Bis(μ-diphenyl­amido-κ²N:N)bis­[tris­(tetra­hydro­furan-κO)potassium(I)]

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.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.169
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C14

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         K1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C15A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.24 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.50 Deg.
              C15A -C14  -C15     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.80 Deg.
              H14A -C14  -H14C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.20 Deg.
              H14B -C14  -H14D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.20 Deg.
              C15  -C16  -C15A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.70 Deg.
              H16B -C16  -H16C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.20 Deg.
              H16A -C16  -H16D    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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).

S3. Refinement

All hydrogen atoms were calculated at idealized positions with C_aromatic—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

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

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)]

Crystal data

[K2(C4H8O)6(C12H10N)2]	F(000) = 912
Mr = 847.24	Dx = 1.178 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15517 reflections
a = 9.6546 (3) Å	θ = 2.8–27.5°
b = 13.9660 (8) Å	µ = 0.25 mm^−1
c = 17.7356 (9) Å	T = 183 K
β = 92.639 (3)°	Prism, colourless
V = 2388.9 (2) Å^3	0.05 × 0.05 × 0.04 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	5438 independent reflections
Radiation source: fine-focus sealed tube	3612 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→12
Tmin = 0.977, Tmax = 0.997	k = −18→15
15517 measured reflections	l = −23→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0746P)^2 + 1.881P] where P = (Fo^2 + 2Fc^2)/3
5438 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
K1	0.93906 (6)	0.41278 (4)	0.08773 (3)	0.04375 (18)
O1	0.7561 (2)	0.26550 (15)	0.09945 (12)	0.0612 (6)
O2	1.1232 (2)	0.3131 (2)	0.17851 (13)	0.0791 (7)
O3	0.8091 (2)	0.48090 (16)	0.20882 (12)	0.0649 (6)
N1	1.0160 (2)	0.60408 (14)	0.06975 (11)	0.0385 (5)
C1	0.9378 (2)	0.68619 (17)	0.06408 (12)	0.0353 (5)
C2	0.7919 (3)	0.67893 (18)	0.07046 (14)	0.0401 (6)
H2A	0.7530	0.6191	0.0836	0.048*
C3	0.7053 (3)	0.7565 (2)	0.05804 (14)	0.0456 (6)
H3A	0.6082	0.7487	0.0624	0.055*
C4	0.7564 (3)	0.8449 (2)	0.03953 (15)	0.0482 (6)
H4A	0.6960	0.8979	0.0313	0.058*
C5	0.8984 (3)	0.8547 (2)	0.03313 (15)	0.0473 (6)
H5A	0.9355	0.9152	0.0201	0.057*
C6	0.9866 (3)	0.77787 (19)	0.04540 (14)	0.0414 (6)
H6A	1.0833	0.7871	0.0411	0.050*
C7	1.1538 (2)	0.60788 (17)	0.09161 (13)	0.0376 (5)
C8	1.2149 (3)	0.6754 (2)	0.14269 (14)	0.0451 (6)
H8A	1.1591	0.7248	0.1622	0.054*
C9	1.3538 (3)	0.6710 (2)	0.16476 (17)	0.0548 (7)
H9A	1.3912	0.7175	0.1990	0.066*
C10	1.4393 (3)	0.6009 (2)	0.13837 (18)	0.0574 (8)
H10A	1.5349	0.5992	0.1536	0.069*
C11	1.3826 (3)	0.5329 (2)	0.08893 (17)	0.0518 (7)
H11A	1.4398	0.4838	0.0702	0.062*
C12	1.2436 (3)	0.53584 (19)	0.06666 (14)	0.0424 (6)
H12A	1.2072	0.4878	0.0334	0.051*
C13	0.6390 (3)	0.2422 (2)	0.05079 (19)	0.0605 (8)
H13A	0.6549	0.2623	−0.0016	0.073*
H13B	0.5548	0.2748	0.0677	0.073*
C14	0.6220 (5)	0.1361 (3)	0.0549 (3)	0.1017 (15)
H14A	0.5362	0.1191	0.0802	0.122*	0.50
H14B	0.6185	0.1075	0.0037	0.122*	0.50
H14C	0.5226	0.1186	0.0532	0.122*	0.50
H14D	0.6665	0.1046	0.0122	0.122*	0.50
C15	0.7479 (10)	0.1027 (7)	0.1000 (6)	0.091 (3)*	0.50
H15A	0.7210	0.0557	0.1385	0.109*	0.50
H15B	0.8136	0.0714	0.0666	0.109*	0.50
C15A	0.6902 (7)	0.1071 (5)	0.1273 (4)	0.0568 (15)*	0.50
H15C	0.7262	0.0408	0.1252	0.068*	0.50
H15D	0.6267	0.1126	0.1694	0.068*	0.50
C16	0.8095 (4)	0.1814 (2)	0.13461 (19)	0.0685 (9)
H16A	0.9112	0.1785	0.1301	0.082*	0.50
H16B	0.7899	0.1819	0.1889	0.082*	0.50
H16C	0.8359	0.1936	0.1883	0.082*	0.50
H16D	0.8920	0.1582	0.1089	0.082*	0.50
C17	1.2484 (4)	0.2853 (2)	0.14584 (18)	0.0630 (8)
H17A	1.2664	0.3262	0.1018	0.076*
H17B	1.2427	0.2178	0.1289	0.076*
C18	1.3586 (4)	0.2967 (4)	0.2044 (2)	0.0874 (12)
H18A	1.3732	0.2365	0.2331	0.105*
H18B	1.4468	0.3152	0.1820	0.105*
C19	1.3105 (5)	0.3717 (3)	0.2526 (2)	0.0923 (14)
H19A	1.3312	0.4358	0.2320	0.111*
H19B	1.3528	0.3663	0.3043	0.111*
C20	1.1599 (5)	0.3541 (4)	0.2516 (2)	0.1056 (17)
H20A	1.1371	0.3091	0.2924	0.127*
H20B	1.1091	0.4147	0.2587	0.127*
C21	0.7134 (4)	0.4283 (3)	0.2490 (2)	0.0849 (11)
H21A	0.7362	0.3592	0.2479	0.102*
H21B	0.6185	0.4373	0.2266	0.102*
C22	0.7228 (6)	0.4653 (4)	0.3292 (3)	0.1159 (18)
H22A	0.7229	0.4119	0.3659	0.139*
H22B	0.6447	0.5089	0.3388	0.139*
C23	0.8591 (6)	0.5181 (3)	0.3334 (2)	0.0988 (15)
H23A	0.8574	0.5718	0.3698	0.119*
H23B	0.9367	0.4746	0.3481	0.119*
C24	0.8709 (4)	0.5535 (3)	0.2550 (2)	0.0758 (10)
H24A	0.8211	0.6150	0.2476	0.091*
H24B	0.9693	0.5628	0.2433	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0544 (4)	0.0404 (3)	0.0360 (3)	−0.0079 (3)	−0.0027 (2)	0.0040 (2)
O1	0.0723 (14)	0.0476 (12)	0.0624 (13)	−0.0130 (10)	−0.0101 (10)	0.0041 (10)
O2	0.0575 (13)	0.122 (2)	0.0572 (14)	0.0033 (13)	−0.0079 (10)	0.0204 (14)
O3	0.0830 (15)	0.0614 (13)	0.0510 (12)	−0.0142 (11)	0.0104 (10)	−0.0085 (10)
N1	0.0393 (11)	0.0356 (11)	0.0404 (11)	−0.0056 (8)	−0.0010 (8)	−0.0034 (9)
C1	0.0412 (13)	0.0376 (13)	0.0271 (11)	−0.0048 (10)	0.0001 (9)	−0.0035 (9)
C2	0.0425 (13)	0.0396 (14)	0.0382 (13)	−0.0068 (11)	0.0003 (10)	−0.0015 (10)
C3	0.0423 (14)	0.0528 (16)	0.0415 (14)	0.0012 (12)	−0.0016 (10)	−0.0049 (12)
C4	0.0566 (17)	0.0420 (15)	0.0451 (15)	0.0080 (12)	−0.0068 (12)	−0.0009 (12)
C5	0.0627 (17)	0.0390 (15)	0.0399 (14)	−0.0062 (12)	−0.0028 (12)	0.0009 (11)
C6	0.0464 (14)	0.0422 (14)	0.0358 (13)	−0.0076 (11)	0.0024 (10)	−0.0009 (11)
C7	0.0410 (13)	0.0397 (14)	0.0322 (12)	−0.0056 (10)	0.0029 (9)	0.0035 (10)
C8	0.0460 (15)	0.0482 (15)	0.0407 (14)	−0.0059 (11)	−0.0008 (11)	−0.0037 (11)
C9	0.0495 (16)	0.0614 (19)	0.0526 (17)	−0.0123 (14)	−0.0078 (12)	0.0009 (14)
C10	0.0407 (15)	0.066 (2)	0.0649 (19)	−0.0081 (14)	−0.0023 (13)	0.0171 (16)
C11	0.0483 (16)	0.0523 (17)	0.0556 (17)	0.0054 (13)	0.0112 (12)	0.0158 (13)
C12	0.0494 (15)	0.0396 (14)	0.0384 (13)	0.0001 (11)	0.0039 (10)	0.0050 (11)
C13	0.0472 (16)	0.070 (2)	0.0640 (19)	−0.0076 (14)	0.0014 (13)	0.0084 (16)
C14	0.115 (3)	0.075 (3)	0.112 (3)	−0.039 (2)	−0.035 (3)	0.002 (2)
C16	0.084 (2)	0.065 (2)	0.0558 (19)	−0.0097 (17)	−0.0108 (16)	0.0130 (16)
C17	0.082 (2)	0.0509 (18)	0.0555 (18)	0.0011 (16)	0.0028 (16)	−0.0037 (14)
C18	0.067 (2)	0.126 (4)	0.069 (2)	−0.008 (2)	−0.0059 (18)	0.003 (2)
C19	0.136 (4)	0.094 (3)	0.046 (2)	−0.045 (3)	0.000 (2)	−0.0012 (19)
C20	0.127 (4)	0.144 (4)	0.047 (2)	0.074 (3)	0.014 (2)	0.005 (2)
C21	0.090 (3)	0.088 (3)	0.079 (3)	−0.014 (2)	0.019 (2)	0.010 (2)
C22	0.155 (5)	0.114 (4)	0.084 (3)	0.012 (4)	0.062 (3)	0.011 (3)
C23	0.153 (4)	0.089 (3)	0.054 (2)	0.034 (3)	−0.007 (2)	−0.011 (2)
C24	0.101 (3)	0.061 (2)	0.065 (2)	−0.0071 (19)	−0.0024 (19)	−0.0148 (17)

Geometric parameters (Å, º)

K1—O3	2.709 (2)	C12—K1^i	3.268 (3)
K1—O2	2.725 (2)	C12—H12A	0.9500
K1—O1	2.726 (2)	C13—C14	1.492 (5)
K1—N1	2.795 (2)	C13—H13A	0.9900
K1—N1^i	2.856 (2)	C13—H13B	0.9900
K1—C12^i	3.268 (3)	C14—C15A	1.474 (8)
K1—C7^i	3.277 (2)	C14—C15	1.499 (10)
K1—C1^i	3.297 (2)	C14—H14A	0.9900
K1—C7	3.423 (2)	C14—H14B	0.9900
K1—C12	3.441 (3)	C14—H14C	0.9900
K1—K1^i	4.1643 (11)	C14—H14D	0.9900
O1—C16	1.416 (4)	C15—C16	1.380 (10)
O1—C13	1.428 (4)	C15—H15A	0.9900
O2—C17	1.418 (4)	C15—H15B	0.9900
O2—C20	1.446 (5)	C15A—C16	1.551 (7)
O3—C21	1.401 (4)	C15A—H15C	0.9900
O3—C24	1.418 (4)	C15A—H15D	0.9900
N1—C7	1.370 (3)	C16—H16A	0.9900
N1—C1	1.374 (3)	C16—H16B	0.9900
N1—K1^i	2.856 (2)	C16—H16C	0.9900
C1—C6	1.409 (3)	C16—H16D	0.9900
C1—C2	1.422 (3)	C17—C18	1.461 (5)
C1—K1^i	3.297 (2)	C17—H17A	0.9900
C2—C3	1.380 (4)	C17—H17B	0.9900
C2—H2A	0.9500	C18—C19	1.442 (6)
C3—C4	1.375 (4)	C18—H18A	0.9900
C3—H3A	0.9500	C18—H18B	0.9900
C4—C5	1.387 (4)	C19—C20	1.473 (6)
C4—H4A	0.9500	C19—H19A	0.9900
C5—C6	1.381 (4)	C19—H19B	0.9900
C5—H5A	0.9500	C20—H20A	0.9900
C6—H6A	0.9500	C20—H20B	0.9900
C7—C8	1.418 (3)	C21—C22	1.511 (6)
C7—C12	1.412 (4)	C21—H21A	0.9900
C7—K1^i	3.277 (2)	C21—H21B	0.9900
C8—C9	1.380 (4)	C22—C23	1.508 (7)
C8—H8A	0.9500	C22—H22A	0.9900
C9—C10	1.377 (4)	C22—H22B	0.9900
C9—H9A	0.9500	C23—C24	1.486 (5)
C10—C11	1.389 (4)	C23—H23A	0.9900
C10—H10A	0.9500	C23—H23B	0.9900
C11—C12	1.381 (4)	C24—H24A	0.9900
C11—H11A	0.9500	C24—H24B	0.9900
O3—K1—O2	91.40 (8)	C11—C12—K1	141.01 (18)
O3—K1—O1	83.05 (7)	C7—C12—K1	77.40 (14)
O2—K1—O1	88.67 (7)	K1^i—C12—K1	76.69 (6)
O3—K1—N1	83.69 (6)	C11—C12—H12A	118.9
O2—K1—N1	112.72 (7)	C7—C12—H12A	118.9
O1—K1—N1	155.04 (7)	K1^i—C12—H12A	57.7
O3—K1—N1^i	154.28 (7)	K1—C12—H12A	54.6
O2—K1—N1^i	114.29 (7)	O1—C13—C14	106.4 (3)
O1—K1—N1^i	98.08 (6)	O1—C13—H13A	110.4
N1—K1—N1^i	85.07 (6)	C14—C13—H13A	110.4
O3—K1—C12^i	109.59 (7)	O1—C13—H13B	110.4
O2—K1—C12^i	156.84 (8)	C14—C13—H13B	110.4
O1—K1—C12^i	84.43 (6)	H13A—C13—H13B	108.6
N1—K1—C12^i	80.24 (6)	C15A—C14—C15	29.5 (4)
N1^i—K1—C12^i	45.49 (6)	C15A—C14—C13	105.6 (4)
O3—K1—C7^i	133.17 (7)	C15—C14—C13	104.3 (4)
O2—K1—C7^i	132.08 (8)	C15A—C14—H14A	83.5
O1—K1—C7^i	81.85 (6)	C15—C14—H14A	110.9
N1—K1—C7^i	92.05 (6)	C13—C14—H14A	110.9
N1^i—K1—C7^i	24.59 (6)	C15A—C14—H14B	133.0
C12^i—K1—C7^i	24.92 (6)	C15—C14—H14B	110.9
O3—K1—C1^i	172.86 (6)	C13—C14—H14B	110.9
O2—K1—C1^i	91.05 (7)	H14A—C14—H14B	108.9
O1—K1—C1^i	90.30 (6)	C15A—C14—H14C	110.6
N1—K1—C1^i	101.53 (6)	C15—C14—H14C	134.4
N1^i—K1—C1^i	24.49 (6)	C13—C14—H14C	110.6
C12^i—K1—C1^i	66.97 (6)	H14A—C14—H14C	28.8
C7^i—K1—C1^i	42.55 (6)	H14B—C14—H14C	83.1
O3—K1—C7	90.39 (6)	C15A—C14—H14D	110.6
O2—K1—C7	90.97 (7)	C15—C14—H14D	84.3
O1—K1—C7	173.42 (7)	C13—C14—H14D	110.6
N1—K1—C7	22.70 (6)	H14A—C14—H14D	129.9
N1^i—K1—C7	88.06 (6)	H14B—C14—H14D	28.2
C12^i—K1—C7	98.34 (6)	H14C—C14—H14D	108.7
C7^i—K1—C7	103.18 (5)	C16—C15—C14	108.1 (6)
C1^i—K1—C7	96.27 (6)	C16—C15—H15A	110.1
O3—K1—C12	109.88 (7)	C14—C15—H15A	110.1
O2—K1—C12	77.41 (7)	C16—C15—H15B	110.1
O1—K1—C12	160.97 (7)	C14—C15—H15B	110.1
N1—K1—C12	43.72 (6)	H15A—C15—H15B	108.4
N1^i—K1—C12	76.47 (6)	C14—C15A—C16	100.9 (4)
C12^i—K1—C12	103.31 (6)	C14—C15A—H15C	111.6
C7^i—K1—C12	97.79 (6)	C16—C15A—H15C	111.6
C1^i—K1—C12	77.21 (6)	C14—C15A—H15D	111.6
C7—K1—C12	23.75 (6)	C16—C15A—H15D	111.6
O3—K1—K1^i	122.96 (5)	H15C—C15A—H15D	109.4
O2—K1—K1^i	122.77 (6)	C15—C16—O1	108.9 (4)
O1—K1—K1^i	134.82 (5)	C15—C16—C15A	29.2 (4)
N1—K1—K1^i	43.10 (4)	O1—C16—C15A	105.3 (3)
N1^i—K1—K1^i	41.97 (4)	C15—C16—H16A	109.9
C12^i—K1—K1^i	53.53 (5)	O1—C16—H16A	109.9
C7^i—K1—K1^i	53.16 (4)	C15A—C16—H16A	134.6
C1^i—K1—K1^i	60.66 (4)	C15—C16—H16B	109.9
C7—K1—K1^i	50.02 (4)	O1—C16—H16B	109.9
C12—K1—K1^i	49.79 (4)	C15A—C16—H16B	84.9
C16—O1—C13	109.8 (2)	H16A—C16—H16B	108.3
C16—O1—K1	115.80 (18)	C15—C16—H16C	130.7
C13—O1—K1	128.60 (18)	O1—C16—H16C	110.7
C17—O2—C20	107.2 (3)	C15A—C16—H16C	110.7
C17—O2—K1	116.32 (18)	H16A—C16—H16C	82.7
C20—O2—K1	117.0 (2)	H16B—C16—H16C	27.7
C21—O3—C24	110.6 (3)	C15—C16—H16D	82.8
C21—O3—K1	124.0 (2)	O1—C16—H16D	110.7
C24—O3—K1	120.7 (2)	C15A—C16—H16D	110.7
C7—N1—C1	120.8 (2)	H16A—C16—H16D	29.2
C7—N1—K1	105.35 (14)	H16B—C16—H16D	130.1
C1—N1—K1	131.14 (15)	H16C—C16—H16D	108.8
C7—N1—K1^i	95.21 (14)	O2—C17—C18	106.6 (3)
C1—N1—K1^i	96.02 (14)	O2—C17—H17A	110.4
K1—N1—K1^i	94.93 (6)	C18—C17—H17A	110.4
N1—C1—C6	126.0 (2)	O2—C17—H17B	110.4
N1—C1—C2	118.5 (2)	C18—C17—H17B	110.4
C6—C1—C2	115.2 (2)	H17A—C17—H17B	108.6
N1—C1—K1^i	59.49 (12)	C19—C18—C17	104.8 (4)
C6—C1—K1^i	92.98 (14)	C19—C18—H18A	110.8
C2—C1—K1^i	115.53 (15)	C17—C18—H18A	110.8
C3—C2—C1	121.8 (2)	C19—C18—H18B	110.8
C3—C2—H2A	119.1	C17—C18—H18B	110.8
C1—C2—H2A	119.1	H18A—C18—H18B	108.9
C4—C3—C2	121.4 (2)	C18—C19—C20	102.5 (3)
C4—C3—H3A	119.3	C18—C19—H19A	111.3
C2—C3—H3A	119.3	C20—C19—H19A	111.3
C3—C4—C5	118.4 (3)	C18—C19—H19B	111.3
C3—C4—H4A	120.8	C20—C19—H19B	111.3
C5—C4—H4A	120.8	H19A—C19—H19B	109.2
C6—C5—C4	121.0 (3)	O2—C20—C19	106.1 (3)
C6—C5—H5A	119.5	O2—C20—H20A	110.5
C4—C5—H5A	119.5	C19—C20—H20A	110.5
C5—C6—C1	122.2 (2)	O2—C20—H20B	110.5
C5—C6—H6A	118.9	C19—C20—H20B	110.5
C1—C6—H6A	118.9	H20A—C20—H20B	108.7
N1—C7—C8	125.2 (2)	O3—C21—C22	106.7 (4)
N1—C7—C12	119.1 (2)	O3—C21—H21A	110.4
C8—C7—C12	115.5 (2)	C22—C21—H21A	110.4
N1—C7—K1^i	60.20 (12)	O3—C21—H21B	110.4
C8—C7—K1^i	140.00 (17)	C22—C21—H21B	110.4
C12—C7—K1^i	77.16 (14)	H21A—C21—H21B	108.6
N1—C7—K1	51.96 (12)	C21—C22—C23	103.2 (3)
C8—C7—K1	140.94 (17)	C21—C22—H22A	111.1
C12—C7—K1	78.85 (14)	C23—C22—H22A	111.1
K1^i—C7—K1	76.82 (5)	C21—C22—H22B	111.1
C9—C8—C7	121.4 (3)	C23—C22—H22B	111.1
C9—C8—H8A	119.3	H22A—C22—H22B	109.1
C7—C8—H8A	119.3	C24—C23—C22	102.7 (4)
C10—C9—C8	121.7 (3)	C24—C23—H23A	111.2
C10—C9—H9A	119.1	C22—C23—H23A	111.2
C8—C9—H9A	119.1	C24—C23—H23B	111.2
C9—C10—C11	118.4 (3)	C22—C23—H23B	111.2
C9—C10—H10A	120.8	H23A—C23—H23B	109.1
C11—C10—H10A	120.8	O3—C24—C23	104.7 (3)
C12—C11—C10	120.6 (3)	O3—C24—H24A	110.8
C12—C11—H11A	119.7	C23—C24—H24A	110.8
C10—C11—H11A	119.7	O3—C24—H24B	110.8
C11—C12—C7	122.3 (3)	C23—C24—H24B	110.8
C11—C12—K1^i	136.53 (17)	H24A—C24—H24B	108.9
C7—C12—K1^i	77.91 (14)

Symmetry code: (i) −x+2, −y+1, −z.