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

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ISSN: 2414-3146

N,N,N-Tris(di­phenyl­phospho­rylmeth­yl)amine

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aEuropean Commission, DG Joint Research Centre, Directorate G - Nuclear Safety and Security, G.I.5 – Advanced Nuclear Knowledge, PO Box 2340, 76125 Karlsruhe, Germany
*Correspondence e-mail: olaf.walter@ec.europa.eu

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 29 September 2017; accepted 12 October 2017; online 20 October 2017)

The structure of N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine, C39H36NO3P3, at 103 K has monoclinic (P21/c) symmetry. Two molecules, each with pseudo-threefold rotation symmetry, crystallize in the asymmetric unit of the monoclinic unit cell. The compound acts as ligand for the stabilization of metal ions with flexible coordination enabling three- or fourfold coordination.

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

Structure description

Phosphine oxides act as ligands for stabilizing oxophilic metal ions via complex formation. Many complexes of phosphine oxides stabilizing lanthanide and actinide ions have been described (some recent examples are: Baulin et al., 2015[Baulin, V. E., Ivanova, I. S., Polyakova, I. N., Pyatova, E. N., Rychkov, V. N., Kirillov, E. V., Kirillov, S. V. & Tsivadze, A. Yu. (2015). Russ. J. Inorg. Chem. 60, 843-847.]; Bowden et al., 2015[Bowden, A., Lees, A. M. J. & Platt, A. W. G. (2015). Polyhedron, 91, 110-119.]; Dong et al., 2015[Dong, Y., Yan, P., Zou, X., Liu, T. & Li, G. (2015). J. Mater. Chem. C, 3, 4407-4415.]; Hasegawa et al., 2015[Hasegawa, Y., Sato, N., Hirai, Y., Nakanishi, T., Kitagawa, Y., Kobayashi, A., Kato, M., Seki, T., Ito, H. & Fushimi, K. (2015). J. Phys. Chem. A, 119, 4825-4833.]; Hirai et al., 2015[Hirai, Y., Nakanishi, T., Kitagawa, Y., Fushimi, K., Seki, T., Ito, H., Fueno, H., Tanaka, K., Satoh, T. & Hasegawa, Y. (2015). Inorg. Chem. 54, 4364-4370.], 2016[Hirai, Y., Nakanishi, T., Kitagawa, Y., Fushimi, K., Seki, T., Ito, H. & Hasegawa, Y. (2016). Angew. Chem. Int. Ed. 55, 12059-12062.]; Tolpygin et al., 2015[Tolpygin, A. O., Glukhova, T. A., Cherkasov, A. V., Fukin, G. K., Aleksanyan, D. V., Cui, D. & Trifonov, A. A. (2015). Dalton Trans. 44, 16465-16474.]; Yanagisawa et al., 2015[Yanagisawa, K., Nakanishi, T., Kitagawa, Y., Seki, T., Akama, T., Kobayashi, M., Taketsugu, T., Ito, H., Fushimi, K. & Hasegawa, Y. (2015). Eur. J. Inorg. Chem. pp. 4769-4774.]). Tripodal ligands form a pocket in which the metal can be embedded via spherical coordination and therefore create a shielded pocket contributing to an even greater stabilization of the complexes (see: Cecconi et al., 2000[Cecconi, F., Ghilardi, C. A., Midollini, S. & Orlandini, A. (2000). Inorg. Chem. Commun. 3, 350-353.], 2001a[Cecconi, F., Ghilardi, C. A., Gili, P., Midollini, S., Luis, P. A. L., Lozano-Gorrin, A. D. & Orlandini, A. (2001a). Inorg. Chim. Acta, 319, 67-74.],b[Cecconi, F., Ghilardi, C. A., Luis, P. A. L., Midollini, S., Orlandini, A., Dakternieks, D., Duthie, A., Dominguez, S., Berti, E. & Vacca, A. (2001b). J. Chem. Soc. Dalton Trans. pp. 211-217.]; Fu et al., 2011[Fu, R., Hu, S. & Wu, X. (2011). J. Solid State Chem. 184, 159-163.]; Li et al., 2010[Li, H., Zhang, L., Li, G., Yu, Y., Huo, Q. & Liu, Y. (2010). Microporous Mesoporous Mater. 131, 186-191.]; Somov & Chausov, 2014[Somov, N. V. & Chausov, F. F. (2014). Crystallogr. Rep. 59, 66-70.], 2015[Somov, N. V. & Chausov, F. F. (2015). Crystallogr. Rep. 60, 210-216.]; Somov et al., 2015[Somov, N. V., Chausov, F. F., Zakirova, R. M. & Fedotova, I. V. (2015). Russ. J. Coord. Chem. 41, 798-804.], 2016[Somov, N. V., Chausov, F. F., Zakirova, R. M., Shumilova, M. A., Aleksandrov, V. A. & Petrov, V. G. (2016). Russ. J. Coord. Chem. 42, 37-43.]).

In the crystal structure of N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine, the two mol­ecules in the asymmetric unit show a comparable arrangement (r.m.s. deviation = 0.5340 Å), even if there are no hydrogen-bond bridges or other external influences (Figs. 1[link] and 2[link]). Both mol­ecules exhibit a polar pocket with a tripodal arrangement of the N(CH2PR2O)3 group; the P and O atoms of this group show a nearly planar arrangement (mean deviation for the selected atoms from this plane for mol­ecule 1 = 0.065 Å and for mol­ecule 2 = 0.074 Å). The mol­ecules are oriented such that the O atoms point always in the direction of a P atom of a neighbouring arm, establishing an average intra­molecular P—O distance of 4.46 (5) Å. The reason of this arrangement is probably found in a dipole–dipole inter­action between the partially negative O atom and the partial positive P atom. This arrangement leads, for both mol­ecules, to the formation of a hydro­phobic outer sphere of the mol­ecules formed by the phenyl rings sitting at the outside and shielding the polar pocket.

[Figure 1]
Figure 1
View of the mol­ecular structure of one of the mol­ecules of N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine in the asymmetric unit, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
View along the pseudo-threefold rotation axis of one of the N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine mol­ecules present in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.

There are no remarkable supra­molecular features present in the structures.

For N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine, coordin­ation with a Be atom has been shown in the complex aqua[N,N,N-tris­(di­phenyl­phospho­rylmeth­yl)amine-κ3O,O′,O′′]beryllium(II) diperchlorate (Cecconi et al., 2000[Cecconi, F., Ghilardi, C. A., Midollini, S. & Orlandini, A. (2000). Inorg. Chem. Commun. 3, 350-353.]). The structure of the ligand itself has not been reported. There exist bidentate ligands incorporating the RN(CH2PR2O)2 moiety (Elsegood et al., 2013[Elsegood, M. R. J., Noble, T. A., Talib, S. & Smith, M. B. (2013). Phosphorus Sulfur Silicon Relat. Elem. 188, 121-127.]; Enthaler & Nagel, 2014[Enthaler, S. & Nagel, A. (2014). Private communication (CCDC 1031247). CCDC, Cambridge, England.]; Hursthouse et al., 2003[Hursthouse, M. B., Light, M. E. & Smith, M. B. (2003). Private communication (CCDC 223214). CCDC, Cambridge, England.]; Musina et al., 2015[Musina, E. I., Wittmann, T. I., Strelnik, I. D., Naumova, O. E., Karasik, A. A., Krivolapov, D. B., Islamov, D. R., Kataeva, O. N., Sinyashin, O. G., Lonnecke, P. & Hey-Hawkins, E. (2015). Polyhedron, 100, 344-350.]; Priya et al., 2003[Priya, S., Balakrishna, M. S., Mague, J. T. & Mobin, S. M. (2003). Inorg. Chem. 42, 1272-1281.]; Yang et al., 2010[Yang, J. Y., Bullock, R. M., Dougherty, W. G., Kassel, W. S., Twamley, B., DuBois, D. L. & DuBois, M. R. (2010). Dalton Trans. 39, 3001-3010.]).

Synthesis and crystallization

To a solution of 3.09 g (15.3 mmol) di­phenyl­phospine oxide dissolved in 20 ml dry tetra­hydro­furan (THF) in a Schlenk tube, 9.7 ml of a 1.6 M solution of methyl­lithium in Et2O were added. This solution was then added to a solution of 0.83 g (5.1 mmol) of tris­(chloro­meth­yl)amine in 20 ml dry THF (Figs. 3[link]). The solvent was removed under vacuum, and the residue was extracted with Et2O. N,N,N-Tris(di­phenyl­phospho­rylmeth­yl)amine was obtained as a crystalline product (yield 80%, 2.5 g).

[Figure 3]
Figure 3
The preparation of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. H atoms attached to C atoms were fixed geometrically with fixed bond lengths and refined isotropically using a riding model.

Table 1
Experimental details

Crystal data
Chemical formula C39H36NO3P3
Mr 659.60
Crystal system, space group Monoclinic, P21/c
Temperature (K) 103
a, b, c (Å) 10.9219 (10), 25.078 (2), 24.870 (2)
β (°) 95.515 (1)
V3) 6780.3 (10)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.22
Crystal size (mm) 0.10 × 0.07 × 0.05
 
Data collection
Diffractometer Bruker APEXII Quazar
Absorption correction Multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEXII, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.953, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections 122037, 16105, 11728
Rint 0.061
(sin θ/λ)max−1) 0.666
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.109, 1.01
No. of reflections 16105
No. of parameters 843
H-atom treatment Only H-atom displacement parameters refined
Δρmax, Δρmin (e Å−3) 0.45, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEXII, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2017 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), XPMA (Zsolnai, 1996[Zsolnai, L. (1996). XPMA. University of Heidelberg, Germany.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: XPMA (Zsolnai, 1996) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

N,N,N-Tris(diphenylphosphorylmethyl)amine top
Crystal data top
C39H36NO3P3F(000) = 2768
Mr = 659.60Dx = 1.292 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.9219 (10) ÅCell parameters from 9834 reflections
b = 25.078 (2) Åθ = 2.3–27.7°
c = 24.870 (2) ŵ = 0.22 mm1
β = 95.515 (1)°T = 103 K
V = 6780.3 (10) Å3Plates, colourless
Z = 80.10 × 0.07 × 0.05 mm
Data collection top
Bruker APEXII Quazar
diffractometer
16105 independent reflections
Radiation source: fine-focus sealed tube11728 reflections with I > 2σ(I)
Detector resolution: 66 pixels mm-1Rint = 0.061
combined ω– and phi–scanθmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan
(sadabs)
h = 1414
Tmin = 0.953, Tmax = 0.99k = 3332
122037 measured reflectionsl = 3332
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045Only H-atom displacement parameters refined
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0396P)2 + 5.4914P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
16105 reflectionsΔρmax = 0.45 e Å3
843 parametersΔρmin = 0.40 e Å3
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
P10.79011 (5)0.62151 (2)0.12042 (2)0.01831 (11)
P20.63329 (5)0.62870 (2)0.05351 (2)0.02301 (12)
P30.55451 (5)0.76785 (2)0.07543 (2)0.01861 (11)
P40.36014 (5)0.88739 (2)0.12751 (2)0.01853 (11)
P50.10685 (5)0.86584 (2)0.04030 (2)0.01839 (11)
P60.10461 (5)0.73715 (2)0.09964 (2)0.02016 (11)
O10.80469 (13)0.66437 (6)0.16077 (5)0.0241 (3)
O20.70905 (15)0.57987 (6)0.04848 (6)0.0312 (4)
O30.49328 (13)0.77722 (6)0.02502 (5)0.0229 (3)
O40.39175 (13)0.84659 (6)0.17029 (5)0.0239 (3)
O50.17959 (13)0.91595 (6)0.04209 (5)0.0246 (3)
O60.02638 (14)0.71782 (6)0.05104 (5)0.0260 (3)
N10.68834 (15)0.68040 (6)0.03998 (6)0.0171 (3)
N20.21699 (15)0.82391 (6)0.05487 (6)0.0171 (3)
C10.78999 (18)0.64463 (8)0.05105 (7)0.0194 (4)
H1A0.7877690.6130500.0272800.026 (2)*
H1B0.8685700.6634030.0409090.026 (2)*
C20.68655 (19)0.68687 (8)0.01902 (7)0.0197 (4)
H2A0.6328040.7174420.0258160.026 (2)*
H2B0.7707380.6957090.0348580.026 (2)*
C30.70148 (18)0.73311 (8)0.06518 (7)0.0184 (4)
H3A0.7353060.7284870.1004200.026 (2)*
H3B0.7603330.7549780.0418000.026 (2)*
C40.91934 (18)0.57623 (8)0.11559 (8)0.0211 (4)
C51.01796 (19)0.58845 (9)0.14473 (8)0.0251 (5)
H51.0152730.6195440.1666280.033 (3)*
C61.1202 (2)0.55553 (10)0.14201 (9)0.0312 (5)
H61.1876780.5642350.1618060.033 (3)*
C71.1242 (2)0.50998 (9)0.11049 (9)0.0311 (5)
H71.1940050.4872450.1090670.033 (3)*
C81.0270 (2)0.49743 (9)0.08104 (10)0.0321 (5)
H81.0303930.4662570.0592450.033 (3)*
C90.9242 (2)0.53038 (9)0.08331 (9)0.0283 (5)
H90.8575450.5218130.0630050.033 (3)*
C100.65566 (18)0.58094 (8)0.13825 (8)0.0199 (4)
C110.6439 (2)0.55947 (9)0.19059 (8)0.0258 (5)
H110.7056130.5661000.2141950.035 (3)*
C120.5426 (2)0.52867 (9)0.20789 (9)0.0283 (5)
H120.5350000.5142310.2433690.035 (3)*
C130.4526 (2)0.51881 (9)0.17379 (9)0.0290 (5)
H130.3837960.4971610.1855330.035 (3)*
C140.4630 (2)0.54062 (10)0.12242 (9)0.0348 (6)
H140.4005140.5342970.0991380.035 (3)*
C150.5643 (2)0.57171 (10)0.10467 (8)0.0301 (5)
H150.5705940.5866310.0693960.035 (3)*
C160.4747 (2)0.61749 (9)0.02914 (8)0.0241 (4)
C170.3925 (2)0.65785 (9)0.01293 (9)0.0283 (5)
H170.4195290.6938690.0134790.041 (3)*
C180.2703 (2)0.64576 (10)0.00418 (9)0.0336 (5)
H180.2137090.6735880.0143080.041 (3)*
C190.2315 (2)0.59315 (10)0.00640 (9)0.0364 (6)
H190.1481330.5850130.0179150.041 (3)*
C200.3136 (2)0.55230 (10)0.00808 (9)0.0364 (6)
H200.2872730.5162190.0053900.041 (3)*
C210.4344 (2)0.56429 (9)0.02652 (9)0.0313 (5)
H210.4901860.5363780.0374160.041 (3)*
C220.6376 (2)0.65232 (9)0.12251 (8)0.0283 (5)
C230.5647 (2)0.69389 (11)0.13777 (9)0.0368 (6)
H230.5085420.7106890.1115170.055 (4)*
C240.5729 (2)0.71128 (12)0.19125 (10)0.0438 (7)
H240.5228290.7398030.2015110.055 (4)*
C250.6549 (3)0.68649 (12)0.22928 (9)0.0485 (8)
H250.6607560.6980530.2658100.055 (4)*
C260.7274 (3)0.64563 (11)0.21475 (10)0.0475 (7)
H260.7827040.6288050.2412990.055 (4)*
C270.7208 (3)0.62830 (10)0.16103 (9)0.0395 (6)
H270.7727650.6003770.1509420.055 (4)*
C280.46179 (19)0.72860 (8)0.12457 (8)0.0211 (4)
C290.3384 (2)0.72150 (9)0.11850 (9)0.0319 (5)
H290.3045920.7356140.0877180.040 (3)*
C300.2635 (2)0.69362 (11)0.15750 (11)0.0404 (6)
H300.1786190.6888000.1534470.040 (3)*
C310.3138 (2)0.67300 (10)0.20219 (9)0.0360 (6)
H310.2630190.6540550.2288610.040 (3)*
C320.4365 (2)0.67979 (9)0.20817 (8)0.0315 (5)
H320.4702000.6651760.2387510.040 (3)*
C330.5112 (2)0.70773 (9)0.16998 (8)0.0258 (5)
H330.5957890.7127510.1745430.040 (3)*
C340.58512 (19)0.82821 (8)0.11178 (7)0.0210 (4)
C350.4843 (2)0.85512 (9)0.13775 (9)0.0309 (5)
H350.4036380.8414530.1359930.039 (3)*
C360.5013 (2)0.90163 (9)0.16603 (10)0.0353 (6)
H360.4321980.9196750.1836360.039 (3)*
C370.6176 (2)0.92196 (9)0.16885 (9)0.0335 (6)
H370.6285480.9538300.1884830.039 (3)*
C380.7184 (2)0.89605 (9)0.14316 (8)0.0326 (5)
H380.7986530.9101830.1448820.039 (3)*
C390.7021 (2)0.84904 (9)0.11468 (8)0.0274 (5)
H390.7715540.8311680.0971510.039 (3)*
C400.32483 (18)0.85967 (8)0.06036 (7)0.0189 (4)
H40A0.3101700.8893940.0343400.025 (2)*
H40B0.3974260.8396290.0504180.025 (2)*
C410.18464 (18)0.81164 (8)0.00284 (7)0.0181 (4)
H41A0.1309350.7797610.0057170.025 (2)*
H41B0.2607510.8027810.0195790.025 (2)*
C420.24160 (18)0.77409 (8)0.08536 (7)0.0193 (4)
H42A0.2897770.7827090.1200310.025 (2)*
H42B0.2930730.7507400.0646380.025 (2)*
C430.48673 (18)0.93204 (8)0.11987 (7)0.0195 (4)
C440.59703 (19)0.92280 (9)0.15184 (8)0.0258 (5)
H440.6036010.8937740.1764880.035 (3)*
C450.6969 (2)0.95618 (10)0.14745 (8)0.0300 (5)
H450.7719010.9499740.1691950.035 (3)*
C460.6877 (2)0.99845 (9)0.11155 (9)0.0285 (5)
H460.7564331.0211280.1086230.035 (3)*
C470.5783 (2)1.00775 (9)0.07983 (8)0.0271 (5)
H470.5721561.0368110.0552090.035 (3)*
C480.47797 (19)0.97482 (8)0.08394 (8)0.0240 (4)
H480.4030500.9813790.0622600.035 (3)*
C490.23395 (18)0.92915 (8)0.14350 (8)0.0195 (4)
C500.2382 (2)0.94835 (9)0.19651 (8)0.0247 (5)
H500.3059170.9394530.2217830.035 (3)*
C510.1448 (2)0.98013 (9)0.21241 (8)0.0295 (5)
H510.1497710.9938690.2481530.035 (3)*
C520.0439 (2)0.99198 (9)0.17623 (9)0.0291 (5)
H520.0211731.0131890.1873830.035 (3)*
C530.0381 (2)0.97288 (9)0.12388 (9)0.0296 (5)
H530.0311250.9810430.0991290.035 (3)*
C540.13244 (19)0.94193 (9)0.10734 (8)0.0260 (5)
H540.1281110.9293160.0711910.035 (3)*
C550.03716 (18)0.87709 (8)0.01214 (7)0.0197 (4)
C560.0857 (2)0.92877 (9)0.01684 (8)0.0248 (5)
H560.0402490.9562370.0321520.028 (3)*
C570.1992 (2)0.94012 (9)0.00061 (8)0.0294 (5)
H570.2314780.9752730.0026450.028 (3)*
C580.2659 (2)0.90017 (9)0.02284 (8)0.0284 (5)
H580.3447890.9077470.0340030.028 (3)*
C590.2178 (2)0.84918 (9)0.02886 (8)0.0260 (5)
H590.2632770.8220980.0447620.028 (3)*
C600.10332 (19)0.83740 (8)0.01176 (7)0.0219 (4)
H600.0702630.8024750.0163230.028 (3)*
C610.06819 (18)0.83747 (8)0.10663 (7)0.0196 (4)
C620.0980 (2)0.86625 (9)0.15147 (8)0.0271 (5)
H620.1409420.8990940.1465980.034 (3)*
C630.0650 (2)0.84708 (10)0.20344 (9)0.0351 (6)
H630.0847680.8670370.2339050.034 (3)*
C640.0037 (2)0.79910 (10)0.21069 (8)0.0313 (5)
H640.0181710.7860770.2461890.034 (3)*
C650.0261 (2)0.76992 (9)0.16672 (8)0.0272 (5)
H650.0684750.7369630.1719220.034 (3)*
C660.00615 (19)0.78899 (9)0.11479 (8)0.0237 (4)
H660.0142040.7688500.0845480.034 (3)*
C670.01997 (19)0.77783 (8)0.14301 (7)0.0196 (4)
C680.0756 (2)0.81575 (9)0.17843 (8)0.0240 (4)
H680.1613900.8223140.1792340.038 (3)*
C690.0053 (2)0.84393 (9)0.21253 (8)0.0284 (5)
H690.0435580.8697830.2365110.038 (3)*
C700.1194 (2)0.83469 (9)0.21189 (8)0.0285 (5)
H700.1665620.8536790.2357350.038 (3)*
C710.1752 (2)0.79776 (10)0.17645 (9)0.0324 (5)
H710.2613150.7918240.1754720.038 (3)*
C720.1065 (2)0.76929 (9)0.14229 (8)0.0278 (5)
H720.1456660.7437750.1181930.038 (3)*
C730.1731 (2)0.68403 (8)0.14147 (8)0.0247 (5)
C740.2498 (2)0.69481 (10)0.18835 (10)0.0356 (6)
H740.2614820.7305900.2002810.076 (5)*
C750.3089 (2)0.65381 (11)0.21757 (11)0.0431 (6)
H750.3608250.6612600.2495500.076 (5)*
C760.2917 (3)0.60195 (12)0.19984 (11)0.0559 (8)
H760.3335420.5737190.2193390.076 (5)*
C770.2156 (4)0.59091 (12)0.15480 (12)0.0760 (12)
H770.2029070.5549570.1435850.076 (5)*
C780.1562 (3)0.63188 (10)0.12494 (10)0.0547 (9)
H780.1040300.6239000.0931730.076 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0175 (3)0.0196 (3)0.0183 (2)0.0006 (2)0.00430 (19)0.00088 (19)
P20.0280 (3)0.0239 (3)0.0174 (2)0.0019 (2)0.0036 (2)0.0001 (2)
P30.0182 (3)0.0195 (3)0.0180 (2)0.0006 (2)0.00107 (19)0.00319 (19)
P40.0155 (2)0.0242 (3)0.0155 (2)0.0027 (2)0.00039 (18)0.00124 (19)
P50.0182 (3)0.0198 (3)0.0168 (2)0.0024 (2)0.00013 (19)0.00007 (19)
P60.0229 (3)0.0189 (3)0.0187 (2)0.0019 (2)0.00194 (19)0.00013 (19)
O10.0273 (8)0.0235 (8)0.0221 (7)0.0012 (6)0.0060 (6)0.0025 (6)
O20.0385 (10)0.0269 (9)0.0285 (8)0.0035 (7)0.0053 (7)0.0053 (6)
O30.0225 (8)0.0254 (8)0.0215 (7)0.0004 (6)0.0048 (6)0.0044 (6)
O40.0224 (8)0.0291 (8)0.0195 (7)0.0030 (6)0.0015 (6)0.0045 (6)
O50.0245 (8)0.0237 (8)0.0248 (7)0.0065 (6)0.0009 (6)0.0013 (6)
O60.0300 (8)0.0248 (8)0.0225 (7)0.0066 (7)0.0002 (6)0.0036 (6)
N10.0168 (8)0.0192 (9)0.0156 (7)0.0009 (7)0.0035 (6)0.0024 (6)
N20.0168 (8)0.0188 (9)0.0154 (7)0.0015 (7)0.0006 (6)0.0011 (6)
C10.0172 (10)0.0211 (11)0.0199 (9)0.0000 (8)0.0014 (7)0.0025 (7)
C20.0218 (10)0.0213 (11)0.0159 (9)0.0022 (8)0.0014 (7)0.0028 (7)
C30.0195 (10)0.0180 (10)0.0178 (9)0.0020 (8)0.0022 (7)0.0016 (7)
C40.0178 (10)0.0231 (11)0.0225 (9)0.0016 (8)0.0017 (8)0.0048 (8)
C50.0238 (11)0.0310 (12)0.0209 (9)0.0005 (9)0.0043 (8)0.0022 (8)
C60.0202 (11)0.0451 (15)0.0293 (11)0.0014 (10)0.0070 (9)0.0067 (10)
C70.0228 (12)0.0323 (13)0.0374 (12)0.0075 (10)0.0018 (9)0.0119 (10)
C80.0294 (13)0.0235 (12)0.0421 (13)0.0027 (10)0.0041 (10)0.0023 (10)
C90.0212 (11)0.0266 (12)0.0378 (12)0.0025 (9)0.0061 (9)0.0019 (9)
C100.0184 (10)0.0193 (10)0.0218 (9)0.0026 (8)0.0007 (8)0.0004 (8)
C110.0244 (11)0.0290 (12)0.0247 (10)0.0001 (9)0.0052 (8)0.0036 (8)
C120.0272 (12)0.0284 (12)0.0284 (11)0.0019 (10)0.0019 (9)0.0061 (9)
C130.0206 (11)0.0298 (13)0.0348 (11)0.0039 (9)0.0066 (9)0.0013 (9)
C140.0234 (12)0.0531 (16)0.0280 (11)0.0104 (11)0.0035 (9)0.0023 (10)
C150.0259 (12)0.0447 (14)0.0199 (10)0.0071 (10)0.0028 (8)0.0028 (9)
C160.0286 (12)0.0272 (12)0.0180 (9)0.0051 (9)0.0093 (8)0.0046 (8)
C170.0289 (12)0.0259 (12)0.0313 (11)0.0054 (10)0.0083 (9)0.0084 (9)
C180.0273 (13)0.0355 (14)0.0395 (13)0.0061 (10)0.0108 (10)0.0101 (10)
C190.0295 (13)0.0449 (16)0.0365 (12)0.0140 (11)0.0124 (10)0.0120 (11)
C200.0432 (15)0.0324 (14)0.0364 (12)0.0189 (12)0.0183 (11)0.0091 (10)
C210.0404 (14)0.0274 (13)0.0279 (11)0.0077 (11)0.0121 (10)0.0006 (9)
C220.0354 (13)0.0314 (13)0.0186 (9)0.0094 (10)0.0047 (9)0.0002 (8)
C230.0328 (13)0.0521 (16)0.0259 (11)0.0039 (12)0.0040 (9)0.0096 (11)
C240.0404 (15)0.0606 (18)0.0323 (12)0.0130 (13)0.0127 (11)0.0173 (12)
C250.066 (2)0.0595 (19)0.0205 (11)0.0260 (16)0.0075 (12)0.0062 (11)
C260.069 (2)0.0476 (17)0.0244 (11)0.0149 (15)0.0053 (12)0.0054 (11)
C270.0555 (17)0.0350 (14)0.0269 (11)0.0068 (12)0.0019 (11)0.0044 (10)
C280.0214 (10)0.0193 (11)0.0219 (9)0.0004 (8)0.0014 (8)0.0018 (8)
C290.0261 (12)0.0335 (13)0.0359 (12)0.0011 (10)0.0022 (9)0.0101 (10)
C300.0222 (12)0.0453 (16)0.0521 (15)0.0059 (11)0.0043 (11)0.0124 (12)
C310.0386 (14)0.0305 (13)0.0352 (12)0.0013 (11)0.0155 (10)0.0088 (10)
C320.0416 (14)0.0292 (13)0.0217 (10)0.0060 (11)0.0070 (9)0.0048 (9)
C330.0271 (12)0.0296 (12)0.0199 (9)0.0029 (9)0.0015 (8)0.0025 (8)
C340.0256 (11)0.0190 (10)0.0182 (9)0.0025 (8)0.0016 (8)0.0051 (7)
C350.0271 (12)0.0268 (12)0.0387 (12)0.0041 (10)0.0028 (10)0.0001 (10)
C360.0423 (15)0.0238 (12)0.0390 (13)0.0112 (11)0.0005 (11)0.0012 (10)
C370.0548 (16)0.0200 (12)0.0255 (11)0.0012 (11)0.0035 (10)0.0010 (9)
C380.0409 (14)0.0311 (13)0.0250 (10)0.0116 (11)0.0008 (10)0.0000 (9)
C390.0308 (12)0.0292 (12)0.0211 (9)0.0048 (10)0.0027 (8)0.0015 (8)
C400.0157 (10)0.0233 (11)0.0179 (8)0.0017 (8)0.0025 (7)0.0002 (7)
C410.0188 (10)0.0193 (10)0.0162 (8)0.0005 (8)0.0018 (7)0.0008 (7)
C420.0198 (10)0.0203 (10)0.0181 (9)0.0021 (8)0.0026 (7)0.0010 (7)
C430.0159 (10)0.0252 (11)0.0179 (9)0.0027 (8)0.0033 (7)0.0029 (8)
C440.0213 (11)0.0354 (13)0.0204 (9)0.0044 (9)0.0001 (8)0.0011 (9)
C450.0203 (11)0.0436 (14)0.0259 (10)0.0064 (10)0.0002 (8)0.0039 (10)
C460.0246 (12)0.0306 (13)0.0314 (11)0.0107 (10)0.0085 (9)0.0090 (9)
C470.0321 (12)0.0228 (12)0.0279 (10)0.0021 (9)0.0100 (9)0.0000 (8)
C480.0218 (11)0.0270 (12)0.0232 (10)0.0006 (9)0.0021 (8)0.0019 (8)
C490.0167 (10)0.0202 (10)0.0218 (9)0.0045 (8)0.0036 (7)0.0004 (8)
C500.0243 (11)0.0278 (12)0.0215 (9)0.0044 (9)0.0014 (8)0.0009 (8)
C510.0339 (13)0.0328 (13)0.0223 (10)0.0016 (10)0.0053 (9)0.0047 (9)
C520.0254 (12)0.0294 (13)0.0340 (11)0.0011 (10)0.0108 (9)0.0004 (9)
C530.0208 (11)0.0375 (14)0.0304 (11)0.0033 (10)0.0012 (9)0.0045 (10)
C540.0218 (11)0.0359 (13)0.0201 (9)0.0003 (9)0.0011 (8)0.0012 (9)
C550.0186 (10)0.0251 (11)0.0146 (8)0.0001 (8)0.0021 (7)0.0030 (7)
C560.0278 (12)0.0243 (11)0.0214 (9)0.0004 (9)0.0019 (8)0.0009 (8)
C570.0304 (12)0.0309 (13)0.0259 (10)0.0099 (10)0.0016 (9)0.0019 (9)
C580.0228 (11)0.0373 (14)0.0249 (10)0.0052 (10)0.0011 (8)0.0083 (9)
C590.0246 (11)0.0302 (12)0.0231 (10)0.0019 (9)0.0020 (8)0.0040 (9)
C600.0243 (11)0.0224 (11)0.0189 (9)0.0010 (9)0.0006 (8)0.0032 (8)
C610.0162 (10)0.0235 (11)0.0188 (9)0.0002 (8)0.0001 (7)0.0019 (8)
C620.0324 (13)0.0260 (12)0.0236 (10)0.0066 (10)0.0056 (9)0.0006 (8)
C630.0444 (15)0.0407 (14)0.0205 (10)0.0044 (12)0.0056 (9)0.0032 (9)
C640.0349 (13)0.0386 (14)0.0202 (10)0.0001 (11)0.0011 (9)0.0078 (9)
C650.0226 (11)0.0292 (12)0.0295 (11)0.0044 (9)0.0011 (9)0.0063 (9)
C660.0215 (11)0.0271 (12)0.0229 (10)0.0030 (9)0.0037 (8)0.0019 (8)
C670.0217 (10)0.0198 (10)0.0172 (9)0.0012 (8)0.0021 (7)0.0042 (7)
C680.0223 (11)0.0280 (12)0.0219 (9)0.0025 (9)0.0031 (8)0.0016 (8)
C690.0337 (13)0.0280 (12)0.0242 (10)0.0018 (10)0.0054 (9)0.0043 (9)
C700.0280 (12)0.0358 (13)0.0231 (10)0.0065 (10)0.0099 (9)0.0013 (9)
C710.0207 (12)0.0467 (15)0.0304 (11)0.0047 (10)0.0057 (9)0.0029 (10)
C720.0244 (11)0.0347 (13)0.0240 (10)0.0058 (10)0.0018 (8)0.0017 (9)
C730.0292 (12)0.0218 (11)0.0240 (10)0.0034 (9)0.0083 (8)0.0039 (8)
C740.0347 (14)0.0287 (13)0.0416 (13)0.0033 (11)0.0054 (11)0.0102 (10)
C750.0382 (15)0.0423 (16)0.0478 (15)0.0036 (12)0.0004 (12)0.0169 (12)
C760.084 (2)0.0392 (17)0.0452 (16)0.0284 (16)0.0095 (15)0.0129 (12)
C770.157 (4)0.0220 (15)0.0446 (17)0.0199 (19)0.013 (2)0.0017 (12)
C780.103 (3)0.0271 (14)0.0306 (13)0.0006 (15)0.0106 (14)0.0010 (10)
Geometric parameters (Å, º) top
P1—O11.4893 (15)C24—C251.386 (4)
P1—C101.806 (2)C25—C261.364 (4)
P1—C41.806 (2)C26—C271.400 (3)
P1—C11.8203 (19)C28—C291.382 (3)
P2—O21.4900 (17)C28—C331.399 (3)
P2—C161.802 (2)C29—C301.395 (3)
P2—C221.812 (2)C30—C311.386 (4)
P2—C21.816 (2)C31—C321.373 (4)
P3—O31.4950 (14)C32—C331.382 (3)
P3—C281.8027 (19)C34—C391.389 (3)
P3—C341.811 (2)C34—C351.396 (3)
P3—C31.823 (2)C35—C361.384 (3)
P4—O41.4923 (14)C36—C371.377 (4)
P4—C431.804 (2)C37—C381.381 (3)
P4—C491.805 (2)C38—C391.395 (3)
P4—C401.8159 (19)C43—C481.394 (3)
P5—O51.4897 (15)C43—C441.397 (3)
P5—C551.804 (2)C44—C451.387 (3)
P5—C611.8089 (19)C45—C461.383 (3)
P5—C411.8124 (19)C46—C471.388 (3)
P6—O61.4926 (14)C47—C481.383 (3)
P6—C671.803 (2)C49—C541.396 (3)
P6—C731.807 (2)C49—C501.400 (3)
P6—C421.824 (2)C50—C511.382 (3)
N1—C11.474 (2)C51—C521.387 (3)
N1—C31.476 (2)C52—C531.383 (3)
N1—C21.478 (2)C53—C541.384 (3)
N2—C421.473 (2)C55—C601.396 (3)
N2—C401.476 (2)C55—C561.401 (3)
N2—C411.477 (2)C56—C571.382 (3)
C4—C51.389 (3)C57—C581.384 (3)
C4—C91.401 (3)C58—C591.385 (3)
C5—C61.385 (3)C59—C601.390 (3)
C6—C71.384 (3)C61—C621.393 (3)
C7—C81.383 (3)C61—C661.397 (3)
C8—C91.390 (3)C62—C631.394 (3)
C10—C151.381 (3)C63—C641.380 (3)
C10—C111.403 (3)C64—C651.380 (3)
C11—C121.383 (3)C65—C661.390 (3)
C12—C131.381 (3)C67—C681.395 (3)
C13—C141.384 (3)C67—C721.396 (3)
C14—C151.390 (3)C68—C691.390 (3)
C16—C171.387 (3)C69—C701.381 (3)
C16—C211.404 (3)C70—C711.380 (3)
C17—C181.395 (3)C71—C721.385 (3)
C18—C191.385 (3)C73—C781.378 (3)
C19—C201.386 (4)C73—C741.395 (3)
C20—C211.388 (3)C74—C751.383 (3)
C22—C231.387 (3)C75—C761.380 (4)
C22—C271.393 (3)C76—C771.358 (4)
C23—C241.395 (3)C77—C781.391 (4)
O1—P1—C10112.22 (9)C22—C23—C24120.7 (2)
O1—P1—C4111.41 (9)C25—C24—C23119.3 (3)
C10—P1—C4105.90 (9)C26—C25—C24120.6 (2)
O1—P1—C1114.74 (9)C25—C26—C27120.5 (3)
C10—P1—C1109.72 (9)C22—C27—C26119.5 (3)
C4—P1—C1102.06 (9)C29—C28—C33119.72 (19)
O2—P2—C16111.55 (10)C29—C28—P3119.11 (16)
O2—P2—C22112.59 (10)C33—C28—P3121.09 (16)
C16—P2—C22107.84 (10)C28—C29—C30120.1 (2)
O2—P2—C2114.51 (10)C31—C30—C29119.6 (2)
C16—P2—C2107.93 (10)C32—C31—C30120.4 (2)
C22—P2—C2101.79 (9)C31—C32—C33120.4 (2)
O3—P3—C28112.76 (9)C32—C33—C28119.7 (2)
O3—P3—C34113.96 (9)C39—C34—C35118.9 (2)
C28—P3—C34103.69 (9)C39—C34—P3123.74 (16)
O3—P3—C3114.64 (8)C35—C34—P3117.38 (17)
C28—P3—C3105.29 (9)C36—C35—C34120.3 (2)
C34—P3—C3105.48 (9)C37—C36—C35120.5 (2)
O4—P4—C43111.94 (9)C36—C37—C38120.0 (2)
O4—P4—C49111.71 (9)C37—C38—C39119.8 (2)
C43—P4—C49105.80 (9)C34—C39—C38120.5 (2)
O4—P4—C40114.03 (9)N2—C40—P4114.49 (13)
C43—P4—C40103.76 (9)N2—C41—P5113.55 (13)
C49—P4—C40108.99 (9)N2—C42—P6114.76 (13)
O5—P5—C55111.53 (9)C48—C43—C44119.66 (19)
O5—P5—C61112.51 (9)C48—C43—P4122.65 (15)
C55—P5—C61106.24 (9)C44—C43—P4117.69 (16)
O5—P5—C41115.03 (9)C45—C44—C43119.8 (2)
C55—P5—C41107.51 (9)C46—C45—C44120.3 (2)
C61—P5—C41103.33 (9)C45—C46—C47120.1 (2)
O6—P6—C67112.44 (9)C48—C47—C46120.2 (2)
O6—P6—C73113.57 (9)C47—C48—C43120.06 (19)
C67—P6—C73106.28 (9)C54—C49—C50118.68 (19)
O6—P6—C42115.07 (9)C54—C49—P4124.56 (15)
C67—P6—C42107.85 (9)C50—C49—P4116.74 (15)
C73—P6—C42100.65 (10)C51—C50—C49120.61 (19)
C1—N1—C3111.10 (15)C50—C51—C52120.0 (2)
C1—N1—C2109.53 (15)C53—C52—C51119.9 (2)
C3—N1—C2109.53 (14)C52—C53—C54120.4 (2)
C42—N2—C40111.31 (14)C53—C54—C49120.36 (19)
C42—N2—C41109.76 (15)C60—C55—C56119.20 (19)
C40—N2—C41109.30 (15)C60—C55—P5124.05 (16)
N1—C1—P1116.12 (12)C56—C55—P5116.71 (16)
N1—C2—P2114.58 (13)C57—C56—C55120.5 (2)
N1—C3—P3111.54 (13)C56—C57—C58119.9 (2)
C5—C4—C9119.4 (2)C57—C58—C59120.2 (2)
C5—C4—P1117.83 (16)C58—C59—C60120.4 (2)
C9—C4—P1122.74 (16)C59—C60—C55119.7 (2)
C6—C5—C4120.3 (2)C62—C61—C66118.81 (18)
C7—C6—C5120.1 (2)C62—C61—P5118.32 (15)
C8—C7—C6120.3 (2)C66—C61—P5122.83 (15)
C7—C8—C9120.1 (2)C61—C62—C63120.3 (2)
C8—C9—C4119.8 (2)C64—C63—C62120.0 (2)
C15—C10—C11119.31 (19)C63—C64—C65120.46 (19)
C15—C10—P1124.32 (15)C64—C65—C66119.7 (2)
C11—C10—P1116.33 (16)C65—C66—C61120.68 (19)
C12—C11—C10120.1 (2)C68—C67—C72118.86 (19)
C13—C12—C11120.3 (2)C68—C67—P6123.12 (16)
C12—C13—C14119.7 (2)C72—C67—P6117.97 (15)
C13—C14—C15120.5 (2)C69—C68—C67120.0 (2)
C10—C15—C14120.1 (2)C70—C69—C68120.6 (2)
C17—C16—C21119.3 (2)C71—C70—C69119.7 (2)
C17—C16—P2123.95 (17)C70—C71—C72120.4 (2)
C21—C16—P2116.76 (18)C71—C72—C67120.5 (2)
C16—C17—C18120.2 (2)C78—C73—C74119.0 (2)
C19—C18—C17120.0 (2)C78—C73—P6119.46 (17)
C18—C19—C20120.4 (2)C74—C73—P6121.34 (17)
C19—C20—C21119.8 (2)C75—C74—C73120.5 (2)
C20—C21—C16120.3 (2)C76—C75—C74119.4 (3)
C23—C22—C27119.4 (2)C77—C76—C75120.6 (3)
C23—C22—P2122.79 (17)C76—C77—C78120.5 (3)
C27—C22—P2117.78 (19)C73—C78—C77120.0 (3)
 

Funding information

Funding for this research was provided by: Joint Research Centre.

References

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