N,N,N-Tris(di­phenyl­phospho­rylmeth­yl)amine

Walter, O.

doi:10.1107/S2414314617014791

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171479

https://doi.org/10.1107/S2414314617014791

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N,N,N-Tris(diphenylphosphorylmethyl)amine

Olaf Walter ^a ^*

^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

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 29 September 2017; accepted 12 October 2017; online 20 October 2017)

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 asymmetric unit of the monoclinic unit cell. 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

Phosphine oxides act as ligands for stabilizing oxophilic metal ions via complex formation. Many complexes of phosphine oxides 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 ).

In the crystal structure of N,N,N-tris(diphenylphosphorylmethyl)amine, the two molecules in the asymmetric unit 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.

Figure 1
View of the molecular structure of one of the molecules of N,N,N-tris(diphenylphosphorylmethyl)amine in the asymmetric unit, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
View along the pseudo-threefold rotation axis of one of the N,N,N-tris(diphenylphosphorylmethyl)amine molecules present in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.

There 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).

Figure 3
The preparation of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms attached to C atoms were fixed geometrically with fixed bond lengths and refined isotropically using a riding model.

Table 1
Experimental details

Crystal data
Chemical formula	C₃₉H₃₆NO₃P₃
M_r	659.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	103
a, b, c (Å)	10.9219 (10), 25.078 (2), 24.870 (2)
β (°)	95.515 (1)
V (Å³)	6780.3 (10)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.22
Crystal size (mm)	0.10 × 0.07 × 0.05

Data collection
Diffractometer	Bruker APEXII Quazar
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.953, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	122037, 16105, 11728
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.109, 1.01
No. of reflections	16105
No. of parameters	843
H-atom treatment	Only H-atom displacement parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2007), SHELXS2013 (Sheldrick, 2008 ), SHELXL2017 (Sheldrick, 2015 ), XPMA (Zsolnai, 1996 ), ORTEP-3 for Windows (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1579667

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014791/vm4029sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

N,N,N-Tris(diphenylphosphorylmethyl)amine top

Crystal data top

C₃₉H₃₆NO₃P₃	F(000) = 2768
M_r = 659.60	D_x = 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

Data collection top

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	R_int = 0.061
combined ω– and phi–scan	θ_max = 28.3°, θ_min = 1.2°
Absorption correction: multi-scan (sadabs)	h = −14→14
T_min = 0.953, T_max = 0.99	k = −33→32
122037 measured reflections	l = −33→32

Refinement top

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(F_o²) + (0.0396P)² + 5.4914P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
16105 reflections	Δρ_max = 0.45 e Å⁻³
843 parameters	Δρ_min = −0.40 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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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