Crystal structures of two ytterbium(III) complexes comprising alkynylamidinate ligands.

Two ytterbium(III) complexes comprising alkynylamidinate ligands, namely bis-(η5-cyclo-penta-dien-yl)(3-cyclo-propyl-N,N'-diiso-propyl-propynamidinato-κ2N,N')ytterbium(III), [Yb(C5H5)2(C12H19N2)] or Cp2Yb[( i Pr2N)2C-C≡C-c-C3H5] (1) and tris-(3-phenyl-N,N'-di-cyclo-hexyl-propynamidinato-κ2N,N')ytterbium(III), [Yb(C21H27N2)3] or Yb[(CyN)2C-C≡C-Ph]3 (Cy = cyclo-hex-yl) (2) have been synthesized and structurally characterized. Both complexes are monomers; for complex 2, the contribution to the scattering from highly disordered toluene solvent molecules in these voids was removed with the SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9-18] in PLATON. The stated crystal data for Mr, μ etc. do not take these into account.

Chemical context

Anionic amidinate ligands of the type [RC(NR′)2]− (R = H, alkyl, aryl; R′ = alkyl, cyclo­alkyl, aryl, SiMe3) are highly useful and versatile spectator ligands in organolanthanide chemistry. These readily available N-chelating ligands are generally regarded as sterically demanding cyclo­penta­dienyl equivalents (Collins, 2011 ▸; Edelmann, 2013 ▸). Mono-, di- and tris­ubstituted lanthanide amidinate complexes are all accessible, in close analogy to the long known mono-, di- and tri­cyclo­penta­dienyl complexes. Over the past ca 25 years, lanthanide amidinates have witnessed an impressive transformation from laboratory curiosities to homogeneous catalysts as well as valuable precursors in materials science. Rare-earth metal amidinates have been reported to be highly active homogeneous catalysts e.g. for ring-opening polymerization reactions of lactones, the guanylation of amines or the addition of terminal alkynes to carbodi­imides (Edelmann, 2009 ▸, 2012 ▸). In materials science, certain homoleptic alkyl-substituted lanthanide tris(amidinate) complexes are highly volatile and can be used as precursors for ALD (atomic layer deposition) and MOCVD (metal–organic chemical vapor deposition) processes, e.g. for the deposition of lanthanide oxide (Ln 2O3) or lanthanide nitride (LnN) thin films (Devi, 2013 ▸).

Introduction of alkynyl groups to the central C atom in amidines provides alkynyl­amidines of the general type R—C≡C—C(NR′)(NHR′). In organic synthesis, alkynyl­amidines have been frequently employed in the preparation of various heterocycles (Ong et al., 2006 ▸; Xu et al., 2008 ▸; Weingärtner & Maas, 2012 ▸). Alkynyl­amidines are also useful for diverse applications in biological and pharmacological systems (Rowley et al., 2005 ▸; Sienkiewicz et al., 2005 ▸). Thus far, only a few lanthanide complexes containing alkynylamidinate ligands have been described. Previously used alkynylamidinate ligands include e.g. phenyl­ethynyl derivatives [Ph—C≡C—C(NR)2]− (R = Pr, Bu) (Dröse et al., 2010a ▸,b ▸; Xu et al., 2013 ▸) and the tri­methyl­silyl-substituted anions [Me3Si—C≡C—C(NR)2]− [R = cyclo­hexyl (Cy), Pr] (Seidel et al., 2012 ▸).

We recently initiated a study of alkynylamidinates derived from cyclo­propyl­acetyl­ene (Sroor et al., 2015c ▸). The cyclo­propyl group was chosen because of the well-known electron-donating ability of this substituent to an adjacent electron-deficient atom or group. This would give us the rare chance to electronically influence the amidinate ligand system rather than altering only its steric demand. We now describe the synthesis and structural characterization of two new ytterbium(III) alkynylamidinate complexes, namely Cp2Yb[(PrN)2C—C≡C—c-C3H5] (1) and Yb[(CyN)2C—C≡C—Ph]3 (Cy = cyclo­hexyl; 2), shown in Figs. 1 ▸ and 2 ▸.

Figure 1

The mol­ecular structure of compound 1.

Figure 2

The mol­ecular structure of compound 2. Displacement ellipsoids are at the 50% probability level and H atoms have been omitted for clarity. Only one orientation of the disordered cyclo­hexyl group at N2 is shown. The Yb atom is located on a threefold rotation axis parallel to the crystallographic c axis. [Symmetry operators to generate equivalent atoms: (′) 1 − y, −1 + x − y, z; (′′) 2 − x + y, 1 − x, z.]

Structural commentary

The structural analyses revealed that both title compounds are monomeric in the solid state, with the alkynylamidinate anion acting as an N,N′-chelating ligand. Compound 1 crystallizes in the ortho­rhom­bic space group Pbca with one complex mol­ecule in the asymmetric unit. The two cyclo­penta­dienyl ligands feature a typical symmetric η5-coordination with Yb–centroid(Cp) distances of 2.315 and 2.321 Å. The Yb—Cp distances are therefore slightly larger than in the related chloride [Cp2YbCl]2 [Yb–centroid(Cp) 2.300 and 2.307 Å; Lamberts et al., 1987 ▸; Lueken et al., 1987 ▸, 1989 ▸], possibly due to the steric demand of the two N-isopropyl groups close to the ytterbium atom. Probably for the same reason, the product does not contain coordinating THF even though the complex was prepared in THF solution. Accordingly the coordination geometry around Yb can be described as distorted pseudo-tetra­hedral. At 131.1°, the Cp—Yb—Cp angle is close to that observed in [Cp2YbCl]2 (Cp—Yb—Cp 130.0°; Lamberts et al., 1987 ▸; Lueken et al., 1987 ▸, 1989 ▸) and compound 1 is therefore a typical bent metallocene complex of trivalent ytterbium. Due to the low formal coordination number of four around the Yb atom, the Yb—N bond lengths of 2.274 (2) and 2.293 (2) Å are short compared to those observed in other late lanthanide amidinates, such as [Yb2{(DippN)2CH}4(μ-OCPh=C6H4-4-CPh2O)(THF)] [Yb—N 2.285 (2)–2.391 (2) Å; Deacon et al., 2014 ▸], [Ho{N(SiMe3)2}{(CyN)2C—C≡C—c-C3H5}2] [Ho—N 2.303 (2)–2.348 (4) Å; Sroor et al., 2015b ▸] and [Ho(η8-COT){(CyN)2C—C≡C—c-C3H5}(THF)] [Ho—N 2.342 (3) and 2.349 (3) Å; Sroor et al., 2016 ▸].

Compound 2 crystallizes in the trigonal space group R c, with the Yb atom located on a threefold rotation axis along the crystallographic c axis. The complex mol­ecule is therefore C3 symmetric. The Yb atom is coordinated by the three symmetry-equivalent chelating amidinate ligands in a distorted octa­hedral fashion with C1—Yb—C1′ angles of 120° and an angle of 90±3° between the YbN2C planes. The cyclo­hexyl group attached to N2 is disordered over two orientations by rotation around the N2—C16 vector. As a result of the higher coordination number, the Yb—N bonds [2.310 (2) and 2.320 (2) Å] are slightly longer than in compound 1. However, in consequence of the small size of the Yb3+ ion, the Yb—N bonds in compound 2 are significantly shorter than in corres­ponding hexa­coordinated lanthanide(III) amidinates, e.g. [Ln{(PrN)2C–Bu}3] [Ln = Ce: Ce—N 2.469 (2)–2.550 (2) Å; Ln = Eu: Eu—N 2.402 (4)–2.457 (4) Å; Ln = Tb: Tb—N 2.391 (3)–2.409 (3) Å; Dröse et al., 2011 ▸] and [Ho{(CyN)2C—C≡C—c-C3H5}3] [Ho—N 2.342 (2)–2.383 (3) Å] (Sroor et al., 2015a ▸).

The N—Yb—N angle in compound 2 [58.2 (1)°] is slightly smaller than in compound 1 [59.1 (1)°], but larger than in other homoleptic lanthanide (III) amidinates {e.g. [Ln{(PrN)2C–Bu}3], Ln = Ce: N—Ce—N 51.81 (4)–52.72 (4)°; Ln = Eu: N—Eu—N 53.9 (1)–54.4 (2)°; Ln = Tb: N—Tb—N 54.9 (1)–55.0 (1)°; Dröse et al., 2011 ▸} and [Ho{(CyN)2C—C≡C—c-C3H5}3] [N—Ho—N 57.1 (1)–57.7 (1)°; Sroor et al., 2015a ▸]. The N—Ln—N angle therefore correlates clearly with the Ln—N bond length, decreasing with rising Ln—N distance (i.e. with rising coordination number of the metal and within the lanthanide series from right to left). The C1—N bond lengths of the amidinate ligand are very similar [1: 1.332 (3) and 1.334 (3) Å; 2: 1.321 (4) and 1.324 (4) Å], indicating a typical delocalization of the negative charge within the NCN fragment (Sroor et al., 2016 ▸).

Supra­molecular features

Compounds 1 and 2 do not exhibit any specific inter­molecular inter­actions. In compound 1, the closest inter­molecular C—C contacts are found between Cp ligands and cyclo­propyl substituents, 3.510–3.625 Å. Compound 2 features one inter­molecular phen­yl–cyclo­hexyl contact where the shortest C—C distance is 3.567 Å, and various cyclo­hex­yl–cyclo­hexyl contacts with C—C distances of 3.441–3.576 Å. The crystal structure of compound 2 comprises a large void of ca 220 Å3 that is probably filled with a highly disordered toluene mol­ecule. The content of the voids was corrected for using the SQUEEZE method (Spek, 2015 ▸), yielding a solvent-accessible volume of 1316 Å3 and 138 electrons, or about 1.5 solvate mol­ecules per unit cell. The composition of the crystal can therefore be assumed to be 2·0.166 toluene.

Database survey

For other lanthanide(III) complexes with amidinate ligands, see Richter et al. (2004 ▸), Edelmann (2009 ▸, 2012 ▸) and Deacon et al. (2014 ▸). For related bent sandwich complexes of the lanthanides, see Lueken et al. (1987 ▸, 1989 ▸), Schumann et al. (1998 ▸) and Kühling et al. (2015 ▸).

Synthesis and crystallization

Synthesis of Cp Pr≡C– -C

This compound was prepared by treatment of Cp2YbCl (Maginn et al., 1963 ▸) with Li[(Pr2N)2C—C≡C—c-C3H5] (Sroor et al., 2013 ▸) in a molar ratio of 1:1. Treatment of Cp2YbCl (0.68 g, 2.0 mmol) with Li[(Pr2N)2C—C≡C—c-C3H5] (2.0 mmol, prepared in situ from Li—C≡C—c-C3H5 and N,N′-diiso­propyl­carbodi­imide) in 30 ml of THF produced a bright-orange solution and a white precipitate (LiCl). After filtration and evaporation to dryness, the product was extracted with n-pentane (2 × 20 ml). The extract was filtered again and concentrated to a total volume of ca 10 ml. Crystallization at 253 K afforded 1 as orange air- and moisture-sensitive crystals. Yield: 0.53 g, 73%. M.p.: 478 K. Analysis calculated for C22H20N2Yb: C 53.43, H 5.91, N 5.66%; found: C 53.61, H 5.766, N 5.86%. MS (EI, M = 494.54): m/z (%) 450 (5) [M − 3CH3]+, 407 (5) [M − 2Pr]+, 384 (7), 369 (13) [M − 2Cp + 3H]+, 355 (5), 341 (66) [M − Cp − 2Pr]+, 328 (5), 313 (4) [YbNPr—C(CH)—NPr]+, 299 (7) [YbNPr—C—NPr]+, 284 (10) [YbNPr—C—NCCH3]+, 274 (100) [YbNPr—C—NCH3]+, 258 (25) [YbNPr—CN]+, 243 (8), 232 (10), 215 (12) [YbNCN]+. IR (KBr) ν (cm−1): 3093 (w), 2963 (m), 2922 (w), 2871 (w), 2609 (w), 2215 (m, C≡C), 2070 (w), 1985 (w), 1746 (w), 1609 (m, NCN), 1450 (s), 1367 (m), 1327 (m), 1258 (w), 1224 (m), 1177 (m), 1055 (w), 1012 (m), 968 (m), 878 (w), 766 (vs), 695 (m), 531 (w), 481 (w), 393 (w), 328 (w). 1H NMR (400 MHz, [D6]-benzene, 298 K): δ 0.92 (overlapped, m, CH-cyclo­prop­yl), 0.47–0.51 (m, 2H, CH 2-cyclo­prop­yl), 0.25–0.20 (m, 2H, CH 2-cyclo­prop­yl), −1.5 (br s, 10H, CH Cp), −7.2 (1H, sept, CH Pr), −10.8 (1H, sept, CH Pr), −36.9 (br s, CH 3 Pr). 13C NMR (100.6 MHz, [D6]-benzene, 298 K): δ 152.3 (s, NCN), 96.4 (s, C≡C–C), 69.7 (s, CH–C≡C), 65.3 (s, CH Cp), 2.5–2.6 (s, CH Pr), 1.1 (br s, CH3 Pr), 8.4 (s, CH2 cyclo­prop­yl), −0.4 (s, CH cyclo­prop­yl).

Synthesis of Yb[(CyN)≡C—Ph]

Anhydrous ytterbium(III) trichloride (1.40 g, 5.0 mmol) (Freeman & Smith, 1958 ▸) was suspended in THF (50 ml) and treated with a solution of Li[Ph—C≡C—C(NCy)2] (4.72 g, 15.0 mmol) (prepared in situ by addition of lithium phenyl­acetyl­ide to N,N′-di­cyclo­hexyl­carbodi­imide) in THF (60 ml). The reaction mixture was refluxed for 3 h. After cooling to room temperature, the white precipitate (LiCl) was removed by filtration, and the clear filtrate was evaporated to dryness. Off-white air- and moisture-sensitive solid. Yield: 3.07 g, 56%. M.p.: 505 K. Single crystal suitable for X-ray structure determination were obtained from a saturated toluene solution at 281 K. Analysis calculated for C63H81N6Yb: C 69.07, H 7.45, N 7.67%; found: C 69.21, H 7.50, N 7.47%. MS (EI, M = 1095.42): m/z (%) 1014 (23) [M – Cy]+, 1006 (7) [M – PhC]+, 998 (15), 964 (14), 949 (16), 899 (46), 849 (30), 833 (20), 811 (12), 799 (23), 787 (75) [M − NCy—C(C≡C—Ph)—NCy]+, 783 (35), 733 (62), 711 (6) [M − NCy—C(C≡C—Ph)-NCy – Ph]+, 683 (45), 667 (100) [M − NCy—C(C≡C—Ph)-NCy − Ph – C3H8]+, 645 (29). IR (KBr) ν (cm−1): 2922 (s), 2850 (m), 2661 (w), 2208 (w, C≡C), 1982 (w), 1598 (w), 1574 (w, NCN), 1491 (m), 1461 (vs), 1449 (s), 1411 (m), 1398 (m), 1343 (s), 1311 (m), 1256 (m), 1192 (m), 1170 (m), 1137 (m), 1070 (m), 1027 (w), 995 (m), 914 (w), 898 (m), 887 (m), 844 (w), 798 (w), 754 (s), 702 (m), 688 (s), 628 (s), 553 (w), 529 (m), 504 (w), 488 (w), 452 (w), 411 (m), 355 (m), 316 (m), 273 (w). 1H NMR (400.1 MHz, [D8]-THF, 298 K): 14.12 (br s, CH 2, Cy), 6.88 (br s,CH 2, Cy), 4.54 (m, 3H, p-CH Ph), 3.94 (m, 6H, m-CH Ph), 1.29 (br s, CH 2, Cy), −0.15 (d, 6H, o-CH Ph), −14.62 (br s, N—CH, Cy). 13C NMR (100.6 MHz, [D8]-THF, 298 K): 126.4 (s, p-CH Ph), 126.0 (s, m-CH Ph), 124.6 (s, o-CH Ph), 111.2 (s, i-C Ph), 71.0 (s, ≡C-Ph), 46.0 (s, N-CH, Cy), 36.1 (s, CH2, Cy), 35.7 (s, CH2, Cy), 35.0 (s, CH2, Cy), ≡C-C(NCy)2 and NCN not observed.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1 ▸. In the case of compound 2, C atoms C17–C21 of the disordered cyclo­hexyl substituent have been split over two sites, with a freely refined occupancy ratio. The N-bonded C atom C16 was refined as not disordered using EXYZ and EADP commands but the different orientation of the corresponding H atom H17 was taken into account. The contribution to the scattering from the solvent molecule in compound 2 was removed with the SQUEEZE routine (Spek, 2015 ▸) in PLATON (Spek, 2009 ▸), yielding a solvent accessible volume of 1316 Å3 and 138 electrons. H atoms were fixed geometrically and refined using a riding model with U(H) = 1.20U eq(C).

Table 1

Experimental details

	1	2
Crystal data
Chemical formula	[Yb(C5H5)2(C12H19N2)]	[Yb(C21H27N2)3]
M r	494.51	1095.37
Crystal system, space group	Orthorhombic, P b c a	Trigonal, R c:H
Temperature (K)	153	153
a, b, c (Å)	9.4578 (2), 19.2910 (6), 22.2114 (5)	20.3469 (3), 20.3469 (3), 50.3074 (11)
α, β, γ (°)	90, 90, 90	90, 90, 120
V (Å3)	4052.48 (18)	18036.8 (7)
Z	8	12
Radiation type	Mo Kα	Mo Kα
μ (mm−1)	4.62	1.60
Crystal size (mm)	0.33 × 0.31 × 0.25	0.36 × 0.35 × 0.24
Data collection
Diffractometer	Stoe IPDS 2T	Stoe IPDS 2T
Absorption correction	Numerical (X-AREA and X-RED; Stoe & Cie, 2002 ▸)	Numerical (X-AREA and X-RED; Stoe & Cie, 2002 ▸)
T min, T max	0.326, 0.448	0.621, 0.722
No. of measured, independent and observed [I > 2σ(I)] reflections	21905, 4045, 3263	36832, 3578, 2774
R int	0.051	0.065
(sin θ/λ)max (Å−1)	0.620	0.597
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.018, 0.040, 0.98	0.029, 0.071, 1.07
No. of reflections	4045	3578
No. of parameters	227	257
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.50, −0.72	0.31, −1.18

Computer programs: X-AREA and X-RED (Stoe & Cie, 2002 ▸), SHELXS2013 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸) and DIAMOND (Brandenburg, 1999 ▸).

Crystal structure: contains datablock(s) li0090, li0065_sq. DOI: 10.1107/S2056989016012135/zl2671sup1.cif

Structure factors: contains datablock(s) li0090. DOI: 10.1107/S2056989016012135/zl2671li0090sup2.hkl

Structure factors: contains datablock(s) li0065_sq. DOI: 10.1107/S2056989016012135/zl2671li0065_sqsup4.hkl

CCDC references: 1492937, 1492936

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Yb(C5H5)2(C12H19N2)]	Dx = 1.621 Mg m−3
Mr = 494.51	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 21907 reflections
a = 9.4578 (2) Å	θ = 1.8–26.2°
b = 19.2910 (6) Å	µ = 4.62 mm−1
c = 22.2114 (5) Å	T = 153 K
V = 4052.48 (18) Å3	Block, orange
Z = 8	0.33 × 0.31 × 0.25 mm
F(000) = 1960

Stoe IPDS 2T diffractometer	4045 independent reflections
Radiation source: fine-focus sealed tube	3263 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.051
area detector scans	θmax = 26.2°, θmin = 2.3°
Absorption correction: numerical (X-AREA and X-RED; Stoe & Cie, 2002)	h = −11→10
Tmin = 0.326, Tmax = 0.448	k = −23→22
21905 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018	H-atom parameters constrained
wR(F2) = 0.040	w = 1/[σ2(Fo2) + (0.0189P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
4045 reflections	Δρmax = 0.50 e Å−3
227 parameters	Δρmin = −0.72 e Å−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: heavy-atom method	Extinction coefficient: 0.00042 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.3923 (3)	0.02660 (12)	0.12656 (11)	0.0209 (5)
C2	0.4476 (3)	−0.03844 (14)	0.14935 (12)	0.0243 (5)
C3	0.5016 (3)	−0.08748 (13)	0.17234 (12)	0.0237 (5)
C4	0.5728 (3)	−0.14441 (13)	0.20074 (11)	0.0239 (5)
H1	0.5401	−0.1564	0.2423	0.029*
C5	0.7285 (3)	−0.15415 (18)	0.18859 (17)	0.0451 (9)
H3	0.7748	−0.1214	0.1605	0.054*
H2	0.7888	−0.1699	0.2224	0.054*
C6	0.6272 (4)	−0.20392 (15)	0.16337 (14)	0.0363 (7)
H4	0.6240	−0.2509	0.1813	0.044*
H5	0.6100	−0.2024	0.1194	0.044*
C7	0.1682 (3)	0.00848 (14)	0.17826 (13)	0.0279 (6)
H6	0.2233	−0.0186	0.2086	0.033*
C8	0.0678 (3)	0.05675 (15)	0.21099 (14)	0.0354 (7)
H9	0.0013	0.0294	0.2351	0.042*
H7	0.1218	0.0876	0.2375	0.042*
H8	0.0153	0.0845	0.1816	0.042*
C9	0.0881 (3)	−0.04153 (15)	0.13814 (15)	0.0396 (7)
H11	0.0232	−0.0693	0.1627	0.048*
H10	0.0341	−0.0154	0.1081	0.048*
H12	0.1553	−0.0722	0.1177	0.048*
C10	0.6091 (3)	0.04894 (13)	0.07174 (12)	0.0265 (6)
H13	0.6102	−0.0018	0.0627	0.032*
C11	0.7191 (3)	0.06331 (19)	0.12009 (15)	0.0407 (8)
H15	0.8127	0.0496	0.1054	0.049*
H16	0.7193	0.1129	0.1297	0.049*
H14	0.6961	0.0367	0.1564	0.049*
C12	0.6454 (3)	0.08777 (16)	0.01454 (14)	0.0361 (7)
H18	0.7412	0.0753	0.0017	0.043*
H17	0.5779	0.0753	−0.0171	0.043*
H19	0.6406	0.1378	0.0221	0.043*
C13	0.3678 (4)	0.19289 (17)	0.20356 (15)	0.0468 (9)
H20	0.3727	0.1576	0.2333	0.056*
C14	0.4768 (4)	0.21487 (18)	0.16796 (18)	0.0513 (10)
H21	0.5707	0.1974	0.1690	0.062*
C15	0.4272 (4)	0.26772 (16)	0.12948 (17)	0.0458 (9)
H22	0.4803	0.2920	0.0999	0.055*
C16	0.2837 (3)	0.27732 (14)	0.14360 (13)	0.0333 (7)
H23	0.2215	0.3098	0.1254	0.040*
C17	0.2495 (4)	0.23090 (15)	0.18876 (14)	0.0368 (7)
H24	0.1588	0.2260	0.2067	0.044*
C18	0.2309 (3)	0.20903 (15)	−0.00641 (12)	0.0292 (6)
H25	0.2880	0.2466	−0.0196	0.035*
C19	0.1094 (3)	0.21427 (15)	0.02902 (12)	0.0308 (6)
H26	0.0686	0.2558	0.0441	0.037*
C20	0.0589 (3)	0.14683 (19)	0.03826 (14)	0.0456 (9)
H27	−0.0230	0.1346	0.0606	0.055*
C21	0.1492 (4)	0.10076 (17)	0.00905 (15)	0.0470 (9)
H28	0.1402	0.0517	0.0086	0.056*
C22	0.2543 (4)	0.13851 (15)	−0.01913 (13)	0.0368 (7)
H29	0.3290	0.1201	−0.0429	0.044*
N1	0.2658 (2)	0.05054 (11)	0.14281 (10)	0.0212 (4)
N2	0.4664 (2)	0.06799 (10)	0.09026 (10)	0.0216 (4)
Yb	0.29970 (2)	0.15407 (2)	0.09600 (2)	0.01886 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0188 (12)	0.0168 (11)	0.0271 (13)	−0.0009 (10)	−0.0038 (11)	−0.0017 (9)
C2	0.0197 (13)	0.0225 (12)	0.0308 (13)	0.0006 (11)	0.0012 (10)	−0.0002 (11)
C3	0.0191 (13)	0.0243 (13)	0.0276 (14)	−0.0013 (12)	0.0011 (11)	−0.0005 (10)
C4	0.0233 (13)	0.0235 (13)	0.0248 (13)	0.0024 (11)	0.0008 (10)	0.0049 (10)
C5	0.0207 (16)	0.0513 (19)	0.063 (2)	0.0067 (15)	−0.0007 (14)	0.0297 (17)
C6	0.044 (2)	0.0315 (15)	0.0335 (16)	0.0146 (15)	0.0064 (14)	0.0086 (12)
C7	0.0194 (14)	0.0286 (14)	0.0356 (15)	0.0005 (11)	0.0026 (11)	0.0138 (12)
C8	0.0289 (15)	0.0425 (17)	0.0347 (15)	0.0003 (13)	0.0108 (13)	0.0069 (13)
C9	0.0248 (15)	0.0255 (14)	0.069 (2)	−0.0048 (14)	0.0090 (15)	0.0011 (14)
C10	0.0189 (13)	0.0207 (13)	0.0400 (14)	0.0017 (11)	0.0080 (12)	−0.0030 (11)
C11	0.0202 (16)	0.057 (2)	0.0453 (18)	0.0026 (14)	0.0030 (13)	0.0037 (15)
C12	0.0281 (15)	0.0424 (17)	0.0377 (17)	−0.0037 (14)	0.0093 (12)	−0.0038 (13)
C13	0.065 (2)	0.0368 (17)	0.0390 (18)	0.0037 (18)	−0.0226 (18)	−0.0134 (14)
C14	0.0307 (18)	0.0423 (19)	0.081 (3)	0.0127 (16)	−0.0246 (18)	−0.0393 (19)
C15	0.047 (2)	0.0275 (15)	0.063 (2)	−0.0175 (16)	0.0116 (17)	−0.0182 (15)
C16	0.0367 (18)	0.0198 (12)	0.0434 (16)	0.0058 (13)	−0.0073 (14)	−0.0059 (11)
C17	0.0409 (17)	0.0318 (15)	0.0377 (16)	−0.0032 (15)	0.0032 (14)	−0.0113 (12)
C18	0.0290 (17)	0.0302 (14)	0.0284 (14)	0.0040 (12)	−0.0004 (12)	0.0090 (11)
C19	0.0239 (14)	0.0404 (16)	0.0281 (14)	0.0095 (13)	−0.0019 (12)	0.0060 (12)
C20	0.0282 (16)	0.068 (2)	0.0405 (18)	−0.0194 (17)	−0.0139 (13)	0.0210 (17)
C21	0.069 (3)	0.0321 (16)	0.0396 (19)	−0.0118 (18)	−0.0301 (17)	0.0043 (13)
C22	0.0532 (19)	0.0357 (16)	0.0216 (14)	0.0131 (14)	−0.0055 (13)	0.0006 (11)
N1	0.0165 (11)	0.0190 (10)	0.0281 (11)	0.0019 (9)	0.0014 (9)	0.0040 (8)
N2	0.0169 (11)	0.0182 (10)	0.0298 (12)	0.0014 (8)	0.0024 (9)	−0.0018 (9)
Yb	0.01845 (6)	0.01490 (6)	0.02324 (6)	0.00096 (4)	−0.00219 (4)	0.00011 (4)

C1—N1	1.332 (3)	C12—H19	0.9800
C1—N2	1.334 (3)	C13—C14	1.367 (6)
C1—C2	1.451 (4)	C13—C17	1.378 (5)
C1—Yb	2.697 (2)	C13—Yb	2.585 (3)
C2—C3	1.190 (4)	C13—H20	0.9500
C3—C4	1.434 (4)	C14—C15	1.411 (5)
C4—C6	1.507 (4)	C14—Yb	2.595 (3)
C4—C5	1.509 (4)	C14—H21	0.9500
C4—H1	1.0000	C15—C16	1.405 (5)
C5—C6	1.468 (5)	C15—Yb	2.610 (3)
C5—H3	0.9900	C15—H22	0.9500
C5—H2	0.9900	C16—C17	1.383 (4)
C6—H4	0.9900	C16—Yb	2.607 (3)
C6—H5	0.9900	C16—H23	0.9500
C7—N1	1.460 (3)	C17—Yb	2.582 (3)
C7—C9	1.516 (4)	C17—H24	0.9500
C7—C8	1.516 (4)	C18—C19	1.396 (4)
C7—H6	1.0000	C18—C22	1.407 (4)
C8—H9	0.9800	C18—Yb	2.592 (3)
C8—H7	0.9800	C18—H25	0.9500
C8—H8	0.9800	C19—C20	1.401 (4)
C9—H11	0.9800	C19—Yb	2.608 (3)
C9—H10	0.9800	C19—H26	0.9500
C9—H12	0.9800	C20—C21	1.393 (5)
C10—N2	1.458 (3)	C20—Yb	2.617 (3)
C10—C12	1.514 (4)	C20—H27	0.9500
C10—C11	1.521 (4)	C21—C22	1.382 (5)
C10—H13	1.0000	C21—Yb	2.610 (3)
C11—H15	0.9800	C21—H28	0.9500
C11—H16	0.9800	C22—Yb	2.610 (3)
C11—H14	0.9800	C22—H29	0.9500
C12—H18	0.9800	N1—Yb	2.274 (2)
C12—H17	0.9800	N2—Yb	2.293 (2)
N1—C1—N2	115.4 (2)	Yb—C18—H25	116.2
N1—C1—C2	122.0 (2)	C18—C19—C20	107.2 (3)
N2—C1—C2	122.6 (2)	C18—C19—Yb	73.82 (16)
N1—C1—Yb	57.36 (12)	C20—C19—Yb	74.83 (16)
N2—C1—Yb	58.18 (12)	C18—C19—H26	126.4
C2—C1—Yb	173.46 (18)	C20—C19—H26	126.4
C3—C2—C1	172.8 (3)	Yb—C19—H26	117.1
C2—C3—C4	177.1 (3)	C21—C20—C19	108.4 (3)
C3—C4—C6	120.1 (2)	C21—C20—Yb	74.25 (18)
C3—C4—C5	118.3 (2)	C19—C20—Yb	74.06 (16)
C6—C4—C5	58.2 (2)	C21—C20—H27	125.8
C3—C4—H1	116.0	C19—C20—H27	125.8
C6—C4—H1	116.0	Yb—C20—H27	117.8
C5—C4—H1	116.0	C22—C21—C20	108.4 (3)
C6—C5—C4	60.8 (2)	C22—C21—Yb	74.66 (18)
C6—C5—H3	117.7	C20—C21—Yb	74.84 (18)
C4—C5—H3	117.7	C22—C21—H28	125.8
C6—C5—H2	117.7	C20—C21—H28	125.8
C4—C5—H2	117.7	Yb—C21—H28	116.7
H3—C5—H2	114.8	C21—C22—C18	107.8 (3)
C5—C6—C4	61.0 (2)	C21—C22—Yb	74.64 (18)
C5—C6—H4	117.7	C18—C22—Yb	73.61 (16)
C4—C6—H4	117.7	C21—C22—H29	126.1
C5—C6—H5	117.7	C18—C22—H29	126.1
C4—C6—H5	117.7	Yb—C22—H29	117.7
H4—C6—H5	114.8	C1—N1—C7	121.4 (2)
N1—C7—C9	110.6 (2)	C1—N1—Yb	93.09 (15)
N1—C7—C8	108.3 (2)	C7—N1—Yb	145.49 (16)
C9—C7—C8	111.1 (2)	C1—N2—C10	120.4 (2)
N1—C7—H6	108.9	C1—N2—Yb	92.20 (15)
C9—C7—H6	108.9	C10—N2—Yb	146.57 (16)
C8—C7—H6	108.9	N1—Yb—N2	59.11 (7)
C7—C8—H9	109.5	N1—Yb—C17	96.51 (9)
C7—C8—H7	109.5	N2—Yb—C17	125.91 (9)
H9—C8—H7	109.5	N1—Yb—C13	82.36 (10)
C7—C8—H8	109.5	N2—Yb—C13	95.16 (10)
H9—C8—H8	109.5	C17—Yb—C13	30.92 (11)
H7—C8—H8	109.5	N1—Yb—C18	136.46 (9)
C7—C9—H11	109.5	N2—Yb—C18	114.82 (8)
C7—C9—H10	109.5	C17—Yb—C18	114.78 (10)
H11—C9—H10	109.5	C13—Yb—C18	139.01 (10)
C7—C9—H12	109.5	N1—Yb—C14	101.91 (11)
H11—C9—H12	109.5	N2—Yb—C14	85.28 (9)
H10—C9—H12	109.5	C17—Yb—C14	50.80 (11)
N2—C10—C12	108.8 (2)	C13—Yb—C14	30.60 (12)
N2—C10—C11	112.8 (2)	C18—Yb—C14	121.15 (12)
C12—C10—C11	110.3 (2)	N1—Yb—C16	127.40 (9)
N2—C10—H13	108.3	N2—Yb—C16	136.29 (9)
C12—C10—H13	108.3	C17—Yb—C16	30.92 (10)
C11—C10—H13	108.3	C13—Yb—C16	51.34 (10)
C10—C11—H15	109.5	C18—Yb—C16	88.18 (9)
C10—C11—H16	109.5	C14—Yb—C16	51.34 (10)
H15—C11—H16	109.5	N1—Yb—C19	123.68 (8)
C10—C11—H14	109.5	N2—Yb—C19	139.92 (8)
H15—C11—H14	109.5	C17—Yb—C19	94.16 (10)
H16—C11—H14	109.5	C13—Yb—C19	124.76 (10)
C10—C12—H18	109.5	C18—Yb—C19	31.15 (9)
C10—C12—H17	109.5	C14—Yb—C19	126.54 (11)
H18—C12—H17	109.5	C16—Yb—C19	77.60 (9)
C10—C12—H19	109.5	N1—Yb—C21	85.14 (9)
H18—C12—H19	109.5	N2—Yb—C21	92.78 (10)
H17—C12—H19	109.5	C17—Yb—C21	135.74 (12)
C14—C13—C17	108.0 (3)	C13—Yb—C21	159.02 (13)
C14—C13—Yb	75.12 (19)	C18—Yb—C21	51.33 (10)
C17—C13—Yb	74.42 (17)	C14—Yb—C21	170.27 (13)
C14—C13—H20	126.0	C16—Yb—C21	128.90 (10)
C17—C13—H20	126.0	C19—Yb—C21	51.47 (10)
Yb—C13—H20	116.6	N1—Yb—C15	132.26 (10)
C13—C14—C15	108.9 (3)	N2—Yb—C15	107.84 (10)
C13—C14—Yb	74.29 (19)	C17—Yb—C15	51.36 (10)
C15—C14—Yb	74.87 (18)	C13—Yb—C15	51.56 (12)
C13—C14—H21	125.5	C18—Yb—C15	91.28 (11)
C15—C14—H21	125.5	C14—Yb—C15	31.44 (12)
Yb—C14—H21	117.2	C16—Yb—C15	31.25 (10)
C16—C15—C14	106.3 (3)	C19—Yb—C15	96.16 (11)
C16—C15—Yb	74.22 (17)	C21—Yb—C15	142.52 (11)
C14—C15—Yb	73.69 (17)	N1—Yb—C22	108.89 (9)
C16—C15—H22	126.8	N2—Yb—C22	88.59 (9)
C14—C15—H22	126.8	C17—Yb—C22	144.82 (10)
Yb—C15—H22	117.4	C13—Yb—C22	168.41 (11)
C17—C16—C15	107.6 (3)	C18—Yb—C22	31.38 (9)
C17—C16—Yb	73.57 (16)	C14—Yb—C22	139.59 (13)
C15—C16—Yb	74.53 (16)	C16—Yb—C22	119.52 (9)
C17—C16—H23	126.2	C19—Yb—C22	51.59 (9)
C15—C16—H23	126.2	C21—Yb—C22	30.70 (11)
Yb—C16—H23	117.7	C15—Yb—C22	116.85 (11)
C13—C17—C16	109.1 (3)	N1—Yb—C20	93.12 (9)
C13—C17—Yb	74.66 (17)	N2—Yb—C20	122.16 (10)
C16—C17—Yb	75.52 (17)	C17—Yb—C20	105.16 (12)
C13—C17—H24	125.4	C13—Yb—C20	133.23 (12)
C16—C17—H24	125.4	C18—Yb—C20	51.22 (9)
Yb—C17—H24	116.3	C14—Yb—C20	152.55 (11)
C19—C18—C22	108.2 (3)	C16—Yb—C20	101.36 (11)
C19—C18—Yb	75.03 (15)	C19—Yb—C20	31.11 (10)
C22—C18—Yb	75.01 (16)	C21—Yb—C20	30.91 (11)
C19—C18—H25	125.9	C15—Yb—C20	125.90 (12)
C22—C18—H25	125.9	C22—Yb—C20	51.00 (11)
C3—C4—C5—C6	−109.6 (3)	C19—C20—C21—Yb	66.8 (2)
C3—C4—C6—C5	106.6 (3)	C20—C21—C22—C18	1.1 (3)
C17—C13—C14—C15	−0.3 (3)	Yb—C21—C22—C18	−66.7 (2)
Yb—C13—C14—C15	67.5 (2)	C20—C21—C22—Yb	67.8 (2)
C17—C13—C14—Yb	−67.7 (2)	C19—C18—C22—C21	−0.9 (3)
C13—C14—C15—C16	0.5 (3)	Yb—C18—C22—C21	67.4 (2)
Yb—C14—C15—C16	67.6 (2)	C19—C18—C22—Yb	−68.3 (2)
C13—C14—C15—Yb	−67.1 (2)	N2—C1—N1—C7	174.8 (2)
C14—C15—C16—C17	−0.6 (3)	C2—C1—N1—C7	−8.1 (4)
Yb—C15—C16—C17	66.7 (2)	Yb—C1—N1—C7	179.6 (3)
C14—C15—C16—Yb	−67.2 (2)	N2—C1—N1—Yb	−4.8 (2)
C14—C13—C17—C16	−0.1 (3)	C2—C1—N1—Yb	172.3 (2)
Yb—C13—C17—C16	−68.3 (2)	C9—C7—N1—C1	−81.7 (3)
C14—C13—C17—Yb	68.2 (2)	C8—C7—N1—C1	156.3 (2)
C15—C16—C17—C13	0.4 (3)	C9—C7—N1—Yb	97.6 (3)
Yb—C16—C17—C13	67.7 (2)	C8—C7—N1—Yb	−24.4 (4)
C15—C16—C17—Yb	−67.3 (2)	N1—C1—N2—C10	177.0 (2)
C22—C18—C19—C20	0.3 (3)	C2—C1—N2—C10	0.0 (4)
Yb—C18—C19—C20	−68.0 (2)	Yb—C1—N2—C10	172.3 (3)
C22—C18—C19—Yb	68.3 (2)	N1—C1—N2—Yb	4.7 (2)
C18—C19—C20—C21	0.4 (3)	C2—C1—N2—Yb	−172.3 (2)
Yb—C19—C20—C21	−66.9 (2)	C12—C10—N2—C1	158.5 (2)
C18—C19—C20—Yb	67.3 (2)	C11—C10—N2—C1	−78.8 (3)
C19—C20—C21—C22	−0.9 (4)	C12—C10—N2—Yb	−35.6 (4)
Yb—C20—C21—C22	−67.7 (2)	C11—C10—N2—Yb	87.2 (4)

[Yb(C21H27N2)3]	Dx = 1.210 Mg m−3
Mr = 1095.37	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c:H	Cell parameters from 36835 reflections
a = 20.3469 (3) Å	θ = 2.0–25.1°
c = 50.3074 (11) Å	µ = 1.60 mm−1
V = 18036.8 (7) Å3	T = 153 K
Z = 12	Block, light yellow
F(000) = 6852	0.36 × 0.35 × 0.24 mm

Stoe IPDS 2T diffractometer	3578 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.065
area detector scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: numerical (X-AREA and X-RED; Stoe & Cie, 2002)	h = −24→24
Tmin = 0.621, Tmax = 0.722	k = −24→24
36832 measured reflections	l = −59→59

Refinement on F2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0274P)2 + 35.9511P] where P = (Fo2 + 2Fc2)/3
3578 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −1.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. PLATON SQUEEZE (Spek, 2015)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.11736 (16)	0.97236 (16)	0.14621 (6)	0.0488 (7)
C2	0.18462 (17)	0.96500 (16)	0.14454 (7)	0.0553 (8)
C3	0.24269 (17)	0.96456 (16)	0.14323 (7)	0.0569 (8)
C4	0.31432 (16)	0.96673 (17)	0.14298 (7)	0.0552 (8)
C5	0.36272 (19)	0.9967 (2)	0.16454 (8)	0.0644 (9)
H1	0.3477	1.0145	0.1795	0.077*
C6	0.4328 (2)	1.0010 (2)	0.16442 (9)	0.0773 (11)
H2	0.4658	1.0217	0.1792	0.093*
C7	0.4543 (2)	0.9751 (2)	0.14279 (10)	0.0853 (13)
H3	0.5017	0.9768	0.1429	0.102*
C8	0.4074 (2)	0.9468 (2)	0.12089 (10)	0.0847 (13)
H4	0.4233	0.9302	0.1058	0.102*
C9	0.3374 (2)	0.9423 (2)	0.12084 (9)	0.0712 (10)
H5	0.3052	0.9228	0.1058	0.085*
C10	0.06136 (18)	0.8906 (2)	0.10821 (7)	0.0610 (9)
H6	0.0980	0.8741	0.1138	0.073*
C11	0.0855 (2)	0.9272 (3)	0.08192 (8)	0.0935 (14)
H8	0.1378	0.9707	0.0831	0.112*
H7	0.0518	0.9468	0.0764	0.112*
C12	0.0825 (3)	0.8709 (3)	0.06098 (11)	0.134 (2)
H10	0.0972	0.8960	0.0434	0.161*
H9	0.1190	0.8540	0.0657	0.161*
C13	0.0034 (3)	0.8030 (3)	0.05952 (11)	0.131 (2)
H12	−0.0324	0.8195	0.0536	0.157*
H11	0.0023	0.7663	0.0463	0.157*
C14	−0.0206 (2)	0.7657 (3)	0.08578 (11)	0.1059 (18)
H13	0.0125	0.7450	0.0910	0.127*
H14	−0.0733	0.7227	0.0846	0.127*
C15	−0.0164 (2)	0.82102 (19)	0.10691 (8)	0.0691 (10)
H15	−0.0544	0.8365	0.1029	0.083*
H16	−0.0290	0.7955	0.1244	0.083*
C16A	0.17017 (18)	1.05213 (17)	0.18498 (7)	0.0566 (8)	0.442 (4)
H17A	0.2173	1.0728	0.1739	0.068*	0.442 (4)
C16B	0.17017 (18)	1.05213 (17)	0.18498 (7)	0.0566 (8)	0.558 (4)
H17B	0.1932	1.0199	0.1891	0.068*	0.558 (4)
C17A	0.1797 (4)	1.0071 (4)	0.20382 (16)	0.065 (2)	0.442 (4)
H18A	0.1894	0.9698	0.1946	0.078*	0.442 (4)
H19A	0.1324	0.9786	0.2142	0.078*	0.442 (4)
C17B	0.1324 (4)	1.0618 (3)	0.21256 (12)	0.0644 (17)	0.558 (4)
H18B	0.1064	1.0909	0.2087	0.077*	0.558 (4)
H19B	0.0938	1.0111	0.2191	0.077*	0.558 (4)
C18A	0.2455 (6)	1.0543 (5)	0.2227 (2)	0.091 (3)	0.442 (4)
H20A	0.2459	1.0217	0.2373	0.109*	0.442 (4)
H21A	0.2942	1.0753	0.2130	0.109*	0.442 (4)
C18B	0.1916 (6)	1.1025 (6)	0.23422 (18)	0.080 (3)	0.558 (4)
H20B	0.1677	1.1124	0.2497	0.096*	0.558 (4)
H21B	0.2121	1.0699	0.2402	0.096*	0.558 (4)
C19A	0.2374 (8)	1.1184 (9)	0.2342 (2)	0.089 (4)	0.442 (4)
H22A	0.2808	1.1492	0.2462	0.106*	0.442 (4)
H23A	0.1904	1.0971	0.2450	0.106*	0.442 (4)
C19B	0.2552 (6)	1.1765 (6)	0.2237 (2)	0.074 (3)	0.558 (4)
H22B	0.2949	1.2007	0.2375	0.088*	0.558 (4)
H23B	0.2354	1.2111	0.2198	0.088*	0.558 (4)
C20A	0.2345 (7)	1.1693 (8)	0.2125 (2)	0.067 (3)	0.442 (4)
H24A	0.2269	1.2094	0.2206	0.080*	0.442 (4)
H25A	0.2829	1.1940	0.2026	0.080*	0.442 (4)
C20B	0.2903 (3)	1.1658 (3)	0.19873 (14)	0.0672 (18)	0.558 (4)
H24B	0.3151	1.1359	0.2029	0.081*	0.558 (4)
H25B	0.3294	1.2159	0.1919	0.081*	0.558 (4)
C21A	0.1690 (4)	1.1208 (4)	0.19379 (14)	0.0533 (19)	0.442 (4)
H26A	0.1203	1.1055	0.2029	0.064*	0.442 (4)
H27A	0.1720	1.1514	0.1780	0.064*	0.442 (4)
C21B	0.2294 (3)	1.1248 (3)	0.17762 (11)	0.0516 (14)	0.558 (4)
H26B	0.2070	1.1568	0.1730	0.062*	0.558 (4)
H27B	0.2540	1.1196	0.1614	0.062*	0.558 (4)
N1	0.06247 (13)	0.94267 (14)	0.12836 (5)	0.0520 (6)
N2	0.10931 (13)	1.01127 (13)	0.16578 (5)	0.0481 (6)
Yb	0.0000	1.0000	0.14748 (2)	0.04418 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0332 (15)	0.0310 (14)	0.080 (2)	0.0142 (12)	0.0002 (14)	0.0028 (14)
C2	0.0374 (16)	0.0342 (16)	0.091 (2)	0.0153 (13)	−0.0050 (16)	−0.0062 (15)
C3	0.0392 (17)	0.0312 (15)	0.096 (2)	0.0146 (13)	−0.0032 (16)	−0.0028 (15)
C4	0.0349 (15)	0.0358 (15)	0.094 (2)	0.0166 (13)	−0.0007 (16)	−0.0010 (16)
C5	0.0480 (18)	0.063 (2)	0.086 (2)	0.0308 (17)	−0.0031 (18)	−0.0010 (19)
C6	0.050 (2)	0.082 (3)	0.101 (3)	0.035 (2)	−0.013 (2)	−0.006 (2)
C7	0.044 (2)	0.081 (3)	0.139 (4)	0.037 (2)	−0.006 (2)	−0.009 (3)
C8	0.058 (2)	0.085 (3)	0.121 (4)	0.044 (2)	0.005 (2)	−0.019 (3)
C9	0.052 (2)	0.062 (2)	0.105 (3)	0.0325 (18)	−0.010 (2)	−0.015 (2)
C10	0.0388 (16)	0.062 (2)	0.083 (2)	0.0258 (15)	−0.0023 (16)	−0.0217 (18)
C11	0.070 (3)	0.095 (3)	0.086 (3)	0.018 (2)	0.015 (2)	−0.016 (2)
C12	0.084 (3)	0.155 (5)	0.106 (4)	0.017 (3)	0.026 (3)	−0.054 (4)
C13	0.060 (3)	0.167 (5)	0.121 (4)	0.024 (3)	0.004 (3)	−0.089 (4)
C14	0.058 (2)	0.089 (3)	0.163 (5)	0.031 (2)	−0.004 (3)	−0.065 (3)
C15	0.055 (2)	0.054 (2)	0.090 (3)	0.0210 (17)	0.0019 (19)	−0.0201 (19)
C16A	0.0441 (17)	0.0423 (17)	0.084 (2)	0.0221 (15)	−0.0159 (17)	−0.0112 (16)
C16B	0.0441 (17)	0.0423 (17)	0.084 (2)	0.0221 (15)	−0.0159 (17)	−0.0112 (16)
C17A	0.055 (5)	0.052 (4)	0.077 (5)	0.019 (4)	−0.015 (4)	0.006 (4)
C17B	0.054 (3)	0.044 (3)	0.070 (3)	0.006 (3)	0.007 (3)	−0.003 (3)
C18A	0.097 (7)	0.074 (6)	0.091 (7)	0.034 (6)	−0.042 (6)	0.006 (5)
C18B	0.085 (6)	0.058 (5)	0.068 (4)	0.014 (6)	−0.002 (5)	−0.003 (4)
C19A	0.091 (9)	0.088 (10)	0.066 (6)	0.029 (10)	−0.021 (7)	−0.011 (6)
C19B	0.066 (6)	0.051 (5)	0.078 (7)	0.010 (5)	−0.014 (5)	−0.010 (5)
C20A	0.065 (7)	0.058 (6)	0.067 (7)	0.024 (6)	−0.017 (5)	−0.015 (6)
C20B	0.043 (3)	0.045 (3)	0.099 (5)	0.012 (3)	−0.006 (3)	−0.003 (3)
C21A	0.053 (4)	0.055 (4)	0.048 (4)	0.023 (4)	−0.003 (3)	−0.006 (3)
C21B	0.044 (3)	0.035 (3)	0.067 (3)	0.014 (2)	0.002 (2)	0.003 (2)
N1	0.0380 (13)	0.0476 (14)	0.0731 (15)	0.0234 (11)	−0.0043 (13)	−0.0122 (13)
N2	0.0356 (13)	0.0367 (12)	0.0716 (16)	0.0177 (11)	−0.0075 (12)	−0.0059 (12)
Yb	0.03321 (10)	0.03321 (10)	0.06610 (15)	0.01661 (5)	0.000	0.000

C1—N1	1.321 (4)	C16B—N2	1.459 (4)
C1—N2	1.324 (4)	C16B—C17B	1.645 (7)
C1—C2	1.451 (4)	C16B—H17B	1.0000
C1—Yb	2.714 (3)	C17A—C18A	1.528 (11)
C2—C3	1.188 (4)	C17A—H18A	0.9900
C3—C4	1.436 (4)	C17A—H19A	0.9900
C4—C5	1.385 (5)	C17B—C18B	1.526 (11)
C4—C9	1.393 (5)	C17B—H18B	0.9900
C5—C6	1.384 (5)	C17B—H19B	0.9900
C5—H1	0.9500	C18A—C19A	1.509 (18)
C6—C7	1.372 (6)	C18A—H20A	0.9900
C6—H2	0.9500	C18A—H21A	0.9900
C7—C8	1.381 (6)	C18B—C19B	1.508 (15)
C7—H3	0.9500	C18B—H20B	0.9900
C8—C9	1.382 (5)	C18B—H21B	0.9900
C8—H4	0.9500	C19A—C20A	1.53 (2)
C9—H5	0.9500	C19A—H22A	0.9900
C10—N1	1.458 (4)	C19A—H23A	0.9900
C10—C11	1.476 (6)	C19B—C20B	1.511 (13)
C10—C15	1.507 (4)	C19B—H22B	0.9900
C10—H6	1.0000	C19B—H23B	0.9900
C11—C12	1.536 (6)	C20A—C21A	1.525 (12)
C11—H8	0.9900	C20A—H24A	0.9900
C11—H7	0.9900	C20A—H25A	0.9900
C12—C13	1.510 (6)	C20B—C21B	1.524 (8)
C12—H10	0.9900	C20B—H24B	0.9900
C12—H9	0.9900	C20B—H25B	0.9900
C13—C14	1.480 (7)	C21A—H26A	0.9900
C13—H12	0.9900	C21A—H27A	0.9900
C13—H11	0.9900	C21B—H26B	0.9900
C14—C15	1.520 (5)	C21B—H27B	0.9900
C14—H13	0.9900	N1—Yb	2.320 (2)
C14—H14	0.9900	N2—Yb	2.310 (2)
C15—H15	0.9900	Yb—N2i	2.310 (2)
C15—H16	0.9900	Yb—N2ii	2.310 (2)
C16A—C17A	1.398 (8)	Yb—N1i	2.320 (2)
C16A—N2	1.459 (4)	Yb—N1ii	2.320 (2)
C16A—C21A	1.477 (8)	Yb—C1ii	2.714 (3)
C16A—H17A	1.0000	Yb—C1i	2.714 (3)
C16B—C21B	1.412 (6)
N1—C1—N2	116.7 (3)	C19A—C18A—H21A	109.7
N1—C1—C2	122.6 (3)	C17A—C18A—H21A	109.7
N2—C1—C2	120.6 (3)	H20A—C18A—H21A	108.2
N1—C1—Yb	58.68 (15)	C19B—C18B—C17B	109.9 (7)
N2—C1—Yb	58.25 (15)	C19B—C18B—H20B	109.7
C2—C1—Yb	174.4 (2)	C17B—C18B—H20B	109.7
C3—C2—C1	175.2 (3)	C19B—C18B—H21B	109.7
C2—C3—C4	176.7 (4)	C17B—C18B—H21B	109.7
C5—C4—C9	119.4 (3)	H20B—C18B—H21B	108.2
C5—C4—C3	119.6 (3)	C18A—C19A—C20A	111.7 (10)
C9—C4—C3	120.9 (3)	C18A—C19A—H22A	109.3
C6—C5—C4	120.5 (4)	C20A—C19A—H22A	109.3
C6—C5—H1	119.8	C18A—C19A—H23A	109.3
C4—C5—H1	119.8	C20A—C19A—H23A	109.3
C7—C6—C5	119.7 (4)	H22A—C19A—H23A	107.9
C7—C6—H2	120.2	C18B—C19B—C20B	112.3 (8)
C5—C6—H2	120.2	C18B—C19B—H22B	109.1
C6—C7—C8	120.5 (4)	C20B—C19B—H22B	109.1
C6—C7—H3	119.7	C18B—C19B—H23B	109.1
C8—C7—H3	119.7	C20B—C19B—H23B	109.1
C9—C8—C7	120.2 (4)	H22B—C19B—H23B	107.9
C9—C8—H4	119.9	C21A—C20A—C19A	108.8 (10)
C7—C8—H4	119.9	C21A—C20A—H24A	109.9
C8—C9—C4	119.7 (4)	C19A—C20A—H24A	109.9
C8—C9—H5	120.2	C21A—C20A—H25A	109.9
C4—C9—H5	120.2	C19A—C20A—H25A	109.9
N1—C10—C11	112.1 (3)	H24A—C20A—H25A	108.3
N1—C10—C15	109.9 (3)	C19B—C20B—C21B	110.1 (6)
C11—C10—C15	111.3 (3)	C19B—C20B—H24B	109.6
N1—C10—H6	107.8	C21B—C20B—H24B	109.6
C11—C10—H6	107.8	C19B—C20B—H25B	109.6
C15—C10—H6	107.8	C21B—C20B—H25B	109.6
C10—C11—C12	111.1 (4)	H24B—C20B—H25B	108.1
C10—C11—H8	109.4	C16A—C21A—C20A	112.0 (7)
C12—C11—H8	109.4	C16A—C21A—H26A	109.2
C10—C11—H7	109.4	C20A—C21A—H26A	109.2
C12—C11—H7	109.4	C16A—C21A—H27A	109.2
H8—C11—H7	108.0	C20A—C21A—H27A	109.2
C13—C12—C11	109.9 (4)	H26A—C21A—H27A	107.9
C13—C12—H10	109.7	C16B—C21B—C20B	115.1 (5)
C11—C12—H10	109.7	C16B—C21B—H26B	108.5
C13—C12—H9	109.7	C20B—C21B—H26B	108.5
C11—C12—H9	109.7	C16B—C21B—H27B	108.5
H10—C12—H9	108.2	C20B—C21B—H27B	108.5
C14—C13—C12	110.7 (4)	H26B—C21B—H27B	107.5
C14—C13—H12	109.5	C1—N1—C10	120.5 (3)
C12—C13—H12	109.5	C1—N1—Yb	92.22 (18)
C14—C13—H11	109.5	C10—N1—Yb	147.1 (2)
C12—C13—H11	109.5	C1—N2—C16B	120.6 (2)
H12—C13—H11	108.1	C1—N2—C16A	120.6 (2)
C13—C14—C15	111.2 (4)	C1—N2—Yb	92.59 (18)
C13—C14—H13	109.4	C16B—N2—Yb	145.21 (19)
C15—C14—H13	109.4	C16A—N2—Yb	145.21 (19)
C13—C14—H14	109.4	N2i—Yb—N2ii	105.17 (7)
C15—C14—H14	109.4	N2i—Yb—N2	105.17 (7)
H13—C14—H14	108.0	N2ii—Yb—N2	105.17 (7)
C10—C15—C14	111.8 (3)	N2i—Yb—N1i	58.20 (9)
C10—C15—H15	109.3	N2ii—Yb—N1i	156.22 (8)
C14—C15—H15	109.3	N2—Yb—N1i	96.18 (9)
C10—C15—H16	109.3	N2i—Yb—N1ii	96.18 (9)
C14—C15—H16	109.3	N2ii—Yb—N1ii	58.19 (9)
H15—C15—H16	107.9	N2—Yb—N1ii	156.22 (8)
C17A—C16A—N2	115.6 (4)	N1i—Yb—N1ii	104.02 (8)
C17A—C16A—C21A	119.3 (5)	N2i—Yb—N1	156.22 (8)
N2—C16A—C21A	109.1 (3)	N2ii—Yb—N1	96.18 (8)
C17A—C16A—H17A	103.5	N2—Yb—N1	58.19 (9)
N2—C16A—H17A	103.5	N1i—Yb—N1	104.02 (8)
C21A—C16A—H17A	103.5	N1ii—Yb—N1	104.02 (8)
C21B—C16B—N2	117.4 (4)	N2i—Yb—C1ii	103.62 (8)
C21B—C16B—C17B	107.5 (4)	N2ii—Yb—C1ii	29.16 (9)
N2—C16B—C17B	108.2 (3)	N2—Yb—C1ii	131.74 (9)
C21B—C16B—H17B	107.8	N1i—Yb—C1ii	131.99 (9)
N2—C16B—H17B	107.8	N1ii—Yb—C1ii	29.10 (9)
C17B—C16B—H17B	107.8	N1—Yb—C1ii	100.12 (8)
C16A—C17A—C18A	112.0 (6)	N2i—Yb—C1i	29.16 (9)
C16A—C17A—H18A	109.2	N2ii—Yb—C1i	131.74 (9)
C18A—C17A—H18A	109.2	N2—Yb—C1i	103.62 (8)
C16A—C17A—H19A	109.2	N1i—Yb—C1i	29.10 (9)
C18A—C17A—H19A	109.2	N1ii—Yb—C1i	100.12 (8)
H18A—C17A—H19A	107.9	N1—Yb—C1i	131.99 (9)
C18B—C17B—C16B	112.2 (6)	C1ii—Yb—C1i	119.946 (6)
C18B—C17B—H18B	109.2	N2i—Yb—C1	131.74 (9)
C16B—C17B—H18B	109.2	N2ii—Yb—C1	103.62 (8)
C18B—C17B—H19B	109.2	N2—Yb—C1	29.16 (9)
C16B—C17B—H19B	109.2	N1i—Yb—C1	100.12 (8)
H18B—C17B—H19B	107.9	N1ii—Yb—C1	131.98 (9)
C19A—C18A—C17A	110.0 (8)	N1—Yb—C1	29.10 (9)
C19A—C18A—H20A	109.7	C1ii—Yb—C1	119.947 (6)
C17A—C18A—H20A	109.7	C1i—Yb—C1	119.945 (6)
C9—C4—C5—C6	−1.4 (5)	N2—C16B—C21B—C20B	178.3 (4)
C3—C4—C5—C6	−178.4 (3)	C17B—C16B—C21B—C20B	56.2 (6)
C4—C5—C6—C7	−0.2 (6)	C19B—C20B—C21B—C16B	−59.6 (8)
C5—C6—C7—C8	1.7 (7)	N2—C1—N1—C10	−171.7 (3)
C6—C7—C8—C9	−1.7 (7)	C2—C1—N1—C10	9.7 (4)
C7—C8—C9—C4	0.0 (6)	Yb—C1—N1—C10	−176.7 (3)
C5—C4—C9—C8	1.5 (6)	N2—C1—N1—Yb	4.9 (3)
C3—C4—C9—C8	178.5 (3)	C2—C1—N1—Yb	−173.6 (3)
N1—C10—C11—C12	−179.1 (3)	C11—C10—N1—C1	−104.2 (4)
C15—C10—C11—C12	−55.5 (5)	C15—C10—N1—C1	131.5 (3)
C10—C11—C12—C13	57.3 (7)	C11—C10—N1—Yb	81.9 (5)
C11—C12—C13—C14	−57.7 (7)	C15—C10—N1—Yb	−42.4 (6)
C12—C13—C14—C15	56.7 (6)	N1—C1—N2—C16B	−174.1 (3)
N1—C10—C15—C14	179.0 (4)	C2—C1—N2—C16B	4.5 (4)
C11—C10—C15—C14	54.2 (5)	Yb—C1—N2—C16B	−169.2 (3)
C13—C14—C15—C10	−54.7 (5)	N1—C1—N2—C16A	−174.1 (3)
N2—C16A—C17A—C18A	178.9 (6)	C2—C1—N2—C16A	4.5 (4)
C21A—C16A—C17A—C18A	−47.8 (9)	Yb—C1—N2—C16A	−169.2 (3)
C21B—C16B—C17B—C18B	−53.7 (7)	N1—C1—N2—Yb	−5.0 (3)
N2—C16B—C17B—C18B	178.6 (6)	C2—C1—N2—Yb	173.6 (3)
C16A—C17A—C18A—C19A	51.2 (11)	C21B—C16B—N2—C1	82.5 (4)
C16B—C17B—C18B—C19B	52.9 (11)	C17B—C16B—N2—C1	−155.7 (3)
C17A—C18A—C19A—C20A	−57.9 (14)	C21B—C16B—N2—Yb	−78.2 (5)
C17B—C18B—C19B—C20B	−55.0 (12)	C17B—C16B—N2—Yb	43.5 (5)
C18A—C19A—C20A—C21A	57.1 (14)	C17A—C16A—N2—C1	−74.5 (5)
C18B—C19B—C20B—C21B	55.8 (11)	C21A—C16A—N2—C1	147.7 (4)
C17A—C16A—C21A—C20A	47.8 (9)	C17A—C16A—N2—Yb	124.7 (5)
N2—C16A—C21A—C20A	−176.2 (7)	C21A—C16A—N2—Yb	−13.1 (6)
C19A—C20A—C21A—C16A	−49.3 (12)