{μ-[2-(Dimethyl-amino)phen-yl](2-fluoro-phen-yl)methano-lato}penta-methyl-dialuminum(III).

Each of the Al atoms in the title compound, [Al(2)(CH(3))(5)(C(15)H(15)FNO)], is four-coordinated in a distorted tetra-hedral geometry. The dimethyl-aluminium centre is bound by the N and the O atoms of the (2-dimethyl-amino-phen-yl)(2-fluoro-phen-yl)methano-late ligand. The second Al atom is bound by the methano-late 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 = 373.41

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.130

S = 1.09

4318 reflections

233 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −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.

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

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

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

[Al2(CH3)5(C15H15FNO)]	Dx = 1.128 Mg m−3
Mr = 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

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

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(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3
4318 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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