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New phosphoramidates with the formula RC(O)N(H)P(O)X2, R = 2-NO2—C6H4, 3-NO2—C6H4 and 4-NO2—C6H4, X = N(CH2CH3) (1)–(3), NC4H8 (4)–(6), and NC4H8O (7)–(9) were synthesized and characterized by 1H, 13C, 31P NMR and IR spectroscopy, and elemental analysis. The reaction of (9) with hydrated lanthanide(III) nitrate leads to ten- or nine-coordinated complexes, (10)–(13). The crystal structure has been determined for (3), (5), (9), (10) and (13). In contrast to all of the previously reported similar phosphoramidate compounds, the —C(O)—N(H)—P(O) skeleton in the free ligand (9) shows a cisoid conformation, with the C=O and P=O double bonds adopting a nearly syn conformation. Quantum chemical calculations were applied for clarifying this exceptional conformational behavior. The monodentate neutral ligand (9) is coordinated to the metal ions via the phosphoryl O atom, adopting the usual anti conformation between the C=O and P=O groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110018550/ps5006sup1.cif
Contains datablocks global, 3, 9, 10, 13, 5

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110018550/ps50063sup2.fcf
Contains datablock 3

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110018550/ps50065sup3.fcf
Contains datablock 5

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110018550/ps50069sup4.fcf
Contains datablock 9

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110018550/ps500610sup5.fcf
Contains datablock 10

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110018550/ps500613sup6.fcf
Contains datablock 13

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110018550/ps5006sup7.pdf
NMR and IR spectra, and powder diffraction plots

CCDC references: 678070; 678074; 691914; 709114; 713519

Computing details top

Data collection: SMART (Bruker, 1998b) for (3), (9); CrysAlis CCD (Oxford diffraction, 2007) for (5); Bruker APEX II for (10); X-AREA V1.35 (Stoe & Cie, 2006) for (13). Cell refinement: SAINTPlus (Bruker, 1998a) for (3), (9); CrysAlis RED (Oxford diffraction, 2007) for (5); Bruker SAINT for (10); X-AREA V1.35 for (13). Data reduction: SAINTPlus (Bruker, 1998a) for (3), (9); CrysAlis RED (Oxford diffraction, 2007) for (5); Bruker SAINT for (10); X-RED32 V1.31 (Stoe & Cie, 2006) for (13). Program(s) used to solve structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Superflip(Palatinus L., Chapuis G., 2007) for (5); SHELXS97 (Sheldrick, 1997) for (10); SHELXS97 (Sheldrick, 2008) for (13). Program(s) used to refine structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Jana2006 (Petricek, Dusek & Palatinus, 2006) for (5); SHELXL97 (Sheldrick, 1997) for (10); SHELXL97 (Sheldrick, 2008) for (13). Molecular graphics: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Diamond (Brandenburg & Putz, 2005) for (5); Bruker SHELXTL for (10); ORTEP-3 (Farrugia, 1997) & PLATON (Spek, 2003) for (13). Software used to prepare material for publication: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Jana2006 (Petricek, Dusek & Palatinus, 2006) for (5); Bruker SHELXTL for (10); SHELXL97 for (13).

(3) top
Crystal data top
C15H25N4O4PF(000) = 760
Mr = 356.36Dx = 1.327 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 282 reflections
a = 9.9548 (8) Åθ = 3–27°
b = 20.3681 (16) ŵ = 0.18 mm1
c = 8.8471 (7) ÅT = 120 K
β = 96.125 (2)°Prism, colorless
V = 1783.6 (2) Å30.30 × 0.26 × 0.22 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
3882 independent reflections
Radiation source: fine-focus sealed tube2498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
phi and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
SADABS (Sheldrick, 1998a)
h = 1212
Tmin = 0.945, Tmax = 0.963k = 2526
16991 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: mixed
wR(F2) = 0.123H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.030P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
3882 reflections(Δ/σ)max = 0.001
221 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.29 e Å3
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
P10.47911 (6)0.42644 (3)0.19450 (7)0.02303 (17)
O10.44076 (17)0.49667 (8)0.17400 (19)0.0286 (4)
O20.67356 (18)0.31382 (9)0.1506 (2)0.0316 (4)
O31.0652 (2)0.29200 (10)0.4422 (2)0.0483 (6)
O41.0988 (2)0.39665 (10)0.4259 (2)0.0479 (6)
N10.58241 (19)0.41046 (10)0.0589 (2)0.0228 (5)
H1N0.57800.43870.01520.027*
N20.5543 (2)0.41485 (9)0.3662 (2)0.0231 (5)
N30.3566 (2)0.37308 (11)0.1670 (2)0.0270 (5)
N41.0434 (2)0.34648 (12)0.3906 (2)0.0321 (5)
C10.6529 (3)0.46413 (13)0.4305 (3)0.0293 (6)
H1A0.65840.46240.54280.035*
H1B0.62060.50840.39800.035*
C20.7933 (3)0.45344 (15)0.3815 (3)0.0408 (7)
H2A0.85850.48110.44310.061*
H2B0.79300.46510.27400.061*
H2C0.81880.40720.39590.061*
C30.5636 (3)0.35060 (12)0.4445 (3)0.0259 (6)
H3A0.65980.33790.46520.031*
H3B0.51770.31690.37680.031*
C40.4997 (3)0.35200 (13)0.5940 (3)0.0317 (6)
H4A0.51750.31030.64770.048*
H4B0.40200.35850.57280.048*
H4C0.53880.38810.65740.048*
C50.2479 (3)0.37638 (16)0.2668 (3)0.0377 (7)
H5A0.26880.41190.34200.045*
H5B0.24570.33450.32350.045*
C60.1086 (3)0.38878 (15)0.1826 (3)0.0397 (7)
H6A0.04190.39210.25610.059*
H6B0.08440.35230.11270.059*
H6C0.11000.42980.12500.059*
C70.3464 (3)0.32153 (14)0.0515 (3)0.0383 (7)
H7A0.28740.28610.08340.046*
H7B0.43720.30250.04550.046*
C80.2909 (3)0.3451 (2)0.1048 (3)0.0613 (11)
H8A0.28640.30820.17630.092*
H8B0.35020.37930.13880.092*
H8C0.20010.36320.10060.092*
C90.6704 (2)0.35874 (12)0.0589 (3)0.0226 (5)
C100.7662 (2)0.35858 (12)0.0615 (3)0.0224 (5)
C110.8041 (3)0.29821 (13)0.1147 (3)0.0290 (6)
H11A0.76830.25920.07570.035*
C120.8933 (3)0.29370 (13)0.2238 (3)0.0300 (6)
H12A0.91820.25220.26130.036*
C130.9450 (2)0.35078 (13)0.2765 (3)0.0245 (6)
C140.9100 (3)0.41189 (13)0.2268 (3)0.0273 (6)
H14A0.94760.45050.26530.033*
C150.8184 (2)0.41585 (12)0.1192 (3)0.0253 (6)
H15A0.79130.45750.08500.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0215 (3)0.0266 (4)0.0221 (3)0.0032 (3)0.0072 (3)0.0020 (3)
O10.0336 (10)0.0295 (10)0.0241 (9)0.0096 (8)0.0099 (8)0.0041 (8)
O20.0340 (11)0.0311 (10)0.0324 (10)0.0075 (8)0.0157 (8)0.0089 (8)
O30.0496 (13)0.0513 (14)0.0490 (13)0.0013 (11)0.0280 (11)0.0175 (11)
O40.0492 (13)0.0493 (13)0.0510 (14)0.0016 (11)0.0322 (11)0.0075 (11)
N10.0223 (11)0.0286 (12)0.0187 (10)0.0011 (9)0.0081 (8)0.0048 (9)
N20.0218 (11)0.0220 (11)0.0263 (11)0.0017 (8)0.0068 (9)0.0035 (9)
N30.0240 (11)0.0366 (13)0.0217 (11)0.0012 (9)0.0089 (9)0.0007 (9)
N40.0267 (12)0.0455 (15)0.0255 (12)0.0053 (11)0.0095 (10)0.0028 (11)
C10.0322 (15)0.0282 (14)0.0275 (14)0.0045 (12)0.0025 (12)0.0001 (11)
C20.0342 (16)0.0532 (19)0.0353 (16)0.0107 (14)0.0054 (13)0.0010 (14)
C30.0279 (14)0.0262 (14)0.0241 (13)0.0023 (11)0.0048 (11)0.0027 (11)
C40.0390 (16)0.0314 (15)0.0253 (14)0.0009 (12)0.0065 (12)0.0029 (11)
C50.0279 (15)0.0588 (19)0.0281 (15)0.0080 (14)0.0107 (12)0.0016 (14)
C60.0277 (15)0.057 (2)0.0364 (17)0.0017 (14)0.0114 (13)0.0058 (14)
C70.0265 (15)0.0381 (17)0.0525 (19)0.0070 (12)0.0146 (13)0.0112 (14)
C80.0381 (19)0.114 (3)0.0322 (18)0.012 (2)0.0070 (14)0.0267 (19)
C90.0201 (12)0.0252 (13)0.0234 (13)0.0018 (10)0.0073 (10)0.0008 (11)
C100.0187 (12)0.0289 (14)0.0205 (12)0.0017 (10)0.0067 (10)0.0018 (10)
C110.0310 (15)0.0251 (14)0.0330 (15)0.0040 (11)0.0133 (12)0.0022 (11)
C120.0297 (15)0.0268 (14)0.0351 (15)0.0003 (11)0.0107 (12)0.0084 (12)
C130.0175 (12)0.0375 (15)0.0195 (12)0.0020 (11)0.0068 (10)0.0033 (11)
C140.0253 (13)0.0306 (15)0.0272 (14)0.0018 (11)0.0083 (11)0.0052 (11)
C150.0247 (13)0.0269 (14)0.0251 (13)0.0037 (11)0.0059 (11)0.0012 (11)
Geometric parameters (Å, º) top
P1—O11.4866 (18)C4—H4C0.9800
P1—N31.632 (2)C5—C61.523 (4)
P1—N21.637 (2)C5—H5A0.9900
P1—N11.693 (2)C5—H5B0.9900
O2—C91.221 (3)C6—H6A0.9800
O3—N41.228 (3)C6—H6B0.9800
O4—N41.217 (3)C6—H6C0.9800
N1—C91.370 (3)C7—C81.512 (4)
N1—H1N0.8699C7—H7A0.9900
N2—C11.475 (3)C7—H7B0.9900
N2—C31.479 (3)C8—H8A0.9800
N3—C71.461 (3)C8—H8B0.9800
N3—C51.469 (3)C8—H8C0.9800
N4—C131.483 (3)C9—C101.504 (3)
C1—C21.523 (4)C10—C111.383 (3)
C1—H1A0.9900C10—C151.396 (3)
C1—H1B0.9900C11—C121.383 (3)
C2—H2A0.9800C11—H11A0.9500
C2—H2B0.9800C12—C131.373 (4)
C2—H2C0.9800C12—H12A0.9500
C3—C41.528 (3)C13—C141.377 (3)
C3—H3A0.9900C14—C151.389 (3)
C3—H3B0.9900C14—H14A0.9500
C4—H4A0.9800C15—H15A0.9500
C4—H4B0.9800
O1—P1—N3116.39 (11)C6—C5—H5A108.8
O1—P1—N2109.75 (10)N3—C5—H5B108.8
N3—P1—N2107.62 (11)C6—C5—H5B108.8
O1—P1—N1105.43 (10)H5A—C5—H5B107.7
N3—P1—N1105.49 (10)C5—C6—H6A109.5
N2—P1—N1112.16 (10)C5—C6—H6B109.5
C9—N1—P1125.78 (17)H6A—C6—H6B109.5
C9—N1—H1N119.3C5—C6—H6C109.5
P1—N1—H1N114.9H6A—C6—H6C109.5
C1—N2—C3114.6 (2)H6B—C6—H6C109.5
C1—N2—P1118.66 (16)N3—C7—C8113.7 (3)
C3—N2—P1124.17 (17)N3—C7—H7A108.8
C7—N3—C5116.9 (2)C8—C7—H7A108.8
C7—N3—P1125.28 (17)N3—C7—H7B108.8
C5—N3—P1117.79 (18)C8—C7—H7B108.8
O4—N4—O3124.1 (2)H7A—C7—H7B107.7
O4—N4—C13118.4 (2)C7—C8—H8A109.5
O3—N4—C13117.5 (2)C7—C8—H8B109.5
N2—C1—C2112.7 (2)H8A—C8—H8B109.5
N2—C1—H1A109.1C7—C8—H8C109.5
C2—C1—H1A109.1H8A—C8—H8C109.5
N2—C1—H1B109.1H8B—C8—H8C109.5
C2—C1—H1B109.1O2—C9—N1123.2 (2)
H1A—C1—H1B107.8O2—C9—C10119.7 (2)
C1—C2—H2A109.5N1—C9—C10117.1 (2)
C1—C2—H2B109.5C11—C10—C15119.5 (2)
H2A—C2—H2B109.5C11—C10—C9117.4 (2)
C1—C2—H2C109.5C15—C10—C9123.1 (2)
H2A—C2—H2C109.5C12—C11—C10121.0 (2)
H2B—C2—H2C109.5C12—C11—H11A119.5
N2—C3—C4112.2 (2)C10—C11—H11A119.5
N2—C3—H3A109.2C13—C12—C11118.2 (2)
C4—C3—H3A109.2C13—C12—H12A120.9
N2—C3—H3B109.2C11—C12—H12A120.9
C4—C3—H3B109.2C12—C13—C14122.7 (2)
H3A—C3—H3B107.9C12—C13—N4118.7 (2)
C3—C4—H4A109.5C14—C13—N4118.6 (2)
C3—C4—H4B109.5C13—C14—C15118.6 (2)
H4A—C4—H4B109.5C13—C14—H14A120.7
C3—C4—H4C109.5C15—C14—H14A120.7
H4A—C4—H4C109.5C14—C15—C10120.0 (2)
H4B—C4—H4C109.5C14—C15—H15A120.0
N3—C5—C6113.8 (2)C10—C15—H15A120.0
N3—C5—H5A108.8
O1—P1—N1—C9161.2 (2)P1—N3—C7—C881.2 (3)
N3—P1—N1—C975.1 (2)P1—N1—C9—O28.1 (4)
N2—P1—N1—C941.8 (2)P1—N1—C9—C10172.03 (17)
O1—P1—N2—C141.5 (2)O2—C9—C10—C1131.7 (4)
N3—P1—N2—C1169.07 (17)N1—C9—C10—C11148.2 (2)
N1—P1—N2—C175.33 (19)O2—C9—C10—C15147.6 (3)
O1—P1—N2—C3157.84 (18)N1—C9—C10—C1532.5 (3)
N3—P1—N2—C330.3 (2)C15—C10—C11—C120.3 (4)
N1—P1—N2—C385.3 (2)C9—C10—C11—C12179.1 (2)
O1—P1—N3—C7118.7 (2)C10—C11—C12—C130.9 (4)
N2—P1—N3—C7117.7 (2)C11—C12—C13—C141.0 (4)
N1—P1—N3—C72.3 (2)C11—C12—C13—N4178.5 (2)
O1—P1—N3—C561.8 (2)O4—N4—C13—C12173.0 (2)
N2—P1—N3—C561.8 (2)O3—N4—C13—C126.1 (3)
N1—P1—N3—C5178.31 (19)O4—N4—C13—C146.6 (4)
C3—N2—C1—C278.5 (3)O3—N4—C13—C14174.4 (2)
P1—N2—C1—C283.9 (2)C12—C13—C14—C150.1 (4)
C1—N2—C3—C477.5 (3)N4—C13—C14—C15179.6 (2)
P1—N2—C3—C4121.2 (2)C13—C14—C15—C101.4 (4)
C7—N3—C5—C660.8 (3)C11—C10—C15—C141.4 (4)
P1—N3—C5—C6119.7 (2)C9—C10—C15—C14177.9 (2)
C5—N3—C7—C899.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.871.922.789 (3)177
Symmetry code: (i) x+1, y+1, z.
(5) top
Crystal data top
C15H21N4O4PZ = 2
Mr = 352.3F(000) = 372
Triclinic, P1Dx = 1.405 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1631 (2) ÅCell parameters from 10101 reflections
b = 9.3224 (2) Åθ = 3.0–39.2°
c = 11.4353 (3) ŵ = 0.19 mm1
α = 109.909 (2)°T = 120 K
β = 110.445 (2)°Irregular shape, yellow
γ = 96.024 (2)°0.98 × 0.36 × 0.22 mm
V = 832.33 (4) Å3
Data collection top
Oxford Diffraction CCD
diffractometer
3460 independent reflections
Radiation source: X-ray tube2983 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.3438 pixels mm-1θmax = 26.5°, θmin = 3.0°
Rotation method data acquisition using ω scansh = 1111
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.16 (release 23-01-2008 CrysAlis171 .NET) (compiled Jan 23 2008,18:08:03) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1111
Tmin = 0.942, Tmax = 1.000l = 1414
10200 measured reflections
Refinement top
Refinement on F2100 constraints
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.096Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 3.18(Δ/σ)max = 0.039
3460 reflectionsΔρmax = 0.49 e Å3
225 parametersΔρmin = 0.44 e Å3
0 restraints
Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger then the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.02647 (4)0.93374 (4)0.79195 (4)0.01391 (16)
O30.04741 (14)1.18415 (13)0.68630 (11)0.0252 (5)
O20.36096 (14)1.60495 (13)1.14465 (12)0.0289 (5)
O40.06262 (13)0.87341 (12)0.90077 (10)0.0199 (5)
N40.18622 (15)0.97270 (15)0.76514 (12)0.0178 (5)
N30.11539 (15)0.82348 (15)0.64081 (13)0.0199 (5)
N10.31501 (17)1.48699 (16)1.10040 (14)0.0255 (6)
O10.3149 (2)1.38104 (17)1.14088 (16)0.0548 (9)
N20.04586 (14)1.09204 (14)0.84661 (12)0.0159 (5)
C90.3724 (2)0.6772 (2)0.46523 (17)0.0328 (7)
C150.19684 (19)0.99653 (19)0.64674 (15)0.0204 (6)
C80.28773 (18)0.82184 (19)0.60091 (16)0.0238 (7)
C30.22089 (19)1.56754 (18)0.83442 (17)0.0225 (7)
C110.0963 (2)0.67406 (19)0.55265 (17)0.0301 (7)
C50.26115 (17)1.46975 (17)0.99024 (15)0.0181 (6)
C100.2653 (2)0.5639 (2)0.47975 (17)0.0330 (8)
C60.19759 (17)1.34261 (17)0.94756 (14)0.0164 (6)
C20.15817 (18)1.44106 (17)0.78814 (16)0.0197 (6)
C120.34973 (17)0.99383 (18)0.86483 (15)0.0208 (6)
C10.14612 (17)1.32818 (16)0.84387 (14)0.0155 (6)
C40.27361 (18)1.58278 (17)0.93653 (16)0.0201 (6)
C70.07531 (17)1.19632 (17)0.78584 (14)0.0165 (6)
C13a0.4548 (8)1.0126 (8)0.7927 (6)0.0247 (12)0.336 (5)
C13b0.4420 (3)0.9339 (4)0.7760 (3)0.0247 (12)0.664 (5)
C14a0.3391 (10)0.9305 (11)0.6332 (9)0.033 (3)0.644 (17)
C14b0.3674 (18)0.9798 (14)0.6637 (12)0.033 (3)0.356 (17)
H1n20.0657771.1084090.9184630.019*
H1c20.1225191.430960.7167930.0237*
H1c30.227641.6443480.7955080.027*
H1c40.3176141.6693180.9692690.0241*
H1c60.1894231.2673350.9881190.0197*
H1c80.3049890.9152050.5861390.0286*
H2c80.3216120.8066280.6673020.0286*
H1c90.3734070.7059630.3920180.0393*
H2c90.4767550.6313090.4561450.0393*
H1c100.2835590.5161530.5373760.0396*
H2c100.2802190.491940.3908390.0396*
H1c110.024940.6322220.6087270.0361*
H2c110.0631480.6918850.4867630.0361*
H1c120.3493690.9124830.8984360.0249*
H2c120.3876931.0990820.9345930.0249*
H1c13a0.4965391.1227670.8182220.0297*0.336 (5)
H2c13a0.5376160.9583820.8124760.0297*0.336 (5)
H1c150.2063971.1056530.6622450.0244*
H2c150.1085560.9230410.5644950.0244*
H1c13b0.419450.8209880.7420110.0297*0.6639
H2c13b0.5534450.9904260.8254380.0297*0.6639
H1c14a0.3105230.8182010.6046980.0393*0.644 (17)
H2c14a0.382360.9758930.5846750.0393*0.644 (17)
H1c14b0.4326361.0781610.6803120.0393*0.3555
H2c14b0.3622750.902090.5806660.0393*0.3555
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0174 (2)0.0141 (2)0.0123 (2)0.00635 (15)0.00758 (15)0.00546 (14)
O30.0383 (7)0.0297 (6)0.0192 (6)0.0186 (5)0.0177 (5)0.0142 (5)
O20.0319 (6)0.0240 (6)0.0283 (6)0.0126 (5)0.0168 (5)0.0018 (5)
O40.0290 (6)0.0210 (5)0.0201 (6)0.0130 (5)0.0157 (5)0.0124 (5)
N40.0169 (6)0.0266 (7)0.0131 (6)0.0074 (5)0.0064 (5)0.0108 (5)
N30.0197 (6)0.0190 (7)0.0167 (6)0.0051 (5)0.0086 (5)0.0009 (5)
N10.0312 (7)0.0246 (7)0.0265 (7)0.0129 (6)0.0175 (6)0.0096 (6)
O10.1049 (13)0.0508 (9)0.0648 (11)0.0515 (9)0.0698 (11)0.0427 (8)
N20.0228 (6)0.0174 (6)0.0112 (6)0.0091 (5)0.0098 (5)0.0061 (5)
C90.0281 (9)0.0375 (10)0.0217 (9)0.0082 (8)0.0040 (7)0.0108 (8)
C150.0244 (8)0.0255 (8)0.0179 (8)0.0081 (7)0.0124 (7)0.0122 (6)
C80.0181 (8)0.0308 (9)0.0206 (8)0.0032 (7)0.0061 (6)0.0110 (7)
C30.0241 (8)0.0188 (8)0.0282 (9)0.0080 (7)0.0091 (7)0.0145 (7)
C110.0360 (10)0.0205 (8)0.0256 (9)0.0036 (7)0.0165 (8)0.0031 (7)
C50.0173 (7)0.0179 (7)0.0174 (7)0.0047 (6)0.0075 (6)0.0047 (6)
C100.0449 (11)0.0250 (9)0.0193 (8)0.0055 (8)0.0121 (8)0.0030 (7)
C60.0186 (7)0.0150 (7)0.0160 (7)0.0054 (6)0.0062 (6)0.0072 (6)
C20.0203 (7)0.0215 (8)0.0197 (8)0.0066 (6)0.0084 (6)0.0104 (6)
C120.0179 (7)0.0251 (8)0.0170 (8)0.0085 (6)0.0048 (6)0.0073 (6)
C10.0147 (7)0.0154 (7)0.0138 (7)0.0039 (6)0.0033 (6)0.0053 (6)
C40.0175 (7)0.0149 (7)0.0255 (8)0.0069 (6)0.0072 (6)0.0064 (6)
C70.0179 (7)0.0169 (7)0.0130 (7)0.0051 (6)0.0053 (6)0.0051 (6)
C13a0.0206 (10)0.0291 (19)0.0258 (12)0.0097 (16)0.0107 (10)0.0105 (16)
C13b0.0206 (10)0.0291 (19)0.0258 (12)0.0097 (16)0.0107 (10)0.0105 (16)
C14a0.035 (3)0.053 (4)0.020 (3)0.025 (3)0.017 (3)0.016 (3)
C14b0.035 (3)0.053 (4)0.020 (3)0.025 (3)0.017 (3)0.016 (3)
Geometric parameters (Å, º) top
P1—O41.4840 (14)C11—C101.526 (2)
P1—N41.6268 (16)C11—H1c110.96
P1—N31.6351 (10)C11—H2c110.96
P1—N21.6954 (14)C5—C61.390 (2)
O3—C71.223 (2)C5—C41.385 (3)
O2—N11.229 (2)C10—H1c100.96
N4—C151.478 (3)C10—H2c100.96
N4—C121.4747 (18)C6—C11.393 (3)
N3—C81.480 (2)C6—H1c60.96
N3—C111.485 (2)C2—C11.399 (3)
N1—O11.225 (3)C2—H1c20.96
N1—C51.473 (3)C12—C13a1.501 (9)
N2—C71.373 (2)C12—C13b1.540 (4)
N2—H1n20.87C12—H1c120.96
C9—C81.5306 (19)C12—H2c120.96
C9—C101.526 (3)C1—C71.512 (2)
C9—H1c90.96C4—H1c40.96
C9—H2c90.96C13a—C14a1.602 (10)
C15—C14a1.532 (10)C13a—H1c13a0.96
C15—C14b1.538 (17)C13a—H2c13a0.96
C15—H1c150.96C13b—C14b1.456 (15)
C15—H2c150.96C13b—H1c13b0.96
C8—H1c80.96C13b—H2c13b0.96
C8—H2c80.96C14a—H1c14a0.96
C3—C21.389 (2)C14a—H2c14a0.96
C3—C41.383 (3)C14b—H1c14b0.96
C3—H1c30.96C14b—H2c14b0.96
O4—P1—N4110.38 (7)C11—C10—H1c10109.471
O4—P1—N3118.96 (7)C11—C10—H2c10109.471
O4—P1—N2105.02 (7)H1c10—C10—H2c10115.596
N4—P1—N3104.98 (7)C5—C6—C1117.70 (17)
N4—P1—N2114.44 (7)C5—C6—H1c6121.15
N3—P1—N2103.24 (6)C1—C6—H1c6121.149
P1—N4—C15128.41 (10)C3—C2—C1121.05 (18)
P1—N4—C12122.38 (13)C3—C2—H1c2119.473
C15—N4—C12109.19 (14)C1—C2—H1c2119.473
P1—N3—C8124.07 (11)N4—C12—C13a103.7 (3)
P1—N3—C11121.00 (11)N4—C12—C13b103.97 (15)
C8—N3—C11110.68 (11)N4—C12—H1c12109.471
O2—N1—O1123.52 (19)N4—C12—H2c12109.471
O2—N1—C5118.34 (16)C13a—C12—H1c12120.993
O1—N1—C5118.12 (16)C13a—C12—H2c1297.842
P1—N2—C7124.81 (12)C13b—C12—H1c1298.036
P1—N2—H1n2117.594C13b—C12—H2c12120.583
C7—N2—H1n2117.594H1c12—C12—H2c12114.269
C8—C9—C10103.69 (13)C6—C1—C2119.61 (15)
C8—C9—H1c9109.471C6—C1—C7124.05 (16)
C8—C9—H2c9109.471C2—C1—C7116.34 (16)
C10—C9—H1c9109.471C3—C4—C5118.15 (16)
C10—C9—H2c9109.471C3—C4—H1c4120.924
H1c9—C9—H2c9114.695C5—C4—H1c4120.924
N4—C15—C14a103.4 (5)O3—C7—N2121.91 (15)
N4—C15—C14b101.8 (6)O3—C7—C1119.72 (16)
N4—C15—H1c15109.471N2—C7—C1118.37 (15)
N4—C15—H2c15109.471C12—C13a—C14a105.7 (5)
C14a—C15—H1c15116.58C12—C13a—H1c13a109.472
C14a—C15—H2c15101.549C12—C13a—H2c13a109.472
C14b—C15—H1c15102.268C14a—C13a—H2c12125.399
C14b—C15—H2c15117.305C14a—C13a—H1c13a109.47
H1c15—C15—H2c15115.435C14a—C13a—H2c13a109.471
N3—C8—C9103.60 (14)H2c12—C13a—H1c13a80.56
N3—C8—H1c8109.471H2c12—C13a—H2c13a115.094
N3—C8—H2c8109.471H1c13a—C13a—H2c13a113.027
C9—C8—H1c8109.471C12—C13b—C14b101.6 (7)
C9—C8—H2c8109.471C12—C13b—H1c13b109.471
H1c8—C8—H2c8114.769C12—C13b—H2c13b109.471
C2—C3—C4120.00 (18)C14b—C13b—H1c13b109.471
C2—C3—H1c3120C14b—C13b—H2c13b109.472
C4—C3—H1c3119.999H1c13b—C13b—H2c13b116.338
N3—C11—C10104.03 (15)C15—C14a—C13a95.6 (6)
N3—C11—H1c11109.471C15—C14a—H1c14a109.471
N3—C11—H2c11109.471C15—C14a—H2c14a109.471
C10—C11—H1c11109.471C13a—C14a—H1c14a109.471
C10—C11—H2c11109.471C13a—C14a—H2c14a109.471
H1c11—C11—H2c11114.418H1c14a—C14a—H2c14a120.483
N1—C5—C6118.26 (16)C15—C14b—C13b111.3 (11)
N1—C5—C4118.26 (15)C15—C14b—H1c14b109.471
C6—C5—C4123.47 (18)C15—C14b—H2c14b109.471
C9—C10—C11102.56 (14)C13b—C14b—H1c14b109.471
C9—C10—H1c10109.471C13b—C14b—H2c14b109.472
C9—C10—H2c10109.471H1c14b—C14b—H2c14b107.552
(9) top
Crystal data top
C15H21N4O6PF(000) = 808
Mr = 384.33Dx = 1.497 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 316 reflections
a = 16.2973 (12) Åθ = 3–30°
b = 11.1318 (8) ŵ = 0.20 mm1
c = 9.4354 (7) ÅT = 120 K
β = 94.881 (2)°Prism, colorless
V = 1705.5 (2) Å30.28 × 0.26 × 0.18 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
4958 independent reflections
Radiation source: fine-focus sealed tube3709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
phi and ω scansθmax = 30.0°, θmin = 1.3°
Absorption correction: multi-scan
SADABS (Sheldrick, 1998a)
h = 2222
Tmin = 0.941, Tmax = 0.968k = 1515
19538 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: mixed
wR(F2) = 0.126H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.050P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
4958 reflections(Δ/σ)max = 0.001
247 parametersΔρmax = 0.45 e Å3
11 restraintsΔρmin = 0.41 e Å3
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*/UeqOcc. (<1)
P10.72756 (3)0.15976 (4)0.43644 (4)0.01736 (11)
O10.75864 (7)0.18520 (12)0.58549 (12)0.0214 (3)
O20.53805 (9)0.43820 (14)0.29983 (15)0.0331 (3)
O40.88392 (8)0.03195 (12)0.44666 (13)0.0255 (3)
O51.18502 (9)0.06092 (15)0.01625 (18)0.0406 (4)
O61.12161 (9)0.20653 (14)0.12942 (15)0.0334 (3)
N10.65724 (8)0.25956 (13)0.38296 (15)0.0195 (3)
N20.68430 (9)0.02940 (13)0.40839 (15)0.0240 (3)
N30.80206 (8)0.16713 (13)0.32300 (14)0.0173 (3)
H3N0.79240.20870.24530.021*
N41.12866 (9)0.13335 (14)0.03249 (16)0.0237 (3)
C10.67575 (11)0.38799 (17)0.4032 (2)0.0242 (4)
H1A0.71390.39890.48960.029*
H1B0.70320.41860.32080.029*
C20.59725 (12)0.45904 (19)0.4182 (2)0.0294 (4)
H2A0.61040.54580.42430.035*
H2B0.57350.43530.50720.035*
C30.51835 (11)0.3135 (2)0.2909 (2)0.0324 (4)
H3A0.49590.28770.38020.039*
H3B0.47530.30040.21190.039*
C40.59334 (10)0.23747 (19)0.26617 (19)0.0254 (4)
H4A0.61430.25910.17410.030*
H4B0.57820.15130.26330.030*
C90.87345 (10)0.10135 (15)0.34665 (17)0.0184 (3)
C100.93955 (10)0.11669 (15)0.24531 (17)0.0176 (3)
C111.00347 (11)0.03303 (16)0.25795 (19)0.0217 (3)
H11A1.00370.02820.32820.026*
C121.06684 (11)0.03870 (16)0.16839 (19)0.0229 (3)
H12A1.11030.01850.17530.028*
C131.06469 (10)0.13000 (16)0.06906 (17)0.0191 (3)
C141.00412 (10)0.21729 (16)0.05804 (18)0.0212 (3)
H14A1.00590.28080.00890.025*
C150.94035 (10)0.21009 (16)0.14730 (18)0.0203 (3)
H15A0.89770.26850.14130.024*
C5A0.70139 (11)0.06211 (15)0.30444 (19)0.0279 (4)
H5AA0.65260.07850.23730.033*
H5AB0.74850.03950.25040.033*
C6A0.7221 (3)0.1689 (3)0.4032 (4)0.0388 (10)0.55
H6AA0.77190.14860.46620.047*0.55
H6AB0.73610.23840.34430.047*0.55
C7A0.6402 (3)0.1081 (3)0.5808 (4)0.0345 (8)0.55
H7AA0.59510.13210.63900.041*0.55
H7AB0.68930.08930.64610.041*0.55
C8A0.6145 (2)0.0027 (4)0.4942 (5)0.0249 (8)0.55
H8AA0.60430.07100.55750.030*0.55
H8AB0.56370.01330.43180.030*0.55
O3A0.6586 (2)0.2048 (3)0.4899 (4)0.0360 (6)0.55
O3B0.6765 (3)0.2305 (4)0.4420 (4)0.0360 (6)0.45
C8B0.6384 (3)0.0313 (4)0.5156 (6)0.0249 (8)0.45
H8BA0.63820.02110.60030.030*0.45
H8BB0.58060.04190.47640.030*0.45
C7B0.6733 (4)0.1527 (3)0.5615 (4)0.0345 (8)0.45
H7BA0.63840.18930.63090.041*0.45
H7BB0.72940.14220.60890.041*0.45
C6B0.7341 (4)0.1843 (3)0.3512 (6)0.0388 (10)0.45
H6BA0.78930.17700.40300.047*0.45
H6BB0.73810.23760.26810.047*0.45
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01551 (19)0.0226 (2)0.0142 (2)0.00298 (16)0.00293 (14)0.00134 (16)
O10.0180 (6)0.0304 (7)0.0157 (6)0.0040 (5)0.0019 (4)0.0031 (5)
O20.0301 (7)0.0425 (9)0.0268 (7)0.0121 (6)0.0038 (6)0.0041 (6)
O40.0239 (6)0.0316 (7)0.0212 (6)0.0027 (5)0.0037 (5)0.0079 (5)
O50.0305 (8)0.0445 (9)0.0495 (10)0.0168 (7)0.0192 (7)0.0110 (7)
O60.0309 (7)0.0448 (9)0.0262 (7)0.0050 (6)0.0108 (6)0.0085 (6)
N10.0159 (6)0.0242 (7)0.0185 (6)0.0007 (5)0.0021 (5)0.0013 (5)
N20.0286 (8)0.0269 (8)0.0176 (7)0.0112 (6)0.0087 (6)0.0040 (6)
N30.0149 (6)0.0237 (7)0.0138 (6)0.0002 (5)0.0036 (5)0.0026 (5)
N40.0197 (7)0.0290 (8)0.0231 (7)0.0009 (6)0.0059 (6)0.0015 (6)
C10.0246 (8)0.0248 (9)0.0235 (9)0.0017 (7)0.0030 (7)0.0004 (7)
C20.0337 (10)0.0306 (10)0.0242 (9)0.0064 (8)0.0056 (8)0.0007 (7)
C30.0173 (8)0.0506 (13)0.0294 (10)0.0036 (8)0.0023 (7)0.0012 (9)
C40.0168 (8)0.0376 (10)0.0213 (8)0.0008 (7)0.0001 (6)0.0033 (7)
C90.0169 (7)0.0223 (8)0.0159 (7)0.0005 (6)0.0017 (6)0.0009 (6)
C100.0156 (7)0.0211 (8)0.0161 (7)0.0006 (6)0.0013 (6)0.0011 (6)
C110.0212 (8)0.0214 (8)0.0225 (8)0.0021 (6)0.0026 (6)0.0032 (6)
C120.0201 (8)0.0218 (8)0.0272 (9)0.0043 (6)0.0040 (7)0.0006 (7)
C130.0150 (7)0.0247 (8)0.0182 (7)0.0004 (6)0.0044 (6)0.0030 (6)
C140.0187 (8)0.0247 (9)0.0206 (8)0.0017 (6)0.0031 (6)0.0042 (7)
C150.0164 (7)0.0238 (8)0.0210 (8)0.0030 (6)0.0031 (6)0.0034 (6)
C5A0.0240 (9)0.0264 (9)0.0336 (10)0.0029 (7)0.0047 (7)0.0101 (8)
C6A0.0289 (17)0.0164 (13)0.071 (3)0.0063 (11)0.007 (2)0.0174 (18)
C7A0.058 (3)0.0213 (19)0.0246 (14)0.0122 (14)0.0086 (15)0.0009 (14)
C8A0.031 (2)0.022 (2)0.0227 (16)0.0094 (14)0.0113 (17)0.0023 (13)
O3A0.0516 (19)0.0181 (15)0.039 (2)0.0062 (12)0.0061 (13)0.0013 (12)
O3B0.0516 (19)0.0181 (15)0.039 (2)0.0062 (12)0.0061 (13)0.0013 (12)
C8B0.031 (2)0.022 (2)0.0227 (16)0.0094 (14)0.0113 (17)0.0023 (13)
C7B0.058 (3)0.0213 (19)0.0246 (14)0.0122 (14)0.0086 (15)0.0009 (14)
C6B0.0289 (17)0.0164 (13)0.071 (3)0.0063 (11)0.007 (2)0.0174 (18)
Geometric parameters (Å, º) top
P1—O11.4811 (12)C11—C121.390 (2)
P1—N21.6251 (15)C11—H11A0.9500
P1—N11.6443 (15)C12—C131.381 (2)
P1—N31.6875 (14)C12—H12A0.9500
O2—C31.426 (3)C13—C141.383 (2)
O2—C21.431 (2)C14—C151.395 (2)
O4—C91.220 (2)C14—H14A0.9500
O5—N41.222 (2)C15—H15A0.9500
O6—N41.223 (2)C5A—C6B1.513 (3)
N1—C11.470 (2)C5A—C6A1.530 (3)
N1—C41.471 (2)C5A—H5AA0.9900
N2—C5A1.4573 (18)C5A—H5AB0.9900
N2—C8B1.472 (3)C6A—O3A1.430 (3)
N2—C8A1.481 (2)C6A—H6AA0.9900
N3—C91.377 (2)C6A—H6AB0.9900
N3—H3N0.8700C7A—O3A1.424 (3)
N4—C131.475 (2)C7A—C8A1.518 (3)
C1—C21.521 (3)C7A—H7AA0.9900
C1—H1A0.9900C7A—H7AB0.9900
C1—H1B0.9900C8A—H8AA0.9900
C2—H2A0.9900C8A—H8AB0.9900
C2—H2B0.9900O3B—C6B1.421 (3)
C3—C41.521 (3)O3B—C7B1.427 (3)
C3—H3A0.9900C8B—C7B1.515 (3)
C3—H3B0.9900C8B—H8BA0.9900
C4—H4A0.9900C8B—H8BB0.9900
C4—H4B0.9900C7B—H7BA0.9900
C9—C101.510 (2)C7B—H7BB0.9900
C10—C151.392 (2)C6B—H6BA0.9900
C10—C111.395 (2)C6B—H6BB0.9900
O1—P1—N2115.72 (8)C12—C13—C14123.02 (15)
O1—P1—N1109.59 (7)C12—C13—N4118.74 (15)
N2—P1—N1105.78 (8)C14—C13—N4118.22 (15)
O1—P1—N3112.74 (7)C13—C14—C15118.57 (16)
N2—P1—N3105.41 (7)C13—C14—H14A120.7
N1—P1—N3107.03 (7)C15—C14—H14A120.7
C3—O2—C2109.73 (15)C10—C15—C14119.58 (15)
C1—N1—C4112.60 (14)C10—C15—H15A120.2
C1—N1—P1119.16 (11)C14—C15—H15A120.2
C4—N1—P1123.18 (12)N2—C5A—C6B121.0 (3)
C5A—N2—C8B106.2 (3)N2—C5A—C6A100.28 (19)
C5A—N2—C8A115.3 (2)N2—C5A—H5AA111.7
C5A—N2—P1128.95 (11)C6B—C5A—H5AA105.4
C8B—N2—P1122.4 (3)C6A—C5A—H5AA111.7
C8A—N2—P1115.6 (2)N2—C5A—H5AB111.7
C9—N3—P1121.00 (11)C6B—C5A—H5AB96.3
C9—N3—H3N120.6C6A—C5A—H5AB111.7
P1—N3—H3N118.2H5AA—C5A—H5AB109.5
O5—N4—O6123.72 (15)O3A—C6A—C5A115.6 (3)
O5—N4—C13117.84 (15)O3A—C6A—H6AA108.4
O6—N4—C13118.42 (15)C5A—C6A—H6AA108.4
N1—C1—C2110.66 (15)O3A—C6A—H6AB108.4
N1—C1—H1A109.5C5A—C6A—H6AB108.4
C2—C1—H1A109.5H6AA—C6A—H6AB107.4
N1—C1—H1B109.5O3A—C7A—C8A110.6 (3)
C2—C1—H1B109.5O3A—C7A—H7AA109.5
H1A—C1—H1B108.1C8A—C7A—H7AA109.5
O2—C2—C1111.10 (15)O3A—C7A—H7AB109.5
O2—C2—H2A109.4C8A—C7A—H7AB109.5
C1—C2—H2A109.4H7AA—C7A—H7AB108.1
O2—C2—H2B109.4N2—C8A—C7A105.5 (2)
C1—C2—H2B109.4N2—C8A—H8AA110.6
H2A—C2—H2B108.0C7A—C8A—H8AA110.6
O2—C3—C4111.77 (16)N2—C8A—H8AB110.6
O2—C3—H3A109.3C7A—C8A—H8AB110.6
C4—C3—H3A109.3H8AA—C8A—H8AB108.8
O2—C3—H3B109.3C7A—O3A—C6A109.5 (3)
C4—C3—H3B109.3C6B—O3B—C7B109.1 (4)
H3A—C3—H3B107.9N2—C8B—C7B113.9 (3)
N1—C4—C3108.60 (15)N2—C8B—H8BA108.8
N1—C4—H4A110.0C7B—C8B—H8BA108.8
C3—C4—H4A110.0N2—C8B—H8BB108.8
N1—C4—H4B110.0C7B—C8B—H8BB108.8
C3—C4—H4B110.0H8BA—C8B—H8BB107.7
H4A—C4—H4B108.4O3B—C7B—C8B110.7 (4)
O4—C9—N3121.52 (15)O3B—C7B—H7BA109.5
O4—C9—C10120.07 (15)C8B—C7B—H7BA109.5
N3—C9—C10118.42 (14)O3B—C7B—H7BB109.5
C15—C10—C11120.42 (15)C8B—C7B—H7BB109.5
C15—C10—C9123.55 (15)H7BA—C7B—H7BB108.1
C11—C10—C9115.99 (15)O3B—C6B—C5A105.5 (3)
C12—C11—C10120.37 (16)O3B—C6B—H6BA110.6
C12—C11—H11A119.8C5A—C6B—H6BA110.6
C10—C11—H11A119.8O3B—C6B—H6BB110.6
C13—C12—C11117.95 (16)C5A—C6B—H6BB110.6
C13—C12—H12A121.0H6BA—C6B—H6BB108.8
C11—C12—H12A121.0
O1—P1—N1—C150.57 (14)C10—C11—C12—C130.8 (3)
N2—P1—N1—C1175.97 (12)C11—C12—C13—C142.1 (3)
N3—P1—N1—C171.98 (14)C11—C12—C13—N4176.43 (15)
O1—P1—N1—C4156.48 (13)O5—N4—C13—C126.2 (2)
N2—P1—N1—C431.08 (15)O6—N4—C13—C12172.40 (17)
N3—P1—N1—C480.96 (14)O5—N4—C13—C14175.22 (17)
O1—P1—N2—C5A127.90 (16)O6—N4—C13—C146.2 (2)
N1—P1—N2—C5A110.57 (17)C12—C13—C14—C152.7 (3)
N3—P1—N2—C5A2.61 (18)N4—C13—C14—C15175.75 (15)
O1—P1—N2—C8B32.0 (3)C11—C10—C15—C142.2 (3)
N1—P1—N2—C8B89.5 (3)C9—C10—C15—C14179.83 (15)
N3—P1—N2—C8B157.3 (2)C13—C14—C15—C100.6 (3)
O1—P1—N2—C8A56.2 (2)C8B—N2—C5A—C6B46.2 (4)
N1—P1—N2—C8A65.3 (2)C8A—N2—C5A—C6B67.9 (4)
N3—P1—N2—C8A178.52 (19)P1—N2—C5A—C6B116.2 (3)
O1—P1—N3—C953.76 (15)C8B—N2—C5A—C6A39.8 (3)
N2—P1—N3—C973.37 (15)C8A—N2—C5A—C6A61.5 (3)
N1—P1—N3—C9174.33 (13)P1—N2—C5A—C6A122.6 (2)
C4—N1—C1—C252.44 (19)N2—C5A—C6A—O3A59.0 (4)
P1—N1—C1—C2151.91 (13)C6B—C5A—C6A—O3A136.0 (13)
C3—O2—C2—C159.5 (2)C5A—N2—C8A—C7A64.2 (4)
N1—C1—C2—O254.8 (2)C8B—N2—C8A—C7A5.8 (9)
C2—O2—C3—C461.8 (2)P1—N2—C8A—C7A119.4 (3)
C1—N1—C4—C353.1 (2)O3A—C7A—C8A—N257.6 (4)
P1—N1—C4—C3152.34 (14)C8A—C7A—O3A—C6A57.6 (4)
O2—C3—C4—N158.0 (2)C5A—C6A—O3A—C7A61.0 (5)
P1—N3—C9—O43.1 (2)C5A—N2—C8B—C7B43.9 (5)
P1—N3—C9—C10176.93 (11)C8A—N2—C8B—C7B161.7 (16)
O4—C9—C10—C15166.37 (17)P1—N2—C8B—C7B120.0 (4)
N3—C9—C10—C1513.6 (2)C6B—O3B—C7B—C8B66.0 (6)
O4—C9—C10—C1111.3 (2)N2—C8B—C7B—O3B57.2 (6)
N3—C9—C10—C11168.65 (15)C7B—O3B—C6B—C5A61.2 (6)
C15—C10—C11—C122.9 (3)N2—C5A—C6B—O3B55.8 (5)
C9—C10—C11—C12179.28 (16)C6A—C5A—C6B—O3B38.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O1i0.871.962.8205 (18)172
Symmetry code: (i) x, y1/2, z1/2.
(10) top
Crystal data top
C33H50LaN11O23P2F(000) = 2384
Mr = 1169.69Dx = 1.688 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 989 reflections
a = 8.8631 (10) Åθ = 3–29°
b = 33.466 (4) ŵ = 1.10 mm1
c = 15.5399 (18) ÅT = 100 K
β = 93.195 (3)°Plate, colorless
V = 4602.2 (9) Å30.47 × 0.33 × 0.20 mm
Z = 4
Data collection top
Bruker APEX II CCD area detector'
diffractometer
12056 independent reflections
Radiation source: fine-focus sealed tube9147 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
ω scansθmax = 29.0°, θmin = 1.2°
Absorption correction: multi-scan
SADABS
h = 1212
Tmin = 0.657, Tmax = 0.801k = 4545
54317 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: mixed
wR(F2) = 0.112H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0141P)2 + 17.2485P]
where P = (Fo2 + 2Fc2)/3
12056 reflections(Δ/σ)max = 0.002
687 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = 1.44 e Å3
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*/UeqOcc. (<1)
La10.21219 (3)0.162084 (7)0.416286 (16)0.01963 (6)
P10.30762 (11)0.15883 (3)0.65977 (7)0.0229 (2)
P20.24369 (11)0.13787 (3)0.17453 (7)0.0203 (2)
O10.1963 (3)0.23304 (8)0.48952 (19)0.0242 (6)
O20.1005 (3)0.22984 (8)0.35884 (19)0.0241 (6)
O30.0515 (4)0.28073 (9)0.4400 (2)0.0318 (7)
O40.1344 (3)0.08474 (9)0.36440 (19)0.0267 (6)
O50.0890 (3)0.10120 (8)0.49486 (19)0.0261 (6)
O60.0109 (4)0.04378 (9)0.4440 (2)0.0326 (7)
O70.0672 (4)0.15073 (9)0.3599 (2)0.0322 (7)
O80.0438 (4)0.17936 (9)0.4847 (2)0.0310 (7)
O90.2673 (4)0.16616 (13)0.4287 (3)0.0587 (12)
O100.3085 (3)0.16053 (9)0.56381 (19)0.0253 (6)
O110.1977 (4)0.11817 (12)0.8228 (2)0.0398 (8)
O120.7891 (3)0.15015 (10)0.7497 (2)0.0318 (7)
O130.1117 (4)0.27018 (9)0.7618 (2)0.0344 (8)
O140.3940 (4)0.01828 (10)0.6739 (2)0.0343 (7)
O150.3628 (4)0.02387 (10)0.8127 (2)0.0353 (8)
O160.2561 (3)0.15357 (8)0.26427 (19)0.0242 (6)
O170.1043 (4)0.08087 (11)0.0389 (2)0.0359 (8)
O180.7100 (3)0.11607 (9)0.0956 (2)0.0276 (6)
O190.0581 (4)0.23205 (10)0.0029 (2)0.0368 (8)
O210.4230 (4)0.04874 (9)0.2397 (2)0.0328 (7)
O200.4755 (4)0.05014 (11)0.1018 (2)0.0391 (8)
O1W0.4420 (3)0.20339 (9)0.3986 (2)0.0306 (7)
H1W10.46280.22320.43560.037*
H2W10.51300.20250.36030.037*
N10.1156 (4)0.24862 (10)0.4300 (2)0.0220 (7)
N20.0761 (4)0.07590 (10)0.4342 (2)0.0235 (7)
N30.1305 (4)0.16570 (11)0.4247 (3)0.0335 (9)
N50.1852 (4)0.12145 (10)0.6770 (2)0.0227 (7)
H5N0.13320.11340.63280.027*
N60.2417 (4)0.19710 (11)0.7100 (3)0.0326 (9)
N70.4788 (4)0.15196 (11)0.6986 (2)0.0239 (7)
N80.3313 (4)0.00935 (10)0.7439 (3)0.0273 (8)
N90.1150 (4)0.10073 (10)0.1776 (2)0.0206 (7)
H9N0.09000.09390.22750.025*
N100.4083 (4)0.12428 (10)0.1456 (2)0.0221 (7)
N110.1777 (4)0.16832 (11)0.0997 (3)0.0291 (8)
N120.4026 (4)0.03781 (11)0.1658 (3)0.0287 (8)
C10.1412 (5)0.10650 (13)0.7543 (3)0.0283 (9)
C20.0173 (5)0.07598 (12)0.7483 (3)0.0240 (8)
C30.0265 (5)0.05644 (13)0.6712 (3)0.0262 (9)
H3A0.02280.06200.62140.031*
C40.1425 (5)0.02891 (12)0.6690 (3)0.0257 (9)
H4A0.17360.01610.61800.031*
C50.2113 (5)0.02101 (12)0.7450 (3)0.0241 (8)
C60.1690 (5)0.03933 (13)0.8218 (3)0.0268 (9)
H6A0.21710.03310.87180.032*
C70.0544 (5)0.06701 (14)0.8232 (3)0.0271 (9)
H7A0.02460.07980.87450.033*
C80.5902 (5)0.13294 (14)0.6451 (3)0.0294 (9)
H8A0.59870.10480.65920.035*
H8B0.55770.13530.58470.035*
C90.7396 (5)0.15283 (15)0.6612 (3)0.0328 (10)
H9A0.73150.18070.64460.039*
H9B0.81350.14030.62630.039*
C100.6829 (5)0.16947 (15)0.8023 (3)0.0323 (10)
H10A0.71810.16750.86240.039*
H10B0.67660.19760.78740.039*
C110.5275 (5)0.15078 (15)0.7903 (3)0.0306 (10)
H11A0.45630.16540.82370.037*
H11B0.53080.12330.81040.037*
C120.0768 (6)0.20654 (17)0.6937 (4)0.0247 (14)0.774 (10)
H12A0.06000.21970.63830.030*0.774 (10)
H12B0.01770.18210.69310.030*0.774 (10)
C130.0308 (6)0.23368 (17)0.7651 (5)0.0253 (14)0.774 (10)
H13A0.05230.22090.82040.030*0.774 (10)
H13B0.07690.23890.75880.030*0.774 (10)
C140.2719 (6)0.26266 (16)0.7769 (4)0.0254 (14)0.774 (10)
H14A0.32680.28780.77790.031*0.774 (10)
H14B0.29060.24970.83220.031*0.774 (10)
C150.3264 (6)0.23621 (19)0.7060 (5)0.0254 (14)0.774 (10)
H15A0.43430.23160.71440.031*0.774 (10)
H15B0.30650.24880.65030.031*0.774 (10)
C12'0.0826 (19)0.1977 (5)0.7525 (15)0.022 (5)0.226 (10)
H12C0.09350.20010.81470.027*0.226 (10)
H12D0.02270.17420.73710.027*0.226 (10)
C13'0.020 (2)0.2332 (6)0.7128 (19)0.028 (5)0.226 (10)
H13C0.03650.23340.65150.034*0.226 (10)
H13D0.08700.23510.72070.034*0.226 (10)
C14'0.260 (2)0.2646 (7)0.7164 (14)0.029 (5)0.226 (10)
H14C0.32460.28780.72580.034*0.226 (10)
H14D0.23940.26130.65480.034*0.226 (10)
C15'0.334 (2)0.2292 (6)0.7525 (15)0.021 (4)0.226 (10)
H15C0.43890.22760.73760.025*0.226 (10)
H15D0.32950.22820.81470.025*0.226 (10)
C160.0600 (4)0.07706 (13)0.1110 (3)0.0232 (8)
C170.0588 (4)0.04707 (12)0.1310 (3)0.0204 (8)
C180.1063 (5)0.03914 (12)0.2129 (3)0.0223 (8)
H18A0.06260.05280.26020.027*
C190.2190 (5)0.01093 (12)0.2249 (3)0.0244 (8)
H19A0.25030.00520.27970.029*
C200.2829 (5)0.00829 (12)0.1530 (3)0.0245 (8)
C210.2394 (5)0.00083 (14)0.0706 (3)0.0290 (10)
H21A0.28550.01390.02330.035*
C220.1260 (5)0.02655 (14)0.0603 (3)0.0282 (9)
H22A0.09340.03150.00550.034*
C230.4396 (5)0.10863 (14)0.0601 (3)0.0275 (9)
H23A0.44280.07970.06180.033*
H23B0.35970.11660.01840.033*
C240.5900 (5)0.12474 (14)0.0332 (3)0.0273 (9)
H24A0.58240.15350.02560.033*
H24B0.61300.11310.02160.033*
C250.6777 (5)0.13313 (13)0.1763 (3)0.0264 (9)
H25A0.76140.12800.21780.032*
H25B0.66700.16180.17000.032*
C260.5345 (4)0.11600 (13)0.2097 (3)0.0243 (8)
H26A0.51430.12820.26450.029*
H26B0.54540.08740.21830.029*
C270.0130 (5)0.17653 (15)0.0915 (4)0.0262 (13)0.845 (9)
H27A0.04340.15190.09680.031*0.845 (9)
H27B0.01500.19470.13660.031*0.845 (9)
C280.0221 (7)0.1951 (2)0.0041 (5)0.0331 (14)0.845 (9)
H28A0.12990.19990.00390.040*0.845 (9)
H28B0.00700.17680.04060.040*0.845 (9)
C290.2173 (6)0.22426 (19)0.0044 (5)0.0351 (15)0.845 (9)
H29A0.24370.20610.04110.042*0.845 (9)
H29B0.27210.24900.00270.042*0.845 (9)
C300.2626 (6)0.20632 (15)0.0901 (4)0.0273 (13)0.845 (9)
H30A0.23970.22470.13580.033*0.845 (9)
H30B0.37040.20110.09390.033*0.845 (9)
C27'0.031 (3)0.1624 (8)0.0344 (16)0.018 (6)*0.155 (9)
H27C0.03560.14180.05460.022*0.155 (9)
H27D0.05920.15580.02330.022*0.155 (9)
C28'0.037 (3)0.2007 (9)0.037 (2)0.016 (6)*0.155 (9)
H28C0.13580.19980.00660.019*0.155 (9)
H28D0.05210.20780.09660.019*0.155 (9)
C29'0.208 (3)0.2333 (8)0.0522 (19)0.018 (6)*0.155 (9)
H29C0.18830.23870.11190.022*0.155 (9)
H29D0.27200.25440.03180.022*0.155 (9)
C30'0.283 (3)0.1942 (9)0.045 (2)0.026 (7)*0.155 (9)
H30C0.28300.18520.01430.031*0.155 (9)
H30D0.38600.19480.06980.031*0.155 (9)
O1S0.4337 (4)0.11083 (9)0.4241 (2)0.0289 (7)
C1S0.4988 (5)0.08145 (12)0.4558 (3)0.0265 (9)
C2S0.6548 (5)0.07059 (15)0.4332 (3)0.0337 (10)
H2SA0.68170.08580.38400.051*
H2SB0.72450.07630.48110.051*
H2SC0.65870.04260.41980.051*
C3S0.4258 (6)0.05516 (14)0.5204 (3)0.0343 (10)
H3SA0.35480.07060.55100.051*
H3SB0.37400.03350.49090.051*
H3SC0.50200.04460.56050.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.01413 (10)0.01609 (10)0.02842 (12)0.00030 (9)0.00104 (7)0.00166 (10)
P10.0146 (4)0.0218 (5)0.0319 (5)0.0002 (4)0.0007 (4)0.0071 (4)
P20.0147 (5)0.0179 (5)0.0284 (5)0.0002 (4)0.0018 (4)0.0052 (4)
O10.0222 (15)0.0216 (14)0.0283 (16)0.0023 (11)0.0031 (12)0.0035 (12)
O20.0225 (15)0.0217 (14)0.0280 (16)0.0022 (11)0.0005 (12)0.0015 (12)
O30.0355 (18)0.0208 (15)0.0394 (19)0.0096 (13)0.0057 (14)0.0008 (13)
O40.0265 (16)0.0270 (15)0.0266 (16)0.0022 (12)0.0001 (12)0.0018 (12)
O50.0308 (16)0.0208 (14)0.0261 (15)0.0045 (12)0.0024 (12)0.0023 (12)
O60.0320 (18)0.0214 (15)0.045 (2)0.0071 (13)0.0075 (14)0.0041 (13)
O70.0242 (16)0.0283 (16)0.0430 (19)0.0007 (12)0.0076 (14)0.0035 (14)
O80.0247 (16)0.0264 (16)0.0428 (19)0.0032 (12)0.0084 (14)0.0030 (14)
O90.0169 (17)0.053 (2)0.106 (4)0.0002 (16)0.0042 (19)0.001 (2)
O100.0202 (14)0.0228 (14)0.0323 (16)0.0017 (12)0.0040 (11)0.0009 (13)
O110.0307 (18)0.061 (2)0.0279 (17)0.0174 (16)0.0031 (14)0.0086 (16)
O120.0166 (15)0.0417 (19)0.0365 (18)0.0019 (13)0.0030 (12)0.0032 (14)
O130.0218 (16)0.0234 (16)0.059 (2)0.0033 (12)0.0079 (15)0.0020 (15)
O140.0313 (18)0.0339 (18)0.0372 (19)0.0062 (14)0.0013 (14)0.0084 (14)
O150.0351 (18)0.0303 (17)0.0403 (19)0.0054 (14)0.0020 (15)0.0093 (14)
O160.0214 (14)0.0201 (15)0.0316 (16)0.0021 (11)0.0046 (12)0.0033 (11)
O170.0338 (18)0.054 (2)0.0206 (16)0.0184 (16)0.0048 (13)0.0007 (14)
O180.0164 (14)0.0319 (16)0.0346 (17)0.0005 (12)0.0027 (12)0.0007 (13)
O190.0216 (16)0.0343 (18)0.054 (2)0.0014 (13)0.0043 (15)0.0208 (16)
O210.0327 (18)0.0267 (16)0.0401 (19)0.0091 (13)0.0110 (14)0.0008 (14)
O200.0299 (18)0.044 (2)0.043 (2)0.0173 (15)0.0019 (15)0.0128 (16)
O1W0.0152 (14)0.0298 (16)0.047 (2)0.0053 (12)0.0076 (13)0.0133 (14)
N10.0194 (16)0.0195 (16)0.0273 (18)0.0031 (13)0.0027 (13)0.0007 (14)
N20.0216 (17)0.0196 (17)0.0290 (19)0.0013 (13)0.0018 (14)0.0010 (14)
N30.0201 (17)0.0229 (18)0.057 (3)0.0006 (15)0.0019 (17)0.0033 (18)
N50.0191 (17)0.0183 (16)0.0302 (19)0.0058 (13)0.0022 (14)0.0042 (14)
N60.0116 (16)0.028 (2)0.058 (3)0.0013 (14)0.0010 (16)0.0219 (18)
N70.0142 (15)0.0325 (19)0.0248 (18)0.0014 (13)0.0000 (13)0.0098 (14)
N80.0261 (19)0.0180 (17)0.038 (2)0.0014 (14)0.0013 (16)0.0006 (15)
N90.0182 (16)0.0210 (16)0.0228 (17)0.0021 (13)0.0029 (13)0.0055 (13)
N100.0149 (16)0.0287 (18)0.0225 (17)0.0013 (13)0.0001 (13)0.0043 (14)
N110.0155 (16)0.0246 (19)0.047 (2)0.0036 (13)0.0039 (15)0.0146 (16)
N120.0249 (19)0.0254 (18)0.036 (2)0.0059 (15)0.0042 (16)0.0073 (16)
C10.024 (2)0.032 (2)0.029 (2)0.0019 (17)0.0014 (17)0.0056 (18)
C20.0191 (19)0.025 (2)0.028 (2)0.0002 (15)0.0005 (16)0.0020 (17)
C30.023 (2)0.031 (2)0.024 (2)0.0014 (17)0.0024 (16)0.0033 (17)
C40.028 (2)0.022 (2)0.027 (2)0.0017 (16)0.0034 (17)0.0032 (16)
C50.0186 (19)0.0198 (19)0.033 (2)0.0022 (15)0.0037 (16)0.0010 (16)
C60.023 (2)0.036 (2)0.021 (2)0.0006 (17)0.0008 (16)0.0009 (17)
C70.021 (2)0.036 (2)0.023 (2)0.0007 (17)0.0017 (16)0.0042 (18)
C80.020 (2)0.033 (2)0.035 (2)0.0045 (17)0.0008 (17)0.0093 (19)
C90.020 (2)0.044 (3)0.034 (2)0.0010 (18)0.0024 (18)0.002 (2)
C100.023 (2)0.042 (3)0.031 (2)0.0059 (18)0.0018 (17)0.004 (2)
C110.021 (2)0.042 (3)0.028 (2)0.0053 (18)0.0039 (17)0.0069 (19)
C120.015 (2)0.029 (3)0.031 (4)0.002 (2)0.005 (2)0.007 (3)
C130.018 (3)0.021 (3)0.037 (4)0.000 (2)0.003 (3)0.006 (3)
C140.018 (3)0.024 (3)0.035 (4)0.001 (2)0.002 (2)0.006 (2)
C150.019 (3)0.028 (3)0.031 (4)0.004 (2)0.011 (3)0.011 (3)
C12'0.013 (8)0.020 (9)0.034 (12)0.011 (6)0.003 (7)0.000 (8)
C13'0.025 (10)0.016 (9)0.042 (14)0.000 (7)0.005 (10)0.017 (9)
C14'0.011 (8)0.052 (13)0.023 (12)0.003 (8)0.001 (7)0.018 (9)
C15'0.028 (10)0.019 (9)0.016 (10)0.010 (7)0.016 (8)0.009 (8)
C160.0160 (18)0.028 (2)0.025 (2)0.0003 (15)0.0002 (15)0.0004 (16)
C170.0169 (18)0.0206 (18)0.024 (2)0.0015 (14)0.0013 (15)0.0008 (15)
C180.0202 (19)0.025 (2)0.021 (2)0.0016 (15)0.0008 (15)0.0011 (16)
C190.025 (2)0.022 (2)0.027 (2)0.0007 (16)0.0037 (16)0.0018 (16)
C200.0177 (19)0.023 (2)0.033 (2)0.0011 (15)0.0017 (16)0.0019 (17)
C210.025 (2)0.037 (2)0.025 (2)0.0067 (18)0.0022 (17)0.0054 (18)
C220.024 (2)0.036 (2)0.025 (2)0.0057 (18)0.0003 (17)0.0005 (18)
C230.024 (2)0.031 (2)0.028 (2)0.0028 (17)0.0032 (17)0.0002 (17)
C240.023 (2)0.031 (2)0.028 (2)0.0018 (17)0.0038 (17)0.0017 (18)
C250.0165 (19)0.029 (2)0.033 (2)0.0003 (16)0.0003 (16)0.0018 (18)
C260.0177 (19)0.030 (2)0.025 (2)0.0032 (16)0.0020 (15)0.0030 (17)
C270.017 (2)0.026 (2)0.035 (3)0.0017 (18)0.001 (2)0.007 (2)
C280.022 (3)0.040 (4)0.036 (4)0.003 (2)0.002 (3)0.010 (3)
C290.021 (3)0.039 (3)0.045 (4)0.001 (2)0.003 (2)0.018 (3)
C300.020 (3)0.020 (2)0.042 (3)0.0036 (18)0.001 (2)0.008 (2)
O1S0.0272 (16)0.0246 (15)0.0344 (18)0.0044 (12)0.0017 (13)0.0054 (13)
C1S0.025 (2)0.021 (2)0.033 (2)0.0034 (16)0.0029 (17)0.0070 (17)
C2S0.028 (2)0.037 (3)0.036 (3)0.0089 (19)0.0009 (19)0.004 (2)
C3S0.034 (3)0.035 (3)0.034 (3)0.004 (2)0.001 (2)0.003 (2)
Geometric parameters (Å, º) top
La1—O102.402 (3)C8—H8A0.9700
La1—O162.432 (3)C8—H8B0.9700
La1—O1W2.489 (3)C9—H9A0.9700
La1—O1S2.605 (3)C9—H9B0.9700
La1—O72.608 (3)C10—C111.515 (6)
La1—O22.611 (3)C10—H10A0.9700
La1—O82.623 (3)C10—H10B0.9700
La1—O12.640 (3)C11—H11A0.9700
La1—O52.642 (3)C11—H11B0.9700
La1—O42.786 (3)C12—C131.508 (9)
La1—N13.031 (3)C12—H12A0.9700
La1—N33.049 (4)C12—H12B0.9700
P1—O101.493 (3)C13—H13A0.9700
P1—N71.618 (3)C13—H13B0.9700
P1—N61.625 (4)C14—C151.513 (9)
P1—N51.687 (3)C14—H14A0.9700
P2—O161.489 (3)C14—H14B0.9700
P2—N101.616 (4)C15—H15A0.9700
P2—N111.630 (4)C15—H15B0.9700
P2—N91.690 (3)C12'—C13'1.44 (3)
O1—N11.251 (4)C12'—H12C0.9700
O2—N11.272 (4)C12'—H12D0.9700
O3—N11.229 (4)C13'—H13C0.9700
O4—N21.263 (5)C13'—H13D0.9700
O5—N21.267 (4)C14'—C15'1.45 (3)
O6—N21.234 (4)C14'—H14C0.9700
O7—N31.281 (5)C14'—H14D0.9700
O8—N31.261 (5)C15'—H15C0.9700
O9—N31.218 (5)C15'—H15D0.9700
O11—C11.215 (5)C16—C171.500 (6)
O12—C91.422 (5)C17—C181.389 (6)
O12—C101.435 (6)C17—C221.399 (6)
O13—C131.419 (6)C18—C191.394 (6)
O13—C141.449 (6)C18—H18A0.9300
O13—C14'1.539 (18)C19—C201.382 (6)
O13—C13'1.64 (2)C19—H19A0.9300
O14—N81.231 (5)C20—C211.381 (6)
O15—N81.222 (5)C21—C221.376 (6)
O17—C161.214 (5)C21—H21A0.9300
O18—C251.423 (5)C22—H22A0.9300
O18—C241.427 (5)C23—C241.518 (6)
O19—C291.433 (6)C23—H23A0.9700
O19—C281.435 (7)C23—H23B0.9700
O19—C28'1.50 (3)C24—H24A0.9700
O19—C29'1.54 (3)C24—H24B0.9700
O21—N121.229 (5)C25—C261.511 (6)
O20—N121.227 (5)C25—H25A0.9700
O1W—H1W10.8904C25—H25B0.9700
O1W—H2W10.8900C26—H26A0.9700
N5—C11.377 (6)C26—H26B0.9700
N5—H5N0.8502C27—C281.510 (8)
N6—C15'1.484 (19)C27—H27A0.9700
N6—C121.503 (6)C27—H27B0.9700
N6—C151.512 (7)C28—H28A0.9700
N6—C12'1.590 (18)C28—H28B0.9700
N7—C111.467 (5)C29—C301.496 (8)
N7—C81.470 (5)C29—H29A0.9700
N8—C51.470 (5)C29—H29B0.9700
N9—C161.371 (5)C30—H30A0.9700
N9—H9N0.8501C30—H30B0.9700
N10—C231.469 (5)C27'—C28'1.42 (4)
N10—C261.482 (5)C27'—H27C0.9700
N11—C271.484 (6)C27'—H27D0.9700
N11—C301.489 (6)C28'—H28C0.9700
N11—C30'1.56 (3)C28'—H28D0.9700
N11—C27'1.62 (2)C29'—C30'1.48 (4)
N12—C201.471 (5)C29'—H29C0.9700
C1—C21.499 (6)C29'—H29D0.9700
C2—C71.390 (6)C30'—H30C0.9700
C2—C31.400 (6)C30'—H30D0.9700
C3—C41.380 (6)O1S—C1S1.229 (5)
C3—H3A0.9300C1S—C2S1.491 (6)
C4—C51.384 (6)C1S—C3S1.508 (7)
C4—H4A0.9300C2S—H2SA0.9600
C5—C61.375 (6)C2S—H2SB0.9600
C6—C71.375 (6)C2S—H2SC0.9600
C6—H6A0.9300C3S—H3SA0.9600
C7—H7A0.9300C3S—H3SB0.9600
C8—C91.490 (6)C3S—H3SC0.9600
O10—La1—O16148.98 (10)O12—C9—C8110.9 (4)
O10—La1—O1W82.42 (10)O12—C9—H9A109.5
O16—La1—O1W77.39 (10)C8—C9—H9A109.5
O10—La1—O1S73.39 (10)O12—C9—H9B109.5
O16—La1—O1S78.90 (10)C8—C9—H9B109.5
O1W—La1—O1S75.62 (10)H9A—C9—H9B108.0
O10—La1—O7126.71 (10)O12—C10—C11111.4 (4)
O16—La1—O781.77 (10)O12—C10—H10A109.4
O1W—La1—O7144.20 (11)C11—C10—H10A109.4
O1S—La1—O7128.23 (10)O12—C10—H10B109.4
O10—La1—O2116.93 (10)C11—C10—H10B109.4
O16—La1—O281.24 (9)H10A—C10—H10B108.0
O1W—La1—O277.11 (10)N7—C11—C10108.9 (4)
O1S—La1—O2149.10 (10)N7—C11—H11A109.9
O7—La1—O271.15 (9)C10—C11—H11A109.9
O10—La1—O883.51 (10)N7—C11—H11B109.9
O16—La1—O8127.48 (10)C10—C11—H11B109.9
O1W—La1—O8130.82 (10)H11A—C11—H11B108.3
O1S—La1—O8142.44 (10)N6—C12—C13107.6 (5)
O7—La1—O848.86 (10)N6—C12—H12A110.2
O2—La1—O868.13 (10)C13—C12—H12A110.2
O10—La1—O168.45 (9)N6—C12—H12B110.2
O16—La1—O1122.63 (9)C13—C12—H12B110.2
O1W—La1—O167.15 (9)H12A—C12—H12B108.5
O1S—La1—O1129.06 (9)O13—C13—C12109.5 (5)
O7—La1—O1101.74 (9)O13—C13—H13A109.8
O2—La1—O148.56 (9)C12—C13—H13A109.8
O8—La1—O163.83 (9)O13—C13—H13B109.8
O10—La1—O571.10 (9)C12—C13—H13B109.8
O16—La1—O5116.81 (9)H13A—C13—H13B108.2
O1W—La1—O5147.22 (10)O13—C14—C15109.5 (5)
O1S—La1—O578.48 (10)O13—C14—H14A109.8
O7—La1—O568.54 (10)C15—C14—H14A109.8
O2—La1—O5132.00 (9)O13—C14—H14B109.8
O8—La1—O566.03 (9)C15—C14—H14B109.8
O1—La1—O5117.45 (9)H14A—C14—H14B108.2
O10—La1—O4108.97 (9)N6—C15—C14107.3 (5)
O16—La1—O470.16 (9)N6—C15—H15A110.3
O1W—La1—O4132.43 (9)C14—C15—H15A110.3
O1S—La1—O464.88 (9)N6—C15—H15B110.3
O7—La1—O463.41 (9)C14—C15—H15B110.3
O2—La1—O4128.66 (9)H15A—C15—H15B108.5
O8—La1—O496.69 (9)C13'—C12'—N699.2 (16)
O1—La1—O4160.38 (9)C13'—C12'—H12C111.9
O5—La1—O446.80 (9)N6—C12'—H12C111.9
O10—La1—N192.32 (10)C13'—C12'—H12D111.9
O16—La1—N1103.96 (9)N6—C12'—H12D111.9
O1W—La1—N173.33 (9)H12C—C12'—H12D109.6
O1S—La1—N1147.25 (9)C12'—C13'—O13105.0 (17)
O7—La1—N184.04 (9)C12'—C13'—H13C110.8
O2—La1—N124.66 (9)O13—C13'—H13C110.8
O8—La1—N160.45 (9)C12'—C13'—H13D110.8
O1—La1—N124.26 (9)O13—C13'—H13D110.8
O5—La1—N1125.36 (9)H13C—C13'—H13D108.8
O4—La1—N1147.32 (9)C15'—C14'—O13107.5 (17)
O10—La1—N3105.18 (11)C15'—C14'—H14C110.2
O16—La1—N3105.05 (11)O13—C14'—H14C110.2
O1W—La1—N3143.67 (10)C15'—C14'—H14D110.2
O1S—La1—N3140.71 (10)O13—C14'—H14D110.2
O7—La1—N324.62 (11)H14C—C14'—H14D108.5
O2—La1—N367.72 (10)C14'—C15'—N6101.0 (17)
O8—La1—N324.23 (11)C14'—C15'—H15C111.6
O1—La1—N382.47 (10)N6—C15'—H15C111.6
O5—La1—N364.71 (10)C14'—C15'—H15D111.6
O4—La1—N379.52 (10)N6—C15'—H15D111.6
N1—La1—N370.93 (10)H15C—C15'—H15D109.4
O10—P1—N7108.74 (17)O17—C16—N9121.1 (4)
O10—P1—N6118.1 (2)O17—C16—C17121.9 (4)
N7—P1—N6106.70 (18)N9—C16—C17117.0 (4)
O10—P1—N5103.07 (17)C18—C17—C22119.2 (4)
N7—P1—N5115.68 (19)C18—C17—C16124.7 (4)
N6—P1—N5104.86 (19)C22—C17—C16116.1 (4)
O16—P2—N10109.83 (18)C17—C18—C19120.5 (4)
O16—P2—N11116.93 (19)C17—C18—H18A119.8
N10—P2—N11105.71 (19)C19—C18—H18A119.8
O16—P2—N9104.36 (17)C20—C19—C18118.2 (4)
N10—P2—N9114.98 (18)C20—C19—H19A120.9
N11—P2—N9105.31 (17)C18—C19—H19A120.9
N1—O1—La195.6 (2)C21—C20—C19122.9 (4)
N1—O2—La196.5 (2)C21—C20—N12119.1 (4)
N2—O4—La194.3 (2)C19—C20—N12118.0 (4)
N2—O5—La1101.2 (2)C22—C21—C20118.1 (4)
N3—O7—La197.3 (2)C22—C21—H21A120.9
N3—O8—La197.2 (2)C20—C21—H21A120.9
P1—O10—La1158.91 (18)C21—C22—C17121.2 (4)
C9—O12—C10110.3 (3)C21—C22—H22A119.4
C13—O13—C14109.7 (4)C17—C22—H22A119.4
C13—O13—C14'111.1 (9)N10—C23—C24109.5 (4)
C14—O13—C13'113.4 (8)N10—C23—H23A109.8
C14'—O13—C13'96.2 (11)C24—C23—H23A109.8
P2—O16—La1160.70 (17)N10—C23—H23B109.8
C25—O18—C24109.8 (3)C24—C23—H23B109.8
C29—O19—C28109.1 (4)H23A—C23—H23B108.2
C29—O19—C28'114.5 (12)O18—C24—C23111.9 (4)
C28—O19—C29'113.4 (10)O18—C24—H24A109.2
C28'—O19—C29'106.1 (16)C23—C24—H24A109.2
La1—O1W—H1W1119.0O18—C24—H24B109.2
La1—O1W—H2W1131.9C23—C24—H24B109.2
H1W1—O1W—H2W1109.1H24A—C24—H24B107.9
O3—N1—O1121.3 (4)O18—C25—C26111.4 (3)
O3—N1—O2121.0 (3)O18—C25—H25A109.3
O1—N1—O2117.7 (3)C26—C25—H25A109.3
O3—N1—La1168.1 (3)O18—C25—H25B109.3
O1—N1—La160.11 (19)C26—C25—H25B109.3
O2—N1—La158.88 (19)H25A—C25—H25B108.0
O6—N2—O4121.8 (3)N10—C26—C25108.4 (3)
O6—N2—O5120.9 (4)N10—C26—H26A110.0
O4—N2—O5117.3 (3)C25—C26—H26A110.0
O9—N3—O8121.6 (4)N10—C26—H26B110.0
O9—N3—O7121.7 (4)C25—C26—H26B110.0
O8—N3—O7116.6 (4)H26A—C26—H26B108.4
O9—N3—La1178.4 (3)N11—C27—C28107.8 (4)
O8—N3—La158.6 (2)N11—C27—H27A110.2
O7—N3—La158.0 (2)C28—C27—H27A110.2
C1—N5—P1128.6 (3)N11—C27—H27B110.2
C1—N5—H5N115.0C28—C27—H27B110.2
P1—N5—H5N115.5H27A—C27—H27B108.5
C15'—N6—C12115.6 (9)O19—C28—C27110.1 (5)
C12—N6—C15107.0 (4)O19—C28—H28A109.6
C15'—N6—C12'106.7 (10)C27—C28—H28A109.6
C15—N6—C12'117.4 (7)O19—C28—H28B109.6
C15'—N6—P1125.4 (8)C27—C28—H28B109.6
C12—N6—P1117.2 (3)H28A—C28—H28B108.1
C15—N6—P1118.0 (3)O19—C29—C30110.9 (5)
C12'—N6—P1124.0 (7)O19—C29—H29A109.5
C11—N7—C8111.5 (3)C30—C29—H29A109.5
C11—N7—P1125.8 (3)O19—C29—H29B109.5
C8—N7—P1119.7 (3)C30—C29—H29B109.5
O15—N8—O14124.3 (4)H29A—C29—H29B108.0
O15—N8—C5117.7 (4)N11—C30—C29108.6 (5)
O14—N8—C5118.0 (4)N11—C30—H30A110.0
C16—N9—P2128.0 (3)C29—C30—H30A110.0
C16—N9—H9N115.8N11—C30—H30B110.0
P2—N9—H9N115.7C29—C30—H30B110.0
C23—N10—C26111.6 (3)H30A—C30—H30B108.3
C23—N10—P2124.8 (3)C28'—C27'—N11102 (2)
C26—N10—P2121.7 (3)C28'—C27'—H27C111.5
C27—N11—C30109.5 (4)N11—C27'—H27C111.5
C27—N11—C30'117.8 (11)C28'—C27'—H27D111.5
C30—N11—C27'115.8 (9)N11—C27'—H27D111.5
C30'—N11—C27'102.3 (14)H27C—C27'—H27D109.3
C27—N11—P2119.2 (3)C27'—C28'—O19112 (2)
C30—N11—P2116.2 (3)C27'—C28'—H28C109.3
C30'—N11—P2122.3 (11)O19—C28'—H28C109.3
C27'—N11—P2128.0 (9)C27'—C28'—H28D109.3
O20—N12—O21124.0 (4)O19—C28'—H28D109.3
O20—N12—C20117.9 (4)H28C—C28'—H28D108.0
O21—N12—C20118.1 (4)C30'—C29'—O19108 (2)
O11—C1—N5121.6 (4)C30'—C29'—H29C110.0
O11—C1—C2122.6 (4)O19—C29'—H29C110.0
N5—C1—C2115.8 (4)C30'—C29'—H29D110.0
C7—C2—C3119.8 (4)O19—C29'—H29D110.0
C7—C2—C1117.5 (4)H29C—C29'—H29D108.4
C3—C2—C1122.6 (4)C29'—C30'—N1199 (2)
C4—C3—C2120.3 (4)C29'—C30'—H30C111.9
C4—C3—H3A119.9N11—C30'—H30C111.9
C2—C3—H3A119.9C29'—C30'—H30D111.9
C3—C4—C5118.0 (4)N11—C30'—H30D111.9
C3—C4—H4A121.0H30C—C30'—H30D109.6
C5—C4—H4A121.0C1S—O1S—La1151.8 (3)
C6—C5—C4123.0 (4)O1S—C1S—C2S121.4 (4)
C6—C5—N8118.7 (4)O1S—C1S—C3S121.6 (4)
C4—C5—N8118.3 (4)C2S—C1S—C3S117.0 (4)
C7—C6—C5118.6 (4)C1S—C2S—H2SA109.5
C7—C6—H6A120.7C1S—C2S—H2SB109.5
C5—C6—H6A120.7H2SA—C2S—H2SB109.5
C6—C7—C2120.3 (4)C1S—C2S—H2SC109.5
C6—C7—H7A119.9H2SA—C2S—H2SC109.5
C2—C7—H7A119.9H2SB—C2S—H2SC109.5
N7—C8—C9109.3 (4)C1S—C3S—H3SA109.5
N7—C8—H8A109.8C1S—C3S—H3SB109.5
C9—C8—H8A109.8H3SA—C3S—H3SB109.5
N7—C8—H8B109.8C1S—C3S—H3SC109.5
C9—C8—H8B109.8H3SA—C3S—H3SC109.5
H8A—C8—H8B108.3H3SB—C3S—H3SC109.5
O10—La1—O1—N1169.1 (2)N5—P1—N6—C15179.3 (4)
O16—La1—O1—N143.7 (3)O10—P1—N6—C12'106.2 (10)
O1W—La1—O1—N1100.2 (2)N7—P1—N6—C12'131.0 (10)
O1S—La1—O1—N1146.7 (2)N5—P1—N6—C12'7.8 (10)
O7—La1—O1—N144.0 (2)O10—P1—N7—C11176.4 (3)
O2—La1—O1—N17.4 (2)N6—P1—N7—C1148.0 (4)
O8—La1—O1—N175.7 (2)N5—P1—N7—C1168.2 (4)
O5—La1—O1—N1115.8 (2)O10—P1—N7—C824.5 (4)
O4—La1—O1—N182.9 (3)N6—P1—N7—C8152.9 (4)
N3—La1—O1—N159.4 (2)N5—P1—N7—C890.9 (4)
O10—La1—O2—N13.6 (2)O16—P2—N9—C16178.5 (3)
O16—La1—O2—N1157.0 (2)N10—P2—N9—C1661.2 (4)
O1W—La1—O2—N178.1 (2)N11—P2—N9—C1654.8 (4)
O1S—La1—O2—N1106.6 (3)O16—P2—N10—C23177.8 (3)
O7—La1—O2—N1118.7 (2)N11—P2—N10—C2350.9 (4)
O8—La1—O2—N166.5 (2)N9—P2—N10—C2364.8 (4)
O1—La1—O2—N17.3 (2)O16—P2—N10—C2619.3 (4)
O5—La1—O2—N184.6 (2)N11—P2—N10—C26146.3 (3)
O4—La1—O2—N1147.2 (2)N9—P2—N10—C2698.0 (3)
N3—La1—O2—N192.7 (2)O16—P2—N11—C2776.2 (4)
O10—La1—O4—N241.2 (2)N10—P2—N11—C27161.2 (4)
O16—La1—O4—N2171.7 (2)N9—P2—N11—C2739.1 (4)
O1W—La1—O4—N2138.4 (2)O16—P2—N11—C3058.4 (4)
O1S—La1—O4—N2101.6 (2)N10—P2—N11—C3064.2 (4)
O7—La1—O4—N281.1 (2)N9—P2—N11—C30173.7 (4)
O2—La1—O4—N2111.4 (2)O16—P2—N11—C30'94.3 (15)
O8—La1—O4—N244.2 (2)N10—P2—N11—C30'28.3 (15)
O1—La1—O4—N237.7 (4)N9—P2—N11—C30'150.4 (15)
O5—La1—O4—N23.7 (2)O16—P2—N11—C27'121.4 (12)
N1—La1—O4—N286.7 (3)N10—P2—N11—C27'116.0 (12)
N3—La1—O4—N261.4 (2)N9—P2—N11—C27'6.1 (12)
O10—La1—O5—N2146.2 (2)P1—N5—C1—O114.9 (7)
O16—La1—O5—N21.2 (3)P1—N5—C1—C2173.6 (3)
O1W—La1—O5—N2108.3 (3)O11—C1—C2—C713.0 (7)
O1S—La1—O5—N270.0 (2)N5—C1—C2—C7165.4 (4)
O7—La1—O5—N269.4 (2)O11—C1—C2—C3166.4 (5)
O2—La1—O5—N2104.2 (2)N5—C1—C2—C315.1 (6)
O8—La1—O5—N2122.6 (2)C7—C2—C3—C41.3 (6)
O1—La1—O5—N2161.8 (2)C1—C2—C3—C4179.2 (4)
O4—La1—O5—N23.7 (2)C2—C3—C4—C51.0 (6)
N1—La1—O5—N2134.8 (2)C3—C4—C5—C60.0 (6)
N3—La1—O5—N295.9 (2)C3—C4—C5—N8177.8 (4)
O10—La1—O7—N332.5 (3)O15—N8—C5—C617.2 (6)
O16—La1—O7—N3161.0 (3)O14—N8—C5—C6162.3 (4)
O1W—La1—O7—N3106.3 (3)O15—N8—C5—C4160.7 (4)
O1S—La1—O7—N3130.2 (2)O14—N8—C5—C419.8 (6)
O2—La1—O7—N377.5 (2)C4—C5—C6—C70.7 (7)
O8—La1—O7—N30.4 (2)N8—C5—C6—C7178.5 (4)
O1—La1—O7—N339.2 (3)C5—C6—C7—C20.3 (7)
O5—La1—O7—N375.9 (2)C3—C2—C7—C60.7 (7)
O4—La1—O7—N3127.2 (3)C1—C2—C7—C6179.9 (4)
N1—La1—O7—N355.9 (2)C11—N7—C8—C956.7 (5)
O10—La1—O8—N3153.5 (3)P1—N7—C8—C9141.5 (3)
O16—La1—O8—N325.0 (3)C10—O12—C9—C860.5 (5)
O1W—La1—O8—N3132.4 (2)N7—C8—C9—O1258.8 (5)
O1S—La1—O8—N3101.8 (3)C9—O12—C10—C1159.1 (5)
O7—La1—O8—N30.5 (2)C8—N7—C11—C1054.9 (5)
O2—La1—O8—N384.1 (2)P1—N7—C11—C10144.6 (3)
O1—La1—O8—N3137.4 (3)O12—C10—C11—N755.9 (5)
O5—La1—O8—N381.3 (2)C15'—N6—C12—C1332.0 (12)
O4—La1—O8—N345.1 (3)C15—N6—C12—C1362.3 (7)
N1—La1—O8—N3110.1 (3)C12'—N6—C12—C1351.3 (11)
N7—P1—O10—La1169.9 (5)P1—N6—C12—C13162.6 (4)
N6—P1—O10—La168.4 (6)C14—O13—C13—C1263.1 (7)
N5—P1—O10—La146.6 (5)C14'—O13—C13—C1224.0 (11)
O16—La1—O10—P1161.9 (4)C13'—O13—C13—C1239.8 (15)
O1W—La1—O10—P1148.6 (5)N6—C12—C13—O1363.4 (7)
O1S—La1—O10—P1134.2 (5)C13—O13—C14—C1562.7 (7)
O7—La1—O10—P18.6 (6)C14'—O13—C14—C1536.4 (14)
O2—La1—O10—P177.2 (5)C13'—O13—C14—C1530.9 (14)
O8—La1—O10—P115.8 (5)C15'—N6—C15—C1450.5 (17)
O1—La1—O10—P180.2 (5)C12—N6—C15—C1461.6 (7)
O5—La1—O10—P151.0 (5)C12'—N6—C15—C1424.3 (12)
O4—La1—O10—P179.1 (5)P1—N6—C15—C14163.7 (4)
N1—La1—O10—P175.7 (5)O13—C14—C15—N661.7 (7)
N3—La1—O10—P14.9 (5)C15'—N6—C12'—C13'73.8 (19)
N10—P2—O16—La1125.1 (5)C12—N6—C12'—C13'36.9 (12)
N11—P2—O16—La1114.5 (5)C15—N6—C12'—C13'44.1 (18)
N9—P2—O16—La11.3 (6)P1—N6—C12'—C13'127.4 (12)
O10—La1—O16—P2118.6 (5)N6—C12'—C13'—O1373.9 (17)
O1W—La1—O16—P2169.2 (6)C13—O13—C13'—C12'47.6 (16)
O1S—La1—O16—P291.7 (6)C14—O13—C13'—C12'41 (2)
O7—La1—O16—P240.1 (5)C14'—O13—C13'—C12'75 (2)
O2—La1—O16—P2112.1 (6)C13—O13—C14'—C15'47.0 (17)
O8—La1—O16—P258.5 (6)C14—O13—C14'—C15'48.0 (14)
O1—La1—O16—P2138.8 (5)C13'—O13—C14'—C15'73.6 (18)
O5—La1—O16—P220.8 (6)O13—C14'—C15'—N675.7 (16)
O4—La1—O16—P224.6 (5)C12—N6—C15'—C14'34.1 (17)
N1—La1—O16—P2121.8 (5)C15—N6—C15'—C14'44.9 (16)
N3—La1—O16—P248.2 (6)C12'—N6—C15'—C14'71.6 (18)
La1—O1—N1—O3166.2 (3)P1—N6—C15'—C14'129.9 (11)
La1—O1—N1—O212.9 (3)P2—N9—C16—O170.9 (6)
La1—O2—N1—O3166.0 (3)P2—N9—C16—C17177.8 (3)
La1—O2—N1—O113.1 (3)O17—C16—C17—C18175.0 (4)
O10—La1—N1—O390.2 (14)N9—C16—C17—C186.3 (6)
O16—La1—N1—O3116.4 (14)O17—C16—C17—C226.0 (6)
O1W—La1—N1—O3171.6 (14)N9—C16—C17—C22172.7 (4)
O1S—La1—N1—O3152.5 (13)C22—C17—C18—C190.4 (6)
O7—La1—N1—O336.5 (14)C16—C17—C18—C19179.3 (4)
O2—La1—N1—O393.0 (14)C17—C18—C19—C200.9 (6)
O8—La1—N1—O39.0 (13)C18—C19—C20—C210.3 (6)
O1—La1—N1—O3100.4 (14)C18—C19—C20—N12179.5 (4)
O5—La1—N1—O321.9 (14)O20—N12—C20—C2111.1 (6)
O4—La1—N1—O341.5 (14)O21—N12—C20—C21168.5 (4)
N3—La1—N1—O315.0 (13)O20—N12—C20—C19168.7 (4)
O10—La1—N1—O110.2 (2)O21—N12—C20—C1911.6 (6)
O16—La1—N1—O1143.2 (2)C19—C20—C21—C220.9 (7)
O1W—La1—N1—O171.2 (2)N12—C20—C21—C22179.2 (4)
O1S—La1—N1—O152.1 (3)C20—C21—C22—C171.6 (7)
O7—La1—N1—O1136.8 (2)C18—C17—C22—C210.9 (7)
O2—La1—N1—O1166.6 (4)C16—C17—C22—C21178.1 (4)
O8—La1—N1—O191.4 (2)C26—N10—C23—C2454.1 (5)
O5—La1—N1—O178.5 (2)P2—N10—C23—C24141.5 (3)
O4—La1—N1—O1141.9 (2)C25—O18—C24—C2359.0 (5)
N3—La1—N1—O1115.4 (2)N10—C23—C24—O1855.5 (5)
O10—La1—N1—O2176.8 (2)C24—O18—C25—C2661.2 (4)
O16—La1—N1—O223.4 (2)C23—N10—C26—C2555.8 (4)
O1W—La1—N1—O295.4 (2)P2—N10—C26—C25139.3 (3)
O1S—La1—N1—O2114.5 (2)O18—C25—C26—N1059.2 (4)
O7—La1—N1—O256.6 (2)C30—N11—C27—C2859.0 (6)
O8—La1—N1—O2102.0 (2)C30'—N11—C27—C2825.4 (16)
O1—La1—N1—O2166.6 (4)C27'—N11—C27—C2848.3 (15)
O5—La1—N1—O2114.9 (2)P2—N11—C27—C28163.7 (4)
O4—La1—N1—O251.5 (3)C29—O19—C28—C2762.4 (7)
N3—La1—N1—O278.0 (2)C28'—O19—C28—C2746 (3)
La1—O4—N2—O6174.8 (3)C29'—O19—C28—C2729.0 (15)
La1—O4—N2—O56.3 (3)N11—C27—C28—O1961.4 (6)
La1—O5—N2—O6174.3 (3)C28—O19—C29—C3061.5 (7)
La1—O5—N2—O46.7 (4)C28'—O19—C29—C3038.3 (15)
La1—O8—N3—O9178.1 (4)C29'—O19—C29—C3042.4 (19)
La1—O8—N3—O70.8 (4)C27—N11—C30—C2958.2 (6)
La1—O7—N3—O9178.1 (4)C30'—N11—C30—C2953 (2)
La1—O7—N3—O80.8 (4)C27'—N11—C30—C2917.1 (12)
O10—La1—N3—O827.4 (3)P2—N11—C30—C29163.1 (4)
O16—La1—N3—O8159.7 (2)O19—C29—C30—N1159.3 (7)
O1W—La1—N3—O870.6 (3)C27—N11—C27'—C28'45.4 (16)
O1S—La1—N3—O8109.6 (3)C30—N11—C27'—C28'44 (2)
O7—La1—N3—O8179.2 (4)C30'—N11—C27'—C28'74 (2)
O2—La1—N3—O886.0 (2)P2—N11—C27'—C28'136.1 (16)
O1—La1—N3—O837.8 (2)N11—C27'—C28'—O1967 (2)
O5—La1—N3—O887.4 (3)C29—O19—C28'—C27'30 (3)
O4—La1—N3—O8134.4 (3)C28—O19—C28'—C27'51 (3)
N1—La1—N3—O859.8 (2)C29'—O19—C28'—C27'62 (3)
O10—La1—N3—O7153.5 (2)C29—O19—C29'—C30'47.3 (19)
O16—La1—N3—O719.5 (3)C28—O19—C29'—C30'41 (3)
O1W—La1—N3—O7108.6 (3)C28'—O19—C29'—C30'64 (3)
O1S—La1—N3—O771.3 (3)O19—C29'—C30'—N1172 (2)
O2—La1—N3—O793.2 (3)C27—N11—C30'—C29'39 (2)
O8—La1—N3—O7179.2 (4)C30—N11—C30'—C29'43.6 (18)
O1—La1—N3—O7141.4 (2)C27'—N11—C30'—C29'76 (2)
O5—La1—N3—O793.4 (2)P2—N11—C30'—C29'132.0 (16)
O4—La1—N3—O746.5 (2)O10—La1—O1S—C1S51.5 (6)
N1—La1—N3—O7119.4 (3)O16—La1—O1S—C1S142.6 (6)
O10—P1—N5—C1179.5 (4)O1W—La1—O1S—C1S137.7 (6)
N7—P1—N5—C161.0 (4)O7—La1—O1S—C1S72.5 (6)
N6—P1—N5—C156.3 (4)O2—La1—O1S—C1S166.5 (5)
O10—P1—N6—C15'98.9 (12)O8—La1—O1S—C1S3.0 (7)
N7—P1—N6—C15'23.9 (12)O1—La1—O1S—C1S94.1 (6)
N5—P1—N6—C15'147.1 (12)O5—La1—O1S—C1S22.0 (6)
O10—P1—N6—C1264.9 (4)O4—La1—O1S—C1S69.5 (6)
N7—P1—N6—C12172.4 (4)N1—La1—O1S—C1S118.8 (6)
N5—P1—N6—C1249.2 (4)N3—La1—O1S—C1S42.3 (7)
O10—P1—N6—C1565.2 (5)La1—O1S—C1S—C2S169.7 (4)
N7—P1—N6—C1557.5 (5)La1—O1S—C1S—C3S9.3 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O19i0.891.942.810 (7)164
O1W—H2W1···O13ii0.892.022.815 (6)147
N5—H5N···O50.852.192.988 (5)155
N9—H9N···O40.852.162.948 (5)153
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x1/2, y1/2, z+1/2.
(13) top
Crystal data top
C30H44ErN11O22P2·0.5(C3H6O)·0.5(CH4O)F(000) = 2400
Mr = 1185.02Dx = 1.749 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 39011 reflections
a = 8.7152 (4) Åθ = 1.5–26.1°
b = 33.5889 (14) ŵ = 2.03 mm1
c = 15.3815 (8) ÅT = 173 K
β = 92.113 (4)°Rod, colourless
V = 4499.6 (4) Å30.33 × 0.27 × 0.21 mm
Z = 4
Data collection top
STOE IPDS-2
diffractometer
8492 independent reflections
Radiation source: fine-focus sealed tube6850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi + ω scansθmax = 25.7°, θmin = 1.5°
Absorption correction: multi-scan
MULscanABS (Spek, 2003)
h = 1010
Tmin = 0.607, Tmax = 0.657k = 3740
42064 measured reflectionsl = 1818
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0638P)2 + 7.5884P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
8492 reflectionsΔρmax = 2.07 e Å3
590 parametersΔρmin = 1.59 e Å3
5 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0040 (2)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. A region of diffuse electron density, 114 electrons for a Potential Solvent Accessible Void of 341.9 Å3, was equated to 0.5 actetone and 0.5 methanol per molecule of complex, using the Squeeze routine in PLATON (Spek, 2003).

Restraints in final refinement: DFIX 0.88. 02 N1 H1N N5 H5N DFIX 0.84. 02 O1W H1WA O1W H1WB EADP O3 O4 O10 EADP O21 O20

The water O—H distances were restrained to 0.84 (2) Å, and the N—H distances were restrained to 0.88 (2) Å, with Uiso(H) = 1.5Ueq(parent O-atom) and 1.2Ueq(parent N-atom). C-bound H-atoms were included in calculated positons and treated as riding atoms: C—H = 0.95 - 0.99 Å, with Uiso(H) = 1.2Ueq(C).

One of the nitro groups undergoes considerable thermal motion. The anisotropic thermal parameters were restrained as above. No improvement was possible by trying to split the O-atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Er10.28773 (3)0.16647 (1)0.12397 (1)0.0254 (1)
P10.26077 (14)0.14013 (4)0.35288 (8)0.0226 (3)
P20.24187 (14)0.15775 (4)0.11277 (8)0.0238 (4)
O10.2304 (4)0.15914 (10)0.2662 (2)0.0254 (10)
O1W0.0579 (4)0.20088 (12)0.1238 (2)0.0324 (11)
O20.3949 (5)0.06963 (14)0.4590 (3)0.0484 (14)
O30.9214 (8)0.06254 (19)0.3052 (4)0.0909 (16)
O40.9044 (8)0.03457 (19)0.1794 (5)0.0909 (16)
O50.4546 (4)0.23338 (12)0.5322 (2)0.0363 (12)
O60.1930 (4)0.11725 (12)0.4560 (2)0.0367 (11)
O70.2558 (4)0.15008 (11)0.0173 (2)0.0276 (10)
O80.3382 (5)0.14371 (12)0.2970 (2)0.0389 (11)
O90.8673 (6)0.00816 (18)0.4293 (4)0.074 (2)
O100.8488 (8)0.0239 (2)0.3105 (4)0.0909 (16)
O110.4030 (4)0.27042 (11)0.2322 (2)0.0337 (11)
O120.2551 (4)0.14972 (14)0.1870 (3)0.0420 (14)
O130.3225 (4)0.22907 (11)0.0460 (2)0.0336 (11)
O140.3908 (4)0.22861 (11)0.1821 (2)0.0337 (11)
O150.4508 (5)0.27945 (12)0.1016 (3)0.0469 (14)
O160.5364 (4)0.15239 (12)0.2025 (2)0.0334 (11)
O170.5465 (5)0.16789 (14)0.0680 (2)0.0446 (14)
O180.7576 (5)0.15361 (18)0.1408 (3)0.0599 (18)
O190.3390 (5)0.09685 (11)0.1314 (2)0.0353 (12)
O200.0856 (7)0.11548 (16)0.1204 (4)0.0709 (14)
O210.1535 (7)0.05022 (16)0.1146 (4)0.0709 (14)
N10.3965 (5)0.10586 (12)0.3361 (3)0.0259 (11)
N20.8719 (7)0.03690 (19)0.2558 (5)0.062 (3)
N30.3316 (4)0.16967 (12)0.4291 (3)0.0257 (11)
N40.1047 (5)0.12263 (13)0.3902 (2)0.0264 (11)
N50.3618 (5)0.12437 (13)0.1556 (3)0.0285 (11)
N60.8174 (6)0.00459 (17)0.3568 (4)0.0474 (17)
N70.2981 (4)0.20032 (12)0.1486 (3)0.0260 (12)
N80.0647 (5)0.15312 (13)0.1452 (3)0.0290 (12)
N90.3905 (5)0.24697 (14)0.1101 (3)0.0327 (14)
N100.6190 (5)0.15745 (14)0.1371 (3)0.0349 (14)
N110.1956 (9)0.0863 (2)0.1231 (4)0.067 (2)
C10.4426 (6)0.07476 (16)0.3865 (3)0.0303 (17)
C20.5587 (6)0.04672 (16)0.3491 (3)0.0300 (17)
C30.6214 (7)0.01756 (18)0.4020 (4)0.0444 (19)
C40.7259 (7)0.0096 (2)0.3732 (5)0.052 (2)
C50.7643 (6)0.00700 (18)0.2894 (4)0.0437 (19)
C60.7092 (8)0.0221 (2)0.2324 (5)0.056 (3)
C70.6040 (8)0.04932 (19)0.2632 (4)0.0478 (19)
C80.4988 (5)0.17567 (16)0.4410 (3)0.0277 (16)
C90.5339 (6)0.19628 (17)0.5262 (4)0.0355 (17)
C100.2914 (6)0.22607 (18)0.5264 (4)0.0385 (17)
C110.2477 (6)0.20716 (16)0.4400 (4)0.0338 (17)
C120.0287 (6)0.11262 (18)0.3329 (3)0.0329 (17)
C130.1693 (6)0.13131 (18)0.3691 (3)0.0346 (17)
C140.0638 (6)0.12686 (19)0.5119 (3)0.0368 (19)
C150.0829 (6)0.10893 (17)0.4801 (3)0.0328 (17)
C160.3955 (6)0.12147 (16)0.2424 (3)0.0302 (17)
C170.5071 (6)0.08970 (16)0.2681 (3)0.0296 (17)
C180.5571 (7)0.05943 (18)0.2137 (4)0.0419 (19)
C190.6611 (8)0.0315 (2)0.2417 (4)0.047 (2)
C200.7120 (6)0.03463 (17)0.3252 (4)0.0373 (17)
C210.6624 (7)0.06394 (18)0.3816 (4)0.0418 (17)
C220.5584 (7)0.09139 (17)0.3524 (4)0.0412 (19)
C230.4618 (6)0.21065 (16)0.1490 (3)0.0296 (17)
C240.4934 (6)0.23515 (16)0.2287 (3)0.0338 (17)
C250.2419 (6)0.26064 (16)0.2332 (3)0.0300 (16)
C260.2038 (6)0.23672 (15)0.1528 (3)0.0273 (16)
C270.0065 (6)0.15796 (17)0.2359 (3)0.0333 (17)
C280.1541 (7)0.17411 (19)0.2349 (4)0.0406 (19)
C290.1979 (6)0.1457 (2)0.0988 (4)0.0435 (19)
C300.0406 (6)0.12749 (19)0.0959 (4)0.0413 (19)
H1WA0.039 (8)0.2212 (13)0.094 (4)0.0490*
H1N0.429 (5)0.1119 (10)0.286 (2)0.0310*
H1WB0.005 (6)0.203 (2)0.168 (3)0.0490*
H30.591300.016100.460600.0530*
H40.769300.029300.410900.0620*
H5N0.402 (6)0.1090 (14)0.116 (3)0.0340*
H60.742200.023400.174300.0670*
H8A0.536700.192000.392700.0330*
H8B0.551900.149600.440300.0330*
H9A0.504000.178700.574400.0420*
H9B0.645800.201100.532600.0420*
H10A0.235300.251500.532400.0470*
H10B0.262200.208200.574200.0470*
H11A0.135900.201900.436800.0410*
H11B0.271800.225700.392300.0410*
H12A0.041500.083400.329700.0390*
H12B0.013000.122800.273400.0390*
H13A0.157400.160600.369900.0420*
H13B0.260100.124700.331300.0420*
H14A0.081800.116900.571200.0440*
H14B0.052500.156200.515200.0440*
H15A0.171100.117300.518200.0390*
H15B0.076500.079500.481500.0390*
H180.520100.057700.156500.0500*
H190.696400.010600.204300.0560*
H210.698700.065300.439000.0500*
H220.521300.111800.390500.0490*
H23A0.524300.186000.149000.0350*
H23B0.490700.226000.095900.0350*
H24A0.603500.242400.228000.0400*
H24B0.470600.219000.281500.0400*
H25A0.214700.245000.286100.0360*
H25B0.180500.285400.235100.0360*
H26A0.224400.253000.099900.0330*
H26B0.093600.229500.155200.0330*
H27A0.006800.132000.266200.0400*
H27B0.073200.176500.267200.0400*
H28A0.151300.201100.209000.0490*
H28B0.195300.176600.295500.0490*
H29A0.268500.128800.066000.0520*
H29B0.193600.172200.070700.0520*
H30A0.002200.125000.034800.0500*
H30B0.045100.100500.121900.0500*
H770.563100.069600.226000.0570*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Er10.0246 (1)0.0324 (1)0.0195 (1)0.0044 (1)0.0039 (1)0.0020 (1)
P10.0190 (6)0.0289 (6)0.0202 (5)0.0013 (5)0.0032 (4)0.0006 (5)
P20.0219 (6)0.0290 (7)0.0206 (6)0.0020 (5)0.0015 (5)0.0003 (5)
O10.0286 (18)0.0327 (19)0.0153 (15)0.0042 (14)0.0078 (13)0.0026 (13)
O1W0.0266 (19)0.037 (2)0.034 (2)0.0098 (16)0.0085 (15)0.0082 (16)
O20.045 (2)0.066 (3)0.035 (2)0.019 (2)0.0143 (18)0.018 (2)
O30.095 (3)0.074 (2)0.104 (3)0.046 (2)0.008 (2)0.017 (2)
O40.095 (3)0.074 (2)0.104 (3)0.046 (2)0.008 (2)0.017 (2)
O50.034 (2)0.037 (2)0.038 (2)0.0050 (17)0.0021 (16)0.0098 (17)
O60.0243 (19)0.052 (2)0.0345 (19)0.0023 (17)0.0109 (15)0.0073 (17)
O70.0320 (19)0.0359 (19)0.0149 (15)0.0038 (15)0.0017 (13)0.0003 (14)
O80.049 (2)0.044 (2)0.0239 (18)0.0162 (19)0.0045 (16)0.0000 (16)
O90.065 (3)0.082 (4)0.077 (4)0.027 (3)0.017 (3)0.027 (3)
O100.095 (3)0.074 (2)0.104 (3)0.046 (2)0.008 (2)0.017 (2)
O110.034 (2)0.036 (2)0.0316 (18)0.0005 (16)0.0069 (15)0.0054 (16)
O120.025 (2)0.055 (3)0.046 (2)0.0005 (18)0.0001 (17)0.0017 (19)
O130.042 (2)0.035 (2)0.0237 (17)0.0036 (17)0.0019 (15)0.0000 (15)
O140.042 (2)0.035 (2)0.0238 (17)0.0020 (17)0.0037 (15)0.0019 (15)
O150.052 (3)0.036 (2)0.053 (2)0.016 (2)0.005 (2)0.0031 (19)
O160.0259 (19)0.045 (2)0.0294 (18)0.0020 (16)0.0027 (15)0.0077 (16)
O170.032 (2)0.073 (3)0.0293 (19)0.005 (2)0.0093 (16)0.0045 (19)
O180.020 (2)0.100 (4)0.060 (3)0.012 (2)0.0046 (19)0.002 (3)
O190.038 (2)0.032 (2)0.036 (2)0.0028 (17)0.0037 (16)0.0027 (16)
O200.091 (3)0.048 (2)0.074 (2)0.016 (2)0.009 (2)0.0027 (18)
O210.091 (3)0.048 (2)0.074 (2)0.016 (2)0.009 (2)0.0027 (18)
N10.027 (2)0.030 (2)0.0211 (19)0.0063 (18)0.0063 (16)0.0049 (16)
N20.051 (4)0.049 (4)0.086 (5)0.009 (3)0.000 (3)0.024 (3)
N30.0180 (19)0.032 (2)0.027 (2)0.0010 (17)0.0009 (15)0.0027 (17)
N40.019 (2)0.039 (2)0.0213 (19)0.0071 (17)0.0013 (15)0.0007 (17)
N50.032 (2)0.034 (2)0.0198 (19)0.0090 (19)0.0038 (17)0.0033 (17)
N60.038 (3)0.049 (3)0.055 (3)0.008 (2)0.001 (2)0.023 (3)
N70.020 (2)0.028 (2)0.030 (2)0.0029 (17)0.0021 (16)0.0021 (17)
N80.026 (2)0.034 (2)0.027 (2)0.0014 (18)0.0020 (17)0.0047 (17)
N90.029 (2)0.040 (3)0.029 (2)0.006 (2)0.0013 (18)0.0035 (19)
N100.025 (2)0.044 (3)0.036 (2)0.001 (2)0.0071 (19)0.001 (2)
N110.095 (5)0.057 (4)0.047 (3)0.008 (4)0.003 (3)0.002 (3)
C10.025 (3)0.037 (3)0.029 (3)0.000 (2)0.002 (2)0.004 (2)
C20.024 (3)0.031 (3)0.035 (3)0.000 (2)0.001 (2)0.000 (2)
C30.048 (4)0.040 (3)0.045 (3)0.009 (3)0.001 (3)0.008 (3)
C40.045 (4)0.045 (4)0.065 (4)0.015 (3)0.006 (3)0.006 (3)
C50.028 (3)0.032 (3)0.071 (4)0.008 (2)0.001 (3)0.013 (3)
C60.064 (5)0.052 (4)0.052 (4)0.016 (3)0.020 (3)0.007 (3)
C70.057 (4)0.042 (3)0.045 (3)0.017 (3)0.012 (3)0.003 (3)
C80.016 (2)0.034 (3)0.033 (3)0.0001 (19)0.0002 (19)0.001 (2)
C90.027 (3)0.040 (3)0.039 (3)0.000 (2)0.004 (2)0.005 (2)
C100.033 (3)0.043 (3)0.040 (3)0.001 (3)0.007 (2)0.014 (3)
C110.028 (3)0.032 (3)0.041 (3)0.006 (2)0.002 (2)0.005 (2)
C120.025 (3)0.045 (3)0.029 (3)0.007 (2)0.004 (2)0.006 (2)
C130.024 (3)0.045 (3)0.035 (3)0.000 (2)0.003 (2)0.009 (2)
C140.029 (3)0.054 (4)0.028 (3)0.002 (3)0.008 (2)0.002 (2)
C150.025 (3)0.044 (3)0.030 (3)0.001 (2)0.009 (2)0.008 (2)
C160.030 (3)0.030 (3)0.031 (3)0.001 (2)0.008 (2)0.003 (2)
C170.026 (3)0.033 (3)0.030 (3)0.000 (2)0.005 (2)0.004 (2)
C180.051 (4)0.043 (3)0.032 (3)0.012 (3)0.005 (3)0.001 (2)
C190.051 (4)0.049 (4)0.041 (3)0.019 (3)0.001 (3)0.003 (3)
C200.028 (3)0.038 (3)0.046 (3)0.003 (2)0.004 (2)0.012 (3)
C210.046 (3)0.038 (3)0.043 (3)0.001 (3)0.022 (3)0.007 (3)
C220.050 (4)0.032 (3)0.043 (3)0.000 (3)0.019 (3)0.000 (2)
C230.024 (3)0.034 (3)0.031 (3)0.002 (2)0.002 (2)0.001 (2)
C240.030 (3)0.037 (3)0.035 (3)0.001 (2)0.011 (2)0.001 (2)
C250.029 (3)0.036 (3)0.025 (2)0.002 (2)0.003 (2)0.005 (2)
C260.028 (3)0.028 (3)0.026 (2)0.004 (2)0.004 (2)0.0019 (19)
C270.031 (3)0.039 (3)0.030 (3)0.001 (2)0.001 (2)0.000 (2)
C280.031 (3)0.050 (4)0.040 (3)0.004 (3)0.009 (2)0.004 (3)
C290.027 (3)0.060 (4)0.044 (3)0.002 (3)0.010 (2)0.003 (3)
C300.027 (3)0.046 (4)0.051 (3)0.004 (2)0.005 (2)0.007 (3)
Geometric parameters (Å, º) top
Er1—O12.275 (3)C3—C41.374 (9)
Er1—O1W2.313 (4)C4—C51.346 (10)
Er1—O72.249 (3)C5—C61.387 (9)
Er1—O132.445 (4)C6—C71.390 (10)
Er1—O142.430 (4)C8—C91.504 (8)
Er1—O162.487 (3)C10—C111.509 (9)
Er1—O172.444 (4)C12—C131.502 (8)
Er1—O192.383 (4)C14—C151.511 (8)
Er1—O202.456 (6)C16—C171.506 (7)
P1—O11.493 (3)C17—C221.388 (8)
P1—N11.677 (4)C17—C181.377 (8)
P1—N31.639 (4)C18—C191.384 (9)
P1—N41.607 (4)C19—C201.378 (9)
P2—O71.491 (3)C20—C211.372 (8)
P2—N51.684 (5)C21—C221.380 (8)
P2—N71.615 (4)C23—C241.510 (7)
P2—N81.613 (5)C25—C261.522 (7)
O2—C11.217 (7)C27—C281.502 (8)
O3—N21.217 (9)C29—C301.500 (8)
O4—N21.221 (11)C3—H30.9500
O5—C91.430 (7)C4—H40.9500
O5—C101.443 (6)C6—H60.9500
O6—C131.440 (6)C7—H770.9500
O6—C141.428 (6)C8—H8A0.9900
O8—C161.217 (6)C8—H8B0.9900
O9—N61.218 (9)C9—H9A0.9900
O10—N61.218 (9)C9—H9B0.9900
O11—C241.423 (6)C10—H10A0.9900
O11—C251.442 (6)C10—H10B0.9900
O12—C281.427 (8)C11—H11A0.9900
O12—C291.434 (8)C11—H11B0.9900
O13—N91.281 (6)C12—H12A0.9900
O14—N91.268 (6)C12—H12B0.9900
O15—N91.220 (6)C13—H13A0.9900
O16—N101.270 (6)C13—H13B0.9900
O17—N101.266 (6)C14—H14A0.9900
O18—N101.214 (6)C14—H14B0.9900
O19—N111.301 (9)C15—H15A0.9900
O20—N111.371 (9)C15—H15B0.9900
O21—N111.272 (9)C18—H180.9500
O1W—H1WA0.84 (5)C19—H190.9500
O1W—H1WB0.84 (5)C21—H210.9500
N1—C11.353 (7)C22—H220.9500
N2—C51.480 (9)C23—H23A0.9900
N3—C81.476 (6)C23—H23B0.9900
N3—C111.469 (7)C24—H24A0.9900
N4—C121.472 (6)C24—H24B0.9900
N4—C151.476 (6)C25—H25A0.9900
N5—C161.381 (7)C25—H25B0.9900
N6—C201.460 (8)C26—H26A0.9900
N7—C231.469 (6)C26—H26B0.9900
N7—C261.473 (6)C27—H27A0.9900
N8—C301.487 (7)C27—H27B0.9900
N8—C271.476 (7)C28—H28A0.9900
N1—H1N0.86 (3)C28—H28B0.9900
N5—H5N0.86 (5)C29—H29A0.9900
C1—C21.512 (7)C29—H29B0.9900
C2—C31.374 (8)C30—H30A0.9900
C2—C71.396 (8)C30—H30B0.9900
O1—Er1—O1W80.46 (12)O8—C16—N5121.8 (5)
O1—Er1—O7151.50 (13)O8—C16—C17120.4 (4)
O1—Er1—O13126.89 (11)N5—C16—C17117.8 (4)
O1—Er1—O1480.24 (11)C16—C17—C18123.8 (5)
O1—Er1—O1674.38 (11)C16—C17—C22116.7 (5)
O1—Er1—O17125.38 (12)C18—C17—C22119.5 (5)
O1—Er1—O1983.98 (11)C17—C18—C19120.5 (6)
O1—Er1—O2076.31 (17)C18—C19—C20118.4 (6)
O1W—Er1—O792.58 (12)N6—C20—C19119.1 (5)
O1W—Er1—O1372.10 (12)N6—C20—C21118.2 (5)
O1W—Er1—O1483.08 (13)C19—C20—C21122.7 (6)
O1W—Er1—O16146.59 (12)C20—C21—C22118.0 (6)
O1W—Er1—O17143.16 (14)C17—C22—C21121.0 (5)
O1W—Er1—O19130.65 (14)N7—C23—C24109.8 (4)
O1W—Er1—O2074.22 (17)O11—C24—C23111.5 (4)
O7—Er1—O1375.51 (12)O11—C25—C26110.7 (4)
O7—Er1—O14126.64 (12)N7—C26—C25109.6 (4)
O7—Er1—O16119.82 (12)N8—C27—C28108.6 (4)
O7—Er1—O1775.36 (12)O12—C28—C27113.0 (5)
O7—Er1—O1979.77 (12)O12—C29—C30110.6 (5)
O7—Er1—O2075.20 (17)N8—C30—C29109.2 (5)
O13—Er1—O1452.48 (11)C2—C3—H3119.00
O13—Er1—O16106.27 (12)C4—C3—H3119.00
O13—Er1—O1771.20 (13)C3—C4—H4121.00
O13—Er1—O19147.26 (12)C5—C4—H4122.00
O13—Er1—O20133.67 (16)C5—C6—H6121.00
O14—Er1—O1671.39 (12)C7—C6—H6121.00
O14—Er1—O1777.26 (13)C2—C7—H77120.00
O14—Er1—O19139.40 (12)C6—C7—H77120.00
O14—Er1—O20149.59 (16)N3—C8—H8A110.00
O16—Er1—O1751.39 (11)N3—C8—H8B110.00
O16—Er1—O1968.38 (13)C9—C8—H8A110.00
O16—Er1—O20119.32 (16)C9—C8—H8B110.00
O17—Er1—O1982.08 (15)H8A—C8—H8B108.00
O17—Er1—O20132.54 (17)O5—C9—H9A109.00
O19—Er1—O2056.62 (17)O5—C9—H9B109.00
O1—P1—N1105.0 (2)C8—C9—H9A109.00
O1—P1—N3115.4 (2)C8—C9—H9B109.00
O1—P1—N4110.5 (2)H9A—C9—H9B108.00
N1—P1—N3106.0 (2)O5—C10—H10A110.00
N1—P1—N4114.5 (2)O5—C10—H10B110.00
N3—P1—N4105.5 (2)C11—C10—H10A110.00
O7—P2—N5104.0 (2)C11—C10—H10B110.00
O7—P2—N7118.3 (2)H10A—C10—H10B108.00
O7—P2—N8109.3 (2)N3—C11—H11A110.00
N5—P2—N7104.8 (2)N3—C11—H11B110.00
N5—P2—N8114.6 (2)C10—C11—H11A110.00
N7—P2—N8106.2 (2)C10—C11—H11B110.00
Er1—O1—P1150.1 (2)H11A—C11—H11B108.00
C9—O5—C10109.0 (4)N4—C12—H12A110.00
C13—O6—C14110.4 (4)N4—C12—H12B110.00
Er1—O7—P2155.8 (2)C13—C12—H12A110.00
C24—O11—C25110.4 (4)C13—C12—H12B110.00
C28—O12—C29110.1 (4)H12A—C12—H12B108.00
Er1—O13—N995.1 (3)O6—C13—H13A109.00
Er1—O14—N996.2 (3)O6—C13—H13B109.00
Er1—O16—N1095.7 (3)C12—C13—H13A109.00
Er1—O17—N1097.9 (3)C12—C13—H13B110.00
Er1—O19—N1194.9 (4)H13A—C13—H13B108.00
Er1—O20—N1189.9 (4)O6—C14—H14A109.00
H1WA—O1W—H1WB106 (6)O6—C14—H14B109.00
Er1—O1W—H1WA124 (5)C15—C14—H14A109.00
Er1—O1W—H1WB123 (4)C15—C14—H14B109.00
P1—N1—C1129.6 (4)H14A—C14—H14B108.00
O4—N2—C5117.7 (6)N4—C15—H15A110.00
O3—N2—O4123.8 (7)N4—C15—H15B110.00
O3—N2—C5118.5 (7)C14—C15—H15A110.00
P1—N3—C8121.0 (3)C14—C15—H15B110.00
P1—N3—C11115.1 (3)H15A—C15—H15B108.00
C8—N3—C11111.2 (4)C17—C18—H18120.00
P1—N4—C12122.0 (3)C19—C18—H18120.00
C12—N4—C15111.3 (4)C18—C19—H19121.00
P1—N4—C15126.1 (3)C20—C19—H19121.00
P2—N5—C16125.6 (4)C20—C21—H21121.00
O10—N6—C20118.6 (6)C22—C21—H21121.00
O9—N6—O10122.2 (6)C17—C22—H22119.00
O9—N6—C20119.2 (6)C21—C22—H22120.00
P2—N7—C23121.2 (3)N7—C23—H23A110.00
P2—N7—C26125.0 (3)N7—C23—H23B110.00
C23—N7—C26110.1 (4)C24—C23—H23A110.00
P2—N8—C27125.0 (4)C24—C23—H23B110.00
P2—N8—C30120.0 (4)H23A—C23—H23B108.00
C27—N8—C30110.4 (4)O11—C24—H24A109.00
O13—N9—O15121.7 (5)O11—C24—H24B109.00
O13—N9—O14115.5 (4)C23—C24—H24A109.00
O14—N9—O15122.8 (5)C23—C24—H24B109.00
O16—N10—O17115.0 (4)H24A—C24—H24B108.00
O16—N10—O18122.7 (5)O11—C25—H25A109.00
O17—N10—O18122.3 (5)O11—C25—H25B110.00
O20—N11—O21118.7 (7)C26—C25—H25A110.00
O19—N11—O21122.8 (7)C26—C25—H25B110.00
O19—N11—O20118.5 (6)H25A—C25—H25B108.00
C1—N1—H1N127 (3)N7—C26—H26A110.00
P1—N1—H1N104 (3)N7—C26—H26B110.00
C16—N5—H5N123 (3)C25—C26—H26A110.00
P2—N5—H5N111 (3)C25—C26—H26B110.00
N1—C1—C2116.9 (4)H26A—C26—H26B108.00
O2—C1—N1122.0 (5)N8—C27—H27A110.00
O2—C1—C2121.1 (5)N8—C27—H27B110.00
C1—C2—C3118.4 (4)C28—C27—H27A110.00
C1—C2—C7122.6 (5)C28—C27—H27B110.00
C3—C2—C7119.0 (5)H27A—C27—H27B108.00
C2—C3—C4122.4 (6)O12—C28—H28A109.00
C3—C4—C5117.2 (6)O12—C28—H28B109.00
N2—C5—C4118.3 (6)C27—C28—H28A109.00
N2—C5—C6117.8 (6)C27—C28—H28B109.00
C4—C5—C6123.9 (6)H28A—C28—H28B108.00
C5—C6—C7117.7 (6)O12—C29—H29A110.00
C2—C7—C6119.6 (6)O12—C29—H29B110.00
N3—C8—C9109.8 (4)C30—C29—H29A110.00
O5—C9—C8112.0 (4)C30—C29—H29B110.00
O5—C10—C11110.0 (4)H29A—C29—H29B108.00
N3—C11—C10110.5 (5)N8—C30—H30A110.00
N4—C12—C13108.7 (4)N8—C30—H30B110.00
O6—C13—C12110.7 (4)C29—C30—H30A110.00
O6—C14—C15111.9 (4)C29—C30—H30B110.00
N4—C15—C14108.6 (4)H30A—C30—H30B108.00
O1W—Er1—O1—P1169.5 (4)N8—P2—N7—C23165.8 (4)
O7—Er1—O1—P191.9 (5)N8—P2—N7—C2638.0 (5)
O13—Er1—O1—P1131.5 (4)O7—P2—N8—C27179.1 (4)
O14—Er1—O1—P1105.9 (4)O7—P2—N8—C3025.5 (5)
O16—Er1—O1—P132.7 (4)N5—P2—N8—C2763.0 (5)
O17—Er1—O1—P139.3 (5)N5—P2—N8—C3090.7 (4)
O19—Er1—O1—P136.5 (4)N7—P2—N8—C2752.2 (5)
O20—Er1—O1—P193.6 (4)N7—P2—N8—C30154.1 (4)
O1—Er1—O7—P2140.6 (5)C10—O5—C9—C861.2 (5)
O1W—Er1—O7—P265.9 (5)C9—O5—C10—C1161.2 (6)
O13—Er1—O7—P24.9 (5)C14—O6—C13—C1259.8 (6)
O14—Er1—O7—P217.4 (6)C13—O6—C14—C1558.7 (6)
O16—Er1—O7—P2105.5 (5)C25—O11—C24—C2358.9 (5)
O17—Er1—O7—P278.8 (5)C24—O11—C25—C2658.6 (5)
O19—Er1—O7—P2163.2 (6)C29—O12—C28—C2758.7 (6)
O20—Er1—O7—P2138.8 (6)C28—O12—C29—C3059.1 (6)
O1—Er1—O13—N937.7 (3)Er1—O13—N9—O148.8 (4)
O1W—Er1—O13—N9100.3 (3)Er1—O13—N9—O15171.0 (4)
O7—Er1—O13—N9162.1 (3)Er1—O14—N9—O138.9 (4)
O14—Er1—O13—N95.2 (2)Er1—O14—N9—O15170.9 (4)
O16—Er1—O13—N944.7 (3)Er1—O16—N10—O172.3 (5)
O17—Er1—O13—N982.9 (3)Er1—O16—N10—O18179.5 (5)
O19—Er1—O13—N9119.9 (3)Er1—O17—N10—O162.4 (5)
O20—Er1—O13—N9145.6 (3)Er1—O17—N10—O18179.5 (5)
O1—Er1—O14—N9159.5 (3)Er1—O19—N11—O204.3 (6)
O1W—Er1—O14—N978.0 (3)Er1—O19—N11—O21173.4 (6)
O7—Er1—O14—N910.1 (3)Er1—O20—N11—O194.2 (6)
O13—Er1—O14—N95.3 (2)Er1—O20—N11—O21173.6 (6)
O16—Er1—O14—N9123.9 (3)P1—N1—C1—O26.5 (8)
O17—Er1—O14—N970.7 (3)P1—N1—C1—C2174.4 (4)
O19—Er1—O14—N9131.9 (3)O3—N2—C5—C40.1 (9)
O20—Er1—O14—N9119.6 (4)O3—N2—C5—C6179.8 (6)
O1—Er1—O16—N10174.5 (3)O4—N2—C5—C4179.1 (6)
O1W—Er1—O16—N10131.9 (3)O4—N2—C5—C61.0 (9)
O7—Er1—O16—N1032.5 (3)P1—N3—C8—C9167.3 (4)
O13—Er1—O16—N1049.9 (3)C11—N3—C8—C952.7 (6)
O14—Er1—O16—N1089.7 (3)P1—N3—C11—C10163.3 (4)
O17—Er1—O16—N101.4 (3)C8—N3—C11—C1054.3 (6)
O19—Er1—O16—N1095.9 (3)P1—N4—C12—C13130.6 (4)
O20—Er1—O16—N10121.6 (3)C15—N4—C12—C1358.0 (6)
O1—Er1—O17—N109.6 (4)P1—N4—C15—C14132.7 (4)
O1W—Er1—O17—N10137.1 (3)C12—N4—C15—C1456.3 (6)
O7—Er1—O17—N10148.6 (3)P2—N5—C16—O80.3 (8)
O13—Er1—O17—N10132.0 (3)P2—N5—C16—C17179.5 (4)
O14—Er1—O17—N1077.6 (3)O9—N6—C20—C19177.1 (6)
O16—Er1—O17—N101.4 (3)O9—N6—C20—C215.7 (8)
O19—Er1—O17—N1067.2 (3)O10—N6—C20—C195.1 (9)
O20—Er1—O17—N1095.4 (4)O10—N6—C20—C21172.1 (6)
O1—Er1—O19—N1180.1 (3)P2—N7—C23—C24144.0 (4)
O1W—Er1—O19—N118.2 (4)C26—N7—C23—C2456.6 (5)
O7—Er1—O19—N1176.4 (3)P2—N7—C26—C25144.8 (4)
O13—Er1—O19—N11117.7 (4)C23—N7—C26—C2556.8 (5)
O14—Er1—O19—N11147.5 (3)P2—N8—C27—C28148.4 (4)
O16—Er1—O19—N11155.7 (3)C30—N8—C27—C2855.7 (6)
O17—Er1—O19—N11152.9 (3)P2—N8—C30—C29144.9 (4)
O20—Er1—O19—N112.5 (3)C27—N8—C30—C2957.9 (6)
O1—Er1—O20—N1194.2 (4)O2—C1—C2—C36.6 (8)
O1W—Er1—O20—N11178.0 (4)O2—C1—C2—C7173.3 (6)
O7—Er1—O20—N1185.0 (4)N1—C1—C2—C3172.6 (5)
O13—Er1—O20—N11137.4 (3)N1—C1—C2—C77.6 (8)
O14—Er1—O20—N11134.8 (4)C1—C2—C3—C4179.0 (5)
O16—Er1—O20—N1131.2 (4)C7—C2—C3—C40.9 (9)
O17—Er1—O20—N1131.6 (5)C1—C2—C7—C6178.8 (6)
O19—Er1—O20—N112.4 (3)C3—C2—C7—C61.1 (9)
N1—P1—O1—Er15.6 (5)C2—C3—C4—C50.8 (9)
N3—P1—O1—Er1110.8 (4)C3—C4—C5—N2177.6 (6)
N4—P1—O1—Er1129.6 (4)C3—C4—C5—C62.5 (10)
O1—P1—N1—C1164.2 (5)N2—C5—C6—C7177.8 (6)
N3—P1—N1—C173.1 (5)C4—C5—C6—C72.3 (10)
N4—P1—N1—C142.8 (5)C5—C6—C7—C20.4 (10)
O1—P1—N3—C888.0 (4)N3—C8—C9—O556.8 (6)
O1—P1—N3—C1150.5 (4)O5—C10—C11—N358.4 (6)
N1—P1—N3—C827.8 (4)N4—C12—C13—O659.0 (6)
N1—P1—N3—C11166.3 (4)O6—C14—C15—N456.4 (6)
N4—P1—N3—C8149.7 (4)O8—C16—C17—C18168.9 (5)
N4—P1—N3—C1171.8 (4)O8—C16—C17—C2210.0 (8)
O1—P1—N4—C1222.6 (5)N5—C16—C17—C1811.4 (8)
O1—P1—N4—C15167.3 (4)N5—C16—C17—C22169.8 (5)
N1—P1—N4—C1295.7 (4)C16—C17—C18—C19179.4 (6)
N1—P1—N4—C1574.4 (5)C22—C17—C18—C191.9 (9)
N3—P1—N4—C12148.1 (4)C16—C17—C22—C21179.1 (5)
N3—P1—N4—C1541.8 (5)C18—C17—C22—C212.1 (9)
N5—P2—O7—Er1131.6 (5)C17—C18—C19—C200.5 (9)
N7—P2—O7—Er116.0 (6)C18—C19—C20—N6177.8 (6)
N8—P2—O7—Er1105.6 (5)C18—C19—C20—C210.8 (9)
O7—P2—N5—C16175.8 (4)N6—C20—C21—C22177.6 (5)
N7—P2—N5—C1651.0 (5)C19—C20—C21—C220.6 (9)
N8—P2—N5—C1665.0 (5)C20—C21—C22—C170.8 (9)
O7—P2—N7—C2371.1 (4)N7—C23—C24—O1158.0 (5)
O7—P2—N7—C2685.2 (4)O11—C25—C26—N757.7 (5)
N5—P2—N7—C2344.1 (4)N8—C27—C28—O1256.7 (6)
N5—P2—N7—C26159.6 (4)O12—C29—C30—N859.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O5i0.84 (5)1.93 (5)2.753 (5)169 (7)
N1—H1N···O160.86 (3)2.11 (3)2.887 (6)150 (3)
N1—H1N···O190.86 (3)2.53 (3)3.184 (6)134 (3)
O1W—H1WB···O11ii0.84 (5)2.01 (5)2.807 (5)158 (6)
C3—H3···O20.952.482.802 (8)100
C8—H8B···O6iii0.992.483.328 (6)144
C8—H8B···N10.992.532.965 (7)106
C12—H12B···O10.992.452.960 (6)111
C12—H12B···O200.992.553.453 (8)152
C14—H14B···O15ii0.992.543.437 (7)151
C21—H21···O6iv0.952.583.357 (7)139
C22—H22···O80.952.442.760 (7)100
C23—H23A···O12iii0.992.373.275 (7)152
C23—H23A···N50.992.513.027 (7)112
C26—H26A···O130.992.503.202 (6)127
C26—H26B···N80.992.583.063 (7)110
C27—H27A···O3v0.992.493.443 (8)161
C28—H28B···O15i0.992.543.125 (8)118
C30—H30A···O70.992.412.912 (6)111
C30—H30A···O200.992.503.489 (9)177
C7—H77···O190.952.563.413 (8)149
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y, z1; (v) x+1, y, z.
 

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