Tris(N,N'-diisopropyl-benzamidinato)cerium(III).

The title compound, [Ce(C(13)H(19)N(2))(3)], was obtained in moderate yield (67%) by treatment of anhydrous cerium trichloride with three equivalents of Li[PhC(N(i)Pr)(2)] in tetra-hydro-furan. It is the first homoleptic lanthanide complex of this amidinate ligand. The central Ce(III) ion is coordinated by three chelating benzamidinate anions in a distorted octa-hedral fashion, with Ce-N distances in the narrow range 2.482 (2)-2.492 (2) Å. The dihedral angles between the phenyl rings and the chelating N-C-N units are in the range 73.3-87.9°, thus preventing conjugation between the two π-systems. The mol-ecule is located on a twofold rotation axis, and one of the phenyl rings is equally disordered over two alternative symmetry-equivalent positions around this axis.

Related literature

For general background to lanthanide coordination complexes, see: Bailey & Pace (2001 ▶); Edelmann et al. (2002 ▶); Edelmann (2009 ▶). Wedler et al. (1992 ▶) describe complexes related to the title compound. For applications of homoleptic metal amid­inato complexes, see: Lim et al. (2003 ▶); Päiväsaari et al. (2005 ▶).

Experimental

Crystal data

[Ce(C13H19N2)3]

M = 750.03

Monoclinic,

a = 14.1225 (4) Å

b = 18.5957 (6) Å

c = 15.6544 (4) Å

β = 98.324 (2)°

V = 4067.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.15 mm−1

T = 133 K

0.30 × 0.20 × 0.10 mm

Data collection

Stoe IPDS 2T diffractometer

32963 measured reflections

5485 independent reflections

5147 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.061

S = 1.11

5485 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −1.00 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042704/zl2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042704/zl2316Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ce(C13H19N2)3]	F(000) = 1564
Mr = 750.03	Dx = 1.225 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1225 (4) Å	Cell parameters from 58857 reflections
b = 18.5957 (6) Å	θ = 2.1–29.6°
c = 15.6544 (4) Å	µ = 1.15 mm−1
β = 98.324 (2)°	T = 133 K
V = 4067.8 (2) Å3	Prism, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Stoe IPDS 2T diffractometer	5147 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
plane graphite	θmax = 29.2°, θmin = 2.1°
Detector resolution: 6.67 pixels mm-1	h = −19→19
rotation method scans	k = −25→25
32963 measured reflections	l = −21→20
5485 independent 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.031P)2 + 1.6552P] where P = (Fo2 + 2Fc2)/3
5485 reflections	(Δ/σ)max = 0.002
230 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −1.00 e Å−3

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. The phenyl ring with two carbon atoms located on the C2 rotation axis lies in two alternative symmetry related positions.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ce	0.5000	0.699350 (7)	0.7500	0.03398 (5)
N1	0.56280 (13)	0.78730 (10)	0.86347 (14)	0.0595 (5)
N2	0.41661 (11)	0.74104 (9)	0.87036 (11)	0.0465 (4)
N3	0.57059 (11)	0.57999 (8)	0.79492 (11)	0.0471 (4)
C1	0.48506 (13)	0.78591 (10)	0.90212 (13)	0.0444 (4)
C2	0.47606 (12)	0.83394 (10)	0.97814 (12)	0.0413 (4)
C3	0.52818 (15)	0.82015 (13)	1.05786 (14)	0.0526 (4)
H3	0.5700	0.7799	1.0648	0.063*
C4	0.52048 (16)	0.86400 (15)	1.12785 (15)	0.0599 (5)
H4	0.5566	0.8536	1.1825	0.072*
C5	0.46115 (17)	0.92218 (13)	1.11859 (15)	0.0592 (5)
H5	0.4554	0.9521	1.1667	0.071*
C6	0.40972 (18)	0.93729 (12)	1.03927 (16)	0.0606 (5)
H6	0.3692	0.9783	1.0325	0.073*
C7	0.41652 (16)	0.89307 (11)	0.96895 (14)	0.0521 (4)
H7	0.3801	0.9036	0.9145	0.062*
C8	0.33639 (13)	0.72355 (12)	0.91592 (13)	0.0475 (4)
H8	0.3350	0.7586	0.9641	0.057*
C9	0.3499 (2)	0.64907 (17)	0.9530 (2)	0.0829 (9)
H9A	0.3575	0.6149	0.9068	0.124*
H9B	0.2938	0.6357	0.9798	0.124*
H9C	0.4071	0.6480	0.9966	0.124*
C10	0.24360 (16)	0.7286 (2)	0.85526 (17)	0.0734 (7)
H10A	0.2345	0.7780	0.8338	0.110*
H10B	0.1904	0.7153	0.8860	0.110*
H10C	0.2454	0.6958	0.8065	0.110*
C11	0.63744 (17)	0.84142 (15)	0.88303 (17)	0.0688 (7)
H11	0.6314	0.8656	0.9391	0.083*
C12	0.6317 (3)	0.89570 (16)	0.8125 (3)	0.1140 (15)
H12A	0.6431	0.8721	0.7589	0.171*
H12B	0.6803	0.9329	0.8280	0.171*
H12C	0.5680	0.9178	0.8040	0.171*
C13	0.7336 (2)	0.8035 (2)	0.8890 (3)	0.1099 (14)
H13A	0.7361	0.7641	0.9309	0.165*
H13B	0.7851	0.8378	0.9076	0.165*
H13C	0.7414	0.7840	0.8322	0.165*
C14	0.5000	0.54307 (13)	0.7500	0.0408 (5)
C15	0.5009 (10)	0.46299 (10)	0.7603 (6)	0.0382 (13)	0.50
C16	0.4568 (8)	0.4312 (3)	0.8245 (4)	0.068 (2)	0.50
H16	0.4272	0.4603	0.8630	0.081*	0.50
C17	0.4559 (5)	0.3567 (3)	0.8326 (3)	0.088 (2)	0.50
H17	0.4258	0.3350	0.8765	0.105*	0.50
C18	0.4992 (6)	0.31412 (11)	0.7763 (4)	0.074 (2)	0.50
H18	0.4986	0.2633	0.7818	0.089*	0.50
C17A	0.5434 (4)	0.3460 (2)	0.7121 (3)	0.0754 (19)	0.50
H17A	0.5729	0.3168	0.6736	0.090*	0.50
C16A	0.5442 (7)	0.4204 (2)	0.7040 (4)	0.0574 (15)	0.50
H16A	0.5744	0.4421	0.6601	0.069*	0.50
C19	0.64510 (15)	0.54478 (12)	0.85451 (16)	0.0561 (5)
H19	0.6431	0.4920	0.8424	0.067*
C20	0.74139 (19)	0.5732 (2)	0.8419 (3)	0.0961 (11)
H20A	0.7531	0.5625	0.7830	0.144*
H20B	0.7909	0.5502	0.8833	0.144*
H20C	0.7432	0.6253	0.8511	0.144*
C21	0.6265 (3)	0.5570 (3)	0.9468 (2)	0.1027 (12)
H21A	0.6280	0.6086	0.9593	0.154*
H21B	0.6759	0.5326	0.9869	0.154*
H21C	0.5635	0.5376	0.9536	0.154*

	U11	U22	U33	U12	U13	U23
Ce	0.03793 (7)	0.03059 (7)	0.03552 (7)	0.000	0.01243 (5)	0.000
N1	0.0504 (9)	0.0655 (11)	0.0698 (12)	−0.0243 (8)	0.0333 (8)	−0.0329 (9)
N2	0.0442 (7)	0.0518 (9)	0.0486 (8)	−0.0133 (7)	0.0235 (7)	−0.0136 (7)
N3	0.0468 (8)	0.0351 (7)	0.0554 (9)	0.0003 (6)	−0.0058 (7)	0.0001 (6)
C1	0.0440 (8)	0.0453 (9)	0.0476 (9)	−0.0064 (7)	0.0195 (7)	−0.0107 (7)
C2	0.0411 (8)	0.0422 (9)	0.0439 (9)	−0.0063 (7)	0.0174 (7)	−0.0080 (7)
C3	0.0478 (10)	0.0607 (11)	0.0509 (11)	0.0047 (9)	0.0124 (8)	−0.0057 (9)
C4	0.0549 (11)	0.0809 (15)	0.0447 (10)	−0.0078 (11)	0.0102 (9)	−0.0118 (10)
C5	0.0656 (12)	0.0619 (13)	0.0543 (11)	−0.0135 (10)	0.0229 (10)	−0.0223 (10)
C6	0.0748 (14)	0.0459 (10)	0.0651 (13)	0.0059 (10)	0.0232 (11)	−0.0104 (10)
C7	0.0615 (11)	0.0483 (10)	0.0481 (10)	0.0035 (9)	0.0138 (8)	−0.0037 (8)
C8	0.0432 (9)	0.0557 (10)	0.0478 (10)	−0.0125 (8)	0.0215 (8)	−0.0093 (8)
C9	0.0660 (15)	0.0777 (18)	0.112 (2)	−0.0061 (13)	0.0372 (15)	0.0276 (17)
C10	0.0447 (11)	0.117 (2)	0.0627 (14)	−0.0066 (12)	0.0206 (10)	−0.0024 (15)
C11	0.0597 (12)	0.0783 (16)	0.0766 (15)	−0.0355 (12)	0.0377 (11)	−0.0441 (13)
C12	0.093 (2)	0.0517 (15)	0.193 (4)	−0.0297 (15)	0.006 (3)	0.003 (2)
C13	0.0566 (15)	0.127 (3)	0.139 (4)	−0.0321 (17)	−0.0075 (19)	0.001 (3)
C14	0.0412 (11)	0.0337 (11)	0.0476 (13)	0.000	0.0075 (10)	0.000
C15	0.0347 (11)	0.0388 (12)	0.041 (4)	0.004 (2)	0.005 (3)	−0.0062 (17)
C16	0.079 (4)	0.047 (3)	0.087 (6)	0.006 (3)	0.043 (5)	0.005 (3)
C17	0.097 (5)	0.056 (3)	0.120 (7)	0.005 (3)	0.053 (5)	0.017 (4)
C18	0.076 (3)	0.0347 (19)	0.113 (7)	−0.001 (2)	0.021 (5)	0.004 (2)
C17A	0.089 (4)	0.035 (3)	0.111 (6)	0.008 (3)	0.045 (4)	−0.013 (3)
C16A	0.071 (3)	0.038 (2)	0.070 (4)	0.003 (2)	0.035 (3)	−0.004 (2)
C19	0.0502 (10)	0.0450 (10)	0.0678 (13)	0.0025 (8)	−0.0093 (9)	0.0033 (9)
C20	0.0523 (13)	0.106 (2)	0.124 (3)	−0.0045 (14)	−0.0092 (15)	0.042 (2)
C21	0.098 (2)	0.143 (3)	0.0621 (17)	0.027 (2)	−0.0057 (16)	0.018 (2)

Ce—N1	2.4820 (17)	C10—H10B	0.9800
Ce—N1i	2.4820 (17)	C10—H10C	0.9800
Ce—N2	2.4860 (14)	C11—C12	1.490 (5)
Ce—N2i	2.4860 (14)	C11—C13	1.521 (5)
Ce—N3i	2.4924 (15)	C11—H11	1.0000
Ce—N3	2.4924 (15)	C12—H12A	0.9800
Ce—C14	2.906 (2)	C12—H12B	0.9800
Ce—C1	2.9071 (18)	C12—H12C	0.9800
Ce—C1i	2.9071 (18)	C13—H13A	0.9800
N1—C1	1.328 (2)	C13—H13B	0.9800
N1—C11	1.458 (2)	C13—H13C	0.9800
N2—C1	1.319 (2)	C14—N3i	1.325 (2)
N2—C8	1.460 (2)	C14—C15i	1.498 (3)
N3—C14	1.325 (2)	C14—C15	1.498 (3)
N3—C19	1.457 (2)	C15—C16	1.3900
C1—C2	1.508 (2)	C15—C16A	1.3900
C2—C3	1.378 (3)	C16—C17	1.3900
C2—C7	1.379 (3)	C16—H16	0.9500
C3—C4	1.383 (3)	C17—C18	1.3900
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.363 (4)	C18—C17A	1.3900
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.374 (4)	C17A—C16A	1.3900
C5—H5	0.9500	C17A—H17A	0.9500
C6—C7	1.389 (3)	C16A—H16A	0.9500
C6—H6	0.9500	C19—C20	1.498 (4)
C7—H7	0.9500	C19—C21	1.522 (4)
C8—C9	1.503 (4)	C19—H19	1.0000
C8—C10	1.506 (3)	C20—H20A	0.9800
C8—H8	1.0000	C20—H20B	0.9800
C9—H9A	0.9800	C20—H20C	0.9800
C9—H9B	0.9800	C21—H21A	0.9800
C9—H9C	0.9800	C21—H21B	0.9800
C10—H10A	0.9800	C21—H21C	0.9800
N1—Ce—N1i	97.57 (11)	C8—C9—H9C	109.5
N1—Ce—N2	53.95 (5)	H9A—C9—H9C	109.5
N1i—Ce—N2	100.23 (6)	H9B—C9—H9C	109.5
N1—Ce—N2i	100.23 (6)	C8—C10—H10A	109.5
N1i—Ce—N2i	53.95 (5)	C8—C10—H10B	109.5
N2—Ce—N2i	143.66 (8)	H10A—C10—H10B	109.5
N1—Ce—N3i	151.12 (7)	C8—C10—H10C	109.5
N1i—Ce—N3i	107.34 (7)	H10A—C10—H10C	109.5
N2—Ce—N3i	106.11 (6)	H10B—C10—H10C	109.5
N2i—Ce—N3i	106.13 (6)	N1—C11—C12	110.6 (2)
N1—Ce—N3	107.34 (7)	N1—C11—C13	107.7 (2)
N1i—Ce—N3	151.12 (7)	C12—C11—C13	108.2 (3)
N2—Ce—N3	106.13 (6)	N1—C11—H11	110.1
N2i—Ce—N3	106.11 (6)	C12—C11—H11	110.1
N3i—Ce—N3	54.12 (7)	C13—C11—H11	110.1
N1—Ce—C14	131.22 (6)	C11—C12—H12A	109.5
N1i—Ce—C14	131.22 (6)	C11—C12—H12B	109.5
N2—Ce—C14	108.17 (4)	H12A—C12—H12B	109.5
N2i—Ce—C14	108.17 (4)	C11—C12—H12C	109.5
N1i—Ce—C1	99.24 (7)	H12A—C12—H12C	109.5
N2i—Ce—C1	123.14 (6)	H12B—C12—H12C	109.5
N3i—Ce—C1	130.59 (6)	C11—C13—H13A	109.5
N3—Ce—C1	109.60 (6)	C11—C13—H13B	109.5
C14—Ce—C1	123.62 (4)	H13A—C13—H13B	109.5
N1—Ce—C1i	99.24 (7)	C11—C13—H13C	109.5
N2—Ce—C1i	123.14 (6)	H13A—C13—H13C	109.5
N3i—Ce—C1i	109.60 (6)	H13B—C13—H13C	109.5
N3—Ce—C1i	130.59 (6)	N3—C14—N3i	117.6 (2)
C14—Ce—C1i	123.62 (4)	N3—C14—C15i	124.5 (6)
C1—Ce—C1i	112.76 (8)	N3i—C14—C15i	117.6 (6)
C1—N1—C11	122.56 (17)	N3—C14—C15	117.6 (6)
C1—N1—Ce	94.58 (12)	N3i—C14—C15	124.5 (6)
C11—N1—Ce	141.07 (13)	N3—C14—Ce	58.81 (11)
C1—N2—C8	122.34 (16)	N3i—C14—Ce	58.81 (11)
C1—N2—Ce	94.66 (10)	C15i—C14—Ce	173.9 (3)
C8—N2—Ce	141.91 (12)	C15—C14—Ce	173.9 (3)
C14—N3—C19	121.67 (16)	C16—C15—C16A	120.0
C14—N3—Ce	94.14 (12)	C16—C15—C14	120.2 (5)
C19—N3—Ce	143.45 (13)	C16A—C15—C14	119.8 (5)
N2—C1—N1	116.73 (16)	C17—C16—C15	120.0
N2—C1—C2	122.10 (15)	C17—C16—H16	120.0
N1—C1—C2	121.17 (16)	C15—C16—H16	120.0
N2—C1—Ce	58.46 (9)	C16—C17—C18	120.0
N1—C1—Ce	58.33 (10)	C16—C17—H17	120.0
C2—C1—Ce	177.18 (14)	C18—C17—H17	120.0
C3—C2—C7	118.72 (18)	C17A—C18—C17	120.0
C3—C2—C1	120.63 (18)	C17A—C18—H18	120.0
C7—C2—C1	120.65 (18)	C17—C18—H18	120.0
C2—C3—C4	121.0 (2)	C18—C17A—C16A	120.0
C2—C3—H3	119.5	C18—C17A—H17A	120.0
C4—C3—H3	119.5	C16A—C17A—H17A	120.0
C5—C4—C3	120.1 (2)	C17A—C16A—C15	120.0
C5—C4—H4	120.0	C17A—C16A—H16A	120.0
C3—C4—H4	120.0	C15—C16A—H16A	120.0
C4—C5—C6	119.7 (2)	N3—C19—C20	110.0 (2)
C4—C5—H5	120.2	N3—C19—C21	109.4 (2)
C6—C5—H5	120.2	C20—C19—C21	111.0 (3)
C5—C6—C7	120.5 (2)	N3—C19—H19	108.8
C5—C6—H6	119.8	C20—C19—H19	108.8
C7—C6—H6	119.8	C21—C19—H19	108.8
C2—C7—C6	120.0 (2)	C19—C20—H20A	109.5
C2—C7—H7	120.0	C19—C20—H20B	109.5
C6—C7—H7	120.0	H20A—C20—H20B	109.5
N2—C8—C9	109.27 (18)	C19—C20—H20C	109.5
N2—C8—C10	110.12 (17)	H20A—C20—H20C	109.5
C9—C8—C10	110.5 (2)	H20B—C20—H20C	109.5
N2—C8—H8	109.0	C19—C21—H21A	109.5
C9—C8—H8	109.0	C19—C21—H21B	109.5
C10—C8—H8	109.0	H21A—C21—H21B	109.5
C8—C9—H9A	109.5	C19—C21—H21C	109.5
C8—C9—H9B	109.5	H21A—C21—H21C	109.5
H9A—C9—H9B	109.5	H21B—C21—H21C	109.5
N1i—Ce—N1—C1	95.52 (15)	C14—Ce—C1—N2	−61.08 (14)
N2—Ce—N1—C1	−1.66 (13)	C1i—Ce—C1—N2	118.92 (14)
N2i—Ce—N1—C1	150.12 (14)	N1i—Ce—C1—N1	−88.55 (18)
N3i—Ce—N1—C1	−54.1 (2)	N2—Ce—C1—N1	177.0 (2)
N3—Ce—N1—C1	−99.29 (15)	N2i—Ce—C1—N1	−35.84 (17)
C14—Ce—N1—C1	−84.48 (15)	N3i—Ce—C1—N1	148.96 (14)
C1i—Ce—N1—C1	122.86 (14)	N3—Ce—C1—N1	89.91 (15)
N1i—Ce—N1—C11	−67.9 (3)	C14—Ce—C1—N1	115.96 (14)
N2—Ce—N1—C11	−165.1 (3)	C1i—Ce—C1—N1	−64.04 (14)
N2i—Ce—N1—C11	−13.3 (3)	N2—C1—C2—C3	107.5 (2)
N3i—Ce—N1—C11	142.4 (3)	N1—C1—C2—C3	−73.0 (3)
N3—Ce—N1—C11	97.3 (3)	N2—C1—C2—C7	−73.4 (3)
C14—Ce—N1—C11	112.1 (3)	N1—C1—C2—C7	106.2 (2)
C1—Ce—N1—C11	−163.4 (4)	C7—C2—C3—C4	0.7 (3)
C1i—Ce—N1—C11	−40.5 (3)	C1—C2—C3—C4	179.88 (19)
N1—Ce—N2—C1	1.67 (13)	C2—C3—C4—C5	−0.4 (4)
N1i—Ce—N2—C1	−90.29 (14)	C3—C4—C5—C6	−0.5 (4)
N2i—Ce—N2—C1	−50.10 (12)	C4—C5—C6—C7	1.1 (4)
N3i—Ce—N2—C1	158.16 (12)	C3—C2—C7—C6	−0.2 (3)
N3—Ce—N2—C1	101.64 (13)	C1—C2—C7—C6	−179.3 (2)
C14—Ce—N2—C1	129.90 (12)	C5—C6—C7—C2	−0.8 (4)
C1i—Ce—N2—C1	−74.56 (17)	C1—N2—C8—C9	−105.7 (3)
N1—Ce—N2—C8	−165.3 (3)	Ce—N2—C8—C9	58.8 (3)
N1i—Ce—N2—C8	102.8 (2)	C1—N2—C8—C10	132.7 (2)
N2i—Ce—N2—C8	143.0 (2)	Ce—N2—C8—C10	−62.8 (3)
N3i—Ce—N2—C8	−8.8 (2)	C1—N1—C11—C12	−104.8 (3)
N3—Ce—N2—C8	−65.3 (2)	Ce—N1—C11—C12	55.4 (4)
C14—Ce—N2—C8	−37.0 (2)	C1—N1—C11—C13	137.2 (3)
C1—Ce—N2—C8	−166.9 (3)	Ce—N1—C11—C13	−62.6 (4)
C1i—Ce—N2—C8	118.5 (2)	C19—N3—C14—N3i	172.3 (2)
N1—Ce—N3—C14	155.00 (8)	C19—N3—C14—C15i	−13.8 (4)
N1i—Ce—N3—C14	−56.63 (17)	Ce—N3—C14—C15i	173.9 (3)
N2—Ce—N3—C14	98.47 (9)	C19—N3—C14—C15	−2.0 (4)
N2i—Ce—N3—C14	−98.51 (9)	Ce—N3—C14—C15	−174.3 (3)
C1—Ce—N3—C14	126.50 (9)	C19—N3—C14—Ce	172.3 (2)
C1i—Ce—N3—C14	−85.72 (11)	N1—Ce—C14—N3	−32.43 (11)
N1—Ce—N3—C19	−14.0 (3)	N1i—Ce—C14—N3	147.57 (11)
N1i—Ce—N3—C19	134.4 (2)	N2—Ce—C14—N3	−90.02 (10)
N2—Ce—N3—C19	−70.5 (3)	N2i—Ce—C14—N3	89.98 (10)
N2i—Ce—N3—C19	92.5 (3)	C1—Ce—C14—N3	−65.41 (11)
N3i—Ce—N3—C19	−169.0 (3)	C1i—Ce—C14—N3	114.59 (11)
C14—Ce—N3—C19	−169.0 (3)	N1—Ce—C14—N3i	147.57 (11)
C1—Ce—N3—C19	−42.5 (3)	N1i—Ce—C14—N3i	−32.43 (11)
C1i—Ce—N3—C19	105.3 (3)	N2—Ce—C14—N3i	89.98 (10)
C8—N2—C1—N1	167.7 (2)	N2i—Ce—C14—N3i	−90.02 (10)
Ce—N2—C1—N1	−2.8 (2)	C1—Ce—C14—N3i	114.59 (11)
C8—N2—C1—C2	−12.8 (3)	C1i—Ce—C14—N3i	−65.41 (11)
Ce—N2—C1—C2	176.75 (17)	N3—C14—C15—C16	88.9 (6)
C8—N2—C1—Ce	170.5 (2)	N3i—C14—C15—C16	−85.0 (5)
C11—N1—C1—N2	170.5 (2)	C15i—C14—C15—C16	−144 (5)
Ce—N1—C1—N2	2.8 (2)	N3—C14—C15—C16A	−92.6 (5)
C11—N1—C1—C2	−9.0 (4)	N3i—C14—C15—C16A	93.5 (6)
Ce—N1—C1—C2	−176.75 (17)	C15i—C14—C15—C16A	34 (4)
C11—N1—C1—Ce	167.7 (3)	C14—C15—C16—C17	178.5 (11)
N1—Ce—C1—N2	−177.0 (2)	C14—C15—C16A—C17A	−178.5 (11)
N1i—Ce—C1—N2	94.41 (13)	C14—N3—C19—C20	134.4 (2)
N2i—Ce—C1—N2	147.12 (11)	Ce—N3—C19—C20	−58.5 (4)
N3i—Ce—C1—N2	−28.07 (16)	C14—N3—C19—C21	−103.4 (3)
N3—Ce—C1—N2	−87.12 (13)	Ce—N3—C19—C21	63.7 (3)