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

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ISSN: 2056-9890

Tetra­kis[2-(benzyl­amino­carbonyl)phenox­ymeth­yl]methane

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: songxq@mail.lzjtu.cn

(Received 1 September 2008; accepted 4 September 2008; online 13 September 2008)

The title compound, C61H56N4O8, is arranged with all four salicylamide arms disposed in a circular fashion. Each arm has a similar conformation and they are extended so that their terminal groups can fold back. The four carbonyl O atoms are located on the outside of the mol­ecule. The structure is stabilized by intra- and inter­molecular N—H⋯O hydrogen-bonding inter­actions.

Related literature

For details of the advantages of salicylamide ligands, see: Zhang et al. (2002[Zhang, J., Tang, Y., Tang, N., Tan, M.-Y., Liu, W.-S. & Yu, K.-B. (2002). J. Chem. Soc. Dalton Trans. pp. 832-833.]); Tang et al. (2005[Tang, Y., Zhang, J., Liu, W.-S., Tan, M.-Y. & Yu, K.-B. (2005). Polyhedron, 24, 1160-1166.]). Salicylamide-derived ligands are excellent complexing agents for lanthanide ions because of their attractive sensitization of lanthanide luminescence as well as the construction of novel metal–organic frameworks, see: Song, Dou et al. (2007[Song, X.-Q., Dou, W., Liu, W.-S., Yao, J.-N., Guo, Y.-L. & Tang, X.-L. (2007). Inorg. Chem. Commun. 10, 1058-1062.]); Song, Liu et al. (2007[Song, X.-Q., Liu, W.-S., Dou, W., Wang, Y.-W., Zheng, J.-R. & Zang, Z.-P. (2007). Eur. J. Inorg. Chem. pp. 1901-1912.]); Song et al. (2008[Song, X.-Q., Liu, W.-S., Dou, W., Zheng, J.-R., Tang, X.-L., Zhang, H.-R. & Wang, D.-Q. (2008). Dalton Trans. pp. 3582-3591.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related literature, see: Farber & Conley (1974[Farber, S. & Conley, R. T. (1974). Synth. Commun. 4, 243-245.]); Jiri et al. (1994[Jiri, Z., Magdalena, P., Petri, H. & Milos, T. (1994). Synthesis, 110, 1132-1135.]).

[Scheme 1]

Experimental

Crystal data
  • C61H56N4O8

  • Mr = 973.10

  • Triclinic, [P \overline 1]

  • a = 13.0505 (4) Å

  • b = 13.6943 (4) Å

  • c = 14.3577 (4) Å

  • α = 92.519 (1)°

  • β = 102.677 (1)°

  • γ = 92.737 (1)°

  • V = 2496.66 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 153 (2) K

  • 0.39 × 0.36 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: none

  • 20607 measured reflections

  • 9277 independent reflections

  • 7923 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.119

  • S = 0.98

  • 9277 reflections

  • 659 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.88 2.12 2.7705 (16) 130
N2—H2⋯O3 0.88 1.96 2.6731 (14) 137
N3—H3⋯O5 0.88 2.27 2.7399 (14) 113
N4—H8⋯O7 0.88 2.16 2.7341 (16) 122
N4—H8⋯O4i 0.88 2.54 3.1841 (17) 131
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In the last decade, synthetic studies on salicylamide delived ligands have been carried out because of their attractive sensitization of lanthanide luminescence as well as construction of novel metal–organic frameworks (Zhang et al., 2002; Tang et al., 2005) we are systematically studying the structure and the photophysical properties of complexing salicylamide ligands of capable of sensitizing Eu(III) and Tb(III) emission recently. So far, some intriguing supramolecular complexes based on salicylamide derivatives have been reported (Song, Dou et al., 2007; Song, Liu et al., 2007; Song et al., 2008). However, the tetrapodal ligand featuring salicylamide pendant arms, which is analogues of the ligands studies above, is still unprecedented. In view of this, we report here the synthesis and crystal structure of the title compound (I) which is a part of our studies.

The molecular structure of the title compound (I) is shown in Fig. 1. All bond lengths and angles in (I) are generally within normal ranges (Allen et al., 1987). Four benzylsalicylamide arms are linked together by the quarternary carbon atom at the tetrahedry position and are severely twisted with a ca 65° dihedral angle between phenyl rings. The amide hydrogen atoms (H1, H2, H3 and H4) are hydrogen bonded to the ether oxygen atoms (O1, O3, O5 and O7) to provide four hydrogen bonded six-membered rings. It is no doubt to note that the robust intramolecular hydrogen bond have a template effect and participate in the stabilization of the complete structure (Table 1). Interestingly, the title compound was arranged with all four salicylamide arms in a circular fashion and each salicylamide arm had a similar conformation and the arm is so long that their terminal groups can "fold back". Four oxygen atoms of the carbonyl groups of the compound, namely, O2, O4, O6 and, O8, are located in the outer part of the whole molecule.

Related literature top

For details of the advantages of salicylamide ligands, see: Zhang et al. (2002); Tang et al. (2005). Salicylamide-derived ligands are excellent complexing agents for lanthanide ions because of their attractive sensitization of lanthanide luminescence as well as the construction of novel metal–organic frameworks, see: (Song, Dou et al. (2007); Song, Liu et al. (2007); Song et al. (2008). For bond-length data, see: Allen et al. (1987). For related literature, see: Farber & Conley (1974); Jiri et al. (1994).

Experimental top

The title compound was synthesized by the following method. To a solution of pentaerythritol benzenesulfonate (2.32 g, 3.3 mmol) (Farber et al.,1974) in dry DMF was added K2CO3 (0.69 g, 5 mmol) and the mixture stirred and heated for 10 min, N-benzylsalicylamide (3.40 g, 15 mmol) (Jiri et al.,1994) in 50 ml DMF was added dropwise in 30 min and the resulting solution stirred and heated to reflux for 12 h. After cooling down, inorganic salts was separated by filtration and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by chromatography on silica, gradient elution from petroleum to 10:1 petroleum–ethyl acetate to give a white powder. Colourless single crystals were grown from methanol and ethyl acetate mixed solution (v:v =1:5) with slow evaporation at room temperature. The crystals were isolated, washed three times with ethyl acetate and dried in vacuum desiccator using anhydrous CaCl2 (yield 87.4%). Analysis found (%): C 75.59, H 5.59, N 5.18; calculated for C61H56N4O8: C 75.29, H 5.61, N 5.20.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 and 0.99 Å and N—H =distance of 0.88 Å, with Uiso(H) = 1.2Ueq(C, N).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP plot of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. For the sake of clarity, H atoms have been omitted.
Tetrakis[2-(benzylaminocarbonyl)phenoxymethyl]methane top
Crystal data top
C61H56N4O8Z = 2
Mr = 973.10F(000) = 1028
Triclinic, P1Dx = 1.294 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.0505 (4) ÅCell parameters from 19896 reflections
b = 13.6943 (4) Åθ = 3.0–27.5°
c = 14.3577 (4) ŵ = 0.09 mm1
α = 92.519 (1)°T = 153 K
β = 102.677 (1)°Block, colourless
γ = 92.737 (1)°0.39 × 0.36 × 0.10 mm
V = 2496.66 (13) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
7923 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.026
Graphite monochromatorθmax = 25.5°, θmin = 3.0°
ω scansh = 1515
20607 measured reflectionsk = 1616
9277 independent reflectionsl = 1417
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.458P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
9277 reflectionsΔρmax = 0.33 e Å3
659 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0058 (9)
Crystal data top
C61H56N4O8γ = 92.737 (1)°
Mr = 973.10V = 2496.66 (13) Å3
Triclinic, P1Z = 2
a = 13.0505 (4) ÅMo Kα radiation
b = 13.6943 (4) ŵ = 0.09 mm1
c = 14.3577 (4) ÅT = 153 K
α = 92.519 (1)°0.39 × 0.36 × 0.10 mm
β = 102.677 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
7923 reflections with I > 2σ(I)
20607 measured reflectionsRint = 0.026
9277 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 0.98Δρmax = 0.33 e Å3
9277 reflectionsΔρmin = 0.28 e Å3
659 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.71522 (7)0.40146 (6)0.74396 (7)0.0307 (2)
O20.54601 (10)0.64429 (8)0.78693 (12)0.0661 (4)
O30.55519 (6)0.13763 (6)0.61990 (6)0.0280 (2)
O40.34649 (7)0.10874 (7)0.59740 (7)0.0393 (2)
O50.74512 (6)0.23924 (7)0.88530 (6)0.0311 (2)
O60.96952 (7)0.15816 (7)1.09691 (7)0.0380 (2)
O70.83899 (6)0.15492 (6)0.64490 (6)0.0286 (2)
O81.04764 (10)0.26366 (12)0.50380 (11)0.0738 (4)
N10.54553 (10)0.48316 (9)0.79809 (11)0.0468 (3)
H10.57910.42910.79620.056*
N20.49599 (9)0.03234 (8)0.68268 (8)0.0327 (3)
H20.54120.01860.68860.039*
N30.95367 (8)0.25842 (9)0.97542 (8)0.0353 (3)
H30.91350.29940.94090.042*
N40.87460 (10)0.22638 (11)0.47927 (9)0.0463 (3)
H80.82480.19200.49800.056*
C10.70914 (9)0.22638 (9)0.71619 (8)0.0239 (3)
C20.77547 (9)0.32277 (9)0.72051 (9)0.0259 (3)
H2A0.84160.32110.76970.031*
H2B0.79360.33230.65800.031*
C30.76371 (10)0.49411 (9)0.75546 (9)0.0286 (3)
C40.86715 (11)0.51142 (10)0.74710 (11)0.0375 (3)
H40.90680.45830.73350.045*
C50.91243 (12)0.60600 (11)0.75858 (12)0.0443 (4)
H50.98290.61730.75230.053*
C60.85659 (12)0.68387 (11)0.77900 (12)0.0438 (4)
H60.88780.74870.78680.053*
C70.75427 (12)0.66593 (10)0.78797 (10)0.0380 (3)
H70.71580.71950.80270.046*
C80.70542 (10)0.57233 (9)0.77623 (9)0.0309 (3)
C90.59294 (12)0.56872 (10)0.78709 (11)0.0383 (3)
C100.43784 (13)0.47788 (12)0.81327 (16)0.0571 (5)
H10A0.39030.50620.75900.068*
H10B0.43570.51720.87230.068*
C110.39984 (11)0.37408 (11)0.82190 (12)0.0413 (3)
C120.37785 (11)0.34375 (12)0.90675 (12)0.0438 (4)
H120.38780.38900.96050.053*
C130.34145 (11)0.24789 (13)0.91390 (13)0.0475 (4)
H130.32660.22790.97230.057*
C140.32691 (12)0.18217 (13)0.83652 (14)0.0526 (4)
H140.30250.11650.84140.063*
C150.34770 (13)0.21148 (13)0.75205 (14)0.0537 (4)
H150.33730.16600.69840.064*
C160.38371 (12)0.30678 (13)0.74455 (13)0.0475 (4)
H160.39750.32630.68560.057*
C170.62289 (9)0.22442 (9)0.62503 (9)0.0256 (3)
H17A0.58160.28320.62540.031*
H17B0.65480.22480.56850.031*
C180.46197 (9)0.13203 (9)0.55231 (9)0.0260 (3)
C190.43425 (10)0.20619 (10)0.49037 (9)0.0318 (3)
H190.48250.26050.49090.038*
C200.33656 (11)0.20148 (10)0.42781 (10)0.0356 (3)
H200.31740.25350.38710.043*
C210.26687 (10)0.12169 (11)0.42430 (10)0.0356 (3)
H210.19940.11900.38230.043*
C220.29651 (10)0.04574 (10)0.48274 (9)0.0312 (3)
H220.24950.01030.47800.037*
C230.39317 (9)0.04838 (9)0.54858 (9)0.0265 (3)
C240.41076 (10)0.03741 (9)0.61097 (9)0.0280 (3)
C250.51685 (12)0.10807 (10)0.75153 (10)0.0394 (3)
H25A0.53470.16860.71980.047*
H25B0.45320.12330.77630.047*
C260.60712 (11)0.07326 (9)0.83336 (10)0.0315 (3)
C270.58850 (11)0.02576 (10)0.91483 (10)0.0367 (3)
H270.51840.01460.91910.044*
C280.67124 (12)0.00558 (11)0.98991 (10)0.0385 (3)
H280.65750.03861.04510.046*
C290.77350 (11)0.01078 (10)0.98518 (10)0.0372 (3)
H290.82990.00941.03760.045*
C300.79369 (11)0.05673 (10)0.90374 (11)0.0370 (3)
H300.86400.06760.89960.044*
C310.71047 (11)0.08675 (9)0.82822 (10)0.0343 (3)
H310.72450.11710.77190.041*
C320.66037 (9)0.22090 (9)0.80331 (9)0.0255 (3)
H32A0.60750.27070.80180.031*
H32B0.62540.15530.80460.031*
C330.72272 (9)0.24358 (9)0.97413 (9)0.0262 (3)
C340.62222 (10)0.25612 (10)0.98859 (10)0.0321 (3)
H340.56490.25980.93530.039*
C350.60552 (11)0.26319 (11)1.08030 (10)0.0367 (3)
H350.53700.27331.09000.044*
C360.68784 (12)0.25563 (12)1.15780 (10)0.0408 (3)
H360.67650.26191.22090.049*
C370.78727 (11)0.23888 (11)1.14329 (10)0.0352 (3)
H370.84300.23081.19680.042*
C380.80706 (10)0.23364 (9)1.05186 (9)0.0275 (3)
C390.91648 (9)0.21274 (9)1.04265 (9)0.0282 (3)
C401.05744 (10)0.24398 (11)0.95624 (11)0.0360 (3)
H40A1.05590.18080.91950.043*
H40B1.10970.24151.01740.043*
C411.08952 (9)0.32610 (10)0.90026 (10)0.0324 (3)
C421.09177 (10)0.31052 (12)0.80485 (10)0.0379 (3)
H421.07170.24750.77410.046*
C431.12294 (11)0.38555 (14)0.75333 (12)0.0473 (4)
H431.12340.37390.68770.057*
C441.15308 (12)0.47663 (13)0.79751 (14)0.0509 (4)
H441.17530.52800.76270.061*
C451.15102 (13)0.49342 (12)0.89261 (14)0.0520 (4)
H451.17170.55650.92300.062*
C461.11900 (12)0.41904 (11)0.94406 (12)0.0421 (3)
H461.11710.43141.00930.051*
C470.78129 (9)0.14156 (9)0.71751 (9)0.0259 (3)
H47A0.83020.14090.78080.031*
H47B0.73910.07850.70510.031*
C480.92985 (9)0.10594 (9)0.65096 (9)0.0273 (3)
C490.95748 (10)0.03237 (10)0.71371 (10)0.0325 (3)
H490.91250.01320.75440.039*
C501.05103 (11)0.01316 (11)0.71690 (11)0.0406 (3)
H501.06950.06400.75930.049*
C511.11723 (12)0.01496 (12)0.65892 (12)0.0467 (4)
H511.18100.01640.66100.056*
C521.08965 (11)0.08932 (12)0.59773 (11)0.0427 (4)
H521.13630.10970.55910.051*
C530.99582 (10)0.13506 (10)0.59111 (9)0.0315 (3)
C540.97484 (11)0.21445 (11)0.52165 (10)0.0377 (3)
C550.84401 (15)0.29339 (17)0.40364 (12)0.0637 (5)
H55A0.79990.25650.34690.076*
H55B0.90800.32030.38520.076*
C560.78409 (12)0.37703 (13)0.43166 (10)0.0441 (4)
C570.67621 (12)0.36546 (11)0.41968 (11)0.0431 (4)
H570.64080.30480.39370.052*
C580.61886 (15)0.44075 (13)0.44489 (15)0.0585 (5)
H580.54470.43140.43620.070*
C590.6685 (2)0.52872 (14)0.48233 (16)0.0722 (6)
H590.62890.57990.50040.087*
C600.7743 (2)0.54280 (17)0.49355 (17)0.0846 (8)
H600.80850.60430.51830.102*
C610.83257 (16)0.46757 (19)0.46893 (14)0.0722 (6)
H610.90660.47790.47760.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0263 (4)0.0208 (4)0.0463 (5)0.0030 (3)0.0111 (4)0.0001 (4)
O20.0619 (8)0.0310 (6)0.1181 (12)0.0166 (5)0.0434 (8)0.0095 (6)
O30.0249 (4)0.0248 (4)0.0310 (5)0.0007 (3)0.0015 (3)0.0057 (4)
O40.0340 (5)0.0315 (5)0.0485 (6)0.0058 (4)0.0017 (4)0.0037 (4)
O50.0216 (4)0.0466 (6)0.0251 (4)0.0047 (4)0.0047 (3)0.0030 (4)
O60.0281 (5)0.0404 (6)0.0435 (6)0.0037 (4)0.0009 (4)0.0138 (4)
O70.0259 (4)0.0320 (5)0.0302 (5)0.0094 (4)0.0089 (3)0.0049 (4)
O80.0427 (7)0.0941 (11)0.0848 (10)0.0071 (7)0.0081 (6)0.0503 (8)
N10.0374 (7)0.0287 (6)0.0814 (10)0.0114 (5)0.0253 (6)0.0092 (6)
N20.0340 (6)0.0263 (5)0.0348 (6)0.0038 (5)0.0011 (5)0.0074 (5)
N30.0238 (5)0.0451 (7)0.0388 (6)0.0098 (5)0.0069 (5)0.0149 (5)
N40.0364 (6)0.0707 (9)0.0362 (7)0.0135 (6)0.0122 (5)0.0195 (6)
C10.0227 (6)0.0216 (6)0.0272 (6)0.0033 (5)0.0046 (5)0.0039 (5)
C20.0231 (6)0.0234 (6)0.0320 (6)0.0041 (5)0.0072 (5)0.0024 (5)
C30.0292 (6)0.0231 (6)0.0312 (6)0.0002 (5)0.0012 (5)0.0040 (5)
C40.0308 (7)0.0290 (7)0.0513 (8)0.0022 (6)0.0054 (6)0.0056 (6)
C50.0324 (7)0.0355 (8)0.0600 (10)0.0055 (6)0.0005 (7)0.0106 (7)
C60.0449 (8)0.0263 (7)0.0522 (9)0.0046 (6)0.0062 (7)0.0070 (6)
C70.0453 (8)0.0253 (7)0.0392 (8)0.0041 (6)0.0002 (6)0.0035 (6)
C80.0362 (7)0.0254 (6)0.0292 (6)0.0033 (5)0.0023 (5)0.0035 (5)
C90.0442 (8)0.0272 (7)0.0465 (8)0.0104 (6)0.0147 (6)0.0038 (6)
C100.0445 (9)0.0403 (9)0.0981 (14)0.0166 (7)0.0362 (9)0.0141 (9)
C110.0267 (7)0.0384 (8)0.0636 (10)0.0137 (6)0.0164 (6)0.0112 (7)
C120.0274 (7)0.0525 (9)0.0519 (9)0.0116 (6)0.0076 (6)0.0040 (7)
C130.0305 (7)0.0582 (10)0.0581 (10)0.0115 (7)0.0134 (7)0.0240 (8)
C140.0383 (8)0.0413 (9)0.0830 (13)0.0059 (7)0.0212 (8)0.0123 (9)
C150.0446 (9)0.0491 (10)0.0722 (12)0.0073 (7)0.0238 (8)0.0040 (9)
C160.0404 (8)0.0525 (9)0.0570 (10)0.0138 (7)0.0228 (7)0.0108 (8)
C170.0244 (6)0.0222 (6)0.0296 (6)0.0015 (5)0.0042 (5)0.0046 (5)
C180.0234 (6)0.0281 (6)0.0254 (6)0.0053 (5)0.0033 (5)0.0015 (5)
C190.0337 (7)0.0295 (7)0.0300 (7)0.0027 (5)0.0018 (5)0.0029 (5)
C200.0386 (7)0.0348 (7)0.0306 (7)0.0101 (6)0.0002 (6)0.0034 (6)
C210.0285 (6)0.0425 (8)0.0319 (7)0.0077 (6)0.0017 (5)0.0025 (6)
C220.0253 (6)0.0346 (7)0.0324 (7)0.0017 (5)0.0051 (5)0.0056 (5)
C230.0264 (6)0.0268 (6)0.0270 (6)0.0046 (5)0.0072 (5)0.0019 (5)
C240.0268 (6)0.0260 (6)0.0317 (6)0.0011 (5)0.0087 (5)0.0021 (5)
C250.0453 (8)0.0296 (7)0.0391 (8)0.0058 (6)0.0002 (6)0.0106 (6)
C260.0381 (7)0.0208 (6)0.0349 (7)0.0006 (5)0.0048 (5)0.0099 (5)
C270.0343 (7)0.0363 (7)0.0414 (8)0.0059 (6)0.0107 (6)0.0071 (6)
C280.0460 (8)0.0334 (7)0.0364 (7)0.0042 (6)0.0097 (6)0.0004 (6)
C290.0395 (7)0.0289 (7)0.0393 (8)0.0003 (6)0.0004 (6)0.0086 (6)
C300.0335 (7)0.0298 (7)0.0490 (8)0.0085 (6)0.0090 (6)0.0125 (6)
C310.0450 (8)0.0238 (6)0.0364 (7)0.0074 (6)0.0121 (6)0.0053 (5)
C320.0198 (5)0.0268 (6)0.0290 (6)0.0032 (5)0.0029 (5)0.0032 (5)
C330.0275 (6)0.0238 (6)0.0284 (6)0.0035 (5)0.0082 (5)0.0019 (5)
C340.0283 (6)0.0343 (7)0.0353 (7)0.0073 (5)0.0088 (5)0.0046 (6)
C350.0327 (7)0.0404 (8)0.0410 (8)0.0062 (6)0.0165 (6)0.0006 (6)
C360.0426 (8)0.0507 (9)0.0316 (7)0.0025 (7)0.0158 (6)0.0042 (6)
C370.0348 (7)0.0409 (8)0.0285 (7)0.0019 (6)0.0048 (5)0.0012 (6)
C380.0276 (6)0.0247 (6)0.0299 (6)0.0001 (5)0.0058 (5)0.0015 (5)
C390.0248 (6)0.0289 (6)0.0282 (6)0.0004 (5)0.0005 (5)0.0003 (5)
C400.0256 (6)0.0411 (8)0.0430 (8)0.0074 (6)0.0092 (5)0.0088 (6)
C410.0205 (6)0.0375 (7)0.0397 (7)0.0073 (5)0.0062 (5)0.0058 (6)
C420.0269 (6)0.0471 (8)0.0388 (8)0.0048 (6)0.0048 (5)0.0026 (6)
C430.0343 (7)0.0681 (11)0.0432 (8)0.0130 (7)0.0116 (6)0.0177 (8)
C440.0363 (8)0.0517 (10)0.0707 (11)0.0127 (7)0.0177 (7)0.0274 (9)
C450.0467 (9)0.0335 (8)0.0757 (12)0.0056 (7)0.0123 (8)0.0058 (8)
C460.0402 (8)0.0398 (8)0.0464 (8)0.0085 (6)0.0091 (6)0.0004 (7)
C470.0242 (6)0.0253 (6)0.0293 (6)0.0050 (5)0.0071 (5)0.0033 (5)
C480.0226 (6)0.0261 (6)0.0317 (6)0.0037 (5)0.0035 (5)0.0044 (5)
C490.0303 (6)0.0286 (7)0.0391 (7)0.0058 (5)0.0081 (5)0.0020 (6)
C500.0370 (7)0.0347 (7)0.0501 (9)0.0133 (6)0.0067 (6)0.0057 (6)
C510.0344 (7)0.0509 (9)0.0584 (10)0.0199 (7)0.0138 (7)0.0052 (8)
C520.0314 (7)0.0532 (9)0.0474 (8)0.0102 (6)0.0153 (6)0.0039 (7)
C530.0262 (6)0.0353 (7)0.0331 (7)0.0040 (5)0.0069 (5)0.0019 (6)
C540.0330 (7)0.0472 (8)0.0342 (7)0.0032 (6)0.0094 (6)0.0043 (6)
C550.0551 (10)0.1062 (16)0.0386 (9)0.0305 (10)0.0188 (7)0.0325 (10)
C560.0438 (8)0.0583 (10)0.0304 (7)0.0020 (7)0.0051 (6)0.0206 (7)
C570.0460 (8)0.0356 (8)0.0474 (9)0.0008 (7)0.0086 (7)0.0082 (6)
C580.0576 (10)0.0480 (10)0.0729 (12)0.0112 (8)0.0174 (9)0.0133 (9)
C590.1052 (18)0.0374 (10)0.0767 (14)0.0108 (11)0.0235 (12)0.0103 (9)
C600.127 (2)0.0469 (12)0.0695 (14)0.0276 (14)0.0072 (14)0.0029 (10)
C610.0579 (11)0.0937 (17)0.0551 (11)0.0284 (12)0.0053 (9)0.0208 (11)
Geometric parameters (Å, º) top
O1—C31.3771 (14)C25—C261.5116 (19)
O1—C21.4346 (15)C25—H25A0.9900
O2—C91.2272 (18)C25—H25B0.9900
O3—C181.3763 (14)C26—C271.387 (2)
O3—C171.4359 (14)C26—C311.388 (2)
O4—C241.2365 (15)C27—C281.384 (2)
O5—C331.3689 (15)C27—H270.9500
O5—C321.4312 (14)C28—C291.379 (2)
O6—C391.2283 (16)C28—H280.9500
O7—C481.3782 (15)C29—C301.385 (2)
O7—C471.4267 (14)C29—H290.9500
O8—C541.2179 (18)C30—C311.388 (2)
N1—C91.3305 (19)C30—H300.9500
N1—C101.4677 (19)C31—H310.9500
N1—H10.8800C32—H32A0.9900
N2—C241.3363 (17)C32—H32B0.9900
N2—C251.4580 (18)C33—C341.3894 (17)
N2—H20.8800C33—C381.4015 (17)
N3—C391.3374 (17)C34—C351.3811 (19)
N3—C401.4605 (16)C34—H340.9500
N3—H30.8800C35—C361.378 (2)
N4—C541.3372 (19)C35—H350.9500
N4—C551.454 (2)C36—C371.387 (2)
N4—H80.8800C36—H360.9500
C1—C171.5258 (16)C37—C381.3920 (18)
C1—C321.5259 (17)C37—H370.9500
C1—C471.5280 (17)C38—C391.5023 (17)
C1—C21.5349 (16)C40—C411.506 (2)
C2—H2A0.9900C40—H40A0.9900
C2—H2B0.9900C40—H40B0.9900
C3—C41.3915 (19)C41—C421.384 (2)
C3—C81.4016 (19)C41—C461.393 (2)
C4—C51.3853 (19)C42—C431.388 (2)
C4—H40.9500C42—H420.9500
C5—C61.376 (2)C43—C441.374 (3)
C5—H50.9500C43—H430.9500
C6—C71.381 (2)C44—C451.381 (3)
C6—H60.9500C44—H440.9500
C7—C81.3906 (18)C45—C461.385 (2)
C7—H70.9500C45—H450.9500
C8—C91.509 (2)C46—H460.9500
C10—C111.502 (2)C47—H47A0.9900
C10—H10A0.9900C47—H47B0.9900
C10—H10B0.9900C48—C491.3888 (19)
C11—C161.384 (2)C48—C531.4003 (18)
C11—C121.388 (2)C49—C501.3898 (19)
C12—C131.390 (2)C49—H490.9500
C12—H120.9500C50—C511.378 (2)
C13—C141.372 (3)C50—H500.9500
C13—H130.9500C51—C521.383 (2)
C14—C151.372 (3)C51—H510.9500
C14—H140.9500C52—C531.389 (2)
C15—C161.383 (2)C52—H520.9500
C15—H150.9500C53—C541.502 (2)
C16—H160.9500C55—C561.506 (3)
C17—H17A0.9900C55—H55A0.9900
C17—H17B0.9900C55—H55B0.9900
C18—C191.3880 (19)C56—C571.381 (2)
C18—C231.4129 (17)C56—C611.394 (3)
C19—C201.3859 (18)C57—C581.384 (2)
C19—H190.9500C57—H570.9500
C20—C211.380 (2)C58—C591.369 (3)
C20—H200.9500C58—H580.9500
C21—C221.381 (2)C59—C601.359 (4)
C21—H210.9500C59—H590.9500
C22—C231.3984 (17)C60—C611.387 (4)
C22—H220.9500C60—H600.9500
C23—C241.5045 (18)C61—H610.9500
C3—O1—C2116.95 (9)C29—C28—H28119.8
C18—O3—C17117.31 (9)C27—C28—H28119.8
C33—O5—C32118.74 (9)C28—C29—C30119.75 (13)
C48—O7—C47117.86 (10)C28—C29—H29120.1
C9—N1—C10120.73 (13)C30—C29—H29120.1
C9—N1—H1119.6C29—C30—C31119.47 (13)
C10—N1—H1119.6C29—C30—H30120.3
C24—N2—C25122.40 (11)C31—C30—H30120.3
C24—N2—H2118.8C26—C31—C30121.25 (13)
C25—N2—H2118.8C26—C31—H31119.4
C39—N3—C40123.53 (11)C30—C31—H31119.4
C39—N3—H3118.2O5—C32—C1106.28 (9)
C40—N3—H3118.2O5—C32—H32A110.5
C54—N4—C55123.08 (14)C1—C32—H32A110.5
C54—N4—H8118.5O5—C32—H32B110.5
C55—N4—H8118.5C1—C32—H32B110.5
C17—C1—C32110.10 (9)H32A—C32—H32B108.7
C17—C1—C47112.88 (10)O5—C33—C34122.96 (11)
C32—C1—C47107.79 (10)O5—C33—C38116.52 (11)
C17—C1—C2106.86 (10)C34—C33—C38120.52 (12)
C32—C1—C2110.77 (10)C35—C34—C33120.08 (12)
C47—C1—C2108.47 (9)C35—C34—H34120.0
O1—C2—C1108.32 (9)C33—C34—H34120.0
O1—C2—H2A110.0C36—C35—C34120.25 (13)
C1—C2—H2A110.0C36—C35—H35119.9
O1—C2—H2B110.0C34—C35—H35119.9
C1—C2—H2B110.0C35—C36—C37119.70 (13)
H2A—C2—H2B108.4C35—C36—H36120.1
O1—C3—C4122.13 (12)C37—C36—H36120.1
O1—C3—C8117.87 (11)C36—C37—C38121.35 (13)
C4—C3—C8120.00 (12)C36—C37—H37119.3
C5—C4—C3120.10 (14)C38—C37—H37119.3
C5—C4—H4120.0C37—C38—C33118.00 (12)
C3—C4—H4120.0C37—C38—C39117.74 (11)
C6—C5—C4120.85 (14)C33—C38—C39124.19 (11)
C6—C5—H5119.6O6—C39—N3122.24 (12)
C4—C5—H5119.6O6—C39—C38120.67 (11)
C5—C6—C7118.67 (13)N3—C39—C38117.05 (11)
C5—C6—H6120.7N3—C40—C41110.43 (11)
C7—C6—H6120.7N3—C40—H40A109.6
C6—C7—C8122.42 (14)C41—C40—H40A109.6
C6—C7—H7118.8N3—C40—H40B109.6
C8—C7—H7118.8C41—C40—H40B109.6
C7—C8—C3117.97 (12)H40A—C40—H40B108.1
C7—C8—C9114.13 (12)C42—C41—C46118.69 (14)
C3—C8—C9127.90 (12)C42—C41—C40120.80 (13)
O2—C9—N1120.31 (14)C46—C41—C40120.50 (13)
O2—C9—C8120.21 (13)C41—C42—C43121.04 (15)
N1—C9—C8119.47 (12)C41—C42—H42119.5
N1—C10—C11111.43 (13)C43—C42—H42119.5
N1—C10—H10A109.3C44—C43—C42119.81 (16)
C11—C10—H10A109.3C44—C43—H43120.1
N1—C10—H10B109.3C42—C43—H43120.1
C11—C10—H10B109.3C43—C44—C45119.85 (15)
H10A—C10—H10B108.0C43—C44—H44120.1
C16—C11—C12118.32 (15)C45—C44—H44120.1
C16—C11—C10120.68 (16)C44—C45—C46120.55 (16)
C12—C11—C10120.99 (16)C44—C45—H45119.7
C11—C12—C13120.70 (16)C46—C45—H45119.7
C11—C12—H12119.7C45—C46—C41120.06 (15)
C13—C12—H12119.7C45—C46—H46120.0
C14—C13—C12119.98 (16)C41—C46—H46120.0
C14—C13—H13120.0O7—C47—C1107.87 (10)
C12—C13—H13120.0O7—C47—H47A110.1
C15—C14—C13119.85 (16)C1—C47—H47A110.1
C15—C14—H14120.1O7—C47—H47B110.1
C13—C14—H14120.1C1—C47—H47B110.1
C14—C15—C16120.37 (17)H47A—C47—H47B108.4
C14—C15—H15119.8O7—C48—C49122.89 (12)
C16—C15—H15119.8O7—C48—C53116.60 (11)
C15—C16—C11120.78 (16)C49—C48—C53120.50 (12)
C15—C16—H16119.6C48—C49—C50119.85 (13)
C11—C16—H16119.6C48—C49—H49120.1
O3—C17—C1109.11 (9)C50—C49—H49120.1
O3—C17—H17A109.9C51—C50—C49120.44 (14)
C1—C17—H17A109.9C51—C50—H50119.8
O3—C17—H17B109.9C49—C50—H50119.8
C1—C17—H17B109.9C50—C51—C52119.20 (14)
H17A—C17—H17B108.3C50—C51—H51120.4
O3—C18—C19121.87 (11)C52—C51—H51120.4
O3—C18—C23117.83 (11)C51—C52—C53121.98 (14)
C19—C18—C23120.29 (11)C51—C52—H52119.0
C20—C19—C18120.37 (12)C53—C52—H52119.0
C20—C19—H19119.8C52—C53—C48118.00 (13)
C18—C19—H19119.8C52—C53—C54116.83 (12)
C21—C20—C19120.46 (13)C48—C53—C54125.15 (12)
C21—C20—H20119.8O8—C54—N4122.24 (15)
C19—C20—H20119.8O8—C54—C53120.27 (13)
C20—C21—C22119.11 (12)N4—C54—C53117.46 (12)
C20—C21—H21120.4N4—C55—C56113.42 (13)
C22—C21—H21120.4N4—C55—H55A108.9
C21—C22—C23122.39 (12)C56—C55—H55A108.9
C21—C22—H22118.8N4—C55—H55B108.9
C23—C22—H22118.8C56—C55—H55B108.9
C22—C23—C18117.27 (12)H55A—C55—H55B107.7
C22—C23—C24115.81 (11)C57—C56—C61117.51 (18)
C18—C23—C24126.87 (11)C57—C56—C55119.61 (16)
O4—C24—N2121.56 (12)C61—C56—C55122.88 (17)
O4—C24—C23120.61 (11)C56—C57—C58121.06 (16)
N2—C24—C23117.79 (10)C56—C57—H57119.5
N2—C25—C26109.82 (10)C58—C57—H57119.5
N2—C25—H25A109.7C59—C58—C57120.33 (19)
C26—C25—H25A109.7C59—C58—H58119.8
N2—C25—H25B109.7C57—C58—H58119.8
C26—C25—H25B109.7C60—C59—C58120.0 (2)
H25A—C25—H25B108.2C60—C59—H59120.0
C27—C26—C31118.45 (12)C58—C59—H59120.0
C27—C26—C25120.67 (13)C59—C60—C61120.13 (19)
C31—C26—C25120.88 (13)C59—C60—H60119.9
C28—C27—C26120.58 (13)C61—C60—H60119.9
C28—C27—H27119.7C60—C61—C56121.01 (19)
C26—C27—H27119.7C60—C61—H61119.5
C29—C28—C27120.45 (14)C56—C61—H61119.5
C3—O1—C2—C1177.12 (10)C33—O5—C32—C1176.76 (10)
C17—C1—C2—O172.69 (12)C17—C1—C32—O5170.75 (9)
C32—C1—C2—O147.24 (13)C47—C1—C32—O565.73 (12)
C47—C1—C2—O1165.34 (10)C2—C1—C32—O552.78 (12)
C2—O1—C3—C41.43 (18)C32—O5—C33—C3416.97 (17)
C2—O1—C3—C8178.57 (11)C32—O5—C33—C38162.40 (11)
O1—C3—C4—C5179.53 (13)O5—C33—C34—C35177.82 (12)
C8—C3—C4—C50.5 (2)C38—C33—C34—C352.8 (2)
C3—C4—C5—C60.5 (2)C33—C34—C35—C361.5 (2)
C4—C5—C6—C70.1 (2)C34—C35—C36—C371.3 (2)
C5—C6—C7—C80.6 (2)C35—C36—C37—C382.8 (2)
C6—C7—C8—C30.6 (2)C36—C37—C38—C331.4 (2)
C6—C7—C8—C9178.86 (14)C36—C37—C38—C39178.50 (13)
O1—C3—C8—C7179.94 (11)O5—C33—C38—C37179.24 (11)
C4—C3—C8—C70.05 (19)C34—C33—C38—C371.37 (19)
O1—C3—C8—C90.7 (2)O5—C33—C38—C393.91 (18)
C4—C3—C8—C9179.34 (14)C34—C33—C38—C39175.48 (12)
C10—N1—C9—O22.0 (3)C40—N3—C39—O63.6 (2)
C10—N1—C9—C8177.15 (15)C40—N3—C39—C38178.52 (12)
C7—C8—C9—O213.6 (2)C37—C38—C39—O634.71 (17)
C3—C8—C9—O2165.82 (15)C33—C38—C39—O6142.15 (13)
C7—C8—C9—N1165.53 (14)C37—C38—C39—N3143.22 (13)
C3—C8—C9—N115.1 (2)C33—C38—C39—N339.92 (18)
C9—N1—C10—C11178.91 (15)C39—N3—C40—C41162.40 (13)
N1—C10—C11—C1666.5 (2)N3—C40—C41—C42108.13 (14)
N1—C10—C11—C12114.90 (17)N3—C40—C41—C4672.80 (16)
C16—C11—C12—C130.6 (2)C46—C41—C42—C430.2 (2)
C10—C11—C12—C13179.19 (13)C40—C41—C42—C43178.93 (12)
C11—C12—C13—C140.0 (2)C41—C42—C43—C440.6 (2)
C12—C13—C14—C150.4 (2)C42—C43—C44—C450.8 (2)
C13—C14—C15—C160.3 (3)C43—C44—C45—C460.2 (2)
C14—C15—C16—C110.3 (2)C44—C45—C46—C410.6 (2)
C12—C11—C16—C150.7 (2)C42—C41—C46—C450.8 (2)
C10—C11—C16—C15179.33 (15)C40—C41—C46—C45178.31 (13)
C18—O3—C17—C1168.19 (10)C48—O7—C47—C1160.79 (10)
C32—C1—C17—O356.82 (13)C17—C1—C47—O766.85 (12)
C47—C1—C17—O363.67 (13)C32—C1—C47—O7171.34 (9)
C2—C1—C17—O3177.18 (9)C2—C1—C47—O751.36 (12)
C17—O3—C18—C190.83 (17)C47—O7—C48—C4911.48 (16)
C17—O3—C18—C23178.04 (10)C47—O7—C48—C53167.43 (10)
O3—C18—C19—C20175.35 (12)O7—C48—C49—C50179.20 (12)
C23—C18—C19—C203.49 (19)C53—C48—C49—C500.33 (19)
C18—C19—C20—C211.9 (2)C48—C49—C50—C510.7 (2)
C19—C20—C21—C221.2 (2)C49—C50—C51—C520.2 (2)
C20—C21—C22—C232.8 (2)C50—C51—C52—C531.6 (2)
C21—C22—C23—C181.24 (19)C51—C52—C53—C482.0 (2)
C21—C22—C23—C24176.44 (12)C51—C52—C53—C54179.74 (14)
O3—C18—C23—C22176.99 (11)O7—C48—C53—C52177.95 (12)
C19—C18—C23—C221.90 (18)C49—C48—C53—C520.99 (19)
O3—C18—C23—C240.40 (18)O7—C48—C53—C540.17 (18)
C19—C18—C23—C24179.28 (12)C49—C48—C53—C54179.11 (12)
C25—N2—C24—O42.4 (2)C55—N4—C54—O84.7 (3)
C25—N2—C24—C23175.58 (12)C55—N4—C54—C53173.51 (15)
C22—C23—C24—O46.19 (18)C52—C53—C54—O829.9 (2)
C18—C23—C24—O4176.39 (12)C48—C53—C54—O8148.21 (16)
C22—C23—C24—N2171.85 (12)C52—C53—C54—N4148.30 (14)
C18—C23—C24—N25.57 (19)C48—C53—C54—N433.6 (2)
C24—N2—C25—C26169.71 (12)C54—N4—C55—C56114.61 (18)
N2—C25—C26—C2791.87 (16)N4—C55—C56—C5787.02 (19)
N2—C25—C26—C3187.18 (16)N4—C55—C56—C6193.6 (2)
C31—C26—C27—C281.3 (2)C61—C56—C57—C580.7 (2)
C25—C26—C27—C28179.64 (13)C55—C56—C57—C58179.85 (15)
C26—C27—C28—C290.6 (2)C56—C57—C58—C590.1 (3)
C27—C28—C29—C301.6 (2)C57—C58—C59—C601.0 (3)
C28—C29—C30—C310.7 (2)C58—C59—C60—C611.3 (3)
C27—C26—C31—C302.19 (19)C59—C60—C61—C560.6 (3)
C25—C26—C31—C30178.74 (12)C57—C56—C61—C600.4 (3)
C29—C30—C31—C261.2 (2)C55—C56—C61—C60179.81 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.882.122.7705 (16)130
N2—H2···O30.881.962.6731 (14)137
N3—H3···O50.882.272.7399 (14)113
N4—H8···O70.882.162.7341 (16)122
N4—H8···O4i0.882.543.1841 (17)131
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC61H56N4O8
Mr973.10
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)13.0505 (4), 13.6943 (4), 14.3577 (4)
α, β, γ (°)92.519 (1), 102.677 (1), 92.737 (1)
V3)2496.66 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.39 × 0.36 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20607, 9277, 7923
Rint0.026
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.119, 0.98
No. of reflections9277
No. of parameters659
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.28

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.88002.12002.7705 (16)130.00
N2—H2···O30.88001.96002.6731 (14)137.00
N3—H3···O50.88002.27002.7399 (14)113.00
N4—H8···O70.88002.16002.7341 (16)122.00
N4—H8···O4i0.88002.54003.1841 (17)131.00
Symmetry code: (i) x+1, y, z+1.
 

References

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First citationSong, X.-Q., Liu, W.-S., Dou, W., Zheng, J.-R., Tang, X.-L., Zhang, H.-R. & Wang, D.-Q. (2008). Dalton Trans. pp. 3582–3591.  Web of Science CSD CrossRef PubMed Google Scholar
First citationTang, Y., Zhang, J., Liu, W.-S., Tan, M.-Y. & Yu, K.-B. (2005). Polyhedron, 24, 1160–1166.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhang, J., Tang, Y., Tang, N., Tan, M.-Y., Liu, W.-S. & Yu, K.-B. (2002). J. Chem. Soc. Dalton Trans. pp. 832–833.  Web of Science CSD CrossRef Google Scholar

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