Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102018608/bm0058sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00583sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00584sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00585sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00586sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00587sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00588sup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102018608/bm0058sup8.pdf |
CCDC references: 201638; 201639; 201640; 201641; 201642; 201643
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).
C20H26Cl2N3O5P3 | F(000) = 1144 |
Mr = 552.25 | Dx = 1.462 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 17.618 (4) Å | Cell parameters from 7188 reflections |
b = 8.1109 (16) Å | θ = 2.9–27.5° |
c = 19.284 (4) Å | µ = 0.49 mm−1 |
β = 114.44 (3)° | T = 150 K |
V = 2508.8 (9) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.28 × 0.13 mm |
Nonius KappaCCD diffractometer | 5657 independent reflections |
Radiation source: Nonius FR591 rotating anode | 4268 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ϕ and ω scans | h = −22→22 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −9→10 |
Tmin = 0.860, Tmax = 0.939 | l = −24→25 |
17345 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-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 reflections | Δρmax = 0.32 e Å−3 |
299 parameters | Δρmin = −0.46 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0041 (7) |
C20H26Cl2N3O5P3 | V = 2508.8 (9) Å3 |
Mr = 552.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 17.618 (4) Å | µ = 0.49 mm−1 |
b = 8.1109 (16) Å | T = 150 K |
c = 19.284 (4) Å | 0.32 × 0.28 × 0.13 mm |
β = 114.44 (3)° |
Nonius KappaCCD diffractometer | 5657 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 4268 reflections with I > 2σ(I) |
Tmin = 0.860, Tmax = 0.939 | Rint = 0.045 |
17345 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.32 e Å−3 |
5657 reflections | Δρmin = −0.46 e Å−3 |
299 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.34690 (14) | 0.3650 (3) | 0.08190 (13) | 0.0353 (5) | |
H1A | 0.3652 | 0.3039 | 0.0471 | 0.042* | |
H1B | 0.3723 | 0.4762 | 0.0906 | 0.042* | |
C2 | 0.25355 (14) | 0.3779 (3) | 0.04826 (14) | 0.0351 (5) | |
H2A | 0.2353 | 0.4285 | 0.0855 | 0.042* | |
H2B | 0.2338 | 0.4480 | 0.0021 | 0.042* | |
C3 | 0.13197 (13) | 0.2129 (3) | 0.00253 (13) | 0.0324 (5) | |
H3A | 0.1057 | 0.2725 | −0.0465 | 0.039* | |
H3B | 0.1146 | 0.2663 | 0.0398 | 0.039* | |
C4 | 0.10552 (13) | 0.0361 (3) | −0.00783 (12) | 0.0314 (5) | |
H4A | 0.0441 | 0.0287 | −0.0355 | 0.038* | |
H4B | 0.1310 | −0.0217 | −0.0381 | 0.038* | |
C5 | 0.12177 (14) | −0.2125 (3) | 0.06105 (12) | 0.0314 (5) | |
H5A | 0.1535 | −0.2607 | 0.0339 | 0.038* | |
H5B | 0.0622 | −0.2408 | 0.0323 | 0.038* | |
C6 | 0.15258 (14) | −0.2830 (3) | 0.13942 (13) | 0.0332 (5) | |
H6A | 0.1305 | −0.2179 | 0.1704 | 0.040* | |
H6B | 0.1328 | −0.3980 | 0.1369 | 0.040* | |
C7 | 0.27381 (15) | −0.3424 (3) | 0.24890 (13) | 0.0343 (5) | |
H7A | 0.2556 | −0.4579 | 0.2487 | 0.041* | |
H7B | 0.2535 | −0.2762 | 0.2809 | 0.041* | |
C8 | 0.36667 (14) | −0.3344 (3) | 0.28008 (13) | 0.0329 (5) | |
H8A | 0.3916 | −0.3913 | 0.3299 | 0.039* | |
H8B | 0.3865 | −0.3892 | 0.2448 | 0.039* | |
C9 | 0.42545 (13) | −0.1990 (2) | 0.05410 (11) | 0.0232 (4) | |
C10 | 0.45124 (14) | −0.2951 (3) | 0.00783 (11) | 0.0286 (5) | |
H10 | 0.5089 | −0.3171 | 0.0230 | 0.034* | |
C11 | 0.39313 (15) | −0.3588 (3) | −0.06037 (12) | 0.0337 (5) | |
H11 | 0.4110 | −0.4242 | −0.0917 | 0.040* | |
C12 | 0.30945 (14) | −0.3269 (3) | −0.08254 (12) | 0.0325 (5) | |
H12 | 0.2696 | −0.3698 | −0.1293 | 0.039* | |
C13 | 0.28353 (14) | −0.2326 (3) | −0.03664 (13) | 0.0341 (5) | |
H13 | 0.2258 | −0.2119 | −0.0519 | 0.041* | |
C14 | 0.34047 (13) | −0.1682 (3) | 0.03104 (12) | 0.0306 (5) | |
H14 | 0.3219 | −0.1030 | 0.0620 | 0.037* | |
C15 | 0.59947 (13) | −0.1647 (2) | 0.15535 (11) | 0.0242 (4) | |
C16 | 0.64688 (13) | −0.2713 (3) | 0.21393 (11) | 0.0274 (5) | |
H16 | 0.6255 | −0.3092 | 0.2490 | 0.033* | |
C17 | 0.72477 (14) | −0.3224 (3) | 0.22145 (13) | 0.0340 (5) | |
H17 | 0.7569 | −0.3946 | 0.2617 | 0.041* | |
C18 | 0.75587 (14) | −0.2685 (3) | 0.17056 (13) | 0.0349 (5) | |
H18 | 0.8089 | −0.3058 | 0.1752 | 0.042* | |
C19 | 0.71016 (14) | −0.1602 (3) | 0.11262 (13) | 0.0344 (5) | |
H19 | 0.7322 | −0.1223 | 0.0781 | 0.041* | |
C20 | 0.63259 (14) | −0.1077 (3) | 0.10513 (12) | 0.0295 (5) | |
H20 | 0.6016 | −0.0325 | 0.0658 | 0.035* | |
N1 | 0.45554 (11) | 0.0985 (2) | 0.26501 (10) | 0.0286 (4) | |
N2 | 0.47795 (11) | −0.1963 (2) | 0.20964 (9) | 0.0246 (4) | |
N3 | 0.48236 (11) | 0.0870 (2) | 0.13602 (9) | 0.0268 (4) | |
O1 | 0.37151 (9) | 0.27752 (18) | 0.15361 (8) | 0.0302 (3) | |
O2 | 0.21987 (9) | 0.21724 (18) | 0.02925 (9) | 0.0320 (4) | |
O3 | 0.13151 (10) | −0.03846 (19) | 0.06479 (8) | 0.0338 (4) | |
O4 | 0.24094 (9) | −0.2794 (2) | 0.17365 (8) | 0.0332 (4) | |
O5 | 0.39105 (9) | −0.16149 (18) | 0.28902 (9) | 0.0322 (4) | |
P1 | 0.45731 (3) | 0.18753 (6) | 0.19288 (3) | 0.02392 (14) | |
P2 | 0.46451 (3) | −0.09408 (6) | 0.27249 (3) | 0.02262 (14) | |
P3 | 0.49581 (3) | −0.10982 (6) | 0.14295 (3) | 0.02192 (14) | |
Cl1 | 0.53581 (4) | 0.38143 (7) | 0.22985 (4) | 0.04032 (17) | |
Cl2 | 0.56344 (4) | −0.13776 (9) | 0.37365 (3) | 0.0519 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0336 (13) | 0.0305 (13) | 0.0424 (13) | 0.0002 (10) | 0.0162 (11) | 0.0135 (10) |
C2 | 0.0325 (12) | 0.0246 (12) | 0.0456 (13) | 0.0024 (10) | 0.0135 (11) | 0.0101 (10) |
C3 | 0.0240 (11) | 0.0332 (13) | 0.0419 (12) | 0.0045 (9) | 0.0156 (10) | 0.0057 (10) |
C4 | 0.0276 (11) | 0.0338 (13) | 0.0337 (11) | 0.0016 (10) | 0.0137 (10) | 0.0013 (9) |
C5 | 0.0312 (12) | 0.0272 (12) | 0.0397 (12) | −0.0041 (9) | 0.0184 (10) | −0.0030 (9) |
C6 | 0.0347 (13) | 0.0282 (12) | 0.0451 (13) | −0.0030 (10) | 0.0250 (11) | 0.0012 (10) |
C7 | 0.0440 (14) | 0.0302 (12) | 0.0380 (12) | −0.0012 (10) | 0.0264 (11) | 0.0074 (10) |
C8 | 0.0436 (14) | 0.0245 (12) | 0.0375 (12) | −0.0003 (10) | 0.0237 (11) | 0.0059 (9) |
C9 | 0.0274 (11) | 0.0193 (10) | 0.0277 (10) | 0.0008 (8) | 0.0162 (9) | 0.0032 (8) |
C10 | 0.0300 (11) | 0.0290 (12) | 0.0288 (11) | 0.0054 (9) | 0.0143 (9) | 0.0015 (9) |
C11 | 0.0415 (14) | 0.0318 (13) | 0.0288 (11) | 0.0025 (10) | 0.0156 (10) | −0.0048 (9) |
C12 | 0.0351 (13) | 0.0281 (12) | 0.0297 (11) | −0.0039 (10) | 0.0088 (10) | 0.0017 (9) |
C13 | 0.0253 (11) | 0.0348 (13) | 0.0427 (13) | −0.0027 (10) | 0.0145 (10) | 0.0017 (10) |
C14 | 0.0291 (12) | 0.0298 (12) | 0.0385 (12) | 0.0008 (9) | 0.0197 (10) | −0.0011 (10) |
C15 | 0.0274 (11) | 0.0213 (11) | 0.0260 (10) | −0.0013 (8) | 0.0132 (9) | −0.0031 (8) |
C16 | 0.0316 (12) | 0.0241 (11) | 0.0268 (10) | −0.0011 (9) | 0.0124 (9) | −0.0020 (8) |
C17 | 0.0323 (12) | 0.0317 (13) | 0.0328 (11) | 0.0030 (10) | 0.0081 (10) | −0.0018 (10) |
C18 | 0.0233 (11) | 0.0340 (13) | 0.0458 (13) | −0.0006 (10) | 0.0128 (10) | −0.0088 (11) |
C19 | 0.0353 (13) | 0.0329 (13) | 0.0449 (13) | −0.0047 (10) | 0.0265 (11) | −0.0053 (10) |
C20 | 0.0324 (12) | 0.0269 (12) | 0.0336 (11) | −0.0017 (9) | 0.0180 (10) | 0.0020 (9) |
N1 | 0.0407 (11) | 0.0202 (9) | 0.0305 (9) | 0.0028 (8) | 0.0203 (8) | −0.0016 (7) |
N2 | 0.0350 (10) | 0.0176 (9) | 0.0294 (9) | 0.0021 (7) | 0.0214 (8) | 0.0017 (7) |
N3 | 0.0409 (11) | 0.0167 (9) | 0.0311 (9) | 0.0012 (8) | 0.0231 (8) | 0.0027 (7) |
O1 | 0.0280 (8) | 0.0298 (8) | 0.0361 (8) | 0.0056 (6) | 0.0166 (7) | 0.0069 (7) |
O2 | 0.0262 (8) | 0.0267 (8) | 0.0459 (9) | 0.0026 (6) | 0.0177 (7) | 0.0048 (7) |
O3 | 0.0453 (9) | 0.0266 (8) | 0.0342 (8) | −0.0009 (7) | 0.0212 (7) | −0.0001 (6) |
O4 | 0.0325 (9) | 0.0387 (9) | 0.0343 (8) | −0.0017 (7) | 0.0198 (7) | 0.0065 (7) |
O5 | 0.0402 (9) | 0.0263 (8) | 0.0424 (8) | −0.0044 (7) | 0.0296 (7) | −0.0039 (7) |
P1 | 0.0268 (3) | 0.0171 (3) | 0.0312 (3) | 0.0005 (2) | 0.0153 (2) | −0.0005 (2) |
P2 | 0.0265 (3) | 0.0220 (3) | 0.0221 (3) | 0.0024 (2) | 0.0127 (2) | 0.0011 (2) |
P3 | 0.0285 (3) | 0.0175 (3) | 0.0251 (3) | 0.0013 (2) | 0.0163 (2) | 0.0015 (2) |
Cl1 | 0.0380 (3) | 0.0280 (3) | 0.0562 (4) | −0.0102 (2) | 0.0208 (3) | −0.0094 (3) |
Cl2 | 0.0503 (4) | 0.0567 (4) | 0.0311 (3) | 0.0141 (3) | −0.0008 (3) | 0.0012 (3) |
C1—O1 | 1.452 (3) | C10—C11 | 1.390 (3) |
C1—C2 | 1.501 (3) | C10—H10 | 0.9500 |
C1—H1A | 0.9900 | C11—C12 | 1.379 (3) |
C1—H1B | 0.9900 | C11—H11 | 0.9500 |
C2—O2 | 1.416 (3) | C12—C13 | 1.383 (3) |
C2—H2A | 0.9900 | C12—H12 | 0.9500 |
C2—H2B | 0.9900 | C13—C14 | 1.378 (3) |
C3—O2 | 1.416 (3) | C13—H13 | 0.9500 |
C3—C4 | 1.495 (3) | C14—H14 | 0.9500 |
C3—H3A | 0.9900 | C15—C16 | 1.393 (3) |
C3—H3B | 0.9900 | C15—C20 | 1.400 (3) |
C4—O3 | 1.416 (3) | C15—P3 | 1.797 (2) |
C4—H4A | 0.9900 | C16—C17 | 1.382 (3) |
C4—H4B | 0.9900 | C16—H16 | 0.9500 |
C5—O3 | 1.421 (3) | C17—C18 | 1.378 (3) |
C5—C6 | 1.492 (3) | C17—H17 | 0.9500 |
C5—H5A | 0.9900 | C18—C19 | 1.387 (3) |
C5—H5B | 0.9900 | C18—H18 | 0.9500 |
C6—O4 | 1.418 (3) | C19—C20 | 1.381 (3) |
C6—H6A | 0.9900 | C19—H19 | 0.9500 |
C6—H6B | 0.9900 | C20—H20 | 0.9500 |
C7—O4 | 1.417 (3) | N1—P2 | 1.5703 (18) |
C7—C8 | 1.493 (3) | N1—P1 | 1.5792 (17) |
C7—H7A | 0.9900 | N2—P2 | 1.5653 (16) |
C7—H7B | 0.9900 | N2—P3 | 1.6064 (16) |
C8—O5 | 1.456 (3) | N3—P1 | 1.5694 (17) |
C8—H8A | 0.9900 | N3—P3 | 1.6110 (17) |
C8—H8B | 0.9900 | O1—P1 | 1.5633 (16) |
C9—C10 | 1.395 (3) | O5—P2 | 1.5547 (15) |
C9—C14 | 1.397 (3) | P1—Cl1 | 2.0196 (8) |
C9—P3 | 1.799 (2) | P2—Cl2 | 2.0387 (11) |
O1—C1—C2 | 106.71 (17) | C12—C11—H11 | 120.1 |
O1—C1—H1A | 110.4 | C10—C11—H11 | 120.1 |
C2—C1—H1A | 110.4 | C11—C12—C13 | 119.9 (2) |
O1—C1—H1B | 110.4 | C11—C12—H12 | 120.0 |
C2—C1—H1B | 110.4 | C13—C12—H12 | 120.0 |
H1A—C1—H1B | 108.6 | C14—C13—C12 | 120.8 (2) |
O2—C2—C1 | 108.36 (18) | C14—C13—H13 | 119.6 |
O2—C2—H2A | 110.0 | C12—C13—H13 | 119.6 |
C1—C2—H2A | 110.0 | C13—C14—C9 | 119.9 (2) |
O2—C2—H2B | 110.0 | C13—C14—H14 | 120.1 |
C1—C2—H2B | 110.0 | C9—C14—H14 | 120.1 |
H2A—C2—H2B | 108.4 | C16—C15—C20 | 118.97 (19) |
O2—C3—C4 | 107.83 (17) | C16—C15—P3 | 119.82 (15) |
O2—C3—H3A | 110.1 | C20—C15—P3 | 121.16 (16) |
C4—C3—H3A | 110.1 | C17—C16—C15 | 120.5 (2) |
O2—C3—H3B | 110.1 | C17—C16—H16 | 119.8 |
C4—C3—H3B | 110.1 | C15—C16—H16 | 119.8 |
H3A—C3—H3B | 108.5 | C18—C17—C16 | 120.0 (2) |
O3—C4—C3 | 108.78 (18) | C18—C17—H17 | 120.0 |
O3—C4—H4A | 109.9 | C16—C17—H17 | 120.0 |
C3—C4—H4A | 109.9 | C17—C18—C19 | 120.3 (2) |
O3—C4—H4B | 109.9 | C17—C18—H18 | 119.8 |
C3—C4—H4B | 109.9 | C19—C18—H18 | 119.8 |
H4A—C4—H4B | 108.3 | C20—C19—C18 | 120.0 (2) |
O3—C5—C6 | 110.09 (18) | C20—C19—H19 | 120.0 |
O3—C5—H5A | 109.6 | C18—C19—H19 | 120.0 |
C6—C5—H5A | 109.6 | C19—C20—C15 | 120.2 (2) |
O3—C5—H5B | 109.6 | C19—C20—H20 | 119.9 |
C6—C5—H5B | 109.6 | C15—C20—H20 | 119.9 |
H5A—C5—H5B | 108.2 | P2—N1—P1 | 119.86 (10) |
O4—C6—C5 | 109.46 (17) | P2—N2—P3 | 122.07 (11) |
O4—C6—H6A | 109.8 | P1—N3—P3 | 122.09 (10) |
C5—C6—H6A | 109.8 | C1—O1—P1 | 122.52 (13) |
O4—C6—H6B | 109.8 | C2—O2—C3 | 113.29 (16) |
C5—C6—H6B | 109.8 | C4—O3—C5 | 113.05 (16) |
H6A—C6—H6B | 108.2 | C6—O4—C7 | 111.99 (16) |
O4—C7—C8 | 108.20 (17) | C8—O5—P2 | 122.98 (13) |
O4—C7—H7A | 110.1 | O1—P1—N3 | 113.53 (9) |
C8—C7—H7A | 110.1 | O1—P1—N1 | 105.83 (9) |
O4—C7—H7B | 110.1 | N3—P1—N1 | 119.44 (9) |
C8—C7—H7B | 110.1 | O1—P1—Cl1 | 101.02 (7) |
H7A—C7—H7B | 108.4 | N3—P1—Cl1 | 107.58 (7) |
O5—C8—C7 | 108.07 (18) | N1—P1—Cl1 | 107.79 (8) |
O5—C8—H8A | 110.1 | O5—P2—N2 | 112.20 (9) |
C7—C8—H8A | 110.1 | O5—P2—N1 | 107.93 (9) |
O5—C8—H8B | 110.1 | N2—P2—N1 | 119.85 (9) |
C7—C8—H8B | 110.1 | O5—P2—Cl2 | 101.38 (7) |
H8A—C8—H8B | 108.4 | N2—P2—Cl2 | 107.79 (7) |
C10—C9—C14 | 119.1 (2) | N1—P2—Cl2 | 105.92 (7) |
C10—C9—P3 | 123.73 (16) | N2—P3—N3 | 115.37 (9) |
C14—C9—P3 | 117.18 (15) | N2—P3—C15 | 108.06 (9) |
C11—C10—C9 | 120.4 (2) | N3—P3—C15 | 111.30 (9) |
C11—C10—H10 | 119.8 | N2—P3—C9 | 107.51 (9) |
C9—C10—H10 | 119.8 | N3—P3—C9 | 107.42 (9) |
C12—C11—C10 | 119.9 (2) | C15—P3—C9 | 106.80 (9) |
C24H30F6N3O7P3 | F(000) = 1400 |
Mr = 679.42 | Dx = 1.562 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.3839 (4) Å | Cell parameters from 10029 reflections |
b = 8.0685 (2) Å | θ = 2.9–27.5° |
c = 24.1935 (9) Å | µ = 0.29 mm−1 |
β = 105.877 (1)° | T = 120 K |
V = 2888.46 (15) Å3 | Plate, colourless |
Z = 4 | 0.18 × 0.10 × 0.03 mm |
Nonius KappaCCD diffractometer | 6488 independent reflections |
Radiation source: Nonius FR591 rotating anode | 3777 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −19→19 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −10→8 |
Tmin = 0.949, Tmax = 0.991 | l = −31→31 |
22797 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.38 e Å−3 |
389 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0013 (3) |
C24H30F6N3O7P3 | V = 2888.46 (15) Å3 |
Mr = 679.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.3839 (4) Å | µ = 0.29 mm−1 |
b = 8.0685 (2) Å | T = 120 K |
c = 24.1935 (9) Å | 0.18 × 0.10 × 0.03 mm |
β = 105.877 (1)° |
Nonius KappaCCD diffractometer | 6488 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 3777 reflections with I > 2σ(I) |
Tmin = 0.949, Tmax = 0.991 | Rint = 0.083 |
22797 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.38 e Å−3 |
6488 reflections | Δρmin = −0.38 e Å−3 |
389 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.30632 (19) | 0.4338 (4) | 0.06173 (11) | 0.0266 (7) | |
H1A | 0.2541 | 0.4680 | 0.0756 | 0.032* | |
H1B | 0.3253 | 0.3214 | 0.0767 | 0.032* | |
C2 | 0.28124 (19) | 0.4340 (4) | −0.00210 (12) | 0.0269 (7) | |
C3 | 0.17222 (17) | 0.9621 (4) | 0.11787 (11) | 0.0233 (6) | |
H3A | 0.1375 | 1.0577 | 0.1262 | 0.028* | |
H3B | 0.1631 | 0.8671 | 0.1416 | 0.028* | |
C4 | 0.14009 (19) | 0.9187 (4) | 0.05592 (12) | 0.0269 (7) | |
C5 | 0.42024 (18) | 0.4028 (4) | 0.23410 (11) | 0.0242 (6) | |
H5A | 0.4098 | 0.2839 | 0.2401 | 0.029* | |
H5B | 0.3717 | 0.4672 | 0.2439 | 0.029* | |
C6 | 0.51021 (19) | 0.4538 (4) | 0.27284 (11) | 0.0259 (7) | |
H6A | 0.5600 | 0.4020 | 0.2604 | 0.031* | |
H6B | 0.5173 | 0.5758 | 0.2725 | 0.031* | |
C7 | 0.59025 (19) | 0.4441 (4) | 0.37193 (12) | 0.0302 (7) | |
H7A | 0.6436 | 0.4048 | 0.3603 | 0.036* | |
H7B | 0.5901 | 0.3860 | 0.4080 | 0.036* | |
C8 | 0.60045 (18) | 0.6261 (4) | 0.38397 (12) | 0.0271 (7) | |
H8A | 0.6563 | 0.6474 | 0.4151 | 0.032* | |
H8B | 0.6050 | 0.6860 | 0.3491 | 0.032* | |
C9 | 0.52831 (18) | 0.8561 (4) | 0.41135 (13) | 0.0290 (7) | |
H9A | 0.5325 | 0.9164 | 0.3765 | 0.035* | |
H9B | 0.5827 | 0.8825 | 0.4430 | 0.035* | |
C10 | 0.44546 (18) | 0.9086 (4) | 0.42728 (12) | 0.0283 (7) | |
H10A | 0.4440 | 0.8518 | 0.4633 | 0.034* | |
H10B | 0.4489 | 1.0293 | 0.4349 | 0.034* | |
C11 | 0.34972 (19) | 0.9633 (4) | 0.33199 (11) | 0.0264 (7) | |
H11A | 0.4027 | 1.0345 | 0.3334 | 0.032* | |
H11B | 0.2957 | 1.0350 | 0.3260 | 0.032* | |
C12 | 0.3367 (2) | 0.8411 (4) | 0.28409 (11) | 0.0278 (7) | |
H12A | 0.3954 | 0.7913 | 0.2838 | 0.033* | |
H12B | 0.2957 | 0.7512 | 0.2891 | 0.033* | |
C13 | 0.54897 (17) | 0.9977 (3) | 0.11897 (11) | 0.0221 (6) | |
C14 | 0.60246 (19) | 0.9212 (4) | 0.08832 (12) | 0.0291 (7) | |
H14 | 0.6233 | 0.8111 | 0.0976 | 0.035* | |
C15 | 0.6252 (2) | 1.0045 (4) | 0.04477 (13) | 0.0369 (8) | |
H15 | 0.6619 | 0.9518 | 0.0241 | 0.044* | |
C16 | 0.5950 (2) | 1.1645 (4) | 0.03084 (13) | 0.0353 (8) | |
H16 | 0.6100 | 1.2209 | 0.0002 | 0.042* | |
C17 | 0.54328 (19) | 1.2420 (4) | 0.06134 (13) | 0.0323 (8) | |
H17 | 0.5231 | 1.3524 | 0.0520 | 0.039* | |
C18 | 0.52048 (18) | 1.1603 (4) | 0.10542 (12) | 0.0267 (7) | |
H18 | 0.4853 | 1.2150 | 0.1266 | 0.032* | |
C19 | 0.60959 (17) | 0.8989 (3) | 0.23775 (11) | 0.0199 (6) | |
C20 | 0.61259 (18) | 1.0190 (3) | 0.27932 (12) | 0.0237 (6) | |
H20 | 0.5640 | 1.0952 | 0.2747 | 0.028* | |
C21 | 0.68568 (18) | 1.0286 (4) | 0.32734 (12) | 0.0265 (7) | |
H21 | 0.6869 | 1.1105 | 0.3558 | 0.032* | |
C22 | 0.75699 (18) | 0.9198 (4) | 0.33423 (12) | 0.0282 (7) | |
H22 | 0.8077 | 0.9280 | 0.3670 | 0.034* | |
C23 | 0.75470 (19) | 0.7992 (4) | 0.29360 (12) | 0.0337 (8) | |
H23 | 0.8035 | 0.7233 | 0.2986 | 0.040* | |
C24 | 0.68116 (18) | 0.7885 (4) | 0.24537 (12) | 0.0289 (7) | |
H24 | 0.6798 | 0.7051 | 0.2174 | 0.035* | |
N1 | 0.33017 (13) | 0.7066 (3) | 0.16249 (9) | 0.0198 (5) | |
N2 | 0.43216 (14) | 0.9822 (3) | 0.18728 (9) | 0.0209 (5) | |
N3 | 0.50191 (13) | 0.6960 (3) | 0.15597 (9) | 0.0202 (5) | |
O1 | 0.37931 (11) | 0.5486 (2) | 0.08091 (7) | 0.0220 (4) | |
O2 | 0.26641 (11) | 1.0034 (2) | 0.13145 (7) | 0.0217 (4) | |
O3 | 0.41684 (12) | 0.4304 (2) | 0.17469 (7) | 0.0217 (4) | |
O4 | 0.51064 (13) | 0.3981 (2) | 0.32838 (7) | 0.0279 (5) | |
O5 | 0.52409 (12) | 0.6830 (2) | 0.40069 (8) | 0.0272 (5) | |
O6 | 0.36358 (12) | 0.8736 (2) | 0.38419 (8) | 0.0274 (5) | |
O7 | 0.29802 (12) | 0.9283 (2) | 0.23075 (7) | 0.0227 (4) | |
F1 | 0.35004 (11) | 0.3951 (2) | −0.02316 (7) | 0.0376 (5) | |
F2 | 0.21548 (12) | 0.3238 (2) | −0.02294 (7) | 0.0463 (5) | |
F3 | 0.25101 (11) | 0.5803 (2) | −0.02512 (7) | 0.0338 (4) | |
F4 | 0.18624 (12) | 0.7925 (2) | 0.04156 (8) | 0.0503 (5) | |
F5 | 0.14593 (12) | 1.0434 (2) | 0.02171 (7) | 0.0453 (5) | |
F6 | 0.05335 (11) | 0.8715 (2) | 0.04226 (7) | 0.0391 (5) | |
P1 | 0.40851 (4) | 0.60711 (9) | 0.14597 (3) | 0.01907 (18) | |
P2 | 0.33745 (4) | 0.89744 (9) | 0.17773 (3) | 0.01903 (18) | |
P3 | 0.51600 (4) | 0.88728 (9) | 0.17412 (3) | 0.01985 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0275 (16) | 0.0292 (19) | 0.0224 (15) | −0.0102 (13) | 0.0055 (12) | −0.0007 (13) |
C2 | 0.0274 (17) | 0.0273 (19) | 0.0244 (16) | −0.0056 (13) | 0.0042 (12) | −0.0062 (14) |
C3 | 0.0178 (15) | 0.0258 (17) | 0.0242 (15) | 0.0007 (12) | 0.0024 (11) | 0.0011 (13) |
C4 | 0.0252 (17) | 0.0261 (19) | 0.0268 (16) | 0.0028 (13) | 0.0026 (12) | −0.0013 (14) |
C5 | 0.0293 (16) | 0.0214 (17) | 0.0220 (15) | 0.0009 (12) | 0.0069 (12) | 0.0025 (13) |
C6 | 0.0327 (17) | 0.0224 (17) | 0.0217 (16) | 0.0011 (12) | 0.0060 (12) | 0.0027 (13) |
C7 | 0.0291 (17) | 0.034 (2) | 0.0227 (16) | 0.0077 (13) | −0.0007 (12) | 0.0011 (14) |
C8 | 0.0218 (16) | 0.035 (2) | 0.0228 (15) | 0.0050 (13) | 0.0038 (12) | 0.0013 (14) |
C9 | 0.0273 (17) | 0.0243 (19) | 0.0324 (17) | −0.0019 (12) | 0.0030 (13) | 0.0009 (14) |
C10 | 0.0301 (17) | 0.0284 (19) | 0.0216 (15) | 0.0007 (13) | −0.0009 (12) | −0.0049 (13) |
C11 | 0.0272 (16) | 0.0287 (18) | 0.0227 (16) | 0.0072 (13) | 0.0057 (12) | 0.0013 (13) |
C12 | 0.0363 (17) | 0.0285 (18) | 0.0172 (15) | 0.0080 (13) | 0.0047 (12) | 0.0041 (13) |
C13 | 0.0211 (15) | 0.0197 (17) | 0.0228 (15) | −0.0030 (12) | 0.0015 (11) | −0.0028 (13) |
C14 | 0.0369 (18) | 0.0258 (19) | 0.0293 (17) | −0.0008 (13) | 0.0172 (13) | −0.0024 (14) |
C15 | 0.0431 (19) | 0.039 (2) | 0.0346 (19) | −0.0091 (16) | 0.0205 (15) | −0.0083 (16) |
C16 | 0.0375 (18) | 0.040 (2) | 0.0249 (17) | −0.0162 (15) | 0.0028 (13) | 0.0027 (15) |
C17 | 0.0318 (17) | 0.0271 (19) | 0.0330 (18) | −0.0033 (13) | 0.0002 (14) | 0.0059 (15) |
C18 | 0.0222 (15) | 0.0278 (19) | 0.0272 (16) | 0.0005 (12) | 0.0018 (12) | 0.0016 (14) |
C19 | 0.0184 (14) | 0.0211 (17) | 0.0200 (14) | −0.0001 (12) | 0.0052 (11) | 0.0024 (13) |
C20 | 0.0249 (16) | 0.0188 (17) | 0.0265 (16) | 0.0004 (12) | 0.0057 (12) | 0.0018 (13) |
C21 | 0.0311 (17) | 0.0244 (18) | 0.0232 (16) | −0.0054 (13) | 0.0060 (12) | −0.0042 (13) |
C22 | 0.0226 (16) | 0.034 (2) | 0.0245 (16) | −0.0037 (13) | −0.0001 (12) | 0.0024 (14) |
C23 | 0.0241 (16) | 0.042 (2) | 0.0324 (18) | 0.0106 (14) | 0.0034 (13) | 0.0006 (16) |
C24 | 0.0280 (16) | 0.0311 (19) | 0.0264 (16) | 0.0044 (13) | 0.0058 (12) | −0.0045 (14) |
N1 | 0.0189 (12) | 0.0187 (14) | 0.0223 (12) | −0.0008 (9) | 0.0066 (9) | −0.0003 (10) |
N2 | 0.0212 (12) | 0.0146 (13) | 0.0271 (13) | 0.0000 (9) | 0.0068 (10) | −0.0033 (10) |
N3 | 0.0183 (12) | 0.0164 (13) | 0.0248 (12) | 0.0010 (9) | 0.0041 (9) | −0.0031 (10) |
O1 | 0.0263 (11) | 0.0209 (11) | 0.0184 (10) | −0.0057 (8) | 0.0054 (8) | −0.0037 (8) |
O2 | 0.0175 (10) | 0.0227 (12) | 0.0227 (10) | −0.0001 (8) | 0.0018 (7) | 0.0025 (8) |
O3 | 0.0312 (11) | 0.0159 (11) | 0.0181 (10) | 0.0009 (8) | 0.0067 (8) | −0.0003 (8) |
O4 | 0.0355 (12) | 0.0285 (13) | 0.0172 (10) | 0.0023 (9) | 0.0028 (8) | 0.0045 (9) |
O5 | 0.0242 (11) | 0.0248 (13) | 0.0334 (12) | −0.0005 (8) | 0.0093 (8) | −0.0019 (9) |
O6 | 0.0250 (11) | 0.0361 (13) | 0.0192 (10) | 0.0004 (9) | 0.0031 (8) | 0.0011 (9) |
O7 | 0.0256 (10) | 0.0230 (12) | 0.0198 (10) | 0.0050 (8) | 0.0067 (8) | 0.0016 (8) |
F1 | 0.0409 (11) | 0.0447 (12) | 0.0277 (10) | 0.0095 (8) | 0.0102 (8) | −0.0097 (8) |
F2 | 0.0553 (12) | 0.0455 (13) | 0.0307 (10) | −0.0281 (9) | −0.0007 (8) | −0.0076 (9) |
F3 | 0.0355 (10) | 0.0327 (11) | 0.0290 (9) | 0.0060 (8) | 0.0017 (7) | 0.0034 (8) |
F4 | 0.0462 (12) | 0.0542 (14) | 0.0426 (11) | 0.0211 (10) | −0.0012 (9) | −0.0229 (10) |
F5 | 0.0498 (12) | 0.0541 (14) | 0.0262 (10) | −0.0051 (9) | 0.0008 (8) | 0.0107 (9) |
F6 | 0.0292 (10) | 0.0410 (12) | 0.0382 (10) | −0.0032 (8) | −0.0060 (7) | −0.0069 (9) |
P1 | 0.0211 (4) | 0.0172 (4) | 0.0181 (4) | 0.0004 (3) | 0.0040 (3) | −0.0006 (3) |
P2 | 0.0185 (4) | 0.0194 (4) | 0.0183 (4) | 0.0018 (3) | 0.0033 (3) | −0.0004 (3) |
P3 | 0.0175 (4) | 0.0200 (4) | 0.0211 (4) | 0.0007 (3) | 0.0037 (3) | −0.0026 (3) |
C1—O1 | 1.431 (3) | C11—H11B | 0.9900 |
C1—C2 | 1.486 (4) | C12—O7 | 1.447 (3) |
C1—H1A | 0.9900 | C12—H12A | 0.9900 |
C1—H1B | 0.9900 | C12—H12B | 0.9900 |
C2—F1 | 1.332 (3) | C13—C14 | 1.393 (4) |
C2—F3 | 1.333 (3) | C13—C18 | 1.394 (4) |
C2—F2 | 1.338 (3) | C13—P3 | 1.789 (3) |
C3—O2 | 1.434 (3) | C14—C15 | 1.373 (4) |
C3—C4 | 1.486 (4) | C14—H14 | 0.9500 |
C3—H3A | 0.9900 | C15—C16 | 1.382 (5) |
C3—H3B | 0.9900 | C15—H15 | 0.9500 |
C4—F5 | 1.322 (3) | C16—C17 | 1.375 (4) |
C4—F6 | 1.339 (3) | C16—H16 | 0.9500 |
C4—F4 | 1.340 (3) | C17—C18 | 1.378 (4) |
C5—O3 | 1.441 (3) | C17—H17 | 0.9500 |
C5—C6 | 1.501 (4) | C18—H18 | 0.9500 |
C5—H5A | 0.9900 | C19—C24 | 1.389 (4) |
C5—H5B | 0.9900 | C19—C20 | 1.389 (4) |
C6—O4 | 1.415 (3) | C19—P3 | 1.800 (3) |
C6—H6A | 0.9900 | C20—C21 | 1.380 (4) |
C6—H6B | 0.9900 | C20—H20 | 0.9500 |
C7—O4 | 1.429 (3) | C21—C22 | 1.379 (4) |
C7—C8 | 1.497 (4) | C21—H21 | 0.9500 |
C7—H7A | 0.9900 | C22—C23 | 1.377 (4) |
C7—H7B | 0.9900 | C22—H22 | 0.9500 |
C8—O5 | 1.419 (3) | C23—C24 | 1.388 (4) |
C8—H8A | 0.9900 | C23—H23 | 0.9500 |
C8—H8B | 0.9900 | C24—H24 | 0.9500 |
C9—O5 | 1.418 (3) | N1—P2 | 1.581 (2) |
C9—C10 | 1.491 (4) | N1—P1 | 1.587 (2) |
C9—H9A | 0.9900 | N2—P2 | 1.569 (2) |
C9—H9B | 0.9900 | N2—P3 | 1.605 (2) |
C10—O6 | 1.426 (3) | N3—P1 | 1.565 (2) |
C10—H10A | 0.9900 | N3—P3 | 1.603 (2) |
C10—H10B | 0.9900 | O1—P1 | 1.5861 (18) |
C11—O6 | 1.420 (3) | O2—P2 | 1.5840 (18) |
C11—C12 | 1.493 (4) | O3—P1 | 1.5763 (19) |
C11—H11A | 0.9900 | O7—P2 | 1.5814 (18) |
O1—C1—C2 | 107.1 (2) | C11—C12—H12A | 110.1 |
O1—C1—H1A | 110.3 | O7—C12—H12B | 110.1 |
C2—C1—H1A | 110.3 | C11—C12—H12B | 110.1 |
O1—C1—H1B | 110.3 | H12A—C12—H12B | 108.5 |
C2—C1—H1B | 110.3 | C14—C13—C18 | 119.0 (3) |
H1A—C1—H1B | 108.6 | C14—C13—P3 | 120.4 (2) |
F1—C2—F3 | 105.8 (2) | C18—C13—P3 | 120.6 (2) |
F1—C2—F2 | 107.3 (2) | C15—C14—C13 | 120.2 (3) |
F3—C2—F2 | 106.8 (2) | C15—C14—H14 | 119.9 |
F1—C2—C1 | 113.0 (2) | C13—C14—H14 | 119.9 |
F3—C2—C1 | 113.4 (2) | C14—C15—C16 | 120.3 (3) |
F2—C2—C1 | 110.2 (2) | C14—C15—H15 | 119.9 |
O2—C3—C4 | 108.8 (2) | C16—C15—H15 | 119.9 |
O2—C3—H3A | 109.9 | C17—C16—C15 | 119.9 (3) |
C4—C3—H3A | 109.9 | C17—C16—H16 | 120.0 |
O2—C3—H3B | 109.9 | C15—C16—H16 | 120.0 |
C4—C3—H3B | 109.9 | C16—C17—C18 | 120.4 (3) |
H3A—C3—H3B | 108.3 | C16—C17—H17 | 119.8 |
F5—C4—F6 | 107.2 (2) | C18—C17—H17 | 119.8 |
F5—C4—F4 | 106.5 (2) | C17—C18—C13 | 120.1 (3) |
F6—C4—F4 | 106.4 (2) | C17—C18—H18 | 119.9 |
F5—C4—C3 | 113.0 (2) | C13—C18—H18 | 119.9 |
F6—C4—C3 | 110.5 (2) | C24—C19—C20 | 118.9 (2) |
F4—C4—C3 | 112.8 (2) | C24—C19—P3 | 120.0 (2) |
O3—C5—C6 | 110.9 (2) | C20—C19—P3 | 121.1 (2) |
O3—C5—H5A | 109.5 | C21—C20—C19 | 120.4 (3) |
C6—C5—H5A | 109.5 | C21—C20—H20 | 119.8 |
O3—C5—H5B | 109.5 | C19—C20—H20 | 119.8 |
C6—C5—H5B | 109.5 | C22—C21—C20 | 120.3 (3) |
H5A—C5—H5B | 108.1 | C22—C21—H21 | 119.9 |
O4—C6—C5 | 105.6 (2) | C20—C21—H21 | 119.9 |
O4—C6—H6A | 110.6 | C23—C22—C21 | 120.0 (3) |
C5—C6—H6A | 110.6 | C23—C22—H22 | 120.0 |
O4—C6—H6B | 110.6 | C21—C22—H22 | 120.0 |
C5—C6—H6B | 110.6 | C22—C23—C24 | 120.0 (3) |
H6A—C6—H6B | 108.7 | C22—C23—H23 | 120.0 |
O4—C7—C8 | 114.9 (2) | C24—C23—H23 | 120.0 |
O4—C7—H7A | 108.5 | C23—C24—C19 | 120.4 (3) |
C8—C7—H7A | 108.5 | C23—C24—H24 | 119.8 |
O4—C7—H7B | 108.5 | C19—C24—H24 | 119.8 |
C8—C7—H7B | 108.5 | P2—N1—P1 | 122.76 (13) |
H7A—C7—H7B | 107.5 | P2—N2—P3 | 121.81 (14) |
O5—C8—C7 | 108.8 (2) | P1—N3—P3 | 122.24 (13) |
O5—C8—H8A | 109.9 | C1—O1—P1 | 119.89 (16) |
C7—C8—H8A | 109.9 | C3—O2—P2 | 119.68 (17) |
O5—C8—H8B | 109.9 | C5—O3—P1 | 123.76 (17) |
C7—C8—H8B | 109.9 | C6—O4—C7 | 113.4 (2) |
H8A—C8—H8B | 108.3 | C9—O5—C8 | 111.7 (2) |
O5—C9—C10 | 109.1 (2) | C11—O6—C10 | 115.9 (2) |
O5—C9—H9A | 109.9 | C12—O7—P2 | 119.43 (17) |
C10—C9—H9A | 109.9 | N3—P1—O3 | 112.73 (11) |
O5—C9—H9B | 109.9 | N3—P1—O1 | 106.78 (11) |
C10—C9—H9B | 109.9 | O3—P1—O1 | 97.76 (10) |
H9A—C9—H9B | 108.3 | N3—P1—N1 | 117.24 (12) |
O6—C10—C9 | 113.7 (2) | O3—P1—N1 | 108.79 (11) |
O6—C10—H10A | 108.8 | O1—P1—N1 | 111.83 (11) |
C9—C10—H10A | 108.8 | N2—P2—N1 | 117.58 (12) |
O6—C10—H10B | 108.8 | N2—P2—O7 | 111.04 (11) |
C9—C10—H10B | 108.8 | N1—P2—O7 | 108.91 (11) |
H10A—C10—H10B | 107.7 | N2—P2—O2 | 107.59 (11) |
O6—C11—C12 | 108.0 (2) | N1—P2—O2 | 111.70 (11) |
O6—C11—H11A | 110.1 | O7—P2—O2 | 98.33 (10) |
C12—C11—H11A | 110.1 | N3—P3—N2 | 117.27 (11) |
O6—C11—H11B | 110.1 | N3—P3—C13 | 108.64 (12) |
C12—C11—H11B | 110.1 | N2—P3—C13 | 108.51 (13) |
H11A—C11—H11B | 108.4 | N3—P3—C19 | 107.51 (12) |
O7—C12—C11 | 107.8 (2) | N2—P3—C19 | 107.68 (12) |
O7—C12—H12A | 110.1 | C13—P3—C19 | 106.76 (12) |
O1—C1—C2—F1 | 57.5 (3) | C5—O3—P1—N3 | 84.1 (2) |
O1—C1—C2—F3 | −62.8 (3) | C5—O3—P1—O1 | −164.04 (18) |
O1—C1—C2—F2 | 177.5 (2) | C5—O3—P1—N1 | −47.8 (2) |
O2—C3—C4—F5 | −62.9 (3) | C1—O1—P1—N3 | 167.0 (2) |
O2—C3—C4—F6 | 177.0 (2) | C1—O1—P1—O3 | 50.4 (2) |
O2—C3—C4—F4 | 58.0 (3) | C1—O1—P1—N1 | −63.5 (2) |
O3—C5—C6—O4 | −171.3 (2) | P2—N1—P1—N3 | 10.9 (2) |
O4—C7—C8—O5 | 58.3 (3) | P2—N1—P1—O3 | 140.30 (14) |
O5—C9—C10—O6 | −58.9 (3) | P2—N1—P1—O1 | −112.85 (15) |
O6—C11—C12—O7 | 164.2 (2) | P3—N2—P2—N1 | 8.0 (2) |
C18—C13—C14—C15 | −1.1 (4) | P3—N2—P2—O7 | 134.31 (15) |
P3—C13—C14—C15 | 177.9 (2) | P3—N2—P2—O2 | −119.14 (16) |
C13—C14—C15—C16 | −0.2 (4) | P1—N1—P2—N2 | −11.0 (2) |
C14—C15—C16—C17 | 1.2 (4) | P1—N1—P2—O7 | −138.35 (14) |
C15—C16—C17—C18 | −0.7 (4) | P1—N1—P2—O2 | 114.12 (15) |
C16—C17—C18—C13 | −0.7 (4) | C12—O7—P2—N2 | −73.2 (2) |
C14—C13—C18—C17 | 1.6 (4) | C12—O7—P2—N1 | 57.8 (2) |
P3—C13—C18—C17 | −177.4 (2) | C12—O7—P2—O2 | 174.21 (19) |
C24—C19—C20—C21 | 0.1 (4) | C3—O2—P2—N2 | −174.73 (18) |
P3—C19—C20—C21 | −178.7 (2) | C3—O2—P2—N1 | 54.8 (2) |
C19—C20—C21—C22 | 0.7 (4) | C3—O2—P2—O7 | −59.45 (19) |
C20—C21—C22—C23 | −1.1 (4) | P1—N3—P3—N2 | 5.3 (2) |
C21—C22—C23—C24 | 0.8 (4) | P1—N3—P3—C13 | −118.16 (16) |
C22—C23—C24—C19 | 0.0 (4) | P1—N3—P3—C19 | 126.65 (16) |
C20—C19—C24—C23 | −0.5 (4) | P2—N2—P3—N3 | −5.2 (2) |
P3—C19—C24—C23 | 178.3 (2) | P2—N2—P3—C13 | 118.26 (16) |
C2—C1—O1—P1 | 166.95 (18) | P2—N2—P3—C19 | −126.53 (16) |
C4—C3—O2—P2 | −119.2 (2) | C14—C13—P3—N3 | −33.9 (3) |
C6—C5—O3—P1 | −73.5 (3) | C18—C13—P3—N3 | 145.1 (2) |
C5—C6—O4—C7 | −176.9 (2) | C14—C13—P3—N2 | −162.4 (2) |
C8—C7—O4—C6 | 67.3 (3) | C18—C13—P3—N2 | 16.6 (2) |
C10—C9—O5—C8 | 178.6 (2) | C14—C13—P3—C19 | 81.8 (2) |
C7—C8—O5—C9 | −178.5 (2) | C18—C13—P3—C19 | −99.2 (2) |
C12—C11—O6—C10 | 123.1 (2) | C24—C19—P3—N3 | 33.5 (3) |
C9—C10—O6—C11 | −66.5 (3) | C20—C19—P3—N3 | −147.7 (2) |
C11—C12—O7—P2 | 134.7 (2) | C24—C19—P3—N2 | 160.7 (2) |
P3—N3—P1—O3 | −135.42 (14) | C20—C19—P3—N2 | −20.5 (3) |
P3—N3—P1—O1 | 118.37 (15) | C24—C19—P3—C13 | −82.9 (2) |
P3—N3—P1—N1 | −7.9 (2) | C20—C19—P3—C13 | 95.8 (2) |
C32H36N3O7P3 | Z = 2 |
Mr = 667.55 | F(000) = 700 |
Triclinic, P1 | Dx = 1.385 Mg m−3 |
a = 10.166 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.105 (2) Å | Cell parameters from 13461 reflections |
c = 13.313 (3) Å | θ = 2.9–27.5° |
α = 88.86 (3)° | µ = 0.24 mm−1 |
β = 86.54 (3)° | T = 150 K |
γ = 78.14 (3)° | Block, colourless |
V = 1600.4 (6) Å3 | 0.20 × 0.15 × 0.10 mm |
Bruker-Nonius KappaCCD diffractometer | 12306 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 8750 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ϕ & ω scans | h = −13→11 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −15→13 |
Tmin = 0.954, Tmax = 0.977 | l = −17→16 |
24220 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 0.94 | Δρmax = 0.81 e Å−3 |
12306 reflections | Δρmin = −0.40 e Å−3 |
824 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
22 restraints | Extinction coefficient: 0.0054 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (7) |
C32H36N3O7P3 | γ = 78.14 (3)° |
Mr = 667.55 | V = 1600.4 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.166 (2) Å | Mo Kα radiation |
b = 12.105 (2) Å | µ = 0.24 mm−1 |
c = 13.313 (3) Å | T = 150 K |
α = 88.86 (3)° | 0.20 × 0.15 × 0.10 mm |
β = 86.54 (3)° |
Bruker-Nonius KappaCCD diffractometer | 12306 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 8750 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.977 | Rint = 0.061 |
24220 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | Δρmax = 0.81 e Å−3 |
S = 0.94 | Δρmin = −0.40 e Å−3 |
12306 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
824 parameters | Absolute structure parameter: 0.03 (7) |
22 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6413 (4) | 0.3165 (4) | 0.7512 (3) | 0.0331 (10) | |
C2 | 0.7215 (5) | 0.3322 (4) | 0.8277 (3) | 0.0451 (12) | |
H2 | 0.7506 | 0.4015 | 0.8326 | 0.054* | |
C3 | 0.7592 (5) | 0.2472 (6) | 0.8971 (4) | 0.0608 (16) | |
H3 | 0.8151 | 0.2575 | 0.9493 | 0.073* | |
C4 | 0.7162 (6) | 0.1488 (6) | 0.8906 (4) | 0.0634 (17) | |
H4 | 0.7429 | 0.0901 | 0.9382 | 0.076* | |
C5 | 0.6339 (6) | 0.1332 (5) | 0.8155 (4) | 0.0563 (14) | |
H5 | 0.6035 | 0.0643 | 0.8118 | 0.068* | |
C6 | 0.5956 (5) | 0.2186 (4) | 0.7453 (3) | 0.0419 (11) | |
H6 | 0.5383 | 0.2089 | 0.6938 | 0.050* | |
C7 | 0.4772 (4) | 0.1248 (3) | 0.4866 (3) | 0.0287 (9) | |
C8 | 0.3498 (4) | 0.1431 (4) | 0.5301 (3) | 0.0407 (11) | |
H8 | 0.2823 | 0.2033 | 0.5076 | 0.049* | |
C9 | 0.3204 (5) | 0.0721 (5) | 0.6078 (4) | 0.0545 (14) | |
H9 | 0.2309 | 0.0821 | 0.6366 | 0.065* | |
C10 | 0.4186 (5) | −0.0122 (4) | 0.6437 (4) | 0.0483 (13) | |
H10 | 0.3984 | −0.0589 | 0.6982 | 0.058* | |
C11 | 0.5449 (5) | −0.0277 (4) | 0.5998 (4) | 0.0452 (12) | |
H11 | 0.6128 | −0.0861 | 0.6245 | 0.054* | |
C12 | 0.5784 (4) | 0.0388 (4) | 0.5200 (3) | 0.0369 (11) | |
H12 | 0.6670 | 0.0262 | 0.4894 | 0.044* | |
C13 | 0.7370 (5) | 0.5866 (4) | 0.6018 (3) | 0.0389 (11) | |
H13A | 0.8254 | 0.5373 | 0.6132 | 0.047* | |
H13B | 0.6919 | 0.6109 | 0.6680 | 0.047* | |
C14 | 0.7560 (5) | 0.6874 (4) | 0.5402 (4) | 0.0462 (12) | |
H14A | 0.6678 | 0.7301 | 0.5196 | 0.055* | |
H14B | 0.7974 | 0.7378 | 0.5803 | 0.055* | |
C15 | 0.8038 (6) | 0.7150 (4) | 0.3664 (4) | 0.0607 (16) | |
H15A | 0.8084 | 0.7946 | 0.3779 | 0.073* | |
H15B | 0.7100 | 0.7125 | 0.3523 | 0.073* | |
C16 | 0.8930 (7) | 0.6717 (5) | 0.2809 (4) | 0.0639 (16) | |
H16A | 0.8767 | 0.7250 | 0.2235 | 0.077* | |
H16B | 0.9877 | 0.6644 | 0.2983 | 0.077* | |
C17 | 0.9586 (5) | 0.5201 (4) | 0.1709 (3) | 0.0418 (12) | |
H17A | 1.0528 | 0.5196 | 0.1862 | 0.050* | |
H17B | 0.9373 | 0.5677 | 0.1103 | 0.050* | |
C18 | 0.9424 (4) | 0.4047 (4) | 0.1522 (3) | 0.0401 (11) | |
H18A | 1.0162 | 0.3678 | 0.1046 | 0.048* | |
H18B | 0.9502 | 0.3614 | 0.2162 | 0.048* | |
C19 | 0.7362 (5) | 0.3359 (4) | 0.1681 (3) | 0.0378 (11) | |
H19A | 0.7957 | 0.2682 | 0.1954 | 0.045* | |
H19B | 0.6742 | 0.3101 | 0.1234 | 0.045* | |
C20 | 0.6557 (4) | 0.4026 (4) | 0.2535 (3) | 0.0342 (10) | |
H20A | 0.7169 | 0.4217 | 0.3025 | 0.041* | |
H20B | 0.6016 | 0.4737 | 0.2276 | 0.041* | |
C21 | 1.0072 (4) | 0.2632 (3) | 0.4118 (3) | 0.0265 (9) | |
C22 | 1.0357 (4) | 0.3692 (4) | 0.4182 (3) | 0.0328 (10) | |
H22 | 0.9797 | 0.4242 | 0.4603 | 0.039* | |
C23 | 1.1454 (5) | 0.3964 (4) | 0.3636 (3) | 0.0399 (11) | |
H23 | 1.1645 | 0.4695 | 0.3693 | 0.048* | |
C24 | 1.2276 (4) | 0.3175 (4) | 0.3008 (4) | 0.0429 (12) | |
H24 | 1.3030 | 0.3360 | 0.2637 | 0.052* | |
C25 | 1.1980 (5) | 0.2116 (4) | 0.2930 (4) | 0.0395 (11) | |
C26 | 1.0892 (4) | 0.1839 (4) | 0.3477 (3) | 0.0351 (10) | |
H26 | 1.0699 | 0.1109 | 0.3418 | 0.042* | |
C27 | 0.9209 (4) | 0.0982 (3) | 0.5444 (3) | 0.0282 (9) | |
C28 | 0.9400 (4) | 0.0970 (4) | 0.6463 (3) | 0.0361 (11) | |
C29 | 0.9899 (5) | −0.0047 (4) | 0.6948 (4) | 0.0459 (13) | |
H29 | 1.0030 | −0.0053 | 0.7649 | 0.055* | |
C30 | 1.0201 (4) | −0.1037 (4) | 0.6426 (4) | 0.0500 (14) | |
H30 | 1.0559 | −0.1722 | 0.6763 | 0.060* | |
C31 | 0.9988 (5) | −0.1050 (4) | 0.5408 (4) | 0.0454 (12) | |
H31 | 1.0184 | −0.1740 | 0.5050 | 0.055* | |
C32 | 0.9480 (4) | −0.0034 (4) | 0.4915 (4) | 0.0395 (11) | |
H32 | 0.9320 | −0.0034 | 0.4220 | 0.047* | |
C33 | 0.0458 (4) | 0.9098 (3) | 0.9875 (3) | 0.0291 (10) | |
C34 | 0.0976 (5) | 0.9953 (4) | 1.0268 (4) | 0.0443 (12) | |
H34 | 0.1770 | 1.0155 | 0.9976 | 0.053* | |
C35 | 0.0282 (6) | 1.0515 (4) | 1.1119 (4) | 0.0506 (13) | |
C36 | −0.0859 (6) | 1.0204 (4) | 1.1542 (4) | 0.0458 (12) | |
H36 | −0.1319 | 1.0589 | 1.2117 | 0.055* | |
C37 | −0.1327 (5) | 0.9345 (4) | 1.1137 (4) | 0.0479 (13) | |
H37 | −0.2110 | 0.9130 | 1.1435 | 0.057* | |
C38 | −0.0665 (5) | 0.8777 (4) | 1.0285 (4) | 0.0415 (12) | |
H38 | −0.0993 | 0.8180 | 1.0000 | 0.050* | |
C39 | 0.2650 (4) | 0.7026 (4) | 1.2527 (3) | 0.0302 (10) | |
C40 | 0.2273 (5) | 0.8133 (4) | 1.2833 (4) | 0.0407 (11) | |
H40 | 0.1687 | 0.8674 | 1.2453 | 0.049* | |
C41 | 0.2776 (5) | 0.8433 (5) | 1.3715 (4) | 0.0505 (13) | |
H41 | 0.2526 | 0.9190 | 1.3945 | 0.061* | |
C42 | 0.3632 (5) | 0.7643 (5) | 1.4257 (4) | 0.0541 (14) | |
H42 | 0.3982 | 0.7851 | 1.4855 | 0.065* | |
C43 | 0.3970 (5) | 0.6557 (5) | 1.3923 (4) | 0.0502 (13) | |
H43 | 0.4564 | 0.6012 | 1.4293 | 0.060* | |
C44 | 0.3479 (4) | 0.6240 (4) | 1.3078 (4) | 0.0382 (11) | |
C45 | 0.3484 (4) | 0.6531 (4) | 0.7381 (3) | 0.0354 (10) | |
H45A | 0.3940 | 0.5990 | 0.7880 | 0.042* | |
H45B | 0.4138 | 0.6965 | 0.7083 | 0.042* | |
C46 | 0.2970 (5) | 0.5914 (4) | 0.6580 (3) | 0.0379 (11) | |
H46A | 0.2412 | 0.6456 | 0.6132 | 0.045* | |
H46B | 0.3732 | 0.5467 | 0.6169 | 0.045* | |
C47 | 0.1847 (8) | 0.4425 (6) | 0.6381 (5) | 0.0812 (11) | |
H47A | 0.2663 | 0.4009 | 0.6007 | 0.097* | |
H47B | 0.1226 | 0.4834 | 0.5890 | 0.097* | |
C48 | 0.1178 (7) | 0.3620 (5) | 0.6990 (4) | 0.0670 (17) | |
H48A | 0.0446 | 0.4038 | 0.7444 | 0.080* | |
H48B | 0.0790 | 0.3143 | 0.6542 | 0.080* | |
C49 | 0.1786 (7) | 0.2199 (5) | 0.8270 (4) | 0.0812 (11) | |
H49A | 0.0972 | 0.1961 | 0.8054 | 0.097* | |
H49B | 0.2507 | 0.1517 | 0.8327 | 0.097* | |
C50 | 0.1476 (7) | 0.2783 (6) | 0.9297 (4) | 0.0812 (11) | |
H50A | 0.0805 | 0.3489 | 0.9196 | 0.097* | |
H50B | 0.1026 | 0.2291 | 0.9742 | 0.097* | |
C51 | 0.3242 (5) | 0.3829 (4) | 0.9362 (4) | 0.0468 (12) | |
H51A | 0.2619 | 0.4480 | 0.9076 | 0.056* | |
H51B | 0.3850 | 0.3447 | 0.8808 | 0.056* | |
C52 | 0.4052 (5) | 0.4229 (4) | 1.0141 (4) | 0.0461 (12) | |
H52A | 0.4550 | 0.3566 | 1.0503 | 0.055* | |
H52B | 0.4720 | 0.4619 | 0.9798 | 0.055* | |
C53 | 0.6390 (4) | 0.7226 (3) | 0.9300 (3) | 0.0275 (9) | |
C54 | 0.7292 (4) | 0.6270 (4) | 0.9567 (3) | 0.0357 (10) | |
H54 | 0.7044 | 0.5801 | 1.0096 | 0.043* | |
C55 | 0.8546 (4) | 0.5984 (4) | 0.9082 (3) | 0.0386 (11) | |
H55 | 0.9153 | 0.5317 | 0.9273 | 0.046* | |
C56 | 0.8927 (5) | 0.6657 (4) | 0.8319 (4) | 0.0409 (12) | |
C57 | 0.8018 (5) | 0.7609 (4) | 0.8038 (3) | 0.0417 (12) | |
H57 | 0.8267 | 0.8073 | 0.7506 | 0.050* | |
C58 | 0.6765 (4) | 0.7895 (4) | 0.8515 (3) | 0.0338 (10) | |
H58 | 0.6151 | 0.8551 | 0.8311 | 0.041* | |
C59 | 0.4922 (4) | 0.8812 (4) | 1.0727 (3) | 0.0284 (9) | |
C60 | 0.4746 (5) | 0.9894 (4) | 1.0319 (4) | 0.0382 (11) | |
C61 | 0.4885 (5) | 1.0797 (4) | 1.0905 (4) | 0.0460 (12) | |
H61 | 0.4764 | 1.1536 | 1.0623 | 0.055* | |
C62 | 0.5198 (5) | 1.0618 (4) | 1.1886 (4) | 0.0448 (12) | |
H62 | 0.5314 | 1.1231 | 1.2282 | 0.054* | |
C63 | 0.5347 (5) | 0.9544 (4) | 1.2310 (4) | 0.0441 (12) | |
H63 | 0.5535 | 0.9430 | 1.2999 | 0.053* | |
C64 | 0.5223 (4) | 0.8640 (4) | 1.1729 (3) | 0.0355 (10) | |
H64 | 0.5343 | 0.7903 | 1.2014 | 0.043* | |
N1 | 0.5592 (3) | 0.3621 (3) | 0.4977 (3) | 0.0306 (8) | |
N2 | 0.7557 (3) | 0.2107 (3) | 0.4021 (2) | 0.0267 (8) | |
N3 | 0.8121 (3) | 0.3259 (3) | 0.5637 (2) | 0.0269 (8) | |
N4 | 0.2159 (3) | 0.6647 (3) | 0.9743 (3) | 0.0333 (8) | |
N5 | 0.4455 (3) | 0.6635 (3) | 1.0654 (2) | 0.0281 (8) | |
N6 | 0.3679 (3) | 0.8139 (3) | 0.9135 (3) | 0.0308 (8) | |
O1 | 0.6040 (3) | 0.4035 (2) | 0.6831 (2) | 0.0337 (7) | |
O2 | 0.5028 (3) | 0.1934 (2) | 0.4043 (2) | 0.0308 (7) | |
O3 | 0.6561 (3) | 0.5265 (2) | 0.5483 (2) | 0.0336 (7) | |
O4 | 0.8407 (3) | 0.6500 (3) | 0.4540 (2) | 0.0461 (8) | |
O5 | 0.8707 (3) | 0.5642 (3) | 0.2530 (2) | 0.0455 (8) | |
O6 | 0.8151 (3) | 0.4011 (3) | 0.1116 (2) | 0.0367 (7) | |
O7 | 0.5671 (3) | 0.3340 (2) | 0.3024 (2) | 0.0327 (7) | |
O8 | 0.1070 (3) | 0.8590 (3) | 0.8981 (2) | 0.0365 (7) | |
O9 | 0.2117 (3) | 0.6751 (3) | 1.1640 (2) | 0.0442 (8) | |
O10 | 0.2334 (3) | 0.7287 (3) | 0.7860 (2) | 0.0389 (8) | |
O11 | 0.2198 (3) | 0.5201 (3) | 0.7055 (2) | 0.0454 (8) | |
O12 | 0.2194 (5) | 0.2939 (4) | 0.7559 (3) | 0.0854 (14) | |
O13 | 0.2498 (3) | 0.3065 (3) | 0.9829 (2) | 0.0481 (9) | |
O14 | 0.3225 (3) | 0.4986 (2) | 1.0860 (2) | 0.0382 (7) | |
P1 | 0.66234 (11) | 0.39684 (9) | 0.56834 (8) | 0.0281 (2) | |
P2 | 0.60464 (10) | 0.27688 (9) | 0.40729 (8) | 0.0269 (2) | |
P3 | 0.86202 (10) | 0.22965 (9) | 0.48078 (8) | 0.0251 (2) | |
P4 | 0.24002 (11) | 0.76270 (10) | 0.89930 (8) | 0.0303 (3) | |
P5 | 0.30434 (11) | 0.62864 (10) | 1.06672 (8) | 0.0303 (3) | |
P6 | 0.47563 (11) | 0.76544 (9) | 0.99517 (8) | 0.0266 (2) | |
H25 | 1.256 (4) | 0.158 (3) | 0.251 (3) | 0.021 (10)* | |
H28 | 0.927 (3) | 0.169 (3) | 0.690 (2) | 0.001 (8)* | |
H35 | 0.068 (5) | 1.123 (4) | 1.148 (3) | 0.048 (13)* | |
H44 | 0.371 (5) | 0.546 (4) | 1.286 (3) | 0.041 (13)* | |
H56 | 0.979 (5) | 0.648 (4) | 0.795 (3) | 0.038 (12)* | |
H60 | 0.441 (4) | 1.001 (3) | 0.964 (3) | 0.025 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.034 (2) | 0.037 (3) | 0.025 (2) | −0.003 (2) | 0.0033 (18) | −0.0053 (19) |
C2 | 0.036 (3) | 0.063 (3) | 0.037 (3) | −0.014 (2) | 0.003 (2) | −0.014 (2) |
C3 | 0.042 (3) | 0.108 (5) | 0.033 (3) | −0.017 (3) | −0.004 (2) | 0.000 (3) |
C4 | 0.059 (4) | 0.078 (4) | 0.041 (3) | 0.008 (3) | 0.010 (3) | 0.018 (3) |
C5 | 0.078 (4) | 0.046 (3) | 0.043 (3) | −0.012 (3) | 0.006 (3) | 0.009 (2) |
C6 | 0.046 (3) | 0.048 (3) | 0.034 (3) | −0.015 (2) | −0.001 (2) | −0.006 (2) |
C7 | 0.033 (2) | 0.031 (2) | 0.026 (2) | −0.0150 (19) | −0.0025 (18) | −0.0034 (18) |
C8 | 0.025 (2) | 0.049 (3) | 0.048 (3) | −0.010 (2) | −0.002 (2) | 0.008 (2) |
C9 | 0.034 (3) | 0.073 (4) | 0.057 (3) | −0.016 (3) | 0.010 (2) | 0.012 (3) |
C10 | 0.051 (3) | 0.046 (3) | 0.049 (3) | −0.013 (3) | 0.002 (3) | 0.009 (2) |
C11 | 0.057 (3) | 0.029 (3) | 0.048 (3) | −0.004 (2) | −0.004 (3) | 0.003 (2) |
C12 | 0.031 (2) | 0.033 (2) | 0.045 (3) | −0.0025 (19) | 0.001 (2) | −0.006 (2) |
C13 | 0.045 (3) | 0.036 (3) | 0.038 (3) | −0.014 (2) | 0.000 (2) | −0.004 (2) |
C14 | 0.054 (3) | 0.032 (3) | 0.053 (3) | −0.010 (2) | 0.009 (3) | −0.013 (2) |
C15 | 0.085 (4) | 0.030 (3) | 0.066 (4) | −0.011 (3) | −0.003 (3) | 0.004 (3) |
C16 | 0.101 (5) | 0.044 (3) | 0.049 (3) | −0.022 (3) | −0.003 (3) | 0.008 (3) |
C17 | 0.039 (3) | 0.055 (3) | 0.034 (3) | −0.017 (2) | −0.005 (2) | 0.011 (2) |
C18 | 0.027 (2) | 0.058 (3) | 0.033 (3) | −0.006 (2) | 0.0038 (19) | 0.003 (2) |
C19 | 0.036 (3) | 0.041 (3) | 0.038 (3) | −0.011 (2) | −0.002 (2) | 0.002 (2) |
C20 | 0.027 (2) | 0.035 (3) | 0.039 (3) | −0.0058 (19) | 0.0041 (19) | 0.006 (2) |
C21 | 0.0155 (19) | 0.035 (2) | 0.029 (2) | −0.0065 (17) | −0.0024 (16) | 0.0057 (18) |
C22 | 0.035 (2) | 0.032 (3) | 0.032 (2) | −0.0094 (19) | 0.0017 (19) | −0.0021 (19) |
C23 | 0.039 (3) | 0.049 (3) | 0.038 (3) | −0.024 (2) | −0.001 (2) | 0.007 (2) |
C24 | 0.023 (2) | 0.065 (3) | 0.042 (3) | −0.013 (2) | −0.004 (2) | 0.012 (2) |
C25 | 0.027 (2) | 0.043 (3) | 0.045 (3) | −0.003 (2) | 0.007 (2) | −0.003 (2) |
C26 | 0.029 (2) | 0.042 (3) | 0.032 (2) | −0.003 (2) | −0.0002 (19) | 0.003 (2) |
C27 | 0.0147 (19) | 0.031 (2) | 0.038 (2) | −0.0032 (17) | 0.0011 (17) | 0.0060 (19) |
C28 | 0.026 (2) | 0.048 (3) | 0.036 (3) | −0.010 (2) | −0.0015 (19) | 0.003 (2) |
C29 | 0.032 (2) | 0.054 (3) | 0.048 (3) | −0.004 (2) | −0.005 (2) | 0.025 (3) |
C30 | 0.025 (2) | 0.046 (3) | 0.074 (4) | 0.000 (2) | 0.005 (2) | 0.031 (3) |
C31 | 0.039 (3) | 0.033 (3) | 0.061 (3) | −0.005 (2) | 0.012 (2) | 0.011 (2) |
C32 | 0.033 (2) | 0.037 (3) | 0.047 (3) | −0.006 (2) | 0.003 (2) | 0.007 (2) |
C33 | 0.023 (2) | 0.035 (2) | 0.025 (2) | 0.0032 (18) | −0.0017 (17) | −0.0003 (18) |
C34 | 0.045 (3) | 0.038 (3) | 0.049 (3) | −0.010 (2) | 0.004 (2) | −0.010 (2) |
C35 | 0.067 (4) | 0.038 (3) | 0.045 (3) | −0.006 (3) | 0.000 (3) | −0.007 (2) |
C36 | 0.057 (3) | 0.039 (3) | 0.032 (3) | 0.010 (2) | 0.006 (2) | −0.002 (2) |
C37 | 0.042 (3) | 0.046 (3) | 0.050 (3) | −0.002 (2) | 0.010 (2) | 0.005 (3) |
C38 | 0.032 (3) | 0.040 (3) | 0.052 (3) | −0.003 (2) | −0.007 (2) | −0.006 (2) |
C39 | 0.019 (2) | 0.046 (3) | 0.026 (2) | −0.0094 (19) | 0.0063 (17) | −0.0040 (19) |
C40 | 0.029 (2) | 0.041 (3) | 0.048 (3) | −0.002 (2) | 0.006 (2) | 0.008 (2) |
C41 | 0.048 (3) | 0.050 (3) | 0.054 (3) | −0.014 (3) | 0.014 (3) | −0.021 (3) |
C42 | 0.041 (3) | 0.091 (4) | 0.033 (3) | −0.020 (3) | 0.001 (2) | −0.009 (3) |
C43 | 0.035 (3) | 0.073 (4) | 0.038 (3) | −0.002 (3) | 0.000 (2) | 0.013 (3) |
C44 | 0.031 (2) | 0.037 (3) | 0.045 (3) | −0.006 (2) | 0.010 (2) | 0.002 (2) |
C45 | 0.026 (2) | 0.043 (3) | 0.035 (3) | −0.0025 (19) | 0.0033 (19) | −0.005 (2) |
C46 | 0.036 (2) | 0.045 (3) | 0.028 (2) | 0.002 (2) | 0.0024 (19) | −0.005 (2) |
C47 | 0.107 (3) | 0.087 (3) | 0.066 (2) | −0.057 (2) | −0.012 (2) | 0.0037 (19) |
C48 | 0.086 (5) | 0.082 (4) | 0.047 (3) | −0.047 (4) | −0.021 (3) | 0.001 (3) |
C49 | 0.107 (3) | 0.087 (3) | 0.066 (2) | −0.057 (2) | −0.012 (2) | 0.0037 (19) |
C50 | 0.107 (3) | 0.087 (3) | 0.066 (2) | −0.057 (2) | −0.012 (2) | 0.0037 (19) |
C51 | 0.047 (3) | 0.040 (3) | 0.055 (3) | −0.018 (2) | 0.013 (2) | −0.009 (2) |
C52 | 0.036 (3) | 0.027 (2) | 0.075 (4) | −0.002 (2) | −0.008 (2) | 0.000 (2) |
C53 | 0.025 (2) | 0.028 (2) | 0.029 (2) | −0.0046 (18) | −0.0038 (18) | 0.0010 (18) |
C54 | 0.035 (2) | 0.035 (3) | 0.036 (3) | −0.005 (2) | 0.000 (2) | −0.001 (2) |
C55 | 0.031 (2) | 0.043 (3) | 0.039 (3) | 0.000 (2) | 0.003 (2) | −0.012 (2) |
C56 | 0.024 (2) | 0.056 (3) | 0.042 (3) | −0.007 (2) | 0.002 (2) | −0.018 (2) |
C57 | 0.046 (3) | 0.051 (3) | 0.034 (3) | −0.025 (2) | 0.010 (2) | 0.000 (2) |
C58 | 0.033 (2) | 0.033 (2) | 0.036 (3) | −0.0073 (19) | −0.002 (2) | −0.0010 (19) |
C59 | 0.020 (2) | 0.035 (2) | 0.028 (2) | −0.0019 (17) | 0.0043 (17) | −0.0024 (18) |
C60 | 0.042 (3) | 0.034 (3) | 0.038 (3) | −0.007 (2) | 0.000 (2) | −0.001 (2) |
C61 | 0.053 (3) | 0.035 (3) | 0.051 (3) | −0.011 (2) | −0.001 (2) | −0.005 (2) |
C62 | 0.034 (3) | 0.045 (3) | 0.055 (3) | −0.006 (2) | 0.008 (2) | −0.026 (2) |
C63 | 0.037 (3) | 0.061 (3) | 0.036 (3) | −0.014 (2) | −0.002 (2) | −0.010 (2) |
C64 | 0.035 (3) | 0.038 (3) | 0.035 (3) | −0.011 (2) | 0.000 (2) | −0.005 (2) |
N1 | 0.0219 (18) | 0.0280 (19) | 0.042 (2) | −0.0053 (14) | 0.0026 (15) | −0.0061 (16) |
N2 | 0.0212 (17) | 0.0284 (19) | 0.0295 (19) | −0.0034 (14) | 0.0006 (14) | −0.0024 (15) |
N3 | 0.0236 (18) | 0.0324 (19) | 0.0261 (18) | −0.0091 (15) | −0.0008 (14) | 0.0001 (14) |
N4 | 0.0255 (19) | 0.037 (2) | 0.039 (2) | −0.0082 (16) | −0.0056 (16) | −0.0048 (16) |
N5 | 0.0280 (18) | 0.033 (2) | 0.0255 (18) | −0.0113 (15) | −0.0027 (15) | 0.0049 (15) |
N6 | 0.0292 (19) | 0.030 (2) | 0.033 (2) | −0.0058 (15) | −0.0048 (15) | 0.0046 (15) |
O1 | 0.0366 (17) | 0.0317 (16) | 0.0295 (16) | −0.0009 (13) | 0.0054 (13) | −0.0058 (13) |
O2 | 0.0262 (15) | 0.0413 (17) | 0.0291 (16) | −0.0158 (13) | −0.0043 (12) | 0.0012 (13) |
O3 | 0.0325 (16) | 0.0274 (16) | 0.0421 (17) | −0.0084 (13) | −0.0047 (13) | 0.0008 (13) |
O4 | 0.051 (2) | 0.044 (2) | 0.0422 (19) | −0.0095 (16) | 0.0046 (16) | 0.0004 (16) |
O5 | 0.051 (2) | 0.043 (2) | 0.044 (2) | −0.0147 (16) | −0.0035 (16) | 0.0007 (15) |
O6 | 0.0334 (17) | 0.0501 (19) | 0.0288 (16) | −0.0142 (14) | −0.0036 (13) | 0.0088 (14) |
O7 | 0.0225 (15) | 0.0445 (18) | 0.0319 (16) | −0.0092 (13) | −0.0038 (12) | 0.0099 (13) |
O8 | 0.0289 (16) | 0.0456 (18) | 0.0298 (16) | 0.0056 (13) | −0.0024 (13) | −0.0061 (13) |
O9 | 0.0270 (16) | 0.068 (2) | 0.0390 (19) | −0.0145 (15) | 0.0045 (14) | −0.0121 (16) |
O10 | 0.0278 (17) | 0.053 (2) | 0.0319 (17) | 0.0039 (14) | −0.0061 (13) | −0.0094 (14) |
O11 | 0.050 (2) | 0.059 (2) | 0.0338 (18) | −0.0275 (17) | 0.0051 (15) | −0.0112 (15) |
O12 | 0.107 (4) | 0.105 (4) | 0.064 (3) | −0.066 (3) | −0.025 (3) | 0.032 (3) |
O13 | 0.047 (2) | 0.0448 (19) | 0.055 (2) | −0.0160 (16) | −0.0053 (17) | 0.0049 (16) |
O14 | 0.0465 (19) | 0.0353 (18) | 0.0368 (18) | −0.0170 (15) | −0.0062 (15) | 0.0074 (14) |
P1 | 0.0245 (6) | 0.0286 (6) | 0.0306 (6) | −0.0040 (4) | −0.0002 (4) | −0.0023 (5) |
P2 | 0.0200 (5) | 0.0322 (6) | 0.0289 (6) | −0.0064 (4) | −0.0020 (4) | 0.0012 (5) |
P3 | 0.0204 (5) | 0.0292 (6) | 0.0252 (6) | −0.0043 (4) | −0.0008 (4) | 0.0011 (4) |
P4 | 0.0251 (6) | 0.0359 (7) | 0.0287 (6) | −0.0022 (5) | −0.0040 (5) | −0.0036 (5) |
P5 | 0.0275 (6) | 0.0365 (7) | 0.0288 (6) | −0.0111 (5) | 0.0000 (5) | −0.0009 (5) |
P6 | 0.0232 (5) | 0.0305 (6) | 0.0262 (6) | −0.0055 (4) | −0.0012 (4) | 0.0006 (4) |
C1—C6 | 1.364 (6) | C37—H37 | 0.9500 |
C1—C2 | 1.382 (6) | C38—H38 | 0.9500 |
C1—O1 | 1.384 (5) | C39—C44 | 1.367 (6) |
C2—C3 | 1.379 (7) | C39—O9 | 1.402 (5) |
C2—H2 | 0.9500 | C39—C40 | 1.378 (6) |
C3—C4 | 1.355 (8) | C40—C41 | 1.393 (7) |
C3—H3 | 0.9500 | C40—H40 | 0.9500 |
C4—C5 | 1.382 (8) | C41—C42 | 1.379 (8) |
C4—H4 | 0.9500 | C41—H41 | 0.9500 |
C5—C6 | 1.391 (7) | C42—C43 | 1.365 (8) |
C5—H5 | 0.9500 | C42—H42 | 0.9500 |
C6—H6 | 0.9500 | C43—C44 | 1.351 (7) |
C7—C8 | 1.363 (6) | C43—H43 | 0.9500 |
C7—C12 | 1.391 (6) | C44—H44 | 0.97 (5) |
C7—O2 | 1.405 (5) | C45—O10 | 1.452 (5) |
C8—C9 | 1.389 (7) | C45—C46 | 1.491 (6) |
C8—H8 | 0.9500 | C45—H45A | 0.9900 |
C9—C10 | 1.374 (7) | C45—H45B | 0.9900 |
C9—H9 | 0.9500 | C46—O11 | 1.399 (6) |
C10—C11 | 1.357 (7) | C46—H46A | 0.9900 |
C10—H10 | 0.9500 | C46—H46B | 0.9900 |
C11—C12 | 1.388 (6) | C47—O11 | 1.422 (7) |
C11—H11 | 0.9500 | C47—C48 | 1.497 (8) |
C12—H12 | 0.9500 | C47—H47A | 0.9900 |
C13—O3 | 1.432 (5) | C47—H47B | 0.9900 |
C13—C14 | 1.495 (6) | C48—O12 | 1.428 (7) |
C13—H13A | 0.9900 | C48—H48A | 0.9900 |
C13—H13B | 0.9900 | C48—H48B | 0.9900 |
C14—O4 | 1.415 (5) | C49—C50 | 1.5378 (11) |
C14—H14A | 0.9900 | C49—O12 | 1.394 (7) |
C14—H14B | 0.9900 | C49—H49A | 0.9900 |
C15—O4 | 1.419 (6) | C49—H49B | 0.9900 |
C15—C16 | 1.448 (8) | C50—O13 | 1.394 (7) |
C15—H15A | 0.9900 | C50—H50A | 0.9900 |
C15—H15B | 0.9900 | C50—H50B | 0.9900 |
C16—O5 | 1.426 (6) | C51—O13 | 1.421 (5) |
C16—H16A | 0.9900 | C51—C52 | 1.508 (7) |
C16—H16B | 0.9900 | C51—H51A | 0.9900 |
C17—O5 | 1.410 (6) | C51—H51B | 0.9900 |
C17—C18 | 1.467 (7) | C52—O14 | 1.444 (6) |
C17—H17A | 0.9900 | C52—H52A | 0.9900 |
C17—H17B | 0.9900 | C52—H52B | 0.9900 |
C18—O6 | 1.442 (5) | C53—C54 | 1.376 (6) |
C18—H18A | 0.9900 | C53—C58 | 1.392 (6) |
C18—H18B | 0.9900 | C53—P6 | 1.808 (4) |
C19—O6 | 1.413 (5) | C54—C55 | 1.376 (6) |
C19—C20 | 1.506 (6) | C54—H54 | 0.9500 |
C19—H19A | 0.9900 | C55—C56 | 1.376 (7) |
C19—H19B | 0.9900 | C55—H55 | 0.9500 |
C20—O7 | 1.462 (5) | C56—C57 | 1.381 (7) |
C20—H20A | 0.9900 | C56—H56 | 0.97 (5) |
C20—H20B | 0.9900 | C57—C58 | 1.370 (6) |
C21—C22 | 1.378 (6) | C57—H57 | 0.9500 |
C21—C26 | 1.401 (6) | C58—H58 | 0.9500 |
C21—P3 | 1.804 (4) | C59—C60 | 1.388 (6) |
C22—C23 | 1.387 (6) | C59—C64 | 1.388 (6) |
C22—H22 | 0.9500 | C59—P6 | 1.798 (4) |
C23—C24 | 1.390 (7) | C60—C61 | 1.390 (7) |
C23—H23 | 0.9500 | C60—H60 | 0.98 (4) |
C24—C25 | 1.382 (7) | C61—C62 | 1.366 (7) |
C24—H24 | 0.9500 | C61—H61 | 0.9500 |
C25—C26 | 1.383 (6) | C62—C63 | 1.390 (7) |
C25—H25 | 0.95 (4) | C62—H62 | 0.9500 |
C26—H26 | 0.9500 | C63—C64 | 1.384 (6) |
C27—C28 | 1.381 (6) | C63—H63 | 0.9500 |
C27—C32 | 1.398 (6) | C64—H64 | 0.9500 |
C27—P3 | 1.795 (4) | N1—P1 | 1.574 (4) |
C28—C29 | 1.394 (6) | N1—P2 | 1.585 (4) |
C28—H28 | 1.04 (3) | N2—P2 | 1.577 (3) |
C29—C30 | 1.368 (7) | N2—P3 | 1.602 (3) |
C29—H29 | 0.9500 | N3—P1 | 1.585 (3) |
C30—C31 | 1.385 (7) | N3—P3 | 1.605 (3) |
C30—H30 | 0.9500 | N4—P5 | 1.569 (3) |
C31—C32 | 1.399 (6) | N4—P4 | 1.584 (4) |
C31—H31 | 0.9500 | N5—P5 | 1.575 (3) |
C32—H32 | 0.9500 | N5—P6 | 1.602 (3) |
C33—C38 | 1.361 (6) | N6—P4 | 1.574 (4) |
C33—C34 | 1.379 (6) | N6—P6 | 1.606 (3) |
C33—O8 | 1.402 (5) | O1—P1 | 1.602 (3) |
C34—C35 | 1.407 (7) | O2—P2 | 1.591 (3) |
C34—H34 | 0.9500 | O3—P1 | 1.576 (3) |
C35—C36 | 1.377 (8) | O7—P2 | 1.578 (3) |
C35—H35 | 1.15 (5) | O8—P4 | 1.595 (3) |
C36—C37 | 1.362 (7) | O9—P5 | 1.596 (3) |
C36—H36 | 0.9500 | O10—P4 | 1.580 (3) |
C37—C38 | 1.400 (7) | O14—P5 | 1.565 (3) |
C6—C1—C2 | 120.5 (4) | C43—C42—H42 | 120.5 |
C6—C1—O1 | 120.6 (4) | C41—C42—H42 | 120.5 |
C2—C1—O1 | 118.8 (4) | C44—C43—C42 | 121.5 (5) |
C1—C2—C3 | 119.9 (5) | C44—C43—H43 | 119.2 |
C1—C2—H2 | 120.0 | C42—C43—H43 | 119.2 |
C3—C2—H2 | 120.0 | C43—C44—C39 | 119.6 (5) |
C4—C3—C2 | 119.9 (5) | C43—C44—H44 | 121 (3) |
C4—C3—H3 | 120.1 | C39—C44—H44 | 120 (3) |
C2—C3—H3 | 120.1 | O10—C45—C46 | 107.4 (3) |
C3—C4—C5 | 120.6 (5) | O10—C45—H45A | 110.2 |
C3—C4—H4 | 119.7 | C46—C45—H45A | 110.2 |
C5—C4—H4 | 119.7 | O10—C45—H45B | 110.2 |
C4—C5—C6 | 119.8 (5) | C46—C45—H45B | 110.2 |
C4—C5—H5 | 120.1 | H45A—C45—H45B | 108.5 |
C6—C5—H5 | 120.1 | O11—C46—C45 | 107.7 (4) |
C1—C6—C5 | 119.2 (5) | O11—C46—H46A | 110.2 |
C1—C6—H6 | 120.4 | C45—C46—H46A | 110.2 |
C5—C6—H6 | 120.4 | O11—C46—H46B | 110.2 |
C8—C7—C12 | 121.5 (4) | C45—C46—H46B | 110.2 |
C8—C7—O2 | 118.0 (4) | H46A—C46—H46B | 108.5 |
C12—C7—O2 | 120.5 (4) | O11—C47—C48 | 108.0 (5) |
C7—C8—C9 | 118.9 (4) | O11—C47—H47A | 110.1 |
C7—C8—H8 | 120.6 | C48—C47—H47A | 110.1 |
C9—C8—H8 | 120.6 | O11—C47—H47B | 110.1 |
C10—C9—C8 | 121.0 (5) | C48—C47—H47B | 110.1 |
C10—C9—H9 | 119.5 | H47A—C47—H47B | 108.4 |
C8—C9—H9 | 119.5 | O12—C48—C47 | 106.7 (5) |
C11—C10—C9 | 118.8 (5) | O12—C48—H48A | 110.4 |
C11—C10—H10 | 120.6 | C47—C48—H48A | 110.4 |
C9—C10—H10 | 120.6 | O12—C48—H48B | 110.4 |
C10—C11—C12 | 122.3 (4) | C47—C48—H48B | 110.4 |
C10—C11—H11 | 118.9 | H48A—C48—H48B | 108.6 |
C12—C11—H11 | 118.9 | C50—C49—O12 | 109.8 (5) |
C7—C12—C11 | 117.4 (4) | C50—C49—H49A | 109.7 |
C7—C12—H12 | 121.3 | O12—C49—H49A | 109.7 |
C11—C12—H12 | 121.3 | C50—C49—H49B | 109.7 |
O3—C13—C14 | 108.3 (4) | O12—C49—H49B | 109.7 |
O3—C13—H13A | 110.0 | H49A—C49—H49B | 108.2 |
C14—C13—H13A | 110.0 | O13—C50—C49 | 121.0 (5) |
O3—C13—H13B | 110.0 | O13—C50—H50A | 107.1 |
C14—C13—H13B | 110.0 | C49—C50—H50A | 107.1 |
H13A—C13—H13B | 108.4 | O13—C50—H50B | 107.1 |
O4—C14—C13 | 108.7 (4) | C49—C50—H50B | 107.1 |
O4—C14—H14A | 110.0 | H50A—C50—H50B | 106.8 |
C13—C14—H14A | 110.0 | O13—C51—C52 | 108.7 (4) |
O4—C14—H14B | 110.0 | O13—C51—H51A | 110.0 |
C13—C14—H14B | 110.0 | C52—C51—H51A | 110.0 |
H14A—C14—H14B | 108.3 | O13—C51—H51B | 110.0 |
O4—C15—C16 | 110.5 (4) | C52—C51—H51B | 110.0 |
O4—C15—H15A | 109.6 | H51A—C51—H51B | 108.3 |
C16—C15—H15A | 109.6 | O14—C52—C51 | 112.7 (4) |
O4—C15—H15B | 109.6 | O14—C52—H52A | 109.1 |
C16—C15—H15B | 109.6 | C51—C52—H52A | 109.1 |
H15A—C15—H15B | 108.1 | O14—C52—H52B | 109.1 |
O5—C16—C15 | 110.1 (5) | C51—C52—H52B | 109.1 |
O5—C16—H16A | 109.6 | H52A—C52—H52B | 107.8 |
C15—C16—H16A | 109.6 | C54—C53—C58 | 118.6 (4) |
O5—C16—H16B | 109.6 | C54—C53—P6 | 122.2 (3) |
C15—C16—H16B | 109.6 | C58—C53—P6 | 119.2 (3) |
H16A—C16—H16B | 108.2 | C53—C54—C55 | 121.0 (4) |
O5—C17—C18 | 108.7 (4) | C53—C54—H54 | 119.5 |
O5—C17—H17A | 109.9 | C55—C54—H54 | 119.5 |
C18—C17—H17A | 109.9 | C56—C55—C54 | 120.3 (4) |
O5—C17—H17B | 109.9 | C56—C55—H55 | 119.8 |
C18—C17—H17B | 109.9 | C54—C55—H55 | 119.8 |
H17A—C17—H17B | 108.3 | C55—C56—C57 | 118.9 (4) |
O6—C18—C17 | 112.9 (4) | C55—C56—H56 | 123 (3) |
O6—C18—H18A | 109.0 | C57—C56—H56 | 118 (3) |
C17—C18—H18A | 109.0 | C58—C57—C56 | 121.1 (4) |
O6—C18—H18B | 109.0 | C58—C57—H57 | 119.5 |
C17—C18—H18B | 109.0 | C56—C57—H57 | 119.5 |
H18A—C18—H18B | 107.8 | C57—C58—C53 | 120.1 (4) |
O6—C19—C20 | 111.4 (4) | C57—C58—H58 | 120.0 |
O6—C19—H19A | 109.3 | C53—C58—H58 | 120.0 |
C20—C19—H19A | 109.3 | C60—C59—C64 | 119.5 (4) |
O6—C19—H19B | 109.3 | C60—C59—P6 | 119.6 (3) |
C20—C19—H19B | 109.3 | C64—C59—P6 | 120.9 (3) |
H19A—C19—H19B | 108.0 | C59—C60—C61 | 120.4 (4) |
O7—C20—C19 | 108.4 (4) | C59—C60—H60 | 118 (2) |
O7—C20—H20A | 110.0 | C61—C60—H60 | 121 (2) |
C19—C20—H20A | 110.0 | C62—C61—C60 | 119.7 (5) |
O7—C20—H20B | 110.0 | C62—C61—H61 | 120.1 |
C19—C20—H20B | 110.0 | C60—C61—H61 | 120.1 |
H20A—C20—H20B | 108.4 | C61—C62—C63 | 120.5 (4) |
C22—C21—C26 | 118.9 (4) | C61—C62—H62 | 119.7 |
C22—C21—P3 | 120.3 (3) | C63—C62—H62 | 119.7 |
C26—C21—P3 | 120.7 (3) | C64—C63—C62 | 120.0 (4) |
C21—C22—C23 | 120.6 (4) | C64—C63—H63 | 120.0 |
C21—C22—H22 | 119.7 | C62—C63—H63 | 120.0 |
C23—C22—H22 | 119.7 | C63—C64—C59 | 119.8 (4) |
C22—C23—C24 | 120.5 (4) | C63—C64—H64 | 120.1 |
C22—C23—H23 | 119.7 | C59—C64—H64 | 120.1 |
C24—C23—H23 | 119.7 | P1—N1—P2 | 122.5 (2) |
C25—C24—C23 | 119.0 (4) | P2—N2—P3 | 122.9 (2) |
C25—C24—H24 | 120.5 | P1—N3—P3 | 120.8 (2) |
C23—C24—H24 | 120.5 | P5—N4—P4 | 122.3 (2) |
C26—C25—C24 | 120.7 (5) | P5—N5—P6 | 120.4 (2) |
C26—C25—H25 | 121 (2) | P4—N6—P6 | 122.5 (2) |
C24—C25—H25 | 118 (2) | C1—O1—P1 | 122.2 (3) |
C25—C26—C21 | 120.3 (5) | C7—O2—P2 | 122.7 (2) |
C25—C26—H26 | 119.9 | C13—O3—P1 | 120.9 (3) |
C21—C26—H26 | 119.9 | C15—O4—C14 | 113.2 (4) |
C28—C27—C32 | 119.5 (4) | C17—O5—C16 | 110.7 (4) |
C28—C27—P3 | 120.0 (3) | C19—O6—C18 | 114.9 (3) |
C32—C27—P3 | 120.5 (3) | C20—O7—P2 | 118.7 (3) |
C27—C28—C29 | 119.9 (5) | C33—O8—P4 | 121.0 (2) |
C27—C28—H28 | 124.3 (17) | C39—O9—P5 | 122.5 (3) |
C29—C28—H28 | 115.7 (17) | C45—O10—P4 | 118.8 (2) |
C30—C29—C28 | 120.6 (5) | C46—O11—C47 | 112.8 (4) |
C30—C29—H29 | 119.7 | C49—O12—C48 | 117.5 (5) |
C28—C29—H29 | 119.7 | C50—O13—C51 | 117.4 (4) |
C31—C30—C29 | 120.5 (4) | C52—O14—P5 | 118.3 (3) |
C31—C30—H30 | 119.7 | O3—P1—N1 | 105.96 (17) |
C29—C30—H30 | 119.7 | O3—P1—N3 | 112.27 (17) |
C30—C31—C32 | 119.2 (5) | N1—P1—N3 | 118.50 (18) |
C30—C31—H31 | 120.4 | O3—P1—O1 | 98.76 (16) |
C32—C31—H31 | 120.4 | N1—P1—O1 | 110.71 (18) |
C31—C32—C27 | 120.1 (4) | N3—P1—O1 | 108.84 (16) |
C31—C32—H32 | 119.9 | O7—P2—N1 | 112.01 (18) |
C27—C32—H32 | 119.9 | O7—P2—N2 | 110.43 (17) |
C38—C33—C34 | 122.7 (4) | N1—P2—N2 | 116.76 (18) |
C38—C33—O8 | 118.9 (4) | O7—P2—O2 | 94.59 (15) |
C34—C33—O8 | 118.3 (4) | N1—P2—O2 | 109.31 (17) |
C33—C34—C35 | 117.4 (5) | N2—P2—O2 | 111.56 (17) |
C33—C34—H34 | 121.3 | N3—P3—N2 | 117.30 (17) |
C35—C34—H34 | 121.3 | N3—P3—C27 | 108.53 (19) |
C36—C35—C34 | 120.7 (5) | N2—P3—C27 | 108.41 (19) |
C36—C35—H35 | 119 (2) | N3—P3—C21 | 107.34 (19) |
C34—C35—H35 | 120 (2) | N2—P3—C21 | 108.66 (18) |
C37—C36—C35 | 120.0 (5) | C27—P3—C21 | 106.04 (18) |
C37—C36—H36 | 120.0 | O10—P4—N6 | 110.86 (18) |
C35—C36—H36 | 120.0 | O10—P4—N4 | 111.54 (19) |
C36—C37—C38 | 120.6 (5) | N6—P4—N4 | 116.97 (18) |
C36—C37—H37 | 119.7 | O10—P4—O8 | 94.06 (15) |
C38—C37—H37 | 119.7 | N6—P4—O8 | 111.30 (18) |
C33—C38—C37 | 118.5 (5) | N4—P4—O8 | 109.79 (18) |
C33—C38—H38 | 120.7 | O14—P5—N4 | 110.20 (18) |
C37—C38—H38 | 120.7 | O14—P5—N5 | 109.64 (18) |
C44—C39—O9 | 122.3 (4) | N4—P5—N5 | 117.69 (19) |
C44—C39—C40 | 121.2 (4) | O14—P5—O9 | 100.10 (18) |
O9—C39—C40 | 116.4 (4) | N4—P5—O9 | 106.06 (18) |
C41—C40—C39 | 118.0 (4) | N5—P5—O9 | 111.69 (18) |
C41—C40—H40 | 121.0 | N5—P6—N6 | 117.01 (18) |
C39—C40—H40 | 121.0 | N5—P6—C59 | 109.39 (18) |
C42—C41—C40 | 120.6 (5) | N6—P6—C59 | 107.65 (19) |
C42—C41—H41 | 119.7 | N5—P6—C53 | 109.10 (18) |
C40—C41—H41 | 119.7 | N6—P6—C53 | 108.32 (18) |
C43—C42—C41 | 119.0 (5) | C59—P6—C53 | 104.67 (19) |
C6—C1—C2—C3 | 2.0 (7) | C48—C47—O11—C46 | 173.0 (5) |
O1—C1—C2—C3 | 179.5 (4) | C50—C49—O12—C48 | −91.5 (7) |
C1—C2—C3—C4 | −0.7 (8) | C47—C48—O12—C49 | 173.3 (5) |
C2—C3—C4—C5 | −0.5 (8) | C49—C50—O13—C51 | 60.8 (7) |
C3—C4—C5—C6 | 0.6 (8) | C52—C51—O13—C50 | 166.8 (4) |
C2—C1—C6—C5 | −1.9 (7) | C51—C52—O14—P5 | −95.0 (4) |
O1—C1—C6—C5 | −179.4 (4) | C13—O3—P1—N1 | 179.2 (3) |
C4—C5—C6—C1 | 0.7 (8) | C13—O3—P1—N3 | −50.0 (3) |
C12—C7—C8—C9 | −1.6 (7) | C13—O3—P1—O1 | 64.6 (3) |
O2—C7—C8—C9 | 176.4 (4) | P2—N1—P1—O3 | 114.2 (3) |
C7—C8—C9—C10 | 2.8 (8) | P2—N1—P1—N3 | −12.9 (3) |
C8—C9—C10—C11 | −2.0 (8) | P2—N1—P1—O1 | −139.7 (2) |
C9—C10—C11—C12 | 0.1 (8) | P3—N3—P1—O3 | −117.6 (2) |
C8—C7—C12—C11 | −0.2 (7) | P3—N3—P1—N1 | 6.5 (3) |
O2—C7—C12—C11 | −178.2 (4) | P3—N3—P1—O1 | 134.2 (2) |
C10—C11—C12—C7 | 1.0 (7) | C1—O1—P1—O3 | −150.1 (3) |
O3—C13—C14—O4 | −69.7 (5) | C1—O1—P1—N1 | 99.0 (3) |
O4—C15—C16—O5 | 69.1 (6) | C1—O1—P1—N3 | −32.9 (4) |
O5—C17—C18—O6 | 70.3 (5) | C20—O7—P2—N1 | 81.6 (3) |
O6—C19—C20—O7 | 174.5 (3) | C20—O7—P2—N2 | −50.4 (3) |
C26—C21—C22—C23 | −1.3 (6) | C20—O7—P2—O2 | −165.4 (3) |
P3—C21—C22—C23 | −178.6 (3) | P1—N1—P2—O7 | −118.1 (2) |
C21—C22—C23—C24 | 0.7 (7) | P1—N1—P2—N2 | 10.6 (3) |
C22—C23—C24—C25 | 0.3 (7) | P1—N1—P2—O2 | 138.4 (2) |
C23—C24—C25—C26 | −0.7 (7) | P3—N2—P2—O7 | 127.4 (2) |
C24—C25—C26—C21 | 0.1 (7) | P3—N2—P2—N1 | −2.0 (3) |
C22—C21—C26—C25 | 1.0 (6) | P3—N2—P2—O2 | −128.7 (2) |
P3—C21—C26—C25 | 178.2 (3) | C7—O2—P2—O7 | −172.5 (3) |
C32—C27—C28—C29 | 2.0 (6) | C7—O2—P2—N1 | −57.2 (3) |
P3—C27—C28—C29 | −177.9 (3) | C7—O2—P2—N2 | 73.4 (3) |
C27—C28—C29—C30 | −0.1 (7) | P1—N3—P3—N2 | 1.4 (3) |
C28—C29—C30—C31 | −1.4 (7) | P1—N3—P3—C27 | −121.8 (2) |
C29—C30—C31—C32 | 1.1 (7) | P1—N3—P3—C21 | 124.0 (2) |
C30—C31—C32—C27 | 0.8 (7) | P2—N2—P3—N3 | −3.7 (3) |
C28—C27—C32—C31 | −2.3 (6) | P2—N2—P3—C27 | 119.6 (2) |
P3—C27—C32—C31 | 177.6 (3) | P2—N2—P3—C21 | −125.6 (2) |
C38—C33—C34—C35 | −1.1 (7) | C28—C27—P3—N3 | −11.4 (4) |
O8—C33—C34—C35 | 174.8 (4) | C32—C27—P3—N3 | 168.7 (3) |
C33—C34—C35—C36 | 0.8 (7) | C28—C27—P3—N2 | −139.9 (3) |
C34—C35—C36—C37 | −0.1 (7) | C32—C27—P3—N2 | 40.3 (4) |
C35—C36—C37—C38 | −0.5 (7) | C28—C27—P3—C21 | 103.6 (4) |
C34—C33—C38—C37 | 0.5 (6) | C32—C27—P3—C21 | −76.3 (4) |
O8—C33—C38—C37 | −175.4 (3) | C22—C21—P3—N3 | −15.3 (4) |
C36—C37—C38—C33 | 0.3 (7) | C26—C21—P3—N3 | 167.5 (3) |
C44—C39—C40—C41 | 0.8 (7) | C22—C21—P3—N2 | 112.5 (3) |
O9—C39—C40—C41 | 179.5 (4) | C26—C21—P3—N2 | −64.7 (3) |
C39—C40—C41—C42 | 0.5 (7) | C22—C21—P3—C27 | −131.2 (3) |
C40—C41—C42—C43 | −0.7 (8) | C26—C21—P3—C27 | 51.6 (4) |
C41—C42—C43—C44 | −0.3 (8) | C45—O10—P4—N6 | 54.8 (4) |
C42—C43—C44—C39 | 1.6 (7) | C45—O10—P4—N4 | −77.5 (3) |
O9—C39—C44—C43 | 179.6 (4) | C45—O10—P4—O8 | 169.4 (3) |
C40—C39—C44—C43 | −1.8 (7) | P6—N6—P4—O10 | −125.7 (2) |
O10—C45—C46—O11 | −67.7 (4) | P6—N6—P4—N4 | 3.7 (3) |
O11—C47—C48—O12 | −68.9 (7) | P6—N6—P4—O8 | 131.0 (2) |
O12—C49—C50—O13 | −67.9 (8) | P5—N4—P4—O10 | 136.0 (2) |
O13—C51—C52—O14 | −71.4 (5) | P5—N4—P4—N6 | 7.0 (3) |
C58—C53—C54—C55 | 0.8 (6) | P5—N4—P4—O8 | −121.1 (2) |
P6—C53—C54—C55 | −177.8 (3) | C33—O8—P4—O10 | 168.8 (3) |
C53—C54—C55—C56 | 0.5 (7) | C33—O8—P4—N6 | −76.9 (4) |
C54—C55—C56—C57 | −1.3 (7) | C33—O8—P4—N4 | 54.2 (4) |
C55—C56—C57—C58 | 0.9 (7) | C52—O14—P5—N4 | 69.9 (3) |
C56—C57—C58—C53 | 0.3 (7) | C52—O14—P5—N5 | −61.1 (3) |
C54—C53—C58—C57 | −1.2 (6) | C52—O14—P5—O9 | −178.6 (3) |
P6—C53—C58—C57 | 177.4 (3) | P4—N4—P5—O14 | −145.8 (2) |
C64—C59—C60—C61 | 0.7 (7) | P4—N4—P5—N5 | −19.1 (3) |
P6—C59—C60—C61 | −179.3 (4) | P4—N4—P5—O9 | 106.7 (3) |
C59—C60—C61—C62 | 0.1 (7) | P6—N5—P5—O14 | 147.8 (2) |
C60—C61—C62—C63 | −1.5 (7) | P6—N5—P5—N4 | 20.8 (3) |
C61—C62—C63—C64 | 2.1 (7) | P6—N5—P5—O9 | −102.2 (3) |
C62—C63—C64—C59 | −1.3 (7) | C39—O9—P5—O14 | 92.9 (3) |
C60—C59—C64—C63 | −0.1 (6) | C39—O9—P5—N4 | −152.5 (3) |
P6—C59—C64—C63 | 179.9 (3) | C39—O9—P5—N5 | −23.1 (4) |
C6—C1—O1—P1 | −72.7 (5) | P5—N5—P6—N6 | −10.7 (3) |
C2—C1—O1—P1 | 109.8 (4) | P5—N5—P6—C59 | 112.0 (3) |
C8—C7—O2—P2 | 116.6 (4) | P5—N5—P6—C53 | −134.0 (2) |
C12—C7—O2—P2 | −65.4 (5) | P4—N6—P6—N5 | −1.8 (3) |
C14—C13—O3—P1 | 156.1 (3) | P4—N6—P6—C59 | −125.4 (3) |
C16—C15—O4—C14 | −179.3 (4) | P4—N6—P6—C53 | 121.9 (3) |
C13—C14—O4—C15 | 143.1 (4) | C60—C59—P6—N5 | −159.0 (3) |
C18—C17—O5—C16 | 173.7 (4) | C64—C59—P6—N5 | 21.0 (4) |
C15—C16—O5—C17 | −178.9 (4) | C60—C59—P6—N6 | −30.9 (4) |
C20—C19—O6—C18 | 83.6 (4) | C64—C59—P6—N6 | 149.1 (3) |
C17—C18—O6—C19 | −123.4 (4) | C60—C59—P6—C53 | 84.2 (4) |
C19—C20—O7—P2 | 104.7 (3) | C64—C59—P6—C53 | −95.8 (4) |
C38—C33—O8—P4 | −102.3 (4) | C54—C53—P6—N5 | −12.8 (4) |
C34—C33—O8—P4 | 81.7 (4) | C58—C53—P6—N5 | 168.6 (3) |
C44—C39—O9—P5 | −62.6 (5) | C54—C53—P6—N6 | −141.2 (4) |
C40—C39—O9—P5 | 118.7 (4) | C58—C53—P6—N6 | 40.3 (4) |
C46—C45—O10—P4 | 152.5 (3) | C54—C53—P6—C59 | 104.1 (4) |
C45—C46—O11—C47 | −169.7 (4) | C58—C53—P6—C59 | −74.4 (4) |
C22H32N3O7P3 | F(000) = 1144 |
Mr = 543.42 | Dx = 1.387 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8293 (2) Å | Cell parameters from 8163 reflections |
b = 10.3312 (2) Å | θ = 2.9–27.5° |
c = 21.6318 (5) Å | µ = 0.28 mm−1 |
β = 100.203 (1)° | T = 293 K |
V = 2601.84 (9) Å3 | Plate, colourless |
Z = 4 | 0.26 × 0.20 × 0.07 mm |
Nonius KappaCCD diffractometer | 5841 independent reflections |
Radiation source: Nonius FR591 rotating anode | 4160 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ & ω scans | h = −14→15 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −12→13 |
Tmin = 0.932, Tmax = 0.981 | l = −27→28 |
18814 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-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 reflections | Δρmax = 0.46 e Å−3 |
319 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0061 (11) |
C22H32N3O7P3 | V = 2601.84 (9) Å3 |
Mr = 543.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8293 (2) Å | µ = 0.28 mm−1 |
b = 10.3312 (2) Å | T = 293 K |
c = 21.6318 (5) Å | 0.26 × 0.20 × 0.07 mm |
β = 100.203 (1)° |
Nonius KappaCCD diffractometer | 5841 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 4160 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.981 | Rint = 0.038 |
18814 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.46 e Å−3 |
5841 reflections | Δρmin = −0.31 e Å−3 |
319 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3021 (3) | 0.9455 (3) | 0.21276 (16) | 0.0714 (9) | |
H1A | 0.2981 | 0.8961 | 0.1749 | 0.107* | |
H1B | 0.2902 | 0.8893 | 0.2464 | 0.107* | |
H1C | 0.3763 | 0.9855 | 0.2231 | 0.107* | |
C2 | 0.3682 (4) | 0.8899 (3) | 0.03540 (18) | 0.0891 (12) | |
H2A | 0.4067 | 0.9156 | 0.0764 | 0.134* | |
H2B | 0.4220 | 0.8485 | 0.0134 | 0.134* | |
H2C | 0.3073 | 0.8307 | 0.0394 | 0.134* | |
C3 | −0.0040 (2) | 1.1653 (3) | 0.14186 (16) | 0.0641 (8) | |
H3A | −0.0143 | 1.1051 | 0.1748 | 0.077* | |
H3B | −0.0081 | 1.1172 | 0.1030 | 0.077* | |
C4 | −0.0954 (3) | 1.2645 (4) | 0.1345 (2) | 0.0875 (12) | |
H4A | −0.1695 | 1.2237 | 0.1337 | 0.105* | |
H4B | −0.0819 | 1.3243 | 0.1696 | 0.105* | |
C5 | −0.1946 (4) | 1.4066 (5) | 0.0588 (3) | 0.1176 (19) | |
H5A | −0.2036 | 1.4676 | 0.0916 | 0.141* | |
H5B | −0.2615 | 1.3506 | 0.0515 | 0.141* | |
C6 | −0.1849 (4) | 1.4771 (5) | 0.0004 (3) | 0.127 (2) | |
H6A | −0.2529 | 1.5297 | −0.0125 | 0.152* | |
H6B | −0.1187 | 1.5341 | 0.0080 | 0.152* | |
C7 | −0.1367 (4) | 1.4515 (5) | −0.0980 (3) | 0.123 (2) | |
H7A | −0.0759 | 1.5125 | −0.0827 | 0.148* | |
H7B | −0.2002 | 1.4988 | −0.1224 | 0.148* | |
C8 | −0.0949 (4) | 1.3538 (6) | −0.1374 (2) | 0.125 (2) | |
H8A | −0.1514 | 1.2851 | −0.1454 | 0.150* | |
H8B | −0.0892 | 1.3931 | −0.1774 | 0.150* | |
C9 | 0.0084 (3) | 1.2023 (4) | −0.06467 (19) | 0.0818 (10) | |
H9A | −0.0580 | 1.1472 | −0.0775 | 0.098* | |
H9B | 0.0001 | 1.2446 | −0.0257 | 0.098* | |
C10 | 0.1109 (3) | 1.1247 (3) | −0.05482 (17) | 0.0753 (9) | |
H10A | 0.1258 | 1.0950 | −0.0952 | 0.090* | |
H10B | 0.0985 | 1.0490 | −0.0303 | 0.090* | |
C11 | 0.5464 (2) | 1.1787 (2) | 0.17236 (12) | 0.0447 (6) | |
C12 | 0.5809 (3) | 1.2011 (3) | 0.23638 (15) | 0.0684 (8) | |
H12 | 0.5436 | 1.2639 | 0.2562 | 0.082* | |
C13 | 0.6699 (3) | 1.1310 (4) | 0.27077 (19) | 0.0860 (11) | |
H13 | 0.6922 | 1.1469 | 0.3135 | 0.103* | |
C14 | 0.7255 (3) | 1.0382 (4) | 0.2423 (2) | 0.0840 (11) | |
H14 | 0.7850 | 0.9907 | 0.2657 | 0.101* | |
C15 | 0.6930 (3) | 1.0158 (3) | 0.1795 (2) | 0.0780 (10) | |
H15 | 0.7308 | 0.9526 | 0.1603 | 0.094* | |
C16 | 0.6036 (2) | 1.0867 (3) | 0.14346 (15) | 0.0596 (7) | |
H16 | 0.5831 | 1.0717 | 0.1005 | 0.072* | |
C17 | 0.4622 (2) | 1.4311 (2) | 0.13249 (11) | 0.0423 (5) | |
C18 | 0.4390 (2) | 1.5125 (3) | 0.17955 (14) | 0.0555 (7) | |
H18 | 0.4000 | 1.4810 | 0.2101 | 0.067* | |
C19 | 0.4737 (3) | 1.6402 (3) | 0.18127 (17) | 0.0706 (9) | |
H19 | 0.4577 | 1.6944 | 0.2129 | 0.085* | |
C20 | 0.5314 (3) | 1.6870 (3) | 0.13685 (18) | 0.0734 (9) | |
H20 | 0.5546 | 1.7731 | 0.1385 | 0.088* | |
C21 | 0.5554 (3) | 1.6088 (3) | 0.09003 (17) | 0.0726 (9) | |
H21 | 0.5952 | 1.6415 | 0.0600 | 0.087* | |
C22 | 0.5202 (2) | 1.4797 (3) | 0.08718 (14) | 0.0572 (7) | |
H22 | 0.5356 | 1.4265 | 0.0550 | 0.069* | |
N1 | 0.2112 (2) | 1.0827 (2) | 0.08603 (10) | 0.0485 (5) | |
N2 | 0.39368 (18) | 1.2137 (2) | 0.05984 (9) | 0.0462 (5) | |
N3 | 0.32212 (17) | 1.2480 (2) | 0.17228 (9) | 0.0431 (5) | |
O1 | 0.21493 (17) | 1.04370 (18) | 0.20364 (8) | 0.0562 (5) | |
O2 | 0.3218 (2) | 1.00054 (18) | 0.00146 (9) | 0.0650 (6) | |
O4 | −0.0948 (2) | 1.3320 (3) | 0.07766 (15) | 0.0915 (8) | |
O5 | −0.1734 (2) | 1.3896 (3) | −0.04690 (16) | 0.0980 (9) | |
O6 | 0.0136 (2) | 1.2976 (3) | −0.11189 (13) | 0.0977 (9) | |
O7 | 0.21093 (17) | 1.19435 (19) | −0.02255 (8) | 0.0565 (5) | |
O3 | 0.10657 (14) | 1.22816 (17) | 0.15776 (9) | 0.0500 (4) | |
P1 | 0.21922 (5) | 1.15158 (6) | 0.15205 (3) | 0.04093 (18) | |
P2 | 0.28683 (6) | 1.12480 (6) | 0.03577 (3) | 0.04374 (19) | |
P3 | 0.42139 (5) | 1.26306 (6) | 0.13107 (3) | 0.03865 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.093 (2) | 0.0566 (17) | 0.0664 (19) | 0.0088 (17) | 0.0186 (17) | 0.0190 (15) |
C2 | 0.138 (4) | 0.0580 (19) | 0.078 (2) | 0.028 (2) | 0.038 (2) | 0.0070 (17) |
C3 | 0.0464 (15) | 0.0665 (19) | 0.079 (2) | −0.0168 (14) | 0.0105 (14) | −0.0009 (16) |
C4 | 0.0464 (18) | 0.104 (3) | 0.116 (3) | −0.0064 (18) | 0.0236 (19) | −0.005 (3) |
C5 | 0.069 (2) | 0.120 (4) | 0.148 (4) | 0.045 (3) | −0.021 (3) | −0.047 (4) |
C6 | 0.105 (4) | 0.084 (3) | 0.163 (5) | 0.033 (3) | −0.050 (4) | −0.024 (3) |
C7 | 0.068 (2) | 0.104 (3) | 0.190 (6) | 0.010 (2) | 0.000 (3) | 0.069 (4) |
C8 | 0.080 (3) | 0.182 (6) | 0.104 (4) | 0.026 (3) | −0.007 (3) | 0.062 (4) |
C9 | 0.068 (2) | 0.081 (2) | 0.094 (3) | −0.0098 (19) | 0.0084 (19) | 0.011 (2) |
C10 | 0.075 (2) | 0.076 (2) | 0.066 (2) | −0.0119 (18) | −0.0112 (17) | −0.0049 (17) |
C11 | 0.0417 (12) | 0.0418 (13) | 0.0516 (14) | −0.0029 (11) | 0.0107 (11) | 0.0053 (11) |
C12 | 0.0679 (19) | 0.0704 (19) | 0.0599 (18) | 0.0136 (16) | −0.0081 (15) | −0.0015 (15) |
C13 | 0.079 (2) | 0.091 (3) | 0.076 (2) | 0.010 (2) | −0.0186 (19) | 0.010 (2) |
C14 | 0.0554 (19) | 0.075 (2) | 0.114 (3) | 0.0091 (17) | −0.004 (2) | 0.025 (2) |
C15 | 0.0581 (18) | 0.0576 (19) | 0.123 (3) | 0.0151 (16) | 0.029 (2) | 0.007 (2) |
C16 | 0.0533 (16) | 0.0562 (16) | 0.0727 (19) | 0.0017 (13) | 0.0203 (14) | −0.0010 (14) |
C17 | 0.0396 (12) | 0.0427 (13) | 0.0442 (13) | 0.0020 (10) | 0.0060 (10) | 0.0020 (10) |
C18 | 0.0610 (17) | 0.0497 (15) | 0.0563 (16) | 0.0018 (13) | 0.0112 (13) | −0.0051 (12) |
C19 | 0.087 (2) | 0.0439 (16) | 0.077 (2) | 0.0054 (15) | 0.0024 (18) | −0.0079 (14) |
C20 | 0.080 (2) | 0.0395 (15) | 0.092 (3) | −0.0055 (15) | −0.0072 (19) | 0.0068 (16) |
C21 | 0.072 (2) | 0.0608 (19) | 0.086 (2) | −0.0116 (16) | 0.0170 (17) | 0.0233 (17) |
C22 | 0.0599 (17) | 0.0519 (15) | 0.0631 (17) | −0.0024 (13) | 0.0198 (14) | 0.0052 (13) |
N1 | 0.0601 (13) | 0.0423 (11) | 0.0450 (12) | −0.0118 (10) | 0.0141 (10) | −0.0056 (9) |
N2 | 0.0484 (12) | 0.0540 (12) | 0.0380 (11) | −0.0049 (10) | 0.0129 (9) | −0.0030 (9) |
N3 | 0.0423 (11) | 0.0517 (12) | 0.0370 (10) | −0.0070 (9) | 0.0119 (8) | −0.0064 (9) |
O1 | 0.0709 (12) | 0.0512 (10) | 0.0519 (11) | −0.0029 (9) | 0.0252 (9) | 0.0110 (9) |
O2 | 0.0995 (16) | 0.0461 (10) | 0.0537 (11) | 0.0075 (11) | 0.0256 (11) | −0.0072 (9) |
O4 | 0.0530 (13) | 0.0855 (17) | 0.132 (2) | 0.0085 (12) | 0.0061 (14) | 0.0093 (16) |
O5 | 0.0861 (18) | 0.0715 (16) | 0.132 (2) | 0.0000 (14) | 0.0078 (17) | 0.0082 (17) |
O6 | 0.0673 (15) | 0.130 (2) | 0.0927 (19) | 0.0112 (15) | 0.0065 (13) | 0.0477 (17) |
O7 | 0.0669 (12) | 0.0533 (11) | 0.0442 (10) | −0.0085 (9) | −0.0042 (9) | 0.0044 (8) |
O3 | 0.0386 (9) | 0.0487 (10) | 0.0639 (11) | −0.0058 (8) | 0.0124 (8) | −0.0102 (8) |
P1 | 0.0455 (4) | 0.0388 (3) | 0.0404 (3) | −0.0047 (3) | 0.0129 (3) | −0.0006 (2) |
P2 | 0.0569 (4) | 0.0390 (3) | 0.0360 (3) | −0.0024 (3) | 0.0100 (3) | −0.0030 (2) |
P3 | 0.0391 (3) | 0.0416 (3) | 0.0364 (3) | −0.0016 (3) | 0.0097 (2) | −0.0011 (2) |
C1—O1 | 1.435 (4) | C10—H10B | 0.9700 |
C1—H1A | 0.9600 | C11—C16 | 1.379 (4) |
C1—H1B | 0.9600 | C11—C12 | 1.392 (4) |
C1—H1C | 0.9600 | C11—P3 | 1.810 (3) |
C2—O2 | 1.415 (4) | C12—C13 | 1.382 (5) |
C2—H2A | 0.9600 | C12—H12 | 0.9300 |
C2—H2B | 0.9600 | C13—C14 | 1.369 (6) |
C2—H2C | 0.9600 | C13—H13 | 0.9300 |
C3—O3 | 1.446 (3) | C14—C15 | 1.365 (6) |
C3—C4 | 1.477 (5) | C14—H14 | 0.9300 |
C3—H3A | 0.9700 | C15—C16 | 1.404 (5) |
C3—H3B | 0.9700 | C15—H15 | 0.9300 |
C4—O4 | 1.415 (5) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C17—C22 | 1.387 (4) |
C4—H4B | 0.9700 | C17—C18 | 1.385 (4) |
C5—O4 | 1.408 (4) | C17—P3 | 1.800 (3) |
C5—C6 | 1.480 (8) | C18—C19 | 1.380 (4) |
C5—H5A | 0.9700 | C18—H18 | 0.9300 |
C5—H5B | 0.9700 | C19—C20 | 1.362 (5) |
C6—O5 | 1.390 (6) | C19—H19 | 0.9300 |
C6—H6A | 0.9700 | C20—C21 | 1.364 (5) |
C6—H6B | 0.9700 | C20—H20 | 0.9300 |
C7—O5 | 1.409 (6) | C21—C22 | 1.395 (4) |
C7—C8 | 1.463 (8) | C21—H21 | 0.9300 |
C7—H7A | 0.9700 | C22—H22 | 0.9300 |
C7—H7B | 0.9700 | N1—P1 | 1.583 (2) |
C8—O6 | 1.427 (5) | N1—P2 | 1.586 (2) |
C8—H8A | 0.9700 | N2—P2 | 1.575 (2) |
C8—H8B | 0.9700 | N2—P3 | 1.601 (2) |
C9—O6 | 1.428 (4) | N3—P1 | 1.574 (2) |
C9—C10 | 1.437 (5) | N3—P3 | 1.6027 (19) |
C9—H9A | 0.9700 | O1—P1 | 1.5845 (18) |
C9—H9B | 0.9700 | O2—P2 | 1.5745 (19) |
C10—O7 | 1.454 (4) | O7—P2 | 1.5852 (19) |
C10—H10A | 0.9700 | O3—P1 | 1.5733 (18) |
O1—C1—H1A | 109.5 | C12—C11—P3 | 118.7 (2) |
O1—C1—H1B | 109.5 | C13—C12—C11 | 120.6 (3) |
H1A—C1—H1B | 109.5 | C13—C12—H12 | 119.7 |
O1—C1—H1C | 109.5 | C11—C12—H12 | 119.7 |
H1A—C1—H1C | 109.5 | C14—C13—C12 | 120.4 (4) |
H1B—C1—H1C | 109.5 | C14—C13—H13 | 119.8 |
O2—C2—H2A | 109.5 | C12—C13—H13 | 119.8 |
O2—C2—H2B | 109.5 | C13—C14—C15 | 119.5 (3) |
H2A—C2—H2B | 109.5 | C13—C14—H14 | 120.2 |
O2—C2—H2C | 109.5 | C15—C14—H14 | 120.2 |
H2A—C2—H2C | 109.5 | C14—C15—C16 | 121.1 (3) |
H2B—C2—H2C | 109.5 | C14—C15—H15 | 119.4 |
O3—C3—C4 | 109.1 (3) | C16—C15—H15 | 119.4 |
O3—C3—H3A | 109.9 | C11—C16—C15 | 119.3 (3) |
C4—C3—H3A | 109.9 | C11—C16—H16 | 120.4 |
O3—C3—H3B | 109.9 | C15—C16—H16 | 120.4 |
C4—C3—H3B | 109.9 | C22—C17—C18 | 119.1 (2) |
H3A—C3—H3B | 108.3 | C22—C17—P3 | 120.1 (2) |
O4—C4—C3 | 108.6 (3) | C18—C17—P3 | 120.7 (2) |
O4—C4—H4A | 110.0 | C19—C18—C17 | 120.3 (3) |
C3—C4—H4A | 110.0 | C19—C18—H18 | 119.9 |
O4—C4—H4B | 110.0 | C17—C18—H18 | 119.9 |
C3—C4—H4B | 110.0 | C20—C19—C18 | 120.3 (3) |
H4A—C4—H4B | 108.3 | C20—C19—H19 | 119.8 |
O4—C5—C6 | 109.3 (4) | C18—C19—H19 | 119.8 |
O4—C5—H5A | 109.8 | C21—C20—C19 | 120.6 (3) |
C6—C5—H5A | 109.8 | C21—C20—H20 | 119.7 |
O4—C5—H5B | 109.8 | C19—C20—H20 | 119.7 |
C6—C5—H5B | 109.8 | C20—C21—C22 | 119.9 (3) |
H5A—C5—H5B | 108.3 | C20—C21—H21 | 120.0 |
O5—C6—C5 | 109.9 (4) | C22—C21—H21 | 120.0 |
O5—C6—H6A | 109.7 | C17—C22—C21 | 119.8 (3) |
C5—C6—H6A | 109.7 | C17—C22—H22 | 120.1 |
O5—C6—H6B | 109.7 | C21—C22—H22 | 120.1 |
C5—C6—H6B | 109.7 | P1—N1—P2 | 122.96 (13) |
H6A—C6—H6B | 108.2 | P2—N2—P3 | 121.30 (13) |
O5—C7—C8 | 109.1 (4) | P1—N3—P3 | 120.91 (12) |
O5—C7—H7A | 109.9 | C1—O1—P1 | 118.82 (17) |
C8—C7—H7A | 109.9 | C2—O2—P2 | 121.6 (2) |
O5—C7—H7B | 109.9 | C4—O4—C5 | 112.9 (4) |
C8—C7—H7B | 109.9 | C6—O5—C7 | 111.5 (4) |
H7A—C7—H7B | 108.3 | C9—O6—C8 | 114.1 (3) |
O6—C8—C7 | 115.5 (4) | C10—O7—P2 | 117.11 (19) |
O6—C8—H8A | 108.4 | C3—O3—P1 | 119.92 (18) |
C7—C8—H8A | 108.4 | O3—P1—N3 | 106.50 (10) |
O6—C8—H8B | 108.4 | O3—P1—N1 | 112.39 (11) |
C7—C8—H8B | 108.4 | N3—P1—N1 | 117.06 (11) |
H8A—C8—H8B | 107.5 | O3—P1—O1 | 99.50 (10) |
O6—C9—C10 | 110.4 (3) | N3—P1—O1 | 111.66 (11) |
O6—C9—H9A | 109.6 | N1—P1—O1 | 108.35 (11) |
C10—C9—H9A | 109.6 | N2—P2—O2 | 111.65 (12) |
O6—C9—H9B | 109.6 | N2—P2—O7 | 107.88 (11) |
C10—C9—H9B | 109.6 | O2—P2—O7 | 98.83 (11) |
H9A—C9—H9B | 108.1 | N2—P2—N1 | 116.77 (11) |
C9—C10—O7 | 112.9 (3) | O2—P2—N1 | 109.07 (11) |
C9—C10—H10A | 109.0 | O7—P2—N1 | 111.18 (12) |
O7—C10—H10A | 109.0 | N3—P3—N2 | 117.33 (11) |
C9—C10—H10B | 109.0 | N3—P3—C17 | 107.74 (11) |
O7—C10—H10B | 109.0 | N2—P3—C17 | 109.39 (12) |
H10A—C10—H10B | 107.8 | N3—P3—C11 | 107.10 (11) |
C16—C11—C12 | 119.0 (3) | N2—P3—C11 | 109.37 (12) |
C16—C11—P3 | 122.1 (2) | C17—P3—C11 | 105.23 (11) |
O3—C3—C4—O4 | 72.9 (4) | P2—N1—P1—N3 | −11.2 (2) |
O4—C5—C6—O5 | 60.2 (5) | P2—N1—P1—O1 | −138.55 (16) |
O5—C7—C8—O6 | −73.1 (5) | C1—O1—P1—O3 | 177.3 (2) |
O6—C9—C10—O7 | 71.9 (4) | C1—O1—P1—N3 | −70.6 (2) |
C16—C11—C12—C13 | −0.9 (5) | C1—O1—P1—N1 | 59.7 (2) |
P3—C11—C12—C13 | 174.6 (3) | P3—N2—P2—O2 | −128.62 (15) |
C11—C12—C13—C14 | −0.1 (6) | P3—N2—P2—O7 | 123.82 (16) |
C12—C13—C14—C15 | 0.5 (6) | P3—N2—P2—N1 | −2.2 (2) |
C13—C14—C15—C16 | 0.1 (6) | C2—O2—P2—N2 | 82.1 (3) |
C12—C11—C16—C15 | 1.5 (4) | C2—O2—P2—O7 | −164.5 (3) |
P3—C11—C16—C15 | −173.9 (2) | C2—O2—P2—N1 | −48.4 (3) |
C14—C15—C16—C11 | −1.1 (5) | C10—O7—P2—N2 | 176.2 (2) |
C22—C17—C18—C19 | −0.2 (4) | C10—O7—P2—O2 | 59.9 (2) |
P3—C17—C18—C19 | 178.0 (2) | C10—O7—P2—N1 | −54.6 (2) |
C17—C18—C19—C20 | −0.2 (5) | P1—N1—P2—N2 | 15.5 (2) |
C18—C19—C20—C21 | 0.2 (5) | P1—N1—P2—O2 | 143.24 (17) |
C19—C20—C21—C22 | 0.4 (5) | P1—N1—P2—O7 | −108.81 (17) |
C18—C17—C22—C21 | 0.7 (4) | P1—N3—P3—N2 | 18.8 (2) |
P3—C17—C22—C21 | −177.5 (2) | P1—N3—P3—C17 | 142.71 (15) |
C20—C21—C22—C17 | −0.8 (5) | P1—N3—P3—C11 | −104.52 (16) |
C3—C4—O4—C5 | 165.7 (3) | P2—N2—P3—N3 | −14.3 (2) |
C6—C5—O4—C4 | 178.0 (4) | P2—N2—P3—C17 | −137.33 (15) |
C5—C6—O5—C7 | −165.9 (4) | P2—N2—P3—C11 | 107.91 (16) |
C8—C7—O5—C6 | 164.0 (4) | C22—C17—P3—N3 | −161.0 (2) |
C10—C9—O6—C8 | 163.1 (4) | C18—C17—P3—N3 | 20.8 (2) |
C7—C8—O6—C9 | 77.5 (6) | C22—C17—P3—N2 | −32.4 (2) |
C9—C10—O7—P2 | 131.0 (3) | C18—C17—P3—N2 | 149.4 (2) |
C4—C3—O3—P1 | −164.9 (2) | C22—C17—P3—C11 | 85.0 (2) |
C3—O3—P1—N3 | 179.6 (2) | C18—C17—P3—C11 | −93.2 (2) |
C3—O3—P1—N1 | 50.2 (2) | C16—C11—P3—N3 | 127.7 (2) |
C3—O3—P1—O1 | −64.3 (2) | C12—C11—P3—N3 | −47.7 (3) |
P3—N3—P1—O3 | −133.20 (14) | C16—C11—P3—N2 | −0.4 (3) |
P3—N3—P1—N1 | −6.5 (2) | C12—C11—P3—N2 | −175.8 (2) |
P3—N3—P1—O1 | 119.16 (15) | C16—C11—P3—C17 | −117.8 (2) |
P2—N1—P1—O3 | 112.50 (17) | C12—C11—P3—C17 | 66.8 (2) |
C32H40N5O6P3 | Z = 2 |
Mr = 683.60 | F(000) = 720 |
Triclinic, P1 | Dx = 1.368 Mg m−3 |
a = 10.519 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.694 (3) Å | Cell parameters from 11413 reflections |
c = 14.340 (3) Å | θ = 2.9–27.5° |
α = 114.81 (3)° | µ = 0.23 mm−1 |
β = 93.81 (3)° | T = 150 K |
γ = 103.59 (3)° | Block, colourless |
V = 1659.6 (6) Å3 | 0.30 × 0.17 × 0.08 mm |
Nonius KappaCCD diffractometer | 7460 independent reflections |
Radiation source: Nonius FR591 rotating anode | 6157 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ϕ and ω scans | h = −13→13 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −16→15 |
Tmin = 0.934, Tmax = 0.983 | l = −17→18 |
19478 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H 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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C32H40N5O6P3 | γ = 103.59 (3)° |
Mr = 683.60 | V = 1659.6 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.519 (2) Å | Mo Kα radiation |
b = 12.694 (3) Å | µ = 0.23 mm−1 |
c = 14.340 (3) Å | T = 150 K |
α = 114.81 (3)° | 0.30 × 0.17 × 0.08 mm |
β = 93.81 (3)° |
Nonius KappaCCD diffractometer | 7460 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 6157 reflections with I > 2σ(I) |
Tmin = 0.934, Tmax = 0.983 | Rint = 0.033 |
19478 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.65 | Δρmax = 0.28 e Å−3 |
7460 reflections | Δρmin = −0.45 e Å−3 |
431 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O6 | 1.17466 (14) | 0.98464 (12) | 0.45589 (10) | 0.0252 (3) | |
C21 | 0.82058 (17) | 0.76389 (16) | −0.00272 (14) | 0.0222 (4) | |
C22 | 0.93610 (19) | 0.84509 (17) | −0.00216 (15) | 0.0268 (4) | |
H22 | 0.9659 | 0.9253 | 0.0530 | 0.032* | |
C23 | 1.0078 (2) | 0.80890 (19) | −0.08215 (16) | 0.0309 (4) | |
H23 | 1.0865 | 0.8645 | −0.0814 | 0.037* | |
C24 | 0.9651 (2) | 0.69219 (19) | −0.16285 (15) | 0.0303 (4) | |
H24 | 1.0142 | 0.6681 | −0.2175 | 0.036* | |
C25 | 0.8506 (2) | 0.61029 (19) | −0.16403 (16) | 0.0316 (4) | |
H25 | 0.8219 | 0.5299 | −0.2190 | 0.038* | |
C26 | 0.77830 (19) | 0.64609 (18) | −0.08474 (15) | 0.0280 (4) | |
H26 | 0.6994 | 0.5902 | −0.0861 | 0.034* | |
C27 | 0.56009 (17) | 0.75962 (16) | 0.04244 (13) | 0.0224 (4) | |
C28 | 0.5147 (2) | 0.83055 (19) | 0.00353 (16) | 0.0314 (4) | |
H28 | 0.5737 | 0.9037 | 0.0103 | 0.038* | |
C29 | 0.3830 (2) | 0.7939 (2) | −0.04516 (18) | 0.0385 (5) | |
H29 | 0.3513 | 0.8429 | −0.0706 | 0.046* | |
C30 | 0.2974 (2) | 0.6863 (2) | −0.05689 (16) | 0.0365 (5) | |
H30 | 0.2073 | 0.6615 | −0.0907 | 0.044* | |
C31 | 0.34218 (19) | 0.61461 (19) | −0.01972 (15) | 0.0323 (4) | |
H31 | 0.2835 | 0.5403 | −0.0287 | 0.039* | |
C32 | 0.47359 (18) | 0.65191 (17) | 0.03082 (14) | 0.0259 (4) | |
H32 | 0.5044 | 0.6035 | 0.0575 | 0.031* | |
C1 | 0.66710 (17) | 0.68628 (16) | 0.36827 (14) | 0.0211 (3) | |
C2 | 0.62464 (19) | 0.57036 (17) | 0.28489 (15) | 0.0261 (4) | |
H2 | 0.6680 | 0.5510 | 0.2264 | 0.031* | |
C3 | 0.5186 (2) | 0.48309 (17) | 0.28750 (16) | 0.0291 (4) | |
H3 | 0.4895 | 0.4043 | 0.2302 | 0.035* | |
C4 | 0.4553 (2) | 0.50945 (18) | 0.37217 (17) | 0.0320 (4) | |
H4 | 0.3823 | 0.4494 | 0.3729 | 0.038* | |
C5 | 0.4988 (2) | 0.62423 (19) | 0.45628 (16) | 0.0309 (4) | |
H5 | 0.4565 | 0.6426 | 0.5153 | 0.037* | |
C6 | 0.60394 (18) | 0.71218 (17) | 0.45419 (14) | 0.0242 (4) | |
H6 | 0.6331 | 0.7907 | 0.5118 | 0.029* | |
C7 | 0.82853 (17) | 1.21778 (16) | 0.40024 (14) | 0.0225 (4) | |
C8 | 0.8577 (2) | 1.30967 (18) | 0.50242 (15) | 0.0291 (4) | |
H8 | 0.8878 | 1.2953 | 0.5588 | 0.035* | |
C9 | 0.8428 (2) | 1.42195 (19) | 0.52146 (16) | 0.0340 (4) | |
H9 | 0.8626 | 1.4844 | 0.5913 | 0.041* | |
C10 | 0.7993 (2) | 1.44475 (19) | 0.44009 (17) | 0.0327 (4) | |
H10 | 0.7904 | 1.5224 | 0.4537 | 0.039* | |
C11 | 0.7691 (2) | 1.35280 (19) | 0.33912 (17) | 0.0316 (4) | |
H11 | 0.7383 | 1.3672 | 0.2830 | 0.038* | |
C12 | 0.7831 (2) | 1.23971 (18) | 0.31873 (15) | 0.0277 (4) | |
H12 | 0.7617 | 1.1771 | 0.2489 | 0.033* | |
C13 | 1.00165 (19) | 0.65465 (18) | 0.17645 (15) | 0.0296 (4) | |
H13A | 0.9557 | 0.6610 | 0.1174 | 0.036* | |
H13B | 0.9959 | 0.5682 | 0.1538 | 0.036* | |
C14 | 1.14448 (19) | 0.7267 (2) | 0.20252 (15) | 0.0301 (4) | |
H14A | 1.1838 | 0.7031 | 0.1386 | 0.036* | |
H14B | 1.1519 | 0.8141 | 0.2312 | 0.036* | |
C15 | 1.35466 (19) | 0.73185 (19) | 0.28393 (17) | 0.0309 (4) | |
H15A | 1.3752 | 0.7247 | 0.2155 | 0.037* | |
H15B | 1.3858 | 0.6711 | 0.2977 | 0.037* | |
C16 | 1.4309 (2) | 0.85736 (18) | 0.36814 (17) | 0.0321 (4) | |
H16A | 1.4133 | 0.8633 | 0.4369 | 0.038* | |
H16B | 1.5274 | 0.8680 | 0.3693 | 0.038* | |
C17 | 1.4360 (2) | 0.9653 (2) | 0.26494 (17) | 0.0325 (4) | |
H17A | 1.3832 | 0.8937 | 0.2004 | 0.039* | |
H17B | 1.5314 | 0.9703 | 0.2653 | 0.039* | |
C18 | 1.41154 (19) | 1.07805 (19) | 0.26819 (17) | 0.0318 (4) | |
H18A | 1.4695 | 1.1502 | 0.3300 | 0.038* | |
H18B | 1.4319 | 1.0859 | 0.2046 | 0.038* | |
C19 | 1.24327 (19) | 1.17620 (17) | 0.28454 (16) | 0.0280 (4) | |
H19A | 1.2284 | 1.1755 | 0.2153 | 0.034* | |
H19B | 1.3174 | 1.2490 | 0.3309 | 0.034* | |
C20 | 1.11903 (18) | 1.17974 (16) | 0.33047 (15) | 0.0249 (4) | |
H20A | 1.1272 | 1.1632 | 0.3919 | 0.030* | |
H20B | 1.1060 | 1.2611 | 0.3538 | 0.030* | |
N1 | 0.93565 (14) | 0.91753 (13) | 0.31140 (12) | 0.0209 (3) | |
N2 | 0.77713 (15) | 0.94920 (13) | 0.17428 (12) | 0.0221 (3) | |
N3 | 0.74437 (15) | 0.72396 (13) | 0.16301 (11) | 0.0212 (3) | |
N4 | 0.77009 (15) | 0.77953 (14) | 0.36814 (12) | 0.0219 (3) | |
N5 | 0.84618 (16) | 1.10404 (14) | 0.38169 (12) | 0.0241 (3) | |
O1 | 0.93503 (12) | 0.69567 (11) | 0.26425 (10) | 0.0235 (3) | |
O2 | 1.21402 (13) | 0.70438 (14) | 0.27757 (11) | 0.0319 (3) | |
O3 | 1.39789 (14) | 0.95393 (13) | 0.35467 (11) | 0.0295 (3) | |
O4 | 1.27593 (13) | 1.07003 (12) | 0.27390 (12) | 0.0307 (3) | |
O5 | 1.00655 (12) | 1.08896 (11) | 0.25160 (10) | 0.0231 (3) | |
P1 | 0.84447 (4) | 0.78142 (4) | 0.27162 (3) | 0.01863 (11) | |
P2 | 0.88797 (4) | 1.00921 (4) | 0.27737 (3) | 0.01905 (11) | |
P3 | 0.73149 (4) | 0.80545 (4) | 0.10466 (3) | 0.01933 (11) | |
H4N | 0.787 (3) | 0.845 (2) | 0.418 (2) | 0.037 (7)* | |
H5N | 0.843 (2) | 1.086 (2) | 0.429 (2) | 0.034 (6)* | |
H01 | 1.095 (3) | 0.964 (3) | 0.412 (3) | 0.063 (9)* | |
H02 | 1.234 (3) | 0.975 (2) | 0.421 (2) | 0.039 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O6 | 0.0253 (7) | 0.0287 (7) | 0.0187 (6) | 0.0080 (5) | 0.0035 (5) | 0.0079 (5) |
C21 | 0.0230 (8) | 0.0264 (9) | 0.0189 (8) | 0.0091 (7) | 0.0024 (7) | 0.0109 (7) |
C22 | 0.0270 (9) | 0.0270 (9) | 0.0261 (9) | 0.0073 (7) | 0.0059 (7) | 0.0118 (8) |
C23 | 0.0255 (9) | 0.0384 (11) | 0.0337 (10) | 0.0093 (8) | 0.0088 (8) | 0.0203 (9) |
C24 | 0.0316 (10) | 0.0420 (11) | 0.0241 (9) | 0.0183 (9) | 0.0102 (8) | 0.0164 (9) |
C25 | 0.0357 (11) | 0.0321 (10) | 0.0244 (9) | 0.0134 (8) | 0.0057 (8) | 0.0083 (8) |
C26 | 0.0275 (9) | 0.0280 (9) | 0.0238 (9) | 0.0063 (8) | 0.0046 (7) | 0.0081 (8) |
C27 | 0.0217 (8) | 0.0254 (9) | 0.0153 (8) | 0.0083 (7) | 0.0026 (6) | 0.0041 (7) |
C28 | 0.0321 (10) | 0.0319 (10) | 0.0275 (10) | 0.0086 (8) | −0.0017 (8) | 0.0122 (8) |
C29 | 0.0365 (11) | 0.0453 (12) | 0.0344 (11) | 0.0170 (10) | −0.0031 (9) | 0.0171 (10) |
C30 | 0.0236 (10) | 0.0481 (13) | 0.0263 (10) | 0.0099 (9) | −0.0022 (8) | 0.0074 (9) |
C31 | 0.0236 (9) | 0.0362 (11) | 0.0258 (10) | 0.0039 (8) | 0.0030 (7) | 0.0063 (8) |
C32 | 0.0249 (9) | 0.0270 (9) | 0.0223 (9) | 0.0078 (7) | 0.0046 (7) | 0.0076 (7) |
C1 | 0.0190 (8) | 0.0234 (8) | 0.0223 (8) | 0.0047 (7) | 0.0006 (6) | 0.0128 (7) |
C2 | 0.0293 (9) | 0.0228 (9) | 0.0263 (9) | 0.0092 (7) | 0.0047 (7) | 0.0101 (7) |
C3 | 0.0310 (10) | 0.0198 (9) | 0.0331 (10) | 0.0048 (7) | −0.0006 (8) | 0.0110 (8) |
C4 | 0.0275 (10) | 0.0288 (10) | 0.0395 (11) | −0.0004 (8) | 0.0009 (8) | 0.0204 (9) |
C5 | 0.0285 (10) | 0.0340 (10) | 0.0300 (10) | 0.0035 (8) | 0.0052 (8) | 0.0171 (8) |
C6 | 0.0239 (9) | 0.0251 (9) | 0.0213 (8) | 0.0032 (7) | 0.0020 (7) | 0.0107 (7) |
C7 | 0.0224 (8) | 0.0229 (8) | 0.0223 (9) | 0.0079 (7) | 0.0068 (7) | 0.0093 (7) |
C8 | 0.0359 (10) | 0.0293 (10) | 0.0209 (9) | 0.0116 (8) | 0.0057 (8) | 0.0091 (8) |
C9 | 0.0426 (12) | 0.0274 (10) | 0.0263 (10) | 0.0128 (9) | 0.0091 (9) | 0.0051 (8) |
C10 | 0.0377 (11) | 0.0274 (10) | 0.0385 (11) | 0.0164 (8) | 0.0145 (9) | 0.0151 (9) |
C11 | 0.0375 (11) | 0.0353 (11) | 0.0325 (10) | 0.0191 (9) | 0.0119 (8) | 0.0196 (9) |
C12 | 0.0338 (10) | 0.0306 (10) | 0.0214 (9) | 0.0151 (8) | 0.0064 (7) | 0.0110 (8) |
C13 | 0.0276 (9) | 0.0300 (10) | 0.0248 (9) | 0.0133 (8) | 0.0037 (7) | 0.0039 (8) |
C14 | 0.0290 (10) | 0.0401 (11) | 0.0241 (9) | 0.0141 (8) | 0.0069 (8) | 0.0147 (8) |
C15 | 0.0249 (9) | 0.0326 (10) | 0.0364 (11) | 0.0130 (8) | 0.0036 (8) | 0.0144 (9) |
C16 | 0.0300 (10) | 0.0330 (10) | 0.0342 (11) | 0.0135 (8) | 0.0015 (8) | 0.0145 (9) |
C17 | 0.0297 (10) | 0.0374 (11) | 0.0343 (11) | 0.0133 (8) | 0.0131 (8) | 0.0167 (9) |
C18 | 0.0253 (9) | 0.0371 (11) | 0.0364 (11) | 0.0088 (8) | 0.0099 (8) | 0.0192 (9) |
C19 | 0.0259 (9) | 0.0267 (9) | 0.0337 (10) | 0.0047 (7) | 0.0016 (8) | 0.0179 (8) |
C20 | 0.0234 (9) | 0.0202 (8) | 0.0241 (9) | 0.0008 (7) | −0.0033 (7) | 0.0074 (7) |
N1 | 0.0197 (7) | 0.0211 (7) | 0.0206 (7) | 0.0045 (6) | 0.0007 (6) | 0.0093 (6) |
N2 | 0.0239 (7) | 0.0214 (7) | 0.0191 (7) | 0.0067 (6) | 0.0000 (6) | 0.0078 (6) |
N3 | 0.0232 (7) | 0.0191 (7) | 0.0170 (7) | 0.0031 (6) | −0.0011 (6) | 0.0065 (6) |
N4 | 0.0230 (7) | 0.0196 (7) | 0.0184 (7) | 0.0020 (6) | 0.0034 (6) | 0.0066 (6) |
N5 | 0.0335 (9) | 0.0241 (8) | 0.0180 (7) | 0.0108 (6) | 0.0057 (6) | 0.0112 (6) |
O1 | 0.0235 (6) | 0.0240 (6) | 0.0253 (6) | 0.0098 (5) | 0.0054 (5) | 0.0114 (5) |
O2 | 0.0241 (7) | 0.0437 (8) | 0.0320 (7) | 0.0111 (6) | 0.0046 (6) | 0.0201 (6) |
O3 | 0.0322 (7) | 0.0320 (7) | 0.0291 (7) | 0.0149 (6) | 0.0096 (6) | 0.0148 (6) |
O4 | 0.0238 (7) | 0.0275 (7) | 0.0436 (8) | 0.0070 (5) | 0.0065 (6) | 0.0186 (6) |
O5 | 0.0227 (6) | 0.0228 (6) | 0.0210 (6) | 0.0018 (5) | 0.0006 (5) | 0.0101 (5) |
P1 | 0.0182 (2) | 0.0196 (2) | 0.0177 (2) | 0.00543 (16) | 0.00222 (16) | 0.00827 (17) |
P2 | 0.0200 (2) | 0.0188 (2) | 0.0170 (2) | 0.00481 (17) | 0.00134 (16) | 0.00751 (17) |
P3 | 0.0191 (2) | 0.0203 (2) | 0.0165 (2) | 0.00533 (17) | 0.00102 (16) | 0.00692 (17) |
O6—H01 | 0.92 (3) | C10—C11 | 1.381 (3) |
O6—H02 | 0.83 (3) | C10—H10 | 0.9500 |
C21—C22 | 1.394 (3) | C11—C12 | 1.386 (3) |
C21—C26 | 1.400 (3) | C11—H11 | 0.9500 |
C21—P3 | 1.8083 (19) | C12—H12 | 0.9500 |
C22—C23 | 1.390 (3) | C13—O1 | 1.444 (2) |
C22—H22 | 0.9500 | C13—C14 | 1.492 (3) |
C23—C24 | 1.384 (3) | C13—H13A | 0.9900 |
C23—H23 | 0.9500 | C13—H13B | 0.9900 |
C24—C25 | 1.387 (3) | C14—O2 | 1.422 (2) |
C24—H24 | 0.9500 | C14—H14A | 0.9900 |
C25—C26 | 1.386 (3) | C14—H14B | 0.9900 |
C25—H25 | 0.9500 | C15—O2 | 1.425 (2) |
C26—H26 | 0.9500 | C15—C16 | 1.515 (3) |
C27—C28 | 1.392 (3) | C15—H15A | 0.9900 |
C27—C32 | 1.389 (3) | C15—H15B | 0.9900 |
C27—P3 | 1.8009 (19) | C16—O3 | 1.432 (2) |
C28—C29 | 1.385 (3) | C16—H16A | 0.9900 |
C28—H28 | 0.9500 | C16—H16B | 0.9900 |
C29—C30 | 1.384 (3) | C17—O3 | 1.426 (2) |
C29—H29 | 0.9500 | C17—C18 | 1.495 (3) |
C30—C31 | 1.381 (3) | C17—H17A | 0.9900 |
C30—H30 | 0.9500 | C17—H17B | 0.9900 |
C31—C32 | 1.390 (3) | C18—O4 | 1.416 (2) |
C31—H31 | 0.9500 | C18—H18A | 0.9900 |
C32—H32 | 0.9500 | C18—H18B | 0.9900 |
C1—C6 | 1.392 (3) | C19—O4 | 1.418 (2) |
C1—C2 | 1.392 (3) | C19—C20 | 1.504 (3) |
C1—N4 | 1.405 (2) | C19—H19A | 0.9900 |
C2—C3 | 1.390 (3) | C19—H19B | 0.9900 |
C2—H2 | 0.9500 | C20—O5 | 1.447 (2) |
C3—C4 | 1.379 (3) | C20—H20A | 0.9900 |
C3—H3 | 0.9500 | C20—H20B | 0.9900 |
C4—C5 | 1.388 (3) | N1—P1 | 1.5974 (16) |
C4—H4 | 0.9500 | N1—P2 | 1.6007 (15) |
C5—C6 | 1.386 (3) | N2—P2 | 1.5918 (17) |
C5—H5 | 0.9500 | N2—P3 | 1.5978 (17) |
C6—H6 | 0.9500 | N3—P1 | 1.5920 (16) |
C7—C12 | 1.390 (3) | N3—P3 | 1.6017 (15) |
C7—C8 | 1.393 (3) | N4—P1 | 1.6404 (16) |
C7—N5 | 1.414 (2) | N4—H4N | 0.80 (3) |
C8—C9 | 1.384 (3) | N5—P2 | 1.6448 (17) |
C8—H8 | 0.9500 | N5—H5N | 0.80 (3) |
C9—C10 | 1.389 (3) | O1—P1 | 1.5836 (13) |
C9—H9 | 0.9500 | O5—P2 | 1.5808 (14) |
H01—O6—H02 | 109 (3) | C14—C13—H13B | 109.2 |
C22—C21—C26 | 119.06 (17) | H13A—C13—H13B | 107.9 |
C22—C21—P3 | 121.00 (14) | O2—C14—C13 | 109.02 (17) |
C26—C21—P3 | 119.82 (14) | O2—C14—H14A | 109.9 |
C21—C22—C23 | 120.13 (18) | C13—C14—H14A | 109.9 |
C21—C22—H22 | 119.9 | O2—C14—H14B | 109.9 |
C23—C22—H22 | 119.9 | C13—C14—H14B | 109.9 |
C24—C23—C22 | 120.32 (19) | H14A—C14—H14B | 108.3 |
C24—C23—H23 | 119.8 | O2—C15—C16 | 113.79 (17) |
C22—C23—H23 | 119.8 | O2—C15—H15A | 108.8 |
C25—C24—C23 | 120.11 (18) | C16—C15—H15A | 108.8 |
C25—C24—H24 | 119.9 | O2—C15—H15B | 108.8 |
C23—C24—H24 | 119.9 | C16—C15—H15B | 108.8 |
C26—C25—C24 | 119.81 (19) | H15A—C15—H15B | 107.7 |
C26—C25—H25 | 120.1 | O3—C16—C15 | 114.11 (16) |
C24—C25—H25 | 120.1 | O3—C16—H16A | 108.7 |
C25—C26—C21 | 120.56 (19) | C15—C16—H16A | 108.7 |
C25—C26—H26 | 119.7 | O3—C16—H16B | 108.7 |
C21—C26—H26 | 119.7 | C15—C16—H16B | 108.7 |
C28—C27—C32 | 119.78 (17) | H16A—C16—H16B | 107.6 |
C28—C27—P3 | 120.10 (15) | O3—C17—C18 | 108.13 (16) |
C32—C27—P3 | 120.10 (14) | O3—C17—H17A | 110.1 |
C27—C28—C29 | 119.7 (2) | C18—C17—H17A | 110.1 |
C27—C28—H28 | 120.2 | O3—C17—H17B | 110.1 |
C29—C28—H28 | 120.2 | C18—C17—H17B | 110.1 |
C30—C29—C28 | 120.3 (2) | H17A—C17—H17B | 108.4 |
C30—C29—H29 | 119.9 | O4—C18—C17 | 108.10 (16) |
C28—C29—H29 | 119.9 | O4—C18—H18A | 110.1 |
C29—C30—C31 | 120.36 (19) | C17—C18—H18A | 110.1 |
C29—C30—H30 | 119.8 | O4—C18—H18B | 110.1 |
C31—C30—H30 | 119.8 | C17—C18—H18B | 110.1 |
C30—C31—C32 | 119.6 (2) | H18A—C18—H18B | 108.4 |
C30—C31—H31 | 120.2 | O4—C19—C20 | 108.62 (15) |
C32—C31—H31 | 120.2 | O4—C19—H19A | 110.0 |
C31—C32—C27 | 120.25 (19) | C20—C19—H19A | 110.0 |
C31—C32—H32 | 119.9 | O4—C19—H19B | 110.0 |
C27—C32—H32 | 119.9 | C20—C19—H19B | 110.0 |
C6—C1—C2 | 119.21 (17) | H19A—C19—H19B | 108.3 |
C6—C1—N4 | 118.46 (16) | O5—C20—C19 | 108.81 (15) |
C2—C1—N4 | 122.32 (17) | O5—C20—H20A | 109.9 |
C3—C2—C1 | 119.79 (18) | C19—C20—H20A | 109.9 |
C3—C2—H2 | 120.1 | O5—C20—H20B | 109.9 |
C1—C2—H2 | 120.1 | C19—C20—H20B | 109.9 |
C4—C3—C2 | 120.85 (18) | H20A—C20—H20B | 108.3 |
C4—C3—H3 | 119.6 | P1—N1—P2 | 121.03 (9) |
C2—C3—H3 | 119.6 | P2—N2—P3 | 119.80 (10) |
C3—C4—C5 | 119.55 (18) | P1—N3—P3 | 119.90 (9) |
C3—C4—H4 | 120.2 | C1—N4—P1 | 128.73 (13) |
C5—C4—H4 | 120.2 | C1—N4—H4N | 117.0 (19) |
C6—C5—C4 | 120.06 (19) | P1—N4—H4N | 113.4 (19) |
C6—C5—H5 | 120.0 | C7—N5—P2 | 127.16 (13) |
C4—C5—H5 | 120.0 | C7—N5—H5N | 117.4 (18) |
C5—C6—C1 | 120.52 (18) | P2—N5—H5N | 115.1 (18) |
C5—C6—H6 | 119.7 | C13—O1—P1 | 120.18 (12) |
C1—C6—H6 | 119.7 | C14—O2—C15 | 115.21 (16) |
C12—C7—C8 | 119.46 (17) | C17—O3—C16 | 114.01 (15) |
C12—C7—N5 | 121.41 (17) | C18—O4—C19 | 113.03 (15) |
C8—C7—N5 | 119.13 (17) | C20—O5—P2 | 122.78 (12) |
C9—C8—C7 | 119.69 (19) | O1—P1—N3 | 108.57 (8) |
C9—C8—H8 | 120.2 | O1—P1—N1 | 109.90 (8) |
C7—C8—H8 | 120.2 | N3—P1—N1 | 116.23 (9) |
C8—C9—C10 | 121.02 (19) | O1—P1—N4 | 101.60 (8) |
C8—C9—H9 | 119.5 | N3—P1—N4 | 113.24 (8) |
C10—C9—H9 | 119.5 | N1—P1—N4 | 106.30 (9) |
C11—C10—C9 | 118.97 (19) | O5—P2—N2 | 103.21 (8) |
C11—C10—H10 | 120.5 | O5—P2—N1 | 111.49 (8) |
C9—C10—H10 | 120.5 | N2—P2—N1 | 116.27 (8) |
C10—C11—C12 | 120.73 (19) | O5—P2—N5 | 105.94 (8) |
C10—C11—H11 | 119.6 | N2—P2—N5 | 114.05 (9) |
C12—C11—H11 | 119.6 | N1—P2—N5 | 105.54 (8) |
C7—C12—C11 | 120.12 (18) | N2—P3—N3 | 117.25 (8) |
C7—C12—H12 | 119.9 | N2—P3—C27 | 108.31 (9) |
C11—C12—H12 | 119.9 | N3—P3—C27 | 107.84 (9) |
O1—C13—C14 | 112.15 (16) | N2—P3—C21 | 110.36 (9) |
O1—C13—H13A | 109.2 | N3—P3—C21 | 107.95 (8) |
C14—C13—H13A | 109.2 | C27—P3—C21 | 104.34 (8) |
O1—C13—H13B | 109.2 | ||
C26—C21—C22—C23 | 0.0 (3) | C17—C18—O4—C19 | 175.98 (16) |
P3—C21—C22—C23 | 175.91 (15) | C20—C19—O4—C18 | −158.44 (16) |
C21—C22—C23—C24 | 0.0 (3) | C19—C20—O5—P2 | 141.23 (13) |
C22—C23—C24—C25 | −0.4 (3) | C13—O1—P1—N3 | 49.60 (15) |
C23—C24—C25—C26 | 0.7 (3) | C13—O1—P1—N1 | −78.53 (15) |
C24—C25—C26—C21 | −0.7 (3) | C13—O1—P1—N4 | 169.20 (13) |
C22—C21—C26—C25 | 0.4 (3) | P3—N3—P1—O1 | −129.09 (10) |
P3—C21—C26—C25 | −175.60 (15) | P3—N3—P1—N1 | −4.63 (14) |
C32—C27—C28—C29 | 0.9 (3) | P3—N3—P1—N4 | 118.88 (11) |
P3—C27—C28—C29 | 179.34 (16) | P2—N1—P1—O1 | 150.68 (10) |
C27—C28—C29—C30 | −1.2 (3) | P2—N1—P1—N3 | 26.91 (14) |
C28—C29—C30—C31 | 0.3 (3) | P2—N1—P1—N4 | −100.13 (12) |
C29—C30—C31—C32 | 0.8 (3) | C1—N4—P1—O1 | −74.15 (17) |
C30—C31—C32—C27 | −1.1 (3) | C1—N4—P1—N3 | 42.08 (18) |
C28—C27—C32—C31 | 0.2 (3) | C1—N4—P1—N1 | 170.89 (15) |
P3—C27—C32—C31 | −178.23 (14) | C20—O5—P2—N2 | 166.92 (13) |
C6—C1—C2—C3 | 1.3 (3) | C20—O5—P2—N1 | −67.56 (15) |
N4—C1—C2—C3 | −177.38 (17) | C20—O5—P2—N5 | 46.76 (15) |
C1—C2—C3—C4 | −0.5 (3) | P3—N2—P2—O5 | 115.82 (11) |
C2—C3—C4—C5 | −0.7 (3) | P3—N2—P2—N1 | −6.55 (14) |
C3—C4—C5—C6 | 1.0 (3) | P3—N2—P2—N5 | −129.74 (11) |
C4—C5—C6—C1 | −0.3 (3) | P1—N1—P2—O5 | −139.24 (10) |
C2—C1—C6—C5 | −0.9 (3) | P1—N1—P2—N2 | −21.33 (14) |
N4—C1—C6—C5 | 177.81 (17) | P1—N1—P2—N5 | 106.19 (12) |
C12—C7—C8—C9 | −0.8 (3) | C7—N5—P2—O5 | 45.16 (18) |
N5—C7—C8—C9 | 179.04 (18) | C7—N5—P2—N2 | −67.65 (18) |
C7—C8—C9—C10 | −0.1 (3) | C7—N5—P2—N1 | 163.51 (15) |
C8—C9—C10—C11 | 0.9 (3) | P2—N2—P3—N3 | 27.64 (14) |
C9—C10—C11—C12 | −0.7 (3) | P2—N2—P3—C27 | 149.87 (11) |
C8—C7—C12—C11 | 1.0 (3) | P2—N2—P3—C21 | −96.48 (12) |
N5—C7—C12—C11 | −178.83 (18) | P1—N3—P3—N2 | −21.75 (14) |
C10—C11—C12—C7 | −0.3 (3) | P1—N3—P3—C27 | −144.23 (10) |
O1—C13—C14—O2 | 66.6 (2) | P1—N3—P3—C21 | 103.58 (12) |
O2—C15—C16—O3 | −60.6 (2) | C28—C27—P3—N2 | 39.48 (17) |
O3—C17—C18—O4 | −56.3 (2) | C32—C27—P3—N2 | −142.09 (15) |
O4—C19—C20—O5 | −72.65 (19) | C28—C27—P3—N3 | 167.30 (15) |
C6—C1—N4—P1 | −169.29 (14) | C32—C27—P3—N3 | −14.27 (17) |
C2—C1—N4—P1 | 9.3 (3) | C28—C27—P3—C21 | −78.09 (17) |
C12—C7—N5—P2 | 31.2 (3) | C32—C27—P3—C21 | 100.33 (16) |
C8—C7—N5—P2 | −148.62 (16) | C22—C21—P3—N2 | 16.56 (17) |
C14—C13—O1—P1 | 99.94 (17) | C26—C21—P3—N2 | −167.52 (14) |
C13—C14—O2—C15 | 159.52 (16) | C22—C21—P3—N3 | −112.76 (15) |
C16—C15—O2—C14 | 94.9 (2) | C26—C21—P3—N3 | 63.16 (16) |
C18—C17—O3—C16 | −172.93 (16) | C22—C21—P3—C27 | 132.72 (15) |
C15—C16—O3—C17 | −66.6 (2) | C26—C21—P3—C27 | −51.37 (17) |
C28H46N5O5P3 | Z = 2 |
Mr = 625.61 | F(000) = 668 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
a = 9.5003 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4210 (3) Å | Cell parameters from 12052 reflections |
c = 17.1257 (3) Å | θ = 2.9–27.5° |
α = 92.598 (2)° | µ = 0.23 mm−1 |
β = 90.645 (2)° | T = 120 K |
γ = 108.799 (1)° | Block, colourless |
V = 1602.79 (6) Å3 | 0.27 × 0.18 × 0.12 mm |
Nonius KappaCCD diffractometer | 7079 independent reflections |
Radiation source: Nonius FR591 rotating anode | 5682 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | k = −13→13 |
Tmin = 0.941, Tmax = 0.973 | l = −22→19 |
20859 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H 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 reflections | Δρmax = 0.72 e Å−3 |
385 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0032 (15) |
C28H46N5O5P3 | γ = 108.799 (1)° |
Mr = 625.61 | V = 1602.79 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5003 (2) Å | Mo Kα radiation |
b = 10.4210 (3) Å | µ = 0.23 mm−1 |
c = 17.1257 (3) Å | T = 120 K |
α = 92.598 (2)° | 0.27 × 0.18 × 0.12 mm |
β = 90.645 (2)° |
Nonius KappaCCD diffractometer | 7079 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1997) | 5682 reflections with I > 2σ(I) |
Tmin = 0.941, Tmax = 0.973 | Rint = 0.091 |
20859 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.72 e Å−3 |
7079 reflections | Δρmin = −0.48 e Å−3 |
385 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3736 (2) | 0.0629 (2) | 0.31806 (12) | 0.0232 (4) | |
C2 | 0.2276 (2) | −0.0502 (3) | 0.29802 (14) | 0.0344 (5) | |
H2A | 0.1939 | −0.0405 | 0.2450 | 0.052* | |
H2B | 0.1522 | −0.0442 | 0.3353 | 0.052* | |
H2C | 0.2430 | −0.1385 | 0.3009 | 0.052* | |
C3 | 0.3488 (3) | 0.2004 (2) | 0.31825 (15) | 0.0366 (6) | |
H3A | 0.4430 | 0.2726 | 0.3309 | 0.055* | |
H3B | 0.2756 | 0.2038 | 0.3575 | 0.055* | |
H3C | 0.3118 | 0.2132 | 0.2665 | 0.055* | |
C4 | 0.4321 (2) | 0.0396 (3) | 0.39724 (13) | 0.0318 (5) | |
H4A | 0.4464 | −0.0495 | 0.3957 | 0.048* | |
H4B | 0.3604 | 0.0429 | 0.4373 | 0.048* | |
H4C | 0.5273 | 0.1104 | 0.4098 | 0.048* | |
C5 | 0.7337 (2) | 0.6212 (2) | 0.21172 (12) | 0.0227 (4) | |
C6 | 0.7158 (3) | 0.5919 (3) | 0.12430 (14) | 0.0407 (6) | |
H6A | 0.7871 | 0.5473 | 0.1067 | 0.061* | |
H6B | 0.7344 | 0.6772 | 0.0981 | 0.061* | |
H6C | 0.6144 | 0.5322 | 0.1114 | 0.061* | |
C7 | 0.8906 (2) | 0.7206 (2) | 0.23173 (14) | 0.0320 (5) | |
H7A | 0.9040 | 0.7357 | 0.2886 | 0.048* | |
H7B | 0.9025 | 0.8072 | 0.2080 | 0.048* | |
H7C | 0.9652 | 0.6821 | 0.2113 | 0.048* | |
C8 | 0.6204 (3) | 0.6860 (2) | 0.24175 (15) | 0.0350 (5) | |
H8A | 0.5198 | 0.6218 | 0.2328 | 0.053* | |
H8B | 0.6304 | 0.7684 | 0.2139 | 0.053* | |
H8C | 0.6383 | 0.7093 | 0.2979 | 0.053* | |
C9 | 0.8606 (2) | 0.0568 (2) | 0.33826 (12) | 0.0232 (4) | |
H9A | 0.9239 | 0.1262 | 0.3047 | 0.028* | |
H9B | 0.8937 | −0.0241 | 0.3341 | 0.028* | |
C10 | 0.8766 (2) | 0.1117 (2) | 0.42160 (12) | 0.0266 (5) | |
H10A | 0.8363 | 0.1881 | 0.4271 | 0.032* | |
H10B | 0.8214 | 0.0400 | 0.4563 | 0.032* | |
C11 | 1.0599 (2) | 0.2223 (3) | 0.51739 (13) | 0.0320 (5) | |
H11A | 1.0244 | 0.1551 | 0.5578 | 0.038* | |
H11B | 1.0072 | 0.2900 | 0.5231 | 0.038* | |
C12 | 1.2252 (3) | 0.2916 (3) | 0.52765 (13) | 0.0347 (5) | |
H12A | 1.2488 | 0.3227 | 0.5832 | 0.042* | |
H12B | 1.2771 | 0.2253 | 0.5145 | 0.042* | |
C13 | 1.2788 (3) | 0.5310 (3) | 0.51706 (16) | 0.0480 (7) | |
H13A | 1.3458 | 0.5527 | 0.5640 | 0.058* | |
H13B | 1.1772 | 0.5229 | 0.5340 | 0.058* | |
C14 | 1.3291 (3) | 0.6407 (3) | 0.46211 (16) | 0.0452 (7) | |
H14A | 1.3570 | 0.7290 | 0.4923 | 0.054* | |
H14B | 1.4197 | 0.6340 | 0.4366 | 0.054* | |
C15 | 1.2135 (2) | 0.5511 (2) | 0.33720 (14) | 0.0320 (5) | |
H15A | 1.2966 | 0.5136 | 0.3406 | 0.038* | |
H15B | 1.2255 | 0.6029 | 0.2893 | 0.038* | |
C16 | 1.0702 (2) | 0.4370 (2) | 0.33087 (14) | 0.0288 (5) | |
H16A | 1.0746 | 0.3718 | 0.2879 | 0.035* | |
H16B | 1.0539 | 0.3887 | 0.3801 | 0.035* | |
C17 | 0.9988 (2) | 0.1785 (2) | 0.11671 (11) | 0.0194 (4) | |
C18 | 0.9824 (2) | 0.0417 (2) | 0.10682 (12) | 0.0241 (4) | |
H18 | 0.8875 | −0.0243 | 0.1121 | 0.029* | |
C19 | 1.1042 (3) | 0.0007 (2) | 0.08927 (13) | 0.0327 (5) | |
H19 | 1.0927 | −0.0932 | 0.0828 | 0.039* | |
C20 | 1.2408 (3) | 0.0956 (3) | 0.08131 (14) | 0.0360 (6) | |
H20 | 1.3235 | 0.0670 | 0.0687 | 0.043* | |
C21 | 1.2598 (3) | 0.2317 (3) | 0.09129 (16) | 0.0394 (6) | |
H21 | 1.3552 | 0.2967 | 0.0854 | 0.047* | |
C22 | 1.1392 (2) | 0.2742 (2) | 0.11003 (14) | 0.0304 (5) | |
H22 | 1.1524 | 0.3682 | 0.1183 | 0.037* | |
C23 | 0.7737 (2) | 0.24617 (19) | 0.03569 (11) | 0.0181 (4) | |
C24 | 0.6302 (2) | 0.1739 (2) | 0.00908 (13) | 0.0255 (4) | |
H24 | 0.5634 | 0.1151 | 0.0428 | 0.031* | |
C25 | 0.5835 (2) | 0.1867 (2) | −0.06616 (14) | 0.0327 (5) | |
H25 | 0.4852 | 0.1364 | −0.0839 | 0.039* | |
C26 | 0.6799 (2) | 0.2727 (2) | −0.11554 (13) | 0.0296 (5) | |
H26 | 0.6481 | 0.2812 | −0.1673 | 0.036* | |
C27 | 0.8233 (2) | 0.3466 (2) | −0.08931 (12) | 0.0253 (4) | |
H27 | 0.8892 | 0.4067 | −0.1228 | 0.030* | |
C28 | 0.8699 (2) | 0.3326 (2) | −0.01459 (12) | 0.0211 (4) | |
H28 | 0.9685 | 0.3824 | 0.0028 | 0.025* | |
N1 | 0.72087 (17) | 0.26791 (16) | 0.30129 (9) | 0.0182 (3) | |
N2 | 0.88823 (17) | 0.37503 (16) | 0.17868 (9) | 0.0192 (3) | |
N3 | 0.71138 (17) | 0.10801 (16) | 0.17107 (9) | 0.0197 (3) | |
N4 | 0.47903 (18) | 0.05308 (17) | 0.25655 (10) | 0.0199 (4) | |
N5 | 0.7113 (2) | 0.49711 (17) | 0.25515 (10) | 0.0235 (4) | |
O1 | 0.70748 (14) | 0.02057 (13) | 0.31231 (8) | 0.0206 (3) | |
O2 | 1.03044 (15) | 0.15663 (16) | 0.44202 (8) | 0.0274 (3) | |
O3 | 1.27911 (18) | 0.40478 (17) | 0.48005 (9) | 0.0348 (4) | |
O4 | 1.22158 (19) | 0.63974 (18) | 0.40256 (11) | 0.0438 (5) | |
O5 | 0.94914 (15) | 0.48741 (14) | 0.31600 (8) | 0.0235 (3) | |
P1 | 0.65997 (5) | 0.12130 (5) | 0.25830 (3) | 0.01615 (13) | |
P2 | 0.81718 (5) | 0.39971 (5) | 0.25967 (3) | 0.01652 (13) | |
P3 | 0.83675 (5) | 0.22942 (5) | 0.13334 (3) | 0.01621 (13) | |
H5 | 0.610 (3) | 0.450 (3) | 0.2648 (18) | 0.058 (9)* | |
H4 | 0.445 (3) | 0.040 (3) | 0.2153 (17) | 0.041 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0163 (9) | 0.0275 (11) | 0.0223 (11) | 0.0021 (8) | 0.0048 (7) | 0.0020 (8) |
C2 | 0.0179 (10) | 0.0420 (14) | 0.0341 (13) | −0.0033 (9) | 0.0041 (9) | 0.0027 (10) |
C3 | 0.0352 (13) | 0.0341 (13) | 0.0432 (14) | 0.0138 (10) | 0.0161 (10) | 0.0048 (10) |
C4 | 0.0260 (11) | 0.0437 (14) | 0.0212 (11) | 0.0045 (10) | 0.0053 (8) | 0.0043 (9) |
C5 | 0.0256 (10) | 0.0176 (10) | 0.0260 (11) | 0.0080 (8) | 0.0012 (8) | 0.0053 (8) |
C6 | 0.0624 (17) | 0.0337 (13) | 0.0294 (13) | 0.0204 (12) | −0.0063 (11) | 0.0026 (10) |
C7 | 0.0298 (12) | 0.0240 (11) | 0.0397 (14) | 0.0048 (9) | 0.0031 (9) | 0.0056 (9) |
C8 | 0.0383 (13) | 0.0304 (12) | 0.0432 (14) | 0.0200 (10) | 0.0003 (10) | 0.0051 (10) |
C9 | 0.0184 (9) | 0.0251 (11) | 0.0271 (11) | 0.0084 (8) | −0.0013 (8) | 0.0013 (8) |
C10 | 0.0198 (10) | 0.0317 (12) | 0.0270 (11) | 0.0059 (9) | 0.0016 (8) | 0.0053 (9) |
C11 | 0.0297 (12) | 0.0435 (14) | 0.0215 (11) | 0.0096 (10) | −0.0007 (8) | 0.0044 (9) |
C12 | 0.0314 (12) | 0.0474 (15) | 0.0234 (12) | 0.0100 (11) | −0.0047 (9) | 0.0055 (10) |
C13 | 0.0538 (17) | 0.0498 (17) | 0.0346 (15) | 0.0113 (13) | 0.0009 (12) | −0.0188 (12) |
C14 | 0.0422 (15) | 0.0382 (15) | 0.0479 (16) | 0.0060 (12) | −0.0174 (12) | −0.0152 (12) |
C15 | 0.0212 (10) | 0.0359 (13) | 0.0359 (13) | 0.0052 (9) | 0.0005 (9) | 0.0002 (10) |
C16 | 0.0281 (11) | 0.0237 (11) | 0.0349 (13) | 0.0093 (9) | −0.0062 (9) | −0.0021 (9) |
C17 | 0.0197 (9) | 0.0219 (10) | 0.0181 (10) | 0.0086 (8) | 0.0027 (7) | 0.0031 (7) |
C18 | 0.0283 (11) | 0.0249 (11) | 0.0222 (11) | 0.0129 (9) | 0.0010 (8) | 0.0019 (8) |
C19 | 0.0446 (14) | 0.0362 (13) | 0.0272 (12) | 0.0269 (11) | 0.0021 (9) | 0.0007 (9) |
C20 | 0.0322 (12) | 0.0541 (16) | 0.0330 (13) | 0.0291 (12) | 0.0080 (9) | 0.0053 (11) |
C21 | 0.0202 (11) | 0.0484 (16) | 0.0515 (16) | 0.0127 (10) | 0.0087 (10) | 0.0101 (12) |
C22 | 0.0215 (10) | 0.0284 (12) | 0.0425 (14) | 0.0090 (9) | 0.0061 (9) | 0.0047 (9) |
C23 | 0.0182 (9) | 0.0166 (9) | 0.0201 (10) | 0.0067 (7) | 0.0018 (7) | −0.0021 (7) |
C24 | 0.0192 (10) | 0.0249 (11) | 0.0302 (12) | 0.0037 (8) | 0.0012 (8) | 0.0050 (8) |
C25 | 0.0237 (11) | 0.0349 (13) | 0.0366 (13) | 0.0053 (9) | −0.0081 (9) | 0.0043 (10) |
C26 | 0.0344 (12) | 0.0328 (12) | 0.0242 (12) | 0.0140 (10) | −0.0033 (9) | 0.0052 (9) |
C27 | 0.0307 (11) | 0.0217 (10) | 0.0262 (11) | 0.0111 (9) | 0.0079 (8) | 0.0054 (8) |
C28 | 0.0199 (9) | 0.0185 (10) | 0.0237 (11) | 0.0045 (8) | 0.0032 (7) | −0.0004 (7) |
N1 | 0.0183 (8) | 0.0159 (8) | 0.0175 (8) | 0.0020 (6) | 0.0015 (6) | −0.0018 (6) |
N2 | 0.0182 (8) | 0.0143 (8) | 0.0221 (9) | 0.0016 (6) | 0.0016 (6) | −0.0014 (6) |
N3 | 0.0202 (8) | 0.0144 (8) | 0.0204 (9) | 0.0002 (6) | 0.0041 (6) | −0.0024 (6) |
N4 | 0.0142 (8) | 0.0239 (9) | 0.0175 (9) | 0.0006 (6) | 0.0009 (6) | −0.0006 (7) |
N5 | 0.0231 (9) | 0.0193 (9) | 0.0284 (10) | 0.0070 (7) | 0.0020 (7) | 0.0042 (7) |
O1 | 0.0179 (7) | 0.0175 (7) | 0.0251 (8) | 0.0037 (5) | −0.0012 (5) | 0.0027 (5) |
O2 | 0.0201 (7) | 0.0367 (9) | 0.0238 (8) | 0.0069 (6) | −0.0017 (6) | 0.0016 (6) |
O3 | 0.0359 (9) | 0.0374 (9) | 0.0268 (9) | 0.0066 (7) | 0.0007 (6) | −0.0039 (7) |
O4 | 0.0370 (10) | 0.0403 (10) | 0.0521 (12) | 0.0130 (8) | −0.0162 (8) | −0.0181 (8) |
O5 | 0.0204 (7) | 0.0220 (7) | 0.0246 (8) | 0.0025 (6) | −0.0044 (5) | −0.0034 (6) |
P1 | 0.0138 (2) | 0.0141 (2) | 0.0182 (3) | 0.00145 (18) | 0.00126 (17) | −0.00036 (17) |
P2 | 0.0167 (2) | 0.0133 (2) | 0.0184 (3) | 0.00338 (18) | −0.00132 (17) | −0.00102 (17) |
P3 | 0.0140 (2) | 0.0139 (2) | 0.0194 (3) | 0.00269 (18) | 0.00293 (17) | −0.00023 (18) |
C1—N4 | 1.484 (2) | C14—H14A | 0.9900 |
C1—C4 | 1.519 (3) | C14—H14B | 0.9900 |
C1—C3 | 1.526 (3) | C15—O4 | 1.404 (3) |
C1—C2 | 1.526 (3) | C15—C16 | 1.490 (3) |
C2—H2A | 0.9800 | C15—H15A | 0.9900 |
C2—H2B | 0.9800 | C15—H15B | 0.9900 |
C2—H2C | 0.9800 | C16—O5 | 1.435 (3) |
C3—H3A | 0.9800 | C16—H16A | 0.9900 |
C3—H3B | 0.9800 | C16—H16B | 0.9900 |
C3—H3C | 0.9800 | C17—C18 | 1.386 (3) |
C4—H4A | 0.9800 | C17—C22 | 1.394 (3) |
C4—H4B | 0.9800 | C17—P3 | 1.8044 (19) |
C4—H4C | 0.9800 | C18—C19 | 1.388 (3) |
C5—N5 | 1.478 (3) | C18—H18 | 0.9500 |
C5—C6 | 1.511 (3) | C19—C20 | 1.367 (3) |
C5—C8 | 1.525 (3) | C19—H19 | 0.9500 |
C5—C7 | 1.541 (3) | C20—C21 | 1.374 (4) |
C6—H6A | 0.9800 | C20—H20 | 0.9500 |
C6—H6B | 0.9800 | C21—C22 | 1.391 (3) |
C6—H6C | 0.9800 | C21—H21 | 0.9500 |
C7—H7A | 0.9800 | C22—H22 | 0.9500 |
C7—H7B | 0.9800 | C23—C24 | 1.388 (3) |
C7—H7C | 0.9800 | C23—C28 | 1.395 (3) |
C8—H8A | 0.9800 | C23—P3 | 1.805 (2) |
C8—H8B | 0.9800 | C24—C25 | 1.384 (3) |
C8—H8C | 0.9800 | C24—H24 | 0.9500 |
C9—O1 | 1.440 (2) | C25—C26 | 1.384 (3) |
C9—C10 | 1.501 (3) | C25—H25 | 0.9500 |
C9—H9A | 0.9900 | C26—C27 | 1.389 (3) |
C9—H9B | 0.9900 | C26—H26 | 0.9500 |
C10—O2 | 1.418 (2) | C27—C28 | 1.378 (3) |
C10—H10A | 0.9900 | C27—H27 | 0.9500 |
C10—H10B | 0.9900 | C28—H28 | 0.9500 |
C11—O2 | 1.415 (3) | N1—P2 | 1.5891 (16) |
C11—C12 | 1.506 (3) | N1—P1 | 1.5905 (16) |
C11—H11A | 0.9900 | N2—P2 | 1.5957 (16) |
C11—H11B | 0.9900 | N2—P3 | 1.5972 (16) |
C12—O3 | 1.423 (3) | N3—P1 | 1.5908 (16) |
C12—H12A | 0.9900 | N3—P3 | 1.5992 (16) |
C12—H12B | 0.9900 | N4—P1 | 1.6341 (16) |
C13—O3 | 1.434 (3) | N4—H4 | 0.76 (3) |
C13—C14 | 1.476 (4) | N5—P2 | 1.6470 (18) |
C13—H13A | 0.9900 | N5—H5 | 0.95 (3) |
C13—H13B | 0.9900 | O1—P1 | 1.5954 (14) |
C14—O4 | 1.433 (3) | O5—P2 | 1.5786 (14) |
N4—C1—C4 | 109.83 (17) | C13—C14—H14B | 108.6 |
N4—C1—C3 | 110.44 (17) | H14A—C14—H14B | 107.6 |
C4—C1—C3 | 111.09 (19) | O4—C15—C16 | 112.71 (19) |
N4—C1—C2 | 106.50 (17) | O4—C15—H15A | 109.1 |
C4—C1—C2 | 109.04 (18) | C16—C15—H15A | 109.1 |
C3—C1—C2 | 109.82 (19) | O4—C15—H15B | 109.1 |
C1—C2—H2A | 109.5 | C16—C15—H15B | 109.1 |
C1—C2—H2B | 109.5 | H15A—C15—H15B | 107.8 |
H2A—C2—H2B | 109.5 | O5—C16—C15 | 110.32 (18) |
C1—C2—H2C | 109.5 | O5—C16—H16A | 109.6 |
H2A—C2—H2C | 109.5 | C15—C16—H16A | 109.6 |
H2B—C2—H2C | 109.5 | O5—C16—H16B | 109.6 |
C1—C3—H3A | 109.5 | C15—C16—H16B | 109.6 |
C1—C3—H3B | 109.5 | H16A—C16—H16B | 108.1 |
H3A—C3—H3B | 109.5 | C18—C17—C22 | 119.29 (18) |
C1—C3—H3C | 109.5 | C18—C17—P3 | 119.36 (15) |
H3A—C3—H3C | 109.5 | C22—C17—P3 | 121.28 (16) |
H3B—C3—H3C | 109.5 | C17—C18—C19 | 120.2 (2) |
C1—C4—H4A | 109.5 | C17—C18—H18 | 119.9 |
C1—C4—H4B | 109.5 | C19—C18—H18 | 119.9 |
H4A—C4—H4B | 109.5 | C20—C19—C18 | 120.0 (2) |
C1—C4—H4C | 109.5 | C20—C19—H19 | 120.0 |
H4A—C4—H4C | 109.5 | C18—C19—H19 | 120.0 |
H4B—C4—H4C | 109.5 | C19—C20—C21 | 120.8 (2) |
N5—C5—C6 | 112.47 (18) | C19—C20—H20 | 119.6 |
N5—C5—C8 | 106.63 (17) | C21—C20—H20 | 119.6 |
C6—C5—C8 | 111.03 (19) | C20—C21—C22 | 119.9 (2) |
N5—C5—C7 | 108.85 (17) | C20—C21—H21 | 120.1 |
C6—C5—C7 | 109.53 (19) | C22—C21—H21 | 120.1 |
C8—C5—C7 | 108.19 (18) | C21—C22—C17 | 119.8 (2) |
C5—C6—H6A | 109.5 | C21—C22—H22 | 120.1 |
C5—C6—H6B | 109.5 | C17—C22—H22 | 120.1 |
H6A—C6—H6B | 109.5 | C24—C23—C28 | 118.82 (18) |
C5—C6—H6C | 109.5 | C24—C23—P3 | 121.18 (15) |
H6A—C6—H6C | 109.5 | C28—C23—P3 | 119.99 (14) |
H6B—C6—H6C | 109.5 | C25—C24—C23 | 120.68 (19) |
C5—C7—H7A | 109.5 | C25—C24—H24 | 119.7 |
C5—C7—H7B | 109.5 | C23—C24—H24 | 119.7 |
H7A—C7—H7B | 109.5 | C26—C25—C24 | 120.0 (2) |
C5—C7—H7C | 109.5 | C26—C25—H25 | 120.0 |
H7A—C7—H7C | 109.5 | C24—C25—H25 | 120.0 |
H7B—C7—H7C | 109.5 | C25—C26—C27 | 119.9 (2) |
C5—C8—H8A | 109.5 | C25—C26—H26 | 120.1 |
C5—C8—H8B | 109.5 | C27—C26—H26 | 120.1 |
H8A—C8—H8B | 109.5 | C28—C27—C26 | 119.94 (19) |
C5—C8—H8C | 109.5 | C28—C27—H27 | 120.0 |
H8A—C8—H8C | 109.5 | C26—C27—H27 | 120.0 |
H8B—C8—H8C | 109.5 | C27—C28—C23 | 120.69 (18) |
O1—C9—C10 | 109.58 (16) | C27—C28—H28 | 119.7 |
O1—C9—H9A | 109.8 | C23—C28—H28 | 119.7 |
C10—C9—H9A | 109.8 | P2—N1—P1 | 123.56 (10) |
O1—C9—H9B | 109.8 | P2—N2—P3 | 121.21 (10) |
C10—C9—H9B | 109.8 | P1—N3—P3 | 121.55 (10) |
H9A—C9—H9B | 108.2 | C1—N4—P1 | 128.16 (14) |
O2—C10—C9 | 107.31 (16) | C1—N4—H4 | 114 (2) |
O2—C10—H10A | 110.3 | P1—N4—H4 | 113 (2) |
C9—C10—H10A | 110.3 | C5—N5—P2 | 129.13 (14) |
O2—C10—H10B | 110.3 | C5—N5—H5 | 113.7 (19) |
C9—C10—H10B | 110.3 | P2—N5—H5 | 112.8 (19) |
H10A—C10—H10B | 108.5 | C9—O1—P1 | 118.53 (12) |
O2—C11—C12 | 108.55 (18) | C11—O2—C10 | 112.13 (16) |
O2—C11—H11A | 110.0 | C12—O3—C13 | 113.91 (19) |
C12—C11—H11A | 110.0 | C15—O4—C14 | 115.60 (19) |
O2—C11—H11B | 110.0 | C16—O5—P2 | 118.41 (13) |
C12—C11—H11B | 110.0 | N1—P1—N3 | 116.52 (8) |
H11A—C11—H11B | 108.4 | N1—P1—O1 | 106.65 (8) |
O3—C12—C11 | 112.73 (18) | N3—P1—O1 | 110.61 (8) |
O3—C12—H12A | 109.0 | N1—P1—N4 | 114.64 (9) |
C11—C12—H12A | 109.0 | N3—P1—N4 | 106.50 (9) |
O3—C12—H12B | 109.0 | O1—P1—N4 | 100.81 (8) |
C11—C12—H12B | 109.0 | O5—P2—N1 | 110.05 (8) |
H12A—C12—H12B | 107.8 | O5—P2—N2 | 107.11 (8) |
O3—C13—C14 | 110.0 (2) | N1—P2—N2 | 116.41 (8) |
O3—C13—H13A | 109.7 | O5—P2—N5 | 102.25 (8) |
C14—C13—H13A | 109.7 | N1—P2—N5 | 105.62 (9) |
O3—C13—H13B | 109.7 | N2—P2—N5 | 114.48 (9) |
C14—C13—H13B | 109.7 | N2—P3—N3 | 118.32 (8) |
H13A—C13—H13B | 108.2 | N2—P3—C17 | 108.54 (9) |
O4—C14—C13 | 114.8 (2) | N3—P3—C17 | 108.97 (9) |
O4—C14—H14A | 108.6 | N2—P3—C23 | 108.99 (9) |
C13—C14—H14A | 108.6 | N3—P3—C23 | 107.84 (9) |
O4—C14—H14B | 108.6 | C17—P3—C23 | 103.12 (9) |
O1—C9—C10—O2 | −174.98 (15) | P3—N3—P1—O1 | −112.92 (12) |
O2—C11—C12—O3 | 69.5 (3) | P3—N3—P1—N4 | 138.40 (12) |
O3—C13—C14—O4 | 75.1 (3) | C9—O1—P1—N1 | −50.98 (15) |
O4—C15—C16—O5 | 66.0 (3) | C9—O1—P1—N3 | 76.63 (15) |
C22—C17—C18—C19 | −1.0 (3) | C9—O1—P1—N4 | −170.99 (14) |
P3—C17—C18—C19 | 176.09 (16) | C1—N4—P1—N1 | −36.3 (2) |
C17—C18—C19—C20 | −0.3 (3) | C1—N4—P1—N3 | −166.73 (17) |
C18—C19—C20—C21 | 0.7 (4) | C1—N4—P1—O1 | 77.79 (18) |
C19—C20—C21—C22 | 0.3 (4) | C16—O5—P2—N1 | 71.35 (16) |
C20—C21—C22—C17 | −1.6 (4) | C16—O5—P2—N2 | −56.07 (16) |
C18—C17—C22—C21 | 1.9 (3) | C16—O5—P2—N5 | −176.77 (15) |
P3—C17—C22—C21 | −175.09 (18) | P1—N1—P2—O5 | −137.73 (11) |
C28—C23—C24—C25 | 0.4 (3) | P1—N1—P2—N2 | −15.66 (16) |
P3—C23—C24—C25 | −179.43 (17) | P1—N1—P2—N5 | 112.60 (12) |
C23—C24—C25—C26 | −0.3 (3) | P3—N2—P2—O5 | 136.41 (11) |
C24—C25—C26—C27 | −0.3 (3) | P3—N2—P2—N1 | 12.81 (15) |
C25—C26—C27—C28 | 0.9 (3) | P3—N2—P2—N5 | −111.01 (12) |
C26—C27—C28—C23 | −0.9 (3) | C5—N5—P2—O5 | 75.56 (19) |
C24—C23—C28—C27 | 0.2 (3) | C5—N5—P2—N1 | −169.28 (17) |
P3—C23—C28—C27 | −179.95 (15) | C5—N5—P2—N2 | −39.9 (2) |
C4—C1—N4—P1 | −45.8 (2) | P2—N2—P3—N3 | 0.08 (16) |
C3—C1—N4—P1 | 77.1 (2) | P2—N2—P3—C17 | −124.68 (12) |
C2—C1—N4—P1 | −163.68 (16) | P2—N2—P3—C23 | 123.68 (12) |
C6—C5—N5—P2 | 69.8 (2) | P1—N3—P3—N2 | −11.53 (16) |
C8—C5—N5—P2 | −168.29 (16) | P1—N3—P3—C17 | 113.02 (12) |
C7—C5—N5—P2 | −51.8 (2) | P1—N3—P3—C23 | −135.71 (12) |
C10—C9—O1—P1 | 101.89 (17) | C18—C17—P3—N2 | 155.28 (16) |
C12—C11—O2—C10 | −168.37 (18) | C22—C17—P3—N2 | −27.7 (2) |
C9—C10—O2—C11 | 174.44 (18) | C18—C17—P3—N3 | 25.15 (19) |
C11—C12—O3—C13 | 90.4 (2) | C22—C17—P3—N3 | −157.84 (17) |
C14—C13—O3—C12 | −177.1 (2) | C18—C17—P3—C23 | −89.22 (17) |
C16—C15—O4—C14 | 112.9 (2) | C22—C17—P3—C23 | 87.78 (18) |
C13—C14—O4—C15 | −82.5 (3) | C24—C23—P3—N2 | −121.33 (17) |
C15—C16—O5—P2 | 143.27 (16) | C28—C23—P3—N2 | 58.87 (17) |
P2—N1—P1—N3 | 4.97 (16) | C24—C23—P3—N3 | 8.30 (19) |
P2—N1—P1—O1 | 129.01 (11) | C28—C23—P3—N3 | −171.50 (15) |
P2—N1—P1—N4 | −120.35 (12) | C24—C23—P3—C17 | 123.49 (17) |
P3—N3—P1—N1 | 9.06 (16) | C28—C23—P3—C17 | −56.31 (17) |
Experimental details
(3) | (4) | (5) | (6) | |
Crystal data | ||||
Chemical formula | C20H26Cl2N3O5P3 | C24H30F6N3O7P3 | C32H36N3O7P3 | C22H32N3O7P3 |
Mr | 552.25 | 679.42 | 667.55 | 543.42 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Triclinic, P1 | Monoclinic, P21/n |
Temperature (K) | 150 | 120 | 150 | 293 |
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), 90 | 90, 105.877 (1), 90 | 88.86 (3), 86.54 (3), 78.14 (3) | 90, 100.203 (1), 90 |
V (Å3) | 2508.8 (9) | 2888.46 (15) | 1600.4 (6) | 2601.84 (9) |
Z | 4 | 4 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.49 | 0.29 | 0.24 | 0.28 |
Crystal size (mm) | 0.32 × 0.28 × 0.13 | 0.18 × 0.10 × 0.03 | 0.20 × 0.15 × 0.10 | 0.26 × 0.20 × 0.07 |
Data collection | ||||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SORTAV (Blessing, 1997) | Multi-scan SORTAV (Blessing, 1997) | Multi-scan SORTAV (Blessing, 1997) | Multi-scan SORTAV (Blessing, 1997) |
Tmin, Tmax | 0.860, 0.939 | 0.949, 0.991 | 0.954, 0.977 | 0.932, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17345, 5657, 4268 | 22797, 6488, 3777 | 24220, 12306, 8750 | 18814, 5841, 4160 |
Rint | 0.045 | 0.083 | 0.061 | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
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 reflections | 5657 | 6488 | 12306 | 5841 |
No. of parameters | 299 | 389 | 824 | 319 |
No. of restraints | 0 | 0 | 22 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.46 | 0.38, −0.38 | 0.81, −0.40 | 0.46, −0.31 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | ? | ? | 0.03 (7) | ? |
(7) | (8) | |
Crystal data | ||
Chemical formula | C32H40N5O6P3 | C28H46N5O5P3 |
Mr | 683.60 | 625.61 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 120 |
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) |
V (Å3) | 1659.6 (6) | 1602.79 (6) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.23 | 0.23 |
Crystal size (mm) | 0.30 × 0.17 × 0.08 | 0.27 × 0.18 × 0.12 |
Data collection | ||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SORTAV (Blessing, 1997) | Multi-scan SORTAV (Blessing, 1997) |
Tmin, Tmax | 0.934, 0.983 | 0.941, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19478, 7460, 6157 | 20859, 7079, 5682 |
Rint | 0.033 | 0.091 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.120, 0.65 | 0.045, 0.125, 1.01 |
No. of reflections | 7460 | 7079 |
No. of parameters | 431 | 385 |
No. of restraints | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.45 | 0.72, −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).