New phosphoramidates with the formula RC(O)N(H)P(O)X2, R = 2-NO2—C6H4, 3-NO2—C6H4 and 4-NO2—C6H4, X = N(CH2CH3) (1)–(3), NC4H8 (4)–(6), and NC4H8O (7)–(9) were synthesized and characterized by 1H, 13C, 31P NMR and IR spectroscopy, and elemental analysis. The reaction of (9) with hydrated lanthanide(III) nitrate leads to ten- or nine-coordinated complexes, (10)–(13). The crystal structure has been determined for (3), (5), (9), (10) and (13). In contrast to all of the previously reported similar phosphoramidate compounds, the —C(O)—N(H)—P(O) skeleton in the free ligand (9) shows a cisoid conformation, with the C=O and P=O double bonds adopting a nearly syn conformation. Quantum chemical calculations were applied for clarifying this exceptional conformational behavior. The monodentate neutral ligand (9) is coordinated to the metal ions via the phosphoryl O atom, adopting the usual anti conformation between the C=O and P=O groups.
Supporting information
CCDC references: 678070; 678074; 691914; 709114; 713519
Data collection: SMART (Bruker, 1998b) for (3), (9); CrysAlis CCD (Oxford diffraction, 2007) for (5); Bruker APEX II for (10); X-AREA V1.35 (Stoe & Cie, 2006) for (13). Cell refinement: SAINTPlus (Bruker, 1998a) for (3), (9); CrysAlis RED (Oxford diffraction, 2007) for (5); Bruker SAINT for (10); X-AREA V1.35 for (13). Data reduction: SAINTPlus (Bruker, 1998a) for (3), (9); CrysAlis RED (Oxford diffraction, 2007) for (5); Bruker SAINT for (10); X-RED32 V1.31 (Stoe & Cie, 2006) for (13). Program(s) used to solve structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Superflip(Palatinus L., Chapuis G., 2007) for (5); SHELXS97 (Sheldrick, 1997) for (10); SHELXS97 (Sheldrick, 2008) for (13). Program(s) used to refine structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Jana2006 (Petricek, Dusek & Palatinus, 2006) for (5); SHELXL97 (Sheldrick, 1997) for (10); SHELXL97 (Sheldrick, 2008) for (13). Molecular graphics: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Diamond (Brandenburg & Putz, 2005) for (5); Bruker SHELXTL for (10); ORTEP-3 (Farrugia, 1997) & PLATON (Spek, 2003) for (13). Software used to prepare material for publication: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (3), (9); Jana2006 (Petricek, Dusek & Palatinus, 2006) for (5); Bruker SHELXTL for (10); SHELXL97 for (13).
Crystal data top
C15H25N4O4P | F(000) = 760 |
Mr = 356.36 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 282 reflections |
a = 9.9548 (8) Å | θ = 3–27° |
b = 20.3681 (16) Å | µ = 0.18 mm−1 |
c = 8.8471 (7) Å | T = 120 K |
β = 96.125 (2)° | Prism, colorless |
V = 1783.6 (2) Å3 | 0.30 × 0.26 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area detector diffractometer | 3882 independent reflections |
Radiation source: fine-focus sealed tube | 2498 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
phi and ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan SADABS (Sheldrick, 1998a) | h = −12→12 |
Tmin = 0.945, Tmax = 0.963 | k = −25→26 |
16991 measured reflections | l = −11→11 |
Refinement top
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)] = 0.056 | Hydrogen site location: mixed |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.030P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3 |
3882 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.47911 (6) | 0.42644 (3) | 0.19450 (7) | 0.02303 (17) | |
O1 | 0.44076 (17) | 0.49667 (8) | 0.17400 (19) | 0.0286 (4) | |
O2 | 0.67356 (18) | 0.31382 (9) | 0.1506 (2) | 0.0316 (4) | |
O3 | 1.0652 (2) | 0.29200 (10) | −0.4422 (2) | 0.0483 (6) | |
O4 | 1.0988 (2) | 0.39665 (10) | −0.4259 (2) | 0.0479 (6) | |
N1 | 0.58241 (19) | 0.41046 (10) | 0.0589 (2) | 0.0228 (5) | |
H1N | 0.5780 | 0.4387 | −0.0152 | 0.027* | |
N2 | 0.5543 (2) | 0.41485 (9) | 0.3662 (2) | 0.0231 (5) | |
N3 | 0.3566 (2) | 0.37308 (11) | 0.1670 (2) | 0.0270 (5) | |
N4 | 1.0434 (2) | 0.34648 (12) | −0.3906 (2) | 0.0321 (5) | |
C1 | 0.6529 (3) | 0.46413 (13) | 0.4305 (3) | 0.0293 (6) | |
H1A | 0.6584 | 0.4624 | 0.5428 | 0.035* | |
H1B | 0.6206 | 0.5084 | 0.3980 | 0.035* | |
C2 | 0.7933 (3) | 0.45344 (15) | 0.3815 (3) | 0.0408 (7) | |
H2A | 0.8585 | 0.4811 | 0.4431 | 0.061* | |
H2B | 0.7930 | 0.4651 | 0.2740 | 0.061* | |
H2C | 0.8188 | 0.4072 | 0.3959 | 0.061* | |
C3 | 0.5636 (3) | 0.35060 (12) | 0.4445 (3) | 0.0259 (6) | |
H3A | 0.6598 | 0.3379 | 0.4652 | 0.031* | |
H3B | 0.5177 | 0.3169 | 0.3768 | 0.031* | |
C4 | 0.4997 (3) | 0.35200 (13) | 0.5940 (3) | 0.0317 (6) | |
H4A | 0.5175 | 0.3103 | 0.6477 | 0.048* | |
H4B | 0.4020 | 0.3585 | 0.5728 | 0.048* | |
H4C | 0.5388 | 0.3881 | 0.6574 | 0.048* | |
C5 | 0.2479 (3) | 0.37638 (16) | 0.2668 (3) | 0.0377 (7) | |
H5A | 0.2688 | 0.4119 | 0.3420 | 0.045* | |
H5B | 0.2457 | 0.3345 | 0.3235 | 0.045* | |
C6 | 0.1086 (3) | 0.38878 (15) | 0.1826 (3) | 0.0397 (7) | |
H6A | 0.0419 | 0.3921 | 0.2561 | 0.059* | |
H6B | 0.0844 | 0.3523 | 0.1127 | 0.059* | |
H6C | 0.1100 | 0.4298 | 0.1250 | 0.059* | |
C7 | 0.3464 (3) | 0.32153 (14) | 0.0515 (3) | 0.0383 (7) | |
H7A | 0.2874 | 0.2861 | 0.0834 | 0.046* | |
H7B | 0.4372 | 0.3025 | 0.0455 | 0.046* | |
C8 | 0.2909 (3) | 0.3451 (2) | −0.1048 (3) | 0.0613 (11) | |
H8A | 0.2864 | 0.3082 | −0.1763 | 0.092* | |
H8B | 0.3502 | 0.3793 | −0.1388 | 0.092* | |
H8C | 0.2001 | 0.3632 | −0.1006 | 0.092* | |
C9 | 0.6704 (2) | 0.35874 (12) | 0.0589 (3) | 0.0226 (5) | |
C10 | 0.7662 (2) | 0.35858 (12) | −0.0615 (3) | 0.0224 (5) | |
C11 | 0.8041 (3) | 0.29821 (13) | −0.1147 (3) | 0.0290 (6) | |
H11A | 0.7683 | 0.2592 | −0.0757 | 0.035* | |
C12 | 0.8933 (3) | 0.29370 (13) | −0.2238 (3) | 0.0300 (6) | |
H12A | 0.9182 | 0.2522 | −0.2613 | 0.036* | |
C13 | 0.9450 (2) | 0.35078 (13) | −0.2765 (3) | 0.0245 (6) | |
C14 | 0.9100 (3) | 0.41189 (13) | −0.2268 (3) | 0.0273 (6) | |
H14A | 0.9476 | 0.4505 | −0.2653 | 0.033* | |
C15 | 0.8184 (2) | 0.41585 (12) | −0.1192 (3) | 0.0253 (6) | |
H15A | 0.7913 | 0.4575 | −0.0850 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0215 (3) | 0.0266 (4) | 0.0221 (3) | 0.0032 (3) | 0.0072 (3) | 0.0020 (3) |
O1 | 0.0336 (10) | 0.0295 (10) | 0.0241 (9) | 0.0096 (8) | 0.0099 (8) | 0.0041 (8) |
O2 | 0.0340 (11) | 0.0311 (10) | 0.0324 (10) | 0.0075 (8) | 0.0157 (8) | 0.0089 (8) |
O3 | 0.0496 (13) | 0.0513 (14) | 0.0490 (13) | −0.0013 (11) | 0.0280 (11) | −0.0175 (11) |
O4 | 0.0492 (13) | 0.0493 (13) | 0.0510 (14) | 0.0016 (11) | 0.0322 (11) | 0.0075 (11) |
N1 | 0.0223 (11) | 0.0286 (12) | 0.0187 (10) | 0.0011 (9) | 0.0081 (8) | 0.0048 (9) |
N2 | 0.0218 (11) | 0.0220 (11) | 0.0263 (11) | 0.0017 (8) | 0.0068 (9) | 0.0035 (9) |
N3 | 0.0240 (11) | 0.0366 (13) | 0.0217 (11) | −0.0012 (9) | 0.0089 (9) | −0.0007 (9) |
N4 | 0.0267 (12) | 0.0455 (15) | 0.0255 (12) | 0.0053 (11) | 0.0095 (10) | −0.0028 (11) |
C1 | 0.0322 (15) | 0.0282 (14) | 0.0275 (14) | −0.0045 (12) | 0.0025 (12) | 0.0001 (11) |
C2 | 0.0342 (16) | 0.0532 (19) | 0.0353 (16) | −0.0107 (14) | 0.0054 (13) | 0.0010 (14) |
C3 | 0.0279 (14) | 0.0262 (14) | 0.0241 (13) | 0.0023 (11) | 0.0048 (11) | 0.0027 (11) |
C4 | 0.0390 (16) | 0.0314 (15) | 0.0253 (14) | −0.0009 (12) | 0.0065 (12) | 0.0029 (11) |
C5 | 0.0279 (15) | 0.0588 (19) | 0.0281 (15) | −0.0080 (14) | 0.0107 (12) | −0.0016 (14) |
C6 | 0.0277 (15) | 0.057 (2) | 0.0364 (17) | −0.0017 (14) | 0.0114 (13) | −0.0058 (14) |
C7 | 0.0265 (15) | 0.0381 (17) | 0.0525 (19) | −0.0070 (12) | 0.0146 (13) | −0.0112 (14) |
C8 | 0.0381 (19) | 0.114 (3) | 0.0322 (18) | −0.012 (2) | 0.0070 (14) | −0.0267 (19) |
C9 | 0.0201 (12) | 0.0252 (13) | 0.0234 (13) | 0.0018 (10) | 0.0073 (10) | 0.0008 (11) |
C10 | 0.0187 (12) | 0.0289 (14) | 0.0205 (12) | 0.0017 (10) | 0.0067 (10) | 0.0018 (10) |
C11 | 0.0310 (15) | 0.0251 (14) | 0.0330 (15) | −0.0040 (11) | 0.0133 (12) | −0.0022 (11) |
C12 | 0.0297 (15) | 0.0268 (14) | 0.0351 (15) | 0.0003 (11) | 0.0107 (12) | −0.0084 (12) |
C13 | 0.0175 (12) | 0.0375 (15) | 0.0195 (12) | 0.0020 (11) | 0.0068 (10) | −0.0033 (11) |
C14 | 0.0253 (13) | 0.0306 (15) | 0.0272 (14) | 0.0018 (11) | 0.0083 (11) | 0.0052 (11) |
C15 | 0.0247 (13) | 0.0269 (14) | 0.0251 (13) | 0.0037 (11) | 0.0059 (11) | 0.0012 (11) |
Geometric parameters (Å, º) top
P1—O1 | 1.4866 (18) | C4—H4C | 0.9800 |
P1—N3 | 1.632 (2) | C5—C6 | 1.523 (4) |
P1—N2 | 1.637 (2) | C5—H5A | 0.9900 |
P1—N1 | 1.693 (2) | C5—H5B | 0.9900 |
O2—C9 | 1.221 (3) | C6—H6A | 0.9800 |
O3—N4 | 1.228 (3) | C6—H6B | 0.9800 |
O4—N4 | 1.217 (3) | C6—H6C | 0.9800 |
N1—C9 | 1.370 (3) | C7—C8 | 1.512 (4) |
N1—H1N | 0.8699 | C7—H7A | 0.9900 |
N2—C1 | 1.475 (3) | C7—H7B | 0.9900 |
N2—C3 | 1.479 (3) | C8—H8A | 0.9800 |
N3—C7 | 1.461 (3) | C8—H8B | 0.9800 |
N3—C5 | 1.469 (3) | C8—H8C | 0.9800 |
N4—C13 | 1.483 (3) | C9—C10 | 1.504 (3) |
C1—C2 | 1.523 (4) | C10—C11 | 1.383 (3) |
C1—H1A | 0.9900 | C10—C15 | 1.396 (3) |
C1—H1B | 0.9900 | C11—C12 | 1.383 (3) |
C2—H2A | 0.9800 | C11—H11A | 0.9500 |
C2—H2B | 0.9800 | C12—C13 | 1.373 (4) |
C2—H2C | 0.9800 | C12—H12A | 0.9500 |
C3—C4 | 1.528 (3) | C13—C14 | 1.377 (3) |
C3—H3A | 0.9900 | C14—C15 | 1.389 (3) |
C3—H3B | 0.9900 | C14—H14A | 0.9500 |
C4—H4A | 0.9800 | C15—H15A | 0.9500 |
C4—H4B | 0.9800 | | |
| | | |
O1—P1—N3 | 116.39 (11) | C6—C5—H5A | 108.8 |
O1—P1—N2 | 109.75 (10) | N3—C5—H5B | 108.8 |
N3—P1—N2 | 107.62 (11) | C6—C5—H5B | 108.8 |
O1—P1—N1 | 105.43 (10) | H5A—C5—H5B | 107.7 |
N3—P1—N1 | 105.49 (10) | C5—C6—H6A | 109.5 |
N2—P1—N1 | 112.16 (10) | C5—C6—H6B | 109.5 |
C9—N1—P1 | 125.78 (17) | H6A—C6—H6B | 109.5 |
C9—N1—H1N | 119.3 | C5—C6—H6C | 109.5 |
P1—N1—H1N | 114.9 | H6A—C6—H6C | 109.5 |
C1—N2—C3 | 114.6 (2) | H6B—C6—H6C | 109.5 |
C1—N2—P1 | 118.66 (16) | N3—C7—C8 | 113.7 (3) |
C3—N2—P1 | 124.17 (17) | N3—C7—H7A | 108.8 |
C7—N3—C5 | 116.9 (2) | C8—C7—H7A | 108.8 |
C7—N3—P1 | 125.28 (17) | N3—C7—H7B | 108.8 |
C5—N3—P1 | 117.79 (18) | C8—C7—H7B | 108.8 |
O4—N4—O3 | 124.1 (2) | H7A—C7—H7B | 107.7 |
O4—N4—C13 | 118.4 (2) | C7—C8—H8A | 109.5 |
O3—N4—C13 | 117.5 (2) | C7—C8—H8B | 109.5 |
N2—C1—C2 | 112.7 (2) | H8A—C8—H8B | 109.5 |
N2—C1—H1A | 109.1 | C7—C8—H8C | 109.5 |
C2—C1—H1A | 109.1 | H8A—C8—H8C | 109.5 |
N2—C1—H1B | 109.1 | H8B—C8—H8C | 109.5 |
C2—C1—H1B | 109.1 | O2—C9—N1 | 123.2 (2) |
H1A—C1—H1B | 107.8 | O2—C9—C10 | 119.7 (2) |
C1—C2—H2A | 109.5 | N1—C9—C10 | 117.1 (2) |
C1—C2—H2B | 109.5 | C11—C10—C15 | 119.5 (2) |
H2A—C2—H2B | 109.5 | C11—C10—C9 | 117.4 (2) |
C1—C2—H2C | 109.5 | C15—C10—C9 | 123.1 (2) |
H2A—C2—H2C | 109.5 | C12—C11—C10 | 121.0 (2) |
H2B—C2—H2C | 109.5 | C12—C11—H11A | 119.5 |
N2—C3—C4 | 112.2 (2) | C10—C11—H11A | 119.5 |
N2—C3—H3A | 109.2 | C13—C12—C11 | 118.2 (2) |
C4—C3—H3A | 109.2 | C13—C12—H12A | 120.9 |
N2—C3—H3B | 109.2 | C11—C12—H12A | 120.9 |
C4—C3—H3B | 109.2 | C12—C13—C14 | 122.7 (2) |
H3A—C3—H3B | 107.9 | C12—C13—N4 | 118.7 (2) |
C3—C4—H4A | 109.5 | C14—C13—N4 | 118.6 (2) |
C3—C4—H4B | 109.5 | C13—C14—C15 | 118.6 (2) |
H4A—C4—H4B | 109.5 | C13—C14—H14A | 120.7 |
C3—C4—H4C | 109.5 | C15—C14—H14A | 120.7 |
H4A—C4—H4C | 109.5 | C14—C15—C10 | 120.0 (2) |
H4B—C4—H4C | 109.5 | C14—C15—H15A | 120.0 |
N3—C5—C6 | 113.8 (2) | C10—C15—H15A | 120.0 |
N3—C5—H5A | 108.8 | | |
| | | |
O1—P1—N1—C9 | 161.2 (2) | P1—N3—C7—C8 | −81.2 (3) |
N3—P1—N1—C9 | −75.1 (2) | P1—N1—C9—O2 | 8.1 (4) |
N2—P1—N1—C9 | 41.8 (2) | P1—N1—C9—C10 | −172.03 (17) |
O1—P1—N2—C1 | −41.5 (2) | O2—C9—C10—C11 | 31.7 (4) |
N3—P1—N2—C1 | −169.07 (17) | N1—C9—C10—C11 | −148.2 (2) |
N1—P1—N2—C1 | 75.33 (19) | O2—C9—C10—C15 | −147.6 (3) |
O1—P1—N2—C3 | 157.84 (18) | N1—C9—C10—C15 | 32.5 (3) |
N3—P1—N2—C3 | 30.3 (2) | C15—C10—C11—C12 | 0.3 (4) |
N1—P1—N2—C3 | −85.3 (2) | C9—C10—C11—C12 | −179.1 (2) |
O1—P1—N3—C7 | 118.7 (2) | C10—C11—C12—C13 | 0.9 (4) |
N2—P1—N3—C7 | −117.7 (2) | C11—C12—C13—C14 | −1.0 (4) |
N1—P1—N3—C7 | 2.3 (2) | C11—C12—C13—N4 | 178.5 (2) |
O1—P1—N3—C5 | −61.8 (2) | O4—N4—C13—C12 | −173.0 (2) |
N2—P1—N3—C5 | 61.8 (2) | O3—N4—C13—C12 | 6.1 (3) |
N1—P1—N3—C5 | −178.31 (19) | O4—N4—C13—C14 | 6.6 (4) |
C3—N2—C1—C2 | 78.5 (3) | O3—N4—C13—C14 | −174.4 (2) |
P1—N2—C1—C2 | −83.9 (2) | C12—C13—C14—C15 | −0.1 (4) |
C1—N2—C3—C4 | 77.5 (3) | N4—C13—C14—C15 | −179.6 (2) |
P1—N2—C3—C4 | −121.2 (2) | C13—C14—C15—C10 | 1.4 (4) |
C7—N3—C5—C6 | −60.8 (3) | C11—C10—C15—C14 | −1.4 (4) |
P1—N3—C5—C6 | 119.7 (2) | C9—C10—C15—C14 | 177.9 (2) |
C5—N3—C7—C8 | 99.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.87 | 1.92 | 2.789 (3) | 177 |
Symmetry code: (i) −x+1, −y+1, −z. |
Crystal data top
C15H21N4O4P | Z = 2 |
Mr = 352.3 | F(000) = 372 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1631 (2) Å | Cell parameters from 10101 reflections |
b = 9.3224 (2) Å | θ = 3.0–39.2° |
c = 11.4353 (3) Å | µ = 0.19 mm−1 |
α = 109.909 (2)° | T = 120 K |
β = 110.445 (2)° | Irregular shape, yellow |
γ = 96.024 (2)° | 0.98 × 0.36 × 0.22 mm |
V = 832.33 (4) Å3 | |
Data collection top
Oxford Diffraction CCD diffractometer | 3460 independent reflections |
Radiation source: X-ray tube | 2983 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.3438 pixels mm-1 | θmax = 26.5°, θmin = 3.0° |
Rotation method data acquisition using ω scans | h = −11→11 |
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.16 (release 23-01-2008 CrysAlis171 .NET)
(compiled Jan 23 2008,18:08:03)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −11→11 |
Tmin = 0.942, Tmax = 1.000 | l = −14→14 |
10200 measured reflections | |
Refinement top
Refinement on F2 | 100 constraints |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.096 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 3.18 | (Δ/σ)max = 0.039 |
3460 reflections | Δρmax = 0.49 e Å−3 |
225 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | |
Special details top
Refinement. The refinement was carried out against all reflections. The conventional
R-factor is always based on F. The goodness of fit as well as
the weighted R-factor are based on F and F2 for
refinement carried out on F and F2, respectively. The
threshold expression is used only for calculating R-factors etc.
and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on
the experimental expectations, see _refine_ls_weighting_details, that does not
force S to be one. Therefore the values of S are usually larger
then the ones from the SHELX program. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.02647 (4) | 0.93374 (4) | 0.79195 (4) | 0.01391 (16) | |
O3 | −0.04741 (14) | 1.18415 (13) | 0.68630 (11) | 0.0252 (5) | |
O2 | −0.36096 (14) | 1.60495 (13) | 1.14465 (12) | 0.0289 (5) | |
O4 | 0.06262 (13) | 0.87341 (12) | 0.90077 (10) | 0.0199 (5) | |
N4 | 0.18622 (15) | 0.97270 (15) | 0.76514 (12) | 0.0178 (5) | |
N3 | −0.11539 (15) | 0.82348 (15) | 0.64081 (13) | 0.0199 (5) | |
N1 | −0.31501 (17) | 1.48699 (16) | 1.10040 (14) | 0.0255 (6) | |
O1 | −0.3149 (2) | 1.38104 (17) | 1.14088 (16) | 0.0548 (9) | |
N2 | −0.04586 (14) | 1.09204 (14) | 0.84661 (12) | 0.0159 (5) | |
C9 | −0.3724 (2) | 0.6772 (2) | 0.46523 (17) | 0.0328 (7) | |
C15 | 0.19684 (19) | 0.99653 (19) | 0.64674 (15) | 0.0204 (6) | |
C8 | −0.28773 (18) | 0.82184 (19) | 0.60091 (16) | 0.0238 (7) | |
C3 | −0.22089 (19) | 1.56754 (18) | 0.83442 (17) | 0.0225 (7) | |
C11 | −0.0963 (2) | 0.67406 (19) | 0.55265 (17) | 0.0301 (7) | |
C5 | −0.26115 (17) | 1.46975 (17) | 0.99024 (15) | 0.0181 (6) | |
C10 | −0.2653 (2) | 0.5639 (2) | 0.47975 (17) | 0.0330 (8) | |
C6 | −0.19759 (17) | 1.34261 (17) | 0.94756 (14) | 0.0164 (6) | |
C2 | −0.15817 (18) | 1.44106 (17) | 0.78814 (16) | 0.0197 (6) | |
C12 | 0.34973 (17) | 0.99383 (18) | 0.86483 (15) | 0.0208 (6) | |
C1 | −0.14612 (17) | 1.32818 (16) | 0.84387 (14) | 0.0155 (6) | |
C4 | −0.27361 (18) | 1.58278 (17) | 0.93653 (16) | 0.0201 (6) | |
C7 | −0.07531 (17) | 1.19632 (17) | 0.78584 (14) | 0.0165 (6) | |
C13a | 0.4548 (8) | 1.0126 (8) | 0.7927 (6) | 0.0247 (12) | 0.336 (5) |
C13b | 0.4420 (3) | 0.9339 (4) | 0.7760 (3) | 0.0247 (12) | 0.664 (5) |
C14a | 0.3391 (10) | 0.9305 (11) | 0.6332 (9) | 0.033 (3) | 0.644 (17) |
C14b | 0.3674 (18) | 0.9798 (14) | 0.6637 (12) | 0.033 (3) | 0.356 (17) |
H1n2 | −0.065777 | 1.108409 | 0.918463 | 0.019* | |
H1c2 | −0.122519 | 1.43096 | 0.716793 | 0.0237* | |
H1c3 | −0.22764 | 1.644348 | 0.795508 | 0.027* | |
H1c4 | −0.317614 | 1.669318 | 0.969269 | 0.0241* | |
H1c6 | −0.189423 | 1.267335 | 0.988119 | 0.0197* | |
H1c8 | −0.304989 | 0.915205 | 0.586139 | 0.0286* | |
H2c8 | −0.321612 | 0.806628 | 0.667302 | 0.0286* | |
H1c9 | −0.373407 | 0.705963 | 0.392018 | 0.0393* | |
H2c9 | −0.476755 | 0.631309 | 0.456145 | 0.0393* | |
H1c10 | −0.283559 | 0.516153 | 0.537376 | 0.0396* | |
H2c10 | −0.280219 | 0.49194 | 0.390839 | 0.0396* | |
H1c11 | −0.02494 | 0.632222 | 0.608727 | 0.0361* | |
H2c11 | −0.063148 | 0.691885 | 0.486763 | 0.0361* | |
H1c12 | 0.349369 | 0.912483 | 0.898436 | 0.0249* | |
H2c12 | 0.387693 | 1.099082 | 0.934593 | 0.0249* | |
H1c13a | 0.496539 | 1.122767 | 0.818222 | 0.0297* | 0.336 (5) |
H2c13a | 0.537616 | 0.958382 | 0.812476 | 0.0297* | 0.336 (5) |
H1c15 | 0.206397 | 1.105653 | 0.662245 | 0.0244* | |
H2c15 | 0.108556 | 0.923041 | 0.564495 | 0.0244* | |
H1c13b | 0.41945 | 0.820988 | 0.742011 | 0.0297* | 0.6639 |
H2c13b | 0.553445 | 0.990426 | 0.825438 | 0.0297* | 0.6639 |
H1c14a | 0.310523 | 0.818201 | 0.604698 | 0.0393* | 0.644 (17) |
H2c14a | 0.38236 | 0.975893 | 0.584675 | 0.0393* | 0.644 (17) |
H1c14b | 0.432636 | 1.078161 | 0.680312 | 0.0393* | 0.3555 |
H2c14b | 0.362275 | 0.90209 | 0.580666 | 0.0393* | 0.3555 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0174 (2) | 0.0141 (2) | 0.0123 (2) | 0.00635 (15) | 0.00758 (15) | 0.00546 (14) |
O3 | 0.0383 (7) | 0.0297 (6) | 0.0192 (6) | 0.0186 (5) | 0.0177 (5) | 0.0142 (5) |
O2 | 0.0319 (6) | 0.0240 (6) | 0.0283 (6) | 0.0126 (5) | 0.0168 (5) | 0.0018 (5) |
O4 | 0.0290 (6) | 0.0210 (5) | 0.0201 (6) | 0.0130 (5) | 0.0157 (5) | 0.0124 (5) |
N4 | 0.0169 (6) | 0.0266 (7) | 0.0131 (6) | 0.0074 (5) | 0.0064 (5) | 0.0108 (5) |
N3 | 0.0197 (6) | 0.0190 (7) | 0.0167 (6) | 0.0051 (5) | 0.0086 (5) | 0.0009 (5) |
N1 | 0.0312 (7) | 0.0246 (7) | 0.0265 (7) | 0.0129 (6) | 0.0175 (6) | 0.0096 (6) |
O1 | 0.1049 (13) | 0.0508 (9) | 0.0648 (11) | 0.0515 (9) | 0.0698 (11) | 0.0427 (8) |
N2 | 0.0228 (6) | 0.0174 (6) | 0.0112 (6) | 0.0091 (5) | 0.0098 (5) | 0.0061 (5) |
C9 | 0.0281 (9) | 0.0375 (10) | 0.0217 (9) | −0.0082 (8) | 0.0040 (7) | 0.0108 (8) |
C15 | 0.0244 (8) | 0.0255 (8) | 0.0179 (8) | 0.0081 (7) | 0.0124 (7) | 0.0122 (6) |
C8 | 0.0181 (8) | 0.0308 (9) | 0.0206 (8) | 0.0032 (7) | 0.0061 (6) | 0.0110 (7) |
C3 | 0.0241 (8) | 0.0188 (8) | 0.0282 (9) | 0.0080 (7) | 0.0091 (7) | 0.0145 (7) |
C11 | 0.0360 (10) | 0.0205 (8) | 0.0256 (9) | 0.0036 (7) | 0.0165 (8) | −0.0031 (7) |
C5 | 0.0173 (7) | 0.0179 (7) | 0.0174 (7) | 0.0047 (6) | 0.0075 (6) | 0.0047 (6) |
C10 | 0.0449 (11) | 0.0250 (9) | 0.0193 (8) | −0.0055 (8) | 0.0121 (8) | 0.0030 (7) |
C6 | 0.0186 (7) | 0.0150 (7) | 0.0160 (7) | 0.0054 (6) | 0.0062 (6) | 0.0072 (6) |
C2 | 0.0203 (7) | 0.0215 (8) | 0.0197 (8) | 0.0066 (6) | 0.0084 (6) | 0.0104 (6) |
C12 | 0.0179 (7) | 0.0251 (8) | 0.0170 (8) | 0.0085 (6) | 0.0048 (6) | 0.0073 (6) |
C1 | 0.0147 (7) | 0.0154 (7) | 0.0138 (7) | 0.0039 (6) | 0.0033 (6) | 0.0053 (6) |
C4 | 0.0175 (7) | 0.0149 (7) | 0.0255 (8) | 0.0069 (6) | 0.0072 (6) | 0.0064 (6) |
C7 | 0.0179 (7) | 0.0169 (7) | 0.0130 (7) | 0.0051 (6) | 0.0053 (6) | 0.0051 (6) |
C13a | 0.0206 (10) | 0.0291 (19) | 0.0258 (12) | 0.0097 (16) | 0.0107 (10) | 0.0105 (16) |
C13b | 0.0206 (10) | 0.0291 (19) | 0.0258 (12) | 0.0097 (16) | 0.0107 (10) | 0.0105 (16) |
C14a | 0.035 (3) | 0.053 (4) | 0.020 (3) | 0.025 (3) | 0.017 (3) | 0.016 (3) |
C14b | 0.035 (3) | 0.053 (4) | 0.020 (3) | 0.025 (3) | 0.017 (3) | 0.016 (3) |
Geometric parameters (Å, º) top
P1—O4 | 1.4840 (14) | C11—C10 | 1.526 (2) |
P1—N4 | 1.6268 (16) | C11—H1c11 | 0.96 |
P1—N3 | 1.6351 (10) | C11—H2c11 | 0.96 |
P1—N2 | 1.6954 (14) | C5—C6 | 1.390 (2) |
O3—C7 | 1.223 (2) | C5—C4 | 1.385 (3) |
O2—N1 | 1.229 (2) | C10—H1c10 | 0.96 |
N4—C15 | 1.478 (3) | C10—H2c10 | 0.96 |
N4—C12 | 1.4747 (18) | C6—C1 | 1.393 (3) |
N3—C8 | 1.480 (2) | C6—H1c6 | 0.96 |
N3—C11 | 1.485 (2) | C2—C1 | 1.399 (3) |
N1—O1 | 1.225 (3) | C2—H1c2 | 0.96 |
N1—C5 | 1.473 (3) | C12—C13a | 1.501 (9) |
N2—C7 | 1.373 (2) | C12—C13b | 1.540 (4) |
N2—H1n2 | 0.87 | C12—H1c12 | 0.96 |
C9—C8 | 1.5306 (19) | C12—H2c12 | 0.96 |
C9—C10 | 1.526 (3) | C1—C7 | 1.512 (2) |
C9—H1c9 | 0.96 | C4—H1c4 | 0.96 |
C9—H2c9 | 0.96 | C13a—C14a | 1.602 (10) |
C15—C14a | 1.532 (10) | C13a—H1c13a | 0.96 |
C15—C14b | 1.538 (17) | C13a—H2c13a | 0.96 |
C15—H1c15 | 0.96 | C13b—C14b | 1.456 (15) |
C15—H2c15 | 0.96 | C13b—H1c13b | 0.96 |
C8—H1c8 | 0.96 | C13b—H2c13b | 0.96 |
C8—H2c8 | 0.96 | C14a—H1c14a | 0.96 |
C3—C2 | 1.389 (2) | C14a—H2c14a | 0.96 |
C3—C4 | 1.383 (3) | C14b—H1c14b | 0.96 |
C3—H1c3 | 0.96 | C14b—H2c14b | 0.96 |
| | | |
O4—P1—N4 | 110.38 (7) | C11—C10—H1c10 | 109.471 |
O4—P1—N3 | 118.96 (7) | C11—C10—H2c10 | 109.471 |
O4—P1—N2 | 105.02 (7) | H1c10—C10—H2c10 | 115.596 |
N4—P1—N3 | 104.98 (7) | C5—C6—C1 | 117.70 (17) |
N4—P1—N2 | 114.44 (7) | C5—C6—H1c6 | 121.15 |
N3—P1—N2 | 103.24 (6) | C1—C6—H1c6 | 121.149 |
P1—N4—C15 | 128.41 (10) | C3—C2—C1 | 121.05 (18) |
P1—N4—C12 | 122.38 (13) | C3—C2—H1c2 | 119.473 |
C15—N4—C12 | 109.19 (14) | C1—C2—H1c2 | 119.473 |
P1—N3—C8 | 124.07 (11) | N4—C12—C13a | 103.7 (3) |
P1—N3—C11 | 121.00 (11) | N4—C12—C13b | 103.97 (15) |
C8—N3—C11 | 110.68 (11) | N4—C12—H1c12 | 109.471 |
O2—N1—O1 | 123.52 (19) | N4—C12—H2c12 | 109.471 |
O2—N1—C5 | 118.34 (16) | C13a—C12—H1c12 | 120.993 |
O1—N1—C5 | 118.12 (16) | C13a—C12—H2c12 | 97.842 |
P1—N2—C7 | 124.81 (12) | C13b—C12—H1c12 | 98.036 |
P1—N2—H1n2 | 117.594 | C13b—C12—H2c12 | 120.583 |
C7—N2—H1n2 | 117.594 | H1c12—C12—H2c12 | 114.269 |
C8—C9—C10 | 103.69 (13) | C6—C1—C2 | 119.61 (15) |
C8—C9—H1c9 | 109.471 | C6—C1—C7 | 124.05 (16) |
C8—C9—H2c9 | 109.471 | C2—C1—C7 | 116.34 (16) |
C10—C9—H1c9 | 109.471 | C3—C4—C5 | 118.15 (16) |
C10—C9—H2c9 | 109.471 | C3—C4—H1c4 | 120.924 |
H1c9—C9—H2c9 | 114.695 | C5—C4—H1c4 | 120.924 |
N4—C15—C14a | 103.4 (5) | O3—C7—N2 | 121.91 (15) |
N4—C15—C14b | 101.8 (6) | O3—C7—C1 | 119.72 (16) |
N4—C15—H1c15 | 109.471 | N2—C7—C1 | 118.37 (15) |
N4—C15—H2c15 | 109.471 | C12—C13a—C14a | 105.7 (5) |
C14a—C15—H1c15 | 116.58 | C12—C13a—H1c13a | 109.472 |
C14a—C15—H2c15 | 101.549 | C12—C13a—H2c13a | 109.472 |
C14b—C15—H1c15 | 102.268 | C14a—C13a—H2c12 | 125.399 |
C14b—C15—H2c15 | 117.305 | C14a—C13a—H1c13a | 109.47 |
H1c15—C15—H2c15 | 115.435 | C14a—C13a—H2c13a | 109.471 |
N3—C8—C9 | 103.60 (14) | H2c12—C13a—H1c13a | 80.56 |
N3—C8—H1c8 | 109.471 | H2c12—C13a—H2c13a | 115.094 |
N3—C8—H2c8 | 109.471 | H1c13a—C13a—H2c13a | 113.027 |
C9—C8—H1c8 | 109.471 | C12—C13b—C14b | 101.6 (7) |
C9—C8—H2c8 | 109.471 | C12—C13b—H1c13b | 109.471 |
H1c8—C8—H2c8 | 114.769 | C12—C13b—H2c13b | 109.471 |
C2—C3—C4 | 120.00 (18) | C14b—C13b—H1c13b | 109.471 |
C2—C3—H1c3 | 120 | C14b—C13b—H2c13b | 109.472 |
C4—C3—H1c3 | 119.999 | H1c13b—C13b—H2c13b | 116.338 |
N3—C11—C10 | 104.03 (15) | C15—C14a—C13a | 95.6 (6) |
N3—C11—H1c11 | 109.471 | C15—C14a—H1c14a | 109.471 |
N3—C11—H2c11 | 109.471 | C15—C14a—H2c14a | 109.471 |
C10—C11—H1c11 | 109.471 | C13a—C14a—H1c14a | 109.471 |
C10—C11—H2c11 | 109.471 | C13a—C14a—H2c14a | 109.471 |
H1c11—C11—H2c11 | 114.418 | H1c14a—C14a—H2c14a | 120.483 |
N1—C5—C6 | 118.26 (16) | C15—C14b—C13b | 111.3 (11) |
N1—C5—C4 | 118.26 (15) | C15—C14b—H1c14b | 109.471 |
C6—C5—C4 | 123.47 (18) | C15—C14b—H2c14b | 109.471 |
C9—C10—C11 | 102.56 (14) | C13b—C14b—H1c14b | 109.471 |
C9—C10—H1c10 | 109.471 | C13b—C14b—H2c14b | 109.472 |
C9—C10—H2c10 | 109.471 | H1c14b—C14b—H2c14b | 107.552 |
Crystal data top
C15H21N4O6P | F(000) = 808 |
Mr = 384.33 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 316 reflections |
a = 16.2973 (12) Å | θ = 3–30° |
b = 11.1318 (8) Å | µ = 0.20 mm−1 |
c = 9.4354 (7) Å | T = 120 K |
β = 94.881 (2)° | Prism, colorless |
V = 1705.5 (2) Å3 | 0.28 × 0.26 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area detector diffractometer | 4958 independent reflections |
Radiation source: fine-focus sealed tube | 3709 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
phi and ω scans | θmax = 30.0°, θmin = 1.3° |
Absorption correction: multi-scan SADABS (Sheldrick, 1998a) | h = −22→22 |
Tmin = 0.941, Tmax = 0.968 | k = −15→15 |
19538 measured reflections | l = −13→13 |
Refinement top
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)] = 0.049 | Hydrogen site location: mixed |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.050P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3 |
4958 reflections | (Δ/σ)max = 0.001 |
247 parameters | Δρmax = 0.45 e Å−3 |
11 restraints | Δρmin = −0.41 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.72756 (3) | −0.15976 (4) | 0.43644 (4) | 0.01736 (11) | |
O1 | 0.75864 (7) | −0.18520 (12) | 0.58549 (12) | 0.0214 (3) | |
O2 | 0.53805 (9) | −0.43820 (14) | 0.29983 (15) | 0.0331 (3) | |
O4 | 0.88392 (8) | −0.03195 (12) | 0.44666 (13) | 0.0255 (3) | |
O5 | 1.18502 (9) | −0.06092 (15) | −0.01625 (18) | 0.0406 (4) | |
O6 | 1.12161 (9) | −0.20653 (14) | −0.12942 (15) | 0.0334 (3) | |
N1 | 0.65724 (8) | −0.25956 (13) | 0.38296 (15) | 0.0195 (3) | |
N2 | 0.68430 (9) | −0.02940 (13) | 0.40839 (15) | 0.0240 (3) | |
N3 | 0.80206 (8) | −0.16713 (13) | 0.32300 (14) | 0.0173 (3) | |
H3N | 0.7924 | −0.2087 | 0.2453 | 0.021* | |
N4 | 1.12866 (9) | −0.13335 (14) | −0.03249 (16) | 0.0237 (3) | |
C1 | 0.67575 (11) | −0.38799 (17) | 0.4032 (2) | 0.0242 (4) | |
H1A | 0.7139 | −0.3989 | 0.4896 | 0.029* | |
H1B | 0.7032 | −0.4186 | 0.3208 | 0.029* | |
C2 | 0.59725 (12) | −0.45904 (19) | 0.4182 (2) | 0.0294 (4) | |
H2A | 0.6104 | −0.5458 | 0.4243 | 0.035* | |
H2B | 0.5735 | −0.4353 | 0.5072 | 0.035* | |
C3 | 0.51835 (11) | −0.3135 (2) | 0.2909 (2) | 0.0324 (4) | |
H3A | 0.4959 | −0.2877 | 0.3802 | 0.039* | |
H3B | 0.4753 | −0.3004 | 0.2119 | 0.039* | |
C4 | 0.59334 (10) | −0.23747 (19) | 0.26617 (19) | 0.0254 (4) | |
H4A | 0.6143 | −0.2591 | 0.1741 | 0.030* | |
H4B | 0.5782 | −0.1513 | 0.2633 | 0.030* | |
C9 | 0.87345 (10) | −0.10135 (15) | 0.34665 (17) | 0.0184 (3) | |
C10 | 0.93955 (10) | −0.11669 (15) | 0.24531 (17) | 0.0176 (3) | |
C11 | 1.00347 (11) | −0.03303 (16) | 0.25795 (19) | 0.0217 (3) | |
H11A | 1.0037 | 0.0282 | 0.3282 | 0.026* | |
C12 | 1.06684 (11) | −0.03870 (16) | 0.16839 (19) | 0.0229 (3) | |
H12A | 1.1103 | 0.0185 | 0.1753 | 0.028* | |
C13 | 1.06469 (10) | −0.13000 (16) | 0.06906 (17) | 0.0191 (3) | |
C14 | 1.00412 (10) | −0.21729 (16) | 0.05804 (18) | 0.0212 (3) | |
H14A | 1.0059 | −0.2808 | −0.0089 | 0.025* | |
C15 | 0.94035 (10) | −0.21009 (16) | 0.14730 (18) | 0.0203 (3) | |
H15A | 0.8977 | −0.2685 | 0.1413 | 0.024* | |
C5A | 0.70139 (11) | 0.06211 (15) | 0.30444 (19) | 0.0279 (4) | |
H5AA | 0.6526 | 0.0785 | 0.2373 | 0.033* | |
H5AB | 0.7485 | 0.0395 | 0.2504 | 0.033* | |
C6A | 0.7221 (3) | 0.1689 (3) | 0.4032 (4) | 0.0388 (10) | 0.55 |
H6AA | 0.7719 | 0.1486 | 0.4662 | 0.047* | 0.55 |
H6AB | 0.7361 | 0.2384 | 0.3443 | 0.047* | 0.55 |
C7A | 0.6402 (3) | 0.1081 (3) | 0.5808 (4) | 0.0345 (8) | 0.55 |
H7AA | 0.5951 | 0.1321 | 0.6390 | 0.041* | 0.55 |
H7AB | 0.6893 | 0.0893 | 0.6461 | 0.041* | 0.55 |
C8A | 0.6145 (2) | −0.0027 (4) | 0.4942 (5) | 0.0249 (8) | 0.55 |
H8AA | 0.6043 | −0.0710 | 0.5575 | 0.030* | 0.55 |
H8AB | 0.5637 | 0.0133 | 0.4318 | 0.030* | 0.55 |
O3A | 0.6586 (2) | 0.2048 (3) | 0.4899 (4) | 0.0360 (6) | 0.55 |
O3B | 0.6765 (3) | 0.2305 (4) | 0.4420 (4) | 0.0360 (6) | 0.45 |
C8B | 0.6384 (3) | 0.0313 (4) | 0.5156 (6) | 0.0249 (8) | 0.45 |
H8BA | 0.6382 | −0.0211 | 0.6003 | 0.030* | 0.45 |
H8BB | 0.5806 | 0.0419 | 0.4764 | 0.030* | 0.45 |
C7B | 0.6733 (4) | 0.1527 (3) | 0.5615 (4) | 0.0345 (8) | 0.45 |
H7BA | 0.6384 | 0.1893 | 0.6309 | 0.041* | 0.45 |
H7BB | 0.7294 | 0.1422 | 0.6089 | 0.041* | 0.45 |
C6B | 0.7341 (4) | 0.1843 (3) | 0.3512 (6) | 0.0388 (10) | 0.45 |
H6BA | 0.7893 | 0.1770 | 0.4030 | 0.047* | 0.45 |
H6BB | 0.7381 | 0.2376 | 0.2681 | 0.047* | 0.45 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01551 (19) | 0.0226 (2) | 0.0142 (2) | 0.00298 (16) | 0.00293 (14) | 0.00134 (16) |
O1 | 0.0180 (6) | 0.0304 (7) | 0.0157 (6) | 0.0040 (5) | 0.0019 (4) | 0.0031 (5) |
O2 | 0.0301 (7) | 0.0425 (9) | 0.0268 (7) | −0.0121 (6) | 0.0038 (6) | −0.0041 (6) |
O4 | 0.0239 (6) | 0.0316 (7) | 0.0212 (6) | −0.0027 (5) | 0.0037 (5) | −0.0079 (5) |
O5 | 0.0305 (8) | 0.0445 (9) | 0.0495 (10) | −0.0168 (7) | 0.0192 (7) | −0.0110 (7) |
O6 | 0.0309 (7) | 0.0448 (9) | 0.0262 (7) | −0.0050 (6) | 0.0108 (6) | −0.0085 (6) |
N1 | 0.0159 (6) | 0.0242 (7) | 0.0185 (6) | 0.0007 (5) | 0.0021 (5) | 0.0013 (5) |
N2 | 0.0286 (8) | 0.0269 (8) | 0.0176 (7) | 0.0112 (6) | 0.0087 (6) | 0.0040 (6) |
N3 | 0.0149 (6) | 0.0237 (7) | 0.0138 (6) | −0.0002 (5) | 0.0036 (5) | −0.0026 (5) |
N4 | 0.0197 (7) | 0.0290 (8) | 0.0231 (7) | −0.0009 (6) | 0.0059 (6) | 0.0015 (6) |
C1 | 0.0246 (8) | 0.0248 (9) | 0.0235 (9) | 0.0017 (7) | 0.0030 (7) | 0.0004 (7) |
C2 | 0.0337 (10) | 0.0306 (10) | 0.0242 (9) | −0.0064 (8) | 0.0056 (8) | −0.0007 (7) |
C3 | 0.0173 (8) | 0.0506 (13) | 0.0294 (10) | −0.0036 (8) | 0.0023 (7) | −0.0012 (9) |
C4 | 0.0168 (8) | 0.0376 (10) | 0.0213 (8) | 0.0008 (7) | −0.0001 (6) | 0.0033 (7) |
C9 | 0.0169 (7) | 0.0223 (8) | 0.0159 (7) | 0.0005 (6) | 0.0017 (6) | 0.0009 (6) |
C10 | 0.0156 (7) | 0.0211 (8) | 0.0161 (7) | 0.0006 (6) | 0.0013 (6) | 0.0011 (6) |
C11 | 0.0212 (8) | 0.0214 (8) | 0.0225 (8) | −0.0021 (6) | 0.0026 (6) | −0.0032 (6) |
C12 | 0.0201 (8) | 0.0218 (8) | 0.0272 (9) | −0.0043 (6) | 0.0040 (7) | −0.0006 (7) |
C13 | 0.0150 (7) | 0.0247 (8) | 0.0182 (7) | 0.0004 (6) | 0.0044 (6) | 0.0030 (6) |
C14 | 0.0187 (8) | 0.0247 (9) | 0.0206 (8) | −0.0017 (6) | 0.0031 (6) | −0.0042 (7) |
C15 | 0.0164 (7) | 0.0238 (8) | 0.0210 (8) | −0.0030 (6) | 0.0031 (6) | −0.0034 (6) |
C5A | 0.0240 (9) | 0.0264 (9) | 0.0336 (10) | 0.0029 (7) | 0.0047 (7) | 0.0101 (8) |
C6A | 0.0289 (17) | 0.0164 (13) | 0.071 (3) | −0.0063 (11) | 0.007 (2) | 0.0174 (18) |
C7A | 0.058 (3) | 0.0213 (19) | 0.0246 (14) | 0.0122 (14) | 0.0086 (15) | −0.0009 (14) |
C8A | 0.031 (2) | 0.022 (2) | 0.0227 (16) | 0.0094 (14) | 0.0113 (17) | 0.0023 (13) |
O3A | 0.0516 (19) | 0.0181 (15) | 0.039 (2) | 0.0062 (12) | 0.0061 (13) | 0.0013 (12) |
O3B | 0.0516 (19) | 0.0181 (15) | 0.039 (2) | 0.0062 (12) | 0.0061 (13) | 0.0013 (12) |
C8B | 0.031 (2) | 0.022 (2) | 0.0227 (16) | 0.0094 (14) | 0.0113 (17) | 0.0023 (13) |
C7B | 0.058 (3) | 0.0213 (19) | 0.0246 (14) | 0.0122 (14) | 0.0086 (15) | −0.0009 (14) |
C6B | 0.0289 (17) | 0.0164 (13) | 0.071 (3) | −0.0063 (11) | 0.007 (2) | 0.0174 (18) |
Geometric parameters (Å, º) top
P1—O1 | 1.4811 (12) | C11—C12 | 1.390 (2) |
P1—N2 | 1.6251 (15) | C11—H11A | 0.9500 |
P1—N1 | 1.6443 (15) | C12—C13 | 1.381 (2) |
P1—N3 | 1.6875 (14) | C12—H12A | 0.9500 |
O2—C3 | 1.426 (3) | C13—C14 | 1.383 (2) |
O2—C2 | 1.431 (2) | C14—C15 | 1.395 (2) |
O4—C9 | 1.220 (2) | C14—H14A | 0.9500 |
O5—N4 | 1.222 (2) | C15—H15A | 0.9500 |
O6—N4 | 1.223 (2) | C5A—C6B | 1.513 (3) |
N1—C1 | 1.470 (2) | C5A—C6A | 1.530 (3) |
N1—C4 | 1.471 (2) | C5A—H5AA | 0.9900 |
N2—C5A | 1.4573 (18) | C5A—H5AB | 0.9900 |
N2—C8B | 1.472 (3) | C6A—O3A | 1.430 (3) |
N2—C8A | 1.481 (2) | C6A—H6AA | 0.9900 |
N3—C9 | 1.377 (2) | C6A—H6AB | 0.9900 |
N3—H3N | 0.8700 | C7A—O3A | 1.424 (3) |
N4—C13 | 1.475 (2) | C7A—C8A | 1.518 (3) |
C1—C2 | 1.521 (3) | C7A—H7AA | 0.9900 |
C1—H1A | 0.9900 | C7A—H7AB | 0.9900 |
C1—H1B | 0.9900 | C8A—H8AA | 0.9900 |
C2—H2A | 0.9900 | C8A—H8AB | 0.9900 |
C2—H2B | 0.9900 | O3B—C6B | 1.421 (3) |
C3—C4 | 1.521 (3) | O3B—C7B | 1.427 (3) |
C3—H3A | 0.9900 | C8B—C7B | 1.515 (3) |
C3—H3B | 0.9900 | C8B—H8BA | 0.9900 |
C4—H4A | 0.9900 | C8B—H8BB | 0.9900 |
C4—H4B | 0.9900 | C7B—H7BA | 0.9900 |
C9—C10 | 1.510 (2) | C7B—H7BB | 0.9900 |
C10—C15 | 1.392 (2) | C6B—H6BA | 0.9900 |
C10—C11 | 1.395 (2) | C6B—H6BB | 0.9900 |
| | | |
O1—P1—N2 | 115.72 (8) | C12—C13—C14 | 123.02 (15) |
O1—P1—N1 | 109.59 (7) | C12—C13—N4 | 118.74 (15) |
N2—P1—N1 | 105.78 (8) | C14—C13—N4 | 118.22 (15) |
O1—P1—N3 | 112.74 (7) | C13—C14—C15 | 118.57 (16) |
N2—P1—N3 | 105.41 (7) | C13—C14—H14A | 120.7 |
N1—P1—N3 | 107.03 (7) | C15—C14—H14A | 120.7 |
C3—O2—C2 | 109.73 (15) | C10—C15—C14 | 119.58 (15) |
C1—N1—C4 | 112.60 (14) | C10—C15—H15A | 120.2 |
C1—N1—P1 | 119.16 (11) | C14—C15—H15A | 120.2 |
C4—N1—P1 | 123.18 (12) | N2—C5A—C6B | 121.0 (3) |
C5A—N2—C8B | 106.2 (3) | N2—C5A—C6A | 100.28 (19) |
C5A—N2—C8A | 115.3 (2) | N2—C5A—H5AA | 111.7 |
C5A—N2—P1 | 128.95 (11) | C6B—C5A—H5AA | 105.4 |
C8B—N2—P1 | 122.4 (3) | C6A—C5A—H5AA | 111.7 |
C8A—N2—P1 | 115.6 (2) | N2—C5A—H5AB | 111.7 |
C9—N3—P1 | 121.00 (11) | C6B—C5A—H5AB | 96.3 |
C9—N3—H3N | 120.6 | C6A—C5A—H5AB | 111.7 |
P1—N3—H3N | 118.2 | H5AA—C5A—H5AB | 109.5 |
O5—N4—O6 | 123.72 (15) | O3A—C6A—C5A | 115.6 (3) |
O5—N4—C13 | 117.84 (15) | O3A—C6A—H6AA | 108.4 |
O6—N4—C13 | 118.42 (15) | C5A—C6A—H6AA | 108.4 |
N1—C1—C2 | 110.66 (15) | O3A—C6A—H6AB | 108.4 |
N1—C1—H1A | 109.5 | C5A—C6A—H6AB | 108.4 |
C2—C1—H1A | 109.5 | H6AA—C6A—H6AB | 107.4 |
N1—C1—H1B | 109.5 | O3A—C7A—C8A | 110.6 (3) |
C2—C1—H1B | 109.5 | O3A—C7A—H7AA | 109.5 |
H1A—C1—H1B | 108.1 | C8A—C7A—H7AA | 109.5 |
O2—C2—C1 | 111.10 (15) | O3A—C7A—H7AB | 109.5 |
O2—C2—H2A | 109.4 | C8A—C7A—H7AB | 109.5 |
C1—C2—H2A | 109.4 | H7AA—C7A—H7AB | 108.1 |
O2—C2—H2B | 109.4 | N2—C8A—C7A | 105.5 (2) |
C1—C2—H2B | 109.4 | N2—C8A—H8AA | 110.6 |
H2A—C2—H2B | 108.0 | C7A—C8A—H8AA | 110.6 |
O2—C3—C4 | 111.77 (16) | N2—C8A—H8AB | 110.6 |
O2—C3—H3A | 109.3 | C7A—C8A—H8AB | 110.6 |
C4—C3—H3A | 109.3 | H8AA—C8A—H8AB | 108.8 |
O2—C3—H3B | 109.3 | C7A—O3A—C6A | 109.5 (3) |
C4—C3—H3B | 109.3 | C6B—O3B—C7B | 109.1 (4) |
H3A—C3—H3B | 107.9 | N2—C8B—C7B | 113.9 (3) |
N1—C4—C3 | 108.60 (15) | N2—C8B—H8BA | 108.8 |
N1—C4—H4A | 110.0 | C7B—C8B—H8BA | 108.8 |
C3—C4—H4A | 110.0 | N2—C8B—H8BB | 108.8 |
N1—C4—H4B | 110.0 | C7B—C8B—H8BB | 108.8 |
C3—C4—H4B | 110.0 | H8BA—C8B—H8BB | 107.7 |
H4A—C4—H4B | 108.4 | O3B—C7B—C8B | 110.7 (4) |
O4—C9—N3 | 121.52 (15) | O3B—C7B—H7BA | 109.5 |
O4—C9—C10 | 120.07 (15) | C8B—C7B—H7BA | 109.5 |
N3—C9—C10 | 118.42 (14) | O3B—C7B—H7BB | 109.5 |
C15—C10—C11 | 120.42 (15) | C8B—C7B—H7BB | 109.5 |
C15—C10—C9 | 123.55 (15) | H7BA—C7B—H7BB | 108.1 |
C11—C10—C9 | 115.99 (15) | O3B—C6B—C5A | 105.5 (3) |
C12—C11—C10 | 120.37 (16) | O3B—C6B—H6BA | 110.6 |
C12—C11—H11A | 119.8 | C5A—C6B—H6BA | 110.6 |
C10—C11—H11A | 119.8 | O3B—C6B—H6BB | 110.6 |
C13—C12—C11 | 117.95 (16) | C5A—C6B—H6BB | 110.6 |
C13—C12—H12A | 121.0 | H6BA—C6B—H6BB | 108.8 |
C11—C12—H12A | 121.0 | | |
| | | |
O1—P1—N1—C1 | −50.57 (14) | C10—C11—C12—C13 | −0.8 (3) |
N2—P1—N1—C1 | −175.97 (12) | C11—C12—C13—C14 | −2.1 (3) |
N3—P1—N1—C1 | 71.98 (14) | C11—C12—C13—N4 | 176.43 (15) |
O1—P1—N1—C4 | 156.48 (13) | O5—N4—C13—C12 | 6.2 (2) |
N2—P1—N1—C4 | 31.08 (15) | O6—N4—C13—C12 | −172.40 (17) |
N3—P1—N1—C4 | −80.96 (14) | O5—N4—C13—C14 | −175.22 (17) |
O1—P1—N2—C5A | 127.90 (16) | O6—N4—C13—C14 | 6.2 (2) |
N1—P1—N2—C5A | −110.57 (17) | C12—C13—C14—C15 | 2.7 (3) |
N3—P1—N2—C5A | 2.61 (18) | N4—C13—C14—C15 | −175.75 (15) |
O1—P1—N2—C8B | −32.0 (3) | C11—C10—C15—C14 | −2.2 (3) |
N1—P1—N2—C8B | 89.5 (3) | C9—C10—C15—C14 | −179.83 (15) |
N3—P1—N2—C8B | −157.3 (2) | C13—C14—C15—C10 | −0.6 (3) |
O1—P1—N2—C8A | −56.2 (2) | C8B—N2—C5A—C6B | 46.2 (4) |
N1—P1—N2—C8A | 65.3 (2) | C8A—N2—C5A—C6B | 67.9 (4) |
N3—P1—N2—C8A | 178.52 (19) | P1—N2—C5A—C6B | −116.2 (3) |
O1—P1—N3—C9 | −53.76 (15) | C8B—N2—C5A—C6A | 39.8 (3) |
N2—P1—N3—C9 | 73.37 (15) | C8A—N2—C5A—C6A | 61.5 (3) |
N1—P1—N3—C9 | −174.33 (13) | P1—N2—C5A—C6A | −122.6 (2) |
C4—N1—C1—C2 | −52.44 (19) | N2—C5A—C6A—O3A | −59.0 (4) |
P1—N1—C1—C2 | 151.91 (13) | C6B—C5A—C6A—O3A | 136.0 (13) |
C3—O2—C2—C1 | −59.5 (2) | C5A—N2—C8A—C7A | −64.2 (4) |
N1—C1—C2—O2 | 54.8 (2) | C8B—N2—C8A—C7A | 5.8 (9) |
C2—O2—C3—C4 | 61.8 (2) | P1—N2—C8A—C7A | 119.4 (3) |
C1—N1—C4—C3 | 53.1 (2) | O3A—C7A—C8A—N2 | 57.6 (4) |
P1—N1—C4—C3 | −152.34 (14) | C8A—C7A—O3A—C6A | −57.6 (4) |
O2—C3—C4—N1 | −58.0 (2) | C5A—C6A—O3A—C7A | 61.0 (5) |
P1—N3—C9—O4 | −3.1 (2) | C5A—N2—C8B—C7B | −43.9 (5) |
P1—N3—C9—C10 | 176.93 (11) | C8A—N2—C8B—C7B | −161.7 (16) |
O4—C9—C10—C15 | 166.37 (17) | P1—N2—C8B—C7B | 120.0 (4) |
N3—C9—C10—C15 | −13.6 (2) | C6B—O3B—C7B—C8B | −66.0 (6) |
O4—C9—C10—C11 | −11.3 (2) | N2—C8B—C7B—O3B | 57.2 (6) |
N3—C9—C10—C11 | 168.65 (15) | C7B—O3B—C6B—C5A | 61.2 (6) |
C15—C10—C11—C12 | 2.9 (3) | N2—C5A—C6B—O3B | −55.8 (5) |
C9—C10—C11—C12 | −179.28 (16) | C6A—C5A—C6B—O3B | −38.5 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1i | 0.87 | 1.96 | 2.8205 (18) | 172 |
Symmetry code: (i) x, −y−1/2, z−1/2. |
Crystal data top
C33H50LaN11O23P2 | F(000) = 2384 |
Mr = 1169.69 | Dx = 1.688 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 989 reflections |
a = 8.8631 (10) Å | θ = 3–29° |
b = 33.466 (4) Å | µ = 1.10 mm−1 |
c = 15.5399 (18) Å | T = 100 K |
β = 93.195 (3)° | Plate, colorless |
V = 4602.2 (9) Å3 | 0.47 × 0.33 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEX II CCD area detector' diffractometer | 12056 independent reflections |
Radiation source: fine-focus sealed tube | 9147 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
ω scans | θmax = 29.0°, θmin = 1.2° |
Absorption correction: multi-scan SADABS | h = −12→12 |
Tmin = 0.657, Tmax = 0.801 | k = −45→45 |
54317 measured reflections | l = −21→21 |
Refinement top
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)] = 0.055 | Hydrogen site location: mixed |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0141P)2 + 17.2485P] where P = (Fo2 + 2Fc2)/3 |
12056 reflections | (Δ/σ)max = 0.002 |
687 parameters | Δρmax = 1.32 e Å−3 |
0 restraints | Δρmin = −1.44 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
La1 | −0.21219 (3) | −0.162084 (7) | −0.416286 (16) | 0.01963 (6) | |
P1 | −0.30762 (11) | −0.15883 (3) | −0.65977 (7) | 0.0229 (2) | |
P2 | −0.24369 (11) | −0.13787 (3) | −0.17453 (7) | 0.0203 (2) | |
O1 | −0.1963 (3) | −0.23304 (8) | −0.48952 (19) | 0.0242 (6) | |
O2 | −0.1005 (3) | −0.22984 (8) | −0.35884 (19) | 0.0241 (6) | |
O3 | −0.0515 (4) | −0.28073 (9) | −0.4400 (2) | 0.0318 (7) | |
O4 | −0.1344 (3) | −0.08474 (9) | −0.36440 (19) | 0.0267 (6) | |
O5 | −0.0890 (3) | −0.10120 (8) | −0.49486 (19) | 0.0261 (6) | |
O6 | −0.0109 (4) | −0.04378 (9) | −0.4440 (2) | 0.0326 (7) | |
O7 | 0.0672 (4) | −0.15073 (9) | −0.3599 (2) | 0.0322 (7) | |
O8 | 0.0438 (4) | −0.17936 (9) | −0.4847 (2) | 0.0310 (7) | |
O9 | 0.2673 (4) | −0.16616 (13) | −0.4287 (3) | 0.0587 (12) | |
O10 | −0.3085 (3) | −0.16053 (9) | −0.56381 (19) | 0.0253 (6) | |
O11 | −0.1977 (4) | −0.11817 (12) | −0.8228 (2) | 0.0398 (8) | |
O12 | −0.7891 (3) | −0.15015 (10) | −0.7497 (2) | 0.0318 (7) | |
O13 | −0.1117 (4) | −0.27018 (9) | −0.7618 (2) | 0.0344 (8) | |
O14 | 0.3940 (4) | 0.01828 (10) | −0.6739 (2) | 0.0343 (7) | |
O15 | 0.3628 (4) | 0.02387 (10) | −0.8127 (2) | 0.0353 (8) | |
O16 | −0.2561 (3) | −0.15357 (8) | −0.26427 (19) | 0.0242 (6) | |
O17 | −0.1043 (4) | −0.08087 (11) | −0.0389 (2) | 0.0359 (8) | |
O18 | −0.7100 (3) | −0.11607 (9) | −0.0956 (2) | 0.0276 (6) | |
O19 | −0.0581 (4) | −0.23205 (10) | 0.0029 (2) | 0.0368 (8) | |
O21 | 0.4230 (4) | 0.04874 (9) | −0.2397 (2) | 0.0328 (7) | |
O20 | 0.4755 (4) | 0.05014 (11) | −0.1018 (2) | 0.0391 (8) | |
O1W | −0.4420 (3) | −0.20339 (9) | −0.3986 (2) | 0.0306 (7) | |
H1W1 | −0.4628 | −0.2232 | −0.4356 | 0.037* | |
H2W1 | −0.5130 | −0.2025 | −0.3603 | 0.037* | |
N1 | −0.1156 (4) | −0.24862 (10) | −0.4300 (2) | 0.0220 (7) | |
N2 | −0.0761 (4) | −0.07590 (10) | −0.4342 (2) | 0.0235 (7) | |
N3 | 0.1305 (4) | −0.16570 (11) | −0.4247 (3) | 0.0335 (9) | |
N5 | −0.1852 (4) | −0.12145 (10) | −0.6770 (2) | 0.0227 (7) | |
H5N | −0.1332 | −0.1134 | −0.6328 | 0.027* | |
N6 | −0.2417 (4) | −0.19710 (11) | −0.7100 (3) | 0.0326 (9) | |
N7 | −0.4788 (4) | −0.15196 (11) | −0.6986 (2) | 0.0239 (7) | |
N8 | 0.3313 (4) | 0.00935 (10) | −0.7439 (3) | 0.0273 (8) | |
N9 | −0.1150 (4) | −0.10073 (10) | −0.1776 (2) | 0.0206 (7) | |
H9N | −0.0900 | −0.0939 | −0.2275 | 0.025* | |
N10 | −0.4083 (4) | −0.12428 (10) | −0.1456 (2) | 0.0221 (7) | |
N11 | −0.1777 (4) | −0.16832 (11) | −0.0997 (3) | 0.0291 (8) | |
N12 | 0.4026 (4) | 0.03781 (11) | −0.1658 (3) | 0.0287 (8) | |
C1 | −0.1412 (5) | −0.10650 (13) | −0.7543 (3) | 0.0283 (9) | |
C2 | −0.0173 (5) | −0.07598 (12) | −0.7483 (3) | 0.0240 (8) | |
C3 | 0.0265 (5) | −0.05644 (13) | −0.6712 (3) | 0.0262 (9) | |
H3A | −0.0228 | −0.0620 | −0.6214 | 0.031* | |
C4 | 0.1425 (5) | −0.02891 (12) | −0.6690 (3) | 0.0257 (9) | |
H4A | 0.1736 | −0.0161 | −0.6180 | 0.031* | |
C5 | 0.2113 (5) | −0.02101 (12) | −0.7450 (3) | 0.0241 (8) | |
C6 | 0.1690 (5) | −0.03933 (13) | −0.8218 (3) | 0.0268 (9) | |
H6A | 0.2171 | −0.0331 | −0.8718 | 0.032* | |
C7 | 0.0544 (5) | −0.06701 (14) | −0.8232 (3) | 0.0271 (9) | |
H7A | 0.0246 | −0.0798 | −0.8745 | 0.033* | |
C8 | −0.5902 (5) | −0.13294 (14) | −0.6451 (3) | 0.0294 (9) | |
H8A | −0.5987 | −0.1048 | −0.6592 | 0.035* | |
H8B | −0.5577 | −0.1353 | −0.5847 | 0.035* | |
C9 | −0.7396 (5) | −0.15283 (15) | −0.6612 (3) | 0.0328 (10) | |
H9A | −0.7315 | −0.1807 | −0.6446 | 0.039* | |
H9B | −0.8135 | −0.1403 | −0.6263 | 0.039* | |
C10 | −0.6829 (5) | −0.16947 (15) | −0.8023 (3) | 0.0323 (10) | |
H10A | −0.7181 | −0.1675 | −0.8624 | 0.039* | |
H10B | −0.6766 | −0.1976 | −0.7874 | 0.039* | |
C11 | −0.5275 (5) | −0.15078 (15) | −0.7903 (3) | 0.0306 (10) | |
H11A | −0.4563 | −0.1654 | −0.8237 | 0.037* | |
H11B | −0.5308 | −0.1233 | −0.8104 | 0.037* | |
C12 | −0.0768 (6) | −0.20654 (17) | −0.6937 (4) | 0.0247 (14) | 0.774 (10) |
H12A | −0.0600 | −0.2197 | −0.6383 | 0.030* | 0.774 (10) |
H12B | −0.0177 | −0.1821 | −0.6931 | 0.030* | 0.774 (10) |
C13 | −0.0308 (6) | −0.23368 (17) | −0.7651 (5) | 0.0253 (14) | 0.774 (10) |
H13A | −0.0523 | −0.2209 | −0.8204 | 0.030* | 0.774 (10) |
H13B | 0.0769 | −0.2389 | −0.7588 | 0.030* | 0.774 (10) |
C14 | −0.2719 (6) | −0.26266 (16) | −0.7769 (4) | 0.0254 (14) | 0.774 (10) |
H14A | −0.3268 | −0.2878 | −0.7779 | 0.031* | 0.774 (10) |
H14B | −0.2906 | −0.2497 | −0.8322 | 0.031* | 0.774 (10) |
C15 | −0.3264 (6) | −0.23621 (19) | −0.7060 (5) | 0.0254 (14) | 0.774 (10) |
H15A | −0.4343 | −0.2316 | −0.7144 | 0.031* | 0.774 (10) |
H15B | −0.3065 | −0.2488 | −0.6503 | 0.031* | 0.774 (10) |
C12' | −0.0826 (19) | −0.1977 (5) | −0.7525 (15) | 0.022 (5) | 0.226 (10) |
H12C | −0.0935 | −0.2001 | −0.8147 | 0.027* | 0.226 (10) |
H12D | −0.0227 | −0.1742 | −0.7371 | 0.027* | 0.226 (10) |
C13' | −0.020 (2) | −0.2332 (6) | −0.7128 (19) | 0.028 (5) | 0.226 (10) |
H13C | −0.0365 | −0.2334 | −0.6515 | 0.034* | 0.226 (10) |
H13D | 0.0870 | −0.2351 | −0.7207 | 0.034* | 0.226 (10) |
C14' | −0.260 (2) | −0.2646 (7) | −0.7164 (14) | 0.029 (5) | 0.226 (10) |
H14C | −0.3246 | −0.2878 | −0.7258 | 0.034* | 0.226 (10) |
H14D | −0.2394 | −0.2613 | −0.6548 | 0.034* | 0.226 (10) |
C15' | −0.334 (2) | −0.2292 (6) | −0.7525 (15) | 0.021 (4) | 0.226 (10) |
H15C | −0.4389 | −0.2276 | −0.7376 | 0.025* | 0.226 (10) |
H15D | −0.3295 | −0.2282 | −0.8147 | 0.025* | 0.226 (10) |
C16 | −0.0600 (4) | −0.07706 (13) | −0.1110 (3) | 0.0232 (8) | |
C17 | 0.0588 (4) | −0.04707 (12) | −0.1310 (3) | 0.0204 (8) | |
C18 | 0.1063 (5) | −0.03914 (12) | −0.2129 (3) | 0.0223 (8) | |
H18A | 0.0626 | −0.0528 | −0.2602 | 0.027* | |
C19 | 0.2190 (5) | −0.01093 (12) | −0.2249 (3) | 0.0244 (8) | |
H19A | 0.2503 | −0.0052 | −0.2797 | 0.029* | |
C20 | 0.2829 (5) | 0.00829 (12) | −0.1530 (3) | 0.0245 (8) | |
C21 | 0.2394 (5) | 0.00083 (14) | −0.0706 (3) | 0.0290 (10) | |
H21A | 0.2855 | 0.0139 | −0.0233 | 0.035* | |
C22 | 0.1260 (5) | −0.02655 (14) | −0.0603 (3) | 0.0282 (9) | |
H22A | 0.0934 | −0.0315 | −0.0055 | 0.034* | |
C23 | −0.4396 (5) | −0.10863 (14) | −0.0601 (3) | 0.0275 (9) | |
H23A | −0.4428 | −0.0797 | −0.0618 | 0.033* | |
H23B | −0.3597 | −0.1166 | −0.0184 | 0.033* | |
C24 | −0.5900 (5) | −0.12474 (14) | −0.0332 (3) | 0.0273 (9) | |
H24A | −0.5824 | −0.1535 | −0.0256 | 0.033* | |
H24B | −0.6130 | −0.1131 | 0.0216 | 0.033* | |
C25 | −0.6777 (5) | −0.13313 (13) | −0.1763 (3) | 0.0264 (9) | |
H25A | −0.7614 | −0.1280 | −0.2178 | 0.032* | |
H25B | −0.6670 | −0.1618 | −0.1700 | 0.032* | |
C26 | −0.5345 (4) | −0.11600 (13) | −0.2097 (3) | 0.0243 (8) | |
H26A | −0.5143 | −0.1282 | −0.2645 | 0.029* | |
H26B | −0.5454 | −0.0874 | −0.2183 | 0.029* | |
C27 | −0.0130 (5) | −0.17653 (15) | −0.0915 (4) | 0.0262 (13) | 0.845 (9) |
H27A | 0.0434 | −0.1519 | −0.0968 | 0.031* | 0.845 (9) |
H27B | 0.0150 | −0.1947 | −0.1366 | 0.031* | 0.845 (9) |
C28 | 0.0221 (7) | −0.1951 (2) | −0.0041 (5) | 0.0331 (14) | 0.845 (9) |
H28A | 0.1299 | −0.1999 | 0.0039 | 0.040* | 0.845 (9) |
H28B | −0.0070 | −0.1768 | 0.0406 | 0.040* | 0.845 (9) |
C29 | −0.2173 (6) | −0.22426 (19) | −0.0044 (5) | 0.0351 (15) | 0.845 (9) |
H29A | −0.2437 | −0.2061 | 0.0411 | 0.042* | 0.845 (9) |
H29B | −0.2721 | −0.2490 | 0.0027 | 0.042* | 0.845 (9) |
C30 | −0.2626 (6) | −0.20632 (15) | −0.0901 (4) | 0.0273 (13) | 0.845 (9) |
H30A | −0.2397 | −0.2247 | −0.1358 | 0.033* | 0.845 (9) |
H30B | −0.3704 | −0.2011 | −0.0939 | 0.033* | 0.845 (9) |
C27' | −0.031 (3) | −0.1624 (8) | −0.0344 (16) | 0.018 (6)* | 0.155 (9) |
H27C | 0.0356 | −0.1418 | −0.0546 | 0.022* | 0.155 (9) |
H27D | −0.0592 | −0.1558 | 0.0233 | 0.022* | 0.155 (9) |
C28' | 0.037 (3) | −0.2007 (9) | −0.037 (2) | 0.016 (6)* | 0.155 (9) |
H28C | 0.1358 | −0.1998 | −0.0066 | 0.019* | 0.155 (9) |
H28D | 0.0521 | −0.2078 | −0.0966 | 0.019* | 0.155 (9) |
C29' | −0.208 (3) | −0.2333 (8) | −0.0522 (19) | 0.018 (6)* | 0.155 (9) |
H29C | −0.1883 | −0.2387 | −0.1119 | 0.022* | 0.155 (9) |
H29D | −0.2720 | −0.2544 | −0.0318 | 0.022* | 0.155 (9) |
C30' | −0.283 (3) | −0.1942 (9) | −0.045 (2) | 0.026 (7)* | 0.155 (9) |
H30C | −0.2830 | −0.1852 | 0.0143 | 0.031* | 0.155 (9) |
H30D | −0.3860 | −0.1948 | −0.0698 | 0.031* | 0.155 (9) |
O1S | −0.4337 (4) | −0.11083 (9) | −0.4241 (2) | 0.0289 (7) | |
C1S | −0.4988 (5) | −0.08145 (12) | −0.4558 (3) | 0.0265 (9) | |
C2S | −0.6548 (5) | −0.07059 (15) | −0.4332 (3) | 0.0337 (10) | |
H2SA | −0.6817 | −0.0858 | −0.3840 | 0.051* | |
H2SB | −0.7245 | −0.0763 | −0.4811 | 0.051* | |
H2SC | −0.6587 | −0.0426 | −0.4198 | 0.051* | |
C3S | −0.4258 (6) | −0.05516 (14) | −0.5204 (3) | 0.0343 (10) | |
H3SA | −0.3548 | −0.0706 | −0.5510 | 0.051* | |
H3SB | −0.3740 | −0.0335 | −0.4909 | 0.051* | |
H3SC | −0.5020 | −0.0446 | −0.5605 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
La1 | 0.01413 (10) | 0.01609 (10) | 0.02842 (12) | 0.00030 (9) | −0.00104 (7) | −0.00166 (10) |
P1 | 0.0146 (4) | 0.0218 (5) | 0.0319 (5) | −0.0002 (4) | −0.0007 (4) | −0.0071 (4) |
P2 | 0.0147 (5) | 0.0179 (5) | 0.0284 (5) | −0.0002 (4) | 0.0018 (4) | 0.0052 (4) |
O1 | 0.0222 (15) | 0.0216 (14) | 0.0283 (16) | 0.0023 (11) | −0.0031 (12) | −0.0035 (12) |
O2 | 0.0225 (15) | 0.0217 (14) | 0.0280 (16) | 0.0022 (11) | −0.0005 (12) | −0.0015 (12) |
O3 | 0.0355 (18) | 0.0208 (15) | 0.0394 (19) | 0.0096 (13) | 0.0057 (14) | −0.0008 (13) |
O4 | 0.0265 (16) | 0.0270 (15) | 0.0266 (16) | −0.0022 (12) | 0.0001 (12) | −0.0018 (12) |
O5 | 0.0308 (16) | 0.0208 (14) | 0.0261 (15) | −0.0045 (12) | −0.0024 (12) | −0.0023 (12) |
O6 | 0.0320 (18) | 0.0214 (15) | 0.045 (2) | −0.0071 (13) | 0.0075 (14) | −0.0041 (13) |
O7 | 0.0242 (16) | 0.0283 (16) | 0.0430 (19) | 0.0007 (12) | −0.0076 (14) | −0.0035 (14) |
O8 | 0.0247 (16) | 0.0264 (16) | 0.0428 (19) | −0.0032 (12) | 0.0084 (14) | −0.0030 (14) |
O9 | 0.0169 (17) | 0.053 (2) | 0.106 (4) | 0.0002 (16) | 0.0042 (19) | 0.001 (2) |
O10 | 0.0202 (14) | 0.0228 (14) | 0.0323 (16) | −0.0017 (12) | −0.0040 (11) | −0.0009 (13) |
O11 | 0.0307 (18) | 0.061 (2) | 0.0279 (17) | −0.0174 (16) | 0.0031 (14) | −0.0086 (16) |
O12 | 0.0166 (15) | 0.0417 (19) | 0.0365 (18) | 0.0019 (13) | −0.0030 (12) | −0.0032 (14) |
O13 | 0.0218 (16) | 0.0234 (16) | 0.059 (2) | 0.0033 (12) | 0.0079 (15) | −0.0020 (15) |
O14 | 0.0313 (18) | 0.0339 (18) | 0.0372 (19) | −0.0062 (14) | −0.0013 (14) | −0.0084 (14) |
O15 | 0.0351 (18) | 0.0303 (17) | 0.0403 (19) | −0.0054 (14) | 0.0020 (15) | 0.0093 (14) |
O16 | 0.0214 (14) | 0.0201 (15) | 0.0316 (16) | −0.0021 (11) | 0.0046 (12) | −0.0033 (11) |
O17 | 0.0338 (18) | 0.054 (2) | 0.0206 (16) | −0.0184 (16) | 0.0048 (13) | 0.0007 (14) |
O18 | 0.0164 (14) | 0.0319 (16) | 0.0346 (17) | −0.0005 (12) | 0.0027 (12) | −0.0007 (13) |
O19 | 0.0216 (16) | 0.0343 (18) | 0.054 (2) | 0.0014 (13) | −0.0043 (15) | 0.0208 (16) |
O21 | 0.0327 (18) | 0.0267 (16) | 0.0401 (19) | −0.0091 (13) | 0.0110 (14) | −0.0008 (14) |
O20 | 0.0299 (18) | 0.044 (2) | 0.043 (2) | −0.0173 (15) | 0.0019 (15) | −0.0128 (16) |
O1W | 0.0152 (14) | 0.0298 (16) | 0.047 (2) | −0.0053 (12) | 0.0076 (13) | −0.0133 (14) |
N1 | 0.0194 (16) | 0.0195 (16) | 0.0273 (18) | −0.0031 (13) | 0.0027 (13) | 0.0007 (14) |
N2 | 0.0216 (17) | 0.0196 (17) | 0.0290 (19) | 0.0013 (13) | −0.0018 (14) | −0.0010 (14) |
N3 | 0.0201 (17) | 0.0229 (18) | 0.057 (3) | 0.0006 (15) | 0.0019 (17) | 0.0033 (18) |
N5 | 0.0191 (17) | 0.0183 (16) | 0.0302 (19) | −0.0058 (13) | −0.0022 (14) | −0.0042 (14) |
N6 | 0.0116 (16) | 0.028 (2) | 0.058 (3) | −0.0013 (14) | 0.0010 (16) | −0.0219 (18) |
N7 | 0.0142 (15) | 0.0325 (19) | 0.0248 (18) | 0.0014 (13) | 0.0000 (13) | −0.0098 (14) |
N8 | 0.0261 (19) | 0.0180 (17) | 0.038 (2) | 0.0014 (14) | 0.0013 (16) | 0.0006 (15) |
N9 | 0.0182 (16) | 0.0210 (16) | 0.0228 (17) | −0.0021 (13) | 0.0029 (13) | 0.0055 (13) |
N10 | 0.0149 (16) | 0.0287 (18) | 0.0225 (17) | 0.0013 (13) | −0.0001 (13) | 0.0043 (14) |
N11 | 0.0155 (16) | 0.0246 (19) | 0.047 (2) | −0.0036 (13) | −0.0039 (15) | 0.0146 (16) |
N12 | 0.0249 (19) | 0.0254 (18) | 0.036 (2) | −0.0059 (15) | 0.0042 (16) | −0.0073 (16) |
C1 | 0.024 (2) | 0.032 (2) | 0.029 (2) | −0.0019 (17) | 0.0014 (17) | −0.0056 (18) |
C2 | 0.0191 (19) | 0.025 (2) | 0.028 (2) | 0.0002 (15) | 0.0005 (16) | −0.0020 (17) |
C3 | 0.023 (2) | 0.031 (2) | 0.024 (2) | −0.0014 (17) | 0.0024 (16) | −0.0033 (17) |
C4 | 0.028 (2) | 0.022 (2) | 0.027 (2) | 0.0017 (16) | −0.0034 (17) | −0.0032 (16) |
C5 | 0.0186 (19) | 0.0198 (19) | 0.033 (2) | 0.0022 (15) | −0.0037 (16) | 0.0010 (16) |
C6 | 0.023 (2) | 0.036 (2) | 0.021 (2) | −0.0006 (17) | 0.0008 (16) | 0.0009 (17) |
C7 | 0.021 (2) | 0.036 (2) | 0.023 (2) | 0.0007 (17) | −0.0017 (16) | −0.0042 (18) |
C8 | 0.020 (2) | 0.033 (2) | 0.035 (2) | 0.0045 (17) | 0.0008 (17) | −0.0093 (19) |
C9 | 0.020 (2) | 0.044 (3) | 0.034 (2) | 0.0010 (18) | 0.0024 (18) | −0.002 (2) |
C10 | 0.023 (2) | 0.042 (3) | 0.031 (2) | −0.0059 (18) | −0.0018 (17) | −0.004 (2) |
C11 | 0.021 (2) | 0.042 (3) | 0.028 (2) | −0.0053 (18) | −0.0039 (17) | −0.0069 (19) |
C12 | 0.015 (2) | 0.029 (3) | 0.031 (4) | −0.002 (2) | 0.005 (2) | −0.007 (3) |
C13 | 0.018 (3) | 0.021 (3) | 0.037 (4) | 0.000 (2) | 0.003 (3) | −0.006 (3) |
C14 | 0.018 (3) | 0.024 (3) | 0.035 (4) | 0.001 (2) | 0.002 (2) | −0.006 (2) |
C15 | 0.019 (3) | 0.028 (3) | 0.031 (4) | −0.004 (2) | 0.011 (3) | −0.011 (3) |
C12' | 0.013 (8) | 0.020 (9) | 0.034 (12) | −0.011 (6) | 0.003 (7) | 0.000 (8) |
C13' | 0.025 (10) | 0.016 (9) | 0.042 (14) | 0.000 (7) | −0.005 (10) | −0.017 (9) |
C14' | 0.011 (8) | 0.052 (13) | 0.023 (12) | −0.003 (8) | 0.001 (7) | −0.018 (9) |
C15' | 0.028 (10) | 0.019 (9) | 0.016 (10) | −0.010 (7) | 0.016 (8) | −0.009 (8) |
C16 | 0.0160 (18) | 0.028 (2) | 0.025 (2) | −0.0003 (15) | −0.0002 (15) | 0.0004 (16) |
C17 | 0.0169 (18) | 0.0206 (18) | 0.024 (2) | 0.0015 (14) | 0.0013 (15) | 0.0008 (15) |
C18 | 0.0202 (19) | 0.025 (2) | 0.021 (2) | −0.0016 (15) | −0.0008 (15) | −0.0011 (16) |
C19 | 0.025 (2) | 0.022 (2) | 0.027 (2) | −0.0007 (16) | 0.0037 (16) | 0.0018 (16) |
C20 | 0.0177 (19) | 0.023 (2) | 0.033 (2) | −0.0011 (15) | 0.0017 (16) | −0.0019 (17) |
C21 | 0.025 (2) | 0.037 (2) | 0.025 (2) | −0.0067 (18) | −0.0022 (17) | −0.0054 (18) |
C22 | 0.024 (2) | 0.036 (2) | 0.025 (2) | −0.0057 (18) | 0.0003 (17) | 0.0005 (18) |
C23 | 0.024 (2) | 0.031 (2) | 0.028 (2) | −0.0028 (17) | 0.0032 (17) | 0.0002 (17) |
C24 | 0.023 (2) | 0.031 (2) | 0.028 (2) | −0.0018 (17) | 0.0038 (17) | 0.0017 (18) |
C25 | 0.0165 (19) | 0.029 (2) | 0.033 (2) | −0.0003 (16) | −0.0003 (16) | −0.0018 (18) |
C26 | 0.0177 (19) | 0.030 (2) | 0.025 (2) | 0.0032 (16) | −0.0020 (15) | 0.0030 (17) |
C27 | 0.017 (2) | 0.026 (2) | 0.035 (3) | 0.0017 (18) | 0.001 (2) | 0.007 (2) |
C28 | 0.022 (3) | 0.040 (4) | 0.036 (4) | 0.003 (2) | −0.002 (3) | 0.010 (3) |
C29 | 0.021 (3) | 0.039 (3) | 0.045 (4) | 0.001 (2) | 0.003 (2) | 0.018 (3) |
C30 | 0.020 (3) | 0.020 (2) | 0.042 (3) | −0.0036 (18) | 0.001 (2) | 0.008 (2) |
O1S | 0.0272 (16) | 0.0246 (15) | 0.0344 (18) | 0.0044 (12) | −0.0017 (13) | −0.0054 (13) |
C1S | 0.025 (2) | 0.021 (2) | 0.033 (2) | 0.0034 (16) | −0.0029 (17) | −0.0070 (17) |
C2S | 0.028 (2) | 0.037 (3) | 0.036 (3) | 0.0089 (19) | −0.0009 (19) | −0.004 (2) |
C3S | 0.034 (3) | 0.035 (3) | 0.034 (3) | 0.004 (2) | −0.001 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
La1—O10 | 2.402 (3) | C8—H8A | 0.9700 |
La1—O16 | 2.432 (3) | C8—H8B | 0.9700 |
La1—O1W | 2.489 (3) | C9—H9A | 0.9700 |
La1—O1S | 2.605 (3) | C9—H9B | 0.9700 |
La1—O7 | 2.608 (3) | C10—C11 | 1.515 (6) |
La1—O2 | 2.611 (3) | C10—H10A | 0.9700 |
La1—O8 | 2.623 (3) | C10—H10B | 0.9700 |
La1—O1 | 2.640 (3) | C11—H11A | 0.9700 |
La1—O5 | 2.642 (3) | C11—H11B | 0.9700 |
La1—O4 | 2.786 (3) | C12—C13 | 1.508 (9) |
La1—N1 | 3.031 (3) | C12—H12A | 0.9700 |
La1—N3 | 3.049 (4) | C12—H12B | 0.9700 |
P1—O10 | 1.493 (3) | C13—H13A | 0.9700 |
P1—N7 | 1.618 (3) | C13—H13B | 0.9700 |
P1—N6 | 1.625 (4) | C14—C15 | 1.513 (9) |
P1—N5 | 1.687 (3) | C14—H14A | 0.9700 |
P2—O16 | 1.489 (3) | C14—H14B | 0.9700 |
P2—N10 | 1.616 (4) | C15—H15A | 0.9700 |
P2—N11 | 1.630 (4) | C15—H15B | 0.9700 |
P2—N9 | 1.690 (3) | C12'—C13' | 1.44 (3) |
O1—N1 | 1.251 (4) | C12'—H12C | 0.9700 |
O2—N1 | 1.272 (4) | C12'—H12D | 0.9700 |
O3—N1 | 1.229 (4) | C13'—H13C | 0.9700 |
O4—N2 | 1.263 (5) | C13'—H13D | 0.9700 |
O5—N2 | 1.267 (4) | C14'—C15' | 1.45 (3) |
O6—N2 | 1.234 (4) | C14'—H14C | 0.9700 |
O7—N3 | 1.281 (5) | C14'—H14D | 0.9700 |
O8—N3 | 1.261 (5) | C15'—H15C | 0.9700 |
O9—N3 | 1.218 (5) | C15'—H15D | 0.9700 |
O11—C1 | 1.215 (5) | C16—C17 | 1.500 (6) |
O12—C9 | 1.422 (5) | C17—C18 | 1.389 (6) |
O12—C10 | 1.435 (6) | C17—C22 | 1.399 (6) |
O13—C13 | 1.419 (6) | C18—C19 | 1.394 (6) |
O13—C14 | 1.449 (6) | C18—H18A | 0.9300 |
O13—C14' | 1.539 (18) | C19—C20 | 1.382 (6) |
O13—C13' | 1.64 (2) | C19—H19A | 0.9300 |
O14—N8 | 1.231 (5) | C20—C21 | 1.381 (6) |
O15—N8 | 1.222 (5) | C21—C22 | 1.376 (6) |
O17—C16 | 1.214 (5) | C21—H21A | 0.9300 |
O18—C25 | 1.423 (5) | C22—H22A | 0.9300 |
O18—C24 | 1.427 (5) | C23—C24 | 1.518 (6) |
O19—C29 | 1.433 (6) | C23—H23A | 0.9700 |
O19—C28 | 1.435 (7) | C23—H23B | 0.9700 |
O19—C28' | 1.50 (3) | C24—H24A | 0.9700 |
O19—C29' | 1.54 (3) | C24—H24B | 0.9700 |
O21—N12 | 1.229 (5) | C25—C26 | 1.511 (6) |
O20—N12 | 1.227 (5) | C25—H25A | 0.9700 |
O1W—H1W1 | 0.8904 | C25—H25B | 0.9700 |
O1W—H2W1 | 0.8900 | C26—H26A | 0.9700 |
N5—C1 | 1.377 (6) | C26—H26B | 0.9700 |
N5—H5N | 0.8502 | C27—C28 | 1.510 (8) |
N6—C15' | 1.484 (19) | C27—H27A | 0.9700 |
N6—C12 | 1.503 (6) | C27—H27B | 0.9700 |
N6—C15 | 1.512 (7) | C28—H28A | 0.9700 |
N6—C12' | 1.590 (18) | C28—H28B | 0.9700 |
N7—C11 | 1.467 (5) | C29—C30 | 1.496 (8) |
N7—C8 | 1.470 (5) | C29—H29A | 0.9700 |
N8—C5 | 1.470 (5) | C29—H29B | 0.9700 |
N9—C16 | 1.371 (5) | C30—H30A | 0.9700 |
N9—H9N | 0.8501 | C30—H30B | 0.9700 |
N10—C23 | 1.469 (5) | C27'—C28' | 1.42 (4) |
N10—C26 | 1.482 (5) | C27'—H27C | 0.9700 |
N11—C27 | 1.484 (6) | C27'—H27D | 0.9700 |
N11—C30 | 1.489 (6) | C28'—H28C | 0.9700 |
N11—C30' | 1.56 (3) | C28'—H28D | 0.9700 |
N11—C27' | 1.62 (2) | C29'—C30' | 1.48 (4) |
N12—C20 | 1.471 (5) | C29'—H29C | 0.9700 |
C1—C2 | 1.499 (6) | C29'—H29D | 0.9700 |
C2—C7 | 1.390 (6) | C30'—H30C | 0.9700 |
C2—C3 | 1.400 (6) | C30'—H30D | 0.9700 |
C3—C4 | 1.380 (6) | O1S—C1S | 1.229 (5) |
C3—H3A | 0.9300 | C1S—C2S | 1.491 (6) |
C4—C5 | 1.384 (6) | C1S—C3S | 1.508 (7) |
C4—H4A | 0.9300 | C2S—H2SA | 0.9600 |
C5—C6 | 1.375 (6) | C2S—H2SB | 0.9600 |
C6—C7 | 1.375 (6) | C2S—H2SC | 0.9600 |
C6—H6A | 0.9300 | C3S—H3SA | 0.9600 |
C7—H7A | 0.9300 | C3S—H3SB | 0.9600 |
C8—C9 | 1.490 (6) | C3S—H3SC | 0.9600 |
| | | |
O10—La1—O16 | 148.98 (10) | O12—C9—C8 | 110.9 (4) |
O10—La1—O1W | 82.42 (10) | O12—C9—H9A | 109.5 |
O16—La1—O1W | 77.39 (10) | C8—C9—H9A | 109.5 |
O10—La1—O1S | 73.39 (10) | O12—C9—H9B | 109.5 |
O16—La1—O1S | 78.90 (10) | C8—C9—H9B | 109.5 |
O1W—La1—O1S | 75.62 (10) | H9A—C9—H9B | 108.0 |
O10—La1—O7 | 126.71 (10) | O12—C10—C11 | 111.4 (4) |
O16—La1—O7 | 81.77 (10) | O12—C10—H10A | 109.4 |
O1W—La1—O7 | 144.20 (11) | C11—C10—H10A | 109.4 |
O1S—La1—O7 | 128.23 (10) | O12—C10—H10B | 109.4 |
O10—La1—O2 | 116.93 (10) | C11—C10—H10B | 109.4 |
O16—La1—O2 | 81.24 (9) | H10A—C10—H10B | 108.0 |
O1W—La1—O2 | 77.11 (10) | N7—C11—C10 | 108.9 (4) |
O1S—La1—O2 | 149.10 (10) | N7—C11—H11A | 109.9 |
O7—La1—O2 | 71.15 (9) | C10—C11—H11A | 109.9 |
O10—La1—O8 | 83.51 (10) | N7—C11—H11B | 109.9 |
O16—La1—O8 | 127.48 (10) | C10—C11—H11B | 109.9 |
O1W—La1—O8 | 130.82 (10) | H11A—C11—H11B | 108.3 |
O1S—La1—O8 | 142.44 (10) | N6—C12—C13 | 107.6 (5) |
O7—La1—O8 | 48.86 (10) | N6—C12—H12A | 110.2 |
O2—La1—O8 | 68.13 (10) | C13—C12—H12A | 110.2 |
O10—La1—O1 | 68.45 (9) | N6—C12—H12B | 110.2 |
O16—La1—O1 | 122.63 (9) | C13—C12—H12B | 110.2 |
O1W—La1—O1 | 67.15 (9) | H12A—C12—H12B | 108.5 |
O1S—La1—O1 | 129.06 (9) | O13—C13—C12 | 109.5 (5) |
O7—La1—O1 | 101.74 (9) | O13—C13—H13A | 109.8 |
O2—La1—O1 | 48.56 (9) | C12—C13—H13A | 109.8 |
O8—La1—O1 | 63.83 (9) | O13—C13—H13B | 109.8 |
O10—La1—O5 | 71.10 (9) | C12—C13—H13B | 109.8 |
O16—La1—O5 | 116.81 (9) | H13A—C13—H13B | 108.2 |
O1W—La1—O5 | 147.22 (10) | O13—C14—C15 | 109.5 (5) |
O1S—La1—O5 | 78.48 (10) | O13—C14—H14A | 109.8 |
O7—La1—O5 | 68.54 (10) | C15—C14—H14A | 109.8 |
O2—La1—O5 | 132.00 (9) | O13—C14—H14B | 109.8 |
O8—La1—O5 | 66.03 (9) | C15—C14—H14B | 109.8 |
O1—La1—O5 | 117.45 (9) | H14A—C14—H14B | 108.2 |
O10—La1—O4 | 108.97 (9) | N6—C15—C14 | 107.3 (5) |
O16—La1—O4 | 70.16 (9) | N6—C15—H15A | 110.3 |
O1W—La1—O4 | 132.43 (9) | C14—C15—H15A | 110.3 |
O1S—La1—O4 | 64.88 (9) | N6—C15—H15B | 110.3 |
O7—La1—O4 | 63.41 (9) | C14—C15—H15B | 110.3 |
O2—La1—O4 | 128.66 (9) | H15A—C15—H15B | 108.5 |
O8—La1—O4 | 96.69 (9) | C13'—C12'—N6 | 99.2 (16) |
O1—La1—O4 | 160.38 (9) | C13'—C12'—H12C | 111.9 |
O5—La1—O4 | 46.80 (9) | N6—C12'—H12C | 111.9 |
O10—La1—N1 | 92.32 (10) | C13'—C12'—H12D | 111.9 |
O16—La1—N1 | 103.96 (9) | N6—C12'—H12D | 111.9 |
O1W—La1—N1 | 73.33 (9) | H12C—C12'—H12D | 109.6 |
O1S—La1—N1 | 147.25 (9) | C12'—C13'—O13 | 105.0 (17) |
O7—La1—N1 | 84.04 (9) | C12'—C13'—H13C | 110.8 |
O2—La1—N1 | 24.66 (9) | O13—C13'—H13C | 110.8 |
O8—La1—N1 | 60.45 (9) | C12'—C13'—H13D | 110.8 |
O1—La1—N1 | 24.26 (9) | O13—C13'—H13D | 110.8 |
O5—La1—N1 | 125.36 (9) | H13C—C13'—H13D | 108.8 |
O4—La1—N1 | 147.32 (9) | C15'—C14'—O13 | 107.5 (17) |
O10—La1—N3 | 105.18 (11) | C15'—C14'—H14C | 110.2 |
O16—La1—N3 | 105.05 (11) | O13—C14'—H14C | 110.2 |
O1W—La1—N3 | 143.67 (10) | C15'—C14'—H14D | 110.2 |
O1S—La1—N3 | 140.71 (10) | O13—C14'—H14D | 110.2 |
O7—La1—N3 | 24.62 (11) | H14C—C14'—H14D | 108.5 |
O2—La1—N3 | 67.72 (10) | C14'—C15'—N6 | 101.0 (17) |
O8—La1—N3 | 24.23 (11) | C14'—C15'—H15C | 111.6 |
O1—La1—N3 | 82.47 (10) | N6—C15'—H15C | 111.6 |
O5—La1—N3 | 64.71 (10) | C14'—C15'—H15D | 111.6 |
O4—La1—N3 | 79.52 (10) | N6—C15'—H15D | 111.6 |
N1—La1—N3 | 70.93 (10) | H15C—C15'—H15D | 109.4 |
O10—P1—N7 | 108.74 (17) | O17—C16—N9 | 121.1 (4) |
O10—P1—N6 | 118.1 (2) | O17—C16—C17 | 121.9 (4) |
N7—P1—N6 | 106.70 (18) | N9—C16—C17 | 117.0 (4) |
O10—P1—N5 | 103.07 (17) | C18—C17—C22 | 119.2 (4) |
N7—P1—N5 | 115.68 (19) | C18—C17—C16 | 124.7 (4) |
N6—P1—N5 | 104.86 (19) | C22—C17—C16 | 116.1 (4) |
O16—P2—N10 | 109.83 (18) | C17—C18—C19 | 120.5 (4) |
O16—P2—N11 | 116.93 (19) | C17—C18—H18A | 119.8 |
N10—P2—N11 | 105.71 (19) | C19—C18—H18A | 119.8 |
O16—P2—N9 | 104.36 (17) | C20—C19—C18 | 118.2 (4) |
N10—P2—N9 | 114.98 (18) | C20—C19—H19A | 120.9 |
N11—P2—N9 | 105.31 (17) | C18—C19—H19A | 120.9 |
N1—O1—La1 | 95.6 (2) | C21—C20—C19 | 122.9 (4) |
N1—O2—La1 | 96.5 (2) | C21—C20—N12 | 119.1 (4) |
N2—O4—La1 | 94.3 (2) | C19—C20—N12 | 118.0 (4) |
N2—O5—La1 | 101.2 (2) | C22—C21—C20 | 118.1 (4) |
N3—O7—La1 | 97.3 (2) | C22—C21—H21A | 120.9 |
N3—O8—La1 | 97.2 (2) | C20—C21—H21A | 120.9 |
P1—O10—La1 | 158.91 (18) | C21—C22—C17 | 121.2 (4) |
C9—O12—C10 | 110.3 (3) | C21—C22—H22A | 119.4 |
C13—O13—C14 | 109.7 (4) | C17—C22—H22A | 119.4 |
C13—O13—C14' | 111.1 (9) | N10—C23—C24 | 109.5 (4) |
C14—O13—C13' | 113.4 (8) | N10—C23—H23A | 109.8 |
C14'—O13—C13' | 96.2 (11) | C24—C23—H23A | 109.8 |
P2—O16—La1 | 160.70 (17) | N10—C23—H23B | 109.8 |
C25—O18—C24 | 109.8 (3) | C24—C23—H23B | 109.8 |
C29—O19—C28 | 109.1 (4) | H23A—C23—H23B | 108.2 |
C29—O19—C28' | 114.5 (12) | O18—C24—C23 | 111.9 (4) |
C28—O19—C29' | 113.4 (10) | O18—C24—H24A | 109.2 |
C28'—O19—C29' | 106.1 (16) | C23—C24—H24A | 109.2 |
La1—O1W—H1W1 | 119.0 | O18—C24—H24B | 109.2 |
La1—O1W—H2W1 | 131.9 | C23—C24—H24B | 109.2 |
H1W1—O1W—H2W1 | 109.1 | H24A—C24—H24B | 107.9 |
O3—N1—O1 | 121.3 (4) | O18—C25—C26 | 111.4 (3) |
O3—N1—O2 | 121.0 (3) | O18—C25—H25A | 109.3 |
O1—N1—O2 | 117.7 (3) | C26—C25—H25A | 109.3 |
O3—N1—La1 | 168.1 (3) | O18—C25—H25B | 109.3 |
O1—N1—La1 | 60.11 (19) | C26—C25—H25B | 109.3 |
O2—N1—La1 | 58.88 (19) | H25A—C25—H25B | 108.0 |
O6—N2—O4 | 121.8 (3) | N10—C26—C25 | 108.4 (3) |
O6—N2—O5 | 120.9 (4) | N10—C26—H26A | 110.0 |
O4—N2—O5 | 117.3 (3) | C25—C26—H26A | 110.0 |
O9—N3—O8 | 121.6 (4) | N10—C26—H26B | 110.0 |
O9—N3—O7 | 121.7 (4) | C25—C26—H26B | 110.0 |
O8—N3—O7 | 116.6 (4) | H26A—C26—H26B | 108.4 |
O9—N3—La1 | 178.4 (3) | N11—C27—C28 | 107.8 (4) |
O8—N3—La1 | 58.6 (2) | N11—C27—H27A | 110.2 |
O7—N3—La1 | 58.0 (2) | C28—C27—H27A | 110.2 |
C1—N5—P1 | 128.6 (3) | N11—C27—H27B | 110.2 |
C1—N5—H5N | 115.0 | C28—C27—H27B | 110.2 |
P1—N5—H5N | 115.5 | H27A—C27—H27B | 108.5 |
C15'—N6—C12 | 115.6 (9) | O19—C28—C27 | 110.1 (5) |
C12—N6—C15 | 107.0 (4) | O19—C28—H28A | 109.6 |
C15'—N6—C12' | 106.7 (10) | C27—C28—H28A | 109.6 |
C15—N6—C12' | 117.4 (7) | O19—C28—H28B | 109.6 |
C15'—N6—P1 | 125.4 (8) | C27—C28—H28B | 109.6 |
C12—N6—P1 | 117.2 (3) | H28A—C28—H28B | 108.1 |
C15—N6—P1 | 118.0 (3) | O19—C29—C30 | 110.9 (5) |
C12'—N6—P1 | 124.0 (7) | O19—C29—H29A | 109.5 |
C11—N7—C8 | 111.5 (3) | C30—C29—H29A | 109.5 |
C11—N7—P1 | 125.8 (3) | O19—C29—H29B | 109.5 |
C8—N7—P1 | 119.7 (3) | C30—C29—H29B | 109.5 |
O15—N8—O14 | 124.3 (4) | H29A—C29—H29B | 108.0 |
O15—N8—C5 | 117.7 (4) | N11—C30—C29 | 108.6 (5) |
O14—N8—C5 | 118.0 (4) | N11—C30—H30A | 110.0 |
C16—N9—P2 | 128.0 (3) | C29—C30—H30A | 110.0 |
C16—N9—H9N | 115.8 | N11—C30—H30B | 110.0 |
P2—N9—H9N | 115.7 | C29—C30—H30B | 110.0 |
C23—N10—C26 | 111.6 (3) | H30A—C30—H30B | 108.3 |
C23—N10—P2 | 124.8 (3) | C28'—C27'—N11 | 102 (2) |
C26—N10—P2 | 121.7 (3) | C28'—C27'—H27C | 111.5 |
C27—N11—C30 | 109.5 (4) | N11—C27'—H27C | 111.5 |
C27—N11—C30' | 117.8 (11) | C28'—C27'—H27D | 111.5 |
C30—N11—C27' | 115.8 (9) | N11—C27'—H27D | 111.5 |
C30'—N11—C27' | 102.3 (14) | H27C—C27'—H27D | 109.3 |
C27—N11—P2 | 119.2 (3) | C27'—C28'—O19 | 112 (2) |
C30—N11—P2 | 116.2 (3) | C27'—C28'—H28C | 109.3 |
C30'—N11—P2 | 122.3 (11) | O19—C28'—H28C | 109.3 |
C27'—N11—P2 | 128.0 (9) | C27'—C28'—H28D | 109.3 |
O20—N12—O21 | 124.0 (4) | O19—C28'—H28D | 109.3 |
O20—N12—C20 | 117.9 (4) | H28C—C28'—H28D | 108.0 |
O21—N12—C20 | 118.1 (4) | C30'—C29'—O19 | 108 (2) |
O11—C1—N5 | 121.6 (4) | C30'—C29'—H29C | 110.0 |
O11—C1—C2 | 122.6 (4) | O19—C29'—H29C | 110.0 |
N5—C1—C2 | 115.8 (4) | C30'—C29'—H29D | 110.0 |
C7—C2—C3 | 119.8 (4) | O19—C29'—H29D | 110.0 |
C7—C2—C1 | 117.5 (4) | H29C—C29'—H29D | 108.4 |
C3—C2—C1 | 122.6 (4) | C29'—C30'—N11 | 99 (2) |
C4—C3—C2 | 120.3 (4) | C29'—C30'—H30C | 111.9 |
C4—C3—H3A | 119.9 | N11—C30'—H30C | 111.9 |
C2—C3—H3A | 119.9 | C29'—C30'—H30D | 111.9 |
C3—C4—C5 | 118.0 (4) | N11—C30'—H30D | 111.9 |
C3—C4—H4A | 121.0 | H30C—C30'—H30D | 109.6 |
C5—C4—H4A | 121.0 | C1S—O1S—La1 | 151.8 (3) |
C6—C5—C4 | 123.0 (4) | O1S—C1S—C2S | 121.4 (4) |
C6—C5—N8 | 118.7 (4) | O1S—C1S—C3S | 121.6 (4) |
C4—C5—N8 | 118.3 (4) | C2S—C1S—C3S | 117.0 (4) |
C7—C6—C5 | 118.6 (4) | C1S—C2S—H2SA | 109.5 |
C7—C6—H6A | 120.7 | C1S—C2S—H2SB | 109.5 |
C5—C6—H6A | 120.7 | H2SA—C2S—H2SB | 109.5 |
C6—C7—C2 | 120.3 (4) | C1S—C2S—H2SC | 109.5 |
C6—C7—H7A | 119.9 | H2SA—C2S—H2SC | 109.5 |
C2—C7—H7A | 119.9 | H2SB—C2S—H2SC | 109.5 |
N7—C8—C9 | 109.3 (4) | C1S—C3S—H3SA | 109.5 |
N7—C8—H8A | 109.8 | C1S—C3S—H3SB | 109.5 |
C9—C8—H8A | 109.8 | H3SA—C3S—H3SB | 109.5 |
N7—C8—H8B | 109.8 | C1S—C3S—H3SC | 109.5 |
C9—C8—H8B | 109.8 | H3SA—C3S—H3SC | 109.5 |
H8A—C8—H8B | 108.3 | H3SB—C3S—H3SC | 109.5 |
| | | |
O10—La1—O1—N1 | 169.1 (2) | N5—P1—N6—C15 | 179.3 (4) |
O16—La1—O1—N1 | −43.7 (3) | O10—P1—N6—C12' | −106.2 (10) |
O1W—La1—O1—N1 | −100.2 (2) | N7—P1—N6—C12' | 131.0 (10) |
O1S—La1—O1—N1 | −146.7 (2) | N5—P1—N6—C12' | 7.8 (10) |
O7—La1—O1—N1 | 44.0 (2) | O10—P1—N7—C11 | −176.4 (3) |
O2—La1—O1—N1 | −7.4 (2) | N6—P1—N7—C11 | −48.0 (4) |
O8—La1—O1—N1 | 75.7 (2) | N5—P1—N7—C11 | 68.2 (4) |
O5—La1—O1—N1 | 115.8 (2) | O10—P1—N7—C8 | 24.5 (4) |
O4—La1—O1—N1 | 82.9 (3) | N6—P1—N7—C8 | 152.9 (4) |
N3—La1—O1—N1 | 59.4 (2) | N5—P1—N7—C8 | −90.9 (4) |
O10—La1—O2—N1 | 3.6 (2) | O16—P2—N9—C16 | −178.5 (3) |
O16—La1—O2—N1 | 157.0 (2) | N10—P2—N9—C16 | 61.2 (4) |
O1W—La1—O2—N1 | 78.1 (2) | N11—P2—N9—C16 | −54.8 (4) |
O1S—La1—O2—N1 | 106.6 (3) | O16—P2—N10—C23 | 177.8 (3) |
O7—La1—O2—N1 | −118.7 (2) | N11—P2—N10—C23 | 50.9 (4) |
O8—La1—O2—N1 | −66.5 (2) | N9—P2—N10—C23 | −64.8 (4) |
O1—La1—O2—N1 | 7.3 (2) | O16—P2—N10—C26 | −19.3 (4) |
O5—La1—O2—N1 | −84.6 (2) | N11—P2—N10—C26 | −146.3 (3) |
O4—La1—O2—N1 | −147.2 (2) | N9—P2—N10—C26 | 98.0 (3) |
N3—La1—O2—N1 | −92.7 (2) | O16—P2—N11—C27 | 76.2 (4) |
O10—La1—O4—N2 | −41.2 (2) | N10—P2—N11—C27 | −161.2 (4) |
O16—La1—O4—N2 | 171.7 (2) | N9—P2—N11—C27 | −39.1 (4) |
O1W—La1—O4—N2 | −138.4 (2) | O16—P2—N11—C30 | −58.4 (4) |
O1S—La1—O4—N2 | −101.6 (2) | N10—P2—N11—C30 | 64.2 (4) |
O7—La1—O4—N2 | 81.1 (2) | N9—P2—N11—C30 | −173.7 (4) |
O2—La1—O4—N2 | 111.4 (2) | O16—P2—N11—C30' | −94.3 (15) |
O8—La1—O4—N2 | 44.2 (2) | N10—P2—N11—C30' | 28.3 (15) |
O1—La1—O4—N2 | 37.7 (4) | N9—P2—N11—C30' | 150.4 (15) |
O5—La1—O4—N2 | −3.7 (2) | O16—P2—N11—C27' | 121.4 (12) |
N1—La1—O4—N2 | 86.7 (3) | N10—P2—N11—C27' | −116.0 (12) |
N3—La1—O4—N2 | 61.4 (2) | N9—P2—N11—C27' | 6.1 (12) |
O10—La1—O5—N2 | 146.2 (2) | P1—N5—C1—O11 | 4.9 (7) |
O16—La1—O5—N2 | −1.2 (3) | P1—N5—C1—C2 | −173.6 (3) |
O1W—La1—O5—N2 | 108.3 (3) | O11—C1—C2—C7 | −13.0 (7) |
O1S—La1—O5—N2 | 70.0 (2) | N5—C1—C2—C7 | 165.4 (4) |
O7—La1—O5—N2 | −69.4 (2) | O11—C1—C2—C3 | 166.4 (5) |
O2—La1—O5—N2 | −104.2 (2) | N5—C1—C2—C3 | −15.1 (6) |
O8—La1—O5—N2 | −122.6 (2) | C7—C2—C3—C4 | −1.3 (6) |
O1—La1—O5—N2 | −161.8 (2) | C1—C2—C3—C4 | 179.2 (4) |
O4—La1—O5—N2 | 3.7 (2) | C2—C3—C4—C5 | 1.0 (6) |
N1—La1—O5—N2 | −134.8 (2) | C3—C4—C5—C6 | 0.0 (6) |
N3—La1—O5—N2 | −95.9 (2) | C3—C4—C5—N8 | 177.8 (4) |
O10—La1—O7—N3 | −32.5 (3) | O15—N8—C5—C6 | 17.2 (6) |
O16—La1—O7—N3 | 161.0 (3) | O14—N8—C5—C6 | −162.3 (4) |
O1W—La1—O7—N3 | 106.3 (3) | O15—N8—C5—C4 | −160.7 (4) |
O1S—La1—O7—N3 | −130.2 (2) | O14—N8—C5—C4 | 19.8 (6) |
O2—La1—O7—N3 | 77.5 (2) | C4—C5—C6—C7 | −0.7 (7) |
O8—La1—O7—N3 | 0.4 (2) | N8—C5—C6—C7 | −178.5 (4) |
O1—La1—O7—N3 | 39.2 (3) | C5—C6—C7—C2 | 0.3 (7) |
O5—La1—O7—N3 | −75.9 (2) | C3—C2—C7—C6 | 0.7 (7) |
O4—La1—O7—N3 | −127.2 (3) | C1—C2—C7—C6 | −179.9 (4) |
N1—La1—O7—N3 | 55.9 (2) | C11—N7—C8—C9 | 56.7 (5) |
O10—La1—O8—N3 | 153.5 (3) | P1—N7—C8—C9 | −141.5 (3) |
O16—La1—O8—N3 | −25.0 (3) | C10—O12—C9—C8 | 60.5 (5) |
O1W—La1—O8—N3 | −132.4 (2) | N7—C8—C9—O12 | −58.8 (5) |
O1S—La1—O8—N3 | 101.8 (3) | C9—O12—C10—C11 | −59.1 (5) |
O7—La1—O8—N3 | −0.5 (2) | C8—N7—C11—C10 | −54.9 (5) |
O2—La1—O8—N3 | −84.1 (2) | P1—N7—C11—C10 | 144.6 (3) |
O1—La1—O8—N3 | −137.4 (3) | O12—C10—C11—N7 | 55.9 (5) |
O5—La1—O8—N3 | 81.3 (2) | C15'—N6—C12—C13 | 32.0 (12) |
O4—La1—O8—N3 | 45.1 (3) | C15—N6—C12—C13 | 62.3 (7) |
N1—La1—O8—N3 | −110.1 (3) | C12'—N6—C12—C13 | −51.3 (11) |
N7—P1—O10—La1 | −169.9 (5) | P1—N6—C12—C13 | −162.6 (4) |
N6—P1—O10—La1 | 68.4 (6) | C14—O13—C13—C12 | 63.1 (7) |
N5—P1—O10—La1 | −46.6 (5) | C14'—O13—C13—C12 | 24.0 (11) |
O16—La1—O10—P1 | 161.9 (4) | C13'—O13—C13—C12 | −39.8 (15) |
O1W—La1—O10—P1 | −148.6 (5) | N6—C12—C13—O13 | −63.4 (7) |
O1S—La1—O10—P1 | 134.2 (5) | C13—O13—C14—C15 | −62.7 (7) |
O7—La1—O10—P1 | 8.6 (6) | C14'—O13—C14—C15 | 36.4 (14) |
O2—La1—O10—P1 | −77.2 (5) | C13'—O13—C14—C15 | −30.9 (14) |
O8—La1—O10—P1 | −15.8 (5) | C15'—N6—C15—C14 | 50.5 (17) |
O1—La1—O10—P1 | −80.2 (5) | C12—N6—C15—C14 | −61.6 (7) |
O5—La1—O10—P1 | 51.0 (5) | C12'—N6—C15—C14 | −24.3 (12) |
O4—La1—O10—P1 | 79.1 (5) | P1—N6—C15—C14 | 163.7 (4) |
N1—La1—O10—P1 | −75.7 (5) | O13—C14—C15—N6 | 61.7 (7) |
N3—La1—O10—P1 | −4.9 (5) | C15'—N6—C12'—C13' | −73.8 (19) |
N10—P2—O16—La1 | 125.1 (5) | C12—N6—C12'—C13' | 36.9 (12) |
N11—P2—O16—La1 | −114.5 (5) | C15—N6—C12'—C13' | −44.1 (18) |
N9—P2—O16—La1 | 1.3 (6) | P1—N6—C12'—C13' | 127.4 (12) |
O10—La1—O16—P2 | −118.6 (5) | N6—C12'—C13'—O13 | 73.9 (17) |
O1W—La1—O16—P2 | −169.2 (6) | C13—O13—C13'—C12' | 47.6 (16) |
O1S—La1—O16—P2 | −91.7 (6) | C14—O13—C13'—C12' | −41 (2) |
O7—La1—O16—P2 | 40.1 (5) | C14'—O13—C13'—C12' | −75 (2) |
O2—La1—O16—P2 | 112.1 (6) | C13—O13—C14'—C15' | 47.0 (17) |
O8—La1—O16—P2 | 58.5 (6) | C14—O13—C14'—C15' | −48.0 (14) |
O1—La1—O16—P2 | 138.8 (5) | C13'—O13—C14'—C15' | 73.6 (18) |
O5—La1—O16—P2 | −20.8 (6) | O13—C14'—C15'—N6 | −75.7 (16) |
O4—La1—O16—P2 | −24.6 (5) | C12—N6—C15'—C14' | 34.1 (17) |
N1—La1—O16—P2 | 121.8 (5) | C15—N6—C15'—C14' | −44.9 (16) |
N3—La1—O16—P2 | 48.2 (6) | C12'—N6—C15'—C14' | 71.6 (18) |
La1—O1—N1—O3 | −166.2 (3) | P1—N6—C15'—C14' | −129.9 (11) |
La1—O1—N1—O2 | 12.9 (3) | P2—N9—C16—O17 | −0.9 (6) |
La1—O2—N1—O3 | 166.0 (3) | P2—N9—C16—C17 | 177.8 (3) |
La1—O2—N1—O1 | −13.1 (3) | O17—C16—C17—C18 | −175.0 (4) |
O10—La1—N1—O3 | 90.2 (14) | N9—C16—C17—C18 | 6.3 (6) |
O16—La1—N1—O3 | −116.4 (14) | O17—C16—C17—C22 | 6.0 (6) |
O1W—La1—N1—O3 | 171.6 (14) | N9—C16—C17—C22 | −172.7 (4) |
O1S—La1—N1—O3 | 152.5 (13) | C22—C17—C18—C19 | −0.4 (6) |
O7—La1—N1—O3 | −36.5 (14) | C16—C17—C18—C19 | −179.3 (4) |
O2—La1—N1—O3 | −93.0 (14) | C17—C18—C19—C20 | 0.9 (6) |
O8—La1—N1—O3 | 9.0 (13) | C18—C19—C20—C21 | −0.3 (6) |
O1—La1—N1—O3 | 100.4 (14) | C18—C19—C20—N12 | 179.5 (4) |
O5—La1—N1—O3 | 21.9 (14) | O20—N12—C20—C21 | 11.1 (6) |
O4—La1—N1—O3 | −41.5 (14) | O21—N12—C20—C21 | −168.5 (4) |
N3—La1—N1—O3 | −15.0 (13) | O20—N12—C20—C19 | −168.7 (4) |
O10—La1—N1—O1 | −10.2 (2) | O21—N12—C20—C19 | 11.6 (6) |
O16—La1—N1—O1 | 143.2 (2) | C19—C20—C21—C22 | −0.9 (7) |
O1W—La1—N1—O1 | 71.2 (2) | N12—C20—C21—C22 | 179.2 (4) |
O1S—La1—N1—O1 | 52.1 (3) | C20—C21—C22—C17 | 1.6 (7) |
O7—La1—N1—O1 | −136.8 (2) | C18—C17—C22—C21 | −0.9 (7) |
O2—La1—N1—O1 | 166.6 (4) | C16—C17—C22—C21 | 178.1 (4) |
O8—La1—N1—O1 | −91.4 (2) | C26—N10—C23—C24 | 54.1 (5) |
O5—La1—N1—O1 | −78.5 (2) | P2—N10—C23—C24 | −141.5 (3) |
O4—La1—N1—O1 | −141.9 (2) | C25—O18—C24—C23 | 59.0 (5) |
N3—La1—N1—O1 | −115.4 (2) | N10—C23—C24—O18 | −55.5 (5) |
O10—La1—N1—O2 | −176.8 (2) | C24—O18—C25—C26 | −61.2 (4) |
O16—La1—N1—O2 | −23.4 (2) | C23—N10—C26—C25 | −55.8 (4) |
O1W—La1—N1—O2 | −95.4 (2) | P2—N10—C26—C25 | 139.3 (3) |
O1S—La1—N1—O2 | −114.5 (2) | O18—C25—C26—N10 | 59.2 (4) |
O7—La1—N1—O2 | 56.6 (2) | C30—N11—C27—C28 | −59.0 (6) |
O8—La1—N1—O2 | 102.0 (2) | C30'—N11—C27—C28 | −25.4 (16) |
O1—La1—N1—O2 | −166.6 (4) | C27'—N11—C27—C28 | 48.3 (15) |
O5—La1—N1—O2 | 114.9 (2) | P2—N11—C27—C28 | 163.7 (4) |
O4—La1—N1—O2 | 51.5 (3) | C29—O19—C28—C27 | −62.4 (7) |
N3—La1—N1—O2 | 78.0 (2) | C28'—O19—C28—C27 | 46 (3) |
La1—O4—N2—O6 | −174.8 (3) | C29'—O19—C28—C27 | −29.0 (15) |
La1—O4—N2—O5 | 6.3 (3) | N11—C27—C28—O19 | 61.4 (6) |
La1—O5—N2—O6 | 174.3 (3) | C28—O19—C29—C30 | 61.5 (7) |
La1—O5—N2—O4 | −6.7 (4) | C28'—O19—C29—C30 | 38.3 (15) |
La1—O8—N3—O9 | −178.1 (4) | C29'—O19—C29—C30 | −42.4 (19) |
La1—O8—N3—O7 | 0.8 (4) | C27—N11—C30—C29 | 58.2 (6) |
La1—O7—N3—O9 | 178.1 (4) | C30'—N11—C30—C29 | −53 (2) |
La1—O7—N3—O8 | −0.8 (4) | C27'—N11—C30—C29 | 17.1 (12) |
O10—La1—N3—O8 | −27.4 (3) | P2—N11—C30—C29 | −163.1 (4) |
O16—La1—N3—O8 | 159.7 (2) | O19—C29—C30—N11 | −59.3 (7) |
O1W—La1—N3—O8 | 70.6 (3) | C27—N11—C27'—C28' | −45.4 (16) |
O1S—La1—N3—O8 | −109.6 (3) | C30—N11—C27'—C28' | 44 (2) |
O7—La1—N3—O8 | 179.2 (4) | C30'—N11—C27'—C28' | 74 (2) |
O2—La1—N3—O8 | 86.0 (2) | P2—N11—C27'—C28' | −136.1 (16) |
O1—La1—N3—O8 | 37.8 (2) | N11—C27'—C28'—O19 | −67 (2) |
O5—La1—N3—O8 | −87.4 (3) | C29—O19—C28'—C27' | 30 (3) |
O4—La1—N3—O8 | −134.4 (3) | C28—O19—C28'—C27' | −51 (3) |
N1—La1—N3—O8 | 59.8 (2) | C29'—O19—C28'—C27' | 62 (3) |
O10—La1—N3—O7 | 153.5 (2) | C29—O19—C29'—C30' | 47.3 (19) |
O16—La1—N3—O7 | −19.5 (3) | C28—O19—C29'—C30' | −41 (3) |
O1W—La1—N3—O7 | −108.6 (3) | C28'—O19—C29'—C30' | −64 (3) |
O1S—La1—N3—O7 | 71.3 (3) | O19—C29'—C30'—N11 | 72 (2) |
O2—La1—N3—O7 | −93.2 (3) | C27—N11—C30'—C29' | −39 (2) |
O8—La1—N3—O7 | −179.2 (4) | C30—N11—C30'—C29' | 43.6 (18) |
O1—La1—N3—O7 | −141.4 (2) | C27'—N11—C30'—C29' | −76 (2) |
O5—La1—N3—O7 | 93.4 (2) | P2—N11—C30'—C29' | 132.0 (16) |
O4—La1—N3—O7 | 46.5 (2) | O10—La1—O1S—C1S | −51.5 (6) |
N1—La1—N3—O7 | −119.4 (3) | O16—La1—O1S—C1S | 142.6 (6) |
O10—P1—N5—C1 | −179.5 (4) | O1W—La1—O1S—C1S | −137.7 (6) |
N7—P1—N5—C1 | −61.0 (4) | O7—La1—O1S—C1S | 72.5 (6) |
N6—P1—N5—C1 | 56.3 (4) | O2—La1—O1S—C1S | −166.5 (5) |
O10—P1—N6—C15' | 98.9 (12) | O8—La1—O1S—C1S | 3.0 (7) |
N7—P1—N6—C15' | −23.9 (12) | O1—La1—O1S—C1S | −94.1 (6) |
N5—P1—N6—C15' | −147.1 (12) | O5—La1—O1S—C1S | 22.0 (6) |
O10—P1—N6—C12 | −64.9 (4) | O4—La1—O1S—C1S | 69.5 (6) |
N7—P1—N6—C12 | 172.4 (4) | N1—La1—O1S—C1S | −118.8 (6) |
N5—P1—N6—C12 | 49.2 (4) | N3—La1—O1S—C1S | 42.3 (7) |
O10—P1—N6—C15 | 65.2 (5) | La1—O1S—C1S—C2S | 169.7 (4) |
N7—P1—N6—C15 | −57.5 (5) | La1—O1S—C1S—C3S | −9.3 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O19i | 0.89 | 1.94 | 2.810 (7) | 164 |
O1W—H2W1···O13ii | 0.89 | 2.02 | 2.815 (6) | 147 |
N5—H5N···O5 | 0.85 | 2.19 | 2.988 (5) | 155 |
N9—H9N···O4 | 0.85 | 2.16 | 2.948 (5) | 153 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y−1/2, z+1/2. |
Crystal data top
C30H44ErN11O22P2·0.5(C3H6O)·0.5(CH4O) | F(000) = 2400 |
Mr = 1185.02 | Dx = 1.749 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 39011 reflections |
a = 8.7152 (4) Å | θ = 1.5–26.1° |
b = 33.5889 (14) Å | µ = 2.03 mm−1 |
c = 15.3815 (8) Å | T = 173 K |
β = 92.113 (4)° | Rod, colourless |
V = 4499.6 (4) Å3 | 0.33 × 0.27 × 0.21 mm |
Z = 4 | |
Data collection top
STOE IPDS-2 diffractometer | 8492 independent reflections |
Radiation source: fine-focus sealed tube | 6850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
phi + ω scans | θmax = 25.7°, θmin = 1.5° |
Absorption correction: multi-scan MULscanABS (Spek, 2003) | h = −10→10 |
Tmin = 0.607, Tmax = 0.657 | k = −37→40 |
42064 measured reflections | l = −18→18 |
Refinement top
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0638P)2 + 7.5884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
8492 reflections | Δρmax = 2.07 e Å−3 |
590 parameters | Δρmin = −1.59 e Å−3 |
5 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (2) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. A region of diffuse electron density, 114 electrons for a Potential Solvent
Accessible Void of 341.9 Å3, was equated to 0.5 actetone and 0.5 methanol
per molecule of complex, using the Squeeze routine in PLATON (Spek,
2003). Restraints in final refinement: DFIX 0.88. 02 N1 H1N N5 H5N DFIX
0.84. 02 O1W H1WA O1W H1WB EADP O3 O4 O10 EADP O21 O20 The water O—H distances were restrained to 0.84 (2) Å, and the N—H
distances were restrained to 0.88 (2) Å, with Uiso(H) =
1.5Ueq(parent O-atom) and 1.2Ueq(parent N-atom). C-bound H-atoms were included
in calculated positons and treated as riding atoms: C—H = 0.95 - 0.99 Å,
with Uiso(H) = 1.2Ueq(C). One of the nitro groups undergoes considerable thermal motion. The anisotropic
thermal parameters were restrained as above. No improvement was possible by
trying to split the O-atoms. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Er1 | 0.28773 (3) | 0.16647 (1) | 0.12397 (1) | 0.0254 (1) | |
P1 | 0.26077 (14) | 0.14013 (4) | 0.35288 (8) | 0.0226 (3) | |
P2 | 0.24187 (14) | 0.15775 (4) | −0.11277 (8) | 0.0238 (4) | |
O1 | 0.2304 (4) | 0.15914 (10) | 0.2662 (2) | 0.0254 (10) | |
O1W | 0.0579 (4) | 0.20088 (12) | 0.1238 (2) | 0.0324 (11) | |
O2 | 0.3949 (5) | 0.06963 (14) | 0.4590 (3) | 0.0484 (14) | |
O3 | 0.9214 (8) | −0.06254 (19) | 0.3052 (4) | 0.0909 (16) | |
O4 | 0.9044 (8) | −0.03457 (19) | 0.1794 (5) | 0.0909 (16) | |
O5 | 0.4546 (4) | 0.23338 (12) | 0.5322 (2) | 0.0363 (12) | |
O6 | −0.1930 (4) | 0.11725 (12) | 0.4560 (2) | 0.0367 (11) | |
O7 | 0.2558 (4) | 0.15008 (11) | −0.0173 (2) | 0.0276 (10) | |
O8 | 0.3382 (5) | 0.14371 (12) | −0.2970 (2) | 0.0389 (11) | |
O9 | 0.8673 (6) | 0.00816 (18) | −0.4293 (4) | 0.074 (2) | |
O10 | 0.8488 (8) | −0.0239 (2) | −0.3105 (4) | 0.0909 (16) | |
O11 | 0.4030 (4) | 0.27042 (11) | −0.2322 (2) | 0.0337 (11) | |
O12 | −0.2551 (4) | 0.14972 (14) | −0.1870 (3) | 0.0420 (14) | |
O13 | 0.3225 (4) | 0.22907 (11) | 0.0460 (2) | 0.0336 (11) | |
O14 | 0.3908 (4) | 0.22861 (11) | 0.1821 (2) | 0.0337 (11) | |
O15 | 0.4508 (5) | 0.27945 (12) | 0.1016 (3) | 0.0469 (14) | |
O16 | 0.5364 (4) | 0.15239 (12) | 0.2025 (2) | 0.0334 (11) | |
O17 | 0.5465 (5) | 0.16789 (14) | 0.0680 (2) | 0.0446 (14) | |
O18 | 0.7576 (5) | 0.15361 (18) | 0.1408 (3) | 0.0599 (18) | |
O19 | 0.3390 (5) | 0.09685 (11) | 0.1314 (2) | 0.0353 (12) | |
O20 | 0.0856 (7) | 0.11548 (16) | 0.1204 (4) | 0.0709 (14) | |
O21 | 0.1535 (7) | 0.05022 (16) | 0.1146 (4) | 0.0709 (14) | |
N1 | 0.3965 (5) | 0.10586 (12) | 0.3361 (3) | 0.0259 (11) | |
N2 | 0.8719 (7) | −0.03690 (19) | 0.2558 (5) | 0.062 (3) | |
N3 | 0.3316 (4) | 0.16967 (12) | 0.4291 (3) | 0.0257 (11) | |
N4 | 0.1047 (5) | 0.12263 (13) | 0.3902 (2) | 0.0264 (11) | |
N5 | 0.3618 (5) | 0.12437 (13) | −0.1556 (3) | 0.0285 (11) | |
N6 | 0.8174 (6) | 0.00459 (17) | −0.3568 (4) | 0.0474 (17) | |
N7 | 0.2981 (4) | 0.20032 (12) | −0.1486 (3) | 0.0260 (12) | |
N8 | 0.0647 (5) | 0.15312 (13) | −0.1452 (3) | 0.0290 (12) | |
N9 | 0.3905 (5) | 0.24697 (14) | 0.1101 (3) | 0.0327 (14) | |
N10 | 0.6190 (5) | 0.15745 (14) | 0.1371 (3) | 0.0349 (14) | |
N11 | 0.1956 (9) | 0.0863 (2) | 0.1231 (4) | 0.067 (2) | |
C1 | 0.4426 (6) | 0.07476 (16) | 0.3865 (3) | 0.0303 (17) | |
C2 | 0.5587 (6) | 0.04672 (16) | 0.3491 (3) | 0.0300 (17) | |
C3 | 0.6214 (7) | 0.01756 (18) | 0.4020 (4) | 0.0444 (19) | |
C4 | 0.7259 (7) | −0.0096 (2) | 0.3732 (5) | 0.052 (2) | |
C5 | 0.7643 (6) | −0.00700 (18) | 0.2894 (4) | 0.0437 (19) | |
C6 | 0.7092 (8) | 0.0221 (2) | 0.2324 (5) | 0.056 (3) | |
C7 | 0.6040 (8) | 0.04932 (19) | 0.2632 (4) | 0.0478 (19) | |
C8 | 0.4988 (5) | 0.17567 (16) | 0.4410 (3) | 0.0277 (16) | |
C9 | 0.5339 (6) | 0.19628 (17) | 0.5262 (4) | 0.0355 (17) | |
C10 | 0.2914 (6) | 0.22607 (18) | 0.5264 (4) | 0.0385 (17) | |
C11 | 0.2477 (6) | 0.20716 (16) | 0.4400 (4) | 0.0338 (17) | |
C12 | −0.0287 (6) | 0.11262 (18) | 0.3329 (3) | 0.0329 (17) | |
C13 | −0.1693 (6) | 0.13131 (18) | 0.3691 (3) | 0.0346 (17) | |
C14 | −0.0638 (6) | 0.12686 (19) | 0.5119 (3) | 0.0368 (19) | |
C15 | 0.0829 (6) | 0.10893 (17) | 0.4801 (3) | 0.0328 (17) | |
C16 | 0.3955 (6) | 0.12147 (16) | −0.2424 (3) | 0.0302 (17) | |
C17 | 0.5071 (6) | 0.08970 (16) | −0.2681 (3) | 0.0296 (17) | |
C18 | 0.5571 (7) | 0.05943 (18) | −0.2137 (4) | 0.0419 (19) | |
C19 | 0.6611 (8) | 0.0315 (2) | −0.2417 (4) | 0.047 (2) | |
C20 | 0.7120 (6) | 0.03463 (17) | −0.3252 (4) | 0.0373 (17) | |
C21 | 0.6624 (7) | 0.06394 (18) | −0.3816 (4) | 0.0418 (17) | |
C22 | 0.5584 (7) | 0.09139 (17) | −0.3524 (4) | 0.0412 (19) | |
C23 | 0.4618 (6) | 0.21065 (16) | −0.1490 (3) | 0.0296 (17) | |
C24 | 0.4934 (6) | 0.23515 (16) | −0.2287 (3) | 0.0338 (17) | |
C25 | 0.2419 (6) | 0.26064 (16) | −0.2332 (3) | 0.0300 (16) | |
C26 | 0.2038 (6) | 0.23672 (15) | −0.1528 (3) | 0.0273 (16) | |
C27 | 0.0065 (6) | 0.15796 (17) | −0.2359 (3) | 0.0333 (17) | |
C28 | −0.1541 (7) | 0.17411 (19) | −0.2349 (4) | 0.0406 (19) | |
C29 | −0.1979 (6) | 0.1457 (2) | −0.0988 (4) | 0.0435 (19) | |
C30 | −0.0406 (6) | 0.12749 (19) | −0.0959 (4) | 0.0413 (19) | |
H1WA | 0.039 (8) | 0.2212 (13) | 0.094 (4) | 0.0490* | |
H1N | 0.429 (5) | 0.1119 (10) | 0.286 (2) | 0.0310* | |
H1WB | 0.005 (6) | 0.203 (2) | 0.168 (3) | 0.0490* | |
H3 | 0.59130 | 0.01610 | 0.46060 | 0.0530* | |
H4 | 0.76930 | −0.02930 | 0.41090 | 0.0620* | |
H5N | 0.402 (6) | 0.1090 (14) | −0.116 (3) | 0.0340* | |
H6 | 0.74220 | 0.02340 | 0.17430 | 0.0670* | |
H8A | 0.53670 | 0.19200 | 0.39270 | 0.0330* | |
H8B | 0.55190 | 0.14960 | 0.44030 | 0.0330* | |
H9A | 0.50400 | 0.17870 | 0.57440 | 0.0420* | |
H9B | 0.64580 | 0.20110 | 0.53260 | 0.0420* | |
H10A | 0.23530 | 0.25150 | 0.53240 | 0.0470* | |
H10B | 0.26220 | 0.20820 | 0.57420 | 0.0470* | |
H11A | 0.13590 | 0.20190 | 0.43680 | 0.0410* | |
H11B | 0.27180 | 0.22570 | 0.39230 | 0.0410* | |
H12A | −0.04150 | 0.08340 | 0.32970 | 0.0390* | |
H12B | −0.01300 | 0.12280 | 0.27340 | 0.0390* | |
H13A | −0.15740 | 0.16060 | 0.36990 | 0.0420* | |
H13B | −0.26010 | 0.12470 | 0.33130 | 0.0420* | |
H14A | −0.08180 | 0.11690 | 0.57120 | 0.0440* | |
H14B | −0.05250 | 0.15620 | 0.51520 | 0.0440* | |
H15A | 0.17110 | 0.11730 | 0.51820 | 0.0390* | |
H15B | 0.07650 | 0.07950 | 0.48150 | 0.0390* | |
H18 | 0.52010 | 0.05770 | −0.15650 | 0.0500* | |
H19 | 0.69640 | 0.01060 | −0.20430 | 0.0560* | |
H21 | 0.69870 | 0.06530 | −0.43900 | 0.0500* | |
H22 | 0.52130 | 0.11180 | −0.39050 | 0.0490* | |
H23A | 0.52430 | 0.18600 | −0.14900 | 0.0350* | |
H23B | 0.49070 | 0.22600 | −0.09590 | 0.0350* | |
H24A | 0.60350 | 0.24240 | −0.22800 | 0.0400* | |
H24B | 0.47060 | 0.21900 | −0.28150 | 0.0400* | |
H25A | 0.21470 | 0.24500 | −0.28610 | 0.0360* | |
H25B | 0.18050 | 0.28540 | −0.23510 | 0.0360* | |
H26A | 0.22440 | 0.25300 | −0.09990 | 0.0330* | |
H26B | 0.09360 | 0.22950 | −0.15520 | 0.0330* | |
H27A | 0.00680 | 0.13200 | −0.26620 | 0.0400* | |
H27B | 0.07320 | 0.17650 | −0.26720 | 0.0400* | |
H28A | −0.15130 | 0.20110 | −0.20900 | 0.0490* | |
H28B | −0.19530 | 0.17660 | −0.29550 | 0.0490* | |
H29A | −0.26850 | 0.12880 | −0.06600 | 0.0520* | |
H29B | −0.19360 | 0.17220 | −0.07070 | 0.0520* | |
H30A | −0.00220 | 0.12500 | −0.03480 | 0.0500* | |
H30B | −0.04510 | 0.10050 | −0.12190 | 0.0500* | |
H77 | 0.56310 | 0.06960 | 0.22600 | 0.0570* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Er1 | 0.0246 (1) | 0.0324 (1) | 0.0195 (1) | 0.0044 (1) | 0.0039 (1) | 0.0020 (1) |
P1 | 0.0190 (6) | 0.0289 (6) | 0.0202 (5) | 0.0013 (5) | 0.0032 (4) | 0.0006 (5) |
P2 | 0.0219 (6) | 0.0290 (7) | 0.0206 (6) | 0.0020 (5) | 0.0015 (5) | 0.0003 (5) |
O1 | 0.0286 (18) | 0.0327 (19) | 0.0153 (15) | 0.0042 (14) | 0.0078 (13) | 0.0026 (13) |
O1W | 0.0266 (19) | 0.037 (2) | 0.034 (2) | 0.0098 (16) | 0.0085 (15) | 0.0082 (16) |
O2 | 0.045 (2) | 0.066 (3) | 0.035 (2) | 0.019 (2) | 0.0143 (18) | 0.018 (2) |
O3 | 0.095 (3) | 0.074 (2) | 0.104 (3) | 0.046 (2) | 0.008 (2) | −0.017 (2) |
O4 | 0.095 (3) | 0.074 (2) | 0.104 (3) | 0.046 (2) | 0.008 (2) | −0.017 (2) |
O5 | 0.034 (2) | 0.037 (2) | 0.038 (2) | −0.0050 (17) | 0.0021 (16) | −0.0098 (17) |
O6 | 0.0243 (19) | 0.052 (2) | 0.0345 (19) | 0.0023 (17) | 0.0109 (15) | 0.0073 (17) |
O7 | 0.0320 (19) | 0.0359 (19) | 0.0149 (15) | 0.0038 (15) | 0.0017 (13) | −0.0003 (14) |
O8 | 0.049 (2) | 0.044 (2) | 0.0239 (18) | 0.0162 (19) | 0.0045 (16) | 0.0000 (16) |
O9 | 0.065 (3) | 0.082 (4) | 0.077 (4) | 0.027 (3) | 0.017 (3) | −0.027 (3) |
O10 | 0.095 (3) | 0.074 (2) | 0.104 (3) | 0.046 (2) | 0.008 (2) | −0.017 (2) |
O11 | 0.034 (2) | 0.036 (2) | 0.0316 (18) | −0.0005 (16) | 0.0069 (15) | 0.0054 (16) |
O12 | 0.025 (2) | 0.055 (3) | 0.046 (2) | 0.0005 (18) | −0.0001 (17) | −0.0017 (19) |
O13 | 0.042 (2) | 0.035 (2) | 0.0237 (17) | −0.0036 (17) | 0.0019 (15) | 0.0000 (15) |
O14 | 0.042 (2) | 0.035 (2) | 0.0238 (17) | −0.0020 (17) | −0.0037 (15) | 0.0019 (15) |
O15 | 0.052 (3) | 0.036 (2) | 0.053 (2) | −0.016 (2) | 0.005 (2) | 0.0031 (19) |
O16 | 0.0259 (19) | 0.045 (2) | 0.0294 (18) | 0.0020 (16) | 0.0027 (15) | 0.0077 (16) |
O17 | 0.032 (2) | 0.073 (3) | 0.0293 (19) | 0.005 (2) | 0.0093 (16) | 0.0045 (19) |
O18 | 0.020 (2) | 0.100 (4) | 0.060 (3) | 0.012 (2) | 0.0046 (19) | −0.002 (3) |
O19 | 0.038 (2) | 0.032 (2) | 0.036 (2) | 0.0028 (17) | 0.0037 (16) | 0.0027 (16) |
O20 | 0.091 (3) | 0.048 (2) | 0.074 (2) | −0.016 (2) | 0.009 (2) | 0.0027 (18) |
O21 | 0.091 (3) | 0.048 (2) | 0.074 (2) | −0.016 (2) | 0.009 (2) | 0.0027 (18) |
N1 | 0.027 (2) | 0.030 (2) | 0.0211 (19) | 0.0063 (18) | 0.0063 (16) | 0.0049 (16) |
N2 | 0.051 (4) | 0.049 (4) | 0.086 (5) | 0.009 (3) | 0.000 (3) | −0.024 (3) |
N3 | 0.0180 (19) | 0.032 (2) | 0.027 (2) | 0.0010 (17) | 0.0009 (15) | −0.0027 (17) |
N4 | 0.019 (2) | 0.039 (2) | 0.0213 (19) | −0.0071 (17) | 0.0013 (15) | 0.0007 (17) |
N5 | 0.032 (2) | 0.034 (2) | 0.0198 (19) | 0.0090 (19) | 0.0038 (17) | 0.0033 (17) |
N6 | 0.038 (3) | 0.049 (3) | 0.055 (3) | 0.008 (2) | 0.001 (2) | −0.023 (3) |
N7 | 0.020 (2) | 0.028 (2) | 0.030 (2) | 0.0029 (17) | 0.0021 (16) | 0.0021 (17) |
N8 | 0.026 (2) | 0.034 (2) | 0.027 (2) | 0.0014 (18) | 0.0020 (17) | 0.0047 (17) |
N9 | 0.029 (2) | 0.040 (3) | 0.029 (2) | 0.006 (2) | 0.0013 (18) | −0.0035 (19) |
N10 | 0.025 (2) | 0.044 (3) | 0.036 (2) | 0.001 (2) | 0.0071 (19) | −0.001 (2) |
N11 | 0.095 (5) | 0.057 (4) | 0.047 (3) | −0.008 (4) | −0.003 (3) | 0.002 (3) |
C1 | 0.025 (3) | 0.037 (3) | 0.029 (3) | 0.000 (2) | 0.002 (2) | 0.004 (2) |
C2 | 0.024 (3) | 0.031 (3) | 0.035 (3) | 0.000 (2) | 0.001 (2) | 0.000 (2) |
C3 | 0.048 (4) | 0.040 (3) | 0.045 (3) | 0.009 (3) | 0.001 (3) | 0.008 (3) |
C4 | 0.045 (4) | 0.045 (4) | 0.065 (4) | 0.015 (3) | −0.006 (3) | 0.006 (3) |
C5 | 0.028 (3) | 0.032 (3) | 0.071 (4) | 0.008 (2) | −0.001 (3) | −0.013 (3) |
C6 | 0.064 (5) | 0.052 (4) | 0.052 (4) | 0.016 (3) | 0.020 (3) | −0.007 (3) |
C7 | 0.057 (4) | 0.042 (3) | 0.045 (3) | 0.017 (3) | 0.012 (3) | 0.003 (3) |
C8 | 0.016 (2) | 0.034 (3) | 0.033 (3) | 0.0001 (19) | 0.0002 (19) | −0.001 (2) |
C9 | 0.027 (3) | 0.040 (3) | 0.039 (3) | 0.000 (2) | −0.004 (2) | −0.005 (2) |
C10 | 0.033 (3) | 0.043 (3) | 0.040 (3) | −0.001 (3) | 0.007 (2) | −0.014 (3) |
C11 | 0.028 (3) | 0.032 (3) | 0.041 (3) | 0.006 (2) | −0.002 (2) | −0.005 (2) |
C12 | 0.025 (3) | 0.045 (3) | 0.029 (3) | −0.007 (2) | 0.004 (2) | −0.006 (2) |
C13 | 0.024 (3) | 0.045 (3) | 0.035 (3) | 0.000 (2) | 0.003 (2) | 0.009 (2) |
C14 | 0.029 (3) | 0.054 (4) | 0.028 (3) | −0.002 (3) | 0.008 (2) | 0.002 (2) |
C15 | 0.025 (3) | 0.044 (3) | 0.030 (3) | −0.001 (2) | 0.009 (2) | 0.008 (2) |
C16 | 0.030 (3) | 0.030 (3) | 0.031 (3) | −0.001 (2) | 0.008 (2) | −0.003 (2) |
C17 | 0.026 (3) | 0.033 (3) | 0.030 (3) | 0.000 (2) | 0.005 (2) | −0.004 (2) |
C18 | 0.051 (4) | 0.043 (3) | 0.032 (3) | 0.012 (3) | 0.005 (3) | −0.001 (2) |
C19 | 0.051 (4) | 0.049 (4) | 0.041 (3) | 0.019 (3) | −0.001 (3) | −0.003 (3) |
C20 | 0.028 (3) | 0.038 (3) | 0.046 (3) | 0.003 (2) | 0.004 (2) | −0.012 (3) |
C21 | 0.046 (3) | 0.038 (3) | 0.043 (3) | −0.001 (3) | 0.022 (3) | −0.007 (3) |
C22 | 0.050 (4) | 0.032 (3) | 0.043 (3) | 0.000 (3) | 0.019 (3) | 0.000 (2) |
C23 | 0.024 (3) | 0.034 (3) | 0.031 (3) | 0.002 (2) | 0.002 (2) | 0.001 (2) |
C24 | 0.030 (3) | 0.037 (3) | 0.035 (3) | 0.001 (2) | 0.011 (2) | 0.001 (2) |
C25 | 0.029 (3) | 0.036 (3) | 0.025 (2) | 0.002 (2) | 0.003 (2) | 0.005 (2) |
C26 | 0.028 (3) | 0.028 (3) | 0.026 (2) | 0.004 (2) | 0.004 (2) | 0.0019 (19) |
C27 | 0.031 (3) | 0.039 (3) | 0.030 (3) | 0.001 (2) | 0.001 (2) | 0.000 (2) |
C28 | 0.031 (3) | 0.050 (4) | 0.040 (3) | 0.004 (3) | −0.009 (2) | 0.004 (3) |
C29 | 0.027 (3) | 0.060 (4) | 0.044 (3) | −0.002 (3) | 0.010 (2) | 0.003 (3) |
C30 | 0.027 (3) | 0.046 (4) | 0.051 (3) | −0.004 (2) | 0.005 (2) | 0.007 (3) |
Geometric parameters (Å, º) top
Er1—O1 | 2.275 (3) | C3—C4 | 1.374 (9) |
Er1—O1W | 2.313 (4) | C4—C5 | 1.346 (10) |
Er1—O7 | 2.249 (3) | C5—C6 | 1.387 (9) |
Er1—O13 | 2.445 (4) | C6—C7 | 1.390 (10) |
Er1—O14 | 2.430 (4) | C8—C9 | 1.504 (8) |
Er1—O16 | 2.487 (3) | C10—C11 | 1.509 (9) |
Er1—O17 | 2.444 (4) | C12—C13 | 1.502 (8) |
Er1—O19 | 2.383 (4) | C14—C15 | 1.511 (8) |
Er1—O20 | 2.456 (6) | C16—C17 | 1.506 (7) |
P1—O1 | 1.493 (3) | C17—C22 | 1.388 (8) |
P1—N1 | 1.677 (4) | C17—C18 | 1.377 (8) |
P1—N3 | 1.639 (4) | C18—C19 | 1.384 (9) |
P1—N4 | 1.607 (4) | C19—C20 | 1.378 (9) |
P2—O7 | 1.491 (3) | C20—C21 | 1.372 (8) |
P2—N5 | 1.684 (5) | C21—C22 | 1.380 (8) |
P2—N7 | 1.615 (4) | C23—C24 | 1.510 (7) |
P2—N8 | 1.613 (5) | C25—C26 | 1.522 (7) |
O2—C1 | 1.217 (7) | C27—C28 | 1.502 (8) |
O3—N2 | 1.217 (9) | C29—C30 | 1.500 (8) |
O4—N2 | 1.221 (11) | C3—H3 | 0.9500 |
O5—C9 | 1.430 (7) | C4—H4 | 0.9500 |
O5—C10 | 1.443 (6) | C6—H6 | 0.9500 |
O6—C13 | 1.440 (6) | C7—H77 | 0.9500 |
O6—C14 | 1.428 (6) | C8—H8A | 0.9900 |
O8—C16 | 1.217 (6) | C8—H8B | 0.9900 |
O9—N6 | 1.218 (9) | C9—H9A | 0.9900 |
O10—N6 | 1.218 (9) | C9—H9B | 0.9900 |
O11—C24 | 1.423 (6) | C10—H10A | 0.9900 |
O11—C25 | 1.442 (6) | C10—H10B | 0.9900 |
O12—C28 | 1.427 (8) | C11—H11A | 0.9900 |
O12—C29 | 1.434 (8) | C11—H11B | 0.9900 |
O13—N9 | 1.281 (6) | C12—H12A | 0.9900 |
O14—N9 | 1.268 (6) | C12—H12B | 0.9900 |
O15—N9 | 1.220 (6) | C13—H13A | 0.9900 |
O16—N10 | 1.270 (6) | C13—H13B | 0.9900 |
O17—N10 | 1.266 (6) | C14—H14A | 0.9900 |
O18—N10 | 1.214 (6) | C14—H14B | 0.9900 |
O19—N11 | 1.301 (9) | C15—H15A | 0.9900 |
O20—N11 | 1.371 (9) | C15—H15B | 0.9900 |
O21—N11 | 1.272 (9) | C18—H18 | 0.9500 |
O1W—H1WA | 0.84 (5) | C19—H19 | 0.9500 |
O1W—H1WB | 0.84 (5) | C21—H21 | 0.9500 |
N1—C1 | 1.353 (7) | C22—H22 | 0.9500 |
N2—C5 | 1.480 (9) | C23—H23A | 0.9900 |
N3—C8 | 1.476 (6) | C23—H23B | 0.9900 |
N3—C11 | 1.469 (7) | C24—H24A | 0.9900 |
N4—C12 | 1.472 (6) | C24—H24B | 0.9900 |
N4—C15 | 1.476 (6) | C25—H25A | 0.9900 |
N5—C16 | 1.381 (7) | C25—H25B | 0.9900 |
N6—C20 | 1.460 (8) | C26—H26A | 0.9900 |
N7—C23 | 1.469 (6) | C26—H26B | 0.9900 |
N7—C26 | 1.473 (6) | C27—H27A | 0.9900 |
N8—C30 | 1.487 (7) | C27—H27B | 0.9900 |
N8—C27 | 1.476 (7) | C28—H28A | 0.9900 |
N1—H1N | 0.86 (3) | C28—H28B | 0.9900 |
N5—H5N | 0.86 (5) | C29—H29A | 0.9900 |
C1—C2 | 1.512 (7) | C29—H29B | 0.9900 |
C2—C3 | 1.374 (8) | C30—H30A | 0.9900 |
C2—C7 | 1.396 (8) | C30—H30B | 0.9900 |
| | | |
O1—Er1—O1W | 80.46 (12) | O8—C16—N5 | 121.8 (5) |
O1—Er1—O7 | 151.50 (13) | O8—C16—C17 | 120.4 (4) |
O1—Er1—O13 | 126.89 (11) | N5—C16—C17 | 117.8 (4) |
O1—Er1—O14 | 80.24 (11) | C16—C17—C18 | 123.8 (5) |
O1—Er1—O16 | 74.38 (11) | C16—C17—C22 | 116.7 (5) |
O1—Er1—O17 | 125.38 (12) | C18—C17—C22 | 119.5 (5) |
O1—Er1—O19 | 83.98 (11) | C17—C18—C19 | 120.5 (6) |
O1—Er1—O20 | 76.31 (17) | C18—C19—C20 | 118.4 (6) |
O1W—Er1—O7 | 92.58 (12) | N6—C20—C19 | 119.1 (5) |
O1W—Er1—O13 | 72.10 (12) | N6—C20—C21 | 118.2 (5) |
O1W—Er1—O14 | 83.08 (13) | C19—C20—C21 | 122.7 (6) |
O1W—Er1—O16 | 146.59 (12) | C20—C21—C22 | 118.0 (6) |
O1W—Er1—O17 | 143.16 (14) | C17—C22—C21 | 121.0 (5) |
O1W—Er1—O19 | 130.65 (14) | N7—C23—C24 | 109.8 (4) |
O1W—Er1—O20 | 74.22 (17) | O11—C24—C23 | 111.5 (4) |
O7—Er1—O13 | 75.51 (12) | O11—C25—C26 | 110.7 (4) |
O7—Er1—O14 | 126.64 (12) | N7—C26—C25 | 109.6 (4) |
O7—Er1—O16 | 119.82 (12) | N8—C27—C28 | 108.6 (4) |
O7—Er1—O17 | 75.36 (12) | O12—C28—C27 | 113.0 (5) |
O7—Er1—O19 | 79.77 (12) | O12—C29—C30 | 110.6 (5) |
O7—Er1—O20 | 75.20 (17) | N8—C30—C29 | 109.2 (5) |
O13—Er1—O14 | 52.48 (11) | C2—C3—H3 | 119.00 |
O13—Er1—O16 | 106.27 (12) | C4—C3—H3 | 119.00 |
O13—Er1—O17 | 71.20 (13) | C3—C4—H4 | 121.00 |
O13—Er1—O19 | 147.26 (12) | C5—C4—H4 | 122.00 |
O13—Er1—O20 | 133.67 (16) | C5—C6—H6 | 121.00 |
O14—Er1—O16 | 71.39 (12) | C7—C6—H6 | 121.00 |
O14—Er1—O17 | 77.26 (13) | C2—C7—H77 | 120.00 |
O14—Er1—O19 | 139.40 (12) | C6—C7—H77 | 120.00 |
O14—Er1—O20 | 149.59 (16) | N3—C8—H8A | 110.00 |
O16—Er1—O17 | 51.39 (11) | N3—C8—H8B | 110.00 |
O16—Er1—O19 | 68.38 (13) | C9—C8—H8A | 110.00 |
O16—Er1—O20 | 119.32 (16) | C9—C8—H8B | 110.00 |
O17—Er1—O19 | 82.08 (15) | H8A—C8—H8B | 108.00 |
O17—Er1—O20 | 132.54 (17) | O5—C9—H9A | 109.00 |
O19—Er1—O20 | 56.62 (17) | O5—C9—H9B | 109.00 |
O1—P1—N1 | 105.0 (2) | C8—C9—H9A | 109.00 |
O1—P1—N3 | 115.4 (2) | C8—C9—H9B | 109.00 |
O1—P1—N4 | 110.5 (2) | H9A—C9—H9B | 108.00 |
N1—P1—N3 | 106.0 (2) | O5—C10—H10A | 110.00 |
N1—P1—N4 | 114.5 (2) | O5—C10—H10B | 110.00 |
N3—P1—N4 | 105.5 (2) | C11—C10—H10A | 110.00 |
O7—P2—N5 | 104.0 (2) | C11—C10—H10B | 110.00 |
O7—P2—N7 | 118.3 (2) | H10A—C10—H10B | 108.00 |
O7—P2—N8 | 109.3 (2) | N3—C11—H11A | 110.00 |
N5—P2—N7 | 104.8 (2) | N3—C11—H11B | 110.00 |
N5—P2—N8 | 114.6 (2) | C10—C11—H11A | 110.00 |
N7—P2—N8 | 106.2 (2) | C10—C11—H11B | 110.00 |
Er1—O1—P1 | 150.1 (2) | H11A—C11—H11B | 108.00 |
C9—O5—C10 | 109.0 (4) | N4—C12—H12A | 110.00 |
C13—O6—C14 | 110.4 (4) | N4—C12—H12B | 110.00 |
Er1—O7—P2 | 155.8 (2) | C13—C12—H12A | 110.00 |
C24—O11—C25 | 110.4 (4) | C13—C12—H12B | 110.00 |
C28—O12—C29 | 110.1 (4) | H12A—C12—H12B | 108.00 |
Er1—O13—N9 | 95.1 (3) | O6—C13—H13A | 109.00 |
Er1—O14—N9 | 96.2 (3) | O6—C13—H13B | 109.00 |
Er1—O16—N10 | 95.7 (3) | C12—C13—H13A | 109.00 |
Er1—O17—N10 | 97.9 (3) | C12—C13—H13B | 110.00 |
Er1—O19—N11 | 94.9 (4) | H13A—C13—H13B | 108.00 |
Er1—O20—N11 | 89.9 (4) | O6—C14—H14A | 109.00 |
H1WA—O1W—H1WB | 106 (6) | O6—C14—H14B | 109.00 |
Er1—O1W—H1WA | 124 (5) | C15—C14—H14A | 109.00 |
Er1—O1W—H1WB | 123 (4) | C15—C14—H14B | 109.00 |
P1—N1—C1 | 129.6 (4) | H14A—C14—H14B | 108.00 |
O4—N2—C5 | 117.7 (6) | N4—C15—H15A | 110.00 |
O3—N2—O4 | 123.8 (7) | N4—C15—H15B | 110.00 |
O3—N2—C5 | 118.5 (7) | C14—C15—H15A | 110.00 |
P1—N3—C8 | 121.0 (3) | C14—C15—H15B | 110.00 |
P1—N3—C11 | 115.1 (3) | H15A—C15—H15B | 108.00 |
C8—N3—C11 | 111.2 (4) | C17—C18—H18 | 120.00 |
P1—N4—C12 | 122.0 (3) | C19—C18—H18 | 120.00 |
C12—N4—C15 | 111.3 (4) | C18—C19—H19 | 121.00 |
P1—N4—C15 | 126.1 (3) | C20—C19—H19 | 121.00 |
P2—N5—C16 | 125.6 (4) | C20—C21—H21 | 121.00 |
O10—N6—C20 | 118.6 (6) | C22—C21—H21 | 121.00 |
O9—N6—O10 | 122.2 (6) | C17—C22—H22 | 119.00 |
O9—N6—C20 | 119.2 (6) | C21—C22—H22 | 120.00 |
P2—N7—C23 | 121.2 (3) | N7—C23—H23A | 110.00 |
P2—N7—C26 | 125.0 (3) | N7—C23—H23B | 110.00 |
C23—N7—C26 | 110.1 (4) | C24—C23—H23A | 110.00 |
P2—N8—C27 | 125.0 (4) | C24—C23—H23B | 110.00 |
P2—N8—C30 | 120.0 (4) | H23A—C23—H23B | 108.00 |
C27—N8—C30 | 110.4 (4) | O11—C24—H24A | 109.00 |
O13—N9—O15 | 121.7 (5) | O11—C24—H24B | 109.00 |
O13—N9—O14 | 115.5 (4) | C23—C24—H24A | 109.00 |
O14—N9—O15 | 122.8 (5) | C23—C24—H24B | 109.00 |
O16—N10—O17 | 115.0 (4) | H24A—C24—H24B | 108.00 |
O16—N10—O18 | 122.7 (5) | O11—C25—H25A | 109.00 |
O17—N10—O18 | 122.3 (5) | O11—C25—H25B | 110.00 |
O20—N11—O21 | 118.7 (7) | C26—C25—H25A | 110.00 |
O19—N11—O21 | 122.8 (7) | C26—C25—H25B | 110.00 |
O19—N11—O20 | 118.5 (6) | H25A—C25—H25B | 108.00 |
C1—N1—H1N | 127 (3) | N7—C26—H26A | 110.00 |
P1—N1—H1N | 104 (3) | N7—C26—H26B | 110.00 |
C16—N5—H5N | 123 (3) | C25—C26—H26A | 110.00 |
P2—N5—H5N | 111 (3) | C25—C26—H26B | 110.00 |
N1—C1—C2 | 116.9 (4) | H26A—C26—H26B | 108.00 |
O2—C1—N1 | 122.0 (5) | N8—C27—H27A | 110.00 |
O2—C1—C2 | 121.1 (5) | N8—C27—H27B | 110.00 |
C1—C2—C3 | 118.4 (4) | C28—C27—H27A | 110.00 |
C1—C2—C7 | 122.6 (5) | C28—C27—H27B | 110.00 |
C3—C2—C7 | 119.0 (5) | H27A—C27—H27B | 108.00 |
C2—C3—C4 | 122.4 (6) | O12—C28—H28A | 109.00 |
C3—C4—C5 | 117.2 (6) | O12—C28—H28B | 109.00 |
N2—C5—C4 | 118.3 (6) | C27—C28—H28A | 109.00 |
N2—C5—C6 | 117.8 (6) | C27—C28—H28B | 109.00 |
C4—C5—C6 | 123.9 (6) | H28A—C28—H28B | 108.00 |
C5—C6—C7 | 117.7 (6) | O12—C29—H29A | 110.00 |
C2—C7—C6 | 119.6 (6) | O12—C29—H29B | 110.00 |
N3—C8—C9 | 109.8 (4) | C30—C29—H29A | 110.00 |
O5—C9—C8 | 112.0 (4) | C30—C29—H29B | 110.00 |
O5—C10—C11 | 110.0 (4) | H29A—C29—H29B | 108.00 |
N3—C11—C10 | 110.5 (5) | N8—C30—H30A | 110.00 |
N4—C12—C13 | 108.7 (4) | N8—C30—H30B | 110.00 |
O6—C13—C12 | 110.7 (4) | C29—C30—H30A | 110.00 |
O6—C14—C15 | 111.9 (4) | C29—C30—H30B | 110.00 |
N4—C15—C14 | 108.6 (4) | H30A—C30—H30B | 108.00 |
| | | |
O1W—Er1—O1—P1 | 169.5 (4) | N8—P2—N7—C23 | −165.8 (4) |
O7—Er1—O1—P1 | 91.9 (5) | N8—P2—N7—C26 | 38.0 (5) |
O13—Er1—O1—P1 | −131.5 (4) | O7—P2—N8—C27 | −179.1 (4) |
O14—Er1—O1—P1 | −105.9 (4) | O7—P2—N8—C30 | −25.5 (5) |
O16—Er1—O1—P1 | −32.7 (4) | N5—P2—N8—C27 | −63.0 (5) |
O17—Er1—O1—P1 | −39.3 (5) | N5—P2—N8—C30 | 90.7 (4) |
O19—Er1—O1—P1 | 36.5 (4) | N7—P2—N8—C27 | 52.2 (5) |
O20—Er1—O1—P1 | 93.6 (4) | N7—P2—N8—C30 | −154.1 (4) |
O1—Er1—O7—P2 | 140.6 (5) | C10—O5—C9—C8 | 61.2 (5) |
O1W—Er1—O7—P2 | 65.9 (5) | C9—O5—C10—C11 | −61.2 (6) |
O13—Er1—O7—P2 | −4.9 (5) | C14—O6—C13—C12 | 59.8 (6) |
O14—Er1—O7—P2 | −17.4 (6) | C13—O6—C14—C15 | −58.7 (6) |
O16—Er1—O7—P2 | −105.5 (5) | C25—O11—C24—C23 | −58.9 (5) |
O17—Er1—O7—P2 | −78.8 (5) | C24—O11—C25—C26 | 58.6 (5) |
O19—Er1—O7—P2 | −163.2 (6) | C29—O12—C28—C27 | 58.7 (6) |
O20—Er1—O7—P2 | 138.8 (6) | C28—O12—C29—C30 | −59.1 (6) |
O1—Er1—O13—N9 | 37.7 (3) | Er1—O13—N9—O14 | −8.8 (4) |
O1W—Er1—O13—N9 | 100.3 (3) | Er1—O13—N9—O15 | 171.0 (4) |
O7—Er1—O13—N9 | −162.1 (3) | Er1—O14—N9—O13 | 8.9 (4) |
O14—Er1—O13—N9 | 5.2 (2) | Er1—O14—N9—O15 | −170.9 (4) |
O16—Er1—O13—N9 | −44.7 (3) | Er1—O16—N10—O17 | 2.3 (5) |
O17—Er1—O13—N9 | −82.9 (3) | Er1—O16—N10—O18 | −179.5 (5) |
O19—Er1—O13—N9 | −119.9 (3) | Er1—O17—N10—O16 | −2.4 (5) |
O20—Er1—O13—N9 | 145.6 (3) | Er1—O17—N10—O18 | 179.5 (5) |
O1—Er1—O14—N9 | −159.5 (3) | Er1—O19—N11—O20 | −4.3 (6) |
O1W—Er1—O14—N9 | −78.0 (3) | Er1—O19—N11—O21 | 173.4 (6) |
O7—Er1—O14—N9 | 10.1 (3) | Er1—O20—N11—O19 | 4.2 (6) |
O13—Er1—O14—N9 | −5.3 (2) | Er1—O20—N11—O21 | −173.6 (6) |
O16—Er1—O14—N9 | 123.9 (3) | P1—N1—C1—O2 | −6.5 (8) |
O17—Er1—O14—N9 | 70.7 (3) | P1—N1—C1—C2 | 174.4 (4) |
O19—Er1—O14—N9 | 131.9 (3) | O3—N2—C5—C4 | −0.1 (9) |
O20—Er1—O14—N9 | −119.6 (4) | O3—N2—C5—C6 | 179.8 (6) |
O1—Er1—O16—N10 | −174.5 (3) | O4—N2—C5—C4 | 179.1 (6) |
O1W—Er1—O16—N10 | −131.9 (3) | O4—N2—C5—C6 | −1.0 (9) |
O7—Er1—O16—N10 | 32.5 (3) | P1—N3—C8—C9 | −167.3 (4) |
O13—Er1—O16—N10 | −49.9 (3) | C11—N3—C8—C9 | 52.7 (6) |
O14—Er1—O16—N10 | −89.7 (3) | P1—N3—C11—C10 | 163.3 (4) |
O17—Er1—O16—N10 | −1.4 (3) | C8—N3—C11—C10 | −54.3 (6) |
O19—Er1—O16—N10 | 95.9 (3) | P1—N4—C12—C13 | −130.6 (4) |
O20—Er1—O16—N10 | 121.6 (3) | C15—N4—C12—C13 | 58.0 (6) |
O1—Er1—O17—N10 | 9.6 (4) | P1—N4—C15—C14 | 132.7 (4) |
O1W—Er1—O17—N10 | 137.1 (3) | C12—N4—C15—C14 | −56.3 (6) |
O7—Er1—O17—N10 | −148.6 (3) | P2—N5—C16—O8 | −0.3 (8) |
O13—Er1—O17—N10 | 132.0 (3) | P2—N5—C16—C17 | 179.5 (4) |
O14—Er1—O17—N10 | 77.6 (3) | O9—N6—C20—C19 | −177.1 (6) |
O16—Er1—O17—N10 | 1.4 (3) | O9—N6—C20—C21 | 5.7 (8) |
O19—Er1—O17—N10 | −67.2 (3) | O10—N6—C20—C19 | 5.1 (9) |
O20—Er1—O17—N10 | −95.4 (4) | O10—N6—C20—C21 | −172.1 (6) |
O1—Er1—O19—N11 | 80.1 (3) | P2—N7—C23—C24 | 144.0 (4) |
O1W—Er1—O19—N11 | 8.2 (4) | C26—N7—C23—C24 | −56.6 (5) |
O7—Er1—O19—N11 | −76.4 (3) | P2—N7—C26—C25 | −144.8 (4) |
O13—Er1—O19—N11 | −117.7 (4) | C23—N7—C26—C25 | 56.8 (5) |
O14—Er1—O19—N11 | 147.5 (3) | P2—N8—C27—C28 | −148.4 (4) |
O16—Er1—O19—N11 | 155.7 (3) | C30—N8—C27—C28 | 55.7 (6) |
O17—Er1—O19—N11 | −152.9 (3) | P2—N8—C30—C29 | 144.9 (4) |
O20—Er1—O19—N11 | 2.5 (3) | C27—N8—C30—C29 | −57.9 (6) |
O1—Er1—O20—N11 | −94.2 (4) | O2—C1—C2—C3 | −6.6 (8) |
O1W—Er1—O20—N11 | −178.0 (4) | O2—C1—C2—C7 | 173.3 (6) |
O7—Er1—O20—N11 | 85.0 (4) | N1—C1—C2—C3 | 172.6 (5) |
O13—Er1—O20—N11 | 137.4 (3) | N1—C1—C2—C7 | −7.6 (8) |
O14—Er1—O20—N11 | −134.8 (4) | C1—C2—C3—C4 | 179.0 (5) |
O16—Er1—O20—N11 | −31.2 (4) | C7—C2—C3—C4 | −0.9 (9) |
O17—Er1—O20—N11 | 31.6 (5) | C1—C2—C7—C6 | −178.8 (6) |
O19—Er1—O20—N11 | −2.4 (3) | C3—C2—C7—C6 | 1.1 (9) |
N1—P1—O1—Er1 | −5.6 (5) | C2—C3—C4—C5 | −0.8 (9) |
N3—P1—O1—Er1 | 110.8 (4) | C3—C4—C5—N2 | −177.6 (6) |
N4—P1—O1—Er1 | −129.6 (4) | C3—C4—C5—C6 | 2.5 (10) |
O1—P1—N1—C1 | −164.2 (5) | N2—C5—C6—C7 | 177.8 (6) |
N3—P1—N1—C1 | 73.1 (5) | C4—C5—C6—C7 | −2.3 (10) |
N4—P1—N1—C1 | −42.8 (5) | C5—C6—C7—C2 | 0.4 (10) |
O1—P1—N3—C8 | −88.0 (4) | N3—C8—C9—O5 | −56.8 (6) |
O1—P1—N3—C11 | 50.5 (4) | O5—C10—C11—N3 | 58.4 (6) |
N1—P1—N3—C8 | 27.8 (4) | N4—C12—C13—O6 | −59.0 (6) |
N1—P1—N3—C11 | 166.3 (4) | O6—C14—C15—N4 | 56.4 (6) |
N4—P1—N3—C8 | 149.7 (4) | O8—C16—C17—C18 | −168.9 (5) |
N4—P1—N3—C11 | −71.8 (4) | O8—C16—C17—C22 | 10.0 (8) |
O1—P1—N4—C12 | 22.6 (5) | N5—C16—C17—C18 | 11.4 (8) |
O1—P1—N4—C15 | −167.3 (4) | N5—C16—C17—C22 | −169.8 (5) |
N1—P1—N4—C12 | −95.7 (4) | C16—C17—C18—C19 | −179.4 (6) |
N1—P1—N4—C15 | 74.4 (5) | C22—C17—C18—C19 | 1.9 (9) |
N3—P1—N4—C12 | 148.1 (4) | C16—C17—C22—C21 | 179.1 (5) |
N3—P1—N4—C15 | −41.8 (5) | C18—C17—C22—C21 | −2.1 (9) |
N5—P2—O7—Er1 | 131.6 (5) | C17—C18—C19—C20 | −0.5 (9) |
N7—P2—O7—Er1 | 16.0 (6) | C18—C19—C20—N6 | −177.8 (6) |
N8—P2—O7—Er1 | −105.6 (5) | C18—C19—C20—C21 | −0.8 (9) |
O7—P2—N5—C16 | −175.8 (4) | N6—C20—C21—C22 | 177.6 (5) |
N7—P2—N5—C16 | −51.0 (5) | C19—C20—C21—C22 | 0.6 (9) |
N8—P2—N5—C16 | 65.0 (5) | C20—C21—C22—C17 | 0.8 (9) |
O7—P2—N7—C23 | 71.1 (4) | N7—C23—C24—O11 | 58.0 (5) |
O7—P2—N7—C26 | −85.2 (4) | O11—C25—C26—N7 | −57.7 (5) |
N5—P2—N7—C23 | −44.1 (4) | N8—C27—C28—O12 | −56.7 (6) |
N5—P2—N7—C26 | 159.6 (4) | O12—C29—C30—N8 | 59.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O5i | 0.84 (5) | 1.93 (5) | 2.753 (5) | 169 (7) |
N1—H1N···O16 | 0.86 (3) | 2.11 (3) | 2.887 (6) | 150 (3) |
N1—H1N···O19 | 0.86 (3) | 2.53 (3) | 3.184 (6) | 134 (3) |
O1W—H1WB···O11ii | 0.84 (5) | 2.01 (5) | 2.807 (5) | 158 (6) |
C3—H3···O2 | 0.95 | 2.48 | 2.802 (8) | 100 |
C8—H8B···O6iii | 0.99 | 2.48 | 3.328 (6) | 144 |
C8—H8B···N1 | 0.99 | 2.53 | 2.965 (7) | 106 |
C12—H12B···O1 | 0.99 | 2.45 | 2.960 (6) | 111 |
C12—H12B···O20 | 0.99 | 2.55 | 3.453 (8) | 152 |
C14—H14B···O15ii | 0.99 | 2.54 | 3.437 (7) | 151 |
C21—H21···O6iv | 0.95 | 2.58 | 3.357 (7) | 139 |
C22—H22···O8 | 0.95 | 2.44 | 2.760 (7) | 100 |
C23—H23A···O12iii | 0.99 | 2.37 | 3.275 (7) | 152 |
C23—H23A···N5 | 0.99 | 2.51 | 3.027 (7) | 112 |
C26—H26A···O13 | 0.99 | 2.50 | 3.202 (6) | 127 |
C26—H26B···N8 | 0.99 | 2.58 | 3.063 (7) | 110 |
C27—H27A···O3v | 0.99 | 2.49 | 3.443 (8) | 161 |
C28—H28B···O15i | 0.99 | 2.54 | 3.125 (8) | 118 |
C30—H30A···O7 | 0.99 | 2.41 | 2.912 (6) | 111 |
C30—H30A···O20 | 0.99 | 2.50 | 3.489 (9) | 177 |
C7—H77···O19 | 0.95 | 2.56 | 3.413 (8) | 149 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y, z−1; (v) −x+1, −y, −z. |