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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1681.
Published online 2009 November 25. doi:  10.1107/S1600536809049812
PMCID: PMC2972076

Tris(methyl 3-oxobutanoato-κ2 O,O′)aluminium(III)

Abstract

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

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

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Object name is e-65-m1681-scheme1.jpg

Experimental

Crystal data

  • [Al(C5H7O3)3]
  • M r = 372.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1681-efi1.jpg
  • a = 6.476 (1) Å
  • b = 9.986 (2) Å
  • c = 14.368 (2) Å
  • α = 90.478 (2)°
  • β = 92.229 (2)°
  • γ = 99.337 (2)°
  • V = 916.1 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 293 K
  • 0.5 × 0.4 × 0.2 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan SADABS (Sheldrick, 1996 [triangle]) T min = 0.927, T max = 0.970
  • 8801 measured reflections
  • 3207 independent reflections
  • 2304 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.189
  • S = 1.02
  • 3207 reflections
  • 232 parameters
  • H-atom parameters constrained
  • Δρmax = 1.26 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049812/xu2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049812/xu2684Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

[Al(C5H7O3)3]Z = 2
Mr = 372.30F(000) = 392
Triclinic, P1Dx = 1.350 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer3207 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

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 = 1.02w = 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 Å3
0 restraintsΔρmin = −0.28 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2684).

References

  • 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. [PubMed]
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography