Triphen­yl(tetra­hydro­furan)­aluminium(III)

Chen, C.-R.; Gau, H.-M.

doi:10.1107/S1600536808032091

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1381

doi:10.1107/S1600536808032091

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Triphenyl(tetrahydrofuran)aluminium(III)

Chi-Ren Chen ^a and Han-Mou Gau ^a ^*

^aDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
^*Correspondence e-mail: hmgau@dragon.nchu.edu.tw

(Received 24 September 2008; accepted 6 October 2008; online 11 October 2008)

In the title compound, [Al(C₆H₅)₃(C₄H₈O)], the Al atom has a distorted tetrahedral geometry. The C—Al—C angles range from 113.25 (7) to 116.27 (8)°, much larger than the O—Al—C angles, which range from 103.39 (7) to 103.90 (6)°. The tetrahydrofuran ring adopts an envelope conformation. The crystal packing is stabilized by C—H⋯π interactions.

Related literature

For general background, see: Chen et al. (2007 ); Ku et al. (2007 ); Wu & Gau (2006 ). For related structures, see: Barber et al. (1982 ); De Mel & Oliver (1989 ); Jerius et al. (1986 ); Malone & McDonald (1967 ).

Experimental

Crystal data

[Al(C₆H₅)₃(C₄H₈O)]
M_r = 330.38
Monoclinic, P 2₁ /c
a = 9.649 (2) Å
b = 12.966 (3) Å
c = 16.038 (4) Å
β = 104.210 (4)°
V = 1945.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.58 × 0.42 × 0.21 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.799, T_max = 1.000 (expected range = 0.781–0.977)
10682 measured reflections
3804 independent reflections
2971 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.162
S = 1.33
3804 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Al1—O1	1.8972 (13)
Al1—C1	1.9783 (18)
Al1—C13	1.9800 (18)
Al1—C7	1.9809 (19)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯Cg1ⁱ	0.93	2.78	3.654 (4)	156
C19—H19A⋯Cg1ⁱⁱ	0.97	2.81	3.600 (4)	139
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032091/ci2683sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032091/ci2683Isup2.hkl

checkCIF report

Comment top

Triphenylaluminium was first reported 40 years ago and the solid-state study revealed a dimeric Al₂Ph₆ structure bridging through two phenyl groups (Malone & McDonald, 1967). For synthesis of monomeric triarylaluminium complexes, two synthetic strategies were used. The first route employed a reaction of dimesitylmercury with Al/HgCl₂, furnishing three-coordinate trimesitylaluminium (Jerius et al., 1986) which possesses a trigonal planar structure. The second synthetic route used a strategy of providing an additional neutral ligand, such as tetrahydrofuran (THF) or diethyl ether (OEt₂), giving four-coordinate monomeric AlAr₃(L) complexes (L = THF or OEt₂) (Barber et al., 1982; De Mel & Oliver, 1989). In addition to structural studies, organoaluminium reagents had been demonstrated as excellent nucleophiles in organic synthesis, owing to their higher reactivity and the Lewis acidity of the aluminium center. Recently, we reported applications of AlAr₃(THF) in asymmetric aryl additions to aldehydes (Wu & Gau, 2006) and to ketones (Chen et al., 2007) and in coupling reactions (Ku et al., 2007). Due to their diversified applications in catalysis, we report herein the synthesis and structure of a four-coordinate triphenylaluminium compound, [Al(C₆H₅)₃(OC₄H₈)].

The molecule of the title compound contains unsubstituted phenyl ligands and has a distorted tetrahedral geometry around the aluminium metal center (Fig. 1). The Al—O(THF) bond length of 1.8972 (13) Å is shorter by 0.08 Å than the Al—C bond distances of 1.9783 (18), 1.9800 (18) and 1.9809 (19) Å. This complex has similar Al—C bond distances with the four-coordinate (o-tol)₃Al(OEt₂) complex (Barber et al., 1982). The C—Al—O bond angles in the title complex [103.39 (7), 103.90 (6) and 103.75 (7)°] are much smaller than the C—Al—C bond angles [113.25 (7), 114.23 (7) and 116.27 (8)°]. In contrast, the bulky mesityl ligands in trimesityl(tetrahydrofuran)aluminium complex (De Mel & Oliver, 1989) repel each other, giving longer Al—C bond lengths of 2.011 (7), 2.020 (7) and 2.021 (6) Å. Similarly, the Al—O(THF) bond distance of 1.969 (5) Å in the above complex is longer by 0.07 Å than the Al—O(THF) bond length in the title compound.

Related literature top

For general background, see: Chen et al. (2007); Ku et al. (2007); Wu & Gau (2006). For related structures, see: Barber et al. (1982); De Mel & Oliver (1989); Jerius et al. (1986); Malone & McDonald (1967).

Experimental top

A solution of phenylmagnesium bromide (90.0 mmol) in THF (50 ml) was slowly added to a solution of AlCl₃ (4.00 g, 30.0 mmol) in THF (20 ml) at 273 K. The mixture was stirred at room temperature for 12 h and the solvent was removed under reduced pressure to afford a residue which was extracted with toluene (2 × 40 ml). The extracts were combined and concentrated to about 50 ml. Colourless crystals of the title compound (8.92 g, 90.0% yield) were obtained by cooling the concentrated solution at 273 K. The above synthetic procedures were conducted strictly under nitrogen atmosphere. ¹H NMR (CDCl₃, 400 MHz): δ 7.80–7.76 (m, 6H), 7.34–7.30 (m, 9H), 4.16 (m, 4H), 2.01 (m, 4H) p.p.m. ¹³C{¹H} NMR (CDCl₃, 100 MHz): δ 146.74, 137.99, 127.50, 127.06, 75.59, 24.97 p.p.m. Analysis calculated for C₂₂H₂₃OAl: C 79.97, H 7.02%;found: C 79.44, H 6.75%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with atom-numbering and displacement ellipsoids drawn at the 20% probability level.

Triphenyl(tetrahydrofuran)aluminium(III) top

Crystal data top

[Al(C₆H₅)₃(C₄H₈O)]	F(000) = 704
M_r = 330.38	D_x = 1.128 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3804 reflections
a = 9.649 (2) Å	θ = 2.1–26.0°
b = 12.966 (3) Å	µ = 0.11 mm⁻¹
c = 16.038 (4) Å	T = 293 K
β = 104.210 (4)°	Block, colourless
V = 1945.1 (8) Å³	0.58 × 0.42 × 0.21 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3804 independent reflections
Radiation source: fine-focus sealed tube	2971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
T_min = 0.799, T_max = 1.000	k = −15→15
10682 measured reflections	l = −19→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.33	w = 1/[σ²(F_o²) + (0.0861P)²] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Al(C₆H₅)₃(C₄H₈O)]	V = 1945.1 (8) Å³
M_r = 330.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.649 (2) Å	µ = 0.11 mm⁻¹
b = 12.966 (3) Å	T = 293 K
c = 16.038 (4) Å	0.58 × 0.42 × 0.21 mm
β = 104.210 (4)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2971 reflections with I > 2σ(I)
T_min = 0.799, T_max = 1.000	R_int = 0.023
10682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.33	Δρ_max = 0.27 e Å⁻³
3804 reflections	Δρ_min = −0.23 e Å⁻³
217 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

	x	y	z	U_iso*/U_eq
Al1	0.39089 (5)	0.69171 (4)	0.18576 (3)	0.0508 (2)
O1	0.38837 (12)	0.75437 (10)	0.29228 (7)	0.0623 (4)
C1	0.27597 (17)	0.56515 (13)	0.18473 (11)	0.0540 (4)
C2	0.2690 (2)	0.51194 (15)	0.25899 (13)	0.0668 (5)
H2	0.3158	0.5394	0.3120	0.080*
C3	0.1956 (3)	0.42013 (17)	0.25735 (17)	0.0818 (6)
H3	0.1936	0.3872	0.3086	0.098*
C4	0.1265 (2)	0.37804 (17)	0.1810 (2)	0.0880 (7)
H4	0.0771	0.3162	0.1797	0.106*
C5	0.1296 (2)	0.42674 (18)	0.10597 (17)	0.0836 (7)
H5	0.0820	0.3982	0.0536	0.100*
C6	0.2037 (2)	0.51857 (15)	0.10780 (13)	0.0672 (5)
H6	0.2053	0.5503	0.0560	0.081*
C7	0.30029 (18)	0.79599 (14)	0.09920 (11)	0.0573 (4)
C8	0.1554 (2)	0.78994 (17)	0.05675 (12)	0.0699 (5)
H8	0.1016	0.7356	0.0700	0.084*
C9	0.0891 (2)	0.8605 (2)	−0.00356 (15)	0.0864 (7)
H9	−0.0075	0.8535	−0.0302	0.104*
C10	0.1641 (3)	0.9404 (2)	−0.02443 (16)	0.0907 (7)
H10	0.1195	0.9879	−0.0658	0.109*
C11	0.3064 (3)	0.95119 (19)	0.01558 (16)	0.0891 (7)
H11	0.3581	1.0065	0.0019	0.107*
C12	0.3729 (2)	0.87933 (16)	0.07661 (13)	0.0728 (5)
H12	0.4694	0.8875	0.1032	0.087*
C13	0.59598 (17)	0.66352 (14)	0.19566 (12)	0.0585 (4)
C14	0.6632 (2)	0.68758 (18)	0.13121 (16)	0.0793 (6)
H14	0.6130	0.7237	0.0831	0.095*
C15	0.8054 (3)	0.6587 (3)	0.1368 (3)	0.1220 (12)
H15	0.8478	0.6752	0.0924	0.146*
C16	0.8810 (3)	0.6072 (3)	0.2061 (4)	0.1415 (18)
H16	0.9759	0.5898	0.2100	0.170*
C17	0.8176 (3)	0.5803 (2)	0.2712 (3)	0.1196 (13)
H17	0.8686	0.5430	0.3183	0.144*
C18	0.6776 (2)	0.60906 (17)	0.26599 (15)	0.0801 (6)
H18	0.6364	0.5916	0.3108	0.096*
C19	0.5018 (3)	0.8175 (3)	0.3436 (2)	0.1160 (11)
H19A	0.5475	0.8572	0.3066	0.139*
H19B	0.5734	0.7742	0.3805	0.139*
C20	0.4384 (3)	0.8856 (2)	0.39505 (16)	0.0958 (8)
H20A	0.4383	0.9560	0.3745	0.115*
H20B	0.4921	0.8834	0.4547	0.115*
C21	0.2920 (3)	0.8503 (2)	0.38737 (17)	0.1015 (8)
H21A	0.2860	0.8115	0.4381	0.122*
H21B	0.2275	0.9087	0.3815	0.122*
C22	0.2540 (3)	0.7853 (2)	0.31139 (17)	0.0937 (8)
H22A	0.1952	0.8232	0.2634	0.112*
H22B	0.2013	0.7253	0.3223	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Al1	0.0376 (3)	0.0578 (3)	0.0577 (3)	−0.00033 (19)	0.0129 (2)	−0.0031 (2)
O1	0.0481 (7)	0.0751 (8)	0.0667 (8)	−0.0054 (6)	0.0197 (5)	−0.0148 (6)
C1	0.0381 (8)	0.0582 (10)	0.0664 (10)	0.0042 (7)	0.0140 (7)	−0.0002 (7)
C2	0.0603 (11)	0.0681 (11)	0.0727 (12)	0.0086 (9)	0.0174 (9)	0.0077 (9)
C3	0.0814 (15)	0.0639 (12)	0.1086 (17)	0.0102 (11)	0.0395 (13)	0.0202 (12)
C4	0.0677 (13)	0.0540 (11)	0.152 (2)	−0.0030 (10)	0.0462 (15)	−0.0004 (14)
C5	0.0645 (13)	0.0739 (14)	0.1074 (17)	−0.0091 (10)	0.0115 (12)	−0.0236 (12)
C6	0.0617 (11)	0.0696 (12)	0.0696 (11)	−0.0052 (9)	0.0147 (8)	−0.0044 (9)
C7	0.0494 (10)	0.0637 (10)	0.0604 (10)	0.0024 (8)	0.0166 (7)	−0.0036 (7)
C8	0.0520 (11)	0.0782 (13)	0.0780 (13)	0.0087 (9)	0.0132 (9)	0.0022 (10)
C9	0.0616 (12)	0.1058 (18)	0.0869 (14)	0.0202 (13)	0.0090 (10)	0.0061 (13)
C10	0.0918 (17)	0.0995 (17)	0.0817 (14)	0.0332 (14)	0.0230 (12)	0.0228 (12)
C11	0.0990 (19)	0.0791 (14)	0.0950 (16)	0.0011 (13)	0.0351 (14)	0.0210 (12)
C12	0.0638 (12)	0.0744 (12)	0.0788 (12)	−0.0017 (10)	0.0149 (9)	0.0058 (10)
C13	0.0416 (8)	0.0606 (10)	0.0736 (11)	−0.0031 (8)	0.0149 (7)	−0.0177 (8)
C14	0.0639 (12)	0.0857 (14)	0.0985 (15)	−0.0117 (10)	0.0397 (11)	−0.0284 (12)
C15	0.0816 (19)	0.121 (2)	0.192 (3)	−0.0240 (18)	0.088 (2)	−0.069 (2)
C16	0.0459 (14)	0.126 (3)	0.248 (5)	0.0064 (16)	0.027 (2)	−0.093 (3)
C17	0.0632 (16)	0.0994 (19)	0.167 (3)	0.0286 (14)	−0.0274 (18)	−0.054 (2)
C18	0.0604 (12)	0.0780 (14)	0.0911 (14)	0.0149 (10)	−0.0020 (10)	−0.0159 (11)
C19	0.0805 (16)	0.150 (3)	0.124 (2)	−0.0434 (17)	0.0365 (15)	−0.0780 (19)
C20	0.115 (2)	0.0881 (16)	0.0816 (15)	−0.0032 (15)	0.0194 (13)	−0.0192 (12)
C21	0.125 (2)	0.0909 (17)	0.1067 (19)	0.0074 (16)	0.0622 (16)	−0.0156 (14)
C22	0.0641 (13)	0.122 (2)	0.1058 (17)	−0.0033 (13)	0.0421 (12)	−0.0335 (15)

Geometric parameters (Å, º) top

Al1—O1	1.8972 (13)	C11—C12	1.389 (3)
Al1—C1	1.9783 (18)	C11—H11	0.93
Al1—C13	1.9800 (18)	C12—H12	0.93
Al1—C7	1.9809 (19)	C13—C14	1.384 (3)
O1—C19	1.450 (2)	C13—C18	1.398 (3)
O1—C22	1.460 (2)	C14—C15	1.404 (4)
C1—C2	1.392 (3)	C14—H14	0.93
C1—C6	1.397 (3)	C15—C16	1.346 (5)
C2—C3	1.382 (3)	C15—H15	0.93
C2—H2	0.93	C16—C17	1.378 (5)
C3—C4	1.357 (3)	C16—H16	0.93
C3—H3	0.93	C17—C18	1.384 (4)
C4—C5	1.365 (3)	C17—H17	0.93
C4—H4	0.93	C18—H18	0.93
C5—C6	1.385 (3)	C19—C20	1.443 (3)
C5—H5	0.93	C19—H19A	0.97
C6—H6	0.93	C19—H19B	0.97
C7—C12	1.384 (3)	C20—C21	1.461 (4)
C7—C8	1.399 (2)	C20—H20A	0.97
C8—C9	1.371 (3)	C20—H20B	0.97
C8—H8	0.93	C21—C22	1.452 (3)
C9—C10	1.351 (4)	C21—H21A	0.97
C9—H9	0.93	C21—H21B	0.97
C10—C11	1.372 (4)	C22—H22A	0.97
C10—H10	0.93	C22—H22B	0.97

O1—Al1—C1	103.39 (7)	C11—C12—H12	118.9
O1—Al1—C13	103.90 (6)	C14—C13—C18	116.2 (2)
C1—Al1—C13	113.25 (7)	C14—C13—Al1	122.74 (16)
O1—Al1—C7	103.75 (7)	C18—C13—Al1	120.78 (16)
C1—Al1—C7	114.23 (7)	C15—C14—C13	121.4 (3)
C13—Al1—C7	116.27 (8)	C15—C14—H14	119.3
C19—O1—C22	108.11 (17)	C13—C14—H14	119.3
C19—O1—Al1	125.33 (13)	C14—C15—C16	120.6 (3)
C22—O1—Al1	121.01 (12)	C14—C15—H15	119.7
C2—C1—C6	115.02 (17)	C16—C15—H15	119.7
C2—C1—Al1	123.27 (13)	C15—C16—C17	119.9 (3)
C6—C1—Al1	121.56 (14)	C15—C16—H16	120.0
C3—C2—C1	122.9 (2)	C17—C16—H16	120.0
C3—C2—H2	118.6	C18—C17—C16	119.6 (3)
C1—C2—H2	118.6	C18—C17—H17	120.2
C4—C3—C2	120.0 (2)	C16—C17—H17	120.2
C4—C3—H3	120.0	C17—C18—C13	122.2 (3)
C2—C3—H3	120.0	C17—C18—H18	118.9
C3—C4—C5	119.8 (2)	C13—C18—H18	118.9
C3—C4—H4	120.1	O1—C19—C20	107.6 (2)
C5—C4—H4	120.1	O1—C19—H19A	110.2
C6—C5—C4	120.1 (2)	C20—C19—H19A	110.2
C6—C5—H5	119.9	O1—C19—H19B	110.2
C4—C5—H5	119.9	C20—C19—H19B	110.2
C5—C6—C1	122.2 (2)	H19A—C19—H19B	108.5
C5—C6—H6	118.9	C19—C20—C21	107.3 (2)
C1—C6—H6	118.9	C19—C20—H20A	110.3
C12—C7—C8	115.23 (18)	C21—C20—H20A	110.3
C12—C7—Al1	123.50 (14)	C19—C20—H20B	110.3
C8—C7—Al1	121.27 (15)	C21—C20—H20B	110.3
C9—C8—C7	122.9 (2)	H20A—C20—H20B	108.5
C9—C8—H8	118.6	C22—C21—C20	107.0 (2)
C7—C8—H8	118.6	C22—C21—H21A	110.3
C10—C9—C8	120.1 (2)	C20—C21—H21A	110.3
C10—C9—H9	120.0	C22—C21—H21B	110.3
C8—C9—H9	120.0	C20—C21—H21B	110.3
C9—C10—C11	119.8 (2)	H21A—C21—H21B	108.6
C9—C10—H10	120.1	C21—C22—O1	106.4 (2)
C11—C10—H10	120.1	C21—C22—H22A	110.5
C12—C11—C10	119.8 (2)	O1—C22—H22A	110.5
C12—C11—H11	120.1	C21—C22—H22B	110.5
C10—C11—H11	120.1	O1—C22—H22B	110.5
C7—C12—C11	122.2 (2)	H22A—C22—H22B	108.6
C7—C12—H12	118.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Cg1ⁱ	0.93	2.78	3.654 (4)	156
C19—H19A···Cg1ⁱⁱ	0.97	2.81	3.600 (4)	139

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Al(C₆H₅)₃(C₄H₈O)]
M_r	330.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.649 (2), 12.966 (3), 16.038 (4)
β (°)	104.210 (4)
V (Å³)	1945.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.58 × 0.42 × 0.21

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.799, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10682, 3804, 2971
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.162, 1.33
No. of reflections	3804
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Al1—O1	1.8972 (13)	Al1—C13	1.9800 (18)
Al1—C1	1.9783 (18)	Al1—C7	1.9809 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Cg1ⁱ	0.93	2.78	3.654 (4)	156
C19—H19A···Cg1ⁱⁱ	0.97	2.81	3.600 (4)	139

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by a grant from the National Science Council of Taiwan (grant No. NSC 96-2113-M-005-007-MY3)

References

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