(18-Crown-6)potassium [(1,2,5,6-η)-cyclo-octa-1,5-diene][(1,2,3,4-η)-naph-tha-lene]-ferrate(-I).

The title salt, [K(C(12)H(24)O(6))][Fe(C(8)H(12))(C(10)H(8))], is the only known naphthalene complex containing iron in a formally negative oxidation state. Each (naphthalene)(1,5-cod)ferrate(-I) anion is in contact with one (18-crown-6)potassium cation via K⋯C contacts to the outer four carbon atoms of the naphthalene ligand (cod = 1,5-cyclo-octa-diene, 18-crown-6 = 1,4,7,10,13,16-hexa-oxacyclo-octa-deca-ne). When using the midpoints of the coordinating olefin bonds, the overall geometry of the coordination sphere around iron can be best described as distorted tetra-hedral. The naphthalene fold angle between the plane of the iron-coordinating butadiene unit and the plane containing the exo-benzene moiety is 19.2 (1)°.

Related literature

For the known complexes that contain iron in a formally negative oxidation state with solely olefinic ligands, see: Jonas (1979 ▶, 1981 ▶); Jonas et al. (1979 ▶); Jonas & Krüger (1980 ▶); Brennessel et al. (2007 ▶). For the various syntheses of the cobalt analog of the title complex, see: Brennessel et al. (2006 ▶); Brennessel & Ellis (2012 ▶). For an example of a diamagnetic, formally Fe(0) naphthalene­ferrate(−I), see: Schnökelborg et al. (2012 ▶). For details of the preparation and purification of reagents and solvents, and for descriptions of the equipment and techniques, see: Brennessel (2009 ▶). For a discussion of polyaromatic hydro­carbons and their Dewar’s resonance energies, see: Milun et al. (1972 ▶).

Experimental

Crystal data

[K(C12H24O6)][Fe(C8H12)(C10H8)]

M = 595.60

Triclinic,

a = 9.244 (1) Å

b = 10.5285 (12) Å

c = 15.971 (2) Å

α = 76.085 (2)°

β = 89.651 (2)°

γ = 74.949 (2)°

V = 1454.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.70 mm−1

T = 173 K

0.42 × 0.32 × 0.22 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.666, T max = 0.746

17413 measured reflections

6610 independent reflections

5576 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.073

S = 1.04

6610 reflections

423 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203704X/wm2674sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203704X/wm2674Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[K(C12H24O6)][Fe(C8H12)(C10H8)]	Z = 2
Mr = 595.60	F(000) = 634
Triclinic, P1	Dx = 1.360 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.244 (1) Å	Cell parameters from 3650 reflections
b = 10.5285 (12) Å	θ = 2.3–27.5°
c = 15.971 (2) Å	µ = 0.70 mm−1
α = 76.085 (2)°	T = 173 K
β = 89.651 (2)°	Block, dark red
γ = 74.949 (2)°	0.42 × 0.32 × 0.22 mm
V = 1454.4 (3) Å3

Siemens SMART CCD diffractometer	6610 independent reflections
Radiation source: normal-focus sealed tube	5576 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans per φ	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −12→11
Tmin = 0.666, Tmax = 0.746	k = −13→13
17413 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0321P)2 + 0.4038P] where P = (Fo2 + 2Fc2)/3
6610 reflections	(Δ/σ)max = 0.001
423 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
Fe1	0.66405 (2)	0.07626 (2)	0.327243 (13)	0.02107 (7)
C1	0.42748 (18)	0.15429 (16)	0.29524 (11)	0.0273 (3)
H1	0.364 (2)	0.1109 (18)	0.2718 (11)	0.033 (5)*
C2	0.46028 (19)	0.12384 (16)	0.38572 (11)	0.0300 (4)
H2	0.420 (2)	0.058 (2)	0.4266 (13)	0.041 (5)*
C3	0.5629 (2)	0.18225 (16)	0.41542 (11)	0.0296 (4)
H3	0.597 (2)	0.1600 (19)	0.4752 (13)	0.036 (5)*
C4	0.62680 (19)	0.27169 (16)	0.35391 (10)	0.0271 (3)
H4	0.704 (2)	0.3085 (17)	0.3709 (11)	0.029 (5)*
C5	0.57720 (19)	0.45705 (16)	0.21584 (11)	0.0292 (4)
H5	0.644 (2)	0.4972 (18)	0.2374 (11)	0.029 (5)*
C6	0.5125 (2)	0.50782 (18)	0.13140 (12)	0.0347 (4)
H6	0.535 (2)	0.583 (2)	0.0952 (12)	0.038 (5)*
C7	0.4159 (2)	0.44642 (19)	0.10107 (12)	0.0363 (4)
H7	0.370 (2)	0.4835 (19)	0.0440 (13)	0.038 (5)*
C8	0.38090 (19)	0.33404 (17)	0.15534 (11)	0.0304 (4)
H8	0.312 (2)	0.2921 (18)	0.1354 (11)	0.033 (5)*
C9	0.44646 (17)	0.27912 (15)	0.23910 (10)	0.0245 (3)
C10	0.54882 (17)	0.34143 (15)	0.27027 (10)	0.0241 (3)
C11	0.83151 (18)	0.08378 (17)	0.24371 (10)	0.0252 (3)
H11	0.8227 (19)	0.1757 (18)	0.2129 (11)	0.029 (5)*
C12	0.72907 (18)	0.02003 (16)	0.21617 (10)	0.0249 (3)
H12	0.658 (2)	0.0732 (18)	0.1659 (11)	0.030 (5)*
C13	0.7681 (2)	−0.13215 (17)	0.22562 (11)	0.0291 (4)
H13A	0.681 (2)	−0.1568 (18)	0.2049 (11)	0.033 (5)*
H13B	0.853 (2)	−0.1600 (18)	0.1890 (12)	0.034 (5)*
C14	0.8100 (2)	−0.21363 (17)	0.32012 (12)	0.0311 (4)
H14A	0.916 (2)	−0.2459 (18)	0.3285 (11)	0.032 (5)*
H14B	0.772 (2)	−0.2956 (19)	0.3322 (12)	0.036 (5)*
C15	0.74815 (18)	−0.12962 (16)	0.38461 (10)	0.0274 (3)
H15	0.6795 (19)	−0.1666 (17)	0.4243 (11)	0.025 (4)*
C16	0.83112 (19)	−0.05207 (17)	0.41517 (11)	0.0294 (4)
H16	0.813 (2)	−0.0428 (18)	0.4740 (12)	0.035 (5)*
C17	0.9833 (2)	−0.0384 (2)	0.38516 (12)	0.0369 (4)
H17A	1.063 (2)	−0.122 (2)	0.4099 (12)	0.042 (5)*
H17B	1.006 (2)	0.033 (2)	0.4088 (12)	0.037 (5)*
C18	0.98569 (19)	0.00363 (19)	0.28624 (12)	0.0321 (4)
H18A	1.0232 (19)	−0.0742 (18)	0.2615 (11)	0.030 (5)*
H18B	1.058 (2)	0.0561 (19)	0.2702 (12)	0.038 (5)*
K1	0.20189 (4)	0.61844 (4)	0.21260 (2)	0.02749 (9)
O1	0.15085 (12)	0.44660 (11)	0.36324 (7)	0.0284 (2)
O2	−0.03471 (13)	0.48729 (11)	0.21687 (7)	0.0286 (2)
O3	0.02462 (13)	0.65530 (12)	0.05729 (7)	0.0315 (3)
O4	0.18316 (13)	0.85078 (12)	0.06839 (7)	0.0330 (3)
O5	0.37379 (13)	0.80421 (11)	0.21515 (7)	0.0310 (3)
O6	0.29972 (12)	0.64416 (11)	0.37056 (7)	0.0256 (2)
C19	0.02914 (19)	0.38609 (17)	0.36605 (11)	0.0316 (4)
H19A	−0.0635	0.4477	0.3797	0.038*
H19B	0.0515	0.2998	0.4114	0.038*
C20	0.00795 (19)	0.35982 (16)	0.27952 (11)	0.0308 (4)
H20A	0.1025	0.3025	0.2644	0.037*
H20B	−0.0710	0.3115	0.2808	0.037*
C21	−0.06693 (19)	0.47181 (18)	0.13330 (11)	0.0310 (4)
H21A	−0.1514	0.4298	0.1351	0.037*
H21B	0.0219	0.4120	0.1145	0.037*
C22	−0.10719 (19)	0.60868 (19)	0.07117 (11)	0.0332 (4)
H22A	−0.1490	0.6027	0.0158	0.040*
H22B	−0.1841	0.6730	0.0950	0.040*
C23	−0.0027 (2)	0.78647 (17)	−0.00035 (11)	0.0355 (4)
H23A	−0.0771	0.8532	0.0232	0.043*
H23B	−0.0440	0.7849	−0.0570	0.043*
C24	0.1409 (2)	0.82724 (18)	−0.01150 (11)	0.0358 (4)
H24A	0.2202	0.7543	−0.0266	0.043*
H24B	0.1270	0.9108	−0.0586	0.043*
C25	0.31741 (19)	0.89400 (18)	0.06443 (11)	0.0342 (4)
H25A	0.3073	0.9753	0.0160	0.041*
H25B	0.4031	0.8211	0.0547	0.041*
C26	0.3439 (2)	0.92658 (17)	0.14826 (11)	0.0330 (4)
H26A	0.4303	0.9665	0.1451	0.040*
H26B	0.2542	0.9933	0.1605	0.040*
C30	0.17578 (18)	0.48077 (17)	0.44181 (10)	0.0278 (3)
H30A	0.1836	0.4013	0.4912	0.033*
H30B	0.0907	0.5555	0.4499	0.033*
C31	0.31821 (18)	0.52392 (16)	0.43816 (10)	0.0272 (3)
H31A	0.3414	0.5416	0.4940	0.033*
H31B	0.4024	0.4511	0.4270	0.033*
C32	0.43081 (17)	0.69279 (16)	0.36395 (10)	0.0267 (3)
H32A	0.5150	0.6267	0.3462	0.032*
H32B	0.4602	0.7039	0.4207	0.032*
C33	0.39767 (18)	0.82636 (16)	0.29834 (11)	0.0283 (3)
H33A	0.3070	0.8895	0.3128	0.034*
H33B	0.4829	0.8672	0.2981	0.034*

	U11	U22	U33	U12	U13	U23
Fe1	0.02165 (12)	0.02075 (11)	0.01995 (11)	−0.00350 (8)	0.00137 (8)	−0.00573 (8)
C1	0.0217 (8)	0.0211 (8)	0.0376 (9)	−0.0045 (6)	0.0020 (7)	−0.0057 (7)
C2	0.0292 (9)	0.0237 (8)	0.0328 (9)	−0.0032 (7)	0.0117 (7)	−0.0034 (7)
C3	0.0367 (9)	0.0258 (8)	0.0231 (8)	−0.0009 (7)	0.0062 (7)	−0.0082 (7)
C4	0.0287 (8)	0.0261 (8)	0.0290 (8)	−0.0057 (7)	0.0028 (7)	−0.0130 (7)
C5	0.0276 (8)	0.0233 (8)	0.0380 (9)	−0.0077 (7)	0.0099 (7)	−0.0090 (7)
C6	0.0368 (10)	0.0258 (9)	0.0352 (10)	−0.0050 (7)	0.0134 (8)	0.0002 (7)
C7	0.0351 (10)	0.0371 (10)	0.0271 (9)	0.0003 (8)	0.0024 (8)	−0.0006 (8)
C8	0.0251 (8)	0.0314 (9)	0.0320 (9)	−0.0026 (7)	−0.0015 (7)	−0.0076 (7)
C9	0.0201 (7)	0.0213 (7)	0.0301 (8)	−0.0004 (6)	0.0048 (6)	−0.0085 (6)
C10	0.0229 (8)	0.0206 (7)	0.0289 (8)	−0.0021 (6)	0.0076 (6)	−0.0105 (6)
C11	0.0265 (8)	0.0252 (8)	0.0247 (8)	−0.0075 (6)	0.0057 (6)	−0.0072 (6)
C12	0.0248 (8)	0.0284 (8)	0.0213 (7)	−0.0048 (6)	0.0025 (6)	−0.0082 (6)
C13	0.0287 (9)	0.0295 (9)	0.0327 (9)	−0.0068 (7)	0.0040 (7)	−0.0157 (7)
C14	0.0304 (9)	0.0230 (8)	0.0389 (10)	−0.0042 (7)	0.0006 (7)	−0.0088 (7)
C15	0.0276 (8)	0.0239 (8)	0.0257 (8)	−0.0029 (7)	0.0000 (7)	−0.0009 (6)
C16	0.0296 (9)	0.0297 (9)	0.0244 (8)	−0.0009 (7)	−0.0048 (7)	−0.0054 (7)
C17	0.0275 (9)	0.0385 (10)	0.0422 (11)	−0.0033 (8)	−0.0098 (8)	−0.0112 (8)
C18	0.0213 (8)	0.0342 (9)	0.0443 (10)	−0.0077 (7)	0.0053 (7)	−0.0160 (8)
K1	0.03164 (19)	0.03177 (19)	0.02181 (17)	−0.01498 (15)	0.00019 (14)	−0.00468 (14)
O1	0.0298 (6)	0.0331 (6)	0.0255 (6)	−0.0146 (5)	0.0039 (5)	−0.0066 (5)
O2	0.0335 (6)	0.0279 (6)	0.0285 (6)	−0.0118 (5)	0.0009 (5)	−0.0107 (5)
O3	0.0300 (6)	0.0322 (6)	0.0298 (6)	−0.0080 (5)	−0.0047 (5)	−0.0032 (5)
O4	0.0394 (7)	0.0395 (7)	0.0219 (6)	−0.0168 (5)	0.0009 (5)	−0.0040 (5)
O5	0.0396 (7)	0.0238 (6)	0.0294 (6)	−0.0127 (5)	−0.0057 (5)	−0.0015 (5)
O6	0.0245 (6)	0.0247 (6)	0.0260 (6)	−0.0074 (4)	−0.0034 (4)	−0.0025 (4)
C19	0.0328 (9)	0.0314 (9)	0.0324 (9)	−0.0158 (7)	0.0047 (7)	−0.0033 (7)
C20	0.0303 (9)	0.0268 (8)	0.0388 (9)	−0.0132 (7)	0.0045 (7)	−0.0089 (7)
C21	0.0294 (9)	0.0406 (10)	0.0323 (9)	−0.0158 (7)	0.0051 (7)	−0.0196 (8)
C22	0.0258 (8)	0.0476 (11)	0.0297 (9)	−0.0094 (8)	−0.0020 (7)	−0.0164 (8)
C23	0.0460 (11)	0.0296 (9)	0.0270 (9)	−0.0037 (8)	−0.0110 (8)	−0.0063 (7)
C24	0.0544 (12)	0.0294 (9)	0.0215 (8)	−0.0106 (8)	−0.0001 (8)	−0.0028 (7)
C25	0.0330 (9)	0.0304 (9)	0.0340 (9)	−0.0094 (7)	0.0034 (7)	0.0031 (7)
C26	0.0327 (9)	0.0252 (8)	0.0382 (10)	−0.0126 (7)	−0.0038 (7)	0.0033 (7)
C30	0.0311 (9)	0.0301 (8)	0.0198 (8)	−0.0080 (7)	0.0016 (6)	−0.0018 (6)
C31	0.0292 (8)	0.0284 (8)	0.0209 (8)	−0.0050 (7)	−0.0024 (6)	−0.0028 (6)
C32	0.0229 (8)	0.0299 (8)	0.0288 (8)	−0.0075 (6)	−0.0032 (6)	−0.0096 (7)
C33	0.0256 (8)	0.0268 (8)	0.0352 (9)	−0.0096 (7)	−0.0019 (7)	−0.0095 (7)

Fe1—C12	2.0410 (15)	C18—H18B	0.972 (19)
Fe1—C11	2.0421 (15)	K1—O1	2.7604 (11)
Fe1—C16	2.0525 (16)	K1—O6	2.7818 (11)
Fe1—C3	2.0736 (16)	K1—O5	2.8294 (11)
Fe1—C15	2.0786 (16)	K1—O2	2.8664 (11)
Fe1—C2	2.0940 (16)	K1—O3	2.8715 (12)
Fe1—C4	2.1413 (16)	K1—O4	2.8972 (12)
Fe1—C1	2.1441 (16)	O1—C30	1.4216 (19)
C1—C2	1.420 (2)	O1—C19	1.4254 (19)
C1—C9	1.454 (2)	O2—C21	1.4252 (19)
C1—H1	0.960 (18)	O2—C20	1.4289 (19)
C2—C3	1.397 (2)	O3—C23	1.424 (2)
C2—H2	0.98 (2)	O3—C22	1.425 (2)
C3—C4	1.427 (2)	O4—C25	1.425 (2)
C3—H3	0.961 (19)	O4—C24	1.432 (2)
C4—C10	1.452 (2)	O5—C26	1.4263 (18)
C4—H4	0.961 (18)	O5—C33	1.4310 (19)
C5—C6	1.400 (3)	O6—C31	1.4247 (18)
C5—C10	1.400 (2)	O6—C32	1.4271 (18)
C5—K1	3.4387 (17)	C19—C20	1.497 (2)
C5—H5	0.941 (18)	C19—H19A	0.9900
C6—C7	1.380 (3)	C19—H19B	0.9900
C6—K1	3.1978 (18)	C20—H20A	0.9900
C6—H6	0.932 (19)	C20—H20B	0.9900
C7—C8	1.399 (2)	C21—C22	1.496 (2)
C7—K1	3.1647 (19)	C21—H21A	0.9900
C7—H7	0.955 (19)	C21—H21B	0.9900
C8—C9	1.395 (2)	C22—H22A	0.9900
C8—K1	3.3565 (18)	C22—H22B	0.9900
C8—H8	0.959 (18)	C23—C24	1.494 (3)
C9—C10	1.435 (2)	C23—H23A	0.9900
C11—C12	1.420 (2)	C23—H23B	0.9900
C11—C18	1.522 (2)	C24—H24A	0.9900
C11—H11	0.957 (18)	C24—H24B	0.9900
C12—C13	1.518 (2)	C25—C26	1.496 (2)
C12—H12	0.994 (18)	C25—H25A	0.9900
C13—C14	1.541 (2)	C25—H25B	0.9900
C13—H13A	0.986 (18)	C26—H26A	0.9900
C13—H13B	0.997 (19)	C26—H26B	0.9900
C14—C15	1.529 (2)	C30—C31	1.497 (2)
C14—H14A	0.944 (19)	C30—H30A	0.9900
C14—H14B	0.993 (19)	C30—H30B	0.9900
C15—C16	1.419 (2)	C31—H31A	0.9900
C15—H15	0.980 (17)	C31—H31B	0.9900
C16—C17	1.514 (3)	C32—C33	1.497 (2)
C16—H16	0.977 (19)	C32—H32A	0.9900
C17—C18	1.537 (3)	C32—H32B	0.9900
C17—H17A	0.98 (2)	C33—H33A	0.9900
C17—H17B	0.99 (2)	C33—H33B	0.9900
C18—H18A	0.977 (18)
C12—Fe1—C11	40.72 (6)	C18—C17—H17B	108.4 (11)
C12—Fe1—C16	101.66 (7)	H17A—C17—H17B	106.2 (16)
C11—Fe1—C16	85.08 (7)	C11—C18—C17	112.01 (14)
C12—Fe1—C3	163.78 (7)	C11—C18—H18A	108.9 (10)
C11—Fe1—C3	137.43 (7)	C17—C18—H18A	112.3 (10)
C16—Fe1—C3	93.69 (7)	C11—C18—H18B	110.4 (11)
C12—Fe1—C15	83.82 (7)	C17—C18—H18B	109.6 (11)
C11—Fe1—C15	94.47 (7)	H18A—C18—H18B	103.1 (15)
C16—Fe1—C15	40.18 (6)	O1—K1—O6	60.69 (3)
C3—Fe1—C15	111.66 (7)	O1—K1—O5	121.15 (3)
C12—Fe1—C2	135.35 (7)	O6—K1—O5	60.68 (3)
C11—Fe1—C2	162.51 (7)	O1—K1—O2	59.38 (3)
C16—Fe1—C2	111.20 (7)	O6—K1—O2	116.23 (3)
C3—Fe1—C2	39.17 (7)	O5—K1—O2	165.04 (4)
C15—Fe1—C2	102.14 (7)	O1—K1—O3	119.37 (3)
C12—Fe1—C4	128.82 (6)	O6—K1—O3	162.63 (4)
C11—Fe1—C4	100.06 (6)	O5—K1—O3	117.93 (3)
C16—Fe1—C4	105.99 (7)	O2—K1—O3	60.05 (3)
C3—Fe1—C4	39.54 (6)	O1—K1—O4	163.85 (4)
C15—Fe1—C4	141.78 (6)	O6—K1—O4	115.14 (3)
C2—Fe1—C4	70.01 (6)	O5—K1—O4	58.73 (3)
C12—Fe1—C1	99.01 (7)	O2—K1—O4	116.06 (3)
C11—Fe1—C1	126.64 (6)	O3—K1—O4	59.37 (3)
C16—Fe1—C1	146.94 (7)	C30—O1—C19	112.41 (12)
C3—Fe1—C1	69.83 (7)	C30—O1—K1	116.80 (9)
C15—Fe1—C1	118.39 (6)	C19—O1—K1	120.44 (9)
C2—Fe1—C1	39.12 (7)	C21—O2—C20	111.93 (12)
C4—Fe1—C1	79.83 (6)	C21—O2—K1	110.68 (9)
C2—C1—C9	120.56 (15)	C20—O2—K1	108.68 (9)
C2—C1—Fe1	68.54 (9)	C23—O3—C22	112.93 (13)
C9—C1—Fe1	92.17 (10)	C23—O3—K1	114.91 (9)
C2—C1—H1	120.7 (11)	C22—O3—K1	114.12 (9)
C9—C1—H1	115.8 (11)	C25—O4—C24	112.73 (13)
Fe1—C1—H1	126.7 (11)	C25—O4—K1	111.39 (9)
C3—C2—C1	118.02 (15)	C24—O4—K1	112.03 (9)
C3—C2—Fe1	69.62 (9)	C26—O5—C33	112.31 (12)
C1—C2—Fe1	72.35 (9)	C26—O5—K1	118.54 (9)
C3—C2—H2	120.0 (11)	C33—O5—K1	114.97 (9)
C1—C2—H2	121.8 (11)	C31—O6—C32	111.88 (11)
Fe1—C2—H2	124.6 (11)	C31—O6—K1	113.19 (8)
C2—C3—C4	118.71 (15)	C32—O6—K1	112.13 (9)
C2—C3—Fe1	71.20 (9)	O1—C19—C20	108.19 (13)
C4—C3—Fe1	72.78 (9)	O1—C19—H19A	110.1
C2—C3—H3	122.6 (11)	C20—C19—H19A	110.1
C4—C3—H3	118.6 (11)	O1—C19—H19B	110.1
Fe1—C3—H3	123.8 (11)	C20—C19—H19B	110.1
C3—C4—C10	120.06 (15)	H19A—C19—H19B	108.4
C3—C4—Fe1	67.67 (9)	O2—C20—C19	108.37 (13)
C10—C4—Fe1	92.85 (10)	O2—C20—H20A	110.0
C3—C4—H4	121.5 (10)	C19—C20—H20A	110.0
C10—C4—H4	116.0 (10)	O2—C20—H20B	110.0
Fe1—C4—H4	125.3 (10)	C19—C20—H20B	110.0
C6—C5—C10	120.95 (16)	H20A—C20—H20B	108.4
C6—C5—H5	121.4 (11)	O2—C21—C22	108.77 (13)
C10—C5—H5	117.6 (11)	O2—C21—H21A	109.9
K1—C5—H5	116.1 (11)	C22—C21—H21A	109.9
C7—C6—C5	120.30 (16)	O2—C21—H21B	109.9
C7—C6—H6	119.6 (12)	C22—C21—H21B	109.9
C5—C6—H6	120.1 (12)	H21A—C21—H21B	108.3
K1—C6—H6	106.6 (12)	O3—C22—C21	108.65 (13)
C6—C7—C8	119.87 (17)	O3—C22—H22A	110.0
C6—C7—H7	119.7 (12)	C21—C22—H22A	110.0
C8—C7—H7	120.4 (12)	O3—C22—H22B	110.0
K1—C7—H7	103.4 (12)	C21—C22—H22B	110.0
C9—C8—C7	121.13 (16)	H22A—C22—H22B	108.3
C9—C8—H8	118.3 (11)	O3—C23—C24	109.44 (14)
C7—C8—H8	120.6 (11)	O3—C23—H23A	109.8
K1—C8—H8	111.7 (11)	C24—C23—H23A	109.8
C8—C9—C10	119.06 (15)	O3—C23—H23B	109.8
C8—C9—C1	123.75 (15)	C24—C23—H23B	109.8
C10—C9—C1	116.98 (14)	H23A—C23—H23B	108.2
C5—C10—C9	118.62 (15)	O4—C24—C23	107.90 (14)
C5—C10—C4	124.29 (15)	O4—C24—H24A	110.1
C9—C10—C4	116.83 (14)	C23—C24—H24A	110.1
C12—C11—C18	122.17 (15)	O4—C24—H24B	110.1
C12—C11—Fe1	69.60 (9)	C23—C24—H24B	110.1
C18—C11—Fe1	112.75 (11)	H24A—C24—H24B	108.4
C12—C11—H11	116.2 (10)	O4—C25—C26	108.20 (14)
C18—C11—H11	116.0 (10)	O4—C25—H25A	110.1
Fe1—C11—H11	110.0 (10)	C26—C25—H25A	110.1
C11—C12—C13	121.97 (14)	O4—C25—H25B	110.1
C11—C12—Fe1	69.68 (9)	C26—C25—H25B	110.1
C13—C12—Fe1	113.82 (11)	H25A—C25—H25B	108.4
C11—C12—H12	117.4 (10)	O5—C26—C25	108.47 (13)
C13—C12—H12	113.5 (10)	O5—C26—H26A	110.0
Fe1—C12—H12	112.3 (10)	C25—C26—H26A	110.0
C12—C13—C14	112.40 (13)	O5—C26—H26B	110.0
C12—C13—H13A	109.6 (10)	C25—C26—H26B	110.0
C14—C13—H13A	108.0 (10)	H26A—C26—H26B	108.4
C12—C13—H13B	110.3 (10)	O1—C30—C31	108.80 (13)
C14—C13—H13B	109.5 (10)	O1—C30—H30A	109.9
H13A—C13—H13B	106.9 (14)	C31—C30—H30A	109.9
C15—C14—C13	112.34 (13)	O1—C30—H30B	109.9
C15—C14—H14A	110.1 (11)	C31—C30—H30B	109.9
C13—C14—H14A	109.2 (11)	H30A—C30—H30B	108.3
C15—C14—H14B	108.8 (11)	O6—C31—C30	108.64 (12)
C13—C14—H14B	110.3 (11)	O6—C31—H31A	110.0
H14A—C14—H14B	105.9 (15)	C30—C31—H31A	110.0
C16—C15—C14	122.00 (15)	O6—C31—H31B	110.0
C16—C15—Fe1	68.92 (9)	C30—C31—H31B	110.0
C14—C15—Fe1	113.32 (11)	H31A—C31—H31B	108.3
C16—C15—H15	116.8 (10)	O6—C32—C33	108.81 (12)
C14—C15—H15	114.3 (10)	O6—C32—H32A	109.9
Fe1—C15—H15	112.9 (10)	C33—C32—H32A	109.9
C15—C16—C17	124.39 (16)	O6—C32—H32B	109.9
C15—C16—Fe1	70.90 (9)	C33—C32—H32B	109.9
C17—C16—Fe1	110.35 (12)	H32A—C32—H32B	108.3
C15—C16—H16	115.1 (11)	O5—C33—C32	108.60 (12)
C17—C16—H16	114.7 (11)	O5—C33—H33A	110.0
Fe1—C16—H16	112.2 (11)	C32—C33—H33A	110.0
C16—C17—C18	112.64 (14)	O5—C33—H33B	110.0
C16—C17—H17A	111.2 (11)	C32—C33—H33B	110.0
C18—C17—H17A	111.3 (12)	H33A—C33—H33B	108.4
C16—C17—H17B	106.7 (11)
C12—Fe1—C1—C2	161.21 (10)	C7—C6—K1—O3	−41.08 (10)
C11—Fe1—C1—C2	−165.77 (10)	C5—C6—K1—O3	−163.09 (10)
C16—Fe1—C1—C2	33.00 (16)	C7—C6—K1—O4	−99.33 (11)
C3—Fe1—C1—C2	−30.98 (10)	C5—C6—K1—O4	138.66 (11)
C15—Fe1—C1—C2	73.40 (11)	C5—C6—K1—C7	−122.01 (16)
C4—Fe1—C1—C2	−70.74 (10)	C7—C6—K1—C8	31.25 (10)
C12—Fe1—C1—C9	−76.67 (10)	C5—C6—K1—C8	−90.76 (11)
C11—Fe1—C1—C9	−43.65 (13)	C7—C6—K1—C5	122.01 (16)
C16—Fe1—C1—C9	155.12 (11)	C9—C8—K1—O1	−41.96 (10)
C3—Fe1—C1—C9	91.14 (11)	C7—C8—K1—O1	−165.52 (11)
C15—Fe1—C1—C9	−164.48 (9)	C9—C8—K1—O6	12.38 (11)
C2—Fe1—C1—C9	122.12 (14)	C7—C8—K1—O6	−111.18 (11)
C4—Fe1—C1—C9	51.38 (10)	C9—C8—K1—O5	80.62 (10)
C9—C1—C2—C3	−25.0 (2)	C7—C8—K1—O5	−42.94 (12)
Fe1—C1—C2—C3	54.32 (13)	C9—C8—K1—O2	−101.61 (10)
C9—C1—C2—Fe1	−79.35 (14)	C7—C8—K1—O2	134.83 (11)
C12—Fe1—C2—C3	−157.02 (10)	C9—C8—K1—O3	−162.66 (10)
C11—Fe1—C2—C3	−89.1 (2)	C7—C8—K1—O3	73.78 (11)
C16—Fe1—C2—C3	68.48 (11)	C9—C8—K1—O4	144.42 (9)
C15—Fe1—C2—C3	109.48 (10)	C7—C8—K1—O4	20.86 (11)
C4—Fe1—C2—C3	−31.50 (10)	C9—C8—K1—C7	123.56 (16)
C1—Fe1—C2—C3	−130.10 (14)	C9—C8—K1—C6	91.65 (11)
C12—Fe1—C2—C1	−26.92 (14)	C7—C8—K1—C6	−31.91 (10)
C11—Fe1—C2—C1	41.0 (3)	C9—C8—K1—C5	58.67 (10)
C16—Fe1—C2—C1	−161.42 (9)	C7—C8—K1—C5	−64.89 (11)
C3—Fe1—C2—C1	130.10 (14)	C6—C5—K1—O1	145.42 (11)
C15—Fe1—C2—C1	−120.42 (10)	C10—C5—K1—O1	21.06 (10)
C4—Fe1—C2—C1	98.60 (10)	C6—C5—K1—O6	−155.54 (11)
C1—C2—C3—C4	1.5 (2)	C10—C5—K1—O6	80.10 (10)
Fe1—C2—C3—C4	57.12 (13)	C6—C5—K1—O5	−93.22 (11)
C1—C2—C3—Fe1	−55.66 (13)	C10—C5—K1—O5	142.42 (11)
C12—Fe1—C3—C2	79.2 (3)	C6—C5—K1—O2	89.50 (11)
C11—Fe1—C3—C2	153.62 (10)	C10—C5—K1—O2	−34.86 (11)
C16—Fe1—C3—C2	−119.64 (10)	C6—C5—K1—O3	18.96 (11)
C15—Fe1—C3—C2	−82.59 (11)	C10—C5—K1—O3	−105.40 (10)
C4—Fe1—C3—C2	129.54 (15)	C6—C5—K1—O4	−41.51 (11)
C1—Fe1—C3—C2	30.94 (10)	C10—C5—K1—O4	−165.87 (10)
C12—Fe1—C3—C4	−50.3 (3)	C6—C5—K1—C7	32.05 (10)
C11—Fe1—C3—C4	24.08 (15)	C10—C5—K1—C7	−92.31 (11)
C16—Fe1—C3—C4	110.82 (10)	C10—C5—K1—C6	−124.36 (16)
C15—Fe1—C3—C4	147.87 (10)	C6—C5—K1—C8	65.84 (11)
C2—Fe1—C3—C4	−129.54 (15)	C10—C5—K1—C8	−58.52 (10)
C1—Fe1—C3—C4	−98.60 (11)	O6—K1—O1—C30	12.09 (9)
C2—C3—C4—C10	23.5 (2)	O5—K1—O1—C30	17.53 (11)
Fe1—C3—C4—C10	79.89 (13)	O2—K1—O1—C30	−145.04 (11)
C2—C3—C4—Fe1	−56.34 (13)	O3—K1—O1—C30	−147.96 (10)
C12—Fe1—C4—C3	163.98 (10)	O4—K1—O1—C30	−67.09 (16)
C11—Fe1—C4—C3	−163.72 (10)	C7—K1—O1—C30	128.75 (10)
C16—Fe1—C4—C3	−76.00 (11)	C6—K1—O1—C30	102.26 (11)
C15—Fe1—C4—C3	−53.04 (15)	C8—K1—O1—C30	135.07 (10)
C2—Fe1—C4—C3	31.22 (10)	C5—K1—O1—C30	87.59 (10)
C1—Fe1—C4—C3	70.55 (11)	O6—K1—O1—C19	154.46 (12)
C12—Fe1—C4—C10	42.54 (13)	O5—K1—O1—C19	159.91 (10)
C11—Fe1—C4—C10	74.83 (10)	O2—K1—O1—C19	−2.66 (10)
C16—Fe1—C4—C10	162.55 (10)	O3—K1—O1—C19	−5.58 (12)
C3—Fe1—C4—C10	−121.45 (15)	O4—K1—O1—C19	75.29 (17)
C15—Fe1—C4—C10	−174.49 (10)	C7—K1—O1—C19	−88.88 (12)
C2—Fe1—C4—C10	−90.23 (11)	C6—K1—O1—C19	−115.36 (11)
C1—Fe1—C4—C10	−50.90 (10)	C8—K1—O1—C19	−82.56 (11)
C10—C5—C6—C7	1.7 (3)	C5—K1—O1—C19	−130.04 (11)
K1—C5—C6—C7	−72.46 (15)	O1—K1—O2—C21	−153.62 (11)
C10—C5—C6—K1	74.20 (15)	O6—K1—O2—C21	−175.82 (9)
C5—C6—C7—C8	0.9 (3)	O5—K1—O2—C21	109.87 (15)
K1—C6—C7—C8	−78.03 (16)	O3—K1—O2—C21	23.44 (9)
C5—C6—C7—K1	78.91 (15)	O4—K1—O2—C21	44.00 (11)
C6—C7—C8—C9	−2.5 (3)	C7—K1—O2—C21	−45.06 (10)
K1—C7—C8—C9	−76.77 (15)	C6—K1—O2—C21	−51.82 (11)
C6—C7—C8—K1	74.31 (16)	C8—K1—O2—C21	−62.31 (10)
C7—C8—C9—C10	1.4 (2)	C5—K1—O2—C21	−80.10 (11)
K1—C8—C9—C10	−64.79 (13)	O1—K1—O2—C20	−30.31 (9)
C7—C8—C9—C1	−173.11 (16)	O6—K1—O2—C20	−52.52 (10)
K1—C8—C9—C1	120.69 (14)	O5—K1—O2—C20	−126.82 (14)
C2—C1—C9—C8	−162.24 (15)	O3—K1—O2—C20	146.75 (10)
Fe1—C1—C9—C8	131.52 (14)	O4—K1—O2—C20	167.31 (9)
C2—C1—C9—C10	23.1 (2)	C7—K1—O2—C20	78.25 (10)
Fe1—C1—C9—C10	−43.11 (14)	C6—K1—O2—C20	71.48 (10)
C6—C5—C10—C9	−2.7 (2)	C8—K1—O2—C20	60.99 (9)
K1—C5—C10—C9	60.69 (13)	C5—K1—O2—C20	43.21 (10)
C6—C5—C10—C4	171.20 (15)	O1—K1—O3—C23	147.96 (10)
K1—C5—C10—C4	−125.37 (14)	O6—K1—O3—C23	62.70 (16)
C8—C9—C10—C5	1.2 (2)	O5—K1—O3—C23	−17.99 (12)
C1—C9—C10—C5	176.05 (14)	O2—K1—O3—C23	145.06 (12)
C8—C9—C10—C4	−173.22 (14)	O4—K1—O3—C23	−13.44 (10)
C1—C9—C10—C4	1.7 (2)	C7—K1—O3—C23	−108.02 (11)
C3—C4—C10—C5	161.21 (15)	C6—K1—O3—C23	−91.28 (11)
Fe1—C4—C10—C5	−133.04 (14)	C8—K1—O3—C23	−132.41 (11)
C3—C4—C10—C9	−24.8 (2)	C5—K1—O3—C23	−98.89 (11)
Fe1—C4—C10—C9	41.00 (14)	O1—K1—O3—C22	15.21 (11)
C16—Fe1—C11—C12	114.26 (10)	O6—K1—O3—C22	−70.04 (16)
C3—Fe1—C11—C12	−155.64 (10)	O5—K1—O3—C22	−150.74 (10)
C15—Fe1—C11—C12	75.15 (10)	O2—K1—O3—C22	12.31 (10)
C2—Fe1—C11—C12	−86.6 (2)	O4—K1—O3—C22	−146.18 (11)
C4—Fe1—C11—C12	−140.34 (10)	C7—K1—O3—C22	119.24 (11)
C1—Fe1—C11—C12	−55.59 (12)	C6—K1—O3—C22	135.97 (11)
C12—Fe1—C11—C18	−117.39 (16)	C8—K1—O3—C22	94.84 (11)
C16—Fe1—C11—C18	−3.13 (12)	C5—K1—O3—C22	128.36 (10)
C3—Fe1—C11—C18	86.97 (14)	O1—K1—O4—C25	120.25 (14)
C15—Fe1—C11—C18	−42.24 (12)	O6—K1—O4—C25	49.17 (11)
C2—Fe1—C11—C18	156.0 (2)	O5—K1—O4—C25	25.78 (10)
C4—Fe1—C11—C18	102.27 (12)	O2—K1—O4—C25	−170.22 (10)
C1—Fe1—C11—C18	−172.98 (11)	O3—K1—O4—C25	−149.51 (11)
C18—C11—C12—C13	−1.4 (2)	C7—K1—O4—C25	−74.70 (11)
Fe1—C11—C12—C13	−106.05 (15)	C6—K1—O4—C25	−49.95 (11)
C18—C11—C12—Fe1	104.69 (15)	C8—K1—O4—C25	−83.23 (11)
C16—Fe1—C12—C11	−68.04 (10)	C5—K1—O4—C25	−34.13 (11)
C3—Fe1—C12—C11	92.7 (3)	O1—K1—O4—C24	−112.43 (15)
C15—Fe1—C12—C11	−104.24 (10)	O6—K1—O4—C24	176.48 (10)
C2—Fe1—C12—C11	154.72 (10)	O5—K1—O4—C24	153.09 (12)
C4—Fe1—C12—C11	53.76 (12)	O2—K1—O4—C24	−42.90 (12)
C1—Fe1—C12—C11	137.91 (10)	O3—K1—O4—C24	−22.19 (10)
C11—Fe1—C12—C13	116.98 (16)	C7—K1—O4—C24	52.62 (11)
C16—Fe1—C12—C13	48.94 (13)	C6—K1—O4—C24	77.37 (11)
C3—Fe1—C12—C13	−150.3 (2)	C8—K1—O4—C24	44.09 (12)
C15—Fe1—C12—C13	12.74 (12)	C5—K1—O4—C24	93.18 (11)
C2—Fe1—C12—C13	−88.29 (14)	O1—K1—O5—C26	−152.12 (11)
C4—Fe1—C12—C13	170.74 (11)	O6—K1—O5—C26	−146.68 (12)
C1—Fe1—C12—C13	−105.10 (12)	O2—K1—O5—C26	−64.62 (18)
C11—C12—C13—C14	57.8 (2)	O3—K1—O5—C26	13.57 (12)
Fe1—C12—C13—C14	−22.33 (18)	O4—K1—O5—C26	8.98 (11)
C12—C13—C14—C15	21.5 (2)	C7—K1—O5—C26	90.30 (12)
C13—C14—C15—C16	−90.26 (19)	C6—K1—O5—C26	99.05 (12)
C13—C14—C15—Fe1	−11.36 (18)	C8—K1—O5—C26	106.87 (11)
C12—Fe1—C15—C16	116.31 (11)	C5—K1—O5—C26	124.11 (12)
C11—Fe1—C15—C16	76.95 (10)	O1—K1—O5—C33	−15.23 (11)
C3—Fe1—C15—C16	−68.72 (11)	O6—K1—O5—C33	−9.79 (9)
C2—Fe1—C15—C16	−108.57 (11)	O2—K1—O5—C33	72.27 (17)
C4—Fe1—C15—C16	−35.54 (15)	O3—K1—O5—C33	150.46 (9)
C1—Fe1—C15—C16	−146.77 (10)	O4—K1—O5—C33	145.87 (11)
C12—Fe1—C15—C14	−0.58 (12)	C7—K1—O5—C33	−132.82 (10)
C11—Fe1—C15—C14	−39.94 (13)	C6—K1—O5—C33	−124.07 (10)
C16—Fe1—C15—C14	−116.89 (16)	C8—K1—O5—C33	−116.25 (10)
C3—Fe1—C15—C14	174.39 (12)	C5—K1—O5—C33	−99.00 (10)
C2—Fe1—C15—C14	134.54 (12)	O1—K1—O6—C31	22.09 (9)
C4—Fe1—C15—C14	−152.43 (12)	O5—K1—O6—C31	−152.57 (10)
C1—Fe1—C15—C14	96.34 (13)	O2—K1—O6—C31	43.99 (10)
C14—C15—C16—C17	3.0 (2)	O3—K1—O6—C31	117.20 (13)
Fe1—C15—C16—C17	−102.06 (16)	O4—K1—O6—C31	−175.47 (9)
C14—C15—C16—Fe1	105.03 (15)	C7—K1—O6—C31	−73.40 (10)
C12—Fe1—C16—C15	−65.50 (11)	C6—K1—O6—C31	−89.36 (10)
C11—Fe1—C16—C15	−102.89 (10)	C8—K1—O6—C31	−46.19 (10)
C3—Fe1—C16—C15	119.79 (10)	C5—K1—O6—C31	−79.46 (10)
C2—Fe1—C16—C15	83.71 (11)	O1—K1—O6—C32	149.82 (10)
C4—Fe1—C16—C15	158.04 (10)	O5—K1—O6—C32	−24.84 (9)
C1—Fe1—C16—C15	62.09 (16)	O2—K1—O6—C32	171.72 (9)
C12—Fe1—C16—C17	55.10 (13)	O3—K1—O6—C32	−115.07 (13)
C11—Fe1—C16—C17	17.71 (12)	O4—K1—O6—C32	−47.74 (10)
C3—Fe1—C16—C17	−119.61 (13)	C7—K1—O6—C32	54.33 (10)
C15—Fe1—C16—C17	120.60 (17)	C6—K1—O6—C32	38.37 (10)
C2—Fe1—C16—C17	−155.69 (12)	C8—K1—O6—C32	81.55 (10)
C4—Fe1—C16—C17	−81.36 (13)	C5—K1—O6—C32	48.27 (9)
C1—Fe1—C16—C17	−177.31 (12)	C30—O1—C19—C20	177.53 (13)
C15—C16—C17—C18	51.3 (2)	K1—O1—C19—C20	33.64 (17)
Fe1—C16—C17—C18	−29.01 (19)	C21—O2—C20—C19	−176.10 (13)
C12—C11—C18—C17	−91.52 (19)	K1—O2—C20—C19	61.35 (13)
Fe1—C11—C18—C17	−12.05 (18)	O1—C19—C20—O2	−63.86 (17)
C16—C17—C18—C11	26.9 (2)	C20—O2—C21—C22	−178.76 (13)
C6—C7—K1—O1	−106.36 (10)	K1—O2—C21—C22	−57.35 (14)
C8—C7—K1—O1	15.32 (12)	C23—O3—C22—C21	−179.16 (13)
C6—C7—K1—O6	−39.48 (12)	K1—O3—C22—C21	−45.48 (15)
C8—C7—K1—O6	82.20 (11)	O2—C21—C22—O3	70.65 (16)
C6—C7—K1—O5	20.15 (11)	C22—O3—C23—C24	−179.81 (14)
C8—C7—K1—O5	141.83 (10)	K1—O3—C23—C24	46.89 (16)
C6—C7—K1—O2	−166.17 (10)	C25—O4—C24—C23	−178.44 (13)
C8—C7—K1—O2	−44.50 (11)	K1—O4—C24—C23	54.97 (15)
C6—C7—K1—O3	137.27 (11)	O3—C23—C24—O4	−69.17 (17)
C8—C7—K1—O3	−101.06 (11)	C24—O4—C25—C26	175.34 (13)
C6—C7—K1—O4	78.00 (10)	K1—O4—C25—C26	−57.72 (14)
C8—C7—K1—O4	−160.32 (11)	C33—O5—C26—C25	−178.84 (13)
C8—C7—K1—C6	121.68 (16)	K1—O5—C26—C25	−40.89 (16)
C6—C7—K1—C8	−121.68 (16)	O4—C25—C26—O5	65.82 (17)
C6—C7—K1—C5	−30.64 (9)	C19—O1—C30—C31	171.64 (13)
C8—C7—K1—C5	91.03 (12)	K1—O1—C30—C31	−43.07 (15)
C7—C6—K1—O1	83.65 (11)	C32—O6—C31—C30	179.12 (13)
C5—C6—K1—O1	−38.36 (12)	K1—O6—C31—C30	−53.02 (14)
C7—C6—K1—O6	146.61 (10)	O1—C30—C31—O6	63.81 (16)
C5—C6—K1—O6	24.60 (11)	C31—O6—C32—C33	−174.09 (13)
C7—C6—K1—O5	−159.10 (11)	K1—O6—C32—C33	57.49 (13)
C5—C6—K1—O5	78.89 (10)	C26—O5—C33—C32	−179.00 (13)
C7—C6—K1—O2	16.05 (12)	K1—O5—C33—C32	41.47 (14)
C5—C6—K1—O2	−105.96 (11)	O6—C32—C33—O5	−66.62 (16)