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Acta Cryst. (2007). E63, m2289    [ doi:10.1107/S1600536807037439 ]

Bis([mu]-diphenylamido-[kappa]2N:N)bis[tris(tetrahydrofuran-[kappa]O)potassium(I)]

M. Gärtner, H. Görls and M. Westerhausen

Abstract top

The title compound, [K2(C4H8O)6(C12H10N)2], contains two K atoms which are coordinated by two bridging diphenylamide ligands to yield a centrosymmetric four-membered KNKN ring. Each K atom is additionally coordinated by three molecules of tetrahydrofuran, yielding a square pyramid in which one tetrahydrofuran molecule occupies the apical position. One CH2 group and four H atoms are disordered equally over two positions.

Comment top

One the one hand, potassium diphenylamide has been used for the synthesis of various transition metal diphenylamides, for example those of Cr (Seidel & Reichardt, 1974), Pd (Villanueva et al., 1994), Th (Barnhart et al., 1995), Nb (Tayebani et al., 1998), Y and Sm (Gamer et al., 2001), Yb (Hitchcock et al., 2002), and Re (Hevia et al., 2002). On the other hand, lactones and α,β-unsaturated cycloketones (Longi et al., 1965), octamethylcyclotetrasiloxane (Kucera & Jelinek, 1959), and isocyanates (Grogler & Windemuth, 1966) could be polymerized with potassium diphenylamide as a catalyst. Though this compound is often cited in literature (Barnhart et al., 1995; Bergstrom et al., 1942; Cheshko & Goncharenko, 1971; Fröhlich, 1975), neither an exact synthetic approach nor structural or spectroscopic data have been published. Here we present a straightforward synthesis of potassium diphenylamide and the first molecular structure of a simple potassium amide. KNPh2 was made of potassium and diphenylamine in boiling THF. Cooling a solution to −90 °C led to the formation of single crystals of (thf)3K(µ2-NPh2)2K(thf)3. In the crystalline state, potassium diphenylamide forms a dimeric centrosymmetric molecule with a four-membered KNKiNi ring [symmetry code: (i) 2 − x, 1 − y, −z]. Additionally, each K atom is saturated with three THF molecules. The coordination sphere of K is square-pyramidal with O2 occupying the apical position and N1, N1i, O1, and O3 lying on the basal positions.

Related literature top

Synthesis of various transition metal diphenylamides: Seidel & Reichardt (1974); Villanueva et al. (1994); Barnhart et al. (1995); Tayebani et al. (1998); Gamer et al. (2001); Hitchcock et al. (2002); Hevia et al. (2002). Potassium diphenylamide as a catalyst in polymerization reactions: Longi et al. (1965); Kucera & Jelinek (1959); Grogler & Windemuth (1966). Synthesis of the title compound: Barnhart et al. (1995); Bergstrom et al. (1942); Cheshko & Goncharenko (1971); Fröhlich (1975).

Experimental top

All manipulations were carried out in an atmosphere of argon using standard Schlenk techniques. THF was dried (Na/benzophenone) and distilled prior to use. K and diphenylamine were purchased form Aldrich. 1H NMR and 13C NMR spectra were recorded at [D8]THF solution at ambient temperature on a Bruker AC 400 MHz s pectrometer and were referenced to deuterated THF as an internal standard. A suspension of potassium (4.4 g, 112.5 mmol) and diphenylamine (15.2 g, 90.0 mmol, 0.8 eq.) in THF (100 ml) was heated under reflux for 2 h. Thereafter the suspension was cooled to ambient temperature and the excess of K was removed by filtation. The yield of 92% was determined by acidic titration of an hydrolysed aliquot. Cooling of this solution to −90 °C yields single crystals within 12 h, which were suitable for X-ray diffraction studies. Physical data: Mp: 100 °C (decomposition). 1H NMR (400 MHz) δ 1.77 (thf), 3.60 (thf), 6.12–6.18 (m, 4H), 6.85–6.87 (m, 16H). 13C NMR (100 MHz) δ 25.2 (thf), 67.3 (thf), 112.1 (4 C, p–C), 118.0 (8 C, o–C), 129.7 (8 C, m–C), 158.5 (4 C, i–C).

Refinement top

All hydrogen atoms were calculated at idealized positions with Caromatic—H = 0.95Å or C-methylene-H = 0.99Å and were refined with 1.5 times the isotropic displacement parameter of the corresponding carbon atoms. The tetrahydrofuran carbon atom C15 has a 50:50 occupancy disorder over two positions. Although the other tetrahedrofuran carbon atoms show high values for U(eq) no disorder could be resolved.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoides and the atom-numbering scheme. H atoms have been omitted for clarity.
Bis(µ-diphenylamido-κ2N:N)bis[tris(tetrahydrofuran-κO)potassium(I)] top
Crystal data top
[K2(C4H8O)6(C12H10N)2]F000 = 912
Mr = 847.24Dx = 1.178 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15517 reflections
a = 9.6546 (3) Åθ = 2.8–27.5º
b = 13.9660 (8) ŵ = 0.25 mm−1
c = 17.7356 (9) ÅT = 183 (2) K
β = 92.639 (3)ºPrism, colourless
V = 2388.9 (2) Å30.05 × 0.05 × 0.04 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer		5438 independent reflections
Radiation source: fine-focus sealed tube3612 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.050
T = 183(2) Kθmax = 27.5º
φ and ω scansθmin = 2.8º
Absorption correction: multi-scan
(Blessing, 1995)		h = −10→12
Tmin = 0.977, Tmax = 0.997k = −18→15
15517 measured reflectionsl = −23→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.169  w = 1/[σ2(Fo2) + (0.0746P)2 + 1.881P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
5438 reflectionsΔρmax = 0.39 e Å−3
261 parametersΔρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[K2(C4H8O)6(C12H10N)2]V = 2388.9 (2) Å3
Mr = 847.24Z = 2
Monoclinic, P21/cMo Kα
a = 9.6546 (3) ŵ = 0.25 mm−1
b = 13.9660 (8) ÅT = 183 (2) K
c = 17.7356 (9) Å0.05 × 0.05 × 0.04 mm
β = 92.639 (3)º
Data collection top
Nonius KappaCCD
diffractometer		5438 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		3612 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.997Rint = 0.050
15517 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060261 parameters
wR(F2) = 0.169H-atom parameters constrained
S = 0.95Δρmax = 0.39 e Å−3
5438 reflectionsΔρmin = −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
xyzUiso*/UeqOcc. (<1)
K10.93906 (6)0.41278 (4)0.08773 (3)0.04375 (18)
O10.7561 (2)0.26550 (15)0.09945 (12)0.0612 (6)
O21.1232 (2)0.3131 (2)0.17851 (13)0.0791 (7)
O30.8091 (2)0.48090 (16)0.20882 (12)0.0649 (6)
N11.0160 (2)0.60408 (14)0.06975 (11)0.0385 (5)
C10.9378 (2)0.68619 (17)0.06408 (12)0.0353 (5)
C20.7919 (3)0.67893 (18)0.07046 (14)0.0401 (6)
H2A0.75300.61910.08360.048*
C30.7053 (3)0.7565 (2)0.05804 (14)0.0456 (6)
H3A0.60820.74870.06240.055*
C40.7564 (3)0.8449 (2)0.03953 (15)0.0482 (6)
H4A0.69600.89790.03130.058*
C50.8984 (3)0.8547 (2)0.03313 (15)0.0473 (6)
H5A0.93550.91520.02010.057*
C60.9866 (3)0.77787 (19)0.04540 (14)0.0414 (6)
H6A1.08330.78710.04110.050*
C71.1538 (2)0.60788 (17)0.09161 (13)0.0376 (5)
C81.2149 (3)0.6754 (2)0.14269 (14)0.0451 (6)
H8A1.15910.72480.16220.054*
C91.3538 (3)0.6710 (2)0.16476 (17)0.0548 (7)
H9A1.39120.71750.19900.066*
C101.4393 (3)0.6009 (2)0.13837 (18)0.0574 (8)
H10A1.53490.59920.15360.069*
C111.3826 (3)0.5329 (2)0.08893 (17)0.0518 (7)
H11A1.43980.48380.07020.062*
C121.2436 (3)0.53584 (19)0.06666 (14)0.0424 (6)
H12A1.20720.48780.03340.051*
C130.6390 (3)0.2422 (2)0.05079 (19)0.0605 (8)
H13A0.65490.2623−0.00160.073*
H13B0.55480.27480.06770.073*
C140.6220 (5)0.1361 (3)0.0549 (3)0.1017 (15)
H14A0.53620.11910.08020.122*0.50
H14B0.61850.10750.00370.122*0.50
H14C0.52260.11860.05320.122*0.50
H14D0.66650.10460.01220.122*0.50
C150.7479 (10)0.1027 (7)0.1000 (6)0.091 (3)*0.50
H15A0.72100.05570.13850.109*0.50
H15B0.81360.07140.06660.109*0.50
C15A0.6902 (7)0.1071 (5)0.1273 (4)0.0568 (15)*0.50
H15C0.72620.04080.12520.068*0.50
H15D0.62670.11260.16940.068*0.50
C160.8095 (4)0.1814 (2)0.13461 (19)0.0685 (9)
H16A0.91120.17850.13010.082*0.50
H16B0.78990.18190.18890.082*0.50
H16C0.83590.19360.18830.082*0.50
H16D0.89200.15820.10890.082*0.50
C171.2484 (4)0.2853 (2)0.14584 (18)0.0630 (8)
H17A1.26640.32620.10180.076*
H17B1.24270.21780.12890.076*
C181.3586 (4)0.2967 (4)0.2044 (2)0.0874 (12)
H18A1.37320.23650.23310.105*
H18B1.44680.31520.18200.105*
C191.3105 (5)0.3717 (3)0.2526 (2)0.0923 (14)
H19A1.33120.43580.23200.111*
H19B1.35280.36630.30430.111*
C201.1599 (5)0.3541 (4)0.2516 (2)0.1056 (17)
H20A1.13710.30910.29240.127*
H20B1.10910.41470.25870.127*
C210.7134 (4)0.4283 (3)0.2490 (2)0.0849 (11)
H21A0.73620.35920.24790.102*
H21B0.61850.43730.22660.102*
C220.7228 (6)0.4653 (4)0.3292 (3)0.1159 (18)
H22A0.72290.41190.36590.139*
H22B0.64470.50890.33880.139*
C230.8591 (6)0.5181 (3)0.3334 (2)0.0988 (15)
H23A0.85740.57180.36980.119*
H23B0.93670.47460.34810.119*
C240.8709 (4)0.5535 (3)0.2550 (2)0.0758 (10)
H24A0.82110.61500.24760.091*
H24B0.96930.56280.24330.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0544 (4)0.0404 (3)0.0360 (3)−0.0079 (3)−0.0027 (2)0.0040 (2)
O10.0723 (14)0.0476 (12)0.0624 (13)−0.0130 (10)−0.0101 (10)0.0041 (10)
O20.0575 (13)0.122 (2)0.0572 (14)0.0033 (13)−0.0079 (10)0.0204 (14)
O30.0830 (15)0.0614 (13)0.0510 (12)−0.0142 (11)0.0104 (10)−0.0085 (10)
N10.0393 (11)0.0356 (11)0.0404 (11)−0.0056 (8)−0.0010 (8)−0.0034 (9)
C10.0412 (13)0.0376 (13)0.0271 (11)−0.0048 (10)0.0001 (9)−0.0035 (9)
C20.0425 (13)0.0396 (14)0.0382 (13)−0.0068 (11)0.0003 (10)−0.0015 (10)
C30.0423 (14)0.0528 (16)0.0415 (14)0.0012 (12)−0.0016 (10)−0.0049 (12)
C40.0566 (17)0.0420 (15)0.0451 (15)0.0080 (12)−0.0068 (12)−0.0009 (12)
C50.0627 (17)0.0390 (15)0.0399 (14)−0.0062 (12)−0.0028 (12)0.0009 (11)
C60.0464 (14)0.0422 (14)0.0358 (13)−0.0076 (11)0.0024 (10)−0.0009 (11)
C70.0410 (13)0.0397 (14)0.0322 (12)−0.0056 (10)0.0029 (9)0.0035 (10)
C80.0460 (15)0.0482 (15)0.0407 (14)−0.0059 (11)−0.0008 (11)−0.0037 (11)
C90.0495 (16)0.0614 (19)0.0526 (17)−0.0123 (14)−0.0078 (12)0.0009 (14)
C100.0407 (15)0.066 (2)0.0649 (19)−0.0081 (14)−0.0023 (13)0.0171 (16)
C110.0483 (16)0.0523 (17)0.0556 (17)0.0054 (13)0.0112 (12)0.0158 (13)
C120.0494 (15)0.0396 (14)0.0384 (13)0.0001 (11)0.0039 (10)0.0050 (11)
C130.0472 (16)0.070 (2)0.0640 (19)−0.0076 (14)0.0014 (13)0.0084 (16)
C140.115 (3)0.075 (3)0.112 (3)−0.039 (2)−0.035 (3)0.002 (2)
C160.084 (2)0.065 (2)0.0558 (19)−0.0097 (17)−0.0108 (16)0.0130 (16)
C170.082 (2)0.0509 (18)0.0555 (18)0.0011 (16)0.0028 (16)−0.0037 (14)
C180.067 (2)0.126 (4)0.069 (2)−0.008 (2)−0.0059 (18)0.003 (2)
C190.136 (4)0.094 (3)0.046 (2)−0.045 (3)0.000 (2)−0.0012 (19)
C200.127 (4)0.144 (4)0.047 (2)0.074 (3)0.014 (2)0.005 (2)
C210.090 (3)0.088 (3)0.079 (3)−0.014 (2)0.019 (2)0.010 (2)
C220.155 (5)0.114 (4)0.084 (3)0.012 (4)0.062 (3)0.011 (3)
C230.153 (4)0.089 (3)0.054 (2)0.034 (3)−0.007 (2)−0.011 (2)
C240.101 (3)0.061 (2)0.065 (2)−0.0071 (19)−0.0024 (19)−0.0148 (17)
Geometric parameters (Å, °) top
K1—O32.709 (2)C12—K1i3.268 (3)
K1—O22.725 (2)C12—H12A0.9500
K1—O12.726 (2)C13—C141.492 (5)
K1—N12.795 (2)C13—H13A0.9900
K1—N1i2.856 (2)C13—H13B0.9900
K1—C12i3.268 (3)C14—C15A1.474 (8)
K1—C7i3.277 (2)C14—C151.499 (10)
K1—C1i3.297 (2)C14—H14A0.9900
K1—C73.423 (2)C14—H14B0.9900
K1—C123.441 (3)C14—H14C0.9900
K1—K1i4.1643 (11)C14—H14D0.9900
O1—C161.416 (4)C15—C161.380 (10)
O1—C131.428 (4)C15—H15A0.9900
O2—C171.418 (4)C15—H15B0.9900
O2—C201.446 (5)C15A—C161.551 (7)
O3—C211.401 (4)C15A—H15C0.9900
O3—C241.418 (4)C15A—H15D0.9900
N1—C71.370 (3)C16—H16A0.9900
N1—C11.374 (3)C16—H16B0.9900
N1—K1i2.856 (2)C16—H16C0.9900
C1—C61.409 (3)C16—H16D0.9900
C1—C21.422 (3)C17—C181.461 (5)
C1—K1i3.297 (2)C17—H17A0.9900
C2—C31.380 (4)C17—H17B0.9900
C2—H2A0.9500C18—C191.442 (6)
C3—C41.375 (4)C18—H18A0.9900
C3—H3A0.9500C18—H18B0.9900
C4—C51.387 (4)C19—C201.473 (6)
C4—H4A0.9500C19—H19A0.9900
C5—C61.381 (4)C19—H19B0.9900
C5—H5A0.9500C20—H20A0.9900
C6—H6A0.9500C20—H20B0.9900
C7—C81.418 (3)C21—C221.511 (6)
C7—C121.412 (4)C21—H21A0.9900
C7—K1i3.277 (2)C21—H21B0.9900
C8—C91.380 (4)C22—C231.508 (7)
C8—H8A0.9500C22—H22A0.9900
C9—C101.377 (4)C22—H22B0.9900
C9—H9A0.9500C23—C241.486 (5)
C10—C111.389 (4)C23—H23A0.9900
C10—H10A0.9500C23—H23B0.9900
C11—C121.381 (4)C24—H24A0.9900
C11—H11A0.9500C24—H24B0.9900
O3—K1—O291.40 (8)C11—C12—K1141.01 (18)
O3—K1—O183.05 (7)C7—C12—K177.40 (14)
O2—K1—O188.67 (7)K1i—C12—K176.69 (6)
O3—K1—N183.69 (6)C11—C12—H12A118.9
O2—K1—N1112.72 (7)C7—C12—H12A118.9
O1—K1—N1155.04 (7)K1i—C12—H12A57.7
O3—K1—N1i154.28 (7)K1—C12—H12A54.6
O2—K1—N1i114.29 (7)O1—C13—C14106.4 (3)
O1—K1—N1i98.08 (6)O1—C13—H13A110.4
N1—K1—N1i85.07 (6)C14—C13—H13A110.4
O3—K1—C12i109.59 (7)O1—C13—H13B110.4
O2—K1—C12i156.84 (8)C14—C13—H13B110.4
O1—K1—C12i84.43 (6)H13A—C13—H13B108.6
N1—K1—C12i80.24 (6)C15A—C14—C1529.5 (4)
N1i—K1—C12i45.49 (6)C15A—C14—C13105.6 (4)
O3—K1—C7i133.17 (7)C15—C14—C13104.3 (4)
O2—K1—C7i132.08 (8)C15A—C14—H14A83.5
O1—K1—C7i81.85 (6)C15—C14—H14A110.9
N1—K1—C7i92.05 (6)C13—C14—H14A110.9
N1i—K1—C7i24.59 (6)C15A—C14—H14B133.0
C12i—K1—C7i24.92 (6)C15—C14—H14B110.9
O3—K1—C1i172.86 (6)C13—C14—H14B110.9
O2—K1—C1i91.05 (7)H14A—C14—H14B108.9
O1—K1—C1i90.30 (6)C15A—C14—H14C110.6
N1—K1—C1i101.53 (6)C15—C14—H14C134.4
N1i—K1—C1i24.49 (6)C13—C14—H14C110.6
C12i—K1—C1i66.97 (6)H14A—C14—H14C28.8
C7i—K1—C1i42.55 (6)H14B—C14—H14C83.1
O3—K1—C790.39 (6)C15A—C14—H14D110.6
O2—K1—C790.97 (7)C15—C14—H14D84.3
O1—K1—C7173.42 (7)C13—C14—H14D110.6
N1—K1—C722.70 (6)H14A—C14—H14D129.9
N1i—K1—C788.06 (6)H14B—C14—H14D28.2
C12i—K1—C798.34 (6)H14C—C14—H14D108.7
C7i—K1—C7103.18 (5)C16—C15—C14108.1 (6)
C1i—K1—C796.27 (6)C16—C15—H15A110.1
O3—K1—C12109.88 (7)C14—C15—H15A110.1
O2—K1—C1277.41 (7)C16—C15—H15B110.1
O1—K1—C12160.97 (7)C14—C15—H15B110.1
N1—K1—C1243.72 (6)H15A—C15—H15B108.4
N1i—K1—C1276.47 (6)C14—C15A—C16100.9 (4)
C12i—K1—C12103.31 (6)C14—C15A—H15C111.6
C7i—K1—C1297.79 (6)C16—C15A—H15C111.6
C1i—K1—C1277.21 (6)C14—C15A—H15D111.6
C7—K1—C1223.75 (6)C16—C15A—H15D111.6
O3—K1—K1i122.96 (5)H15C—C15A—H15D109.4
O2—K1—K1i122.77 (6)C15—C16—O1108.9 (4)
O1—K1—K1i134.82 (5)C15—C16—C15A29.2 (4)
N1—K1—K1i43.10 (4)O1—C16—C15A105.3 (3)
N1i—K1—K1i41.97 (4)C15—C16—H16A109.9
C12i—K1—K1i53.53 (5)O1—C16—H16A109.9
C7i—K1—K1i53.16 (4)C15A—C16—H16A134.6
C1i—K1—K1i60.66 (4)C15—C16—H16B109.9
C7—K1—K1i50.02 (4)O1—C16—H16B109.9
C12—K1—K1i49.79 (4)C15A—C16—H16B84.9
C16—O1—C13109.8 (2)H16A—C16—H16B108.3
C16—O1—K1115.80 (18)C15—C16—H16C130.7
C13—O1—K1128.60 (18)O1—C16—H16C110.7
C17—O2—C20107.2 (3)C15A—C16—H16C110.7
C17—O2—K1116.32 (18)H16A—C16—H16C82.7
C20—O2—K1117.0 (2)H16B—C16—H16C27.7
C21—O3—C24110.6 (3)C15—C16—H16D82.8
C21—O3—K1124.0 (2)O1—C16—H16D110.7
C24—O3—K1120.7 (2)C15A—C16—H16D110.7
C7—N1—C1120.8 (2)H16A—C16—H16D29.2
C7—N1—K1105.35 (14)H16B—C16—H16D130.1
C1—N1—K1131.14 (15)H16C—C16—H16D108.8
C7—N1—K1i95.21 (14)O2—C17—C18106.6 (3)
C1—N1—K1i96.02 (14)O2—C17—H17A110.4
K1—N1—K1i94.93 (6)C18—C17—H17A110.4
N1—C1—C6126.0 (2)O2—C17—H17B110.4
N1—C1—C2118.5 (2)C18—C17—H17B110.4
C6—C1—C2115.2 (2)H17A—C17—H17B108.6
N1—C1—K1i59.49 (12)C19—C18—C17104.8 (4)
C6—C1—K1i92.98 (14)C19—C18—H18A110.8
C2—C1—K1i115.53 (15)C17—C18—H18A110.8
C3—C2—C1121.8 (2)C19—C18—H18B110.8
C3—C2—H2A119.1C17—C18—H18B110.8
C1—C2—H2A119.1H18A—C18—H18B108.9
C4—C3—C2121.4 (2)C18—C19—C20102.5 (3)
C4—C3—H3A119.3C18—C19—H19A111.3
C2—C3—H3A119.3C20—C19—H19A111.3
C3—C4—C5118.4 (3)C18—C19—H19B111.3
C3—C4—H4A120.8C20—C19—H19B111.3
C5—C4—H4A120.8H19A—C19—H19B109.2
C6—C5—C4121.0 (3)O2—C20—C19106.1 (3)
C6—C5—H5A119.5O2—C20—H20A110.5
C4—C5—H5A119.5C19—C20—H20A110.5
C5—C6—C1122.2 (2)O2—C20—H20B110.5
C5—C6—H6A118.9C19—C20—H20B110.5
C1—C6—H6A118.9H20A—C20—H20B108.7
N1—C7—C8125.2 (2)O3—C21—C22106.7 (4)
N1—C7—C12119.1 (2)O3—C21—H21A110.4
C8—C7—C12115.5 (2)C22—C21—H21A110.4
N1—C7—K1i60.20 (12)O3—C21—H21B110.4
C8—C7—K1i140.00 (17)C22—C21—H21B110.4
C12—C7—K1i77.16 (14)H21A—C21—H21B108.6
N1—C7—K151.96 (12)C21—C22—C23103.2 (3)
C8—C7—K1140.94 (17)C21—C22—H22A111.1
C12—C7—K178.85 (14)C23—C22—H22A111.1
K1i—C7—K176.82 (5)C21—C22—H22B111.1
C9—C8—C7121.4 (3)C23—C22—H22B111.1
C9—C8—H8A119.3H22A—C22—H22B109.1
C7—C8—H8A119.3C24—C23—C22102.7 (4)
C10—C9—C8121.7 (3)C24—C23—H23A111.2
C10—C9—H9A119.1C22—C23—H23A111.2
C8—C9—H9A119.1C24—C23—H23B111.2
C9—C10—C11118.4 (3)C22—C23—H23B111.2
C9—C10—H10A120.8H23A—C23—H23B109.1
C11—C10—H10A120.8O3—C24—C23104.7 (3)
C12—C11—C10120.6 (3)O3—C24—H24A110.8
C12—C11—H11A119.7C23—C24—H24A110.8
C10—C11—H11A119.7O3—C24—H24B110.8
C11—C12—C7122.3 (3)C23—C24—H24B110.8
C11—C12—K1i136.53 (17)H24A—C24—H24B108.9
C7—C12—K1i77.91 (14)
Symmetry codes: (i) −x+2, −y+1, −z.
Acknowledgements top

We thank the Deutsche Forschungsgemeinschaft (DFG, Bonn–Band Godesberg, Germany) for generous financial support. We also acknowledge the funding of the Fonds der Chemischen Industrie (Frankfurt/Main, Germany). In addition, MG is very grateful to the Verband der Chemischen Industrie (VCI/FCI) for a scholarship.

references
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