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A systematic study of the products of nucleophilic substitution reactions of cis-ansa N3P3Ph2[O(CH2CH2O)4]Cl2 (3) is reported. These reactions give a number of new structures with the general formula N3P3Ph2[O(CH2CH2O)4]R2 [where R = OCH2CF3 (4), OPh (5), OMe (6), NHPh (7·H2O), NHBut (8)]. A comparison has been made between the sum of the substituent basicity constants, \textstyle\sumαR, that are obtained in nitrobenzene solution and eight molecular parameters of the N3P3 ring [the P—N bond lengths a, b, c; the internal bond angles α, β, γ, δ; and the difference between the bond lengths a and b, Δ(P—N)]. It is found that the systematic changes in the molecular parameters of (3)–(8) are in line with changes in αR values. This result implies the similarity in relative electron-releasing capacity of substituents R in the solid state and in solution.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102018608/bm0058sup1.cif
Contains datablocks 3, 4, 5, 6, 7, 8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00583sup2.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00584sup3.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00585sup4.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00586sup5.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00587sup6.hkl
Contains datablock 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00588sup7.hkl
Contains datablock 8

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102018608/bm0058sup8.pdf
Preparation of the compounds

CCDC references: 201638; 201639; 201640; 201641; 201642; 201643

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (3), (4), (7), (8); DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for (5), (6). For all compounds, cell refinement: DENZO & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(3) top
Crystal data top
C20H26Cl2N3O5P3F(000) = 1144
Mr = 552.25Dx = 1.462 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 17.618 (4) ÅCell parameters from 7188 reflections
b = 8.1109 (16) Åθ = 2.9–27.5°
c = 19.284 (4) ŵ = 0.49 mm1
β = 114.44 (3)°T = 150 K
V = 2508.8 (9) Å3Block, colourless
Z = 40.32 × 0.28 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
5657 independent reflections
Radiation source: Nonius FR591 rotating anode4268 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
ϕ and ω scansh = 2222
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 910
Tmin = 0.860, Tmax = 0.939l = 2425
17345 measured reflections
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0421P)2 + 1.1841P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
5657 reflectionsΔρmax = 0.32 e Å3
299 parametersΔρmin = 0.46 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0041 (7)
Crystal data top
C20H26Cl2N3O5P3V = 2508.8 (9) Å3
Mr = 552.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.618 (4) ŵ = 0.49 mm1
b = 8.1109 (16) ÅT = 150 K
c = 19.284 (4) Å0.32 × 0.28 × 0.13 mm
β = 114.44 (3)°
Data collection top
Nonius KappaCCD
diffractometer
5657 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
4268 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.939Rint = 0.045
17345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.01Δρmax = 0.32 e Å3
5657 reflectionsΔρmin = 0.46 e Å3
299 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.34690 (14)0.3650 (3)0.08190 (13)0.0353 (5)
H1A0.36520.30390.04710.042*
H1B0.37230.47620.09060.042*
C20.25355 (14)0.3779 (3)0.04826 (14)0.0351 (5)
H2A0.23530.42850.08550.042*
H2B0.23380.44800.00210.042*
C30.13197 (13)0.2129 (3)0.00253 (13)0.0324 (5)
H3A0.10570.27250.04650.039*
H3B0.11460.26630.03980.039*
C40.10552 (13)0.0361 (3)0.00783 (12)0.0314 (5)
H4A0.04410.02870.03550.038*
H4B0.13100.02170.03810.038*
C50.12177 (14)0.2125 (3)0.06105 (12)0.0314 (5)
H5A0.15350.26070.03390.038*
H5B0.06220.24080.03230.038*
C60.15258 (14)0.2830 (3)0.13942 (13)0.0332 (5)
H6A0.13050.21790.17040.040*
H6B0.13280.39800.13690.040*
C70.27381 (15)0.3424 (3)0.24890 (13)0.0343 (5)
H7A0.25560.45790.24870.041*
H7B0.25350.27620.28090.041*
C80.36667 (14)0.3344 (3)0.28008 (13)0.0329 (5)
H8A0.39160.39130.32990.039*
H8B0.38650.38920.24480.039*
C90.42545 (13)0.1990 (2)0.05410 (11)0.0232 (4)
C100.45124 (14)0.2951 (3)0.00783 (11)0.0286 (5)
H100.50890.31710.02300.034*
C110.39313 (15)0.3588 (3)0.06037 (12)0.0337 (5)
H110.41100.42420.09170.040*
C120.30945 (14)0.3269 (3)0.08254 (12)0.0325 (5)
H120.26960.36980.12930.039*
C130.28353 (14)0.2326 (3)0.03664 (13)0.0341 (5)
H130.22580.21190.05190.041*
C140.34047 (13)0.1682 (3)0.03104 (12)0.0306 (5)
H140.32190.10300.06200.037*
C150.59947 (13)0.1647 (2)0.15535 (11)0.0242 (4)
C160.64688 (13)0.2713 (3)0.21393 (11)0.0274 (5)
H160.62550.30920.24900.033*
C170.72477 (14)0.3224 (3)0.22145 (13)0.0340 (5)
H170.75690.39460.26170.041*
C180.75587 (14)0.2685 (3)0.17056 (13)0.0349 (5)
H180.80890.30580.17520.042*
C190.71016 (14)0.1602 (3)0.11262 (13)0.0344 (5)
H190.73220.12230.07810.041*
C200.63259 (14)0.1077 (3)0.10513 (12)0.0295 (5)
H200.60160.03250.06580.035*
N10.45554 (11)0.0985 (2)0.26501 (10)0.0286 (4)
N20.47795 (11)0.1963 (2)0.20964 (9)0.0246 (4)
N30.48236 (11)0.0870 (2)0.13602 (9)0.0268 (4)
O10.37151 (9)0.27752 (18)0.15361 (8)0.0302 (3)
O20.21987 (9)0.21724 (18)0.02925 (9)0.0320 (4)
O30.13151 (10)0.03846 (19)0.06479 (8)0.0338 (4)
O40.24094 (9)0.2794 (2)0.17365 (8)0.0332 (4)
O50.39105 (9)0.16149 (18)0.28902 (9)0.0322 (4)
P10.45731 (3)0.18753 (6)0.19288 (3)0.02392 (14)
P20.46451 (3)0.09408 (6)0.27249 (3)0.02262 (14)
P30.49581 (3)0.10982 (6)0.14295 (3)0.02192 (14)
Cl10.53581 (4)0.38143 (7)0.22985 (4)0.04032 (17)
Cl20.56344 (4)0.13776 (9)0.37365 (3)0.0519 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0336 (13)0.0305 (13)0.0424 (13)0.0002 (10)0.0162 (11)0.0135 (10)
C20.0325 (12)0.0246 (12)0.0456 (13)0.0024 (10)0.0135 (11)0.0101 (10)
C30.0240 (11)0.0332 (13)0.0419 (12)0.0045 (9)0.0156 (10)0.0057 (10)
C40.0276 (11)0.0338 (13)0.0337 (11)0.0016 (10)0.0137 (10)0.0013 (9)
C50.0312 (12)0.0272 (12)0.0397 (12)0.0041 (9)0.0184 (10)0.0030 (9)
C60.0347 (13)0.0282 (12)0.0451 (13)0.0030 (10)0.0250 (11)0.0012 (10)
C70.0440 (14)0.0302 (12)0.0380 (12)0.0012 (10)0.0264 (11)0.0074 (10)
C80.0436 (14)0.0245 (12)0.0375 (12)0.0003 (10)0.0237 (11)0.0059 (9)
C90.0274 (11)0.0193 (10)0.0277 (10)0.0008 (8)0.0162 (9)0.0032 (8)
C100.0300 (11)0.0290 (12)0.0288 (11)0.0054 (9)0.0143 (9)0.0015 (9)
C110.0415 (14)0.0318 (13)0.0288 (11)0.0025 (10)0.0156 (10)0.0048 (9)
C120.0351 (13)0.0281 (12)0.0297 (11)0.0039 (10)0.0088 (10)0.0017 (9)
C130.0253 (11)0.0348 (13)0.0427 (13)0.0027 (10)0.0145 (10)0.0017 (10)
C140.0291 (12)0.0298 (12)0.0385 (12)0.0008 (9)0.0197 (10)0.0011 (10)
C150.0274 (11)0.0213 (11)0.0260 (10)0.0013 (8)0.0132 (9)0.0031 (8)
C160.0316 (12)0.0241 (11)0.0268 (10)0.0011 (9)0.0124 (9)0.0020 (8)
C170.0323 (12)0.0317 (13)0.0328 (11)0.0030 (10)0.0081 (10)0.0018 (10)
C180.0233 (11)0.0340 (13)0.0458 (13)0.0006 (10)0.0128 (10)0.0088 (11)
C190.0353 (13)0.0329 (13)0.0449 (13)0.0047 (10)0.0265 (11)0.0053 (10)
C200.0324 (12)0.0269 (12)0.0336 (11)0.0017 (9)0.0180 (10)0.0020 (9)
N10.0407 (11)0.0202 (9)0.0305 (9)0.0028 (8)0.0203 (8)0.0016 (7)
N20.0350 (10)0.0176 (9)0.0294 (9)0.0021 (7)0.0214 (8)0.0017 (7)
N30.0409 (11)0.0167 (9)0.0311 (9)0.0012 (8)0.0231 (8)0.0027 (7)
O10.0280 (8)0.0298 (8)0.0361 (8)0.0056 (6)0.0166 (7)0.0069 (7)
O20.0262 (8)0.0267 (8)0.0459 (9)0.0026 (6)0.0177 (7)0.0048 (7)
O30.0453 (9)0.0266 (8)0.0342 (8)0.0009 (7)0.0212 (7)0.0001 (6)
O40.0325 (9)0.0387 (9)0.0343 (8)0.0017 (7)0.0198 (7)0.0065 (7)
O50.0402 (9)0.0263 (8)0.0424 (8)0.0044 (7)0.0296 (7)0.0039 (7)
P10.0268 (3)0.0171 (3)0.0312 (3)0.0005 (2)0.0153 (2)0.0005 (2)
P20.0265 (3)0.0220 (3)0.0221 (3)0.0024 (2)0.0127 (2)0.0011 (2)
P30.0285 (3)0.0175 (3)0.0251 (3)0.0013 (2)0.0163 (2)0.0015 (2)
Cl10.0380 (3)0.0280 (3)0.0562 (4)0.0102 (2)0.0208 (3)0.0094 (3)
Cl20.0503 (4)0.0567 (4)0.0311 (3)0.0141 (3)0.0008 (3)0.0012 (3)
Geometric parameters (Å, º) top
C1—O11.452 (3)C10—C111.390 (3)
C1—C21.501 (3)C10—H100.9500
C1—H1A0.9900C11—C121.379 (3)
C1—H1B0.9900C11—H110.9500
C2—O21.416 (3)C12—C131.383 (3)
C2—H2A0.9900C12—H120.9500
C2—H2B0.9900C13—C141.378 (3)
C3—O21.416 (3)C13—H130.9500
C3—C41.495 (3)C14—H140.9500
C3—H3A0.9900C15—C161.393 (3)
C3—H3B0.9900C15—C201.400 (3)
C4—O31.416 (3)C15—P31.797 (2)
C4—H4A0.9900C16—C171.382 (3)
C4—H4B0.9900C16—H160.9500
C5—O31.421 (3)C17—C181.378 (3)
C5—C61.492 (3)C17—H170.9500
C5—H5A0.9900C18—C191.387 (3)
C5—H5B0.9900C18—H180.9500
C6—O41.418 (3)C19—C201.381 (3)
C6—H6A0.9900C19—H190.9500
C6—H6B0.9900C20—H200.9500
C7—O41.417 (3)N1—P21.5703 (18)
C7—C81.493 (3)N1—P11.5792 (17)
C7—H7A0.9900N2—P21.5653 (16)
C7—H7B0.9900N2—P31.6064 (16)
C8—O51.456 (3)N3—P11.5694 (17)
C8—H8A0.9900N3—P31.6110 (17)
C8—H8B0.9900O1—P11.5633 (16)
C9—C101.395 (3)O5—P21.5547 (15)
C9—C141.397 (3)P1—Cl12.0196 (8)
C9—P31.799 (2)P2—Cl22.0387 (11)
O1—C1—C2106.71 (17)C12—C11—H11120.1
O1—C1—H1A110.4C10—C11—H11120.1
C2—C1—H1A110.4C11—C12—C13119.9 (2)
O1—C1—H1B110.4C11—C12—H12120.0
C2—C1—H1B110.4C13—C12—H12120.0
H1A—C1—H1B108.6C14—C13—C12120.8 (2)
O2—C2—C1108.36 (18)C14—C13—H13119.6
O2—C2—H2A110.0C12—C13—H13119.6
C1—C2—H2A110.0C13—C14—C9119.9 (2)
O2—C2—H2B110.0C13—C14—H14120.1
C1—C2—H2B110.0C9—C14—H14120.1
H2A—C2—H2B108.4C16—C15—C20118.97 (19)
O2—C3—C4107.83 (17)C16—C15—P3119.82 (15)
O2—C3—H3A110.1C20—C15—P3121.16 (16)
C4—C3—H3A110.1C17—C16—C15120.5 (2)
O2—C3—H3B110.1C17—C16—H16119.8
C4—C3—H3B110.1C15—C16—H16119.8
H3A—C3—H3B108.5C18—C17—C16120.0 (2)
O3—C4—C3108.78 (18)C18—C17—H17120.0
O3—C4—H4A109.9C16—C17—H17120.0
C3—C4—H4A109.9C17—C18—C19120.3 (2)
O3—C4—H4B109.9C17—C18—H18119.8
C3—C4—H4B109.9C19—C18—H18119.8
H4A—C4—H4B108.3C20—C19—C18120.0 (2)
O3—C5—C6110.09 (18)C20—C19—H19120.0
O3—C5—H5A109.6C18—C19—H19120.0
C6—C5—H5A109.6C19—C20—C15120.2 (2)
O3—C5—H5B109.6C19—C20—H20119.9
C6—C5—H5B109.6C15—C20—H20119.9
H5A—C5—H5B108.2P2—N1—P1119.86 (10)
O4—C6—C5109.46 (17)P2—N2—P3122.07 (11)
O4—C6—H6A109.8P1—N3—P3122.09 (10)
C5—C6—H6A109.8C1—O1—P1122.52 (13)
O4—C6—H6B109.8C2—O2—C3113.29 (16)
C5—C6—H6B109.8C4—O3—C5113.05 (16)
H6A—C6—H6B108.2C6—O4—C7111.99 (16)
O4—C7—C8108.20 (17)C8—O5—P2122.98 (13)
O4—C7—H7A110.1O1—P1—N3113.53 (9)
C8—C7—H7A110.1O1—P1—N1105.83 (9)
O4—C7—H7B110.1N3—P1—N1119.44 (9)
C8—C7—H7B110.1O1—P1—Cl1101.02 (7)
H7A—C7—H7B108.4N3—P1—Cl1107.58 (7)
O5—C8—C7108.07 (18)N1—P1—Cl1107.79 (8)
O5—C8—H8A110.1O5—P2—N2112.20 (9)
C7—C8—H8A110.1O5—P2—N1107.93 (9)
O5—C8—H8B110.1N2—P2—N1119.85 (9)
C7—C8—H8B110.1O5—P2—Cl2101.38 (7)
H8A—C8—H8B108.4N2—P2—Cl2107.79 (7)
C10—C9—C14119.1 (2)N1—P2—Cl2105.92 (7)
C10—C9—P3123.73 (16)N2—P3—N3115.37 (9)
C14—C9—P3117.18 (15)N2—P3—C15108.06 (9)
C11—C10—C9120.4 (2)N3—P3—C15111.30 (9)
C11—C10—H10119.8N2—P3—C9107.51 (9)
C9—C10—H10119.8N3—P3—C9107.42 (9)
C12—C11—C10119.9 (2)C15—P3—C9106.80 (9)
(4) top
Crystal data top
C24H30F6N3O7P3F(000) = 1400
Mr = 679.42Dx = 1.562 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.3839 (4) ÅCell parameters from 10029 reflections
b = 8.0685 (2) Åθ = 2.9–27.5°
c = 24.1935 (9) ŵ = 0.29 mm1
β = 105.877 (1)°T = 120 K
V = 2888.46 (15) Å3Plate, colourless
Z = 40.18 × 0.10 × 0.03 mm
Data collection top
Nonius KappaCCD
diffractometer
6488 independent reflections
Radiation source: Nonius FR591 rotating anode3777 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 1919
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 108
Tmin = 0.949, Tmax = 0.991l = 3131
22797 measured reflections
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0463P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.006
6488 reflectionsΔρmax = 0.38 e Å3
389 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0013 (3)
Crystal data top
C24H30F6N3O7P3V = 2888.46 (15) Å3
Mr = 679.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.3839 (4) ŵ = 0.29 mm1
b = 8.0685 (2) ÅT = 120 K
c = 24.1935 (9) Å0.18 × 0.10 × 0.03 mm
β = 105.877 (1)°
Data collection top
Nonius KappaCCD
diffractometer
6488 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
3777 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.991Rint = 0.083
22797 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 0.98Δρmax = 0.38 e Å3
6488 reflectionsΔρmin = 0.38 e Å3
389 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.30632 (19)0.4338 (4)0.06173 (11)0.0266 (7)
H1A0.25410.46800.07560.032*
H1B0.32530.32140.07670.032*
C20.28124 (19)0.4340 (4)0.00210 (12)0.0269 (7)
C30.17222 (17)0.9621 (4)0.11787 (11)0.0233 (6)
H3A0.13751.05770.12620.028*
H3B0.16310.86710.14160.028*
C40.14009 (19)0.9187 (4)0.05592 (12)0.0269 (7)
C50.42024 (18)0.4028 (4)0.23410 (11)0.0242 (6)
H5A0.40980.28390.24010.029*
H5B0.37170.46720.24390.029*
C60.51021 (19)0.4538 (4)0.27284 (11)0.0259 (7)
H6A0.56000.40200.26040.031*
H6B0.51730.57580.27250.031*
C70.59025 (19)0.4441 (4)0.37193 (12)0.0302 (7)
H7A0.64360.40480.36030.036*
H7B0.59010.38600.40800.036*
C80.60045 (18)0.6261 (4)0.38397 (12)0.0271 (7)
H8A0.65630.64740.41510.032*
H8B0.60500.68600.34910.032*
C90.52831 (18)0.8561 (4)0.41135 (13)0.0290 (7)
H9A0.53250.91640.37650.035*
H9B0.58270.88250.44300.035*
C100.44546 (18)0.9086 (4)0.42728 (12)0.0283 (7)
H10A0.44400.85180.46330.034*
H10B0.44891.02930.43490.034*
C110.34972 (19)0.9633 (4)0.33199 (11)0.0264 (7)
H11A0.40271.03450.33340.032*
H11B0.29571.03500.32600.032*
C120.3367 (2)0.8411 (4)0.28409 (11)0.0278 (7)
H12A0.39540.79130.28380.033*
H12B0.29570.75120.28910.033*
C130.54897 (17)0.9977 (3)0.11897 (11)0.0221 (6)
C140.60246 (19)0.9212 (4)0.08832 (12)0.0291 (7)
H140.62330.81110.09760.035*
C150.6252 (2)1.0045 (4)0.04477 (13)0.0369 (8)
H150.66190.95180.02410.044*
C160.5950 (2)1.1645 (4)0.03084 (13)0.0353 (8)
H160.61001.22090.00020.042*
C170.54328 (19)1.2420 (4)0.06134 (13)0.0323 (8)
H170.52311.35240.05200.039*
C180.52048 (18)1.1603 (4)0.10542 (12)0.0267 (7)
H180.48531.21500.12660.032*
C190.60959 (17)0.8989 (3)0.23775 (11)0.0199 (6)
C200.61259 (18)1.0190 (3)0.27932 (12)0.0237 (6)
H200.56401.09520.27470.028*
C210.68568 (18)1.0286 (4)0.32734 (12)0.0265 (7)
H210.68691.11050.35580.032*
C220.75699 (18)0.9198 (4)0.33423 (12)0.0282 (7)
H220.80770.92800.36700.034*
C230.75470 (19)0.7992 (4)0.29360 (12)0.0337 (8)
H230.80350.72330.29860.040*
C240.68116 (18)0.7885 (4)0.24537 (12)0.0289 (7)
H240.67980.70510.21740.035*
N10.33017 (13)0.7066 (3)0.16249 (9)0.0198 (5)
N20.43216 (14)0.9822 (3)0.18728 (9)0.0209 (5)
N30.50191 (13)0.6960 (3)0.15597 (9)0.0202 (5)
O10.37931 (11)0.5486 (2)0.08091 (7)0.0220 (4)
O20.26641 (11)1.0034 (2)0.13145 (7)0.0217 (4)
O30.41684 (12)0.4304 (2)0.17469 (7)0.0217 (4)
O40.51064 (13)0.3981 (2)0.32838 (7)0.0279 (5)
O50.52409 (12)0.6830 (2)0.40069 (8)0.0272 (5)
O60.36358 (12)0.8736 (2)0.38419 (8)0.0274 (5)
O70.29802 (12)0.9283 (2)0.23075 (7)0.0227 (4)
F10.35004 (11)0.3951 (2)0.02316 (7)0.0376 (5)
F20.21548 (12)0.3238 (2)0.02294 (7)0.0463 (5)
F30.25101 (11)0.5803 (2)0.02512 (7)0.0338 (4)
F40.18624 (12)0.7925 (2)0.04156 (8)0.0503 (5)
F50.14593 (12)1.0434 (2)0.02171 (7)0.0453 (5)
F60.05335 (11)0.8715 (2)0.04226 (7)0.0391 (5)
P10.40851 (4)0.60711 (9)0.14597 (3)0.01907 (18)
P20.33745 (4)0.89744 (9)0.17773 (3)0.01903 (18)
P30.51600 (4)0.88728 (9)0.17412 (3)0.01985 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0275 (16)0.0292 (19)0.0224 (15)0.0102 (13)0.0055 (12)0.0007 (13)
C20.0274 (17)0.0273 (19)0.0244 (16)0.0056 (13)0.0042 (12)0.0062 (14)
C30.0178 (15)0.0258 (17)0.0242 (15)0.0007 (12)0.0024 (11)0.0011 (13)
C40.0252 (17)0.0261 (19)0.0268 (16)0.0028 (13)0.0026 (12)0.0013 (14)
C50.0293 (16)0.0214 (17)0.0220 (15)0.0009 (12)0.0069 (12)0.0025 (13)
C60.0327 (17)0.0224 (17)0.0217 (16)0.0011 (12)0.0060 (12)0.0027 (13)
C70.0291 (17)0.034 (2)0.0227 (16)0.0077 (13)0.0007 (12)0.0011 (14)
C80.0218 (16)0.035 (2)0.0228 (15)0.0050 (13)0.0038 (12)0.0013 (14)
C90.0273 (17)0.0243 (19)0.0324 (17)0.0019 (12)0.0030 (13)0.0009 (14)
C100.0301 (17)0.0284 (19)0.0216 (15)0.0007 (13)0.0009 (12)0.0049 (13)
C110.0272 (16)0.0287 (18)0.0227 (16)0.0072 (13)0.0057 (12)0.0013 (13)
C120.0363 (17)0.0285 (18)0.0172 (15)0.0080 (13)0.0047 (12)0.0041 (13)
C130.0211 (15)0.0197 (17)0.0228 (15)0.0030 (12)0.0015 (11)0.0028 (13)
C140.0369 (18)0.0258 (19)0.0293 (17)0.0008 (13)0.0172 (13)0.0024 (14)
C150.0431 (19)0.039 (2)0.0346 (19)0.0091 (16)0.0205 (15)0.0083 (16)
C160.0375 (18)0.040 (2)0.0249 (17)0.0162 (15)0.0028 (13)0.0027 (15)
C170.0318 (17)0.0271 (19)0.0330 (18)0.0033 (13)0.0002 (14)0.0059 (15)
C180.0222 (15)0.0278 (19)0.0272 (16)0.0005 (12)0.0018 (12)0.0016 (14)
C190.0184 (14)0.0211 (17)0.0200 (14)0.0001 (12)0.0052 (11)0.0024 (13)
C200.0249 (16)0.0188 (17)0.0265 (16)0.0004 (12)0.0057 (12)0.0018 (13)
C210.0311 (17)0.0244 (18)0.0232 (16)0.0054 (13)0.0060 (12)0.0042 (13)
C220.0226 (16)0.034 (2)0.0245 (16)0.0037 (13)0.0001 (12)0.0024 (14)
C230.0241 (16)0.042 (2)0.0324 (18)0.0106 (14)0.0034 (13)0.0006 (16)
C240.0280 (16)0.0311 (19)0.0264 (16)0.0044 (13)0.0058 (12)0.0045 (14)
N10.0189 (12)0.0187 (14)0.0223 (12)0.0008 (9)0.0066 (9)0.0003 (10)
N20.0212 (12)0.0146 (13)0.0271 (13)0.0000 (9)0.0068 (10)0.0033 (10)
N30.0183 (12)0.0164 (13)0.0248 (12)0.0010 (9)0.0041 (9)0.0031 (10)
O10.0263 (11)0.0209 (11)0.0184 (10)0.0057 (8)0.0054 (8)0.0037 (8)
O20.0175 (10)0.0227 (12)0.0227 (10)0.0001 (8)0.0018 (7)0.0025 (8)
O30.0312 (11)0.0159 (11)0.0181 (10)0.0009 (8)0.0067 (8)0.0003 (8)
O40.0355 (12)0.0285 (13)0.0172 (10)0.0023 (9)0.0028 (8)0.0045 (9)
O50.0242 (11)0.0248 (13)0.0334 (12)0.0005 (8)0.0093 (8)0.0019 (9)
O60.0250 (11)0.0361 (13)0.0192 (10)0.0004 (9)0.0031 (8)0.0011 (9)
O70.0256 (10)0.0230 (12)0.0198 (10)0.0050 (8)0.0067 (8)0.0016 (8)
F10.0409 (11)0.0447 (12)0.0277 (10)0.0095 (8)0.0102 (8)0.0097 (8)
F20.0553 (12)0.0455 (13)0.0307 (10)0.0281 (9)0.0007 (8)0.0076 (9)
F30.0355 (10)0.0327 (11)0.0290 (9)0.0060 (8)0.0017 (7)0.0034 (8)
F40.0462 (12)0.0542 (14)0.0426 (11)0.0211 (10)0.0012 (9)0.0229 (10)
F50.0498 (12)0.0541 (14)0.0262 (10)0.0051 (9)0.0008 (8)0.0107 (9)
F60.0292 (10)0.0410 (12)0.0382 (10)0.0032 (8)0.0060 (7)0.0069 (9)
P10.0211 (4)0.0172 (4)0.0181 (4)0.0004 (3)0.0040 (3)0.0006 (3)
P20.0185 (4)0.0194 (4)0.0183 (4)0.0018 (3)0.0033 (3)0.0004 (3)
P30.0175 (4)0.0200 (4)0.0211 (4)0.0007 (3)0.0037 (3)0.0026 (3)
Geometric parameters (Å, º) top
C1—O11.431 (3)C11—H11B0.9900
C1—C21.486 (4)C12—O71.447 (3)
C1—H1A0.9900C12—H12A0.9900
C1—H1B0.9900C12—H12B0.9900
C2—F11.332 (3)C13—C141.393 (4)
C2—F31.333 (3)C13—C181.394 (4)
C2—F21.338 (3)C13—P31.789 (3)
C3—O21.434 (3)C14—C151.373 (4)
C3—C41.486 (4)C14—H140.9500
C3—H3A0.9900C15—C161.382 (5)
C3—H3B0.9900C15—H150.9500
C4—F51.322 (3)C16—C171.375 (4)
C4—F61.339 (3)C16—H160.9500
C4—F41.340 (3)C17—C181.378 (4)
C5—O31.441 (3)C17—H170.9500
C5—C61.501 (4)C18—H180.9500
C5—H5A0.9900C19—C241.389 (4)
C5—H5B0.9900C19—C201.389 (4)
C6—O41.415 (3)C19—P31.800 (3)
C6—H6A0.9900C20—C211.380 (4)
C6—H6B0.9900C20—H200.9500
C7—O41.429 (3)C21—C221.379 (4)
C7—C81.497 (4)C21—H210.9500
C7—H7A0.9900C22—C231.377 (4)
C7—H7B0.9900C22—H220.9500
C8—O51.419 (3)C23—C241.388 (4)
C8—H8A0.9900C23—H230.9500
C8—H8B0.9900C24—H240.9500
C9—O51.418 (3)N1—P21.581 (2)
C9—C101.491 (4)N1—P11.587 (2)
C9—H9A0.9900N2—P21.569 (2)
C9—H9B0.9900N2—P31.605 (2)
C10—O61.426 (3)N3—P11.565 (2)
C10—H10A0.9900N3—P31.603 (2)
C10—H10B0.9900O1—P11.5861 (18)
C11—O61.420 (3)O2—P21.5840 (18)
C11—C121.493 (4)O3—P11.5763 (19)
C11—H11A0.9900O7—P21.5814 (18)
O1—C1—C2107.1 (2)C11—C12—H12A110.1
O1—C1—H1A110.3O7—C12—H12B110.1
C2—C1—H1A110.3C11—C12—H12B110.1
O1—C1—H1B110.3H12A—C12—H12B108.5
C2—C1—H1B110.3C14—C13—C18119.0 (3)
H1A—C1—H1B108.6C14—C13—P3120.4 (2)
F1—C2—F3105.8 (2)C18—C13—P3120.6 (2)
F1—C2—F2107.3 (2)C15—C14—C13120.2 (3)
F3—C2—F2106.8 (2)C15—C14—H14119.9
F1—C2—C1113.0 (2)C13—C14—H14119.9
F3—C2—C1113.4 (2)C14—C15—C16120.3 (3)
F2—C2—C1110.2 (2)C14—C15—H15119.9
O2—C3—C4108.8 (2)C16—C15—H15119.9
O2—C3—H3A109.9C17—C16—C15119.9 (3)
C4—C3—H3A109.9C17—C16—H16120.0
O2—C3—H3B109.9C15—C16—H16120.0
C4—C3—H3B109.9C16—C17—C18120.4 (3)
H3A—C3—H3B108.3C16—C17—H17119.8
F5—C4—F6107.2 (2)C18—C17—H17119.8
F5—C4—F4106.5 (2)C17—C18—C13120.1 (3)
F6—C4—F4106.4 (2)C17—C18—H18119.9
F5—C4—C3113.0 (2)C13—C18—H18119.9
F6—C4—C3110.5 (2)C24—C19—C20118.9 (2)
F4—C4—C3112.8 (2)C24—C19—P3120.0 (2)
O3—C5—C6110.9 (2)C20—C19—P3121.1 (2)
O3—C5—H5A109.5C21—C20—C19120.4 (3)
C6—C5—H5A109.5C21—C20—H20119.8
O3—C5—H5B109.5C19—C20—H20119.8
C6—C5—H5B109.5C22—C21—C20120.3 (3)
H5A—C5—H5B108.1C22—C21—H21119.9
O4—C6—C5105.6 (2)C20—C21—H21119.9
O4—C6—H6A110.6C23—C22—C21120.0 (3)
C5—C6—H6A110.6C23—C22—H22120.0
O4—C6—H6B110.6C21—C22—H22120.0
C5—C6—H6B110.6C22—C23—C24120.0 (3)
H6A—C6—H6B108.7C22—C23—H23120.0
O4—C7—C8114.9 (2)C24—C23—H23120.0
O4—C7—H7A108.5C23—C24—C19120.4 (3)
C8—C7—H7A108.5C23—C24—H24119.8
O4—C7—H7B108.5C19—C24—H24119.8
C8—C7—H7B108.5P2—N1—P1122.76 (13)
H7A—C7—H7B107.5P2—N2—P3121.81 (14)
O5—C8—C7108.8 (2)P1—N3—P3122.24 (13)
O5—C8—H8A109.9C1—O1—P1119.89 (16)
C7—C8—H8A109.9C3—O2—P2119.68 (17)
O5—C8—H8B109.9C5—O3—P1123.76 (17)
C7—C8—H8B109.9C6—O4—C7113.4 (2)
H8A—C8—H8B108.3C9—O5—C8111.7 (2)
O5—C9—C10109.1 (2)C11—O6—C10115.9 (2)
O5—C9—H9A109.9C12—O7—P2119.43 (17)
C10—C9—H9A109.9N3—P1—O3112.73 (11)
O5—C9—H9B109.9N3—P1—O1106.78 (11)
C10—C9—H9B109.9O3—P1—O197.76 (10)
H9A—C9—H9B108.3N3—P1—N1117.24 (12)
O6—C10—C9113.7 (2)O3—P1—N1108.79 (11)
O6—C10—H10A108.8O1—P1—N1111.83 (11)
C9—C10—H10A108.8N2—P2—N1117.58 (12)
O6—C10—H10B108.8N2—P2—O7111.04 (11)
C9—C10—H10B108.8N1—P2—O7108.91 (11)
H10A—C10—H10B107.7N2—P2—O2107.59 (11)
O6—C11—C12108.0 (2)N1—P2—O2111.70 (11)
O6—C11—H11A110.1O7—P2—O298.33 (10)
C12—C11—H11A110.1N3—P3—N2117.27 (11)
O6—C11—H11B110.1N3—P3—C13108.64 (12)
C12—C11—H11B110.1N2—P3—C13108.51 (13)
H11A—C11—H11B108.4N3—P3—C19107.51 (12)
O7—C12—C11107.8 (2)N2—P3—C19107.68 (12)
O7—C12—H12A110.1C13—P3—C19106.76 (12)
O1—C1—C2—F157.5 (3)C5—O3—P1—N384.1 (2)
O1—C1—C2—F362.8 (3)C5—O3—P1—O1164.04 (18)
O1—C1—C2—F2177.5 (2)C5—O3—P1—N147.8 (2)
O2—C3—C4—F562.9 (3)C1—O1—P1—N3167.0 (2)
O2—C3—C4—F6177.0 (2)C1—O1—P1—O350.4 (2)
O2—C3—C4—F458.0 (3)C1—O1—P1—N163.5 (2)
O3—C5—C6—O4171.3 (2)P2—N1—P1—N310.9 (2)
O4—C7—C8—O558.3 (3)P2—N1—P1—O3140.30 (14)
O5—C9—C10—O658.9 (3)P2—N1—P1—O1112.85 (15)
O6—C11—C12—O7164.2 (2)P3—N2—P2—N18.0 (2)
C18—C13—C14—C151.1 (4)P3—N2—P2—O7134.31 (15)
P3—C13—C14—C15177.9 (2)P3—N2—P2—O2119.14 (16)
C13—C14—C15—C160.2 (4)P1—N1—P2—N211.0 (2)
C14—C15—C16—C171.2 (4)P1—N1—P2—O7138.35 (14)
C15—C16—C17—C180.7 (4)P1—N1—P2—O2114.12 (15)
C16—C17—C18—C130.7 (4)C12—O7—P2—N273.2 (2)
C14—C13—C18—C171.6 (4)C12—O7—P2—N157.8 (2)
P3—C13—C18—C17177.4 (2)C12—O7—P2—O2174.21 (19)
C24—C19—C20—C210.1 (4)C3—O2—P2—N2174.73 (18)
P3—C19—C20—C21178.7 (2)C3—O2—P2—N154.8 (2)
C19—C20—C21—C220.7 (4)C3—O2—P2—O759.45 (19)
C20—C21—C22—C231.1 (4)P1—N3—P3—N25.3 (2)
C21—C22—C23—C240.8 (4)P1—N3—P3—C13118.16 (16)
C22—C23—C24—C190.0 (4)P1—N3—P3—C19126.65 (16)
C20—C19—C24—C230.5 (4)P2—N2—P3—N35.2 (2)
P3—C19—C24—C23178.3 (2)P2—N2—P3—C13118.26 (16)
C2—C1—O1—P1166.95 (18)P2—N2—P3—C19126.53 (16)
C4—C3—O2—P2119.2 (2)C14—C13—P3—N333.9 (3)
C6—C5—O3—P173.5 (3)C18—C13—P3—N3145.1 (2)
C5—C6—O4—C7176.9 (2)C14—C13—P3—N2162.4 (2)
C8—C7—O4—C667.3 (3)C18—C13—P3—N216.6 (2)
C10—C9—O5—C8178.6 (2)C14—C13—P3—C1981.8 (2)
C7—C8—O5—C9178.5 (2)C18—C13—P3—C1999.2 (2)
C12—C11—O6—C10123.1 (2)C24—C19—P3—N333.5 (3)
C9—C10—O6—C1166.5 (3)C20—C19—P3—N3147.7 (2)
C11—C12—O7—P2134.7 (2)C24—C19—P3—N2160.7 (2)
P3—N3—P1—O3135.42 (14)C20—C19—P3—N220.5 (3)
P3—N3—P1—O1118.37 (15)C24—C19—P3—C1382.9 (2)
P3—N3—P1—N17.9 (2)C20—C19—P3—C1395.8 (2)
(5) top
Crystal data top
C32H36N3O7P3Z = 2
Mr = 667.55F(000) = 700
Triclinic, P1Dx = 1.385 Mg m3
a = 10.166 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.105 (2) ÅCell parameters from 13461 reflections
c = 13.313 (3) Åθ = 2.9–27.5°
α = 88.86 (3)°µ = 0.24 mm1
β = 86.54 (3)°T = 150 K
γ = 78.14 (3)°Block, colourless
V = 1600.4 (6) Å30.20 × 0.15 × 0.10 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
12306 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode8750 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ & ω scansh = 1311
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 1513
Tmin = 0.954, Tmax = 0.977l = 1716
24220 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0651P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132(Δ/σ)max = 0.002
S = 0.94Δρmax = 0.81 e Å3
12306 reflectionsΔρmin = 0.40 e Å3
824 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
22 restraintsExtinction coefficient: 0.0054 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (7)
Crystal data top
C32H36N3O7P3γ = 78.14 (3)°
Mr = 667.55V = 1600.4 (6) Å3
Triclinic, P1Z = 2
a = 10.166 (2) ÅMo Kα radiation
b = 12.105 (2) ŵ = 0.24 mm1
c = 13.313 (3) ÅT = 150 K
α = 88.86 (3)°0.20 × 0.15 × 0.10 mm
β = 86.54 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
12306 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
8750 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.977Rint = 0.061
24220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132Δρmax = 0.81 e Å3
S = 0.94Δρmin = 0.40 e Å3
12306 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
824 parametersAbsolute structure parameter: 0.03 (7)
22 restraints
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
C10.6413 (4)0.3165 (4)0.7512 (3)0.0331 (10)
C20.7215 (5)0.3322 (4)0.8277 (3)0.0451 (12)
H20.75060.40150.83260.054*
C30.7592 (5)0.2472 (6)0.8971 (4)0.0608 (16)
H30.81510.25750.94930.073*
C40.7162 (6)0.1488 (6)0.8906 (4)0.0634 (17)
H40.74290.09010.93820.076*
C50.6339 (6)0.1332 (5)0.8155 (4)0.0563 (14)
H50.60350.06430.81180.068*
C60.5956 (5)0.2186 (4)0.7453 (3)0.0419 (11)
H60.53830.20890.69380.050*
C70.4772 (4)0.1248 (3)0.4866 (3)0.0287 (9)
C80.3498 (4)0.1431 (4)0.5301 (3)0.0407 (11)
H80.28230.20330.50760.049*
C90.3204 (5)0.0721 (5)0.6078 (4)0.0545 (14)
H90.23090.08210.63660.065*
C100.4186 (5)0.0122 (4)0.6437 (4)0.0483 (13)
H100.39840.05890.69820.058*
C110.5449 (5)0.0277 (4)0.5998 (4)0.0452 (12)
H110.61280.08610.62450.054*
C120.5784 (4)0.0388 (4)0.5200 (3)0.0369 (11)
H120.66700.02620.48940.044*
C130.7370 (5)0.5866 (4)0.6018 (3)0.0389 (11)
H13A0.82540.53730.61320.047*
H13B0.69190.61090.66800.047*
C140.7560 (5)0.6874 (4)0.5402 (4)0.0462 (12)
H14A0.66780.73010.51960.055*
H14B0.79740.73780.58030.055*
C150.8038 (6)0.7150 (4)0.3664 (4)0.0607 (16)
H15A0.80840.79460.37790.073*
H15B0.71000.71250.35230.073*
C160.8930 (7)0.6717 (5)0.2809 (4)0.0639 (16)
H16A0.87670.72500.22350.077*
H16B0.98770.66440.29830.077*
C170.9586 (5)0.5201 (4)0.1709 (3)0.0418 (12)
H17A1.05280.51960.18620.050*
H17B0.93730.56770.11030.050*
C180.9424 (4)0.4047 (4)0.1522 (3)0.0401 (11)
H18A1.01620.36780.10460.048*
H18B0.95020.36140.21620.048*
C190.7362 (5)0.3359 (4)0.1681 (3)0.0378 (11)
H19A0.79570.26820.19540.045*
H19B0.67420.31010.12340.045*
C200.6557 (4)0.4026 (4)0.2535 (3)0.0342 (10)
H20A0.71690.42170.30250.041*
H20B0.60160.47370.22760.041*
C211.0072 (4)0.2632 (3)0.4118 (3)0.0265 (9)
C221.0357 (4)0.3692 (4)0.4182 (3)0.0328 (10)
H220.97970.42420.46030.039*
C231.1454 (5)0.3964 (4)0.3636 (3)0.0399 (11)
H231.16450.46950.36930.048*
C241.2276 (4)0.3175 (4)0.3008 (4)0.0429 (12)
H241.30300.33600.26370.052*
C251.1980 (5)0.2116 (4)0.2930 (4)0.0395 (11)
C261.0892 (4)0.1839 (4)0.3477 (3)0.0351 (10)
H261.06990.11090.34180.042*
C270.9209 (4)0.0982 (3)0.5444 (3)0.0282 (9)
C280.9400 (4)0.0970 (4)0.6463 (3)0.0361 (11)
C290.9899 (5)0.0047 (4)0.6948 (4)0.0459 (13)
H291.00300.00530.76490.055*
C301.0201 (4)0.1037 (4)0.6426 (4)0.0500 (14)
H301.05590.17220.67630.060*
C310.9988 (5)0.1050 (4)0.5408 (4)0.0454 (12)
H311.01840.17400.50500.055*
C320.9480 (4)0.0034 (4)0.4915 (4)0.0395 (11)
H320.93200.00340.42200.047*
C330.0458 (4)0.9098 (3)0.9875 (3)0.0291 (10)
C340.0976 (5)0.9953 (4)1.0268 (4)0.0443 (12)
H340.17701.01550.99760.053*
C350.0282 (6)1.0515 (4)1.1119 (4)0.0506 (13)
C360.0859 (6)1.0204 (4)1.1542 (4)0.0458 (12)
H360.13191.05891.21170.055*
C370.1327 (5)0.9345 (4)1.1137 (4)0.0479 (13)
H370.21100.91301.14350.057*
C380.0665 (5)0.8777 (4)1.0285 (4)0.0415 (12)
H380.09930.81801.00000.050*
C390.2650 (4)0.7026 (4)1.2527 (3)0.0302 (10)
C400.2273 (5)0.8133 (4)1.2833 (4)0.0407 (11)
H400.16870.86741.24530.049*
C410.2776 (5)0.8433 (5)1.3715 (4)0.0505 (13)
H410.25260.91901.39450.061*
C420.3632 (5)0.7643 (5)1.4257 (4)0.0541 (14)
H420.39820.78511.48550.065*
C430.3970 (5)0.6557 (5)1.3923 (4)0.0502 (13)
H430.45640.60121.42930.060*
C440.3479 (4)0.6240 (4)1.3078 (4)0.0382 (11)
C450.3484 (4)0.6531 (4)0.7381 (3)0.0354 (10)
H45A0.39400.59900.78800.042*
H45B0.41380.69650.70830.042*
C460.2970 (5)0.5914 (4)0.6580 (3)0.0379 (11)
H46A0.24120.64560.61320.045*
H46B0.37320.54670.61690.045*
C470.1847 (8)0.4425 (6)0.6381 (5)0.0812 (11)
H47A0.26630.40090.60070.097*
H47B0.12260.48340.58900.097*
C480.1178 (7)0.3620 (5)0.6990 (4)0.0670 (17)
H48A0.04460.40380.74440.080*
H48B0.07900.31430.65420.080*
C490.1786 (7)0.2199 (5)0.8270 (4)0.0812 (11)
H49A0.09720.19610.80540.097*
H49B0.25070.15170.83270.097*
C500.1476 (7)0.2783 (6)0.9297 (4)0.0812 (11)
H50A0.08050.34890.91960.097*
H50B0.10260.22910.97420.097*
C510.3242 (5)0.3829 (4)0.9362 (4)0.0468 (12)
H51A0.26190.44800.90760.056*
H51B0.38500.34470.88080.056*
C520.4052 (5)0.4229 (4)1.0141 (4)0.0461 (12)
H52A0.45500.35661.05030.055*
H52B0.47200.46190.97980.055*
C530.6390 (4)0.7226 (3)0.9300 (3)0.0275 (9)
C540.7292 (4)0.6270 (4)0.9567 (3)0.0357 (10)
H540.70440.58011.00960.043*
C550.8546 (4)0.5984 (4)0.9082 (3)0.0386 (11)
H550.91530.53170.92730.046*
C560.8927 (5)0.6657 (4)0.8319 (4)0.0409 (12)
C570.8018 (5)0.7609 (4)0.8038 (3)0.0417 (12)
H570.82670.80730.75060.050*
C580.6765 (4)0.7895 (4)0.8515 (3)0.0338 (10)
H580.61510.85510.83110.041*
C590.4922 (4)0.8812 (4)1.0727 (3)0.0284 (9)
C600.4746 (5)0.9894 (4)1.0319 (4)0.0382 (11)
C610.4885 (5)1.0797 (4)1.0905 (4)0.0460 (12)
H610.47641.15361.06230.055*
C620.5198 (5)1.0618 (4)1.1886 (4)0.0448 (12)
H620.53141.12311.22820.054*
C630.5347 (5)0.9544 (4)1.2310 (4)0.0441 (12)
H630.55350.94301.29990.053*
C640.5223 (4)0.8640 (4)1.1729 (3)0.0355 (10)
H640.53430.79031.20140.043*
N10.5592 (3)0.3621 (3)0.4977 (3)0.0306 (8)
N20.7557 (3)0.2107 (3)0.4021 (2)0.0267 (8)
N30.8121 (3)0.3259 (3)0.5637 (2)0.0269 (8)
N40.2159 (3)0.6647 (3)0.9743 (3)0.0333 (8)
N50.4455 (3)0.6635 (3)1.0654 (2)0.0281 (8)
N60.3679 (3)0.8139 (3)0.9135 (3)0.0308 (8)
O10.6040 (3)0.4035 (2)0.6831 (2)0.0337 (7)
O20.5028 (3)0.1934 (2)0.4043 (2)0.0308 (7)
O30.6561 (3)0.5265 (2)0.5483 (2)0.0336 (7)
O40.8407 (3)0.6500 (3)0.4540 (2)0.0461 (8)
O50.8707 (3)0.5642 (3)0.2530 (2)0.0455 (8)
O60.8151 (3)0.4011 (3)0.1116 (2)0.0367 (7)
O70.5671 (3)0.3340 (2)0.3024 (2)0.0327 (7)
O80.1070 (3)0.8590 (3)0.8981 (2)0.0365 (7)
O90.2117 (3)0.6751 (3)1.1640 (2)0.0442 (8)
O100.2334 (3)0.7287 (3)0.7860 (2)0.0389 (8)
O110.2198 (3)0.5201 (3)0.7055 (2)0.0454 (8)
O120.2194 (5)0.2939 (4)0.7559 (3)0.0854 (14)
O130.2498 (3)0.3065 (3)0.9829 (2)0.0481 (9)
O140.3225 (3)0.4986 (2)1.0860 (2)0.0382 (7)
P10.66234 (11)0.39684 (9)0.56834 (8)0.0281 (2)
P20.60464 (10)0.27688 (9)0.40729 (8)0.0269 (2)
P30.86202 (10)0.22965 (9)0.48078 (8)0.0251 (2)
P40.24002 (11)0.76270 (10)0.89930 (8)0.0303 (3)
P50.30434 (11)0.62864 (10)1.06672 (8)0.0303 (3)
P60.47563 (11)0.76544 (9)0.99517 (8)0.0266 (2)
H251.256 (4)0.158 (3)0.251 (3)0.021 (10)*
H280.927 (3)0.169 (3)0.690 (2)0.001 (8)*
H350.068 (5)1.123 (4)1.148 (3)0.048 (13)*
H440.371 (5)0.546 (4)1.286 (3)0.041 (13)*
H560.979 (5)0.648 (4)0.795 (3)0.038 (12)*
H600.441 (4)1.001 (3)0.964 (3)0.025 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.034 (2)0.037 (3)0.025 (2)0.003 (2)0.0033 (18)0.0053 (19)
C20.036 (3)0.063 (3)0.037 (3)0.014 (2)0.003 (2)0.014 (2)
C30.042 (3)0.108 (5)0.033 (3)0.017 (3)0.004 (2)0.000 (3)
C40.059 (4)0.078 (4)0.041 (3)0.008 (3)0.010 (3)0.018 (3)
C50.078 (4)0.046 (3)0.043 (3)0.012 (3)0.006 (3)0.009 (2)
C60.046 (3)0.048 (3)0.034 (3)0.015 (2)0.001 (2)0.006 (2)
C70.033 (2)0.031 (2)0.026 (2)0.0150 (19)0.0025 (18)0.0034 (18)
C80.025 (2)0.049 (3)0.048 (3)0.010 (2)0.002 (2)0.008 (2)
C90.034 (3)0.073 (4)0.057 (3)0.016 (3)0.010 (2)0.012 (3)
C100.051 (3)0.046 (3)0.049 (3)0.013 (3)0.002 (3)0.009 (2)
C110.057 (3)0.029 (3)0.048 (3)0.004 (2)0.004 (3)0.003 (2)
C120.031 (2)0.033 (2)0.045 (3)0.0025 (19)0.001 (2)0.006 (2)
C130.045 (3)0.036 (3)0.038 (3)0.014 (2)0.000 (2)0.004 (2)
C140.054 (3)0.032 (3)0.053 (3)0.010 (2)0.009 (3)0.013 (2)
C150.085 (4)0.030 (3)0.066 (4)0.011 (3)0.003 (3)0.004 (3)
C160.101 (5)0.044 (3)0.049 (3)0.022 (3)0.003 (3)0.008 (3)
C170.039 (3)0.055 (3)0.034 (3)0.017 (2)0.005 (2)0.011 (2)
C180.027 (2)0.058 (3)0.033 (3)0.006 (2)0.0038 (19)0.003 (2)
C190.036 (3)0.041 (3)0.038 (3)0.011 (2)0.002 (2)0.002 (2)
C200.027 (2)0.035 (3)0.039 (3)0.0058 (19)0.0041 (19)0.006 (2)
C210.0155 (19)0.035 (2)0.029 (2)0.0065 (17)0.0024 (16)0.0057 (18)
C220.035 (2)0.032 (3)0.032 (2)0.0094 (19)0.0017 (19)0.0021 (19)
C230.039 (3)0.049 (3)0.038 (3)0.024 (2)0.001 (2)0.007 (2)
C240.023 (2)0.065 (3)0.042 (3)0.013 (2)0.004 (2)0.012 (2)
C250.027 (2)0.043 (3)0.045 (3)0.003 (2)0.007 (2)0.003 (2)
C260.029 (2)0.042 (3)0.032 (2)0.003 (2)0.0002 (19)0.003 (2)
C270.0147 (19)0.031 (2)0.038 (2)0.0032 (17)0.0011 (17)0.0060 (19)
C280.026 (2)0.048 (3)0.036 (3)0.010 (2)0.0015 (19)0.003 (2)
C290.032 (2)0.054 (3)0.048 (3)0.004 (2)0.005 (2)0.025 (3)
C300.025 (2)0.046 (3)0.074 (4)0.000 (2)0.005 (2)0.031 (3)
C310.039 (3)0.033 (3)0.061 (3)0.005 (2)0.012 (2)0.011 (2)
C320.033 (2)0.037 (3)0.047 (3)0.006 (2)0.003 (2)0.007 (2)
C330.023 (2)0.035 (2)0.025 (2)0.0032 (18)0.0017 (17)0.0003 (18)
C340.045 (3)0.038 (3)0.049 (3)0.010 (2)0.004 (2)0.010 (2)
C350.067 (4)0.038 (3)0.045 (3)0.006 (3)0.000 (3)0.007 (2)
C360.057 (3)0.039 (3)0.032 (3)0.010 (2)0.006 (2)0.002 (2)
C370.042 (3)0.046 (3)0.050 (3)0.002 (2)0.010 (2)0.005 (3)
C380.032 (3)0.040 (3)0.052 (3)0.003 (2)0.007 (2)0.006 (2)
C390.019 (2)0.046 (3)0.026 (2)0.0094 (19)0.0063 (17)0.0040 (19)
C400.029 (2)0.041 (3)0.048 (3)0.002 (2)0.006 (2)0.008 (2)
C410.048 (3)0.050 (3)0.054 (3)0.014 (3)0.014 (3)0.021 (3)
C420.041 (3)0.091 (4)0.033 (3)0.020 (3)0.001 (2)0.009 (3)
C430.035 (3)0.073 (4)0.038 (3)0.002 (3)0.000 (2)0.013 (3)
C440.031 (2)0.037 (3)0.045 (3)0.006 (2)0.010 (2)0.002 (2)
C450.026 (2)0.043 (3)0.035 (3)0.0025 (19)0.0033 (19)0.005 (2)
C460.036 (2)0.045 (3)0.028 (2)0.002 (2)0.0024 (19)0.005 (2)
C470.107 (3)0.087 (3)0.066 (2)0.057 (2)0.012 (2)0.0037 (19)
C480.086 (5)0.082 (4)0.047 (3)0.047 (4)0.021 (3)0.001 (3)
C490.107 (3)0.087 (3)0.066 (2)0.057 (2)0.012 (2)0.0037 (19)
C500.107 (3)0.087 (3)0.066 (2)0.057 (2)0.012 (2)0.0037 (19)
C510.047 (3)0.040 (3)0.055 (3)0.018 (2)0.013 (2)0.009 (2)
C520.036 (3)0.027 (2)0.075 (4)0.002 (2)0.008 (2)0.000 (2)
C530.025 (2)0.028 (2)0.029 (2)0.0046 (18)0.0038 (18)0.0010 (18)
C540.035 (2)0.035 (3)0.036 (3)0.005 (2)0.000 (2)0.001 (2)
C550.031 (2)0.043 (3)0.039 (3)0.000 (2)0.003 (2)0.012 (2)
C560.024 (2)0.056 (3)0.042 (3)0.007 (2)0.002 (2)0.018 (2)
C570.046 (3)0.051 (3)0.034 (3)0.025 (2)0.010 (2)0.000 (2)
C580.033 (2)0.033 (2)0.036 (3)0.0073 (19)0.002 (2)0.0010 (19)
C590.020 (2)0.035 (2)0.028 (2)0.0019 (17)0.0043 (17)0.0024 (18)
C600.042 (3)0.034 (3)0.038 (3)0.007 (2)0.000 (2)0.001 (2)
C610.053 (3)0.035 (3)0.051 (3)0.011 (2)0.001 (2)0.005 (2)
C620.034 (3)0.045 (3)0.055 (3)0.006 (2)0.008 (2)0.026 (2)
C630.037 (3)0.061 (3)0.036 (3)0.014 (2)0.002 (2)0.010 (2)
C640.035 (3)0.038 (3)0.035 (3)0.011 (2)0.000 (2)0.005 (2)
N10.0219 (18)0.0280 (19)0.042 (2)0.0053 (14)0.0026 (15)0.0061 (16)
N20.0212 (17)0.0284 (19)0.0295 (19)0.0034 (14)0.0006 (14)0.0024 (15)
N30.0236 (18)0.0324 (19)0.0261 (18)0.0091 (15)0.0008 (14)0.0001 (14)
N40.0255 (19)0.037 (2)0.039 (2)0.0082 (16)0.0056 (16)0.0048 (16)
N50.0280 (18)0.033 (2)0.0255 (18)0.0113 (15)0.0027 (15)0.0049 (15)
N60.0292 (19)0.030 (2)0.033 (2)0.0058 (15)0.0048 (15)0.0046 (15)
O10.0366 (17)0.0317 (16)0.0295 (16)0.0009 (13)0.0054 (13)0.0058 (13)
O20.0262 (15)0.0413 (17)0.0291 (16)0.0158 (13)0.0043 (12)0.0012 (13)
O30.0325 (16)0.0274 (16)0.0421 (17)0.0084 (13)0.0047 (13)0.0008 (13)
O40.051 (2)0.044 (2)0.0422 (19)0.0095 (16)0.0046 (16)0.0004 (16)
O50.051 (2)0.043 (2)0.044 (2)0.0147 (16)0.0035 (16)0.0007 (15)
O60.0334 (17)0.0501 (19)0.0288 (16)0.0142 (14)0.0036 (13)0.0088 (14)
O70.0225 (15)0.0445 (18)0.0319 (16)0.0092 (13)0.0038 (12)0.0099 (13)
O80.0289 (16)0.0456 (18)0.0298 (16)0.0056 (13)0.0024 (13)0.0061 (13)
O90.0270 (16)0.068 (2)0.0390 (19)0.0145 (15)0.0045 (14)0.0121 (16)
O100.0278 (17)0.053 (2)0.0319 (17)0.0039 (14)0.0061 (13)0.0094 (14)
O110.050 (2)0.059 (2)0.0338 (18)0.0275 (17)0.0051 (15)0.0112 (15)
O120.107 (4)0.105 (4)0.064 (3)0.066 (3)0.025 (3)0.032 (3)
O130.047 (2)0.0448 (19)0.055 (2)0.0160 (16)0.0053 (17)0.0049 (16)
O140.0465 (19)0.0353 (18)0.0368 (18)0.0170 (15)0.0062 (15)0.0074 (14)
P10.0245 (6)0.0286 (6)0.0306 (6)0.0040 (4)0.0002 (4)0.0023 (5)
P20.0200 (5)0.0322 (6)0.0289 (6)0.0064 (4)0.0020 (4)0.0012 (5)
P30.0204 (5)0.0292 (6)0.0252 (6)0.0043 (4)0.0008 (4)0.0011 (4)
P40.0251 (6)0.0359 (7)0.0287 (6)0.0022 (5)0.0040 (5)0.0036 (5)
P50.0275 (6)0.0365 (7)0.0288 (6)0.0111 (5)0.0000 (5)0.0009 (5)
P60.0232 (5)0.0305 (6)0.0262 (6)0.0055 (4)0.0012 (4)0.0006 (4)
Geometric parameters (Å, º) top
C1—C61.364 (6)C37—H370.9500
C1—C21.382 (6)C38—H380.9500
C1—O11.384 (5)C39—C441.367 (6)
C2—C31.379 (7)C39—O91.402 (5)
C2—H20.9500C39—C401.378 (6)
C3—C41.355 (8)C40—C411.393 (7)
C3—H30.9500C40—H400.9500
C4—C51.382 (8)C41—C421.379 (8)
C4—H40.9500C41—H410.9500
C5—C61.391 (7)C42—C431.365 (8)
C5—H50.9500C42—H420.9500
C6—H60.9500C43—C441.351 (7)
C7—C81.363 (6)C43—H430.9500
C7—C121.391 (6)C44—H440.97 (5)
C7—O21.405 (5)C45—O101.452 (5)
C8—C91.389 (7)C45—C461.491 (6)
C8—H80.9500C45—H45A0.9900
C9—C101.374 (7)C45—H45B0.9900
C9—H90.9500C46—O111.399 (6)
C10—C111.357 (7)C46—H46A0.9900
C10—H100.9500C46—H46B0.9900
C11—C121.388 (6)C47—O111.422 (7)
C11—H110.9500C47—C481.497 (8)
C12—H120.9500C47—H47A0.9900
C13—O31.432 (5)C47—H47B0.9900
C13—C141.495 (6)C48—O121.428 (7)
C13—H13A0.9900C48—H48A0.9900
C13—H13B0.9900C48—H48B0.9900
C14—O41.415 (5)C49—C501.5378 (11)
C14—H14A0.9900C49—O121.394 (7)
C14—H14B0.9900C49—H49A0.9900
C15—O41.419 (6)C49—H49B0.9900
C15—C161.448 (8)C50—O131.394 (7)
C15—H15A0.9900C50—H50A0.9900
C15—H15B0.9900C50—H50B0.9900
C16—O51.426 (6)C51—O131.421 (5)
C16—H16A0.9900C51—C521.508 (7)
C16—H16B0.9900C51—H51A0.9900
C17—O51.410 (6)C51—H51B0.9900
C17—C181.467 (7)C52—O141.444 (6)
C17—H17A0.9900C52—H52A0.9900
C17—H17B0.9900C52—H52B0.9900
C18—O61.442 (5)C53—C541.376 (6)
C18—H18A0.9900C53—C581.392 (6)
C18—H18B0.9900C53—P61.808 (4)
C19—O61.413 (5)C54—C551.376 (6)
C19—C201.506 (6)C54—H540.9500
C19—H19A0.9900C55—C561.376 (7)
C19—H19B0.9900C55—H550.9500
C20—O71.462 (5)C56—C571.381 (7)
C20—H20A0.9900C56—H560.97 (5)
C20—H20B0.9900C57—C581.370 (6)
C21—C221.378 (6)C57—H570.9500
C21—C261.401 (6)C58—H580.9500
C21—P31.804 (4)C59—C601.388 (6)
C22—C231.387 (6)C59—C641.388 (6)
C22—H220.9500C59—P61.798 (4)
C23—C241.390 (7)C60—C611.390 (7)
C23—H230.9500C60—H600.98 (4)
C24—C251.382 (7)C61—C621.366 (7)
C24—H240.9500C61—H610.9500
C25—C261.383 (6)C62—C631.390 (7)
C25—H250.95 (4)C62—H620.9500
C26—H260.9500C63—C641.384 (6)
C27—C281.381 (6)C63—H630.9500
C27—C321.398 (6)C64—H640.9500
C27—P31.795 (4)N1—P11.574 (4)
C28—C291.394 (6)N1—P21.585 (4)
C28—H281.04 (3)N2—P21.577 (3)
C29—C301.368 (7)N2—P31.602 (3)
C29—H290.9500N3—P11.585 (3)
C30—C311.385 (7)N3—P31.605 (3)
C30—H300.9500N4—P51.569 (3)
C31—C321.399 (6)N4—P41.584 (4)
C31—H310.9500N5—P51.575 (3)
C32—H320.9500N5—P61.602 (3)
C33—C381.361 (6)N6—P41.574 (4)
C33—C341.379 (6)N6—P61.606 (3)
C33—O81.402 (5)O1—P11.602 (3)
C34—C351.407 (7)O2—P21.591 (3)
C34—H340.9500O3—P11.576 (3)
C35—C361.377 (8)O7—P21.578 (3)
C35—H351.15 (5)O8—P41.595 (3)
C36—C371.362 (7)O9—P51.596 (3)
C36—H360.9500O10—P41.580 (3)
C37—C381.400 (7)O14—P51.565 (3)
C6—C1—C2120.5 (4)C43—C42—H42120.5
C6—C1—O1120.6 (4)C41—C42—H42120.5
C2—C1—O1118.8 (4)C44—C43—C42121.5 (5)
C1—C2—C3119.9 (5)C44—C43—H43119.2
C1—C2—H2120.0C42—C43—H43119.2
C3—C2—H2120.0C43—C44—C39119.6 (5)
C4—C3—C2119.9 (5)C43—C44—H44121 (3)
C4—C3—H3120.1C39—C44—H44120 (3)
C2—C3—H3120.1O10—C45—C46107.4 (3)
C3—C4—C5120.6 (5)O10—C45—H45A110.2
C3—C4—H4119.7C46—C45—H45A110.2
C5—C4—H4119.7O10—C45—H45B110.2
C4—C5—C6119.8 (5)C46—C45—H45B110.2
C4—C5—H5120.1H45A—C45—H45B108.5
C6—C5—H5120.1O11—C46—C45107.7 (4)
C1—C6—C5119.2 (5)O11—C46—H46A110.2
C1—C6—H6120.4C45—C46—H46A110.2
C5—C6—H6120.4O11—C46—H46B110.2
C8—C7—C12121.5 (4)C45—C46—H46B110.2
C8—C7—O2118.0 (4)H46A—C46—H46B108.5
C12—C7—O2120.5 (4)O11—C47—C48108.0 (5)
C7—C8—C9118.9 (4)O11—C47—H47A110.1
C7—C8—H8120.6C48—C47—H47A110.1
C9—C8—H8120.6O11—C47—H47B110.1
C10—C9—C8121.0 (5)C48—C47—H47B110.1
C10—C9—H9119.5H47A—C47—H47B108.4
C8—C9—H9119.5O12—C48—C47106.7 (5)
C11—C10—C9118.8 (5)O12—C48—H48A110.4
C11—C10—H10120.6C47—C48—H48A110.4
C9—C10—H10120.6O12—C48—H48B110.4
C10—C11—C12122.3 (4)C47—C48—H48B110.4
C10—C11—H11118.9H48A—C48—H48B108.6
C12—C11—H11118.9C50—C49—O12109.8 (5)
C7—C12—C11117.4 (4)C50—C49—H49A109.7
C7—C12—H12121.3O12—C49—H49A109.7
C11—C12—H12121.3C50—C49—H49B109.7
O3—C13—C14108.3 (4)O12—C49—H49B109.7
O3—C13—H13A110.0H49A—C49—H49B108.2
C14—C13—H13A110.0O13—C50—C49121.0 (5)
O3—C13—H13B110.0O13—C50—H50A107.1
C14—C13—H13B110.0C49—C50—H50A107.1
H13A—C13—H13B108.4O13—C50—H50B107.1
O4—C14—C13108.7 (4)C49—C50—H50B107.1
O4—C14—H14A110.0H50A—C50—H50B106.8
C13—C14—H14A110.0O13—C51—C52108.7 (4)
O4—C14—H14B110.0O13—C51—H51A110.0
C13—C14—H14B110.0C52—C51—H51A110.0
H14A—C14—H14B108.3O13—C51—H51B110.0
O4—C15—C16110.5 (4)C52—C51—H51B110.0
O4—C15—H15A109.6H51A—C51—H51B108.3
C16—C15—H15A109.6O14—C52—C51112.7 (4)
O4—C15—H15B109.6O14—C52—H52A109.1
C16—C15—H15B109.6C51—C52—H52A109.1
H15A—C15—H15B108.1O14—C52—H52B109.1
O5—C16—C15110.1 (5)C51—C52—H52B109.1
O5—C16—H16A109.6H52A—C52—H52B107.8
C15—C16—H16A109.6C54—C53—C58118.6 (4)
O5—C16—H16B109.6C54—C53—P6122.2 (3)
C15—C16—H16B109.6C58—C53—P6119.2 (3)
H16A—C16—H16B108.2C53—C54—C55121.0 (4)
O5—C17—C18108.7 (4)C53—C54—H54119.5
O5—C17—H17A109.9C55—C54—H54119.5
C18—C17—H17A109.9C56—C55—C54120.3 (4)
O5—C17—H17B109.9C56—C55—H55119.8
C18—C17—H17B109.9C54—C55—H55119.8
H17A—C17—H17B108.3C55—C56—C57118.9 (4)
O6—C18—C17112.9 (4)C55—C56—H56123 (3)
O6—C18—H18A109.0C57—C56—H56118 (3)
C17—C18—H18A109.0C58—C57—C56121.1 (4)
O6—C18—H18B109.0C58—C57—H57119.5
C17—C18—H18B109.0C56—C57—H57119.5
H18A—C18—H18B107.8C57—C58—C53120.1 (4)
O6—C19—C20111.4 (4)C57—C58—H58120.0
O6—C19—H19A109.3C53—C58—H58120.0
C20—C19—H19A109.3C60—C59—C64119.5 (4)
O6—C19—H19B109.3C60—C59—P6119.6 (3)
C20—C19—H19B109.3C64—C59—P6120.9 (3)
H19A—C19—H19B108.0C59—C60—C61120.4 (4)
O7—C20—C19108.4 (4)C59—C60—H60118 (2)
O7—C20—H20A110.0C61—C60—H60121 (2)
C19—C20—H20A110.0C62—C61—C60119.7 (5)
O7—C20—H20B110.0C62—C61—H61120.1
C19—C20—H20B110.0C60—C61—H61120.1
H20A—C20—H20B108.4C61—C62—C63120.5 (4)
C22—C21—C26118.9 (4)C61—C62—H62119.7
C22—C21—P3120.3 (3)C63—C62—H62119.7
C26—C21—P3120.7 (3)C64—C63—C62120.0 (4)
C21—C22—C23120.6 (4)C64—C63—H63120.0
C21—C22—H22119.7C62—C63—H63120.0
C23—C22—H22119.7C63—C64—C59119.8 (4)
C22—C23—C24120.5 (4)C63—C64—H64120.1
C22—C23—H23119.7C59—C64—H64120.1
C24—C23—H23119.7P1—N1—P2122.5 (2)
C25—C24—C23119.0 (4)P2—N2—P3122.9 (2)
C25—C24—H24120.5P1—N3—P3120.8 (2)
C23—C24—H24120.5P5—N4—P4122.3 (2)
C26—C25—C24120.7 (5)P5—N5—P6120.4 (2)
C26—C25—H25121 (2)P4—N6—P6122.5 (2)
C24—C25—H25118 (2)C1—O1—P1122.2 (3)
C25—C26—C21120.3 (5)C7—O2—P2122.7 (2)
C25—C26—H26119.9C13—O3—P1120.9 (3)
C21—C26—H26119.9C15—O4—C14113.2 (4)
C28—C27—C32119.5 (4)C17—O5—C16110.7 (4)
C28—C27—P3120.0 (3)C19—O6—C18114.9 (3)
C32—C27—P3120.5 (3)C20—O7—P2118.7 (3)
C27—C28—C29119.9 (5)C33—O8—P4121.0 (2)
C27—C28—H28124.3 (17)C39—O9—P5122.5 (3)
C29—C28—H28115.7 (17)C45—O10—P4118.8 (2)
C30—C29—C28120.6 (5)C46—O11—C47112.8 (4)
C30—C29—H29119.7C49—O12—C48117.5 (5)
C28—C29—H29119.7C50—O13—C51117.4 (4)
C31—C30—C29120.5 (4)C52—O14—P5118.3 (3)
C31—C30—H30119.7O3—P1—N1105.96 (17)
C29—C30—H30119.7O3—P1—N3112.27 (17)
C30—C31—C32119.2 (5)N1—P1—N3118.50 (18)
C30—C31—H31120.4O3—P1—O198.76 (16)
C32—C31—H31120.4N1—P1—O1110.71 (18)
C31—C32—C27120.1 (4)N3—P1—O1108.84 (16)
C31—C32—H32119.9O7—P2—N1112.01 (18)
C27—C32—H32119.9O7—P2—N2110.43 (17)
C38—C33—C34122.7 (4)N1—P2—N2116.76 (18)
C38—C33—O8118.9 (4)O7—P2—O294.59 (15)
C34—C33—O8118.3 (4)N1—P2—O2109.31 (17)
C33—C34—C35117.4 (5)N2—P2—O2111.56 (17)
C33—C34—H34121.3N3—P3—N2117.30 (17)
C35—C34—H34121.3N3—P3—C27108.53 (19)
C36—C35—C34120.7 (5)N2—P3—C27108.41 (19)
C36—C35—H35119 (2)N3—P3—C21107.34 (19)
C34—C35—H35120 (2)N2—P3—C21108.66 (18)
C37—C36—C35120.0 (5)C27—P3—C21106.04 (18)
C37—C36—H36120.0O10—P4—N6110.86 (18)
C35—C36—H36120.0O10—P4—N4111.54 (19)
C36—C37—C38120.6 (5)N6—P4—N4116.97 (18)
C36—C37—H37119.7O10—P4—O894.06 (15)
C38—C37—H37119.7N6—P4—O8111.30 (18)
C33—C38—C37118.5 (5)N4—P4—O8109.79 (18)
C33—C38—H38120.7O14—P5—N4110.20 (18)
C37—C38—H38120.7O14—P5—N5109.64 (18)
C44—C39—O9122.3 (4)N4—P5—N5117.69 (19)
C44—C39—C40121.2 (4)O14—P5—O9100.10 (18)
O9—C39—C40116.4 (4)N4—P5—O9106.06 (18)
C41—C40—C39118.0 (4)N5—P5—O9111.69 (18)
C41—C40—H40121.0N5—P6—N6117.01 (18)
C39—C40—H40121.0N5—P6—C59109.39 (18)
C42—C41—C40120.6 (5)N6—P6—C59107.65 (19)
C42—C41—H41119.7N5—P6—C53109.10 (18)
C40—C41—H41119.7N6—P6—C53108.32 (18)
C43—C42—C41119.0 (5)C59—P6—C53104.67 (19)
C6—C1—C2—C32.0 (7)C48—C47—O11—C46173.0 (5)
O1—C1—C2—C3179.5 (4)C50—C49—O12—C4891.5 (7)
C1—C2—C3—C40.7 (8)C47—C48—O12—C49173.3 (5)
C2—C3—C4—C50.5 (8)C49—C50—O13—C5160.8 (7)
C3—C4—C5—C60.6 (8)C52—C51—O13—C50166.8 (4)
C2—C1—C6—C51.9 (7)C51—C52—O14—P595.0 (4)
O1—C1—C6—C5179.4 (4)C13—O3—P1—N1179.2 (3)
C4—C5—C6—C10.7 (8)C13—O3—P1—N350.0 (3)
C12—C7—C8—C91.6 (7)C13—O3—P1—O164.6 (3)
O2—C7—C8—C9176.4 (4)P2—N1—P1—O3114.2 (3)
C7—C8—C9—C102.8 (8)P2—N1—P1—N312.9 (3)
C8—C9—C10—C112.0 (8)P2—N1—P1—O1139.7 (2)
C9—C10—C11—C120.1 (8)P3—N3—P1—O3117.6 (2)
C8—C7—C12—C110.2 (7)P3—N3—P1—N16.5 (3)
O2—C7—C12—C11178.2 (4)P3—N3—P1—O1134.2 (2)
C10—C11—C12—C71.0 (7)C1—O1—P1—O3150.1 (3)
O3—C13—C14—O469.7 (5)C1—O1—P1—N199.0 (3)
O4—C15—C16—O569.1 (6)C1—O1—P1—N332.9 (4)
O5—C17—C18—O670.3 (5)C20—O7—P2—N181.6 (3)
O6—C19—C20—O7174.5 (3)C20—O7—P2—N250.4 (3)
C26—C21—C22—C231.3 (6)C20—O7—P2—O2165.4 (3)
P3—C21—C22—C23178.6 (3)P1—N1—P2—O7118.1 (2)
C21—C22—C23—C240.7 (7)P1—N1—P2—N210.6 (3)
C22—C23—C24—C250.3 (7)P1—N1—P2—O2138.4 (2)
C23—C24—C25—C260.7 (7)P3—N2—P2—O7127.4 (2)
C24—C25—C26—C210.1 (7)P3—N2—P2—N12.0 (3)
C22—C21—C26—C251.0 (6)P3—N2—P2—O2128.7 (2)
P3—C21—C26—C25178.2 (3)C7—O2—P2—O7172.5 (3)
C32—C27—C28—C292.0 (6)C7—O2—P2—N157.2 (3)
P3—C27—C28—C29177.9 (3)C7—O2—P2—N273.4 (3)
C27—C28—C29—C300.1 (7)P1—N3—P3—N21.4 (3)
C28—C29—C30—C311.4 (7)P1—N3—P3—C27121.8 (2)
C29—C30—C31—C321.1 (7)P1—N3—P3—C21124.0 (2)
C30—C31—C32—C270.8 (7)P2—N2—P3—N33.7 (3)
C28—C27—C32—C312.3 (6)P2—N2—P3—C27119.6 (2)
P3—C27—C32—C31177.6 (3)P2—N2—P3—C21125.6 (2)
C38—C33—C34—C351.1 (7)C28—C27—P3—N311.4 (4)
O8—C33—C34—C35174.8 (4)C32—C27—P3—N3168.7 (3)
C33—C34—C35—C360.8 (7)C28—C27—P3—N2139.9 (3)
C34—C35—C36—C370.1 (7)C32—C27—P3—N240.3 (4)
C35—C36—C37—C380.5 (7)C28—C27—P3—C21103.6 (4)
C34—C33—C38—C370.5 (6)C32—C27—P3—C2176.3 (4)
O8—C33—C38—C37175.4 (3)C22—C21—P3—N315.3 (4)
C36—C37—C38—C330.3 (7)C26—C21—P3—N3167.5 (3)
C44—C39—C40—C410.8 (7)C22—C21—P3—N2112.5 (3)
O9—C39—C40—C41179.5 (4)C26—C21—P3—N264.7 (3)
C39—C40—C41—C420.5 (7)C22—C21—P3—C27131.2 (3)
C40—C41—C42—C430.7 (8)C26—C21—P3—C2751.6 (4)
C41—C42—C43—C440.3 (8)C45—O10—P4—N654.8 (4)
C42—C43—C44—C391.6 (7)C45—O10—P4—N477.5 (3)
O9—C39—C44—C43179.6 (4)C45—O10—P4—O8169.4 (3)
C40—C39—C44—C431.8 (7)P6—N6—P4—O10125.7 (2)
O10—C45—C46—O1167.7 (4)P6—N6—P4—N43.7 (3)
O11—C47—C48—O1268.9 (7)P6—N6—P4—O8131.0 (2)
O12—C49—C50—O1367.9 (8)P5—N4—P4—O10136.0 (2)
O13—C51—C52—O1471.4 (5)P5—N4—P4—N67.0 (3)
C58—C53—C54—C550.8 (6)P5—N4—P4—O8121.1 (2)
P6—C53—C54—C55177.8 (3)C33—O8—P4—O10168.8 (3)
C53—C54—C55—C560.5 (7)C33—O8—P4—N676.9 (4)
C54—C55—C56—C571.3 (7)C33—O8—P4—N454.2 (4)
C55—C56—C57—C580.9 (7)C52—O14—P5—N469.9 (3)
C56—C57—C58—C530.3 (7)C52—O14—P5—N561.1 (3)
C54—C53—C58—C571.2 (6)C52—O14—P5—O9178.6 (3)
P6—C53—C58—C57177.4 (3)P4—N4—P5—O14145.8 (2)
C64—C59—C60—C610.7 (7)P4—N4—P5—N519.1 (3)
P6—C59—C60—C61179.3 (4)P4—N4—P5—O9106.7 (3)
C59—C60—C61—C620.1 (7)P6—N5—P5—O14147.8 (2)
C60—C61—C62—C631.5 (7)P6—N5—P5—N420.8 (3)
C61—C62—C63—C642.1 (7)P6—N5—P5—O9102.2 (3)
C62—C63—C64—C591.3 (7)C39—O9—P5—O1492.9 (3)
C60—C59—C64—C630.1 (6)C39—O9—P5—N4152.5 (3)
P6—C59—C64—C63179.9 (3)C39—O9—P5—N523.1 (4)
C6—C1—O1—P172.7 (5)P5—N5—P6—N610.7 (3)
C2—C1—O1—P1109.8 (4)P5—N5—P6—C59112.0 (3)
C8—C7—O2—P2116.6 (4)P5—N5—P6—C53134.0 (2)
C12—C7—O2—P265.4 (5)P4—N6—P6—N51.8 (3)
C14—C13—O3—P1156.1 (3)P4—N6—P6—C59125.4 (3)
C16—C15—O4—C14179.3 (4)P4—N6—P6—C53121.9 (3)
C13—C14—O4—C15143.1 (4)C60—C59—P6—N5159.0 (3)
C18—C17—O5—C16173.7 (4)C64—C59—P6—N521.0 (4)
C15—C16—O5—C17178.9 (4)C60—C59—P6—N630.9 (4)
C20—C19—O6—C1883.6 (4)C64—C59—P6—N6149.1 (3)
C17—C18—O6—C19123.4 (4)C60—C59—P6—C5384.2 (4)
C19—C20—O7—P2104.7 (3)C64—C59—P6—C5395.8 (4)
C38—C33—O8—P4102.3 (4)C54—C53—P6—N512.8 (4)
C34—C33—O8—P481.7 (4)C58—C53—P6—N5168.6 (3)
C44—C39—O9—P562.6 (5)C54—C53—P6—N6141.2 (4)
C40—C39—O9—P5118.7 (4)C58—C53—P6—N640.3 (4)
C46—C45—O10—P4152.5 (3)C54—C53—P6—C59104.1 (4)
C45—C46—O11—C47169.7 (4)C58—C53—P6—C5974.4 (4)
(6) top
Crystal data top
C22H32N3O7P3F(000) = 1144
Mr = 543.42Dx = 1.387 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.8293 (2) ÅCell parameters from 8163 reflections
b = 10.3312 (2) Åθ = 2.9–27.5°
c = 21.6318 (5) ŵ = 0.28 mm1
β = 100.203 (1)°T = 293 K
V = 2601.84 (9) Å3Plate, colourless
Z = 40.26 × 0.20 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
5841 independent reflections
Radiation source: Nonius FR591 rotating anode4160 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ & ω scansh = 1415
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 1213
Tmin = 0.932, Tmax = 0.981l = 2728
18814 measured reflections
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)] = 0.052H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0776P)2 + 1.3016P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.061
5841 reflectionsΔρmax = 0.46 e Å3
319 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (11)
Crystal data top
C22H32N3O7P3V = 2601.84 (9) Å3
Mr = 543.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.8293 (2) ŵ = 0.28 mm1
b = 10.3312 (2) ÅT = 293 K
c = 21.6318 (5) Å0.26 × 0.20 × 0.07 mm
β = 100.203 (1)°
Data collection top
Nonius KappaCCD
diffractometer
5841 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
4160 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.981Rint = 0.038
18814 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.00Δρmax = 0.46 e Å3
5841 reflectionsΔρmin = 0.31 e Å3
319 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3021 (3)0.9455 (3)0.21276 (16)0.0714 (9)
H1A0.29810.89610.17490.107*
H1B0.29020.88930.24640.107*
H1C0.37630.98550.22310.107*
C20.3682 (4)0.8899 (3)0.03540 (18)0.0891 (12)
H2A0.40670.91560.07640.134*
H2B0.42200.84850.01340.134*
H2C0.30730.83070.03940.134*
C30.0040 (2)1.1653 (3)0.14186 (16)0.0641 (8)
H3A0.01431.10510.17480.077*
H3B0.00811.11720.10300.077*
C40.0954 (3)1.2645 (4)0.1345 (2)0.0875 (12)
H4A0.16951.22370.13370.105*
H4B0.08191.32430.16960.105*
C50.1946 (4)1.4066 (5)0.0588 (3)0.1176 (19)
H5A0.20361.46760.09160.141*
H5B0.26151.35060.05150.141*
C60.1849 (4)1.4771 (5)0.0004 (3)0.127 (2)
H6A0.25291.52970.01250.152*
H6B0.11871.53410.00800.152*
C70.1367 (4)1.4515 (5)0.0980 (3)0.123 (2)
H7A0.07591.51250.08270.148*
H7B0.20021.49880.12240.148*
C80.0949 (4)1.3538 (6)0.1374 (2)0.125 (2)
H8A0.15141.28510.14540.150*
H8B0.08921.39310.17740.150*
C90.0084 (3)1.2023 (4)0.06467 (19)0.0818 (10)
H9A0.05801.14720.07750.098*
H9B0.00011.24460.02570.098*
C100.1109 (3)1.1247 (3)0.05482 (17)0.0753 (9)
H10A0.12581.09500.09520.090*
H10B0.09851.04900.03030.090*
C110.5464 (2)1.1787 (2)0.17236 (12)0.0447 (6)
C120.5809 (3)1.2011 (3)0.23638 (15)0.0684 (8)
H120.54361.26390.25620.082*
C130.6699 (3)1.1310 (4)0.27077 (19)0.0860 (11)
H130.69221.14690.31350.103*
C140.7255 (3)1.0382 (4)0.2423 (2)0.0840 (11)
H140.78500.99070.26570.101*
C150.6930 (3)1.0158 (3)0.1795 (2)0.0780 (10)
H150.73080.95260.16030.094*
C160.6036 (2)1.0867 (3)0.14346 (15)0.0596 (7)
H160.58311.07170.10050.072*
C170.4622 (2)1.4311 (2)0.13249 (11)0.0423 (5)
C180.4390 (2)1.5125 (3)0.17955 (14)0.0555 (7)
H180.40001.48100.21010.067*
C190.4737 (3)1.6402 (3)0.18127 (17)0.0706 (9)
H190.45771.69440.21290.085*
C200.5314 (3)1.6870 (3)0.13685 (18)0.0734 (9)
H200.55461.77310.13850.088*
C210.5554 (3)1.6088 (3)0.09003 (17)0.0726 (9)
H210.59521.64150.06000.087*
C220.5202 (2)1.4797 (3)0.08718 (14)0.0572 (7)
H220.53561.42650.05500.069*
N10.2112 (2)1.0827 (2)0.08603 (10)0.0485 (5)
N20.39368 (18)1.2137 (2)0.05984 (9)0.0462 (5)
N30.32212 (17)1.2480 (2)0.17228 (9)0.0431 (5)
O10.21493 (17)1.04370 (18)0.20364 (8)0.0562 (5)
O20.3218 (2)1.00054 (18)0.00146 (9)0.0650 (6)
O40.0948 (2)1.3320 (3)0.07766 (15)0.0915 (8)
O50.1734 (2)1.3896 (3)0.04690 (16)0.0980 (9)
O60.0136 (2)1.2976 (3)0.11189 (13)0.0977 (9)
O70.21093 (17)1.19435 (19)0.02255 (8)0.0565 (5)
O30.10657 (14)1.22816 (17)0.15776 (9)0.0500 (4)
P10.21922 (5)1.15158 (6)0.15205 (3)0.04093 (18)
P20.28683 (6)1.12480 (6)0.03577 (3)0.04374 (19)
P30.42139 (5)1.26306 (6)0.13107 (3)0.03865 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.093 (2)0.0566 (17)0.0664 (19)0.0088 (17)0.0186 (17)0.0190 (15)
C20.138 (4)0.0580 (19)0.078 (2)0.028 (2)0.038 (2)0.0070 (17)
C30.0464 (15)0.0665 (19)0.079 (2)0.0168 (14)0.0105 (14)0.0009 (16)
C40.0464 (18)0.104 (3)0.116 (3)0.0064 (18)0.0236 (19)0.005 (3)
C50.069 (2)0.120 (4)0.148 (4)0.045 (3)0.021 (3)0.047 (4)
C60.105 (4)0.084 (3)0.163 (5)0.033 (3)0.050 (4)0.024 (3)
C70.068 (2)0.104 (3)0.190 (6)0.010 (2)0.000 (3)0.069 (4)
C80.080 (3)0.182 (6)0.104 (4)0.026 (3)0.007 (3)0.062 (4)
C90.068 (2)0.081 (2)0.094 (3)0.0098 (19)0.0084 (19)0.011 (2)
C100.075 (2)0.076 (2)0.066 (2)0.0119 (18)0.0112 (17)0.0049 (17)
C110.0417 (12)0.0418 (13)0.0516 (14)0.0029 (11)0.0107 (11)0.0053 (11)
C120.0679 (19)0.0704 (19)0.0599 (18)0.0136 (16)0.0081 (15)0.0015 (15)
C130.079 (2)0.091 (3)0.076 (2)0.010 (2)0.0186 (19)0.010 (2)
C140.0554 (19)0.075 (2)0.114 (3)0.0091 (17)0.004 (2)0.025 (2)
C150.0581 (18)0.0576 (19)0.123 (3)0.0151 (16)0.029 (2)0.007 (2)
C160.0533 (16)0.0562 (16)0.0727 (19)0.0017 (13)0.0203 (14)0.0010 (14)
C170.0396 (12)0.0427 (13)0.0442 (13)0.0020 (10)0.0060 (10)0.0020 (10)
C180.0610 (17)0.0497 (15)0.0563 (16)0.0018 (13)0.0112 (13)0.0051 (12)
C190.087 (2)0.0439 (16)0.077 (2)0.0054 (15)0.0024 (18)0.0079 (14)
C200.080 (2)0.0395 (15)0.092 (3)0.0055 (15)0.0072 (19)0.0068 (16)
C210.072 (2)0.0608 (19)0.086 (2)0.0116 (16)0.0170 (17)0.0233 (17)
C220.0599 (17)0.0519 (15)0.0631 (17)0.0024 (13)0.0198 (14)0.0052 (13)
N10.0601 (13)0.0423 (11)0.0450 (12)0.0118 (10)0.0141 (10)0.0056 (9)
N20.0484 (12)0.0540 (12)0.0380 (11)0.0049 (10)0.0129 (9)0.0030 (9)
N30.0423 (11)0.0517 (12)0.0370 (10)0.0070 (9)0.0119 (8)0.0064 (9)
O10.0709 (12)0.0512 (10)0.0519 (11)0.0029 (9)0.0252 (9)0.0110 (9)
O20.0995 (16)0.0461 (10)0.0537 (11)0.0075 (11)0.0256 (11)0.0072 (9)
O40.0530 (13)0.0855 (17)0.132 (2)0.0085 (12)0.0061 (14)0.0093 (16)
O50.0861 (18)0.0715 (16)0.132 (2)0.0000 (14)0.0078 (17)0.0082 (17)
O60.0673 (15)0.130 (2)0.0927 (19)0.0112 (15)0.0065 (13)0.0477 (17)
O70.0669 (12)0.0533 (11)0.0442 (10)0.0085 (9)0.0042 (9)0.0044 (8)
O30.0386 (9)0.0487 (10)0.0639 (11)0.0058 (8)0.0124 (8)0.0102 (8)
P10.0455 (4)0.0388 (3)0.0404 (3)0.0047 (3)0.0129 (3)0.0006 (2)
P20.0569 (4)0.0390 (3)0.0360 (3)0.0024 (3)0.0100 (3)0.0030 (2)
P30.0391 (3)0.0416 (3)0.0364 (3)0.0016 (3)0.0097 (2)0.0011 (2)
Geometric parameters (Å, º) top
C1—O11.435 (4)C10—H10B0.9700
C1—H1A0.9600C11—C161.379 (4)
C1—H1B0.9600C11—C121.392 (4)
C1—H1C0.9600C11—P31.810 (3)
C2—O21.415 (4)C12—C131.382 (5)
C2—H2A0.9600C12—H120.9300
C2—H2B0.9600C13—C141.369 (6)
C2—H2C0.9600C13—H130.9300
C3—O31.446 (3)C14—C151.365 (6)
C3—C41.477 (5)C14—H140.9300
C3—H3A0.9700C15—C161.404 (5)
C3—H3B0.9700C15—H150.9300
C4—O41.415 (5)C16—H160.9300
C4—H4A0.9700C17—C221.387 (4)
C4—H4B0.9700C17—C181.385 (4)
C5—O41.408 (4)C17—P31.800 (3)
C5—C61.480 (8)C18—C191.380 (4)
C5—H5A0.9700C18—H180.9300
C5—H5B0.9700C19—C201.362 (5)
C6—O51.390 (6)C19—H190.9300
C6—H6A0.9700C20—C211.364 (5)
C6—H6B0.9700C20—H200.9300
C7—O51.409 (6)C21—C221.395 (4)
C7—C81.463 (8)C21—H210.9300
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700N1—P11.583 (2)
C8—O61.427 (5)N1—P21.586 (2)
C8—H8A0.9700N2—P21.575 (2)
C8—H8B0.9700N2—P31.601 (2)
C9—O61.428 (4)N3—P11.574 (2)
C9—C101.437 (5)N3—P31.6027 (19)
C9—H9A0.9700O1—P11.5845 (18)
C9—H9B0.9700O2—P21.5745 (19)
C10—O71.454 (4)O7—P21.5852 (19)
C10—H10A0.9700O3—P11.5733 (18)
O1—C1—H1A109.5C12—C11—P3118.7 (2)
O1—C1—H1B109.5C13—C12—C11120.6 (3)
H1A—C1—H1B109.5C13—C12—H12119.7
O1—C1—H1C109.5C11—C12—H12119.7
H1A—C1—H1C109.5C14—C13—C12120.4 (4)
H1B—C1—H1C109.5C14—C13—H13119.8
O2—C2—H2A109.5C12—C13—H13119.8
O2—C2—H2B109.5C13—C14—C15119.5 (3)
H2A—C2—H2B109.5C13—C14—H14120.2
O2—C2—H2C109.5C15—C14—H14120.2
H2A—C2—H2C109.5C14—C15—C16121.1 (3)
H2B—C2—H2C109.5C14—C15—H15119.4
O3—C3—C4109.1 (3)C16—C15—H15119.4
O3—C3—H3A109.9C11—C16—C15119.3 (3)
C4—C3—H3A109.9C11—C16—H16120.4
O3—C3—H3B109.9C15—C16—H16120.4
C4—C3—H3B109.9C22—C17—C18119.1 (2)
H3A—C3—H3B108.3C22—C17—P3120.1 (2)
O4—C4—C3108.6 (3)C18—C17—P3120.7 (2)
O4—C4—H4A110.0C19—C18—C17120.3 (3)
C3—C4—H4A110.0C19—C18—H18119.9
O4—C4—H4B110.0C17—C18—H18119.9
C3—C4—H4B110.0C20—C19—C18120.3 (3)
H4A—C4—H4B108.3C20—C19—H19119.8
O4—C5—C6109.3 (4)C18—C19—H19119.8
O4—C5—H5A109.8C21—C20—C19120.6 (3)
C6—C5—H5A109.8C21—C20—H20119.7
O4—C5—H5B109.8C19—C20—H20119.7
C6—C5—H5B109.8C20—C21—C22119.9 (3)
H5A—C5—H5B108.3C20—C21—H21120.0
O5—C6—C5109.9 (4)C22—C21—H21120.0
O5—C6—H6A109.7C17—C22—C21119.8 (3)
C5—C6—H6A109.7C17—C22—H22120.1
O5—C6—H6B109.7C21—C22—H22120.1
C5—C6—H6B109.7P1—N1—P2122.96 (13)
H6A—C6—H6B108.2P2—N2—P3121.30 (13)
O5—C7—C8109.1 (4)P1—N3—P3120.91 (12)
O5—C7—H7A109.9C1—O1—P1118.82 (17)
C8—C7—H7A109.9C2—O2—P2121.6 (2)
O5—C7—H7B109.9C4—O4—C5112.9 (4)
C8—C7—H7B109.9C6—O5—C7111.5 (4)
H7A—C7—H7B108.3C9—O6—C8114.1 (3)
O6—C8—C7115.5 (4)C10—O7—P2117.11 (19)
O6—C8—H8A108.4C3—O3—P1119.92 (18)
C7—C8—H8A108.4O3—P1—N3106.50 (10)
O6—C8—H8B108.4O3—P1—N1112.39 (11)
C7—C8—H8B108.4N3—P1—N1117.06 (11)
H8A—C8—H8B107.5O3—P1—O199.50 (10)
O6—C9—C10110.4 (3)N3—P1—O1111.66 (11)
O6—C9—H9A109.6N1—P1—O1108.35 (11)
C10—C9—H9A109.6N2—P2—O2111.65 (12)
O6—C9—H9B109.6N2—P2—O7107.88 (11)
C10—C9—H9B109.6O2—P2—O798.83 (11)
H9A—C9—H9B108.1N2—P2—N1116.77 (11)
C9—C10—O7112.9 (3)O2—P2—N1109.07 (11)
C9—C10—H10A109.0O7—P2—N1111.18 (12)
O7—C10—H10A109.0N3—P3—N2117.33 (11)
C9—C10—H10B109.0N3—P3—C17107.74 (11)
O7—C10—H10B109.0N2—P3—C17109.39 (12)
H10A—C10—H10B107.8N3—P3—C11107.10 (11)
C16—C11—C12119.0 (3)N2—P3—C11109.37 (12)
C16—C11—P3122.1 (2)C17—P3—C11105.23 (11)
O3—C3—C4—O472.9 (4)P2—N1—P1—N311.2 (2)
O4—C5—C6—O560.2 (5)P2—N1—P1—O1138.55 (16)
O5—C7—C8—O673.1 (5)C1—O1—P1—O3177.3 (2)
O6—C9—C10—O771.9 (4)C1—O1—P1—N370.6 (2)
C16—C11—C12—C130.9 (5)C1—O1—P1—N159.7 (2)
P3—C11—C12—C13174.6 (3)P3—N2—P2—O2128.62 (15)
C11—C12—C13—C140.1 (6)P3—N2—P2—O7123.82 (16)
C12—C13—C14—C150.5 (6)P3—N2—P2—N12.2 (2)
C13—C14—C15—C160.1 (6)C2—O2—P2—N282.1 (3)
C12—C11—C16—C151.5 (4)C2—O2—P2—O7164.5 (3)
P3—C11—C16—C15173.9 (2)C2—O2—P2—N148.4 (3)
C14—C15—C16—C111.1 (5)C10—O7—P2—N2176.2 (2)
C22—C17—C18—C190.2 (4)C10—O7—P2—O259.9 (2)
P3—C17—C18—C19178.0 (2)C10—O7—P2—N154.6 (2)
C17—C18—C19—C200.2 (5)P1—N1—P2—N215.5 (2)
C18—C19—C20—C210.2 (5)P1—N1—P2—O2143.24 (17)
C19—C20—C21—C220.4 (5)P1—N1—P2—O7108.81 (17)
C18—C17—C22—C210.7 (4)P1—N3—P3—N218.8 (2)
P3—C17—C22—C21177.5 (2)P1—N3—P3—C17142.71 (15)
C20—C21—C22—C170.8 (5)P1—N3—P3—C11104.52 (16)
C3—C4—O4—C5165.7 (3)P2—N2—P3—N314.3 (2)
C6—C5—O4—C4178.0 (4)P2—N2—P3—C17137.33 (15)
C5—C6—O5—C7165.9 (4)P2—N2—P3—C11107.91 (16)
C8—C7—O5—C6164.0 (4)C22—C17—P3—N3161.0 (2)
C10—C9—O6—C8163.1 (4)C18—C17—P3—N320.8 (2)
C7—C8—O6—C977.5 (6)C22—C17—P3—N232.4 (2)
C9—C10—O7—P2131.0 (3)C18—C17—P3—N2149.4 (2)
C4—C3—O3—P1164.9 (2)C22—C17—P3—C1185.0 (2)
C3—O3—P1—N3179.6 (2)C18—C17—P3—C1193.2 (2)
C3—O3—P1—N150.2 (2)C16—C11—P3—N3127.7 (2)
C3—O3—P1—O164.3 (2)C12—C11—P3—N347.7 (3)
P3—N3—P1—O3133.20 (14)C16—C11—P3—N20.4 (3)
P3—N3—P1—N16.5 (2)C12—C11—P3—N2175.8 (2)
P3—N3—P1—O1119.16 (15)C16—C11—P3—C17117.8 (2)
P2—N1—P1—O3112.50 (17)C12—C11—P3—C1766.8 (2)
(7) top
Crystal data top
C32H40N5O6P3Z = 2
Mr = 683.60F(000) = 720
Triclinic, P1Dx = 1.368 Mg m3
a = 10.519 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.694 (3) ÅCell parameters from 11413 reflections
c = 14.340 (3) Åθ = 2.9–27.5°
α = 114.81 (3)°µ = 0.23 mm1
β = 93.81 (3)°T = 150 K
γ = 103.59 (3)°Block, colourless
V = 1659.6 (6) Å30.30 × 0.17 × 0.08 mm
Data collection top
Nonius KappaCCD
diffractometer
7460 independent reflections
Radiation source: Nonius FR591 rotating anode6157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ and ω scansh = 1313
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 1615
Tmin = 0.934, Tmax = 0.983l = 1718
19478 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.65 w = 1/[σ2(Fo2) + (0.0981P)2 + 3.4222P]
where P = (Fo2 + 2Fc2)/3
7460 reflections(Δ/σ)max = 0.005
431 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C32H40N5O6P3γ = 103.59 (3)°
Mr = 683.60V = 1659.6 (6) Å3
Triclinic, P1Z = 2
a = 10.519 (2) ÅMo Kα radiation
b = 12.694 (3) ŵ = 0.23 mm1
c = 14.340 (3) ÅT = 150 K
α = 114.81 (3)°0.30 × 0.17 × 0.08 mm
β = 93.81 (3)°
Data collection top
Nonius KappaCCD
diffractometer
7460 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
6157 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.983Rint = 0.033
19478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.65Δρmax = 0.28 e Å3
7460 reflectionsΔρmin = 0.45 e Å3
431 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O61.17466 (14)0.98464 (12)0.45589 (10)0.0252 (3)
C210.82058 (17)0.76389 (16)0.00272 (14)0.0222 (4)
C220.93610 (19)0.84509 (17)0.00216 (15)0.0268 (4)
H220.96590.92530.05300.032*
C231.0078 (2)0.80890 (19)0.08215 (16)0.0309 (4)
H231.08650.86450.08140.037*
C240.9651 (2)0.69219 (19)0.16285 (15)0.0303 (4)
H241.01420.66810.21750.036*
C250.8506 (2)0.61029 (19)0.16403 (16)0.0316 (4)
H250.82190.52990.21900.038*
C260.77830 (19)0.64609 (18)0.08474 (15)0.0280 (4)
H260.69940.59020.08610.034*
C270.56009 (17)0.75962 (16)0.04244 (13)0.0224 (4)
C280.5147 (2)0.83055 (19)0.00353 (16)0.0314 (4)
H280.57370.90370.01030.038*
C290.3830 (2)0.7939 (2)0.04516 (18)0.0385 (5)
H290.35130.84290.07060.046*
C300.2974 (2)0.6863 (2)0.05689 (16)0.0365 (5)
H300.20730.66150.09070.044*
C310.34218 (19)0.61461 (19)0.01972 (15)0.0323 (4)
H310.28350.54030.02870.039*
C320.47359 (18)0.65191 (17)0.03082 (14)0.0259 (4)
H320.50440.60350.05750.031*
C10.66710 (17)0.68628 (16)0.36827 (14)0.0211 (3)
C20.62464 (19)0.57036 (17)0.28489 (15)0.0261 (4)
H20.66800.55100.22640.031*
C30.5186 (2)0.48309 (17)0.28750 (16)0.0291 (4)
H30.48950.40430.23020.035*
C40.4553 (2)0.50945 (18)0.37217 (17)0.0320 (4)
H40.38230.44940.37290.038*
C50.4988 (2)0.62423 (19)0.45628 (16)0.0309 (4)
H50.45650.64260.51530.037*
C60.60394 (18)0.71218 (17)0.45419 (14)0.0242 (4)
H60.63310.79070.51180.029*
C70.82853 (17)1.21778 (16)0.40024 (14)0.0225 (4)
C80.8577 (2)1.30967 (18)0.50242 (15)0.0291 (4)
H80.88781.29530.55880.035*
C90.8428 (2)1.42195 (19)0.52146 (16)0.0340 (4)
H90.86261.48440.59130.041*
C100.7993 (2)1.44475 (19)0.44009 (17)0.0327 (4)
H100.79041.52240.45370.039*
C110.7691 (2)1.35280 (19)0.33912 (17)0.0316 (4)
H110.73831.36720.28300.038*
C120.7831 (2)1.23971 (18)0.31873 (15)0.0277 (4)
H120.76171.17710.24890.033*
C131.00165 (19)0.65465 (18)0.17645 (15)0.0296 (4)
H13A0.95570.66100.11740.036*
H13B0.99590.56820.15380.036*
C141.14448 (19)0.7267 (2)0.20252 (15)0.0301 (4)
H14A1.18380.70310.13860.036*
H14B1.15190.81410.23120.036*
C151.35466 (19)0.73185 (19)0.28393 (17)0.0309 (4)
H15A1.37520.72470.21550.037*
H15B1.38580.67110.29770.037*
C161.4309 (2)0.85736 (18)0.36814 (17)0.0321 (4)
H16A1.41330.86330.43690.038*
H16B1.52740.86800.36930.038*
C171.4360 (2)0.9653 (2)0.26494 (17)0.0325 (4)
H17A1.38320.89370.20040.039*
H17B1.53140.97030.26530.039*
C181.41154 (19)1.07805 (19)0.26819 (17)0.0318 (4)
H18A1.46951.15020.33000.038*
H18B1.43191.08590.20460.038*
C191.24327 (19)1.17620 (17)0.28454 (16)0.0280 (4)
H19A1.22841.17550.21530.034*
H19B1.31741.24900.33090.034*
C201.11903 (18)1.17974 (16)0.33047 (15)0.0249 (4)
H20A1.12721.16320.39190.030*
H20B1.10601.26110.35380.030*
N10.93565 (14)0.91753 (13)0.31140 (12)0.0209 (3)
N20.77713 (15)0.94920 (13)0.17428 (12)0.0221 (3)
N30.74437 (15)0.72396 (13)0.16301 (11)0.0212 (3)
N40.77009 (15)0.77953 (14)0.36814 (12)0.0219 (3)
N50.84618 (16)1.10404 (14)0.38169 (12)0.0241 (3)
O10.93503 (12)0.69567 (11)0.26425 (10)0.0235 (3)
O21.21402 (13)0.70438 (14)0.27757 (11)0.0319 (3)
O31.39789 (14)0.95393 (13)0.35467 (11)0.0295 (3)
O41.27593 (13)1.07003 (12)0.27390 (12)0.0307 (3)
O51.00655 (12)1.08896 (11)0.25160 (10)0.0231 (3)
P10.84447 (4)0.78142 (4)0.27162 (3)0.01863 (11)
P20.88797 (4)1.00921 (4)0.27737 (3)0.01905 (11)
P30.73149 (4)0.80545 (4)0.10466 (3)0.01933 (11)
H4N0.787 (3)0.845 (2)0.418 (2)0.037 (7)*
H5N0.843 (2)1.086 (2)0.429 (2)0.034 (6)*
H011.095 (3)0.964 (3)0.412 (3)0.063 (9)*
H021.234 (3)0.975 (2)0.421 (2)0.039 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0253 (7)0.0287 (7)0.0187 (6)0.0080 (5)0.0035 (5)0.0079 (5)
C210.0230 (8)0.0264 (9)0.0189 (8)0.0091 (7)0.0024 (7)0.0109 (7)
C220.0270 (9)0.0270 (9)0.0261 (9)0.0073 (7)0.0059 (7)0.0118 (8)
C230.0255 (9)0.0384 (11)0.0337 (10)0.0093 (8)0.0088 (8)0.0203 (9)
C240.0316 (10)0.0420 (11)0.0241 (9)0.0183 (9)0.0102 (8)0.0164 (9)
C250.0357 (11)0.0321 (10)0.0244 (9)0.0134 (8)0.0057 (8)0.0083 (8)
C260.0275 (9)0.0280 (9)0.0238 (9)0.0063 (8)0.0046 (7)0.0081 (8)
C270.0217 (8)0.0254 (9)0.0153 (8)0.0083 (7)0.0026 (6)0.0041 (7)
C280.0321 (10)0.0319 (10)0.0275 (10)0.0086 (8)0.0017 (8)0.0122 (8)
C290.0365 (11)0.0453 (12)0.0344 (11)0.0170 (10)0.0031 (9)0.0171 (10)
C300.0236 (10)0.0481 (13)0.0263 (10)0.0099 (9)0.0022 (8)0.0074 (9)
C310.0236 (9)0.0362 (11)0.0258 (10)0.0039 (8)0.0030 (7)0.0063 (8)
C320.0249 (9)0.0270 (9)0.0223 (9)0.0078 (7)0.0046 (7)0.0076 (7)
C10.0190 (8)0.0234 (8)0.0223 (8)0.0047 (7)0.0006 (6)0.0128 (7)
C20.0293 (9)0.0228 (9)0.0263 (9)0.0092 (7)0.0047 (7)0.0101 (7)
C30.0310 (10)0.0198 (9)0.0331 (10)0.0048 (7)0.0006 (8)0.0110 (8)
C40.0275 (10)0.0288 (10)0.0395 (11)0.0004 (8)0.0009 (8)0.0204 (9)
C50.0285 (10)0.0340 (10)0.0300 (10)0.0035 (8)0.0052 (8)0.0171 (8)
C60.0239 (9)0.0251 (9)0.0213 (8)0.0032 (7)0.0020 (7)0.0107 (7)
C70.0224 (8)0.0229 (8)0.0223 (9)0.0079 (7)0.0068 (7)0.0093 (7)
C80.0359 (10)0.0293 (10)0.0209 (9)0.0116 (8)0.0057 (8)0.0091 (8)
C90.0426 (12)0.0274 (10)0.0263 (10)0.0128 (9)0.0091 (9)0.0051 (8)
C100.0377 (11)0.0274 (10)0.0385 (11)0.0164 (8)0.0145 (9)0.0151 (9)
C110.0375 (11)0.0353 (11)0.0325 (10)0.0191 (9)0.0119 (8)0.0196 (9)
C120.0338 (10)0.0306 (10)0.0214 (9)0.0151 (8)0.0064 (7)0.0110 (8)
C130.0276 (9)0.0300 (10)0.0248 (9)0.0133 (8)0.0037 (7)0.0039 (8)
C140.0290 (10)0.0401 (11)0.0241 (9)0.0141 (8)0.0069 (8)0.0147 (8)
C150.0249 (9)0.0326 (10)0.0364 (11)0.0130 (8)0.0036 (8)0.0144 (9)
C160.0300 (10)0.0330 (10)0.0342 (11)0.0135 (8)0.0015 (8)0.0145 (9)
C170.0297 (10)0.0374 (11)0.0343 (11)0.0133 (8)0.0131 (8)0.0167 (9)
C180.0253 (9)0.0371 (11)0.0364 (11)0.0088 (8)0.0099 (8)0.0192 (9)
C190.0259 (9)0.0267 (9)0.0337 (10)0.0047 (7)0.0016 (8)0.0179 (8)
C200.0234 (9)0.0202 (8)0.0241 (9)0.0008 (7)0.0033 (7)0.0074 (7)
N10.0197 (7)0.0211 (7)0.0206 (7)0.0045 (6)0.0007 (6)0.0093 (6)
N20.0239 (7)0.0214 (7)0.0191 (7)0.0067 (6)0.0000 (6)0.0078 (6)
N30.0232 (7)0.0191 (7)0.0170 (7)0.0031 (6)0.0011 (6)0.0065 (6)
N40.0230 (7)0.0196 (7)0.0184 (7)0.0020 (6)0.0034 (6)0.0066 (6)
N50.0335 (9)0.0241 (8)0.0180 (7)0.0108 (6)0.0057 (6)0.0112 (6)
O10.0235 (6)0.0240 (6)0.0253 (6)0.0098 (5)0.0054 (5)0.0114 (5)
O20.0241 (7)0.0437 (8)0.0320 (7)0.0111 (6)0.0046 (6)0.0201 (6)
O30.0322 (7)0.0320 (7)0.0291 (7)0.0149 (6)0.0096 (6)0.0148 (6)
O40.0238 (7)0.0275 (7)0.0436 (8)0.0070 (5)0.0065 (6)0.0186 (6)
O50.0227 (6)0.0228 (6)0.0210 (6)0.0018 (5)0.0006 (5)0.0101 (5)
P10.0182 (2)0.0196 (2)0.0177 (2)0.00543 (16)0.00222 (16)0.00827 (17)
P20.0200 (2)0.0188 (2)0.0170 (2)0.00481 (17)0.00134 (16)0.00751 (17)
P30.0191 (2)0.0203 (2)0.0165 (2)0.00533 (17)0.00102 (16)0.00692 (17)
Geometric parameters (Å, º) top
O6—H010.92 (3)C10—C111.381 (3)
O6—H020.83 (3)C10—H100.9500
C21—C221.394 (3)C11—C121.386 (3)
C21—C261.400 (3)C11—H110.9500
C21—P31.8083 (19)C12—H120.9500
C22—C231.390 (3)C13—O11.444 (2)
C22—H220.9500C13—C141.492 (3)
C23—C241.384 (3)C13—H13A0.9900
C23—H230.9500C13—H13B0.9900
C24—C251.387 (3)C14—O21.422 (2)
C24—H240.9500C14—H14A0.9900
C25—C261.386 (3)C14—H14B0.9900
C25—H250.9500C15—O21.425 (2)
C26—H260.9500C15—C161.515 (3)
C27—C281.392 (3)C15—H15A0.9900
C27—C321.389 (3)C15—H15B0.9900
C27—P31.8009 (19)C16—O31.432 (2)
C28—C291.385 (3)C16—H16A0.9900
C28—H280.9500C16—H16B0.9900
C29—C301.384 (3)C17—O31.426 (2)
C29—H290.9500C17—C181.495 (3)
C30—C311.381 (3)C17—H17A0.9900
C30—H300.9500C17—H17B0.9900
C31—C321.390 (3)C18—O41.416 (2)
C31—H310.9500C18—H18A0.9900
C32—H320.9500C18—H18B0.9900
C1—C61.392 (3)C19—O41.418 (2)
C1—C21.392 (3)C19—C201.504 (3)
C1—N41.405 (2)C19—H19A0.9900
C2—C31.390 (3)C19—H19B0.9900
C2—H20.9500C20—O51.447 (2)
C3—C41.379 (3)C20—H20A0.9900
C3—H30.9500C20—H20B0.9900
C4—C51.388 (3)N1—P11.5974 (16)
C4—H40.9500N1—P21.6007 (15)
C5—C61.386 (3)N2—P21.5918 (17)
C5—H50.9500N2—P31.5978 (17)
C6—H60.9500N3—P11.5920 (16)
C7—C121.390 (3)N3—P31.6017 (15)
C7—C81.393 (3)N4—P11.6404 (16)
C7—N51.414 (2)N4—H4N0.80 (3)
C8—C91.384 (3)N5—P21.6448 (17)
C8—H80.9500N5—H5N0.80 (3)
C9—C101.389 (3)O1—P11.5836 (13)
C9—H90.9500O5—P21.5808 (14)
H01—O6—H02109 (3)C14—C13—H13B109.2
C22—C21—C26119.06 (17)H13A—C13—H13B107.9
C22—C21—P3121.00 (14)O2—C14—C13109.02 (17)
C26—C21—P3119.82 (14)O2—C14—H14A109.9
C21—C22—C23120.13 (18)C13—C14—H14A109.9
C21—C22—H22119.9O2—C14—H14B109.9
C23—C22—H22119.9C13—C14—H14B109.9
C24—C23—C22120.32 (19)H14A—C14—H14B108.3
C24—C23—H23119.8O2—C15—C16113.79 (17)
C22—C23—H23119.8O2—C15—H15A108.8
C25—C24—C23120.11 (18)C16—C15—H15A108.8
C25—C24—H24119.9O2—C15—H15B108.8
C23—C24—H24119.9C16—C15—H15B108.8
C26—C25—C24119.81 (19)H15A—C15—H15B107.7
C26—C25—H25120.1O3—C16—C15114.11 (16)
C24—C25—H25120.1O3—C16—H16A108.7
C25—C26—C21120.56 (19)C15—C16—H16A108.7
C25—C26—H26119.7O3—C16—H16B108.7
C21—C26—H26119.7C15—C16—H16B108.7
C28—C27—C32119.78 (17)H16A—C16—H16B107.6
C28—C27—P3120.10 (15)O3—C17—C18108.13 (16)
C32—C27—P3120.10 (14)O3—C17—H17A110.1
C27—C28—C29119.7 (2)C18—C17—H17A110.1
C27—C28—H28120.2O3—C17—H17B110.1
C29—C28—H28120.2C18—C17—H17B110.1
C30—C29—C28120.3 (2)H17A—C17—H17B108.4
C30—C29—H29119.9O4—C18—C17108.10 (16)
C28—C29—H29119.9O4—C18—H18A110.1
C29—C30—C31120.36 (19)C17—C18—H18A110.1
C29—C30—H30119.8O4—C18—H18B110.1
C31—C30—H30119.8C17—C18—H18B110.1
C30—C31—C32119.6 (2)H18A—C18—H18B108.4
C30—C31—H31120.2O4—C19—C20108.62 (15)
C32—C31—H31120.2O4—C19—H19A110.0
C31—C32—C27120.25 (19)C20—C19—H19A110.0
C31—C32—H32119.9O4—C19—H19B110.0
C27—C32—H32119.9C20—C19—H19B110.0
C6—C1—C2119.21 (17)H19A—C19—H19B108.3
C6—C1—N4118.46 (16)O5—C20—C19108.81 (15)
C2—C1—N4122.32 (17)O5—C20—H20A109.9
C3—C2—C1119.79 (18)C19—C20—H20A109.9
C3—C2—H2120.1O5—C20—H20B109.9
C1—C2—H2120.1C19—C20—H20B109.9
C4—C3—C2120.85 (18)H20A—C20—H20B108.3
C4—C3—H3119.6P1—N1—P2121.03 (9)
C2—C3—H3119.6P2—N2—P3119.80 (10)
C3—C4—C5119.55 (18)P1—N3—P3119.90 (9)
C3—C4—H4120.2C1—N4—P1128.73 (13)
C5—C4—H4120.2C1—N4—H4N117.0 (19)
C6—C5—C4120.06 (19)P1—N4—H4N113.4 (19)
C6—C5—H5120.0C7—N5—P2127.16 (13)
C4—C5—H5120.0C7—N5—H5N117.4 (18)
C5—C6—C1120.52 (18)P2—N5—H5N115.1 (18)
C5—C6—H6119.7C13—O1—P1120.18 (12)
C1—C6—H6119.7C14—O2—C15115.21 (16)
C12—C7—C8119.46 (17)C17—O3—C16114.01 (15)
C12—C7—N5121.41 (17)C18—O4—C19113.03 (15)
C8—C7—N5119.13 (17)C20—O5—P2122.78 (12)
C9—C8—C7119.69 (19)O1—P1—N3108.57 (8)
C9—C8—H8120.2O1—P1—N1109.90 (8)
C7—C8—H8120.2N3—P1—N1116.23 (9)
C8—C9—C10121.02 (19)O1—P1—N4101.60 (8)
C8—C9—H9119.5N3—P1—N4113.24 (8)
C10—C9—H9119.5N1—P1—N4106.30 (9)
C11—C10—C9118.97 (19)O5—P2—N2103.21 (8)
C11—C10—H10120.5O5—P2—N1111.49 (8)
C9—C10—H10120.5N2—P2—N1116.27 (8)
C10—C11—C12120.73 (19)O5—P2—N5105.94 (8)
C10—C11—H11119.6N2—P2—N5114.05 (9)
C12—C11—H11119.6N1—P2—N5105.54 (8)
C7—C12—C11120.12 (18)N2—P3—N3117.25 (8)
C7—C12—H12119.9N2—P3—C27108.31 (9)
C11—C12—H12119.9N3—P3—C27107.84 (9)
O1—C13—C14112.15 (16)N2—P3—C21110.36 (9)
O1—C13—H13A109.2N3—P3—C21107.95 (8)
C14—C13—H13A109.2C27—P3—C21104.34 (8)
O1—C13—H13B109.2
C26—C21—C22—C230.0 (3)C17—C18—O4—C19175.98 (16)
P3—C21—C22—C23175.91 (15)C20—C19—O4—C18158.44 (16)
C21—C22—C23—C240.0 (3)C19—C20—O5—P2141.23 (13)
C22—C23—C24—C250.4 (3)C13—O1—P1—N349.60 (15)
C23—C24—C25—C260.7 (3)C13—O1—P1—N178.53 (15)
C24—C25—C26—C210.7 (3)C13—O1—P1—N4169.20 (13)
C22—C21—C26—C250.4 (3)P3—N3—P1—O1129.09 (10)
P3—C21—C26—C25175.60 (15)P3—N3—P1—N14.63 (14)
C32—C27—C28—C290.9 (3)P3—N3—P1—N4118.88 (11)
P3—C27—C28—C29179.34 (16)P2—N1—P1—O1150.68 (10)
C27—C28—C29—C301.2 (3)P2—N1—P1—N326.91 (14)
C28—C29—C30—C310.3 (3)P2—N1—P1—N4100.13 (12)
C29—C30—C31—C320.8 (3)C1—N4—P1—O174.15 (17)
C30—C31—C32—C271.1 (3)C1—N4—P1—N342.08 (18)
C28—C27—C32—C310.2 (3)C1—N4—P1—N1170.89 (15)
P3—C27—C32—C31178.23 (14)C20—O5—P2—N2166.92 (13)
C6—C1—C2—C31.3 (3)C20—O5—P2—N167.56 (15)
N4—C1—C2—C3177.38 (17)C20—O5—P2—N546.76 (15)
C1—C2—C3—C40.5 (3)P3—N2—P2—O5115.82 (11)
C2—C3—C4—C50.7 (3)P3—N2—P2—N16.55 (14)
C3—C4—C5—C61.0 (3)P3—N2—P2—N5129.74 (11)
C4—C5—C6—C10.3 (3)P1—N1—P2—O5139.24 (10)
C2—C1—C6—C50.9 (3)P1—N1—P2—N221.33 (14)
N4—C1—C6—C5177.81 (17)P1—N1—P2—N5106.19 (12)
C12—C7—C8—C90.8 (3)C7—N5—P2—O545.16 (18)
N5—C7—C8—C9179.04 (18)C7—N5—P2—N267.65 (18)
C7—C8—C9—C100.1 (3)C7—N5—P2—N1163.51 (15)
C8—C9—C10—C110.9 (3)P2—N2—P3—N327.64 (14)
C9—C10—C11—C120.7 (3)P2—N2—P3—C27149.87 (11)
C8—C7—C12—C111.0 (3)P2—N2—P3—C2196.48 (12)
N5—C7—C12—C11178.83 (18)P1—N3—P3—N221.75 (14)
C10—C11—C12—C70.3 (3)P1—N3—P3—C27144.23 (10)
O1—C13—C14—O266.6 (2)P1—N3—P3—C21103.58 (12)
O2—C15—C16—O360.6 (2)C28—C27—P3—N239.48 (17)
O3—C17—C18—O456.3 (2)C32—C27—P3—N2142.09 (15)
O4—C19—C20—O572.65 (19)C28—C27—P3—N3167.30 (15)
C6—C1—N4—P1169.29 (14)C32—C27—P3—N314.27 (17)
C2—C1—N4—P19.3 (3)C28—C27—P3—C2178.09 (17)
C12—C7—N5—P231.2 (3)C32—C27—P3—C21100.33 (16)
C8—C7—N5—P2148.62 (16)C22—C21—P3—N216.56 (17)
C14—C13—O1—P199.94 (17)C26—C21—P3—N2167.52 (14)
C13—C14—O2—C15159.52 (16)C22—C21—P3—N3112.76 (15)
C16—C15—O2—C1494.9 (2)C26—C21—P3—N363.16 (16)
C18—C17—O3—C16172.93 (16)C22—C21—P3—C27132.72 (15)
C15—C16—O3—C1766.6 (2)C26—C21—P3—C2751.37 (17)
(8) top
Crystal data top
C28H46N5O5P3Z = 2
Mr = 625.61F(000) = 668
Triclinic, P1Dx = 1.296 Mg m3
a = 9.5003 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4210 (3) ÅCell parameters from 12052 reflections
c = 17.1257 (3) Åθ = 2.9–27.5°
α = 92.598 (2)°µ = 0.23 mm1
β = 90.645 (2)°T = 120 K
γ = 108.799 (1)°Block, colourless
V = 1602.79 (6) Å30.27 × 0.18 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
7079 independent reflections
Radiation source: Nonius FR591 rotating anode5682 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
k = 1313
Tmin = 0.941, Tmax = 0.973l = 2219
20859 measured reflections
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)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0461P)2 + 1.1656P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.029
7079 reflectionsΔρmax = 0.72 e Å3
385 parametersΔρmin = 0.48 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0032 (15)
Crystal data top
C28H46N5O5P3γ = 108.799 (1)°
Mr = 625.61V = 1602.79 (6) Å3
Triclinic, P1Z = 2
a = 9.5003 (2) ÅMo Kα radiation
b = 10.4210 (3) ŵ = 0.23 mm1
c = 17.1257 (3) ÅT = 120 K
α = 92.598 (2)°0.27 × 0.18 × 0.12 mm
β = 90.645 (2)°
Data collection top
Nonius KappaCCD
diffractometer
7079 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1997)
5682 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.973Rint = 0.091
20859 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.72 e Å3
7079 reflectionsΔρmin = 0.48 e Å3
385 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3736 (2)0.0629 (2)0.31806 (12)0.0232 (4)
C20.2276 (2)0.0502 (3)0.29802 (14)0.0344 (5)
H2A0.19390.04050.24500.052*
H2B0.15220.04420.33530.052*
H2C0.24300.13850.30090.052*
C30.3488 (3)0.2004 (2)0.31825 (15)0.0366 (6)
H3A0.44300.27260.33090.055*
H3B0.27560.20380.35750.055*
H3C0.31180.21320.26650.055*
C40.4321 (2)0.0396 (3)0.39724 (13)0.0318 (5)
H4A0.44640.04950.39570.048*
H4B0.36040.04290.43730.048*
H4C0.52730.11040.40980.048*
C50.7337 (2)0.6212 (2)0.21172 (12)0.0227 (4)
C60.7158 (3)0.5919 (3)0.12430 (14)0.0407 (6)
H6A0.78710.54730.10670.061*
H6B0.73440.67720.09810.061*
H6C0.61440.53220.11140.061*
C70.8906 (2)0.7206 (2)0.23173 (14)0.0320 (5)
H7A0.90400.73570.28860.048*
H7B0.90250.80720.20800.048*
H7C0.96520.68210.21130.048*
C80.6204 (3)0.6860 (2)0.24175 (15)0.0350 (5)
H8A0.51980.62180.23280.053*
H8B0.63040.76840.21390.053*
H8C0.63830.70930.29790.053*
C90.8606 (2)0.0568 (2)0.33826 (12)0.0232 (4)
H9A0.92390.12620.30470.028*
H9B0.89370.02410.33410.028*
C100.8766 (2)0.1117 (2)0.42160 (12)0.0266 (5)
H10A0.83630.18810.42710.032*
H10B0.82140.04000.45630.032*
C111.0599 (2)0.2223 (3)0.51739 (13)0.0320 (5)
H11A1.02440.15510.55780.038*
H11B1.00720.29000.52310.038*
C121.2252 (3)0.2916 (3)0.52765 (13)0.0347 (5)
H12A1.24880.32270.58320.042*
H12B1.27710.22530.51450.042*
C131.2788 (3)0.5310 (3)0.51706 (16)0.0480 (7)
H13A1.34580.55270.56400.058*
H13B1.17720.52290.53400.058*
C141.3291 (3)0.6407 (3)0.46211 (16)0.0452 (7)
H14A1.35700.72900.49230.054*
H14B1.41970.63400.43660.054*
C151.2135 (2)0.5511 (2)0.33720 (14)0.0320 (5)
H15A1.29660.51360.34060.038*
H15B1.22550.60290.28930.038*
C161.0702 (2)0.4370 (2)0.33087 (14)0.0288 (5)
H16A1.07460.37180.28790.035*
H16B1.05390.38870.38010.035*
C170.9988 (2)0.1785 (2)0.11671 (11)0.0194 (4)
C180.9824 (2)0.0417 (2)0.10682 (12)0.0241 (4)
H180.88750.02430.11210.029*
C191.1042 (3)0.0007 (2)0.08927 (13)0.0327 (5)
H191.09270.09320.08280.039*
C201.2408 (3)0.0956 (3)0.08131 (14)0.0360 (6)
H201.32350.06700.06870.043*
C211.2598 (3)0.2317 (3)0.09129 (16)0.0394 (6)
H211.35520.29670.08540.047*
C221.1392 (2)0.2742 (2)0.11003 (14)0.0304 (5)
H221.15240.36820.11830.037*
C230.7737 (2)0.24617 (19)0.03569 (11)0.0181 (4)
C240.6302 (2)0.1739 (2)0.00908 (13)0.0255 (4)
H240.56340.11510.04280.031*
C250.5835 (2)0.1867 (2)0.06616 (14)0.0327 (5)
H250.48520.13640.08390.039*
C260.6799 (2)0.2727 (2)0.11554 (13)0.0296 (5)
H260.64810.28120.16730.036*
C270.8233 (2)0.3466 (2)0.08931 (12)0.0253 (4)
H270.88920.40670.12280.030*
C280.8699 (2)0.3326 (2)0.01459 (12)0.0211 (4)
H280.96850.38240.00280.025*
N10.72087 (17)0.26791 (16)0.30129 (9)0.0182 (3)
N20.88823 (17)0.37503 (16)0.17868 (9)0.0192 (3)
N30.71138 (17)0.10801 (16)0.17107 (9)0.0197 (3)
N40.47903 (18)0.05308 (17)0.25655 (10)0.0199 (4)
N50.7113 (2)0.49711 (17)0.25515 (10)0.0235 (4)
O10.70748 (14)0.02057 (13)0.31231 (8)0.0206 (3)
O21.03044 (15)0.15663 (16)0.44202 (8)0.0274 (3)
O31.27911 (18)0.40478 (17)0.48005 (9)0.0348 (4)
O41.22158 (19)0.63974 (18)0.40256 (11)0.0438 (5)
O50.94914 (15)0.48741 (14)0.31600 (8)0.0235 (3)
P10.65997 (5)0.12130 (5)0.25830 (3)0.01615 (13)
P20.81718 (5)0.39971 (5)0.25967 (3)0.01652 (13)
P30.83675 (5)0.22942 (5)0.13334 (3)0.01621 (13)
H50.610 (3)0.450 (3)0.2648 (18)0.058 (9)*
H40.445 (3)0.040 (3)0.2153 (17)0.041 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0163 (9)0.0275 (11)0.0223 (11)0.0021 (8)0.0048 (7)0.0020 (8)
C20.0179 (10)0.0420 (14)0.0341 (13)0.0033 (9)0.0041 (9)0.0027 (10)
C30.0352 (13)0.0341 (13)0.0432 (14)0.0138 (10)0.0161 (10)0.0048 (10)
C40.0260 (11)0.0437 (14)0.0212 (11)0.0045 (10)0.0053 (8)0.0043 (9)
C50.0256 (10)0.0176 (10)0.0260 (11)0.0080 (8)0.0012 (8)0.0053 (8)
C60.0624 (17)0.0337 (13)0.0294 (13)0.0204 (12)0.0063 (11)0.0026 (10)
C70.0298 (12)0.0240 (11)0.0397 (14)0.0048 (9)0.0031 (9)0.0056 (9)
C80.0383 (13)0.0304 (12)0.0432 (14)0.0200 (10)0.0003 (10)0.0051 (10)
C90.0184 (9)0.0251 (11)0.0271 (11)0.0084 (8)0.0013 (8)0.0013 (8)
C100.0198 (10)0.0317 (12)0.0270 (11)0.0059 (9)0.0016 (8)0.0053 (9)
C110.0297 (12)0.0435 (14)0.0215 (11)0.0096 (10)0.0007 (8)0.0044 (9)
C120.0314 (12)0.0474 (15)0.0234 (12)0.0100 (11)0.0047 (9)0.0055 (10)
C130.0538 (17)0.0498 (17)0.0346 (15)0.0113 (13)0.0009 (12)0.0188 (12)
C140.0422 (15)0.0382 (15)0.0479 (16)0.0060 (12)0.0174 (12)0.0152 (12)
C150.0212 (10)0.0359 (13)0.0359 (13)0.0052 (9)0.0005 (9)0.0002 (10)
C160.0281 (11)0.0237 (11)0.0349 (13)0.0093 (9)0.0062 (9)0.0021 (9)
C170.0197 (9)0.0219 (10)0.0181 (10)0.0086 (8)0.0027 (7)0.0031 (7)
C180.0283 (11)0.0249 (11)0.0222 (11)0.0129 (9)0.0010 (8)0.0019 (8)
C190.0446 (14)0.0362 (13)0.0272 (12)0.0269 (11)0.0021 (9)0.0007 (9)
C200.0322 (12)0.0541 (16)0.0330 (13)0.0291 (12)0.0080 (9)0.0053 (11)
C210.0202 (11)0.0484 (16)0.0515 (16)0.0127 (10)0.0087 (10)0.0101 (12)
C220.0215 (10)0.0284 (12)0.0425 (14)0.0090 (9)0.0061 (9)0.0047 (9)
C230.0182 (9)0.0166 (9)0.0201 (10)0.0067 (7)0.0018 (7)0.0021 (7)
C240.0192 (10)0.0249 (11)0.0302 (12)0.0037 (8)0.0012 (8)0.0050 (8)
C250.0237 (11)0.0349 (13)0.0366 (13)0.0053 (9)0.0081 (9)0.0043 (10)
C260.0344 (12)0.0328 (12)0.0242 (12)0.0140 (10)0.0033 (9)0.0052 (9)
C270.0307 (11)0.0217 (10)0.0262 (11)0.0111 (9)0.0079 (8)0.0054 (8)
C280.0199 (9)0.0185 (10)0.0237 (11)0.0045 (8)0.0032 (7)0.0004 (7)
N10.0183 (8)0.0159 (8)0.0175 (8)0.0020 (6)0.0015 (6)0.0018 (6)
N20.0182 (8)0.0143 (8)0.0221 (9)0.0016 (6)0.0016 (6)0.0014 (6)
N30.0202 (8)0.0144 (8)0.0204 (9)0.0002 (6)0.0041 (6)0.0024 (6)
N40.0142 (8)0.0239 (9)0.0175 (9)0.0006 (6)0.0009 (6)0.0006 (7)
N50.0231 (9)0.0193 (9)0.0284 (10)0.0070 (7)0.0020 (7)0.0042 (7)
O10.0179 (7)0.0175 (7)0.0251 (8)0.0037 (5)0.0012 (5)0.0027 (5)
O20.0201 (7)0.0367 (9)0.0238 (8)0.0069 (6)0.0017 (6)0.0016 (6)
O30.0359 (9)0.0374 (9)0.0268 (9)0.0066 (7)0.0007 (6)0.0039 (7)
O40.0370 (10)0.0403 (10)0.0521 (12)0.0130 (8)0.0162 (8)0.0181 (8)
O50.0204 (7)0.0220 (7)0.0246 (8)0.0025 (6)0.0044 (5)0.0034 (6)
P10.0138 (2)0.0141 (2)0.0182 (3)0.00145 (18)0.00126 (17)0.00036 (17)
P20.0167 (2)0.0133 (2)0.0184 (3)0.00338 (18)0.00132 (17)0.00102 (17)
P30.0140 (2)0.0139 (2)0.0194 (3)0.00269 (18)0.00293 (17)0.00023 (18)
Geometric parameters (Å, º) top
C1—N41.484 (2)C14—H14A0.9900
C1—C41.519 (3)C14—H14B0.9900
C1—C31.526 (3)C15—O41.404 (3)
C1—C21.526 (3)C15—C161.490 (3)
C2—H2A0.9800C15—H15A0.9900
C2—H2B0.9800C15—H15B0.9900
C2—H2C0.9800C16—O51.435 (3)
C3—H3A0.9800C16—H16A0.9900
C3—H3B0.9800C16—H16B0.9900
C3—H3C0.9800C17—C181.386 (3)
C4—H4A0.9800C17—C221.394 (3)
C4—H4B0.9800C17—P31.8044 (19)
C4—H4C0.9800C18—C191.388 (3)
C5—N51.478 (3)C18—H180.9500
C5—C61.511 (3)C19—C201.367 (3)
C5—C81.525 (3)C19—H190.9500
C5—C71.541 (3)C20—C211.374 (4)
C6—H6A0.9800C20—H200.9500
C6—H6B0.9800C21—C221.391 (3)
C6—H6C0.9800C21—H210.9500
C7—H7A0.9800C22—H220.9500
C7—H7B0.9800C23—C241.388 (3)
C7—H7C0.9800C23—C281.395 (3)
C8—H8A0.9800C23—P31.805 (2)
C8—H8B0.9800C24—C251.384 (3)
C8—H8C0.9800C24—H240.9500
C9—O11.440 (2)C25—C261.384 (3)
C9—C101.501 (3)C25—H250.9500
C9—H9A0.9900C26—C271.389 (3)
C9—H9B0.9900C26—H260.9500
C10—O21.418 (2)C27—C281.378 (3)
C10—H10A0.9900C27—H270.9500
C10—H10B0.9900C28—H280.9500
C11—O21.415 (3)N1—P21.5891 (16)
C11—C121.506 (3)N1—P11.5905 (16)
C11—H11A0.9900N2—P21.5957 (16)
C11—H11B0.9900N2—P31.5972 (16)
C12—O31.423 (3)N3—P11.5908 (16)
C12—H12A0.9900N3—P31.5992 (16)
C12—H12B0.9900N4—P11.6341 (16)
C13—O31.434 (3)N4—H40.76 (3)
C13—C141.476 (4)N5—P21.6470 (18)
C13—H13A0.9900N5—H50.95 (3)
C13—H13B0.9900O1—P11.5954 (14)
C14—O41.433 (3)O5—P21.5786 (14)
N4—C1—C4109.83 (17)C13—C14—H14B108.6
N4—C1—C3110.44 (17)H14A—C14—H14B107.6
C4—C1—C3111.09 (19)O4—C15—C16112.71 (19)
N4—C1—C2106.50 (17)O4—C15—H15A109.1
C4—C1—C2109.04 (18)C16—C15—H15A109.1
C3—C1—C2109.82 (19)O4—C15—H15B109.1
C1—C2—H2A109.5C16—C15—H15B109.1
C1—C2—H2B109.5H15A—C15—H15B107.8
H2A—C2—H2B109.5O5—C16—C15110.32 (18)
C1—C2—H2C109.5O5—C16—H16A109.6
H2A—C2—H2C109.5C15—C16—H16A109.6
H2B—C2—H2C109.5O5—C16—H16B109.6
C1—C3—H3A109.5C15—C16—H16B109.6
C1—C3—H3B109.5H16A—C16—H16B108.1
H3A—C3—H3B109.5C18—C17—C22119.29 (18)
C1—C3—H3C109.5C18—C17—P3119.36 (15)
H3A—C3—H3C109.5C22—C17—P3121.28 (16)
H3B—C3—H3C109.5C17—C18—C19120.2 (2)
C1—C4—H4A109.5C17—C18—H18119.9
C1—C4—H4B109.5C19—C18—H18119.9
H4A—C4—H4B109.5C20—C19—C18120.0 (2)
C1—C4—H4C109.5C20—C19—H19120.0
H4A—C4—H4C109.5C18—C19—H19120.0
H4B—C4—H4C109.5C19—C20—C21120.8 (2)
N5—C5—C6112.47 (18)C19—C20—H20119.6
N5—C5—C8106.63 (17)C21—C20—H20119.6
C6—C5—C8111.03 (19)C20—C21—C22119.9 (2)
N5—C5—C7108.85 (17)C20—C21—H21120.1
C6—C5—C7109.53 (19)C22—C21—H21120.1
C8—C5—C7108.19 (18)C21—C22—C17119.8 (2)
C5—C6—H6A109.5C21—C22—H22120.1
C5—C6—H6B109.5C17—C22—H22120.1
H6A—C6—H6B109.5C24—C23—C28118.82 (18)
C5—C6—H6C109.5C24—C23—P3121.18 (15)
H6A—C6—H6C109.5C28—C23—P3119.99 (14)
H6B—C6—H6C109.5C25—C24—C23120.68 (19)
C5—C7—H7A109.5C25—C24—H24119.7
C5—C7—H7B109.5C23—C24—H24119.7
H7A—C7—H7B109.5C26—C25—C24120.0 (2)
C5—C7—H7C109.5C26—C25—H25120.0
H7A—C7—H7C109.5C24—C25—H25120.0
H7B—C7—H7C109.5C25—C26—C27119.9 (2)
C5—C8—H8A109.5C25—C26—H26120.1
C5—C8—H8B109.5C27—C26—H26120.1
H8A—C8—H8B109.5C28—C27—C26119.94 (19)
C5—C8—H8C109.5C28—C27—H27120.0
H8A—C8—H8C109.5C26—C27—H27120.0
H8B—C8—H8C109.5C27—C28—C23120.69 (18)
O1—C9—C10109.58 (16)C27—C28—H28119.7
O1—C9—H9A109.8C23—C28—H28119.7
C10—C9—H9A109.8P2—N1—P1123.56 (10)
O1—C9—H9B109.8P2—N2—P3121.21 (10)
C10—C9—H9B109.8P1—N3—P3121.55 (10)
H9A—C9—H9B108.2C1—N4—P1128.16 (14)
O2—C10—C9107.31 (16)C1—N4—H4114 (2)
O2—C10—H10A110.3P1—N4—H4113 (2)
C9—C10—H10A110.3C5—N5—P2129.13 (14)
O2—C10—H10B110.3C5—N5—H5113.7 (19)
C9—C10—H10B110.3P2—N5—H5112.8 (19)
H10A—C10—H10B108.5C9—O1—P1118.53 (12)
O2—C11—C12108.55 (18)C11—O2—C10112.13 (16)
O2—C11—H11A110.0C12—O3—C13113.91 (19)
C12—C11—H11A110.0C15—O4—C14115.60 (19)
O2—C11—H11B110.0C16—O5—P2118.41 (13)
C12—C11—H11B110.0N1—P1—N3116.52 (8)
H11A—C11—H11B108.4N1—P1—O1106.65 (8)
O3—C12—C11112.73 (18)N3—P1—O1110.61 (8)
O3—C12—H12A109.0N1—P1—N4114.64 (9)
C11—C12—H12A109.0N3—P1—N4106.50 (9)
O3—C12—H12B109.0O1—P1—N4100.81 (8)
C11—C12—H12B109.0O5—P2—N1110.05 (8)
H12A—C12—H12B107.8O5—P2—N2107.11 (8)
O3—C13—C14110.0 (2)N1—P2—N2116.41 (8)
O3—C13—H13A109.7O5—P2—N5102.25 (8)
C14—C13—H13A109.7N1—P2—N5105.62 (9)
O3—C13—H13B109.7N2—P2—N5114.48 (9)
C14—C13—H13B109.7N2—P3—N3118.32 (8)
H13A—C13—H13B108.2N2—P3—C17108.54 (9)
O4—C14—C13114.8 (2)N3—P3—C17108.97 (9)
O4—C14—H14A108.6N2—P3—C23108.99 (9)
C13—C14—H14A108.6N3—P3—C23107.84 (9)
O4—C14—H14B108.6C17—P3—C23103.12 (9)
O1—C9—C10—O2174.98 (15)P3—N3—P1—O1112.92 (12)
O2—C11—C12—O369.5 (3)P3—N3—P1—N4138.40 (12)
O3—C13—C14—O475.1 (3)C9—O1—P1—N150.98 (15)
O4—C15—C16—O566.0 (3)C9—O1—P1—N376.63 (15)
C22—C17—C18—C191.0 (3)C9—O1—P1—N4170.99 (14)
P3—C17—C18—C19176.09 (16)C1—N4—P1—N136.3 (2)
C17—C18—C19—C200.3 (3)C1—N4—P1—N3166.73 (17)
C18—C19—C20—C210.7 (4)C1—N4—P1—O177.79 (18)
C19—C20—C21—C220.3 (4)C16—O5—P2—N171.35 (16)
C20—C21—C22—C171.6 (4)C16—O5—P2—N256.07 (16)
C18—C17—C22—C211.9 (3)C16—O5—P2—N5176.77 (15)
P3—C17—C22—C21175.09 (18)P1—N1—P2—O5137.73 (11)
C28—C23—C24—C250.4 (3)P1—N1—P2—N215.66 (16)
P3—C23—C24—C25179.43 (17)P1—N1—P2—N5112.60 (12)
C23—C24—C25—C260.3 (3)P3—N2—P2—O5136.41 (11)
C24—C25—C26—C270.3 (3)P3—N2—P2—N112.81 (15)
C25—C26—C27—C280.9 (3)P3—N2—P2—N5111.01 (12)
C26—C27—C28—C230.9 (3)C5—N5—P2—O575.56 (19)
C24—C23—C28—C270.2 (3)C5—N5—P2—N1169.28 (17)
P3—C23—C28—C27179.95 (15)C5—N5—P2—N239.9 (2)
C4—C1—N4—P145.8 (2)P2—N2—P3—N30.08 (16)
C3—C1—N4—P177.1 (2)P2—N2—P3—C17124.68 (12)
C2—C1—N4—P1163.68 (16)P2—N2—P3—C23123.68 (12)
C6—C5—N5—P269.8 (2)P1—N3—P3—N211.53 (16)
C8—C5—N5—P2168.29 (16)P1—N3—P3—C17113.02 (12)
C7—C5—N5—P251.8 (2)P1—N3—P3—C23135.71 (12)
C10—C9—O1—P1101.89 (17)C18—C17—P3—N2155.28 (16)
C12—C11—O2—C10168.37 (18)C22—C17—P3—N227.7 (2)
C9—C10—O2—C11174.44 (18)C18—C17—P3—N325.15 (19)
C11—C12—O3—C1390.4 (2)C22—C17—P3—N3157.84 (17)
C14—C13—O3—C12177.1 (2)C18—C17—P3—C2389.22 (17)
C16—C15—O4—C14112.9 (2)C22—C17—P3—C2387.78 (18)
C13—C14—O4—C1582.5 (3)C24—C23—P3—N2121.33 (17)
C15—C16—O5—P2143.27 (16)C28—C23—P3—N258.87 (17)
P2—N1—P1—N34.97 (16)C24—C23—P3—N38.30 (19)
P2—N1—P1—O1129.01 (11)C28—C23—P3—N3171.50 (15)
P2—N1—P1—N4120.35 (12)C24—C23—P3—C17123.49 (17)
P3—N3—P1—N19.06 (16)C28—C23—P3—C1756.31 (17)

Experimental details

(3)(4)(5)(6)
Crystal data
Chemical formulaC20H26Cl2N3O5P3C24H30F6N3O7P3C32H36N3O7P3C22H32N3O7P3
Mr552.25679.42667.55543.42
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nTriclinic, P1Monoclinic, P21/n
Temperature (K)150120150293
a, b, c (Å)17.618 (4), 8.1109 (16), 19.284 (4)15.3839 (4), 8.0685 (2), 24.1935 (9)10.166 (2), 12.105 (2), 13.313 (3)11.8293 (2), 10.3312 (2), 21.6318 (5)
α, β, γ (°)90, 114.44 (3), 9090, 105.877 (1), 9088.86 (3), 86.54 (3), 78.14 (3)90, 100.203 (1), 90
V3)2508.8 (9)2888.46 (15)1600.4 (6)2601.84 (9)
Z4424
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.490.290.240.28
Crystal size (mm)0.32 × 0.28 × 0.130.18 × 0.10 × 0.030.20 × 0.15 × 0.100.26 × 0.20 × 0.07
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1997)
Multi-scan
SORTAV (Blessing, 1997)
Multi-scan
SORTAV (Blessing, 1997)
Multi-scan
SORTAV (Blessing, 1997)
Tmin, Tmax0.860, 0.9390.949, 0.9910.954, 0.9770.932, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
17345, 5657, 4268 22797, 6488, 3777 24220, 12306, 8750 18814, 5841, 4160
Rint0.0450.0830.0610.038
(sin θ/λ)max1)0.6490.6490.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 1.01 0.050, 0.114, 0.98 0.054, 0.132, 0.94 0.052, 0.153, 1.00
No. of reflections56576488123065841
No. of parameters299389824319
No. of restraints00220
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.460.38, 0.380.81, 0.400.46, 0.31
Absolute structure??Flack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter??0.03 (7)?


(7)(8)
Crystal data
Chemical formulaC32H40N5O6P3C28H46N5O5P3
Mr683.60625.61
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)150120
a, b, c (Å)10.519 (2), 12.694 (3), 14.340 (3)9.5003 (2), 10.4210 (3), 17.1257 (3)
α, β, γ (°)114.81 (3), 93.81 (3), 103.59 (3)92.598 (2), 90.645 (2), 108.799 (1)
V3)1659.6 (6)1602.79 (6)
Z22
Radiation typeMo KαMo Kα
µ (mm1)0.230.23
Crystal size (mm)0.30 × 0.17 × 0.080.27 × 0.18 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1997)
Multi-scan
SORTAV (Blessing, 1997)
Tmin, Tmax0.934, 0.9830.941, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
19478, 7460, 6157 20859, 7079, 5682
Rint0.0330.091
(sin θ/λ)max1)0.6490.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.120, 0.65 0.045, 0.125, 1.01
No. of reflections74607079
No. of parameters431385
No. of restraints00
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.450.72, 0.48
Absolute structure??
Absolute structure parameter??

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998), DENZO & COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).

 

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