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

Two ytterbium(III) complexes comprising alkynylamidinate ligands, Cp₂Yb[(ⁱPr₂N)₂C—C[triple bond]C—c-C₃H₅] (1) and Yb[(CyN)₂C—C[triple bond]C—Ph]₃ (Cy = cyclo­hex­yl) (2) have been synthesized and structurally characterized. Both complexes are monomers without any coordinated solvent in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.004 Å
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.018
• wR factor = 0.040
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Datablock: li0090



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.462 Check

Alert level G
PLAT371_ALERT_2_G Long    C(sp2)-C(sp1) Bond  C1     -   C2     ..       1.45 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: li0065_sq



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      8.543 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.406 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.597          9 Report

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      35.95 Why ?
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C16B   --  C17B    ..        5.3 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C16B   --  C21B    ..        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         25 Note
PLAT371_ALERT_2_G Long    C(sp2)-C(sp1) Bond  C1     -   C2     ..       1.45 Ang.
PLAT371_ALERT_2_G Long    C(sp2)-C(sp1) Bond  C3     -   C4     ..       1.44 Ang.
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in Structure ...        220 A   3  
PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed           ! Info
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          60 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          1 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          1 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-AREA and X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(li0090) Bis(η⁵-cyclopentadienyl)(3-cyclopropyl-N,N'-diisopropylpropynamidinato-κ²N,N')ytterbium(III)

Crystal data

[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) Å^3	Block, orange
Z = 8	0.33 × 0.31 × 0.25 mm
F(000) = 1960

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.040	w = 1/[σ^2(Fo^2) + (0.0189P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: heavy-atom method	Extinction coefficient: 0.00042 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(li0065_sq) Tris(3-phenyl-N,N'-dicyclohexylpropynamidinato-κ²N,N')ytterbium(III)

Crystal data

[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) Å^3	T = 153 K
Z = 12	Block, light yellow
F(000) = 6852	0.36 × 0.35 × 0.24 mm

Data collection

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

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

Special details

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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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

Geometric parameters (Å, º)

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—N2^i	2.310 (2)
C15—H16	0.9900	Yb—N2^ii	2.310 (2)
C16A—C17A	1.398 (8)	Yb—N1^i	2.320 (2)
C16A—N2	1.459 (4)	Yb—N1^ii	2.320 (2)
C16A—C21A	1.477 (8)	Yb—C1^ii	2.714 (3)
C16A—H17A	1.0000	Yb—C1^i	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	N2^i—Yb—N2^ii	105.17 (7)
C15—C14—H14	109.4	N2^i—Yb—N2	105.17 (7)
H13—C14—H14	108.0	N2^ii—Yb—N2	105.17 (7)
C10—C15—C14	111.8 (3)	N2^i—Yb—N1^i	58.20 (9)
C10—C15—H15	109.3	N2^ii—Yb—N1^i	156.22 (8)
C14—C15—H15	109.3	N2—Yb—N1^i	96.18 (9)
C10—C15—H16	109.3	N2^i—Yb—N1^ii	96.18 (9)
C14—C15—H16	109.3	N2^ii—Yb—N1^ii	58.19 (9)
H15—C15—H16	107.9	N2—Yb—N1^ii	156.22 (8)
C17A—C16A—N2	115.6 (4)	N1^i—Yb—N1^ii	104.02 (8)
C17A—C16A—C21A	119.3 (5)	N2^i—Yb—N1	156.22 (8)
N2—C16A—C21A	109.1 (3)	N2^ii—Yb—N1	96.18 (8)
C17A—C16A—H17A	103.5	N2—Yb—N1	58.19 (9)
N2—C16A—H17A	103.5	N1^i—Yb—N1	104.02 (8)
C21A—C16A—H17A	103.5	N1^ii—Yb—N1	104.02 (8)
C21B—C16B—N2	117.4 (4)	N2^i—Yb—C1^ii	103.62 (8)
C21B—C16B—C17B	107.5 (4)	N2^ii—Yb—C1^ii	29.16 (9)
N2—C16B—C17B	108.2 (3)	N2—Yb—C1^ii	131.74 (9)
C21B—C16B—H17B	107.8	N1^i—Yb—C1^ii	131.99 (9)
N2—C16B—H17B	107.8	N1^ii—Yb—C1^ii	29.10 (9)
C17B—C16B—H17B	107.8	N1—Yb—C1^ii	100.12 (8)
C16A—C17A—C18A	112.0 (6)	N2^i—Yb—C1^i	29.16 (9)
C16A—C17A—H18A	109.2	N2^ii—Yb—C1^i	131.74 (9)
C18A—C17A—H18A	109.2	N2—Yb—C1^i	103.62 (8)
C16A—C17A—H19A	109.2	N1^i—Yb—C1^i	29.10 (9)
C18A—C17A—H19A	109.2	N1^ii—Yb—C1^i	100.12 (8)
H18A—C17A—H19A	107.9	N1—Yb—C1^i	131.99 (9)
C18B—C17B—C16B	112.2 (6)	C1^ii—Yb—C1^i	119.946 (6)
C18B—C17B—H18B	109.2	N2^i—Yb—C1	131.74 (9)
C16B—C17B—H18B	109.2	N2^ii—Yb—C1	103.62 (8)
C18B—C17B—H19B	109.2	N2—Yb—C1	29.16 (9)
C16B—C17B—H19B	109.2	N1^i—Yb—C1	100.12 (8)
H18B—C17B—H19B	107.9	N1^ii—Yb—C1	131.98 (9)
C19A—C18A—C17A	110.0 (8)	N1—Yb—C1	29.10 (9)
C19A—C18A—H20A	109.7	C1^ii—Yb—C1	119.947 (6)
C17A—C18A—H20A	109.7	C1^i—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)

Symmetry codes: (i) −y+1, x−y+2, z; (ii) −x+y−1, −x+1, z.