Tris(2-acetyl-cyclo-pentan-1-onato-κ(2)O,O')aluminium.

In the title compound, [Al(C(7)H(9)O(2))(3)], the Al(III) cation is coordinated by six O atoms from three 2-acetyl-cyclo-penta-nonate ligands in a slightly distorted octa-hedral environment, with Al-O bond lengths in the range 1.882 (2)-1.896 (2) Å. In the crystal, mol-ecules are linked together via C-H⋯O inter-actions. One of the C atoms in one ring has a large thermal motion compared to the other atoms, indicating some possible disorder. However, the treatment of this C atom as disordered over two positions did not give a significant improvement.

Related literature

For applications of metal complexes with β-diketones, see: Bray et al. (2007 ▶); Garibay et al. (2009 ▶); Lutz et al. (1989 ▶); Perdih (2011 ▶); Vreshch et al. (2004 ▶); Wu & Wang (2009 ▶). For related structures, see: Hon & Pfluger (1973 ▶); Schröder et al. (2011 ▶).

Experimental

Crystal data

[Al(C7H9O2)3]

M = 402.41

Monoclinic,

a = 8.1785 (3) Å

b = 15.7494 (6) Å

c = 15.6615 (5) Å

β = 94.039 (2)°

V = 2012.29 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.25 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.967, T max = 0.989

8554 measured reflections

4523 independent reflections

3007 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.228

S = 1.03

4523 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021848/fj2551sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021848/fj2551Isup2.hkl

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

[Al(C7H9O2)3]	F(000) = 856
Mr = 402.41	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4677 reflections
a = 8.1785 (3) Å	θ = 2.6–27.5°
b = 15.7494 (6) Å	µ = 0.14 mm−1
c = 15.6615 (5) Å	T = 293 K
β = 94.039 (2)°	Prism, pink
V = 2012.29 (12) Å3	0.25 × 0.15 × 0.08 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	4523 independent reflections
Graphite monochromator	3007 reflections with I > 2σ(I)
Detector resolution: 0.055 pixels mm-1	Rint = 0.031
ω scans	θmax = 27.4°, θmin = 5.4°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.967, Tmax = 0.989	k = −19→20
8554 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1175P)2 + 1.0495P] where P = (Fo2 + 2Fc2)/3
4523 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. 259 frames in 6 sets of ω scans. Rotation/frame = 1.6 °. Crystal-detector distance = 25.00 mm. Measuring time = 135 s/°.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Al1	0.14039 (11)	0.17092 (6)	0.83613 (6)	0.0532 (3)
O1	0.1108 (3)	0.05260 (14)	0.85125 (16)	0.0650 (6)
O2	0.2377 (3)	0.18225 (13)	0.94807 (14)	0.0597 (5)
O3	0.1711 (3)	0.28903 (15)	0.82273 (15)	0.0652 (6)
O4	−0.0712 (3)	0.18733 (13)	0.87403 (15)	0.0614 (6)
O5	0.0428 (3)	0.16358 (16)	0.72368 (15)	0.0680 (6)
O6	0.3511 (3)	0.15136 (16)	0.79798 (14)	0.0643 (6)
C1	0.1271 (5)	−0.0881 (2)	0.9056 (3)	0.0782 (11)
H1A	0.0111	−0.0969	0.8962	0.117*
H1B	0.1669	−0.1168	0.957	0.117*
H1C	0.1812	−0.1102	0.8579	0.117*
C2	0.1616 (4)	0.0054 (2)	0.9145 (2)	0.0615 (8)
C3	0.2455 (4)	0.0367 (2)	0.9884 (2)	0.0592 (8)
C4	0.2763 (4)	0.1222 (2)	1.0002 (2)	0.0558 (7)
C5	0.3627 (5)	0.1393 (3)	1.0861 (2)	0.0723 (9)
H5A	0.292	0.1706	1.1221	0.087*
H5B	0.4615	0.1722	1.08	0.087*
C6	0.4041 (6)	0.0539 (3)	1.1243 (3)	0.0898 (12)
H6A	0.3712	0.051	1.1825	0.108*
H6B	0.5212	0.0437	1.1251	0.108*
C7	0.3097 (5)	−0.0125 (3)	1.0675 (3)	0.0827 (11)
H7A	0.382	−0.0581	1.0521	0.099*
H7B	0.22	−0.0366	1.0969	0.099*
C8	0.1261 (6)	0.4374 (3)	0.8147 (4)	0.0965 (14)
H8A	0.2406	0.4399	0.8328	0.145*
H8B	0.0665	0.4755	0.8489	0.145*
H8C	0.1105	0.4536	0.7556	0.145*
C9	0.0646 (4)	0.3488 (2)	0.8254 (2)	0.0618 (8)
C10	−0.0975 (4)	0.3343 (2)	0.8415 (2)	0.0613 (8)
C11	−0.1526 (4)	0.25647 (19)	0.86725 (19)	0.0544 (7)
C12	−0.3253 (4)	0.2623 (2)	0.8937 (3)	0.0708 (9)
H12A	−0.3274	0.2635	0.9555	0.085*
H12B	−0.3908	0.2149	0.8714	0.085*
C13	−0.3866 (5)	0.3453 (3)	0.8545 (4)	0.0978 (14)
H13A	−0.4617	0.3728	0.8909	0.117*
H13B	−0.4427	0.3356	0.7987	0.117*
C14	−0.2323 (5)	0.4006 (3)	0.8464 (3)	0.0885 (12)
H14A	−0.2423	0.4352	0.7951	0.106*
H14B	−0.212	0.4371	0.8959	0.106*
C15	0.0005 (6)	0.1580 (4)	0.5720 (3)	0.1018 (15)
H15A	−0.1099	0.1444	0.5841	0.153*
H15B	0.0376	0.1184	0.5309	0.153*
H15C	0.0041	0.2145	0.5492	0.153*
C16	0.1110 (5)	0.1527 (2)	0.6540 (2)	0.0656 (8)
C17	0.2757 (4)	0.1371 (2)	0.6491 (2)	0.0637 (8)
C18	0.3859 (4)	0.1378 (2)	0.7208 (2)	0.0601 (8)
C19	0.5569 (5)	0.1223 (3)	0.6982 (3)	0.0901 (13)
H19A	0.605	0.0743	0.7296	0.108*
H19B	0.625	0.172	0.7096	0.108*
C20	0.5346 (8)	0.1031 (6)	0.5998 (4)	0.146 (3)
H20A	0.6077	0.1387	0.5693	0.175*
H20B	0.562	0.0442	0.5893	0.175*
C21	0.3599 (6)	0.1200 (3)	0.5679 (2)	0.0795 (11)
H21A	0.3123	0.0711	0.5378	0.095*
H21B	0.3525	0.1688	0.5301	0.095*

	U11	U22	U33	U12	U13	U23
Al1	0.0445 (5)	0.0518 (5)	0.0634 (6)	0.0021 (4)	0.0050 (4)	0.0008 (4)
O1	0.0590 (13)	0.0509 (12)	0.0843 (15)	0.0013 (10)	−0.0007 (11)	−0.0063 (11)
O2	0.0647 (13)	0.0506 (11)	0.0634 (12)	−0.0003 (10)	0.0028 (10)	0.0003 (10)
O3	0.0507 (12)	0.0577 (13)	0.0871 (16)	−0.0048 (10)	0.0049 (11)	0.0115 (11)
O4	0.0499 (12)	0.0530 (12)	0.0826 (15)	−0.0004 (9)	0.0134 (10)	0.0020 (11)
O5	0.0501 (12)	0.0859 (17)	0.0672 (14)	0.0022 (11)	−0.0006 (10)	0.0017 (12)
O6	0.0453 (11)	0.0830 (16)	0.0647 (13)	0.0085 (10)	0.0057 (9)	−0.0047 (11)
C1	0.070 (2)	0.0508 (18)	0.114 (3)	−0.0067 (16)	0.007 (2)	−0.0023 (19)
C2	0.0438 (15)	0.0476 (16)	0.095 (2)	0.0028 (12)	0.0168 (15)	0.0003 (16)
C3	0.0484 (16)	0.0518 (16)	0.078 (2)	0.0044 (13)	0.0108 (14)	0.0075 (15)
C4	0.0490 (16)	0.0591 (17)	0.0602 (17)	0.0036 (13)	0.0098 (13)	0.0031 (14)
C5	0.072 (2)	0.077 (2)	0.067 (2)	−0.0015 (18)	−0.0044 (17)	0.0000 (17)
C6	0.093 (3)	0.088 (3)	0.088 (3)	0.010 (2)	−0.005 (2)	0.006 (2)
C7	0.069 (2)	0.079 (2)	0.101 (3)	0.0039 (19)	0.009 (2)	0.026 (2)
C8	0.084 (3)	0.058 (2)	0.146 (4)	−0.0124 (19)	−0.004 (3)	0.022 (2)
C9	0.0634 (19)	0.0520 (16)	0.0686 (19)	−0.0011 (15)	−0.0040 (15)	0.0059 (14)
C10	0.0619 (19)	0.0563 (17)	0.0654 (18)	0.0077 (15)	0.0026 (15)	0.0013 (15)
C11	0.0469 (15)	0.0561 (17)	0.0598 (17)	0.0030 (13)	0.0016 (12)	−0.0059 (13)
C12	0.0502 (18)	0.080 (2)	0.083 (2)	0.0036 (16)	0.0112 (16)	−0.0066 (19)
C13	0.067 (2)	0.102 (3)	0.124 (4)	0.023 (2)	0.012 (2)	0.008 (3)
C14	0.087 (3)	0.074 (2)	0.105 (3)	0.028 (2)	0.010 (2)	0.005 (2)
C15	0.104 (4)	0.122 (4)	0.077 (3)	−0.016 (3)	−0.013 (2)	0.010 (3)
C16	0.069 (2)	0.0590 (18)	0.068 (2)	−0.0097 (16)	0.0007 (16)	0.0029 (15)
C17	0.071 (2)	0.0559 (17)	0.0649 (19)	−0.0040 (16)	0.0126 (16)	0.0000 (15)
C18	0.0561 (17)	0.0505 (16)	0.075 (2)	0.0022 (13)	0.0158 (15)	0.0019 (15)
C19	0.071 (2)	0.089 (3)	0.114 (3)	0.012 (2)	0.030 (2)	0.000 (2)
C20	0.108 (4)	0.223 (8)	0.111 (4)	0.045 (5)	0.040 (3)	0.004 (5)
C21	0.097 (3)	0.080 (2)	0.064 (2)	0.004 (2)	0.0191 (19)	−0.0013 (18)

Al1—O2	1.882 (2)	C8—H8B	0.96
Al1—O5	1.885 (2)	C8—H8C	0.96
Al1—O4	1.887 (2)	C9—C10	1.386 (5)
Al1—O6	1.889 (2)	C10—C11	1.377 (4)
Al1—O3	1.891 (2)	C10—C14	1.524 (5)
Al1—O1	1.896 (2)	C11—C12	1.502 (4)
O1—C2	1.284 (4)	C12—C13	1.514 (6)
O2—C4	1.274 (4)	C12—H12A	0.97
O3—C9	1.285 (4)	C12—H12B	0.97
O4—C11	1.277 (4)	C13—C14	1.545 (7)
O5—C16	1.272 (4)	C13—H13A	0.97
O6—C18	1.279 (4)	C13—H13B	0.97
C1—C2	1.504 (5)	C14—H14A	0.97
C1—H1A	0.96	C14—H14B	0.97
C1—H1B	0.96	C15—C16	1.519 (5)
C1—H1C	0.96	C15—H15A	0.96
C2—C3	1.392 (5)	C15—H15B	0.96
C3—C4	1.380 (4)	C15—H15C	0.96
C3—C7	1.524 (5)	C16—C17	1.376 (5)
C4—C5	1.499 (5)	C17—C18	1.389 (5)
C5—C6	1.501 (6)	C17—C21	1.512 (5)
C5—H5A	0.97	C18—C19	1.486 (5)
C5—H5B	0.97	C19—C20	1.569 (7)
C6—C7	1.544 (6)	C19—H19A	0.97
C6—H6A	0.97	C19—H19B	0.97
C6—H6B	0.97	C20—C21	1.504 (7)
C7—H7A	0.97	C20—H20A	0.97
C7—H7B	0.97	C20—H20B	0.97
C8—C9	1.496 (5)	C21—H21A	0.97
C8—H8A	0.96	C21—H21B	0.97
O2—Al1—O5	178.08 (11)	O3—C9—C10	123.0 (3)
O2—Al1—O4	91.78 (11)	O3—C9—C8	116.5 (3)
O5—Al1—O4	87.99 (11)	C10—C9—C8	120.4 (3)
O2—Al1—O6	88.54 (10)	C11—C10—C9	122.5 (3)
O5—Al1—O6	91.73 (10)	C11—C10—C14	110.0 (3)
O4—Al1—O6	178.47 (11)	C9—C10—C14	127.0 (3)
O2—Al1—O3	87.68 (10)	O4—C11—C10	127.2 (3)
O5—Al1—O3	90.43 (11)	O4—C11—C12	121.6 (3)
O4—Al1—O3	91.84 (10)	C10—C11—C12	111.1 (3)
O6—Al1—O3	89.67 (11)	C11—C12—C13	103.4 (3)
O2—Al1—O1	91.50 (10)	C11—C12—H12A	111.1
O5—Al1—O1	90.40 (11)	C13—C12—H12A	111.1
O4—Al1—O1	88.12 (10)	C11—C12—H12B	111.1
O6—Al1—O1	90.38 (11)	C13—C12—H12B	111.1
O3—Al1—O1	179.17 (12)	H12A—C12—H12B	109
C2—O1—Al1	128.9 (2)	C12—C13—C14	105.7 (3)
C4—O2—Al1	126.6 (2)	C12—C13—H13A	110.6
C9—O3—Al1	128.4 (2)	C14—C13—H13A	110.6
C11—O4—Al1	125.1 (2)	C12—C13—H13B	110.6
C16—O5—Al1	128.9 (2)	C14—C13—H13B	110.6
C18—O6—Al1	126.5 (2)	H13A—C13—H13B	108.7
C2—C1—H1A	109.5	C10—C14—C13	102.5 (3)
C2—C1—H1B	109.5	C10—C14—H14A	111.3
H1A—C1—H1B	109.5	C13—C14—H14A	111.3
C2—C1—H1C	109.5	C10—C14—H14B	111.3
H1A—C1—H1C	109.5	C13—C14—H14B	111.3
H1B—C1—H1C	109.5	H14A—C14—H14B	109.2
O1—C2—C3	123.4 (3)	C16—C15—H15A	109.5
O1—C2—C1	116.5 (3)	C16—C15—H15B	109.5
C3—C2—C1	120.1 (3)	H15A—C15—H15B	109.5
C4—C3—C2	122.1 (3)	C16—C15—H15C	109.5
C4—C3—C7	109.8 (3)	H15A—C15—H15C	109.5
C2—C3—C7	128.1 (3)	H15B—C15—H15C	109.5
O2—C4—C3	127.1 (3)	O5—C16—C17	124.2 (3)
O2—C4—C5	121.4 (3)	O5—C16—C15	116.5 (4)
C3—C4—C5	111.4 (3)	C17—C16—C15	119.3 (4)
C4—C5—C6	106.0 (3)	C16—C17—C18	122.4 (3)
C4—C5—H5A	110.5	C16—C17—C21	125.7 (3)
C6—C5—H5A	110.5	C18—C17—C21	111.9 (3)
C4—C5—H5B	110.5	O6—C18—C17	126.2 (3)
C6—C5—H5B	110.5	O6—C18—C19	121.8 (3)
H5A—C5—H5B	108.7	C17—C18—C19	112.0 (3)
C5—C6—C7	106.8 (3)	C18—C19—C20	102.7 (4)
C5—C6—H6A	110.4	C18—C19—H19A	111.2
C7—C6—H6A	110.4	C20—C19—H19A	111.2
C5—C6—H6B	110.4	C18—C19—H19B	111.2
C7—C6—H6B	110.4	C20—C19—H19B	111.2
H6A—C6—H6B	108.6	H19A—C19—H19B	109.1
C3—C7—C6	104.6 (3)	C21—C20—C19	109.5 (4)
C3—C7—H7A	110.8	C21—C20—H20A	109.8
C6—C7—H7A	110.8	C19—C20—H20A	109.8
C3—C7—H7B	110.8	C21—C20—H20B	109.8
C6—C7—H7B	110.8	C19—C20—H20B	109.8
H7A—C7—H7B	108.9	H20A—C20—H20B	108.2
C9—C8—H8A	109.5	C20—C21—C17	103.4 (4)
C9—C8—H8B	109.5	C20—C21—H21A	111.1
H8A—C8—H8B	109.5	C17—C21—H21A	111.1
C9—C8—H8C	109.5	C20—C21—H21B	111.1
H8A—C8—H8C	109.5	C17—C21—H21B	111.1
H8B—C8—H8C	109.5	H21A—C21—H21B	109.1
O2—Al1—O1—C2	−6.5 (3)	C4—C3—C7—C6	−7.2 (4)
O5—Al1—O1—C2	173.8 (3)	C2—C3—C7—C6	175.3 (3)
O4—Al1—O1—C2	−98.2 (3)	C5—C6—C7—C3	11.3 (4)
O6—Al1—O1—C2	82.0 (3)	Al1—O3—C9—C10	1.7 (5)
O4—Al1—O2—C4	95.2 (2)	Al1—O3—C9—C8	178.5 (3)
O6—Al1—O2—C4	−83.3 (3)	O3—C9—C10—C11	8.9 (5)
O3—Al1—O2—C4	−173.0 (3)	C8—C9—C10—C11	−167.7 (4)
O1—Al1—O2—C4	7.1 (3)	O3—C9—C10—C14	179.6 (4)
O2—Al1—O3—C9	−102.5 (3)	C8—C9—C10—C14	3.0 (6)
O5—Al1—O3—C9	77.2 (3)	Al1—O4—C11—C10	−8.6 (5)
O4—Al1—O3—C9	−10.8 (3)	Al1—O4—C11—C12	175.7 (2)
O6—Al1—O3—C9	169.0 (3)	C9—C10—C11—O4	−5.3 (6)
O2—Al1—O4—C11	101.5 (3)	C14—C10—C11—O4	−177.4 (3)
O5—Al1—O4—C11	−76.6 (3)	C9—C10—C11—C12	170.8 (3)
O3—Al1—O4—C11	13.7 (3)	C14—C10—C11—C12	−1.3 (4)
O1—Al1—O4—C11	−167.1 (3)	O4—C11—C12—C13	−166.0 (3)
O4—Al1—O5—C16	179.1 (3)	C10—C11—C12—C13	17.6 (4)
O6—Al1—O5—C16	−2.4 (3)	C11—C12—C13—C14	−26.3 (5)
O3—Al1—O5—C16	87.3 (3)	C11—C10—C14—C13	−15.1 (4)
O1—Al1—O5—C16	−92.8 (3)	C9—C10—C14—C13	173.2 (4)
O2—Al1—O6—C18	−179.3 (3)	C12—C13—C14—C10	25.4 (5)
O5—Al1—O6—C18	−1.2 (3)	Al1—O5—C16—C17	5.4 (5)
O3—Al1—O6—C18	−91.6 (3)	Al1—O5—C16—C15	−174.2 (3)
O1—Al1—O6—C18	89.2 (3)	O5—C16—C17—C18	−4.6 (5)
Al1—O1—C2—C3	3.3 (5)	C15—C16—C17—C18	175.0 (3)
Al1—O1—C2—C1	−176.4 (2)	O5—C16—C17—C21	177.1 (3)
O1—C2—C3—C4	1.9 (5)	C15—C16—C17—C21	−3.3 (6)
C1—C2—C3—C4	−178.4 (3)	Al1—O6—C18—C17	2.0 (5)
O1—C2—C3—C7	179.2 (3)	Al1—O6—C18—C19	−179.4 (3)
C1—C2—C3—C7	−1.1 (5)	C16—C17—C18—O6	0.8 (5)
Al1—O2—C4—C3	−4.8 (5)	C21—C17—C18—O6	179.3 (3)
Al1—O2—C4—C5	176.3 (2)	C16—C17—C18—C19	−177.9 (3)
C2—C3—C4—O2	−1.1 (5)	C21—C17—C18—C19	0.6 (4)
C7—C3—C4—O2	−178.9 (3)	O6—C18—C19—C20	176.1 (4)
C2—C3—C4—C5	177.9 (3)	C17—C18—C19—C20	−5.1 (5)
C7—C3—C4—C5	0.1 (4)	C18—C19—C20—C21	7.8 (6)
O2—C4—C5—C6	−173.7 (3)	C19—C20—C21—C17	−7.5 (6)
C3—C4—C5—C6	7.2 (4)	C16—C17—C21—C20	−177.1 (5)
C4—C5—C6—C7	−11.3 (4)	C18—C17—C21—C20	4.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O6i	0.97	2.54	3.427 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯O6i	0.97	2.54	3.427 (4)	153

Symmetry code: (i) .