11)
H11A1.19110.26950.01040.070*
H11B1.14620.31570.11120.070*
H11C1.04240.37660.02440.070*
C120.7677 (7)0.2051 (5)0.1104 (3)0.0380 (10)
C130.5996 (7)0.0964 (4)0.1146 (3)0.0403 (10)
H130.60480.01830.07960.048*
C140.4322 (7)0.1000 (4)0.1665 (3)0.0379 (10)
C150.2460 (7)−0.0173 (4)0.1643 (3)0.0434 (11)
H15A0.11780.01820.15450.065*
H15B0.2434−0.06390.22250.065*
H15C0.2605−0.07950.11450.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Al10.0348 (7)0.0243 (6)0.0268 (6)0.0046 (5)0.0003 (5)0.0002 (4)
O10.0298 (14)0.0295 (14)0.0295 (14)0.0021 (11)0.0035 (11)−0.0032 (11)
O20.0372 (17)0.0351 (15)0.0484 (18)0.0012 (13)0.0016 (14)0.0019 (13)
O30.0390 (16)0.0275 (14)0.0395 (16)0.0099 (12)0.0002 (13)0.0030 (12)
O40.0289 (14)0.0320 (14)0.0233 (13)0.0055 (11)0.0028 (11)0.0030 (11)
O50.0450 (17)0.0441 (17)0.0313 (15)0.0179 (14)0.0079 (13)0.0078 (12)
O60.0277 (14)0.0289 (14)0.0385 (16)0.0035 (11)0.0059 (12)0.0016 (12)
O70.0491 (17)0.0345 (15)0.0217 (14)0.0136 (13)0.0050 (12)−0.0011 (11)
O80.0407 (18)0.058 (2)0.0421 (18)0.0050 (15)0.0080 (14)−0.0004 (15)
O90.0457 (17)0.0283 (14)0.0366 (16)0.0027 (12)−0.0069 (13)−0.0013 (12)
C10.030 (2)0.051 (3)0.044 (3)0.0045 (19)0.0002 (19)−0.001 (2)
C20.030 (2)0.027 (2)0.032 (2)−0.0037 (16)0.0129 (17)−0.0102 (16)
C30.047 (3)0.027 (2)0.037 (2)0.0094 (18)0.0084 (19)0.0068 (17)
C40.040 (2)0.033 (2)0.028 (2)0.0124 (18)0.0097 (17)−0.0013 (16)
C50.055 (3)0.037 (2)0.038 (2)0.022 (2)0.004 (2)0.0085 (18)
C60.044 (3)0.047 (3)0.041 (2)0.023 (2)0.006 (2)0.007 (2)
C70.030 (2)0.0283 (19)0.0240 (19)0.0028 (16)−0.0050 (16)0.0005 (15)
C90.029 (2)0.029 (2)0.034 (2)−0.0040 (16)0.0020 (17)−0.0061 (17)
C80.038 (2)0.035 (2)0.026 (2)−0.0002 (18)0.0076 (17)0.0030 (16)
C100.039 (2)0.044 (2)0.047 (3)0.002 (2)0.021 (2)−0.006 (2)
C110.030 (2)0.074 (3)0.036 (2)0.008 (2)0.0128 (19)0.003 (2)
C120.044 (2)0.058 (3)0.0174 (19)0.026 (2)0.0062 (17)0.0084 (18)
C130.058 (3)0.022 (2)0.039 (2)0.0031 (19)−0.007 (2)−0.0040 (17)
C140.049 (3)0.036 (2)0.030 (2)0.0126 (19)−0.0016 (19)0.0033 (18)
C150.051 (3)0.033 (2)0.044 (3)−0.001 (2)0.009 (2)−0.0113 (19)
Geometric parameters (Å, °) top
Al1—O11.905 (3)C4—C51.518 (6)
Al1—O31.859 (3)C5—H5A0.9600
Al1—O41.909 (3)C5—H5B0.9600
Al1—O61.849 (3)C5—H5C0.9600
Al1—O71.904 (3)C6—H6A0.9600
Al1—O91.869 (3)C6—H6B0.9600
O1—C21.267 (5)C6—H6C0.9600
O2—C21.322 (4)C7—C81.406 (5)
O2—C11.432 (5)C9—C81.367 (6)
O3—C41.284 (5)C9—C101.517 (5)
O4—C71.258 (4)C8—H80.9300
O5—C71.329 (4)C10—H10A0.9600
O5—C61.450 (5)C10—H10B0.9600
O6—C91.286 (5)C10—H10C0.9600
O7—C121.273 (5)C11—H11A0.9600
O8—C121.322 (5)C11—H11B0.9600
O8—C111.403 (5)C11—H11C0.9600
O9—C141.263 (5)C12—C131.411 (6)
C1—H1A0.9600C13—C141.345 (6)
C1—H1B0.9600C13—H130.9300
C1—H1C0.9600C14—C151.538 (6)
C2—C31.401 (6)C15—H15A0.9600
C3—C41.352 (6)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
O6—Al1—O392.13 (12)H5B—C5—H5C109.5
O6—Al1—O990.45 (13)O5—C6—H6A109.5
O3—Al1—O991.19 (13)O5—C6—H6B109.5
O6—Al1—O191.76 (12)H6A—C6—H6B109.5
O3—Al1—O190.98 (12)O5—C6—H6C109.5
O9—Al1—O1176.85 (13)H6A—C6—H6C109.5
O6—Al1—O7176.44 (13)H6B—C6—H6C109.5
O3—Al1—O790.98 (12)O4—C7—O5118.6 (3)
O9—Al1—O791.22 (13)O4—C7—C8125.3 (3)
O1—Al1—O786.45 (12)O5—C7—C8116.1 (3)
O6—Al1—O490.71 (12)O6—C9—C8124.9 (4)
O3—Al1—O4177.05 (13)O6—C9—C10114.6 (3)
O9—Al1—O489.59 (12)C8—C9—C10120.5 (4)
O1—Al1—O488.13 (12)C9—C8—C7121.4 (3)
O7—Al1—O486.16 (12)C9—C8—H8119.3
C2—O1—Al1126.1 (3)C7—C8—H8119.3
C2—O2—C1116.9 (3)C9—C10—H10A109.5
C4—O3—Al1129.5 (3)C9—C10—H10B109.5
C7—O4—Al1125.6 (2)H10A—C10—H10B109.5
C7—O5—C6116.8 (3)C9—C10—H10C109.5
C9—O6—Al1127.3 (2)H10A—C10—H10C109.5
C12—O7—Al1123.6 (3)H10B—C10—H10C109.5
C12—O8—C11117.6 (4)O8—C11—H11A109.5
C14—O9—Al1129.2 (3)O8—C11—H11B109.5
O2—C1—H1A109.5H11A—C11—H11B109.5
O2—C1—H1B109.5O8—C11—H11C109.5
H1A—C1—H1B109.5H11A—C11—H11C109.5
O2—C1—H1C109.5H11B—C11—H11C109.5
H1A—C1—H1C109.5O7—C12—O8117.0 (4)
H1B—C1—H1C109.5O7—C12—C13126.0 (4)
O1—C2—O2118.0 (4)O8—C12—C13116.9 (4)
O1—C2—C3125.9 (3)C14—C13—C12123.3 (4)
O2—C2—C3116.1 (3)C14—C13—H13118.4
C4—C3—C2122.4 (4)C12—C13—H13118.4
C4—C3—H3118.8O9—C14—C13122.9 (4)
C2—C3—H3118.8O9—C14—C15115.5 (4)
O3—C4—C3124.0 (4)C13—C14—C15121.6 (4)
O3—C4—C5114.0 (4)C14—C15—H15A109.5
C3—C4—C5122.0 (4)C14—C15—H15B109.5
C4—C5—H5A109.5H15A—C15—H15B109.5
C4—C5—H5B109.5C14—C15—H15C109.5
H5A—C5—H5B109.5H15A—C15—H15C109.5
C4—C5—H5C109.5H15B—C15—H15C109.5
H5A—C5—H5C109.5
O6—Al1—O1—C2−102.8 (3)C1—O2—C2—C3−176.1 (3)
O3—Al1—O1—C2−10.6 (3)O1—C2—C3—C4−2.0 (6)
O7—Al1—O1—C280.3 (3)O2—C2—C3—C4178.1 (4)
O4—Al1—O1—C2166.6 (3)Al1—O3—C4—C3−8.0 (6)
O6—Al1—O3—C4102.4 (3)Al1—O3—C4—C5172.5 (3)
O9—Al1—O3—C4−167.1 (3)C2—C3—C4—O31.4 (6)
O1—Al1—O3—C410.6 (3)C2—C3—C4—C5−179.1 (4)
O7—Al1—O3—C4−75.8 (3)Al1—O4—C7—O5166.7 (2)
O6—Al1—O4—C722.3 (3)Al1—O4—C7—C8−14.6 (5)
O9—Al1—O4—C7−68.1 (3)C6—O5—C7—O4−6.2 (5)
O1—Al1—O4—C7114.0 (3)C6—O5—C7—C8175.0 (3)
O7—Al1—O4—C7−159.4 (3)Al1—O6—C9—C814.4 (5)
O3—Al1—O6—C9158.5 (3)Al1—O6—C9—C10−167.3 (3)
O9—Al1—O6—C967.3 (3)O6—C9—C8—C72.3 (6)
O1—Al1—O6—C9−110.5 (3)C10—C9—C8—C7−175.8 (4)
O4—Al1—O6—C9−22.3 (3)O4—C7—C8—C9−1.8 (6)
O3—Al1—O7—C12−110.4 (3)O5—C7—C8—C9176.9 (3)
O9—Al1—O7—C12−19.2 (3)Al1—O7—C12—O8−169.6 (2)
O1—Al1—O7—C12158.7 (3)Al1—O7—C12—C1312.8 (5)
O4—Al1—O7—C1270.3 (3)C11—O8—C12—O74.5 (5)
O6—Al1—O9—C14−157.2 (3)C11—O8—C12—C13−177.6 (4)
O3—Al1—O9—C14110.6 (3)O7—C12—C13—C142.2 (7)
O7—Al1—O9—C1419.6 (3)O8—C12—C13—C14−175.4 (4)
O4—Al1—O9—C14−66.5 (3)Al1—O9—C14—C13−11.6 (6)
Al1—O1—C2—O2−171.6 (2)Al1—O9—C14—C15168.8 (3)
Al1—O1—C2—C38.6 (5)C12—C13—C14—O9−3.4 (7)
C1—O2—C2—O14.1 (5)C12—C13—C14—C15176.2 (4)
Table 1
Selected geometric parameters (Å) top
Al1—O11.905 (3)Al1—O61.849 (3)
Al1—O31.859 (3)Al1—O71.904 (3)
Al1—O41.909 (3)Al1—O91.869 (3)
Acknowledgements top

We acknowledge the use of the X-ray CCD facility at the Indian Institute of Science, Bangalore under the IRHPA/DST program, and we thank the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Chrzanowski, L. S. von, Lutz, M. & Spek, A. L. (2007). Acta Cryst. C63, m129–m134.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.