organic compounds
N,N,N-Tris(diphenylphosphorylmethyl)amine
aEuropean Commission, DG Joint Research Centre, Directorate G - Nuclear Safety and Security, G.I.5 – Advanced Nuclear Knowledge, PO Box 2340, 76125 Karlsruhe, Germany
*Correspondence e-mail: olaf.walter@ec.europa.eu
The structure of N,N,N-tris(diphenylphosphorylmethyl)amine, C39H36NO3P3, at 103 K has monoclinic (P21/c) symmetry. Two molecules, each with pseudo-threefold rotation symmetry, crystallize in the of the monoclinic The compound acts as ligand for the stabilization of metal ions with flexible coordination enabling three- or fourfold coordination.
Keywords: crystal structure; phosphine oxide; tripodal ligand.
CCDC reference: 1579667
Structure description
via complex formation. Many complexes of stabilizing lanthanide and actinide ions have been described (some recent examples are: Baulin et al., 2015; Bowden et al., 2015; Dong et al., 2015; Hasegawa et al., 2015; Hirai et al., 2015, 2016; Tolpygin et al., 2015; Yanagisawa et al., 2015). Tripodal ligands form a pocket in which the metal can be embedded via spherical coordination and therefore create a shielded pocket contributing to an even greater stabilization of the complexes (see: Cecconi et al., 2000, 2001a,b; Fu et al., 2011; Li et al., 2010; Somov & Chausov, 2014, 2015; Somov et al., 2015, 2016).
act as ligands for stabilizing oxophilic metal ionsIn the N,N,N-tris(diphenylphosphorylmethyl)amine, the two molecules in the show a comparable arrangement (r.m.s. deviation = 0.5340 Å), even if there are no hydrogen-bond bridges or other external influences (Figs. 1 and 2). Both molecules exhibit a polar pocket with a tripodal arrangement of the N(CH2PR2O)3 group; the P and O atoms of this group show a nearly planar arrangement (mean deviation for the selected atoms from this plane for molecule 1 = 0.065 Å and for molecule 2 = 0.074 Å). The molecules are oriented such that the O atoms point always in the direction of a P atom of a neighbouring arm, establishing an average intramolecular P—O distance of 4.46 (5) Å. The reason of this arrangement is probably found in a dipole–dipole interaction between the partially negative O atom and the partial positive P atom. This arrangement leads, for both molecules, to the formation of a hydrophobic outer sphere of the molecules formed by the phenyl rings sitting at the outside and shielding the polar pocket.
ofThere are no remarkable supramolecular features present in the structures.
For N,N,N-tris(diphenylphosphorylmethyl)amine, coordination with a Be atom has been shown in the complex aqua[N,N,N-tris(diphenylphosphorylmethyl)amine-κ3O,O′,O′′]beryllium(II) diperchlorate (Cecconi et al., 2000). The structure of the ligand itself has not been reported. There exist bidentate ligands incorporating the RN(CH2PR′2O)2 moiety (Elsegood et al., 2013; Enthaler & Nagel, 2014; Hursthouse et al., 2003; Musina et al., 2015; Priya et al., 2003; Yang et al., 2010).
Synthesis and crystallization
To a solution of 3.09 g (15.3 mmol) diphenylphospine oxide dissolved in 20 ml dry tetrahydrofuran (THF) in a Schlenk tube, 9.7 ml of a 1.6 M solution of methyllithium in Et2O were added. This solution was then added to a solution of 0.83 g (5.1 mmol) of tris(chloromethyl)amine in 20 ml dry THF (Figs. 3). The solvent was removed under vacuum, and the residue was extracted with Et2O. N,N,N-Tris(diphenylphosphorylmethyl)amine was obtained as a crystalline product (yield 80%, 2.5 g).
Refinement
Crystal data, data collection and structure . H atoms attached to C atoms were fixed geometrically with fixed bond lengths and refined isotropically using a riding model.
details are summarized in Table 1Structural data
CCDC reference: 1579667
https://doi.org/10.1107/S2414314617014791/vm4029sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014791/vm4029Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617014791/vm4029Isup3.cml
Data collection: APEX2 (Bruker, 2007); cell
APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: XPMA (Zsolnai, 1996) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).C39H36NO3P3 | F(000) = 2768 |
Mr = 659.60 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9219 (10) Å | Cell parameters from 9834 reflections |
b = 25.078 (2) Å | θ = 2.3–27.7° |
c = 24.870 (2) Å | µ = 0.22 mm−1 |
β = 95.515 (1)° | T = 103 K |
V = 6780.3 (10) Å3 | Plates, colourless |
Z = 8 | 0.10 × 0.07 × 0.05 mm |
Bruker APEXII Quazar diffractometer | 16105 independent reflections |
Radiation source: fine-focus sealed tube | 11728 reflections with I > 2σ(I) |
Detector resolution: 66 pixels mm-1 | Rint = 0.061 |
combined ω– and phi–scan | θmax = 28.3°, θmin = 1.2° |
Absorption correction: multi-scan (sadabs) | h = −14→14 |
Tmin = 0.953, Tmax = 0.99 | k = −33→32 |
122037 measured reflections | l = −33→32 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | Only H-atom displacement parameters refined |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0396P)2 + 5.4914P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
16105 reflections | Δρmax = 0.45 e Å−3 |
843 parameters | Δρmin = −0.40 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.79011 (5) | 0.62151 (2) | −0.12042 (2) | 0.01831 (11) | |
P2 | 0.63329 (5) | 0.62870 (2) | 0.05351 (2) | 0.02301 (12) | |
P3 | 0.55451 (5) | 0.76785 (2) | −0.07543 (2) | 0.01861 (11) | |
P4 | 0.36014 (5) | 0.88739 (2) | 0.12751 (2) | 0.01853 (11) | |
P5 | 0.10685 (5) | 0.86584 (2) | −0.04030 (2) | 0.01839 (11) | |
P6 | 0.10461 (5) | 0.73715 (2) | 0.09964 (2) | 0.02016 (11) | |
O1 | 0.80469 (13) | 0.66437 (6) | −0.16077 (5) | 0.0241 (3) | |
O2 | 0.70905 (15) | 0.57987 (6) | 0.04848 (6) | 0.0312 (4) | |
O3 | 0.49328 (13) | 0.77722 (6) | −0.02502 (5) | 0.0229 (3) | |
O4 | 0.39175 (13) | 0.84659 (6) | 0.17029 (5) | 0.0239 (3) | |
O5 | 0.17959 (13) | 0.91595 (6) | −0.04209 (5) | 0.0246 (3) | |
O6 | 0.02638 (14) | 0.71782 (6) | 0.05104 (5) | 0.0260 (3) | |
N1 | 0.68834 (15) | 0.68040 (6) | −0.03998 (6) | 0.0171 (3) | |
N2 | 0.21699 (15) | 0.82391 (6) | 0.05487 (6) | 0.0171 (3) | |
C1 | 0.78999 (18) | 0.64463 (8) | −0.05105 (7) | 0.0194 (4) | |
H1A | 0.787769 | 0.613050 | −0.027280 | 0.026 (2)* | |
H1B | 0.868570 | 0.663403 | −0.040909 | 0.026 (2)* | |
C2 | 0.68655 (19) | 0.68687 (8) | 0.01902 (7) | 0.0197 (4) | |
H2A | 0.632804 | 0.717442 | 0.025816 | 0.026 (2)* | |
H2B | 0.770738 | 0.695709 | 0.034858 | 0.026 (2)* | |
C3 | 0.70148 (18) | 0.73311 (8) | −0.06518 (7) | 0.0184 (4) | |
H3A | 0.735306 | 0.728487 | −0.100420 | 0.026 (2)* | |
H3B | 0.760333 | 0.754978 | −0.041800 | 0.026 (2)* | |
C4 | 0.91934 (18) | 0.57623 (8) | −0.11559 (8) | 0.0211 (4) | |
C5 | 1.01796 (19) | 0.58845 (9) | −0.14473 (8) | 0.0251 (5) | |
H5 | 1.015273 | 0.619544 | −0.166628 | 0.033 (3)* | |
C6 | 1.1202 (2) | 0.55553 (10) | −0.14201 (9) | 0.0312 (5) | |
H6 | 1.187678 | 0.564235 | −0.161806 | 0.033 (3)* | |
C7 | 1.1242 (2) | 0.50998 (9) | −0.11049 (9) | 0.0311 (5) | |
H7 | 1.194005 | 0.487245 | −0.109067 | 0.033 (3)* | |
C8 | 1.0270 (2) | 0.49743 (9) | −0.08104 (10) | 0.0321 (5) | |
H8 | 1.030393 | 0.466257 | −0.059245 | 0.033 (3)* | |
C9 | 0.9242 (2) | 0.53038 (9) | −0.08331 (9) | 0.0283 (5) | |
H9 | 0.857545 | 0.521813 | −0.063005 | 0.033 (3)* | |
C10 | 0.65566 (18) | 0.58094 (8) | −0.13825 (8) | 0.0199 (4) | |
C11 | 0.6439 (2) | 0.55947 (9) | −0.19059 (8) | 0.0258 (5) | |
H11 | 0.705613 | 0.566100 | −0.214195 | 0.035 (3)* | |
C12 | 0.5426 (2) | 0.52867 (9) | −0.20789 (9) | 0.0283 (5) | |
H12 | 0.535000 | 0.514231 | −0.243369 | 0.035 (3)* | |
C13 | 0.4526 (2) | 0.51881 (9) | −0.17379 (9) | 0.0290 (5) | |
H13 | 0.383796 | 0.497161 | −0.185533 | 0.035 (3)* | |
C14 | 0.4630 (2) | 0.54062 (10) | −0.12242 (9) | 0.0348 (6) | |
H14 | 0.400514 | 0.534297 | −0.099138 | 0.035 (3)* | |
C15 | 0.5643 (2) | 0.57171 (10) | −0.10467 (8) | 0.0301 (5) | |
H15 | 0.570594 | 0.586631 | −0.069396 | 0.035 (3)* | |
C16 | 0.4747 (2) | 0.61749 (9) | 0.02914 (8) | 0.0241 (4) | |
C17 | 0.3925 (2) | 0.65785 (9) | 0.01293 (9) | 0.0283 (5) | |
H17 | 0.419529 | 0.693869 | 0.013479 | 0.041 (3)* | |
C18 | 0.2703 (2) | 0.64576 (10) | −0.00418 (9) | 0.0336 (5) | |
H18 | 0.213709 | 0.673588 | −0.014308 | 0.041 (3)* | |
C19 | 0.2315 (2) | 0.59315 (10) | −0.00640 (9) | 0.0364 (6) | |
H19 | 0.148133 | 0.585013 | −0.017915 | 0.041 (3)* | |
C20 | 0.3136 (2) | 0.55230 (10) | 0.00808 (9) | 0.0364 (6) | |
H20 | 0.287273 | 0.516219 | 0.005390 | 0.041 (3)* | |
C21 | 0.4344 (2) | 0.56429 (9) | 0.02652 (9) | 0.0313 (5) | |
H21 | 0.490186 | 0.536378 | 0.037416 | 0.041 (3)* | |
C22 | 0.6376 (2) | 0.65232 (9) | 0.12251 (8) | 0.0283 (5) | |
C23 | 0.5647 (2) | 0.69389 (11) | 0.13777 (9) | 0.0368 (6) | |
H23 | 0.508542 | 0.710689 | 0.111517 | 0.055 (4)* | |
C24 | 0.5729 (2) | 0.71128 (12) | 0.19125 (10) | 0.0438 (7) | |
H24 | 0.522829 | 0.739803 | 0.201511 | 0.055 (4)* | |
C25 | 0.6549 (3) | 0.68649 (12) | 0.22928 (9) | 0.0485 (8) | |
H25 | 0.660756 | 0.698053 | 0.265810 | 0.055 (4)* | |
C26 | 0.7274 (3) | 0.64563 (11) | 0.21475 (10) | 0.0475 (7) | |
H26 | 0.782704 | 0.628805 | 0.241299 | 0.055 (4)* | |
C27 | 0.7208 (3) | 0.62830 (10) | 0.16103 (9) | 0.0395 (6) | |
H27 | 0.772765 | 0.600377 | 0.150942 | 0.055 (4)* | |
C28 | 0.46179 (19) | 0.72860 (8) | −0.12457 (8) | 0.0211 (4) | |
C29 | 0.3384 (2) | 0.72150 (9) | −0.11850 (9) | 0.0319 (5) | |
H29 | 0.304592 | 0.735614 | −0.087718 | 0.040 (3)* | |
C30 | 0.2635 (2) | 0.69362 (11) | −0.15750 (11) | 0.0404 (6) | |
H30 | 0.178619 | 0.688800 | −0.153447 | 0.040 (3)* | |
C31 | 0.3138 (2) | 0.67300 (10) | −0.20219 (9) | 0.0360 (6) | |
H31 | 0.263019 | 0.654055 | −0.228861 | 0.040 (3)* | |
C32 | 0.4365 (2) | 0.67979 (9) | −0.20817 (8) | 0.0315 (5) | |
H32 | 0.470200 | 0.665176 | −0.238751 | 0.040 (3)* | |
C33 | 0.5112 (2) | 0.70773 (9) | −0.16998 (8) | 0.0258 (5) | |
H33 | 0.595789 | 0.712751 | −0.174543 | 0.040 (3)* | |
C34 | 0.58512 (19) | 0.82821 (8) | −0.11178 (7) | 0.0210 (4) | |
C35 | 0.4843 (2) | 0.85512 (9) | −0.13775 (9) | 0.0309 (5) | |
H35 | 0.403638 | 0.841453 | −0.135993 | 0.039 (3)* | |
C36 | 0.5013 (2) | 0.90163 (9) | −0.16603 (10) | 0.0353 (6) | |
H36 | 0.432198 | 0.919675 | −0.183636 | 0.039 (3)* | |
C37 | 0.6176 (2) | 0.92196 (9) | −0.16885 (9) | 0.0335 (6) | |
H37 | 0.628548 | 0.953830 | −0.188483 | 0.039 (3)* | |
C38 | 0.7184 (2) | 0.89605 (9) | −0.14316 (8) | 0.0326 (5) | |
H38 | 0.798653 | 0.910183 | −0.144882 | 0.039 (3)* | |
C39 | 0.7021 (2) | 0.84904 (9) | −0.11468 (8) | 0.0274 (5) | |
H39 | 0.771554 | 0.831168 | −0.097151 | 0.039 (3)* | |
C40 | 0.32483 (18) | 0.85967 (8) | 0.06036 (7) | 0.0189 (4) | |
H40A | 0.310170 | 0.889394 | 0.034340 | 0.025 (2)* | |
H40B | 0.397426 | 0.839629 | 0.050418 | 0.025 (2)* | |
C41 | 0.18464 (18) | 0.81164 (8) | −0.00284 (7) | 0.0181 (4) | |
H41A | 0.130935 | 0.779761 | −0.005717 | 0.025 (2)* | |
H41B | 0.260751 | 0.802781 | −0.019579 | 0.025 (2)* | |
C42 | 0.24160 (18) | 0.77409 (8) | 0.08536 (7) | 0.0193 (4) | |
H42A | 0.289777 | 0.782709 | 0.120031 | 0.025 (2)* | |
H42B | 0.293073 | 0.750740 | 0.064638 | 0.025 (2)* | |
C43 | 0.48673 (18) | 0.93204 (8) | 0.11987 (7) | 0.0195 (4) | |
C44 | 0.59703 (19) | 0.92280 (9) | 0.15184 (8) | 0.0258 (5) | |
H44 | 0.603601 | 0.893774 | 0.176488 | 0.035 (3)* | |
C45 | 0.6969 (2) | 0.95618 (10) | 0.14745 (8) | 0.0300 (5) | |
H45 | 0.771901 | 0.949974 | 0.169195 | 0.035 (3)* | |
C46 | 0.6877 (2) | 0.99845 (9) | 0.11155 (9) | 0.0285 (5) | |
H46 | 0.756433 | 1.021128 | 0.108623 | 0.035 (3)* | |
C47 | 0.5783 (2) | 1.00775 (9) | 0.07983 (8) | 0.0271 (5) | |
H47 | 0.572156 | 1.036811 | 0.055209 | 0.035 (3)* | |
C48 | 0.47797 (19) | 0.97482 (8) | 0.08394 (8) | 0.0240 (4) | |
H48 | 0.403050 | 0.981379 | 0.062260 | 0.035 (3)* | |
C49 | 0.23395 (18) | 0.92915 (8) | 0.14350 (8) | 0.0195 (4) | |
C50 | 0.2382 (2) | 0.94835 (9) | 0.19651 (8) | 0.0247 (5) | |
H50 | 0.305917 | 0.939453 | 0.221783 | 0.035 (3)* | |
C51 | 0.1448 (2) | 0.98013 (9) | 0.21241 (8) | 0.0295 (5) | |
H51 | 0.149771 | 0.993869 | 0.248153 | 0.035 (3)* | |
C52 | 0.0439 (2) | 0.99198 (9) | 0.17623 (9) | 0.0291 (5) | |
H52 | −0.021173 | 1.013189 | 0.187383 | 0.035 (3)* | |
C53 | 0.0381 (2) | 0.97288 (9) | 0.12388 (9) | 0.0296 (5) | |
H53 | −0.031125 | 0.981043 | 0.099129 | 0.035 (3)* | |
C54 | 0.13244 (19) | 0.94193 (9) | 0.10734 (8) | 0.0260 (5) | |
H54 | 0.128111 | 0.929316 | 0.071191 | 0.035 (3)* | |
C55 | −0.03716 (18) | 0.87709 (8) | −0.01214 (7) | 0.0197 (4) | |
C56 | −0.0857 (2) | 0.92877 (9) | −0.01684 (8) | 0.0248 (5) | |
H56 | −0.040249 | 0.956237 | −0.032152 | 0.028 (3)* | |
C57 | −0.1992 (2) | 0.94012 (9) | 0.00061 (8) | 0.0294 (5) | |
H57 | −0.231478 | 0.975273 | −0.002645 | 0.028 (3)* | |
C58 | −0.2659 (2) | 0.90017 (9) | 0.02284 (8) | 0.0284 (5) | |
H58 | −0.344789 | 0.907747 | 0.034003 | 0.028 (3)* | |
C59 | −0.2178 (2) | 0.84918 (9) | 0.02886 (8) | 0.0260 (5) | |
H59 | −0.263277 | 0.822098 | 0.044762 | 0.028 (3)* | |
C60 | −0.10332 (19) | 0.83740 (8) | 0.01176 (7) | 0.0219 (4) | |
H60 | −0.070263 | 0.802475 | 0.016323 | 0.028 (3)* | |
C61 | 0.06819 (18) | 0.83747 (8) | −0.10663 (7) | 0.0196 (4) | |
C62 | 0.0980 (2) | 0.86625 (9) | −0.15147 (8) | 0.0271 (5) | |
H62 | 0.140942 | 0.899094 | −0.146598 | 0.034 (3)* | |
C63 | 0.0650 (2) | 0.84708 (10) | −0.20344 (9) | 0.0351 (6) | |
H63 | 0.084768 | 0.867037 | −0.233905 | 0.034 (3)* | |
C64 | 0.0037 (2) | 0.79910 (10) | −0.21069 (8) | 0.0313 (5) | |
H64 | −0.018171 | 0.786077 | −0.246189 | 0.034 (3)* | |
C65 | −0.0261 (2) | 0.76992 (9) | −0.16672 (8) | 0.0272 (5) | |
H65 | −0.068475 | 0.736963 | −0.171922 | 0.034 (3)* | |
C66 | 0.00615 (19) | 0.78899 (9) | −0.11479 (8) | 0.0237 (4) | |
H66 | −0.014204 | 0.768850 | −0.084548 | 0.034 (3)* | |
C67 | 0.01997 (19) | 0.77783 (8) | 0.14301 (7) | 0.0196 (4) | |
C68 | 0.0756 (2) | 0.81575 (9) | 0.17843 (8) | 0.0240 (4) | |
H68 | 0.161390 | 0.822314 | 0.179234 | 0.038 (3)* | |
C69 | 0.0053 (2) | 0.84393 (9) | 0.21253 (8) | 0.0284 (5) | |
H69 | 0.043558 | 0.869783 | 0.236511 | 0.038 (3)* | |
C70 | −0.1194 (2) | 0.83469 (9) | 0.21189 (8) | 0.0285 (5) | |
H70 | −0.166562 | 0.853679 | 0.235735 | 0.038 (3)* | |
C71 | −0.1752 (2) | 0.79776 (10) | 0.17645 (9) | 0.0324 (5) | |
H71 | −0.261315 | 0.791824 | 0.175472 | 0.038 (3)* | |
C72 | −0.1065 (2) | 0.76929 (9) | 0.14229 (8) | 0.0278 (5) | |
H72 | −0.145666 | 0.743775 | 0.118193 | 0.038 (3)* | |
C73 | 0.1731 (2) | 0.68403 (8) | 0.14147 (8) | 0.0247 (5) | |
C74 | 0.2498 (2) | 0.69481 (10) | 0.18835 (10) | 0.0356 (6) | |
H74 | 0.261482 | 0.730590 | 0.200281 | 0.076 (5)* | |
C75 | 0.3089 (2) | 0.65381 (11) | 0.21757 (11) | 0.0431 (6) | |
H75 | 0.360825 | 0.661260 | 0.249550 | 0.076 (5)* | |
C76 | 0.2917 (3) | 0.60195 (12) | 0.19984 (11) | 0.0559 (8) | |
H76 | 0.333542 | 0.573719 | 0.219339 | 0.076 (5)* | |
C77 | 0.2156 (4) | 0.59091 (12) | 0.15480 (12) | 0.0760 (12) | |
H77 | 0.202907 | 0.554957 | 0.143585 | 0.076 (5)* | |
C78 | 0.1562 (3) | 0.63188 (10) | 0.12494 (10) | 0.0547 (9) | |
H78 | 0.104030 | 0.623900 | 0.093173 | 0.076 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0175 (3) | 0.0196 (3) | 0.0183 (2) | −0.0006 (2) | 0.00430 (19) | −0.00088 (19) |
P2 | 0.0280 (3) | 0.0239 (3) | 0.0174 (2) | −0.0019 (2) | 0.0036 (2) | −0.0001 (2) |
P3 | 0.0182 (3) | 0.0195 (3) | 0.0180 (2) | −0.0006 (2) | 0.00107 (19) | −0.00319 (19) |
P4 | 0.0155 (2) | 0.0242 (3) | 0.0155 (2) | −0.0027 (2) | −0.00039 (18) | 0.00124 (19) |
P5 | 0.0182 (3) | 0.0198 (3) | 0.0168 (2) | −0.0024 (2) | −0.00013 (19) | 0.00007 (19) |
P6 | 0.0229 (3) | 0.0189 (3) | 0.0187 (2) | −0.0019 (2) | 0.00194 (19) | −0.00013 (19) |
O1 | 0.0273 (8) | 0.0235 (8) | 0.0221 (7) | −0.0012 (6) | 0.0060 (6) | 0.0025 (6) |
O2 | 0.0385 (10) | 0.0269 (9) | 0.0285 (8) | 0.0035 (7) | 0.0053 (7) | 0.0053 (6) |
O3 | 0.0225 (8) | 0.0254 (8) | 0.0215 (7) | −0.0004 (6) | 0.0048 (6) | −0.0044 (6) |
O4 | 0.0224 (8) | 0.0291 (8) | 0.0195 (7) | −0.0030 (6) | −0.0015 (6) | 0.0045 (6) |
O5 | 0.0245 (8) | 0.0237 (8) | 0.0248 (7) | −0.0065 (6) | −0.0009 (6) | 0.0013 (6) |
O6 | 0.0300 (8) | 0.0248 (8) | 0.0225 (7) | −0.0066 (7) | −0.0002 (6) | −0.0036 (6) |
N1 | 0.0168 (8) | 0.0192 (9) | 0.0156 (7) | 0.0009 (7) | 0.0035 (6) | −0.0024 (6) |
N2 | 0.0168 (8) | 0.0188 (9) | 0.0154 (7) | −0.0015 (7) | 0.0006 (6) | 0.0011 (6) |
C1 | 0.0172 (10) | 0.0211 (11) | 0.0199 (9) | 0.0000 (8) | 0.0014 (7) | −0.0025 (7) |
C2 | 0.0218 (10) | 0.0213 (11) | 0.0159 (9) | −0.0022 (8) | 0.0014 (7) | −0.0028 (7) |
C3 | 0.0195 (10) | 0.0180 (10) | 0.0178 (9) | −0.0020 (8) | 0.0022 (7) | −0.0016 (7) |
C4 | 0.0178 (10) | 0.0231 (11) | 0.0225 (9) | −0.0016 (8) | 0.0017 (8) | −0.0048 (8) |
C5 | 0.0238 (11) | 0.0310 (12) | 0.0209 (9) | 0.0005 (9) | 0.0043 (8) | −0.0022 (8) |
C6 | 0.0202 (11) | 0.0451 (15) | 0.0293 (11) | 0.0014 (10) | 0.0070 (9) | −0.0067 (10) |
C7 | 0.0228 (12) | 0.0323 (13) | 0.0374 (12) | 0.0075 (10) | −0.0018 (9) | −0.0119 (10) |
C8 | 0.0294 (13) | 0.0235 (12) | 0.0421 (13) | 0.0027 (10) | −0.0041 (10) | 0.0023 (10) |
C9 | 0.0212 (11) | 0.0266 (12) | 0.0378 (12) | −0.0025 (9) | 0.0061 (9) | 0.0019 (9) |
C10 | 0.0184 (10) | 0.0193 (10) | 0.0218 (9) | 0.0026 (8) | 0.0007 (8) | 0.0004 (8) |
C11 | 0.0244 (11) | 0.0290 (12) | 0.0247 (10) | −0.0001 (9) | 0.0052 (8) | −0.0036 (8) |
C12 | 0.0272 (12) | 0.0284 (12) | 0.0284 (11) | 0.0019 (10) | −0.0019 (9) | −0.0061 (9) |
C13 | 0.0206 (11) | 0.0298 (13) | 0.0348 (11) | −0.0039 (9) | −0.0066 (9) | 0.0013 (9) |
C14 | 0.0234 (12) | 0.0531 (16) | 0.0280 (11) | −0.0104 (11) | 0.0035 (9) | 0.0023 (10) |
C15 | 0.0259 (12) | 0.0447 (14) | 0.0199 (10) | −0.0071 (10) | 0.0028 (8) | −0.0028 (9) |
C16 | 0.0286 (12) | 0.0272 (12) | 0.0180 (9) | −0.0051 (9) | 0.0093 (8) | −0.0046 (8) |
C17 | 0.0289 (12) | 0.0259 (12) | 0.0313 (11) | −0.0054 (10) | 0.0083 (9) | −0.0084 (9) |
C18 | 0.0273 (13) | 0.0355 (14) | 0.0395 (13) | −0.0061 (10) | 0.0108 (10) | −0.0101 (10) |
C19 | 0.0295 (13) | 0.0449 (16) | 0.0365 (12) | −0.0140 (11) | 0.0124 (10) | −0.0120 (11) |
C20 | 0.0432 (15) | 0.0324 (14) | 0.0364 (12) | −0.0189 (12) | 0.0183 (11) | −0.0091 (10) |
C21 | 0.0404 (14) | 0.0274 (13) | 0.0279 (11) | −0.0077 (11) | 0.0121 (10) | −0.0006 (9) |
C22 | 0.0354 (13) | 0.0314 (13) | 0.0186 (9) | −0.0094 (10) | 0.0047 (9) | 0.0002 (8) |
C23 | 0.0328 (13) | 0.0521 (16) | 0.0259 (11) | −0.0039 (12) | 0.0040 (9) | −0.0096 (11) |
C24 | 0.0404 (15) | 0.0606 (18) | 0.0323 (12) | −0.0130 (13) | 0.0127 (11) | −0.0173 (12) |
C25 | 0.066 (2) | 0.0595 (19) | 0.0205 (11) | −0.0260 (16) | 0.0075 (12) | −0.0062 (11) |
C26 | 0.069 (2) | 0.0476 (17) | 0.0244 (11) | −0.0149 (15) | −0.0053 (12) | 0.0054 (11) |
C27 | 0.0555 (17) | 0.0350 (14) | 0.0269 (11) | −0.0068 (12) | −0.0019 (11) | 0.0044 (10) |
C28 | 0.0214 (10) | 0.0193 (11) | 0.0219 (9) | −0.0004 (8) | −0.0014 (8) | −0.0018 (8) |
C29 | 0.0261 (12) | 0.0335 (13) | 0.0359 (12) | −0.0011 (10) | 0.0022 (9) | −0.0101 (10) |
C30 | 0.0222 (12) | 0.0453 (16) | 0.0521 (15) | −0.0059 (11) | −0.0043 (11) | −0.0124 (12) |
C31 | 0.0386 (14) | 0.0305 (13) | 0.0352 (12) | −0.0013 (11) | −0.0155 (10) | −0.0088 (10) |
C32 | 0.0416 (14) | 0.0292 (13) | 0.0217 (10) | 0.0060 (11) | −0.0070 (9) | −0.0048 (9) |
C33 | 0.0271 (12) | 0.0296 (12) | 0.0199 (9) | 0.0029 (9) | −0.0015 (8) | −0.0025 (8) |
C34 | 0.0256 (11) | 0.0190 (10) | 0.0182 (9) | 0.0025 (8) | 0.0016 (8) | −0.0051 (7) |
C35 | 0.0271 (12) | 0.0268 (12) | 0.0387 (12) | 0.0041 (10) | 0.0028 (10) | −0.0001 (10) |
C36 | 0.0423 (15) | 0.0238 (12) | 0.0390 (13) | 0.0112 (11) | −0.0005 (11) | 0.0012 (10) |
C37 | 0.0548 (16) | 0.0200 (12) | 0.0255 (11) | −0.0012 (11) | 0.0035 (10) | −0.0010 (9) |
C38 | 0.0409 (14) | 0.0311 (13) | 0.0250 (10) | −0.0116 (11) | −0.0008 (10) | 0.0000 (9) |
C39 | 0.0308 (12) | 0.0292 (12) | 0.0211 (9) | −0.0048 (10) | −0.0027 (8) | 0.0015 (8) |
C40 | 0.0157 (10) | 0.0233 (11) | 0.0179 (8) | −0.0017 (8) | 0.0025 (7) | 0.0002 (7) |
C41 | 0.0188 (10) | 0.0193 (10) | 0.0162 (8) | 0.0005 (8) | 0.0018 (7) | −0.0008 (7) |
C42 | 0.0198 (10) | 0.0203 (10) | 0.0181 (9) | 0.0021 (8) | 0.0026 (7) | 0.0010 (7) |
C43 | 0.0159 (10) | 0.0252 (11) | 0.0179 (9) | −0.0027 (8) | 0.0033 (7) | −0.0029 (8) |
C44 | 0.0213 (11) | 0.0354 (13) | 0.0204 (9) | −0.0044 (9) | 0.0001 (8) | 0.0011 (9) |
C45 | 0.0203 (11) | 0.0436 (14) | 0.0259 (10) | −0.0064 (10) | 0.0002 (8) | −0.0039 (10) |
C46 | 0.0246 (12) | 0.0306 (13) | 0.0314 (11) | −0.0107 (10) | 0.0085 (9) | −0.0090 (9) |
C47 | 0.0321 (12) | 0.0228 (12) | 0.0279 (10) | −0.0021 (9) | 0.0100 (9) | 0.0000 (8) |
C48 | 0.0218 (11) | 0.0270 (12) | 0.0232 (10) | −0.0006 (9) | 0.0021 (8) | −0.0019 (8) |
C49 | 0.0167 (10) | 0.0202 (10) | 0.0218 (9) | −0.0045 (8) | 0.0036 (7) | 0.0004 (8) |
C50 | 0.0243 (11) | 0.0278 (12) | 0.0215 (9) | −0.0044 (9) | −0.0014 (8) | −0.0009 (8) |
C51 | 0.0339 (13) | 0.0328 (13) | 0.0223 (10) | −0.0016 (10) | 0.0053 (9) | −0.0047 (9) |
C52 | 0.0254 (12) | 0.0294 (13) | 0.0340 (11) | 0.0011 (10) | 0.0108 (9) | 0.0004 (9) |
C53 | 0.0208 (11) | 0.0375 (14) | 0.0304 (11) | 0.0033 (10) | 0.0012 (9) | 0.0045 (10) |
C54 | 0.0218 (11) | 0.0359 (13) | 0.0201 (9) | −0.0003 (9) | 0.0011 (8) | −0.0012 (9) |
C55 | 0.0186 (10) | 0.0251 (11) | 0.0146 (8) | −0.0001 (8) | −0.0021 (7) | −0.0030 (7) |
C56 | 0.0278 (12) | 0.0243 (11) | 0.0214 (9) | −0.0004 (9) | −0.0019 (8) | 0.0009 (8) |
C57 | 0.0304 (12) | 0.0309 (13) | 0.0259 (10) | 0.0099 (10) | −0.0016 (9) | −0.0019 (9) |
C58 | 0.0228 (11) | 0.0373 (14) | 0.0249 (10) | 0.0052 (10) | 0.0011 (8) | −0.0083 (9) |
C59 | 0.0246 (11) | 0.0302 (12) | 0.0231 (10) | −0.0019 (9) | 0.0020 (8) | −0.0040 (9) |
C60 | 0.0243 (11) | 0.0224 (11) | 0.0189 (9) | −0.0010 (9) | 0.0006 (8) | −0.0032 (8) |
C61 | 0.0162 (10) | 0.0235 (11) | 0.0188 (9) | 0.0002 (8) | −0.0001 (7) | −0.0019 (8) |
C62 | 0.0324 (13) | 0.0260 (12) | 0.0236 (10) | −0.0066 (10) | 0.0056 (9) | 0.0006 (8) |
C63 | 0.0444 (15) | 0.0407 (14) | 0.0205 (10) | −0.0044 (12) | 0.0056 (9) | 0.0032 (9) |
C64 | 0.0349 (13) | 0.0386 (14) | 0.0202 (10) | 0.0001 (11) | 0.0011 (9) | −0.0078 (9) |
C65 | 0.0226 (11) | 0.0292 (12) | 0.0295 (11) | −0.0044 (9) | 0.0011 (9) | −0.0063 (9) |
C66 | 0.0215 (11) | 0.0271 (12) | 0.0229 (10) | −0.0030 (9) | 0.0037 (8) | 0.0019 (8) |
C67 | 0.0217 (10) | 0.0198 (10) | 0.0172 (9) | −0.0012 (8) | 0.0021 (7) | 0.0042 (7) |
C68 | 0.0223 (11) | 0.0280 (12) | 0.0219 (9) | −0.0025 (9) | 0.0031 (8) | −0.0016 (8) |
C69 | 0.0337 (13) | 0.0280 (12) | 0.0242 (10) | −0.0018 (10) | 0.0054 (9) | −0.0043 (9) |
C70 | 0.0280 (12) | 0.0358 (13) | 0.0231 (10) | 0.0065 (10) | 0.0099 (9) | 0.0013 (9) |
C71 | 0.0207 (12) | 0.0467 (15) | 0.0304 (11) | −0.0047 (10) | 0.0057 (9) | 0.0029 (10) |
C72 | 0.0244 (11) | 0.0347 (13) | 0.0240 (10) | −0.0058 (10) | 0.0018 (8) | −0.0017 (9) |
C73 | 0.0292 (12) | 0.0218 (11) | 0.0240 (10) | 0.0034 (9) | 0.0083 (8) | 0.0039 (8) |
C74 | 0.0347 (14) | 0.0287 (13) | 0.0416 (13) | −0.0033 (11) | −0.0054 (11) | 0.0102 (10) |
C75 | 0.0382 (15) | 0.0423 (16) | 0.0478 (15) | 0.0036 (12) | −0.0004 (12) | 0.0169 (12) |
C76 | 0.084 (2) | 0.0392 (17) | 0.0452 (16) | 0.0284 (16) | 0.0095 (15) | 0.0129 (12) |
C77 | 0.157 (4) | 0.0220 (15) | 0.0446 (17) | 0.0199 (19) | −0.013 (2) | −0.0017 (12) |
C78 | 0.103 (3) | 0.0271 (14) | 0.0306 (13) | 0.0006 (15) | −0.0106 (14) | −0.0010 (10) |
P1—O1 | 1.4893 (15) | C24—C25 | 1.386 (4) |
P1—C10 | 1.806 (2) | C25—C26 | 1.364 (4) |
P1—C4 | 1.806 (2) | C26—C27 | 1.400 (3) |
P1—C1 | 1.8203 (19) | C28—C29 | 1.382 (3) |
P2—O2 | 1.4900 (17) | C28—C33 | 1.399 (3) |
P2—C16 | 1.802 (2) | C29—C30 | 1.395 (3) |
P2—C22 | 1.812 (2) | C30—C31 | 1.386 (4) |
P2—C2 | 1.816 (2) | C31—C32 | 1.373 (4) |
P3—O3 | 1.4950 (14) | C32—C33 | 1.382 (3) |
P3—C28 | 1.8027 (19) | C34—C39 | 1.389 (3) |
P3—C34 | 1.811 (2) | C34—C35 | 1.396 (3) |
P3—C3 | 1.823 (2) | C35—C36 | 1.384 (3) |
P4—O4 | 1.4923 (14) | C36—C37 | 1.377 (4) |
P4—C43 | 1.804 (2) | C37—C38 | 1.381 (3) |
P4—C49 | 1.805 (2) | C38—C39 | 1.395 (3) |
P4—C40 | 1.8159 (19) | C43—C48 | 1.394 (3) |
P5—O5 | 1.4897 (15) | C43—C44 | 1.397 (3) |
P5—C55 | 1.804 (2) | C44—C45 | 1.387 (3) |
P5—C61 | 1.8089 (19) | C45—C46 | 1.383 (3) |
P5—C41 | 1.8124 (19) | C46—C47 | 1.388 (3) |
P6—O6 | 1.4926 (14) | C47—C48 | 1.383 (3) |
P6—C67 | 1.803 (2) | C49—C54 | 1.396 (3) |
P6—C73 | 1.807 (2) | C49—C50 | 1.400 (3) |
P6—C42 | 1.824 (2) | C50—C51 | 1.382 (3) |
N1—C1 | 1.474 (2) | C51—C52 | 1.387 (3) |
N1—C3 | 1.476 (2) | C52—C53 | 1.383 (3) |
N1—C2 | 1.478 (2) | C53—C54 | 1.384 (3) |
N2—C42 | 1.473 (2) | C55—C60 | 1.396 (3) |
N2—C40 | 1.476 (2) | C55—C56 | 1.401 (3) |
N2—C41 | 1.477 (2) | C56—C57 | 1.382 (3) |
C4—C5 | 1.389 (3) | C57—C58 | 1.384 (3) |
C4—C9 | 1.401 (3) | C58—C59 | 1.385 (3) |
C5—C6 | 1.385 (3) | C59—C60 | 1.390 (3) |
C6—C7 | 1.384 (3) | C61—C62 | 1.393 (3) |
C7—C8 | 1.383 (3) | C61—C66 | 1.397 (3) |
C8—C9 | 1.390 (3) | C62—C63 | 1.394 (3) |
C10—C15 | 1.381 (3) | C63—C64 | 1.380 (3) |
C10—C11 | 1.403 (3) | C64—C65 | 1.380 (3) |
C11—C12 | 1.383 (3) | C65—C66 | 1.390 (3) |
C12—C13 | 1.381 (3) | C67—C68 | 1.395 (3) |
C13—C14 | 1.384 (3) | C67—C72 | 1.396 (3) |
C14—C15 | 1.390 (3) | C68—C69 | 1.390 (3) |
C16—C17 | 1.387 (3) | C69—C70 | 1.381 (3) |
C16—C21 | 1.404 (3) | C70—C71 | 1.380 (3) |
C17—C18 | 1.395 (3) | C71—C72 | 1.385 (3) |
C18—C19 | 1.385 (3) | C73—C78 | 1.378 (3) |
C19—C20 | 1.386 (4) | C73—C74 | 1.395 (3) |
C20—C21 | 1.388 (3) | C74—C75 | 1.383 (3) |
C22—C23 | 1.387 (3) | C75—C76 | 1.380 (4) |
C22—C27 | 1.393 (3) | C76—C77 | 1.358 (4) |
C23—C24 | 1.395 (3) | C77—C78 | 1.391 (4) |
O1—P1—C10 | 112.22 (9) | C22—C23—C24 | 120.7 (2) |
O1—P1—C4 | 111.41 (9) | C25—C24—C23 | 119.3 (3) |
C10—P1—C4 | 105.90 (9) | C26—C25—C24 | 120.6 (2) |
O1—P1—C1 | 114.74 (9) | C25—C26—C27 | 120.5 (3) |
C10—P1—C1 | 109.72 (9) | C22—C27—C26 | 119.5 (3) |
C4—P1—C1 | 102.06 (9) | C29—C28—C33 | 119.72 (19) |
O2—P2—C16 | 111.55 (10) | C29—C28—P3 | 119.11 (16) |
O2—P2—C22 | 112.59 (10) | C33—C28—P3 | 121.09 (16) |
C16—P2—C22 | 107.84 (10) | C28—C29—C30 | 120.1 (2) |
O2—P2—C2 | 114.51 (10) | C31—C30—C29 | 119.6 (2) |
C16—P2—C2 | 107.93 (10) | C32—C31—C30 | 120.4 (2) |
C22—P2—C2 | 101.79 (9) | C31—C32—C33 | 120.4 (2) |
O3—P3—C28 | 112.76 (9) | C32—C33—C28 | 119.7 (2) |
O3—P3—C34 | 113.96 (9) | C39—C34—C35 | 118.9 (2) |
C28—P3—C34 | 103.69 (9) | C39—C34—P3 | 123.74 (16) |
O3—P3—C3 | 114.64 (8) | C35—C34—P3 | 117.38 (17) |
C28—P3—C3 | 105.29 (9) | C36—C35—C34 | 120.3 (2) |
C34—P3—C3 | 105.48 (9) | C37—C36—C35 | 120.5 (2) |
O4—P4—C43 | 111.94 (9) | C36—C37—C38 | 120.0 (2) |
O4—P4—C49 | 111.71 (9) | C37—C38—C39 | 119.8 (2) |
C43—P4—C49 | 105.80 (9) | C34—C39—C38 | 120.5 (2) |
O4—P4—C40 | 114.03 (9) | N2—C40—P4 | 114.49 (13) |
C43—P4—C40 | 103.76 (9) | N2—C41—P5 | 113.55 (13) |
C49—P4—C40 | 108.99 (9) | N2—C42—P6 | 114.76 (13) |
O5—P5—C55 | 111.53 (9) | C48—C43—C44 | 119.66 (19) |
O5—P5—C61 | 112.51 (9) | C48—C43—P4 | 122.65 (15) |
C55—P5—C61 | 106.24 (9) | C44—C43—P4 | 117.69 (16) |
O5—P5—C41 | 115.03 (9) | C45—C44—C43 | 119.8 (2) |
C55—P5—C41 | 107.51 (9) | C46—C45—C44 | 120.3 (2) |
C61—P5—C41 | 103.33 (9) | C45—C46—C47 | 120.1 (2) |
O6—P6—C67 | 112.44 (9) | C48—C47—C46 | 120.2 (2) |
O6—P6—C73 | 113.57 (9) | C47—C48—C43 | 120.06 (19) |
C67—P6—C73 | 106.28 (9) | C54—C49—C50 | 118.68 (19) |
O6—P6—C42 | 115.07 (9) | C54—C49—P4 | 124.56 (15) |
C67—P6—C42 | 107.85 (9) | C50—C49—P4 | 116.74 (15) |
C73—P6—C42 | 100.65 (10) | C51—C50—C49 | 120.61 (19) |
C1—N1—C3 | 111.10 (15) | C50—C51—C52 | 120.0 (2) |
C1—N1—C2 | 109.53 (15) | C53—C52—C51 | 119.9 (2) |
C3—N1—C2 | 109.53 (14) | C52—C53—C54 | 120.4 (2) |
C42—N2—C40 | 111.31 (14) | C53—C54—C49 | 120.36 (19) |
C42—N2—C41 | 109.76 (15) | C60—C55—C56 | 119.20 (19) |
C40—N2—C41 | 109.30 (15) | C60—C55—P5 | 124.05 (16) |
N1—C1—P1 | 116.12 (12) | C56—C55—P5 | 116.71 (16) |
N1—C2—P2 | 114.58 (13) | C57—C56—C55 | 120.5 (2) |
N1—C3—P3 | 111.54 (13) | C56—C57—C58 | 119.9 (2) |
C5—C4—C9 | 119.4 (2) | C57—C58—C59 | 120.2 (2) |
C5—C4—P1 | 117.83 (16) | C58—C59—C60 | 120.4 (2) |
C9—C4—P1 | 122.74 (16) | C59—C60—C55 | 119.7 (2) |
C6—C5—C4 | 120.3 (2) | C62—C61—C66 | 118.81 (18) |
C7—C6—C5 | 120.1 (2) | C62—C61—P5 | 118.32 (15) |
C8—C7—C6 | 120.3 (2) | C66—C61—P5 | 122.83 (15) |
C7—C8—C9 | 120.1 (2) | C61—C62—C63 | 120.3 (2) |
C8—C9—C4 | 119.8 (2) | C64—C63—C62 | 120.0 (2) |
C15—C10—C11 | 119.31 (19) | C63—C64—C65 | 120.46 (19) |
C15—C10—P1 | 124.32 (15) | C64—C65—C66 | 119.7 (2) |
C11—C10—P1 | 116.33 (16) | C65—C66—C61 | 120.68 (19) |
C12—C11—C10 | 120.1 (2) | C68—C67—C72 | 118.86 (19) |
C13—C12—C11 | 120.3 (2) | C68—C67—P6 | 123.12 (16) |
C12—C13—C14 | 119.7 (2) | C72—C67—P6 | 117.97 (15) |
C13—C14—C15 | 120.5 (2) | C69—C68—C67 | 120.0 (2) |
C10—C15—C14 | 120.1 (2) | C70—C69—C68 | 120.6 (2) |
C17—C16—C21 | 119.3 (2) | C71—C70—C69 | 119.7 (2) |
C17—C16—P2 | 123.95 (17) | C70—C71—C72 | 120.4 (2) |
C21—C16—P2 | 116.76 (18) | C71—C72—C67 | 120.5 (2) |
C16—C17—C18 | 120.2 (2) | C78—C73—C74 | 119.0 (2) |
C19—C18—C17 | 120.0 (2) | C78—C73—P6 | 119.46 (17) |
C18—C19—C20 | 120.4 (2) | C74—C73—P6 | 121.34 (17) |
C19—C20—C21 | 119.8 (2) | C75—C74—C73 | 120.5 (2) |
C20—C21—C16 | 120.3 (2) | C76—C75—C74 | 119.4 (3) |
C23—C22—C27 | 119.4 (2) | C77—C76—C75 | 120.6 (3) |
C23—C22—P2 | 122.79 (17) | C76—C77—C78 | 120.5 (3) |
C27—C22—P2 | 117.78 (19) | C73—C78—C77 | 120.0 (3) |
Funding information
Funding for this research was provided by: Joint Research Centre.
References
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