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ISSN: 2056-9890

Crystal structure and Hirshfeld surface analysis of ((S,S)-2,2′-{[(1,2-di­phenyl­ethane-1,2-di­yl)bis­­[(aza­n­ium­ylyl­­idene)methanylyl­­idene]}bis­­(6-meth­­oxy­phenolato))trinitratosamarium(III)

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aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
*Correspondence e-mail: akitsu2@rs.tus.ac.jp

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 12 April 2021; accepted 26 April 2021; online 30 April 2021)

In the title complex, [Sm(NO3)3(C30H28N2O4)], the Sm atom is surrounded by ten O atoms. The (S,S)-2,2′-{[(1,2-di­phenyl­ethane-1,2-di­yl)bis­[(aza­niumylyl­idene)methanylyl­idene]}bis­(6-meth­oxy­phenolate) ligand, obtained from o-vanillin and (1S,2S)-(−)-1,2-di­phenyl­ethyl­enedi­amine, exhibits a slightly distorted planar arrangement of the four coordinated O atoms. In the crystal, the complex shows intra­molecular N—H⋯O hydrogen bonds and weak inter­molecular C—H⋯O hydrogen bonds. The Hirshfeld surface analysis indicates that the most important contributions to the packing are from H⋯H (33.5%), O⋯H (34.1%) and C⋯H (21.7%) contacts.

1. Chemical context

Lanthanide metal complexes can have attractive functions such as magnetism and fluorescence when synthesized with properly designed ligands (Yao et al., 2019[Yao, Y., Yin, H. Y., Ning, Y., Wang, J., Meng, Y. S., Huang, X., Zhang, W., Kang, L. & Zhang, J. L. (2019). Inorg. Chem. 58, 1806-1814.]; Lin et al., 2009[Lin, P. H., Burchell, T. J., Ungur, L., Chibotaru, L. F., Wernsdorfer, W. & Murugesu, M. (2009). Angew. Chem. Int. Ed. 48, 9489-9492.]). In recent years, lanthanide complexes that act as single-mol­ecule magnets (SMM) have received much attention (Then et al., 2015[Then, P. L., Takehara, C., Kataoka, Y., Nakano, M., Yamamura, T. & Kajiwara, T. (2015). Dalton Trans. 44, 18038-18048.]). In these complexes, distortion of the coordination geometry is an important factor for magnetic anisotropy and for the resulting SMM properties. However, the coordination chemistry of lanthanides is complicated, and it is necessary to prepare complexes with coordination environments suitable for the required properties. On the other hand, salen ligands are known to form stable chelate complexes with many metals (Cozzi et al., 2004[Cozzi, P. G. (2004). Chem. Soc. Rev. 33, 410-421.]). By incorporating a substituent group into salen ligands, it is possible to easily add more coordination sites and optical functionality such as the antenna effect that depend on inter­molecular inter­actions and arrangements. Hence, functional lanthanide salen complexes have attracted attention (Ren et al., 2016[Ren, M., Xu, Z.-L., Bao, S.-S., Wang, T.-T., Zheng, Z.-H., Ferreira, R. A. S., Zheng, L.-M. & Carlos, L. D. (2016). Dalton Trans. 45, 2974-2982.]). Accurate data such as bond angles and the geometry of coordination sites obtained based on crystal structure analysis and Hirshfeld surface analysis will be useful for the mol­ecular design of new lanthanide and salen complexes. In this study, we prepared a new SmIII–salen complex and report herein on its crystal structure and Hirshfeld surface analysis.

2. Structural commentary

The title SmIII complex crystallizes in the monoclinic space group C2. The asymmetric unit contains two crystallographically independent mol­ecules. This distorted prismatic [SmO10] complex consists of three bidentate nitrate ions and two pairs of phenolate and meth­oxy groups of the salen ligand, which is slightly distorted from planar.

[Scheme 1]

The bond distances between the metal center and ligating atoms range from 2.333 (5) to 2.373 (4) Å for the phenolato oxygen atoms, and from 2.606 (5) to 2.621 (6) Å for meth­oxy oxygen atoms. The bond lengths between the metal center and the nitrate oxygen atoms range from 2.475 (5) to 2.633 (5) Å, showing more flexibility than those of the Schiff base ligand. In the Schiff base ligand, the imine moieties are protonated to form iminium cations, but the C=N bond lengths remain close to those of normal imine bonds at 1.287 (8) and 1.30 (1) Å.

Intra­molecular hydrogen bonds occur between the iminium protons and the phenolic oxygen atoms, with lengths of 1.71–1.89 Å (Table 1[link], Fig. 1[link]). The bond distances and angles in the ligand are similar to those of analogous complexes (Hayashi et al., 2013[Hayashi, T., Shibata, H., Orita, S. & Akitsu, T. (2013). Eur. Chem. Bull. 2, 49-57.]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C98—H98A⋯O9i 0.98 2.58 3.419 (9) 144
C91—H91⋯O27ii 0.95 2.59 3.097 (8) 114
C91—H91⋯O12iii 0.95 2.33 3.227 (8) 156
C77—H77⋯O24iv 1.00 2.29 3.264 (8) 164
C76—H76⋯O21iv 0.95 2.50 3.399 (9) 158
C69—H69A⋯O14v 0.98 2.44 3.323 (10) 150
C68—H68A⋯O10 0.98 2.55 3.214 (11) 125
C68—H68A⋯O9 0.98 2.66 3.224 (11) 117
C65—H65⋯O20vi 0.95 2.64 3.485 (8) 148
C61—H61⋯O13vi 0.95 2.49 3.429 (8) 172
C54—H54⋯O11vi 1.00 2.30 3.277 (8) 165
C46—H46⋯O25 0.95 2.32 3.211 (8) 155
C46—H46⋯O8i 0.95 2.56 3.054 (8) 113
C39—H39A⋯O27i 0.98 2.54 3.338 (9) 138
N38—H38⋯O18 0.86 1.87 2.550 (6) 135
N33—H33⋯O4 0.86 1.87 2.545 (7) 134
N37—H37⋯O17 0.83 1.89 2.582 (7) 139
N32—H32⋯O5 1.04 1.71 2.578 (6) 138
Symmetry codes: (i) [-x+1, y, -z+1]; (ii) [-x+1, y, -z]; (iii) [x, y, z-1]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z]; (v) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+1]; (vi) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1].
[Figure 1]
Figure 1
View of the two independent complex mol­ecules of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Intra­molecular hydrogen bonds are shown as dashed lines. All non-H atoms should be labelled

3. Supra­molecular features

Though some weak C—H⋯O inter­molecular inter­actions are found (Table 1[link]), no strong inter­actions such as O—H⋯O hydrogen bonds between mol­ecules are observed in the crystal. Hirshfeld surface analysis (Spackman et al., 2009[Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19-32.]) was performed to investigate inter­actions in the crystal packing. Hirshfeld surfaces and fingerprint plots (McKinnon et al., 2004[McKinnon, J. J., Spackman, M. A. & Mitchell, A. S. (2004). Acta Cryst. B60, 627-668.]) were calculated using CrystalExplorer17.5 (Turner et al., 2017[Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17.5. University of Western Australia. https://hirshfeldsuface.net]). Hydrogen bonds are strong inter­actions and they are indicated as red dots on the surface (Fig. 2[link]) or two sharp spikes in the fingerprint plot (Fig. 3[link]). `Wings' in the fingerprint plots and diagonal plots at 1.8 Å are regarded as a characteristic feature potentially resulting from aromatic rings (Spackman et al., 2002[Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378-392.])The contributions to the Hirshfeld surface are H⋯H (33.5%), O⋯H (34.1%) and C⋯H (21.7%) contacts.

[Figure 2]
Figure 2
Hirshfeld surfaces plotted over of dnorm for (a) all inter­actions and (b) O⋯H/H⋯O, (c) C⋯C and (d) C⋯H/H⋯C contacts.
[Figure 3]
Figure 3
Two-dimensional fingerprint plots and contributions for various inter­actions.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.41, update of November 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for similar structures returned two relevant entries: (N,N′-ethane-1,2-diylbis{[2-(­oxy)-3-(meth­oxy)phen­yl]methaniminiumato})tris(nitrato)samarium (refcode MOLNEI; Yang et al., 2013[Yang, Y., Yan, P. F., Gao, P., Gao, T., Hou, G. F. & Li, G. M. (2013). J. Inorg. Organomet. Polym. 23, 1211-1218.]) and (S,S)-{μ-[2,2′-{(1,2-di­phenyl­ethane-1,2-di­yl)bis­[(aza­nylyl­idene)methylyl­idene]}bis[6-(meth­oxy)phenolato]]}trinitratoeuropium(III)nickel(II) (JIWNEL; Mayans et al., 2019[Mayans, J., Saez, Q., Font-Bardia, M. & Escuer, A. (2019). Dalton Trans. 48, 641-652.]). In MOLNEI, a similar intra­molecular N—H⋯O hydrogen bond is observed. Although the ligand of JIWNEL is similar to that in the title compound, the coordinating sites are filled with europium(III) and nickel(II) ions. For both MOLNEI and JIWNEL, the crystal packing is dominated by van der Waals inter­actions and C—H⋯O hydrogen bonds.

5. Synthesis and crystallization

(1S,2S)-(−)-1,2-Di­phenyl­ethyl­enedi­amine (0.100 g, 0.471 mmol) and o-vanillin (0.143 g, 0.940 mmol) were dissolved in ethanol (30 mL) and the resulting mixture was stirred at 313 K for 1 h to afford a yellow solution. To this solution, samarium nitrate hexa­hydrate (0.208 g, 0.468 mmol) was added and it was stirred at 313 K for 2 h. A yellow precipitate appeared immediately. The precipitate was filtered and washed with ethanol and hexane. The title compound (0.299 g, 0.366 mmol, yield 78.2%) was obtained as a yellow solid. IR (KBr, cm−1) : 1624 (C=N double bond). Fluorescence bands in methanol solution were observed at 562 (4G5/26H5/2), 597 (4G5/26H7/2) and 644 (4G5/26H 9/2) nm. Single crystals suitable for X-ray diffraction were obtained by recrystallization from methanol and diethyl ether (1:4, v/v) solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All C-bound H atoms were placed in geometrically calculated positions (C—H = 0.93–0.98 Å) and were constrained using a riding model with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-meth­yl). SIMU, ISOR and AFIX 66 commands were used for C55, C56, C57, C58, C59, C60 to suppress temperature anisotropy and restrain bond lengths to appropriate values.

Table 2
Experimental details

Crystal data
Chemical formula [Sm(NO3)3(C30H28N2O4)]
Mr 816.92
Crystal system, space group Monoclinic, C2
Temperature (K) 173
a, b, c (Å) 18.9105 (6), 15.7993 (5), 21.5738 (7)
β (°) 98.727 (1)
V3) 6371.0 (4)
Z 8
Radiation type Mo Kα
μ (mm−1) 1.92
Crystal size (mm) 0.59 × 0.30 × 0.10
 
Data collection
Diffractometer Bruker APEXIII CCD
Absorption correction Multi-scan
Tmin, Tmax 0.40, 0.83
No. of measured, independent and observed [I > 2σ(I)] reflections 40695, 15028, 12523
Rint 0.042
(sin θ/λ)max−1) 0.732
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.116, 0.83
No. of reflections 15028
No. of parameters 881
No. of restraints 49
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.84, −1.58
Absolute structure Flack x determined using 4865 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.009 (9)
Computer programs: APEX3 and SAINT (Bruker, 2017[Bruker (2017). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014/5 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016/6 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), shelXle (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Computing details top

Data collection: APEX3 (Bruker, 2017); cell refinement: APEX3 (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle et al., 2011); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

((S,S)-2,2'-{(1,2-diphenylethane-1,2-diyl)bis[(azaniumylylidene)methanylylidene]}bis(6-methoxyphenolato))trinitratosamarium(III) top
Crystal data top
[Sm(NO3)3(C30H28N2O4)]F(000) = 3272
Mr = 816.92Dx = 1.703 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 18.9105 (6) ÅCell parameters from 859 reflections
b = 15.7993 (5) Åθ = 1.7–28.6°
c = 21.5738 (7) ŵ = 1.92 mm1
β = 98.727 (1)°T = 173 K
V = 6371.0 (4) Å3Prism, yellow
Z = 80.59 × 0.30 × 0.10 mm
Data collection top
Bruker APEXIII CCD
diffractometer
15028 independent reflections
Radiation source: fine-focus sealed tube12523 reflections with I > 2σ(I)
Detector resolution: 7.3910 pixels mm-1Rint = 0.042
φ and ω scansθmax = 31.3°, θmin = 1.9°
Absorption correction: multi-scanh = 2727
Tmin = 0.40, Tmax = 0.83k = 2021
40695 measured reflectionsl = 2830
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.1P)2 + 0.6514P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.001
S = 0.83Δρmax = 0.84 e Å3
15028 reflectionsΔρmin = 1.58 e Å3
881 parametersAbsolute structure: Flack x determined using 4865 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
49 restraintsAbsolute structure parameter: 0.009 (9)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Sm10.34946 (2)0.59358 (2)0.63113 (2)0.03104 (10)
Sm20.34751 (2)0.39584 (2)0.13107 (2)0.03191 (11)
O30.4131 (3)0.4594 (4)0.5968 (2)0.0440 (13)
O40.3665 (2)0.5842 (4)0.52494 (19)0.0336 (10)
O50.3218 (3)0.7237 (3)0.5804 (2)0.0342 (11)
O60.3492 (3)0.7271 (4)0.7027 (2)0.0398 (12)
H320.3122100.7497660.5027810.05 (2)*
O70.4735 (3)0.6447 (5)0.6256 (3)0.065 (2)
O90.4581 (3)0.5828 (6)0.7107 (2)0.0519 (16)
O80.5637 (3)0.6337 (7)0.7015 (3)0.081 (3)
O100.3289 (3)0.5319 (4)0.7402 (2)0.0497 (14)
O110.2958 (3)0.4561 (4)0.6585 (2)0.0401 (12)
O120.2771 (3)0.4098 (5)0.7490 (2)0.0501 (16)
O130.2293 (3)0.5689 (4)0.5608 (2)0.0416 (13)
O140.2255 (3)0.6244 (4)0.6515 (2)0.0509 (15)
O150.1278 (3)0.6161 (6)0.5828 (4)0.081 (3)
O160.4178 (3)0.5280 (4)0.0995 (2)0.0423 (13)
O170.3733 (2)0.4025 (4)0.02689 (18)0.0361 (11)
O180.3128 (3)0.2709 (3)0.0773 (2)0.0392 (11)
O190.3455 (3)0.2594 (4)0.1986 (2)0.0449 (13)
O200.2196 (3)0.3731 (4)0.1473 (2)0.0473 (13)
O210.2315 (3)0.4286 (4)0.0572 (2)0.0438 (14)
O220.1272 (3)0.3899 (7)0.0772 (3)0.082 (2)
O230.3243 (3)0.4607 (3)0.2386 (2)0.0399 (12)
H370.3368160.3423490.0468330.06 (2)*
O240.2953 (3)0.5368 (4)0.1565 (2)0.0407 (13)
O250.2780 (2)0.5849 (4)0.24702 (19)0.0387 (11)
O260.4537 (3)0.4042 (5)0.2154 (2)0.0456 (13)
O270.5601 (3)0.3585 (5)0.2082 (2)0.0656 (19)
O280.4709 (3)0.3425 (6)0.1312 (3)0.074 (2)
N290.1918 (3)0.6040 (6)0.5969 (3)0.0446 (17)
N300.3004 (3)0.4638 (5)0.7169 (3)0.0369 (15)
N310.5005 (3)0.6206 (7)0.6799 (3)0.059 (3)
N320.3003 (2)0.8029 (3)0.4747 (2)0.0295 (10)
N330.3249 (3)0.6451 (4)0.4163 (2)0.0274 (10)
H330.3303490.6521210.4562980.033*
N340.1893 (3)0.3978 (6)0.0936 (3)0.0458 (15)
N350.2982 (3)0.5279 (4)0.2156 (2)0.0334 (14)
N360.4974 (3)0.3681 (5)0.1853 (3)0.0427 (18)
N370.3445 (3)0.3371 (4)0.0837 (2)0.0290 (11)
N380.2753 (2)0.2045 (3)0.0304 (2)0.0283 (10)
H380.2817830.2493610.0076280.034*
C390.4367 (4)0.3910 (7)0.6385 (3)0.051 (2)
H39A0.4459940.4122740.6816990.077*
H39B0.4806600.3667180.6272540.077*
H39C0.3994640.3474010.6352580.077*
C400.4033 (4)0.4420 (5)0.5336 (3)0.0346 (17)
C410.4114 (3)0.3647 (4)0.5056 (3)0.0370 (17)
H410.4250500.3165320.5309570.044*
C420.3999 (4)0.3567 (5)0.4409 (3)0.0450 (18)
H420.4040840.3030860.4218990.054*
C430.3821 (4)0.4278 (5)0.4040 (3)0.0390 (17)
H430.3773680.4232800.3596720.047*
C440.3710 (3)0.5060 (5)0.4313 (3)0.0306 (14)
C450.3808 (3)0.5142 (5)0.4972 (3)0.0261 (13)
C460.3426 (3)0.5731 (5)0.3933 (3)0.0287 (15)
H460.3360290.5661350.3490230.034*
C470.2838 (3)0.7123 (4)0.3798 (2)0.0294 (11)
H470.2962230.7105750.3364100.035*
C480.2038 (3)0.6939 (4)0.3748 (3)0.0314 (13)
C490.1730 (3)0.6685 (5)0.4268 (3)0.0353 (14)
H490.2018240.6633850.4667310.042*
C500.1002 (4)0.6509 (5)0.4202 (4)0.0455 (18)
H500.0793760.6333470.4554760.055*
C510.0585 (4)0.6587 (5)0.3627 (4)0.051 (2)
H510.0089720.6454440.3583180.062*
C530.1603 (4)0.7029 (5)0.3165 (3)0.0361 (15)
H530.1806230.7205950.2809870.043*
C520.0877 (4)0.6858 (6)0.3107 (4)0.0477 (18)
H520.0580450.6926890.2713750.057*
C540.3039 (3)0.8011 (4)0.4069 (2)0.0307 (11)
H540.2663890.8409830.3865310.037*
C550.37537 (19)0.8350 (3)0.3938 (3)0.0392 (13)
C560.3759 (2)0.9062 (4)0.3560 (3)0.069 (2)
H560.3321340.9314500.3376640.083*
C570.4406 (3)0.9405 (4)0.3451 (3)0.079 (3)
H570.4410100.9891640.3192820.095*
C580.5047 (2)0.9036 (5)0.3720 (4)0.073 (2)
H580.5489250.9270440.3645090.087*
C590.50415 (19)0.8324 (5)0.4098 (4)0.118 (4)
H590.5479640.8072120.4281180.141*
C600.4395 (2)0.7981 (4)0.4207 (3)0.106 (3)
H600.4390880.7494980.4465010.128*
C610.2952 (3)0.8720 (4)0.5059 (3)0.0283 (12)
H610.2859570.9237580.4837510.034*
C620.3030 (3)0.8722 (5)0.5719 (3)0.0312 (15)
C630.3003 (4)0.9513 (5)0.6042 (4)0.0373 (16)
H630.2903801.0020880.5809410.045*
C640.3119 (4)0.9538 (6)0.6681 (4)0.0469 (19)
H640.3095071.0062120.6891940.056*
C650.3274 (4)0.8795 (5)0.7026 (3)0.0397 (17)
H650.3349730.8824980.7471410.048*
C660.3318 (4)0.8029 (5)0.6744 (3)0.0354 (15)
C670.3177 (3)0.7977 (5)0.6067 (3)0.0281 (14)
C680.3680 (4)0.7271 (6)0.7700 (3)0.0499 (19)
H68A0.3842190.6704270.7842310.075*
H68B0.3260800.7427480.7891530.075*
H68C0.4065010.7680060.7823670.075*
C690.3627 (5)0.2536 (6)0.2657 (3)0.057 (2)
H69A0.3222450.2287280.2827720.085*
H69B0.3724510.3103480.2833180.085*
H69C0.4050730.2178860.2767650.085*
C700.3310 (4)0.1831 (5)0.1664 (3)0.0342 (15)
C710.3305 (4)0.1039 (6)0.1932 (3)0.0419 (17)
H710.3389440.0978750.2374820.050*
C720.3176 (4)0.0323 (5)0.1545 (4)0.0423 (17)
H720.3184840.0224870.1728390.051*
C730.3036 (4)0.0408 (5)0.0901 (3)0.0387 (16)
H730.2964860.0080630.0641780.046*
C740.3000 (3)0.1208 (5)0.0631 (3)0.0323 (16)
C750.3144 (4)0.1955 (5)0.1012 (3)0.0326 (15)
C760.2819 (3)0.1313 (4)0.0040 (3)0.0307 (13)
H760.2745960.0822150.0295710.037*
C770.2589 (3)0.2203 (3)0.0980 (2)0.0289 (10)
H770.2513410.1640190.1191070.035*
C780.1892 (3)0.2715 (4)0.1156 (3)0.0320 (13)
C790.1580 (5)0.2715 (5)0.1764 (4)0.0464 (19)
H790.1812220.2436220.2067140.056*
C800.0928 (5)0.3114 (6)0.1954 (4)0.062 (2)
H800.0724110.3117220.2384580.074*
C810.0583 (4)0.3498 (6)0.1523 (5)0.064 (3)
H810.0128080.3753850.1644740.077*
C820.0911 (4)0.3511 (6)0.0897 (5)0.057 (2)
H820.059 (4)0.370 (6)0.064 (4)0.06 (2)*
C830.1553 (4)0.3129 (5)0.0719 (4)0.0423 (16)
H830.1769790.3145610.0291800.051*
C840.3251 (3)0.2616 (4)0.1208 (2)0.0329 (11)
H840.3113820.2787650.1655890.039*
C860.3769 (3)0.1272 (4)0.1558 (3)0.0393 (14)
H860.3334390.1198030.1837560.047*
C850.3858 (3)0.1973 (4)0.1169 (3)0.0322 (11)
C870.4309 (4)0.0681 (6)0.1540 (4)0.0556 (19)
H870.4229100.0192030.1797430.067*
C890.5036 (4)0.1445 (7)0.0774 (5)0.088 (4)
H890.5464990.1490870.0483870.106*
C880.4945 (4)0.0776 (6)0.1170 (5)0.063 (2)
H880.5321610.0382660.1186880.076*
C900.4500 (4)0.2080 (5)0.0785 (4)0.0558 (18)
H900.4585920.2570540.0529280.067*
C910.3504 (3)0.4121 (5)0.1058 (3)0.0297 (14)
H910.3413920.4199840.1499960.036*
C920.3701 (3)0.4843 (5)0.0666 (3)0.0269 (13)
C930.3750 (4)0.5661 (5)0.0934 (4)0.0389 (17)
H930.3644890.5731230.1375290.047*
C940.3946 (4)0.6338 (5)0.0564 (4)0.0402 (16)
H940.3978980.6879580.0748570.048*
C950.4104 (4)0.6247 (5)0.0098 (3)0.0403 (19)
H950.4247910.6723830.0354500.048*
C960.4046 (3)0.5466 (5)0.0363 (3)0.0302 (15)
C970.3825 (3)0.4752 (5)0.0004 (3)0.0324 (15)
C980.4469 (4)0.5942 (7)0.1414 (3)0.0467 (18)
H98A0.4565070.5721190.1843230.070*
H98B0.4125600.6408950.1395440.070*
H98C0.4916360.6147980.1290010.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.0435 (2)0.0290 (2)0.02008 (18)0.00589 (17)0.00313 (14)0.00049 (14)
Sm20.0474 (2)0.0301 (2)0.01812 (17)0.00325 (17)0.00465 (15)0.00037 (14)
O30.064 (3)0.034 (3)0.036 (3)0.019 (3)0.013 (2)0.010 (2)
O40.050 (2)0.028 (3)0.0227 (19)0.010 (2)0.0059 (17)0.001 (2)
O50.054 (3)0.024 (2)0.024 (2)0.005 (2)0.0048 (18)0.0034 (19)
O60.059 (3)0.033 (3)0.028 (2)0.002 (3)0.005 (2)0.004 (2)
O70.054 (3)0.107 (6)0.033 (3)0.017 (4)0.004 (2)0.002 (3)
O90.048 (3)0.071 (5)0.034 (2)0.010 (3)0.001 (2)0.004 (3)
O80.042 (3)0.157 (8)0.044 (3)0.005 (4)0.000 (2)0.007 (4)
O100.072 (3)0.044 (3)0.031 (3)0.018 (3)0.001 (2)0.011 (3)
O110.048 (3)0.036 (3)0.036 (3)0.004 (2)0.005 (2)0.007 (2)
O120.052 (3)0.052 (4)0.043 (3)0.018 (3)0.004 (2)0.011 (3)
O130.050 (3)0.042 (3)0.032 (2)0.004 (2)0.003 (2)0.004 (2)
O140.061 (3)0.056 (4)0.038 (3)0.012 (3)0.016 (2)0.005 (3)
O150.052 (3)0.096 (6)0.093 (5)0.019 (4)0.009 (3)0.024 (5)
O160.057 (3)0.050 (4)0.021 (2)0.014 (3)0.007 (2)0.009 (2)
O170.060 (3)0.029 (3)0.0190 (19)0.009 (3)0.0066 (18)0.001 (2)
O180.064 (3)0.029 (3)0.026 (2)0.005 (2)0.007 (2)0.004 (2)
O190.076 (3)0.038 (3)0.020 (2)0.007 (3)0.004 (2)0.007 (2)
O200.053 (3)0.049 (3)0.042 (3)0.008 (3)0.012 (2)0.001 (2)
O210.054 (3)0.049 (3)0.026 (2)0.003 (3)0.001 (2)0.004 (2)
O220.043 (3)0.126 (7)0.074 (4)0.004 (4)0.001 (3)0.025 (5)
O230.061 (3)0.033 (3)0.024 (2)0.005 (3)0.001 (2)0.001 (2)
O240.068 (3)0.036 (3)0.019 (2)0.001 (3)0.011 (2)0.004 (2)
O250.049 (2)0.040 (3)0.027 (2)0.001 (3)0.0064 (18)0.009 (2)
O260.053 (3)0.057 (4)0.028 (2)0.002 (3)0.010 (2)0.006 (3)
O270.053 (3)0.101 (6)0.044 (3)0.007 (3)0.009 (2)0.003 (3)
O280.063 (4)0.119 (7)0.038 (3)0.014 (4)0.000 (3)0.035 (4)
N290.041 (3)0.046 (4)0.047 (4)0.008 (3)0.006 (3)0.010 (3)
N300.046 (3)0.037 (4)0.028 (3)0.000 (3)0.005 (2)0.006 (3)
N310.039 (3)0.099 (8)0.037 (3)0.007 (4)0.002 (3)0.011 (4)
N320.030 (2)0.025 (3)0.032 (2)0.002 (2)0.0013 (18)0.0037 (18)
N330.032 (2)0.027 (3)0.024 (2)0.003 (2)0.0046 (18)0.0007 (19)
N340.048 (3)0.042 (4)0.047 (4)0.001 (3)0.007 (3)0.016 (3)
N350.034 (3)0.034 (4)0.029 (3)0.004 (3)0.002 (2)0.001 (3)
N360.046 (3)0.055 (5)0.028 (3)0.000 (3)0.005 (2)0.004 (3)
N370.034 (2)0.034 (3)0.018 (2)0.001 (2)0.0028 (18)0.0017 (19)
N380.033 (2)0.028 (2)0.024 (2)0.001 (2)0.0035 (17)0.0024 (18)
C390.071 (5)0.048 (5)0.037 (4)0.022 (5)0.015 (3)0.012 (4)
C400.045 (4)0.031 (4)0.029 (3)0.003 (3)0.010 (3)0.004 (3)
C410.042 (3)0.019 (4)0.052 (4)0.009 (3)0.014 (3)0.006 (3)
C420.059 (4)0.037 (4)0.039 (4)0.005 (4)0.008 (3)0.017 (3)
C430.050 (4)0.036 (4)0.029 (3)0.007 (3)0.001 (3)0.007 (3)
C440.029 (3)0.035 (4)0.027 (3)0.002 (3)0.002 (2)0.006 (3)
C450.026 (3)0.031 (4)0.021 (3)0.003 (3)0.000 (2)0.001 (3)
C460.027 (3)0.037 (4)0.022 (3)0.001 (3)0.001 (2)0.005 (3)
C470.038 (3)0.030 (3)0.021 (2)0.002 (2)0.005 (2)0.004 (2)
C480.031 (3)0.024 (3)0.036 (3)0.004 (2)0.004 (2)0.003 (2)
C490.034 (3)0.032 (3)0.038 (3)0.006 (3)0.002 (2)0.003 (3)
C500.039 (3)0.036 (4)0.062 (4)0.004 (3)0.010 (3)0.011 (3)
C510.029 (3)0.037 (4)0.083 (6)0.008 (3)0.008 (3)0.005 (4)
C530.042 (3)0.033 (4)0.030 (3)0.007 (3)0.004 (2)0.001 (3)
C520.040 (3)0.041 (4)0.054 (4)0.005 (3)0.018 (3)0.000 (4)
C540.033 (2)0.030 (3)0.029 (2)0.002 (2)0.005 (2)0.003 (2)
C550.027 (2)0.036 (3)0.055 (3)0.002 (3)0.009 (2)0.002 (3)
C560.048 (4)0.084 (6)0.070 (5)0.020 (4)0.005 (3)0.038 (4)
C570.050 (4)0.092 (6)0.093 (6)0.036 (4)0.003 (4)0.032 (5)
C580.040 (3)0.076 (6)0.106 (6)0.009 (4)0.024 (4)0.010 (5)
C590.044 (4)0.087 (7)0.223 (9)0.007 (5)0.020 (6)0.060 (7)
C600.039 (4)0.076 (6)0.202 (8)0.005 (4)0.012 (5)0.065 (6)
C610.026 (2)0.021 (3)0.038 (3)0.006 (2)0.003 (2)0.002 (2)
C620.023 (3)0.031 (4)0.039 (3)0.006 (3)0.004 (2)0.001 (3)
C630.037 (3)0.022 (3)0.055 (4)0.004 (3)0.014 (3)0.009 (3)
C640.047 (4)0.035 (4)0.061 (5)0.001 (3)0.016 (3)0.020 (3)
C650.042 (3)0.041 (4)0.040 (3)0.005 (3)0.017 (3)0.014 (3)
C660.042 (3)0.041 (4)0.025 (3)0.001 (3)0.010 (3)0.009 (3)
C670.028 (3)0.023 (3)0.034 (3)0.004 (3)0.005 (2)0.009 (3)
C680.076 (5)0.046 (4)0.026 (3)0.004 (4)0.001 (3)0.008 (3)
C690.093 (6)0.050 (5)0.025 (3)0.001 (5)0.001 (4)0.011 (3)
C700.039 (3)0.028 (4)0.035 (3)0.006 (3)0.006 (3)0.006 (3)
C710.043 (3)0.039 (4)0.043 (4)0.004 (3)0.002 (3)0.017 (3)
C720.039 (3)0.032 (4)0.054 (4)0.001 (3)0.001 (3)0.016 (3)
C730.039 (3)0.033 (4)0.043 (4)0.007 (3)0.006 (3)0.006 (3)
C740.030 (3)0.027 (4)0.040 (3)0.004 (3)0.009 (3)0.001 (3)
C750.038 (3)0.033 (4)0.029 (3)0.001 (3)0.011 (2)0.008 (3)
C760.029 (2)0.025 (3)0.040 (3)0.003 (2)0.009 (2)0.001 (2)
C770.034 (3)0.026 (3)0.025 (2)0.001 (2)0.0019 (19)0.0051 (19)
C780.035 (3)0.021 (3)0.038 (3)0.000 (3)0.003 (2)0.006 (2)
C790.053 (4)0.034 (4)0.048 (4)0.005 (3)0.005 (3)0.002 (3)
C800.066 (5)0.038 (5)0.069 (5)0.002 (4)0.029 (4)0.002 (4)
C810.046 (4)0.031 (4)0.104 (7)0.010 (3)0.023 (4)0.011 (4)
C820.048 (4)0.033 (4)0.089 (6)0.001 (3)0.011 (4)0.014 (4)
C830.045 (3)0.029 (3)0.053 (4)0.004 (3)0.009 (3)0.011 (3)
C840.045 (3)0.033 (3)0.021 (2)0.000 (3)0.006 (2)0.003 (2)
C860.040 (3)0.033 (3)0.043 (3)0.006 (3)0.001 (2)0.013 (3)
C850.036 (3)0.032 (3)0.031 (3)0.001 (2)0.013 (2)0.000 (2)
C870.061 (4)0.043 (4)0.064 (5)0.011 (4)0.013 (4)0.014 (4)
C890.022 (3)0.095 (8)0.143 (9)0.004 (4)0.004 (4)0.027 (7)
C880.048 (4)0.040 (4)0.105 (7)0.012 (4)0.023 (4)0.005 (5)
C900.041 (3)0.047 (4)0.080 (5)0.006 (3)0.010 (3)0.011 (4)
C910.033 (3)0.031 (4)0.025 (3)0.000 (3)0.005 (2)0.000 (3)
C920.026 (3)0.029 (3)0.026 (3)0.003 (3)0.004 (2)0.000 (3)
C930.042 (4)0.031 (4)0.043 (4)0.001 (3)0.003 (3)0.006 (3)
C940.044 (4)0.023 (3)0.054 (4)0.005 (3)0.008 (3)0.003 (3)
C950.042 (4)0.037 (5)0.043 (4)0.010 (3)0.012 (3)0.009 (3)
C960.028 (3)0.030 (4)0.033 (3)0.005 (3)0.006 (3)0.004 (3)
C970.038 (3)0.024 (4)0.038 (4)0.006 (3)0.015 (3)0.006 (3)
C980.050 (3)0.045 (4)0.046 (4)0.013 (4)0.009 (3)0.024 (4)
Geometric parameters (Å, º) top
Sm1—O52.350 (5)C50—H500.9500
Sm1—O42.366 (4)C51—C521.392 (11)
Sm1—O92.476 (5)C51—H510.9500
Sm1—O142.498 (5)C53—C521.386 (10)
Sm1—O72.500 (6)C53—H530.9500
Sm1—O112.505 (6)C52—H520.9500
Sm1—O132.563 (5)C54—C551.520 (6)
Sm1—O32.601 (5)C54—H541.0000
Sm1—O62.614 (5)C55—C561.3900
Sm1—O102.630 (5)C55—C601.3900
Sm1—N312.922 (6)C56—C571.3900
Sm1—N292.965 (6)C56—H560.9500
Sm2—O182.333 (5)C57—C581.3900
Sm2—O172.373 (4)C57—H570.9500
Sm2—O282.481 (6)C58—C591.3900
Sm2—O262.500 (5)C58—H580.9500
Sm2—O202.522 (5)C59—C601.3900
Sm2—O242.530 (6)C59—H590.9500
Sm2—O212.561 (5)C60—H600.9500
Sm2—O192.606 (5)C61—C621.409 (9)
Sm2—O162.621 (6)C61—H610.9500
Sm2—O232.634 (4)C62—C671.402 (10)
Sm2—N362.930 (6)C62—C631.435 (10)
Sm2—N342.978 (6)C63—C641.363 (11)
O3—C401.375 (8)C63—H630.9500
O3—C391.433 (10)C64—C651.397 (12)
O4—C451.304 (8)C64—H640.9500
O5—C671.306 (8)C65—C661.363 (11)
O6—C661.362 (10)C65—H650.9500
O6—C681.442 (7)C66—C671.447 (9)
O7—N311.263 (9)C68—H68A0.9800
O9—N311.267 (10)C68—H68B0.9800
O8—N311.232 (8)C68—H68C0.9800
O10—N301.272 (9)C69—H69A0.9800
O11—N301.255 (7)C69—H69B0.9800
O12—N301.223 (8)C69—H69C0.9800
O13—N291.259 (8)C70—C711.378 (11)
O14—N291.291 (9)C70—C751.408 (10)
O15—N291.219 (9)C71—C721.406 (12)
O16—C961.380 (8)C71—H710.9500
O16—C981.437 (10)C72—C731.382 (11)
O17—C971.315 (9)C72—H720.9500
O18—C751.295 (9)C73—C741.389 (11)
O19—C701.397 (9)C73—H730.9500
O19—C691.438 (7)C74—C751.439 (11)
O20—N341.273 (9)C74—C761.445 (9)
O21—N341.296 (9)C76—H760.9500
O22—N341.181 (8)C77—C781.544 (8)
O23—N351.241 (8)C77—C841.555 (7)
O24—N351.278 (7)C77—H771.0000
O25—N351.222 (8)C78—C791.353 (10)
O26—N361.260 (8)C78—C831.383 (9)
O27—N361.223 (8)C79—C801.391 (12)
O28—N361.265 (8)C79—H790.9500
N32—C611.292 (8)C80—C811.357 (12)
N32—C541.475 (6)C80—H800.9500
N32—H321.0395C81—C821.399 (14)
N33—C461.305 (9)C81—H810.9500
N33—C471.473 (7)C82—C831.358 (11)
N33—H330.8600C82—H820.92 (8)
N37—C911.290 (9)C83—H830.9500
N37—C841.451 (8)C84—C851.526 (8)
N37—H370.8345C84—H841.0000
N38—C761.287 (8)C86—C871.380 (10)
N38—C771.466 (6)C86—C851.383 (8)
N38—H380.8600C86—H860.9500
C39—H39A0.9800C85—C901.374 (9)
C39—H39B0.9800C87—C881.349 (12)
C39—H39C0.9800C87—H870.9500
C40—C411.381 (10)C89—C881.352 (13)
C40—C451.414 (10)C89—C901.424 (12)
C41—C421.386 (9)C89—H890.9500
C41—H410.9500C88—H880.9500
C42—C431.387 (12)C90—H900.9500
C42—H420.9500C91—C921.436 (10)
C43—C441.397 (11)C91—H910.9500
C43—H430.9500C92—C971.420 (9)
C44—C461.397 (11)C92—C931.424 (11)
C44—C451.413 (8)C93—C941.352 (11)
C46—H460.9500C93—H930.9500
C47—C481.527 (8)C94—C951.421 (10)
C47—C541.545 (8)C94—H940.9500
C47—H471.0000C95—C961.371 (11)
C48—C491.399 (9)C95—H950.9500
C48—C531.402 (9)C96—C971.404 (9)
C49—C501.391 (9)C98—H98A0.9800
C49—H490.9500C98—H98B0.9800
C50—C511.370 (12)C98—H98C0.9800
O5—Sm1—O469.96 (17)O3—C39—H39B109.5
O5—Sm1—O9119.1 (2)H39A—C39—H39B109.5
O4—Sm1—O9116.53 (16)O3—C39—H39C109.5
O5—Sm1—O1476.29 (18)H39A—C39—H39C109.5
O4—Sm1—O14116.86 (16)H39B—C39—H39C109.5
O9—Sm1—O14126.43 (17)O3—C40—C41127.1 (7)
O5—Sm1—O780.7 (2)O3—C40—C45111.9 (6)
O4—Sm1—O772.98 (17)C41—C40—C45121.0 (6)
O9—Sm1—O750.9 (2)C40—C41—C42120.7 (7)
O14—Sm1—O7149.1 (3)C40—C41—H41119.7
O5—Sm1—O11143.01 (17)C42—C41—H41119.7
O4—Sm1—O11107.06 (18)C41—C42—C43119.4 (7)
O9—Sm1—O1195.7 (2)C41—C42—H42120.3
O14—Sm1—O1172.73 (19)C43—C42—H42120.3
O7—Sm1—O11135.0 (2)C42—C43—C44120.9 (6)
O5—Sm1—O1375.13 (18)C42—C43—H43119.6
O4—Sm1—O1369.89 (14)C44—C43—H43119.6
O9—Sm1—O13165.4 (2)C46—C44—C43119.5 (6)
O14—Sm1—O1350.38 (17)C46—C44—C45120.1 (6)
O7—Sm1—O13140.77 (17)C43—C44—C45120.0 (7)
O11—Sm1—O1369.70 (17)O4—C45—C44122.4 (6)
O5—Sm1—O3131.33 (15)O4—C45—C40119.7 (5)
O4—Sm1—O362.37 (17)C44—C45—C40117.8 (6)
O9—Sm1—O376.7 (2)N33—C46—C44122.4 (6)
O14—Sm1—O3134.1 (2)N33—C46—H46118.8
O7—Sm1—O376.8 (2)C44—C46—H46118.8
O11—Sm1—O365.28 (18)N33—C47—C48109.7 (5)
O13—Sm1—O396.56 (19)N33—C47—C54111.9 (4)
O5—Sm1—O663.17 (16)C48—C47—C54112.6 (5)
O4—Sm1—O6129.40 (18)N33—C47—H47107.5
O9—Sm1—O673.8 (2)C48—C47—H47107.5
O14—Sm1—O669.72 (18)C54—C47—H47107.5
O7—Sm1—O681.6 (2)C49—C48—C53119.3 (6)
O11—Sm1—O6121.57 (16)C49—C48—C47121.8 (5)
O13—Sm1—O6113.06 (17)C53—C48—C47118.9 (6)
O3—Sm1—O6150.26 (17)C50—C49—C48120.1 (7)
O5—Sm1—O10133.49 (17)C50—C49—H49120.0
O4—Sm1—O10154.62 (18)C48—C49—H49120.0
O9—Sm1—O1064.75 (18)C51—C50—C49120.0 (7)
O14—Sm1—O1069.20 (18)C51—C50—H50120.0
O7—Sm1—O10115.43 (18)C49—C50—H50120.0
O11—Sm1—O1049.29 (17)C50—C51—C52120.8 (7)
O13—Sm1—O10103.59 (16)C50—C51—H51119.6
O3—Sm1—O1095.18 (18)C52—C51—H51119.6
O6—Sm1—O1075.95 (17)C52—C53—C48120.0 (7)
O5—Sm1—N31100.1 (2)C52—C53—H53120.0
O4—Sm1—N3195.06 (16)C48—C53—H53120.0
O9—Sm1—N3125.5 (2)C53—C52—C51119.8 (7)
O14—Sm1—N31143.2 (2)C53—C52—H52120.1
O7—Sm1—N3125.4 (2)C51—C52—H52120.1
O11—Sm1—N31116.8 (2)N32—C54—C55110.7 (4)
O13—Sm1—N31164.95 (16)N32—C54—C47110.3 (4)
O3—Sm1—N3175.6 (2)C55—C54—C47115.2 (4)
O6—Sm1—N3176.0 (2)N32—C54—H54106.7
O10—Sm1—N3190.08 (19)C55—C54—H54106.7
O5—Sm1—N2972.0 (2)C47—C54—H54106.7
O4—Sm1—N2992.41 (17)C56—C55—C60120.0
O9—Sm1—N29150.90 (17)C56—C55—C54118.8 (4)
O14—Sm1—N2925.56 (18)C60—C55—C54121.2 (4)
O7—Sm1—N29152.3 (2)C55—C56—C57120.0
O11—Sm1—N2971.3 (2)C55—C56—H56120.0
O13—Sm1—N2924.99 (18)C57—C56—H56120.0
O3—Sm1—N29117.7 (2)C58—C57—C56120.0
O6—Sm1—N2990.6 (2)C58—C57—H57120.0
O10—Sm1—N2987.92 (18)C56—C57—H57120.0
N31—Sm1—N29166.6 (3)C59—C58—C57120.0
O18—Sm2—O1769.48 (17)C59—C58—H58120.0
O18—Sm2—O2884.7 (2)C57—C58—H58120.0
O17—Sm2—O2871.80 (19)C60—C59—C58120.0
O18—Sm2—O26122.7 (2)C60—C59—H59120.0
O17—Sm2—O26115.40 (15)C58—C59—H59120.0
O28—Sm2—O2650.61 (17)C59—C60—C55120.0
O18—Sm2—O2075.22 (19)C59—C60—H60120.0
O17—Sm2—O20118.48 (16)C55—C60—H60120.0
O28—Sm2—O20150.9 (3)N32—C61—C62121.5 (6)
O26—Sm2—O20126.03 (15)N32—C61—H61119.2
O18—Sm2—O24139.72 (18)C62—C61—H61119.2
O17—Sm2—O24108.00 (18)C67—C62—C61121.4 (6)
O28—Sm2—O24134.2 (2)C67—C62—C63119.3 (6)
O26—Sm2—O2495.3 (2)C61—C62—C63119.2 (7)
O20—Sm2—O2471.40 (19)C64—C63—C62120.3 (8)
O18—Sm2—O2173.25 (19)C64—C63—H63119.9
O17—Sm2—O2171.42 (15)C62—C63—H63119.9
O28—Sm2—O21141.83 (17)C63—C64—C65120.3 (7)
O26—Sm2—O21163.7 (2)C63—C64—H64119.9
O20—Sm2—O2150.65 (17)C65—C64—H64119.9
O24—Sm2—O2168.35 (18)C66—C65—C64122.0 (7)
O18—Sm2—O1963.28 (17)C66—C65—H65119.0
O17—Sm2—O19126.05 (19)C64—C65—H65119.0
O28—Sm2—O1979.2 (2)O6—C66—C65127.5 (6)
O26—Sm2—O1973.5 (2)O6—C66—C67113.4 (6)
O20—Sm2—O1973.06 (19)C65—C66—C67119.2 (7)
O24—Sm2—O19124.63 (16)O5—C67—C62122.6 (6)
O21—Sm2—O19115.52 (19)O5—C67—C66118.4 (7)
O18—Sm2—O16131.36 (15)C62—C67—C66119.0 (7)
O17—Sm2—O1662.19 (17)O6—C68—H68A109.5
O28—Sm2—O1675.9 (2)O6—C68—H68B109.5
O26—Sm2—O1676.33 (19)H68A—C68—H68B109.5
O20—Sm2—O16133.2 (2)O6—C68—H68C109.5
O24—Sm2—O1665.47 (17)H68A—C68—H68C109.5
O21—Sm2—O1695.62 (18)H68B—C68—H68C109.5
O19—Sm2—O16148.86 (17)O19—C69—H69A109.5
O18—Sm2—O23134.04 (16)O19—C69—H69B109.5
O17—Sm2—O23154.52 (18)H69A—C69—H69B109.5
O28—Sm2—O23114.47 (17)O19—C69—H69C109.5
O26—Sm2—O2364.02 (15)H69A—C69—H69C109.5
O20—Sm2—O2368.97 (16)H69B—C69—H69C109.5
O24—Sm2—O2348.99 (15)C71—C70—O19125.9 (7)
O21—Sm2—O23103.15 (15)C71—C70—C75122.1 (8)
O19—Sm2—O2379.12 (16)O19—C70—C75112.0 (6)
O16—Sm2—O2394.47 (15)C70—C71—C72119.6 (7)
O18—Sm2—N36104.7 (2)C70—C71—H71120.2
O17—Sm2—N3693.42 (16)C72—C71—H71120.2
O28—Sm2—N3625.34 (18)C73—C72—C71120.5 (7)
O26—Sm2—N3625.28 (15)C73—C72—H72119.7
O20—Sm2—N36144.42 (17)C71—C72—H72119.7
O24—Sm2—N36115.51 (18)C72—C73—C74120.0 (8)
O21—Sm2—N36164.57 (15)C72—C73—H73120.0
O19—Sm2—N3675.45 (19)C74—C73—H73120.0
O16—Sm2—N3674.01 (19)C73—C74—C75121.0 (6)
O23—Sm2—N3689.26 (15)C73—C74—C76120.8 (6)
O18—Sm2—N3471.2 (2)C75—C74—C76118.2 (6)
O17—Sm2—N3494.85 (16)O18—C75—C70120.9 (7)
O28—Sm2—N34155.5 (2)O18—C75—C74122.4 (6)
O26—Sm2—N34149.31 (16)C70—C75—C74116.7 (7)
O20—Sm2—N3425.05 (18)N38—C76—C74122.6 (6)
O24—Sm2—N3468.9 (2)N38—C76—H76118.7
O21—Sm2—N3425.66 (18)C74—C76—H76118.7
O19—Sm2—N3493.5 (2)N38—C77—C78112.2 (4)
O16—Sm2—N34116.7 (2)N38—C77—C84109.1 (4)
O23—Sm2—N3486.55 (16)C78—C77—C84113.6 (5)
N36—Sm2—N34168.7 (2)N38—C77—H77107.2
C40—O3—C39117.1 (6)C78—C77—H77107.2
C40—O3—Sm1116.5 (4)C84—C77—H77107.2
C39—O3—Sm1123.2 (4)C79—C78—C83118.8 (7)
C45—O4—Sm1124.4 (4)C79—C78—C77118.0 (6)
C67—O5—Sm1127.2 (4)C83—C78—C77123.1 (6)
C66—O6—C68117.2 (6)C78—C79—C80121.5 (8)
C66—O6—Sm1117.9 (4)C78—C79—H79119.2
C68—O6—Sm1124.9 (5)C80—C79—H79119.2
N31—O7—Sm196.3 (5)C81—C80—C79119.8 (8)
N31—O9—Sm197.3 (4)C81—C80—H80120.1
N30—O10—Sm194.0 (4)C79—C80—H80120.1
N30—O11—Sm1100.6 (5)C80—C81—C82118.6 (8)
N29—O13—Sm195.7 (4)C80—C81—H81120.7
N29—O14—Sm197.9 (4)C82—C81—H81120.7
C96—O16—C98117.5 (7)C83—C82—C81121.0 (9)
C96—O16—Sm2113.8 (4)C83—C82—H82128 (5)
C98—O16—Sm2125.3 (4)C81—C82—H82110 (5)
C97—O17—Sm2121.5 (4)C82—C83—C78120.2 (8)
C75—O18—Sm2126.3 (4)C82—C83—H83119.9
C70—O19—C69116.4 (6)C78—C83—H83119.9
C70—O19—Sm2117.0 (4)N37—C84—C85113.1 (5)
C69—O19—Sm2126.5 (5)N37—C84—C77108.5 (4)
N34—O20—Sm298.0 (4)C85—C84—C77109.8 (5)
N34—O21—Sm295.5 (4)N37—C84—H84108.4
N35—O23—Sm295.2 (4)C85—C84—H84108.4
N35—O24—Sm299.2 (4)C77—C84—H84108.4
N36—O26—Sm296.8 (4)C87—C86—C85120.2 (6)
N36—O28—Sm297.6 (4)C87—C86—H86119.9
O15—N29—O13123.1 (8)C85—C86—H86119.9
O15—N29—O14121.5 (8)C90—C85—C86118.7 (6)
O13—N29—O14115.3 (6)C90—C85—C84122.6 (6)
O15—N29—Sm1174.1 (8)C86—C85—C84118.6 (5)
O13—N29—Sm159.3 (3)C88—C87—C86122.1 (8)
O14—N29—Sm156.6 (3)C88—C87—H87119.0
O12—N30—O11121.7 (7)C86—C87—H87119.0
O12—N30—O10122.2 (6)C88—C89—C90121.3 (8)
O11—N30—O10116.1 (6)C88—C89—H89119.4
O8—N31—O7122.2 (8)C90—C89—H89119.4
O8—N31—O9122.3 (7)C87—C88—C89118.5 (7)
O7—N31—O9115.5 (6)C87—C88—H88120.8
O8—N31—Sm1178.3 (7)C89—C88—H88120.8
O7—N31—Sm158.3 (4)C85—C90—C89118.9 (8)
O9—N31—Sm157.2 (3)C85—C90—H90120.5
C61—N32—C54123.4 (5)C89—C90—H90120.5
C61—N32—H32114.0N37—C91—C92122.8 (6)
C54—N32—H32121.5N37—C91—H91118.6
C46—N33—C47124.8 (5)C92—C91—H91118.6
C46—N33—H33119.8C97—C92—C93119.3 (7)
C47—N33—H33114.6C97—C92—C91120.1 (6)
O22—N34—O20122.0 (8)C93—C92—C91120.6 (6)
O22—N34—O21122.3 (8)C94—C93—C92120.5 (7)
O20—N34—O21115.7 (6)C94—C93—H93119.7
O22—N34—Sm2173.1 (8)C92—C93—H93119.7
O20—N34—Sm257.0 (3)C93—C94—C95120.7 (7)
O21—N34—Sm258.9 (3)C93—C94—H94119.7
O25—N35—O23123.2 (5)C95—C94—H94119.7
O25—N35—O24120.2 (6)C96—C95—C94119.5 (7)
O23—N35—O24116.6 (6)C96—C95—H95120.3
O27—N36—O26121.3 (6)C94—C95—H95120.3
O27—N36—O28123.8 (7)C95—C96—O16126.2 (7)
O26—N36—O28114.9 (6)C95—C96—C97121.6 (6)
O27—N36—Sm2178.5 (7)O16—C96—C97112.3 (6)
O26—N36—Sm257.9 (3)O17—C97—C96119.9 (6)
O28—N36—Sm257.0 (4)O17—C97—C92121.7 (6)
C91—N37—C84125.5 (5)C96—C97—C92118.4 (6)
C91—N37—H37107.3O16—C98—H98A109.5
C84—N37—H37122.8O16—C98—H98B109.5
C76—N38—C77125.8 (5)H98A—C98—H98B109.5
C76—N38—H38119.5O16—C98—H98C109.5
C77—N38—H38114.7H98A—C98—H98C109.5
O3—C39—H39A109.5H98B—C98—H98C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C98—H98A···O9i0.982.583.419 (9)144
C91—H91···O27ii0.952.593.097 (8)114
C91—H91···O12iii0.952.333.227 (8)156
C77—H77···O24iv1.002.293.264 (8)164
C76—H76···O21iv0.952.503.399 (9)158
C69—H69A···O14v0.982.443.323 (10)150
C68—H68A···O100.982.553.214 (11)125
C68—H68A···O90.982.663.224 (11)117
C65—H65···O20vi0.952.643.485 (8)148
C61—H61···O13vi0.952.493.429 (8)172
C54—H54···O11vi1.002.303.277 (8)165
C46—H46···O250.952.323.211 (8)155
C46—H46···O8i0.952.563.054 (8)113
C39—H39A···O27i0.982.543.338 (9)138
N38—H38···O180.861.872.550 (6)135
N33—H33···O40.861.872.545 (7)134
N37—H37···O170.831.892.582 (7)139
N32—H32···O51.041.712.578 (6)138
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x, y, z1; (iv) x+1/2, y1/2, z; (v) x+1/2, y1/2, z+1; (vi) x+1/2, y+1/2, z+1.
 

Funding information

This work was supported by a Grant-in-Aid for Scientific Research (A) KAKENHI (20H00336).

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