Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o955-o956
https://doi.org/10.1107/S2056989015021301

Crystal structure of hexa­prop-2-en-1-yl 4,4′,4′′,4′′′,4′′′′,4′′′′′-[1,3,5,2λ5,4λ5,6λ5-tri­aza­triphosphinine-2,2,4,4,6,6-hexa­yl­hexa­kis­(­­oxy)]hexa­benzoate

Jing Zhu,a* Qian Li,a Fu-Wei Zheng,a Juan Hea and Ling-Bo Qua

aCollege of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, People's Republic of China
*Correspondence e-mail: zhujing1960@126.com

Edited by O. Blacque, University of Zürich, Switzerland (Received 14 August 2015; accepted 10 November 2015; online 18 November 2015)

In the title compound, C60H54N3O18P3, the central phosphazene ring is essentially planar, with an r.m.s. deviation of the six fitted atoms of 0.068 Å. The P—N bond lengths are within the narrow range 1.575 (2)–1.585 (2) Å, indicating the electrons are delocalized within the ring. The two ethenyl benzoate substituents on each P atom are located up and down with respect to the plane of the central P3N3 ring. The atoms of two terminal propenyl groups are disordered over two sets of sites, with refined site-occupancy ratios of 0.249 (12):0.751 (12) and 0.476 (9):0.524 (9). No intermolecular interactions are observed.

CCDC reference: 1436029

Similar articles

1. Related literature

Cyclo­triphosphazene derivatives feature a planar six-membered ring consisting of alternating N and P atoms (Wu et al., 2011[Wu, X., Zhou, Y., Liu, S. Z., Guo, Y. N., Qiu, J. J. & Liu, C. M. (2011). Polymer, 52, 1004-1012.]). Their potential applications include solid polymer electrolytes (Allcock et al., 2001[Allcock, H. R., Prange, R. & Hartle, T. J. (2001). Macromolecules, 34, 5463-5470.]; Chen-Yang et al., 2000[Chen-Yang, Y. W., Hwang, J. J. & Huang, A. Y. (2000). Macromolecules, 33, 1237-1244.]), flame retardants (Levchik et al., 2000[Levchik, G. F., Grigoriev, Y. V., Balabanovich, A. I., Levchik, S. V. & Klatt, M. (2000). Polym. Int. 49, 1095-1100.]), non-linear optics (Rojo et al., 2000[Rojo, G., Agulló-López, F., Carriedo, G. A., García Alonso, F. J. & Fidalgo Martinez, J. I. (2000). Polym. Bull. 45, 145-150.]) and biodegradable materials (Ibim et al., 1997[Ibim, S. E. M., Ambrosio, A. M. A., Kwon, M. S., El-Amin, S. F., Allcock, H. R. & Laurencin, C. (1997). Biomaterials, 18, 1565-1569.]). The title compound was prepared according to a literature procedure (Guo et al., 2009[Guo, Y. N., Zhao, C., Liu, S. Z., Li, D., Wang, S. J., Qiu, J. J. & Liu, C. M. (2009). Polym. Bull. 62, 421-431.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C60H54N3O18P3

  • Mr = 1197.97

  • Monoclinic, P 21 /c

  • a = 7.97548 (11) Å

  • b = 16.9389 (3) Å

  • c = 43.0661 (7) Å

  • β = 93.6340 (14)°

  • V = 5806.36 (16) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.59 mm−1

  • T = 291 K

  • 0.22 × 0.16 × 0.15 mm

2.2. Data collection

  • Agilent Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.664, Tmax = 1.000

  • 21543 measured reflections

  • 10382 independent reflections

  • 7375 reflections with I > 2σ(I)

  • Rint = 0.027

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.150

  • S = 1.03

  • 10382 reflections

  • 774 parameters

  • 11 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Selected bond lengths (Å)

N1—P1 1.580 (2)
N1—P2 1.582 (2)
N2—P2 1.575 (2)
N2—P3 1.579 (2)
N3—P1 1.578 (2)
N3—P3 1.585 (2)

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1436029

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021301/zq2233sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021301/zq2233Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021301/zq2233Isup3.cml

checkCIF report


Comment top

Cyclotriphosphazene derivatives are typical classes of organic-inorganic compounds with a planar six-membered ring consisting of alternating N and P atoms (Wu et al., 2011). Their potential applications include solid polymer electrolytes (Allcock et al., 2001; Chen-Yang et al., 2000), flame retardants (Levchik et al., 2000), nonlinear optics (Rojo et al., 2000) and biodegradable materials (Ibim et al., 1997). The title compound was prepared according to a literature report (Guo et al., 2009).

Related literature top

Cyclotriphosphazene derivatives feature a planar six-membered ring consisting of alternating N and P atoms (Wu et al., 2011). Their potential applications include solid polymer electrolytes (Allcock et al., 2001; Chen-Yang et al., 2000), flame retardants (Levchik et al., 2000), non-linear optics (Rojo et al., 2000) and biodegradable materials (Ibim et al., 1997). The title compound was prepared according to a literature procedure (Guo et al., 2009).

Experimental top

A mixture of hexachlorocyclotriphosphazene (1.04 g, 3 mmol), allyl 4-hydroxybenzoate (3.75 g, 21 mmol), and activated potassium carbonate (3.5 g, 253 mmol) in tetrahydrofuran (50 ml) was stirred at 66 °C for 45 h under nitrogen. The resulting suspension mixture was filtered and the filtrate was concentrated, leading to the formation of a faint yellow viscous liquid. It was dissolve in 20 ml ethyl acetate, and the solution was added dropwise to methanol. Colourless needle crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvent after about 2 days.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Hydrogen atoms were placed and refined at idealized positions riding on the carbon atoms with isotropic displacement parameters Uiso(H) = 1.2 Ueq(C) and aromatic C–H = 0.93 Å and methylene C–H = 0.97 Å. The atoms of two terminal propenyl groups are disordered over two sets of sites with refined site-occupancy ratios of 0.249 (12):0.751 (12) and 0.476 (9):0.524 (9). Some restraints were used to correct the geometry and the thermal parameters of the terminal propenyl ligands and the corresponding atoms.

Structure description top

Cyclotriphosphazene derivatives are typical classes of organic-inorganic compounds with a planar six-membered ring consisting of alternating N and P atoms (Wu et al., 2011). Their potential applications include solid polymer electrolytes (Allcock et al., 2001; Chen-Yang et al., 2000), flame retardants (Levchik et al., 2000), nonlinear optics (Rojo et al., 2000) and biodegradable materials (Ibim et al., 1997). The title compound was prepared according to a literature report (Guo et al., 2009).

Cyclotriphosphazene derivatives feature a planar six-membered ring consisting of alternating N and P atoms (Wu et al., 2011). Their potential applications include solid polymer electrolytes (Allcock et al., 2001; Chen-Yang et al., 2000), flame retardants (Levchik et al., 2000), non-linear optics (Rojo et al., 2000) and biodegradable materials (Ibim et al., 1997). The title compound was prepared according to a literature procedure (Guo et al., 2009).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids (some disordered parts are omitted for clarity).
Hexaprop-2-en-1-yl 4,4',4'',4''',4'''',4'''''-[1,3,5,2λ5,4λ5,6λ5-triazatriphosphinine-2,2,4,4,6,6-hexaylhexakis(oxy)]hexabenzoate top
Crystal data top
C60H54N3O18P3F(000) = 2496
Mr = 1197.97Dx = 1.370 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 7.97548 (11) ÅCell parameters from 6834 reflections
b = 16.9389 (3) Åθ = 4.1–72.3°
c = 43.0661 (7) ŵ = 1.59 mm−1
β = 93.6340 (14)°T = 291 K
V = 5806.36 (16) Å3Block, colourless
Z = 40.22 × 0.16 × 0.15 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer		10382 independent reflections
Radiation source: Enhance (Cu) X-ray Source7375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 16.2312 pixels mm-1θmax = 67.1°, θmin = 3.3°
ω scansh = −9→7
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		k = −20→15
Tmin = 0.664, Tmax = 1.000l = −51→50
21543 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.078P)2 + 0.6732P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
10382 reflectionsΔρmax = 0.28 e Å−3
774 parametersΔρmin = −0.30 e Å−3
11 restraints
Crystal data top
C60H54N3O18P3V = 5806.36 (16) Å3
Mr = 1197.97Z = 4
Monoclinic, P21/cCu Kα radiation
a = 7.97548 (11) ŵ = 1.59 mm−1
b = 16.9389 (3) ÅT = 291 K
c = 43.0661 (7) Å0.22 × 0.16 × 0.15 mm
β = 93.6340 (14)°
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer		10382 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		7375 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 1.000Rint = 0.027
21543 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05211 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å−3
10382 reflectionsΔρmin = −0.30 e Å−3
774 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.6244 (3)0.11071 (16)0.40893 (6)0.0541 (6)
C20.6114 (3)0.10471 (19)0.44061 (6)0.0642 (7)
H20.56640.05960.44910.077*
C30.6654 (4)0.1660 (2)0.45932 (6)0.0696 (8)
H30.65790.16210.48070.084*
C40.7309 (3)0.23365 (19)0.44693 (6)0.0645 (7)
C50.7474 (3)0.23766 (18)0.41498 (6)0.0626 (7)
H50.79420.28240.40650.075*
C60.6950 (3)0.17606 (17)0.39577 (6)0.0591 (6)
H60.70710.17850.37450.071*
C70.7807 (4)0.3006 (2)0.46779 (7)0.0805 (9)
C80.8574 (8)0.4358 (3)0.47158 (11)0.1331 (19)
H8A0.76790.44740.48510.160*
H8B0.95950.42600.48440.160*
C90.8811 (7)0.5006 (3)0.45159 (14)0.1336 (18)
H90.94050.49070.43410.160*
C100.8301 (8)0.5704 (4)0.45499 (16)0.164 (2)
H10A0.77010.58340.47210.196*
H10B0.85260.60880.44040.196*
C110.6976 (3)0.03458 (16)0.30966 (6)0.0570 (6)
C120.7519 (3)−0.03787 (17)0.29997 (7)0.0674 (7)
H120.7694−0.07910.31400.081*
C130.7798 (4)−0.04811 (18)0.26889 (7)0.0684 (7)
H130.8159−0.09690.26200.082*
C140.7551 (3)0.01275 (18)0.24782 (7)0.0634 (7)
C150.6996 (4)0.08501 (18)0.25824 (8)0.0726 (8)
H150.68100.12630.24420.087*
C160.6717 (4)0.09615 (17)0.28926 (8)0.0706 (8)
H160.63570.14490.29620.085*
C170.7906 (4)−0.0018 (2)0.21482 (8)0.0823 (9)
C180.778 (7)0.075 (3)0.1662 (13)0.187 (6)0.249 (12)
H18A0.68150.10660.15940.225*0.249 (12)
H18B0.76920.02460.15530.225*0.249 (12)
C18A0.824 (3)0.0479 (6)0.1652 (4)0.187 (6)0.751 (12)
H18C0.91160.00840.16480.225*0.751 (12)
H18D0.72690.02940.15250.225*0.751 (12)
C190.940 (6)0.1168 (15)0.1587 (9)0.158 (4)0.249 (12)
H191.04260.09110.16250.189*0.249 (12)
C19A0.8830 (17)0.1235 (7)0.1533 (3)0.158 (4)0.751 (12)
H19A0.93440.12180.13460.189*0.751 (12)
C200.939 (5)0.1908 (17)0.1466 (6)0.171 (4)0.249 (12)
H20C0.83730.21720.14260.205*0.249 (12)
H20D1.03910.21520.14220.205*0.249 (12)
C20A0.8722 (14)0.1868 (6)0.1651 (2)0.171 (4)0.751 (12)
H20A0.82190.19190.18390.205*0.751 (12)
H20B0.91430.23120.15550.205*0.751 (12)
C210.1451 (4)−0.05609 (17)0.39968 (7)0.0636 (7)
C220.2751 (4)−0.07835 (17)0.42059 (7)0.0692 (7)
H220.3548−0.11480.41490.083*
C230.2849 (4)−0.04589 (17)0.44979 (7)0.0674 (7)
H230.3700−0.06150.46420.081*
C240.1684 (3)0.01032 (17)0.45792 (6)0.0603 (6)
C250.0372 (3)0.03084 (18)0.43663 (7)0.0662 (7)
H25−0.04290.06730.44220.079*
C260.0250 (3)−0.00250 (19)0.40739 (7)0.0666 (7)
H26−0.06280.01100.39310.080*
C270.1922 (4)0.04851 (19)0.48899 (7)0.0687 (7)
C280.1005 (5)0.1519 (2)0.52103 (8)0.0896 (10)
H28A0.15380.12120.53790.107*
H28B−0.00700.17050.52750.107*
C290.2074 (7)0.2197 (3)0.51407 (10)0.1106 (13)
H290.15810.25760.50080.133*
C300.3543 (7)0.2326 (4)0.52357 (13)0.146 (2)
H30A0.41070.19690.53690.175*
H30B0.40850.27810.51740.175*
C310.2102 (3)−0.12102 (16)0.28705 (7)0.0602 (6)
C320.1303 (4)−0.18309 (18)0.27119 (8)0.0712 (8)
H320.0567−0.21580.28110.085*
C330.1619 (4)−0.19549 (18)0.24055 (7)0.0712 (8)
H330.1093−0.23710.22970.085*
C340.2695 (3)−0.14752 (17)0.22575 (7)0.0613 (7)
C350.3457 (3)−0.08538 (18)0.24187 (7)0.0660 (7)
H350.4174−0.05200.23180.079*
C360.3169 (3)−0.07213 (18)0.27280 (7)0.0672 (7)
H360.3695−0.03060.28360.081*
C370.3047 (4)−0.16567 (19)0.19295 (7)0.0693 (8)
C380.4739 (6)−0.1337 (3)0.15172 (10)0.1140 (15)
H38A0.4526−0.18850.14620.137*
H38B0.5935−0.12420.15090.137*
C390.3816 (9)−0.0826 (4)0.12904 (12)0.135 (2)
H390.4000−0.09180.10820.162*
C400.2810 (12)−0.0279 (4)0.13427 (17)0.186 (3)
H40A0.2576−0.01590.15460.223*
H40B0.22990.00060.11780.223*
C410.1543 (3)0.22081 (17)0.38323 (6)0.0589 (6)
C420.2401 (4)0.20936 (19)0.41142 (7)0.0709 (8)
H420.26620.15870.41850.085*
C430.2871 (4)0.2743 (2)0.42918 (7)0.0761 (8)
H430.34490.26720.44840.091*
C440.2497 (4)0.3495 (2)0.41884 (7)0.0694 (7)
C450.1597 (4)0.35902 (19)0.39029 (7)0.0720 (8)
H450.13240.40950.38320.086*
C460.1106 (4)0.29416 (18)0.37242 (7)0.0672 (7)
H460.04930.30040.35350.081*
C470.3088 (5)0.4170 (2)0.43880 (9)0.0899 (10)
C480.3453 (7)0.5550 (3)0.44269 (12)0.1274 (17)
H48A0.26970.56510.45900.153*
H48B0.45710.54590.45220.153*
C490.3467 (9)0.6198 (3)0.42206 (13)0.159 (3)
H490.40050.61260.40370.191*
C500.2793 (10)0.6890 (3)0.42633 (14)0.187 (3)
H50A0.22420.69900.44430.225*
H50B0.28660.72830.41140.225*
C510.2073 (3)0.17633 (17)0.28273 (6)0.0604 (7)
C520.1644 (4)0.11589 (19)0.26258 (7)0.0733 (8)
H520.10110.07340.26890.088*
C530.2171 (4)0.11929 (19)0.23266 (7)0.0783 (9)
H530.19070.07820.21890.094*
C540.3091 (4)0.18341 (18)0.22297 (7)0.0694 (7)
C550.3487 (4)0.24375 (18)0.24349 (7)0.0725 (8)
H550.40940.28710.23710.087*
C560.2988 (4)0.24022 (17)0.27351 (7)0.0700 (8)
H560.32670.28070.28750.084*
C570.3593 (5)0.1855 (2)0.19026 (9)0.0864 (9)
C580.4440 (7)0.2653 (3)0.14879 (10)0.1182 (15)
H58A0.49780.31610.14630.142*0.524 (9)
H58B0.52420.22460.14410.142*0.524 (9)
H58C0.47160.21420.14030.142*0.476 (9)
H58D0.54120.29940.14780.142*0.476 (9)
C590.300 (2)0.2597 (7)0.1268 (3)0.129 (3)0.524 (9)
H590.23910.21310.12370.155*0.524 (9)
C59A0.298 (3)0.3000 (9)0.1303 (4)0.129 (3)0.476 (9)
H59A0.25730.34770.13740.155*0.476 (9)
C600.260 (2)0.3244 (8)0.1116 (3)0.145 (4)0.524 (9)
H60A0.32290.37000.11520.175*0.524 (9)
H60B0.16820.32500.09710.175*0.524 (9)
C60A0.222 (2)0.2706 (10)0.1051 (3)0.145 (4)0.476 (9)
H60C0.25800.22310.09710.175*0.476 (9)
H60D0.13140.29730.09530.175*0.476 (9)
N10.4142 (3)−0.03827 (13)0.34966 (6)0.0611 (5)
N20.1214 (3)0.03232 (14)0.33232 (6)0.0646 (6)
N30.3977 (2)0.12059 (12)0.34622 (5)0.0525 (5)
O10.5647 (2)0.04576 (11)0.39149 (4)0.0623 (5)
O20.7857 (4)0.29681 (18)0.49581 (6)0.1182 (10)
O30.8136 (4)0.36594 (16)0.45250 (5)0.0978 (8)
O40.6794 (2)0.04569 (12)0.34135 (4)0.0628 (5)
O50.8288 (5)−0.0643 (2)0.20453 (7)0.1317 (11)
O60.7770 (6)0.0616 (2)0.19797 (7)0.1519 (15)
O70.1338 (3)−0.08998 (12)0.36977 (5)0.0729 (5)
O80.3057 (3)0.03484 (16)0.50763 (5)0.0985 (8)
O90.0748 (3)0.10293 (15)0.49350 (5)0.0820 (6)
O100.1743 (3)−0.11468 (12)0.31813 (5)0.0729 (5)
O110.2382 (3)−0.21739 (15)0.17770 (5)0.0927 (7)
O120.4256 (3)−0.11996 (16)0.18287 (5)0.0939 (7)
O130.1013 (2)0.15318 (12)0.36631 (5)0.0672 (5)
O140.3671 (5)0.4108 (2)0.46479 (8)0.1449 (13)
O150.2883 (4)0.48591 (16)0.42427 (6)0.0997 (8)
O160.1472 (2)0.17717 (12)0.31240 (5)0.0684 (5)
O170.3589 (5)0.12874 (18)0.17373 (7)0.1382 (13)
O180.4004 (4)0.25671 (15)0.18104 (6)0.1042 (8)
P10.50200 (8)0.04433 (4)0.35587 (2)0.05211 (17)
P20.21804 (8)−0.04575 (4)0.34213 (2)0.05849 (18)
P30.20045 (8)0.11649 (4)0.33920 (2)0.05513 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0474 (13)0.0592 (15)0.0551 (14)0.0035 (11)−0.0022 (10)0.0019 (12)
C20.0604 (15)0.0723 (18)0.0592 (15)−0.0039 (13)−0.0004 (12)0.0131 (14)
C30.0712 (17)0.088 (2)0.0489 (14)0.0054 (16)−0.0019 (12)0.0040 (14)
C40.0612 (15)0.0780 (19)0.0534 (15)0.0001 (14)−0.0039 (12)−0.0053 (14)
C50.0603 (15)0.0688 (17)0.0584 (15)−0.0101 (13)0.0015 (12)−0.0002 (13)
C60.0587 (14)0.0692 (17)0.0495 (13)−0.0047 (13)0.0051 (11)0.0000 (12)
C70.086 (2)0.092 (2)0.0621 (19)−0.0028 (18)−0.0086 (15)−0.0119 (17)
C80.196 (5)0.106 (3)0.092 (3)−0.048 (3)−0.032 (3)−0.024 (3)
C90.154 (5)0.100 (4)0.142 (4)−0.020 (3)−0.029 (3)−0.034 (3)
C100.186 (6)0.114 (4)0.184 (6)0.000 (4)−0.040 (5)−0.042 (4)
C110.0389 (12)0.0616 (16)0.0707 (16)−0.0037 (11)0.0051 (11)−0.0085 (13)
C120.0586 (15)0.0586 (16)0.084 (2)0.0042 (13)0.0009 (13)−0.0022 (14)
C130.0608 (16)0.0594 (17)0.085 (2)0.0078 (13)0.0034 (14)−0.0188 (15)
C140.0495 (14)0.0664 (17)0.0746 (17)−0.0072 (12)0.0059 (12)−0.0117 (15)
C150.079 (2)0.0592 (17)0.080 (2)0.0002 (15)0.0150 (15)0.0006 (15)
C160.0751 (19)0.0506 (15)0.088 (2)0.0061 (13)0.0166 (15)−0.0078 (15)
C170.081 (2)0.088 (2)0.079 (2)−0.0108 (18)0.0066 (16)−0.015 (2)
C180.380 (18)0.108 (9)0.081 (3)0.001 (9)0.069 (7)−0.009 (7)
C18A0.380 (18)0.108 (9)0.081 (3)0.001 (9)0.069 (7)−0.009 (7)
C190.197 (12)0.185 (8)0.090 (6)0.028 (7)−0.006 (6)0.017 (6)
C19A0.197 (12)0.185 (8)0.090 (6)0.028 (7)−0.006 (6)0.017 (6)
C200.258 (11)0.148 (7)0.109 (6)0.018 (7)0.038 (6)−0.016 (6)
C20A0.258 (11)0.148 (7)0.109 (6)0.018 (7)0.038 (6)−0.016 (6)
C210.0635 (16)0.0571 (16)0.0716 (17)−0.0125 (13)0.0159 (13)−0.0035 (13)
C220.0723 (18)0.0559 (16)0.0813 (19)0.0079 (14)0.0197 (15)0.0031 (14)
C230.0669 (17)0.0659 (17)0.0702 (17)0.0072 (14)0.0102 (13)0.0164 (14)
C240.0591 (15)0.0614 (16)0.0617 (15)−0.0038 (12)0.0144 (12)0.0077 (13)
C250.0560 (15)0.0740 (19)0.0693 (17)0.0030 (13)0.0108 (12)−0.0036 (14)
C260.0519 (14)0.0763 (19)0.0719 (17)−0.0005 (13)0.0056 (12)−0.0075 (15)
C270.0709 (18)0.0712 (19)0.0650 (17)−0.0030 (15)0.0114 (14)0.0125 (14)
C280.104 (3)0.091 (3)0.074 (2)−0.004 (2)0.0143 (18)−0.0147 (19)
C290.125 (4)0.107 (3)0.100 (3)−0.008 (3)0.009 (3)−0.022 (3)
C300.134 (4)0.151 (5)0.156 (5)−0.027 (4)0.024 (4)−0.050 (4)
C310.0513 (14)0.0569 (15)0.0727 (17)−0.0012 (12)0.0051 (12)−0.0202 (13)
C320.0625 (16)0.0614 (17)0.090 (2)−0.0149 (14)0.0090 (14)−0.0191 (15)
C330.0642 (17)0.0661 (18)0.0824 (19)−0.0119 (14)−0.0029 (14)−0.0271 (16)
C340.0486 (13)0.0603 (16)0.0735 (17)0.0015 (12)−0.0080 (12)−0.0123 (13)
C350.0581 (15)0.0654 (17)0.0741 (18)−0.0115 (13)0.0024 (13)−0.0150 (14)
C360.0581 (15)0.0647 (17)0.0783 (18)−0.0159 (13)0.0010 (13)−0.0233 (15)
C370.0648 (17)0.0702 (18)0.0710 (17)0.0051 (14)−0.0095 (14)−0.0148 (15)
C380.121 (3)0.140 (4)0.085 (3)−0.018 (3)0.033 (2)−0.023 (3)
C390.187 (6)0.127 (4)0.095 (3)−0.052 (4)0.030 (3)−0.017 (3)
C400.302 (11)0.118 (5)0.134 (5)0.005 (6)−0.015 (6)−0.009 (4)
C410.0483 (13)0.0645 (16)0.0651 (16)0.0056 (12)0.0138 (11)−0.0068 (13)
C420.0695 (17)0.0688 (18)0.0746 (18)0.0117 (15)0.0074 (14)0.0016 (15)
C430.0735 (19)0.087 (2)0.0670 (18)0.0105 (16)−0.0003 (14)−0.0033 (16)
C440.0651 (17)0.079 (2)0.0649 (17)−0.0006 (15)0.0095 (13)−0.0102 (15)
C450.080 (2)0.0605 (17)0.0754 (19)0.0045 (15)0.0076 (15)0.0004 (15)
C460.0680 (17)0.0689 (18)0.0644 (16)0.0054 (14)0.0008 (13)−0.0014 (14)
C470.098 (3)0.089 (3)0.083 (2)−0.005 (2)0.0072 (19)−0.016 (2)
C480.162 (5)0.101 (3)0.117 (4)−0.042 (3)−0.008 (3)−0.030 (3)
C490.260 (8)0.108 (4)0.111 (4)−0.075 (5)0.018 (4)−0.017 (3)
C500.344 (11)0.088 (4)0.128 (5)−0.031 (5)0.005 (5)−0.026 (3)
C510.0522 (14)0.0610 (16)0.0661 (16)0.0090 (12)−0.0119 (12)−0.0015 (13)
C520.0741 (18)0.0656 (18)0.0782 (19)−0.0167 (15)−0.0116 (15)0.0003 (15)
C530.098 (2)0.0636 (18)0.0709 (19)−0.0127 (17)−0.0123 (16)−0.0090 (15)
C540.0754 (18)0.0580 (16)0.0729 (18)0.0040 (14)−0.0105 (14)0.0032 (14)
C550.0800 (19)0.0546 (16)0.081 (2)−0.0059 (14)−0.0089 (15)0.0043 (15)
C560.0765 (18)0.0522 (15)0.079 (2)−0.0031 (14)−0.0151 (15)−0.0060 (14)
C570.105 (3)0.069 (2)0.085 (2)−0.0004 (19)0.0067 (19)−0.0038 (18)
C580.163 (4)0.106 (3)0.089 (3)−0.024 (3)0.028 (3)0.012 (2)
C590.203 (7)0.112 (9)0.072 (4)−0.035 (10)0.005 (4)0.003 (7)
C59A0.203 (7)0.112 (9)0.072 (4)−0.035 (10)0.005 (4)0.003 (7)
C600.195 (9)0.148 (10)0.094 (6)0.013 (10)0.008 (5)0.003 (7)
C60A0.195 (9)0.148 (10)0.094 (6)0.013 (10)0.008 (5)0.003 (7)
N10.0539 (12)0.0540 (13)0.0753 (14)0.0042 (10)0.0040 (10)−0.0087 (11)
N20.0466 (11)0.0671 (15)0.0793 (15)−0.0016 (10)−0.0028 (10)−0.0134 (12)
N30.0499 (11)0.0504 (12)0.0571 (11)−0.0024 (9)0.0019 (9)−0.0003 (9)
O10.0656 (11)0.0577 (11)0.0623 (11)−0.0030 (9)−0.0058 (8)0.0030 (9)
O20.173 (3)0.117 (2)0.0617 (15)−0.011 (2)−0.0181 (15)−0.0168 (14)
O30.133 (2)0.0871 (17)0.0714 (14)−0.0286 (15)−0.0079 (13)−0.0201 (13)
O40.0448 (9)0.0748 (12)0.0687 (11)0.0009 (8)0.0026 (8)−0.0096 (9)
O50.182 (3)0.119 (3)0.096 (2)0.020 (2)0.023 (2)−0.0315 (19)
O60.271 (5)0.108 (2)0.0799 (18)0.002 (3)0.040 (2)0.0021 (18)
O70.0786 (13)0.0614 (12)0.0806 (13)−0.0176 (10)0.0198 (10)−0.0163 (10)
O80.1113 (19)0.111 (2)0.0703 (14)0.0221 (15)−0.0137 (13)0.0055 (13)
O90.0830 (14)0.0920 (16)0.0710 (13)0.0067 (12)0.0046 (10)−0.0146 (12)
O100.0726 (12)0.0652 (12)0.0821 (13)−0.0170 (10)0.0149 (10)−0.0229 (10)
O110.1110 (18)0.0880 (17)0.0777 (14)−0.0159 (14)−0.0061 (12)−0.0286 (13)
O120.0950 (16)0.1080 (19)0.0796 (14)−0.0235 (15)0.0133 (12)−0.0245 (13)
O130.0559 (10)0.0619 (11)0.0851 (13)0.0016 (9)0.0144 (9)−0.0115 (10)
O140.206 (4)0.120 (3)0.102 (2)−0.014 (2)−0.045 (2)−0.0251 (19)
O150.119 (2)0.0800 (16)0.0997 (18)−0.0174 (15)0.0022 (15)−0.0193 (14)
O160.0643 (11)0.0674 (12)0.0723 (12)0.0169 (9)−0.0042 (9)−0.0010 (10)
O170.235 (4)0.0822 (19)0.102 (2)−0.016 (2)0.045 (2)−0.0106 (17)
O180.151 (2)0.0760 (16)0.0851 (16)−0.0177 (16)0.0050 (15)0.0073 (13)
P10.0452 (3)0.0521 (4)0.0588 (4)0.0009 (3)0.0015 (3)−0.0048 (3)
P20.0542 (4)0.0528 (4)0.0691 (4)−0.0064 (3)0.0090 (3)−0.0149 (3)
P30.0467 (3)0.0549 (4)0.0635 (4)0.0036 (3)0.0016 (3)−0.0064 (3)
Geometric parameters (Å, º) top
C1—C21.379 (4)C33—C341.369 (4)
C1—C61.380 (4)C34—C351.381 (4)
C1—O11.398 (3)C34—C371.489 (4)
C2—H20.9300C35—H350.9300
C2—C31.367 (4)C35—C361.384 (4)
C3—H30.9300C36—H360.9300
C3—C41.380 (4)C37—O111.198 (3)
C4—C51.392 (4)C37—O121.331 (4)
C4—C71.486 (4)C38—H38A0.9700
C5—H50.9300C38—H38B0.9700
C5—C61.380 (4)C38—C391.468 (7)
C6—H60.9300C38—O121.438 (4)
C7—O21.207 (4)C39—H390.9300
C7—O31.322 (4)C39—C401.255 (8)
C8—H8A0.9700C40—H40A0.9300
C8—H8B0.9700C40—H40B0.9300
C8—C91.415 (7)C41—C421.369 (4)
C8—O31.471 (4)C41—C461.364 (4)
C9—H90.9300C41—O131.408 (3)
C9—C101.262 (7)C42—H420.9300
C10—H10A0.9300C42—C431.379 (4)
C10—H10B0.9300C43—H430.9300
C11—C121.375 (4)C43—C441.375 (4)
C11—C161.371 (4)C44—C451.393 (4)
C11—O41.394 (3)C44—C471.489 (5)
C12—H120.9300C45—H450.9300
C12—C131.382 (4)C45—C461.384 (4)
C13—H130.9300C46—H460.9300
C13—C141.379 (4)C47—O141.190 (4)
C14—C151.386 (4)C47—O151.330 (5)
C14—C171.487 (5)C48—H48A0.9700
C15—H150.9300C48—H48B0.9700
C15—C161.381 (4)C48—C491.413 (7)
C16—H160.9300C48—O151.469 (4)
C17—O51.194 (4)C49—H490.9300
C17—O61.297 (5)C49—C501.308 (8)
C18—H18A0.9700C50—H50A0.9300
C18—H18B0.9700C50—H50B0.9300
C18—C191.54 (2)C51—C521.371 (4)
C18—O61.39 (5)C51—C561.377 (4)
C18A—H18C0.9700C51—O161.393 (3)
C18A—H18D0.9700C52—H520.9300
C18A—C19A1.469 (12)C52—C531.381 (5)
C18A—O61.500 (14)C53—H530.9300
C19—H190.9300C53—C541.390 (4)
C19—C201.358 (19)C54—C551.375 (4)
C19A—H19A0.9300C54—C571.489 (5)
C19A—C20A1.192 (12)C55—H550.9300
C20—H20C0.9300C55—C561.378 (4)
C20—H20D0.9300C56—H560.9300
C20A—H20A0.9300C57—O171.197 (4)
C20A—H20B0.9300C57—O181.317 (4)
C21—C221.382 (4)C58—H58A0.9700
C21—C261.376 (4)C58—H58B0.9700
C21—O71.408 (3)C58—H58C0.9700
C22—H220.9300C58—H58D0.9700
C22—C231.370 (4)C58—C591.448 (14)
C23—H230.9300C58—C59A1.49 (2)
C23—C241.391 (4)C58—O181.460 (5)
C24—C251.391 (4)C59—H590.9300
C24—C271.488 (4)C59—C601.306 (17)
C25—H250.9300C59A—H59A0.9300
C25—C261.378 (4)C59A—C60A1.31 (2)
C26—H260.9300C60—H60A0.9300
C27—O81.194 (4)C60—H60B0.9300
C27—O91.337 (4)C60A—H60C0.9300
C28—H28A0.9700C60A—H60D0.9300
C28—H28B0.9700N1—P11.580 (2)
C28—C291.473 (6)N1—P21.582 (2)
C28—O91.451 (4)N2—P21.575 (2)
C29—H290.9300N2—P31.579 (2)
C29—C301.235 (6)N3—P11.578 (2)
C30—H30A0.9300N3—P31.585 (2)
C30—H30B0.9300O1—P11.5833 (19)
C31—C321.387 (4)O4—P11.5826 (18)
C31—C361.361 (4)O7—P21.591 (2)
C31—O101.391 (3)O10—P21.5834 (19)
C32—H320.9300O13—P31.579 (2)
C32—C331.375 (4)O16—P31.583 (2)
C33—H330.9300
C2—C1—C6121.6 (3)C35—C36—H36120.6
C2—C1—O1115.4 (2)O11—C37—C34124.6 (3)
C6—C1—O1123.0 (2)O11—C37—O12123.4 (3)
C1—C2—H2120.4O12—C37—C34111.9 (2)
C3—C2—C1119.1 (3)H38A—C38—H38B107.9
C3—C2—H2120.4C39—C38—H38A109.2
C2—C3—H3119.5C39—C38—H38B109.2
C2—C3—C4121.0 (3)O12—C38—H38A109.2
C4—C3—H3119.5O12—C38—H38B109.2
C3—C4—C5119.0 (3)O12—C38—C39111.9 (4)
C3—C4—C7119.6 (3)C38—C39—H39116.0
C5—C4—C7121.5 (3)C40—C39—C38128.0 (6)
C4—C5—H5119.6C40—C39—H39116.0
C6—C5—C4120.8 (3)C39—C40—H40A120.0
C6—C5—H5119.6C39—C40—H40B120.0
C1—C6—H6120.8H40A—C40—H40B120.0
C5—C6—C1118.5 (2)C42—C41—O13117.4 (3)
C5—C6—H6120.8C46—C41—C42122.3 (3)
O2—C7—C4123.6 (4)C46—C41—O13120.2 (2)
O2—C7—O3123.2 (3)C41—C42—H42120.6
O3—C7—C4113.1 (3)C41—C42—C43118.8 (3)
H8A—C8—H8B108.3C43—C42—H42120.6
C9—C8—H8A110.0C42—C43—H43119.5
C9—C8—H8B110.0C44—C43—C42120.9 (3)
C9—C8—O3108.7 (4)C44—C43—H43119.5
O3—C8—H8A110.0C43—C44—C45118.8 (3)
O3—C8—H8B110.0C43—C44—C47118.0 (3)
C8—C9—H9116.6C45—C44—C47123.2 (3)
C10—C9—C8126.8 (7)C44—C45—H45119.6
C10—C9—H9116.6C46—C45—C44120.7 (3)
C9—C10—H10A120.0C46—C45—H45119.6
C9—C10—H10B120.0C41—C46—C45118.4 (3)
H10A—C10—H10B120.0C41—C46—H46120.8
C12—C11—O4118.2 (3)C45—C46—H46120.8
C16—C11—C12121.5 (3)O14—C47—C44124.5 (4)
C16—C11—O4120.2 (2)O14—C47—O15123.3 (4)
C11—C12—H12120.7O15—C47—C44112.2 (3)
C11—C12—C13118.6 (3)H48A—C48—H48B108.6
C13—C12—H12120.7C49—C48—H48A110.3
C12—C13—H13119.4C49—C48—H48B110.3
C14—C13—C12121.2 (3)C49—C48—O15107.1 (4)
C14—C13—H13119.4O15—C48—H48A110.3
C13—C14—C15118.8 (3)O15—C48—H48B110.3
C13—C14—C17118.5 (3)C48—C49—H49117.0
C15—C14—C17122.7 (3)C50—C49—C48126.1 (6)
C14—C15—H15119.7C50—C49—H49117.0
C16—C15—C14120.6 (3)C49—C50—H50A120.0
C16—C15—H15119.7C49—C50—H50B120.0
C11—C16—C15119.3 (3)H50A—C50—H50B120.0
C11—C16—H16120.4C52—C51—C56121.3 (3)
C15—C16—H16120.4C52—C51—O16120.1 (3)
O5—C17—C14124.8 (4)C56—C51—O16118.4 (3)
O5—C17—O6122.7 (4)C51—C52—H52120.6
O6—C17—C14112.5 (3)C51—C52—C53118.7 (3)
H18A—C18—H18B108.2C53—C52—H52120.6
C19—C18—H18A109.7C52—C53—H53119.7
C19—C18—H18B109.7C52—C53—C54120.7 (3)
O6—C18—H18A109.7C54—C53—H53119.7
O6—C18—H18B109.7C53—C54—C57118.8 (3)
O6—C18—C19110 (4)C55—C54—C53119.5 (3)
H18C—C18A—H18D108.5C55—C54—C57121.7 (3)
C19A—C18A—H18C110.3C54—C55—H55119.9
C19A—C18A—H18D110.3C54—C55—C56120.2 (3)
C19A—C18A—O6107.3 (8)C56—C55—H55119.9
O6—C18A—H18C110.3C51—C56—C55119.6 (3)
O6—C18A—H18D110.3C51—C56—H56120.2
C18—C19—H19119.2C55—C56—H56120.2
C20—C19—C18122 (3)O17—C57—C54123.5 (4)
C20—C19—H19119.2O17—C57—O18123.2 (4)
C18A—C19A—H19A116.5O18—C57—C54113.2 (3)
C20A—C19A—C18A127.1 (12)H58A—C58—H58B107.8
C20A—C19A—H19A116.5H58C—C58—H58D108.3
C19—C20—H20C120.0C59—C58—H58A109.0
C19—C20—H20D120.0C59—C58—H58B109.0
H20C—C20—H20D120.0C59—C58—O18112.8 (8)
C19A—C20A—H20A120.0C59A—C58—H58C109.9
C19A—C20A—H20B120.0C59A—C58—H58D109.9
H20A—C20A—H20B120.0O18—C58—H58A109.0
C22—C21—O7119.1 (3)O18—C58—H58B109.0
C26—C21—C22121.9 (3)O18—C58—H58C109.9
C26—C21—O7119.0 (3)O18—C58—H58D109.9
C21—C22—H22120.5O18—C58—C59A108.9 (9)
C23—C22—C21119.1 (3)C58—C59—H59122.2
C23—C22—H22120.5C60—C59—C58115.6 (13)
C22—C23—H23119.8C60—C59—H59122.2
C22—C23—C24120.4 (3)C58—C59A—H59A116.6
C24—C23—H23119.8C60A—C59A—C58126.9 (17)
C23—C24—C25119.5 (3)C60A—C59A—H59A116.6
C23—C24—C27118.4 (3)C59—C60—H60A120.0
C25—C24—C27122.1 (3)C59—C60—H60B120.0
C24—C25—H25119.8H60A—C60—H60B120.0
C26—C25—C24120.4 (3)C59A—C60A—H60C120.0
C26—C25—H25119.8C59A—C60A—H60D120.0
C21—C26—C25118.8 (3)H60C—C60A—H60D120.0
C21—C26—H26120.6P1—N1—P2121.83 (14)
C25—C26—H26120.6P2—N2—P3121.66 (14)
O8—C27—C24124.6 (3)P1—N3—P3120.99 (13)
O8—C27—O9123.0 (3)C1—O1—P1127.46 (16)
O9—C27—C24112.3 (3)C7—O3—C8116.3 (3)
H28A—C28—H28B108.2C11—O4—P1122.43 (15)
C29—C28—H28A109.8C17—O6—C18132.7 (17)
C29—C28—H28B109.8C17—O6—C18A112.4 (6)
O9—C28—H28A109.8C21—O7—P2119.14 (17)
O9—C28—H28B109.8C27—O9—C28116.7 (3)
O9—C28—C29109.4 (3)C31—O10—P2129.42 (18)
C28—C29—H29115.8C37—O12—C38116.9 (3)
C30—C29—C28128.3 (6)C41—O13—P3123.69 (17)
C30—C29—H29115.8C47—O15—C48114.9 (3)
C29—C30—H30A120.0C51—O16—P3124.73 (17)
C29—C30—H30B120.0C57—O18—C58117.2 (3)
H30A—C30—H30B120.0N1—P1—O1106.67 (12)
C32—C31—O10114.6 (3)N1—P1—O4110.10 (11)
C36—C31—C32121.3 (3)N3—P1—N1117.38 (11)
C36—C31—O10124.0 (2)N3—P1—O1111.80 (11)
C31—C32—H32120.6N3—P1—O4110.71 (11)
C33—C32—C31118.8 (3)O4—P1—O198.48 (10)
C33—C32—H32120.6N1—P2—O7110.08 (13)
C32—C33—H33119.5N1—P2—O10111.51 (11)
C34—C33—C32121.0 (3)N2—P2—N1116.65 (12)
C34—C33—H33119.5N2—P2—O7111.92 (13)
C33—C34—C35119.2 (3)N2—P2—O10111.12 (12)
C33—C34—C37118.7 (3)O10—P2—O793.16 (11)
C35—C34—C37122.1 (3)N2—P3—N3117.08 (12)
C34—C35—H35119.6N2—P3—O16111.34 (12)
C34—C35—C36120.9 (3)O13—P3—N2106.32 (12)
C36—C35—H35119.6O13—P3—N3112.30 (11)
C31—C36—C35118.8 (3)O13—P3—O1699.19 (11)
C31—C36—H36120.6O16—P3—N3109.16 (11)
C1—C2—C3—C40.6 (4)C41—O13—P3—O16−77.2 (2)
C1—O1—P1—N1−168.6 (2)C42—C41—C46—C452.0 (4)
C1—O1—P1—N3−39.0 (2)C42—C41—O13—P3−97.7 (3)
C1—O1—P1—O477.4 (2)C42—C43—C44—C451.4 (5)
C2—C1—C6—C5−2.5 (4)C42—C43—C44—C47−178.2 (3)
C2—C1—O1—P1156.6 (2)C43—C44—C45—C46−0.8 (5)
C2—C3—C4—C5−2.4 (4)C43—C44—C47—O14−10.1 (6)
C2—C3—C4—C7177.0 (3)C43—C44—C47—O15170.1 (3)
C3—C4—C5—C61.8 (4)C44—C45—C46—C41−0.8 (5)
C3—C4—C7—O28.8 (5)C44—C47—O15—C48−179.6 (3)
C3—C4—C7—O3−169.0 (3)C45—C44—C47—O14170.3 (4)
C4—C5—C6—C10.6 (4)C45—C44—C47—O15−9.5 (5)
C4—C7—O3—C8177.7 (4)C46—C41—C42—C43−1.4 (4)
C5—C4—C7—O2−171.7 (3)C46—C41—O13—P386.5 (3)
C5—C4—C7—O310.4 (4)C47—C44—C45—C46178.8 (3)
C6—C1—C2—C31.9 (4)C49—C48—O15—C47168.2 (5)
C6—C1—O1—P1−24.7 (3)C51—C52—C53—C54−1.2 (5)
C7—C4—C5—C6−177.7 (3)C51—O16—P3—N2−72.4 (2)
C9—C8—O3—C7−177.4 (4)C51—O16—P3—N358.4 (2)
C11—C12—C13—C140.3 (4)C51—O16—P3—O13176.0 (2)
C11—O4—P1—N160.0 (2)C52—C51—C56—C55−0.1 (4)
C11—O4—P1—N3−71.5 (2)C52—C51—O16—P368.2 (3)
C11—O4—P1—O1171.3 (2)C52—C53—C54—C550.4 (5)
C12—C11—C16—C150.4 (4)C52—C53—C54—C57−178.4 (3)
C12—C11—O4—P1−102.4 (2)C53—C54—C55—C560.6 (5)
C12—C13—C14—C15−0.6 (4)C53—C54—C57—O17−17.3 (6)
C12—C13—C14—C17178.8 (3)C53—C54—C57—O18161.2 (3)
C13—C14—C15—C160.8 (4)C54—C55—C56—C51−0.7 (4)
C13—C14—C17—O55.2 (5)C54—C57—O18—C58−177.3 (3)
C13—C14—C17—O6−174.2 (3)C55—C54—C57—O17164.0 (4)
C14—C15—C16—C11−0.7 (5)C55—C54—C57—O18−17.6 (5)
C14—C17—O6—C18−171 (3)C56—C51—C52—C531.0 (4)
C14—C17—O6—C18A176.3 (9)C56—C51—O16—P3−116.8 (3)
C15—C14—C17—O5−175.3 (4)C57—C54—C55—C56179.3 (3)
C15—C14—C17—O65.2 (5)C59—C58—O18—C5772.7 (7)
C16—C11—C12—C13−0.2 (4)C59A—C58—O18—C57102.0 (7)
C16—C11—O4—P181.5 (3)O1—C1—C2—C3−179.4 (2)
C17—C14—C15—C16−178.6 (3)O1—C1—C6—C5178.8 (2)
C19—C18—O6—C17−110 (3)O2—C7—O3—C8−0.2 (6)
C19A—C18A—O6—C17−153.1 (10)O3—C8—C9—C10137.7 (6)
C21—C22—C23—C24−1.8 (4)O4—C11—C12—C13−176.3 (2)
C21—O7—P2—N161.4 (2)O4—C11—C16—C15176.4 (3)
C21—O7—P2—N2−70.0 (2)O5—C17—O6—C1810 (3)
C21—O7—P2—O10175.7 (2)O5—C17—O6—C18A−3.1 (10)
C22—C21—C26—C251.3 (5)O6—C18—C19—C20−116 (4)
C22—C21—O7—P2−93.3 (3)O6—C18A—C19A—C20A−11 (2)
C22—C23—C24—C252.9 (4)O7—C21—C22—C23−179.4 (2)
C22—C23—C24—C27−175.2 (3)O7—C21—C26—C25−179.6 (3)
C23—C24—C25—C26−1.8 (4)O8—C27—O9—C286.5 (5)
C23—C24—C27—O80.6 (5)O9—C28—C29—C30−109.5 (5)
C23—C24—C27—O9178.1 (3)O10—C31—C32—C33−178.2 (3)
C24—C25—C26—C21−0.2 (4)O10—C31—C36—C35178.5 (3)
C24—C27—O9—C28−171.1 (3)O11—C37—O12—C381.3 (5)
C25—C24—C27—O8−177.4 (3)O12—C38—C39—C405.4 (9)
C25—C24—C27—O90.1 (4)O13—C41—C42—C43−177.1 (3)
C26—C21—C22—C23−0.3 (4)O13—C41—C46—C45177.6 (2)
C26—C21—O7—P287.6 (3)O14—C47—O15—C480.6 (6)
C27—C24—C25—C26176.1 (3)O15—C48—C49—C50130.4 (7)
C29—C28—O9—C2785.8 (4)O16—C51—C52—C53175.9 (3)
C31—C32—C33—C34−0.2 (5)O16—C51—C56—C55−175.0 (2)
C31—O10—P2—N1−66.2 (3)O17—C57—O18—C581.2 (6)
C31—O10—P2—N265.8 (3)O18—C58—C59—C60113.3 (14)
C31—O10—P2—O7−179.2 (2)O18—C58—C59A—C60A−124.6 (19)
C32—C31—C36—C35−0.2 (5)P1—N1—P2—N215.8 (2)
C32—C31—O10—P2−169.9 (2)P1—N1—P2—O7−113.10 (17)
C32—C33—C34—C35−0.7 (5)P1—N1—P2—O10144.95 (16)
C32—C33—C34—C37177.4 (3)P1—N3—P3—N2−17.9 (2)
C33—C34—C35—C361.2 (4)P1—N3—P3—O13105.55 (16)
C33—C34—C37—O114.2 (5)P1—N3—P3—O16−145.47 (14)
C33—C34—C37—O12−172.7 (3)P2—N1—P1—N3−15.0 (2)
C34—C35—C36—C31−0.7 (5)P2—N1—P1—O1111.30 (17)
C34—C37—O12—C38178.3 (3)P2—N1—P1—O4−142.83 (16)
C35—C34—C37—O11−177.7 (3)P2—N2—P3—N319.0 (2)
C35—C34—C37—O125.4 (4)P2—N2—P3—O13−107.40 (18)
C36—C31—C32—C330.7 (5)P2—N2—P3—O16145.56 (16)
C36—C31—O10—P211.3 (4)P3—N2—P2—N1−17.9 (2)
C37—C34—C35—C36−176.9 (3)P3—N2—P2—O7110.11 (18)
C39—C38—O12—C3793.4 (5)P3—N2—P2—O10−147.22 (16)
C41—C42—C43—C44−0.3 (5)P3—N3—P1—N115.9 (2)
C41—O13—P3—N2167.2 (2)P3—N3—P1—O1−107.78 (15)
C41—O13—P3—N338.0 (2)P3—N3—P1—O4143.49 (14)
Selected bond lengths (Å) top
N1—P11.580 (2)N2—P31.579 (2)
N1—P21.582 (2)N3—P11.578 (2)
N2—P21.575 (2)N3—P31.585 (2)
 

Acknowledgements

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the High-level Talents Foundation of Henan University of Technology.

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
 First citationAllcock, H. R., Prange, R. & Hartle, T. J. (2001). Macromolecules, 34, 5463–5470.  Web of Science CrossRef CAS Google Scholar
 First citationChen-Yang, Y. W., Hwang, J. J. & Huang, A. Y. (2000). Macromolecules, 33, 1237–1244.  CAS Google Scholar
 First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationGuo, Y. N., Zhao, C., Liu, S. Z., Li, D., Wang, S. J., Qiu, J. J. & Liu, C. M. (2009). Polym. Bull. 62, 421–431.  Web of Science CrossRef CAS Google Scholar
 First citationIbim, S. E. M., Ambrosio, A. M. A., Kwon, M. S., El-Amin, S. F., Allcock, H. R. & Laurencin, C. (1997). Biomaterials, 18, 1565–1569.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationLevchik, G. F., Grigoriev, Y. V., Balabanovich, A. I., Levchik, S. V. & Klatt, M. (2000). Polym. Int. 49, 1095–1100.  CrossRef CAS Google Scholar
 First citationRojo, G., Agulló-López, F., Carriedo, G. A., García Alonso, F. J. & Fidalgo Martinez, J. I. (2000). Polym. Bull. 45, 145–150.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWu, X., Zhou, Y., Liu, S. Z., Guo, Y. N., Qiu, J. J. & Liu, C. M. (2011). Polymer, 52, 1004–1012.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o955-o956
https://doi.org/10.1107/S2056989015021301
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS