supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2169    [ doi:10.1107/S1600536807034435 ]

[[mu]-1-Benzyl-4-(4-tert-butylphenyl)piperazine-[kappa]2N:N']bis[trimethylaluminium(III)]

L.-C. Yang, Q.-G. Xu, J.-B. Ou, Y.-Z. Li and L. Wu

Abstract top

In the title compound, [Al2(CH3)6(C21H28N2)], the piperazine ring adopts a chair conformation. The Al-N bond lengths range from 2.089 (2) to 2.121 (2) Å. The four-coordinate environment of the Al atoms is defined by one piperazine N atom and three methyl ligands. The structure contains two independent molecules in the asymmetric unit. Both molecules have almost the same conformation, except for the benzyl groups which show different rotations in the two molecules. The independent molecules are related to one another by a pseudorotation in combination with a translation along the a axis. Intermolecular C-H...[pi] contacts or stacking between the benzyl or phenyl rings are not observed.

Comment top

MOCVD (metalorganic chemical vapour deposition) is a well known technique for growth of thin films of metals (Das et al., 2007). The purity of metallorganic precursors plays an important role in the technique (Aguero et al., 2005). Coordination is a good way to get the high purity of metallorganic precursors (Reier et al., 1988). So, we synthesized the title compound and found two independent molecules (Z' = 2) in the asymmetric unit of the cell (Brock & Dunitz, 1994; Steiner, 2000) (Fig.1). Conformational differences of the molecules are distinguished by opposite rotation of their benzyl moieties: in molecule 1 the π system of the benzyl ring approaches H22C of a methyl of Al1, whereas in molecule 2, the benzyl ring rotates towards the opposite Al4 to approach H51B of a methyl group. The main part of the molecules (piperazine, both trimethylaluminum and tert-butylphenyl) have almost identical conformation. Intermolecular C—H···π contacts and stacking between benzyl or phenyl rings could not be observed. In a b,c-projection of the unit cell, the main part of the independent molecules seem to be related via a twofold symmetry, the axis running along a at 3/4b and ca 1/2c. In the a,c-projection of the unit cell (Fig. 2) however, one can imagine that after rotation around the pseudo-rotation axis at c/2, a translation of ca 0.65 along the a axis is necessary to find the molecules at identical positions, except of the benzyl moieties. The presented structure is found to agree well with the majority of triclinic structures with Z' = 2 in respect to symmetry relation between the independent molecules. Only few examples were found to have pseudoinversion centers between independent molecules (Desiraju et al., 1991). In both molecules of the title compound, the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The four-coordinate environment of the Al atoms is completed by one N atom and three methyl ligands. The Al—N bond lengths range from 2.089 (2) Å to 2.121 (2) Å.

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature, see: Aguero et al., (2005); Das & Shivashankar, (2007); Reier et al., (1988). For information about Z' = 2 structures, see: Desiraju et al., (1991); Brock & Dunitz, (1994); Steiner (2000).

Experimental top

In the absence of oxygen and under anhydrous conditions, to a solution of 1-benzyl-4-(4-tert-butylphenyl)piperazine (1 mmol) in petroleum ether (2 mL) was added the solution of trimethylaluminum (2 mol/L) in petroleum ether (1 mL) and heated to reflux. The resulting mixture was cooled to room temperature and white solid was obtained. It was solved in the petroleum ether and evaporated in the N2 atmosphere. Then colourless block-shaped crystals suitable for X-ray diffraction were obtained after several days, these were filtered off and washed with petroleum ether (yield 73%).

Refinement top

The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H distances in the range of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(parent atom), or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The independent molecules of the title compound viewed along the b-axis of the unit cell.
[µ-1-Benzyl-4-(4-tert-butylphenyl)piperazine- κ2N:N']bis[trimethylaluminium(III)] top
Crystal data top
[Al2(CH3)6(C21H28N2)]Z = 4
Mr = 452.62F(000) = 992
Triclinic, P1Dx = 1.051 Mg m−3
Hall symbol: -P 1Melting point: 443 K
a = 11.191 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.809 (3) ÅCell parameters from 4614 reflections
c = 20.489 (5) Åθ = 2.5–28.0°
α = 101.419 (3)°µ = 0.12 mm−1
β = 96.138 (4)°T = 291 K
γ = 90.242 (4)°Block, colourless
V = 2861.5 (13) Å30.30 × 0.26 × 0.24 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		10970 independent reflections
Radiation source: sealed tube7250 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −7→13
Tmin = 0.892, Tmax = 0.975k = −15→14
15540 measured reflectionsl = −25→25
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.05P)2 + 1.55P]
where P = (Fo2 + 2Fc2)/3
10970 reflections(Δ/σ)max < 0.001
577 parametersΔρmax = 0.60 e Å−3
0 restraintsΔρmin = −0.63 e Å−3
Crystal data top
[Al2(CH3)6(C21H28N2)]γ = 90.242 (4)°
Mr = 452.62V = 2861.5 (13) Å3
Triclinic, P1Z = 4
a = 11.191 (3) ÅMo Kα radiation
b = 12.809 (3) ŵ = 0.12 mm−1
c = 20.489 (5) ÅT = 291 K
α = 101.419 (3)°0.30 × 0.26 × 0.24 mm
β = 96.138 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		10970 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		7250 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.975Rint = 0.031
15540 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.135Δρmax = 0.60 e Å−3
S = 1.01Δρmin = −0.63 e Å−3
10970 reflectionsAbsolute structure: ?
577 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Al10.64159 (7)0.89507 (6)0.14885 (4)0.03113 (18)
Al21.21587 (7)0.91358 (6)0.30146 (4)0.03029 (18)
Al30.27837 (7)0.61368 (7)0.85482 (4)0.03272 (19)
Al40.79296 (7)0.58930 (6)0.70435 (4)0.02890 (18)
C10.8858 (2)0.8244 (2)0.16797 (13)0.0310 (6)
H1A0.88030.78460.12220.037*
H1B0.84360.78330.19380.037*
C21.0182 (2)0.8382 (2)0.19682 (12)0.0320 (6)
H2A1.05490.76900.19240.038*
H2B1.06060.88060.17190.038*
C30.9768 (2)1.0013 (2)0.26989 (13)0.0303 (6)
H3A1.02411.03900.24440.036*
H3B0.98191.04210.31540.036*
C40.8461 (2)0.9936 (2)0.23917 (13)0.0335 (6)
H4A0.79820.96180.26730.040*
H4B0.81761.06500.23910.040*
C50.8775 (2)0.9940 (2)0.12317 (13)0.0308 (6)
H5A0.83431.05990.12580.037*
H5B0.96081.01250.14000.037*
C60.8722 (2)0.9393 (2)0.05030 (13)0.0325 (6)
C70.9613 (2)0.8707 (2)0.02695 (13)0.0340 (6)
H71.02440.85660.05710.041*
C80.9583 (3)0.8229 (2)−0.03992 (13)0.0397 (7)
H81.01700.7753−0.05440.048*
C90.8659 (3)0.8473 (2)−0.08512 (14)0.0412 (7)
H90.86360.8165−0.13030.049*
C100.7781 (3)0.9165 (2)−0.06377 (14)0.0398 (7)
H100.71710.9322−0.09460.048*
C110.7800 (2)0.9630 (2)0.00359 (13)0.0353 (6)
H110.72041.00980.01780.042*
C120.9765 (2)0.8347 (2)0.31560 (13)0.0311 (6)
C130.9627 (3)0.7213 (2)0.30128 (13)0.0340 (6)
H130.98520.68340.26110.041*
C140.9186 (3)0.6675 (2)0.34359 (13)0.0354 (6)
H140.91130.59360.33190.043*
C150.8835 (2)0.7196 (2)0.40471 (13)0.0305 (6)
C160.8951 (3)0.8298 (2)0.41933 (13)0.0356 (6)
H160.87170.86670.45960.043*
C170.9407 (2)0.8876 (2)0.37573 (12)0.0324 (6)
H170.94690.96150.38720.039*
C180.8331 (3)0.6590 (2)0.45344 (14)0.0377 (6)
C190.8319 (3)0.5369 (3)0.42843 (18)0.0562 (9)
H19A0.80530.50240.46200.084*
H19B0.91150.51470.41980.084*
H19C0.77810.51790.38790.084*
C200.9149 (3)0.6837 (3)0.52033 (15)0.0492 (8)
H20A0.93120.75910.53290.074*
H20B0.98910.64710.51530.074*
H20C0.87530.66030.55440.074*
C210.7067 (3)0.6965 (3)0.46511 (19)0.0615 (10)
H21A0.71030.77030.48670.092*
H21B0.67250.65510.49300.092*
H21C0.65760.68780.42290.092*
C220.6199 (3)0.7823 (2)0.06713 (13)0.0365 (6)
H22A0.53570.76640.05460.055*
H22B0.65970.71930.07570.055*
H22C0.65380.80630.03140.055*
C230.5732 (3)1.0357 (2)0.14290 (15)0.0402 (7)
H23A0.55591.04040.09670.060*
H23B0.63011.09110.16500.060*
H23C0.50041.04360.16410.060*
C240.6038 (3)0.8411 (2)0.22921 (13)0.0395 (7)
H24A0.52130.81720.22320.059*
H24B0.61720.89730.26810.059*
H24C0.65490.78290.23510.059*
C251.2746 (2)0.9738 (2)0.22833 (14)0.0351 (6)
H25A1.35491.00230.24210.053*
H25B1.22281.02960.21850.053*
H25C1.27450.91880.18900.053*
C261.2214 (3)1.0128 (2)0.38873 (13)0.0397 (7)
H26A1.19030.97740.42070.060*
H26B1.17351.07340.38390.060*
H26C1.30311.03610.40410.060*
C271.2719 (2)0.7689 (2)0.30281 (14)0.0361 (6)
H27A1.35430.77240.32200.054*
H27B1.26550.72800.25790.054*
H27C1.22340.73560.32920.054*
C280.4553 (2)0.5047 (2)0.77416 (12)0.0291 (6)
H28A0.39410.52940.74390.035*
H28B0.43120.43350.77780.035*
C290.5737 (2)0.49806 (19)0.74267 (12)0.0259 (5)
H29A0.63260.46330.76880.031*
H29B0.56100.45500.69780.031*
C300.6428 (2)0.6655 (2)0.81280 (13)0.0330 (6)
H30A0.69740.62560.83800.040*
H30B0.67940.73520.81530.040*
C310.5237 (2)0.6781 (2)0.84352 (13)0.0334 (6)
H31A0.53950.71530.88980.040*
H31B0.47220.72240.81990.040*
C320.4999 (2)0.5226 (2)0.90057 (13)0.0365 (7)
H32A0.49060.57330.94160.044*
H32B0.44550.46280.89890.044*
C330.6261 (2)0.4825 (2)0.90633 (13)0.0301 (6)
C340.6475 (2)0.3752 (2)0.88124 (13)0.0301 (6)
H340.58500.33000.85830.036*
C350.7626 (3)0.3365 (2)0.89078 (14)0.0376 (6)
H350.77640.26530.87370.045*
C360.8557 (3)0.4011 (3)0.92486 (14)0.0438 (7)
H360.93180.37360.93140.053*
C370.8367 (3)0.5082 (3)0.94981 (15)0.0449 (7)
H370.90020.55290.97210.054*
C380.7214 (3)0.5479 (2)0.94111 (13)0.0397 (7)
H380.70800.61890.95880.048*
C390.5475 (2)0.6626 (2)0.69475 (13)0.0320 (6)
C400.5367 (3)0.7738 (2)0.70635 (14)0.0364 (6)
H400.57320.81320.74670.044*
C410.4777 (2)0.8268 (2)0.66354 (13)0.0328 (6)
H410.47550.90080.67430.039*
C420.4195 (2)0.7718 (2)0.60283 (14)0.0344 (6)
C430.4286 (2)0.6624 (2)0.58951 (13)0.0336 (6)
H430.39200.62410.54890.040*
C440.4894 (2)0.6068 (2)0.63361 (13)0.0345 (6)
H440.49170.53290.62280.041*
C450.3507 (2)0.8302 (2)0.55320 (14)0.0367 (6)
C460.2207 (3)0.7874 (3)0.53678 (17)0.0520 (9)
H46A0.22020.71290.51690.078*
H46B0.17810.82530.50600.078*
H46C0.18230.79710.57720.078*
C470.3529 (3)0.9526 (3)0.57814 (18)0.0555 (9)
H47A0.31510.98570.54340.083*
H47B0.43470.97830.58950.083*
H47C0.31040.96970.61700.083*
C480.4120 (3)0.8086 (2)0.48701 (14)0.0425 (7)
H48A0.42150.73340.47280.064*
H48B0.48950.84410.49470.064*
H48C0.36280.83520.45290.064*
C490.8475 (3)0.7362 (2)0.70366 (15)0.0407 (7)
H49A0.85040.77870.74800.061*
H49B0.79240.76640.67370.061*
H49C0.92620.73480.68890.061*
C500.7598 (3)0.4889 (2)0.61685 (13)0.0381 (7)
H50A0.83440.46790.59960.057*
H50B0.71230.52330.58580.057*
H50C0.71680.42710.62280.057*
C510.8883 (2)0.5318 (2)0.77515 (14)0.0352 (6)
H51A0.96670.51450.76200.053*
H51B0.84870.46880.78190.053*
H51C0.89580.58420.81610.053*
C520.2199 (3)0.6759 (3)0.77589 (16)0.0478 (8)
H52A0.14370.70790.78270.072*
H52B0.21100.62060.73640.072*
H52C0.27690.72900.77060.072*
C530.2949 (3)0.7196 (2)0.94034 (15)0.0439 (7)
H53A0.21760.74780.94910.066*
H53B0.34890.77640.93720.066*
H53C0.32630.68570.97610.066*
C540.2034 (3)0.4745 (3)0.85564 (17)0.0492 (8)
H54A0.24060.44720.89300.074*
H54B0.21410.42570.81480.074*
H54C0.11910.48290.85950.074*
N10.82603 (19)0.92951 (17)0.16896 (10)0.0292 (5)
N21.02877 (19)0.89295 (16)0.27066 (10)0.0294 (5)
N30.62219 (19)0.60702 (17)0.73935 (11)0.0309 (5)
N40.45731 (19)0.57570 (17)0.84175 (10)0.0304 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Al10.0286 (4)0.0340 (4)0.0311 (4)0.0010 (3)0.0052 (3)0.0062 (3)
Al20.0318 (4)0.0320 (4)0.0277 (4)0.0001 (3)0.0005 (3)0.0092 (3)
Al30.0294 (4)0.0345 (4)0.0383 (5)0.0049 (3)0.0066 (3)0.0152 (4)
Al40.0282 (4)0.0324 (4)0.0294 (4)0.0031 (3)0.0115 (3)0.0097 (3)
C10.0304 (14)0.0297 (14)0.0336 (14)0.0013 (11)0.0043 (11)0.0076 (11)
C20.0317 (14)0.0350 (15)0.0283 (13)0.0027 (11)0.0027 (11)0.0043 (11)
C30.0312 (14)0.0307 (14)0.0299 (13)−0.0002 (11)0.0007 (11)0.0092 (11)
C40.0323 (15)0.0317 (14)0.0350 (14)0.0006 (11)0.0018 (11)0.0037 (11)
C50.0328 (14)0.0278 (14)0.0348 (14)−0.0021 (11)0.0043 (11)0.0134 (11)
C60.0352 (15)0.0292 (14)0.0337 (14)−0.0047 (11)0.0010 (11)0.0095 (11)
C70.0297 (14)0.0437 (16)0.0316 (14)−0.0017 (12)0.0096 (11)0.0118 (12)
C80.0371 (16)0.0519 (18)0.0319 (15)−0.0052 (13)0.0139 (12)0.0074 (13)
C90.0426 (17)0.0513 (18)0.0299 (14)−0.0241 (14)0.0084 (12)0.0070 (13)
C100.0356 (16)0.0568 (19)0.0301 (14)−0.0108 (14)−0.0035 (12)0.0201 (13)
C110.0325 (15)0.0473 (17)0.0286 (14)−0.0034 (12)−0.0030 (11)0.0172 (12)
C120.0305 (14)0.0349 (14)0.0303 (13)−0.0002 (11)0.0069 (11)0.0107 (11)
C130.0419 (16)0.0321 (14)0.0299 (14)0.0039 (12)0.0141 (12)0.0052 (11)
C140.0419 (16)0.0343 (15)0.0335 (14)−0.0037 (12)0.0118 (12)0.0111 (12)
C150.0372 (15)0.0304 (14)0.0283 (13)−0.0017 (11)0.0106 (11)0.0127 (11)
C160.0473 (17)0.0315 (14)0.0305 (14)0.0020 (12)0.0142 (12)0.0066 (11)
C170.0373 (15)0.0349 (15)0.0280 (13)0.0048 (12)0.0131 (11)0.0082 (11)
C180.0368 (15)0.0436 (16)0.0396 (15)−0.0011 (12)0.0189 (12)0.0172 (13)
C190.055 (2)0.050 (2)0.066 (2)−0.0124 (16)0.0168 (17)0.0138 (17)
C200.052 (2)0.053 (2)0.0437 (18)−0.0154 (15)0.0083 (15)0.0115 (15)
C210.055 (2)0.069 (2)0.068 (2)0.0145 (18)0.0209 (18)0.0229 (19)
C220.0335 (15)0.0365 (15)0.0358 (15)−0.0101 (12)0.0004 (11)0.0003 (12)
C230.0302 (15)0.0399 (16)0.0534 (18)0.0088 (12)0.0123 (13)0.0120 (14)
C240.0381 (16)0.0514 (18)0.0321 (15)−0.0080 (13)0.0124 (12)0.0113 (13)
C250.0300 (14)0.0392 (15)0.0388 (15)−0.0090 (12)0.0033 (11)0.0150 (12)
C260.0441 (17)0.0393 (16)0.0329 (15)0.0024 (13)−0.0039 (12)0.0048 (12)
C270.0341 (15)0.0330 (15)0.0434 (16)0.0041 (12)−0.0005 (12)0.0152 (12)
C280.0289 (14)0.0270 (13)0.0329 (14)−0.0015 (11)0.0115 (11)0.0055 (11)
C290.0281 (13)0.0238 (12)0.0298 (13)0.0027 (10)0.0123 (10)0.0097 (10)
C300.0310 (14)0.0330 (14)0.0346 (15)0.0011 (11)0.0042 (11)0.0054 (11)
C310.0332 (15)0.0330 (15)0.0341 (14)0.0043 (12)0.0057 (11)0.0057 (11)
C320.0344 (15)0.0481 (17)0.0356 (15)0.0200 (13)0.0148 (12)0.0230 (13)
C330.0274 (13)0.0343 (14)0.0318 (14)0.0044 (11)0.0085 (11)0.0113 (11)
C340.0325 (14)0.0308 (14)0.0311 (13)0.0090 (11)0.0075 (11)0.0140 (11)
C350.0344 (15)0.0390 (16)0.0437 (16)0.0103 (13)0.0130 (13)0.0136 (13)
C360.0387 (17)0.060 (2)0.0358 (16)0.0147 (15)0.0070 (13)0.0154 (14)
C370.0368 (17)0.0536 (19)0.0422 (17)0.0015 (14)−0.0099 (13)0.0121 (14)
C380.0446 (17)0.0422 (17)0.0302 (14)0.0056 (13)−0.0025 (12)0.0056 (12)
C390.0327 (14)0.0322 (14)0.0320 (14)0.0009 (11)0.0056 (11)0.0079 (11)
C400.0420 (16)0.0312 (14)0.0348 (15)0.0011 (12)−0.0004 (12)0.0062 (12)
C410.0338 (15)0.0294 (14)0.0352 (14)0.0023 (11)0.0001 (11)0.0085 (11)
C420.0336 (15)0.0351 (15)0.0366 (15)0.0024 (12)0.0029 (11)0.0126 (12)
C430.0305 (14)0.0349 (15)0.0327 (14)−0.0022 (11)−0.0046 (11)0.0046 (11)
C440.0346 (15)0.0358 (15)0.0301 (14)−0.0004 (12)−0.0043 (11)0.0038 (11)
C450.0306 (15)0.0443 (16)0.0344 (15)0.0038 (12)−0.0084 (11)0.0119 (12)
C460.051 (2)0.051 (2)0.0533 (19)−0.0211 (15)−0.0185 (15)0.0215 (16)
C470.049 (2)0.049 (2)0.068 (2)0.0183 (16)−0.0039 (17)0.0165 (17)
C480.0428 (17)0.0464 (17)0.0377 (16)0.0100 (14)−0.0105 (13)0.0149 (13)
C490.0431 (17)0.0312 (15)0.0544 (18)−0.0028 (13)0.0220 (14)0.0158 (13)
C500.0492 (18)0.0377 (16)0.0298 (14)0.0044 (13)0.0183 (12)0.0054 (12)
C510.0267 (14)0.0404 (16)0.0383 (15)0.0041 (12)0.0041 (11)0.0070 (12)
C520.0330 (16)0.058 (2)0.057 (2)0.0065 (14)−0.0002 (14)0.0276 (16)
C530.0395 (17)0.0460 (18)0.0494 (18)0.0131 (14)0.0192 (14)0.0095 (14)
C540.0364 (17)0.0496 (19)0.066 (2)−0.0027 (14)0.0051 (15)0.0230 (16)
N10.0291 (11)0.0277 (11)0.0310 (11)−0.0016 (9)0.0054 (9)0.0053 (9)
N20.0317 (12)0.0261 (11)0.0325 (12)0.0028 (9)0.0060 (9)0.0091 (9)
N30.0308 (12)0.0300 (12)0.0337 (12)0.0018 (9)0.0089 (9)0.0080 (9)
N40.0312 (12)0.0334 (12)0.0300 (11)0.0042 (9)0.0085 (9)0.0118 (9)
Geometric parameters (Å, °) top
Al1—C221.975 (3)C25—H25B0.9600
Al1—C231.980 (3)C25—H25C0.9600
Al1—C241.991 (3)C26—H26A0.9600
Al1—N12.089 (2)C26—H26B0.9600
Al2—C271.963 (3)C26—H26C0.9600
Al2—C261.973 (3)C27—H27A0.9600
Al2—C251.984 (3)C27—H27B0.9600
Al2—N22.121 (2)C27—H27C0.9600
Al3—C541.971 (3)C28—N41.497 (3)
Al3—C531.983 (3)C28—C291.530 (3)
Al3—C521.991 (3)C28—H28A0.9700
Al3—N42.095 (2)C28—H28B0.9700
Al4—C511.970 (3)C29—N31.512 (3)
Al4—C491.979 (3)C29—H29A0.9700
Al4—C501.986 (3)C29—H29B0.9700
Al4—N32.109 (2)C30—C311.530 (4)
C1—N11.504 (3)C30—N31.535 (3)
C1—C21.531 (4)C30—H30A0.9700
C1—H1A0.9700C30—H30B0.9700
C1—H1B0.9700C31—N41.497 (3)
C2—N21.528 (3)C31—H31A0.9700
C2—H2A0.9700C31—H31B0.9700
C2—H2B0.9700C32—C331.505 (4)
C3—N21.509 (3)C32—N41.532 (3)
C3—C41.524 (4)C32—H32A0.9700
C3—H3A0.9700C32—H32B0.9700
C3—H3B0.9700C33—C381.393 (4)
C4—N11.502 (3)C33—C341.401 (4)
C4—H4A0.9700C34—C351.389 (4)
C4—H4B0.9700C34—H340.9300
C5—C61.513 (4)C35—C361.367 (4)
C5—N11.521 (3)C35—H350.9300
C5—H5A0.9700C36—C371.391 (4)
C5—H5B0.9700C36—H360.9300
C6—C71.392 (4)C37—C381.395 (4)
C6—C111.407 (4)C37—H370.9300
C7—C81.382 (4)C38—H380.9300
C7—H70.9300C39—C441.404 (4)
C8—C91.392 (4)C39—C401.404 (4)
C8—H80.9300C39—N31.463 (3)
C9—C101.373 (4)C40—C411.335 (4)
C9—H90.9300C40—H400.9300
C10—C111.389 (4)C41—C421.394 (4)
C10—H100.9300C41—H410.9300
C11—H110.9300C42—C431.381 (4)
C12—C171.384 (3)C42—C451.525 (4)
C12—C131.428 (4)C43—C441.383 (4)
C12—N21.460 (3)C43—H430.9300
C13—C141.340 (4)C44—H440.9300
C13—H130.9300C45—C461.531 (4)
C14—C151.394 (4)C45—C471.550 (4)
C14—H140.9300C45—C481.562 (4)
C15—C161.387 (4)C46—H46A0.9600
C15—C181.530 (3)C46—H46B0.9600
C16—C171.401 (4)C46—H46C0.9600
C16—H160.9300C47—H47A0.9600
C17—H170.9300C47—H47B0.9600
C18—C211.525 (4)C47—H47C0.9600
C18—C201.541 (4)C48—H48A0.9600
C18—C191.546 (4)C48—H48B0.9600
C19—H19A0.9600C48—H48C0.9600
C19—H19B0.9600C49—H49A0.9600
C19—H19C0.9600C49—H49B0.9600
C20—H20A0.9600C49—H49C0.9600
C20—H20B0.9600C50—H50A0.9600
C20—H20C0.9600C50—H50B0.9600
C21—H21A0.9600C50—H50C0.9600
C21—H21B0.9600C51—H51A0.9600
C21—H21C0.9600C51—H51B0.9600
C22—H22A0.9600C51—H51C0.9600
C22—H22B0.9600C52—H52A0.9600
C22—H22C0.9600C52—H52B0.9600
C23—H23A0.9600C52—H52C0.9600
C23—H23B0.9600C53—H53A0.9600
C23—H23C0.9600C53—H53B0.9600
C24—H24A0.9600C53—H53C0.9600
C24—H24B0.9600C54—H54A0.9600
C24—H24C0.9600C54—H54B0.9600
C25—H25A0.9600C54—H54C0.9600
C22—Al1—C23117.28 (13)N4—C28—C29115.9 (2)
C22—Al1—C24111.64 (13)N4—C28—H28A108.3
C23—Al1—C24113.85 (13)C29—C28—H28A108.3
C22—Al1—N1106.49 (11)N4—C28—H28B108.3
C23—Al1—N1102.93 (11)C29—C28—H28B108.3
C24—Al1—N1102.83 (11)H28A—C28—H28B107.4
C27—Al2—C26116.72 (13)N3—C29—C28111.82 (19)
C27—Al2—C25112.84 (13)N3—C29—H29A109.3
C26—Al2—C25115.29 (13)C28—C29—H29A109.3
C27—Al2—N2104.44 (11)N3—C29—H29B109.3
C26—Al2—N2102.78 (11)C28—C29—H29B109.3
C25—Al2—N2102.35 (10)H29A—C29—H29B107.9
C54—Al3—C53116.88 (14)C31—C30—N3110.5 (2)
C54—Al3—C52114.34 (14)C31—C30—H30A109.5
C53—Al3—C52113.25 (14)N3—C30—H30A109.5
C54—Al3—N4102.92 (12)C31—C30—H30B109.5
C53—Al3—N4102.49 (11)N3—C30—H30B109.5
C52—Al3—N4104.70 (11)H30A—C30—H30B108.1
C51—Al4—C49110.99 (13)N4—C31—C30114.7 (2)
C51—Al4—C50115.34 (12)N4—C31—H31A108.6
C49—Al4—C50117.80 (13)C30—C31—H31A108.6
C51—Al4—N3102.76 (10)N4—C31—H31B108.6
C49—Al4—N3104.58 (11)C30—C31—H31B108.6
C50—Al4—N3103.16 (11)H31A—C31—H31B107.6
N1—C1—C2112.2 (2)C33—C32—N4119.1 (2)
N1—C1—H1A109.2C33—C32—H32A107.6
C2—C1—H1A109.2N4—C32—H32A107.6
N1—C1—H1B109.2C33—C32—H32B107.6
C2—C1—H1B109.2N4—C32—H32B107.6
H1A—C1—H1B107.9H32A—C32—H32B107.0
N2—C2—C1110.2 (2)C38—C33—C34118.7 (2)
N2—C2—H2A109.6C38—C33—C32121.3 (3)
C1—C2—H2A109.6C34—C33—C32119.8 (2)
N2—C2—H2B109.6C35—C34—C33119.8 (3)
C1—C2—H2B109.6C35—C34—H34120.1
H2A—C2—H2B108.1C33—C34—H34120.1
N2—C3—C4112.0 (2)C36—C35—C34121.2 (3)
N2—C3—H3A109.2C36—C35—H35119.4
C4—C3—H3A109.2C34—C35—H35119.4
N2—C3—H3B109.2C35—C36—C37120.0 (3)
C4—C3—H3B109.2C35—C36—H36120.0
H3A—C3—H3B107.9C37—C36—H36120.0
N1—C4—C3114.2 (2)C36—C37—C38119.4 (3)
N1—C4—H4A108.7C36—C37—H37120.3
C3—C4—H4A108.7C38—C37—H37120.3
N1—C4—H4B108.7C33—C38—C37121.0 (3)
C3—C4—H4B108.7C33—C38—H38119.5
H4A—C4—H4B107.6C37—C38—H38119.5
C6—C5—N1115.5 (2)C44—C39—C40115.4 (2)
C6—C5—H5A108.4C44—C39—N3120.8 (2)
N1—C5—H5A108.4C40—C39—N3123.6 (2)
C6—C5—H5B108.4C41—C40—C39124.6 (3)
N1—C5—H5B108.4C41—C40—H40117.7
H5A—C5—H5B107.5C39—C40—H40117.7
C7—C6—C11118.4 (3)C40—C41—C42120.3 (3)
C7—C6—C5121.6 (2)C40—C41—H41119.9
C11—C6—C5119.9 (2)C42—C41—H41119.9
C8—C7—C6121.7 (3)C43—C42—C41116.8 (2)
C8—C7—H7119.2C43—C42—C45121.7 (2)
C6—C7—H7119.2C41—C42—C45121.5 (2)
C7—C8—C9118.8 (3)C42—C43—C44123.2 (3)
C7—C8—H8120.6C42—C43—H43118.4
C9—C8—H8120.6C44—C43—H43118.4
C10—C9—C8120.8 (3)C43—C44—C39119.7 (3)
C10—C9—H9119.6C43—C44—H44120.2
C8—C9—H9119.6C39—C44—H44120.2
C9—C10—C11120.4 (3)C42—C45—C46110.3 (2)
C9—C10—H10119.8C42—C45—C47113.0 (2)
C11—C10—H10119.8C46—C45—C47110.2 (2)
C10—C11—C6119.9 (3)C42—C45—C48108.3 (2)
C10—C11—H11120.0C46—C45—C48108.1 (2)
C6—C11—H11120.0C47—C45—C48106.8 (3)
C17—C12—C13116.6 (2)C45—C46—H46A109.5
C17—C12—N2121.0 (2)C45—C46—H46B109.5
C13—C12—N2122.4 (2)H46A—C46—H46B109.5
C14—C13—C12122.5 (2)C45—C46—H46C109.5
C14—C13—H13118.8H46A—C46—H46C109.5
C12—C13—H13118.8H46B—C46—H46C109.5
C13—C14—C15121.6 (3)C45—C47—H47A109.5
C13—C14—H14119.2C45—C47—H47B109.5
C15—C14—H14119.2H47A—C47—H47B109.5
C16—C15—C14116.9 (2)C45—C47—H47C109.5
C16—C15—C18121.1 (2)H47A—C47—H47C109.5
C14—C15—C18122.1 (2)H47B—C47—H47C109.5
C15—C16—C17122.4 (2)C45—C48—H48A109.5
C15—C16—H16118.8C45—C48—H48B109.5
C17—C16—H16118.8H48A—C48—H48B109.5
C12—C17—C16120.0 (2)C45—C48—H48C109.5
C12—C17—H17120.0H48A—C48—H48C109.5
C16—C17—H17120.0H48B—C48—H48C109.5
C21—C18—C15109.2 (2)Al4—C49—H49A109.5
C21—C18—C20109.3 (3)Al4—C49—H49B109.5
C15—C18—C20108.4 (2)H49A—C49—H49B109.5
C21—C18—C19110.3 (3)Al4—C49—H49C109.5
C15—C18—C19112.6 (2)H49A—C49—H49C109.5
C20—C18—C19107.0 (3)H49B—C49—H49C109.5
C18—C19—H19A109.5Al4—C50—H50A109.5
C18—C19—H19B109.5Al4—C50—H50B109.5
H19A—C19—H19B109.5H50A—C50—H50B109.5
C18—C19—H19C109.5Al4—C50—H50C109.5
H19A—C19—H19C109.5H50A—C50—H50C109.5
H19B—C19—H19C109.5H50B—C50—H50C109.5
C18—C20—H20A109.5Al4—C51—H51A109.5
C18—C20—H20B109.5Al4—C51—H51B109.5
H20A—C20—H20B109.5H51A—C51—H51B109.5
C18—C20—H20C109.5Al4—C51—H51C109.5
H20A—C20—H20C109.5H51A—C51—H51C109.5
H20B—C20—H20C109.5H51B—C51—H51C109.5
C18—C21—H21A109.5Al3—C52—H52A109.5
C18—C21—H21B109.5Al3—C52—H52B109.5
H21A—C21—H21B109.5H52A—C52—H52B109.5
C18—C21—H21C109.5Al3—C52—H52C109.5
H21A—C21—H21C109.5H52A—C52—H52C109.5
H21B—C21—H21C109.5H52B—C52—H52C109.5
Al1—C22—H22A109.5Al3—C53—H53A109.5
Al1—C22—H22B109.5Al3—C53—H53B109.5
H22A—C22—H22B109.5H53A—C53—H53B109.5
Al1—C22—H22C109.5Al3—C53—H53C109.5
H22A—C22—H22C109.5H53A—C53—H53C109.5
H22B—C22—H22C109.5H53B—C53—H53C109.5
Al1—C23—H23A109.5Al3—C54—H54A109.5
Al1—C23—H23B109.5Al3—C54—H54B109.5
H23A—C23—H23B109.5H54A—C54—H54B109.5
Al1—C23—H23C109.5Al3—C54—H54C109.5
H23A—C23—H23C109.5H54A—C54—H54C109.5
H23B—C23—H23C109.5H54B—C54—H54C109.5
Al1—C24—H24A109.5C4—N1—C1108.1 (2)
Al1—C24—H24B109.5C4—N1—C5107.71 (19)
H24A—C24—H24B109.5C1—N1—C5112.8 (2)
Al1—C24—H24C109.5C4—N1—Al1106.49 (15)
H24A—C24—H24C109.5C1—N1—Al1106.19 (15)
H24B—C24—H24C109.5C5—N1—Al1115.23 (16)
Al2—C25—H25A109.5C12—N2—C3114.3 (2)
Al2—C25—H25B109.5C12—N2—C2116.1 (2)
H25A—C25—H25B109.5C3—N2—C2104.13 (19)
Al2—C25—H25C109.5C12—N2—Al2107.98 (16)
H25A—C25—H25C109.5C3—N2—Al2108.25 (15)
H25B—C25—H25C109.5C2—N2—Al2105.53 (15)
Al2—C26—H26A109.5C39—N3—C29114.5 (2)
Al2—C26—H26B109.5C39—N3—C30115.1 (2)
H26A—C26—H26B109.5C29—N3—C30104.30 (19)
Al2—C26—H26C109.5C39—N3—Al4107.48 (15)
H26A—C26—H26C109.5C29—N3—Al4108.44 (15)
H26B—C26—H26C109.5C30—N3—Al4106.70 (15)
Al2—C27—H27A109.5C28—N4—C31110.38 (19)
Al2—C27—H27B109.5C28—N4—C32114.7 (2)
H27A—C27—H27B109.5C31—N4—C32113.1 (2)
Al2—C27—H27C109.5C28—N4—Al3106.48 (15)
H27A—C27—H27C109.5C31—N4—Al3106.98 (15)
H27B—C27—H27C109.5C32—N4—Al3104.54 (15)
N1—C1—C2—N263.3 (3)C24—Al1—N1—C4−48.49 (18)
N2—C3—C4—N1−57.4 (3)C22—Al1—N1—C1−50.98 (18)
N1—C5—C6—C7−85.1 (3)C23—Al1—N1—C1−174.93 (17)
N1—C5—C6—C1199.2 (3)C24—Al1—N1—C166.53 (18)
C11—C6—C7—C8−2.5 (4)C22—Al1—N1—C574.66 (19)
C5—C6—C7—C8−178.2 (2)C23—Al1—N1—C5−49.29 (19)
C6—C7—C8—C92.3 (4)C24—Al1—N1—C5−167.83 (17)
C7—C8—C9—C10−0.9 (4)C17—C12—N2—C3−34.8 (3)
C8—C9—C10—C11−0.2 (4)C13—C12—N2—C3147.0 (2)
C9—C10—C11—C60.0 (4)C17—C12—N2—C2−156.1 (2)
C7—C6—C11—C101.3 (4)C13—C12—N2—C225.7 (3)
C5—C6—C11—C10177.1 (2)C17—C12—N2—Al285.7 (3)
C17—C12—C13—C14−0.6 (4)C13—C12—N2—Al2−92.5 (3)
N2—C12—C13—C14177.6 (3)C4—C3—N2—C12−67.5 (3)
C12—C13—C14—C15−0.1 (5)C4—C3—N2—C260.2 (3)
C13—C14—C15—C160.7 (4)C4—C3—N2—Al2172.11 (17)
C13—C14—C15—C18−179.9 (3)C1—C2—N2—C1263.5 (3)
C14—C15—C16—C17−0.5 (4)C1—C2—N2—C3−63.1 (2)
C18—C15—C16—C17−179.9 (3)C1—C2—N2—Al2−177.02 (17)
C13—C12—C17—C160.8 (4)C27—Al2—N2—C1254.28 (18)
N2—C12—C17—C16−177.5 (2)C26—Al2—N2—C12−68.03 (18)
C15—C16—C17—C12−0.2 (4)C25—Al2—N2—C12172.10 (17)
C16—C15—C18—C2159.0 (4)C27—Al2—N2—C3178.53 (16)
C14—C15—C18—C21−120.3 (3)C26—Al2—N2—C356.22 (18)
C16—C15—C18—C20−60.0 (3)C25—Al2—N2—C3−63.65 (18)
C14—C15—C18—C20120.7 (3)C27—Al2—N2—C2−70.47 (17)
C16—C15—C18—C19−178.1 (3)C26—Al2—N2—C2167.22 (16)
C14—C15—C18—C192.5 (4)C25—Al2—N2—C247.35 (18)
N4—C28—C29—N3−54.3 (3)C44—C39—N3—C29−38.2 (3)
N3—C30—C31—N458.4 (3)C40—C39—N3—C29147.3 (3)
N4—C32—C33—C3889.4 (3)C44—C39—N3—C30−159.0 (2)
N4—C32—C33—C34−96.0 (3)C40—C39—N3—C3026.5 (3)
C38—C33—C34—C35−0.7 (4)C44—C39—N3—Al482.3 (3)
C32—C33—C34—C35−175.4 (2)C40—C39—N3—Al4−92.2 (3)
C33—C34—C35—C360.6 (4)C28—C29—N3—C39−65.6 (3)
C34—C35—C36—C37−1.0 (4)C28—C29—N3—C3061.0 (3)
C35—C36—C37—C381.6 (4)C28—C29—N3—Al4174.39 (16)
C34—C33—C38—C371.3 (4)C31—C30—N3—C3963.1 (3)
C32—C33—C38—C37175.9 (3)C31—C30—N3—C29−63.1 (2)
C36—C37—C38—C33−1.7 (4)C31—C30—N3—Al4−177.73 (17)
C44—C39—C40—C41−0.9 (4)C51—Al4—N3—C39172.68 (17)
N3—C39—C40—C41173.8 (3)C49—Al4—N3—C3956.67 (19)
C39—C40—C41—C421.1 (5)C50—Al4—N3—C39−67.08 (18)
C40—C41—C42—C43−1.3 (4)C51—Al4—N3—C29−63.09 (18)
C40—C41—C42—C45179.5 (3)C49—Al4—N3—C29−179.10 (17)
C41—C42—C43—C441.4 (4)C50—Al4—N3—C2957.15 (18)
C45—C42—C43—C44−179.4 (3)C51—Al4—N3—C3048.73 (18)
C42—C43—C44—C39−1.3 (4)C49—Al4—N3—C30−67.27 (18)
C40—C39—C44—C430.9 (4)C50—Al4—N3—C30168.97 (16)
N3—C39—C44—C43−174.0 (2)C29—C28—N4—C3143.4 (3)
C43—C42—C45—C4656.6 (4)C29—C28—N4—C32−85.8 (3)
C41—C42—C45—C46−124.3 (3)C29—C28—N4—Al3159.12 (17)
C43—C42—C45—C47−179.6 (3)C30—C31—N4—C28−45.6 (3)
C41—C42—C45—C47−0.5 (4)C30—C31—N4—C3284.4 (3)
C43—C42—C45—C48−61.5 (3)C30—C31—N4—Al3−161.01 (18)
C41—C42—C45—C48117.6 (3)C33—C32—N4—C2862.6 (3)
C3—C4—N1—C150.7 (3)C33—C32—N4—C31−65.1 (3)
C3—C4—N1—C5−71.4 (3)C33—C32—N4—Al3178.8 (2)
C3—C4—N1—Al1164.42 (18)C54—Al3—N4—C2864.43 (18)
C2—C1—N1—C4−53.5 (3)C53—Al3—N4—C28−173.84 (17)
C2—C1—N1—C565.4 (3)C52—Al3—N4—C28−55.40 (19)
C2—C1—N1—Al1−167.47 (17)C54—Al3—N4—C31−177.54 (18)
C6—C5—N1—C4176.5 (2)C53—Al3—N4—C31−55.81 (18)
C6—C5—N1—C157.4 (3)C52—Al3—N4—C3162.63 (19)
C6—C5—N1—Al1−64.8 (3)C54—Al3—N4—C32−57.3 (2)
C22—Al1—N1—C4−166.00 (17)C53—Al3—N4—C3264.4 (2)
C23—Al1—N1—C470.06 (18)C52—Al3—N4—C32−177.15 (19)
Table 1
Selected geometric parameters (°) top
N1—C5—C6—C1199.2 (3)C13—C12—N2—Al2−92.5 (3)
C2—C1—N1—C4−53.5 (3)C4—C3—N2—C260.2 (3)
references
References top

Aguero, A., Garcia, M. & Gutierrez, M. (2005). Mater. Corros. 56, 937–941.

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Brock, C. P. & Dunitz, J. D. (1994). Chem. Mater. 6, 1118–1127.

Bruker (2000). SADABS (Version 2.01), SMART (Version 5.630), SAINT (Version 6.36) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.

Das, M. & Shivashankar, S. A. (2007). Appl. Organomet. Chem. 21, 15–25.

Desiraju, G. R., Calabrese, J. C. & Harlow, R. L. (1991). Acta Cryst. B47, 77–86.

Reier, F. W., Wolfram, P. & Schumann, H. (1988). J. Cryst. Growth, 93, 41–44.

Steiner, T. (2000). Acta Cryst. B56, 673–676.