Bis(2-methyl­quinolin-8-olato-κ2N,O)(6-phenyl-2-naphtholato-κO)aluminium(III)

Rajeswaran, M.; Place, D.W.; Bakos, V.W.; Deaton, J.C.; Brown, C.T.; Lenhart, W.C.

doi:10.1107/S160053680605104X

Buy article online - an online subscription or single-article purchase is required to access this article.

Bis(2-methylquinolin-8-olato-κ²N,O)(6-phenyl-2-naphtholato-κO)aluminium(III)

M. Rajeswaran, D. W. Place, V. W. Bakos, J. C. Deaton, C. T. Brown and W. C. Lenhart

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605104X/ng2167sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680605104X/ng2167Isup2.hkl Contains datablock I

CCDC reference: 633965

checkCIF report

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

Computing details top

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
M_r = 562.58	D_x = 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	R_int = 0.095
Detector resolution: 9 pixels mm^-1	θ_max = 27.4°, θ_min = 4.0°
φ and ω scans	h = −15→15
Absorption correction: multi-scan [from symmetry-related measurements; SORTAV (Blessing, 1995)]	k = −21→21
T_min = 0.786, T_max = 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(F_o²) + (0.0723P)²] where P = (F_o² + 2F_c²)/3
6568 reflections	(Δ/σ)_max < 0.001
381 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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 top

Proton 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)

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page