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The disproportionation of AlCl(THF)n (THF is tetra­hydro­furan) in the presence of lithium amidinate species gives aluminium(III) amidinate complexes with partial or full chloride substitution. Three aluminium amidinate complexes formed during the reaction between aluminium mono­chloride and lithium amidinates are presented. The homoleptic complex tris­(N,N'-diiso­propyl­benz­imid­amido)­aluminium(III), [Al(C13H19N2)3] or Al{PhC[N(i-Pr)]2}3, (I), crystallizes from the same solution as the heteroleptic complex chlorido­bis(N,N'-diiso­propyl­benz­imid­amido)­aluminium(III), [Al(C13H19N2)2Cl] or Al{PhC[N(i-Pr)]2}2Cl, (II). Both have two crystallographically independent mol­ecules per asymmetric unit (Z' = 2) and (I) shows disorder in four of its N(i-Pr) groups. Changing the ligand substituent to the bulkier cyclo­hexyl allows the isolation of the partial THF solvate chlorido­bis­(N,N'-di­cyclo­hexyl­benz­imid­amido)­aluminium(III) tetra­hydro­furan 0.675-solvate, [Al(C19H27N2)2Cl]·0.675C4H8O or Al[PhC(NCy)2]2Cl·0.675THF, (III). Despite having a two­fold rotation axis running through its Al and Cl atoms, (III) has a similar mol­ecular structure to that of (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113023135/ky3026sup1.cif
Contains datablocks AlPhCNiPr23, AlPhCNiPr22Cl, AlPhCNCy22Cl, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113023135/ky3026AlPhCNiPr23sup2.hkl
Contains datablock AlPhCNiPr23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113023135/ky3026AlPhCNiPr22Clsup3.hkl
Contains datablock AlPhCNiPr22Cl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113023135/ky3026AlPhCNCy22Clsup4.hkl
Contains datablock AlPhCNCy22Cl

CCDC references: 969447; 969448; 969449

Introduction top

Metastable aluminium(I) halides are known to undergo disproportionation reactions to form aluminium metal and aluminium trihalides at temperatures above 195 K (equation 1 of Schnoeckel, 2010), i.e.

3 AlCl 2 Al + AlCl3.

In order to stabilize metalloid aluminium clusters (AlnRmXy or AlnRm where n > m + y), nucleophilic ligand compounds with the potential to undergo ligand metathesis reactions are added. Due to the high reactivity of many aluminium monohalide solutions, these reactions are typically initiated in solution at 195 K and subsequently allowed to warm to room temperature.

The majority of ligands used in metalloid aluminium cluster chemistry have been monodentate nitro­gen- or oxygen-based species. To study the effect of ligand denticity on metalloid aluminium cluster formation, amidinate ligands were selected for use in the present study. Amidinate and guanidate ligands containing bulky alkyl groups have previously been used to stabilize reduced oxidation state alane derivatives and are known to form crystalline aluminium(III) compounds in the presence of aluminium monohalides (Bonyhady et al., 2010; Dange et al., 2012). Nitro­gen-bound alkyl groups of varying steric bulk (iso­propyl and cyclo­hexyl) were selected in this study in an attempt to probe the effect of ligand sterics on metal-cluster formation. Lithium amidinates were generated in situ through reaction of phenyl­lithium with the corresponding carbodi­imide reagent (Luo et al., 2002). The reaction of AlCl(THF)n (THF is tetra­hydro­furan) with lithium amidinates resulted in the formation of three novel aluminium(III) amidinate complexes, (I)–(III) (see scheme).

Experimental top

Synthesis and crystallization top

For the preparation of Al{PhC[N(i—Pr)]2}3, (I), and Al{PhC[N(i—Pr)]2}2Cl, (II), Li{PhC[N(i—Pr)]2} (1.45 g, 7.0 mmol) was dissolved in toluene (10 ml) and cooled to 195 K. To this suspension was added cold AlCl(THF)n (6.6 mmol, 17.6 ml of a 380 mmol solution in toluene–THF 3:1 v/v) via syringe. The resultant brown reaction mixture was warmed to room temperature over the course of 2 h and then heated to 333 K for 16 h. The reaction mixture was subsequently cooled to room temperature and the solvent removed in vacuo. Extraction of the brown residue into pentane (50 ml) and filtration via cannula resulted in a dark-brown solution. This solution was concentrated to approximately 10 ml, from which colourless blocks of (I) were obtained. Further filtration and concentration of the solution resulted in a few pale-yellow crystals of (II).

For the preparation of Al[PhC(NCy)2]2Cl, (III), di­cyclo­hexyl­carbodi­imide (1.044 g, 5.06 mmol) was dissolved in toluene (10 ml) at room temperature. To this solution was added phenyl­lithium (5.06 mmol, 2.5 ml of a 2.0 M solution in di­butyl ether) and the reaction mixture stirred for 1 h. The resultant yellow solution was cooled to 195 K and cold AlCl(THF)n (4.82 mmol, 20 ml of a 240 mM solution in toluene–THF 3:1 v/v) was added quickly via syringe. The resultant brown solution was slowly warmed to room temperature overnight. The reaction mixture was subsequently concentrated to ca 10 ml, filtered via cannula and stored at 258 K for 10 d, after which a few pale-yellow plates of (III) formed on the glass wall.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were positioned geometrically and refined in riding mode, with C—H = 0.95, 0.98, 0.99 and 1.00 Å for sp2, CH3, CH2 and sp3 H atoms, respectively. Uiso(H) values were set to 1.5Ueq(C) for CH3 groups and 1.2Ueq(C) for other atoms. Four iso­propyl groups in (I) were modelled as disordered over two sites. A total of 58 rigid-bond, equivalent displacement parameter and distance restraints were required to give a chemically sensible model.

Results and discussion top

The reaction with Li{PhC[N(i—Pr)]2} gave two separate crystalline products. The initial product formed was the homoleptic aluminium amidinate Al{PhC[N(i—Pr)]2}3, (I), which crystallized out of the reaction mixture as colourless blocks (Fig. 1). Two crystallographically independent molecules (Z' = 2) with similar core coordination geometries are present within the crystal structure. Each has a central six-coordinate AlIII cation, which is distorted from o­cta­hedral geometry due to the demands of bonding to three chelating ligands. The Al—N bond lengths are in the range 1.9826 (15)–2.0344 (15) Å in one molecule and 2.0156 (15)–2.0382 (15) Å in the other (Table 2). Of these, the Al1—N1A bond is noticably shorter than the others. However, as this is one of four N atoms which is bound to a disordered iso­propyl group, this may not be chemically significant. The N—C(N) bond lengths in the amidinate ligands are in the ranges 1.320 (2)–1.330 (2) and 1.326 (2)–1.329 (2) Å for the two independent molecules (see Supplementary materials). The Al—N metric parameters are very similar to those of the homoleptic AlIII guanidinate complex reported by Kenney et al. (2005); indeed, the bond lengths and angles agree to within ±0.02 Å and ±1°, respectively (excepting the differing guanidinate C—N connectivity).

From the same reaction mixture that formed (I), yellow plates of the heteroleptic Al{PhC[N(i—Pr)]2}2Cl complex, (II), formed upon further cooling of the solution (Fig. 2). Again, there are two crystallographically independent (Z' = 2) but geometrically similar molecules present. Differences between the two molecules are most pronounced in the orientations of the iso­propyl substituents. Both display a five-coordinate AlIII centre with slightly wider N—Al—N chelate bite angles than those seen in six-coordinate (I) (all approximately 68°, compared with approximately 65.5°). The Al—N bond lengths in (II) are in the ranges 1.9102 (18)–1.9932 (18) and 1.9046 (18)–2.0076 (18) Å, with Al—Cl bond lengths of 2.2046 (8) and 2.2027 (8) Å for the two molecules (Table 3). As expected, the Al—N distances are thus systematically shorter than those in the lower coordination number complex, (I). The N—C(N) bond lengths are in the range 1.317 (3)–1.346 (3) Å and the N—Ci-Pr bond lengths are in the range 1.464 (3)–1.477 (3) Å. The bond lengths in (II) are in close agreement with those in the heteroleptic aluminium amidinate Al{MeC[N(i—Pr)]2}2Cl reported by Coles et al. (1997). Despite the size and electronic differences between Ph and Me, the structural differences between (II) and Al{MeC[N(i—Pr)]2}2Cl are minor, resulting in bond lengths that generally agree to within 0.02 Å.

The reaction between AlCl(THF)n and Li[PhC(NCy)2] resulted in a dark-brown solution which yielded Al[PhC(NCy)2]2Cl, (III), as yellow plate crystals (Fig. 3). Each molecule is bis­ected by a twofold rotation axis that runs through the Al and Cl atoms, and thus the two PhC(NCy)2 ligands are identical and Z' = 0.5. The central AlIII cation in (III) has a similar coordination geometry to that of (II), with Al—N bond lengths of 1.9260 (12) and 1.9952 (12) Å and an Al—Cl bond length of 2.1855 (9) Å (Table 4). The N—C(N) bond lengths are 1.3213 (18) and 1.3407 (18) Å, and the N—Ci-Pr bond lengths are 1.4647 (18) and 1.4680 (18) Å. The bond lengths and angles in (III) are quite similar to those in Al[t-BuC(NCy)2]2Cl (Coles et al., 1997). In general, the bond lengths of (III) are within 0.02 Å of those reported in Al[t-BuC(NCy)2]2Cl, and the bond angles in (III) are similarly close. The amidinate ligand groups in (II) and (III) are also similar, such that the bond angles and lengths between the ligand and AlIII cation generally agree to within 1° and 0.01 Å, respectively. The structure of (III) contains THF solvent, which was found to be both disordered and partially present. As this could not be refined satisfactorily, the SQUEEZE procedure of PLATON (Spek, 2009) was used to remove the effects of approximately 2.7 THF molecules from the unit cell. The disorder of these molecules may be related to the channel solvate nature of the packed structure, with the channels running parallel to the crystallographic c direction.

Related literature top

For related literature, see: Bonyhady et al. (2010); Coles et al. (1997); Dange et al. (2012); Kenney et al. (2005); Luo et al. (2002); Schnoeckel (2010); Spek (2009).

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2010); cell refinement: APEX2 (Bruker, 2010); data reduction: APEX2 and SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012); molecular graphics: XSHEL (Bruker, 2004); software used to prepare material for publication: APEX2 (Bruker, 2010) and SHELXL2012 (Sheldrick, 2012).

Figures top
[Figure 1] Fig. 1. A view of (I), showing the two crystallographically independent molecules and the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms and the isopropyl groups of the minor-disorder components have been omitted for clarity. (Colour key in the electronic version of the paper: aluminium = light blue, carbon = black and nitrogen = blue.)
[Figure 2] Fig. 2. A view of (II), showing the two crystallographically independent molecules and the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. (Colour key in the electronic version of the paper: aluminium = light blue, carbon = black, chlorine = green and nitrogen = blue.)
[Figure 3] Fig. 3. The molecular structure of (III), showing the coordination geometry at the AlIII cation and the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. The colour key is as in Fig. 2. [Symmetry code: (i) -x + 1, y, -z + 1/2.]
(AlPhCNiPr23) Tris(N,N'-diisopropylbenzimidamido)aluminium(III) top
Crystal data top
[Al(C13H19N2)3]Dx = 1.128 Mg m3
Mr = 636.88Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 18169 reflections
a = 31.286 (3) Åθ = 2.3–22.3°
b = 33.409 (3) ŵ = 0.09 mm1
c = 14.3488 (12) ÅT = 150 K
V = 14998 (2) Å3Prism, colourless
Z = 160.35 × 0.30 × 0.11 mm
F(000) = 5536
Data collection top
Bruker SMART APEXII area-detector
diffractometer
14753 independent reflections
Radiation source: sealed tube10759 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
Detector resolution: 11.198 pixels mm-1θmax = 26.0°, θmin = 1.7°
φ and ω scansh = 038
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008)
k = 041
Tmin = 0.930, Tmax = 0.990l = 017
242499 measured reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.010P)2 + 9.5P]
where P = (Fo2 + 2Fc2)/3
14753 reflections(Δ/σ)max = 0.001
901 parametersΔρmax = 0.22 e Å3
58 restraintsΔρmin = 0.23 e Å3
Crystal data top
[Al(C13H19N2)3]V = 14998 (2) Å3
Mr = 636.88Z = 16
Orthorhombic, PccnMo Kα radiation
a = 31.286 (3) ŵ = 0.09 mm1
b = 33.409 (3) ÅT = 150 K
c = 14.3488 (12) Å0.35 × 0.30 × 0.11 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
14753 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008)
10759 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.990Rint = 0.086
242499 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05058 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
14753 reflectionsΔρmin = 0.23 e Å3
901 parameters
Special details top

Experimental. Crystal was split into 2 domains tilted \sim5° from each other. After integration of the twin, reflections were merged into single domain set and used in all further refinements. Using 2 domains reflection set yields worse agreement between calculated and observed intensities.

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. 4 of 12 iso-propyl groups are disordered in 2 alternatiove orientations which geometry was restrained to be similar to each other and anisotropic adp's were retrained to rigid body motions.

H atoms were positioned from geometric consideration and refined as riding on the attached atoms with orientation of CH3 groups optimized. Uiso of H atoms were constrained to value 20% larger than Ueqv of attached atoms (50% larger for CH3 groups).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Al10.37698 (2)0.36642 (2)0.11857 (4)0.02437 (12)
C1A0.37432 (6)0.29394 (5)0.09789 (12)0.0284 (4)
C2A0.37184 (6)0.24948 (6)0.08663 (13)0.0338 (4)
C3A0.40335 (7)0.22501 (6)0.12315 (15)0.0489 (6)
H3A0.42760.23650.15280.059*
C4A0.39974 (9)0.18382 (6)0.11669 (17)0.0598 (7)
H4A0.42150.16720.14200.072*
C5A0.36490 (8)0.16680 (6)0.07382 (17)0.0568 (7)
H5A0.36230.13850.07060.068*
C6A0.33390 (8)0.19065 (6)0.03580 (16)0.0527 (6)
H6A0.31010.17890.00520.063*
C7A0.33738 (7)0.23199 (6)0.04205 (14)0.0417 (5)
H7A0.31580.24840.01540.050*
N1A0.35255 (5)0.31477 (4)0.16089 (10)0.0285 (3)
C8A0.42881 (9)0.30258 (13)0.0230 (2)0.0388 (6)0.866 (6)
H8A0.42630.27270.02450.047*0.866 (6)
C9A0.41914 (8)0.31832 (12)0.11927 (17)0.0531 (9)0.866 (6)
H9A10.39000.31080.13690.080*0.866 (6)
H9A20.43940.30690.16400.080*0.866 (6)
H9A30.42170.34760.11940.080*0.866 (6)
C10A0.47426 (9)0.31317 (15)0.0056 (2)0.0755 (13)0.866 (6)
H10A0.47650.34220.01490.113*0.866 (6)
H10B0.49420.30480.04340.113*0.866 (6)
H10C0.48140.29930.06390.113*0.866 (6)
C14A0.4342 (5)0.3029 (8)0.0110 (12)0.0388 (6)0.134 (6)
H14A0.44660.27860.01930.047*0.134 (6)
C15A0.4170 (6)0.2915 (7)0.1056 (12)0.0531 (9)0.134 (6)
H15A0.40020.31370.13100.080*0.134 (6)
H15B0.39880.26780.09970.080*0.134 (6)
H15C0.44090.28550.14770.080*0.134 (6)
C16A0.4692 (7)0.3341 (8)0.0227 (17)0.0755 (13)0.134 (6)
H16A0.49170.32350.06310.113*0.134 (6)
H16B0.48130.34070.03840.113*0.134 (6)
H16C0.45710.35830.05090.113*0.134 (6)
N2A0.39878 (5)0.31796 (4)0.04708 (10)0.0295 (3)
C11A0.32115 (9)0.30161 (8)0.22974 (18)0.0364 (7)0.853 (4)
H11A0.32090.32270.27910.044*0.853 (4)
C12A0.27625 (13)0.30108 (10)0.1887 (3)0.0428 (9)0.853 (4)
H12A0.27020.32700.15940.064*0.853 (4)
H12B0.25540.29620.23850.064*0.853 (4)
H12C0.27420.27980.14200.064*0.853 (4)
C13A0.33126 (9)0.26254 (8)0.27962 (18)0.0490 (8)0.853 (4)
H13A0.32740.24010.23640.073*0.853 (4)
H13B0.31200.25930.33290.073*0.853 (4)
H13C0.36090.26310.30170.073*0.853 (4)
C17A0.3173 (4)0.2924 (6)0.2075 (9)0.0364 (7)0.147 (4)
H17A0.31600.26520.17850.044*0.147 (4)
C18A0.2738 (8)0.3122 (8)0.193 (2)0.0428 (9)0.147 (4)
H18A0.27510.34020.21320.064*0.147 (4)
H18B0.25210.29790.22900.064*0.147 (4)
H18C0.26630.31120.12640.064*0.147 (4)
C19A0.3252 (5)0.2866 (5)0.3120 (9)0.0490 (8)0.147 (4)
H19A0.35030.26950.32110.073*0.147 (4)
H19B0.30020.27400.34050.073*0.147 (4)
H19C0.33030.31270.34130.073*0.147 (4)
C1B0.31026 (5)0.40381 (5)0.10400 (12)0.0255 (4)
C2B0.26968 (5)0.42727 (5)0.09307 (12)0.0274 (4)
C3B0.26978 (6)0.46290 (6)0.04392 (14)0.0385 (5)
H3B0.29570.47250.01750.046*
C4B0.23256 (6)0.48476 (6)0.03284 (15)0.0433 (5)
H4B0.23300.50910.00120.052*
C5B0.19492 (6)0.47118 (6)0.07120 (14)0.0366 (5)
H5B0.16940.48630.06400.044*
C6B0.19430 (6)0.43573 (5)0.11999 (14)0.0358 (5)
H6B0.16830.42630.14620.043*
C7B0.23155 (6)0.41387 (5)0.13095 (13)0.0333 (4)
H7B0.23100.38940.16480.040*
N1B0.33336 (4)0.40256 (4)0.18092 (10)0.0255 (3)
C8B0.32265 (6)0.42696 (5)0.26272 (13)0.0327 (4)
H8B0.30130.44760.24320.039*
C9B0.36203 (7)0.44842 (6)0.29873 (14)0.0460 (5)
H9B10.38300.42870.32030.069*
H9B20.35400.46600.35060.069*
H9B30.37450.46450.24850.069*
C10B0.30292 (7)0.40195 (6)0.34012 (14)0.0461 (5)
H10D0.27760.38810.31630.069*
H10E0.29470.41940.39190.069*
H10F0.32380.38220.36200.069*
C11B0.30466 (6)0.37478 (6)0.05187 (13)0.0354 (5)
H11B0.27610.38810.04750.042*
C12B0.32803 (8)0.39243 (7)0.13483 (14)0.0550 (6)
H12D0.32740.42170.13090.082*
H12E0.31400.38380.19250.082*
H12F0.35780.38320.13470.082*
N2B0.32770 (4)0.38256 (4)0.03550 (10)0.0266 (3)
C13B0.29714 (6)0.33021 (6)0.06506 (14)0.0419 (5)
H13D0.32470.31630.06740.063*
H13E0.28160.32570.12350.063*
H13F0.28020.31990.01280.063*
C1C0.44314 (6)0.40129 (5)0.15950 (13)0.0319 (4)
C2C0.48328 (6)0.42313 (6)0.18523 (14)0.0384 (5)
C3C0.52062 (7)0.41680 (7)0.13534 (19)0.0568 (6)
H3C0.52090.39820.08520.068*
C40.55767 (7)0.43756 (8)0.1585 (2)0.0696 (8)
H40.58320.43290.12440.083*
C5C0.55746 (8)0.46472 (8)0.2303 (2)0.0672 (8)
H5C0.58290.47870.24620.081*
C6C0.52063 (9)0.47162 (8)0.27891 (19)0.0705 (8)
H6C0.52030.49080.32780.085*
C7C0.48369 (8)0.45065 (7)0.25692 (17)0.0578 (6)
H7C0.45830.45530.29170.069*
N1C0.42638 (5)0.37157 (4)0.20806 (10)0.0290 (3)
C8C0.42788 (6)0.44607 (6)0.02949 (14)0.0401 (5)
H8C0.45010.46230.06230.048*
C9C0.38766 (6)0.47131 (6)0.02092 (15)0.0417 (5)
H9C10.39430.49620.01210.063*
H9C20.37680.47760.08320.063*
H9C30.36590.45640.01390.063*
C10C0.44466 (8)0.43558 (7)0.06678 (16)0.0648 (7)
H10G0.47080.41960.06070.097*
H10H0.45100.46020.10110.097*
H10I0.42300.42020.10060.097*
N2C0.41959 (5)0.40996 (4)0.08501 (11)0.0325 (4)
C11C0.44864 (6)0.35231 (6)0.28607 (13)0.0353 (5)
H11C0.47400.36920.30260.042*
C12C0.42030 (7)0.34970 (8)0.37019 (15)0.0637 (7)
H12G0.41360.37670.39230.096*
H12H0.43500.33480.41950.096*
H12I0.39380.33580.35360.096*
C13C0.46464 (9)0.31132 (7)0.25844 (18)0.0791 (9)
H13G0.44060.29510.23620.119*
H13H0.47780.29830.31250.119*
H13I0.48590.31400.20870.119*
Al20.37998 (2)0.64639 (2)0.36001 (4)0.02457 (12)
C1D0.31649 (5)0.60332 (5)0.34917 (12)0.0274 (4)
C2D0.27771 (5)0.57700 (5)0.34328 (12)0.0282 (4)
C3D0.24150 (6)0.58567 (5)0.39528 (13)0.0345 (4)
H3D0.24120.60860.43450.041*
C4D0.20570 (6)0.56131 (6)0.39077 (14)0.0384 (5)
H4D0.18120.56760.42690.046*
C5D0.20555 (6)0.52816 (6)0.33425 (14)0.0376 (5)
H5D0.18100.51150.33120.045*
C6D0.24119 (6)0.51914 (6)0.28200 (15)0.0424 (5)
H6D0.24110.49620.24270.051*
C7D0.27713 (6)0.54332 (6)0.28648 (14)0.0386 (5)
H7D0.30160.53680.25040.046*
N1D0.32807 (5)0.62932 (4)0.28395 (10)0.0307 (4)
C8D0.29988 (6)0.63924 (6)0.20547 (13)0.0381 (5)
H8D0.27170.62600.21650.046*
C9D0.29233 (6)0.68411 (6)0.20005 (14)0.0447 (5)
H9D10.27900.69330.25800.067*
H9D20.27340.69010.14740.067*
H9D30.31970.69790.19130.067*
C10D0.31777 (7)0.62359 (7)0.11355 (14)0.0542 (6)
H10J0.34650.63450.10370.081*
H10K0.29910.63190.06230.081*
H10L0.31930.59430.11560.081*
N2D0.34371 (4)0.60324 (4)0.42005 (10)0.0274 (3)
C11D0.34084 (6)0.57323 (5)0.49438 (13)0.0328 (4)
H11D0.32170.55120.47230.039*
C12D0.38475 (6)0.55526 (6)0.51400 (15)0.0424 (5)
H12J0.39490.54110.45850.064*
H12K0.38270.53650.56620.064*
H12L0.40480.57670.52990.064*
C13D0.32180 (7)0.59037 (6)0.58335 (14)0.0457 (5)
H13J0.34040.61160.60730.069*
H13K0.31930.56910.63010.069*
H13L0.29340.60150.57000.069*
C1E0.37174 (5)0.71908 (5)0.35371 (12)0.0256 (4)
C2E0.36747 (6)0.76381 (5)0.34912 (12)0.0296 (4)
C3E0.40107 (7)0.78807 (6)0.37688 (14)0.0395 (5)
H3E0.42660.77630.40000.047*
C4E0.39782 (8)0.82927 (6)0.37125 (16)0.0523 (6)
H4E0.42100.84560.39110.063*
C5E0.36123 (8)0.84666 (6)0.33711 (17)0.0559 (6)
H5E0.35930.87500.33210.067*
C6E0.32771 (7)0.82312 (7)0.31042 (17)0.0555 (6)
H6E0.30220.83510.28780.067*
C7E0.33065 (6)0.78179 (6)0.31620 (15)0.0430 (5)
H7E0.30720.76570.29740.052*
N1E0.39597 (4)0.69803 (4)0.29583 (10)0.0258 (3)
C8E0.42244 (6)0.71676 (5)0.22381 (12)0.0305 (4)
H8E0.41530.74590.22150.037*
C9E0.41301 (7)0.69879 (6)0.12889 (13)0.0441 (5)
H9E10.41860.66990.13050.066*
H9E20.43140.71140.08190.066*
H9E30.38300.70350.11290.066*
C10E0.46953 (6)0.71261 (6)0.24634 (14)0.0437 (5)
H10M0.47580.72680.30450.066*
H10N0.48650.72410.19560.066*
H10O0.47670.68420.25350.066*
N2E0.35260 (4)0.69555 (4)0.41534 (10)0.0277 (3)
C11E0.32134 (12)0.71432 (9)0.4803 (2)0.0287 (8)0.669 (3)
H11E0.31970.74370.46740.034*0.669 (3)
C12E0.2776 (3)0.6956 (5)0.4651 (9)0.0474 (19)0.669 (3)
H12M0.26840.70030.40070.071*0.669 (3)
H12N0.25690.70770.50800.071*0.669 (3)
H12O0.27920.66670.47660.071*0.669 (3)
C13E0.33384 (10)0.70779 (11)0.5821 (2)0.0458 (8)0.669 (3)
H13M0.33680.67910.59420.069*0.669 (3)
H13N0.31170.71900.62270.069*0.669 (3)
H13O0.36110.72120.59460.069*0.669 (3)
C17E0.3205 (3)0.6996 (2)0.4887 (6)0.0287 (8)0.331 (3)
H17E0.32330.67590.53090.034*0.331 (3)
C18E0.2755 (5)0.6997 (10)0.450 (2)0.0474 (19)0.331 (3)
H18M0.27180.72270.40870.071*0.331 (3)
H18N0.25500.70150.50190.071*0.331 (3)
H18O0.27050.67490.41550.071*0.331 (3)
C19E0.3304 (2)0.7364 (2)0.5451 (4)0.0458 (8)0.331 (3)
H19M0.31140.73760.59930.069*0.331 (3)
H19N0.32610.76030.50650.069*0.331 (3)
H19O0.36020.73540.56610.069*0.331 (3)
C1F0.45074 (5)0.61603 (5)0.38032 (13)0.0277 (4)
C2F0.49321 (6)0.59610 (5)0.39381 (14)0.0323 (4)
C3F0.52564 (6)0.60114 (5)0.32799 (15)0.0381 (5)
H3F0.52090.61780.27540.046*
C4F0.56468 (6)0.58206 (6)0.33873 (17)0.0465 (6)
H4F0.58670.58600.29400.056*
C5F0.57158 (6)0.55745 (6)0.41426 (17)0.0492 (6)
H5F0.59830.54430.42150.059*
C6F0.53976 (7)0.55191 (6)0.47929 (17)0.0483 (6)
H6F0.54450.53480.53110.058*
C7F0.50078 (6)0.57133 (6)0.46940 (15)0.0406 (5)
H7F0.47910.56760.51490.049*
N1F0.42561 (4)0.60969 (4)0.30707 (10)0.0288 (3)
C8F0.43367 (6)0.57660 (6)0.24177 (14)0.0384 (5)
H8F0.45950.56180.26380.046*
C9F0.39648 (8)0.54767 (7)0.24042 (17)0.0628 (7)
H9F10.39240.53650.30290.094*
H9F20.40250.52600.19630.094*
H9F30.37050.56180.22120.094*
C10F0.44222 (7)0.59103 (7)0.14327 (15)0.0507 (6)
H10P0.41650.60400.11860.076*
H10Q0.44970.56820.10380.076*
H10R0.46590.61020.14380.076*
N2F0.43312 (4)0.64145 (4)0.44012 (10)0.0262 (3)
C11F0.45671 (18)0.65933 (17)0.5185 (3)0.0301 (5)0.764 (14)
H11F0.48650.64850.51730.036*0.764 (14)
C12F0.4593 (2)0.70472 (13)0.5101 (4)0.0388 (11)0.764 (14)
H12P0.47610.71180.45500.058*0.764 (14)
H12Q0.47290.71580.56590.058*0.764 (14)
H12R0.43040.71580.50400.058*0.764 (14)
C13F0.43651 (18)0.64762 (17)0.6113 (3)0.0400 (10)0.764 (14)
H13P0.40590.65390.61000.060*0.764 (14)
H13Q0.45030.66250.66180.060*0.764 (14)
H13R0.44030.61880.62160.060*0.764 (14)
C17F0.4560 (6)0.6575 (5)0.5216 (8)0.0301 (5)0.236 (14)
H17F0.48050.63960.53770.036*0.236 (14)
C18F0.4727 (6)0.6986 (5)0.4939 (12)0.0388 (11)0.236 (14)
H18D0.49570.69550.44820.058*0.236 (14)
H18E0.48370.71240.54920.058*0.236 (14)
H18F0.44940.71430.46650.058*0.236 (14)
C19F0.4254 (5)0.6602 (5)0.6042 (11)0.0400 (10)0.236 (14)
H19D0.39990.67530.58590.060*0.236 (14)
H19E0.43960.67380.65610.060*0.236 (14)
H19F0.41710.63320.62350.060*0.236 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Al10.0253 (3)0.0241 (3)0.0238 (3)0.0048 (2)0.0012 (2)0.0003 (2)
C1A0.0315 (10)0.0271 (9)0.0265 (9)0.0074 (8)0.0059 (8)0.0010 (8)
C2A0.0423 (11)0.0277 (10)0.0313 (10)0.0055 (9)0.0032 (9)0.0021 (8)
C3A0.0627 (15)0.0315 (11)0.0526 (14)0.0119 (10)0.0115 (12)0.0035 (10)
C4A0.0845 (19)0.0311 (12)0.0637 (16)0.0194 (12)0.0080 (14)0.0018 (11)
C5A0.0870 (19)0.0254 (11)0.0579 (15)0.0006 (12)0.0159 (14)0.0039 (11)
C6A0.0624 (15)0.0372 (12)0.0585 (15)0.0069 (11)0.0056 (12)0.0111 (11)
C7A0.0481 (13)0.0350 (11)0.0421 (12)0.0043 (10)0.0024 (10)0.0048 (10)
N1A0.0324 (8)0.0259 (8)0.0272 (8)0.0050 (7)0.0015 (7)0.0006 (7)
C8A0.0411 (13)0.0387 (11)0.0365 (14)0.0117 (11)0.0082 (11)0.0038 (11)
C9A0.0438 (15)0.082 (3)0.0333 (13)0.0136 (16)0.0090 (11)0.0041 (16)
C10A0.0319 (15)0.147 (4)0.047 (2)0.0269 (19)0.0039 (13)0.013 (2)
C14A0.0411 (13)0.0387 (11)0.0365 (14)0.0117 (11)0.0082 (11)0.0038 (11)
C15A0.0438 (15)0.082 (3)0.0333 (13)0.0136 (16)0.0090 (11)0.0041 (16)
C16A0.0319 (15)0.147 (4)0.047 (2)0.0269 (19)0.0039 (13)0.013 (2)
N2A0.0316 (8)0.0285 (8)0.0284 (8)0.0065 (7)0.0028 (7)0.0017 (7)
C11A0.0471 (13)0.0342 (17)0.0279 (15)0.0006 (11)0.0094 (12)0.0019 (11)
C12A0.0421 (14)0.035 (2)0.0508 (15)0.0102 (16)0.0107 (11)0.0005 (17)
C13A0.0726 (18)0.0359 (16)0.0384 (15)0.0073 (14)0.0044 (13)0.0073 (12)
C17A0.0471 (13)0.0342 (17)0.0279 (15)0.0006 (11)0.0094 (12)0.0019 (11)
C18A0.0421 (14)0.035 (2)0.0508 (15)0.0102 (16)0.0107 (11)0.0005 (17)
C19A0.0726 (18)0.0359 (16)0.0384 (15)0.0073 (14)0.0044 (13)0.0073 (12)
C1B0.0258 (9)0.0204 (9)0.0302 (10)0.0010 (7)0.0025 (8)0.0046 (8)
C2B0.0271 (9)0.0247 (9)0.0304 (10)0.0044 (8)0.0000 (8)0.0005 (8)
C3B0.0285 (10)0.0349 (11)0.0521 (13)0.0068 (9)0.0091 (9)0.0129 (10)
C4B0.0349 (11)0.0346 (11)0.0606 (14)0.0109 (9)0.0064 (10)0.0192 (10)
C5B0.0259 (10)0.0340 (11)0.0498 (13)0.0094 (8)0.0016 (9)0.0015 (9)
C6B0.0244 (10)0.0337 (11)0.0495 (12)0.0009 (8)0.0030 (9)0.0029 (9)
C7B0.0311 (10)0.0264 (10)0.0424 (12)0.0035 (8)0.0006 (9)0.0063 (9)
N1B0.0296 (8)0.0233 (8)0.0237 (8)0.0048 (6)0.0002 (6)0.0007 (6)
C8B0.0382 (11)0.0282 (10)0.0316 (10)0.0075 (8)0.0016 (9)0.0063 (8)
C9B0.0607 (14)0.0376 (12)0.0397 (12)0.0143 (10)0.0088 (11)0.0122 (10)
C10B0.0486 (13)0.0547 (13)0.0349 (12)0.0136 (11)0.0137 (10)0.0155 (10)
C11B0.0363 (11)0.0408 (11)0.0291 (10)0.0110 (9)0.0076 (9)0.0013 (9)
C12B0.0770 (17)0.0590 (15)0.0290 (12)0.0033 (13)0.0071 (11)0.0049 (10)
N2B0.0283 (8)0.0288 (8)0.0228 (8)0.0067 (6)0.0025 (6)0.0008 (6)
C13B0.0442 (12)0.0474 (13)0.0342 (11)0.0005 (10)0.0101 (9)0.0065 (10)
C1C0.0288 (10)0.0308 (10)0.0362 (11)0.0023 (8)0.0014 (9)0.0010 (9)
C2C0.0326 (11)0.0379 (11)0.0448 (12)0.0037 (9)0.0094 (9)0.0097 (10)
C3C0.0345 (12)0.0500 (14)0.0860 (19)0.0015 (10)0.0036 (12)0.0006 (13)
C40.0317 (13)0.0650 (17)0.112 (2)0.0060 (12)0.0047 (14)0.0138 (17)
C5C0.0510 (16)0.0610 (17)0.090 (2)0.0246 (13)0.0288 (15)0.0212 (15)
C6C0.0722 (19)0.0729 (18)0.0663 (18)0.0340 (15)0.0143 (15)0.0027 (14)
C7C0.0523 (15)0.0671 (16)0.0542 (15)0.0218 (12)0.0043 (12)0.0078 (13)
N1C0.0290 (8)0.0291 (8)0.0288 (8)0.0020 (7)0.0051 (7)0.0018 (7)
C8C0.0323 (11)0.0416 (12)0.0464 (13)0.0050 (9)0.0032 (9)0.0160 (10)
C9C0.0459 (12)0.0335 (11)0.0458 (13)0.0002 (9)0.0017 (10)0.0111 (9)
C10C0.0559 (15)0.0760 (18)0.0624 (16)0.0209 (13)0.0293 (13)0.0333 (14)
N2C0.0290 (8)0.0351 (9)0.0334 (9)0.0008 (7)0.0029 (7)0.0081 (7)
C11C0.0373 (11)0.0341 (11)0.0345 (11)0.0012 (9)0.0135 (9)0.0047 (9)
C12C0.0582 (15)0.0860 (18)0.0470 (14)0.0063 (14)0.0031 (12)0.0311 (13)
C13C0.114 (2)0.0538 (15)0.0697 (18)0.0389 (16)0.0516 (17)0.0077 (14)
Al20.0230 (3)0.0267 (3)0.0240 (3)0.0040 (2)0.0014 (2)0.0007 (2)
C1D0.0246 (9)0.0285 (9)0.0292 (10)0.0024 (8)0.0016 (8)0.0062 (8)
C2D0.0240 (9)0.0300 (10)0.0304 (10)0.0038 (8)0.0023 (8)0.0024 (8)
C3D0.0317 (11)0.0319 (10)0.0400 (12)0.0043 (8)0.0020 (9)0.0059 (9)
C4D0.0255 (10)0.0406 (12)0.0490 (13)0.0027 (9)0.0029 (9)0.0003 (10)
C5D0.0270 (10)0.0346 (11)0.0511 (13)0.0084 (8)0.0100 (9)0.0029 (10)
C6D0.0348 (12)0.0359 (11)0.0564 (14)0.0053 (9)0.0065 (10)0.0145 (10)
C7D0.0271 (10)0.0416 (12)0.0472 (12)0.0030 (9)0.0001 (9)0.0130 (10)
N1D0.0284 (8)0.0395 (9)0.0241 (8)0.0069 (7)0.0031 (7)0.0010 (7)
C8D0.0305 (10)0.0565 (13)0.0274 (10)0.0112 (10)0.0063 (8)0.0028 (9)
C9D0.0370 (12)0.0638 (15)0.0334 (11)0.0003 (10)0.0092 (9)0.0116 (10)
C10D0.0597 (15)0.0732 (16)0.0298 (11)0.0090 (12)0.0100 (11)0.0066 (11)
N2D0.0264 (8)0.0264 (8)0.0293 (8)0.0056 (6)0.0032 (7)0.0020 (7)
C11D0.0311 (10)0.0275 (10)0.0398 (11)0.0093 (8)0.0041 (9)0.0074 (9)
C12D0.0402 (12)0.0318 (10)0.0552 (13)0.0055 (9)0.0093 (10)0.0106 (10)
C13D0.0490 (13)0.0501 (13)0.0380 (12)0.0064 (10)0.0033 (10)0.0151 (10)
C1E0.0229 (9)0.0311 (10)0.0227 (9)0.0007 (7)0.0040 (8)0.0011 (8)
C2E0.0330 (10)0.0302 (10)0.0255 (10)0.0068 (8)0.0067 (8)0.0031 (8)
C3E0.0449 (12)0.0318 (11)0.0419 (12)0.0039 (9)0.0067 (10)0.0029 (9)
C4E0.0622 (15)0.0304 (11)0.0643 (15)0.0008 (11)0.0064 (13)0.0042 (11)
C5E0.0653 (16)0.0306 (12)0.0718 (17)0.0098 (11)0.0083 (13)0.0072 (11)
C6E0.0461 (14)0.0461 (14)0.0742 (17)0.0143 (11)0.0049 (12)0.0209 (12)
C7E0.0339 (11)0.0411 (12)0.0541 (13)0.0018 (9)0.0023 (10)0.0132 (10)
N1E0.0252 (8)0.0277 (8)0.0246 (8)0.0006 (6)0.0039 (6)0.0015 (6)
C8E0.0341 (10)0.0262 (9)0.0312 (10)0.0020 (8)0.0081 (8)0.0019 (8)
C9E0.0456 (12)0.0573 (13)0.0293 (11)0.0098 (10)0.0085 (9)0.0023 (10)
C10E0.0364 (12)0.0534 (13)0.0413 (12)0.0103 (10)0.0090 (10)0.0023 (10)
N2E0.0249 (8)0.0357 (9)0.0225 (8)0.0022 (7)0.0019 (6)0.0018 (7)
C11E0.0370 (12)0.020 (2)0.0289 (13)0.0057 (18)0.0117 (10)0.0067 (17)
C12E0.0303 (14)0.073 (3)0.039 (5)0.0018 (16)0.0073 (14)0.004 (3)
C13E0.0498 (17)0.058 (2)0.0295 (16)0.0005 (17)0.0079 (14)0.0090 (14)
C17E0.0370 (12)0.020 (2)0.0289 (13)0.0057 (18)0.0117 (10)0.0067 (17)
C18E0.0303 (14)0.073 (3)0.039 (5)0.0018 (16)0.0073 (14)0.004 (3)
C19E0.0498 (17)0.058 (2)0.0295 (16)0.0005 (17)0.0079 (14)0.0090 (14)
C1F0.0241 (9)0.0207 (9)0.0383 (11)0.0049 (7)0.0006 (8)0.0029 (8)
C2F0.0283 (10)0.0213 (9)0.0472 (12)0.0022 (8)0.0019 (9)0.0039 (9)
C3F0.0307 (11)0.0287 (10)0.0549 (13)0.0046 (8)0.0008 (10)0.0013 (9)
C4F0.0283 (11)0.0370 (11)0.0742 (16)0.0025 (9)0.0069 (11)0.0048 (11)
C5F0.0280 (11)0.0376 (12)0.0819 (18)0.0047 (9)0.0029 (11)0.0031 (12)
C6F0.0388 (12)0.0401 (12)0.0659 (16)0.0062 (10)0.0067 (11)0.0064 (11)
C7F0.0308 (11)0.0366 (11)0.0544 (14)0.0006 (9)0.0001 (10)0.0011 (10)
N1F0.0277 (8)0.0247 (8)0.0339 (9)0.0039 (6)0.0006 (7)0.0057 (7)
C8F0.0385 (11)0.0297 (10)0.0471 (12)0.0021 (9)0.0013 (10)0.0121 (9)
C9F0.0778 (18)0.0485 (14)0.0622 (16)0.0260 (13)0.0190 (14)0.0264 (12)
C10F0.0494 (13)0.0539 (14)0.0490 (14)0.0049 (11)0.0136 (11)0.0199 (11)
N2F0.0242 (8)0.0246 (8)0.0297 (8)0.0021 (6)0.0032 (6)0.0012 (6)
C11F0.0284 (10)0.0277 (11)0.0342 (11)0.0001 (8)0.0085 (8)0.0006 (9)
C12F0.047 (3)0.0295 (17)0.040 (2)0.0042 (17)0.014 (2)0.0041 (15)
C13F0.044 (2)0.041 (2)0.0354 (14)0.0033 (18)0.0091 (15)0.0017 (17)
C17F0.0284 (10)0.0277 (11)0.0342 (11)0.0001 (8)0.0085 (8)0.0006 (9)
C18F0.047 (3)0.0295 (17)0.040 (2)0.0042 (17)0.014 (2)0.0041 (15)
C19F0.044 (2)0.041 (2)0.0354 (14)0.0033 (18)0.0091 (15)0.0017 (17)
Geometric parameters (Å, º) top
Al1—N1A1.9826 (15)Al2—N2E2.0156 (15)
Al1—N1C2.0168 (15)Al2—N1E2.0185 (15)
Al1—N2B2.0220 (14)Al2—N2D2.0267 (15)
Al1—N1B2.0299 (14)Al2—N2F2.0279 (14)
Al1—N2C2.0310 (16)Al2—N1F2.0295 (15)
Al1—N2A2.0344 (15)Al2—N1D2.0382 (15)
C1A—N2A1.327 (2)C1D—N2D1.326 (2)
C1A—N1A1.329 (2)C1D—N1D1.327 (2)
C1A—C2A1.496 (2)C1D—C2D1.501 (2)
C2A—C7A1.383 (3)C2D—C3D1.387 (2)
C2A—C3A1.384 (3)C2D—C7D1.389 (2)
C3A—C4A1.384 (3)C3D—C4D1.386 (2)
C3A—H3A0.9500C3D—H3D0.9500
C4A—C5A1.375 (3)C4D—C5D1.373 (3)
C4A—H4A0.9500C4D—H4D0.9500
C5A—C6A1.369 (3)C5D—C6D1.377 (3)
C5A—H5A0.9500C5D—H5D0.9500
C6A—C7A1.388 (3)C6D—C7D1.386 (3)
C6A—H6A0.9500C6D—H6D0.9500
C7A—H7A0.9500C7D—H7D0.9500
N1A—C11A1.461 (3)N1D—C8D1.468 (2)
N1A—C17A1.490 (7)C8D—C9D1.519 (3)
C8A—N2A1.469 (3)C8D—C10D1.525 (3)
C8A—C9A1.508 (4)C8D—H8D1.0000
C8A—C10A1.522 (4)C9D—H9D10.9800
C8A—H8A1.0000C9D—H9D20.9800
C9A—H9A10.9800C9D—H9D30.9800
C9A—H9A20.9800C10D—H10J0.9800
C9A—H9A30.9800C10D—H10K0.9800
C10A—H10A0.9800C10D—H10L0.9800
C10A—H10B0.9800N2D—C11D1.467 (2)
C10A—H10C0.9800C11D—C13D1.521 (3)
C14A—N2A1.475 (8)C11D—C12D1.525 (3)
C14A—C15A1.509 (10)C11D—H11D1.0000
C14A—C16A1.522 (10)C12D—H12J0.9800
C14A—H14A1.0000C12D—H12K0.9800
C15A—H15A0.9800C12D—H12L0.9800
C15A—H15B0.9800C13D—H13J0.9800
C15A—H15C0.9800C13D—H13K0.9800
C16A—H16A0.9800C13D—H13L0.9800
C16A—H16B0.9800C1E—N2E1.326 (2)
C16A—H16C0.9800C1E—N1E1.326 (2)
C11A—C13A1.522 (3)C1E—C2E1.502 (2)
C11A—C12A1.523 (3)C2E—C7E1.382 (3)
C11A—H11A1.0000C2E—C3E1.386 (3)
C12A—H12A0.9800C3E—C4E1.383 (3)
C12A—H12B0.9800C3E—H3E0.9500
C12A—H12C0.9800C4E—C5E1.374 (3)
C13A—H13A0.9800C4E—H4E0.9500
C13A—H13B0.9800C5E—C6E1.366 (3)
C13A—H13C0.9800C5E—H5E0.9500
C17A—C18A1.527 (10)C6E—C7E1.387 (3)
C17A—C19A1.532 (9)C6E—H6E0.9500
C17A—H17A1.0000C7E—H7E0.9500
C18A—H18A0.9800N1E—C8E1.465 (2)
C18A—H18B0.9800C8E—C10E1.515 (3)
C18A—H18C0.9800C8E—C9E1.517 (3)
C19A—H19A0.9800C8E—H8E1.0000
C19A—H19B0.9800C9E—H9E10.9800
C19A—H19C0.9800C9E—H9E20.9800
C1B—N1B1.320 (2)C9E—H9E30.9800
C1B—N2B1.329 (2)C10E—H10M0.9800
C1B—C2B1.500 (2)C10E—H10N0.9800
C2B—C3B1.384 (2)C10E—H10O0.9800
C2B—C7B1.385 (2)N2E—C17E1.461 (6)
C3B—C4B1.384 (2)N2E—C11E1.490 (3)
C3B—H3B0.9500C11E—C12E1.521 (7)
C4B—C5B1.377 (3)C11E—C13E1.527 (4)
C4B—H4B0.9500C11E—H11E1.0000
C5B—C6B1.376 (3)C12E—H12M0.9800
C5B—H5B0.9500C12E—H12N0.9800
C6B—C7B1.384 (2)C12E—H12O0.9800
C6B—H6B0.9500C13E—H13M0.9800
C7B—H7B0.9500C13E—H13N0.9800
N1B—C8B1.468 (2)C13E—H13O0.9800
C8B—C9B1.516 (3)C17E—C19E1.505 (7)
C8B—C10B1.520 (3)C17E—C18E1.512 (9)
C8B—H8B1.0000C17E—H17E1.0000
C9B—H9B10.9800C18E—H18M0.9800
C9B—H9B20.9800C18E—H18N0.9800
C9B—H9B30.9800C18E—H18O0.9800
C10B—H10D0.9800C19E—H19M0.9800
C10B—H10E0.9800C19E—H19N0.9800
C10B—H10F0.9800C19E—H19O0.9800
C11B—N2B1.469 (2)C1F—N2F1.327 (2)
C11B—C12B1.516 (3)C1F—N1F1.329 (2)
C11B—C13B1.519 (3)C1F—C2F1.499 (2)
C11B—H11B1.0000C2F—C7F1.385 (3)
C12B—H12D0.9800C2F—C3F1.396 (3)
C12B—H12E0.9800C3F—C4F1.386 (3)
C12B—H12F0.9800C3F—H3F0.9500
C13B—H13D0.9800C4F—C5F1.377 (3)
C13B—H13E0.9800C4F—H4F0.9500
C13B—H13F0.9800C5F—C6F1.377 (3)
C1C—N1C1.322 (2)C5F—H5F0.9500
C1C—N2C1.330 (2)C6F—C7F1.389 (3)
C1C—C2C1.499 (3)C6F—H6F0.9500
C2C—C7C1.380 (3)C7F—H7F0.9500
C2C—C3C1.386 (3)N1F—C8F1.471 (2)
C3C—C41.391 (3)C8F—C9F1.513 (3)
C3C—H3C0.9500C8F—C10F1.517 (3)
C4—C5C1.373 (4)C8F—H8F1.0000
C4—H40.9500C9F—H9F10.9800
C5C—C6C1.367 (4)C9F—H9F20.9800
C5C—H5C0.9500C9F—H9F30.9800
C6C—C7C1.388 (3)C10F—H10P0.9800
C6C—H6C0.9500C10F—H10Q0.9800
C7C—H7C0.9500C10F—H10R0.9800
N1C—C11C1.467 (2)N2F—C11F1.472 (3)
C8C—N2C1.469 (2)N2F—C17F1.473 (7)
C8C—C10C1.519 (3)C11F—C12F1.523 (4)
C8C—C9C1.520 (3)C11F—C13F1.525 (4)
C8C—H8C1.0000C11F—H11F1.0000
C9C—H9C10.9800C12F—H12P0.9800
C9C—H9C20.9800C12F—H12Q0.9800
C9C—H9C30.9800C12F—H12R0.9800
C10C—H10G0.9800C13F—H13P0.9800
C10C—H10H0.9800C13F—H13Q0.9800
C10C—H10I0.9800C13F—H13R0.9800
C11C—C12C1.500 (3)C17F—C18F1.520 (8)
C11C—C13C1.511 (3)C17F—C19F1.526 (9)
C11C—H11C1.0000C17F—H17F1.0000
C12C—H12G0.9800C18F—H18D0.9800
C12C—H12H0.9800C18F—H18E0.9800
C12C—H12I0.9800C18F—H18F0.9800
C13C—H13G0.9800C19F—H19D0.9800
C13C—H13H0.9800C19F—H19E0.9800
C13C—H13I0.9800C19F—H19F0.9800
N1A—Al1—N1C100.06 (6)N2E—Al2—N1E65.70 (6)
N1A—Al1—N2B96.82 (6)N2E—Al2—N2D100.03 (6)
N1C—Al1—N2B159.54 (6)N1E—Al2—N2D160.14 (6)
N1A—Al1—N1B97.10 (6)N2E—Al2—N2F101.04 (6)
N1C—Al1—N1B100.60 (6)N1E—Al2—N2F97.19 (6)
N2B—Al1—N1B65.71 (6)N2D—Al2—N2F99.21 (6)
N1A—Al1—N2C161.62 (6)N2E—Al2—N1F159.86 (6)
N1C—Al1—N2C65.60 (6)N1E—Al2—N1F99.87 (6)
N2B—Al1—N2C99.77 (6)N2D—Al2—N1F97.08 (6)
N1B—Al1—N2C96.88 (6)N2F—Al2—N1F65.56 (6)
N1A—Al1—N2A65.85 (6)N2E—Al2—N1D95.75 (6)
N1C—Al1—N2A97.58 (6)N1E—Al2—N1D101.08 (6)
N2B—Al1—N2A99.83 (6)N2D—Al2—N1D65.32 (6)
N1B—Al1—N2A157.07 (6)N2F—Al2—N1D159.07 (6)
N2C—Al1—N2A103.32 (6)N1F—Al2—N1D101.02 (6)
N2A—C1A—N1A110.66 (15)N2D—C1D—N1D111.51 (15)
N2A—C1A—C2A124.81 (16)N2D—C1D—C2D124.13 (16)
N1A—C1A—C2A124.53 (16)N1D—C1D—C2D124.36 (16)
C7A—C2A—C3A118.75 (18)C3D—C2D—C7D118.31 (16)
C7A—C2A—C1A120.65 (17)C3D—C2D—C1D120.49 (16)
C3A—C2A—C1A120.57 (18)C7D—C2D—C1D121.20 (16)
C2A—C3A—C4A120.3 (2)C4D—C3D—C2D120.81 (17)
C2A—C3A—H3A119.9C4D—C3D—H3D119.6
C4A—C3A—H3A119.9C2D—C3D—H3D119.6
C5A—C4A—C3A120.4 (2)C5D—C4D—C3D120.28 (18)
C5A—C4A—H4A119.8C5D—C4D—H4D119.9
C3A—C4A—H4A119.8C3D—C4D—H4D119.9
C6A—C5A—C4A120.0 (2)C4D—C5D—C6D119.69 (17)
C6A—C5A—H5A120.0C4D—C5D—H5D120.2
C4A—C5A—H5A120.0C6D—C5D—H5D120.2
C5A—C6A—C7A119.9 (2)C5D—C6D—C7D120.27 (18)
C5A—C6A—H6A120.1C5D—C6D—H6D119.9
C7A—C6A—H6A120.1C7D—C6D—H6D119.9
C2A—C7A—C6A120.7 (2)C6D—C7D—C2D120.65 (18)
C2A—C7A—H7A119.6C6D—C7D—H7D119.7
C6A—C7A—H7A119.6C2D—C7D—H7D119.7
C1A—N1A—C11A130.33 (17)C1D—N1D—C8D121.64 (15)
C1A—N1A—C17A115.0 (8)C1D—N1D—Al291.32 (11)
C1A—N1A—Al192.86 (11)C8D—N1D—Al2145.71 (12)
C11A—N1A—Al1136.74 (14)N1D—C8D—C9D110.81 (15)
C17A—N1A—Al1149.2 (8)N1D—C8D—C10D111.43 (16)
N2A—C8A—C9A112.1 (2)C9D—C8D—C10D110.55 (17)
N2A—C8A—C10A109.3 (2)N1D—C8D—H8D108.0
C9A—C8A—C10A110.7 (3)C9D—C8D—H8D108.0
N2A—C8A—H8A108.2C10D—C8D—H8D108.0
C9A—C8A—H8A108.2C8D—C9D—H9D1109.5
C10A—C8A—H8A108.2C8D—C9D—H9D2109.5
C8A—C9A—H9A1109.5H9D1—C9D—H9D2109.5
C8A—C9A—H9A2109.5C8D—C9D—H9D3109.5
H9A1—C9A—H9A2109.5H9D1—C9D—H9D3109.5
C8A—C9A—H9A3109.5H9D2—C9D—H9D3109.5
H9A1—C9A—H9A3109.5C8D—C10D—H10J109.5
H9A2—C9A—H9A3109.5C8D—C10D—H10K109.5
C8A—C10A—H10A109.5H10J—C10D—H10K109.5
C8A—C10A—H10B109.5C8D—C10D—H10L109.5
H10A—C10A—H10B109.5H10J—C10D—H10L109.5
C8A—C10A—H10C109.5H10K—C10D—H10L109.5
H10A—C10A—H10C109.5C1D—N2D—C11D121.30 (14)
H10B—C10A—H10C109.5C1D—N2D—Al291.84 (11)
N2A—C14A—C15A109.1 (13)C11D—N2D—Al2146.06 (11)
N2A—C14A—C16A111.6 (16)N2D—C11D—C13D112.15 (15)
C15A—C14A—C16A109.3 (13)N2D—C11D—C12D110.37 (15)
N2A—C14A—H14A108.9C13D—C11D—C12D110.24 (16)
C15A—C14A—H14A108.9N2D—C11D—H11D108.0
C16A—C14A—H14A108.9C13D—C11D—H11D108.0
C14A—C15A—H15A109.5C12D—C11D—H11D108.0
C14A—C15A—H15B109.5C11D—C12D—H12J109.5
H15A—C15A—H15B109.5C11D—C12D—H12K109.5
C14A—C15A—H15C109.5H12J—C12D—H12K109.5
H15A—C15A—H15C109.5C11D—C12D—H12L109.5
H15B—C15A—H15C109.5H12J—C12D—H12L109.5
C14A—C16A—H16A109.5H12K—C12D—H12L109.5
C14A—C16A—H16B109.5C11D—C13D—H13J109.5
H16A—C16A—H16B109.5C11D—C13D—H13K109.5
C14A—C16A—H16C109.5H13J—C13D—H13K109.5
H16A—C16A—H16C109.5C11D—C13D—H13L109.5
H16B—C16A—H16C109.5H13J—C13D—H13L109.5
C1A—N2A—C8A122.2 (2)H13K—C13D—H13L109.5
C1A—N2A—C14A122.5 (11)N2E—C1E—N1E111.20 (15)
C1A—N2A—Al190.62 (10)N2E—C1E—C2E125.37 (15)
C8A—N2A—Al1146.9 (2)N1E—C1E—C2E123.43 (15)
C14A—N2A—Al1144.0 (10)C7E—C2E—C3E118.45 (17)
N1A—C11A—C13A115.9 (2)C7E—C2E—C1E121.43 (17)
N1A—C11A—C12A111.3 (3)C3E—C2E—C1E120.11 (16)
C13A—C11A—C12A111.3 (2)C4E—C3E—C2E120.63 (19)
N1A—C11A—H11A105.9C4E—C3E—H3E119.7
C13A—C11A—H11A105.9C2E—C3E—H3E119.7
C12A—C11A—H11A105.9C5E—C4E—C3E120.2 (2)
C11A—C12A—H12A109.5C5E—C4E—H4E119.9
C11A—C12A—H12B109.5C3E—C4E—H4E119.9
H12A—C12A—H12B109.5C6E—C5E—C4E119.8 (2)
C11A—C12A—H12C109.5C6E—C5E—H5E120.1
H12A—C12A—H12C109.5C4E—C5E—H5E120.1
H12B—C12A—H12C109.5C5E—C6E—C7E120.4 (2)
C11A—C13A—H13A109.5C5E—C6E—H6E119.8
C11A—C13A—H13B109.5C7E—C6E—H6E119.8
H13A—C13A—H13B109.5C2E—C7E—C6E120.6 (2)
C11A—C13A—H13C109.5C2E—C7E—H7E119.7
H13A—C13A—H13C109.5C6E—C7E—H7E119.7
H13B—C13A—H13C109.5C1E—N1E—C8E122.58 (14)
N1A—C17A—C18A112.4 (18)C1E—N1E—Al291.48 (10)
N1A—C17A—C19A112.5 (10)C8E—N1E—Al2145.80 (12)
C18A—C17A—C19A109.6 (12)N1E—C8E—C10E111.12 (15)
N1A—C17A—H17A107.4N1E—C8E—C9E110.76 (14)
C18A—C17A—H17A107.4C10E—C8E—C9E110.15 (16)
C19A—C17A—H17A107.4N1E—C8E—H8E108.2
C17A—C18A—H18A109.5C10E—C8E—H8E108.2
C17A—C18A—H18B109.5C9E—C8E—H8E108.2
H18A—C18A—H18B109.5C8E—C9E—H9E1109.5
C17A—C18A—H18C109.5C8E—C9E—H9E2109.5
H18A—C18A—H18C109.5H9E1—C9E—H9E2109.5
H18B—C18A—H18C109.5C8E—C9E—H9E3109.5
C17A—C19A—H19A109.5H9E1—C9E—H9E3109.5
C17A—C19A—H19B109.5H9E2—C9E—H9E3109.5
H19A—C19A—H19B109.5C8E—C10E—H10M109.5
C17A—C19A—H19C109.5C8E—C10E—H10N109.5
H19A—C19A—H19C109.5H10M—C10E—H10N109.5
H19B—C19A—H19C109.5C8E—C10E—H10O109.5
N1B—C1B—N2B112.13 (15)H10M—C10E—H10O109.5
N1B—C1B—C2B124.56 (15)H10N—C10E—H10O109.5
N2B—C1B—C2B123.29 (15)C1E—N2E—C17E137.4 (3)
C3B—C2B—C7B118.69 (16)C1E—N2E—C11E117.69 (17)
C3B—C2B—C1B120.04 (16)C1E—N2E—Al291.62 (10)
C7B—C2B—C1B121.27 (15)C17E—N2E—Al2130.6 (3)
C2B—C3B—C4B120.71 (18)C11E—N2E—Al2150.30 (15)
C2B—C3B—H3B119.6N2E—C11E—C12E109.1 (6)
C4B—C3B—H3B119.6N2E—C11E—C13E111.7 (3)
C5B—C4B—C3B120.00 (18)C12E—C11E—C13E108.0 (6)
C5B—C4B—H4B120.0N2E—C11E—H11E109.3
C3B—C4B—H4B120.0C12E—C11E—H11E109.3
C6B—C5B—C4B119.94 (17)C13E—C11E—H11E109.3
C6B—C5B—H5B120.0C11E—C12E—H12M109.5
C4B—C5B—H5B120.0C11E—C12E—H12N109.5
C5B—C6B—C7B120.01 (17)H12M—C12E—H12N109.5
C5B—C6B—H6B120.0C11E—C12E—H12O109.5
C7B—C6B—H6B120.0H12M—C12E—H12O109.5
C6B—C7B—C2B120.65 (17)H12N—C12E—H12O109.5
C6B—C7B—H7B119.7C11E—C13E—H13M109.5
C2B—C7B—H7B119.7C11E—C13E—H13N109.5
C1B—N1B—C8B121.75 (14)H13M—C13E—H13N109.5
C1B—N1B—Al191.05 (10)C11E—C13E—H13O109.5
C8B—N1B—Al1146.75 (12)H13M—C13E—H13O109.5
N1B—C8B—C9B110.45 (15)H13N—C13E—H13O109.5
N1B—C8B—C10B111.82 (15)N2E—C17E—C19E108.7 (5)
C9B—C8B—C10B109.92 (16)N2E—C17E—C18E112.2 (14)
N1B—C8B—H8B108.2C19E—C17E—C18E112.8 (11)
C9B—C8B—H8B108.2N2E—C17E—H17E107.6
C10B—C8B—H8B108.2C19E—C17E—H17E107.6
C8B—C9B—H9B1109.5C18E—C17E—H17E107.6
C8B—C9B—H9B2109.5C17E—C18E—H18M109.5
H9B1—C9B—H9B2109.5C17E—C18E—H18N109.5
C8B—C9B—H9B3109.5H18M—C18E—H18N109.5
H9B1—C9B—H9B3109.5C17E—C18E—H18O109.5
H9B2—C9B—H9B3109.5H18M—C18E—H18O109.5
C8B—C10B—H10D109.5H18N—C18E—H18O109.5
C8B—C10B—H10E109.5C17E—C19E—H19M109.5
H10D—C10B—H10E109.5C17E—C19E—H19N109.5
C8B—C10B—H10F109.5H19M—C19E—H19N109.5
H10D—C10B—H10F109.5C17E—C19E—H19O109.5
H10E—C10B—H10F109.5H19M—C19E—H19O109.5
N2B—C11B—C12B111.38 (16)H19N—C19E—H19O109.5
N2B—C11B—C13B110.85 (15)N2F—C1F—N1F111.56 (15)
C12B—C11B—C13B110.97 (17)N2F—C1F—C2F124.68 (16)
N2B—C11B—H11B107.8N1F—C1F—C2F123.75 (16)
C12B—C11B—H11B107.8C7F—C2F—C3F118.52 (18)
C13B—C11B—H11B107.8C7F—C2F—C1F121.23 (17)
C11B—C12B—H12D109.5C3F—C2F—C1F120.22 (17)
C11B—C12B—H12E109.5C4F—C3F—C2F120.6 (2)
H12D—C12B—H12E109.5C4F—C3F—H3F119.7
C11B—C12B—H12F109.5C2F—C3F—H3F119.7
H12D—C12B—H12F109.5C5F—C4F—C3F120.0 (2)
H12E—C12B—H12F109.5C5F—C4F—H4F120.0
C1B—N2B—C11B121.61 (14)C3F—C4F—H4F120.0
C1B—N2B—Al191.12 (10)C6F—C5F—C4F120.01 (19)
C11B—N2B—Al1146.07 (12)C6F—C5F—H5F120.0
C11B—C13B—H13D109.5C4F—C5F—H5F120.0
C11B—C13B—H13E109.5C5F—C6F—C7F120.2 (2)
H13D—C13B—H13E109.5C5F—C6F—H6F119.9
C11B—C13B—H13F109.5C7F—C6F—H6F119.9
H13D—C13B—H13F109.5C2F—C7F—C6F120.6 (2)
H13E—C13B—H13F109.5C2F—C7F—H7F119.7
N1C—C1C—N2C111.56 (16)C6F—C7F—H7F119.7
N1C—C1C—C2C124.64 (17)C1F—N1F—C8F121.47 (15)
N2C—C1C—C2C123.80 (17)C1F—N1F—Al291.36 (11)
C7C—C2C—C3C118.6 (2)C8F—N1F—Al2144.40 (12)
C7C—C2C—C1C121.05 (19)N1F—C8F—C9F110.87 (16)
C3C—C2C—C1C120.32 (19)N1F—C8F—C10F112.63 (16)
C2C—C3C—C4120.2 (2)C9F—C8F—C10F109.06 (18)
C2C—C3C—H3C119.9N1F—C8F—H8F108.0
C4—C3C—H3C119.9C9F—C8F—H8F108.0
C5C—C4—C3C120.3 (3)C10F—C8F—H8F108.0
C5C—C4—H4119.8C8F—C9F—H9F1109.5
C3C—C4—H4119.8C8F—C9F—H9F2109.5
C6C—C5C—C4119.9 (2)H9F1—C9F—H9F2109.5
C6C—C5C—H5C120.0C8F—C9F—H9F3109.5
C4—C5C—H5C120.0H9F1—C9F—H9F3109.5
C5C—C6C—C7C120.1 (3)H9F2—C9F—H9F3109.5
C5C—C6C—H6C120.0C8F—C10F—H10P109.5
C7C—C6C—H6C120.0C8F—C10F—H10Q109.5
C2C—C7C—C6C120.9 (2)H10P—C10F—H10Q109.5
C2C—C7C—H7C119.5C8F—C10F—H10R109.5
C6C—C7C—H7C119.5H10P—C10F—H10R109.5
C1C—N1C—C11C122.93 (15)H10Q—C10F—H10R109.5
C1C—N1C—Al191.86 (11)C1F—N2F—C11F123.1 (3)
C11C—N1C—Al1144.32 (12)C1F—N2F—C17F123.0 (8)
N2C—C8C—C10C111.39 (17)C1F—N2F—Al291.50 (11)
N2C—C8C—C9C110.70 (15)C11F—N2F—Al2144.2 (3)
C10C—C8C—C9C109.91 (17)C17F—N2F—Al2145.0 (8)
N2C—C8C—H8C108.2N2F—C11F—C12F111.7 (4)
C10C—C8C—H8C108.2N2F—C11F—C13F110.8 (3)
C9C—C8C—H8C108.2C12F—C11F—C13F110.3 (3)
C8C—C9C—H9C1109.5N2F—C11F—H11F108.0
C8C—C9C—H9C2109.5C12F—C11F—H11F108.0
H9C1—C9C—H9C2109.5C13F—C11F—H11F108.0
C8C—C9C—H9C3109.5C11F—C12F—H12P109.5
H9C1—C9C—H9C3109.5C11F—C12F—H12Q109.5
H9C2—C9C—H9C3109.5H12P—C12F—H12Q109.5
C8C—C10C—H10G109.5C11F—C12F—H12R109.5
C8C—C10C—H10H109.5H12P—C12F—H12R109.5
H10G—C10C—H10H109.5H12Q—C12F—H12R109.5
C8C—C10C—H10I109.5C11F—C13F—H13P109.5
H10G—C10C—H10I109.5C11F—C13F—H13Q109.5
H10H—C10C—H10I109.5H13P—C13F—H13Q109.5
C1C—N2C—C8C121.12 (16)C11F—C13F—H13R109.5
C1C—N2C—Al190.98 (11)H13P—C13F—H13R109.5
C8C—N2C—Al1146.38 (12)H13Q—C13F—H13R109.5
N1C—C11C—C12C111.03 (16)N2F—C17F—C18F106.8 (12)
N1C—C11C—C13C110.77 (16)N2F—C17F—C19F109.4 (12)
C12C—C11C—C13C110.7 (2)C18F—C17F—C19F111.4 (11)
N1C—C11C—H11C108.1N2F—C17F—H17F109.7
C12C—C11C—H11C108.1C18F—C17F—H17F109.7
C13C—C11C—H11C108.1C19F—C17F—H17F109.7
C11C—C12C—H12G109.5C17F—C18F—H18D109.5
C11C—C12C—H12H109.5C17F—C18F—H18E109.5
H12G—C12C—H12H109.5H18D—C18F—H18E109.5
C11C—C12C—H12I109.5C17F—C18F—H18F109.5
H12G—C12C—H12I109.5H18D—C18F—H18F109.5
H12H—C12C—H12I109.5H18E—C18F—H18F109.5
C11C—C13C—H13G109.5C17F—C19F—H19D109.5
C11C—C13C—H13H109.5C17F—C19F—H19E109.5
H13G—C13C—H13H109.5H19D—C19F—H19E109.5
C11C—C13C—H13I109.5C17F—C19F—H19F109.5
H13G—C13C—H13I109.5H19D—C19F—H19F109.5
H13H—C13C—H13I109.5H19E—C19F—H19F109.5
N2A—C1A—C2A—C7A103.1 (2)N2D—C1D—C2D—C3D76.0 (2)
N1A—C1A—C2A—C7A77.6 (2)N1D—C1D—C2D—C3D104.6 (2)
N2A—C1A—C2A—C3A78.9 (2)N2D—C1D—C2D—C7D103.5 (2)
N1A—C1A—C2A—C3A100.5 (2)N1D—C1D—C2D—C7D75.9 (2)
C7A—C2A—C3A—C4A1.4 (3)C7D—C2D—C3D—C4D0.1 (3)
C1A—C2A—C3A—C4A176.6 (2)C1D—C2D—C3D—C4D179.46 (17)
C2A—C3A—C4A—C5A0.1 (4)C2D—C3D—C4D—C5D0.2 (3)
C3A—C4A—C5A—C6A1.1 (4)C3D—C4D—C5D—C6D0.1 (3)
C4A—C5A—C6A—C7A1.1 (4)C4D—C5D—C6D—C7D0.1 (3)
C3A—C2A—C7A—C6A1.4 (3)C5D—C6D—C7D—C2D0.2 (3)
C1A—C2A—C7A—C6A176.62 (19)C3D—C2D—C7D—C6D0.1 (3)
C5A—C6A—C7A—C2A0.2 (3)C1D—C2D—C7D—C6D179.68 (18)
N2A—C1A—N1A—C11A178.1 (2)N2D—C1D—N1D—C8D170.76 (16)
C2A—C1A—N1A—C11A2.4 (3)C2D—C1D—N1D—C8D9.8 (3)
N2A—C1A—N1A—C17A167.2 (7)N2D—C1D—N1D—Al20.72 (15)
C2A—C1A—N1A—C17A13.3 (7)C2D—C1D—N1D—Al2179.81 (15)
N2A—C1A—N1A—Al10.87 (15)C1D—N1D—C8D—C9D124.70 (18)
C2A—C1A—N1A—Al1179.68 (15)Al2—N1D—C8D—C9D37.4 (3)
N1A—C1A—N2A—C8A175.16 (19)C1D—N1D—C8D—C10D111.8 (2)
C2A—C1A—N2A—C8A4.3 (3)Al2—N1D—C8D—C10D86.1 (3)
N1A—C1A—N2A—C14A164.0 (9)N1D—C1D—N2D—C11D171.62 (15)
C2A—C1A—N2A—C14A15.4 (9)C2D—C1D—N2D—C11D7.9 (3)
N1A—C1A—N2A—Al10.85 (14)N1D—C1D—N2D—Al20.72 (15)
C2A—C1A—N2A—Al1179.70 (16)C2D—C1D—N2D—Al2179.80 (15)
C9A—C8A—N2A—C1A120.5 (3)C1D—N2D—C11D—C13D104.30 (19)
C10A—C8A—N2A—C1A116.3 (3)Al2—N2D—C11D—C13D89.5 (2)
C9A—C8A—N2A—C14A145 (8)C1D—N2D—C11D—C12D132.35 (17)
C10A—C8A—N2A—C14A22 (7)Al2—N2D—C11D—C12D33.8 (3)
C9A—C8A—N2A—Al166.9 (4)N2E—C1E—C2E—C7E73.9 (2)
C10A—C8A—N2A—Al156.3 (5)N1E—C1E—C2E—C7E106.8 (2)
C15A—C14A—N2A—C1A87.2 (18)N2E—C1E—C2E—C3E107.1 (2)
C16A—C14A—N2A—C1A152.0 (12)N1E—C1E—C2E—C3E72.3 (2)
C15A—C14A—N2A—C8A4 (6)C7E—C2E—C3E—C4E0.3 (3)
C16A—C14A—N2A—C8A116 (8)C1E—C2E—C3E—C4E178.73 (18)
C15A—C14A—N2A—Al1119.1 (15)C2E—C3E—C4E—C5E0.6 (3)
C16A—C14A—N2A—Al12 (2)C3E—C4E—C5E—C6E1.3 (4)
C1A—N1A—C11A—C13A40.9 (4)C4E—C5E—C6E—C7E1.0 (4)
C17A—N1A—C11A—C13A75 (3)C3E—C2E—C7E—C6E0.6 (3)
Al1—N1A—C11A—C13A143.0 (2)C1E—C2E—C7E—C6E178.46 (19)
C1A—N1A—C11A—C12A87.5 (3)C5E—C6E—C7E—C2E0.1 (3)
C17A—N1A—C11A—C12A53 (3)N2E—C1E—N1E—C8E176.80 (15)
Al1—N1A—C11A—C12A88.5 (3)C2E—C1E—N1E—C8E2.6 (3)
C1A—N1A—C17A—C18A120.7 (14)N2E—C1E—N1E—Al20.01 (14)
C11A—N1A—C17A—C18A87 (3)C2E—C1E—N1E—Al2179.40 (15)
Al1—N1A—C17A—C18A32 (2)C1E—N1E—C8E—C10E110.61 (19)
C1A—N1A—C17A—C19A115.1 (13)Al2—N1E—C8E—C10E63.7 (3)
C11A—N1A—C17A—C19A36.8 (18)C1E—N1E—C8E—C9E126.61 (18)
Al1—N1A—C17A—C19A92.3 (17)Al2—N1E—C8E—C9E59.1 (3)
N1B—C1B—C2B—C3B103.6 (2)N1E—C1E—N2E—C17E173.4 (6)
N2B—C1B—C2B—C3B74.5 (2)C2E—C1E—N2E—C17E7.2 (6)
N1B—C1B—C2B—C7B76.8 (2)N1E—C1E—N2E—C11E175.0 (2)
N2B—C1B—C2B—C7B105.1 (2)C2E—C1E—N2E—C11E5.6 (3)
C7B—C2B—C3B—C4B0.0 (3)N1E—C1E—N2E—Al20.01 (14)
C1B—C2B—C3B—C4B179.67 (18)C2E—C1E—N2E—Al2179.39 (15)
C2B—C3B—C4B—C5B0.2 (3)C1E—N2E—C11E—C12E118.7 (6)
C3B—C4B—C5B—C6B0.4 (3)C17E—N2E—C11E—C12E58.1 (16)
C4B—C5B—C6B—C7B0.4 (3)Al2—N2E—C11E—C12E51.1 (8)
C5B—C6B—C7B—C2B0.1 (3)C1E—N2E—C11E—C13E121.9 (3)
C3B—C2B—C7B—C6B0.1 (3)C17E—N2E—C11E—C13E61.3 (14)
C1B—C2B—C7B—C6B179.73 (17)Al2—N2E—C11E—C13E68.3 (5)
N2B—C1B—N1B—C8B173.84 (15)C1E—N2E—C17E—C19E44.8 (10)
C2B—C1B—N1B—C8B4.5 (3)C11E—N2E—C17E—C19E40.6 (10)
N2B—C1B—N1B—Al10.36 (14)Al2—N2E—C17E—C19E143.9 (4)
C2B—C1B—N1B—Al1178.70 (15)C1E—N2E—C17E—C18E80.7 (15)
C1B—N1B—C8B—C9B131.79 (18)C11E—N2E—C17E—C18E85 (2)
Al1—N1B—C8B—C9B37.6 (3)Al2—N2E—C17E—C18E90.6 (14)
C1B—N1B—C8B—C10B105.45 (19)N2F—C1F—C2F—C7F60.3 (2)
Al1—N1B—C8B—C10B85.2 (2)N1F—C1F—C2F—C7F118.3 (2)
N1B—C1B—N2B—C11B170.92 (15)N2F—C1F—C2F—C3F121.9 (2)
C2B—C1B—N2B—C11B10.7 (2)N1F—C1F—C2F—C3F59.4 (2)
N1B—C1B—N2B—Al10.36 (14)C7F—C2F—C3F—C4F0.6 (3)
C2B—C1B—N2B—Al1178.73 (14)C1F—C2F—C3F—C4F178.45 (17)
C12B—C11B—N2B—C1B118.59 (19)C2F—C3F—C4F—C5F0.8 (3)
C13B—C11B—N2B—C1B117.33 (18)C3F—C4F—C5F—C6F0.2 (3)
C12B—C11B—N2B—Al178.5 (3)C4F—C5F—C6F—C7F0.5 (3)
C13B—C11B—N2B—Al145.6 (3)C3F—C2F—C7F—C6F0.1 (3)
N1C—C1C—C2C—C7C75.1 (3)C1F—C2F—C7F—C6F177.67 (18)
N2C—C1C—C2C—C7C104.0 (2)C5F—C6F—C7F—C2F0.7 (3)
N1C—C1C—C2C—C3C106.8 (2)N2F—C1F—N1F—C8F166.75 (15)
N2C—C1C—C2C—C3C74.2 (3)C2F—C1F—N1F—C8F12.1 (3)
C7C—C2C—C3C—C40.8 (3)N2F—C1F—N1F—Al21.25 (14)
C1C—C2C—C3C—C4179.0 (2)C2F—C1F—N1F—Al2177.56 (15)
C2C—C3C—C4—C5C0.6 (4)C1F—N1F—C8F—C9F118.5 (2)
C3C—C4—C5C—C6C0.5 (4)Al2—N1F—C8F—C9F36.0 (3)
C4—C5C—C6C—C7C1.2 (4)C1F—N1F—C8F—C10F118.93 (19)
C3C—C2C—C7C—C6C0.0 (3)Al2—N1F—C8F—C10F86.5 (2)
C1C—C2C—C7C—C6C178.2 (2)N1F—C1F—N2F—C11F168.8 (3)
C5C—C6C—C7C—C2C1.0 (4)C2F—C1F—N2F—C11F12.4 (3)
N2C—C1C—N1C—C11C171.40 (15)N1F—C1F—N2F—C17F172.5 (8)
C2C—C1C—N1C—C11C9.4 (3)C2F—C1F—N2F—C17F8.7 (8)
N2C—C1C—N1C—Al10.18 (16)N1F—C1F—N2F—Al21.26 (14)
C2C—C1C—N1C—Al1178.99 (17)C2F—C1F—N2F—Al2177.55 (15)
N1C—C1C—N2C—C8C169.67 (16)C1F—N2F—C11F—C12F117.7 (4)
C2C—C1C—N2C—C8C9.5 (3)C17F—N2F—C11F—C12F152 (21)
N1C—C1C—N2C—Al10.17 (15)Al2—N2F—C11F—C12F45.2 (6)
C2C—C1C—N2C—Al1179.00 (17)C1F—N2F—C11F—C13F118.9 (5)
C10C—C8C—N2C—C1C112.2 (2)C17F—N2F—C11F—C13F29 (20)
C9C—C8C—N2C—C1C125.21 (19)Al2—N2F—C11F—C13F78.2 (6)
C10C—C8C—N2C—Al187.1 (3)C1F—N2F—C17F—C18F97.8 (13)
C9C—C8C—N2C—Al135.6 (3)C11F—N2F—C17F—C18F6 (19)
C1C—N1C—C11C—C12C130.3 (2)Al2—N2F—C17F—C18F71.2 (16)
Al1—N1C—C11C—C12C64.2 (3)C1F—N2F—C17F—C19F141.5 (10)
C1C—N1C—C11C—C13C106.2 (2)C11F—N2F—C17F—C19F127 (21)
Al1—N1C—C11C—C13C59.3 (3)Al2—N2F—C17F—C19F49.5 (18)
(AlPhCNiPr22Cl) Chloridobis(N,N'-diisopropylbenzimidamido)aluminium(III) top
Crystal data top
[Al(C13H19N2)2Cl]F(000) = 2016
Mr = 469.03Dx = 1.149 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.205 (1) ÅCell parameters from 8832 reflections
b = 16.4832 (9) Åθ = 2.2–25.1°
c = 17.8498 (10) ŵ = 0.19 mm1
β = 106.287 (1)°T = 100 K
V = 5423.8 (5) Å3Prism, yellow
Z = 80.21 × 0.20 × 0.14 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
10641 independent reflections
Radiation source: sealed tube7375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 8.333 pixels mm-1θmax = 26.0°, θmin = 1.7°
φ and ω scansh = 023
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008)
k = 200
Tmin = 0.858, Tmax = 0.973l = 2221
100296 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.010P)2 + 4.680P]
where P = (Fo2 + 2Fc2)/3
10641 reflections(Δ/σ)max = 0.001
593 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Al(C13H19N2)2Cl]V = 5423.8 (5) Å3
Mr = 469.03Z = 8
Monoclinic, P21/cMo Kα radiation
a = 19.205 (1) ŵ = 0.19 mm1
b = 16.4832 (9) ÅT = 100 K
c = 17.8498 (10) Å0.21 × 0.20 × 0.14 mm
β = 106.287 (1)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
10641 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008)
7375 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 0.973Rint = 0.080
100296 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.00Δρmax = 0.45 e Å3
10641 reflectionsΔρmin = 0.31 e Å3
593 parameters
Special details top

Experimental. Integrated as non-merohedrally split crystal. Single reflection set is generated based on the reflections of the first component and overlapped reflections of the first and second components.

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. H atoms were positioned from geometric considerations and refined as riding on the attached atoms with orientation of CH3 groups optimized. Uiso of H atoms were contrained to be 20% larger than Ueqv of the attached atom (50% larger for CH3 groups).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Al10.40996 (3)0.30415 (4)0.46657 (4)0.02013 (15)
Cl10.48446 (3)0.33724 (3)0.39740 (3)0.02442 (13)
C1A0.45647 (11)0.34633 (12)0.59834 (13)0.0226 (5)
C2A0.48630 (12)0.37850 (13)0.67933 (12)0.0229 (5)
C3A0.51624 (12)0.45585 (13)0.69101 (13)0.0269 (5)
H3A0.51710.48860.64750.032*
C4A0.54482 (12)0.48525 (14)0.76596 (14)0.0311 (6)
H4A0.56610.53770.77380.037*
C5A0.54242 (13)0.43847 (15)0.82921 (14)0.0362 (6)
H5A0.56140.45910.88060.043*
C6A0.51261 (14)0.36187 (15)0.81813 (14)0.0382 (6)
H6A0.51140.32980.86190.046*
C7A0.48443 (13)0.33143 (14)0.74348 (13)0.0312 (6)
H7A0.46390.27860.73600.037*
N1A0.39906 (9)0.37715 (10)0.54562 (10)0.0239 (4)
C11A0.34861 (12)0.43629 (14)0.56244 (13)0.0281 (5)
H11A0.36870.45580.61730.034*
C12A0.27567 (13)0.39630 (16)0.55493 (16)0.0400 (6)
H12A0.25580.37590.50160.060*
H12B0.24220.43610.56650.060*
H12C0.28200.35110.59190.060*
C13A0.34198 (13)0.50824 (14)0.50763 (15)0.0356 (6)
H13A0.38980.53290.51480.053*
H13B0.30880.54840.51920.053*
H13C0.32300.48980.45350.053*
N2A0.48408 (9)0.28481 (10)0.56825 (10)0.0223 (4)
C21A0.55718 (12)0.25225 (13)0.60462 (14)0.0276 (5)
H21A0.56350.24500.66180.033*
C22A0.56353 (13)0.16986 (14)0.56882 (14)0.0338 (6)
H22A0.52860.13220.58080.051*
H22B0.61280.14880.59050.051*
H22C0.55330.17550.51210.051*
C23A0.61602 (13)0.30916 (15)0.59374 (16)0.0415 (7)
H23A0.61060.31640.53790.062*
H23B0.66380.28590.61890.062*
H23C0.61160.36180.61740.062*
C1B0.30417 (11)0.24168 (13)0.38434 (12)0.0212 (5)
C2B0.24110 (11)0.19646 (13)0.33379 (12)0.0227 (5)
C3B0.25077 (12)0.14563 (14)0.27549 (13)0.0283 (5)
H3B0.29710.14120.26660.034*
C4B0.19276 (13)0.10123 (15)0.23016 (14)0.0344 (6)
H4B0.19920.06750.18940.041*
C5B0.12579 (14)0.10598 (16)0.24418 (15)0.0393 (6)
H5B0.08630.07490.21360.047*
C6B0.11620 (13)0.15570 (16)0.30243 (15)0.0388 (6)
H6B0.07010.15870.31210.047*
C7B0.17323 (12)0.20128 (14)0.34691 (13)0.0295 (5)
H7B0.16610.23600.38660.035*
N1B0.35512 (9)0.20577 (10)0.44238 (10)0.0213 (4)
C11B0.34447 (12)0.12476 (13)0.47142 (13)0.0256 (5)
H11B0.29340.10790.44520.031*
C12B0.35318 (13)0.12823 (15)0.55884 (13)0.0348 (6)
H12D0.40280.14470.58620.052*
H12E0.34350.07450.57730.052*
H12F0.31890.16760.56930.052*
C13B0.39439 (13)0.06279 (13)0.45069 (14)0.0329 (6)
H13D0.38590.06160.39390.049*
H13E0.38450.00910.46890.049*
H13F0.44500.07770.47580.049*
N2B0.31993 (9)0.31941 (10)0.38067 (10)0.0220 (4)
C21B0.28949 (12)0.37497 (13)0.31475 (13)0.0272 (5)
H21B0.31800.42640.32750.033*
C22B0.21167 (13)0.39796 (15)0.30638 (15)0.0383 (6)
H22D0.18040.35060.28920.058*
H22E0.19710.44140.26770.058*
H22F0.20690.41680.35680.058*
C23B0.30095 (13)0.34464 (14)0.23853 (13)0.0319 (6)
H23D0.35210.33060.24680.048*
H23E0.28720.38730.19880.048*
H23F0.27090.29650.22090.048*
Al20.09906 (3)0.69869 (4)0.04045 (4)0.01958 (14)
Cl20.03433 (3)0.64402 (3)0.11154 (3)0.02421 (13)
C1C0.19838 (11)0.77567 (12)0.11760 (12)0.0207 (5)
C2C0.25703 (11)0.82799 (13)0.16634 (12)0.0212 (5)
C3C0.32648 (12)0.82681 (13)0.15708 (13)0.0265 (5)
H3C0.33760.79070.12060.032*
C4C0.37958 (13)0.87813 (14)0.20084 (13)0.0308 (6)
H4C0.42680.87760.19380.037*
C5C0.36378 (13)0.93017 (14)0.25483 (13)0.0308 (6)
H5C0.40010.96580.28440.037*
C6C0.29541 (13)0.93037 (14)0.26565 (13)0.0309 (6)
H6C0.28510.96500.30370.037*
C7C0.24181 (12)0.88011 (13)0.22103 (13)0.0267 (5)
H7C0.19450.88120.22780.032*
N1C0.19321 (9)0.69659 (10)0.12535 (10)0.0217 (4)
C11C0.23760 (12)0.65363 (13)0.19509 (13)0.0272 (5)
H11C0.28560.68170.21330.033*
C12C0.25070 (15)0.56752 (14)0.17359 (15)0.0420 (7)
H12G0.20410.53940.15430.063*
H12H0.28060.53930.21970.063*
H12I0.27580.56800.13280.063*
C13C0.20164 (13)0.65577 (15)0.26103 (13)0.0359 (6)
H13G0.19670.71220.27610.054*
H13H0.23150.62580.30600.054*
H13I0.15350.63070.24340.054*
N2C0.14207 (9)0.80444 (10)0.06068 (10)0.0201 (4)
C21C0.14526 (12)0.88486 (13)0.02560 (13)0.0247 (5)
H21C0.19540.90670.04780.030*
C22C0.13202 (14)0.87677 (14)0.06213 (13)0.0347 (6)
H22G0.16760.83920.07290.052*
H22H0.13700.93000.08450.052*
H22I0.08300.85580.08560.052*
C23C0.09284 (13)0.94365 (13)0.04646 (14)0.0303 (6)
H23G0.04320.92330.02600.045*
H23H0.09690.99690.02360.045*
H23I0.10460.94870.10330.045*
C1D0.04966 (11)0.66175 (12)0.09242 (12)0.0209 (5)
C2D0.02093 (11)0.63235 (13)0.17414 (12)0.0214 (5)
C3D0.02412 (12)0.68126 (14)0.23634 (13)0.0283 (5)
H3D0.04350.73450.22690.034*
C4D0.00084 (13)0.65272 (14)0.31228 (14)0.0329 (6)
H4D0.00190.68620.35470.039*
C5D0.02962 (12)0.57563 (14)0.32616 (13)0.0309 (6)
H5D0.04690.55620.37820.037*
C6D0.03325 (12)0.52686 (14)0.26466 (13)0.0286 (5)
H6D0.05340.47400.27450.034*
C7D0.00768 (12)0.55463 (13)0.18853 (13)0.0263 (5)
H7D0.00970.52060.14630.032*
N1D0.01586 (9)0.71126 (10)0.05597 (10)0.0227 (4)
C11D0.06152 (12)0.73053 (14)0.08691 (13)0.0282 (5)
H11D0.07290.73800.14470.034*
C12D0.07695 (13)0.80964 (16)0.05082 (14)0.0407 (7)
H12J0.06280.80440.00610.061*
H12K0.12890.82200.06960.061*
H12L0.04910.85360.06570.061*
C13D0.10924 (13)0.66258 (16)0.07050 (15)0.0421 (7)
H13J0.09880.61210.09430.063*
H13K0.16040.67690.09270.063*
H13L0.09910.65510.01400.063*
N2D0.11453 (9)0.63989 (11)0.04533 (10)0.0227 (4)
C21D0.16736 (13)0.59264 (15)0.07247 (14)0.0355 (6)
H21D0.15140.59190.13080.043*
C22D0.24112 (13)0.63313 (18)0.04624 (16)0.0460 (7)
H22J0.23860.68660.07080.069*
H22K0.27690.59950.06160.069*
H22L0.25550.63940.01060.069*
C23D0.16898 (15)0.50588 (16)0.04362 (18)0.0570 (9)
H23J0.18400.50540.01360.086*
H23K0.20350.47420.06300.086*
H23L0.12050.48200.06280.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Al10.0243 (3)0.0176 (3)0.0185 (3)0.0012 (3)0.0061 (3)0.0007 (3)
Cl10.0279 (3)0.0244 (3)0.0238 (3)0.0044 (2)0.0118 (2)0.0012 (2)
C1A0.0272 (12)0.0177 (11)0.0240 (12)0.0022 (9)0.0088 (10)0.0009 (9)
C2A0.0270 (12)0.0220 (12)0.0192 (12)0.0010 (9)0.0056 (9)0.0022 (9)
C3A0.0319 (13)0.0223 (12)0.0260 (13)0.0006 (10)0.0071 (10)0.0006 (10)
C4A0.0342 (14)0.0247 (13)0.0323 (14)0.0038 (11)0.0058 (11)0.0062 (11)
C5A0.0458 (16)0.0365 (15)0.0225 (13)0.0030 (12)0.0034 (11)0.0093 (11)
C6A0.0579 (17)0.0338 (14)0.0222 (13)0.0019 (13)0.0102 (12)0.0031 (11)
C7A0.0418 (15)0.0236 (12)0.0276 (13)0.0065 (11)0.0086 (11)0.0004 (10)
N1A0.0276 (10)0.0213 (10)0.0221 (10)0.0072 (8)0.0057 (8)0.0026 (8)
C11A0.0302 (13)0.0292 (13)0.0247 (13)0.0075 (10)0.0074 (10)0.0060 (10)
C12A0.0387 (15)0.0424 (16)0.0443 (16)0.0083 (12)0.0201 (13)0.0004 (13)
C13A0.0384 (15)0.0240 (13)0.0438 (16)0.0084 (11)0.0106 (12)0.0027 (11)
N2A0.0257 (10)0.0187 (9)0.0209 (10)0.0031 (8)0.0037 (8)0.0015 (8)
C21A0.0253 (12)0.0270 (12)0.0264 (13)0.0055 (10)0.0004 (10)0.0015 (10)
C22A0.0336 (14)0.0313 (13)0.0321 (14)0.0105 (11)0.0017 (11)0.0036 (11)
C23A0.0277 (14)0.0375 (15)0.0548 (18)0.0023 (12)0.0044 (12)0.0082 (13)
C1B0.0213 (11)0.0263 (12)0.0175 (11)0.0017 (9)0.0079 (9)0.0010 (9)
C2B0.0262 (12)0.0210 (11)0.0198 (12)0.0003 (10)0.0045 (9)0.0056 (9)
C3B0.0258 (12)0.0320 (13)0.0259 (13)0.0011 (10)0.0054 (10)0.0022 (10)
C4B0.0389 (15)0.0341 (14)0.0257 (13)0.0047 (12)0.0020 (11)0.0011 (11)
C5B0.0338 (15)0.0415 (15)0.0356 (15)0.0142 (12)0.0018 (12)0.0086 (12)
C6B0.0281 (13)0.0473 (16)0.0403 (16)0.0046 (12)0.0082 (11)0.0138 (13)
C7B0.0277 (13)0.0335 (13)0.0278 (13)0.0017 (11)0.0085 (10)0.0056 (11)
N1B0.0241 (10)0.0198 (9)0.0193 (10)0.0009 (8)0.0051 (8)0.0042 (8)
C11B0.0276 (12)0.0212 (12)0.0265 (13)0.0042 (10)0.0052 (10)0.0065 (10)
C12B0.0443 (15)0.0322 (14)0.0305 (14)0.0056 (12)0.0146 (12)0.0117 (11)
C13B0.0461 (15)0.0202 (12)0.0300 (14)0.0035 (11)0.0070 (12)0.0007 (10)
N2B0.0295 (10)0.0172 (9)0.0191 (10)0.0033 (8)0.0066 (8)0.0021 (7)
C21B0.0347 (13)0.0219 (12)0.0244 (13)0.0042 (10)0.0073 (10)0.0052 (10)
C22B0.0385 (15)0.0381 (15)0.0379 (15)0.0080 (12)0.0099 (12)0.0133 (12)
C23B0.0419 (14)0.0289 (13)0.0237 (13)0.0024 (11)0.0071 (11)0.0045 (10)
Al20.0237 (3)0.0166 (3)0.0190 (3)0.0011 (3)0.0068 (3)0.0000 (3)
Cl20.0264 (3)0.0266 (3)0.0213 (3)0.0061 (2)0.0096 (2)0.0024 (2)
C1C0.0255 (12)0.0221 (12)0.0179 (11)0.0014 (9)0.0116 (9)0.0005 (9)
C2C0.0246 (11)0.0190 (11)0.0191 (11)0.0012 (9)0.0044 (9)0.0040 (9)
C3C0.0320 (13)0.0261 (12)0.0232 (12)0.0007 (10)0.0109 (10)0.0008 (10)
C4C0.0294 (13)0.0336 (14)0.0306 (14)0.0058 (11)0.0107 (11)0.0024 (11)
C5C0.0360 (14)0.0287 (13)0.0247 (13)0.0096 (11)0.0034 (11)0.0005 (10)
C6C0.0371 (14)0.0298 (13)0.0250 (13)0.0024 (11)0.0073 (11)0.0046 (10)
C7C0.0265 (12)0.0305 (13)0.0235 (12)0.0003 (10)0.0075 (10)0.0014 (10)
N1C0.0249 (10)0.0178 (9)0.0214 (10)0.0018 (8)0.0048 (8)0.0032 (8)
C11C0.0293 (12)0.0236 (12)0.0255 (13)0.0014 (10)0.0024 (10)0.0075 (10)
C12C0.0542 (17)0.0272 (14)0.0401 (16)0.0095 (12)0.0060 (13)0.0113 (12)
C13C0.0395 (14)0.0409 (15)0.0245 (13)0.0002 (12)0.0043 (11)0.0081 (11)
N2C0.0234 (9)0.0172 (9)0.0192 (10)0.0012 (8)0.0051 (8)0.0032 (8)
C21C0.0285 (12)0.0190 (11)0.0272 (13)0.0010 (10)0.0089 (10)0.0047 (9)
C22C0.0518 (16)0.0281 (13)0.0272 (14)0.0052 (12)0.0159 (12)0.0077 (11)
C23C0.0362 (14)0.0203 (12)0.0329 (14)0.0025 (10)0.0071 (11)0.0010 (10)
C1D0.0268 (12)0.0156 (11)0.0213 (12)0.0010 (9)0.0082 (9)0.0005 (9)
C2D0.0221 (11)0.0207 (11)0.0219 (12)0.0024 (9)0.0070 (9)0.0021 (9)
C3D0.0356 (14)0.0245 (12)0.0251 (13)0.0038 (10)0.0090 (10)0.0020 (10)
C4D0.0427 (15)0.0339 (14)0.0233 (13)0.0026 (12)0.0111 (11)0.0021 (11)
C5D0.0348 (14)0.0380 (14)0.0206 (13)0.0026 (11)0.0088 (10)0.0085 (11)
C6D0.0302 (13)0.0237 (12)0.0312 (14)0.0036 (10)0.0073 (11)0.0077 (10)
C7D0.0308 (13)0.0229 (12)0.0253 (13)0.0000 (10)0.0078 (10)0.0017 (10)
N1D0.0226 (10)0.0217 (10)0.0233 (10)0.0037 (8)0.0056 (8)0.0020 (8)
C11D0.0252 (12)0.0345 (13)0.0225 (12)0.0078 (10)0.0027 (10)0.0044 (10)
C12D0.0341 (14)0.0491 (16)0.0333 (15)0.0189 (13)0.0001 (11)0.0098 (12)
C13D0.0254 (13)0.0557 (18)0.0434 (16)0.0025 (13)0.0065 (11)0.0035 (14)
N2D0.0236 (10)0.0227 (10)0.0218 (10)0.0038 (8)0.0066 (8)0.0020 (8)
C21D0.0312 (14)0.0446 (16)0.0294 (14)0.0120 (12)0.0063 (11)0.0124 (12)
C22D0.0268 (14)0.072 (2)0.0414 (16)0.0052 (14)0.0137 (12)0.0041 (15)
C23D0.0465 (18)0.0330 (16)0.077 (2)0.0167 (13)0.0068 (15)0.0219 (15)
Geometric parameters (Å, º) top
Al1—N1A1.9102 (18)Al2—N2D1.9046 (18)
Al1—N1B1.9157 (18)Al2—N2C1.9194 (18)
Al1—N2B1.9791 (18)Al2—N1D2.0039 (18)
Al1—N2A1.9932 (18)Al2—N1C2.0076 (18)
Al1—Cl12.2046 (8)Al2—Cl22.2027 (8)
C1A—N2A1.326 (3)C1C—N1C1.317 (3)
C1A—N1A1.333 (3)C1C—N2C1.345 (3)
C1A—C2A1.495 (3)C1C—C2C1.490 (3)
C2A—C3A1.390 (3)C2C—C3C1.389 (3)
C2A—C7A1.392 (3)C2C—C7C1.392 (3)
C3A—C4A1.383 (3)C3C—C4C1.385 (3)
C3A—H3A0.9500C3C—H3C0.9500
C4A—C5A1.379 (3)C4C—C5C1.386 (3)
C4A—H4A0.9500C4C—H4C0.9500
C5A—C6A1.378 (3)C5C—C6C1.380 (3)
C5A—H5A0.9500C5C—H5C0.9500
C6A—C7A1.384 (3)C6C—C7C1.386 (3)
C6A—H6A0.9500C6C—H6C0.9500
C7A—H7A0.9500C7C—H7C0.9500
N1A—C11A1.464 (3)N1C—C11C1.477 (3)
C11A—C12A1.520 (3)C11C—C12C1.510 (3)
C11A—C13A1.520 (3)C11C—C13C1.523 (3)
C11A—H11A1.0000C11C—H11C1.0000
C12A—H12A0.9800C12C—H12G0.9800
C12A—H12B0.9800C12C—H12H0.9800
C12A—H12C0.9800C12C—H12I0.9800
C13A—H13A0.9800C13C—H13G0.9800
C13A—H13B0.9800C13C—H13H0.9800
C13A—H13C0.9800C13C—H13I0.9800
N2A—C21A1.473 (3)N2C—C21C1.475 (3)
C21A—C22A1.520 (3)C21C—C23C1.517 (3)
C21A—C23A1.522 (3)C21C—C22C1.520 (3)
C21A—H21A1.0000C21C—H21C1.0000
C22A—H22A0.9800C22C—H22G0.9800
C22A—H22B0.9800C22C—H22H0.9800
C22A—H22C0.9800C22C—H22I0.9800
C23A—H23A0.9800C23C—H23G0.9800
C23A—H23B0.9800C23C—H23H0.9800
C23A—H23C0.9800C23C—H23I0.9800
C1B—N2B1.322 (3)C1D—N1D1.322 (3)
C1B—N1B1.346 (3)C1D—N2D1.342 (3)
C1B—C2B1.491 (3)C1D—C2D1.489 (3)
C2B—C3B1.388 (3)C2D—C3D1.387 (3)
C2B—C7B1.390 (3)C2D—C7D1.389 (3)
C3B—C4B1.388 (3)C3D—C4D1.387 (3)
C3B—H3B0.9500C3D—H3D0.9500
C4B—C5B1.380 (3)C4D—C5D1.380 (3)
C4B—H4B0.9500C4D—H4D0.9500
C5B—C6B1.376 (4)C5D—C6D1.378 (3)
C5B—H5B0.9500C5D—H5D0.9500
C6B—C7B1.381 (3)C6D—C7D1.387 (3)
C6B—H6B0.9500C6D—H6D0.9500
C7B—H7B0.9500C7D—H7D0.9500
N1B—C11B1.467 (3)N1D—C11D1.468 (3)
C11B—C13B1.516 (3)C11D—C12D1.520 (3)
C11B—C12B1.523 (3)C11D—C13D1.527 (3)
C11B—H11B1.0000C11D—H11D1.0000
C12B—H12D0.9800C12D—H12J0.9800
C12B—H12E0.9800C12D—H12K0.9800
C12B—H12F0.9800C12D—H12L0.9800
C13B—H13D0.9800C13D—H13J0.9800
C13B—H13E0.9800C13D—H13K0.9800
C13B—H13F0.9800C13D—H13L0.9800
N2B—C21B1.476 (3)N2D—C21D1.465 (3)
C21B—C22B1.508 (3)C21D—C22D1.516 (3)
C21B—C23B1.522 (3)C21D—C23D1.517 (4)
C21B—H21B1.0000C21D—H21D1.0000
C22B—H22D0.9800C22D—H22J0.9800
C22B—H22E0.9800C22D—H22K0.9800
C22B—H22F0.9800C22D—H22L0.9800
C23B—H23D0.9800C23D—H23J0.9800
C23B—H23E0.9800C23D—H23K0.9800
C23B—H23F0.9800C23D—H23L0.9800
N1A—Al1—N1B122.18 (8)N2D—Al2—N2C117.22 (8)
N1A—Al1—N2B103.84 (8)N2D—Al2—N1D68.20 (7)
N1B—Al1—N2B68.12 (7)N2C—Al2—N1D105.37 (8)
N1A—Al1—N2A68.06 (7)N2D—Al2—N1C106.71 (8)
N1B—Al1—N2A106.08 (8)N2C—Al2—N1C67.95 (7)
N2B—Al1—N2A166.28 (8)N1D—Al2—N1C169.27 (8)
N1A—Al1—Cl1118.73 (6)N2D—Al2—Cl2119.70 (6)
N1B—Al1—Cl1119.03 (6)N2C—Al2—Cl2123.08 (6)
N2B—Al1—Cl195.62 (6)N1D—Al2—Cl295.41 (6)
N2A—Al1—Cl198.02 (6)N1C—Al2—Cl295.31 (6)
N2A—C1A—N1A110.55 (19)N1C—C1C—N2C111.09 (19)
N2A—C1A—C2A125.08 (19)N1C—C1C—C2C125.32 (19)
N1A—C1A—C2A124.35 (19)N2C—C1C—C2C123.57 (18)
C3A—C2A—C7A119.5 (2)C3C—C2C—C7C119.3 (2)
C3A—C2A—C1A120.04 (19)C3C—C2C—C1C121.08 (19)
C7A—C2A—C1A120.43 (19)C7C—C2C—C1C119.59 (19)
C4A—C3A—C2A120.1 (2)C4C—C3C—C2C120.3 (2)
C4A—C3A—H3A119.9C4C—C3C—H3C119.9
C2A—C3A—H3A119.9C2C—C3C—H3C119.9
C5A—C4A—C3A120.0 (2)C3C—C4C—C5C120.0 (2)
C5A—C4A—H4A120.0C3C—C4C—H4C120.0
C3A—C4A—H4A120.0C5C—C4C—H4C120.0
C6A—C5A—C4A120.2 (2)C6C—C5C—C4C120.1 (2)
C6A—C5A—H5A119.9C6C—C5C—H5C120.0
C4A—C5A—H5A119.9C4C—C5C—H5C120.0
C5A—C6A—C7A120.3 (2)C5C—C6C—C7C120.1 (2)
C5A—C6A—H6A119.8C5C—C6C—H6C120.0
C7A—C6A—H6A119.8C7C—C6C—H6C120.0
C6A—C7A—C2A119.8 (2)C6C—C7C—C2C120.3 (2)
C6A—C7A—H7A120.1C6C—C7C—H7C119.9
C2A—C7A—H7A120.1C2C—C7C—H7C119.9
C1A—N1A—C11A124.96 (18)C1C—N1C—C11C121.34 (18)
C1A—N1A—Al192.36 (13)C1C—N1C—Al288.97 (13)
C11A—N1A—Al1141.91 (15)C11C—N1C—Al2146.00 (14)
N1A—C11A—C12A109.87 (19)N1C—C11C—C12C109.53 (19)
N1A—C11A—C13A109.18 (18)N1C—C11C—C13C111.13 (18)
C12A—C11A—C13A111.9 (2)C12C—C11C—C13C111.2 (2)
N1A—C11A—H11A108.6N1C—C11C—H11C108.3
C12A—C11A—H11A108.6C12C—C11C—H11C108.3
C13A—C11A—H11A108.6C13C—C11C—H11C108.3
C11A—C12A—H12A109.5C11C—C12C—H12G109.5
C11A—C12A—H12B109.5C11C—C12C—H12H109.5
H12A—C12A—H12B109.5H12G—C12C—H12H109.5
C11A—C12A—H12C109.5C11C—C12C—H12I109.5
H12A—C12A—H12C109.5H12G—C12C—H12I109.5
H12B—C12A—H12C109.5H12H—C12C—H12I109.5
C11A—C13A—H13A109.5C11C—C13C—H13G109.5
C11A—C13A—H13B109.5C11C—C13C—H13H109.5
H13A—C13A—H13B109.5H13G—C13C—H13H109.5
C11A—C13A—H13C109.5C11C—C13C—H13I109.5
H13A—C13A—H13C109.5H13G—C13C—H13I109.5
H13B—C13A—H13C109.5H13H—C13C—H13I109.5
C1A—N2A—C21A122.71 (18)C1C—N2C—C21C121.15 (17)
C1A—N2A—Al188.97 (13)C1C—N2C—Al291.97 (13)
C21A—N2A—Al1143.97 (15)C21C—N2C—Al2143.46 (14)
N2A—C21A—C22A108.62 (18)N2C—C21C—C23C111.14 (18)
N2A—C21A—C23A111.66 (19)N2C—C21C—C22C110.10 (18)
C22A—C21A—C23A110.3 (2)C23C—C21C—C22C112.21 (19)
N2A—C21A—H21A108.7N2C—C21C—H21C107.7
C22A—C21A—H21A108.7C23C—C21C—H21C107.7
C23A—C21A—H21A108.7C22C—C21C—H21C107.7
C21A—C22A—H22A109.5C21C—C22C—H22G109.5
C21A—C22A—H22B109.5C21C—C22C—H22H109.5
H22A—C22A—H22B109.5H22G—C22C—H22H109.5
C21A—C22A—H22C109.5C21C—C22C—H22I109.5
H22A—C22A—H22C109.5H22G—C22C—H22I109.5
H22B—C22A—H22C109.5H22H—C22C—H22I109.5
C21A—C23A—H23A109.5C21C—C23C—H23G109.5
C21A—C23A—H23B109.5C21C—C23C—H23H109.5
H23A—C23A—H23B109.5H23G—C23C—H23H109.5
C21A—C23A—H23C109.5C21C—C23C—H23I109.5
H23A—C23A—H23C109.5H23G—C23C—H23I109.5
H23B—C23A—H23C109.5H23H—C23C—H23I109.5
N2B—C1B—N1B109.70 (18)N1D—C1D—N2D110.81 (18)
N2B—C1B—C2B127.78 (19)N1D—C1D—C2D125.81 (19)
N1B—C1B—C2B122.53 (19)N2D—C1D—C2D123.38 (18)
C3B—C2B—C7B119.3 (2)C3D—C2D—C7D119.5 (2)
C3B—C2B—C1B119.90 (19)C3D—C2D—C1D120.51 (19)
C7B—C2B—C1B120.7 (2)C7D—C2D—C1D120.01 (19)
C4B—C3B—C2B120.1 (2)C4D—C3D—C2D120.3 (2)
C4B—C3B—H3B120.0C4D—C3D—H3D119.9
C2B—C3B—H3B120.0C2D—C3D—H3D119.9
C5B—C4B—C3B120.1 (2)C5D—C4D—C3D119.9 (2)
C5B—C4B—H4B120.0C5D—C4D—H4D120.0
C3B—C4B—H4B120.0C3D—C4D—H4D120.0
C6B—C5B—C4B120.0 (2)C6D—C5D—C4D120.1 (2)
C6B—C5B—H5B120.0C6D—C5D—H5D120.0
C4B—C5B—H5B120.0C4D—C5D—H5D120.0
C5B—C6B—C7B120.4 (2)C5D—C6D—C7D120.3 (2)
C5B—C6B—H6B119.8C5D—C6D—H6D119.8
C7B—C6B—H6B119.8C7D—C6D—H6D119.8
C6B—C7B—C2B120.1 (2)C6D—C7D—C2D119.9 (2)
C6B—C7B—H7B119.9C6D—C7D—H7D120.0
C2B—C7B—H7B119.9C2D—C7D—H7D120.0
C1B—N1B—C11B121.91 (18)C1D—N1D—C11D122.25 (18)
C1B—N1B—Al192.08 (13)C1D—N1D—Al288.60 (13)
C11B—N1B—Al1144.38 (14)C11D—N1D—Al2145.58 (15)
N1B—C11B—C13B111.50 (18)N1D—C11D—C12D108.87 (18)
N1B—C11B—C12B109.98 (18)N1D—C11D—C13D111.59 (19)
C13B—C11B—C12B112.34 (19)C12D—C11D—C13D110.4 (2)
N1B—C11B—H11B107.6N1D—C11D—H11D108.6
C13B—C11B—H11B107.6C12D—C11D—H11D108.6
C12B—C11B—H11B107.6C13D—C11D—H11D108.6
C11B—C12B—H12D109.5C11D—C12D—H12J109.5
C11B—C12B—H12E109.5C11D—C12D—H12K109.5
H12D—C12B—H12E109.5H12J—C12D—H12K109.5
C11B—C12B—H12F109.5C11D—C12D—H12L109.5
H12D—C12B—H12F109.5H12J—C12D—H12L109.5
H12E—C12B—H12F109.5H12K—C12D—H12L109.5
C11B—C13B—H13D109.5C11D—C13D—H13J109.5
C11B—C13B—H13E109.5C11D—C13D—H13K109.5
H13D—C13B—H13E109.5H13J—C13D—H13K109.5
C11B—C13B—H13F109.5C11D—C13D—H13L109.5
H13D—C13B—H13F109.5H13J—C13D—H13L109.5
H13E—C13B—H13F109.5H13K—C13D—H13L109.5
C1B—N2B—C21B126.56 (18)C1D—N2D—C21D122.89 (18)
C1B—N2B—Al190.04 (13)C1D—N2D—Al292.30 (13)
C21B—N2B—Al1139.55 (15)C21D—N2D—Al2144.59 (15)
N2B—C21B—C22B113.25 (18)N2D—C21D—C22D109.7 (2)
N2B—C21B—C23B112.61 (18)N2D—C21D—C23D109.8 (2)
C22B—C21B—C23B112.4 (2)C22D—C21D—C23D112.4 (2)
N2B—C21B—H21B105.9N2D—C21D—H21D108.2
C22B—C21B—H21B105.9C22D—C21D—H21D108.2
C23B—C21B—H21B105.9C23D—C21D—H21D108.2
C21B—C22B—H22D109.5C21D—C22D—H22J109.5
C21B—C22B—H22E109.5C21D—C22D—H22K109.5
H22D—C22B—H22E109.5H22J—C22D—H22K109.5
C21B—C22B—H22F109.5C21D—C22D—H22L109.5
H22D—C22B—H22F109.5H22J—C22D—H22L109.5
H22E—C22B—H22F109.5H22K—C22D—H22L109.5
C21B—C23B—H23D109.5C21D—C23D—H23J109.5
C21B—C23B—H23E109.5C21D—C23D—H23K109.5
H23D—C23B—H23E109.5H23J—C23D—H23K109.5
C21B—C23B—H23F109.5C21D—C23D—H23L109.5
H23D—C23B—H23F109.5H23J—C23D—H23L109.5
H23E—C23B—H23F109.5H23K—C23D—H23L109.5
N2A—C1A—C2A—C3A113.2 (2)N1C—C1C—C2C—C3C73.6 (3)
N1A—C1A—C2A—C3A65.1 (3)N2C—C1C—C2C—C3C108.4 (2)
N2A—C1A—C2A—C7A66.8 (3)N1C—C1C—C2C—C7C107.6 (3)
N1A—C1A—C2A—C7A115.0 (3)N2C—C1C—C2C—C7C70.4 (3)
C7A—C2A—C3A—C4A0.9 (3)C7C—C2C—C3C—C4C1.2 (3)
C1A—C2A—C3A—C4A179.1 (2)C1C—C2C—C3C—C4C177.5 (2)
C2A—C3A—C4A—C5A1.2 (3)C2C—C3C—C4C—C5C0.8 (3)
C3A—C4A—C5A—C6A1.0 (4)C3C—C4C—C5C—C6C0.7 (4)
C4A—C5A—C6A—C7A0.4 (4)C4C—C5C—C6C—C7C1.8 (4)
C5A—C6A—C7A—C2A0.0 (4)C5C—C6C—C7C—C2C1.4 (3)
C3A—C2A—C7A—C6A0.3 (3)C3C—C2C—C7C—C6C0.1 (3)
C1A—C2A—C7A—C6A179.7 (2)C1C—C2C—C7C—C6C178.7 (2)
N2A—C1A—N1A—C11A169.42 (19)N2C—C1C—N1C—C11C165.00 (18)
C2A—C1A—N1A—C11A12.1 (3)C2C—C1C—N1C—C11C13.2 (3)
N2A—C1A—N1A—Al12.45 (18)N2C—C1C—N1C—Al21.29 (17)
C2A—C1A—N1A—Al1176.06 (18)C2C—C1C—N1C—Al2176.93 (19)
C1A—N1A—C11A—C12A109.8 (2)C1C—N1C—C11C—C12C151.4 (2)
Al1—N1A—C11A—C12A56.9 (3)Al2—N1C—C11C—C12C58.7 (3)
C1A—N1A—C11A—C13A127.1 (2)C1C—N1C—C11C—C13C85.3 (2)
Al1—N1A—C11A—C13A66.1 (3)Al2—N1C—C11C—C13C64.6 (3)
N1A—C1A—N2A—C21A164.08 (19)N1C—C1C—N2C—C21C162.41 (18)
C2A—C1A—N2A—C21A14.4 (3)C2C—C1C—N2C—C21C19.3 (3)
N1A—C1A—N2A—Al12.35 (17)N1C—C1C—N2C—Al21.35 (18)
C2A—C1A—N2A—Al1176.15 (19)C2C—C1C—N2C—Al2176.91 (17)
C1A—N2A—C21A—C22A164.8 (2)C1C—N2C—C21C—C23C112.2 (2)
Al1—N2A—C21A—C22A47.4 (3)Al2—N2C—C21C—C23C95.8 (3)
C1A—N2A—C21A—C23A73.4 (3)C1C—N2C—C21C—C22C122.8 (2)
Al1—N2A—C21A—C23A74.4 (3)Al2—N2C—C21C—C22C29.1 (3)
N2B—C1B—C2B—C3B103.6 (3)N1D—C1D—C2D—C3D79.8 (3)
N1B—C1B—C2B—C3B75.9 (3)N2D—C1D—C2D—C3D100.9 (3)
N2B—C1B—C2B—C7B79.7 (3)N1D—C1D—C2D—C7D101.8 (3)
N1B—C1B—C2B—C7B100.7 (3)N2D—C1D—C2D—C7D77.4 (3)
C7B—C2B—C3B—C4B1.0 (3)C7D—C2D—C3D—C4D0.2 (3)
C1B—C2B—C3B—C4B177.7 (2)C1D—C2D—C3D—C4D178.2 (2)
C2B—C3B—C4B—C5B1.6 (4)C2D—C3D—C4D—C5D0.6 (4)
C3B—C4B—C5B—C6B1.0 (4)C3D—C4D—C5D—C6D0.3 (4)
C4B—C5B—C6B—C7B0.2 (4)C4D—C5D—C6D—C7D0.4 (3)
C5B—C6B—C7B—C2B0.8 (4)C5D—C6D—C7D—C2D0.8 (3)
C3B—C2B—C7B—C6B0.2 (3)C3D—C2D—C7D—C6D0.5 (3)
C1B—C2B—C7B—C6B176.5 (2)C1D—C2D—C7D—C6D178.9 (2)
N2B—C1B—N1B—C11B166.65 (18)N2D—C1D—N1D—C11D166.39 (19)
C2B—C1B—N1B—C11B13.7 (3)C2D—C1D—N1D—C11D13.0 (3)
N2B—C1B—N1B—Al12.16 (17)N2D—C1D—N1D—Al22.60 (17)
C2B—C1B—N1B—Al1177.48 (17)C2D—C1D—N1D—Al2176.75 (19)
C1B—N1B—C11B—C13B111.4 (2)C1D—N1D—C11D—C12D158.9 (2)
Al1—N1B—C11B—C13B88.1 (3)Al2—N1D—C11D—C12D50.7 (3)
C1B—N1B—C11B—C12B123.3 (2)C1D—N1D—C11D—C13D79.0 (3)
Al1—N1B—C11B—C12B37.2 (3)Al2—N1D—C11D—C13D71.5 (3)
N1B—C1B—N2B—C21B163.53 (19)N1D—C1D—N2D—C21D173.06 (19)
C2B—C1B—N2B—C21B16.1 (3)C2D—C1D—N2D—C21D7.6 (3)
N1B—C1B—N2B—Al12.08 (17)N1D—C1D—N2D—Al22.74 (18)
C2B—C1B—N2B—Al1177.5 (2)C2D—C1D—N2D—Al2176.63 (18)
C1B—N2B—C21B—C22B72.6 (3)C1D—N2D—C21D—C22D130.6 (2)
Al1—N2B—C21B—C22B136.8 (2)Al2—N2D—C21D—C22D42.1 (4)
C1B—N2B—C21B—C23B56.4 (3)C1D—N2D—C21D—C23D105.3 (2)
Al1—N2B—C21B—C23B94.2 (2)Al2—N2D—C21D—C23D81.9 (3)
(AlPhCNCy22Cl) Chloridobis(N,N'-dicyclohexylbenzimidamido)aluminium(III) tetrahydrofuran 0.675-solvate top
Crystal data top
[Al(C19H27N2)2Cl]·0.675C4H8OF(000) = 1468
Mr = 677.95Dx = 1.099 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.042 (4) ÅCell parameters from 10954 reflections
b = 16.007 (3) Åθ = 2.5–30.4°
c = 12.852 (2) ŵ = 0.15 mm1
β = 115.396 (2)°T = 150 K
V = 4096.6 (12) Å3Plate, colourless
Z = 40.40 × 0.34 × 0.12 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
4038 independent reflections
Radiation source: sealed tube3577 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 11.198 pixels mm-1θmax = 26.0°, θmin = 2.1°
ω and φ scansh = 2727
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
k = 1919
Tmin = 0.872, Tmax = 0.982l = 1515
20863 measured reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.010P)2 + 6.580P]
where P = (Fo2 + 2Fc2)/3
4038 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
[Al(C19H27N2)2Cl]·0.675C4H8OV = 4096.6 (12) Å3
Mr = 677.95Z = 4
Monoclinic, C2/cMo Kα radiation
a = 22.042 (4) ŵ = 0.15 mm1
b = 16.007 (3) ÅT = 150 K
c = 12.852 (2) Å0.40 × 0.34 × 0.12 mm
β = 115.396 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
4038 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
3577 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.982Rint = 0.023
20863 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.00Δρmax = 0.28 e Å3
4038 reflectionsΔρmin = 0.25 e Å3
200 parameters
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. C4H8O solvent showed strong disorder along 0, 1/2,z channels and was was treated using SQUEEZE procedure from PLATON software (Spek, 2009). See details in platon_squeeze_void_*).

Total removed eletron density corresponds to 108 electrons which in turn corresponds to 2.7 THF molecues of solvent.

H atoms were positioned from geometric consideration and refined as riding on the attached atom. Uiso of H atoms were constrained to be 20% larger than Ueqv of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.50000.48000 (3)0.25000.03380 (14)
Al10.50000.61653 (4)0.25000.02219 (14)
N10.41384 (6)0.62964 (7)0.10908 (10)0.0240 (3)
N20.51084 (6)0.68318 (7)0.13434 (10)0.0242 (3)
C10.44562 (7)0.67531 (9)0.06238 (12)0.0235 (3)
C20.41364 (7)0.71313 (9)0.05510 (12)0.0253 (3)
C30.42589 (8)0.67932 (11)0.14389 (13)0.0351 (4)
H30.45540.63300.12950.042*
C40.39503 (9)0.71323 (12)0.25332 (14)0.0419 (4)
H40.40300.68970.31420.050*
C50.35279 (9)0.78104 (12)0.27447 (14)0.0407 (4)
H50.33170.80410.34980.049*
C60.34115 (9)0.81544 (11)0.18641 (15)0.0411 (4)
H60.31250.86260.20090.049*
C70.37119 (8)0.78128 (10)0.07669 (13)0.0332 (4)
H70.36270.80460.01630.040*
C110.34714 (7)0.59362 (9)0.04118 (12)0.0255 (3)
H110.31930.63590.01700.031*
C120.35123 (7)0.51470 (10)0.02295 (13)0.0300 (3)
H12A0.37160.52870.07610.036*
H12B0.38050.47310.03320.036*
C130.28158 (8)0.47686 (10)0.09147 (14)0.0345 (4)
H13A0.25350.51650.15210.041*
H13B0.28580.42490.12960.041*
C140.24766 (9)0.45747 (11)0.01311 (17)0.0430 (4)
H14A0.27310.41310.04210.052*
H14B0.20170.43640.06000.052*
C150.24402 (9)0.53480 (12)0.05303 (16)0.0416 (4)
H15A0.22510.51920.10770.050*
H15B0.21350.57620.00160.050*
C160.31316 (8)0.57422 (11)0.11943 (14)0.0341 (4)
H16A0.30830.62650.15640.041*
H16B0.34180.53550.18100.041*
C210.55462 (7)0.74495 (9)0.11687 (12)0.0254 (3)
H210.52630.78110.05020.030*
C220.60763 (8)0.70273 (10)0.08836 (14)0.0325 (3)
H22A0.58520.67180.01490.039*
H22B0.63290.66190.14950.039*
C230.65675 (9)0.76595 (12)0.07778 (15)0.0412 (4)
H23A0.69240.73570.06580.049*
H23B0.63260.80190.00970.049*
C240.68864 (9)0.82035 (12)0.18457 (16)0.0443 (4)
H24A0.71670.78530.25140.053*
H24B0.71800.86250.17300.053*
C250.63515 (9)0.86403 (11)0.20905 (16)0.0398 (4)
H25A0.60940.90250.14490.048*
H25B0.65680.89750.28040.048*
C260.58753 (8)0.80053 (10)0.22304 (13)0.0316 (3)
H26A0.55220.83040.23650.038*
H26B0.61280.76520.29130.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0398 (3)0.0233 (3)0.0315 (3)0.0000.0088 (2)0.000
Al10.0253 (3)0.0220 (3)0.0178 (3)0.0000.0078 (2)0.000
N10.0254 (6)0.0251 (6)0.0188 (6)0.0020 (5)0.0069 (5)0.0015 (5)
N20.0260 (6)0.0251 (6)0.0198 (6)0.0009 (5)0.0082 (5)0.0020 (5)
C10.0282 (7)0.0212 (7)0.0203 (7)0.0021 (6)0.0096 (6)0.0031 (5)
C20.0258 (7)0.0263 (7)0.0218 (7)0.0010 (6)0.0082 (6)0.0009 (6)
C30.0413 (9)0.0360 (9)0.0278 (8)0.0093 (7)0.0146 (7)0.0015 (7)
C40.0516 (10)0.0513 (11)0.0239 (8)0.0052 (9)0.0173 (8)0.0010 (7)
C50.0434 (10)0.0484 (11)0.0256 (8)0.0041 (8)0.0102 (7)0.0121 (7)
C60.0414 (10)0.0410 (10)0.0366 (9)0.0148 (8)0.0128 (8)0.0122 (8)
C70.0374 (9)0.0350 (9)0.0276 (8)0.0077 (7)0.0141 (7)0.0026 (7)
C110.0251 (7)0.0258 (7)0.0220 (7)0.0009 (6)0.0069 (6)0.0025 (6)
C120.0284 (8)0.0315 (8)0.0278 (8)0.0007 (6)0.0100 (6)0.0075 (6)
C130.0294 (8)0.0326 (9)0.0346 (8)0.0008 (7)0.0072 (7)0.0128 (7)
C140.0360 (9)0.0384 (10)0.0539 (11)0.0121 (8)0.0187 (8)0.0145 (8)
C150.0369 (9)0.0465 (11)0.0478 (10)0.0113 (8)0.0242 (8)0.0144 (8)
C160.0360 (9)0.0373 (9)0.0319 (8)0.0083 (7)0.0174 (7)0.0098 (7)
C210.0265 (7)0.0261 (7)0.0227 (7)0.0002 (6)0.0097 (6)0.0036 (6)
C220.0385 (9)0.0341 (9)0.0306 (8)0.0032 (7)0.0202 (7)0.0022 (7)
C230.0419 (10)0.0496 (11)0.0430 (10)0.0018 (8)0.0285 (8)0.0074 (8)
C240.0344 (9)0.0551 (12)0.0463 (10)0.0106 (8)0.0200 (8)0.0049 (9)
C250.0397 (9)0.0378 (9)0.0412 (9)0.0117 (8)0.0167 (8)0.0040 (8)
C260.0321 (8)0.0330 (8)0.0330 (8)0.0045 (7)0.0170 (7)0.0048 (7)
Geometric parameters (Å, º) top
Cl1—Al12.1855 (9)C13—C141.522 (2)
Al1—N21.9260 (12)C13—H13A0.9900
Al1—N2i1.9261 (12)C13—H13B0.9900
Al1—N11.9952 (12)C14—C151.523 (2)
Al1—N1i1.9953 (12)C14—H14A0.9900
Al1—C1i2.3785 (14)C14—H14B0.9900
N1—C11.3213 (18)C15—C161.528 (2)
N1—C111.4680 (18)C15—H15A0.9900
N2—C11.3407 (18)C15—H15B0.9900
N2—C211.4647 (18)C16—H16A0.9900
C1—C21.4935 (19)C16—H16B0.9900
C2—C71.386 (2)C21—C221.524 (2)
C2—C31.390 (2)C21—C261.527 (2)
C3—C41.384 (2)C21—H211.0000
C3—H30.9500C22—C231.530 (2)
C4—C51.379 (3)C22—H22A0.9900
C4—H40.9500C22—H22B0.9900
C5—C61.378 (2)C23—C241.519 (3)
C5—H50.9500C23—H23A0.9900
C6—C71.388 (2)C23—H23B0.9900
C6—H60.9500C24—C251.515 (2)
C7—H70.9500C24—H24A0.9900
C11—C161.521 (2)C24—H24B0.9900
C11—C121.532 (2)C25—C261.526 (2)
C11—H111.0000C25—H25A0.9900
C12—C131.530 (2)C25—H25B0.9900
C12—H12A0.9900C26—H26A0.9900
C12—H12B0.9900C26—H26B0.9900
N2—Al1—N2i112.73 (8)C14—C13—H13B109.5
N2—Al1—N168.04 (5)C12—C13—H13B109.5
N2i—Al1—N1104.92 (5)H13A—C13—H13B108.1
N2—Al1—N1i104.92 (5)C13—C14—C15111.23 (14)
N2i—Al1—N1i68.04 (5)C13—C14—H14A109.4
N1—Al1—N1i167.92 (8)C15—C14—H14A109.4
N2—Al1—Cl1123.64 (4)C13—C14—H14B109.4
N2i—Al1—Cl1123.64 (4)C15—C14—H14B109.4
N1—Al1—Cl196.04 (4)H14A—C14—H14B108.0
N1i—Al1—Cl196.04 (4)C14—C15—C16111.64 (14)
N2—Al1—C1i112.83 (5)C14—C15—H15A109.3
N2i—Al1—C1i34.30 (5)C16—C15—H15A109.3
N1—Al1—C1i138.45 (5)C14—C15—H15B109.3
N1i—Al1—C1i33.74 (5)C16—C15—H15B109.3
Cl1—Al1—C1i113.30 (4)H15A—C15—H15B108.0
C1—N1—C11122.56 (12)C11—C16—C15111.78 (13)
C1—N1—Al189.24 (9)C11—C16—H16A109.3
C11—N1—Al1144.99 (10)C15—C16—H16A109.3
C1—N2—C21122.66 (12)C11—C16—H16B109.3
C1—N2—Al191.67 (9)C15—C16—H16B109.3
C21—N2—Al1143.16 (9)H16A—C16—H16B107.9
N1—C1—N2111.05 (12)N2—C21—C22111.15 (12)
N1—C1—C2124.84 (13)N2—C21—C26110.37 (11)
N2—C1—C2124.11 (13)C22—C21—C26110.72 (12)
C7—C2—C3119.63 (14)N2—C21—H21108.2
C7—C2—C1120.46 (13)C22—C21—H21108.2
C3—C2—C1119.91 (13)C26—C21—H21108.2
C4—C3—C2119.85 (15)C21—C22—C23111.88 (13)
C4—C3—H3120.1C21—C22—H22A109.2
C2—C3—H3120.1C23—C22—H22A109.2
C5—C4—C3120.34 (16)C21—C22—H22B109.2
C5—C4—H4119.8C23—C22—H22B109.2
C3—C4—H4119.8H22A—C22—H22B107.9
C6—C5—C4120.03 (15)C24—C23—C22111.69 (13)
C6—C5—H5120.0C24—C23—H23A109.3
C4—C5—H5120.0C22—C23—H23A109.3
C5—C6—C7120.09 (16)C24—C23—H23B109.3
C5—C6—H6120.0C22—C23—H23B109.3
C7—C6—H6120.0H23A—C23—H23B107.9
C2—C7—C6120.05 (15)C25—C24—C23110.63 (14)
C2—C7—H7120.0C25—C24—H24A109.5
C6—C7—H7120.0C23—C24—H24A109.5
N1—C11—C16109.79 (12)C25—C24—H24B109.5
N1—C11—C12111.63 (12)C23—C24—H24B109.5
C16—C11—C12110.28 (13)H24A—C24—H24B108.1
N1—C11—H11108.4C24—C25—C26110.66 (14)
C16—C11—H11108.4C24—C25—H25A109.5
C12—C11—H11108.4C26—C25—H25A109.5
C13—C12—C11111.11 (12)C24—C25—H25B109.5
C13—C12—H12A109.4C26—C25—H25B109.5
C11—C12—H12A109.4H25A—C25—H25B108.1
C13—C12—H12B109.4C25—C26—C21111.72 (13)
C11—C12—H12B109.4C25—C26—H26A109.3
H12A—C12—H12B108.0C21—C26—H26A109.3
C14—C13—C12110.88 (13)C25—C26—H26B109.3
C14—C13—H13A109.5C21—C26—H26B109.3
C12—C13—H13A109.5H26A—C26—H26B107.9
C11—N1—C1—N2164.48 (12)C1—N1—C11—C1278.85 (17)
Al1—N1—C1—N20.02 (11)Al1—N1—C11—C1273.3 (2)
C11—N1—C1—C215.3 (2)N1—C11—C12—C13178.91 (13)
Al1—N1—C1—C2179.75 (13)C16—C11—C12—C1356.57 (17)
C21—N2—C1—N1165.84 (12)C11—C12—C13—C1456.96 (18)
Al1—N2—C1—N10.02 (12)C12—C13—C14—C1555.59 (19)
C21—N2—C1—C214.4 (2)C13—C14—C15—C1654.5 (2)
Al1—N2—C1—C2179.75 (12)N1—C11—C16—C15178.78 (13)
N1—C1—C2—C773.0 (2)C12—C11—C16—C1555.38 (18)
N2—C1—C2—C7107.29 (17)C14—C15—C16—C1154.7 (2)
N1—C1—C2—C3106.33 (18)C1—N2—C21—C22112.74 (15)
N2—C1—C2—C373.4 (2)Al1—N2—C21—C2291.30 (18)
C7—C2—C3—C40.8 (2)C1—N2—C21—C26124.01 (14)
C1—C2—C3—C4178.53 (15)Al1—N2—C21—C2631.9 (2)
C2—C3—C4—C50.8 (3)N2—C21—C22—C23176.17 (12)
C3—C4—C5—C60.0 (3)C26—C21—C22—C2353.12 (17)
C4—C5—C6—C70.8 (3)C21—C22—C23—C2454.26 (19)
C3—C2—C7—C60.0 (2)C22—C23—C24—C2556.0 (2)
C1—C2—C7—C6179.31 (15)C23—C24—C25—C2657.18 (19)
C5—C6—C7—C20.8 (3)C24—C25—C26—C2157.18 (19)
C1—N1—C11—C16158.54 (13)N2—C21—C26—C25178.32 (13)
Al1—N1—C11—C1649.3 (2)C22—C21—C26—C2554.82 (17)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

(AlPhCNiPr23)(AlPhCNiPr22Cl)(AlPhCNCy22Cl)
Crystal data
Chemical formula[Al(C13H19N2)3][Al(C13H19N2)2Cl][Al(C19H27N2)2Cl]·0.675C4H8O
Mr636.88469.03677.95
Crystal system, space groupOrthorhombic, PccnMonoclinic, P21/cMonoclinic, C2/c
Temperature (K)150100150
a, b, c (Å)31.286 (3), 33.409 (3), 14.3488 (12)19.205 (1), 16.4832 (9), 17.8498 (10)22.042 (4), 16.007 (3), 12.852 (2)
α, β, γ (°)90, 90, 9090, 106.287 (1), 9090, 115.396 (2), 90
V3)14998 (2)5423.8 (5)4096.6 (12)
Z1684
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.190.15
Crystal size (mm)0.35 × 0.30 × 0.110.21 × 0.20 × 0.140.40 × 0.34 × 0.12
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Bruker SMART APEXII area-detector
diffractometer
Bruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(TWINABS; Sheldrick, 2008)
Multi-scan
(TWINABS; Sheldrick, 2008)
Multi-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.930, 0.9900.858, 0.9730.872, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
242499, 14753, 10759 100296, 10641, 7375 20863, 4038, 3577
Rint0.0860.0800.023
(sin θ/λ)max1)0.6170.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.087, 1.03 0.046, 0.090, 1.00 0.037, 0.082, 1.00
No. of reflections14753106414038
No. of parameters901593200
No. of restraints5800
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.230.45, 0.310.28, 0.25

Computer programs: APEX2 and SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), XSHEL (Bruker, 2004), APEX2 (Bruker, 2010) and SHELXL2012 (Sheldrick, 2012).

Selected bond lengths (Å) for (AlPhCNiPr23) top
Al1—N1A1.9826 (15)Al2—N2E2.0156 (15)
Al1—N1C2.0168 (15)Al2—N1E2.0185 (15)
Al1—N2B2.0220 (14)Al2—N2D2.0267 (15)
Al1—N1B2.0299 (14)Al2—N2F2.0279 (14)
Al1—N2C2.0310 (16)Al2—N1F2.0295 (15)
Al1—N2A2.0344 (15)Al2—N1D2.0382 (15)
Selected geometric parameters (Å, º) for (AlPhCNiPr22Cl) top
Al1—N1A1.9102 (18)Al2—N2D1.9046 (18)
Al1—N1B1.9157 (18)Al2—N2C1.9194 (18)
Al1—N2B1.9791 (18)Al2—N1D2.0039 (18)
Al1—N2A1.9932 (18)Al2—N1C2.0076 (18)
Al1—Cl12.2046 (8)Al2—Cl22.2027 (8)
N1A—Al1—N1B122.18 (8)N2D—Al2—N2C117.22 (8)
N1A—Al1—N2B103.84 (8)N2D—Al2—N1D68.20 (7)
N1B—Al1—N2B68.12 (7)N2C—Al2—N1D105.37 (8)
N1A—Al1—N2A68.06 (7)N2D—Al2—N1C106.71 (8)
N1B—Al1—N2A106.08 (8)N2C—Al2—N1C67.95 (7)
N2B—Al1—N2A166.28 (8)N1D—Al2—N1C169.27 (8)
N1A—Al1—Cl1118.73 (6)N2D—Al2—Cl2119.70 (6)
N1B—Al1—Cl1119.03 (6)N2C—Al2—Cl2123.08 (6)
N2B—Al1—Cl195.62 (6)N1D—Al2—Cl295.41 (6)
N2A—Al1—Cl198.02 (6)N1C—Al2—Cl295.31 (6)
Selected geometric parameters (Å, º) for (AlPhCNCy22Cl) top
Cl1—Al12.1855 (9)Al1—N11.9952 (12)
Al1—N21.9260 (12)
N2—Al1—N2i112.73 (8)N1—Al1—N1i167.92 (8)
N2—Al1—N168.04 (5)N2—Al1—Cl1123.64 (4)
N2i—Al1—N1104.92 (5)N1—Al1—Cl196.04 (4)
Symmetry code: (i) x+1, y, z+1/2.
 

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