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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1675–m1676.
Published online 2010 November 27. doi:  10.1107/S1600536810048531
PMCID: PMC3011607

[N,N′-Bis(2,6-diisopropyl­phen­yl)methanimidamidato][η8-1,4-bis­(tri­methyl­sil­yl)cyclo­octa­tetra­enyl](tetra­hydro­furan)­samarium(III) toluene monosolvate

Abstract

The title compound, [Sm(C25H35N2)(C14H24Si2)(C4H8O)]·C7H8, was prepared by treatment of anhydrous samarium trichloride with a 1:1 mixture of in situ-prepared Li(DippForm) [DippFormH = N,N′-bis­(2,6-diisopropyl­phen­yl)methanimidamide] and Li2(COT′′) [COT′′ = 1,4-bis­(trimethyl­sil­yl)cyclo­octa­tetra­enyl] in tetra­hydro­furan (THF). Despite the presence of two very bulky ligands (COT′′ and DippForm), the mol­ecule still contains one coordinated THF ligand. The overall coordination geometry around the SmIII atom resembles a three-legged piano-stool with the COT′′ ligand being η8-coordinated and the DippForm anion acting as an N,N′-chelating ligand [Sm—N = 2.5555 (15) and 2.4699 (15) Å]. The asymmetric unit also contains a disordered mol­ecule of toluene, the refined ratio of the two components being 0.80 (4):0.20 (4).

Related literature

For review articles on the search for alternative specta­tor ligands other than cyclo­penta­dienyls which are able to satisfy the coordination requirements of the large lanthanide cations, see: Edelmann (1995 [triangle], 2009 [triangle]); Bailey & Pace (2001 [triangle]); Edelmann et al. (2002 [triangle]). For related complexes, see: Schumann et al. (1995 [triangle]). For bulky formamidinate ligands, see: Cole et al. (2007 [triangle]); Junk & Cole (2007 [triangle]). For the COT′′ ligand, see: Burton et al. (1989 [triangle],1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1675-scheme1.jpg

Experimental

Crystal data

  • [Sm(C25H35N2)(C14H24Si2)(C4H8O)]·C7H8
  • M r = 926.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1675-efi1.jpg
  • a = 18.490 (4) Å
  • b = 11.166 (2) Å
  • c = 24.865 (5) Å
  • β = 107.80 (3)°
  • V = 4887.9 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.29 mm−1
  • T = 133 K
  • 0.40 × 0.22 × 0.14 mm

Data collection

  • Stoe IPDS 2T diffractometer
  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.978, T max = 0.992
  • 13121 measured reflections
  • 13121 independent reflections
  • 10516 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.056
  • S = 0.90
  • 13121 reflections
  • 511 parameters
  • 10 restraints
  • H-atom parameters constrained
  • Δρmax = 1.35 e Å−3
  • Δρmin = −1.81 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Siemens, 1994 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048531/zs2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048531/zs2077Isup2.hkl

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

Acknowledgments

This work was generously supported by the Deutsche Forschungsgemeinschaft DFG (SPP-1166 "Lanthanoid-spezifische Funktionalitäten in Molekül und Material"). Financial support work by the Otto-von-Guericke-Universität Magdeburg is also gratefully acknowledged.

supplementary crystallographic information

Comment

A hot topic in current organolanthanide chemistry is the search for alternative spectator ligands other than cyclopentadienyls which are able to satisfy the coordination requirements of the large lanthanide cations (Edelmann et al., 2002). Among the most successful approaches in this field is the use of amidinate ligands of the general type [RC(NR')2]- (R = H, alkyl, aryl; R' = alkyl, cycloalkyl, aryl, SiMe3) which can be regarded as steric cyclopentadienyl equivalents (Bailey & Pace, 2001; Edelmann, 2009). Closely related very bulky N,N'-disubstituted formamidinate ligands such as DippForm- [DippFormH = N,N'-bis(2,6-diisopropylphenyl)methanimidamide] have also been frequently employed in this area (Cole et al., 2007; Junk & Cole, 2007]. Another ligand system besides cyclopentadienyl, which is traditionally very important in organolanthanide chemistry, is the cyclooctatetraenyl dianion (= COT) (Edelmann, 1995) and its ring-substituted derivatives such as 1,4-bis(trimethylsilyl)cyclooctatetraenyl (= COT'') (Burton et al., 1989; Burton et al., 1993). Rare-earth metal complexes of the type (COT)Ln[RC(NR')2](THF) have been reported by Schumann et al. (1995). These compounds all comprise the unsubstituted COT ligand and moderately bulky N,N'-bis(trimethylsilyl) benzamidinate ligands (Schumann et al., 1995). We were interested in the question if THF-free compounds of this type would be accessible by combining both the bulky COT'' and the DippForm ligand in the coordination sphere of a lanthanide ion. The first compound of this series, [η8-1,4-bis(trimethylsilyl)cyclooctatetraenyl][N,N'-bis(2,6-diisopropyl­phenyl)formamidinato](tetrahydrofuran)samarium(III) [= (COT'')Sm­(DippForm)(THF), was synthesized by treatment of anhydrous samarium trichloride simultaneously with in situ-prepared Li(DippForm) and Li2(COT'') in THF. Work-up followed by recrystallization from toluene afforded the dark red title compound. Besides X-ray crystallography, the title compound was also characterized by elemental analysis and spectroscopic methods. Dark red, highly air-sensitive, rod-like single crystals of the title compound were obtained by slow cooling of a saturated solution in toluene to 278 K. Surprisingly, despite the presence of two very bulky ligands, COT'' and DippForm, the molecule still contains one coordinated THF ligand. Thus the overall coordination geometry around Sm resembles a three-legged piano-stool with the COT'' ligand being η8-coordinated and the DippForm- anion acting as N,N'-chelating ligand (Sm—N distances: Sm1—N1, 2.5555 (15); Sm1—N2, 2.4699 (15) Å). The N1—C15—N2 angle of the formamidinate unit is 120.10 (15)°.

Experimental

Preparation of [η8-1,4-bis(trimethylsilyl)cyclooctatetraenyl][N,N'-bis(2,6-diisopropyl­phenyl)formamidinato](tetrahydrofuran)samarium(III): The reaction was carried out under rigorous exclusion of air and moisture. In a 100 ml-Schlenk-flask, a mixture of 1,4-bis(trimethylsilyl)cycloocta-2,5,7-triene (2.00 g, 8.1 mmol) and N,N'-bis(2,6-diisopropylphenyl)methanimidamide (= DippFormH, 2.90 g, 8.1 mmol) were dissolved in THF (25 ml) and a 1.6 N solution of n-butyllithium in n-hexane (15 ml, 24 mmol) was added. Metalation as completed by stirring for 3 h at room temperature. Anhydrous SmCl3 (2.1 g, 8.1 mmol) was added as solid and stirring was continued for 24 h. A white precipitate (LiCl) was removed by filtration, and the clear red.brown flitrate was evaporated to dryness. The residue was extracted with warm (ca 323 K) toluene (2x20 ml), the combined axtracts were filtered again and diluted with n-pentane (30 ml). Cooling to 278 K for 2–3 d afforded 5.27 g (78%) of [η8-1,4-bis(trimethylsilyl)cyclooctatetraenyl][N,N'-bis(2,6-diisopropylphenyl)formamidinato](tetrahydrofuran)samarium(III) as a dark red microcrystalline solid. Dark red, rod-like X-ray quality single-crystals of the mono-toluene solvate were obtained by recrystallization from toluene. Anal. calcd for C43H67N2OSi2Sm (834.55 g/mol): C 61.89, H 8.09, N 3.36; found: C 62.56, H 8.14, N 3.50%. IR (KBr pellet): νmax 2961 (versus), 2867 (m), 1665 (s), 1643 (m), 1588 (m), 1528 (versus), 1456 (m), 1438 (m), 1383 (w), 1361 (w), 1332 (m), 1320 (m), 1319 (s), 1285 (s), 1248 (versus), 1190 (m), 1160 (s), 1099 (m), 1046 (m), 937 (m), 837 (versus), 799 (m), 754 (s) cm-1. 1H NMR (400.1 MHz, THF-d8, 298 K): d = 12.99 (s br, 2H), 9.28 (s br, 2H), 8.60 (s br, 2H) (COT'' ring-H); 8.34 (s, 1H, N—CH-N); 7.07–7.21 (m, 11H, phenyl ring-H, DippForm + toluene); 3.60 (m, 4H, THF); 2.94 (m, 4H, CH(CH3)2); 2.31 (s, 3H, C6H5—CH3); (1.77 (m, 4H, THF); 1.17 (d, 24H, CH(CH3)2); 0.74 (s, 18H, Si(CH3)3) p.p.m.. 13C NMR (100.6 MHz, THF-d8, 298 K): δ = 190.6 (N-CH—N), 144.6, 141.9, 124.4, 123.8 (phenyl ring-C, DippForm); 138.3, 129.5, 128.8, 125.9 (C6H5—CH3); 95.1, 90.3, 84.2, 83.8 (COT'' ring-C); 68.1 (THF); 29.8 (CH(CH3)2); 28.1 CH(CH3)2); 26.2 (THF); 21.4 (H3C-C6H5); -0.27 (Si(CH3)3) p.p.m.. 29Si NMR (79.5 MHz, THF-d8, 298 K): δ = -54.4 (SiMe3) p.p.m.. EI—MS: m/z 834.2 (18%) [M]+, 514.9 (100%) [Sm(DippForm)]+, 399.7 (3") [Sm(COT'')]+, 365.0 (88%) [DippFormH]+, 72.9 (16%) [THF]+.

Refinement

The asymmetric unit contains a disordered molecule of toluene. The refined ratio of the two components is 0.80 (4):0.20 (4). Since the refined ratio of the second component is only 20% it was not possible to find the maxima for the hydrogen atoms of the methyl group. Also the carbon atoms of the second component were refined isotropically. The hydrogen atoms were included using a riding model, with aromatic C—H = 0.95 Å, methine C—H = 1.00 Å, methylene C—H = 0.99 Å [Uiso(H) = 1.2Ueq(C)] and methyl C—H = 0.98 Å [Uiso(H) = 1.5Ueq(C)].

Figures

Fig. 1.
The molecule of the title compound in the crystal. Thermal ellipsoids represent 50% probability levels.

Crystal data

[Sm(C25H35N2)(C14H24Si2)(C4H8O)]·C7H8F(000) = 1948
Mr = 926.65Dx = 1.259 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2203 reflections
a = 18.490 (4) Åθ = 2.0–29.3°
b = 11.166 (2) ŵ = 1.29 mm1
c = 24.865 (5) ÅT = 133 K
β = 107.80 (3)°Rod, red
V = 4887.9 (19) Å30.40 × 0.22 × 0.14 mm
Z = 4

Data collection

Stoe IPDS 2T diffractometer13121 independent reflections
Radiation source: fine-focus sealed tube10516 reflections with I > 2σ(I)
graphiteRint = 0.0000
ω scansθmax = 29.3°, θmin = 2.0°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2002)h = −25→24
Tmin = 0.978, Tmax = 0.992k = 0→15
13121 measured reflectionsl = 0→34

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
13121 reflections(Δ/σ)max = 0.003
511 parametersΔρmax = 1.35 e Å3
10 restraintsΔρmin = −1.80 e Å3

Special details

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 asymmetric unit contains a disordered molecule of toluene. The refined ratio of the two components is 0.80 (4):0.20 (4). Since the refined ratio of the second component is only 20% it was not possible to find the maxima for the hydrogen atoms of the methyl group. Also the carbon atoms of the second component were refined isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Sm10.405603 (5)0.266319 (7)0.245665 (4)0.01538 (3)
Si10.21411 (3)0.30376 (5)0.10579 (2)0.02413 (11)
Si20.35521 (3)0.30346 (5)0.39783 (2)0.02455 (11)
N10.55006 (8)0.26252 (14)0.26855 (6)0.0187 (3)
N20.47622 (8)0.28076 (14)0.17613 (6)0.0189 (3)
O1L0.42110 (8)0.48577 (12)0.25701 (6)0.0266 (3)
C1L0.36356 (13)0.58031 (18)0.24756 (11)0.0330 (5)
H1LA0.34590.59010.28110.040*
H1LB0.31930.56140.21450.040*
C2L0.40251 (16)0.6908 (2)0.23726 (15)0.0518 (7)
H2LA0.39850.69870.19680.062*
H2LB0.38060.76310.24940.062*
C3L0.48233 (17)0.6729 (2)0.27211 (19)0.0707 (11)
H3LA0.48980.69710.31180.085*
H3LB0.51730.71980.25700.085*
C4L0.49522 (13)0.5411 (2)0.26807 (11)0.0352 (5)
H4LA0.51680.52400.23700.042*
H4LB0.53070.51070.30380.042*
C10.26614 (9)0.23910 (16)0.17715 (7)0.0194 (3)
C20.30412 (10)0.12855 (16)0.17700 (8)0.0199 (3)
H20.29860.10120.13980.024*
C30.34796 (10)0.04931 (16)0.21837 (8)0.0199 (3)
H30.3616−0.02110.20230.024*
C40.37646 (10)0.04961 (16)0.27783 (8)0.0198 (3)
H40.4047−0.02090.29200.024*
C50.37376 (10)0.12785 (17)0.32168 (8)0.0208 (3)
H50.40340.09960.35770.025*
C60.33760 (10)0.23866 (17)0.32523 (7)0.0203 (3)
C70.28865 (10)0.31161 (17)0.28213 (8)0.0200 (3)
H70.27040.37830.29790.024*
C80.25975 (10)0.31212 (17)0.22249 (8)0.0192 (3)
H80.22750.37900.20910.023*
C90.23547 (15)0.2177 (2)0.04801 (9)0.0405 (5)
H9A0.29040.21830.05390.061*
H9B0.20920.25470.01150.061*
H9C0.21810.13480.04830.061*
C100.24198 (14)0.4632 (2)0.10097 (10)0.0367 (5)
H10A0.29670.46760.10620.055*
H10B0.23000.51020.13040.055*
H10C0.21400.49530.06380.055*
C110.10940 (12)0.3030 (2)0.09541 (10)0.0344 (5)
H11A0.08250.33660.05830.052*
H11B0.09860.35130.12490.052*
H11C0.09230.22050.09760.052*
C120.39430 (18)0.4586 (3)0.40028 (11)0.0494 (7)
H12A0.40340.49190.43820.074*
H12B0.35780.50910.37270.074*
H12C0.44220.45610.39110.074*
C130.26264 (13)0.3122 (2)0.41321 (10)0.0367 (5)
H13A0.24130.23160.41220.055*
H13B0.22730.36260.38480.055*
H13C0.27070.34710.45080.055*
C140.42327 (15)0.2115 (3)0.45355 (10)0.0460 (6)
H14A0.40360.12980.45260.069*
H14B0.42930.24710.49070.069*
H14C0.47260.20950.44650.069*
C150.54287 (9)0.25826 (16)0.21399 (7)0.0185 (3)
H150.58550.23910.20190.022*
C160.62515 (10)0.25293 (16)0.30688 (7)0.0204 (3)
C170.63883 (10)0.16724 (17)0.35098 (8)0.0225 (4)
C180.71151 (12)0.1569 (2)0.38879 (10)0.0324 (4)
H18A0.72070.10030.41870.039*
C190.77072 (13)0.2270 (2)0.38395 (11)0.0426 (6)
H19A0.82030.21750.40970.051*
C200.75717 (12)0.3110 (2)0.34141 (11)0.0382 (5)
H20A0.79810.35930.33840.046*
C210.68516 (11)0.32726 (18)0.30256 (9)0.0261 (4)
C220.57698 (11)0.08184 (18)0.35439 (8)0.0247 (4)
H22A0.52740.12470.33950.030*
C230.57511 (13)−0.0257 (2)0.31580 (10)0.0353 (5)
H23A0.57060.00270.27760.053*
H23B0.5315−0.07650.31470.053*
H23C0.6221−0.07200.33040.053*
C240.58400 (13)0.0399 (2)0.41440 (10)0.0365 (5)
H24A0.58510.10960.43850.055*
H24B0.6310−0.00620.42940.055*
H24C0.5404−0.01070.41360.055*
C250.67652 (11)0.42579 (19)0.25866 (9)0.0272 (4)
H25A0.62180.42870.23550.033*
C260.69770 (14)0.5494 (2)0.28573 (10)0.0376 (5)
H26A0.66760.56580.31120.056*
H26B0.68720.61070.25610.056*
H26C0.75190.55070.30710.056*
C270.72306 (14)0.3984 (2)0.21843 (11)0.0411 (6)
H27A0.70880.31940.20120.062*
H27B0.77730.39870.23960.062*
H27C0.71280.45950.18880.062*
C280.46910 (9)0.25978 (18)0.11824 (7)0.0208 (3)
C290.47324 (10)0.14315 (19)0.09802 (8)0.0234 (4)
C300.46624 (12)0.1284 (2)0.04083 (9)0.0334 (5)
H30A0.46940.05010.02670.040*
C310.45484 (13)0.2243 (3)0.00446 (9)0.0396 (5)
H31A0.45110.2123−0.03410.047*
C320.44880 (13)0.3383 (2)0.02441 (9)0.0352 (5)
H32A0.43960.4040−0.00100.042*
C330.45594 (11)0.3585 (2)0.08093 (8)0.0259 (4)
C340.48399 (11)0.03259 (18)0.13561 (9)0.0263 (4)
H34A0.47470.05670.17170.032*
C350.56497 (13)−0.0169 (2)0.15032 (10)0.0348 (5)
H35A0.60130.04640.16770.052*
H35B0.5746−0.04510.11580.052*
H35C0.5708−0.08380.17680.052*
C360.42773 (14)−0.0665 (2)0.10883 (11)0.0388 (5)
H36A0.3758−0.03520.09930.058*
H36B0.4337−0.13300.13560.058*
H36C0.4375−0.09500.07440.058*
C370.45387 (13)0.4857 (2)0.10222 (9)0.0319 (5)
H37A0.43390.48230.13530.038*
C380.53453 (15)0.5380 (2)0.12273 (11)0.0441 (6)
H38A0.56750.48410.15080.066*
H38B0.53320.61660.13990.066*
H38C0.55430.54650.09060.066*
C390.40268 (16)0.5706 (2)0.05834 (11)0.0449 (6)
H39A0.35120.53750.04490.067*
H39B0.42290.57950.02640.067*
H39C0.40130.64910.07570.067*
C5L0.81056 (15)0.0907 (2)0.06760 (10)0.0519 (10)0.800 (5)
C6L0.81808 (14)0.2116 (2)0.08157 (11)0.0462 (9)0.800 (5)
H6L0.86670.24850.09140.055*0.800 (5)
C7L0.75450 (18)0.27851 (18)0.08111 (12)0.0606 (11)0.800 (5)
H7L0.75960.36110.09070.073*0.800 (5)
C8L0.68339 (14)0.2245 (3)0.06669 (12)0.0651 (14)0.800 (5)
H8L0.63990.27020.06640.078*0.800 (5)
C9L0.67587 (14)0.1036 (3)0.05272 (12)0.0628 (13)0.800 (5)
H9L0.62730.06670.04290.075*0.800 (5)
C10L0.73945 (18)0.03674 (19)0.05318 (11)0.069 (2)0.800 (5)
H10L0.7343−0.04590.04360.083*0.800 (5)
C11L0.8786 (3)0.0161 (5)0.06959 (18)0.0745 (15)0.800 (5)
H11D0.92460.06500.08320.112*0.800 (5)
H11E0.8739−0.01390.03160.112*0.800 (5)
H11F0.8817−0.05170.09530.112*0.800 (5)
C410.7366 (5)0.1612 (8)0.0655 (5)0.055 (4)*0.200 (5)
C420.7972 (6)0.2407 (7)0.0768 (5)0.038 (4)*0.200 (5)
H420.78890.32390.08030.046*0.200 (5)
C430.8701 (5)0.1984 (9)0.0830 (5)0.051 (4)*0.200 (5)
H430.91150.25280.09070.061*0.200 (5)
C440.8822 (5)0.0767 (9)0.0778 (5)0.062 (5)*0.200 (5)
H440.93200.04790.08200.075*0.200 (5)
C450.8216 (6)−0.0028 (7)0.0665 (6)0.060 (4)*0.200 (5)
H450.8299−0.08600.06290.072*0.200 (5)
C460.7487 (5)0.0394 (8)0.0603 (6)0.049 (6)*0.200 (5)
H460.7073−0.01490.05260.059*0.200 (5)
C470.6630 (18)0.205 (2)0.0605 (13)0.098 (10)*0.200 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sm10.01623 (4)0.01574 (4)0.01597 (4)−0.00062 (3)0.00758 (3)−0.00064 (3)
Si10.0259 (3)0.0278 (3)0.0180 (2)0.0036 (2)0.0057 (2)0.00060 (19)
Si20.0272 (3)0.0298 (3)0.0179 (2)0.0023 (2)0.0087 (2)−0.00247 (19)
N10.0165 (6)0.0232 (7)0.0158 (6)−0.0016 (6)0.0039 (5)−0.0016 (6)
N20.0187 (7)0.0236 (8)0.0152 (7)−0.0011 (6)0.0062 (5)−0.0009 (6)
O1L0.0267 (7)0.0185 (6)0.0371 (8)−0.0012 (5)0.0135 (6)−0.0028 (5)
C1L0.0320 (11)0.0212 (10)0.0480 (13)0.0030 (8)0.0155 (10)0.0002 (9)
C2L0.0521 (15)0.0253 (11)0.088 (2)0.0059 (11)0.0357 (15)0.0123 (13)
C3L0.0451 (16)0.0280 (14)0.141 (4)−0.0092 (11)0.0318 (19)−0.0171 (17)
C4L0.0299 (11)0.0251 (11)0.0512 (14)−0.0061 (8)0.0132 (10)−0.0071 (9)
C10.0174 (7)0.0227 (9)0.0187 (8)−0.0003 (6)0.0064 (6)−0.0009 (6)
C20.0209 (8)0.0200 (9)0.0201 (8)−0.0029 (6)0.0084 (7)−0.0041 (6)
C30.0214 (8)0.0164 (8)0.0242 (9)−0.0014 (6)0.0104 (7)−0.0027 (6)
C40.0203 (8)0.0185 (8)0.0232 (9)0.0006 (6)0.0104 (7)0.0036 (6)
C50.0217 (8)0.0229 (9)0.0198 (8)0.0016 (7)0.0095 (7)0.0042 (7)
C60.0216 (8)0.0226 (9)0.0195 (8)−0.0002 (7)0.0106 (6)−0.0002 (7)
C70.0191 (8)0.0228 (8)0.0208 (8)0.0015 (7)0.0101 (7)−0.0016 (7)
C80.0167 (8)0.0207 (8)0.0207 (8)0.0021 (6)0.0065 (6)0.0004 (7)
C90.0493 (14)0.0501 (14)0.0207 (10)0.0122 (11)0.0088 (9)−0.0021 (9)
C100.0444 (13)0.0346 (12)0.0330 (12)0.0013 (10)0.0147 (10)0.0097 (9)
C110.0265 (10)0.0372 (12)0.0339 (11)0.0048 (8)0.0010 (9)−0.0007 (9)
C120.0668 (18)0.0473 (15)0.0345 (13)−0.0208 (13)0.0161 (13)−0.0143 (11)
C130.0368 (12)0.0508 (14)0.0281 (11)0.0104 (10)0.0181 (9)−0.0029 (9)
C140.0472 (14)0.0646 (18)0.0217 (10)0.0222 (12)0.0039 (10)−0.0034 (10)
C150.0167 (7)0.0200 (9)0.0204 (8)−0.0027 (6)0.0081 (6)−0.0030 (6)
C160.0168 (7)0.0241 (10)0.0196 (8)0.0001 (6)0.0044 (6)−0.0030 (6)
C170.0213 (9)0.0236 (9)0.0212 (9)−0.0001 (7)0.0042 (7)−0.0021 (7)
C180.0270 (10)0.0343 (11)0.0295 (11)0.0007 (8)−0.0009 (8)0.0044 (8)
C190.0231 (10)0.0487 (14)0.0440 (13)−0.0043 (10)−0.0076 (9)0.0074 (11)
C200.0209 (10)0.0434 (13)0.0448 (14)−0.0090 (9)0.0019 (9)0.0052 (10)
C210.0214 (9)0.0301 (11)0.0262 (10)−0.0030 (7)0.0063 (7)−0.0011 (8)
C220.0220 (9)0.0252 (10)0.0261 (10)0.0023 (7)0.0061 (7)0.0048 (7)
C230.0340 (11)0.0263 (11)0.0421 (13)−0.0010 (8)0.0066 (10)−0.0027 (9)
C240.0333 (11)0.0452 (13)0.0334 (12)0.0061 (9)0.0138 (10)0.0135 (10)
C250.0232 (9)0.0323 (11)0.0268 (10)−0.0077 (8)0.0087 (8)−0.0003 (8)
C260.0380 (12)0.0345 (12)0.0367 (13)−0.0116 (9)0.0062 (10)0.0008 (9)
C270.0353 (12)0.0526 (15)0.0429 (14)−0.0058 (10)0.0230 (11)0.0034 (11)
C280.0158 (7)0.0324 (10)0.0163 (7)−0.0003 (7)0.0079 (6)−0.0013 (7)
C290.0162 (8)0.0358 (11)0.0201 (9)0.0002 (7)0.0083 (7)−0.0057 (7)
C300.0289 (11)0.0486 (14)0.0243 (11)0.0027 (9)0.0105 (9)−0.0123 (9)
C310.0362 (11)0.0674 (16)0.0164 (9)0.0082 (11)0.0099 (8)−0.0056 (10)
C320.0333 (11)0.0569 (15)0.0180 (10)0.0090 (10)0.0117 (9)0.0069 (9)
C330.0209 (9)0.0391 (11)0.0194 (9)0.0012 (8)0.0087 (7)0.0028 (8)
C340.0259 (9)0.0289 (10)0.0276 (10)−0.0001 (7)0.0134 (8)−0.0083 (8)
C350.0315 (11)0.0360 (12)0.0379 (12)0.0075 (9)0.0124 (9)−0.0014 (9)
C360.0368 (12)0.0381 (13)0.0464 (14)−0.0073 (9)0.0196 (11)−0.0139 (10)
C370.0393 (12)0.0346 (11)0.0273 (11)0.0022 (9)0.0184 (9)0.0079 (8)
C380.0524 (15)0.0481 (15)0.0315 (12)−0.0134 (12)0.0125 (11)0.0088 (10)
C390.0555 (16)0.0442 (14)0.0435 (14)0.0099 (12)0.0279 (12)0.0176 (11)
C5L0.072 (3)0.060 (2)0.0218 (15)−0.0081 (18)0.0130 (15)0.0029 (13)
C6L0.052 (2)0.047 (2)0.0368 (18)−0.0155 (19)0.0085 (15)0.0015 (15)
C7L0.067 (3)0.057 (2)0.055 (2)−0.014 (2)0.0138 (19)0.0053 (18)
C8L0.062 (3)0.091 (4)0.038 (2)−0.005 (3)0.0100 (19)0.010 (2)
C9L0.066 (3)0.090 (3)0.0342 (18)−0.038 (2)0.0181 (18)−0.0124 (18)
C10L0.115 (5)0.073 (3)0.0235 (18)−0.056 (3)0.026 (2)−0.0122 (16)
C11L0.100 (4)0.086 (4)0.035 (2)0.017 (3)0.016 (2)−0.005 (2)

Geometric parameters (Å, °)

Sm1—N22.4699 (15)C20—C211.397 (3)
Sm1—O1L2.4731 (14)C20—H20A0.9500
Sm1—N12.5555 (15)C21—C251.523 (3)
Sm1—C22.6160 (19)C22—C231.530 (3)
Sm1—C82.6297 (18)C22—C241.531 (3)
Sm1—C72.6369 (18)C22—H22A1.0000
Sm1—C12.6377 (19)C23—H23A0.9800
Sm1—C52.6439 (18)C23—H23B0.9800
Sm1—C32.6504 (18)C23—H23C0.9800
Sm1—C42.6549 (18)C24—H24A0.9800
Sm1—C62.6668 (17)C24—H24B0.9800
Sm1—C152.8796 (17)C24—H24C0.9800
Si1—C101.867 (2)C25—C261.533 (3)
Si1—C91.868 (2)C25—C271.536 (3)
Si1—C111.873 (2)C25—H25A1.0000
Si1—C11.8844 (19)C26—H26A0.9800
Si2—C131.867 (2)C26—H26B0.9800
Si2—C141.868 (2)C26—H26C0.9800
Si2—C121.871 (3)C27—H27A0.9800
Si2—C61.8784 (19)C27—H27B0.9800
N1—C151.323 (2)C27—H27C0.9800
N1—C161.428 (2)C28—C291.406 (3)
N2—C151.326 (2)C28—C331.413 (3)
N2—C281.424 (2)C29—C301.397 (3)
O1L—C4L1.451 (2)C29—C341.524 (3)
O1L—C1L1.466 (2)C30—C311.376 (4)
C1L—C2L1.490 (3)C30—H30A0.9500
C1L—H1LA0.9900C31—C321.383 (4)
C1L—H1LB0.9900C31—H31A0.9500
C2L—C3L1.479 (4)C32—C331.389 (3)
C2L—H2LA0.9900C32—H32A0.9500
C2L—H2LB0.9900C33—C371.520 (3)
C3L—C4L1.500 (4)C34—C361.525 (3)
C3L—H3LA0.9900C34—C351.532 (3)
C3L—H3LB0.9900C34—H34A1.0000
C4L—H4LA0.9900C35—H35A0.9800
C4L—H4LB0.9900C35—H35B0.9800
C1—C21.421 (3)C35—H35C0.9800
C1—C81.425 (2)C36—H36A0.9800
C2—C31.410 (3)C36—H36B0.9800
C2—H20.9500C36—H36C0.9800
C3—C41.410 (3)C37—C391.534 (3)
C3—H30.9500C37—C381.536 (3)
C4—C51.410 (3)C37—H37A1.0000
C4—H40.9500C38—H38A0.9800
C5—C61.422 (3)C38—H38B0.9800
C5—H50.9500C38—H38C0.9800
C6—C71.428 (3)C39—H39A0.9800
C7—C81.414 (3)C39—H39B0.9800
C7—H70.9500C39—H39C0.9800
C8—H80.9500C5L—C6L1.3900
C9—H9A0.9800C5L—C10L1.3900
C9—H9B0.9800C5L—C11L1.497 (5)
C9—H9C0.9800C6L—C7L1.3900
C10—H10A0.9800C6L—H6L0.9500
C10—H10B0.9800C7L—C8L1.3900
C10—H10C0.9800C7L—H7L0.9500
C11—H11A0.9800C8L—C9L1.3900
C11—H11B0.9800C8L—H8L0.9500
C11—H11C0.9800C9L—C10L1.3900
C12—H12A0.9800C9L—H9L0.9500
C12—H12B0.9800C10L—H10L0.9500
C12—H12C0.9800C11L—H11D0.9800
C13—H13A0.9800C11L—H11E0.9800
C13—H13B0.9800C11L—H11F0.9800
C13—H13C0.9800C41—C421.3900
C14—H14A0.9800C41—C461.3900
C14—H14B0.9800C41—C471.41 (3)
C14—H14C0.9800C42—C431.3900
C15—H150.9500C42—H420.9500
C16—C211.416 (3)C43—C441.3900
C16—C171.419 (3)C43—H430.9500
C17—C181.389 (3)C44—C451.3900
C17—C221.511 (3)C44—H440.9500
C18—C191.381 (3)C45—C461.3900
C18—H18A0.9500C45—H450.9500
C19—C201.378 (3)C46—H460.9500
C19—H19A0.9500
N2—Sm1—O1L86.99 (5)H11A—C11—H11B109.5
N2—Sm1—N154.31 (5)Si1—C11—H11C109.5
O1L—Sm1—N185.08 (5)H11A—C11—H11C109.5
N2—Sm1—C290.50 (5)H11B—C11—H11C109.5
O1L—Sm1—C2133.79 (5)Si2—C12—H12A109.5
N1—Sm1—C2128.89 (5)Si2—C12—H12B109.5
N2—Sm1—C8124.06 (6)H12A—C12—H12B109.5
O1L—Sm1—C884.70 (5)Si2—C12—H12C109.5
N1—Sm1—C8169.74 (6)H12A—C12—H12C109.5
C2—Sm1—C859.23 (6)H12B—C12—H12C109.5
N2—Sm1—C7153.23 (6)Si2—C13—H13A109.5
O1L—Sm1—C781.34 (5)Si2—C13—H13B109.5
N1—Sm1—C7146.91 (5)H13A—C13—H13B109.5
C2—Sm1—C780.63 (6)Si2—C13—H13C109.5
C8—Sm1—C731.16 (6)H13A—C13—H13C109.5
N2—Sm1—C1100.20 (5)H13B—C13—H13C109.5
O1L—Sm1—C1104.13 (5)Si2—C14—H14A109.5
N1—Sm1—C1152.96 (5)Si2—C14—H14B109.5
C2—Sm1—C131.38 (6)H14A—C14—H14B109.5
C8—Sm1—C131.39 (5)Si2—C14—H14C109.5
C7—Sm1—C160.11 (6)H14A—C14—H14C109.5
N2—Sm1—C5145.04 (5)H14B—C14—H14C109.5
O1L—Sm1—C5122.77 (5)N1—C15—N2120.10 (15)
N1—Sm1—C5106.09 (6)N1—C15—Sm162.55 (9)
C2—Sm1—C581.41 (6)N2—C15—Sm158.86 (9)
C8—Sm1—C580.38 (6)N1—C15—H15120.0
C7—Sm1—C558.74 (6)N2—C15—H15120.0
C1—Sm1—C590.40 (6)Sm1—C15—H15168.4
N2—Sm1—C397.91 (5)C21—C16—C17119.70 (16)
O1L—Sm1—C3163.42 (5)C21—C16—N1122.01 (16)
N1—Sm1—C3110.66 (5)C17—C16—N1118.29 (16)
C2—Sm1—C331.05 (6)C18—C17—C16119.07 (18)
C8—Sm1—C379.43 (6)C18—C17—C22120.12 (18)
C7—Sm1—C387.45 (6)C16—C17—C22120.65 (16)
C1—Sm1—C359.48 (6)C19—C18—C17121.5 (2)
C5—Sm1—C359.24 (6)C19—C18—H18A119.2
N2—Sm1—C4118.02 (5)C17—C18—H18A119.2
O1L—Sm1—C4153.61 (5)C20—C19—C18119.3 (2)
N1—Sm1—C4102.26 (5)C20—C19—H19A120.3
C2—Sm1—C459.30 (6)C18—C19—H19A120.3
C8—Sm1—C487.38 (6)C19—C20—C21122.0 (2)
C7—Sm1—C478.92 (6)C19—C20—H20A119.0
C1—Sm1—C480.86 (6)C21—C20—H20A119.0
C5—Sm1—C430.86 (6)C20—C21—C16118.33 (19)
C3—Sm1—C430.82 (6)C20—C21—C25117.27 (18)
N2—Sm1—C6175.52 (5)C16—C21—C25124.40 (17)
O1L—Sm1—C695.43 (5)C17—C22—C23109.41 (17)
N1—Sm1—C6122.05 (5)C17—C22—C24114.06 (18)
C2—Sm1—C690.53 (6)C23—C22—C24110.47 (18)
C8—Sm1—C660.04 (6)C17—C22—H22A107.6
C7—Sm1—C631.22 (6)C23—C22—H22A107.6
C1—Sm1—C682.89 (6)C24—C22—H22A107.6
C5—Sm1—C631.06 (6)C22—C23—H23A109.5
C3—Sm1—C680.81 (6)C22—C23—H23B109.5
C4—Sm1—C659.06 (6)H23A—C23—H23B109.5
N2—Sm1—C1527.35 (5)C22—C23—H23C109.5
O1L—Sm1—C1588.92 (5)H23A—C23—H23C109.5
N1—Sm1—C1527.34 (5)H23B—C23—H23C109.5
C2—Sm1—C15108.63 (5)C22—C24—H24A109.5
C8—Sm1—C15151.24 (5)C22—C24—H24B109.5
C7—Sm1—C15169.76 (6)H24A—C24—H24B109.5
C1—Sm1—C15126.09 (5)C22—C24—H24C109.5
C5—Sm1—C15125.79 (6)H24A—C24—H24C109.5
C3—Sm1—C15102.73 (5)H24B—C24—H24C109.5
C4—Sm1—C15109.33 (5)C21—C25—C26112.25 (18)
C6—Sm1—C15148.67 (5)C21—C25—C27111.45 (19)
C10—Si1—C9108.28 (12)C26—C25—C27110.28 (18)
C10—Si1—C11106.84 (11)C21—C25—H25A107.5
C9—Si1—C11110.13 (11)C26—C25—H25A107.5
C10—Si1—C1110.74 (10)C27—C25—H25A107.5
C9—Si1—C1111.09 (10)C25—C26—H26A109.5
C11—Si1—C1109.66 (10)C25—C26—H26B109.5
C13—Si2—C14109.18 (12)H26A—C26—H26B109.5
C13—Si2—C12108.30 (13)C25—C26—H26C109.5
C14—Si2—C12108.59 (14)H26A—C26—H26C109.5
C13—Si2—C6108.46 (10)H26B—C26—H26C109.5
C14—Si2—C6112.37 (10)C25—C27—H27A109.5
C12—Si2—C6109.86 (10)C25—C27—H27B109.5
C15—N1—C16117.02 (14)H27A—C27—H27B109.5
C15—N1—Sm190.10 (10)C25—C27—H27C109.5
C16—N1—Sm1152.46 (11)H27A—C27—H27C109.5
C15—N2—C28117.72 (14)H27B—C27—H27C109.5
C15—N2—Sm193.79 (10)C29—C28—C33120.34 (17)
C28—N2—Sm1142.32 (11)C29—C28—N2121.02 (17)
C4L—O1L—C1L108.72 (15)C33—C28—N2118.63 (17)
C4L—O1L—Sm1120.88 (12)C30—C29—C28118.33 (19)
C1L—O1L—Sm1129.95 (12)C30—C29—C34118.85 (19)
O1L—C1L—C2L104.99 (18)C28—C29—C34122.81 (16)
O1L—C1L—H1LA110.7C31—C30—C29121.7 (2)
C2L—C1L—H1LA110.7C31—C30—H30A119.2
O1L—C1L—H1LB110.7C29—C30—H30A119.2
C2L—C1L—H1LB110.7C30—C31—C32119.56 (19)
H1LA—C1L—H1LB108.8C30—C31—H31A120.2
C3L—C2L—C1L103.6 (2)C32—C31—H31A120.2
C3L—C2L—H2LA111.0C31—C32—C33121.3 (2)
C1L—C2L—H2LA111.0C31—C32—H32A119.3
C3L—C2L—H2LB111.0C33—C32—H32A119.3
C1L—C2L—H2LB111.0C32—C33—C28118.7 (2)
H2LA—C2L—H2LB109.0C32—C33—C37119.99 (19)
C2L—C3L—C4L104.1 (2)C28—C33—C37121.19 (17)
C2L—C3L—H3LA110.9C29—C34—C36112.09 (19)
C4L—C3L—H3LA110.9C29—C34—C35111.93 (17)
C2L—C3L—H3LB110.9C36—C34—C35109.20 (18)
C4L—C3L—H3LB110.9C29—C34—H34A107.8
H3LA—C3L—H3LB109.0C36—C34—H34A107.8
O1L—C4L—C3L105.69 (19)C35—C34—H34A107.8
O1L—C4L—H4LA110.6C34—C35—H35A109.5
C3L—C4L—H4LA110.6C34—C35—H35B109.5
O1L—C4L—H4LB110.6H35A—C35—H35B109.5
C3L—C4L—H4LB110.6C34—C35—H35C109.5
H4LA—C4L—H4LB108.7H35A—C35—H35C109.5
C2—C1—C8131.28 (17)H35B—C35—H35C109.5
C2—C1—Si1116.16 (13)C34—C36—H36A109.5
C8—C1—Si1112.56 (13)C34—C36—H36B109.5
C2—C1—Sm173.47 (10)H36A—C36—H36B109.5
C8—C1—Sm173.99 (10)C34—C36—H36C109.5
Si1—C1—Sm1132.91 (9)H36A—C36—H36C109.5
C3—C2—C1135.86 (17)H36B—C36—H36C109.5
C3—C2—Sm175.82 (11)C33—C37—C39113.9 (2)
C1—C2—Sm175.16 (10)C33—C37—C38110.19 (19)
C3—C2—H2112.1C39—C37—C38109.1 (2)
C1—C2—H2112.1C33—C37—H37A107.8
Sm1—C2—H2131.8C39—C37—H37A107.8
C4—C3—C2135.30 (17)C38—C37—H37A107.8
C4—C3—Sm174.76 (10)C37—C38—H38A109.5
C2—C3—Sm173.13 (10)C37—C38—H38B109.5
C4—C3—H3112.3H38A—C38—H38B109.5
C2—C3—H3112.3C37—C38—H38C109.5
Sm1—C3—H3136.7H38A—C38—H38C109.5
C3—C4—C5136.25 (17)H38B—C38—H38C109.5
C3—C4—Sm174.42 (10)C37—C39—H39A109.5
C5—C4—Sm174.14 (10)C37—C39—H39B109.5
C3—C4—H4111.9H39A—C39—H39B109.5
C5—C4—H4111.9C37—C39—H39C109.5
Sm1—C4—H4136.7H39A—C39—H39C109.5
C4—C5—C6135.70 (18)H39B—C39—H39C109.5
C4—C5—Sm175.00 (10)C6L—C5L—C10L120.0
C6—C5—Sm175.36 (10)C6L—C5L—C11L120.9 (3)
C4—C5—H5112.2C10L—C5L—C11L119.1 (3)
C6—C5—H5112.2C7L—C6L—C5L120.0
Sm1—C5—H5132.7C7L—C6L—H6L120.0
C5—C6—C7130.70 (17)C5L—C6L—H6L120.0
C5—C6—Si2116.62 (14)C6L—C7L—C8L120.0
C7—C6—Si2112.67 (13)C6L—C7L—H7L120.0
C5—C6—Sm173.58 (10)C8L—C7L—H7L120.0
C7—C6—Sm173.23 (10)C9L—C8L—C7L120.0
Si2—C6—Sm1133.29 (9)C9L—C8L—H8L120.0
C8—C7—C6137.64 (17)C7L—C8L—H8L120.0
C8—C7—Sm174.14 (10)C8L—C9L—C10L120.0
C6—C7—Sm175.55 (10)C8L—C9L—H9L120.0
C8—C7—H7111.2C10L—C9L—H9L120.0
C6—C7—H7111.2C9L—C10L—C5L120.0
Sm1—C7—H7136.4C9L—C10L—H10L120.0
C7—C8—C1136.98 (17)C5L—C10L—H10L120.0
C7—C8—Sm174.70 (10)C42—C41—C46120.0
C1—C8—Sm174.61 (10)C42—C41—C47119.6 (7)
C7—C8—H8111.5C46—C41—C47120.4 (7)
C1—C8—H8111.5C41—C42—C43120.0
Sm1—C8—H8136.2C41—C42—H42120.0
Si1—C9—H9A109.5C43—C42—H42120.0
Si1—C9—H9B109.5C44—C43—C42120.0
H9A—C9—H9B109.5C44—C43—H43120.0
Si1—C9—H9C109.5C42—C43—H43120.0
H9A—C9—H9C109.5C45—C44—C43120.0
H9B—C9—H9C109.5C45—C44—H44120.0
Si1—C10—H10A109.5C43—C44—H44120.0
Si1—C10—H10B109.5C44—C45—C46120.0
H10A—C10—H10B109.5C44—C45—H45120.0
Si1—C10—H10C109.5C46—C45—H45120.0
H10A—C10—H10C109.5C45—C46—C41120.0
H10B—C10—H10C109.5C45—C46—H46120.0
Si1—C11—H11A109.5C41—C46—H46120.0
Si1—C11—H11B109.5
N2—Sm1—N1—C15−7.36 (10)C2—Sm1—C5—C6−105.61 (11)
O1L—Sm1—N1—C15−97.18 (11)C8—Sm1—C5—C6−45.55 (11)
C2—Sm1—N1—C1548.20 (13)C7—Sm1—C5—C6−21.40 (10)
C8—Sm1—N1—C15−91.8 (3)C1—Sm1—C5—C6−75.44 (11)
C7—Sm1—N1—C15−163.04 (11)C3—Sm1—C5—C6−128.91 (12)
C1—Sm1—N1—C1514.56 (18)C4—Sm1—C5—C6−146.70 (17)
C5—Sm1—N1—C15140.10 (11)C15—Sm1—C5—C6147.57 (10)
C3—Sm1—N1—C1577.50 (11)C4—C5—C6—C70.0 (4)
C4—Sm1—N1—C15108.48 (11)Sm1—C5—C6—C749.45 (19)
C6—Sm1—N1—C15169.48 (10)C4—C5—C6—Si2179.90 (18)
N2—Sm1—N1—C16−177.8 (3)Sm1—C5—C6—Si2−130.69 (11)
O1L—Sm1—N1—C1692.4 (3)C4—C5—C6—Sm1−49.4 (2)
C2—Sm1—N1—C16−122.2 (2)C13—Si2—C6—C5−117.72 (15)
C8—Sm1—N1—C1697.7 (4)C14—Si2—C6—C53.08 (19)
C7—Sm1—N1—C1626.5 (3)C12—Si2—C6—C5124.09 (17)
C1—Sm1—N1—C16−155.9 (2)C13—Si2—C6—C762.17 (16)
C5—Sm1—N1—C16−30.4 (3)C14—Si2—C6—C7−177.03 (15)
C3—Sm1—N1—C16−93.0 (3)C12—Si2—C6—C7−56.02 (17)
C4—Sm1—N1—C16−62.0 (3)C13—Si2—C6—Sm1150.11 (13)
C6—Sm1—N1—C16−1.0 (3)C14—Si2—C6—Sm1−89.10 (16)
C15—Sm1—N1—C16−170.4 (3)C12—Si2—C6—Sm131.91 (17)
O1L—Sm1—N2—C1593.46 (11)O1L—Sm1—C6—C5−153.64 (11)
N1—Sm1—N2—C157.35 (10)N1—Sm1—C6—C5−66.06 (12)
C2—Sm1—N2—C15−132.71 (11)C2—Sm1—C6—C572.24 (11)
C8—Sm1—N2—C15174.99 (10)C8—Sm1—C6—C5125.67 (12)
C7—Sm1—N2—C15157.41 (12)C7—Sm1—C6—C5143.02 (17)
C1—Sm1—N2—C15−162.72 (11)C1—Sm1—C6—C5102.75 (11)
C5—Sm1—N2—C15−57.08 (15)C3—Sm1—C6—C542.63 (11)
C3—Sm1—N2—C15−102.45 (11)C4—Sm1—C6—C519.17 (10)
C4—Sm1—N2—C15−77.71 (12)C15—Sm1—C6—C5−56.78 (15)
O1L—Sm1—N2—C28−118.5 (2)O1L—Sm1—C6—C763.34 (11)
N1—Sm1—N2—C28155.4 (2)N1—Sm1—C6—C7150.93 (10)
C2—Sm1—N2—C2815.3 (2)C2—Sm1—C6—C7−70.77 (11)
C8—Sm1—N2—C28−37.0 (2)C8—Sm1—C6—C7−17.34 (10)
C7—Sm1—N2—C28−54.6 (3)C1—Sm1—C6—C7−40.27 (11)
C1—Sm1—N2—C28−14.7 (2)C5—Sm1—C6—C7−143.02 (17)
C5—Sm1—N2—C2890.9 (2)C3—Sm1—C6—C7−100.38 (11)
C3—Sm1—N2—C2845.6 (2)C4—Sm1—C6—C7−123.84 (12)
C4—Sm1—N2—C2870.3 (2)C15—Sm1—C6—C7160.21 (11)
C15—Sm1—N2—C28148.0 (3)O1L—Sm1—C6—Si2−42.28 (12)
N2—Sm1—O1L—C4L−51.03 (16)N1—Sm1—C6—Si245.31 (14)
N1—Sm1—O1L—C4L3.40 (15)C2—Sm1—C6—Si2−176.39 (12)
C2—Sm1—O1L—C4L−138.83 (15)C8—Sm1—C6—Si2−122.96 (14)
C8—Sm1—O1L—C4L−175.65 (16)C7—Sm1—C6—Si2−105.62 (17)
C7—Sm1—O1L—C4L153.14 (16)C1—Sm1—C6—Si2−145.89 (13)
C1—Sm1—O1L—C4L−150.79 (15)C5—Sm1—C6—Si2111.36 (17)
C5—Sm1—O1L—C4L109.39 (16)C3—Sm1—C6—Si2154.00 (13)
C3—Sm1—O1L—C4L−158.88 (19)C4—Sm1—C6—Si2130.54 (14)
C4—Sm1—O1L—C4L111.23 (17)C15—Sm1—C6—Si254.59 (18)
C6—Sm1—O1L—C4L125.19 (16)C5—C6—C7—C8−4.1 (4)
C15—Sm1—O1L—C4L−23.72 (16)Si2—C6—C7—C8176.01 (19)
N2—Sm1—O1L—C1L120.43 (17)Sm1—C6—C7—C845.4 (2)
N1—Sm1—O1L—C1L174.85 (17)C5—C6—C7—Sm1−49.57 (19)
C2—Sm1—O1L—C1L32.62 (19)Si2—C6—C7—Sm1130.57 (10)
C8—Sm1—O1L—C1L−4.19 (17)N2—Sm1—C7—C828.92 (19)
C7—Sm1—O1L—C1L−35.41 (17)O1L—Sm1—C7—C894.09 (11)
C1—Sm1—O1L—C1L20.66 (17)N1—Sm1—C7—C8160.97 (11)
C5—Sm1—O1L—C1L−79.16 (18)C2—Sm1—C7—C8−43.18 (11)
C3—Sm1—O1L—C1L12.6 (3)C1—Sm1—C7—C8−17.77 (10)
C4—Sm1—O1L—C1L−77.3 (2)C5—Sm1—C7—C8−128.77 (13)
C6—Sm1—O1L—C1L−63.35 (17)C3—Sm1—C7—C8−73.66 (11)
C15—Sm1—O1L—C1L147.73 (17)C4—Sm1—C7—C8−103.52 (12)
C4L—O1L—C1L—C2L15.6 (3)C6—Sm1—C7—C8−150.06 (17)
Sm1—O1L—C1L—C2L−156.70 (17)C15—Sm1—C7—C8112.1 (3)
O1L—C1L—C2L—C3L−31.8 (3)N2—Sm1—C7—C6178.98 (11)
C1L—C2L—C3L—C4L35.9 (3)O1L—Sm1—C7—C6−115.85 (11)
C1L—O1L—C4L—C3L6.7 (3)N1—Sm1—C7—C6−48.97 (16)
Sm1—O1L—C4L—C3L179.8 (2)C2—Sm1—C7—C6106.88 (11)
C2L—C3L—C4L—O1L−26.6 (3)C8—Sm1—C7—C6150.06 (17)
C10—Si1—C1—C2−128.77 (15)C1—Sm1—C7—C6132.29 (13)
C9—Si1—C1—C2−8.41 (17)C5—Sm1—C7—C621.29 (10)
C11—Si1—C1—C2113.56 (15)C3—Sm1—C7—C676.40 (11)
C10—Si1—C1—C851.36 (16)C4—Sm1—C7—C646.54 (11)
C9—Si1—C1—C8171.73 (14)C15—Sm1—C7—C6−97.9 (3)
C11—Si1—C1—C8−66.30 (15)C6—C7—C8—C10.0 (4)
C10—Si1—C1—Sm1−37.41 (15)Sm1—C7—C8—C145.9 (2)
C9—Si1—C1—Sm182.95 (15)C6—C7—C8—Sm1−45.8 (2)
C11—Si1—C1—Sm1−155.07 (12)C2—C1—C8—C73.9 (4)
N2—Sm1—C1—C273.86 (11)Si1—C1—C8—C7−176.27 (19)
O1L—Sm1—C1—C2163.31 (10)Sm1—C1—C8—C7−45.9 (2)
N1—Sm1—C1—C255.93 (16)C2—C1—C8—Sm149.78 (18)
C8—Sm1—C1—C2−143.23 (16)Si1—C1—C8—Sm1−130.38 (10)
C7—Sm1—C1—C2−125.59 (12)N2—Sm1—C8—C7−164.76 (10)
C5—Sm1—C1—C2−72.64 (11)O1L—Sm1—C8—C7−82.02 (11)
C3—Sm1—C1—C2−19.37 (10)N1—Sm1—C8—C7−87.4 (3)
C4—Sm1—C1—C2−43.17 (10)C2—Sm1—C8—C7128.21 (13)
C6—Sm1—C1—C2−102.85 (11)C1—Sm1—C8—C7149.47 (17)
C15—Sm1—C1—C264.14 (12)C5—Sm1—C8—C742.53 (11)
N2—Sm1—C1—C8−142.91 (10)C3—Sm1—C8—C7102.78 (12)
O1L—Sm1—C1—C8−53.46 (11)C4—Sm1—C8—C772.78 (11)
N1—Sm1—C1—C8−160.84 (12)C6—Sm1—C8—C717.37 (10)
C2—Sm1—C1—C8143.23 (16)C15—Sm1—C8—C7−159.98 (11)
C7—Sm1—C1—C817.64 (10)N2—Sm1—C8—C145.77 (12)
C5—Sm1—C1—C870.59 (11)O1L—Sm1—C8—C1128.51 (11)
C3—Sm1—C1—C8123.87 (12)N1—Sm1—C8—C1123.2 (3)
C4—Sm1—C1—C8100.06 (11)C2—Sm1—C8—C1−21.27 (10)
C6—Sm1—C1—C840.38 (11)C7—Sm1—C8—C1−149.47 (17)
C15—Sm1—C1—C8−152.63 (10)C5—Sm1—C8—C1−106.95 (11)
N2—Sm1—C1—Si1−36.74 (12)C3—Sm1—C8—C1−46.69 (10)
O1L—Sm1—C1—Si152.70 (12)C4—Sm1—C8—C1−76.69 (11)
N1—Sm1—C1—Si1−54.68 (19)C6—Sm1—C8—C1−132.10 (12)
C2—Sm1—C1—Si1−110.61 (16)C15—Sm1—C8—C150.55 (16)
C8—Sm1—C1—Si1106.16 (17)C16—N1—C15—N2−172.00 (16)
C7—Sm1—C1—Si1123.81 (14)Sm1—N1—C15—N212.94 (17)
C5—Sm1—C1—Si1176.75 (12)C16—N1—C15—Sm1175.06 (17)
C3—Sm1—C1—Si1−129.97 (13)C28—N2—C15—N1−171.97 (16)
C4—Sm1—C1—Si1−153.78 (12)Sm1—N2—C15—N1−13.42 (18)
C6—Sm1—C1—Si1146.54 (12)C28—N2—C15—Sm1−158.55 (18)
C15—Sm1—C1—Si1−46.47 (14)N2—Sm1—C15—N1166.92 (17)
C8—C1—C2—C30.5 (3)O1L—Sm1—C15—N181.37 (11)
Si1—C1—C2—C3−179.36 (17)C2—Sm1—C15—N1−142.24 (11)
Sm1—C1—C2—C350.4 (2)C8—Sm1—C15—N1158.28 (12)
C8—C1—C2—Sm1−49.96 (18)C7—Sm1—C15—N163.6 (3)
Si1—C1—C2—Sm1130.20 (11)C1—Sm1—C15—N1−171.87 (10)
N2—Sm1—C2—C3104.62 (10)C5—Sm1—C15—N1−49.45 (13)
O1L—Sm1—C2—C3−169.07 (9)C3—Sm1—C15—N1−110.53 (11)
N1—Sm1—C2—C362.56 (12)C4—Sm1—C15—N1−79.15 (11)
C8—Sm1—C2—C3−125.09 (12)C6—Sm1—C15—N1−17.31 (16)
C7—Sm1—C2—C3−100.76 (11)O1L—Sm1—C15—N2−85.55 (11)
C1—Sm1—C2—C3−146.37 (16)N1—Sm1—C15—N2−166.92 (17)
C5—Sm1—C2—C3−41.23 (10)C2—Sm1—C15—N250.84 (12)
C4—Sm1—C2—C3−18.14 (10)C8—Sm1—C15—N2−8.64 (17)
C6—Sm1—C2—C3−71.02 (11)C7—Sm1—C15—N2−103.3 (3)
C15—Sm1—C2—C383.75 (11)C1—Sm1—C15—N221.21 (13)
N2—Sm1—C2—C1−109.01 (10)C5—Sm1—C15—N2143.63 (11)
O1L—Sm1—C2—C1−22.70 (13)C3—Sm1—C15—N282.55 (11)
N1—Sm1—C2—C1−151.07 (9)C4—Sm1—C15—N2113.93 (11)
C8—Sm1—C2—C121.28 (9)C6—Sm1—C15—N2175.77 (11)
C7—Sm1—C2—C145.61 (10)C15—N1—C16—C2152.3 (2)
C5—Sm1—C2—C1105.14 (11)Sm1—N1—C16—C21−138.5 (2)
C3—Sm1—C2—C1146.37 (16)C15—N1—C16—C17−128.79 (18)
C4—Sm1—C2—C1128.23 (12)Sm1—N1—C16—C1740.5 (3)
C6—Sm1—C2—C175.35 (10)C21—C16—C17—C18−0.8 (3)
C15—Sm1—C2—C1−129.88 (10)N1—C16—C17—C18−179.80 (18)
C1—C2—C3—C4−4.4 (4)C21—C16—C17—C22−176.26 (17)
Sm1—C2—C3—C445.8 (2)N1—C16—C17—C224.8 (3)
C1—C2—C3—Sm1−50.2 (2)C16—C17—C18—C19−0.8 (3)
N2—Sm1—C3—C4133.86 (10)C22—C17—C18—C19174.6 (2)
O1L—Sm1—C3—C4−119.81 (18)C17—C18—C19—C201.4 (4)
N1—Sm1—C3—C479.10 (11)C18—C19—C20—C21−0.3 (4)
C2—Sm1—C3—C4−148.49 (16)C19—C20—C21—C16−1.3 (4)
C8—Sm1—C3—C4−102.83 (11)C19—C20—C21—C25177.9 (2)
C7—Sm1—C3—C4−72.49 (11)C17—C16—C21—C201.8 (3)
C1—Sm1—C3—C4−128.93 (12)N1—C16—C21—C20−179.24 (19)
C5—Sm1—C3—C4−17.81 (10)C17—C16—C21—C25−177.29 (18)
C6—Sm1—C3—C4−41.80 (10)N1—C16—C21—C251.6 (3)
C15—Sm1—C3—C4106.47 (11)C18—C17—C22—C23−91.7 (2)
N2—Sm1—C3—C2−77.66 (11)C16—C17—C22—C2383.7 (2)
O1L—Sm1—C3—C228.7 (2)C18—C17—C22—C2432.6 (3)
N1—Sm1—C3—C2−132.42 (10)C16—C17—C22—C24−152.04 (18)
C8—Sm1—C3—C245.66 (10)C20—C21—C25—C26−59.2 (3)
C7—Sm1—C3—C276.00 (11)C16—C21—C25—C26120.0 (2)
C1—Sm1—C3—C219.55 (10)C20—C21—C25—C2765.1 (3)
C5—Sm1—C3—C2130.68 (12)C16—C21—C25—C27−115.8 (2)
C4—Sm1—C3—C2148.49 (16)C15—N2—C28—C2966.6 (2)
C6—Sm1—C3—C2106.68 (11)Sm1—N2—C28—C29−76.8 (2)
C15—Sm1—C3—C2−105.04 (10)C15—N2—C28—C33−114.88 (19)
C2—C3—C4—C50.1 (4)Sm1—N2—C28—C33101.8 (2)
Sm1—C3—C4—C545.4 (2)C33—C28—C29—C301.8 (3)
C2—C3—C4—Sm1−45.3 (2)N2—C28—C29—C30−179.67 (17)
N2—Sm1—C4—C3−54.00 (12)C33—C28—C29—C34−177.38 (17)
O1L—Sm1—C4—C3146.16 (12)N2—C28—C29—C341.1 (3)
N1—Sm1—C4—C3−109.91 (11)C28—C29—C30—C31−0.6 (3)
C2—Sm1—C4—C318.27 (10)C34—C29—C30—C31178.6 (2)
C8—Sm1—C4—C373.64 (11)C29—C30—C31—C32−1.1 (3)
C7—Sm1—C4—C3103.88 (11)C30—C31—C32—C331.7 (4)
C1—Sm1—C4—C342.75 (10)C31—C32—C33—C28−0.5 (3)
C5—Sm1—C4—C3149.18 (17)C31—C32—C33—C37176.2 (2)
C6—Sm1—C4—C3129.90 (12)C29—C28—C33—C32−1.3 (3)
C15—Sm1—C4—C3−82.41 (11)N2—C28—C33—C32−179.86 (17)
N2—Sm1—C4—C5156.81 (10)C29—C28—C33—C37−177.94 (18)
O1L—Sm1—C4—C5−3.02 (18)N2—C28—C33—C373.5 (3)
N1—Sm1—C4—C5100.91 (11)C30—C29—C34—C36−47.3 (2)
C2—Sm1—C4—C5−130.91 (12)C28—C29—C34—C36131.83 (19)
C8—Sm1—C4—C5−75.54 (11)C30—C29—C34—C3575.8 (2)
C7—Sm1—C4—C5−45.31 (11)C28—C29—C34—C35−105.1 (2)
C1—Sm1—C4—C5−106.44 (11)C32—C33—C37—C3932.4 (3)
C3—Sm1—C4—C5−149.18 (17)C28—C33—C37—C39−150.99 (19)
C6—Sm1—C4—C5−19.28 (10)C32—C33—C37—C38−90.5 (2)
C15—Sm1—C4—C5128.40 (11)C28—C33—C37—C3886.1 (2)
C3—C4—C5—C64.0 (4)C10L—C5L—C6L—C7L0.0
Sm1—C4—C5—C649.5 (2)C11L—C5L—C6L—C7L−178.0 (3)
C3—C4—C5—Sm1−45.5 (2)C5L—C6L—C7L—C8L0.0
N2—Sm1—C5—C4−37.34 (16)C6L—C7L—C8L—C9L0.0
O1L—Sm1—C5—C4178.40 (10)C7L—C8L—C9L—C10L0.0
N1—Sm1—C5—C4−87.03 (11)C8L—C9L—C10L—C5L0.0
C2—Sm1—C5—C441.09 (11)C6L—C5L—C10L—C9L0.0
C8—Sm1—C5—C4101.15 (11)C11L—C5L—C10L—C9L178.1 (3)
C7—Sm1—C5—C4125.30 (13)C46—C41—C42—C430.0
C1—Sm1—C5—C471.26 (11)C47—C41—C42—C43178.6 (16)
C3—Sm1—C5—C417.79 (10)C41—C42—C43—C440.0
C6—Sm1—C5—C4146.70 (17)C42—C43—C44—C450.0
C15—Sm1—C5—C4−65.73 (12)C43—C44—C45—C460.0
N2—Sm1—C5—C6175.96 (9)C44—C45—C46—C410.0
O1L—Sm1—C5—C631.71 (13)C42—C41—C46—C450.0
N1—Sm1—C5—C6126.27 (10)C47—C41—C46—C45−178.6 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2077).

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