Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112031952/gz3214sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112031952/gz3214Isup2.hkl | |
Chemdraw file https://doi.org/10.1107/S0108270112031952/gz3214Isup4.cdx |
CCDC reference: 899060
For related literature, see: Allen (2002); Amgoune et al. (2007); Dechy-Cabaret, Martin-Vaca & Bourissou (2004); Du et al. (2009); Guzei & Wendt (2006); Howard et al. (2009); Liu et al. (2000); Ovitt & Coates (1999, 2002); Spassky et al. (1996); Stanford & Dove (2010); Steinhauser et al. (2004); Thomas (2010); Zhong et al. (2003).
A solution of 3,6-di-tert-butyl-1-(isoquinolin-1-yl)-2-naphthol (0.15 g, 0.40 mmol) in toluene (20 ml) was added to a solution of 2.0 M AlMe3 in toluene (0.1 ml, 0.2 mmol). The mixture was left to stir for 4 h. Removal of the volatiles gave a yellow solid. Extraction with toluene (5 ml), concentration to 3 ml and cooling to 278 K yielded small yellow crystals of (II) (0.18 mmol, 0.22 g, 90%). Analysis, calculated for C81H84AlN3O3: C 80.56, H 7.01, N 3.48%; found: C 80.67, H 7.08, N 3.33%. Spectroscopic analysis: 1H NMR (300 MHz, 300 K, C6D6, δ, p.p.m.): 8.18 (s, 3H, aromatic CH), 7.98 (d, 3H, 3J = 6.0 Hz, 3H, aromatic CH), 7.93 (d, 3H, 3J = 1.9 Hz, aromatic CH), 7.62 (d, 3H, 3J = 8.4 Hz, aromatic CH), 7.30–7.09 (m, 9H, aromatic CH), 7.04 (d, 3H, 3J = 6.0 Hz, aromatic CH), 6.91 (d, 3H, 3J = 9.0 Hz, aromatic CH), 6.7 (m, 3H, aromatic CH), 1.94 (s, 27H, CMe3), 1.42 (s, 27H, CMe3); 13C NMR (75 MHz, 300 K, C6D6, δ, p.p.m.): 162.3–114.8 (57 C, Carom), 36.5, 34.4 (CMe3), 31.1, 30.4 (CMe3).
All C-bound H atoms were refined using a riding model, with C—H = 0.95–0.98 Å [Please check added text], and with Uiso(H) = 1.2Ueq(C) for CH groups or 1.5Ueq(C) for methyl groups. The two toluene solvent molecules were constrained such that the aromatic rings were regular hexagons in which the average C≐C bond length was 1.39 Å.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).
[Al(C27H28NO)3]·1.5C7H8 | Z = 2 |
Mr = 1312.70 | F(000) = 1406 |
Triclinic, P1 | Dx = 1.179 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0728 (2) Å | Cell parameters from 60331 reflections |
b = 15.9452 (3) Å | θ = 2.9–27.5° |
c = 19.4565 (4) Å | µ = 0.08 mm−1 |
α = 75.217 (1)° | T = 120 K |
β = 75.262 (1)° | Block, yellow |
γ = 74.200 (1)° | 0.10 × 0.08 × 0.04 mm |
V = 3697.98 (12) Å3 |
Bruker Nonius APEXII CCD area-detector diffractometer on κ-goniostat | 16846 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 11372 reflections with I > 2σ(I) |
10cm confocal mirrors monochromator | Rint = 0.074 |
Detector resolution: 8.25 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ and ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | k = −20→20 |
Tmin = 0.850, Tmax = 0.997 | l = −25→25 |
70540 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0176P)2 + 5.7694P] where P = (Fo2 + 2Fc2)/3 |
16846 reflections | (Δ/σ)max < 0.001 |
915 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
[Al(C27H28NO)3]·1.5C7H8 | γ = 74.200 (1)° |
Mr = 1312.70 | V = 3697.98 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.0728 (2) Å | Mo Kα radiation |
b = 15.9452 (3) Å | µ = 0.08 mm−1 |
c = 19.4565 (4) Å | T = 120 K |
α = 75.217 (1)° | 0.10 × 0.08 × 0.04 mm |
β = 75.262 (1)° |
Bruker Nonius APEXII CCD area-detector diffractometer on κ-goniostat | 16846 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 11372 reflections with I > 2σ(I) |
Tmin = 0.850, Tmax = 0.997 | Rint = 0.074 |
70540 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.52 e Å−3 |
16846 reflections | Δρmin = −0.37 e Å−3 |
915 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | Occ. (<1) | |
Al1 | 0.79485 (6) | 0.07498 (5) | 0.21542 (4) | 0.01929 (16) | |
N1 | 0.81350 (15) | −0.05136 (13) | 0.19670 (11) | 0.0207 (4) | |
O1 | 0.92325 (12) | 0.07448 (11) | 0.14798 (9) | 0.0208 (4) | |
C1 | 1.01245 (18) | 0.01249 (16) | 0.15404 (13) | 0.0192 (5) | |
C2 | 1.11511 (18) | 0.03910 (16) | 0.13199 (13) | 0.0194 (5) | |
C3 | 1.20268 (19) | −0.01984 (16) | 0.15560 (13) | 0.0209 (5) | |
H3 | 1.2707 | −0.0033 | 0.1418 | 0.025* | |
C4 | 1.19593 (18) | −0.10524 (16) | 0.20013 (13) | 0.0205 (5) | |
C5 | 1.09940 (18) | −0.13577 (16) | 0.21254 (13) | 0.0199 (5) | |
C6 | 1.00881 (18) | −0.07736 (16) | 0.18268 (13) | 0.0191 (5) | |
C7 | 1.09617 (19) | −0.21937 (16) | 0.25994 (13) | 0.0211 (5) | |
H7 | 1.0324 | −0.2418 | 0.2703 | 0.025* | |
C8 | 1.18206 (19) | −0.26857 (17) | 0.29106 (14) | 0.0233 (5) | |
H8 | 1.1758 | −0.3237 | 0.3232 | 0.028* | |
C9 | 1.28040 (19) | −0.23986 (17) | 0.27690 (13) | 0.0215 (5) | |
C10 | 1.28441 (19) | −0.15867 (16) | 0.23168 (13) | 0.0215 (5) | |
H10 | 1.3491 | −0.1376 | 0.2212 | 0.026* | |
C11 | 1.1228 (2) | 0.13147 (17) | 0.08573 (14) | 0.0245 (5) | |
C12 | 1.0645 (2) | 0.20481 (18) | 0.12922 (16) | 0.0334 (6) | |
H12A | 0.9872 | 0.2043 | 0.1444 | 0.050* | |
H12B | 1.0732 | 0.2628 | 0.0989 | 0.050* | |
H12C | 1.0959 | 0.1942 | 0.1722 | 0.050* | |
C13 | 1.0733 (2) | 0.14716 (19) | 0.01887 (15) | 0.0333 (6) | |
H13A | 1.1106 | 0.1001 | −0.0086 | 0.050* | |
H13B | 1.0817 | 0.2050 | −0.0118 | 0.050* | |
H13C | 0.9961 | 0.1464 | 0.0343 | 0.050* | |
C14 | 1.2414 (2) | 0.1394 (2) | 0.05839 (18) | 0.0384 (7) | |
H14A | 1.2733 | 0.1365 | 0.0996 | 0.058* | |
H14B | 1.2444 | 0.1962 | 0.0244 | 0.058* | |
H14C | 1.2821 | 0.0904 | 0.0337 | 0.058* | |
C15 | 1.3740 (2) | −0.29659 (17) | 0.31433 (14) | 0.0249 (5) | |
C16 | 1.4797 (2) | −0.2645 (2) | 0.28092 (16) | 0.0325 (6) | |
H16A | 1.5378 | −0.3036 | 0.3050 | 0.049* | |
H16B | 1.4696 | −0.2035 | 0.2873 | 0.049* | |
H16C | 1.4993 | −0.2658 | 0.2291 | 0.049* | |
C17 | 1.3947 (2) | −0.39425 (18) | 0.30809 (17) | 0.0333 (6) | |
H17A | 1.4564 | −0.4293 | 0.3304 | 0.050* | |
H17B | 1.4110 | −0.3981 | 0.2568 | 0.050* | |
H17C | 1.3300 | −0.4177 | 0.3330 | 0.050* | |
C18 | 1.3420 (2) | −0.2897 (2) | 0.39478 (15) | 0.0320 (6) | |
H18A | 1.2745 | −0.3099 | 0.4169 | 0.048* | |
H18B | 1.3315 | −0.2277 | 0.3987 | 0.048* | |
H18C | 1.3998 | −0.3270 | 0.4200 | 0.048* | |
C19 | 0.91083 (18) | −0.10708 (16) | 0.18354 (13) | 0.0191 (5) | |
C20 | 0.91842 (19) | −0.19168 (16) | 0.16552 (13) | 0.0216 (5) | |
C21 | 0.8218 (2) | −0.21953 (17) | 0.17246 (14) | 0.0240 (5) | |
C22 | 0.7216 (2) | −0.15938 (18) | 0.18843 (14) | 0.0265 (6) | |
H22 | 0.6552 | −0.1762 | 0.1936 | 0.032* | |
C23 | 0.72148 (19) | −0.07725 (17) | 0.19630 (13) | 0.0235 (5) | |
H23 | 0.6541 | −0.0353 | 0.2018 | 0.028* | |
C24 | 0.8274 (2) | −0.30369 (18) | 0.15812 (16) | 0.0312 (6) | |
H24 | 0.7627 | −0.3238 | 0.1653 | 0.037* | |
C25 | 0.9251 (2) | −0.35588 (18) | 0.13415 (16) | 0.0313 (6) | |
H25 | 0.9284 | −0.4127 | 0.1255 | 0.038* | |
C26 | 1.0211 (2) | −0.32579 (18) | 0.12214 (15) | 0.0296 (6) | |
H26 | 1.0886 | −0.3613 | 0.1034 | 0.036* | |
C27 | 1.0181 (2) | −0.24578 (17) | 0.13731 (14) | 0.0239 (5) | |
H27 | 1.0836 | −0.2263 | 0.1288 | 0.029* | |
N101 | 0.72309 (16) | 0.13318 (14) | 0.12381 (11) | 0.0214 (4) | |
O101 | 0.77769 (12) | 0.18817 (11) | 0.22871 (9) | 0.0206 (4) | |
C101 | 0.67893 (18) | 0.24122 (16) | 0.23548 (13) | 0.0196 (5) | |
C102 | 0.63538 (19) | 0.28567 (16) | 0.29604 (13) | 0.0220 (5) | |
C103 | 0.5306 (2) | 0.33407 (17) | 0.30276 (14) | 0.0248 (5) | |
H103 | 0.5027 | 0.3658 | 0.3412 | 0.030* | |
C104 | 0.46135 (19) | 0.33949 (16) | 0.25545 (14) | 0.0233 (5) | |
C105 | 0.50497 (19) | 0.29927 (16) | 0.19428 (13) | 0.0217 (5) | |
C106 | 0.61676 (19) | 0.25441 (16) | 0.18303 (13) | 0.0206 (5) | |
C107 | 0.4311 (2) | 0.30089 (17) | 0.15120 (14) | 0.0263 (6) | |
H107 | 0.4571 | 0.2745 | 0.1096 | 0.032* | |
C108 | 0.3232 (2) | 0.33963 (18) | 0.16842 (15) | 0.0277 (6) | |
H108 | 0.2766 | 0.3391 | 0.1383 | 0.033* | |
C109 | 0.2784 (2) | 0.38022 (17) | 0.22903 (14) | 0.0256 (6) | |
C110 | 0.3497 (2) | 0.37995 (17) | 0.27075 (14) | 0.0259 (6) | |
H110 | 0.3227 | 0.4081 | 0.3113 | 0.031* | |
C111 | 0.7017 (2) | 0.27560 (17) | 0.35351 (14) | 0.0243 (5) | |
C112 | 0.6438 (2) | 0.33767 (19) | 0.40696 (15) | 0.0326 (6) | |
H11A | 0.6297 | 0.3993 | 0.3802 | 0.049* | |
H11B | 0.6898 | 0.3315 | 0.4414 | 0.049* | |
H11C | 0.5749 | 0.3219 | 0.4334 | 0.049* | |
C113 | 0.8134 (2) | 0.29730 (19) | 0.31891 (15) | 0.0297 (6) | |
H11D | 0.8532 | 0.2580 | 0.2849 | 0.045* | |
H11E | 0.8543 | 0.2885 | 0.3569 | 0.045* | |
H11F | 0.8039 | 0.3593 | 0.2928 | 0.045* | |
C114 | 0.7137 (2) | 0.17949 (18) | 0.39829 (15) | 0.0293 (6) | |
H11G | 0.6416 | 0.1670 | 0.4197 | 0.044* | |
H11H | 0.7525 | 0.1729 | 0.4370 | 0.044* | |
H11I | 0.7545 | 0.1376 | 0.3666 | 0.044* | |
C115 | 0.1562 (2) | 0.41759 (18) | 0.25217 (15) | 0.0289 (6) | |
C116 | 0.1348 (2) | 0.50850 (19) | 0.27167 (16) | 0.0347 (7) | |
H11J | 0.1681 | 0.5026 | 0.3130 | 0.052* | |
H11K | 0.0565 | 0.5318 | 0.2846 | 0.052* | |
H11L | 0.1663 | 0.5495 | 0.2300 | 0.052* | |
C117 | 0.0946 (2) | 0.4268 (2) | 0.19240 (17) | 0.0374 (7) | |
H11M | 0.1246 | 0.4654 | 0.1482 | 0.056* | |
H11N | 0.0177 | 0.4530 | 0.2083 | 0.056* | |
H11O | 0.1021 | 0.3680 | 0.1824 | 0.056* | |
C118 | 0.1121 (2) | 0.3517 (2) | 0.31856 (18) | 0.0463 (8) | |
H11P | 0.1251 | 0.2936 | 0.3057 | 0.069* | |
H11Q | 0.0340 | 0.3739 | 0.3343 | 0.069* | |
H11R | 0.1491 | 0.3456 | 0.3581 | 0.069* | |
C119 | 0.66822 (18) | 0.21822 (16) | 0.11672 (13) | 0.0211 (5) | |
C120 | 0.66441 (19) | 0.27431 (17) | 0.04623 (13) | 0.0220 (5) | |
C121 | 0.70587 (19) | 0.23521 (17) | −0.01592 (14) | 0.0241 (5) | |
C122 | 0.75517 (19) | 0.14361 (17) | −0.00517 (14) | 0.0246 (5) | |
H122 | 0.7808 | 0.1144 | −0.0452 | 0.030* | |
C123 | 0.76568 (19) | 0.09768 (17) | 0.06243 (14) | 0.0236 (5) | |
H123 | 0.8047 | 0.0375 | 0.0678 | 0.028* | |
C124 | 0.69999 (19) | 0.28941 (18) | −0.08573 (14) | 0.0263 (6) | |
H124 | 0.7232 | 0.2631 | −0.1273 | 0.032* | |
C125 | 0.6611 (2) | 0.37942 (19) | −0.09331 (15) | 0.0292 (6) | |
H125 | 0.6578 | 0.4153 | −0.1402 | 0.035* | |
C126 | 0.6257 (2) | 0.41927 (18) | −0.03197 (15) | 0.0293 (6) | |
H126 | 0.6017 | 0.4821 | −0.0381 | 0.035* | |
C127 | 0.6257 (2) | 0.36827 (17) | 0.03626 (14) | 0.0256 (5) | |
H127 | 0.5997 | 0.3957 | 0.0772 | 0.031* | |
N201 | 0.87696 (15) | 0.02216 (13) | 0.29806 (11) | 0.0197 (4) | |
O201 | 0.66937 (12) | 0.06040 (11) | 0.28366 (9) | 0.0211 (4) | |
C201 | 0.65997 (19) | −0.01451 (16) | 0.33083 (13) | 0.0212 (5) | |
C202 | 0.55507 (19) | −0.03863 (17) | 0.35514 (14) | 0.0242 (5) | |
C203 | 0.5533 (2) | −0.12470 (18) | 0.38974 (14) | 0.0259 (6) | |
H203 | 0.4852 | −0.1409 | 0.4070 | 0.031* | |
C204 | 0.6492 (2) | −0.19119 (17) | 0.40101 (14) | 0.0248 (5) | |
C205 | 0.74845 (19) | −0.16462 (17) | 0.38483 (13) | 0.0228 (5) | |
C206 | 0.74977 (19) | −0.07238 (16) | 0.35701 (13) | 0.0214 (5) | |
C207 | 0.8439 (2) | −0.23242 (17) | 0.39125 (14) | 0.0255 (6) | |
H207 | 0.9122 | −0.2165 | 0.3796 | 0.031* | |
C208 | 0.8395 (2) | −0.31968 (17) | 0.41372 (14) | 0.0266 (6) | |
H208 | 0.9051 | −0.3634 | 0.4164 | 0.032* | |
C209 | 0.7397 (2) | −0.34748 (17) | 0.43326 (14) | 0.0260 (6) | |
C210 | 0.6469 (2) | −0.28247 (17) | 0.42666 (14) | 0.0260 (6) | |
H210 | 0.5790 | −0.2992 | 0.4397 | 0.031* | |
C211 | 0.45107 (19) | 0.03134 (18) | 0.34228 (15) | 0.0276 (6) | |
C212 | 0.3490 (2) | −0.00548 (19) | 0.37958 (17) | 0.0353 (7) | |
H21A | 0.3481 | −0.0259 | 0.4317 | 0.053* | |
H21B | 0.3496 | −0.0555 | 0.3587 | 0.053* | |
H21C | 0.2842 | 0.0414 | 0.3721 | 0.053* | |
C213 | 0.4435 (2) | 0.11224 (19) | 0.37420 (17) | 0.0353 (7) | |
H21D | 0.4419 | 0.0933 | 0.4264 | 0.053* | |
H21E | 0.3772 | 0.1568 | 0.3659 | 0.053* | |
H21F | 0.5068 | 0.1381 | 0.3506 | 0.053* | |
C214 | 0.4480 (2) | 0.0616 (2) | 0.26081 (16) | 0.0346 (7) | |
H21G | 0.3802 | 0.1052 | 0.2545 | 0.052* | |
H21H | 0.4523 | 0.0101 | 0.2407 | 0.052* | |
H21I | 0.5097 | 0.0889 | 0.2355 | 0.052* | |
C215 | 0.7421 (2) | −0.44679 (19) | 0.45816 (17) | 0.0342 (7) | |
C216 | 0.6292 (2) | −0.46525 (19) | 0.48021 (17) | 0.0371 (7) | |
H21J | 0.5874 | −0.4354 | 0.5202 | 0.056* | |
H21K | 0.6345 | −0.5295 | 0.4960 | 0.056* | |
H21L | 0.5928 | −0.4428 | 0.4388 | 0.056* | |
C217 | 0.7983 (3) | −0.4841 (2) | 0.5235 (2) | 0.0549 (10) | |
H21M | 0.7567 | −0.4545 | 0.5637 | 0.082* | |
H21N | 0.8718 | −0.4733 | 0.5099 | 0.082* | |
H21O | 0.8021 | −0.5482 | 0.5387 | 0.082* | |
C218 | 0.8066 (3) | −0.4944 (2) | 0.3963 (2) | 0.0572 (11) | |
H21P | 0.8117 | −0.5586 | 0.4128 | 0.086* | |
H21Q | 0.8796 | −0.4826 | 0.3815 | 0.086* | |
H21R | 0.7698 | −0.4726 | 0.3551 | 0.086* | |
C219 | 0.84518 (18) | −0.03871 (16) | 0.35493 (13) | 0.0200 (5) | |
C220 | 0.90097 (19) | −0.06855 (17) | 0.41487 (14) | 0.0238 (5) | |
C221 | 1.0023 (2) | −0.04704 (17) | 0.40523 (14) | 0.0255 (5) | |
C222 | 1.0337 (2) | 0.01675 (17) | 0.34309 (14) | 0.0251 (5) | |
H222 | 1.1005 | 0.0340 | 0.3353 | 0.030* | |
C223 | 0.96720 (19) | 0.05262 (17) | 0.29521 (14) | 0.0219 (5) | |
H223 | 0.9834 | 0.1013 | 0.2577 | 0.026* | |
C224 | 1.0654 (2) | −0.08487 (19) | 0.45984 (16) | 0.0331 (6) | |
H224 | 1.1360 | −0.0745 | 0.4521 | 0.040* | |
C225 | 1.0249 (2) | −0.1359 (2) | 0.52305 (16) | 0.0358 (7) | |
H225 | 1.0682 | −0.1624 | 0.5588 | 0.043* | |
C226 | 0.9194 (2) | −0.14977 (19) | 0.53581 (15) | 0.0330 (6) | |
H226 | 0.8901 | −0.1823 | 0.5814 | 0.040* | |
C227 | 0.8586 (2) | −0.11699 (17) | 0.48338 (14) | 0.0265 (6) | |
H227 | 0.7873 | −0.1267 | 0.4928 | 0.032* | |
C301 | 0.9026 (4) | 0.4213 (3) | 0.0501 (3) | 0.0852 (15) | |
H30A | 0.8855 | 0.3663 | 0.0474 | 0.128* | |
H30B | 0.9487 | 0.4082 | 0.0859 | 0.128* | |
H30C | 0.9409 | 0.4471 | 0.0025 | 0.128* | |
C302 | 0.80085 (15) | 0.48543 (14) | 0.07232 (12) | 0.0497 (9) | |
C303 | 0.7367 (2) | 0.46572 (13) | 0.14065 (11) | 0.0562 (10) | |
H303 | 0.7594 | 0.4122 | 0.1734 | 0.067* | |
C304 | 0.63942 (19) | 0.52424 (17) | 0.16104 (10) | 0.0629 (11) | |
H304 | 0.5956 | 0.5108 | 0.2077 | 0.075* | |
C305 | 0.60623 (15) | 0.60248 (15) | 0.11309 (13) | 0.0566 (10) | |
H305 | 0.5397 | 0.6425 | 0.1270 | 0.068* | |
C306 | 0.67035 (18) | 0.62220 (12) | 0.04476 (12) | 0.0510 (9) | |
H306 | 0.6477 | 0.6757 | 0.0120 | 0.061* | |
C307 | 0.76766 (16) | 0.56367 (15) | 0.02438 (9) | 0.0480 (8) | |
H307 | 0.8115 | 0.5771 | −0.0223 | 0.058* | |
C401 | 0.4916 (8) | 0.8509 (8) | 0.0559 (6) | 0.045 (2) | 0.50 |
H40A | 0.5536 | 0.8234 | 0.0799 | 0.068* | 0.50 |
H40B | 0.4948 | 0.8185 | 0.0187 | 0.068* | 0.50 |
H40C | 0.4240 | 0.8490 | 0.0919 | 0.068* | 0.50 |
C402 | 0.4953 (4) | 0.9453 (3) | 0.0215 (3) | 0.0356 (14) | 0.50 |
C403 | 0.5125 (4) | 0.9987 (4) | 0.0619 (2) | 0.038 (2) | 0.50 |
H403 | 0.5198 | 0.9754 | 0.1109 | 0.046* | 0.50 |
C404 | 0.5189 (4) | 1.0863 (4) | 0.0306 (4) | 0.0517 (19) | 0.50 |
H404 | 0.5306 | 1.1229 | 0.0583 | 0.062* | 0.50 |
C405 | 0.5081 (4) | 1.1205 (3) | −0.0411 (4) | 0.063 (4) | 0.50 |
H405 | 0.5125 | 1.1803 | −0.0624 | 0.075* | 0.50 |
C406 | 0.4910 (4) | 1.0670 (5) | −0.0815 (2) | 0.053 (2) | 0.50 |
H406 | 0.4836 | 1.0903 | −0.1305 | 0.064* | 0.50 |
C407 | 0.4845 (4) | 0.9794 (5) | −0.0502 (3) | 0.041 (2) | 0.50 |
H407 | 0.4728 | 0.9428 | −0.0778 | 0.049* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Al1 | 0.0171 (3) | 0.0206 (4) | 0.0199 (4) | −0.0027 (3) | −0.0043 (3) | −0.0046 (3) |
N1 | 0.0188 (10) | 0.0231 (11) | 0.0195 (11) | −0.0034 (8) | −0.0049 (8) | −0.0034 (9) |
O1 | 0.0188 (8) | 0.0202 (9) | 0.0212 (9) | −0.0001 (6) | −0.0040 (7) | −0.0046 (7) |
C1 | 0.0191 (11) | 0.0211 (12) | 0.0178 (12) | −0.0017 (9) | −0.0056 (9) | −0.0056 (10) |
C2 | 0.0216 (12) | 0.0205 (12) | 0.0174 (12) | −0.0052 (9) | −0.0024 (9) | −0.0070 (10) |
C3 | 0.0184 (11) | 0.0231 (13) | 0.0228 (13) | −0.0067 (9) | −0.0029 (9) | −0.0065 (10) |
C4 | 0.0192 (11) | 0.0226 (13) | 0.0204 (13) | −0.0031 (9) | −0.0045 (9) | −0.0065 (10) |
C5 | 0.0198 (11) | 0.0208 (12) | 0.0195 (12) | −0.0015 (9) | −0.0028 (9) | −0.0090 (10) |
C6 | 0.0187 (11) | 0.0212 (12) | 0.0188 (12) | −0.0034 (9) | −0.0053 (9) | −0.0058 (10) |
C7 | 0.0209 (12) | 0.0231 (13) | 0.0217 (13) | −0.0070 (9) | −0.0051 (9) | −0.0056 (10) |
C8 | 0.0256 (13) | 0.0222 (13) | 0.0224 (13) | −0.0057 (10) | −0.0059 (10) | −0.0035 (10) |
C9 | 0.0198 (12) | 0.0266 (13) | 0.0187 (12) | −0.0037 (10) | −0.0070 (9) | −0.0042 (10) |
C10 | 0.0170 (11) | 0.0258 (13) | 0.0231 (13) | −0.0046 (9) | −0.0033 (9) | −0.0082 (11) |
C11 | 0.0232 (12) | 0.0224 (13) | 0.0268 (14) | −0.0080 (10) | −0.0050 (10) | 0.0002 (11) |
C12 | 0.0382 (16) | 0.0221 (14) | 0.0385 (17) | −0.0088 (11) | −0.0068 (13) | −0.0023 (12) |
C13 | 0.0366 (15) | 0.0323 (16) | 0.0275 (15) | −0.0098 (12) | −0.0078 (12) | 0.0040 (12) |
C14 | 0.0271 (14) | 0.0313 (16) | 0.0480 (19) | −0.0107 (12) | −0.0031 (13) | 0.0079 (14) |
C15 | 0.0229 (12) | 0.0271 (14) | 0.0249 (14) | −0.0049 (10) | −0.0084 (10) | −0.0024 (11) |
C16 | 0.0247 (13) | 0.0373 (16) | 0.0327 (16) | −0.0052 (11) | −0.0099 (11) | 0.0004 (13) |
C17 | 0.0294 (14) | 0.0295 (15) | 0.0410 (17) | −0.0008 (11) | −0.0142 (12) | −0.0060 (13) |
C18 | 0.0341 (15) | 0.0376 (16) | 0.0248 (14) | −0.0090 (12) | −0.0121 (11) | 0.0002 (12) |
C19 | 0.0212 (12) | 0.0216 (12) | 0.0147 (12) | −0.0044 (9) | −0.0071 (9) | −0.0008 (10) |
C20 | 0.0251 (12) | 0.0227 (13) | 0.0173 (12) | −0.0052 (10) | −0.0065 (10) | −0.0028 (10) |
C21 | 0.0286 (13) | 0.0238 (13) | 0.0228 (13) | −0.0095 (10) | −0.0098 (10) | −0.0017 (11) |
C22 | 0.0229 (13) | 0.0311 (15) | 0.0289 (14) | −0.0109 (10) | −0.0054 (10) | −0.0064 (12) |
C23 | 0.0185 (12) | 0.0308 (14) | 0.0223 (13) | −0.0057 (10) | −0.0052 (10) | −0.0059 (11) |
C24 | 0.0338 (15) | 0.0272 (15) | 0.0369 (16) | −0.0113 (11) | −0.0130 (12) | −0.0031 (12) |
C25 | 0.0436 (16) | 0.0189 (13) | 0.0387 (17) | −0.0074 (11) | −0.0184 (13) | −0.0076 (12) |
C26 | 0.0334 (14) | 0.0255 (14) | 0.0318 (15) | −0.0014 (11) | −0.0136 (12) | −0.0077 (12) |
C27 | 0.0261 (13) | 0.0238 (13) | 0.0239 (14) | −0.0051 (10) | −0.0099 (10) | −0.0038 (11) |
N101 | 0.0205 (10) | 0.0249 (11) | 0.0193 (11) | −0.0023 (8) | −0.0055 (8) | −0.0067 (9) |
O101 | 0.0180 (8) | 0.0221 (9) | 0.0214 (9) | −0.0013 (6) | −0.0053 (7) | −0.0059 (7) |
C101 | 0.0207 (12) | 0.0181 (12) | 0.0195 (12) | −0.0038 (9) | −0.0031 (9) | −0.0041 (10) |
C102 | 0.0242 (12) | 0.0217 (13) | 0.0215 (13) | −0.0050 (10) | −0.0071 (10) | −0.0044 (10) |
C103 | 0.0277 (13) | 0.0260 (14) | 0.0218 (13) | −0.0035 (10) | −0.0054 (10) | −0.0087 (11) |
C104 | 0.0210 (12) | 0.0220 (13) | 0.0250 (14) | −0.0013 (10) | −0.0044 (10) | −0.0051 (11) |
C105 | 0.0230 (12) | 0.0209 (13) | 0.0204 (13) | −0.0009 (9) | −0.0063 (10) | −0.0050 (10) |
C106 | 0.0211 (12) | 0.0193 (12) | 0.0196 (12) | −0.0012 (9) | −0.0030 (9) | −0.0052 (10) |
C107 | 0.0258 (13) | 0.0300 (14) | 0.0226 (14) | 0.0001 (10) | −0.0053 (10) | −0.0103 (11) |
C108 | 0.0236 (13) | 0.0315 (15) | 0.0283 (14) | −0.0015 (10) | −0.0095 (11) | −0.0074 (12) |
C109 | 0.0223 (12) | 0.0219 (13) | 0.0275 (14) | 0.0013 (10) | −0.0046 (10) | −0.0031 (11) |
C110 | 0.0268 (13) | 0.0252 (14) | 0.0244 (14) | 0.0012 (10) | −0.0040 (10) | −0.0111 (11) |
C111 | 0.0240 (12) | 0.0291 (14) | 0.0227 (13) | −0.0039 (10) | −0.0064 (10) | −0.0105 (11) |
C112 | 0.0361 (15) | 0.0382 (16) | 0.0285 (15) | −0.0023 (12) | −0.0093 (12) | −0.0186 (13) |
C113 | 0.0276 (14) | 0.0369 (16) | 0.0302 (15) | −0.0088 (11) | −0.0097 (11) | −0.0110 (12) |
C114 | 0.0321 (14) | 0.0317 (15) | 0.0267 (15) | −0.0054 (11) | −0.0107 (11) | −0.0072 (12) |
C115 | 0.0231 (13) | 0.0295 (15) | 0.0310 (15) | −0.0018 (10) | −0.0038 (11) | −0.0066 (12) |
C116 | 0.0283 (14) | 0.0363 (16) | 0.0366 (17) | 0.0015 (12) | −0.0057 (12) | −0.0122 (13) |
C117 | 0.0258 (14) | 0.0400 (17) | 0.0471 (19) | 0.0027 (12) | −0.0124 (13) | −0.0157 (14) |
C118 | 0.0327 (16) | 0.0441 (19) | 0.049 (2) | −0.0078 (13) | −0.0006 (14) | 0.0052 (16) |
C119 | 0.0173 (11) | 0.0240 (13) | 0.0228 (13) | −0.0008 (9) | −0.0059 (9) | −0.0082 (10) |
C120 | 0.0188 (12) | 0.0261 (13) | 0.0211 (13) | −0.0025 (10) | −0.0061 (9) | −0.0054 (10) |
C121 | 0.0204 (12) | 0.0313 (14) | 0.0223 (13) | −0.0041 (10) | −0.0045 (10) | −0.0097 (11) |
C122 | 0.0231 (12) | 0.0313 (14) | 0.0219 (13) | −0.0023 (10) | −0.0056 (10) | −0.0126 (11) |
C123 | 0.0242 (12) | 0.0233 (13) | 0.0234 (13) | −0.0005 (10) | −0.0067 (10) | −0.0081 (11) |
C124 | 0.0217 (12) | 0.0361 (15) | 0.0202 (13) | −0.0027 (11) | −0.0040 (10) | −0.0082 (11) |
C125 | 0.0241 (13) | 0.0349 (15) | 0.0236 (14) | −0.0037 (11) | −0.0047 (10) | −0.0004 (12) |
C126 | 0.0291 (14) | 0.0271 (14) | 0.0296 (15) | −0.0025 (11) | −0.0077 (11) | −0.0042 (12) |
C127 | 0.0252 (13) | 0.0274 (14) | 0.0248 (14) | −0.0014 (10) | −0.0072 (10) | −0.0088 (11) |
N201 | 0.0180 (10) | 0.0214 (11) | 0.0195 (11) | −0.0029 (8) | −0.0034 (8) | −0.0055 (9) |
O201 | 0.0186 (8) | 0.0229 (9) | 0.0212 (9) | −0.0039 (7) | −0.0042 (7) | −0.0035 (7) |
C201 | 0.0234 (12) | 0.0226 (13) | 0.0195 (13) | −0.0067 (10) | −0.0038 (10) | −0.0062 (10) |
C202 | 0.0193 (12) | 0.0287 (14) | 0.0255 (14) | −0.0057 (10) | −0.0042 (10) | −0.0068 (11) |
C203 | 0.0212 (12) | 0.0335 (15) | 0.0260 (14) | −0.0101 (10) | −0.0011 (10) | −0.0105 (12) |
C204 | 0.0258 (13) | 0.0254 (14) | 0.0242 (14) | −0.0063 (10) | −0.0048 (10) | −0.0059 (11) |
C205 | 0.0233 (12) | 0.0276 (14) | 0.0181 (13) | −0.0059 (10) | −0.0038 (10) | −0.0057 (10) |
C206 | 0.0201 (12) | 0.0247 (13) | 0.0189 (13) | −0.0064 (10) | −0.0022 (9) | −0.0038 (10) |
C207 | 0.0226 (12) | 0.0288 (14) | 0.0256 (14) | −0.0072 (10) | −0.0038 (10) | −0.0054 (11) |
C208 | 0.0267 (13) | 0.0249 (14) | 0.0269 (14) | −0.0026 (10) | −0.0056 (11) | −0.0059 (11) |
C209 | 0.0295 (13) | 0.0247 (14) | 0.0239 (14) | −0.0077 (10) | −0.0022 (10) | −0.0062 (11) |
C210 | 0.0257 (13) | 0.0269 (14) | 0.0280 (14) | −0.0112 (10) | −0.0018 (10) | −0.0075 (11) |
C211 | 0.0182 (12) | 0.0295 (14) | 0.0340 (15) | −0.0054 (10) | −0.0050 (10) | −0.0046 (12) |
C212 | 0.0222 (13) | 0.0344 (16) | 0.0462 (18) | −0.0056 (11) | −0.0012 (12) | −0.0088 (14) |
C213 | 0.0241 (14) | 0.0324 (16) | 0.0488 (19) | −0.0038 (11) | −0.0020 (12) | −0.0148 (14) |
C214 | 0.0239 (13) | 0.0395 (17) | 0.0396 (17) | −0.0036 (12) | −0.0117 (12) | −0.0050 (13) |
C215 | 0.0328 (15) | 0.0263 (15) | 0.0431 (18) | −0.0081 (11) | −0.0029 (13) | −0.0091 (13) |
C216 | 0.0378 (16) | 0.0250 (15) | 0.0455 (18) | −0.0098 (12) | 0.0018 (13) | −0.0087 (13) |
C217 | 0.059 (2) | 0.0387 (19) | 0.066 (2) | −0.0211 (16) | −0.0258 (18) | 0.0149 (17) |
C218 | 0.051 (2) | 0.0401 (19) | 0.079 (3) | −0.0191 (16) | 0.0224 (18) | −0.0340 (19) |
C219 | 0.0198 (11) | 0.0203 (12) | 0.0193 (12) | −0.0012 (9) | −0.0040 (9) | −0.0064 (10) |
C220 | 0.0235 (12) | 0.0235 (13) | 0.0242 (14) | −0.0020 (10) | −0.0059 (10) | −0.0069 (11) |
C221 | 0.0265 (13) | 0.0290 (14) | 0.0232 (13) | −0.0051 (10) | −0.0096 (10) | −0.0055 (11) |
C222 | 0.0231 (12) | 0.0313 (14) | 0.0235 (14) | −0.0088 (10) | −0.0058 (10) | −0.0060 (11) |
C223 | 0.0221 (12) | 0.0234 (13) | 0.0215 (13) | −0.0071 (10) | −0.0025 (10) | −0.0062 (10) |
C224 | 0.0305 (14) | 0.0392 (17) | 0.0331 (16) | −0.0084 (12) | −0.0143 (12) | −0.0047 (13) |
C225 | 0.0381 (16) | 0.0393 (17) | 0.0313 (16) | −0.0040 (13) | −0.0191 (13) | −0.0018 (13) |
C226 | 0.0450 (17) | 0.0325 (16) | 0.0210 (14) | −0.0100 (12) | −0.0086 (12) | −0.0009 (12) |
C227 | 0.0287 (13) | 0.0270 (14) | 0.0234 (14) | −0.0076 (11) | −0.0042 (10) | −0.0039 (11) |
C301 | 0.089 (3) | 0.076 (3) | 0.098 (4) | 0.015 (2) | −0.043 (3) | −0.043 (3) |
C302 | 0.056 (2) | 0.052 (2) | 0.052 (2) | −0.0086 (16) | −0.0236 (17) | −0.0192 (18) |
C303 | 0.078 (3) | 0.048 (2) | 0.052 (2) | −0.0260 (19) | −0.029 (2) | 0.0012 (18) |
C304 | 0.065 (3) | 0.075 (3) | 0.054 (2) | −0.033 (2) | −0.0050 (19) | −0.012 (2) |
C305 | 0.0426 (19) | 0.068 (3) | 0.068 (3) | −0.0147 (17) | −0.0050 (18) | −0.031 (2) |
C306 | 0.053 (2) | 0.055 (2) | 0.051 (2) | −0.0148 (17) | −0.0163 (17) | −0.0106 (18) |
C307 | 0.052 (2) | 0.059 (2) | 0.0331 (18) | −0.0140 (17) | −0.0123 (15) | −0.0035 (16) |
C401 | 0.038 (5) | 0.052 (6) | 0.041 (4) | −0.008 (3) | 0.001 (3) | −0.014 (5) |
C402 | 0.021 (3) | 0.044 (4) | 0.041 (4) | −0.006 (3) | −0.008 (2) | −0.006 (3) |
C403 | 0.017 (4) | 0.052 (6) | 0.043 (5) | 0.002 (3) | −0.009 (3) | −0.013 (4) |
C404 | 0.026 (3) | 0.050 (4) | 0.086 (6) | −0.009 (3) | −0.010 (3) | −0.026 (4) |
C405 | 0.019 (4) | 0.057 (9) | 0.096 (10) | −0.015 (4) | −0.002 (4) | 0.010 (6) |
C406 | 0.027 (3) | 0.059 (5) | 0.059 (5) | −0.009 (3) | −0.006 (3) | 0.011 (4) |
C407 | 0.034 (5) | 0.059 (6) | 0.036 (4) | −0.013 (4) | −0.015 (4) | −0.007 (4) |
Al1—N1 | 2.077 (2) | C118—H11P | 0.9800 |
Al1—N101 | 2.110 (2) | C118—H11Q | 0.9800 |
Al1—N201 | 2.035 (2) | C118—H11R | 0.9800 |
Al1—O1 | 1.8485 (17) | C119—C120 | 1.438 (3) |
Al1—O101 | 1.8338 (18) | C120—C121 | 1.419 (3) |
Al1—O201 | 1.8573 (17) | C120—C127 | 1.424 (4) |
N1—C19 | 1.345 (3) | C121—C122 | 1.412 (4) |
N1—C23 | 1.376 (3) | C121—C124 | 1.420 (4) |
O1—C1 | 1.317 (3) | C122—C123 | 1.353 (4) |
C1—C6 | 1.408 (3) | C122—H122 | 0.9500 |
C1—C2 | 1.445 (3) | C123—H123 | 0.9500 |
C2—C3 | 1.366 (3) | C124—C125 | 1.369 (4) |
C2—C11 | 1.532 (3) | C124—H124 | 0.9500 |
C3—C4 | 1.427 (3) | C125—C126 | 1.410 (4) |
C3—H3 | 0.9500 | C125—H125 | 0.9500 |
C4—C10 | 1.414 (3) | C126—C127 | 1.368 (4) |
C4—C5 | 1.417 (3) | C126—H126 | 0.9500 |
C5—C7 | 1.419 (3) | C127—H127 | 0.9500 |
C5—C6 | 1.442 (3) | N201—C219 | 1.333 (3) |
C6—C19 | 1.477 (3) | N201—C223 | 1.377 (3) |
C7—C8 | 1.366 (3) | O201—C201 | 1.322 (3) |
C7—H7 | 0.9500 | C201—C206 | 1.401 (3) |
C8—C9 | 1.419 (3) | C201—C202 | 1.455 (3) |
C8—H8 | 0.9500 | C202—C203 | 1.369 (4) |
C9—C10 | 1.373 (3) | C202—C211 | 1.536 (3) |
C9—C15 | 1.536 (3) | C203—C204 | 1.429 (4) |
C10—H10 | 0.9500 | C203—H203 | 0.9500 |
C11—C13 | 1.532 (4) | C204—C205 | 1.409 (3) |
C11—C14 | 1.535 (3) | C204—C210 | 1.419 (4) |
C11—C12 | 1.535 (4) | C205—C207 | 1.421 (3) |
C12—H12A | 0.9800 | C205—C206 | 1.435 (3) |
C12—H12B | 0.9800 | C206—C219 | 1.474 (3) |
C12—H12C | 0.9800 | C207—C208 | 1.361 (4) |
C13—H13A | 0.9800 | C207—H207 | 0.9500 |
C13—H13B | 0.9800 | C208—C209 | 1.421 (4) |
C13—H13C | 0.9800 | C208—H208 | 0.9500 |
C14—H14A | 0.9800 | C209—C210 | 1.375 (4) |
C14—H14B | 0.9800 | C209—C215 | 1.527 (4) |
C14—H14C | 0.9800 | C210—H210 | 0.9500 |
C15—C16 | 1.534 (4) | C211—C213 | 1.539 (4) |
C15—C17 | 1.537 (4) | C211—C212 | 1.539 (3) |
C15—C18 | 1.539 (4) | C211—C214 | 1.542 (4) |
C16—H16A | 0.9800 | C212—H21A | 0.9800 |
C16—H16B | 0.9800 | C212—H21B | 0.9800 |
C16—H16C | 0.9800 | C212—H21C | 0.9800 |
C17—H17A | 0.9800 | C213—H21D | 0.9800 |
C17—H17B | 0.9800 | C213—H21E | 0.9800 |
C17—H17C | 0.9800 | C213—H21F | 0.9800 |
C18—H18A | 0.9800 | C214—H21G | 0.9800 |
C18—H18B | 0.9800 | C214—H21H | 0.9800 |
C18—H18C | 0.9800 | C214—H21I | 0.9800 |
C19—C20 | 1.450 (3) | C215—C216 | 1.515 (4) |
C20—C21 | 1.414 (3) | C215—C218 | 1.528 (4) |
C20—C27 | 1.418 (3) | C215—C217 | 1.537 (4) |
C21—C22 | 1.412 (4) | C216—H21J | 0.9800 |
C21—C24 | 1.418 (4) | C216—H21K | 0.9800 |
C22—C23 | 1.356 (4) | C216—H21L | 0.9800 |
C22—H22 | 0.9500 | C217—H21M | 0.9800 |
C23—H23 | 0.9500 | C217—H21N | 0.9800 |
C24—C25 | 1.362 (4) | C217—H21O | 0.9800 |
C24—H24 | 0.9500 | C218—H21P | 0.9800 |
C25—C26 | 1.409 (4) | C218—H21Q | 0.9800 |
C25—H25 | 0.9500 | C218—H21R | 0.9800 |
C26—C27 | 1.369 (4) | C219—C220 | 1.442 (3) |
C26—H26 | 0.9500 | C220—C221 | 1.413 (3) |
C27—H27 | 0.9500 | C220—C227 | 1.419 (4) |
N101—C119 | 1.341 (3) | C221—C222 | 1.418 (4) |
N101—C123 | 1.375 (3) | C221—C224 | 1.421 (4) |
O101—C101 | 1.332 (3) | C222—C223 | 1.349 (3) |
C101—C106 | 1.402 (3) | C222—H222 | 0.9500 |
C101—C102 | 1.442 (3) | C223—H223 | 0.9500 |
C102—C103 | 1.369 (3) | C224—C225 | 1.359 (4) |
C102—C111 | 1.534 (3) | C224—H224 | 0.9500 |
C103—C104 | 1.420 (3) | C225—C226 | 1.407 (4) |
C103—H103 | 0.9500 | C225—H225 | 0.9500 |
C104—C105 | 1.413 (3) | C226—C227 | 1.364 (4) |
C104—C110 | 1.414 (3) | C226—H226 | 0.9500 |
C105—C107 | 1.423 (3) | C227—H227 | 0.9500 |
C105—C106 | 1.429 (3) | C301—C302 | 1.481 (4) |
C106—C119 | 1.475 (3) | C301—H30A | 0.9800 |
C107—C108 | 1.369 (3) | C301—H30B | 0.9800 |
C107—H107 | 0.9500 | C301—H30C | 0.9800 |
C108—C109 | 1.409 (4) | C302—C303 | 1.3900 |
C108—H108 | 0.9500 | C302—C307 | 1.3900 |
C109—C110 | 1.382 (4) | C303—C304 | 1.3900 |
C109—C115 | 1.537 (3) | C303—H303 | 0.9500 |
C110—H110 | 0.9500 | C304—C305 | 1.3900 |
C111—C112 | 1.533 (4) | C304—H304 | 0.9500 |
C111—C113 | 1.537 (3) | C305—C306 | 1.3900 |
C111—C114 | 1.546 (4) | C305—H305 | 0.9500 |
C112—H11A | 0.9800 | C306—C307 | 1.3900 |
C112—H11B | 0.9800 | C306—H306 | 0.9500 |
C112—H11C | 0.9800 | C307—H307 | 0.9500 |
C113—H11D | 0.9800 | C401—C402 | 1.491 (12) |
C113—H11E | 0.9800 | C401—H40A | 0.9800 |
C113—H11F | 0.9800 | C401—H40B | 0.9800 |
C114—H11G | 0.9800 | C401—H40C | 0.9800 |
C114—H11H | 0.9800 | C402—C403 | 1.3900 |
C114—H11I | 0.9800 | C402—C407 | 1.3900 |
C115—C116 | 1.526 (4) | C403—C404 | 1.3900 |
C115—C117 | 1.531 (4) | C403—H403 | 0.9500 |
C115—C118 | 1.537 (4) | C404—C405 | 1.3900 |
C116—H11J | 0.9800 | C404—H404 | 0.9500 |
C116—H11K | 0.9800 | C405—C406 | 1.3900 |
C116—H11L | 0.9800 | C405—H405 | 0.9500 |
C117—H11M | 0.9800 | C406—C407 | 1.3900 |
C117—H11N | 0.9800 | C406—H406 | 0.9500 |
C117—H11O | 0.9800 | C407—H407 | 0.9500 |
O101—Al1—O1 | 95.49 (8) | H11J—C116—H11L | 109.5 |
O101—Al1—O201 | 91.48 (8) | H11K—C116—H11L | 109.5 |
O1—Al1—O201 | 172.89 (9) | C115—C117—H11M | 109.5 |
O101—Al1—N201 | 91.57 (8) | C115—C117—H11N | 109.5 |
O1—Al1—N201 | 91.24 (8) | H11M—C117—H11N | 109.5 |
O101—Al1—N1 | 178.01 (9) | C115—C117—H11O | 109.5 |
N1—Al1—O1 | 83.72 (8) | H11M—C117—H11O | 109.5 |
O201—Al1—N1 | 89.37 (8) | H11N—C117—H11O | 109.5 |
N201—Al1—N1 | 90.27 (8) | C115—C118—H11P | 109.5 |
N101—Al1—O101 | 87.22 (8) | C115—C118—H11Q | 109.5 |
N201—Al1—O201 | 87.13 (8) | H11P—C118—H11Q | 109.5 |
O1—Al1—N101 | 83.70 (8) | C115—C118—H11R | 109.5 |
O201—Al1—N101 | 98.09 (8) | H11P—C118—H11R | 109.5 |
N201—Al1—N101 | 174.66 (9) | H11Q—C118—H11R | 109.5 |
N1—Al1—N101 | 90.88 (8) | N101—C119—C120 | 120.9 (2) |
C19—N1—C23 | 119.4 (2) | N101—C119—C106 | 118.4 (2) |
C19—N1—Al1 | 122.90 (16) | C120—C119—C106 | 120.6 (2) |
C23—N1—Al1 | 117.66 (16) | C121—C120—C127 | 118.7 (2) |
C1—O1—Al1 | 123.63 (15) | C121—C120—C119 | 118.8 (2) |
O1—C1—C6 | 121.4 (2) | C127—C120—C119 | 122.4 (2) |
O1—C1—C2 | 118.3 (2) | C122—C121—C120 | 117.7 (2) |
C6—C1—C2 | 120.3 (2) | C122—C121—C124 | 122.9 (2) |
C3—C2—C1 | 117.6 (2) | C120—C121—C124 | 119.4 (2) |
C3—C2—C11 | 122.1 (2) | C123—C122—C121 | 119.6 (2) |
C1—C2—C11 | 120.3 (2) | C123—C122—H122 | 120.2 |
C2—C3—C4 | 122.6 (2) | C121—C122—H122 | 120.2 |
C2—C3—H3 | 118.7 | C122—C123—N101 | 123.8 (2) |
C4—C3—H3 | 118.7 | C122—C123—H123 | 118.1 |
C10—C4—C5 | 120.4 (2) | N101—C123—H123 | 118.1 |
C10—C4—C3 | 120.4 (2) | C125—C124—C121 | 120.3 (2) |
C5—C4—C3 | 119.3 (2) | C125—C124—H124 | 119.9 |
C4—C5—C7 | 116.4 (2) | C121—C124—H124 | 119.9 |
C4—C5—C6 | 118.7 (2) | C124—C125—C126 | 120.5 (2) |
C7—C5—C6 | 124.6 (2) | C124—C125—H125 | 119.8 |
C1—C6—C5 | 118.5 (2) | C126—C125—H125 | 119.8 |
C1—C6—C19 | 118.7 (2) | C127—C126—C125 | 120.6 (3) |
C5—C6—C19 | 122.7 (2) | C127—C126—H126 | 119.7 |
C8—C7—C5 | 121.9 (2) | C125—C126—H126 | 119.7 |
C8—C7—H7 | 119.0 | C126—C127—C120 | 120.4 (2) |
C5—C7—H7 | 119.0 | C126—C127—H127 | 119.8 |
C7—C8—C9 | 122.0 (2) | C120—C127—H127 | 119.8 |
C7—C8—H8 | 119.0 | C219—N201—C223 | 119.4 (2) |
C9—C8—H8 | 119.0 | C219—N201—Al1 | 122.53 (16) |
C10—C9—C8 | 116.7 (2) | C223—N201—Al1 | 118.06 (16) |
C10—C9—C15 | 123.0 (2) | C201—O201—Al1 | 123.51 (15) |
C8—C9—C15 | 120.1 (2) | O201—C201—C206 | 121.3 (2) |
C9—C10—C4 | 122.5 (2) | O201—C201—C202 | 119.7 (2) |
C9—C10—H10 | 118.7 | C206—C201—C202 | 119.1 (2) |
C4—C10—H10 | 118.7 | C203—C202—C201 | 117.6 (2) |
C13—C11—C2 | 109.7 (2) | C203—C202—C211 | 122.1 (2) |
C13—C11—C14 | 107.2 (2) | C201—C202—C211 | 120.2 (2) |
C2—C11—C14 | 111.1 (2) | C202—C203—C204 | 123.0 (2) |
C13—C11—C12 | 109.8 (2) | C202—C203—H203 | 118.5 |
C2—C11—C12 | 111.4 (2) | C204—C203—H203 | 118.5 |
C14—C11—C12 | 107.6 (2) | C205—C204—C210 | 119.8 (2) |
C11—C12—H12A | 109.5 | C205—C204—C203 | 118.5 (2) |
C11—C12—H12B | 109.5 | C210—C204—C203 | 121.8 (2) |
H12A—C12—H12B | 109.5 | C204—C205—C207 | 117.6 (2) |
C11—C12—H12C | 109.5 | C204—C205—C206 | 119.0 (2) |
H12A—C12—H12C | 109.5 | C207—C205—C206 | 123.2 (2) |
H12B—C12—H12C | 109.5 | C201—C206—C205 | 119.4 (2) |
C11—C13—H13A | 109.5 | C201—C206—C219 | 120.1 (2) |
C11—C13—H13B | 109.5 | C205—C206—C219 | 120.5 (2) |
H13A—C13—H13B | 109.5 | C208—C207—C205 | 121.2 (2) |
C11—C13—H13C | 109.5 | C208—C207—H207 | 119.4 |
H13A—C13—H13C | 109.5 | C205—C207—H207 | 119.4 |
H13B—C13—H13C | 109.5 | C207—C208—C209 | 122.0 (2) |
C11—C14—H14A | 109.5 | C207—C208—H208 | 119.0 |
C11—C14—H14B | 109.5 | C209—C208—H208 | 119.0 |
H14A—C14—H14B | 109.5 | C210—C209—C208 | 117.2 (2) |
C11—C14—H14C | 109.5 | C210—C209—C215 | 124.2 (2) |
H14A—C14—H14C | 109.5 | C208—C209—C215 | 118.6 (2) |
H14B—C14—H14C | 109.5 | C209—C210—C204 | 122.1 (2) |
C16—C15—C9 | 112.0 (2) | C209—C210—H210 | 118.9 |
C16—C15—C17 | 108.2 (2) | C204—C210—H210 | 118.9 |
C9—C15—C17 | 110.3 (2) | C202—C211—C213 | 109.7 (2) |
C16—C15—C18 | 108.5 (2) | C202—C211—C212 | 111.5 (2) |
C9—C15—C18 | 108.2 (2) | C213—C211—C212 | 107.5 (2) |
C17—C15—C18 | 109.6 (2) | C202—C211—C214 | 111.5 (2) |
C15—C16—H16A | 109.5 | C213—C211—C214 | 109.6 (2) |
C15—C16—H16B | 109.5 | C212—C211—C214 | 106.9 (2) |
H16A—C16—H16B | 109.5 | C211—C212—H21A | 109.5 |
C15—C16—H16C | 109.5 | C211—C212—H21B | 109.5 |
H16A—C16—H16C | 109.5 | H21A—C212—H21B | 109.5 |
H16B—C16—H16C | 109.5 | C211—C212—H21C | 109.5 |
C15—C17—H17A | 109.5 | H21A—C212—H21C | 109.5 |
C15—C17—H17B | 109.5 | H21B—C212—H21C | 109.5 |
H17A—C17—H17B | 109.5 | C211—C213—H21D | 109.5 |
C15—C17—H17C | 109.5 | C211—C213—H21E | 109.5 |
H17A—C17—H17C | 109.5 | H21D—C213—H21E | 109.5 |
H17B—C17—H17C | 109.5 | C211—C213—H21F | 109.5 |
C15—C18—H18A | 109.5 | H21D—C213—H21F | 109.5 |
C15—C18—H18B | 109.5 | H21E—C213—H21F | 109.5 |
H18A—C18—H18B | 109.5 | C211—C214—H21G | 109.5 |
C15—C18—H18C | 109.5 | C211—C214—H21H | 109.5 |
H18A—C18—H18C | 109.5 | H21G—C214—H21H | 109.5 |
H18B—C18—H18C | 109.5 | C211—C214—H21I | 109.5 |
N1—C19—C20 | 119.9 (2) | H21G—C214—H21I | 109.5 |
N1—C19—C6 | 118.6 (2) | H21H—C214—H21I | 109.5 |
C20—C19—C6 | 121.4 (2) | C216—C215—C209 | 112.2 (2) |
C21—C20—C27 | 118.1 (2) | C216—C215—C218 | 108.9 (3) |
C21—C20—C19 | 118.8 (2) | C209—C215—C218 | 109.1 (2) |
C27—C20—C19 | 123.0 (2) | C216—C215—C217 | 108.5 (3) |
C22—C21—C20 | 118.5 (2) | C209—C215—C217 | 109.2 (2) |
C22—C21—C24 | 121.6 (2) | C218—C215—C217 | 109.0 (3) |
C20—C21—C24 | 119.8 (2) | C215—C216—H21J | 109.5 |
C23—C22—C21 | 119.0 (2) | C215—C216—H21K | 109.5 |
C23—C22—H22 | 120.5 | H21J—C216—H21K | 109.5 |
C21—C22—H22 | 120.5 | C215—C216—H21L | 109.5 |
C22—C23—N1 | 123.7 (2) | H21J—C216—H21L | 109.5 |
C22—C23—H23 | 118.2 | H21K—C216—H21L | 109.5 |
N1—C23—H23 | 118.2 | C215—C217—H21M | 109.5 |
C25—C24—C21 | 120.4 (2) | C215—C217—H21N | 109.5 |
C25—C24—H24 | 119.8 | H21M—C217—H21N | 109.5 |
C21—C24—H24 | 119.8 | C215—C217—H21O | 109.5 |
C24—C25—C26 | 120.1 (3) | H21M—C217—H21O | 109.5 |
C24—C25—H25 | 119.9 | H21N—C217—H21O | 109.5 |
C26—C25—H25 | 119.9 | C215—C218—H21P | 109.5 |
C27—C26—C25 | 120.6 (3) | C215—C218—H21Q | 109.5 |
C27—C26—H26 | 119.7 | H21P—C218—H21Q | 109.5 |
C25—C26—H26 | 119.7 | C215—C218—H21R | 109.5 |
C26—C27—C20 | 120.8 (2) | H21P—C218—H21R | 109.5 |
C26—C27—H27 | 119.6 | H21Q—C218—H21R | 109.5 |
C20—C27—H27 | 119.6 | N201—C219—C220 | 120.3 (2) |
C119—N101—C123 | 118.5 (2) | N201—C219—C206 | 119.2 (2) |
C119—N101—Al1 | 118.71 (16) | C220—C219—C206 | 120.5 (2) |
C123—N101—Al1 | 118.25 (16) | C221—C220—C227 | 118.3 (2) |
C101—O101—Al1 | 119.10 (15) | C221—C220—C219 | 118.2 (2) |
O101—C101—C106 | 119.7 (2) | C227—C220—C219 | 123.4 (2) |
O101—C101—C102 | 120.7 (2) | C220—C221—C222 | 118.1 (2) |
C106—C101—C102 | 119.5 (2) | C220—C221—C224 | 119.4 (2) |
C103—C102—C101 | 117.9 (2) | C222—C221—C224 | 122.4 (2) |
C103—C102—C111 | 120.6 (2) | C223—C222—C221 | 118.9 (2) |
C101—C102—C111 | 121.4 (2) | C223—C222—H222 | 120.5 |
C102—C103—C104 | 123.6 (2) | C221—C222—H222 | 120.5 |
C102—C103—H103 | 118.2 | C222—C223—N201 | 123.3 (2) |
C104—C103—H103 | 118.2 | C222—C223—H223 | 118.4 |
C105—C104—C110 | 120.2 (2) | N201—C223—H223 | 118.4 |
C105—C104—C103 | 118.6 (2) | C225—C224—C221 | 120.2 (3) |
C110—C104—C103 | 121.1 (2) | C225—C224—H224 | 119.9 |
C104—C105—C107 | 116.7 (2) | C221—C224—H224 | 119.9 |
C104—C105—C106 | 118.5 (2) | C224—C225—C226 | 120.4 (3) |
C107—C105—C106 | 124.6 (2) | C224—C225—H225 | 119.8 |
C101—C106—C105 | 121.0 (2) | C226—C225—H225 | 119.8 |
C101—C106—C119 | 118.5 (2) | C227—C226—C225 | 120.7 (3) |
C105—C106—C119 | 120.4 (2) | C227—C226—H226 | 119.7 |
C108—C107—C105 | 121.4 (2) | C225—C226—H226 | 119.7 |
C108—C107—H107 | 119.3 | C226—C227—C220 | 120.5 (2) |
C105—C107—H107 | 119.3 | C226—C227—H227 | 119.8 |
C107—C108—C109 | 122.7 (2) | C220—C227—H227 | 119.8 |
C107—C108—H108 | 118.6 | C302—C301—H30A | 109.5 |
C109—C108—H108 | 118.6 | C302—C301—H30B | 109.5 |
C110—C109—C108 | 116.4 (2) | H30A—C301—H30B | 109.5 |
C110—C109—C115 | 120.4 (2) | C302—C301—H30C | 109.5 |
C108—C109—C115 | 123.1 (2) | H30A—C301—H30C | 109.5 |
C109—C110—C104 | 122.6 (2) | H30B—C301—H30C | 109.5 |
C109—C110—H110 | 118.7 | C303—C302—C307 | 120.0 |
C104—C110—H110 | 118.7 | C303—C302—C301 | 119.6 (3) |
C112—C111—C102 | 111.7 (2) | C307—C302—C301 | 120.3 (3) |
C112—C111—C113 | 107.3 (2) | C304—C303—C302 | 120.0 |
C102—C111—C113 | 111.6 (2) | C304—C303—H303 | 120.0 |
C112—C111—C114 | 106.8 (2) | C302—C303—H303 | 120.0 |
C102—C111—C114 | 108.5 (2) | C303—C304—C305 | 120.0 |
C113—C111—C114 | 110.8 (2) | C303—C304—H304 | 120.0 |
C111—C112—H11A | 109.5 | C305—C304—H304 | 120.0 |
C111—C112—H11B | 109.5 | C306—C305—C304 | 120.0 |
H11A—C112—H11B | 109.5 | C306—C305—H305 | 120.0 |
C111—C112—H11C | 109.5 | C304—C305—H305 | 120.0 |
H11A—C112—H11C | 109.5 | C307—C306—C305 | 120.0 |
H11B—C112—H11C | 109.5 | C307—C306—H306 | 120.0 |
C111—C113—H11D | 109.5 | C305—C306—H306 | 120.0 |
C111—C113—H11E | 109.5 | C306—C307—C302 | 120.0 |
H11D—C113—H11E | 109.5 | C306—C307—H307 | 120.0 |
C111—C113—H11F | 109.5 | C302—C307—H307 | 120.0 |
H11D—C113—H11F | 109.5 | C403—C402—C407 | 120.0 |
H11E—C113—H11F | 109.5 | C403—C402—C401 | 118.8 (6) |
C111—C114—H11G | 109.5 | C407—C402—C401 | 121.2 (6) |
C111—C114—H11H | 109.5 | C404—C403—C402 | 120.0 |
H11G—C114—H11H | 109.5 | C404—C403—H403 | 120.0 |
C111—C114—H11I | 109.5 | C402—C403—H403 | 120.0 |
H11G—C114—H11I | 109.5 | C403—C404—C405 | 120.0 |
H11H—C114—H11I | 109.5 | C403—C404—H404 | 120.0 |
C116—C115—C117 | 108.5 (2) | C405—C404—H404 | 120.0 |
C116—C115—C118 | 109.7 (2) | C406—C405—C404 | 120.0 |
C117—C115—C118 | 107.8 (2) | C406—C405—H405 | 120.0 |
C116—C115—C109 | 111.0 (2) | C404—C405—H405 | 120.0 |
C117—C115—C109 | 111.8 (2) | C405—C406—C407 | 120.0 |
C118—C115—C109 | 107.8 (2) | C405—C406—H406 | 120.0 |
C115—C116—H11J | 109.5 | C407—C406—H406 | 120.0 |
C115—C116—H11K | 109.5 | C406—C407—C402 | 120.0 |
H11J—C116—H11K | 109.5 | C406—C407—H407 | 120.0 |
C115—C116—H11L | 109.5 | C402—C407—H407 | 120.0 |
O1—Al1—N1—C19 | 35.64 (19) | C108—C109—C115—C116 | −135.8 (3) |
O201—Al1—N1—C19 | −142.71 (19) | C110—C109—C115—C117 | 169.9 (2) |
N201—Al1—N1—C19 | −55.58 (19) | C108—C109—C115—C117 | −14.4 (4) |
N101—Al1—N1—C19 | 119.20 (19) | C110—C109—C115—C118 | −71.7 (3) |
O1—Al1—N1—C23 | −142.82 (18) | C108—C109—C115—C118 | 103.9 (3) |
O201—Al1—N1—C23 | 38.83 (18) | C123—N101—C119—C120 | −7.1 (3) |
N201—Al1—N1—C23 | 125.96 (18) | Al1—N101—C119—C120 | 148.66 (18) |
N101—Al1—N1—C23 | −59.25 (18) | C123—N101—C119—C106 | 176.2 (2) |
O101—Al1—O1—C1 | 126.65 (18) | Al1—N101—C119—C106 | −28.0 (3) |
N201—Al1—O1—C1 | 34.96 (19) | C101—C106—C119—N101 | 49.2 (3) |
N1—Al1—O1—C1 | −55.18 (19) | C105—C106—C119—N101 | −128.7 (2) |
N101—Al1—O1—C1 | −146.76 (19) | C101—C106—C119—C120 | −127.5 (2) |
Al1—O1—C1—C6 | 37.3 (3) | C105—C106—C119—C120 | 54.6 (3) |
Al1—O1—C1—C2 | −141.33 (18) | N101—C119—C120—C121 | 9.3 (3) |
O1—C1—C2—C3 | 163.1 (2) | C106—C119—C120—C121 | −174.2 (2) |
C6—C1—C2—C3 | −15.5 (3) | N101—C119—C120—C127 | −167.4 (2) |
O1—C1—C2—C11 | −15.1 (3) | C106—C119—C120—C127 | 9.2 (4) |
C6—C1—C2—C11 | 166.3 (2) | C127—C120—C121—C122 | 172.8 (2) |
C1—C2—C3—C4 | 0.3 (4) | C119—C120—C121—C122 | −4.0 (3) |
C11—C2—C3—C4 | 178.5 (2) | C127—C120—C121—C124 | −4.9 (3) |
C2—C3—C4—C10 | −170.9 (2) | C119—C120—C121—C124 | 178.3 (2) |
C2—C3—C4—C5 | 8.9 (4) | C120—C121—C122—C123 | −3.0 (4) |
C10—C4—C5—C7 | 2.6 (3) | C124—C121—C122—C123 | 174.6 (2) |
C3—C4—C5—C7 | −177.2 (2) | C121—C122—C123—N101 | 5.4 (4) |
C10—C4—C5—C6 | 176.6 (2) | C119—N101—C123—C122 | −0.2 (4) |
C3—C4—C5—C6 | −3.2 (3) | Al1—N101—C123—C122 | −156.1 (2) |
O1—C1—C6—C5 | −157.6 (2) | C122—C121—C124—C125 | −173.4 (2) |
C2—C1—C6—C5 | 21.0 (3) | C120—C121—C124—C125 | 4.2 (4) |
O1—C1—C6—C19 | 20.1 (3) | C121—C124—C125—C126 | −0.4 (4) |
C2—C1—C6—C19 | −161.4 (2) | C124—C125—C126—C127 | −2.6 (4) |
C4—C5—C6—C1 | −11.4 (3) | C125—C126—C127—C120 | 1.8 (4) |
C7—C5—C6—C1 | 162.1 (2) | C121—C120—C127—C126 | 1.9 (4) |
C4—C5—C6—C19 | 171.1 (2) | C119—C120—C127—C126 | 178.6 (2) |
C7—C5—C6—C19 | −15.4 (4) | O101—Al1—N201—C219 | 123.14 (19) |
C4—C5—C7—C8 | −1.0 (4) | O1—Al1—N201—C219 | −141.33 (19) |
C6—C5—C7—C8 | −174.7 (2) | O201—Al1—N201—C219 | 31.74 (19) |
C5—C7—C8—C9 | −1.1 (4) | N1—Al1—N201—C219 | −57.61 (19) |
C7—C8—C9—C10 | 1.7 (4) | O101—Al1—N201—C223 | −55.32 (18) |
C7—C8—C9—C15 | 178.8 (2) | O1—Al1—N201—C223 | 40.21 (18) |
C8—C9—C10—C4 | −0.1 (4) | O201—Al1—N201—C223 | −146.71 (18) |
C15—C9—C10—C4 | −177.1 (2) | N1—Al1—N201—C223 | 123.93 (18) |
C5—C4—C10—C9 | −2.1 (4) | O101—Al1—O201—C201 | −140.57 (18) |
C3—C4—C10—C9 | 177.7 (2) | N201—Al1—O201—C201 | −49.07 (19) |
C3—C2—C11—C13 | 129.8 (3) | N1—Al1—O201—C201 | 41.22 (19) |
C1—C2—C11—C13 | −52.1 (3) | N101—Al1—O201—C201 | 132.02 (18) |
C3—C2—C11—C14 | 11.4 (3) | Al1—O201—C201—C206 | 30.3 (3) |
C1—C2—C11—C14 | −170.5 (2) | Al1—O201—C201—C202 | −148.44 (19) |
C3—C2—C11—C12 | −108.5 (3) | O201—C201—C202—C203 | 164.8 (2) |
C1—C2—C11—C12 | 69.6 (3) | C206—C201—C202—C203 | −13.9 (4) |
C10—C9—C15—C16 | −14.5 (4) | O201—C201—C202—C211 | −15.6 (4) |
C8—C9—C15—C16 | 168.5 (2) | C206—C201—C202—C211 | 165.7 (2) |
C10—C9—C15—C17 | −135.1 (3) | C201—C202—C203—C204 | −1.7 (4) |
C8—C9—C15—C17 | 48.0 (3) | C211—C202—C203—C204 | 178.8 (2) |
C10—C9—C15—C18 | 105.0 (3) | C202—C203—C204—C205 | 8.9 (4) |
C8—C9—C15—C18 | −71.9 (3) | C202—C203—C204—C210 | −170.0 (3) |
C23—N1—C19—C20 | 3.1 (3) | C210—C204—C205—C207 | 3.5 (4) |
Al1—N1—C19—C20 | −175.34 (16) | C203—C204—C205—C207 | −175.4 (2) |
C23—N1—C19—C6 | 178.7 (2) | C210—C204—C205—C206 | 178.3 (2) |
Al1—N1—C19—C6 | 0.3 (3) | C203—C204—C205—C206 | −0.7 (4) |
C1—C6—C19—N1 | −36.5 (3) | O201—C201—C206—C205 | −156.6 (2) |
C5—C6—C19—N1 | 141.1 (2) | C202—C201—C206—C205 | 22.1 (4) |
C1—C6—C19—C20 | 139.1 (2) | O201—C201—C206—C219 | 22.5 (4) |
C5—C6—C19—C20 | −43.4 (3) | C202—C201—C206—C219 | −158.8 (2) |
N1—C19—C20—C21 | −9.1 (3) | C204—C205—C206—C201 | −14.7 (4) |
C6—C19—C20—C21 | 175.4 (2) | C207—C205—C206—C201 | 159.7 (2) |
N1—C19—C20—C27 | 167.2 (2) | C204—C205—C206—C219 | 166.2 (2) |
C6—C19—C20—C27 | −8.3 (4) | C207—C205—C206—C219 | −19.4 (4) |
C27—C20—C21—C22 | −169.2 (2) | C204—C205—C207—C208 | −1.4 (4) |
C19—C20—C21—C22 | 7.3 (4) | C206—C205—C207—C208 | −175.9 (2) |
C27—C20—C21—C24 | 6.1 (4) | C205—C207—C208—C209 | −1.3 (4) |
C19—C20—C21—C24 | −177.3 (2) | C207—C208—C209—C210 | 1.8 (4) |
C20—C21—C22—C23 | 0.2 (4) | C207—C208—C209—C215 | −179.8 (3) |
C24—C21—C22—C23 | −175.1 (3) | C208—C209—C210—C204 | 0.5 (4) |
C21—C22—C23—N1 | −6.6 (4) | C215—C209—C210—C204 | −177.9 (3) |
C19—N1—C23—C22 | 5.0 (4) | C205—C204—C210—C209 | −3.1 (4) |
Al1—N1—C23—C22 | −176.5 (2) | C203—C204—C210—C209 | 175.8 (3) |
C22—C21—C24—C25 | 171.9 (3) | C203—C202—C211—C213 | 124.9 (3) |
C20—C21—C24—C25 | −3.4 (4) | C201—C202—C211—C213 | −54.7 (3) |
C21—C24—C25—C26 | −1.2 (4) | C203—C202—C211—C212 | 5.9 (4) |
C24—C25—C26—C27 | 2.8 (4) | C201—C202—C211—C212 | −173.7 (2) |
C25—C26—C27—C20 | 0.1 (4) | C203—C202—C211—C214 | −113.6 (3) |
C21—C20—C27—C26 | −4.6 (4) | C201—C202—C211—C214 | 66.9 (3) |
C19—C20—C27—C26 | 179.0 (2) | C210—C209—C215—C216 | −4.2 (4) |
O101—Al1—N101—C119 | −16.36 (18) | C208—C209—C215—C216 | 177.4 (3) |
O1—Al1—N101—C119 | −112.20 (18) | C210—C209—C215—C218 | 116.4 (3) |
O201—Al1—N101—C119 | 74.73 (18) | C208—C209—C215—C218 | −61.9 (4) |
N1—Al1—N101—C119 | 164.22 (18) | C210—C209—C215—C217 | −124.6 (3) |
O101—Al1—N101—C123 | 139.50 (18) | C208—C209—C215—C217 | 57.1 (3) |
O1—Al1—N101—C123 | 43.67 (18) | C223—N201—C219—C220 | 3.6 (3) |
O201—Al1—N101—C123 | −129.40 (18) | Al1—N201—C219—C220 | −174.82 (17) |
N1—Al1—N101—C123 | −39.91 (19) | C223—N201—C219—C206 | −178.8 (2) |
O1—Al1—O101—C101 | 139.92 (17) | Al1—N201—C219—C206 | 2.8 (3) |
O201—Al1—O101—C101 | −41.51 (17) | C201—C206—C219—N201 | −38.0 (3) |
N201—Al1—O101—C101 | −128.68 (17) | C205—C206—C219—N201 | 141.1 (2) |
N101—Al1—O101—C101 | 56.52 (17) | C201—C206—C219—C220 | 139.6 (2) |
Al1—O101—C101—C106 | −52.6 (3) | C205—C206—C219—C220 | −41.3 (3) |
Al1—O101—C101—C102 | 127.7 (2) | N201—C219—C220—C221 | −13.5 (4) |
O101—C101—C102—C103 | −175.3 (2) | C206—C219—C220—C221 | 168.9 (2) |
C106—C101—C102—C103 | 5.0 (4) | N201—C219—C220—C227 | 165.3 (2) |
O101—C101—C102—C111 | 1.6 (4) | C206—C219—C220—C227 | −12.2 (4) |
C106—C101—C102—C111 | −178.1 (2) | C227—C220—C221—C222 | −166.7 (2) |
C101—C102—C103—C104 | 3.0 (4) | C219—C220—C221—C222 | 12.2 (4) |
C111—C102—C103—C104 | −174.0 (2) | C227—C220—C221—C224 | 9.0 (4) |
C102—C103—C104—C105 | −5.7 (4) | C219—C220—C221—C224 | −172.1 (2) |
C102—C103—C104—C110 | 171.0 (2) | C220—C221—C222—C223 | −1.5 (4) |
C110—C104—C105—C107 | −1.0 (4) | C224—C221—C222—C223 | −177.1 (3) |
C103—C104—C105—C107 | 175.7 (2) | C221—C222—C223—N201 | −9.0 (4) |
C110—C104—C105—C106 | −176.3 (2) | C219—N201—C223—C222 | 8.0 (4) |
C103—C104—C105—C106 | 0.4 (4) | Al1—N201—C223—C222 | −173.5 (2) |
O101—C101—C106—C105 | 170.1 (2) | C220—C221—C224—C225 | −4.9 (4) |
C102—C101—C106—C105 | −10.2 (4) | C222—C221—C224—C225 | 170.7 (3) |
O101—C101—C106—C119 | −7.8 (3) | C221—C224—C225—C226 | −1.7 (5) |
C102—C101—C106—C119 | 171.9 (2) | C224—C225—C226—C227 | 4.1 (5) |
C104—C105—C106—C101 | 7.4 (4) | C225—C226—C227—C220 | 0.2 (4) |
C107—C105—C106—C101 | −167.5 (2) | C221—C220—C227—C226 | −6.7 (4) |
C104—C105—C106—C119 | −174.7 (2) | C219—C220—C227—C226 | 174.4 (3) |
C107—C105—C106—C119 | 10.4 (4) | C307—C302—C303—C304 | 0.0 |
C104—C105—C107—C108 | 0.0 (4) | C301—C302—C303—C304 | −178.0 (3) |
C106—C105—C107—C108 | 175.1 (3) | C302—C303—C304—C305 | 0.0 |
C105—C107—C108—C109 | 0.1 (4) | C303—C304—C305—C306 | 0.0 |
C107—C108—C109—C110 | 0.6 (4) | C304—C305—C306—C307 | 0.0 |
C107—C108—C109—C115 | −175.2 (3) | C305—C306—C307—C302 | 0.0 |
C108—C109—C110—C104 | −1.6 (4) | C303—C302—C307—C306 | 0.0 |
C115—C109—C110—C104 | 174.3 (2) | C301—C302—C307—C306 | 178.0 (3) |
C105—C104—C110—C109 | 1.8 (4) | C407—C402—C403—C404 | 0.0 |
C103—C104—C110—C109 | −174.8 (3) | C401—C402—C403—C404 | 178.5 (7) |
C103—C102—C111—C112 | −10.0 (3) | C402—C403—C404—C405 | 0.0 |
C101—C102—C111—C112 | 173.1 (2) | C403—C404—C405—C406 | 0.0 |
C103—C102—C111—C113 | −130.2 (3) | C404—C405—C406—C407 | 0.0 |
C101—C102—C111—C113 | 52.9 (3) | C405—C406—C407—C402 | 0.0 |
C103—C102—C111—C114 | 107.4 (3) | C403—C402—C407—C406 | 0.0 |
C101—C102—C111—C114 | −69.5 (3) | C401—C402—C407—C406 | −178.4 (8) |
C110—C109—C115—C116 | 48.5 (3) |
Experimental details
Crystal data | |
Chemical formula | [Al(C27H28NO)3]·1.5C7H8 |
Mr | 1312.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 13.0728 (2), 15.9452 (3), 19.4565 (4) |
α, β, γ (°) | 75.217 (1), 75.262 (1), 74.200 (1) |
V (Å3) | 3697.98 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.10 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Bruker Nonius APEXII CCD area-detector diffractometer on κ-goniostat |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.850, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 70540, 16846, 11372 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.155, 1.05 |
No. of reflections | 16846 |
No. of parameters | 915 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.37 |
Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).
Al1—N1 | 2.077 (2) | Al1—O1 | 1.8485 (17) |
Al1—N101 | 2.110 (2) | Al1—O101 | 1.8338 (18) |
Al1—N201 | 2.035 (2) | Al1—O201 | 1.8573 (17) |
N1—Al1—O1 | 83.72 (8) | N201—Al1—O201 | 87.13 (8) |
N101—Al1—O101 | 87.22 (8) |
Ligand | Solid angle (steradians) | Equivalent cone angle (°) |
N1—O1 | 4.77 | 152.0 |
N101—O101 | 4.93 | 155.1 |
N201—O201 | 4.79 | 152.6 |
Values calculated using Solid-G (Guzei & Wendt, 2006). |
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The formation of polyesters continues to be a focus of research as a means of producing bio-resourced and biodegradable polymers that can replace polyolefins in a many applications. One particularly attractive route is the synthesis of such polyesters by the ring-opening polymerization of lactones catalysed by metal complexes, and in particular the polymerization of lactide. Polylactide can exist as a number of stereoisomers (Stanford & Dove, 2010; Thomas, 2010; Amgoune et al., 2007; Dechy-Cabaret et al., 2004). Complexes of aluminium bearing a variety of chiral chelating ligands have been investigated as catalysts of choice over several years (Spassky et al., 1996; Ovitt & Coates, 1999; Ovitt & Coates, 2002; Zhong et al., 2003; Du et al., 2009). Whereas many of them show good activity in lactide polymerization, there is no clear correlation between ligand chirality and the ability of the resulting complexes to control the stereoselectivity in the resulting polylactide, and new ligand types continue to be explored.
We have recently reported the synthesis and structural characterization of 3,6-di-tert-butyl-1-(isoquinolin-1-yl)-2-naphthol (LH), (I), which reacts with bis(silyl)amide complexes of magnesium, calcium and zinc to give complexes containing the ligand as N,O-chelates (Howard et al., 2009). We report here the reaction of (I) with trimethylaluminium. Although the molar ratio was adjusted to result in a mixed-ligand complex L2AlMe, in all cases complete substitution of all three methyl ligands was observed, and [Al(L)3] was the only isolable product. In reactions with ε-caprolactone or rac-lactide in tetrahydrofuran at 323 K, this complex produced only traces of polymers. Recrystallization from toluene afforded the title compound, (II), as yellow blocks which were suitable for X-ray crystallography.
Compound (II) (Fig. 1) crystallizes as the toluene sesquisolvate in the space group P1 with no symmetry relationship between the three ligand groups on the Al centre. Two of the three ligands show the same stereochemistry and the third one the opposite, so the complex is a 1:1 mixture of the R,R,S and S,S,R isomers. The arrangement of the three ligands results in meridional coordination geometry for both N and O atoms. A search of the Cambridge Structural Database (CSD, Version 5.33; Allen, 2002) shows that three structures have previously been reported containing pyridinyl–phenolate chelates on Al [CSD refcodes ACEJOH and ACEJUN (Liu et al., 2000), and HALXEY (Steinhauser et al., 2004)]. ACEJOH and ACEJUN feature two chelating N–O ligands, while HALXEY contains two bis(phenolate)pyridinyl groups. In these structures, the N—Al—O angles fall in the range 86.63 (8)–89.89 (9)°. In (II), the two ligands with the same sense of chirality have angles which fall within this range, while the N1—Al1—O1 angle is significantly smaller. This may reflect the steric demand of accommodating three N–O ligands around the Al, with the requirements of three separate ligands at the metal centre forcing one ligand to adopt a sub-optimal bite angle.
Examination of the geometric parameters of the metal coordination sphere (Table 1) shows that the three ligands have statistically different bond distances to the metal. The previously reported structures have Al—N bond distances in the range 2.088 (2)–2.197 (4) Å, and Al—O bond distances in the range 1.741 (2)–1.8823 (17) Å; the values observed for (II) fall within these ranges. Using the Solid-G progam (Guzei & Wendt, 2006), it is possible to caclulate solid-angle and equivalent cone-angle data for the three ligands around the metal (Table 2). The largest cone angle is found for the N101–O101 ligand, which features the shortest Al—O vector and longest Al—N distance. This can be rationalised as the presence of the O atom close to the metal requiring that the tert-butyl group also be closer, increasing the steric crowding caused by the N101–O101 ligand compared with the other two ligand groups. The coordination of the pyridyl group associated with N101 to Al is distinct from the other two ligand groups; the six-membered ring is bent significantly relative to the Al—N bond. The angle subtended by Al1—N101—C121 (C121 is the 4-position relative to the N atom) is 156.71 (11)°, compared with 176.10 (11) and 175.71 (11)° for the other two pyridyl groups. A search of the CSD shows that the range previously reported for this angle is 147.5–179.8° for the 304 structures containing a pyridyl-ligated Al. There are a total of 528 distinct angles reported, of which only 31 are below that seen in (II). This again seems most likely to be due to the steric constraints of packing three bulky ligands around the Al centre.
Overall, compound (II) is very crowded, and we suspect that this high degree of steric hindrance prevents the association of a cyclic ester monomer and the initiation of the subsequent ring-opening step.