Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044388/zl2062sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044388/zl2062Isup2.hkl |
CCDC reference: 663609
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.105
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C7 .. 7.92 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 6.08 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 6.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C23 .. 5.11 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Al1 - C25 .. 6.74 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A solution of ortho-C6H4NH(C6H3-2,6-Me2)(CH=NC6H3-2,6-Me2) (0.20 g, 0.61 mmol) (Liu et al., 2005) in 10 ml of n-hexane was slowly added to a solution of AlMe3 (0.61 mmol) in 15 ml of n-hexane at 273 K with stirring. The mixture was stirred at 273 K for 30 min, and at room temperature for additional 2 h, was then concentrated to about 10 ml and kept at 253 K overnight to let the product crystallize. The product was obtained as orange-green crystals (0.21 g, 90%).
The C-bound H atoms were positioned geometrically with C—H = 0.93–0.96 Å, and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for all other hydrogen atoms.
Organoaluminium complexes are currently generating considerable interest due to their increasing role in polymerization chemistry, such as cationic (Bochmann & Dawson, 1996), anionic (Kuroki et al., 1991) and ring-opening polymerization, (Jegier & Atwood, 1997) and as cocatalysts in transition metal-catalysed olefin polymerization (McKnight & Waymouth, 1998; Britovsek et al., 1999). Previously, a lot of alkylaluminium complexes with bidentate (Gameron et al., 2001; Pappalardo et al., 2002) or tridentate (Gameron et al., 1999; Huang et al., 2001) Schiff base ligands have been reported. Our current research efforts are focused on alkylaluminium complexes with new ligands. Herein we report the structure of the title complex, a mononuclear Schiff base dimethyl aluminium complex.
An ORTEP drawing of the molecular structure of the complex is shown in Fig. 1. The aluminium atom exhibits a distorted tetrahedral geometry. The N—Al—N angle (93.8°) in the complex is similar to that of ortho-C6H4N(C6H4-4-Me)(CH=NC6H4-4-Me)AlMe2 (94.5°, Liu et al., 2005), but larger than those in {tBuC(NCy)2}AlMe2 (Coles et al., 1997) and {(iPr)2ATI}AlMe2 (Dias et al., 1995) with four- and five- membered chelating rings, which exhibit angles of 69° and 84°, respectively. In the title compound the six membered chelating ring is nearly planar and the distance of the aluminium atom from the mean plane made up by the other five atoms of the six membered ring is only 0.1383 (7) Å. The imino C=N bond in the complex retains its double bond character with a bond length of 1.295 (2) Å.
For related literature, see: Bochmann & Dawson (1996); Britovsek et al. (1999); Coles et al. (1997); Dias et al. (1995); Gameron et al. (1999, 2001); Huang et al. (2001); Jegier & Atwood (1997); Kuroki et al. (1991); Liu et al. (2005); Pappalardo et al. (2002); McKnight & Waymouth (1998).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms were omitted for clarity. |
[Al(CH3)2(C23H23N2)] | F(000) = 824 |
Mr = 384.48 | Dx = 1.136 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11340 reflections |
a = 9.0483 (18) Å | θ = 5.8–54.9° |
b = 11.045 (2) Å | µ = 0.10 mm−1 |
c = 24.192 (5) Å | T = 293 K |
β = 111.64 (3)° | Block, yellow |
V = 2247.3 (8) Å3 | 0.19 × 0.18 × 0.15 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5115 independent reflections |
Radiation source: fine-focus sealed tube | 2682 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.981, Tmax = 0.985 | k = −14→14 |
11340 measured reflections | l = −28→31 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0378P)2] where P = (Fo2 + 2Fc2)/3 |
5115 reflections | (Δ/σ)max = 0.002 |
259 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
[Al(CH3)2(C23H23N2)] | V = 2247.3 (8) Å3 |
Mr = 384.48 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0483 (18) Å | µ = 0.10 mm−1 |
b = 11.045 (2) Å | T = 293 K |
c = 24.192 (5) Å | 0.19 × 0.18 × 0.15 mm |
β = 111.64 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5115 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2682 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.985 | Rint = 0.043 |
11340 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.16 e Å−3 |
5115 reflections | Δρmin = −0.18 e Å−3 |
259 parameters |
Experimental. (See detailed section in the paper) |
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. |
x | y | z | Uiso*/Ueq | ||
Al1 | 0.26222 (6) | 0.28378 (5) | 0.10575 (2) | 0.04098 (16) | |
N1 | 0.41224 (16) | 0.39710 (13) | 0.15157 (6) | 0.0402 (4) | |
N2 | 0.39168 (17) | 0.23307 (13) | 0.06112 (6) | 0.0405 (4) | |
C1 | 0.5702 (2) | 0.40123 (15) | 0.16054 (7) | 0.0388 (4) | |
C2 | 0.6757 (2) | 0.47997 (17) | 0.20191 (8) | 0.0499 (5) | |
H2 | 0.6370 | 0.5323 | 0.2235 | 0.060* | |
C3 | 0.8334 (2) | 0.48160 (19) | 0.21122 (9) | 0.0563 (5) | |
H3 | 0.9001 | 0.5342 | 0.2395 | 0.068* | |
C4 | 0.8975 (2) | 0.40686 (19) | 0.17966 (9) | 0.0600 (6) | |
H4 | 1.0057 | 0.4085 | 0.1867 | 0.072* | |
C5 | 0.7995 (2) | 0.33225 (18) | 0.13870 (9) | 0.0539 (5) | |
H5 | 0.8413 | 0.2825 | 0.1171 | 0.065* | |
C6 | 0.6352 (2) | 0.32662 (16) | 0.12728 (8) | 0.0410 (4) | |
C7 | 0.5424 (2) | 0.25570 (16) | 0.07846 (8) | 0.0466 (5) | |
H7 | 0.5956 | 0.2210 | 0.0560 | 0.056* | |
C8 | 0.3519 (2) | 0.48571 (17) | 0.18158 (8) | 0.0435 (5) | |
C9 | 0.3534 (2) | 0.4627 (2) | 0.23841 (9) | 0.0545 (5) | |
C10 | 0.2850 (3) | 0.5477 (3) | 0.26395 (11) | 0.0775 (8) | |
H10 | 0.2853 | 0.5347 | 0.3020 | 0.093* | |
C11 | 0.2172 (3) | 0.6506 (3) | 0.23360 (15) | 0.0872 (9) | |
H11 | 0.1694 | 0.7057 | 0.2509 | 0.105* | |
C12 | 0.2188 (3) | 0.6734 (2) | 0.17843 (14) | 0.0799 (8) | |
H12 | 0.1724 | 0.7439 | 0.1585 | 0.096* | |
C13 | 0.2891 (2) | 0.59224 (18) | 0.15176 (10) | 0.0582 (6) | |
C14 | 0.4301 (3) | 0.3531 (2) | 0.27284 (9) | 0.0817 (7) | |
H14A | 0.4346 | 0.2906 | 0.2459 | 0.123* | |
H14B | 0.3691 | 0.3252 | 0.2955 | 0.123* | |
H14C | 0.5359 | 0.3728 | 0.2993 | 0.123* | |
C15 | 0.3006 (3) | 0.6233 (2) | 0.09329 (11) | 0.0847 (8) | |
H15A | 0.2323 | 0.6907 | 0.0759 | 0.127* | |
H15B | 0.2685 | 0.5548 | 0.0671 | 0.127* | |
H15C | 0.4084 | 0.6442 | 0.0993 | 0.127* | |
C16 | 0.3169 (2) | 0.17614 (18) | 0.00394 (9) | 0.0485 (5) | |
C17 | 0.2837 (3) | 0.0534 (2) | 0.00084 (11) | 0.0667 (6) | |
C18 | 0.1980 (3) | 0.0062 (3) | −0.05477 (15) | 0.0936 (9) | |
H18 | 0.1706 | −0.0754 | −0.0583 | 0.112* | |
C19 | 0.1535 (3) | 0.0758 (4) | −0.10386 (15) | 0.1062 (12) | |
H19 | 0.0949 | 0.0419 | −0.1406 | 0.127* | |
C20 | 0.1932 (3) | 0.1959 (3) | −0.10033 (11) | 0.0879 (8) | |
H20 | 0.1643 | 0.2422 | −0.1348 | 0.106* | |
C21 | 0.2751 (3) | 0.2486 (2) | −0.04632 (9) | 0.0607 (6) | |
C22 | 0.3397 (4) | −0.0260 (2) | 0.05438 (13) | 0.1026 (10) | |
H22A | 0.3767 | 0.0232 | 0.0896 | 0.154* | |
H22B | 0.4250 | −0.0763 | 0.0531 | 0.154* | |
H22C | 0.2535 | −0.0761 | 0.0549 | 0.154* | |
C23 | 0.3145 (3) | 0.3815 (2) | −0.04262 (11) | 0.0872 (8) | |
H23A | 0.2651 | 0.4178 | −0.0811 | 0.131* | |
H23B | 0.4277 | 0.3916 | −0.0294 | 0.131* | |
H23C | 0.2760 | 0.4199 | −0.0150 | 0.131* | |
C24 | 0.0638 (2) | 0.35035 (19) | 0.05008 (9) | 0.0601 (6) | |
H24A | 0.0194 | 0.4049 | 0.0707 | 0.090* | |
H24B | −0.0098 | 0.2857 | 0.0330 | 0.090* | |
H24C | 0.0841 | 0.3932 | 0.0191 | 0.090* | |
C25 | 0.2286 (3) | 0.15255 (19) | 0.15330 (9) | 0.0702 (6) | |
H25A | 0.3293 | 0.1184 | 0.1775 | 0.105* | |
H25B | 0.1638 | 0.0912 | 0.1275 | 0.105* | |
H25C | 0.1761 | 0.1832 | 0.1784 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Al1 | 0.0376 (3) | 0.0463 (3) | 0.0386 (3) | −0.0041 (3) | 0.0135 (2) | 0.0009 (3) |
N1 | 0.0371 (8) | 0.0443 (9) | 0.0402 (9) | −0.0009 (7) | 0.0156 (7) | −0.0046 (7) |
N2 | 0.0405 (8) | 0.0392 (9) | 0.0421 (9) | −0.0055 (7) | 0.0157 (7) | −0.0019 (7) |
C1 | 0.0395 (10) | 0.0405 (10) | 0.0336 (10) | −0.0042 (9) | 0.0101 (8) | 0.0022 (8) |
C2 | 0.0459 (12) | 0.0568 (12) | 0.0485 (12) | −0.0062 (10) | 0.0189 (10) | −0.0105 (10) |
C3 | 0.0451 (12) | 0.0671 (14) | 0.0543 (13) | −0.0140 (11) | 0.0156 (10) | −0.0128 (11) |
C4 | 0.0416 (11) | 0.0752 (15) | 0.0658 (14) | −0.0104 (11) | 0.0230 (11) | −0.0070 (12) |
C5 | 0.0461 (12) | 0.0606 (13) | 0.0611 (13) | −0.0036 (10) | 0.0268 (10) | −0.0095 (11) |
C6 | 0.0388 (10) | 0.0452 (11) | 0.0427 (11) | −0.0041 (9) | 0.0194 (9) | −0.0028 (9) |
C7 | 0.0516 (12) | 0.0442 (11) | 0.0501 (12) | −0.0008 (9) | 0.0258 (10) | −0.0031 (9) |
C8 | 0.0316 (10) | 0.0481 (11) | 0.0469 (12) | −0.0040 (9) | 0.0100 (8) | −0.0101 (10) |
C9 | 0.0418 (11) | 0.0733 (14) | 0.0497 (12) | −0.0071 (11) | 0.0183 (10) | −0.0194 (12) |
C10 | 0.0575 (15) | 0.110 (2) | 0.0721 (17) | −0.0199 (15) | 0.0314 (13) | −0.0425 (16) |
C11 | 0.0515 (15) | 0.088 (2) | 0.127 (3) | −0.0092 (14) | 0.0383 (17) | −0.058 (2) |
C12 | 0.0567 (15) | 0.0547 (14) | 0.116 (2) | 0.0038 (11) | 0.0168 (15) | −0.0218 (15) |
C13 | 0.0479 (12) | 0.0480 (12) | 0.0686 (15) | −0.0024 (11) | 0.0098 (11) | −0.0129 (11) |
C14 | 0.0947 (18) | 0.1040 (19) | 0.0463 (14) | 0.0072 (17) | 0.0257 (13) | 0.0064 (14) |
C15 | 0.0993 (19) | 0.0548 (14) | 0.084 (2) | −0.0010 (14) | 0.0152 (15) | 0.0136 (13) |
C16 | 0.0424 (11) | 0.0557 (12) | 0.0487 (12) | −0.0046 (10) | 0.0183 (9) | −0.0144 (10) |
C17 | 0.0647 (14) | 0.0544 (14) | 0.0845 (18) | −0.0083 (12) | 0.0317 (13) | −0.0254 (13) |
C18 | 0.0756 (19) | 0.0850 (19) | 0.116 (2) | −0.0164 (16) | 0.0305 (19) | −0.054 (2) |
C19 | 0.0681 (18) | 0.157 (3) | 0.083 (2) | −0.012 (2) | 0.0155 (16) | −0.073 (2) |
C20 | 0.0721 (17) | 0.138 (3) | 0.0485 (15) | 0.0066 (18) | 0.0157 (12) | −0.0192 (17) |
C21 | 0.0583 (13) | 0.0787 (16) | 0.0478 (13) | 0.0008 (12) | 0.0228 (10) | −0.0080 (11) |
C22 | 0.137 (3) | 0.0426 (14) | 0.138 (3) | −0.0030 (16) | 0.062 (2) | −0.0014 (16) |
C23 | 0.118 (2) | 0.0892 (19) | 0.0665 (17) | 0.0023 (17) | 0.0486 (16) | 0.0222 (14) |
C24 | 0.0433 (11) | 0.0760 (15) | 0.0568 (13) | 0.0023 (11) | 0.0134 (10) | 0.0072 (11) |
C25 | 0.0751 (16) | 0.0721 (15) | 0.0663 (16) | −0.0134 (13) | 0.0292 (12) | 0.0093 (12) |
Al1—N1 | 1.8783 (15) | C13—C15 | 1.496 (3) |
Al1—C25 | 1.943 (2) | C14—H14A | 0.9600 |
Al1—N2 | 1.9453 (15) | C14—H14B | 0.9600 |
Al1—C24 | 1.948 (2) | C14—H14C | 0.9600 |
N1—C1 | 1.365 (2) | C15—H15A | 0.9600 |
N1—C8 | 1.441 (2) | C15—H15B | 0.9600 |
N2—C7 | 1.295 (2) | C15—H15C | 0.9600 |
N2—C16 | 1.441 (2) | C16—C17 | 1.384 (3) |
C1—C2 | 1.402 (2) | C16—C21 | 1.387 (3) |
C1—C6 | 1.422 (2) | C17—C18 | 1.384 (3) |
C2—C3 | 1.360 (3) | C17—C22 | 1.490 (3) |
C2—H2 | 0.9300 | C18—C19 | 1.346 (4) |
C3—C4 | 1.388 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.369 (4) |
C4—C5 | 1.342 (3) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.371 (3) |
C5—C6 | 1.410 (2) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C23 | 1.506 (3) |
C6—C7 | 1.408 (2) | C22—H22A | 0.9600 |
C7—H7 | 0.9300 | C22—H22B | 0.9600 |
C8—C13 | 1.387 (3) | C22—H22C | 0.9600 |
C8—C9 | 1.393 (3) | C23—H23A | 0.9600 |
C9—C10 | 1.388 (3) | C23—H23B | 0.9600 |
C9—C14 | 1.488 (3) | C23—H23C | 0.9600 |
C10—C11 | 1.369 (3) | C24—H24A | 0.9600 |
C10—H10 | 0.9300 | C24—H24B | 0.9600 |
C11—C12 | 1.364 (4) | C24—H24C | 0.9600 |
C11—H11 | 0.9300 | C25—H25A | 0.9600 |
C12—C13 | 1.389 (3) | C25—H25B | 0.9600 |
C12—H12 | 0.9300 | C25—H25C | 0.9600 |
N1—Al1—C25 | 112.62 (8) | H14A—C14—H14B | 109.5 |
N1—Al1—N2 | 93.86 (6) | C9—C14—H14C | 109.5 |
C25—Al1—N2 | 111.81 (8) | H14A—C14—H14C | 109.5 |
N1—Al1—C24 | 115.96 (8) | H14B—C14—H14C | 109.5 |
C25—Al1—C24 | 112.67 (10) | C13—C15—H15A | 109.5 |
N2—Al1—C24 | 108.36 (8) | C13—C15—H15B | 109.5 |
C1—N1—C8 | 117.81 (14) | H15A—C15—H15B | 109.5 |
C1—N1—Al1 | 127.06 (12) | C13—C15—H15C | 109.5 |
C8—N1—Al1 | 115.10 (10) | H15A—C15—H15C | 109.5 |
C7—N2—C16 | 117.44 (15) | H15B—C15—H15C | 109.5 |
C7—N2—Al1 | 122.85 (12) | C17—C16—C21 | 122.3 (2) |
C16—N2—Al1 | 119.52 (11) | C17—C16—N2 | 119.67 (19) |
N1—C1—C2 | 122.15 (16) | C21—C16—N2 | 118.02 (18) |
N1—C1—C6 | 121.20 (15) | C18—C17—C16 | 117.0 (2) |
C2—C1—C6 | 116.63 (16) | C18—C17—C22 | 120.8 (2) |
C3—C2—C1 | 121.57 (18) | C16—C17—C22 | 122.1 (2) |
C3—C2—H2 | 119.2 | C19—C18—C17 | 121.4 (3) |
C1—C2—H2 | 119.2 | C19—C18—H18 | 119.3 |
C2—C3—C4 | 121.76 (19) | C17—C18—H18 | 119.3 |
C2—C3—H3 | 119.1 | C18—C19—C20 | 120.8 (3) |
C4—C3—H3 | 119.1 | C18—C19—H19 | 119.6 |
C5—C4—C3 | 118.37 (18) | C20—C19—H19 | 119.6 |
C5—C4—H4 | 120.8 | C19—C20—C21 | 120.5 (3) |
C3—C4—H4 | 120.8 | C19—C20—H20 | 119.7 |
C4—C5—C6 | 122.28 (19) | C21—C20—H20 | 119.7 |
C4—C5—H5 | 118.9 | C20—C21—C16 | 117.9 (2) |
C6—C5—H5 | 118.9 | C20—C21—C23 | 120.2 (2) |
C7—C6—C5 | 116.65 (17) | C16—C21—C23 | 121.9 (2) |
C7—C6—C1 | 123.64 (16) | C17—C22—H22A | 109.5 |
C5—C6—C1 | 119.34 (16) | C17—C22—H22B | 109.5 |
N2—C7—C6 | 127.61 (17) | H22A—C22—H22B | 109.5 |
N2—C7—H7 | 116.2 | C17—C22—H22C | 109.5 |
C6—C7—H7 | 116.2 | H22A—C22—H22C | 109.5 |
C13—C8—C9 | 121.40 (18) | H22B—C22—H22C | 109.5 |
C13—C8—N1 | 118.19 (17) | C21—C23—H23A | 109.5 |
C9—C8—N1 | 120.39 (17) | C21—C23—H23B | 109.5 |
C10—C9—C8 | 118.2 (2) | H23A—C23—H23B | 109.5 |
C10—C9—C14 | 119.6 (2) | C21—C23—H23C | 109.5 |
C8—C9—C14 | 122.25 (18) | H23A—C23—H23C | 109.5 |
C11—C10—C9 | 120.5 (2) | H23B—C23—H23C | 109.5 |
C11—C10—H10 | 119.7 | Al1—C24—H24A | 109.5 |
C9—C10—H10 | 119.7 | Al1—C24—H24B | 109.5 |
C12—C11—C10 | 120.9 (2) | H24A—C24—H24B | 109.5 |
C12—C11—H11 | 119.5 | Al1—C24—H24C | 109.5 |
C10—C11—H11 | 119.5 | H24A—C24—H24C | 109.5 |
C11—C12—C13 | 120.5 (2) | H24B—C24—H24C | 109.5 |
C11—C12—H12 | 119.7 | Al1—C25—H25A | 109.5 |
C13—C12—H12 | 119.7 | Al1—C25—H25B | 109.5 |
C8—C13—C12 | 118.4 (2) | H25A—C25—H25B | 109.5 |
C8—C13—C15 | 121.89 (19) | Al1—C25—H25C | 109.5 |
C12—C13—C15 | 119.7 (2) | H25A—C25—H25C | 109.5 |
C9—C14—H14A | 109.5 | H25B—C25—H25C | 109.5 |
C9—C14—H14B | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Al(CH3)2(C23H23N2)] |
Mr | 384.48 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.0483 (18), 11.045 (2), 24.192 (5) |
β (°) | 111.64 (3) |
V (Å3) | 2247.3 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.19 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.981, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11340, 5115, 2682 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.106, 0.96 |
No. of reflections | 5115 |
No. of parameters | 259 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993).
Al1—N1 | 1.8783 (15) | Al1—N2 | 1.9453 (15) |
Al1—C25 | 1.943 (2) | Al1—C24 | 1.948 (2) |
N1—Al1—C25 | 112.62 (8) | N1—Al1—C24 | 115.96 (8) |
N1—Al1—N2 | 93.86 (6) | C25—Al1—C24 | 112.67 (10) |
C25—Al1—N2 | 111.81 (8) | N2—Al1—C24 | 108.36 (8) |
Organoaluminium complexes are currently generating considerable interest due to their increasing role in polymerization chemistry, such as cationic (Bochmann & Dawson, 1996), anionic (Kuroki et al., 1991) and ring-opening polymerization, (Jegier & Atwood, 1997) and as cocatalysts in transition metal-catalysed olefin polymerization (McKnight & Waymouth, 1998; Britovsek et al., 1999). Previously, a lot of alkylaluminium complexes with bidentate (Gameron et al., 2001; Pappalardo et al., 2002) or tridentate (Gameron et al., 1999; Huang et al., 2001) Schiff base ligands have been reported. Our current research efforts are focused on alkylaluminium complexes with new ligands. Herein we report the structure of the title complex, a mononuclear Schiff base dimethyl aluminium complex.
An ORTEP drawing of the molecular structure of the complex is shown in Fig. 1. The aluminium atom exhibits a distorted tetrahedral geometry. The N—Al—N angle (93.8°) in the complex is similar to that of ortho-C6H4N(C6H4-4-Me)(CH=NC6H4-4-Me)AlMe2 (94.5°, Liu et al., 2005), but larger than those in {tBuC(NCy)2}AlMe2 (Coles et al., 1997) and {(iPr)2ATI}AlMe2 (Dias et al., 1995) with four- and five- membered chelating rings, which exhibit angles of 69° and 84°, respectively. In the title compound the six membered chelating ring is nearly planar and the distance of the aluminium atom from the mean plane made up by the other five atoms of the six membered ring is only 0.1383 (7) Å. The imino C=N bond in the complex retains its double bond character with a bond length of 1.295 (2) Å.