metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Tris­(4,4′-di-tert-butyl-2,2′-bi­pyridine)(trans-4-tert-butyl­cyclo­hexa­nolato)­deca-μ-oxido-hepta­oxido­hepta­vanadium aceto­nitrile monosolvate including another unknown solvent mol­ecule

aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan
*Correspondence e-mail: skodama@chem.osakafu-u.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 11 March 2020; accepted 1 April 2020; online 7 April 2020)

The title hepta­nuclear alkoxido(oxido)vanadium(V) oxide cluster complex, [V7(C10H19O)O17(C18H24N2)3]·CH3CN, was obtained by the reaction of [V8O20(C18H24N2)4] with 4-tert-butyl­cyclo­hexa­nol (mixture of cis and trans) in a mixed CHCl3/CH3CN solvent. The complex has a V7O18N6 core with approximately Cs symmetry, which is composed of two VO4 tetra­hedra, two VO6 octa­hedra and three VO4N2 octa­hedra. In the crystal, these complexes are linked together by weak inter­molecular C—H⋯O hydrogen bonds between the 4,4′-di-tert-butyl-2,2′-bi­pyridine ligand and the V7O18N6 core, forming a one-dimensional network along the c-axis direction. Besides the complex, the asymmetric unit contains one CH3CN solvent mol­ecule. The contribution of other disordered solvent mol­ecules to the scattering was removed using the SQUEEZE option in PLATON [Spek (2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]). Acta Cryst. C71, 9–18]. The unknown solvent mol­ecules are not considered in the chemical formula and other crystal data.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

In contrast to anionic vanadium oxide clusters (POVs) (Hayashi, 2011[Hayashi, Y. (2011). Coord. Chem. Rev. 255, 2270-2280.]), isolated non-ionic vanadium oxide clusters are still limited in number, although they have the potential to exhibit chemical properties distinct from those of POVs. In fact, non-ionic vanadium oxide clusters have recently attracted much attention as a catalyst for oxidation of hydro­carbons in a gas-phase study (Dong et al., 2008[Dong, F., Heinbuch, S., Xie, Y., Rocca, J. J., Bernstein, E. R., Wang, Z.-C., Deng, K. & He, S.-G. (2008). J. Am. Chem. Soc. 130, 1932-1943.]). Non-ionic vanadium oxide clusters are typically isolated as organic ligand-functionalized POVs that are often synthesized directly from monomeric oxidovanadium species (Gao et al., 2014[Gao, Y., Chi, Y. & Hu, C. (2014). Polyhedron, 83, 242-258.]). However, most of them have low solubility in common organic solvents, and therefore their chemical properties and structural transformations in solution still remain largely unexplored.

Structural transformations of [V8O20(4,4′-tBubpy)4] (4,4′-tBubpy = 4,4′-di-tert-butyl-2,2′-bi­pyridine) in alcoholic solution have been reported (Kodama et al., 2014[Kodama, S., Taya, N. & Ishii, Y. (2014). Inorg. Chem. 53, 2754-2756.], 2016[Kodama, S., Taya, N., Inoue, Y. & Ishii, Y. (2016). Inorg. Chem. 55, 6712-6718.]; Inoue et al., 2018[Inoue, Y., Kodama, S., Taya, N., Sato, H., Oh-Ishi, K. & Ishii, Y. (2018). Inorg. Chem. 57, 7491-7494.]), where the 2-meth­oxy­ethoxido analogue of the title complex was crystallized from 2-meth­oxy­ethanol solution of [V8O20(4,4′-tBubpy)4]. In the present study, single crystals of the title complex were successfully obtained by dissolving [V8O20(4,4′-tBubpy)4] and an excess amount of 4-tert-butyl­cyclo­hexa­nol (solid at ambient temperature) in a mixed CHCl3/CH3CN solvent, followed by slow diffusion of diethyl ether into the resulting solution. The mol­ecular structure of the title complex is presented in Fig. 1[link]. The V7O18N6 core with approximately Cs symmetry is composed of two VO4 tetra­hedra, two VO6 octa­hedra, and three VO4N2 octa­hedra. The V–Oterminal distances and the V–Obridged distances are within the range of these bonds found in vanadium oxide clusters, although the V3—O13 [2.476 (3) Å] and V5—O13 [2.527 (3) Å] distances are relatively long (Kodama et al., 2016[Kodama, S., Taya, N., Inoue, Y. & Ishii, Y. (2016). Inorg. Chem. 55, 6712-6718.]; Schindler et al., 2000[Schindler, M., Hawthorne, F. C. & Baur, W. H. (2000). Chem. Mater. 12, 1248-1259.]). The crystal packing of the title complex is shown in Fig. 2[link]. Weak inter­molecular C—H⋯O hydrogen bonds were observed between the 4,4′-tBubpy ligand and the V7O18N6 core (Table 1[link]), leading to a one-dimensional network along the c-axis direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19⋯O14i 0.95 2.55 3.417 (7) 152
C30—H30⋯O16i 0.95 2.38 3.122 (6) 135
C37—H37⋯O5i 0.95 2.43 3.264 (7) 146
C40—H40B⋯O16i 0.98 2.58 3.466 (8) 150
C48—H48⋯O8i 0.95 2.32 3.216 (6) 157
Symmetry code: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. The solvent CH3CN mol­ecule and H atoms have been omitted for clarity.
[Figure 2]
Figure 2
A packing diagram of the title complex viewed along the a axis. The C—H⋯O hydrogen bonds are represented by the light blue lines.

Synthesis and crystallization

[V8O20(4,4′-tBubpy)4]·CH2Cl2 was prepared according to the procedure reported previously (Kodama et al., 2016[Kodama, S., Taya, N., Inoue, Y. & Ishii, Y. (2016). Inorg. Chem. 55, 6712-6718.]). [V8O20(4,4′-tBubpy)4]·CH2Cl2 (2.8 mg, 0.0015 mmol) and 4-tert-butyl­cyclo­hexa­nol (cis:trans ratio = 33:67) (23.4 mg, 0.15 mmol) were dissolved in a mixed solvent of CHCl3 (0.1 mL) and CH3CN (0.05 mL) at ambient temperature. Et2O was diffused into the resulting solution to give yellow crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Solvent mol­ecules except the refined CH3CN mol­ecule were too highly disordered to refine the structure, and so they were treated with SQUEEZE in PLATON (Spek, 2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]). This program indicated the total potential solvent-accessible void volume of 2079 Å3 per unit cell and 492 electrons/cell within the void.

Table 2
Experimental details

Crystal data
Chemical formula [V7(C10H19O)O17(C18H24N2)3]·C2H3N
Mr 1630.10
Crystal system, space group Monoclinic, P21/c
Temperature (K) 123
a, b, c (Å) 14.6285 (4), 29.9816 (7), 20.5191 (5)
β (°) 94.548 (7)
V3) 8971.1 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.76
Crystal size (mm) 0.14 × 0.08 × 0.03
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.386, 0.978
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 122082, 16426, 12218
Rint 0.113
(sin θ/λ)max−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.202, 1.02
No. of reflections 16426
No. of parameters 905
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.26, −0.61
Computer programs: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and CrystalStructure (Rigaku, 2018[Rigaku (2018). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Structural data


Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: CrystalStructure (Rigaku, 2018); software used to prepare material for publication: CrystalStructure (Rigaku, 2018).

(I) top
Crystal data top
[V7(C10H19O)O17(C18H24N2)3]·C2H3NF(000) = 3376.00
Mr = 1630.10Dx = 1.207 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 14.6285 (4) ÅCell parameters from 76498 reflections
b = 29.9816 (7) Åθ = 1.8–25.4°
c = 20.5191 (5) ŵ = 0.76 mm1
β = 94.548 (7)°T = 123 K
V = 8971.1 (4) Å3Prism, yellow
Z = 40.14 × 0.08 × 0.03 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
12218 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.113
ω scansθmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1717
Tmin = 0.386, Tmax = 0.978k = 3636
122082 measured reflectionsl = 2424
16426 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.088P)2 + 32.1684P]
where P = (Fo2 + 2Fc2)/3
16426 reflections(Δ/σ)max = 0.001
905 parametersΔρmax = 1.26 e Å3
0 restraintsΔρmin = 0.61 e Å3
Primary atom site location: structure-invariant direct methods
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.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.65605 (6)0.63659 (3)0.78316 (4)0.0301 (2)
V20.48172 (7)0.66199 (3)0.91643 (4)0.0343 (2)
V30.62439 (6)0.72445 (3)0.86078 (4)0.0311 (2)
V40.52186 (6)0.80068 (3)0.77869 (4)0.0297 (2)
V50.62617 (6)0.72668 (3)0.70249 (4)0.0321 (2)
V60.49956 (7)0.65816 (3)0.63388 (4)0.0333 (2)
V70.41093 (6)0.68666 (3)0.76650 (4)0.0292 (2)
O10.7780 (3)0.63573 (12)0.79388 (19)0.0422 (9)
O20.6242 (3)0.58546 (11)0.77893 (16)0.0348 (8)
O30.6049 (2)0.65981 (10)0.85106 (16)0.0310 (8)
O40.6167 (3)0.66100 (10)0.70710 (16)0.0326 (8)
O50.4081 (3)0.66153 (12)0.97006 (18)0.0416 (9)
O60.5234 (3)0.71602 (10)0.91640 (16)0.0339 (8)
O70.4059 (3)0.65768 (11)0.84127 (16)0.0349 (8)
O80.7080 (3)0.72585 (11)0.91539 (19)0.0414 (9)
O90.5963 (2)0.78378 (10)0.84878 (16)0.0314 (8)
O100.6831 (2)0.72266 (10)0.78501 (16)0.0296 (7)
O110.5317 (3)0.85395 (11)0.77907 (17)0.0358 (8)
O120.5908 (2)0.78455 (10)0.71373 (17)0.0318 (8)
O130.4949 (2)0.72681 (10)0.77549 (15)0.0295 (7)
O140.7090 (3)0.73244 (11)0.65780 (18)0.0402 (9)
O150.5251 (3)0.71509 (10)0.63654 (16)0.0342 (8)
O160.4226 (3)0.65306 (12)0.57346 (18)0.0427 (9)
O170.4320 (3)0.64820 (12)0.70402 (18)0.0428 (9)
O180.3134 (3)0.71041 (13)0.7485 (2)0.0543 (11)
N10.5072 (3)0.59125 (13)0.9082 (2)0.0349 (10)
N20.5886 (3)0.64562 (14)0.9907 (2)0.0372 (10)
N30.4088 (3)0.80057 (12)0.8387 (2)0.0294 (9)
N40.4003 (3)0.80220 (12)0.7135 (2)0.0296 (9)
N50.6079 (3)0.65007 (12)0.5689 (2)0.0323 (10)
N60.5363 (3)0.58772 (13)0.63377 (19)0.0344 (10)
N71.0188 (4)0.7972 (3)0.7672 (3)0.078 (2)
C10.8415 (5)0.6056 (2)0.7668 (3)0.0549 (16)
H10.9043350.6185760.7750540.066*
C20.8221 (5)0.6006 (2)0.6941 (3)0.0524 (16)
H2A0.8263550.6302210.6731150.063*
H2B0.7586980.5895000.6846010.063*
C30.8882 (5)0.5689 (2)0.6652 (4)0.0658 (19)
H3A0.9507800.5816400.6706490.079*
H3B0.8712070.5657450.6177330.079*
C40.8888 (5)0.5227 (2)0.6971 (3)0.0572 (17)
H40.8245810.5112060.6903110.069*
C50.9087 (6)0.5288 (2)0.7717 (4)0.070 (2)
H5A0.9047890.4994620.7934770.083*
H5B0.9718700.5402170.7809100.083*
C60.8412 (5)0.5612 (2)0.8002 (4)0.0635 (19)
H6A0.7786070.5483620.7949440.076*
H6B0.8580170.5651070.8474980.076*
C70.9501 (5)0.4877 (2)0.6668 (4)0.073 (2)
C81.0503 (6)0.5018 (3)0.6728 (7)0.123 (4)
H8A1.0881040.4774930.6576460.148*
H8B1.0692970.5085830.7185550.148*
H8C1.0579880.5283610.6459230.148*
C90.9412 (6)0.4425 (2)0.7014 (4)0.080 (2)
H9A0.9762620.4198610.6796050.096*
H9B0.8764630.4337370.6992880.096*
H9C0.9650640.4451590.7471850.096*
C100.9145 (6)0.4823 (3)0.5934 (4)0.087 (3)
H10A0.8473640.4810550.5897400.104*
H10B0.9390420.4546930.5761060.104*
H10C0.9348160.5077790.5683140.104*
C110.4612 (4)0.56539 (18)0.8631 (3)0.0423 (13)
H110.4111800.5779900.8369600.051*
C120.4837 (4)0.52141 (18)0.8532 (3)0.0441 (14)
H120.4481580.5040710.8217480.053*
C130.5577 (4)0.50251 (16)0.8888 (3)0.0420 (14)
C140.6053 (4)0.52938 (17)0.9356 (3)0.0424 (13)
H140.6569260.5178320.9611760.051*
C150.5772 (4)0.57269 (17)0.9448 (3)0.0374 (12)
C160.6198 (4)0.60330 (16)0.9959 (3)0.0367 (12)
C170.6824 (4)0.59046 (18)1.0461 (3)0.0449 (14)
H170.7036870.5605291.0484470.054*
C180.7148 (4)0.62130 (19)1.0939 (3)0.0451 (14)
C190.6807 (4)0.66469 (19)1.0874 (3)0.0463 (14)
H190.6999860.6867941.1187180.056*
C200.6193 (4)0.67539 (17)1.0356 (3)0.0427 (14)
H200.5977640.7052291.0315750.051*
C210.5927 (5)0.45537 (17)0.8758 (3)0.0467 (15)
C220.5206 (6)0.4271 (2)0.8359 (4)0.069 (2)
H22A0.5466310.3979070.8267130.083*
H22B0.5023580.4423360.7945720.083*
H22C0.4667480.4232110.8608340.083*
C230.6773 (5)0.4610 (2)0.8356 (3)0.0541 (16)
H23A0.6971070.4317310.8209420.065*
H23B0.7272970.4750130.8629350.065*
H23C0.6609020.4799460.7975020.065*
C240.6195 (6)0.43094 (19)0.9396 (3)0.066 (2)
H24A0.6747100.4446210.9612010.079*
H24B0.6317020.3995310.9303420.079*
H24C0.5692210.4329570.9683520.079*
C250.7818 (5)0.6071 (2)1.1505 (3)0.0567 (17)
C260.8676 (6)0.5873 (4)1.1234 (5)0.120 (4)
H26A0.9107720.5777981.1597080.144*
H26B0.8967510.6099951.0975130.144*
H26C0.8503360.5616291.0956290.144*
C270.7395 (7)0.5705 (3)1.1907 (4)0.092 (3)
H27A0.6916140.5835081.2156190.110*
H27B0.7872050.5572891.2209020.110*
H27C0.7126670.5474531.1612800.110*
C280.8094 (6)0.6449 (3)1.1956 (4)0.080 (2)
H28A0.8392650.6681331.1712460.096*
H28B0.8522410.6339801.2312030.096*
H28C0.7549210.6572611.2137790.096*
C290.4201 (4)0.79870 (16)0.9050 (2)0.0338 (11)
H290.4803770.7957070.9254300.041*
C300.3486 (4)0.80094 (17)0.9433 (3)0.0392 (13)
H300.3599400.7986500.9894020.047*
C310.2590 (4)0.80653 (18)0.9161 (3)0.0388 (12)
C320.2475 (4)0.80805 (17)0.8481 (3)0.0383 (12)
H320.1877600.8110020.8268610.046*
C330.3234 (3)0.80525 (14)0.8110 (2)0.0282 (11)
C340.3181 (4)0.80821 (15)0.7388 (3)0.0325 (11)
C350.2392 (4)0.81715 (17)0.7002 (3)0.0371 (12)
H350.1831340.8214220.7196660.044*
C360.2411 (4)0.82000 (18)0.6322 (3)0.0433 (13)
C370.3238 (4)0.81104 (18)0.6071 (3)0.0409 (13)
H370.3277730.8106870.5610890.049*
C380.4007 (4)0.80262 (16)0.6483 (3)0.0360 (12)
H380.4567720.7967990.6295170.043*
C390.1785 (4)0.8129 (2)0.9579 (3)0.0533 (16)
C400.2047 (5)0.8057 (3)1.0309 (3)0.0623 (19)
H40A0.1504320.8098041.0554000.075*
H40B0.2519110.8273261.0460960.075*
H40C0.2284910.7753861.0379880.075*
C410.1465 (6)0.8617 (3)0.9489 (4)0.088 (3)
H41A0.1227410.8664250.9034540.106*
H41B0.1984650.8817380.9595620.106*
H41C0.0980840.8678680.9780290.106*
C420.1006 (5)0.7811 (3)0.9365 (3)0.079 (3)
H42A0.0534800.7823980.9678750.095*
H42B0.1244410.7505910.9347420.095*
H42C0.0736320.7897650.8931070.095*
C430.1538 (5)0.8337 (2)0.5900 (3)0.0556 (17)
C440.0790 (5)0.7983 (3)0.5966 (3)0.0637 (19)
H44A0.0632460.7970550.6420890.076*
H44B0.1016680.7691300.5836610.076*
H44C0.0243270.8062320.5682090.076*
C450.1215 (5)0.8792 (3)0.6118 (4)0.077 (2)
H45A0.1699950.9012810.6073230.092*
H45B0.1071590.8776140.6575540.092*
H45C0.0664450.8879940.5844320.092*
C460.1737 (5)0.8368 (3)0.5172 (3)0.074 (2)
H46A0.1977040.8081970.5029770.089*
H46B0.2191330.8602900.5117570.089*
H46C0.1169240.8439340.4906340.089*
C470.6375 (4)0.68457 (16)0.5348 (3)0.0375 (13)
H470.6128140.7133400.5417700.045*
C480.7019 (4)0.68003 (18)0.4902 (3)0.0387 (13)
H480.7209550.7053470.4669220.046*
C490.7394 (4)0.63815 (17)0.4789 (3)0.0365 (12)
C500.7071 (4)0.60286 (17)0.5134 (3)0.0365 (12)
H500.7304460.5737590.5070190.044*
C510.6411 (4)0.60917 (15)0.5575 (2)0.0311 (11)
C520.5974 (4)0.57334 (16)0.5923 (2)0.0339 (12)
C530.6129 (4)0.52825 (16)0.5825 (2)0.0355 (12)
H530.6578590.5194550.5541590.043*
C540.5644 (4)0.49580 (17)0.6130 (3)0.0383 (13)
C550.5055 (4)0.51132 (17)0.6586 (3)0.0426 (14)
H550.4736410.4906570.6836420.051*
C560.4935 (4)0.55659 (17)0.6673 (3)0.0408 (13)
H560.4530870.5661590.6985050.049*
C570.8098 (4)0.6306 (2)0.4276 (3)0.0470 (14)
C580.8408 (5)0.6740 (2)0.3985 (4)0.070 (2)
H58A0.8671410.6934490.4335170.085*
H58B0.7880580.6889090.3753800.085*
H58C0.8871170.6677980.3677390.085*
C590.7637 (5)0.6014 (3)0.3725 (3)0.066 (2)
H59A0.8077050.5953620.3399300.079*
H59B0.7105300.6172150.3515790.079*
H59C0.7437320.5732300.3908120.079*
C600.8915 (5)0.6054 (3)0.4608 (4)0.068 (2)
H60A0.8704900.5769210.4778270.081*
H60B0.9197690.6232970.4968790.081*
H60C0.9365940.5996700.4289240.081*
C610.5756 (4)0.44589 (17)0.5985 (3)0.0445 (14)
C620.6150 (5)0.43821 (18)0.5342 (3)0.0573 (18)
H62A0.5756230.4523840.4992090.069*
H62B0.6184110.4060990.5258020.069*
H62C0.6766020.4511480.5354060.069*
C630.4813 (5)0.42335 (18)0.5962 (3)0.0517 (16)
H63A0.4866410.3924320.5815070.062*
H63B0.4382270.4394990.5657560.062*
H63C0.4588540.4237110.6399690.062*
C640.6387 (5)0.42511 (19)0.6548 (3)0.0528 (16)
H64A0.6084500.4268940.6956660.063*
H64B0.6967500.4415090.6595620.063*
H64C0.6506330.3938050.6446980.063*
C650.9641 (5)0.7705 (3)0.7664 (3)0.066 (2)
C660.8937 (6)0.7368 (4)0.7677 (5)0.104 (3)
H66A0.9184490.7107260.7920020.125*
H66B0.8735250.7279730.7229160.125*
H66C0.8415270.7487810.7892340.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0403 (5)0.0201 (4)0.0304 (4)0.0032 (3)0.0057 (4)0.0015 (3)
V20.0537 (6)0.0216 (4)0.0288 (4)0.0004 (4)0.0098 (4)0.0013 (3)
V30.0417 (5)0.0184 (4)0.0333 (5)0.0000 (3)0.0035 (4)0.0037 (3)
V40.0389 (5)0.0166 (4)0.0338 (5)0.0008 (3)0.0051 (4)0.0023 (3)
V50.0453 (5)0.0181 (4)0.0342 (5)0.0011 (4)0.0106 (4)0.0014 (3)
V60.0525 (6)0.0202 (4)0.0278 (4)0.0028 (4)0.0063 (4)0.0010 (3)
V70.0384 (5)0.0176 (4)0.0320 (4)0.0010 (3)0.0045 (4)0.0013 (3)
O10.050 (2)0.0265 (18)0.051 (2)0.0027 (16)0.0064 (19)0.0082 (17)
O20.051 (2)0.0229 (17)0.0314 (18)0.0007 (15)0.0071 (16)0.0010 (14)
O30.046 (2)0.0170 (16)0.0309 (18)0.0007 (14)0.0100 (15)0.0004 (13)
O40.052 (2)0.0165 (16)0.0301 (18)0.0028 (15)0.0074 (16)0.0017 (14)
O50.058 (3)0.0305 (19)0.038 (2)0.0041 (17)0.0156 (18)0.0035 (16)
O60.052 (2)0.0200 (16)0.0302 (18)0.0016 (15)0.0080 (16)0.0036 (14)
O70.050 (2)0.0271 (18)0.0283 (18)0.0083 (16)0.0064 (16)0.0025 (14)
O80.052 (2)0.0240 (18)0.048 (2)0.0048 (16)0.0019 (18)0.0043 (16)
O90.039 (2)0.0199 (16)0.0356 (18)0.0011 (14)0.0034 (15)0.0073 (14)
O100.039 (2)0.0163 (15)0.0338 (18)0.0017 (14)0.0080 (15)0.0005 (13)
O110.046 (2)0.0186 (16)0.043 (2)0.0003 (15)0.0042 (17)0.0020 (15)
O120.040 (2)0.0180 (16)0.0391 (19)0.0022 (14)0.0106 (16)0.0000 (14)
O130.043 (2)0.0163 (15)0.0296 (17)0.0013 (14)0.0064 (15)0.0036 (13)
O140.050 (2)0.0242 (18)0.048 (2)0.0020 (16)0.0129 (18)0.0005 (16)
O150.049 (2)0.0196 (16)0.0343 (19)0.0002 (15)0.0060 (16)0.0024 (14)
O160.056 (3)0.034 (2)0.039 (2)0.0003 (18)0.0073 (18)0.0029 (17)
O170.064 (3)0.0278 (18)0.038 (2)0.0145 (18)0.0131 (19)0.0077 (16)
O180.043 (2)0.031 (2)0.087 (3)0.0017 (17)0.005 (2)0.005 (2)
N10.053 (3)0.024 (2)0.029 (2)0.005 (2)0.009 (2)0.0007 (18)
N20.057 (3)0.025 (2)0.030 (2)0.000 (2)0.006 (2)0.0010 (18)
N30.036 (2)0.0137 (18)0.039 (2)0.0044 (16)0.0042 (19)0.0056 (17)
N40.043 (3)0.0144 (18)0.033 (2)0.0004 (17)0.0078 (19)0.0004 (16)
N50.054 (3)0.0144 (18)0.030 (2)0.0052 (18)0.009 (2)0.0013 (16)
N60.055 (3)0.025 (2)0.023 (2)0.0098 (19)0.0014 (19)0.0020 (17)
N70.047 (4)0.118 (6)0.070 (4)0.009 (4)0.009 (3)0.003 (4)
C10.048 (4)0.037 (3)0.080 (5)0.009 (3)0.006 (3)0.006 (3)
C20.064 (4)0.041 (3)0.052 (4)0.006 (3)0.006 (3)0.005 (3)
C30.076 (5)0.062 (4)0.061 (4)0.011 (4)0.015 (4)0.009 (4)
C40.062 (4)0.048 (4)0.062 (4)0.006 (3)0.007 (3)0.010 (3)
C50.078 (5)0.047 (4)0.081 (5)0.021 (4)0.012 (4)0.007 (4)
C60.076 (5)0.049 (4)0.064 (4)0.015 (3)0.005 (4)0.008 (3)
C70.070 (5)0.049 (4)0.098 (6)0.013 (4)0.002 (4)0.021 (4)
C80.063 (6)0.080 (6)0.230 (14)0.013 (5)0.032 (7)0.053 (8)
C90.089 (6)0.050 (4)0.099 (6)0.017 (4)0.007 (5)0.017 (4)
C100.103 (7)0.074 (6)0.086 (6)0.016 (5)0.030 (5)0.026 (5)
C110.058 (4)0.033 (3)0.037 (3)0.011 (3)0.009 (3)0.003 (2)
C120.066 (4)0.029 (3)0.039 (3)0.014 (3)0.009 (3)0.000 (2)
C130.074 (4)0.020 (2)0.034 (3)0.009 (3)0.017 (3)0.002 (2)
C140.061 (4)0.024 (3)0.044 (3)0.002 (2)0.013 (3)0.005 (2)
C150.050 (3)0.031 (3)0.033 (3)0.001 (2)0.011 (2)0.006 (2)
C160.052 (3)0.017 (2)0.042 (3)0.001 (2)0.010 (3)0.003 (2)
C170.055 (4)0.028 (3)0.052 (3)0.004 (3)0.004 (3)0.007 (3)
C180.053 (4)0.040 (3)0.042 (3)0.004 (3)0.005 (3)0.007 (3)
C190.062 (4)0.035 (3)0.042 (3)0.004 (3)0.003 (3)0.009 (3)
C200.068 (4)0.023 (3)0.037 (3)0.000 (3)0.010 (3)0.008 (2)
C210.078 (4)0.024 (3)0.040 (3)0.006 (3)0.019 (3)0.004 (2)
C220.103 (6)0.026 (3)0.078 (5)0.008 (3)0.011 (4)0.014 (3)
C230.078 (5)0.040 (3)0.046 (3)0.006 (3)0.019 (3)0.004 (3)
C240.120 (7)0.024 (3)0.055 (4)0.007 (3)0.021 (4)0.003 (3)
C250.052 (4)0.052 (4)0.064 (4)0.003 (3)0.011 (3)0.001 (3)
C260.072 (6)0.197 (12)0.085 (6)0.050 (7)0.028 (5)0.019 (7)
C270.117 (8)0.070 (5)0.080 (6)0.024 (5)0.044 (5)0.018 (4)
C280.104 (7)0.066 (5)0.063 (5)0.002 (4)0.037 (4)0.001 (4)
C290.044 (3)0.025 (2)0.032 (3)0.003 (2)0.002 (2)0.002 (2)
C300.057 (4)0.028 (3)0.035 (3)0.004 (2)0.012 (3)0.009 (2)
C310.046 (3)0.034 (3)0.038 (3)0.001 (2)0.007 (2)0.003 (2)
C320.033 (3)0.032 (3)0.050 (3)0.002 (2)0.004 (2)0.001 (2)
C330.037 (3)0.014 (2)0.035 (3)0.0004 (19)0.009 (2)0.0013 (19)
C340.038 (3)0.016 (2)0.044 (3)0.001 (2)0.001 (2)0.000 (2)
C350.041 (3)0.029 (3)0.041 (3)0.000 (2)0.001 (2)0.003 (2)
C360.047 (3)0.032 (3)0.050 (3)0.004 (2)0.001 (3)0.004 (3)
C370.055 (4)0.032 (3)0.036 (3)0.002 (2)0.005 (3)0.000 (2)
C380.044 (3)0.023 (2)0.041 (3)0.002 (2)0.004 (2)0.001 (2)
C390.050 (4)0.068 (4)0.044 (3)0.008 (3)0.015 (3)0.004 (3)
C400.050 (4)0.089 (5)0.051 (4)0.001 (4)0.018 (3)0.001 (4)
C410.091 (6)0.090 (6)0.089 (6)0.047 (5)0.047 (5)0.021 (5)
C420.036 (4)0.153 (8)0.048 (4)0.011 (4)0.002 (3)0.014 (5)
C430.048 (4)0.069 (4)0.048 (4)0.003 (3)0.009 (3)0.010 (3)
C440.053 (4)0.089 (5)0.048 (4)0.002 (4)0.006 (3)0.007 (4)
C450.067 (5)0.068 (5)0.090 (6)0.018 (4)0.028 (4)0.014 (4)
C460.061 (5)0.103 (6)0.056 (4)0.014 (4)0.013 (4)0.029 (4)
C470.058 (4)0.021 (2)0.034 (3)0.003 (2)0.011 (3)0.007 (2)
C480.053 (4)0.032 (3)0.031 (3)0.001 (2)0.003 (2)0.003 (2)
C490.040 (3)0.031 (3)0.038 (3)0.002 (2)0.001 (2)0.003 (2)
C500.042 (3)0.024 (2)0.043 (3)0.004 (2)0.002 (2)0.005 (2)
C510.048 (3)0.021 (2)0.023 (2)0.001 (2)0.002 (2)0.0010 (19)
C520.048 (3)0.021 (2)0.031 (3)0.004 (2)0.005 (2)0.001 (2)
C530.052 (3)0.022 (2)0.032 (3)0.001 (2)0.001 (2)0.003 (2)
C540.052 (4)0.025 (3)0.035 (3)0.005 (2)0.009 (2)0.000 (2)
C550.071 (4)0.024 (3)0.033 (3)0.011 (3)0.003 (3)0.002 (2)
C560.065 (4)0.027 (3)0.030 (3)0.012 (3)0.006 (3)0.004 (2)
C570.045 (3)0.042 (3)0.056 (4)0.007 (3)0.017 (3)0.005 (3)
C580.070 (5)0.053 (4)0.095 (6)0.005 (4)0.042 (4)0.014 (4)
C590.080 (5)0.070 (5)0.050 (4)0.002 (4)0.028 (4)0.008 (3)
C600.050 (4)0.080 (5)0.074 (5)0.022 (4)0.013 (4)0.009 (4)
C610.066 (4)0.021 (3)0.045 (3)0.000 (3)0.006 (3)0.003 (2)
C620.101 (6)0.021 (3)0.051 (4)0.005 (3)0.007 (4)0.009 (3)
C630.072 (4)0.023 (3)0.057 (4)0.009 (3)0.009 (3)0.002 (3)
C640.067 (4)0.031 (3)0.059 (4)0.001 (3)0.008 (3)0.002 (3)
C650.042 (4)0.108 (6)0.049 (4)0.002 (4)0.002 (3)0.003 (4)
C660.068 (6)0.115 (8)0.128 (9)0.027 (5)0.002 (6)0.009 (7)
Geometric parameters (Å, º) top
V1—O21.603 (3)V4—N42.139 (4)
V1—O31.775 (3)V4—N32.140 (4)
V1—O41.777 (3)V4—O132.250 (3)
V1—O11.780 (4)V5—O141.586 (4)
V2—O51.599 (4)V5—O121.831 (3)
V2—O61.731 (3)V5—O101.831 (3)
V2—O71.831 (4)V5—O151.955 (4)
V2—N22.152 (5)V5—O41.977 (3)
V2—N12.162 (4)V5—V63.0362 (12)
V2—O32.332 (3)V6—O161.614 (4)
V2—V33.0894 (12)V6—O151.747 (3)
V3—O81.592 (4)V6—O171.834 (4)
V3—O101.836 (3)V6—N52.164 (4)
V3—O91.838 (3)V6—N62.179 (4)
V3—O61.954 (4)V6—O42.190 (4)
V3—O31.967 (3)V7—O181.611 (4)
V4—O111.603 (3)V7—O131.720 (3)
V4—O121.800 (3)V7—O171.770 (4)
V4—O91.806 (4)V7—O71.770 (3)
O2—V1—O3106.21 (16)C20—C19—H19120.1
O2—V1—O4105.91 (17)C18—C19—H19120.1
O3—V1—O4113.62 (16)N2—C20—C19122.8 (5)
O2—V1—O1106.06 (18)N2—C20—H20118.6
O3—V1—O1112.90 (17)C19—C20—H20118.6
O4—V1—O1111.45 (18)C24—C21—C13111.1 (5)
O5—V2—O6105.34 (17)C24—C21—C22108.2 (5)
O5—V2—O7100.55 (19)C13—C21—C22112.1 (6)
O6—V2—O7104.80 (16)C24—C21—C23110.4 (6)
O5—V2—N290.13 (19)C13—C21—C23106.4 (4)
O6—V2—N288.73 (17)C22—C21—C23108.6 (5)
O7—V2—N2159.66 (16)C21—C22—H22A109.5
O5—V2—N1100.05 (17)C21—C22—H22B109.5
O6—V2—N1148.79 (18)H22A—C22—H22B109.5
O7—V2—N187.80 (16)C21—C22—H22C109.5
N2—V2—N173.22 (17)H22A—C22—H22C109.5
O5—V2—O3171.45 (18)H22B—C22—H22C109.5
O6—V2—O374.80 (14)C21—C23—H23A109.5
O7—V2—O387.57 (14)C21—C23—H23B109.5
N2—V2—O381.32 (15)H23A—C23—H23B109.5
N1—V2—O377.40 (14)C21—C23—H23C109.5
O5—V2—V3140.43 (14)H23A—C23—H23C109.5
O6—V2—V335.35 (11)H23B—C23—H23C109.5
O7—V2—V396.50 (11)C21—C24—H24A109.5
N2—V2—V385.73 (12)C21—C24—H24B109.5
N1—V2—V3116.12 (12)H24A—C24—H24B109.5
O3—V2—V339.52 (8)C21—C24—H24C109.5
O8—V3—O10102.23 (18)H24A—C24—H24C109.5
O8—V3—O9102.70 (17)H24B—C24—H24C109.5
O10—V3—O991.69 (14)C28—C25—C18112.7 (6)
O8—V3—O699.59 (18)C28—C25—C27108.1 (6)
O10—V3—O6156.55 (16)C18—C25—C27110.4 (6)
O9—V3—O691.84 (14)C28—C25—C26109.1 (7)
O8—V3—O3101.20 (16)C18—C25—C26109.1 (6)
O10—V3—O387.64 (13)C27—C25—C26107.3 (8)
O9—V3—O3155.67 (16)C25—C26—H26A109.5
O6—V3—O379.73 (13)C25—C26—H26B109.5
O8—V3—V2105.03 (14)H26A—C26—H26B109.5
O10—V3—V2132.11 (10)C25—C26—H26C109.5
O9—V3—V2119.07 (11)H26A—C26—H26C109.5
O6—V3—V230.83 (9)H26B—C26—H26C109.5
O3—V3—V248.98 (10)C25—C27—H27A109.5
O11—V4—O12102.46 (17)C25—C27—H27B109.5
O11—V4—O9103.13 (17)H27A—C27—H27B109.5
O12—V4—O9100.16 (16)C25—C27—H27C109.5
O11—V4—N492.97 (17)H27A—C27—H27C109.5
O12—V4—N491.68 (16)H27B—C27—H27C109.5
O9—V4—N4157.31 (15)C25—C28—H28A109.5
O11—V4—N394.14 (16)C25—C28—H28B109.5
O12—V4—N3158.44 (16)H28A—C28—H28B109.5
O9—V4—N389.20 (16)C25—C28—H28C109.5
N4—V4—N373.61 (16)H28A—C28—H28C109.5
O11—V4—O13174.98 (17)H28B—C28—H28C109.5
O12—V4—O1379.69 (13)C30—C29—N3122.6 (5)
O9—V4—O1380.81 (13)C30—C29—H29118.7
N4—V4—O1382.39 (13)N3—C29—H29118.7
N3—V4—O1382.74 (13)C29—C30—C31121.2 (5)
O14—V5—O12101.91 (16)C29—C30—H30119.4
O14—V5—O10103.27 (18)C31—C30—H30119.4
O12—V5—O1093.35 (15)C32—C31—C30116.1 (5)
O14—V5—O15100.93 (18)C32—C31—C39121.5 (5)
O12—V5—O1592.85 (15)C30—C31—C39122.3 (5)
O10—V5—O15153.17 (15)C31—C32—C33120.4 (5)
O14—V5—O4101.27 (16)C31—C32—H32119.8
O12—V5—O4156.45 (15)C33—C32—H32119.8
O10—V5—O485.33 (14)N3—C33—C32121.9 (5)
O15—V5—O478.71 (14)N3—C33—C34113.9 (4)
O14—V5—V6105.74 (14)C32—C33—C34124.2 (5)
O12—V5—V6122.11 (12)N4—C34—C35122.2 (5)
O10—V5—V6126.91 (10)N4—C34—C33113.4 (4)
O15—V5—V632.71 (9)C35—C34—C33124.3 (5)
O4—V5—V646.05 (11)C34—C35—C36120.4 (5)
O16—V6—O15104.53 (18)C34—C35—H35119.8
O16—V6—O17101.61 (19)C36—C35—H35119.8
O15—V6—O17105.18 (16)C37—C36—C35116.6 (5)
O16—V6—N590.95 (18)C37—C36—C43123.6 (5)
O15—V6—N587.92 (15)C35—C36—C43119.7 (5)
O17—V6—N5158.69 (18)C38—C37—C36120.3 (5)
O16—V6—N693.69 (17)C38—C37—H37119.8
O15—V6—N6153.46 (18)C36—C37—H37119.8
O17—V6—N689.49 (16)N4—C38—C37123.3 (5)
N5—V6—N672.41 (15)N4—C38—H38118.4
O16—V6—O4172.24 (17)C37—C38—H38118.4
O15—V6—O477.70 (15)C42—C39—C31110.7 (5)
O17—V6—O484.77 (16)C42—C39—C40108.5 (6)
N5—V6—O481.66 (15)C31—C39—C40112.9 (5)
N6—V6—O481.87 (14)C42—C39—C41110.3 (7)
O16—V6—V5141.52 (14)C31—C39—C41106.9 (5)
O15—V6—V537.21 (12)C40—C39—C41107.5 (6)
O17—V6—V595.34 (12)C39—C40—H40A109.5
N5—V6—V584.93 (11)C39—C40—H40B109.5
N6—V6—V5120.97 (12)H40A—C40—H40B109.5
O4—V6—V540.53 (8)C39—C40—H40C109.5
O18—V7—O13109.11 (18)H40A—C40—H40C109.5
O18—V7—O17108.9 (2)H40B—C40—H40C109.5
O13—V7—O17111.70 (17)C39—C41—H41A109.5
O18—V7—O7108.6 (2)C39—C41—H41B109.5
O13—V7—O7109.22 (16)H41A—C41—H41B109.5
O17—V7—O7109.25 (17)C39—C41—H41C109.5
C1—O1—V1129.3 (4)H41A—C41—H41C109.5
V1—O3—V3113.55 (17)H41B—C41—H41C109.5
V1—O3—V2148.84 (19)C39—C42—H42A109.5
V3—O3—V291.50 (12)C39—C42—H42B109.5
V1—O4—V5115.67 (17)H42A—C42—H42B109.5
V1—O4—V6140.14 (18)C39—C42—H42C109.5
V5—O4—V693.42 (14)H42A—C42—H42C109.5
V2—O6—V3113.82 (17)H42B—C42—H42C109.5
V7—O7—V2129.2 (2)C45—C43—C44110.6 (6)
V4—O9—V3119.51 (18)C45—C43—C36109.7 (5)
V5—O10—V3124.88 (19)C44—C43—C36109.3 (5)
V4—O12—V5121.91 (18)C45—C43—C46108.5 (6)
V7—O13—V4144.53 (19)C44—C43—C46108.4 (6)
V6—O15—V5110.08 (18)C36—C43—C46110.4 (6)
V7—O17—V6126.7 (2)C43—C44—H44A109.5
C15—N1—C11117.6 (5)C43—C44—H44B109.5
C15—N1—V2119.5 (3)H44A—C44—H44B109.5
C11—N1—V2122.6 (4)C43—C44—H44C109.5
C20—N2—C16118.8 (5)H44A—C44—H44C109.5
C20—N2—V2121.5 (4)H44B—C44—H44C109.5
C16—N2—V2119.5 (4)C43—C45—H45A109.5
C33—N3—C29117.8 (4)C43—C45—H45B109.5
C33—N3—V4119.5 (3)H45A—C45—H45B109.5
C29—N3—V4122.6 (4)C43—C45—H45C109.5
C38—N4—C34117.0 (5)H45A—C45—H45C109.5
C38—N4—V4123.8 (4)H45B—C45—H45C109.5
C34—N4—V4118.7 (3)C43—C46—H46A109.5
C47—N5—C51118.4 (4)C43—C46—H46B109.5
C47—N5—V6121.2 (3)H46A—C46—H46B109.5
C51—N5—V6120.1 (3)C43—C46—H46C109.5
C56—N6—C52117.3 (4)H46A—C46—H46C109.5
C56—N6—V6123.2 (4)H46B—C46—H46C109.5
C52—N6—V6119.0 (3)N5—C47—C48122.6 (5)
O1—C1—C6110.9 (5)N5—C47—H47118.7
O1—C1—C2111.6 (5)C48—C47—H47118.7
C6—C1—C2110.9 (5)C47—C48—C49120.0 (5)
O1—C1—H1107.7C47—C48—H48120.0
C6—C1—H1107.7C49—C48—H48120.0
C2—C1—H1107.7C50—C49—C48116.7 (5)
C1—C2—C3112.1 (6)C50—C49—C57120.8 (5)
C1—C2—H2A109.2C48—C49—C57122.4 (5)
C3—C2—H2A109.2C49—C50—C51121.0 (5)
C1—C2—H2B109.2C49—C50—H50119.5
C3—C2—H2B109.2C51—C50—H50119.5
H2A—C2—H2B107.9N5—C51—C50121.1 (4)
C2—C3—C4112.5 (6)N5—C51—C52113.9 (4)
C2—C3—H3A109.1C50—C51—C52124.8 (4)
C4—C3—H3A109.1N6—C52—C53121.6 (5)
C2—C3—H3B109.1N6—C52—C51114.1 (4)
C4—C3—H3B109.1C53—C52—C51124.2 (5)
H3A—C3—H3B107.8C54—C53—C52121.6 (5)
C3—C4—C7115.2 (6)C54—C53—H53119.2
C3—C4—C5108.1 (5)C52—C53—H53119.2
C7—C4—C5114.2 (6)C53—C54—C55115.7 (5)
C3—C4—H4106.2C53—C54—C61122.1 (5)
C7—C4—H4106.2C55—C54—C61122.2 (5)
C5—C4—H4106.2C56—C55—C54120.2 (5)
C6—C5—C4112.1 (6)C56—C55—H55119.9
C6—C5—H5A109.2C54—C55—H55119.9
C4—C5—H5A109.2N6—C56—C55123.2 (5)
C6—C5—H5B109.2N6—C56—H56118.4
C4—C5—H5B109.2C55—C56—H56118.4
H5A—C5—H5B107.9C58—C57—C60110.7 (6)
C1—C6—C5111.3 (6)C58—C57—C59108.9 (6)
C1—C6—H6A109.4C60—C57—C59109.1 (6)
C5—C6—H6A109.4C58—C57—C49112.2 (5)
C1—C6—H6B109.4C60—C57—C49108.0 (5)
C5—C6—H6B109.4C59—C57—C49107.9 (5)
H6A—C6—H6B108.0C57—C58—H58A109.5
C8—C7—C9108.9 (7)C57—C58—H58B109.5
C8—C7—C4111.5 (6)H58A—C58—H58B109.5
C9—C7—C4109.8 (7)C57—C58—H58C109.5
C8—C7—C10110.6 (8)H58A—C58—H58C109.5
C9—C7—C10108.5 (6)H58B—C58—H58C109.5
C4—C7—C10107.4 (6)C57—C59—H59A109.5
C7—C8—H8A109.5C57—C59—H59B109.5
C7—C8—H8B109.5H59A—C59—H59B109.5
H8A—C8—H8B109.5C57—C59—H59C109.5
C7—C8—H8C109.5H59A—C59—H59C109.5
H8A—C8—H8C109.5H59B—C59—H59C109.5
H8B—C8—H8C109.5C57—C60—H60A109.5
C7—C9—H9A109.5C57—C60—H60B109.5
C7—C9—H9B109.5H60A—C60—H60B109.5
H9A—C9—H9B109.5C57—C60—H60C109.5
C7—C9—H9C109.5H60A—C60—H60C109.5
H9A—C9—H9C109.5H60B—C60—H60C109.5
H9B—C9—H9C109.5C62—C61—C63108.2 (5)
C7—C10—H10A109.5C62—C61—C54112.0 (5)
C7—C10—H10B109.5C63—C61—C54109.0 (5)
H10A—C10—H10B109.5C62—C61—C64110.3 (5)
C7—C10—H10C109.5C63—C61—C64109.1 (5)
H10A—C10—H10C109.5C54—C61—C64108.2 (4)
H10B—C10—H10C109.5C61—C62—H62A109.5
N1—C11—C12122.7 (6)C61—C62—H62B109.5
N1—C11—H11118.6H62A—C62—H62B109.5
C12—C11—H11118.6C61—C62—H62C109.5
C11—C12—C13120.1 (5)H62A—C62—H62C109.5
C11—C12—H12120.0H62B—C62—H62C109.5
C13—C12—H12120.0C61—C63—H63A109.5
C12—C13—C14117.1 (5)C61—C63—H63B109.5
C12—C13—C21123.0 (5)H63A—C63—H63B109.5
C14—C13—C21119.8 (6)C61—C63—H63C109.5
C15—C14—C13120.0 (6)H63A—C63—H63C109.5
C15—C14—H14120.0H63B—C63—H63C109.5
C13—C14—H14120.0C61—C64—H64A109.5
N1—C15—C14122.5 (5)C61—C64—H64B109.5
N1—C15—C16113.3 (4)H64A—C64—H64B109.5
C14—C15—C16124.2 (5)C61—C64—H64C109.5
N2—C16—C17121.4 (5)H64A—C64—H64C109.5
N2—C16—C15113.8 (5)H64B—C64—H64C109.5
C17—C16—C15124.7 (5)N7—C65—C66178.0 (9)
C16—C17—C18120.5 (5)C65—C66—H66A109.5
C16—C17—H17119.8C65—C66—H66B109.5
C18—C17—H17119.8H66A—C66—H66B109.5
C19—C18—C17116.7 (6)C65—C66—H66C109.5
C19—C18—C25122.6 (5)H66A—C66—H66C109.5
C17—C18—C25120.7 (5)H66B—C66—H66C109.5
C20—C19—C18119.9 (5)
O2—V1—O1—C135.9 (5)V2—N2—C16—C153.2 (6)
O3—V1—O1—C1151.8 (5)N1—C15—C16—N28.3 (7)
O4—V1—O1—C178.9 (5)C14—C15—C16—N2172.4 (5)
O2—V1—O3—V3174.21 (19)N1—C15—C16—C17169.0 (5)
O4—V1—O3—V358.2 (2)C14—C15—C16—C1710.3 (9)
O1—V1—O3—V370.0 (2)N2—C16—C17—C180.6 (9)
O2—V1—O3—V233.3 (4)C15—C16—C17—C18176.5 (5)
O4—V1—O3—V282.7 (4)C16—C17—C18—C190.1 (9)
O1—V1—O3—V2149.1 (3)C16—C17—C18—C25178.3 (6)
O2—V1—O4—V5169.68 (19)C17—C18—C19—C200.7 (9)
O3—V1—O4—V553.5 (2)C25—C18—C19—C20179.1 (6)
O1—V1—O4—V575.4 (2)C16—N2—C20—C190.6 (8)
O2—V1—O4—V636.9 (3)V2—N2—C20—C19173.3 (4)
O3—V1—O4—V679.3 (3)C18—C19—C20—N21.1 (9)
O1—V1—O4—V6151.8 (3)C12—C13—C21—C24139.4 (6)
O5—V2—O6—V3174.2 (2)C14—C13—C21—C2445.0 (8)
O7—V2—O6—V380.2 (2)C12—C13—C21—C2218.3 (8)
N2—V2—O6—V384.4 (2)C14—C13—C21—C22166.2 (5)
N1—V2—O6—V330.9 (4)C12—C13—C21—C23100.3 (7)
O3—V2—O6—V33.06 (17)C14—C13—C21—C2375.2 (6)
O18—V7—O7—V2125.5 (3)C19—C18—C25—C282.7 (10)
O13—V7—O7—V26.6 (3)C17—C18—C25—C28179.0 (7)
O17—V7—O7—V2115.8 (3)C19—C18—C25—C27118.3 (7)
O5—V2—O7—V7137.4 (3)C17—C18—C25—C2760.0 (8)
O6—V2—O7—V728.3 (3)C19—C18—C25—C26124.0 (8)
N2—V2—O7—V7102.0 (5)C17—C18—C25—C2657.7 (9)
N1—V2—O7—V7122.7 (3)C33—N3—C29—C300.7 (7)
O3—V2—O7—V745.3 (3)V4—N3—C29—C30176.5 (4)
V3—V2—O7—V76.7 (3)N3—C29—C30—C311.7 (8)
O11—V4—O9—V3169.1 (2)C29—C30—C31—C322.2 (8)
O12—V4—O9—V363.7 (2)C29—C30—C31—C39175.0 (5)
N4—V4—O9—V356.7 (5)C30—C31—C32—C331.7 (7)
N3—V4—O9—V396.8 (2)C39—C31—C32—C33175.5 (5)
O13—V4—O9—V314.02 (19)C29—N3—C33—C320.2 (6)
O8—V3—O9—V4166.5 (2)V4—N3—C33—C32176.2 (3)
O10—V3—O9—V463.6 (2)C29—N3—C33—C34178.4 (4)
O6—V3—O9—V493.2 (2)V4—N3—C33—C342.4 (5)
O3—V3—O9—V424.5 (5)C31—C32—C33—N30.7 (7)
V2—V3—O9—V478.1 (2)C31—C32—C33—C34177.7 (5)
O14—V5—O10—V3169.8 (2)C38—N4—C34—C354.0 (7)
O12—V5—O10—V366.7 (2)V4—N4—C34—C35168.7 (4)
O15—V5—O10—V336.4 (4)C38—N4—C34—C33177.4 (4)
O4—V5—O10—V389.7 (2)V4—N4—C34—C339.9 (5)
V6—V5—O10—V368.5 (2)N3—C33—C34—N44.8 (5)
O8—V3—O10—V5173.0 (2)C32—C33—C34—N4176.7 (4)
O9—V3—O10—V569.7 (2)N3—C33—C34—C35173.8 (4)
O6—V3—O10—V528.9 (5)C32—C33—C34—C354.8 (7)
O3—V3—O10—V586.0 (2)N4—C34—C35—C360.6 (7)
V2—V3—O10—V563.3 (2)C33—C34—C35—C36179.0 (5)
O11—V4—O12—V5166.0 (2)C34—C35—C36—C373.4 (8)
O9—V4—O12—V560.0 (2)C34—C35—C36—C43175.1 (5)
N4—V4—O12—V5100.5 (2)C35—C36—C37—C383.9 (8)
N3—V4—O12—V554.5 (5)C43—C36—C37—C38174.6 (5)
O13—V4—O12—V518.6 (2)C34—N4—C38—C373.5 (7)
O14—V5—O12—V4161.7 (2)V4—N4—C38—C37168.8 (4)
O10—V5—O12—V457.3 (2)C36—C37—C38—N40.5 (8)
O15—V5—O12—V496.5 (2)C32—C31—C39—C4252.8 (8)
O4—V5—O12—V428.7 (5)C30—C31—C39—C42130.1 (6)
V6—V5—O12—V481.0 (2)C32—C31—C39—C40174.7 (6)
O18—V7—O13—V46.1 (4)C30—C31—C39—C408.3 (8)
O17—V7—O13—V4126.6 (3)C32—C31—C39—C4167.3 (8)
O7—V7—O13—V4112.4 (3)C30—C31—C39—C41109.7 (7)
O16—V6—O15—V5174.80 (18)C37—C36—C43—C45120.7 (7)
O17—V6—O15—V578.6 (2)C35—C36—C43—C4557.7 (8)
N5—V6—O15—V584.36 (19)C37—C36—C43—C44117.9 (6)
N6—V6—O15—V542.9 (4)C35—C36—C43—C4463.6 (7)
O4—V6—O15—V52.44 (16)C37—C36—C43—C461.3 (9)
O18—V7—O17—V695.8 (3)C35—C36—C43—C46177.2 (6)
O13—V7—O17—V624.8 (3)C51—N5—C47—C481.9 (8)
O7—V7—O17—V6145.7 (3)V6—N5—C47—C48175.8 (4)
O16—V6—O17—V7116.2 (3)N5—C47—C48—C490.0 (9)
O15—V6—O17—V77.5 (3)C47—C48—C49—C501.2 (8)
N5—V6—O17—V7118.8 (4)C47—C48—C49—C57178.0 (5)
N6—V6—O17—V7150.1 (3)C48—C49—C50—C510.5 (8)
O4—V6—O17—V768.2 (3)C57—C49—C50—C51177.3 (5)
V5—V6—O17—V729.0 (3)C47—N5—C51—C502.7 (7)
V1—O1—C1—C674.3 (7)V6—N5—C51—C50176.6 (4)
V1—O1—C1—C250.0 (7)C47—N5—C51—C52174.0 (5)
O1—C1—C2—C3179.8 (5)V6—N5—C51—C520.1 (6)
C6—C1—C2—C355.5 (8)C49—C50—C51—N51.5 (8)
C1—C2—C3—C456.5 (8)C49—C50—C51—C52174.8 (5)
C2—C3—C4—C7176.1 (6)C56—N6—C52—C532.6 (7)
C2—C3—C4—C554.8 (8)V6—N6—C52—C53169.8 (4)
C3—C4—C5—C654.8 (8)C56—N6—C52—C51179.9 (5)
C7—C4—C5—C6175.6 (6)V6—N6—C52—C517.5 (6)
O1—C1—C6—C5180.0 (6)N5—C51—C52—N64.7 (6)
C2—C1—C6—C555.4 (8)C50—C51—C52—N6178.7 (5)
C4—C5—C6—C156.5 (9)N5—C51—C52—C53172.4 (5)
C3—C4—C7—C861.6 (10)C50—C51—C52—C534.1 (8)
C5—C4—C7—C864.4 (10)N6—C52—C53—C542.1 (8)
C3—C4—C7—C9177.6 (7)C51—C52—C53—C54174.8 (5)
C5—C4—C7—C956.4 (9)C52—C53—C54—C555.7 (8)
C3—C4—C7—C1059.7 (9)C52—C53—C54—C61175.2 (5)
C5—C4—C7—C10174.3 (7)C53—C54—C55—C564.7 (8)
C15—N1—C11—C120.4 (8)C61—C54—C55—C56176.2 (5)
V2—N1—C11—C12173.0 (4)C52—N6—C56—C553.6 (8)
N1—C11—C12—C132.0 (8)V6—N6—C56—C55168.4 (4)
C11—C12—C13—C142.0 (8)C54—C55—C56—N60.1 (9)
C11—C12—C13—C21173.7 (5)C50—C49—C57—C58176.3 (6)
C12—C13—C14—C150.4 (8)C48—C49—C57—C587.1 (8)
C21—C13—C14—C15176.2 (5)C50—C49—C57—C6054.0 (7)
C11—N1—C15—C142.8 (8)C48—C49—C57—C60129.3 (6)
V2—N1—C15—C14170.8 (4)C50—C49—C57—C5963.8 (7)
C11—N1—C15—C16176.5 (4)C48—C49—C57—C59112.8 (6)
V2—N1—C15—C169.9 (6)C53—C54—C61—C6220.5 (8)
C13—C14—C15—N12.8 (8)C55—C54—C61—C62160.4 (6)
C13—C14—C15—C16176.4 (5)C53—C54—C61—C63140.2 (5)
C20—N2—C16—C170.2 (8)C55—C54—C61—C6340.7 (7)
V2—N2—C16—C17174.3 (4)C53—C54—C61—C64101.3 (6)
C20—N2—C16—C15177.2 (5)C55—C54—C61—C6477.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O14i0.952.553.417 (7)152
C30—H30···O16i0.952.383.122 (6)135
C37—H37···O5i0.952.433.264 (7)146
C40—H40B···O16i0.982.583.466 (8)150
C48—H48···O8i0.952.323.216 (6)157
Symmetry code: (i) x, y1/2, z1/2.
 

Acknowledgements

The authors acknowledge Dr Shouhei Katao (Nara Institute of Science and Technology) for the single-crystal X-ray diffraction measurement.

Funding information

This work was partly supported by Kyoto-Advanced Nanotechnology Network of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan.

References

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