Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603162X/sj2101sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603162X/sj2101Isup2.hkl |
CCDC reference: 621492
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.119
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.29 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C36 - C37 .. 5.44 su
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.287 Tmax scaled 0.978 Tmin scaled 0.895
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Roles of co-authors are as follows: |
Manju Rajeswaran - Crystallographer David Place - worked on the initial synthesis, adapting it from previous work to include the azeotropic distillations and did some of the early stage optimization. Muhunthan Sathiosatham - developed the ultimate procedure used for synthesis Joseph Deaton - Structure results analysis, comparison with similar structures in literature, device design Christopher Brown - principle investigator for project, participated in all phases of the research for these complexes. William Lenhart - NMR spectra
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Al(C18H13O)(C10H8NO)2] | F(000) = 1232 |
Mr = 588.61 | Dx = 1.298 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 13891 reflections |
a = 15.4526 (3) Å | θ = 1.0–25.7° |
b = 13.0266 (4) Å | µ = 0.11 mm−1 |
c = 15.7570 (3) Å | T = 295 K |
β = 108.205 (2)° | Cube, green |
V = 3013.04 (12) Å3 | 0.32 × 0.30 × 0.20 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 5684 independent reflections |
Radiation source: fine-focus sealed tube | 4167 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 9 pixels mm-1 | θmax = 25.7°, θmin = 3.8° |
φ and ω scans | h = −18→18 |
Absorption correction: multi-scan from symmetry-related measurements; (SORTAV; Blessing, 1995) | k = −14→15 |
Tmin = 0.695, Tmax = 0.760 | l = −18→19 |
22312 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.3029P] where P = (Fo2 + 2Fc2)/3 |
5684 reflections | (Δ/σ)max < 0.001 |
399 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. 1H NMR (500 MHz, tetrachloroethane-d2): (2.77 (s, 6H), 6.45 (m, 2H), 6.53 (m, 4H), 6.71 (dd, J = 7.7, 1 Hz, 2H), 6.89 (t, J = 7.4 Hz, 1H), 7.04 (m, 4H), 7.11 (d, J = 7.4 Hz, 2H), 7.12 (dd, J = 8.1, 1 Hz, 2H), 7.32 (dd, J = 7.7, 8.1 Hz, 2H), 7.41 (d, J = 8.4 Hz, 2H), 8.19 (d, J = 8.4 Hz, 2H)). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Al1 | 0.29070 (3) | 0.43137 (4) | 0.09391 (3) | 0.03792 (14) | |
O1 | 0.35999 (8) | 0.39102 (9) | 0.20235 (7) | 0.0465 (3) | |
O2 | 0.18705 (7) | 0.36774 (9) | 0.03309 (7) | 0.0454 (3) | |
O3 | 0.33021 (8) | 0.53101 (8) | 0.04249 (7) | 0.0435 (3) | |
N1 | 0.22421 (9) | 0.51827 (10) | 0.16355 (8) | 0.0393 (3) | |
N2 | 0.35047 (9) | 0.32152 (11) | 0.03549 (8) | 0.0419 (3) | |
C1 | 0.26982 (10) | 0.50567 (12) | 0.25300 (10) | 0.0390 (4) | |
C2 | 0.34376 (11) | 0.43619 (13) | 0.27246 (11) | 0.0421 (4) | |
C3 | 0.39300 (13) | 0.42007 (15) | 0.36047 (11) | 0.0545 (5) | |
H3 | 0.4418 | 0.3745 | 0.3751 | 0.065* | |
C4 | 0.36998 (14) | 0.47205 (17) | 0.42827 (12) | 0.0596 (5) | |
H4 | 0.4047 | 0.4607 | 0.4874 | 0.072* | |
C5 | 0.29900 (14) | 0.53817 (16) | 0.41066 (12) | 0.0567 (5) | |
H5 | 0.2850 | 0.5711 | 0.4571 | 0.068* | |
C6 | 0.24651 (12) | 0.55663 (13) | 0.32127 (11) | 0.0464 (4) | |
C7 | 0.17157 (14) | 0.62346 (16) | 0.29332 (13) | 0.0602 (5) | |
H7 | 0.1529 | 0.6596 | 0.3354 | 0.072* | |
C8 | 0.12649 (14) | 0.63531 (16) | 0.20492 (13) | 0.0614 (5) | |
H8 | 0.0770 | 0.6797 | 0.1872 | 0.074* | |
C9 | 0.15313 (12) | 0.58178 (14) | 0.13947 (11) | 0.0468 (4) | |
C10 | 0.10220 (13) | 0.59643 (18) | 0.04263 (12) | 0.0587 (5) | |
H10A | 0.1193 | 0.6608 | 0.0228 | 0.088* | |
H10B | 0.0379 | 0.5964 | 0.0342 | 0.088* | |
H10C | 0.1167 | 0.5415 | 0.0087 | 0.088* | |
C11 | 0.28231 (12) | 0.26496 (13) | −0.02132 (10) | 0.0435 (4) | |
C12 | 0.19356 (12) | 0.29237 (13) | −0.02184 (10) | 0.0432 (4) | |
C13 | 0.12115 (13) | 0.23962 (15) | −0.07778 (12) | 0.0557 (5) | |
H13 | 0.0621 | 0.2553 | −0.0787 | 0.067* | |
C14 | 0.13597 (17) | 0.16198 (17) | −0.13366 (13) | 0.0668 (6) | |
H14 | 0.0860 | 0.1278 | −0.1718 | 0.080* | |
C15 | 0.22103 (17) | 0.13517 (16) | −0.13382 (13) | 0.0663 (6) | |
H15 | 0.2287 | 0.0836 | −0.1716 | 0.080* | |
C16 | 0.29733 (14) | 0.18606 (15) | −0.07629 (12) | 0.0549 (5) | |
C17 | 0.38942 (17) | 0.16677 (18) | −0.06793 (15) | 0.0725 (6) | |
H17 | 0.4040 | 0.1151 | −0.1018 | 0.087* | |
C18 | 0.45690 (16) | 0.22280 (18) | −0.01106 (15) | 0.0708 (6) | |
H18 | 0.5173 | 0.2088 | −0.0061 | 0.085* | |
C19 | 0.43655 (12) | 0.30216 (15) | 0.04080 (12) | 0.0531 (5) | |
C20 | 0.51038 (13) | 0.36586 (18) | 0.10129 (16) | 0.0713 (6) | |
H20A | 0.5180 | 0.4273 | 0.0708 | 0.107* | |
H20B | 0.5663 | 0.3276 | 0.1184 | 0.107* | |
H20C | 0.4944 | 0.3837 | 0.1536 | 0.107* | |
C21 | 0.30781 (11) | 0.62731 (13) | 0.01380 (11) | 0.0411 (4) | |
C22 | 0.33615 (11) | 0.71148 (13) | 0.07169 (11) | 0.0440 (4) | |
C23 | 0.31183 (13) | 0.81042 (14) | 0.03884 (13) | 0.0544 (5) | |
H23 | 0.3305 | 0.8662 | 0.0770 | 0.065* | |
C24 | 0.26088 (15) | 0.82720 (16) | −0.04868 (14) | 0.0637 (5) | |
H24 | 0.2462 | 0.8937 | −0.0697 | 0.076* | |
C25 | 0.23196 (13) | 0.74476 (16) | −0.10478 (13) | 0.0577 (5) | |
H25 | 0.1969 | 0.7564 | −0.1637 | 0.069* | |
C26 | 0.25370 (12) | 0.64444 (14) | −0.07582 (11) | 0.0468 (4) | |
C27 | 0.38990 (12) | 0.69954 (13) | 0.16759 (11) | 0.0451 (4) | |
C28 | 0.36518 (13) | 0.75362 (16) | 0.23262 (13) | 0.0582 (5) | |
H28 | 0.3138 | 0.7953 | 0.2156 | 0.070* | |
C29 | 0.41530 (16) | 0.7467 (2) | 0.32189 (14) | 0.0720 (6) | |
H29 | 0.3977 | 0.7836 | 0.3643 | 0.086* | |
C30 | 0.49078 (18) | 0.68558 (19) | 0.34777 (15) | 0.0770 (7) | |
H30 | 0.5248 | 0.6811 | 0.4078 | 0.092* | |
C31 | 0.51657 (15) | 0.63069 (17) | 0.28519 (15) | 0.0712 (6) | |
H31 | 0.5677 | 0.5886 | 0.3031 | 0.085* | |
C32 | 0.46677 (12) | 0.63773 (15) | 0.19569 (13) | 0.0557 (5) | |
H32 | 0.4850 | 0.6006 | 0.1538 | 0.067* | |
C33 | 0.21670 (14) | 0.55866 (15) | −0.13867 (11) | 0.0539 (5) | |
C34 | 0.12471 (16) | 0.5594 (2) | −0.18951 (13) | 0.0743 (6) | |
H34 | 0.0869 | 0.6118 | −0.1821 | 0.089* | |
C35 | 0.0896 (2) | 0.4816 (3) | −0.25143 (15) | 0.0990 (10) | |
H35 | 0.0282 | 0.4816 | −0.2846 | 0.119* | |
C36 | 0.1455 (3) | 0.4047 (3) | −0.26357 (17) | 0.1051 (11) | |
H36 | 0.1221 | 0.3535 | −0.3056 | 0.126* | |
C37 | 0.2357 (2) | 0.4035 (2) | −0.21373 (15) | 0.0877 (8) | |
H37 | 0.2732 | 0.3512 | −0.2219 | 0.105* | |
C38 | 0.27092 (17) | 0.47869 (16) | −0.15194 (12) | 0.0636 (5) | |
H38 | 0.3322 | 0.4764 | −0.1182 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Al1 | 0.0401 (3) | 0.0343 (3) | 0.0410 (3) | 0.0024 (2) | 0.0152 (2) | 0.0000 (2) |
O1 | 0.0498 (7) | 0.0449 (7) | 0.0466 (6) | 0.0130 (5) | 0.0178 (5) | 0.0048 (5) |
O2 | 0.0429 (6) | 0.0426 (7) | 0.0524 (7) | 0.0000 (5) | 0.0171 (5) | −0.0073 (5) |
O3 | 0.0503 (7) | 0.0348 (6) | 0.0487 (6) | 0.0027 (5) | 0.0203 (5) | 0.0035 (5) |
N1 | 0.0402 (7) | 0.0362 (8) | 0.0428 (7) | 0.0022 (6) | 0.0150 (5) | 0.0007 (6) |
N2 | 0.0460 (8) | 0.0376 (8) | 0.0464 (8) | 0.0030 (6) | 0.0209 (6) | 0.0024 (6) |
C1 | 0.0436 (9) | 0.0337 (9) | 0.0407 (8) | −0.0041 (7) | 0.0146 (7) | 0.0001 (7) |
C2 | 0.0453 (9) | 0.0390 (9) | 0.0434 (9) | −0.0007 (7) | 0.0161 (7) | 0.0023 (7) |
C3 | 0.0562 (11) | 0.0545 (12) | 0.0493 (10) | 0.0068 (9) | 0.0115 (8) | 0.0095 (8) |
C4 | 0.0720 (13) | 0.0615 (13) | 0.0404 (9) | −0.0049 (10) | 0.0104 (8) | 0.0035 (9) |
C5 | 0.0751 (13) | 0.0536 (12) | 0.0443 (10) | −0.0065 (10) | 0.0230 (9) | −0.0057 (8) |
C6 | 0.0572 (10) | 0.0388 (9) | 0.0471 (9) | −0.0037 (8) | 0.0220 (8) | −0.0045 (7) |
C7 | 0.0732 (13) | 0.0573 (13) | 0.0573 (11) | 0.0132 (10) | 0.0305 (10) | −0.0059 (9) |
C8 | 0.0610 (12) | 0.0624 (13) | 0.0647 (12) | 0.0251 (10) | 0.0251 (9) | 0.0008 (10) |
C9 | 0.0450 (10) | 0.0455 (10) | 0.0515 (10) | 0.0067 (8) | 0.0174 (7) | 0.0022 (8) |
C10 | 0.0493 (11) | 0.0699 (14) | 0.0559 (11) | 0.0160 (9) | 0.0148 (8) | 0.0063 (10) |
C11 | 0.0566 (10) | 0.0364 (9) | 0.0417 (9) | −0.0006 (8) | 0.0214 (7) | 0.0006 (7) |
C12 | 0.0538 (10) | 0.0358 (9) | 0.0411 (9) | −0.0023 (8) | 0.0164 (7) | 0.0002 (7) |
C13 | 0.0570 (11) | 0.0516 (11) | 0.0542 (10) | −0.0041 (9) | 0.0111 (8) | −0.0044 (9) |
C14 | 0.0830 (16) | 0.0572 (13) | 0.0519 (11) | −0.0132 (11) | 0.0091 (10) | −0.0109 (9) |
C15 | 0.1012 (18) | 0.0501 (12) | 0.0506 (11) | −0.0066 (12) | 0.0282 (11) | −0.0140 (9) |
C16 | 0.0781 (14) | 0.0450 (11) | 0.0506 (10) | 0.0021 (9) | 0.0329 (9) | −0.0034 (8) |
C17 | 0.0934 (17) | 0.0596 (13) | 0.0833 (15) | 0.0104 (12) | 0.0549 (13) | −0.0135 (12) |
C18 | 0.0666 (13) | 0.0680 (15) | 0.0939 (16) | 0.0099 (11) | 0.0483 (12) | −0.0088 (12) |
C19 | 0.0528 (11) | 0.0488 (11) | 0.0665 (11) | 0.0048 (9) | 0.0313 (9) | 0.0032 (9) |
C20 | 0.0463 (11) | 0.0753 (15) | 0.0961 (16) | 0.0001 (11) | 0.0276 (11) | −0.0080 (12) |
C21 | 0.0416 (9) | 0.0389 (9) | 0.0484 (9) | 0.0027 (7) | 0.0222 (7) | 0.0043 (7) |
C22 | 0.0434 (9) | 0.0388 (10) | 0.0541 (10) | 0.0022 (7) | 0.0214 (7) | 0.0020 (8) |
C23 | 0.0620 (12) | 0.0383 (10) | 0.0644 (12) | 0.0046 (9) | 0.0221 (9) | −0.0006 (8) |
C24 | 0.0785 (14) | 0.0436 (11) | 0.0692 (13) | 0.0148 (10) | 0.0233 (10) | 0.0141 (10) |
C25 | 0.0645 (12) | 0.0560 (12) | 0.0533 (11) | 0.0098 (10) | 0.0195 (9) | 0.0121 (9) |
C26 | 0.0517 (10) | 0.0464 (10) | 0.0472 (9) | 0.0021 (8) | 0.0227 (8) | 0.0060 (8) |
C27 | 0.0445 (9) | 0.0380 (9) | 0.0537 (10) | −0.0049 (7) | 0.0169 (7) | 0.0002 (8) |
C28 | 0.0571 (12) | 0.0582 (12) | 0.0627 (12) | −0.0033 (9) | 0.0234 (9) | −0.0087 (9) |
C29 | 0.0821 (16) | 0.0777 (16) | 0.0576 (12) | −0.0149 (13) | 0.0242 (11) | −0.0111 (11) |
C30 | 0.0921 (17) | 0.0695 (16) | 0.0562 (12) | −0.0192 (13) | 0.0040 (11) | 0.0007 (11) |
C31 | 0.0617 (13) | 0.0533 (13) | 0.0819 (15) | −0.0035 (10) | −0.0018 (11) | 0.0038 (11) |
C32 | 0.0510 (11) | 0.0458 (11) | 0.0661 (12) | −0.0015 (9) | 0.0122 (9) | −0.0026 (9) |
C33 | 0.0679 (12) | 0.0567 (12) | 0.0406 (9) | −0.0088 (10) | 0.0219 (8) | 0.0044 (8) |
C34 | 0.0786 (15) | 0.0931 (18) | 0.0499 (11) | −0.0163 (13) | 0.0181 (10) | 0.0035 (11) |
C35 | 0.105 (2) | 0.131 (3) | 0.0514 (13) | −0.052 (2) | 0.0106 (13) | 0.0011 (16) |
C36 | 0.178 (4) | 0.084 (2) | 0.0555 (15) | −0.059 (2) | 0.0396 (19) | −0.0129 (14) |
C37 | 0.155 (3) | 0.0621 (15) | 0.0532 (13) | −0.0171 (16) | 0.0429 (15) | −0.0061 (12) |
C38 | 0.0978 (16) | 0.0525 (12) | 0.0474 (10) | −0.0069 (11) | 0.0329 (10) | 0.0003 (9) |
Al1—O3 | 1.7387 (12) | C17—H17 | 0.9300 |
Al1—O1 | 1.7886 (12) | C18—C19 | 1.413 (3) |
Al1—O2 | 1.7921 (12) | C18—H18 | 0.9300 |
Al1—N1 | 2.0605 (13) | C19—C20 | 1.490 (3) |
Al1—N2 | 2.0686 (14) | C20—H20A | 0.9600 |
O1—C2 | 1.3427 (19) | C20—H20B | 0.9600 |
O2—C12 | 1.3333 (19) | C20—H20C | 0.9600 |
O3—C21 | 1.3418 (19) | C21—C22 | 1.406 (2) |
N1—C9 | 1.332 (2) | C21—C26 | 1.416 (2) |
N1—C1 | 1.3746 (19) | C22—C23 | 1.396 (2) |
N2—C19 | 1.331 (2) | C22—C27 | 1.488 (2) |
N2—C11 | 1.365 (2) | C23—C24 | 1.375 (3) |
C1—C6 | 1.403 (2) | C23—H23 | 0.9300 |
C1—C2 | 1.414 (2) | C24—C25 | 1.374 (3) |
C2—C3 | 1.374 (2) | C24—H24 | 0.9300 |
C3—C4 | 1.401 (3) | C25—C26 | 1.390 (3) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.353 (3) | C26—C33 | 1.484 (3) |
C4—H4 | 0.9300 | C27—C32 | 1.388 (3) |
C5—C6 | 1.409 (2) | C27—C28 | 1.392 (3) |
C5—H5 | 0.9300 | C28—C29 | 1.381 (3) |
C6—C7 | 1.405 (3) | C28—H28 | 0.9300 |
C7—C8 | 1.358 (3) | C29—C30 | 1.365 (3) |
C7—H7 | 0.9300 | C29—H29 | 0.9300 |
C8—C9 | 1.409 (2) | C30—C31 | 1.374 (3) |
C8—H8 | 0.9300 | C30—H30 | 0.9300 |
C9—C10 | 1.495 (2) | C31—C32 | 1.382 (3) |
C10—H10A | 0.9600 | C31—H31 | 0.9300 |
C10—H10B | 0.9600 | C32—H32 | 0.9300 |
C10—H10C | 0.9600 | C33—C38 | 1.393 (3) |
C11—C16 | 1.409 (2) | C33—C34 | 1.397 (3) |
C11—C12 | 1.415 (2) | C34—C35 | 1.394 (4) |
C12—C13 | 1.373 (2) | C34—H34 | 0.9300 |
C13—C14 | 1.406 (3) | C35—C36 | 1.375 (4) |
C13—H13 | 0.9300 | C35—H35 | 0.9300 |
C14—C15 | 1.361 (3) | C36—C37 | 1.368 (4) |
C14—H14 | 0.9300 | C36—H36 | 0.9300 |
C15—C16 | 1.408 (3) | C37—C38 | 1.369 (3) |
C15—H15 | 0.9300 | C37—H37 | 0.9300 |
C16—C17 | 1.410 (3) | C38—H38 | 0.9300 |
C17—C18 | 1.356 (3) | ||
O3—Al1—O1 | 118.16 (6) | C18—C17—C16 | 120.73 (18) |
O3—Al1—O2 | 118.77 (6) | C18—C17—H17 | 119.6 |
O1—Al1—O2 | 122.91 (6) | C16—C17—H17 | 119.6 |
O3—Al1—N1 | 98.29 (5) | C17—C18—C19 | 120.79 (19) |
O1—Al1—N1 | 84.38 (5) | C17—C18—H18 | 119.6 |
O2—Al1—N1 | 91.60 (5) | C19—C18—H18 | 119.6 |
O3—Al1—N2 | 92.20 (5) | N2—C19—C18 | 120.08 (18) |
O1—Al1—N2 | 90.26 (5) | N2—C19—C20 | 119.03 (16) |
O2—Al1—N2 | 83.73 (5) | C18—C19—C20 | 120.88 (18) |
N1—Al1—N2 | 169.50 (6) | C19—C20—H20A | 109.5 |
C2—O1—Al1 | 116.57 (10) | C19—C20—H20B | 109.5 |
C12—O2—Al1 | 116.85 (10) | H20A—C20—H20B | 109.5 |
C21—O3—Al1 | 139.80 (10) | C19—C20—H20C | 109.5 |
C9—N1—C1 | 118.64 (13) | H20A—C20—H20C | 109.5 |
C9—N1—Al1 | 133.90 (11) | H20B—C20—H20C | 109.5 |
C1—N1—Al1 | 107.41 (10) | O3—C21—C22 | 121.02 (14) |
C19—N2—C11 | 119.35 (14) | O3—C21—C26 | 119.54 (15) |
C19—N2—Al1 | 132.82 (12) | C22—C21—C26 | 119.43 (15) |
C11—N2—Al1 | 107.75 (10) | C23—C22—C21 | 119.10 (16) |
N1—C1—C6 | 123.86 (15) | C23—C22—C27 | 118.25 (16) |
N1—C1—C2 | 114.81 (14) | C21—C22—C27 | 122.65 (15) |
C6—C1—C2 | 121.33 (15) | C24—C23—C22 | 121.47 (18) |
O1—C2—C3 | 125.22 (16) | C24—C23—H23 | 119.3 |
O1—C2—C1 | 116.61 (14) | C22—C23—H23 | 119.3 |
C3—C2—C1 | 118.16 (15) | C25—C24—C23 | 119.35 (18) |
C2—C3—C4 | 120.22 (18) | C25—C24—H24 | 120.3 |
C2—C3—H3 | 119.9 | C23—C24—H24 | 120.3 |
C4—C3—H3 | 119.9 | C24—C25—C26 | 121.79 (17) |
C5—C4—C3 | 122.25 (17) | C24—C25—H25 | 119.1 |
C5—C4—H4 | 118.9 | C26—C25—H25 | 119.1 |
C3—C4—H4 | 118.9 | C25—C26—C21 | 118.83 (16) |
C4—C5—C6 | 119.35 (17) | C25—C26—C33 | 119.04 (16) |
C4—C5—H5 | 120.3 | C21—C26—C33 | 122.09 (16) |
C6—C5—H5 | 120.3 | C32—C27—C28 | 117.59 (17) |
C1—C6—C7 | 115.89 (16) | C32—C27—C22 | 122.36 (16) |
C1—C6—C5 | 118.68 (17) | C28—C27—C22 | 120.03 (16) |
C7—C6—C5 | 125.43 (16) | C29—C28—C27 | 121.4 (2) |
C8—C7—C6 | 120.03 (17) | C29—C28—H28 | 119.3 |
C8—C7—H7 | 120.0 | C27—C28—H28 | 119.3 |
C6—C7—H7 | 120.0 | C30—C29—C28 | 119.8 (2) |
C7—C8—C9 | 121.41 (17) | C30—C29—H29 | 120.1 |
C7—C8—H8 | 119.3 | C28—C29—H29 | 120.1 |
C9—C8—H8 | 119.3 | C29—C30—C31 | 120.1 (2) |
N1—C9—C8 | 120.16 (16) | C29—C30—H30 | 119.9 |
N1—C9—C10 | 119.63 (15) | C31—C30—H30 | 119.9 |
C8—C9—C10 | 120.21 (16) | C30—C31—C32 | 120.2 (2) |
C9—C10—H10A | 109.5 | C30—C31—H31 | 119.9 |
C9—C10—H10B | 109.5 | C32—C31—H31 | 119.9 |
H10A—C10—H10B | 109.5 | C31—C32—C27 | 120.80 (19) |
C9—C10—H10C | 109.5 | C31—C32—H32 | 119.6 |
H10A—C10—H10C | 109.5 | C27—C32—H32 | 119.6 |
H10B—C10—H10C | 109.5 | C38—C33—C34 | 118.1 (2) |
N2—C11—C16 | 123.72 (16) | C38—C33—C26 | 122.61 (18) |
N2—C11—C12 | 114.54 (14) | C34—C33—C26 | 119.23 (19) |
C16—C11—C12 | 121.74 (16) | C35—C34—C33 | 120.0 (3) |
O2—C12—C13 | 125.01 (16) | C35—C34—H34 | 120.0 |
O2—C12—C11 | 116.85 (14) | C33—C34—H34 | 120.0 |
C13—C12—C11 | 118.14 (16) | C36—C35—C34 | 120.2 (3) |
C12—C13—C14 | 120.17 (19) | C36—C35—H35 | 119.9 |
C12—C13—H13 | 119.9 | C34—C35—H35 | 119.9 |
C14—C13—H13 | 119.9 | C37—C36—C35 | 120.0 (3) |
C15—C14—C13 | 122.15 (19) | C37—C36—H36 | 120.0 |
C15—C14—H14 | 118.9 | C35—C36—H36 | 120.0 |
C13—C14—H14 | 118.9 | C36—C37—C38 | 120.5 (3) |
C14—C15—C16 | 119.54 (18) | C36—C37—H37 | 119.7 |
C14—C15—H15 | 120.2 | C38—C37—H37 | 119.7 |
C16—C15—H15 | 120.2 | C37—C38—C33 | 121.2 (2) |
C15—C16—C11 | 118.25 (18) | C37—C38—H38 | 119.4 |
C15—C16—C17 | 126.43 (18) | C33—C38—H38 | 119.4 |
C11—C16—C17 | 115.32 (18) | ||
O3—Al1—O1—C2 | 92.06 (12) | N2—C11—C12—O2 | −0.9 (2) |
O2—Al1—O1—C2 | −92.61 (12) | C16—C11—C12—O2 | 179.67 (15) |
N1—Al1—O1—C2 | −4.35 (12) | N2—C11—C12—C13 | 179.49 (15) |
N2—Al1—O1—C2 | −175.31 (12) | C16—C11—C12—C13 | 0.1 (2) |
O3—Al1—O2—C12 | 84.22 (12) | O2—C12—C13—C14 | 179.37 (16) |
O1—Al1—O2—C12 | −91.09 (12) | C11—C12—C13—C14 | −1.1 (3) |
N1—Al1—O2—C12 | −175.42 (11) | C12—C13—C14—C15 | 1.0 (3) |
N2—Al1—O2—C12 | −4.85 (11) | C13—C14—C15—C16 | 0.2 (3) |
O1—Al1—O3—C21 | −116.12 (16) | C14—C15—C16—C11 | −1.1 (3) |
O2—Al1—O3—C21 | 68.34 (17) | C14—C15—C16—C17 | 179.4 (2) |
N1—Al1—O3—C21 | −28.09 (17) | N2—C11—C16—C15 | −178.31 (16) |
N2—Al1—O3—C21 | 152.40 (16) | C12—C11—C16—C15 | 1.0 (3) |
O3—Al1—N1—C9 | 63.51 (17) | N2—C11—C16—C17 | 1.2 (3) |
O1—Al1—N1—C9 | −178.78 (17) | C12—C11—C16—C17 | −179.46 (17) |
O2—Al1—N1—C9 | −55.87 (16) | C15—C16—C17—C18 | 178.7 (2) |
N2—Al1—N1—C9 | −119.2 (3) | C11—C16—C17—C18 | −0.8 (3) |
O3—Al1—N1—C1 | −113.84 (10) | C16—C17—C18—C19 | −0.3 (3) |
O1—Al1—N1—C1 | 3.87 (10) | C11—N2—C19—C18 | −0.9 (3) |
O2—Al1—N1—C1 | 126.78 (10) | Al1—N2—C19—C18 | −177.13 (14) |
N2—Al1—N1—C1 | 63.5 (3) | C11—N2—C19—C20 | 178.53 (17) |
O3—Al1—N2—C19 | 61.92 (16) | Al1—N2—C19—C20 | 2.3 (3) |
O1—Al1—N2—C19 | −56.28 (16) | C17—C18—C19—N2 | 1.3 (3) |
O2—Al1—N2—C19 | −179.38 (16) | C17—C18—C19—C20 | −178.2 (2) |
N1—Al1—N2—C19 | −115.4 (3) | Al1—O3—C21—C22 | 86.9 (2) |
O3—Al1—N2—C11 | −114.64 (11) | Al1—O3—C21—C26 | −92.22 (19) |
O1—Al1—N2—C11 | 127.16 (11) | O3—C21—C22—C23 | 179.55 (15) |
O2—Al1—N2—C11 | 4.06 (10) | C26—C21—C22—C23 | −1.4 (2) |
N1—Al1—N2—C11 | 68.0 (3) | O3—C21—C22—C27 | −1.6 (2) |
C9—N1—C1—C6 | −0.6 (2) | C26—C21—C22—C27 | 177.48 (15) |
Al1—N1—C1—C6 | 177.27 (13) | C21—C22—C23—C24 | 0.0 (3) |
C9—N1—C1—C2 | 179.43 (15) | C27—C22—C23—C24 | −178.88 (17) |
Al1—N1—C1—C2 | −2.75 (16) | C22—C23—C24—C25 | 1.1 (3) |
Al1—O1—C2—C3 | −175.98 (14) | C23—C24—C25—C26 | −0.8 (3) |
Al1—O1—C2—C1 | 4.02 (19) | C24—C25—C26—C21 | −0.6 (3) |
N1—C1—C2—O1 | −0.4 (2) | C24—C25—C26—C33 | 177.19 (18) |
C6—C1—C2—O1 | 179.60 (15) | O3—C21—C26—C25 | −179.27 (15) |
N1—C1—C2—C3 | 179.61 (15) | C22—C21—C26—C25 | 1.6 (2) |
C6—C1—C2—C3 | −0.4 (2) | O3—C21—C26—C33 | 3.1 (2) |
O1—C2—C3—C4 | 179.70 (17) | C22—C21—C26—C33 | −176.06 (16) |
C1—C2—C3—C4 | −0.3 (3) | C23—C22—C27—C32 | −132.73 (19) |
C2—C3—C4—C5 | 0.8 (3) | C21—C22—C27—C32 | 48.4 (2) |
C3—C4—C5—C6 | −0.6 (3) | C23—C22—C27—C28 | 45.4 (2) |
N1—C1—C6—C7 | 0.2 (3) | C21—C22—C27—C28 | −133.42 (18) |
C2—C1—C6—C7 | −179.83 (16) | C32—C27—C28—C29 | 0.3 (3) |
N1—C1—C6—C5 | −179.39 (15) | C22—C27—C28—C29 | −177.93 (18) |
C2—C1—C6—C5 | 0.6 (2) | C27—C28—C29—C30 | −0.2 (3) |
C4—C5—C6—C1 | −0.1 (3) | C28—C29—C30—C31 | −0.3 (4) |
C4—C5—C6—C7 | −179.63 (19) | C29—C30—C31—C32 | 0.6 (3) |
C1—C6—C7—C8 | 0.1 (3) | C30—C31—C32—C27 | −0.4 (3) |
C5—C6—C7—C8 | 179.66 (19) | C28—C27—C32—C31 | 0.0 (3) |
C6—C7—C8—C9 | 0.0 (3) | C22—C27—C32—C31 | 178.17 (17) |
C1—N1—C9—C8 | 0.6 (3) | C25—C26—C33—C38 | 131.40 (19) |
Al1—N1—C9—C8 | −176.47 (14) | C21—C26—C33—C38 | −50.9 (2) |
C1—N1—C9—C10 | −179.76 (16) | C25—C26—C33—C34 | −46.0 (2) |
Al1—N1—C9—C10 | 3.1 (3) | C21—C26—C33—C34 | 131.68 (19) |
C7—C8—C9—N1 | −0.4 (3) | C38—C33—C34—C35 | 0.0 (3) |
C7—C8—C9—C10 | −180.0 (2) | C26—C33—C34—C35 | 177.48 (18) |
C19—N2—C11—C16 | −0.4 (2) | C33—C34—C35—C36 | −0.9 (4) |
Al1—N2—C11—C16 | 176.75 (14) | C34—C35—C36—C37 | 1.1 (4) |
C19—N2—C11—C12 | −179.74 (15) | C35—C36—C37—C38 | −0.3 (4) |
Al1—N2—C11—C12 | −2.63 (16) | C36—C37—C38—C33 | −0.6 (3) |
Al1—O2—C12—C13 | −175.67 (14) | C34—C33—C38—C37 | 0.8 (3) |
Al1—O2—C12—C11 | 4.78 (18) | C26—C33—C38—C37 | −176.62 (17) |