Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034435/si2027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034435/si2027Isup2.hkl |
CCDC reference: 657597
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.135
- Data-to-parameter ratio = 19.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
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).
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%).
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).
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.
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).
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.
[Al2(CH3)6(C21H28N2)] | Z = 4 |
Mr = 452.62 | F(000) = 992 |
Triclinic, P1 | Dx = 1.051 Mg m−3 |
Hall symbol: -P 1 | Melting point: 443 K |
a = 11.191 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.809 (3) Å | Cell parameters from 4614 reflections |
c = 20.489 (5) Å | θ = 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) Å3 | 0.30 × 0.26 × 0.24 mm |
Bruker SMART APEX CCD area-detector diffractometer | 10970 independent reflections |
Radiation source: sealed tube | 7250 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→13 |
Tmin = 0.892, Tmax = 0.975 | k = −15→14 |
15540 measured reflections | l = −25→25 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-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 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Al2(CH3)6(C21H28N2)] | γ = 90.242 (4)° |
Mr = 452.62 | V = 2861.5 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.191 (3) Å | Mo Kα radiation |
b = 12.809 (3) Å | µ = 0.12 mm−1 |
c = 20.489 (5) Å | T = 291 K |
α = 101.419 (3)° | 0.30 × 0.26 × 0.24 mm |
β = 96.138 (4)° |
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 = 0.975 | Rint = 0.031 |
15540 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.60 e Å−3 |
10970 reflections | Δρmin = −0.63 e Å−3 |
577 parameters |
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 | 0.64159 (7) | 0.89507 (6) | 0.14885 (4) | 0.03113 (18) | |
Al2 | 1.21587 (7) | 0.91358 (6) | 0.30146 (4) | 0.03029 (18) | |
Al3 | 0.27837 (7) | 0.61368 (7) | 0.85482 (4) | 0.03272 (19) | |
Al4 | 0.79296 (7) | 0.58930 (6) | 0.70435 (4) | 0.02890 (18) | |
C1 | 0.8858 (2) | 0.8244 (2) | 0.16797 (13) | 0.0310 (6) | |
H1A | 0.8803 | 0.7846 | 0.1222 | 0.037* | |
H1B | 0.8436 | 0.7833 | 0.1938 | 0.037* | |
C2 | 1.0182 (2) | 0.8382 (2) | 0.19682 (12) | 0.0320 (6) | |
H2A | 1.0549 | 0.7690 | 0.1924 | 0.038* | |
H2B | 1.0606 | 0.8806 | 0.1719 | 0.038* | |
C3 | 0.9768 (2) | 1.0013 (2) | 0.26989 (13) | 0.0303 (6) | |
H3A | 1.0241 | 1.0390 | 0.2444 | 0.036* | |
H3B | 0.9819 | 1.0421 | 0.3154 | 0.036* | |
C4 | 0.8461 (2) | 0.9936 (2) | 0.23917 (13) | 0.0335 (6) | |
H4A | 0.7982 | 0.9618 | 0.2673 | 0.040* | |
H4B | 0.8176 | 1.0650 | 0.2391 | 0.040* | |
C5 | 0.8775 (2) | 0.9940 (2) | 0.12317 (13) | 0.0308 (6) | |
H5A | 0.8343 | 1.0599 | 0.1258 | 0.037* | |
H5B | 0.9608 | 1.0125 | 0.1400 | 0.037* | |
C6 | 0.8722 (2) | 0.9393 (2) | 0.05030 (13) | 0.0325 (6) | |
C7 | 0.9613 (2) | 0.8707 (2) | 0.02695 (13) | 0.0340 (6) | |
H7 | 1.0244 | 0.8566 | 0.0571 | 0.041* | |
C8 | 0.9583 (3) | 0.8229 (2) | −0.03992 (13) | 0.0397 (7) | |
H8 | 1.0170 | 0.7753 | −0.0544 | 0.048* | |
C9 | 0.8659 (3) | 0.8473 (2) | −0.08512 (14) | 0.0412 (7) | |
H9 | 0.8636 | 0.8165 | −0.1303 | 0.049* | |
C10 | 0.7781 (3) | 0.9165 (2) | −0.06377 (14) | 0.0398 (7) | |
H10 | 0.7171 | 0.9322 | −0.0946 | 0.048* | |
C11 | 0.7800 (2) | 0.9630 (2) | 0.00359 (13) | 0.0353 (6) | |
H11 | 0.7204 | 1.0098 | 0.0178 | 0.042* | |
C12 | 0.9765 (2) | 0.8347 (2) | 0.31560 (13) | 0.0311 (6) | |
C13 | 0.9627 (3) | 0.7213 (2) | 0.30128 (13) | 0.0340 (6) | |
H13 | 0.9852 | 0.6834 | 0.2611 | 0.041* | |
C14 | 0.9186 (3) | 0.6675 (2) | 0.34359 (13) | 0.0354 (6) | |
H14 | 0.9113 | 0.5936 | 0.3319 | 0.043* | |
C15 | 0.8835 (2) | 0.7196 (2) | 0.40471 (13) | 0.0305 (6) | |
C16 | 0.8951 (3) | 0.8298 (2) | 0.41933 (13) | 0.0356 (6) | |
H16 | 0.8717 | 0.8667 | 0.4596 | 0.043* | |
C17 | 0.9407 (2) | 0.8876 (2) | 0.37573 (12) | 0.0324 (6) | |
H17 | 0.9469 | 0.9615 | 0.3872 | 0.039* | |
C18 | 0.8331 (3) | 0.6590 (2) | 0.45344 (14) | 0.0377 (6) | |
C19 | 0.8319 (3) | 0.5369 (3) | 0.42843 (18) | 0.0562 (9) | |
H19A | 0.8053 | 0.5024 | 0.4620 | 0.084* | |
H19B | 0.9115 | 0.5147 | 0.4198 | 0.084* | |
H19C | 0.7781 | 0.5179 | 0.3879 | 0.084* | |
C20 | 0.9149 (3) | 0.6837 (3) | 0.52033 (15) | 0.0492 (8) | |
H20A | 0.9312 | 0.7591 | 0.5329 | 0.074* | |
H20B | 0.9891 | 0.6471 | 0.5153 | 0.074* | |
H20C | 0.8753 | 0.6603 | 0.5544 | 0.074* | |
C21 | 0.7067 (3) | 0.6965 (3) | 0.46511 (19) | 0.0615 (10) | |
H21A | 0.7103 | 0.7703 | 0.4867 | 0.092* | |
H21B | 0.6725 | 0.6551 | 0.4930 | 0.092* | |
H21C | 0.6576 | 0.6878 | 0.4229 | 0.092* | |
C22 | 0.6199 (3) | 0.7823 (2) | 0.06713 (13) | 0.0365 (6) | |
H22A | 0.5357 | 0.7664 | 0.0546 | 0.055* | |
H22B | 0.6597 | 0.7193 | 0.0757 | 0.055* | |
H22C | 0.6538 | 0.8063 | 0.0314 | 0.055* | |
C23 | 0.5732 (3) | 1.0357 (2) | 0.14290 (15) | 0.0402 (7) | |
H23A | 0.5559 | 1.0404 | 0.0967 | 0.060* | |
H23B | 0.6301 | 1.0911 | 0.1650 | 0.060* | |
H23C | 0.5004 | 1.0436 | 0.1641 | 0.060* | |
C24 | 0.6038 (3) | 0.8411 (2) | 0.22921 (13) | 0.0395 (7) | |
H24A | 0.5213 | 0.8172 | 0.2232 | 0.059* | |
H24B | 0.6172 | 0.8973 | 0.2681 | 0.059* | |
H24C | 0.6549 | 0.7829 | 0.2351 | 0.059* | |
C25 | 1.2746 (2) | 0.9738 (2) | 0.22833 (14) | 0.0351 (6) | |
H25A | 1.3549 | 1.0023 | 0.2421 | 0.053* | |
H25B | 1.2228 | 1.0296 | 0.2185 | 0.053* | |
H25C | 1.2745 | 0.9188 | 0.1890 | 0.053* | |
C26 | 1.2214 (3) | 1.0128 (2) | 0.38873 (13) | 0.0397 (7) | |
H26A | 1.1903 | 0.9774 | 0.4207 | 0.060* | |
H26B | 1.1735 | 1.0734 | 0.3839 | 0.060* | |
H26C | 1.3031 | 1.0361 | 0.4041 | 0.060* | |
C27 | 1.2719 (2) | 0.7689 (2) | 0.30281 (14) | 0.0361 (6) | |
H27A | 1.3543 | 0.7724 | 0.3220 | 0.054* | |
H27B | 1.2655 | 0.7280 | 0.2579 | 0.054* | |
H27C | 1.2234 | 0.7356 | 0.3292 | 0.054* | |
C28 | 0.4553 (2) | 0.5047 (2) | 0.77416 (12) | 0.0291 (6) | |
H28A | 0.3941 | 0.5294 | 0.7439 | 0.035* | |
H28B | 0.4312 | 0.4335 | 0.7778 | 0.035* | |
C29 | 0.5737 (2) | 0.49806 (19) | 0.74267 (12) | 0.0259 (5) | |
H29A | 0.6326 | 0.4633 | 0.7688 | 0.031* | |
H29B | 0.5610 | 0.4550 | 0.6978 | 0.031* | |
C30 | 0.6428 (2) | 0.6655 (2) | 0.81280 (13) | 0.0330 (6) | |
H30A | 0.6974 | 0.6256 | 0.8380 | 0.040* | |
H30B | 0.6794 | 0.7352 | 0.8153 | 0.040* | |
C31 | 0.5237 (2) | 0.6781 (2) | 0.84352 (13) | 0.0334 (6) | |
H31A | 0.5395 | 0.7153 | 0.8898 | 0.040* | |
H31B | 0.4722 | 0.7224 | 0.8199 | 0.040* | |
C32 | 0.4999 (2) | 0.5226 (2) | 0.90057 (13) | 0.0365 (7) | |
H32A | 0.4906 | 0.5733 | 0.9416 | 0.044* | |
H32B | 0.4455 | 0.4628 | 0.8989 | 0.044* | |
C33 | 0.6261 (2) | 0.4825 (2) | 0.90633 (13) | 0.0301 (6) | |
C34 | 0.6475 (2) | 0.3752 (2) | 0.88124 (13) | 0.0301 (6) | |
H34 | 0.5850 | 0.3300 | 0.8583 | 0.036* | |
C35 | 0.7626 (3) | 0.3365 (2) | 0.89078 (14) | 0.0376 (6) | |
H35 | 0.7764 | 0.2653 | 0.8737 | 0.045* | |
C36 | 0.8557 (3) | 0.4011 (3) | 0.92486 (14) | 0.0438 (7) | |
H36 | 0.9318 | 0.3736 | 0.9314 | 0.053* | |
C37 | 0.8367 (3) | 0.5082 (3) | 0.94981 (15) | 0.0449 (7) | |
H37 | 0.9002 | 0.5529 | 0.9721 | 0.054* | |
C38 | 0.7214 (3) | 0.5479 (2) | 0.94111 (13) | 0.0397 (7) | |
H38 | 0.7080 | 0.6189 | 0.9588 | 0.048* | |
C39 | 0.5475 (2) | 0.6626 (2) | 0.69475 (13) | 0.0320 (6) | |
C40 | 0.5367 (3) | 0.7738 (2) | 0.70635 (14) | 0.0364 (6) | |
H40 | 0.5732 | 0.8132 | 0.7467 | 0.044* | |
C41 | 0.4777 (2) | 0.8268 (2) | 0.66354 (13) | 0.0328 (6) | |
H41 | 0.4755 | 0.9008 | 0.6743 | 0.039* | |
C42 | 0.4195 (2) | 0.7718 (2) | 0.60283 (14) | 0.0344 (6) | |
C43 | 0.4286 (2) | 0.6624 (2) | 0.58951 (13) | 0.0336 (6) | |
H43 | 0.3920 | 0.6241 | 0.5489 | 0.040* | |
C44 | 0.4894 (2) | 0.6068 (2) | 0.63361 (13) | 0.0345 (6) | |
H44 | 0.4917 | 0.5329 | 0.6228 | 0.041* | |
C45 | 0.3507 (2) | 0.8302 (2) | 0.55320 (14) | 0.0367 (6) | |
C46 | 0.2207 (3) | 0.7874 (3) | 0.53678 (17) | 0.0520 (9) | |
H46A | 0.2202 | 0.7129 | 0.5169 | 0.078* | |
H46B | 0.1781 | 0.8253 | 0.5060 | 0.078* | |
H46C | 0.1823 | 0.7971 | 0.5772 | 0.078* | |
C47 | 0.3529 (3) | 0.9526 (3) | 0.57814 (18) | 0.0555 (9) | |
H47A | 0.3151 | 0.9857 | 0.5434 | 0.083* | |
H47B | 0.4347 | 0.9783 | 0.5895 | 0.083* | |
H47C | 0.3104 | 0.9697 | 0.6170 | 0.083* | |
C48 | 0.4120 (3) | 0.8086 (2) | 0.48701 (14) | 0.0425 (7) | |
H48A | 0.4215 | 0.7334 | 0.4728 | 0.064* | |
H48B | 0.4895 | 0.8441 | 0.4947 | 0.064* | |
H48C | 0.3628 | 0.8352 | 0.4529 | 0.064* | |
C49 | 0.8475 (3) | 0.7362 (2) | 0.70366 (15) | 0.0407 (7) | |
H49A | 0.8504 | 0.7787 | 0.7480 | 0.061* | |
H49B | 0.7924 | 0.7664 | 0.6737 | 0.061* | |
H49C | 0.9262 | 0.7348 | 0.6889 | 0.061* | |
C50 | 0.7598 (3) | 0.4889 (2) | 0.61685 (13) | 0.0381 (7) | |
H50A | 0.8344 | 0.4679 | 0.5996 | 0.057* | |
H50B | 0.7123 | 0.5233 | 0.5858 | 0.057* | |
H50C | 0.7168 | 0.4271 | 0.6228 | 0.057* | |
C51 | 0.8883 (2) | 0.5318 (2) | 0.77515 (14) | 0.0352 (6) | |
H51A | 0.9667 | 0.5145 | 0.7620 | 0.053* | |
H51B | 0.8487 | 0.4688 | 0.7819 | 0.053* | |
H51C | 0.8958 | 0.5842 | 0.8161 | 0.053* | |
C52 | 0.2199 (3) | 0.6759 (3) | 0.77589 (16) | 0.0478 (8) | |
H52A | 0.1437 | 0.7079 | 0.7827 | 0.072* | |
H52B | 0.2110 | 0.6206 | 0.7364 | 0.072* | |
H52C | 0.2769 | 0.7290 | 0.7706 | 0.072* | |
C53 | 0.2949 (3) | 0.7196 (2) | 0.94034 (15) | 0.0439 (7) | |
H53A | 0.2176 | 0.7478 | 0.9491 | 0.066* | |
H53B | 0.3489 | 0.7764 | 0.9372 | 0.066* | |
H53C | 0.3263 | 0.6857 | 0.9761 | 0.066* | |
C54 | 0.2034 (3) | 0.4745 (3) | 0.85564 (17) | 0.0492 (8) | |
H54A | 0.2406 | 0.4472 | 0.8930 | 0.074* | |
H54B | 0.2141 | 0.4257 | 0.8148 | 0.074* | |
H54C | 0.1191 | 0.4829 | 0.8595 | 0.074* | |
N1 | 0.82603 (19) | 0.92951 (17) | 0.16896 (10) | 0.0292 (5) | |
N2 | 1.02877 (19) | 0.89295 (16) | 0.27066 (10) | 0.0294 (5) | |
N3 | 0.62219 (19) | 0.60702 (17) | 0.73935 (11) | 0.0309 (5) | |
N4 | 0.45731 (19) | 0.57570 (17) | 0.84175 (10) | 0.0304 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Al1 | 0.0286 (4) | 0.0340 (4) | 0.0311 (4) | 0.0010 (3) | 0.0052 (3) | 0.0062 (3) |
Al2 | 0.0318 (4) | 0.0320 (4) | 0.0277 (4) | 0.0001 (3) | 0.0005 (3) | 0.0092 (3) |
Al3 | 0.0294 (4) | 0.0345 (4) | 0.0383 (5) | 0.0049 (3) | 0.0066 (3) | 0.0152 (4) |
Al4 | 0.0282 (4) | 0.0324 (4) | 0.0294 (4) | 0.0031 (3) | 0.0115 (3) | 0.0097 (3) |
C1 | 0.0304 (14) | 0.0297 (14) | 0.0336 (14) | 0.0013 (11) | 0.0043 (11) | 0.0076 (11) |
C2 | 0.0317 (14) | 0.0350 (15) | 0.0283 (13) | 0.0027 (11) | 0.0027 (11) | 0.0043 (11) |
C3 | 0.0312 (14) | 0.0307 (14) | 0.0299 (13) | −0.0002 (11) | 0.0007 (11) | 0.0092 (11) |
C4 | 0.0323 (15) | 0.0317 (14) | 0.0350 (14) | 0.0006 (11) | 0.0018 (11) | 0.0037 (11) |
C5 | 0.0328 (14) | 0.0278 (14) | 0.0348 (14) | −0.0021 (11) | 0.0043 (11) | 0.0134 (11) |
C6 | 0.0352 (15) | 0.0292 (14) | 0.0337 (14) | −0.0047 (11) | 0.0010 (11) | 0.0095 (11) |
C7 | 0.0297 (14) | 0.0437 (16) | 0.0316 (14) | −0.0017 (12) | 0.0096 (11) | 0.0118 (12) |
C8 | 0.0371 (16) | 0.0519 (18) | 0.0319 (15) | −0.0052 (13) | 0.0139 (12) | 0.0074 (13) |
C9 | 0.0426 (17) | 0.0513 (18) | 0.0299 (14) | −0.0241 (14) | 0.0084 (12) | 0.0070 (13) |
C10 | 0.0356 (16) | 0.0568 (19) | 0.0301 (14) | −0.0108 (14) | −0.0035 (12) | 0.0201 (13) |
C11 | 0.0325 (15) | 0.0473 (17) | 0.0286 (14) | −0.0034 (12) | −0.0030 (11) | 0.0172 (12) |
C12 | 0.0305 (14) | 0.0349 (14) | 0.0303 (13) | −0.0002 (11) | 0.0069 (11) | 0.0107 (11) |
C13 | 0.0419 (16) | 0.0321 (14) | 0.0299 (14) | 0.0039 (12) | 0.0141 (12) | 0.0052 (11) |
C14 | 0.0419 (16) | 0.0343 (15) | 0.0335 (14) | −0.0037 (12) | 0.0118 (12) | 0.0111 (12) |
C15 | 0.0372 (15) | 0.0304 (14) | 0.0283 (13) | −0.0017 (11) | 0.0106 (11) | 0.0127 (11) |
C16 | 0.0473 (17) | 0.0315 (14) | 0.0305 (14) | 0.0020 (12) | 0.0142 (12) | 0.0066 (11) |
C17 | 0.0373 (15) | 0.0349 (15) | 0.0280 (13) | 0.0048 (12) | 0.0131 (11) | 0.0082 (11) |
C18 | 0.0368 (15) | 0.0436 (16) | 0.0396 (15) | −0.0011 (12) | 0.0189 (12) | 0.0172 (13) |
C19 | 0.055 (2) | 0.050 (2) | 0.066 (2) | −0.0124 (16) | 0.0168 (17) | 0.0138 (17) |
C20 | 0.052 (2) | 0.053 (2) | 0.0437 (18) | −0.0154 (15) | 0.0083 (15) | 0.0115 (15) |
C21 | 0.055 (2) | 0.069 (2) | 0.068 (2) | 0.0145 (18) | 0.0209 (18) | 0.0229 (19) |
C22 | 0.0335 (15) | 0.0365 (15) | 0.0358 (15) | −0.0101 (12) | 0.0004 (11) | 0.0003 (12) |
C23 | 0.0302 (15) | 0.0399 (16) | 0.0534 (18) | 0.0088 (12) | 0.0123 (13) | 0.0120 (14) |
C24 | 0.0381 (16) | 0.0514 (18) | 0.0321 (15) | −0.0080 (13) | 0.0124 (12) | 0.0113 (13) |
C25 | 0.0300 (14) | 0.0392 (15) | 0.0388 (15) | −0.0090 (12) | 0.0033 (11) | 0.0150 (12) |
C26 | 0.0441 (17) | 0.0393 (16) | 0.0329 (15) | 0.0024 (13) | −0.0039 (12) | 0.0048 (12) |
C27 | 0.0341 (15) | 0.0330 (15) | 0.0434 (16) | 0.0041 (12) | −0.0005 (12) | 0.0152 (12) |
C28 | 0.0289 (14) | 0.0270 (13) | 0.0329 (14) | −0.0015 (11) | 0.0115 (11) | 0.0055 (11) |
C29 | 0.0281 (13) | 0.0238 (12) | 0.0298 (13) | 0.0027 (10) | 0.0123 (10) | 0.0097 (10) |
C30 | 0.0310 (14) | 0.0330 (14) | 0.0346 (15) | 0.0011 (11) | 0.0042 (11) | 0.0054 (11) |
C31 | 0.0332 (15) | 0.0330 (15) | 0.0341 (14) | 0.0043 (12) | 0.0057 (11) | 0.0057 (11) |
C32 | 0.0344 (15) | 0.0481 (17) | 0.0356 (15) | 0.0200 (13) | 0.0148 (12) | 0.0230 (13) |
C33 | 0.0274 (13) | 0.0343 (14) | 0.0318 (14) | 0.0044 (11) | 0.0085 (11) | 0.0113 (11) |
C34 | 0.0325 (14) | 0.0308 (14) | 0.0311 (13) | 0.0090 (11) | 0.0075 (11) | 0.0140 (11) |
C35 | 0.0344 (15) | 0.0390 (16) | 0.0437 (16) | 0.0103 (13) | 0.0130 (13) | 0.0136 (13) |
C36 | 0.0387 (17) | 0.060 (2) | 0.0358 (16) | 0.0147 (15) | 0.0070 (13) | 0.0154 (14) |
C37 | 0.0368 (17) | 0.0536 (19) | 0.0422 (17) | 0.0015 (14) | −0.0099 (13) | 0.0121 (14) |
C38 | 0.0446 (17) | 0.0422 (17) | 0.0302 (14) | 0.0056 (13) | −0.0025 (12) | 0.0056 (12) |
C39 | 0.0327 (14) | 0.0322 (14) | 0.0320 (14) | 0.0009 (11) | 0.0056 (11) | 0.0079 (11) |
C40 | 0.0420 (16) | 0.0312 (14) | 0.0348 (15) | 0.0011 (12) | −0.0004 (12) | 0.0062 (12) |
C41 | 0.0338 (15) | 0.0294 (14) | 0.0352 (14) | 0.0023 (11) | 0.0001 (11) | 0.0085 (11) |
C42 | 0.0336 (15) | 0.0351 (15) | 0.0366 (15) | 0.0024 (12) | 0.0029 (11) | 0.0126 (12) |
C43 | 0.0305 (14) | 0.0349 (15) | 0.0327 (14) | −0.0022 (11) | −0.0046 (11) | 0.0046 (11) |
C44 | 0.0346 (15) | 0.0358 (15) | 0.0301 (14) | −0.0004 (12) | −0.0043 (11) | 0.0038 (11) |
C45 | 0.0306 (15) | 0.0443 (16) | 0.0344 (15) | 0.0038 (12) | −0.0084 (11) | 0.0119 (12) |
C46 | 0.051 (2) | 0.051 (2) | 0.0533 (19) | −0.0211 (15) | −0.0185 (15) | 0.0215 (16) |
C47 | 0.049 (2) | 0.049 (2) | 0.068 (2) | 0.0183 (16) | −0.0039 (17) | 0.0165 (17) |
C48 | 0.0428 (17) | 0.0464 (17) | 0.0377 (16) | 0.0100 (14) | −0.0105 (13) | 0.0149 (13) |
C49 | 0.0431 (17) | 0.0312 (15) | 0.0544 (18) | −0.0028 (13) | 0.0220 (14) | 0.0158 (13) |
C50 | 0.0492 (18) | 0.0377 (16) | 0.0298 (14) | 0.0044 (13) | 0.0183 (12) | 0.0054 (12) |
C51 | 0.0267 (14) | 0.0404 (16) | 0.0383 (15) | 0.0041 (12) | 0.0041 (11) | 0.0070 (12) |
C52 | 0.0330 (16) | 0.058 (2) | 0.057 (2) | 0.0065 (14) | −0.0002 (14) | 0.0276 (16) |
C53 | 0.0395 (17) | 0.0460 (18) | 0.0494 (18) | 0.0131 (14) | 0.0192 (14) | 0.0095 (14) |
C54 | 0.0364 (17) | 0.0496 (19) | 0.066 (2) | −0.0027 (14) | 0.0051 (15) | 0.0230 (16) |
N1 | 0.0291 (11) | 0.0277 (11) | 0.0310 (11) | −0.0016 (9) | 0.0054 (9) | 0.0053 (9) |
N2 | 0.0317 (12) | 0.0261 (11) | 0.0325 (12) | 0.0028 (9) | 0.0060 (9) | 0.0091 (9) |
N3 | 0.0308 (12) | 0.0300 (12) | 0.0337 (12) | 0.0018 (9) | 0.0089 (9) | 0.0080 (9) |
N4 | 0.0312 (12) | 0.0334 (12) | 0.0300 (11) | 0.0042 (9) | 0.0085 (9) | 0.0118 (9) |
Al1—C22 | 1.975 (3) | C25—H25B | 0.9600 |
Al1—C23 | 1.980 (3) | C25—H25C | 0.9600 |
Al1—C24 | 1.991 (3) | C26—H26A | 0.9600 |
Al1—N1 | 2.089 (2) | C26—H26B | 0.9600 |
Al2—C27 | 1.963 (3) | C26—H26C | 0.9600 |
Al2—C26 | 1.973 (3) | C27—H27A | 0.9600 |
Al2—C25 | 1.984 (3) | C27—H27B | 0.9600 |
Al2—N2 | 2.121 (2) | C27—H27C | 0.9600 |
Al3—C54 | 1.971 (3) | C28—N4 | 1.497 (3) |
Al3—C53 | 1.983 (3) | C28—C29 | 1.530 (3) |
Al3—C52 | 1.991 (3) | C28—H28A | 0.9700 |
Al3—N4 | 2.095 (2) | C28—H28B | 0.9700 |
Al4—C51 | 1.970 (3) | C29—N3 | 1.512 (3) |
Al4—C49 | 1.979 (3) | C29—H29A | 0.9700 |
Al4—C50 | 1.986 (3) | C29—H29B | 0.9700 |
Al4—N3 | 2.109 (2) | C30—C31 | 1.530 (4) |
C1—N1 | 1.504 (3) | C30—N3 | 1.535 (3) |
C1—C2 | 1.531 (4) | C30—H30A | 0.9700 |
C1—H1A | 0.9700 | C30—H30B | 0.9700 |
C1—H1B | 0.9700 | C31—N4 | 1.497 (3) |
C2—N2 | 1.528 (3) | C31—H31A | 0.9700 |
C2—H2A | 0.9700 | C31—H31B | 0.9700 |
C2—H2B | 0.9700 | C32—C33 | 1.505 (4) |
C3—N2 | 1.509 (3) | C32—N4 | 1.532 (3) |
C3—C4 | 1.524 (4) | C32—H32A | 0.9700 |
C3—H3A | 0.9700 | C32—H32B | 0.9700 |
C3—H3B | 0.9700 | C33—C38 | 1.393 (4) |
C4—N1 | 1.502 (3) | C33—C34 | 1.401 (4) |
C4—H4A | 0.9700 | C34—C35 | 1.389 (4) |
C4—H4B | 0.9700 | C34—H34 | 0.9300 |
C5—C6 | 1.513 (4) | C35—C36 | 1.367 (4) |
C5—N1 | 1.521 (3) | C35—H35 | 0.9300 |
C5—H5A | 0.9700 | C36—C37 | 1.391 (4) |
C5—H5B | 0.9700 | C36—H36 | 0.9300 |
C6—C7 | 1.392 (4) | C37—C38 | 1.395 (4) |
C6—C11 | 1.407 (4) | C37—H37 | 0.9300 |
C7—C8 | 1.382 (4) | C38—H38 | 0.9300 |
C7—H7 | 0.9300 | C39—C44 | 1.404 (4) |
C8—C9 | 1.392 (4) | C39—C40 | 1.404 (4) |
C8—H8 | 0.9300 | C39—N3 | 1.463 (3) |
C9—C10 | 1.373 (4) | C40—C41 | 1.335 (4) |
C9—H9 | 0.9300 | C40—H40 | 0.9300 |
C10—C11 | 1.389 (4) | C41—C42 | 1.394 (4) |
C10—H10 | 0.9300 | C41—H41 | 0.9300 |
C11—H11 | 0.9300 | C42—C43 | 1.381 (4) |
C12—C17 | 1.384 (3) | C42—C45 | 1.525 (4) |
C12—C13 | 1.428 (4) | C43—C44 | 1.383 (4) |
C12—N2 | 1.460 (3) | C43—H43 | 0.9300 |
C13—C14 | 1.340 (4) | C44—H44 | 0.9300 |
C13—H13 | 0.9300 | C45—C46 | 1.531 (4) |
C14—C15 | 1.394 (4) | C45—C47 | 1.550 (4) |
C14—H14 | 0.9300 | C45—C48 | 1.562 (4) |
C15—C16 | 1.387 (4) | C46—H46A | 0.9600 |
C15—C18 | 1.530 (3) | C46—H46B | 0.9600 |
C16—C17 | 1.401 (4) | C46—H46C | 0.9600 |
C16—H16 | 0.9300 | C47—H47A | 0.9600 |
C17—H17 | 0.9300 | C47—H47B | 0.9600 |
C18—C21 | 1.525 (4) | C47—H47C | 0.9600 |
C18—C20 | 1.541 (4) | C48—H48A | 0.9600 |
C18—C19 | 1.546 (4) | C48—H48B | 0.9600 |
C19—H19A | 0.9600 | C48—H48C | 0.9600 |
C19—H19B | 0.9600 | C49—H49A | 0.9600 |
C19—H19C | 0.9600 | C49—H49B | 0.9600 |
C20—H20A | 0.9600 | C49—H49C | 0.9600 |
C20—H20B | 0.9600 | C50—H50A | 0.9600 |
C20—H20C | 0.9600 | C50—H50B | 0.9600 |
C21—H21A | 0.9600 | C50—H50C | 0.9600 |
C21—H21B | 0.9600 | C51—H51A | 0.9600 |
C21—H21C | 0.9600 | C51—H51B | 0.9600 |
C22—H22A | 0.9600 | C51—H51C | 0.9600 |
C22—H22B | 0.9600 | C52—H52A | 0.9600 |
C22—H22C | 0.9600 | C52—H52B | 0.9600 |
C23—H23A | 0.9600 | C52—H52C | 0.9600 |
C23—H23B | 0.9600 | C53—H53A | 0.9600 |
C23—H23C | 0.9600 | C53—H53B | 0.9600 |
C24—H24A | 0.9600 | C53—H53C | 0.9600 |
C24—H24B | 0.9600 | C54—H54A | 0.9600 |
C24—H24C | 0.9600 | C54—H54B | 0.9600 |
C25—H25A | 0.9600 | C54—H54C | 0.9600 |
C22—Al1—C23 | 117.28 (13) | N4—C28—C29 | 115.9 (2) |
C22—Al1—C24 | 111.64 (13) | N4—C28—H28A | 108.3 |
C23—Al1—C24 | 113.85 (13) | C29—C28—H28A | 108.3 |
C22—Al1—N1 | 106.49 (11) | N4—C28—H28B | 108.3 |
C23—Al1—N1 | 102.93 (11) | C29—C28—H28B | 108.3 |
C24—Al1—N1 | 102.83 (11) | H28A—C28—H28B | 107.4 |
C27—Al2—C26 | 116.72 (13) | N3—C29—C28 | 111.82 (19) |
C27—Al2—C25 | 112.84 (13) | N3—C29—H29A | 109.3 |
C26—Al2—C25 | 115.29 (13) | C28—C29—H29A | 109.3 |
C27—Al2—N2 | 104.44 (11) | N3—C29—H29B | 109.3 |
C26—Al2—N2 | 102.78 (11) | C28—C29—H29B | 109.3 |
C25—Al2—N2 | 102.35 (10) | H29A—C29—H29B | 107.9 |
C54—Al3—C53 | 116.88 (14) | C31—C30—N3 | 110.5 (2) |
C54—Al3—C52 | 114.34 (14) | C31—C30—H30A | 109.5 |
C53—Al3—C52 | 113.25 (14) | N3—C30—H30A | 109.5 |
C54—Al3—N4 | 102.92 (12) | C31—C30—H30B | 109.5 |
C53—Al3—N4 | 102.49 (11) | N3—C30—H30B | 109.5 |
C52—Al3—N4 | 104.70 (11) | H30A—C30—H30B | 108.1 |
C51—Al4—C49 | 110.99 (13) | N4—C31—C30 | 114.7 (2) |
C51—Al4—C50 | 115.34 (12) | N4—C31—H31A | 108.6 |
C49—Al4—C50 | 117.80 (13) | C30—C31—H31A | 108.6 |
C51—Al4—N3 | 102.76 (10) | N4—C31—H31B | 108.6 |
C49—Al4—N3 | 104.58 (11) | C30—C31—H31B | 108.6 |
C50—Al4—N3 | 103.16 (11) | H31A—C31—H31B | 107.6 |
N1—C1—C2 | 112.2 (2) | C33—C32—N4 | 119.1 (2) |
N1—C1—H1A | 109.2 | C33—C32—H32A | 107.6 |
C2—C1—H1A | 109.2 | N4—C32—H32A | 107.6 |
N1—C1—H1B | 109.2 | C33—C32—H32B | 107.6 |
C2—C1—H1B | 109.2 | N4—C32—H32B | 107.6 |
H1A—C1—H1B | 107.9 | H32A—C32—H32B | 107.0 |
N2—C2—C1 | 110.2 (2) | C38—C33—C34 | 118.7 (2) |
N2—C2—H2A | 109.6 | C38—C33—C32 | 121.3 (3) |
C1—C2—H2A | 109.6 | C34—C33—C32 | 119.8 (2) |
N2—C2—H2B | 109.6 | C35—C34—C33 | 119.8 (3) |
C1—C2—H2B | 109.6 | C35—C34—H34 | 120.1 |
H2A—C2—H2B | 108.1 | C33—C34—H34 | 120.1 |
N2—C3—C4 | 112.0 (2) | C36—C35—C34 | 121.2 (3) |
N2—C3—H3A | 109.2 | C36—C35—H35 | 119.4 |
C4—C3—H3A | 109.2 | C34—C35—H35 | 119.4 |
N2—C3—H3B | 109.2 | C35—C36—C37 | 120.0 (3) |
C4—C3—H3B | 109.2 | C35—C36—H36 | 120.0 |
H3A—C3—H3B | 107.9 | C37—C36—H36 | 120.0 |
N1—C4—C3 | 114.2 (2) | C36—C37—C38 | 119.4 (3) |
N1—C4—H4A | 108.7 | C36—C37—H37 | 120.3 |
C3—C4—H4A | 108.7 | C38—C37—H37 | 120.3 |
N1—C4—H4B | 108.7 | C33—C38—C37 | 121.0 (3) |
C3—C4—H4B | 108.7 | C33—C38—H38 | 119.5 |
H4A—C4—H4B | 107.6 | C37—C38—H38 | 119.5 |
C6—C5—N1 | 115.5 (2) | C44—C39—C40 | 115.4 (2) |
C6—C5—H5A | 108.4 | C44—C39—N3 | 120.8 (2) |
N1—C5—H5A | 108.4 | C40—C39—N3 | 123.6 (2) |
C6—C5—H5B | 108.4 | C41—C40—C39 | 124.6 (3) |
N1—C5—H5B | 108.4 | C41—C40—H40 | 117.7 |
H5A—C5—H5B | 107.5 | C39—C40—H40 | 117.7 |
C7—C6—C11 | 118.4 (3) | C40—C41—C42 | 120.3 (3) |
C7—C6—C5 | 121.6 (2) | C40—C41—H41 | 119.9 |
C11—C6—C5 | 119.9 (2) | C42—C41—H41 | 119.9 |
C8—C7—C6 | 121.7 (3) | C43—C42—C41 | 116.8 (2) |
C8—C7—H7 | 119.2 | C43—C42—C45 | 121.7 (2) |
C6—C7—H7 | 119.2 | C41—C42—C45 | 121.5 (2) |
C7—C8—C9 | 118.8 (3) | C42—C43—C44 | 123.2 (3) |
C7—C8—H8 | 120.6 | C42—C43—H43 | 118.4 |
C9—C8—H8 | 120.6 | C44—C43—H43 | 118.4 |
C10—C9—C8 | 120.8 (3) | C43—C44—C39 | 119.7 (3) |
C10—C9—H9 | 119.6 | C43—C44—H44 | 120.2 |
C8—C9—H9 | 119.6 | C39—C44—H44 | 120.2 |
C9—C10—C11 | 120.4 (3) | C42—C45—C46 | 110.3 (2) |
C9—C10—H10 | 119.8 | C42—C45—C47 | 113.0 (2) |
C11—C10—H10 | 119.8 | C46—C45—C47 | 110.2 (2) |
C10—C11—C6 | 119.9 (3) | C42—C45—C48 | 108.3 (2) |
C10—C11—H11 | 120.0 | C46—C45—C48 | 108.1 (2) |
C6—C11—H11 | 120.0 | C47—C45—C48 | 106.8 (3) |
C17—C12—C13 | 116.6 (2) | C45—C46—H46A | 109.5 |
C17—C12—N2 | 121.0 (2) | C45—C46—H46B | 109.5 |
C13—C12—N2 | 122.4 (2) | H46A—C46—H46B | 109.5 |
C14—C13—C12 | 122.5 (2) | C45—C46—H46C | 109.5 |
C14—C13—H13 | 118.8 | H46A—C46—H46C | 109.5 |
C12—C13—H13 | 118.8 | H46B—C46—H46C | 109.5 |
C13—C14—C15 | 121.6 (3) | C45—C47—H47A | 109.5 |
C13—C14—H14 | 119.2 | C45—C47—H47B | 109.5 |
C15—C14—H14 | 119.2 | H47A—C47—H47B | 109.5 |
C16—C15—C14 | 116.9 (2) | C45—C47—H47C | 109.5 |
C16—C15—C18 | 121.1 (2) | H47A—C47—H47C | 109.5 |
C14—C15—C18 | 122.1 (2) | H47B—C47—H47C | 109.5 |
C15—C16—C17 | 122.4 (2) | C45—C48—H48A | 109.5 |
C15—C16—H16 | 118.8 | C45—C48—H48B | 109.5 |
C17—C16—H16 | 118.8 | H48A—C48—H48B | 109.5 |
C12—C17—C16 | 120.0 (2) | C45—C48—H48C | 109.5 |
C12—C17—H17 | 120.0 | H48A—C48—H48C | 109.5 |
C16—C17—H17 | 120.0 | H48B—C48—H48C | 109.5 |
C21—C18—C15 | 109.2 (2) | Al4—C49—H49A | 109.5 |
C21—C18—C20 | 109.3 (3) | Al4—C49—H49B | 109.5 |
C15—C18—C20 | 108.4 (2) | H49A—C49—H49B | 109.5 |
C21—C18—C19 | 110.3 (3) | Al4—C49—H49C | 109.5 |
C15—C18—C19 | 112.6 (2) | H49A—C49—H49C | 109.5 |
C20—C18—C19 | 107.0 (3) | H49B—C49—H49C | 109.5 |
C18—C19—H19A | 109.5 | Al4—C50—H50A | 109.5 |
C18—C19—H19B | 109.5 | Al4—C50—H50B | 109.5 |
H19A—C19—H19B | 109.5 | H50A—C50—H50B | 109.5 |
C18—C19—H19C | 109.5 | Al4—C50—H50C | 109.5 |
H19A—C19—H19C | 109.5 | H50A—C50—H50C | 109.5 |
H19B—C19—H19C | 109.5 | H50B—C50—H50C | 109.5 |
C18—C20—H20A | 109.5 | Al4—C51—H51A | 109.5 |
C18—C20—H20B | 109.5 | Al4—C51—H51B | 109.5 |
H20A—C20—H20B | 109.5 | H51A—C51—H51B | 109.5 |
C18—C20—H20C | 109.5 | Al4—C51—H51C | 109.5 |
H20A—C20—H20C | 109.5 | H51A—C51—H51C | 109.5 |
H20B—C20—H20C | 109.5 | H51B—C51—H51C | 109.5 |
C18—C21—H21A | 109.5 | Al3—C52—H52A | 109.5 |
C18—C21—H21B | 109.5 | Al3—C52—H52B | 109.5 |
H21A—C21—H21B | 109.5 | H52A—C52—H52B | 109.5 |
C18—C21—H21C | 109.5 | Al3—C52—H52C | 109.5 |
H21A—C21—H21C | 109.5 | H52A—C52—H52C | 109.5 |
H21B—C21—H21C | 109.5 | H52B—C52—H52C | 109.5 |
Al1—C22—H22A | 109.5 | Al3—C53—H53A | 109.5 |
Al1—C22—H22B | 109.5 | Al3—C53—H53B | 109.5 |
H22A—C22—H22B | 109.5 | H53A—C53—H53B | 109.5 |
Al1—C22—H22C | 109.5 | Al3—C53—H53C | 109.5 |
H22A—C22—H22C | 109.5 | H53A—C53—H53C | 109.5 |
H22B—C22—H22C | 109.5 | H53B—C53—H53C | 109.5 |
Al1—C23—H23A | 109.5 | Al3—C54—H54A | 109.5 |
Al1—C23—H23B | 109.5 | Al3—C54—H54B | 109.5 |
H23A—C23—H23B | 109.5 | H54A—C54—H54B | 109.5 |
Al1—C23—H23C | 109.5 | Al3—C54—H54C | 109.5 |
H23A—C23—H23C | 109.5 | H54A—C54—H54C | 109.5 |
H23B—C23—H23C | 109.5 | H54B—C54—H54C | 109.5 |
Al1—C24—H24A | 109.5 | C4—N1—C1 | 108.1 (2) |
Al1—C24—H24B | 109.5 | C4—N1—C5 | 107.71 (19) |
H24A—C24—H24B | 109.5 | C1—N1—C5 | 112.8 (2) |
Al1—C24—H24C | 109.5 | C4—N1—Al1 | 106.49 (15) |
H24A—C24—H24C | 109.5 | C1—N1—Al1 | 106.19 (15) |
H24B—C24—H24C | 109.5 | C5—N1—Al1 | 115.23 (16) |
Al2—C25—H25A | 109.5 | C12—N2—C3 | 114.3 (2) |
Al2—C25—H25B | 109.5 | C12—N2—C2 | 116.1 (2) |
H25A—C25—H25B | 109.5 | C3—N2—C2 | 104.13 (19) |
Al2—C25—H25C | 109.5 | C12—N2—Al2 | 107.98 (16) |
H25A—C25—H25C | 109.5 | C3—N2—Al2 | 108.25 (15) |
H25B—C25—H25C | 109.5 | C2—N2—Al2 | 105.53 (15) |
Al2—C26—H26A | 109.5 | C39—N3—C29 | 114.5 (2) |
Al2—C26—H26B | 109.5 | C39—N3—C30 | 115.1 (2) |
H26A—C26—H26B | 109.5 | C29—N3—C30 | 104.30 (19) |
Al2—C26—H26C | 109.5 | C39—N3—Al4 | 107.48 (15) |
H26A—C26—H26C | 109.5 | C29—N3—Al4 | 108.44 (15) |
H26B—C26—H26C | 109.5 | C30—N3—Al4 | 106.70 (15) |
Al2—C27—H27A | 109.5 | C28—N4—C31 | 110.38 (19) |
Al2—C27—H27B | 109.5 | C28—N4—C32 | 114.7 (2) |
H27A—C27—H27B | 109.5 | C31—N4—C32 | 113.1 (2) |
Al2—C27—H27C | 109.5 | C28—N4—Al3 | 106.48 (15) |
H27A—C27—H27C | 109.5 | C31—N4—Al3 | 106.98 (15) |
H27B—C27—H27C | 109.5 | C32—N4—Al3 | 104.54 (15) |
N1—C1—C2—N2 | 63.3 (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—C11 | 99.2 (3) | C24—Al1—N1—C1 | 66.53 (18) |
C11—C6—C7—C8 | −2.5 (4) | C22—Al1—N1—C5 | 74.66 (19) |
C5—C6—C7—C8 | −178.2 (2) | C23—Al1—N1—C5 | −49.29 (19) |
C6—C7—C8—C9 | 2.3 (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—C3 | 147.0 (2) |
C9—C10—C11—C6 | 0.0 (4) | C17—C12—N2—C2 | −156.1 (2) |
C7—C6—C11—C10 | 1.3 (4) | C13—C12—N2—C2 | 25.7 (3) |
C5—C6—C11—C10 | 177.1 (2) | C17—C12—N2—Al2 | 85.7 (3) |
C17—C12—C13—C14 | −0.6 (4) | C13—C12—N2—Al2 | −92.5 (3) |
N2—C12—C13—C14 | 177.6 (3) | C4—C3—N2—C12 | −67.5 (3) |
C12—C13—C14—C15 | −0.1 (5) | C4—C3—N2—C2 | 60.2 (3) |
C13—C14—C15—C16 | 0.7 (4) | C4—C3—N2—Al2 | 172.11 (17) |
C13—C14—C15—C18 | −179.9 (3) | C1—C2—N2—C12 | 63.5 (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—C16 | 0.8 (4) | C27—Al2—N2—C12 | 54.28 (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—C12 | 172.10 (17) |
C16—C15—C18—C21 | 59.0 (4) | C27—Al2—N2—C3 | 178.53 (16) |
C14—C15—C18—C21 | −120.3 (3) | C26—Al2—N2—C3 | 56.22 (18) |
C16—C15—C18—C20 | −60.0 (3) | C25—Al2—N2—C3 | −63.65 (18) |
C14—C15—C18—C20 | 120.7 (3) | C27—Al2—N2—C2 | −70.47 (17) |
C16—C15—C18—C19 | −178.1 (3) | C26—Al2—N2—C2 | 167.22 (16) |
C14—C15—C18—C19 | 2.5 (4) | C25—Al2—N2—C2 | 47.35 (18) |
N4—C28—C29—N3 | −54.3 (3) | C44—C39—N3—C29 | −38.2 (3) |
N3—C30—C31—N4 | 58.4 (3) | C40—C39—N3—C29 | 147.3 (3) |
N4—C32—C33—C38 | 89.4 (3) | C44—C39—N3—C30 | −159.0 (2) |
N4—C32—C33—C34 | −96.0 (3) | C40—C39—N3—C30 | 26.5 (3) |
C38—C33—C34—C35 | −0.7 (4) | C44—C39—N3—Al4 | 82.3 (3) |
C32—C33—C34—C35 | −175.4 (2) | C40—C39—N3—Al4 | −92.2 (3) |
C33—C34—C35—C36 | 0.6 (4) | C28—C29—N3—C39 | −65.6 (3) |
C34—C35—C36—C37 | −1.0 (4) | C28—C29—N3—C30 | 61.0 (3) |
C35—C36—C37—C38 | 1.6 (4) | C28—C29—N3—Al4 | 174.39 (16) |
C34—C33—C38—C37 | 1.3 (4) | C31—C30—N3—C39 | 63.1 (3) |
C32—C33—C38—C37 | 175.9 (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—C39 | 172.68 (17) |
N3—C39—C40—C41 | 173.8 (3) | C49—Al4—N3—C39 | 56.67 (19) |
C39—C40—C41—C42 | 1.1 (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—C45 | 179.5 (3) | C49—Al4—N3—C29 | −179.10 (17) |
C41—C42—C43—C44 | 1.4 (4) | C50—Al4—N3—C29 | 57.15 (18) |
C45—C42—C43—C44 | −179.4 (3) | C51—Al4—N3—C30 | 48.73 (18) |
C42—C43—C44—C39 | −1.3 (4) | C49—Al4—N3—C30 | −67.27 (18) |
C40—C39—C44—C43 | 0.9 (4) | C50—Al4—N3—C30 | 168.97 (16) |
N3—C39—C44—C43 | −174.0 (2) | C29—C28—N4—C31 | 43.4 (3) |
C43—C42—C45—C46 | 56.6 (4) | C29—C28—N4—C32 | −85.8 (3) |
C41—C42—C45—C46 | −124.3 (3) | C29—C28—N4—Al3 | 159.12 (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—C32 | 84.4 (3) |
C43—C42—C45—C48 | −61.5 (3) | C30—C31—N4—Al3 | −161.01 (18) |
C41—C42—C45—C48 | 117.6 (3) | C33—C32—N4—C28 | 62.6 (3) |
C3—C4—N1—C1 | 50.7 (3) | C33—C32—N4—C31 | −65.1 (3) |
C3—C4—N1—C5 | −71.4 (3) | C33—C32—N4—Al3 | 178.8 (2) |
C3—C4—N1—Al1 | 164.42 (18) | C54—Al3—N4—C28 | 64.43 (18) |
C2—C1—N1—C4 | −53.5 (3) | C53—Al3—N4—C28 | −173.84 (17) |
C2—C1—N1—C5 | 65.4 (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—C4 | 176.5 (2) | C53—Al3—N4—C31 | −55.81 (18) |
C6—C5—N1—C1 | 57.4 (3) | C52—Al3—N4—C31 | 62.63 (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—C32 | 64.4 (2) |
C23—Al1—N1—C4 | 70.06 (18) | C52—Al3—N4—C32 | −177.15 (19) |
Experimental details
Crystal data | |
Chemical formula | [Al2(CH3)6(C21H28N2)] |
Mr | 452.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 11.191 (3), 12.809 (3), 20.489 (5) |
α, β, γ (°) | 101.419 (3), 96.138 (4), 90.242 (4) |
V (Å3) | 2861.5 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.892, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15540, 10970, 7250 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.135, 1.01 |
No. of reflections | 10970 |
No. of parameters | 577 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.63 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
N1—C5—C6—C11 | 99.2 (3) | C13—C12—N2—Al2 | −92.5 (3) |
C2—C1—N1—C4 | −53.5 (3) | C4—C3—N2—C2 | 60.2 (3) |
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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.