A cytochrome b model, [Fe(TPP)(4-MeHIm)₂][K(222-cryptand)]₂Cl₂

The mol­ecular structure of the title cytochrome b model, (5-meth­yl-4H-imidazole)(5,10,15,20-tetra­phenyl­porphyrinato)­iron(II) bis­[(222-cryptand)potassium(I)] dichloride, [Fe(C₄₄H₂₈N₈)(C₄H₆N₂)₂][K(C₁₈H₃₆N₂O₆)]₂Cl₂ or [Fe(TPP)(4-MeHIm)₂][K(222-cryptand)]₂Cl₂, is reported. This low-spin Fe^II tetra­phenyl­porphyrinate is cocrystallized with the salt [K(222-cryptand)]Cl. The crystal structure has iron(II) on an inversion center. The average Fe-N_p bond is 1.9952 (8) Å and the Fe-N_Im distance is 2.0154 (8) Å. The porphyrin core is saddled; the two imidazole rings have a relative parallel orientation (N_p = porphyrinate N atom and Im = imidazole).

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.128
• Data-to-parameter ratio = 38.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.90 mm
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Fe1    -   N3      ..      11.25 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N1      ..       7.63 su

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and SHELXTL (Sheldrick, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2004); software used to prepare material for publication: SHELXTL.

(5-methyl-4H-imidazole)(5,10,15,20-tetraphenylporphyrinato)iron(II) bis[(222-cryptand)potassium(I)] dichloride

Crystal data

[Fe(C44H28N8)(C4H6N2)2][K(C18H36N2O6)]2Cl2	Z = 1
Mr = 1734.85	F(000) = 918
Triclinic, P1	Dx = 1.315 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.4441 (2) Å	Cell parameters from 9508 reflections
b = 12.7433 (2) Å	θ = 2.4–36.1°
c = 14.5723 (2) Å	µ = 0.40 mm^−1
α = 73.504 (1)°	T = 100 K
β = 81.836 (1)°	Thick plate, red
γ = 85.061 (1)°	0.90 × 0.57 × 0.27 mm
V = 2190.74 (6) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	20486 independent reflections
Radiation source: fine-focus sealed tube	16529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 8.33 pixels mm^-1	θmax = 36.0°, θmin = 1.7°
ω and φ scans	h = −19→20
Absorption correction: multi-scan (SADABS; Blessing, 1995)	k = −21→21
Tmin = 0.718, Tmax = 0.901	l = −24→24
79801 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.5056P] where P = (Fo^2 + 2Fc^2)/3
20486 reflections	(Δ/σ)max = 0.001
529 parameters	Δρmax = 0.92 e Å^−3
0 restraints	Δρmin = −0.96 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.

The structures were solved by direct methods using SHELXS97 and refined against F² using SHELXL97;subsequent difference Fourier syntheses led to the location of the remaining non-hydrogen atoms. For the structure refinement all data were used including negative intensities. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were idealized with the standard SHELXL97 idealization methods. Hydrogen atoms were placed at calculated geometries and allowed to ride on the position of the parent atom. Hydrogen thermal parameters were set to 1.2× the equivalent isotropic U of the parent atom, 1.5× for methyl H atoms. The program SADABS was applied for the absorption correction.

Crystals were not cut because they crumble on contact.

The structure is a tetraphenyl porphyrin bound axially by two 4-methyl imidazoles. Two potassium kryptand chloride are co-crystallized.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.0000	0.5000	0.5000	0.01128 (4)
N1	−0.12618 (7)	0.57355 (6)	0.43159 (6)	0.01359 (13)
N2	−0.04582 (6)	0.35441 (6)	0.49934 (6)	0.01292 (13)
C1	−0.20453 (8)	0.52347 (8)	0.40297 (7)	0.01528 (15)
C2	−0.28032 (8)	0.60381 (8)	0.35312 (8)	0.01845 (17)
H2B	−0.3426	0.5897	0.3284	0.022*
C3	−0.24558 (9)	0.70367 (8)	0.34823 (8)	0.01799 (17)
H3A	−0.2777	0.7729	0.3177	0.022*
C4	−0.15048 (8)	0.68452 (7)	0.39821 (7)	0.01423 (15)
C5	−0.09083 (8)	0.76737 (7)	0.40898 (7)	0.01395 (14)
C6	−0.00121 (8)	0.74696 (7)	0.46062 (7)	0.01337 (14)
C7	0.05301 (8)	0.83237 (8)	0.48133 (7)	0.01534 (15)
H7A	0.0351	0.9088	0.4623	0.018*
C8	0.13434 (8)	0.78179 (8)	0.53326 (7)	0.01596 (15)
H8A	0.1838	0.8159	0.5584	0.019*
C9	−0.13120 (8)	0.33399 (7)	0.45704 (7)	0.01414 (15)
C10	−0.20784 (8)	0.41150 (8)	0.41390 (7)	0.01560 (15)
C11	−0.11870 (8)	0.88356 (8)	0.35767 (7)	0.01557 (15)
C12	−0.04028 (9)	0.94304 (8)	0.28814 (7)	0.01889 (17)
H12A	0.0303	0.9101	0.2783	0.023*
C13	−0.06338 (10)	1.04911 (9)	0.23322 (8)	0.02201 (19)
H13A	−0.0096	1.0870	0.1852	0.026*
C14	−0.16534 (10)	1.09965 (9)	0.24867 (9)	0.0238 (2)
H14A	−0.1819	1.1718	0.2109	0.029*
C15	−0.24266 (10)	1.04332 (9)	0.31996 (9)	0.0224 (2)
H15A	−0.3115	1.0783	0.3325	0.027*
C16	−0.22023 (9)	0.93556 (8)	0.37352 (8)	0.01848 (17)
H16A	−0.2745	0.8976	0.4210	0.022*
C17	−0.29868 (9)	0.37142 (8)	0.37742 (8)	0.01950 (18)
C18	−0.28603 (10)	0.35674 (9)	0.28466 (9)	0.0228 (2)
H18A	−0.2200	0.3749	0.2435	0.027*
C19	−0.36938 (11)	0.31572 (10)	0.25213 (11)	0.0297 (3)
H19A	−0.3603	0.3066	0.1890	0.036*
C20	−0.46524 (12)	0.28838 (11)	0.31218 (12)	0.0348 (3)
H20A	−0.5212	0.2584	0.2908	0.042*
C21	−0.47990 (12)	0.30440 (13)	0.40301 (12)	0.0381 (3)
H21A	−0.5465	0.2869	0.4435	0.046*
C22	−0.39630 (10)	0.34663 (12)	0.43571 (10)	0.0299 (2)
H22A	−0.4069	0.3582	0.4980	0.036*
N3	0.09052 (7)	0.51419 (6)	0.37129 (6)	0.01439 (13)
N4	0.14106 (8)	0.55232 (7)	0.21428 (6)	0.01834 (15)
H4A	0.1378	0.5767	0.1518	0.022*
C23	0.05972 (8)	0.55849 (8)	0.28470 (7)	0.01773 (16)
H23A	−0.0107	0.5906	0.2736	0.021*
C24	0.22950 (9)	0.50142 (9)	0.25736 (8)	0.02026 (18)
C25	0.19781 (8)	0.47881 (9)	0.35426 (8)	0.01981 (18)
H25A	0.2428	0.4439	0.4028	0.024*
C26	0.33252 (11)	0.47673 (13)	0.19953 (10)	0.0348 (3)
H26A	0.3940	0.4751	0.2352	0.052*
H26B	0.3421	0.5336	0.1379	0.052*
H26C	0.3291	0.4053	0.1875	0.052*
Cl1	0.19634 (2)	0.65173 (2)	−0.01394 (2)	0.02256 (5)
K1	0.278871 (17)	0.116795 (17)	0.123682 (15)	0.01596 (4)
N5	0.38991 (8)	−0.07174 (8)	0.26668 (7)	0.02208 (17)
N6	0.17186 (8)	0.29892 (8)	−0.02007 (7)	0.02182 (17)
O1	0.50409 (7)	0.11545 (8)	0.13736 (6)	0.02476 (16)
O2	0.40966 (8)	0.27337 (7)	−0.01542 (7)	0.02659 (17)
O3	0.14246 (7)	0.27638 (7)	0.18596 (6)	0.02162 (14)
O4	0.22324 (7)	0.08917 (7)	0.31980 (6)	0.02177 (15)
O5	0.25920 (7)	−0.10572 (7)	0.13011 (7)	0.02312 (15)
O6	0.13706 (7)	0.06224 (7)	0.01153 (6)	0.02120 (15)
C27	0.50128 (10)	−0.04495 (13)	0.26985 (9)	0.0306 (3)
H27A	0.5435	−0.1133	0.2977	0.037*
H27B	0.4996	0.0032	0.3128	0.037*
C28	0.55796 (9)	0.01158 (12)	0.17164 (9)	0.0283 (2)
H28A	0.6350	0.0210	0.1762	0.034*
H28B	0.5558	−0.0332	0.1265	0.034*
C29	0.56581 (10)	0.18157 (11)	0.05445 (10)	0.0271 (2)
H29A	0.5775	0.1442	0.0026	0.033*
H29B	0.6377	0.1931	0.0707	0.033*
C30	0.50581 (11)	0.28932 (11)	0.02075 (11)	0.0314 (3)
H30A	0.4864	0.3226	0.0750	0.038*
H30B	0.5526	0.3398	−0.0306	0.038*
C31	0.35582 (12)	0.37527 (11)	−0.05912 (10)	0.0321 (3)
H31A	0.4052	0.4195	−0.1128	0.039*
H31B	0.3348	0.4172	−0.0111	0.039*
C32	0.25590 (12)	0.35227 (11)	−0.09670 (9)	0.0307 (3)
H32A	0.2246	0.4222	−0.1353	0.037*
H32B	0.2776	0.3047	−0.1401	0.037*
C33	0.11460 (11)	0.38052 (9)	0.02601 (9)	0.0258 (2)
H33A	0.0587	0.4217	−0.0142	0.031*
H33B	0.1672	0.4334	0.0285	0.031*
C34	0.06065 (10)	0.33041 (9)	0.12675 (9)	0.02265 (19)
H34A	0.0210	0.3882	0.1532	0.027*
H34B	0.0078	0.2771	0.1255	0.027*
C35	0.10128 (9)	0.24709 (9)	0.28553 (8)	0.02192 (19)
H35A	0.0403	0.1980	0.2973	0.026*
H35B	0.0738	0.3136	0.3054	0.026*
C36	0.19081 (10)	0.19004 (10)	0.34285 (8)	0.02283 (19)
H36A	0.2536	0.2374	0.3277	0.027*
H36B	0.1653	0.1753	0.4126	0.027*
C37	0.29341 (10)	0.02408 (11)	0.38482 (8)	0.0254 (2)
H37A	0.2563	0.0095	0.4516	0.030*
H37B	0.3595	0.0640	0.3806	0.030*
C38	0.32485 (10)	−0.08319 (10)	0.36067 (9)	0.0264 (2)
H38A	0.3665	−0.1308	0.4113	0.032*
H38B	0.2578	−0.1204	0.3620	0.032*
C39	0.39182 (11)	−0.17372 (11)	0.23847 (10)	0.0302 (2)
H39A	0.4105	−0.2359	0.2932	0.036*
H39B	0.4499	−0.1713	0.1840	0.036*
C40	0.28594 (12)	−0.19452 (10)	0.20913 (10)	0.0299 (2)
H40A	0.2930	−0.2638	0.1903	0.036*
H40B	0.2276	−0.2013	0.2640	0.036*
C41	0.16611 (10)	−0.12722 (10)	0.09283 (9)	0.0245 (2)
H41A	0.1003	−0.1233	0.1389	0.029*
H41B	0.1741	−0.2019	0.0841	0.029*
C42	0.15431 (10)	−0.04484 (10)	−0.00158 (9)	0.0229 (2)
H42A	0.2208	−0.0478	−0.0472	0.027*
H42B	0.0921	−0.0621	−0.0293	0.027*
C43	0.13331 (11)	0.14248 (11)	−0.07905 (9)	0.0264 (2)
H43A	0.0836	0.1204	−0.1169	0.032*
H43B	0.2066	0.1488	−0.1163	0.032*
C44	0.09364 (11)	0.25139 (10)	−0.06145 (10)	0.0274 (2)
H44A	0.0778	0.3035	−0.1233	0.033*
H44B	0.0249	0.2415	−0.0172	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01185 (8)	0.01104 (7)	0.01055 (8)	0.00180 (5)	−0.00348 (6)	−0.00201 (6)
N1	0.0144 (3)	0.0127 (3)	0.0134 (3)	0.0014 (2)	−0.0042 (2)	−0.0025 (2)
N2	0.0135 (3)	0.0125 (3)	0.0123 (3)	0.0015 (2)	−0.0037 (2)	−0.0023 (2)
C1	0.0149 (4)	0.0144 (3)	0.0161 (4)	0.0013 (3)	−0.0062 (3)	−0.0020 (3)
C2	0.0177 (4)	0.0165 (4)	0.0215 (4)	0.0023 (3)	−0.0102 (3)	−0.0030 (3)
C3	0.0195 (4)	0.0155 (4)	0.0195 (4)	0.0040 (3)	−0.0101 (3)	−0.0033 (3)
C4	0.0155 (4)	0.0135 (3)	0.0135 (3)	0.0033 (3)	−0.0051 (3)	−0.0030 (3)
C5	0.0166 (4)	0.0127 (3)	0.0126 (3)	0.0034 (3)	−0.0045 (3)	−0.0034 (3)
C6	0.0148 (4)	0.0124 (3)	0.0127 (3)	0.0021 (3)	−0.0033 (3)	−0.0031 (3)
C7	0.0172 (4)	0.0130 (3)	0.0159 (4)	0.0006 (3)	−0.0042 (3)	−0.0034 (3)
C8	0.0169 (4)	0.0142 (4)	0.0166 (4)	−0.0009 (3)	−0.0046 (3)	−0.0027 (3)
C9	0.0142 (4)	0.0137 (3)	0.0139 (4)	−0.0001 (3)	−0.0036 (3)	−0.0019 (3)
C10	0.0147 (4)	0.0149 (4)	0.0167 (4)	0.0001 (3)	−0.0062 (3)	−0.0017 (3)
C11	0.0201 (4)	0.0132 (3)	0.0145 (4)	0.0036 (3)	−0.0075 (3)	−0.0042 (3)
C12	0.0243 (5)	0.0156 (4)	0.0164 (4)	0.0017 (3)	−0.0049 (3)	−0.0034 (3)
C13	0.0313 (5)	0.0159 (4)	0.0185 (4)	−0.0011 (4)	−0.0074 (4)	−0.0023 (3)
C14	0.0329 (6)	0.0144 (4)	0.0253 (5)	0.0032 (4)	−0.0146 (4)	−0.0036 (4)
C15	0.0241 (5)	0.0174 (4)	0.0284 (5)	0.0072 (3)	−0.0135 (4)	−0.0082 (4)
C16	0.0199 (4)	0.0167 (4)	0.0206 (4)	0.0039 (3)	−0.0079 (3)	−0.0066 (3)
C17	0.0180 (4)	0.0152 (4)	0.0246 (5)	−0.0004 (3)	−0.0105 (4)	−0.0006 (3)
C18	0.0246 (5)	0.0191 (4)	0.0273 (5)	0.0019 (3)	−0.0121 (4)	−0.0069 (4)
C19	0.0334 (6)	0.0235 (5)	0.0382 (7)	0.0042 (4)	−0.0217 (5)	−0.0113 (5)
C20	0.0307 (6)	0.0248 (5)	0.0503 (8)	−0.0028 (4)	−0.0243 (6)	−0.0030 (5)
C21	0.0236 (6)	0.0409 (7)	0.0437 (8)	−0.0093 (5)	−0.0098 (5)	0.0031 (6)
C22	0.0211 (5)	0.0368 (6)	0.0279 (6)	−0.0066 (4)	−0.0068 (4)	0.0008 (5)
N3	0.0155 (3)	0.0133 (3)	0.0140 (3)	0.0014 (2)	−0.0037 (3)	−0.0028 (2)
N4	0.0206 (4)	0.0191 (4)	0.0135 (3)	0.0023 (3)	−0.0012 (3)	−0.0029 (3)
C23	0.0181 (4)	0.0205 (4)	0.0134 (4)	0.0026 (3)	−0.0029 (3)	−0.0035 (3)
C24	0.0179 (4)	0.0200 (4)	0.0183 (4)	0.0035 (3)	0.0004 (3)	−0.0006 (3)
C25	0.0165 (4)	0.0220 (4)	0.0170 (4)	0.0043 (3)	−0.0021 (3)	−0.0006 (3)
C26	0.0245 (6)	0.0410 (7)	0.0261 (6)	0.0117 (5)	0.0064 (4)	0.0029 (5)
Cl1	0.02627 (12)	0.01973 (11)	0.02116 (11)	−0.00343 (8)	−0.00230 (9)	−0.00441 (8)
K1	0.01482 (8)	0.01798 (9)	0.01512 (8)	−0.00096 (6)	−0.00240 (6)	−0.00429 (6)
N5	0.0171 (4)	0.0269 (4)	0.0194 (4)	0.0038 (3)	−0.0021 (3)	−0.0032 (3)
N6	0.0258 (4)	0.0195 (4)	0.0191 (4)	0.0006 (3)	−0.0060 (3)	−0.0026 (3)
O1	0.0146 (3)	0.0355 (4)	0.0232 (4)	−0.0019 (3)	0.0011 (3)	−0.0081 (3)
O2	0.0265 (4)	0.0245 (4)	0.0260 (4)	−0.0072 (3)	−0.0016 (3)	−0.0015 (3)
O3	0.0207 (3)	0.0238 (4)	0.0197 (3)	0.0027 (3)	−0.0021 (3)	−0.0063 (3)
O4	0.0238 (4)	0.0242 (4)	0.0171 (3)	0.0037 (3)	−0.0031 (3)	−0.0065 (3)
O5	0.0244 (4)	0.0178 (3)	0.0278 (4)	0.0001 (3)	−0.0056 (3)	−0.0065 (3)
O6	0.0217 (4)	0.0233 (3)	0.0227 (4)	0.0026 (3)	−0.0071 (3)	−0.0120 (3)
C27	0.0172 (5)	0.0482 (7)	0.0225 (5)	0.0034 (5)	−0.0063 (4)	−0.0031 (5)
C28	0.0148 (4)	0.0441 (7)	0.0239 (5)	0.0029 (4)	−0.0034 (4)	−0.0066 (5)
C29	0.0171 (4)	0.0339 (6)	0.0305 (6)	−0.0076 (4)	0.0041 (4)	−0.0105 (5)
C30	0.0229 (5)	0.0313 (6)	0.0399 (7)	−0.0105 (4)	0.0021 (5)	−0.0098 (5)
C31	0.0347 (6)	0.0239 (5)	0.0306 (6)	−0.0077 (5)	0.0008 (5)	0.0036 (4)
C32	0.0377 (7)	0.0288 (6)	0.0193 (5)	−0.0013 (5)	−0.0038 (4)	0.0034 (4)
C33	0.0332 (6)	0.0145 (4)	0.0274 (5)	0.0027 (4)	−0.0059 (4)	−0.0019 (4)
C34	0.0234 (5)	0.0169 (4)	0.0279 (5)	0.0032 (3)	−0.0062 (4)	−0.0063 (4)
C35	0.0212 (5)	0.0250 (5)	0.0214 (5)	0.0013 (4)	−0.0003 (4)	−0.0111 (4)
C36	0.0226 (5)	0.0280 (5)	0.0198 (4)	0.0014 (4)	−0.0018 (4)	−0.0107 (4)
C37	0.0279 (5)	0.0305 (5)	0.0146 (4)	0.0022 (4)	−0.0024 (4)	−0.0022 (4)
C38	0.0261 (5)	0.0265 (5)	0.0195 (5)	0.0036 (4)	0.0006 (4)	0.0021 (4)
C39	0.0287 (6)	0.0254 (5)	0.0326 (6)	0.0114 (4)	−0.0059 (5)	−0.0042 (5)
C40	0.0355 (6)	0.0172 (5)	0.0343 (6)	0.0022 (4)	−0.0056 (5)	−0.0033 (4)
C41	0.0269 (5)	0.0231 (5)	0.0272 (5)	−0.0056 (4)	−0.0009 (4)	−0.0127 (4)
C42	0.0224 (5)	0.0262 (5)	0.0251 (5)	−0.0010 (4)	−0.0020 (4)	−0.0155 (4)
C43	0.0283 (5)	0.0317 (6)	0.0229 (5)	0.0045 (4)	−0.0120 (4)	−0.0111 (4)
C44	0.0290 (6)	0.0278 (5)	0.0281 (5)	0.0077 (4)	−0.0163 (5)	−0.0085 (4)

Geometric parameters (Å, º)

Fe1—N2^i	1.9903 (8)	K1—O5	2.8410 (8)
Fe1—N2	1.9903 (8)	K1—N6	3.0078 (10)
Fe1—N1^i	1.9996 (8)	K1—N5	3.0703 (10)
Fe1—N1	1.9996 (8)	N5—C38	1.4644 (16)
Fe1—N3	2.0154 (8)	N5—C27	1.4657 (16)
Fe1—N3^i	2.0155 (8)	N5—C39	1.4676 (17)
N1—C4	1.3803 (12)	N6—C44	1.4675 (16)
N1—C1	1.3804 (12)	N6—C32	1.4705 (17)
N2—C6^i	1.3749 (11)	N6—C33	1.4741 (16)
N2—C9	1.3789 (12)	O1—C28	1.4206 (16)
C1—C10	1.3936 (13)	O1—C29	1.4246 (15)
C1—C2	1.4392 (13)	O2—C30	1.4257 (16)
C2—C3	1.3587 (14)	O2—C31	1.4292 (17)
C2—H2B	0.9500	O3—C35	1.4217 (14)
C3—C4	1.4438 (13)	O3—C34	1.4305 (14)
C3—H3A	0.9500	O4—C37	1.4185 (14)
C4—C5	1.3972 (13)	O4—C36	1.4302 (14)
C5—C6	1.3982 (13)	O5—C40	1.4216 (15)
C5—C11	1.4927 (13)	O5—C41	1.4248 (15)
C6—N2^i	1.3749 (11)	O6—C42	1.4250 (14)
C6—C7	1.4498 (13)	O6—C43	1.4258 (15)
C7—C8	1.3567 (13)	C27—C28	1.5100 (18)
C7—H7A	0.9500	C27—H27A	0.9900
C8—C9^i	1.4451 (13)	C27—H27B	0.9900
C8—H8A	0.9500	C28—H28A	0.9900
C9—C10	1.3913 (13)	C28—H28B	0.9900
C9—C8^i	1.4451 (13)	C29—C30	1.493 (2)
C10—C17	1.4986 (14)	C29—H29A	0.9900
C11—C16	1.3960 (14)	C29—H29B	0.9900
C11—C12	1.4014 (15)	C30—H30A	0.9900
C12—C13	1.3908 (14)	C30—H30B	0.9900
C12—H12A	0.9500	C31—C32	1.510 (2)
C13—C14	1.3913 (17)	C31—H31A	0.9900
C13—H13A	0.9500	C31—H31B	0.9900
C14—C15	1.3900 (18)	C32—H32A	0.9900
C14—H14A	0.9500	C32—H32B	0.9900
C15—C16	1.4000 (14)	C33—C34	1.5083 (18)
C15—H15A	0.9500	C33—H33A	0.9900
C16—H16A	0.9500	C33—H33B	0.9900
C17—C22	1.3848 (17)	C34—H34A	0.9900
C17—C18	1.4017 (17)	C34—H34B	0.9900
C18—C19	1.3955 (16)	C35—C36	1.4992 (17)
C18—H18A	0.9500	C35—H35A	0.9900
C19—C20	1.383 (2)	C35—H35B	0.9900
C19—H19A	0.9500	C36—H36A	0.9900
C20—C21	1.380 (3)	C36—H36B	0.9900
C20—H20A	0.9500	C37—C38	1.5125 (19)
C21—C22	1.4078 (19)	C37—H37A	0.9900
C21—H21A	0.9500	C37—H37B	0.9900
C22—H22A	0.9500	C38—H38A	0.9900
N3—C23	1.3241 (13)	C38—H38B	0.9900
N3—C25	1.3832 (13)	C39—C40	1.508 (2)
N4—C23	1.3494 (14)	C39—H39A	0.9900
N4—C24	1.3668 (14)	C39—H39B	0.9900
N4—H4A	0.8800	C40—H40A	0.9900
C23—H23A	0.9500	C40—H40B	0.9900
C24—C25	1.3648 (15)	C41—C42	1.4923 (18)
C24—C26	1.4923 (16)	C41—H41A	0.9900
C25—H25A	0.9500	C41—H41B	0.9900
C26—H26A	0.9800	C42—H42A	0.9900
C26—H26B	0.9800	C42—H42B	0.9900
C26—H26C	0.9800	C43—C44	1.5113 (18)
K1—O4	2.7712 (8)	C43—H43A	0.9900
K1—O3	2.8031 (8)	C43—H43B	0.9900
K1—O6	2.8185 (8)	C44—H44A	0.9900
K1—O1	2.8360 (9)	C44—H44B	0.9900
K1—O2	2.8398 (9)
N2^i—Fe1—N2	180.0	C38—N5—C39	110.11 (10)
N2^i—Fe1—N1^i	90.34 (3)	C27—N5—C39	109.60 (10)
N2—Fe1—N1^i	89.66 (3)	C38—N5—K1	106.07 (7)
N2^i—Fe1—N1	89.66 (3)	C27—N5—K1	109.94 (7)
N2—Fe1—N1	90.34 (3)	C39—N5—K1	110.49 (7)
N1^i—Fe1—N1	180.0	C44—N6—C32	109.70 (10)
N2^i—Fe1—N3	89.85 (3)	C44—N6—C33	109.34 (10)
N2—Fe1—N3	90.15 (3)	C32—N6—C33	109.50 (10)
N1^i—Fe1—N3	90.65 (3)	C44—N6—K1	108.42 (7)
N1—Fe1—N3	89.35 (3)	C32—N6—K1	108.66 (7)
N2^i—Fe1—N3^i	90.15 (3)	C33—N6—K1	111.20 (7)
N2—Fe1—N3^i	89.85 (3)	C28—O1—C29	111.13 (9)
N1^i—Fe1—N3^i	89.35 (3)	C28—O1—K1	116.88 (7)
N1—Fe1—N3^i	90.65 (3)	C29—O1—K1	114.79 (7)
N3—Fe1—N3^i	180.00 (4)	C30—O2—C31	111.66 (10)
C4—N1—C1	105.24 (8)	C30—O2—K1	111.40 (7)
C4—N1—Fe1	127.78 (6)	C31—O2—K1	116.26 (7)
C1—N1—Fe1	126.89 (6)	C35—O3—C34	111.85 (9)
C6^i—N2—C9	105.19 (7)	C35—O3—K1	115.54 (6)
C6^i—N2—Fe1	127.75 (6)	C34—O3—K1	117.03 (6)
C9—N2—Fe1	127.06 (6)	C37—O4—C36	110.81 (9)
N1—C1—C10	125.85 (8)	C37—O4—K1	119.10 (7)
N1—C1—C2	110.69 (8)	C36—O4—K1	112.79 (6)
C10—C1—C2	123.32 (9)	C40—O5—C41	111.01 (9)
C3—C2—C1	106.74 (9)	C40—O5—K1	122.75 (7)
C3—C2—H2B	126.6	C41—O5—K1	115.33 (6)
C1—C2—H2B	126.6	C42—O6—C43	110.50 (9)
C2—C3—C4	106.91 (8)	C42—O6—K1	115.76 (6)
C2—C3—H3A	126.5	C43—O6—K1	111.97 (7)
C4—C3—H3A	126.5	N5—C27—C28	112.80 (10)
N1—C4—C5	125.29 (8)	N5—C27—H27A	109.0
N1—C4—C3	110.37 (8)	C28—C27—H27A	109.0
C5—C4—C3	124.33 (8)	N5—C27—H27B	109.0
C4—C5—C6	123.36 (8)	C28—C27—H27B	109.0
C4—C5—C11	118.87 (8)	H27A—C27—H27B	107.8
C6—C5—C11	117.64 (8)	O1—C28—C27	108.50 (10)
N2^i—C6—C5	125.86 (8)	O1—C28—H28A	110.0
N2^i—C6—C7	110.70 (8)	C27—C28—H28A	110.0
C5—C6—C7	123.41 (8)	O1—C28—H28B	110.0
C8—C7—C6	106.59 (8)	C27—C28—H28B	110.0
C8—C7—H7A	126.7	H28A—C28—H28B	108.4
C6—C7—H7A	126.7	O1—C29—C30	109.20 (10)
C7—C8—C9^i	106.76 (8)	O1—C29—H29A	109.8
C7—C8—H8A	126.6	C30—C29—H29A	109.8
C9^i—C8—H8A	126.6	O1—C29—H29B	109.8
N2—C9—C10	125.97 (8)	C30—C29—H29B	109.8
N2—C9—C8^i	110.69 (8)	H29A—C29—H29B	108.3
C10—C9—C8^i	123.30 (9)	O2—C30—C29	109.40 (10)
C9—C10—C1	123.67 (9)	O2—C30—H30A	109.8
C9—C10—C17	117.68 (8)	C29—C30—H30A	109.8
C1—C10—C17	118.65 (8)	O2—C30—H30B	109.8
C16—C11—C12	118.01 (9)	C29—C30—H30B	109.8
C16—C11—C5	123.33 (9)	H30A—C30—H30B	108.2
C12—C11—C5	118.64 (9)	O2—C31—C32	108.78 (11)
C13—C12—C11	121.52 (10)	O2—C31—H31A	109.9
C13—C12—H12A	119.2	C32—C31—H31A	109.9
C11—C12—H12A	119.2	O2—C31—H31B	109.9
C12—C13—C14	119.96 (11)	C32—C31—H31B	109.9
C12—C13—H13A	120.0	H31A—C31—H31B	108.3
C14—C13—H13A	120.0	N6—C32—C31	113.47 (11)
C15—C14—C13	119.21 (10)	N6—C32—H32A	108.9
C15—C14—H14A	120.4	C31—C32—H32A	108.9
C13—C14—H14A	120.4	N6—C32—H32B	108.9
C14—C15—C16	120.75 (10)	C31—C32—H32B	108.9
C14—C15—H15A	119.6	H32A—C32—H32B	107.7
C16—C15—H15A	119.6	N6—C33—C34	113.27 (9)
C11—C16—C15	120.47 (10)	N6—C33—H33A	108.9
C11—C16—H16A	119.8	C34—C33—H33A	108.9
C15—C16—H16A	119.8	N6—C33—H33B	108.9
C22—C17—C18	118.86 (11)	C34—C33—H33B	108.9
C22—C17—C10	120.30 (11)	H33A—C33—H33B	107.7
C18—C17—C10	120.84 (10)	O3—C34—C33	108.74 (10)
C19—C18—C17	120.72 (12)	O3—C34—H34A	109.9
C19—C18—H18A	119.6	C33—C34—H34A	109.9
C17—C18—H18A	119.6	O3—C34—H34B	109.9
C20—C19—C18	119.76 (13)	C33—C34—H34B	109.9
C20—C19—H19A	120.1	H34A—C34—H34B	108.3
C18—C19—H19A	120.1	O3—C35—C36	108.88 (9)
C21—C20—C19	120.27 (12)	O3—C35—H35A	109.9
C21—C20—H20A	119.9	C36—C35—H35A	109.9
C19—C20—H20A	119.9	O3—C35—H35B	109.9
C20—C21—C22	120.07 (14)	C36—C35—H35B	109.9
C20—C21—H21A	120.0	H35A—C35—H35B	108.3
C22—C21—H21A	120.0	O4—C36—C35	109.45 (9)
C17—C22—C21	120.28 (14)	O4—C36—H36A	109.8
C17—C22—H22A	119.9	C35—C36—H36A	109.8
C21—C22—H22A	119.9	O4—C36—H36B	109.8
C23—N3—C25	105.11 (8)	C35—C36—H36B	109.8
C23—N3—Fe1	127.39 (7)	H36A—C36—H36B	108.2
C25—N3—Fe1	127.49 (7)	O4—C37—C38	110.04 (10)
C23—N4—C24	107.73 (9)	O4—C37—H37A	109.7
C23—N4—H4A	126.1	C38—C37—H37A	109.7
C24—N4—H4A	126.1	O4—C37—H37B	109.7
N3—C23—N4	111.42 (9)	C38—C37—H37B	109.7
N3—C23—H23A	124.3	H37A—C37—H37B	108.2
N4—C23—H23A	124.3	N5—C38—C37	114.24 (10)
C25—C24—N4	105.81 (9)	N5—C38—H38A	108.7
C25—C24—C26	132.61 (10)	C37—C38—H38A	108.7
N4—C24—C26	121.52 (10)	N5—C38—H38B	108.7
C24—C25—N3	109.93 (9)	C37—C38—H38B	108.7
C24—C25—H25A	125.0	H38A—C38—H38B	107.6
N3—C25—H25A	125.0	N5—C39—C40	113.99 (10)
C24—C26—H26A	109.5	N5—C39—H39A	108.8
C24—C26—H26B	109.5	C40—C39—H39A	108.8
H26A—C26—H26B	109.5	N5—C39—H39B	108.8
C24—C26—H26C	109.5	C40—C39—H39B	108.8
H26A—C26—H26C	109.5	H39A—C39—H39B	107.6
H26B—C26—H26C	109.5	O5—C40—C39	108.92 (10)
O4—K1—O3	61.01 (2)	O5—C40—H40A	109.9
O4—K1—O6	121.37 (3)	C39—C40—H40A	109.9
O3—K1—O6	97.75 (2)	O5—C40—H40B	109.9
O4—K1—O1	92.66 (3)	C39—C40—H40B	109.9
O3—K1—O1	117.69 (3)	H40A—C40—H40B	108.3
O6—K1—O1	140.37 (3)	O5—C41—C42	109.54 (9)
O4—K1—O2	130.48 (3)	O5—C41—H41A	109.8
O3—K1—O2	93.67 (3)	C42—C41—H41A	109.8
O6—K1—O2	102.58 (3)	O5—C41—H41B	109.8
O1—K1—O2	60.51 (3)	C42—C41—H41B	109.8
O4—K1—O5	95.88 (3)	H41A—C41—H41B	108.2
O3—K1—O5	134.94 (3)	O6—C42—C41	109.97 (9)
O6—K1—O5	59.81 (2)	O6—C42—H42A	109.7
O1—K1—O5	100.25 (3)	C41—C42—H42A	109.7
O2—K1—O5	127.47 (3)	O6—C42—H42B	109.7
O4—K1—N6	120.43 (3)	C41—C42—H42B	109.7
O3—K1—N6	59.90 (3)	H42A—C42—H42B	108.2
O6—K1—N6	61.40 (3)	O6—C43—C44	108.94 (10)
O1—K1—N6	120.72 (3)	O6—C43—H43A	109.9
O2—K1—N6	60.68 (3)	C44—C43—H43A	109.9
O5—K1—N6	120.77 (3)	O6—C43—H43B	109.9
O4—K1—N5	60.85 (3)	C44—C43—H43B	109.9
O3—K1—N5	121.43 (3)	H43A—C43—H43B	108.3
O6—K1—N5	117.76 (3)	N6—C44—C43	113.38 (10)
O1—K1—N5	59.12 (3)	N6—C44—H44A	108.9
O2—K1—N5	118.95 (3)	C43—C44—H44A	108.9
O5—K1—N5	58.27 (3)	N6—C44—H44B	108.9
N6—K1—N5	178.66 (3)	C43—C44—H44B	108.9
C38—N5—C27	110.59 (10)	H44A—C44—H44B	107.7

Symmetry code: (i) −x, −y+1, −z+1.