Tris(2-acetyl­cyclo­pentan-1-onato-κ2O,O′)aluminium

Perdih, F.

doi:10.1107/S1600536812021848

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m781

doi:10.1107/S1600536812021848

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Tris(2-acetylcyclopentan-1-onato-κ²O,O′)aluminium

Franc Perdih ^a ^*

^aFaculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P. O. Box 537, SI-1000 Ljubljana, Slovenia, and CO EN–FIST, Dunajska 156, SI-1000 Ljubljana, Slovenia
^*Correspondence e-mail: franc.perdih@fkkt.uni-lj.si

(Received 30 April 2012; accepted 14 May 2012; online 19 May 2012)

In the title compound, [Al(C₇H₉O₂)₃], the Al^III cation is coordinated by six O atoms from three 2-acetylcyclopentanonate ligands in a slightly distorted octahedral environment, with Al—O bond lengths in the range 1.882 (2)–1.896 (2) Å. In the crystal, molecules are linked together via C—H⋯O interactions. 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_r = 402.41
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.228
S = 1.03
4523 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) x-1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021848/fj2551sup1.cif

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

checkCIF report

Comment top

β-Diketonates have been proven to be versatile ligands for various metal ions. They can be easily derivatized, thus modifying the electronic and steric nature of these ligands to design suitable structure/function relationship (Bray et al., 2007; Garibay et al., 2009; Perdih, 2011). β-diketonate compounds of aluminium have received great attention due to the promise of the construction of cages (Vreshch et al., 2004; Wu & Wang, 2009). Besides that, the title compound is a close analogue of aluminium isomaltolato compound that was prepared for in vivo examinations of ion transport in order to shed some light on the mechanism of transport and the involvement of Al in neurological disorders (Lutz et al., 1989).

In the title molecule (Fig. 1), the aluminium(III) cation is surrounded by six O atoms from three 2-acetylcyclopentanonate ligands in a octahedral environment. The geometry around aluminium is close to the orthogonallity as can be seen from the angles. The Al—O bond lengths in the range 1.882 (2)–1.896 (2) Å and are similar as for example in Al(acac)₃ (Hon & Pfluger, 1973). All three cyclopentyl rings deviates from the expected envelope conformation and they are close to planarity, with torsion angles C3–C4–C5–C6 - 7.2 (4), C10–C11–C12–C13 - 17.6 (4)° and C17–C18–C19–C20 5.0 (5)°. Such small torsion angles are often observed in cyclopentyl and 1,3-dioxolyl rings condensed to aromatic or delocalized systems. This values are somewhat smaller then in analogues iron(III) compound (Schröder et al., 2011). 1-D framework is achieved due to weak intermolecular C12–H12B···O6(x – 1, y, z) interactions (Fig. 2).

Related literature top

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 top

To a clear solution of Al₂(SO₄)₃^.18H₂O (1 mmol, 0.67 g) in water (15 ml) a solution of 2-acetylcyclopentanone (6 mmol, 0.76 g) in methanol (5 ml) was added while stirring. Afterwards the 1 M NaOH (6 ml) was slowly added and the resulting solution stirred at 70°C for 15 minutes. After cooling to the room temperature the light pink product was filtrated and washed with water (20 ml), and subsequently air-dried. Yield: 0.47 g, 58%. Crystals suitable for X-ray analysis were obtained by recrystallization from ethanol.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); 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).

Figures top

	Fig. 1. The molecular structure of the title complex showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A chain formation. Dashed lines indicate intermolecular C12—H12B···O6 hydrogen bonding. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Symmetry code: ⁱ = x – 1, y, z.

Tris(2-acetylcyclopentan-1-onato-κ²O,O')aluminium top

Crystal data top

[Al(C₇H₉O₂)₃]	F(000) = 856
M_r = 402.41	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1175P)² + 1.0495P] where P = (F_o² + 2F_c²)/3
4523 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Al(C₇H₉O₂)₃]	V = 2012.29 (12) Å³
M_r = 402.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1785 (3) Å	µ = 0.14 mm⁻¹
b = 15.7494 (6) Å	T = 293 K
c = 15.6615 (5) Å	0.25 × 0.15 × 0.08 mm
β = 94.039 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	4523 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	3007 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.989	R_int = 0.031
8554 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 1.03	Δρ_max = 0.56 e Å⁻³
4523 reflections	Δρ_min = −0.27 e Å⁻³
256 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Al(C₇H₉O₂)₃]
M_r	402.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1785 (3), 15.7494 (6), 15.6615 (5)
β (°)	94.039 (2)
V (Å³)	2012.29 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.25 × 0.15 × 0.08

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.967, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	8554, 4523, 3007
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.228, 1.03
No. of reflections	4523
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.27

Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Acknowledgements

The author thanks the Ministry of Higher Education, Science and Technology of the Republic of Slovenia and the Slovenian Research Agency for financial support through grants P1–0230–0175 and X–2000.

References

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