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The five-coordinate geometry of the Al atom in the title compound, [Al(C10H8NO)2(C16H11O)], is trigonal–bipyramidal, in which the O-donor atoms of the naphtholate and the two quinolinolate ligands are in the trigonal equatorial plane and the N atoms in the axial positions.
Supporting information
CCDC reference: 633965
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.150
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.786 0.986
Tmin(prime) and Tmax expected: 0.948 0.973
RR(prime) = 0.818
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.18 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16
N2 -AL1 -N1 -C9 -102.50 0.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20
N2 -AL1 -N1 -C1 76.20 0.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24
N1 -AL1 -N2 -C19 -136.50 0.50 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 28
N1 -AL1 -N2 -C11 44.00 0.60 1.555 1.555 1.555 1.555
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
5 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 W. Place - worked on the initial synthesis, adapting it
from previous work to include the azeotropic distillations
and did some of the early stage optimization.
Vincent W. Bakos - developed the ultimate procedure
used for synthesis
Joseph C. Deaton - Structure results analysis, comparison with
similar structures in literature, device design
Christopher T. Brown - principle investigator for project,
participated in all phases of the research for these complexes.
William C. 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: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); 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.
Bis(2-methylquinolin-8-olato-
κ2N,
O)(6-phenyl-2-naphtholato-
κO)aluminium(III)
top
Crystal data top
[Al(C10H8NO)2(C16H11O)] | F(000) = 1176 |
Mr = 562.58 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 10500 reflections |
a = 11.7000 (3) Å | θ = 1.0–27.5° |
b = 16.9930 (4) Å | µ = 0.11 mm−1 |
c = 14.5780 (4) Å | T = 293 K |
β = 93.519 (1)° | Plate, green |
V = 2892.91 (13) Å3 | 0.47 × 0.45 × 0.25 mm |
Z = 4 | |
Data collection top
Noniu KappaCCD area-detector diffractometer | 6568 independent reflections |
Radiation source: fine-focus sealed tube | 3383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
Detector resolution: 9 pixels mm-1 | θmax = 27.4°, θmin = 4.0° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan [from symmetry-related measurements; SORTAV (Blessing, 1995)] | k = −21→21 |
Tmin = 0.786, Tmax = 0.986 | l = −18→18 |
29300 measured reflections | |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0723P)2] where P = (Fo2 + 2Fc2)/3 |
6568 reflections | (Δ/σ)max < 0.001 |
381 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Al1 | 0.70880 (5) | 0.02511 (4) | 0.84731 (4) | 0.04779 (19) | |
O1 | 0.66840 (11) | −0.06573 (9) | 0.89791 (10) | 0.0542 (4) | |
O2 | 0.84804 (12) | 0.03495 (9) | 0.80481 (10) | 0.0591 (4) | |
O3 | 0.60289 (13) | 0.09582 (9) | 0.83407 (11) | 0.0644 (4) | |
N1 | 0.65426 (14) | −0.02821 (11) | 0.72656 (12) | 0.0528 (5) | |
N2 | 0.78387 (14) | 0.06847 (10) | 0.96685 (12) | 0.0497 (4) | |
C1 | 0.61816 (16) | −0.10241 (13) | 0.74577 (16) | 0.0503 (5) | |
C2 | 0.62818 (16) | −0.12226 (13) | 0.83974 (16) | 0.0513 (5) | |
C3 | 0.5978 (2) | −0.19696 (15) | 0.8648 (2) | 0.0703 (7) | |
H3 | 0.6055 | −0.2124 | 0.9261 | 0.084* | |
C4 | 0.5548 (2) | −0.25021 (16) | 0.7967 (3) | 0.0845 (9) | |
H4 | 0.5339 | −0.3005 | 0.8144 | 0.101* | |
C5 | 0.5428 (2) | −0.23034 (18) | 0.7062 (2) | 0.0830 (9) | |
H5 | 0.5129 | −0.2665 | 0.6632 | 0.100* | |
C6 | 0.57565 (18) | −0.15546 (15) | 0.67795 (19) | 0.0628 (7) | |
C7 | 0.5732 (2) | −0.1281 (2) | 0.5868 (2) | 0.0792 (8) | |
H7 | 0.5461 | −0.1606 | 0.5389 | 0.095* | |
C8 | 0.6100 (2) | −0.0551 (2) | 0.56869 (19) | 0.0827 (8) | |
H8 | 0.6085 | −0.0379 | 0.5081 | 0.099* | |
C9 | 0.6508 (2) | −0.00408 (16) | 0.63920 (17) | 0.0672 (7) | |
C10 | 0.6923 (3) | 0.07640 (19) | 0.6193 (2) | 0.0988 (10) | |
H10A | 0.6289 | 0.1084 | 0.5968 | 0.148* | |
H10B | 0.7478 | 0.0736 | 0.5736 | 0.148* | |
H10C | 0.7268 | 0.0992 | 0.6745 | 0.148* | |
C11 | 0.89701 (17) | 0.08302 (12) | 0.95269 (15) | 0.0490 (5) | |
C12 | 0.93056 (17) | 0.06252 (12) | 0.86408 (16) | 0.0527 (6) | |
C13 | 1.04335 (19) | 0.07065 (14) | 0.8461 (2) | 0.0672 (7) | |
H13 | 1.0682 | 0.0566 | 0.7889 | 0.081* | |
C14 | 1.1217 (2) | 0.10048 (16) | 0.9149 (3) | 0.0829 (9) | |
H14 | 1.1984 | 0.1049 | 0.9023 | 0.099* | |
C15 | 1.0896 (2) | 0.12283 (15) | 0.9985 (3) | 0.0787 (8) | |
H15 | 1.1432 | 0.1440 | 1.0414 | 0.094* | |
C16 | 0.9747 (2) | 0.11387 (13) | 1.02035 (19) | 0.0625 (7) | |
C17 | 0.9291 (3) | 0.13121 (15) | 1.1049 (2) | 0.0778 (8) | |
H17 | 0.9761 | 0.1530 | 1.1520 | 0.093* | |
C18 | 0.8176 (3) | 0.11659 (15) | 1.11894 (18) | 0.0730 (7) | |
H18 | 0.7891 | 0.1282 | 1.1755 | 0.088* | |
C19 | 0.7445 (2) | 0.08393 (14) | 1.04855 (16) | 0.0582 (6) | |
C20 | 0.6229 (2) | 0.06460 (19) | 1.06369 (19) | 0.0806 (8) | |
H20A | 0.5734 | 0.0961 | 1.0237 | 0.121* | |
H20B | 0.6078 | 0.0753 | 1.1264 | 0.121* | |
H20C | 0.6092 | 0.0099 | 1.0507 | 0.121* | |
C21 | 0.57153 (18) | 0.17065 (14) | 0.84626 (14) | 0.0519 (5) | |
C22 | 0.46164 (18) | 0.18818 (13) | 0.86610 (15) | 0.0557 (6) | |
H22 | 0.4114 | 0.1474 | 0.8774 | 0.067* | |
C23 | 0.42289 (17) | 0.26620 (13) | 0.86978 (14) | 0.0495 (5) | |
C24 | 0.30695 (19) | 0.28571 (15) | 0.88297 (17) | 0.0638 (6) | |
H24 | 0.2546 | 0.2455 | 0.8914 | 0.077* | |
C25 | 0.27089 (19) | 0.36122 (14) | 0.88355 (17) | 0.0610 (6) | |
H25 | 0.1941 | 0.3717 | 0.8915 | 0.073* | |
C26 | 0.34722 (19) | 0.42483 (14) | 0.87234 (15) | 0.0555 (6) | |
C27 | 0.45897 (18) | 0.40742 (14) | 0.85991 (16) | 0.0572 (6) | |
H27 | 0.5103 | 0.4485 | 0.8530 | 0.069* | |
C28 | 0.49990 (17) | 0.32879 (13) | 0.85706 (15) | 0.0508 (5) | |
C29 | 0.61372 (19) | 0.30932 (15) | 0.84004 (18) | 0.0674 (7) | |
H29 | 0.6663 | 0.3495 | 0.8324 | 0.081* | |
C30 | 0.64847 (19) | 0.23352 (15) | 0.83459 (17) | 0.0652 (7) | |
H30 | 0.7241 | 0.2226 | 0.8230 | 0.078* | |
C31 | 0.3031 (2) | 0.50676 (15) | 0.87157 (16) | 0.0612 (6) | |
C32 | 0.1955 (2) | 0.52375 (18) | 0.82913 (17) | 0.0785 (8) | |
H32 | 0.1523 | 0.4833 | 0.8015 | 0.094* | |
C33 | 0.1524 (3) | 0.5984 (2) | 0.8274 (2) | 0.1016 (11) | |
H33 | 0.0807 | 0.6084 | 0.7988 | 0.122* | |
C34 | 0.2148 (4) | 0.6583 (2) | 0.8675 (3) | 0.1142 (14) | |
H34 | 0.1857 | 0.7093 | 0.8656 | 0.137* | |
C35 | 0.3212 (4) | 0.64385 (18) | 0.9111 (2) | 0.1007 (11) | |
H35 | 0.3632 | 0.6847 | 0.9389 | 0.121* | |
C36 | 0.3648 (3) | 0.56727 (16) | 0.91295 (19) | 0.0773 (8) | |
H36 | 0.4360 | 0.5572 | 0.9424 | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Al1 | 0.0444 (3) | 0.0488 (4) | 0.0502 (4) | 0.0009 (3) | 0.0035 (3) | −0.0033 (3) |
O1 | 0.0540 (8) | 0.0550 (9) | 0.0536 (9) | −0.0035 (7) | 0.0025 (7) | 0.0002 (7) |
O2 | 0.0525 (8) | 0.0651 (10) | 0.0606 (10) | −0.0064 (7) | 0.0111 (7) | −0.0097 (8) |
O3 | 0.0605 (9) | 0.0566 (10) | 0.0750 (11) | 0.0129 (8) | −0.0059 (8) | −0.0097 (8) |
N1 | 0.0510 (10) | 0.0570 (12) | 0.0501 (11) | 0.0034 (9) | 0.0006 (8) | −0.0013 (9) |
N2 | 0.0483 (10) | 0.0493 (11) | 0.0516 (11) | 0.0032 (8) | 0.0026 (8) | −0.0025 (8) |
C1 | 0.0362 (10) | 0.0522 (14) | 0.0625 (15) | 0.0027 (9) | 0.0033 (9) | −0.0103 (11) |
C2 | 0.0416 (11) | 0.0472 (13) | 0.0656 (15) | 0.0012 (9) | 0.0058 (10) | −0.0046 (11) |
C3 | 0.0693 (15) | 0.0581 (17) | 0.0850 (18) | −0.0044 (12) | 0.0173 (14) | 0.0029 (14) |
C4 | 0.0764 (18) | 0.0541 (17) | 0.125 (3) | −0.0110 (13) | 0.0233 (18) | −0.0136 (18) |
C5 | 0.0647 (16) | 0.074 (2) | 0.111 (3) | −0.0095 (14) | 0.0099 (16) | −0.0341 (18) |
C6 | 0.0460 (12) | 0.0624 (16) | 0.0802 (19) | 0.0016 (11) | 0.0045 (12) | −0.0223 (14) |
C7 | 0.0665 (16) | 0.098 (2) | 0.072 (2) | 0.0064 (16) | −0.0058 (14) | −0.0303 (17) |
C8 | 0.0859 (19) | 0.109 (3) | 0.0522 (16) | 0.0105 (18) | −0.0051 (14) | −0.0104 (16) |
C9 | 0.0704 (15) | 0.0770 (18) | 0.0538 (15) | 0.0038 (13) | −0.0004 (12) | −0.0008 (13) |
C10 | 0.137 (3) | 0.093 (2) | 0.0670 (19) | −0.008 (2) | 0.0082 (18) | 0.0218 (17) |
C11 | 0.0467 (12) | 0.0382 (12) | 0.0614 (14) | 0.0011 (9) | −0.0034 (10) | 0.0048 (10) |
C12 | 0.0444 (11) | 0.0406 (12) | 0.0735 (16) | 0.0016 (9) | 0.0079 (11) | 0.0059 (11) |
C13 | 0.0503 (13) | 0.0483 (14) | 0.105 (2) | 0.0029 (11) | 0.0184 (13) | 0.0103 (13) |
C14 | 0.0442 (14) | 0.0553 (17) | 0.148 (3) | −0.0030 (12) | −0.0022 (17) | 0.0221 (19) |
C15 | 0.0592 (16) | 0.0552 (16) | 0.117 (3) | −0.0065 (12) | −0.0295 (16) | 0.0149 (17) |
C16 | 0.0632 (15) | 0.0418 (13) | 0.0792 (19) | −0.0008 (11) | −0.0222 (13) | 0.0067 (12) |
C17 | 0.101 (2) | 0.0550 (16) | 0.0721 (19) | −0.0028 (14) | −0.0333 (17) | −0.0022 (14) |
C18 | 0.097 (2) | 0.0649 (17) | 0.0548 (15) | 0.0093 (15) | −0.0097 (14) | −0.0056 (13) |
C19 | 0.0695 (15) | 0.0521 (14) | 0.0529 (14) | 0.0117 (11) | 0.0037 (12) | −0.0007 (11) |
C20 | 0.0737 (17) | 0.105 (2) | 0.0658 (17) | 0.0120 (15) | 0.0219 (14) | −0.0043 (15) |
C21 | 0.0525 (13) | 0.0518 (14) | 0.0504 (13) | 0.0057 (10) | −0.0060 (10) | −0.0056 (10) |
C22 | 0.0517 (13) | 0.0520 (14) | 0.0637 (15) | −0.0030 (10) | 0.0048 (11) | −0.0012 (11) |
C23 | 0.0451 (11) | 0.0533 (14) | 0.0506 (13) | −0.0003 (10) | 0.0060 (9) | −0.0028 (10) |
C24 | 0.0518 (13) | 0.0587 (15) | 0.0822 (17) | −0.0047 (11) | 0.0155 (12) | −0.0021 (13) |
C25 | 0.0481 (12) | 0.0639 (16) | 0.0720 (16) | 0.0041 (11) | 0.0125 (11) | −0.0042 (13) |
C26 | 0.0586 (13) | 0.0592 (15) | 0.0486 (13) | 0.0106 (11) | 0.0028 (10) | −0.0012 (11) |
C27 | 0.0521 (13) | 0.0540 (14) | 0.0655 (15) | −0.0030 (10) | 0.0039 (11) | 0.0002 (11) |
C28 | 0.0445 (11) | 0.0537 (14) | 0.0542 (13) | −0.0029 (10) | 0.0023 (10) | −0.0027 (10) |
C29 | 0.0471 (13) | 0.0603 (16) | 0.096 (2) | −0.0069 (11) | 0.0105 (12) | −0.0035 (14) |
C30 | 0.0446 (12) | 0.0658 (17) | 0.0850 (18) | 0.0047 (12) | 0.0029 (11) | −0.0064 (14) |
C31 | 0.0755 (15) | 0.0602 (15) | 0.0488 (13) | 0.0152 (13) | 0.0112 (12) | 0.0050 (12) |
C32 | 0.0893 (19) | 0.090 (2) | 0.0559 (15) | 0.0314 (16) | 0.0042 (14) | 0.0093 (14) |
C33 | 0.123 (3) | 0.104 (3) | 0.079 (2) | 0.053 (2) | 0.0186 (19) | 0.029 (2) |
C34 | 0.157 (4) | 0.076 (3) | 0.115 (3) | 0.051 (3) | 0.053 (3) | 0.040 (2) |
C35 | 0.142 (3) | 0.0577 (19) | 0.107 (3) | 0.004 (2) | 0.046 (2) | −0.0018 (17) |
C36 | 0.0943 (19) | 0.0582 (17) | 0.0807 (19) | 0.0080 (14) | 0.0172 (16) | 0.0024 (14) |
Geometric parameters (Å, º) top
Al1—O3 | 1.7284 (16) | C16—C17 | 1.404 (4) |
Al1—O2 | 1.7860 (15) | C17—C18 | 1.356 (4) |
Al1—O1 | 1.7868 (16) | C17—H17 | 0.9300 |
Al1—N2 | 2.0405 (18) | C18—C19 | 1.408 (3) |
Al1—N1 | 2.0466 (18) | C18—H18 | 0.9300 |
O1—C2 | 1.347 (2) | C19—C20 | 1.490 (3) |
O2—C12 | 1.340 (3) | C20—H20A | 0.9600 |
O3—C21 | 1.338 (3) | C20—H20B | 0.9600 |
N1—C9 | 1.336 (3) | C20—H20C | 0.9600 |
N1—C1 | 1.364 (3) | C21—C22 | 1.368 (3) |
N2—C19 | 1.329 (3) | C21—C30 | 1.414 (3) |
N2—C11 | 1.375 (3) | C22—C23 | 1.403 (3) |
C1—C6 | 1.406 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.409 (3) | C23—C28 | 1.413 (3) |
C2—C3 | 1.374 (3) | C23—C24 | 1.421 (3) |
C3—C4 | 1.412 (4) | C24—C25 | 1.351 (3) |
C3—H3 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.362 (4) | C25—C26 | 1.418 (3) |
C4—H4 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.399 (4) | C26—C27 | 1.363 (3) |
C5—H5 | 0.9300 | C26—C31 | 1.485 (3) |
C6—C7 | 1.407 (4) | C27—C28 | 1.421 (3) |
C7—C8 | 1.345 (4) | C27—H27 | 0.9300 |
C7—H7 | 0.9300 | C28—C29 | 1.409 (3) |
C8—C9 | 1.405 (4) | C29—C30 | 1.354 (3) |
C8—H8 | 0.9300 | C29—H29 | 0.9300 |
C9—C10 | 1.486 (4) | C30—H30 | 0.9300 |
C10—H10A | 0.9600 | C31—C36 | 1.374 (4) |
C10—H10B | 0.9600 | C31—C32 | 1.398 (3) |
C10—H10C | 0.9600 | C32—C33 | 1.365 (4) |
C11—C16 | 1.402 (3) | C32—H32 | 0.9300 |
C11—C12 | 1.417 (3) | C33—C34 | 1.363 (5) |
C12—C13 | 1.368 (3) | C33—H33 | 0.9300 |
C13—C14 | 1.411 (4) | C34—C35 | 1.384 (5) |
C13—H13 | 0.9300 | C34—H34 | 0.9300 |
C14—C15 | 1.351 (4) | C35—C36 | 1.397 (4) |
C14—H14 | 0.9300 | C35—H35 | 0.9300 |
C15—C16 | 1.409 (4) | C36—H36 | 0.9300 |
C15—H15 | 0.9300 | | |
| | | |
O3—Al1—O2 | 124.00 (8) | C11—C16—C17 | 115.5 (2) |
O3—Al1—O1 | 116.14 (8) | C11—C16—C15 | 117.9 (3) |
O2—Al1—O1 | 119.61 (7) | C17—C16—C15 | 126.5 (3) |
O3—Al1—N2 | 96.45 (8) | C18—C17—C16 | 121.0 (2) |
O2—Al1—N2 | 84.75 (7) | C18—C17—H17 | 119.5 |
O1—Al1—N2 | 94.03 (7) | C16—C17—H17 | 119.5 |
O3—Al1—N1 | 91.62 (7) | C17—C18—C19 | 120.6 (3) |
O2—Al1—N1 | 89.20 (7) | C17—C18—H18 | 119.7 |
O1—Al1—N1 | 84.04 (7) | C19—C18—H18 | 119.7 |
N2—Al1—N1 | 171.72 (7) | N2—C19—C18 | 120.2 (2) |
C2—O1—Al1 | 116.57 (14) | N2—C19—C20 | 118.4 (2) |
C12—O2—Al1 | 116.46 (13) | C18—C19—C20 | 121.4 (2) |
C21—O3—Al1 | 147.81 (14) | C19—C20—H20A | 109.5 |
C9—N1—C1 | 119.2 (2) | C19—C20—H20B | 109.5 |
C9—N1—Al1 | 132.34 (17) | H20A—C20—H20B | 109.5 |
C1—N1—Al1 | 108.46 (14) | C19—C20—H20C | 109.5 |
C19—N2—C11 | 119.25 (19) | H20A—C20—H20C | 109.5 |
C19—N2—Al1 | 133.01 (15) | H20B—C20—H20C | 109.5 |
C11—N2—Al1 | 107.74 (14) | O3—C21—C22 | 120.3 (2) |
N1—C1—C6 | 123.3 (2) | O3—C21—C30 | 121.3 (2) |
N1—C1—C2 | 114.37 (19) | C22—C21—C30 | 118.3 (2) |
C6—C1—C2 | 122.4 (2) | C21—C22—C23 | 121.6 (2) |
O1—C2—C3 | 125.3 (2) | C21—C22—H22 | 119.2 |
O1—C2—C1 | 116.52 (19) | C23—C22—H22 | 119.2 |
C3—C2—C1 | 118.2 (2) | C22—C23—C28 | 119.73 (19) |
C2—C3—C4 | 119.5 (3) | C22—C23—C24 | 122.6 (2) |
C2—C3—H3 | 120.2 | C28—C23—C24 | 117.6 (2) |
C4—C3—H3 | 120.2 | C25—C24—C23 | 121.6 (2) |
C5—C4—C3 | 122.2 (3) | C25—C24—H24 | 119.2 |
C5—C4—H4 | 118.9 | C23—C24—H24 | 119.2 |
C3—C4—H4 | 118.9 | C24—C25—C26 | 121.6 (2) |
C4—C5—C6 | 119.8 (3) | C24—C25—H25 | 119.2 |
C4—C5—H5 | 120.1 | C26—C25—H25 | 119.2 |
C6—C5—H5 | 120.1 | C27—C26—C25 | 117.8 (2) |
C5—C6—C1 | 117.9 (3) | C27—C26—C31 | 122.6 (2) |
C5—C6—C7 | 126.1 (3) | C25—C26—C31 | 119.6 (2) |
C1—C6—C7 | 116.0 (2) | C26—C27—C28 | 122.4 (2) |
C8—C7—C6 | 120.1 (2) | C26—C27—H27 | 118.8 |
C8—C7—H7 | 119.9 | C28—C27—H27 | 118.8 |
C6—C7—H7 | 119.9 | C29—C28—C23 | 117.6 (2) |
C7—C8—C9 | 121.6 (3) | C29—C28—C27 | 123.4 (2) |
C7—C8—H8 | 119.2 | C23—C28—C27 | 119.02 (19) |
C9—C8—H8 | 119.2 | C30—C29—C28 | 121.6 (2) |
N1—C9—C8 | 119.8 (3) | C30—C29—H29 | 119.2 |
N1—C9—C10 | 118.5 (2) | C28—C29—H29 | 119.2 |
C8—C9—C10 | 121.7 (3) | C29—C30—C21 | 121.1 (2) |
C9—C10—H10A | 109.5 | C29—C30—H30 | 119.5 |
C9—C10—H10B | 109.5 | C21—C30—H30 | 119.5 |
H10A—C10—H10B | 109.5 | C36—C31—C32 | 118.3 (2) |
C9—C10—H10C | 109.5 | C36—C31—C26 | 121.7 (2) |
H10A—C10—H10C | 109.5 | C32—C31—C26 | 120.0 (2) |
H10B—C10—H10C | 109.5 | C33—C32—C31 | 121.4 (3) |
N2—C11—C16 | 123.4 (2) | C33—C32—H32 | 119.3 |
N2—C11—C12 | 114.58 (19) | C31—C32—H32 | 119.3 |
C16—C11—C12 | 122.0 (2) | C34—C33—C32 | 119.9 (3) |
O2—C12—C13 | 125.2 (2) | C34—C33—H33 | 120.0 |
O2—C12—C11 | 116.42 (18) | C32—C33—H33 | 120.0 |
C13—C12—C11 | 118.3 (2) | C33—C34—C35 | 120.4 (3) |
C12—C13—C14 | 119.5 (3) | C33—C34—H34 | 119.8 |
C12—C13—H13 | 120.3 | C35—C34—H34 | 119.8 |
C14—C13—H13 | 120.3 | C34—C35—C36 | 119.4 (3) |
C15—C14—C13 | 122.6 (3) | C34—C35—H35 | 120.3 |
C15—C14—H14 | 118.7 | C36—C35—H35 | 120.3 |
C13—C14—H14 | 118.7 | C31—C36—C35 | 120.5 (3) |
C14—C15—C16 | 119.7 (3) | C31—C36—H36 | 119.8 |
C14—C15—H15 | 120.2 | C35—C36—H36 | 119.8 |
C16—C15—H15 | 120.2 | | |
| | | |
O3—Al1—O1—C2 | 90.58 (15) | Al1—O2—C12—C13 | 176.69 (17) |
O2—Al1—O1—C2 | −83.96 (15) | Al1—O2—C12—C11 | −1.9 (2) |
N2—Al1—O1—C2 | −170.21 (13) | N2—C11—C12—O2 | 2.6 (3) |
N1—Al1—O1—C2 | 1.71 (14) | C16—C11—C12—O2 | −178.82 (18) |
O3—Al1—O2—C12 | 94.88 (16) | N2—C11—C12—C13 | −176.11 (18) |
O1—Al1—O2—C12 | −91.03 (16) | C16—C11—C12—C13 | 2.5 (3) |
N2—Al1—O2—C12 | 0.62 (15) | O2—C12—C13—C14 | −179.9 (2) |
N1—Al1—O2—C12 | −173.72 (15) | C11—C12—C13—C14 | −1.3 (3) |
O2—Al1—O3—C21 | −55.1 (3) | C12—C13—C14—C15 | −1.1 (4) |
O1—Al1—O3—C21 | 130.6 (3) | C13—C14—C15—C16 | 2.4 (4) |
N2—Al1—O3—C21 | 32.9 (3) | N2—C11—C16—C17 | −1.4 (3) |
N1—Al1—O3—C21 | −145.2 (3) | C12—C11—C16—C17 | −179.8 (2) |
O3—Al1—N1—C9 | 64.5 (2) | N2—C11—C16—C15 | 177.2 (2) |
O2—Al1—N1—C9 | −59.5 (2) | C12—C11—C16—C15 | −1.2 (3) |
O1—Al1—N1—C9 | −179.4 (2) | C14—C15—C16—C11 | −1.2 (3) |
N2—Al1—N1—C9 | −102.5 (6) | C14—C15—C16—C17 | 177.3 (2) |
O3—Al1—N1—C1 | −116.81 (14) | C11—C16—C17—C18 | 1.6 (3) |
O2—Al1—N1—C1 | 119.20 (14) | C15—C16—C17—C18 | −176.9 (2) |
O1—Al1—N1—C1 | −0.69 (13) | C16—C17—C18—C19 | −0.3 (4) |
N2—Al1—N1—C1 | 76.2 (6) | C11—N2—C19—C18 | 1.5 (3) |
O3—Al1—N2—C19 | 56.7 (2) | Al1—N2—C19—C18 | −178.05 (17) |
O2—Al1—N2—C19 | −179.6 (2) | C11—N2—C19—C20 | −177.5 (2) |
O1—Al1—N2—C19 | −60.2 (2) | Al1—N2—C19—C20 | 3.0 (3) |
N1—Al1—N2—C19 | −136.5 (5) | C17—C18—C19—N2 | −1.3 (4) |
O3—Al1—N2—C11 | −122.92 (13) | C17—C18—C19—C20 | 177.6 (2) |
O2—Al1—N2—C11 | 0.77 (13) | Al1—O3—C21—C22 | −145.3 (2) |
O1—Al1—N2—C11 | 120.18 (13) | Al1—O3—C21—C30 | 38.0 (4) |
N1—Al1—N2—C11 | 44.0 (6) | O3—C21—C22—C23 | −173.2 (2) |
C9—N1—C1—C6 | −0.8 (3) | C30—C21—C22—C23 | 3.6 (3) |
Al1—N1—C1—C6 | −179.66 (16) | C21—C22—C23—C28 | −3.0 (3) |
C9—N1—C1—C2 | 178.51 (19) | C21—C22—C23—C24 | 174.9 (2) |
Al1—N1—C1—C2 | −0.4 (2) | C22—C23—C24—C25 | −178.0 (2) |
Al1—O1—C2—C3 | 176.85 (17) | C28—C23—C24—C25 | −0.1 (3) |
Al1—O1—C2—C1 | −2.4 (2) | C23—C24—C25—C26 | −0.9 (4) |
N1—C1—C2—O1 | 1.8 (3) | C24—C25—C26—C27 | 0.7 (4) |
C6—C1—C2—O1 | −178.95 (17) | C24—C25—C26—C31 | 178.8 (2) |
N1—C1—C2—C3 | −177.58 (19) | C25—C26—C27—C28 | 0.6 (3) |
C6—C1—C2—C3 | 1.7 (3) | C31—C26—C27—C28 | −177.4 (2) |
O1—C2—C3—C4 | 178.9 (2) | C22—C23—C28—C29 | 0.6 (3) |
C1—C2—C3—C4 | −1.9 (3) | C24—C23—C28—C29 | −177.3 (2) |
C2—C3—C4—C5 | 0.5 (4) | C22—C23—C28—C27 | 179.3 (2) |
C3—C4—C5—C6 | 1.1 (4) | C24—C23—C28—C27 | 1.3 (3) |
C4—C5—C6—C1 | −1.3 (4) | C26—C27—C28—C29 | 176.9 (2) |
C4—C5—C6—C7 | 176.9 (2) | C26—C27—C28—C23 | −1.6 (3) |
N1—C1—C6—C5 | 179.1 (2) | C23—C28—C29—C30 | 1.0 (4) |
C2—C1—C6—C5 | −0.1 (3) | C27—C28—C29—C30 | −177.6 (2) |
N1—C1—C6—C7 | 0.7 (3) | C28—C29—C30—C21 | −0.3 (4) |
C2—C1—C6—C7 | −178.5 (2) | O3—C21—C30—C29 | 174.8 (2) |
C5—C6—C7—C8 | −178.3 (3) | C22—C21—C30—C29 | −2.0 (4) |
C1—C6—C7—C8 | −0.1 (4) | C27—C26—C31—C36 | −40.7 (3) |
C6—C7—C8—C9 | −0.5 (4) | C25—C26—C31—C36 | 141.3 (2) |
C1—N1—C9—C8 | 0.2 (3) | C27—C26—C31—C32 | 140.3 (2) |
Al1—N1—C9—C8 | 178.75 (17) | C25—C26—C31—C32 | −37.7 (3) |
C1—N1—C9—C10 | −179.0 (2) | C36—C31—C32—C33 | 0.8 (4) |
Al1—N1—C9—C10 | −0.4 (4) | C26—C31—C32—C33 | 179.9 (2) |
C7—C8—C9—N1 | 0.5 (4) | C31—C32—C33—C34 | 0.0 (5) |
C7—C8—C9—C10 | 179.6 (3) | C32—C33—C34—C35 | −0.8 (5) |
C19—N2—C11—C16 | −0.1 (3) | C33—C34—C35—C36 | 0.6 (5) |
Al1—N2—C11—C16 | 179.52 (16) | C32—C31—C36—C35 | −1.0 (4) |
C19—N2—C11—C12 | 178.41 (19) | C26—C31—C36—C35 | 180.0 (2) |
Al1—N2—C11—C12 | −1.9 (2) | C34—C35—C36—C31 | 0.3 (4) |
Selected bond lengths (Å) and angles (°) in (I) and (II). top | (I)a | (II)b |
Al—O3 | 1.7284 (16) | 1.7387 (12) |
Al—O2 | 1.7860 (15) | 1.7921 (12) |
Al—O1 | 1.7868 (16) | 1.7886 (12) |
Al—N2 | 2.0405 (18) | 2.0686 (14) |
Al—N1 | 2.0466 (18) | 2.0605 (13) |
| | |
N1—Al—N2 | 171.72 (7) | 169.50 (6) |
O3—Al—N2 | 96.45 (8) | 92.20 (5) |
O3—Al—N1 | 91.62 (7) | 98.29 (5) |
O3—Al—O2 | 124.00 (8) | 118.77 (6) |
O3—Al—O1 | 116.14 (8) | 118.16 (6) |
References: (a) this work; (b) Rajeswaran et al. (2006). |
Chemical shift assignments topProton on atom ID | Chemical shift (p.p.m.) |
C7 and C17 | 8.27 (d, J = 8.3 Hz, 2H) |
C27 | 7.77 (d, J = 1.9 Hz, 1H) |
C31 and C36 | 7.62 (d J = 8.3 and 1.2 Hz, 2H) |
C4 and C14 | 7.51 (t, J = 8.1 Hz, 2H) |
C25 | 7.47 (dd, J = 8.6 and 1.9 Hz, 1H) |
C29 | 7.43 (d, J = 8.8 Hz, 1H) |
C33 and C35 | 7.42 (t, J = 8.3 Hz, 2H) |
C8 and C18 | 7.38 (d, J = 8.3 Hz, 2H) |
C34 | 7.3 (m, 1H) |
C24 | 7.27 (d, J = 8.6 Hz, 1H) |
C5 and C15 | 7.26 (dd, J = 8.1 and 1.0 Hz , 2H) |
C3 and C13 | 7.1 (dd, J = 8.1 and 1.0 Hz, 2H) |
C30 | 6.73 (dd, J = 8.8 and 2.4 Hz, 1H) |
C22 | 6.61 (d, J = 2.4 Hz, 1H) |
C10 and C20 | 3.02 (s, 6H) |
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