[(E)-10-(2,6-Dimethyl­phenyl­imino)-9-methyl-9,10-dihydro­phenanthren-9-olato]penta­methyl­dialuminum(III)

Gao, B.; Su, Q.; Gao, W.; Mu, Y.

doi:10.1107/S1600536811036312

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1374

https://doi.org/10.1107/S1600536811036312

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[(E)-10-(2,6-Dimethylphenylimino)-9-methyl-9,10-dihydrophenanthren-9-olato]pentamethyldialuminum(III)

Bo Gao,^a Qing Su,^b Wei Gao ^b ^* and Ying Mu ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, School of Chemistry, Jilin University, Changchun 130012, People's Republic of China, and ^bSchool of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: gw@jlu.edu.cn, gaobo08@mails.jlu.edu.cn

(Received 10 August 2011; accepted 6 September 2011; online 14 September 2011)

The two Al atoms in the title compound, [Al₂(CH₃)₅(C₂₃H₂₀NO)], are four-coordinated in a distorted tetrahedral environment. The coordination of one Al atom includes three methyl-C atoms and the O atom from the ligand, whereas the second Al atom is surrounded by the O atom and one N atom from the ligand as well as by two methyl-C atoms. In the ligand, the dihedral angle between the two phenyl rings in the 9,10-dihydrophenanthren unit is 20.64 (12)°.

Related literature

For background to Al complexes, see: Wang et al. (2006 ); Evans (1993 ); Liu et al. (2005 , 2006 ); Yao et al. (2008 ); Gao et al. (2009 ). For background to anilido–imine complexes, see: Liu et al. (2005, 2006); Ren et al. (2007 ); Su et al. (2007 ); Yao et al. (2008); Wang et al. (2006). For the synthesis of the ligand, see: Li (2009 ).

Experimental

Crystal data

[Al₂(CH₃)₅(C₂₃H₂₀NO)]
M_r = 455.53
Triclinic, $[P \overline 1]$
a = 10.4535 (17) Å
b = 11.4306 (18) Å
c = 12.221 (2) Å
α = 84.930 (3)°
β = 86.308 (3)°
γ = 64.092 (2)°
V = 1307.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 185 K
0.36 × 0.32 × 0.19 mm

Data collection

SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.955, T_max = 0.976
6899 measured reflections
4966 independent reflections
3558 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.150
S = 1.03
4966 reflections
297 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

Al1—O1	1.9273 (17)
Al1—C25	1.972 (3)
Al1—C26	1.974 (3)
Al1—C24	1.980 (3)
Al2—O1	1.8552 (17)
Al2—C28	1.944 (3)
Al2—C27	1.954 (3)
Al2—N1	1.993 (2)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036312/wm2522sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036312/wm2522Isup2.hkl

checkCIF report

Comment top

Organoaluminum complexes have received considerable attention due to their interesting properties and potential applications in organic synthesis and catalysis. It is known that alkylaluminum reagents are widely applied to Lewis acid-mediated reactions while aluminium acetylides play an important role in addition reaction (Evans, 1993). Organoaluminum complexes supported by anilido-imine, β-diketiminate and salicyaldiminato ligands are of particular interest, owning to their interesting coordination chemistry and catalytic performance (Wang et al., 2006). Furthermore, we have previously reported a series of Zn(II) (Su et al., 2007), Al(III) (Liu et al., 2005; 2006; Yao et al., 2008) and B(III) (Ren et al., 2007) complexes with chelating anilido-imine ligands. As a part of our continuing study, we have investigated the two-step reaction procedures including the 1,2-addition reaction of trimethylaluminium with (E)-10-(2,6-dimethylphenylimino)phenanthren-9(10H)-one), and subseqent reaction with trimethylaluminium to form the corresponding product. Herein, the preparation and crystal structure of the title compound, (I), [Al₂(CH₃)₅(C₂₃H₂₀NO)], is reported.

In the molecule of compound (I), (Fig. 1), the two Al atoms exist in different coordination environments, both adopting distorted tetrahedral geometries. The tetrahedral coordination around Al1 involves three methyl-C atoms and the O1 atom from the ligand. The coordination around the Al2 atom involves the O1 atom and N1 atom from the ligand and two methyl-C atoms. The Al—Al separation distance is 3.1625 (13) Å. The Al2—O1 distance (1.8552 (17) Å) is significantly shorter than the Al1—O1 distance (1.9273 (17) Å), indicating that the former has a more covalent character. The two Al2—O1 and Al1—O1 distances are somewhat longer than the corresponding distances in {µ-[2-(dimethylamino)phenyl] (2-fluorophenyl)methanolato}pentamethyldialuminum(III) (Gao et al., 2009; Al2—O1, 1.8165 (19) Å; Al1—O1, 1.9199 (19) Å), owing to a larger steric disturbance. The five-membered chelate ring, O1/Al2/N1/C13/C14, is nearly planar, with a maximum deviation of 0.059 (2) Å of O1 from the least-squares plane. The dihedral angles between the five-membered chelate ring and the phenyl rings C16—C11, C7—C11 and C1—C6 are 82.78 (12)°, 62.74 (11) ° and 46.99 (11) °, respectively. The coplarity of the 9,10-phenanthrene aromatic rings is not retained after the addition reaction of Al(CH₃)₃ to the C═O bond of (E)-10-(2,6-dimethylphenylimino)phenanthren-9(10H)-one) with the dihedral angle between the two phenyl rings (C7—C12, C1—C6) being 20.64 (12)°.

Related literature top

For background to Al complexes, see: Wang et al. (2006); Evans (1993); Liu et al. (2005, 2006); Yao et al. (2008); Gao et al. (2009). For background to anilido–imine complexes, see: Liu et al. (2005, 2006); Ren et al. (2007); Su et al. (2007); Yao et al. (2008); Wang et al. (2006). For the synthesis of the ligand, see: Li (2009).

Experimental top

The dinuclear aluminium complex was prepared as following. The Schiff base ligand ((E)-10-(2,6-dimethylphenylimino)phenanthren-9(10H)-one) (1.0 mmol) which was synthesized according to the reported literature (Li, 2009), was dissolved in toluene (20 ml), and then trimethylaluminum (1.1 mmol) in hexane solution (1.1 ml, 1M) was added slowly at 243 K. The whole mixture was warmed up to room temperature in 2 h and refluxed for 5 h which provided a clear, yellow solution. Then volatile materials were removed under vacuum. The residue was recrystallized in toluene to give yellow crystalline solid (yield: 61%, 0.277 g). Anal. Calcd. for C₂₈H₃₅Al₂NO (455.55): C 73.82, H 7.74, N 3.07; Found: C 73.80, H 7.72, N 3.04%. ¹H NMR (300 MHz, CDCl₃, 298 K) δ (p.p.m.): -0.93 (s, 3H,Al(CH₃)₂), -0.65(s, 9H,Al(CH₃)₃), -0.45 (s, 3H,Al(CH₃)₂), 1.41(s, 3H, Ar(CH₃)₂), 1.98 (s, 3H, CH₃), 2.44 (s, 3H, Ar (CH₃)₂), 6.65 (m, 1H), 6.88 (m, 1H), 7.05 (m, 1H), 7.12 (m, 1H), 7.19 (m, 1H), 7.44 (m, 2H), 7.55 (m, 1H), 7.69 (m, 1H), 7.84 (m, 1H), 7.95 (m, 1H). ¹³C NMR (75 MHz, CDCl₃, 298 K) δ (p.p.m.): -8.8,-7.2,-5.1,16.9, 18.2, 18.8, 30.6, 48.3, 123.9, 124.3, 124.8, 126.0, 126.4, 127.3, 127.6, 128.2, 128.6, 128.7, 129.1, 129.2, 129.3, 131.3, 131.8, 132.5, 133.9, 136.6.

Structure description top

For background to Al complexes, see: Wang et al. (2006); Evans (1993); Liu et al. (2005, 2006); Yao et al. (2008); Gao et al. (2009). For background to anilido–imine complexes, see: Liu et al. (2005, 2006); Ren et al. (2007); Su et al. (2007); Yao et al. (2008); Wang et al. (2006). For the synthesis of the ligand, see: Li (2009).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of compound (I) showing the atom labelling scheme, with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.

[(E)-10-(2,6-Dimethylphenylimino)-9-methyl-9,10-dihydrophenanthren-9- olato]pentamethyldialuminum(III) top

Crystal data top

[Al₂(CH₃)₅(C₂₃H₂₀NO)]	Z = 2
M_r = 455.53	F(000) = 488
Triclinic, P1	D_x = 1.157 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4535 (17) Å	Cell parameters from 2148 reflections
b = 11.4306 (18) Å	θ = 3.6–52.0°
c = 12.221 (2) Å	µ = 0.13 mm⁻¹
α = 84.930 (3)°	T = 185 K
β = 86.308 (3)°	Block, colorless
γ = 64.092 (2)°	0.36 × 0.32 × 0.19 mm
V = 1307.9 (4) Å³

Data collection top

SMART CCD area-detector diffractometer	4966 independent reflections
Radiation source: fine-focus sealed tube	3558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→12
T_min = 0.955, T_max = 0.976	k = −11→14
6899 measured reflections	l = −15→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0783P)² + 0.4595P] where P = (F_o² + 2F_c²)/3
4966 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Al₂(CH₃)₅(C₂₃H₂₀NO)]	γ = 64.092 (2)°
M_r = 455.53	V = 1307.9 (4) Å³
Triclinic, P1	Z = 2
a = 10.4535 (17) Å	Mo Kα radiation
b = 11.4306 (18) Å	µ = 0.13 mm⁻¹
c = 12.221 (2) Å	T = 185 K
α = 84.930 (3)°	0.36 × 0.32 × 0.19 mm
β = 86.308 (3)°

Data collection top

SMART CCD area-detector diffractometer	4966 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3558 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.976	R_int = 0.020
6899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	Δρ_max = 0.48 e Å⁻³
4966 reflections	Δρ_min = −0.36 e Å⁻³
297 parameters

Special details top

Experimental. see experiment

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	−0.25584 (8)	0.40105 (7)	0.13162 (7)	0.0300 (2)
Al2	−0.06773 (8)	0.36784 (8)	0.33504 (6)	0.0288 (2)
O1	−0.08466 (16)	0.29493 (15)	0.21020 (13)	0.0250 (4)
N1	0.1395 (2)	0.25468 (19)	0.31395 (16)	0.0253 (5)
C1	0.3077 (2)	0.0805 (2)	0.19939 (19)	0.0252 (5)
C2	0.4290 (3)	0.1021 (3)	0.1830 (2)	0.0290 (6)
H2	0.4254	0.1823	0.1968	0.035*
C3	0.5548 (3)	0.0042 (3)	0.1463 (2)	0.0334 (6)
H3	0.6355	0.0188	0.1336	0.040*
C4	0.5597 (3)	−0.1155 (3)	0.1285 (2)	0.0353 (6)
H4	0.6451	−0.1822	0.1060	0.042*
C5	0.4395 (3)	−0.1376 (3)	0.1436 (2)	0.0323 (6)
H5	0.4449	−0.2187	0.1307	0.039*
C6	0.3106 (3)	−0.0396 (2)	0.17803 (19)	0.0269 (5)
C7	0.1771 (3)	−0.0561 (2)	0.19599 (19)	0.0266 (5)
C8	0.1793 (3)	−0.1788 (2)	0.2152 (2)	0.0341 (6)
H8	0.2659	−0.2527	0.2143	0.041*
C9	0.0543 (3)	−0.1924 (3)	0.2355 (2)	0.0360 (6)
H9	0.0570	−0.2750	0.2461	0.043*
C10	−0.0745 (3)	−0.0827 (3)	0.2400 (2)	0.0347 (6)
H10	−0.1581	−0.0917	0.2555	0.042*
C11	−0.0793 (3)	0.0401 (3)	0.2216 (2)	0.0308 (6)
H11	−0.1663	0.1133	0.2251	0.037*
C12	0.0445 (3)	0.0554 (2)	0.19813 (19)	0.0252 (5)
C13	0.0425 (2)	0.1901 (2)	0.17092 (19)	0.0235 (5)
C14	0.1680 (2)	0.1824 (2)	0.23304 (19)	0.0238 (5)
C15	0.0633 (3)	0.2121 (2)	0.0467 (2)	0.0290 (6)
H15A	−0.0174	0.2171	0.0096	0.044*
H15B	0.1479	0.1409	0.0213	0.044*
H15C	0.0723	0.2920	0.0315	0.044*
C16	0.2479 (2)	0.2390 (3)	0.3914 (2)	0.0293 (6)
C17	0.2796 (3)	0.1390 (3)	0.4746 (2)	0.0370 (7)
C18	0.3754 (3)	0.1313 (3)	0.5532 (2)	0.0490 (9)
H18	0.3996	0.0659	0.6096	0.059*
C19	0.4342 (3)	0.2176 (3)	0.5490 (3)	0.0529 (9)
H19	0.4959	0.2111	0.6032	0.064*
C20	0.4026 (3)	0.3144 (3)	0.4649 (3)	0.0462 (8)
H20	0.4444	0.3716	0.4623	0.055*
C21	0.3079 (3)	0.3267 (3)	0.3836 (2)	0.0343 (6)
C22	0.2180 (3)	0.0417 (3)	0.4797 (2)	0.0471 (8)
H22A	0.1166	0.0859	0.4905	0.071*
H22B	0.2580	−0.0219	0.5397	0.071*
H22C	0.2400	−0.0009	0.4121	0.071*
C23	0.2785 (3)	0.4301 (3)	0.2915 (3)	0.0416 (7)
H23A	0.3604	0.4064	0.2428	0.062*
H23B	0.2578	0.5117	0.3211	0.062*
H23C	0.1984	0.4382	0.2518	0.062*
C24	−0.3850 (3)	0.4894 (3)	0.2547 (3)	0.0456 (8)
H24A	−0.3840	0.4254	0.3115	0.068*
H24B	−0.4799	0.5379	0.2287	0.068*
H24C	−0.3538	0.5477	0.2835	0.068*
C25	−0.3291 (3)	0.2930 (3)	0.0638 (3)	0.0489 (8)
H25A	−0.2523	0.2249	0.0271	0.073*
H25B	−0.3996	0.3463	0.0115	0.073*
H25C	−0.3711	0.2552	0.1197	0.073*
C26	−0.2137 (3)	0.5213 (3)	0.0258 (3)	0.0478 (8)
H26A	−0.1576	0.5546	0.0603	0.072*
H26B	−0.3011	0.5923	0.0023	0.072*
H26C	−0.1617	0.4754	−0.0367	0.072*
C27	−0.0914 (3)	0.5476 (3)	0.3150 (3)	0.0488 (8)
H27A	−0.0640	0.5645	0.2410	0.073*
H27B	−0.0326	0.5605	0.3653	0.073*
H27C	−0.1892	0.6061	0.3289	0.073*
C28	−0.1394 (3)	0.3076 (3)	0.4682 (2)	0.0499 (8)
H28A	−0.2332	0.3720	0.4864	0.075*
H28B	−0.0774	0.2940	0.5275	0.075*
H28C	−0.1432	0.2272	0.4566	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Al1	0.0220 (4)	0.0301 (4)	0.0366 (4)	−0.0095 (3)	−0.0072 (3)	−0.0015 (3)
Al2	0.0225 (4)	0.0305 (4)	0.0322 (4)	−0.0090 (3)	−0.0017 (3)	−0.0079 (3)
O1	0.0195 (8)	0.0269 (9)	0.0283 (9)	−0.0090 (7)	−0.0039 (7)	−0.0031 (7)
N1	0.0210 (10)	0.0268 (11)	0.0276 (11)	−0.0090 (9)	−0.0056 (8)	−0.0026 (8)
C1	0.0198 (12)	0.0293 (13)	0.0224 (12)	−0.0065 (10)	−0.0025 (9)	−0.0018 (10)
C2	0.0259 (13)	0.0326 (14)	0.0292 (13)	−0.0125 (11)	−0.0067 (10)	−0.0027 (10)
C3	0.0203 (12)	0.0446 (16)	0.0322 (14)	−0.0109 (12)	−0.0025 (10)	−0.0032 (12)
C4	0.0218 (13)	0.0404 (16)	0.0334 (14)	−0.0032 (12)	−0.0017 (11)	−0.0059 (12)
C5	0.0293 (14)	0.0303 (14)	0.0341 (14)	−0.0091 (11)	−0.0039 (11)	−0.0044 (11)
C6	0.0250 (13)	0.0292 (13)	0.0236 (12)	−0.0090 (11)	−0.0043 (10)	0.0000 (10)
C7	0.0283 (13)	0.0297 (14)	0.0221 (12)	−0.0126 (11)	−0.0018 (10)	−0.0030 (10)
C8	0.0346 (15)	0.0252 (14)	0.0379 (15)	−0.0086 (12)	−0.0028 (12)	−0.0016 (11)
C9	0.0450 (17)	0.0295 (15)	0.0391 (16)	−0.0216 (13)	−0.0042 (13)	0.0010 (11)
C10	0.0357 (15)	0.0413 (16)	0.0344 (15)	−0.0243 (13)	−0.0035 (12)	0.0034 (12)
C11	0.0264 (13)	0.0343 (15)	0.0323 (14)	−0.0139 (11)	−0.0028 (11)	0.0007 (11)
C12	0.0267 (13)	0.0262 (13)	0.0238 (12)	−0.0124 (11)	−0.0028 (10)	−0.0013 (10)
C13	0.0182 (11)	0.0239 (12)	0.0274 (13)	−0.0078 (10)	−0.0012 (9)	−0.0028 (9)
C14	0.0227 (12)	0.0235 (12)	0.0261 (12)	−0.0113 (10)	−0.0041 (10)	0.0028 (9)
C15	0.0258 (13)	0.0310 (14)	0.0286 (13)	−0.0106 (11)	−0.0032 (10)	−0.0014 (10)
C16	0.0192 (12)	0.0353 (15)	0.0275 (13)	−0.0045 (11)	−0.0044 (10)	−0.0098 (11)
C17	0.0312 (14)	0.0365 (15)	0.0284 (14)	−0.0001 (12)	−0.0027 (11)	−0.0055 (11)
C18	0.0433 (17)	0.0500 (19)	0.0288 (15)	0.0046 (15)	−0.0106 (13)	−0.0048 (13)
C19	0.0350 (16)	0.064 (2)	0.0409 (18)	0.0012 (16)	−0.0165 (13)	−0.0203 (16)
C20	0.0278 (15)	0.057 (2)	0.0526 (19)	−0.0130 (14)	−0.0085 (13)	−0.0239 (16)
C21	0.0234 (13)	0.0384 (16)	0.0377 (15)	−0.0077 (12)	−0.0043 (11)	−0.0130 (12)
C22	0.0500 (18)	0.0384 (17)	0.0394 (17)	−0.0088 (15)	0.0020 (14)	0.0058 (13)
C23	0.0346 (16)	0.0386 (17)	0.0578 (19)	−0.0208 (13)	−0.0055 (14)	−0.0047 (14)
C24	0.0261 (14)	0.0463 (18)	0.059 (2)	−0.0099 (13)	−0.0006 (13)	−0.0086 (15)
C25	0.0359 (16)	0.0481 (18)	0.062 (2)	−0.0137 (14)	−0.0192 (15)	−0.0092 (15)
C26	0.0395 (17)	0.0454 (18)	0.0518 (19)	−0.0136 (14)	−0.0099 (14)	0.0106 (14)
C27	0.0315 (15)	0.0367 (17)	0.080 (2)	−0.0140 (13)	−0.0009 (15)	−0.0177 (16)
C28	0.0411 (17)	0.063 (2)	0.0366 (16)	−0.0146 (16)	0.0030 (13)	−0.0062 (14)

Geometric parameters (Å, º) top

Al1—O1	1.9273 (17)	C15—H15A	0.9600
Al1—C25	1.972 (3)	C15—H15B	0.9600
Al1—C26	1.974 (3)	C15—H15C	0.9600
Al1—C24	1.980 (3)	C16—C21	1.389 (4)
Al2—O1	1.8552 (17)	C16—C17	1.399 (4)
Al2—C28	1.944 (3)	C17—C18	1.401 (4)
Al2—C27	1.954 (3)	C17—C22	1.504 (4)
Al2—N1	1.993 (2)	C18—C19	1.367 (5)
O1—C13	1.436 (3)	C18—H18	0.9300
N1—C14	1.281 (3)	C19—C20	1.383 (5)
N1—C16	1.465 (3)	C19—H19	0.9300
C1—C2	1.393 (3)	C20—C21	1.403 (4)
C1—C6	1.407 (3)	C20—H20	0.9300
C1—C14	1.477 (3)	C21—C23	1.499 (4)
C2—C3	1.382 (3)	C22—H22A	0.9600
C2—H2	0.9300	C22—H22B	0.9600
C3—C4	1.382 (4)	C22—H22C	0.9600
C3—H3	0.9300	C23—H23A	0.9600
C4—C5	1.384 (4)	C23—H23B	0.9600
C4—H4	0.9300	C23—H23C	0.9600
C5—C6	1.392 (3)	C24—H24A	0.9600
C5—H5	0.9300	C24—H24B	0.9600
C6—C7	1.489 (3)	C24—H24C	0.9600
C7—C8	1.391 (4)	C25—H25A	0.9600
C7—C12	1.415 (3)	C25—H25B	0.9600
C8—C9	1.386 (4)	C25—H25C	0.9600
C8—H8	0.9300	C26—H26A	0.9600
C9—C10	1.384 (4)	C26—H26B	0.9600
C9—H9	0.9300	C26—H26C	0.9600
C10—C11	1.381 (4)	C27—H27A	0.9600
C10—H10	0.9300	C27—H27B	0.9600
C11—C12	1.388 (3)	C27—H27C	0.9600
C11—H11	0.9300	C28—H28A	0.9600
C12—C13	1.538 (3)	C28—H28B	0.9600
C13—C14	1.523 (3)	C28—H28C	0.9600
C13—C15	1.534 (3)

O1—Al1—C25	111.41 (11)	H15A—C15—H15B	109.5
O1—Al1—C26	107.52 (11)	C13—C15—H15C	109.5
C25—Al1—C26	113.94 (15)	H15A—C15—H15C	109.5
O1—Al1—C24	100.23 (11)	H15B—C15—H15C	109.5
C25—Al1—C24	109.59 (14)	C21—C16—C17	123.2 (2)
C26—Al1—C24	113.30 (14)	C21—C16—N1	119.6 (2)
O1—Al2—C28	113.23 (12)	C17—C16—N1	117.1 (2)
O1—Al2—C27	116.12 (12)	C16—C17—C18	116.5 (3)
C28—Al2—C27	120.52 (15)	C16—C17—C22	122.6 (2)
O1—Al2—N1	84.06 (8)	C18—C17—C22	120.8 (3)
C28—Al2—N1	109.79 (12)	C19—C18—C17	121.7 (3)
C27—Al2—N1	106.33 (11)	C19—C18—H18	119.2
C13—O1—Al2	116.20 (13)	C17—C18—H18	119.2
C13—O1—Al1	128.09 (14)	C18—C19—C20	120.5 (3)
Al2—O1—Al1	113.45 (9)	C18—C19—H19	119.7
C14—N1—C16	121.9 (2)	C20—C19—H19	119.7
C14—N1—Al2	113.25 (16)	C19—C20—C21	120.4 (3)
C16—N1—Al2	124.23 (15)	C19—C20—H20	119.8
C2—C1—C6	121.0 (2)	C21—C20—H20	119.8
C2—C1—C14	122.9 (2)	C16—C21—C20	117.6 (3)
C6—C1—C14	116.0 (2)	C16—C21—C23	123.0 (2)
C3—C2—C1	119.9 (2)	C20—C21—C23	119.4 (3)
C3—C2—H2	120.1	C17—C22—H22A	109.5
C1—C2—H2	120.1	C17—C22—H22B	109.5
C2—C3—C4	119.5 (2)	H22A—C22—H22B	109.5
C2—C3—H3	120.2	C17—C22—H22C	109.5
C4—C3—H3	120.2	H22A—C22—H22C	109.5
C3—C4—C5	121.1 (2)	H22B—C22—H22C	109.5
C3—C4—H4	119.5	C21—C23—H23A	109.5
C5—C4—H4	119.5	C21—C23—H23B	109.5
C4—C5—C6	120.5 (2)	H23A—C23—H23B	109.5
C4—C5—H5	119.7	C21—C23—H23C	109.5
C6—C5—H5	119.7	H23A—C23—H23C	109.5
C5—C6—C1	118.0 (2)	H23B—C23—H23C	109.5
C5—C6—C7	123.6 (2)	Al1—C24—H24A	109.5
C1—C6—C7	118.4 (2)	Al1—C24—H24B	109.5
C8—C7—C12	118.8 (2)	H24A—C24—H24B	109.5
C8—C7—C6	121.6 (2)	Al1—C24—H24C	109.5
C12—C7—C6	119.6 (2)	H24A—C24—H24C	109.5
C9—C8—C7	120.9 (2)	H24B—C24—H24C	109.5
C9—C8—H8	119.5	Al1—C25—H25A	109.5
C7—C8—H8	119.5	Al1—C25—H25B	109.5
C10—C9—C8	119.8 (2)	H25A—C25—H25B	109.5
C10—C9—H9	120.1	Al1—C25—H25C	109.5
C8—C9—H9	120.1	H25A—C25—H25C	109.5
C11—C10—C9	120.2 (3)	H25B—C25—H25C	109.5
C11—C10—H10	119.9	Al1—C26—H26A	109.5
C9—C10—H10	119.9	Al1—C26—H26B	109.5
C10—C11—C12	120.7 (2)	H26A—C26—H26B	109.5
C10—C11—H11	119.7	Al1—C26—H26C	109.5
C12—C11—H11	119.7	H26A—C26—H26C	109.5
C11—C12—C7	119.5 (2)	H26B—C26—H26C	109.5
C11—C12—C13	122.1 (2)	Al2—C27—H27A	109.5
C7—C12—C13	118.3 (2)	Al2—C27—H27B	109.5
O1—C13—C14	108.52 (18)	H27A—C27—H27B	109.5
O1—C13—C15	110.23 (19)	Al2—C27—H27C	109.5
C14—C13—C15	111.17 (19)	H27A—C27—H27C	109.5
O1—C13—C12	113.07 (18)	H27B—C27—H27C	109.5
C14—C13—C12	103.48 (19)	Al2—C28—H28A	109.5
C15—C13—C12	110.20 (19)	Al2—C28—H28B	109.5
N1—C14—C1	127.7 (2)	H28A—C28—H28B	109.5
N1—C14—C13	117.1 (2)	Al2—C28—H28C	109.5
C1—C14—C13	114.8 (2)	H28A—C28—H28C	109.5
C13—C15—H15A	109.5	H28B—C28—H28C	109.5
C13—C15—H15B	109.5

Experimental details

Crystal data
Chemical formula	[Al₂(CH₃)₅(C₂₃H₂₀NO)]
M_r	455.53
Crystal system, space group	Triclinic, P1
Temperature (K)	185
a, b, c (Å)	10.4535 (17), 11.4306 (18), 12.221 (2)
α, β, γ (°)	84.930 (3), 86.308 (3), 64.092 (2)
V (Å³)	1307.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.36 × 0.32 × 0.19

Data collection
Diffractometer	SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.955, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	6899, 4966, 3558
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.150, 1.03
No. of reflections	4966
No. of parameters	297
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.36

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Al1—O1	1.9273 (17)	Al2—O1	1.8552 (17)
Al1—C25	1.972 (3)	Al2—C28	1.944 (3)
Al1—C26	1.974 (3)	Al2—C27	1.954 (3)
Al1—C24	1.980 (3)	Al2—N1	1.993 (2)

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 21074043) for support.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Evans, K. A. (1993). Chemistry of Aluminium, Gallium, Indium and Thallium., edited by A. J. Downs, p. 248. Chapman & Hall: New York. Google Scholar
Gao, A., Su, Q. & Mu, Y. (2009). Acta Cryst. E65, m577. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, L. (2009). ARKIVOC, pp 95–111. Google Scholar
Liu, X.-M., Gao, W., Mu, Y., Li, G.-H., Ye, L., Xia, H., Ren, Y. & Feng, S. (2005). Organometallics, 24, 1614–1619. Web of Science CSD CrossRef CAS Google Scholar
Liu, X.-M., Xia, H., Gao, W., Ye, L., Mu, Y., Su, Q. & Ren, Y. (2006). Eur. J. Inorg. Chem., pp. 1216–1222. Google Scholar
Ren, Y., Liu, X.-M., Gao, W., Xia, H., Ye, L. & Mu, Y. (2007). Eur. J. Inorg. Chem., pp. 1808–1814. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, Q., Gao, W., Wu, Q.-L., Ye, L., Li, G.-H. & Mu, Y. (2007). Eur. J. Inorg. Chem., pp. 4168–4175. Google Scholar
Wang, H.-Y., Meng, X. & Jin, G.-X. (2006). Dalton Trans. pp. 2579–2585. Web of Science CSD CrossRef CAS Google Scholar
Yao, W., Mu, Y., Gao, A.-H., Su, Q., Liu, Y.-J. & Zhang, Y.-Y. (2008). Polymer, 49, 2486–2491. Web of Science CrossRef CAS Google Scholar

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