{μ-[2-(Dimethyl­amino)phen­yl](2-fluoro­phen­yl)methano­lato}penta­methyl­dialuminum(III)

Gao, A.; Su, Q.; Mu, Y.

doi:10.1107/S1600536809012252

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m577

doi:10.1107/S1600536809012252

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{μ-[2-(Dimethylamino)phenyl](2-fluorophenyl)methanolato}pentamethyldialuminum(III)

Aihong Gao,^a Qing Su ^b and Ying Mu ^a ^*

^aState Key Laboratory of Supramolecular Structures 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: ymu@jlu.edu.cn

(Received 2 March 2009; accepted 1 April 2009; online 25 April 2009)

Each of the Al atoms in the title compound, [Al₂(CH₃)₅(C₁₅H₁₅FNO)], is four-coordinated in a distorted tetrahedral geometry. The dimethylaluminium centre is bound by the N and the O atoms of the (2-dimethylaminophenyl)(2-fluorophenyl)methanolate ligand. The second Al atom is bound by the methanolate O atom and by three methyl C atoms. The crystal studied was a racemic twin with a 0.4 (2):0.6 (2) domain ratio.

Related literature

For organoaluminum complexes, see: Atwood & Harvey (2001 ); Dechy-Cabaret et al. (2004 ); Izod (2002 ); Linton et al. (2001 ); Liu et al. (2000 ); Ma et al. (2005 ); Nomura et al. (2005 ). For the synthesis of the ligand, see: Al-Masri et al. (2004a ). For a discussion of chirality in the ligand, see: Al-Masri et al. (2004b ).

Experimental

Crystal data

[Al₂(CH₃)₅(C₁₅H₁₅FNO)]
M_r = 373.41
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1089 (7) Å
b = 13.1601 (10) Å
c = 18.3443 (15) Å
V = 2199.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 295 K
0.21 × 0.13 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.970, T_max = 0.984
12338 measured reflections
4318 independent reflections
3641 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.130
S = 1.09
4318 reflections
233 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012252/tk2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012252/tk2388Isup2.hkl

checkCIF report

Comment top

Organoaluminum complexes have attracted considerable attention due to their rich structural chemistry (Izod, 2002), applications in organic synthesis (Linton et al., 2001) and in catalytic chemistry (Dechy-Cabaret et al., 2004; Liu et al., 2000). A large number of ligands have been used to stabilize organoaluminum complexes and to tune the properties of their complexes. Among them, salen (Atwood & Harvey, 2001), salicylaldimine (Nomura et al., 2005) and 1,4-dithiabutanediylbis(6-tert-butyl-4-methylphenol) ligands (Ma et al., 2005) have attracted considerable attention. The aminophenylalcohol ligand, with a similar framework to the salicylaldimine ligand has been less well investigated. Herein, the structure of the title aluminium complex, (I), with the aminophenylalcohol ligand, is reported.

In the molecule of (I), Fig. 1, the Al atoms exist in different coordination environments, but with both adopting distorted tetrahedral geometries. The tetrahedral coordination around the Al1 atom involves three methyl-C atoms and the O1 atom from the deprotonated aminophenylalcohol ligand. The tetrahedral coordination around the Al2 atom involves the N1 atom and the O1 atom from the ligand and two methyl-C atoms. The (2-dimethylamino-phenyl)(2-fluoro-phenyl)methanolate ligand is therefore tridentate, bridging the two Al atoms via the O1 atom. The Al—Al separation within the dimer is 3.2631 (12) Å. The Al2—O distance (1.8165 (19) Å) is significantly shorter than the Al1—O distance (1.9199 (19) Å) because the former bond has more covalent chartacter. The six-membered chelate ring, O1/Al2/N1/C1/C6/C7, has a boat conformation with the C7 and N1 atoms occupying the apex positions. The dihedral angle between the two phenyl rings is 79.3°. Compound (I) was refined as a racemic twin.

Related literature top

For organoaluminum complexes, see: Atwood & Harvey (2001); Dechy-Cabaret et al. (2004); Izod (2002); Linton et al. (2001); Liu et al. (2000); Ma et al. (2005); Nomura et al. (2005). For the synthesis of the ligand, see: Al-Masri et al. (2004a). For a discussion of chirality in the ligand, see: Al-Masri et al. (2004b).

Experimental top

The precursor compound (2-dimethylamino-phenyl)-(2-fluoro-phenyl)methanol was synthesized according to a modified literature procedure (Al-Masri et al., 2004a). After removal of the solvent of a solution of nBuLi (79 ml, 79 mmol), N,N-dimethylaniline (10.0 ml, 79 mmol) was added at 0 °C with stirring, and the solution was slowly heated to 80 °C for 24 h, during which a yellow solid was formed. 2-FC₆H₄CHO (10.0 g, 79 mmol) in 40 ml of Et₂O was added to the mixture at 0 °C. After stirring for 12 h, the reaction was quenched with H₂O (30 ml), and the organic phase was separated, washed with brine, and dried over magnesium sulfate. The solvent was removed in vacuo to give the crude product as a yellow solid. The pure product was obtained by recrystallization from methanol as a white solid (13.9 g, 82%). The absolute configuration of the ligand could not be determined (Al-Masri et al., 2004b). AlMe₃ (4.0 ml, 1.0 M in toluene, 4.0 mmol) was added to a solution of (2-dimethylamino-phenyl)-(2-fluoro-phenyl)-methanol (0.49 g, 2.0 mmol) in toluene (20 ml) at -10 °C with stirring. The solution was gently heated to 60 °C for 24 h. After removal of the solvent, the product was crystallized from hexane and the desired complex (I) as a yellow crystalline solid (0.64 g, 87%) was obtained.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for reasons of clarity.
	Fig. 2. The formation of the title compound.

{µ-[2-(Dimethylamino)phenyl](2- fluorophenyl)methanolato}pentamethyldialuminum(III) top

Crystal data top

[Al₂(CH₃)₅(C₁₅H₁₅FNO)]	D_x = 1.128 Mg m⁻³
M_r = 373.41	Melting point: not measured K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4318 reflections
a = 9.1089 (7) Å	θ = 1.9–26.4°
b = 13.1601 (10) Å	µ = 0.15 mm⁻¹
c = 18.3443 (15) Å	T = 295 K
V = 2199.0 (3) Å³	Block, yellow
Z = 4	0.21 × 0.13 × 0.11 mm
F(000) = 800

Data collection top

Bruker SMART CCD area-detector diffractometer	4318 independent reflections
Radiation source: fine-focus sealed tube	3641 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 9.00 cm pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ϕ and ω scans	h = −9→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −16→13
T_min = 0.970, T_max = 0.984	l = −22→22
12338 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0726P)²] where P = (F_o² + 2F_c²)/3
4318 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

[Al₂(CH₃)₅(C₁₅H₁₅FNO)]	V = 2199.0 (3) Å³
M_r = 373.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1089 (7) Å	µ = 0.15 mm⁻¹
b = 13.1601 (10) Å	T = 295 K
c = 18.3443 (15) Å	0.21 × 0.13 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4318 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3641 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.984	R_int = 0.039
12338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.09	Δρ_max = 0.65 e Å⁻³
4318 reflections	Δρ_min = −0.17 e Å⁻³
233 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.10860 (9)	0.46062 (7)	0.20698 (4)	0.0355 (2)
Al2	0.88654 (11)	0.37629 (6)	0.08119 (5)	0.0394 (2)
C1	0.7128 (3)	0.5518 (2)	0.04877 (15)	0.0376 (6)
C2	0.6729 (4)	0.6132 (3)	−0.00967 (18)	0.0564 (9)
H2	0.6312	0.5839	−0.0509	0.068*
C3	0.6939 (5)	0.7156 (3)	−0.00766 (19)	0.0622 (11)
H3	0.6659	0.7555	−0.0471	0.075*
C4	0.7561 (5)	0.7600 (3)	0.05242 (19)	0.0570 (10)
H4	0.7724	0.8298	0.0535	0.068*
C5	0.7942 (4)	0.7009 (2)	0.11100 (17)	0.0433 (7)
H5	0.8360	0.7315	0.1517	0.052*
C6	0.7722 (3)	0.5967 (2)	0.11129 (15)	0.0349 (6)
C7	0.8237 (3)	0.5385 (2)	0.17944 (14)	0.0312 (6)
H7	0.8830	0.5865	0.2077	0.037*
C8	0.7058 (3)	0.4993 (2)	0.23137 (14)	0.0326 (6)
C9	0.5929 (3)	0.5616 (2)	0.25606 (15)	0.0376 (7)
C10	0.4867 (3)	0.5293 (3)	0.30503 (17)	0.0490 (8)
H10	0.4127	0.5732	0.3200	0.059*
C11	0.4926 (4)	0.4320 (3)	0.33089 (18)	0.0519 (9)
H11	0.4211	0.4092	0.3631	0.062*
C12	0.6030 (4)	0.3679 (3)	0.30967 (17)	0.0492 (8)
H12	0.6075	0.3022	0.3281	0.059*
C13	0.7082 (3)	0.4015 (2)	0.26058 (16)	0.0391 (7)
H13	0.7827	0.3573	0.2467	0.047*
C14	0.5573 (4)	0.4087 (3)	0.0817 (2)	0.0515 (8)
H14A	0.5575	0.4322	0.1312	0.077*
H14B	0.5498	0.3359	0.0810	0.077*
H14C	0.4752	0.4376	0.0563	0.077*
C15	0.6867 (5)	0.4024 (3)	−0.03245 (18)	0.0603 (10)
H15A	0.5921	0.4194	−0.0520	0.090*
H15B	0.6991	0.3299	−0.0330	0.090*
H15C	0.7620	0.4334	−0.0615	0.090*
C16	1.0316 (4)	0.4098 (3)	0.00634 (19)	0.0651 (11)
H16A	1.0177	0.4788	−0.0093	0.098*
H16B	1.0197	0.3650	−0.0345	0.098*
H16C	1.1286	0.4021	0.0261	0.098*
C17	0.8374 (5)	0.2368 (2)	0.1079 (2)	0.0615 (10)
H17A	0.9130	0.2096	0.1387	0.092*
H17B	0.8296	0.1962	0.0646	0.092*
H17C	0.7455	0.2360	0.1334	0.092*
C18	1.1997 (4)	0.3299 (3)	0.17878 (19)	0.0558 (9)
H18A	1.1376	0.2749	0.1938	0.084*
H18B	1.2937	0.3236	0.2020	0.084*
H18C	1.2121	0.3279	0.1268	0.084*
C19	1.0612 (3)	0.4677 (3)	0.31239 (15)	0.0426 (7)
H19A	0.9969	0.5243	0.3212	0.064*
H19B	1.1500	0.4764	0.3398	0.064*
H19C	1.0136	0.4060	0.3272	0.064*
C20	1.1980 (4)	0.5841 (3)	0.1655 (2)	0.0576 (10)
H20A	1.1874	0.5833	0.1134	0.086*
H20B	1.3004	0.5862	0.1779	0.086*
H20C	1.1498	0.6430	0.1850	0.086*
F1	0.5848 (2)	0.65789 (13)	0.23063 (10)	0.0526 (5)
N1	0.6977 (3)	0.4407 (2)	0.04485 (13)	0.0419 (6)
O1	0.92059 (19)	0.45697 (14)	0.15974 (9)	0.0319 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Al1	0.0302 (4)	0.0426 (5)	0.0336 (4)	0.0007 (4)	−0.0021 (4)	0.0045 (3)
Al2	0.0461 (5)	0.0358 (5)	0.0363 (4)	0.0089 (4)	−0.0048 (4)	−0.0070 (3)
C1	0.0364 (15)	0.0405 (17)	0.0358 (14)	0.0091 (14)	−0.0039 (12)	0.0024 (12)
C2	0.064 (2)	0.064 (2)	0.0409 (17)	0.013 (2)	−0.0107 (16)	0.0046 (15)
C3	0.086 (3)	0.052 (2)	0.049 (2)	0.018 (2)	−0.004 (2)	0.0183 (17)
C4	0.078 (3)	0.0336 (18)	0.059 (2)	0.0099 (18)	0.0115 (19)	0.0106 (15)
C5	0.0482 (19)	0.0369 (17)	0.0449 (16)	0.0039 (15)	0.0052 (15)	0.0023 (13)
C6	0.0342 (15)	0.0350 (16)	0.0355 (14)	0.0051 (13)	0.0041 (12)	0.0003 (12)
C7	0.0328 (14)	0.0279 (13)	0.0331 (13)	0.0020 (12)	−0.0032 (11)	−0.0063 (11)
C8	0.0262 (15)	0.0406 (15)	0.0311 (13)	0.0002 (12)	−0.0038 (11)	−0.0040 (11)
C9	0.0395 (17)	0.0361 (16)	0.0371 (14)	0.0012 (14)	−0.0048 (14)	−0.0040 (12)
C10	0.0313 (16)	0.067 (2)	0.0489 (18)	0.0017 (16)	0.0049 (14)	−0.0135 (17)
C11	0.0396 (18)	0.069 (2)	0.0469 (18)	−0.0107 (17)	0.0071 (15)	0.0043 (17)
C12	0.052 (2)	0.0467 (18)	0.0488 (18)	−0.0114 (17)	−0.0033 (16)	0.0061 (13)
C13	0.0352 (16)	0.0389 (17)	0.0433 (16)	−0.0003 (13)	−0.0017 (13)	−0.0010 (13)
C14	0.0427 (18)	0.051 (2)	0.061 (2)	−0.0049 (15)	−0.0136 (16)	−0.0063 (16)
C15	0.071 (3)	0.066 (2)	0.0437 (18)	0.009 (2)	−0.0214 (18)	−0.0159 (16)
C16	0.063 (2)	0.093 (3)	0.0397 (18)	0.023 (2)	0.0042 (17)	−0.0035 (19)
C17	0.074 (3)	0.0376 (19)	0.073 (2)	0.0052 (17)	−0.020 (2)	−0.0111 (16)
C18	0.049 (2)	0.068 (2)	0.0507 (19)	0.0196 (18)	−0.0025 (16)	0.0013 (17)
C19	0.0427 (17)	0.0503 (19)	0.0349 (15)	0.0009 (15)	−0.0037 (12)	−0.0006 (13)
C20	0.047 (2)	0.062 (2)	0.063 (2)	−0.0124 (18)	−0.0082 (17)	0.0220 (18)
F1	0.0529 (12)	0.0404 (10)	0.0646 (11)	0.0095 (8)	0.0089 (10)	−0.0038 (8)
N1	0.0441 (15)	0.0428 (15)	0.0387 (13)	0.0033 (12)	−0.0117 (12)	−0.0068 (11)
O1	0.0298 (10)	0.0329 (10)	0.0331 (9)	0.0040 (8)	−0.0009 (7)	−0.0037 (7)

Geometric parameters (Å, º) top

Al1—O1	1.9200 (19)	C11—C12	1.369 (5)
Al1—C20	1.971 (3)	C11—H11	0.9300
Al1—C18	1.978 (3)	C12—C13	1.387 (4)
Al1—C19	1.984 (3)	C12—H12	0.9300
Al2—O1	1.8165 (19)	C13—H13	0.9300
Al2—C17	1.952 (4)	C14—N1	1.506 (4)
Al2—C16	1.956 (4)	C14—H14A	0.9600
Al2—N1	2.030 (3)	C14—H14B	0.9600
C1—C2	1.391 (4)	C14—H14C	0.9600
C1—C6	1.399 (4)	C15—N1	1.508 (4)
C1—N1	1.471 (4)	C15—H15A	0.9600
C2—C3	1.361 (5)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.370 (5)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.372 (4)	C16—H16C	0.9600
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.386 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.540 (4)	C18—H18A	0.9600
C7—O1	1.435 (3)	C18—H18B	0.9600
C7—C8	1.525 (4)	C18—H18C	0.9600
C7—H7	0.9800	C19—H19A	0.9600
C8—C9	1.391 (4)	C19—H19B	0.9600
C8—C13	1.395 (4)	C19—H19C	0.9600
C9—F1	1.352 (3)	C20—H20A	0.9600
C9—C10	1.387 (4)	C20—H20B	0.9600
C10—C11	1.366 (5)	C20—H20C	0.9600
C10—H10	0.9300

O1—Al1—C20	102.42 (12)	C8—C13—H13	118.9
O1—Al1—C18	103.56 (13)	N1—C14—H14A	109.5
C20—Al1—C18	116.26 (16)	N1—C14—H14B	109.5
O1—Al1—C19	104.29 (11)	H14A—C14—H14B	109.5
C20—Al1—C19	115.31 (16)	N1—C14—H14C	109.5
C18—Al1—C19	112.79 (14)	H14A—C14—H14C	109.5
O1—Al2—C17	112.96 (14)	H14B—C14—H14C	109.5
O1—Al2—C16	108.04 (14)	N1—C15—H15A	109.5
C17—Al2—C16	122.89 (17)	N1—C15—H15B	109.5
O1—Al2—N1	99.28 (10)	H15A—C15—H15B	109.5
C17—Al2—N1	106.28 (15)	N1—C15—H15C	109.5
C16—Al2—N1	104.34 (14)	H15A—C15—H15C	109.5
C2—C1—C6	119.1 (3)	H15B—C15—H15C	109.5
C2—C1—N1	121.1 (3)	Al2—C16—H16A	109.5
C6—C1—N1	119.8 (2)	Al2—C16—H16B	109.5
C3—C2—C1	121.2 (3)	H16A—C16—H16B	109.5
C3—C2—H2	119.4	Al2—C16—H16C	109.5
C1—C2—H2	119.4	H16A—C16—H16C	109.5
C2—C3—C4	120.2 (3)	H16B—C16—H16C	109.5
C2—C3—H3	119.9	Al2—C17—H17A	109.5
C4—C3—H3	119.9	Al2—C17—H17B	109.5
C3—C4—C5	119.5 (3)	H17A—C17—H17B	109.5
C3—C4—H4	120.2	Al2—C17—H17C	109.5
C5—C4—H4	120.2	H17A—C17—H17C	109.5
C4—C5—C6	121.9 (3)	H17B—C17—H17C	109.5
C4—C5—H5	119.1	Al1—C18—H18A	109.5
C6—C5—H5	119.1	Al1—C18—H18B	109.5
C5—C6—C1	118.1 (3)	H18A—C18—H18B	109.5
C5—C6—C7	116.8 (3)	Al1—C18—H18C	109.5
C1—C6—C7	125.0 (2)	H18A—C18—H18C	109.5
O1—C7—C8	109.7 (2)	H18B—C18—H18C	109.5
O1—C7—C6	110.8 (2)	Al1—C19—H19A	109.5
C8—C7—C6	117.5 (2)	Al1—C19—H19B	109.5
O1—C7—H7	106.0	H19A—C19—H19B	109.5
C8—C7—H7	106.0	Al1—C19—H19C	109.5
C6—C7—H7	106.0	H19A—C19—H19C	109.5
C9—C8—C13	115.5 (3)	H19B—C19—H19C	109.5
C9—C8—C7	121.7 (2)	Al1—C20—H20A	109.5
C13—C8—C7	122.7 (2)	Al1—C20—H20B	109.5
F1—C9—C10	118.2 (3)	H20A—C20—H20B	109.5
F1—C9—C8	118.7 (3)	Al1—C20—H20C	109.5
C10—C9—C8	123.1 (3)	H20A—C20—H20C	109.5
C11—C10—C9	119.0 (3)	H20B—C20—H20C	109.5
C11—C10—H10	120.5	C1—N1—C14	109.6 (2)
C9—C10—H10	120.5	C1—N1—C15	112.6 (2)
C10—C11—C12	120.5 (3)	C14—N1—C15	105.8 (3)
C10—C11—H11	119.8	C1—N1—Al2	108.64 (17)
C12—C11—H11	119.8	C14—N1—Al2	117.10 (19)
C11—C12—C13	119.7 (3)	C15—N1—Al2	103.0 (2)
C11—C12—H12	120.1	C7—O1—Al2	122.10 (15)
C13—C12—H12	120.1	C7—O1—Al1	114.61 (15)
C12—C13—C8	122.2 (3)	Al2—O1—Al1	121.66 (10)
C12—C13—H13	118.9

Experimental details

Crystal data
Chemical formula	[Al₂(CH₃)₅(C₁₅H₁₅FNO)]
M_r	373.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	9.1089 (7), 13.1601 (10), 18.3443 (15)
V (Å³)	2199.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.21 × 0.13 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.970, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	12338, 4318, 3641
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.130, 1.09
No. of reflections	4318
No. of parameters	233
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.17

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

Acknowledgements

We thank the National Natural Science Foundation of China (grant Nos. 20772044 and 20674024).

References

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