Synthesis and characterization of (cryptand-222)potassium (2-methyl­imidazolato)(meso-tetra­phenyl­porphinato)ferrate(II)–2-methyl­imidazole–tetra­hydro­furan (1/1/2)

Metalloporphyrin complexes containing an additional imidazole ligand can provide information about the effect of deprotonation or hydrogen bonding on the axial histidine unit in heme proteins. The title high-spin five-coordinate imidazolate-ligated iron(II) porphyrinate, [K(C₁₈H₃₆N₂O₆)][Fe(C₄H₅N₂)(C₄₄H₂₈N₄)]·C₄H₆N₂·2C₄H₈O, has been synthesized and investigated. The solvated salt crystallizes with one 2-methyl­imidazole mol­ecule, two tetra­hydro­furan solvent mol­ecules and a potassium cation chelated inside a cryptand-222 (4,7,13,16,21,24-hexa­oxa-1,10-di­aza­bicyclo­[8.8.8]hexa­cosa­ne) mol­ecule. The imidazolate ligand is ordered. The average Fe—Np (Np is a porphyrin N atom) bond length is 2.113 (11) Å and the axial Fe—N_Im (N_Im is an imidazolate N atom) is 2.0739 (13) Å. The out-of-plane displacement of the Fe^II atom from the 24-atom mean plane is 0.6098 (5) Å, indicating an apparent doming of the porphyrin core.

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 and SAINT (Bruker, 2013); data reduction: SAINT and XPREP (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)potassium (2-methylimidazolato)(meso-tetraphenylporphinato)ferrate(II)–2-methylimidazole–tetrahydrofuran (1/1/2)

Crystal data

[K(C18H36N2O6)][Fe(C4H5N2)(C44H28N4)]·C4H6N2·2C4H8O	F(000) = 2952
Mr = 1391.55	Dx = 1.294 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0866 (16) Å	Cell parameters from 9389 reflections
b = 21.934 (3) Å	θ = 2.4–27.0°
c = 24.898 (3) Å	µ = 0.33 mm^−1
β = 91.214 (4)°	T = 100 K
V = 7145.1 (16) Å^3	Block, black
Z = 4	0.90 × 0.44 × 0.17 mm

Data collection

Bruker D8 QUEST System with area detector diffractometer	13209 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
φ and ω scans	θmax = 27.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→16
Tmin = 0.839, Tmax = 0.945	k = −28→28
151771 measured reflections	l = −31→31
15806 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 4.8842P] where P = (Fo^2 + 2Fc^2)/3
15806 reflections	(Δ/σ)max = 0.002
1033 parameters	Δρmax = 0.34 e Å^−3
486 restraints	Δρmin = −0.38 e Å^−3

Special details

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.

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 > 2sigma(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)
Fe1	0.19828 (2)	0.71079 (2)	0.33136 (2)	0.01169 (5)
N1	0.16233 (9)	0.68903 (5)	0.25093 (5)	0.0139 (2)
N2	0.04382 (9)	0.73659 (5)	0.33865 (5)	0.0138 (2)
N3	0.22927 (9)	0.77518 (5)	0.39251 (5)	0.0132 (2)
N4	0.34653 (9)	0.73152 (5)	0.30302 (5)	0.0136 (2)
C101	0.22939 (11)	0.67350 (7)	0.21139 (5)	0.0148 (3)
C102	0.06632 (10)	0.67692 (7)	0.23055 (5)	0.0145 (3)
C103	−0.03588 (10)	0.72015 (6)	0.30504 (5)	0.0141 (3)
C104	0.00055 (10)	0.76281 (7)	0.38284 (6)	0.0148 (3)
C105	0.16171 (11)	0.79225 (6)	0.43134 (5)	0.0134 (3)
C106	0.32476 (10)	0.79061 (6)	0.41178 (6)	0.0139 (3)
C107	0.42524 (10)	0.75611 (6)	0.33321 (6)	0.0144 (3)
C108	0.38962 (10)	0.70922 (6)	0.25727 (5)	0.0138 (3)
C201	0.17298 (11)	0.65122 (7)	0.16485 (6)	0.0193 (3)
H20A	0.2011	0.6380	0.1320	0.023*
C202	0.07297 (11)	0.65277 (7)	0.17685 (6)	0.0187 (3)
H20B	0.0175	0.6403	0.1542	0.022*
C203	−0.13174 (11)	0.73762 (7)	0.32825 (6)	0.0174 (3)
H20C	−0.1980	0.7318	0.3127	0.021*
C204	−0.10947 (11)	0.76375 (7)	0.37628 (6)	0.0185 (3)
H20D	−0.1570	0.7797	0.4010	0.022*
C205	0.21713 (11)	0.81759 (6)	0.47685 (6)	0.0153 (3)
H20E	0.1886	0.8320	0.5092	0.018*
C206	0.31725 (11)	0.81699 (7)	0.46470 (6)	0.0160 (3)
H20F	0.3723	0.8312	0.4868	0.019*
C207	0.52043 (11)	0.74880 (7)	0.30564 (6)	0.0168 (3)
H20G	0.5859	0.7622	0.3179	0.020*
C208	0.49890 (11)	0.71945 (7)	0.25919 (6)	0.0164 (3)
H20H	0.5464	0.7077	0.2328	0.020*
C301	0.33594 (10)	0.68091 (6)	0.21451 (5)	0.0141 (3)
C302	−0.02583 (10)	0.68992 (6)	0.25568 (6)	0.0142 (3)
C303	0.05475 (11)	0.78661 (6)	0.42747 (5)	0.0142 (3)
C304	0.41617 (10)	0.78289 (6)	0.38396 (6)	0.0146 (3)
C1	0.39443 (10)	0.65995 (7)	0.16714 (5)	0.0148 (3)
C2	0.45046 (10)	0.70137 (7)	0.13713 (6)	0.0166 (3)
H2A	0.4552	0.7426	0.1486	0.020*
C3	0.49953 (11)	0.68343 (8)	0.09083 (6)	0.0203 (3)
H3A	0.5373	0.7123	0.0708	0.024*
C4	0.49325 (11)	0.62335 (8)	0.07394 (6)	0.0225 (3)
H4A	0.5258	0.6110	0.0420	0.027*
C5	0.43939 (11)	0.58123 (8)	0.10378 (6)	0.0216 (3)
H5A	0.4360	0.5399	0.0925	0.026*
C6	0.39033 (11)	0.59923 (7)	0.15017 (6)	0.0186 (3)
H6A	0.3538	0.5701	0.1704	0.022*
C7	−0.12174 (10)	0.66893 (7)	0.22761 (5)	0.0152 (3)
C8	−0.18489 (11)	0.70883 (7)	0.19900 (6)	0.0176 (3)
H8A	−0.1673	0.7508	0.1969	0.021*
C9	−0.27357 (11)	0.68788 (8)	0.17337 (6)	0.0207 (3)
H9A	−0.3157	0.7154	0.1535	0.025*
C10	−0.30063 (11)	0.62698 (8)	0.17681 (6)	0.0214 (3)
H10A	−0.3621	0.6129	0.1600	0.026*
C11	−0.23802 (12)	0.58678 (8)	0.20473 (6)	0.0228 (3)
H11A	−0.2561	0.5449	0.2069	0.027*
C12	−0.14858 (11)	0.60753 (7)	0.22961 (6)	0.0198 (3)
H12A	−0.1052	0.5795	0.2482	0.024*
C13	−0.00549 (10)	0.80871 (7)	0.47396 (5)	0.0149 (3)
C14	−0.00314 (11)	0.87004 (7)	0.48881 (6)	0.0184 (3)
H14A	0.0351	0.8983	0.4684	0.022*
C15	−0.05635 (11)	0.89018 (8)	0.53323 (6)	0.0220 (3)
H15A	−0.0544	0.9320	0.5430	0.026*
C16	−0.11217 (11)	0.84925 (8)	0.56326 (6)	0.0227 (3)
H16A	−0.1480	0.8630	0.5938	0.027*
C17	−0.11572 (11)	0.78837 (8)	0.54876 (6)	0.0219 (3)
H17A	−0.1541	0.7603	0.5693	0.026*
C18	−0.06303 (11)	0.76820 (7)	0.50412 (6)	0.0181 (3)
H18A	−0.0663	0.7264	0.4941	0.022*
C19	0.51249 (11)	0.80649 (7)	0.41031 (6)	0.0177 (3)
C20	0.55498 (14)	0.86072 (8)	0.39428 (9)	0.0403 (5)
H20I	0.5226	0.8836	0.3664	0.048*
C21	0.64456 (15)	0.88262 (9)	0.41827 (10)	0.0470 (6)
H21A	0.6724	0.9204	0.4069	0.056*
C22	0.69283 (12)	0.85009 (9)	0.45818 (7)	0.0315 (4)
H22A	0.7549	0.8646	0.4740	0.038*
C23	0.65093 (12)	0.79654 (10)	0.47505 (7)	0.0340 (4)
H23A	0.6833	0.7742	0.5034	0.041*
C24	0.56132 (12)	0.77434 (9)	0.45114 (6)	0.0267 (4)
H24A	0.5335	0.7368	0.4630	0.032*
N5	0.20709 (9)	0.63079 (6)	0.37563 (5)	0.0170 (2)
N6	0.20867 (10)	0.53291 (6)	0.40308 (6)	0.0229 (3)
C25	0.22094 (12)	0.62929 (7)	0.43064 (6)	0.0211 (3)
H25A	0.2286	0.6638	0.4534	0.025*
C26	0.22173 (11)	0.57007 (7)	0.44694 (6)	0.0209 (3)
H26A	0.2300	0.5566	0.4830	0.025*
C27	0.20032 (12)	0.57162 (7)	0.36162 (6)	0.0221 (3)
C28	0.1855 (2)	0.55046 (8)	0.30498 (8)	0.0463 (6)
H28A	0.1782	0.5060	0.3044	0.070*
H28B	0.2448	0.5623	0.2840	0.070*
H28C	0.1237	0.5692	0.2894	0.070*
K1	0.27377 (2)	0.95119 (2)	0.13967 (2)	0.01830 (7)
N7	0.44205 (10)	1.04638 (6)	0.15041 (5)	0.0219 (3)
N8	0.10385 (10)	0.85614 (6)	0.12910 (5)	0.0235 (3)
O1	0.22874 (9)	0.87307 (5)	0.22608 (4)	0.0275 (3)
O2	0.37296 (9)	0.96858 (5)	0.23942 (4)	0.0263 (2)
O3	0.07392 (8)	0.98762 (5)	0.10861 (5)	0.0268 (3)
O4	0.23433 (8)	1.07361 (5)	0.10895 (5)	0.0245 (2)
O5	0.29521 (8)	0.85447 (5)	0.06817 (4)	0.0223 (2)
O6	0.46006 (8)	0.93583 (5)	0.08497 (4)	0.0215 (2)
C29	0.09927 (13)	0.81901 (8)	0.17787 (7)	0.0279 (4)
H29A	0.1479	0.7846	0.1750	0.033*
H29B	0.0297	0.8017	0.1807	0.033*
C30	0.12435 (14)	0.85446 (8)	0.22809 (7)	0.0303 (4)
H30A	0.0794	0.8906	0.2304	0.036*
H30B	0.1136	0.8287	0.2601	0.036*
C31	0.26574 (16)	0.89274 (8)	0.27690 (7)	0.0344 (4)
H31A	0.2635	0.8586	0.3029	0.041*
H31B	0.2222	0.9261	0.2903	0.041*
C32	0.37302 (15)	0.91464 (8)	0.27185 (7)	0.0344 (4)
H32A	0.4027	0.9237	0.3079	0.041*
H32B	0.4151	0.8827	0.2550	0.041*
C33	0.46920 (13)	0.99831 (8)	0.24035 (7)	0.0300 (4)
H33A	0.5214	0.9711	0.2250	0.036*
H33B	0.4900	1.0077	0.2779	0.036*
C34	0.46291 (13)	1.05654 (8)	0.20824 (7)	0.0273 (4)
H34A	0.4082	1.0825	0.2228	0.033*
H34B	0.5282	1.0789	0.2126	0.033*
C35	0.00595 (12)	0.88762 (8)	0.11991 (8)	0.0304 (4)
H35A	−0.0200	0.9016	0.1549	0.036*
H35B	−0.0442	0.8582	0.1046	0.036*
C36	0.01289 (13)	0.94154 (8)	0.08273 (8)	0.0298 (4)
H36A	0.0444	0.9291	0.0486	0.036*
H36B	−0.0563	0.9576	0.0744	0.036*
C37	0.06746 (13)	1.04352 (8)	0.07944 (7)	0.0306 (4)
H37A	−0.0047	1.0568	0.0763	0.037*
H37B	0.0938	1.0377	0.0428	0.037*
C38	0.12929 (12)	1.09069 (8)	0.10854 (7)	0.0287 (4)
H38A	0.1206	1.1307	0.0905	0.034*
H38B	0.1055	1.0946	0.1459	0.034*
C39	0.29809 (13)	1.11901 (7)	0.13338 (7)	0.0269 (4)
H39A	0.2852	1.1211	0.1724	0.032*
H39B	0.2824	1.1594	0.1175	0.032*
C40	0.40801 (12)	1.10325 (7)	0.12452 (7)	0.0253 (3)
H40A	0.4189	1.0999	0.0854	0.030*
H40B	0.4513	1.1371	0.1382	0.030*
C41	0.12720 (13)	0.81697 (8)	0.08300 (7)	0.0278 (4)
H41A	0.1066	0.8382	0.0494	0.033*
H41B	0.0865	0.7790	0.0852	0.033*
C42	0.23852 (13)	0.80079 (7)	0.08070 (7)	0.0270 (4)
H42A	0.2623	0.7842	0.1157	0.032*
H42B	0.2490	0.7693	0.0529	0.032*
C43	0.39721 (12)	0.84045 (7)	0.05446 (7)	0.0253 (3)
H43A	0.3973	0.8113	0.0241	0.030*
H43B	0.4333	0.8213	0.0855	0.030*
C44	0.45040 (12)	0.89780 (7)	0.03905 (6)	0.0230 (3)
H44A	0.5189	0.8882	0.0252	0.028*
H44B	0.4106	0.9190	0.0104	0.028*
C45	0.51221 (12)	0.99094 (7)	0.07310 (6)	0.0229 (3)
H45A	0.4691	1.0166	0.0490	0.027*
H45B	0.5766	0.9817	0.0546	0.027*
C46	0.53528 (12)	1.02458 (8)	0.12456 (7)	0.0258 (3)
H46A	0.5730	0.9972	0.1496	0.031*
H46B	0.5799	1.0598	0.1169	0.031*
N9A	0.3285 (2)	0.32139 (14)	0.39617 (15)	0.0347 (7)	0.625 (4)
N10A	0.26303 (16)	0.41324 (10)	0.38173 (11)	0.0257 (7)	0.625 (4)
H10B	0.2327	0.4483	0.3880	0.031*	0.625 (4)
C47A	0.3395 (4)	0.33728 (19)	0.3426 (2)	0.0348 (10)	0.625 (4)
H47A	0.3706	0.3125	0.3162	0.042*	0.625 (4)
C48A	0.2994 (3)	0.39347 (19)	0.33346 (14)	0.0307 (8)	0.625 (4)
H48A	0.2969	0.4149	0.3003	0.037*	0.625 (4)
C49A	0.2826 (4)	0.3690 (3)	0.4174 (2)	0.0262 (11)	0.625 (4)
C50A	0.2529 (6)	0.3744 (2)	0.4754 (3)	0.0302 (13)	0.625 (4)
H50A	0.2940	0.3460	0.4973	0.045*	0.625 (4)
H50B	0.1803	0.3644	0.4788	0.045*	0.625 (4)
H50C	0.2651	0.4161	0.4879	0.045*	0.625 (4)
N9B	0.3201 (3)	0.31654 (18)	0.4324 (2)	0.0275 (11)	0.375 (4)
N10B	0.2661 (3)	0.4124 (2)	0.42472 (16)	0.0218 (11)	0.375 (4)
H10C	0.2507	0.4477	0.4099	0.026*	0.375 (4)
C47B	0.2862 (4)	0.3375 (3)	0.48110 (19)	0.0254 (11)	0.375 (4)
H47B	0.2852	0.3140	0.5131	0.031*	0.375 (4)
C48B	0.2543 (9)	0.3966 (4)	0.4770 (5)	0.0256 (18)	0.375 (4)
H48B	0.2291	0.4216	0.5049	0.031*	0.375 (4)
C49B	0.3064 (6)	0.3629 (5)	0.3995 (3)	0.0225 (17)	0.375 (4)
C50B	0.3328 (6)	0.3646 (4)	0.3415 (3)	0.0334 (17)	0.375 (4)
H50D	0.3302	0.3232	0.3267	0.050*	0.375 (4)
H50E	0.4018	0.3812	0.3377	0.050*	0.375 (4)
H50F	0.2837	0.3905	0.3219	0.050*	0.375 (4)
O7A	0.1587 (9)	0.9742 (10)	0.4504 (5)	0.032 (2)	0.501 (10)
C51A	0.2128 (8)	0.9628 (9)	0.4027 (5)	0.0317 (18)	0.501 (10)
H51A	0.1879	0.9902	0.3737	0.038*	0.501 (10)
H51B	0.2020	0.9201	0.3910	0.038*	0.501 (10)
C52A	0.3254 (4)	0.9741 (3)	0.4143 (2)	0.0351 (12)	0.501 (10)
H52A	0.3569	0.9972	0.3847	0.042*	0.501 (10)
H52B	0.3628	0.9353	0.4197	0.042*	0.501 (10)
C53A	0.3248 (4)	1.0115 (3)	0.4658 (2)	0.0401 (14)	0.501 (10)
H53A	0.3875	1.0047	0.4879	0.048*	0.501 (10)
H53B	0.3174	1.0556	0.4582	0.048*	0.501 (10)
C54A	0.2310 (8)	0.9861 (8)	0.4928 (4)	0.037 (2)	0.501 (10)
H54A	0.2481	0.9481	0.5125	0.044*	0.501 (10)
H54B	0.2033	1.0161	0.5184	0.044*	0.501 (10)
O7B	0.1692 (8)	0.9706 (10)	0.4603 (5)	0.0274 (17)	0.499 (10)
C51B	0.2203 (9)	0.9680 (9)	0.4103 (5)	0.034 (2)	0.499 (10)
H51C	0.1781	0.9867	0.3813	0.041*	0.499 (10)
H51D	0.2354	0.9252	0.4004	0.041*	0.499 (10)
C52B	0.3186 (4)	1.0038 (4)	0.4197 (2)	0.0331 (14)	0.499 (10)
H52C	0.3722	0.9916	0.3943	0.040*	0.499 (10)
H52D	0.3070	1.0483	0.4171	0.040*	0.499 (10)
C53B	0.3452 (4)	0.9843 (3)	0.47670 (18)	0.0325 (12)	0.499 (10)
H53C	0.3815	0.9447	0.4772	0.039*	0.499 (10)
H53D	0.3883	1.0152	0.4952	0.039*	0.499 (10)
C54B	0.2425 (8)	0.9790 (7)	0.5026 (4)	0.0312 (19)	0.499 (10)
H54C	0.2418	0.9439	0.5275	0.037*	0.499 (10)
H54D	0.2272	1.0165	0.5230	0.037*	0.499 (10)
O8A	0.2208 (3)	0.47210 (16)	0.1581 (2)	0.0851 (15)	0.600 (5)
C55A	0.1202 (4)	0.4734 (3)	0.1340 (2)	0.0791 (16)	0.600 (5)
H55A	0.1170	0.4482	0.1011	0.095*	0.600 (5)
H55B	0.0996	0.5156	0.1249	0.095*	0.600 (5)
C56A	0.0523 (5)	0.4472 (4)	0.1767 (3)	0.085 (2)	0.600 (5)
H56A	0.0198	0.4806	0.1970	0.103*	0.600 (5)
H56B	−0.0022	0.4219	0.1599	0.103*	0.600 (5)
C57A	0.1166 (4)	0.4097 (3)	0.2131 (2)	0.0582 (15)	0.600 (5)
H57A	0.0984	0.3660	0.2098	0.070*	0.600 (5)
H57B	0.1090	0.4226	0.2509	0.070*	0.600 (5)
C58A	0.2249 (6)	0.4211 (4)	0.1944 (3)	0.078 (2)	0.600 (5)
H58A	0.2707	0.4304	0.2255	0.094*	0.600 (5)
H58B	0.2514	0.3845	0.1760	0.094*	0.600 (5)
O8B	0.2189 (5)	0.4487 (2)	0.1976 (3)	0.0468 (14)	0.400 (5)
C55B	0.1646 (4)	0.4950 (3)	0.1704 (2)	0.0396 (14)	0.400 (5)
H55C	0.1943	0.5019	0.1346	0.047*	0.400 (5)
H55D	0.1696	0.5335	0.1910	0.047*	0.400 (5)
C56B	0.0547 (5)	0.4766 (3)	0.1639 (4)	0.052 (2)	0.400 (5)
H56C	0.0226	0.4947	0.1313	0.063*	0.400 (5)
H56D	0.0147	0.4878	0.1957	0.063*	0.400 (5)
C57B	0.0663 (5)	0.4086 (3)	0.1588 (3)	0.0495 (16)	0.400 (5)
H57C	0.0873	0.3966	0.1223	0.059*	0.400 (5)
H57D	0.0027	0.3869	0.1680	0.059*	0.400 (5)
C58B	0.1509 (7)	0.3980 (4)	0.2004 (4)	0.056 (2)	0.400 (5)
H58C	0.1220	0.3949	0.2367	0.067*	0.400 (5)
H58D	0.1876	0.3596	0.1926	0.067*	0.400 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01060 (10)	0.01342 (10)	0.01104 (9)	−0.00167 (7)	−0.00018 (7)	−0.00110 (8)
N1	0.0108 (5)	0.0177 (6)	0.0131 (6)	−0.0011 (5)	0.0002 (4)	−0.0012 (5)
N2	0.0121 (6)	0.0164 (6)	0.0130 (6)	−0.0019 (5)	−0.0003 (4)	−0.0024 (5)
N3	0.0117 (5)	0.0149 (6)	0.0130 (6)	−0.0024 (4)	0.0002 (4)	−0.0007 (5)
N4	0.0112 (5)	0.0159 (6)	0.0136 (6)	−0.0014 (5)	0.0000 (4)	−0.0012 (5)
C101	0.0141 (7)	0.0181 (7)	0.0121 (6)	0.0008 (5)	0.0001 (5)	−0.0004 (5)
C102	0.0129 (7)	0.0177 (7)	0.0129 (7)	−0.0011 (5)	−0.0010 (5)	−0.0006 (5)
C103	0.0124 (6)	0.0161 (7)	0.0140 (7)	−0.0028 (5)	0.0008 (5)	−0.0003 (5)
C104	0.0136 (7)	0.0167 (7)	0.0143 (7)	−0.0026 (5)	0.0015 (5)	−0.0015 (5)
C105	0.0161 (7)	0.0119 (6)	0.0124 (6)	−0.0019 (5)	0.0013 (5)	0.0000 (5)
C106	0.0137 (7)	0.0129 (7)	0.0150 (7)	−0.0013 (5)	−0.0026 (5)	0.0004 (5)
C107	0.0121 (6)	0.0146 (7)	0.0164 (7)	−0.0017 (5)	−0.0014 (5)	0.0011 (5)
C108	0.0117 (6)	0.0158 (7)	0.0140 (6)	−0.0002 (5)	0.0012 (5)	0.0023 (5)
C201	0.0163 (7)	0.0287 (8)	0.0129 (7)	0.0018 (6)	−0.0002 (5)	−0.0049 (6)
C202	0.0140 (7)	0.0268 (8)	0.0151 (7)	0.0002 (6)	−0.0031 (5)	−0.0050 (6)
C203	0.0113 (7)	0.0226 (8)	0.0183 (7)	−0.0027 (6)	0.0001 (5)	−0.0038 (6)
C204	0.0131 (7)	0.0244 (8)	0.0182 (7)	−0.0021 (6)	0.0032 (5)	−0.0046 (6)
C205	0.0177 (7)	0.0153 (7)	0.0129 (6)	−0.0005 (6)	−0.0011 (5)	−0.0020 (5)
C206	0.0171 (7)	0.0160 (7)	0.0147 (7)	−0.0009 (6)	−0.0042 (5)	−0.0023 (6)
C207	0.0115 (7)	0.0205 (7)	0.0184 (7)	−0.0023 (5)	−0.0006 (5)	0.0015 (6)
C208	0.0120 (7)	0.0219 (7)	0.0155 (7)	0.0001 (6)	0.0019 (5)	0.0013 (6)
C301	0.0139 (7)	0.0163 (7)	0.0122 (6)	0.0012 (5)	0.0012 (5)	0.0014 (5)
C302	0.0128 (7)	0.0158 (7)	0.0141 (7)	−0.0012 (5)	−0.0012 (5)	−0.0002 (5)
C303	0.0159 (7)	0.0139 (7)	0.0130 (6)	−0.0017 (5)	0.0016 (5)	−0.0006 (5)
C304	0.0130 (7)	0.0148 (7)	0.0158 (7)	−0.0014 (5)	−0.0025 (5)	0.0000 (5)
C1	0.0095 (6)	0.0230 (7)	0.0117 (6)	0.0023 (5)	−0.0025 (5)	−0.0010 (6)
C2	0.0128 (7)	0.0230 (8)	0.0139 (7)	0.0024 (6)	−0.0023 (5)	0.0003 (6)
C3	0.0153 (7)	0.0326 (9)	0.0131 (7)	0.0027 (6)	0.0001 (5)	0.0038 (6)
C4	0.0166 (7)	0.0395 (9)	0.0114 (7)	0.0095 (7)	−0.0011 (5)	−0.0034 (6)
C5	0.0184 (7)	0.0268 (8)	0.0195 (7)	0.0071 (6)	−0.0049 (6)	−0.0075 (6)
C6	0.0138 (7)	0.0238 (8)	0.0181 (7)	0.0019 (6)	−0.0019 (5)	−0.0008 (6)
C7	0.0109 (6)	0.0221 (7)	0.0128 (6)	−0.0019 (5)	0.0018 (5)	−0.0053 (6)
C8	0.0135 (7)	0.0207 (7)	0.0187 (7)	−0.0015 (6)	0.0010 (5)	−0.0035 (6)
C9	0.0121 (7)	0.0313 (9)	0.0188 (7)	0.0010 (6)	−0.0005 (5)	−0.0033 (6)
C10	0.0119 (7)	0.0346 (9)	0.0176 (7)	−0.0052 (6)	0.0010 (5)	−0.0093 (6)
C11	0.0220 (8)	0.0244 (8)	0.0220 (8)	−0.0073 (6)	0.0023 (6)	−0.0074 (6)
C12	0.0178 (7)	0.0224 (8)	0.0191 (7)	−0.0018 (6)	−0.0009 (6)	−0.0032 (6)
C13	0.0114 (6)	0.0208 (7)	0.0124 (6)	−0.0014 (5)	−0.0008 (5)	−0.0025 (6)
C14	0.0162 (7)	0.0212 (8)	0.0179 (7)	−0.0022 (6)	−0.0003 (6)	−0.0026 (6)
C15	0.0169 (7)	0.0276 (8)	0.0213 (8)	0.0026 (6)	−0.0036 (6)	−0.0100 (6)
C16	0.0125 (7)	0.0419 (10)	0.0137 (7)	0.0040 (6)	−0.0008 (5)	−0.0075 (7)
C17	0.0135 (7)	0.0367 (9)	0.0153 (7)	−0.0020 (6)	0.0005 (5)	0.0027 (7)
C18	0.0144 (7)	0.0216 (7)	0.0181 (7)	−0.0024 (6)	−0.0012 (5)	−0.0002 (6)
C19	0.0121 (7)	0.0233 (8)	0.0176 (7)	0.0002 (6)	−0.0011 (5)	−0.0066 (6)
C20	0.0315 (10)	0.0271 (9)	0.0611 (13)	−0.0105 (8)	−0.0273 (9)	0.0112 (9)
C21	0.0341 (11)	0.0288 (10)	0.0768 (16)	−0.0141 (8)	−0.0245 (10)	0.0022 (10)
C22	0.0131 (7)	0.0477 (11)	0.0335 (9)	−0.0027 (7)	−0.0064 (7)	−0.0184 (8)
C23	0.0145 (8)	0.0707 (14)	0.0166 (8)	−0.0019 (8)	−0.0030 (6)	0.0021 (8)
C24	0.0148 (7)	0.0471 (10)	0.0181 (8)	−0.0049 (7)	−0.0003 (6)	0.0062 (7)
N5	0.0161 (6)	0.0167 (6)	0.0183 (6)	−0.0013 (5)	−0.0006 (5)	−0.0002 (5)
N6	0.0216 (7)	0.0179 (6)	0.0291 (7)	−0.0005 (5)	−0.0046 (5)	0.0036 (6)
C25	0.0251 (8)	0.0209 (8)	0.0173 (7)	−0.0016 (6)	0.0006 (6)	−0.0019 (6)
C26	0.0198 (7)	0.0238 (8)	0.0192 (7)	−0.0005 (6)	0.0004 (6)	0.0038 (6)
C27	0.0242 (8)	0.0178 (8)	0.0242 (8)	−0.0005 (6)	−0.0057 (6)	0.0005 (6)
C28	0.0900 (17)	0.0184 (9)	0.0298 (10)	0.0004 (10)	−0.0186 (10)	−0.0049 (8)
K1	0.01733 (15)	0.01990 (16)	0.01767 (15)	0.00142 (12)	0.00037 (12)	0.00023 (12)
N7	0.0190 (6)	0.0220 (7)	0.0248 (7)	−0.0002 (5)	−0.0010 (5)	−0.0045 (6)
N8	0.0195 (7)	0.0238 (7)	0.0273 (7)	0.0001 (5)	0.0016 (5)	0.0020 (6)
O1	0.0345 (7)	0.0281 (6)	0.0199 (6)	−0.0004 (5)	0.0012 (5)	0.0006 (5)
O2	0.0322 (6)	0.0227 (6)	0.0236 (6)	0.0025 (5)	−0.0089 (5)	0.0012 (5)
O3	0.0216 (6)	0.0247 (6)	0.0336 (6)	−0.0007 (5)	−0.0076 (5)	0.0076 (5)
O4	0.0212 (6)	0.0209 (6)	0.0313 (6)	0.0012 (4)	−0.0045 (5)	−0.0007 (5)
O5	0.0223 (6)	0.0174 (5)	0.0274 (6)	−0.0010 (4)	0.0035 (4)	−0.0025 (4)
O6	0.0236 (6)	0.0207 (5)	0.0203 (5)	−0.0022 (4)	0.0047 (4)	−0.0022 (4)
C29	0.0258 (8)	0.0238 (8)	0.0343 (9)	−0.0025 (7)	0.0037 (7)	0.0051 (7)
C30	0.0329 (9)	0.0296 (9)	0.0287 (9)	0.0014 (7)	0.0096 (7)	0.0070 (7)
C31	0.0572 (12)	0.0264 (9)	0.0196 (8)	0.0018 (8)	−0.0030 (8)	0.0026 (7)
C32	0.0509 (11)	0.0275 (9)	0.0241 (9)	0.0049 (8)	−0.0156 (8)	0.0036 (7)
C33	0.0280 (9)	0.0365 (10)	0.0250 (8)	0.0040 (7)	−0.0085 (7)	−0.0059 (7)
C34	0.0250 (8)	0.0286 (9)	0.0281 (9)	−0.0031 (7)	−0.0038 (7)	−0.0098 (7)
C35	0.0168 (8)	0.0308 (9)	0.0436 (10)	−0.0020 (7)	0.0013 (7)	0.0036 (8)
C36	0.0185 (8)	0.0307 (9)	0.0399 (10)	−0.0020 (7)	−0.0077 (7)	0.0022 (8)
C37	0.0259 (9)	0.0302 (9)	0.0353 (10)	0.0018 (7)	−0.0088 (7)	0.0102 (8)
C38	0.0235 (8)	0.0255 (9)	0.0369 (10)	0.0054 (7)	−0.0035 (7)	0.0063 (7)
C39	0.0290 (9)	0.0196 (8)	0.0319 (9)	−0.0001 (7)	−0.0021 (7)	−0.0033 (7)
C40	0.0265 (8)	0.0212 (8)	0.0283 (8)	−0.0050 (7)	0.0009 (7)	−0.0030 (7)
C41	0.0268 (9)	0.0255 (9)	0.0310 (9)	−0.0076 (7)	−0.0010 (7)	−0.0054 (7)
C42	0.0292 (9)	0.0188 (8)	0.0330 (9)	−0.0052 (7)	0.0040 (7)	−0.0059 (7)
C43	0.0265 (8)	0.0218 (8)	0.0278 (8)	0.0030 (7)	0.0062 (7)	−0.0041 (7)
C44	0.0225 (8)	0.0259 (8)	0.0207 (8)	0.0023 (6)	0.0046 (6)	−0.0043 (6)
C45	0.0199 (8)	0.0235 (8)	0.0256 (8)	−0.0023 (6)	0.0052 (6)	0.0014 (6)
C46	0.0175 (8)	0.0270 (9)	0.0329 (9)	−0.0025 (6)	0.0011 (6)	−0.0036 (7)
N9A	0.0349 (15)	0.0178 (16)	0.051 (2)	0.0041 (11)	0.0020 (13)	−0.0023 (14)
N10A	0.0206 (11)	0.0149 (11)	0.0414 (18)	0.0007 (8)	−0.0004 (10)	−0.0020 (10)
C47A	0.0373 (19)	0.020 (2)	0.047 (2)	−0.002 (2)	0.0047 (15)	−0.010 (2)
C48A	0.0306 (18)	0.025 (2)	0.0364 (18)	−0.0050 (14)	−0.0021 (13)	−0.0036 (15)
C49A	0.020 (2)	0.015 (2)	0.043 (3)	−0.0009 (17)	−0.0011 (17)	−0.002 (2)
C50A	0.030 (2)	0.024 (3)	0.037 (2)	−0.001 (3)	0.0013 (14)	0.001 (3)
N9B	0.031 (2)	0.020 (2)	0.032 (3)	−0.0020 (16)	0.0033 (18)	0.0039 (18)
N10B	0.0175 (18)	0.021 (2)	0.026 (2)	0.0009 (15)	−0.0029 (14)	0.0064 (17)
C47B	0.025 (2)	0.025 (3)	0.026 (2)	0.000 (2)	−0.0007 (18)	0.006 (2)
C48B	0.022 (3)	0.022 (5)	0.033 (3)	−0.004 (4)	0.009 (2)	0.004 (4)
C49B	0.019 (4)	0.017 (4)	0.032 (4)	−0.005 (3)	−0.003 (2)	0.000 (3)
C50B	0.055 (5)	0.020 (4)	0.026 (3)	0.000 (4)	0.008 (3)	−0.003 (4)
O7A	0.038 (3)	0.032 (4)	0.028 (4)	−0.009 (3)	0.004 (2)	−0.008 (4)
C51A	0.036 (3)	0.038 (4)	0.021 (3)	−0.007 (3)	0.007 (3)	0.004 (3)
C52A	0.042 (2)	0.024 (3)	0.041 (2)	0.002 (2)	0.0125 (18)	0.006 (2)
C53A	0.037 (2)	0.037 (3)	0.046 (3)	−0.008 (2)	−0.001 (2)	0.004 (2)
C54A	0.055 (4)	0.031 (4)	0.024 (4)	−0.001 (3)	0.002 (3)	0.001 (3)
O7B	0.024 (2)	0.030 (2)	0.028 (4)	−0.007 (2)	0.002 (2)	−0.001 (3)
C51B	0.041 (3)	0.039 (4)	0.021 (4)	−0.005 (3)	−0.009 (2)	0.010 (3)
C52B	0.027 (2)	0.041 (3)	0.031 (2)	−0.010 (2)	−0.0016 (16)	0.011 (2)
C53B	0.040 (2)	0.026 (3)	0.032 (2)	−0.0059 (19)	−0.0138 (17)	0.0075 (19)
C54B	0.050 (3)	0.023 (4)	0.021 (3)	−0.015 (3)	−0.003 (2)	0.000 (3)
O8A	0.066 (2)	0.047 (2)	0.144 (4)	−0.0229 (17)	0.049 (2)	−0.038 (2)
C55A	0.089 (4)	0.074 (3)	0.076 (3)	−0.011 (3)	0.032 (3)	−0.002 (3)
C56A	0.067 (3)	0.104 (6)	0.086 (4)	−0.004 (4)	0.027 (3)	0.014 (4)
C57A	0.040 (3)	0.076 (4)	0.059 (3)	−0.013 (2)	0.012 (2)	−0.021 (2)
C58A	0.065 (3)	0.118 (6)	0.053 (3)	−0.013 (4)	0.012 (2)	−0.009 (4)
O8B	0.059 (3)	0.033 (3)	0.047 (3)	−0.012 (2)	−0.011 (2)	−0.003 (3)
C55B	0.049 (3)	0.038 (3)	0.032 (3)	−0.008 (2)	0.006 (2)	−0.004 (2)
C56B	0.041 (3)	0.039 (4)	0.076 (5)	−0.003 (3)	0.000 (3)	−0.010 (3)
C57B	0.052 (3)	0.052 (4)	0.044 (3)	−0.019 (3)	−0.004 (3)	−0.004 (3)
C58B	0.060 (5)	0.051 (4)	0.055 (4)	−0.025 (3)	−0.008 (4)	0.005 (3)

Geometric parameters (Å, º)

Fe1—N5	2.0739 (13)	O6—C44	1.4189 (18)
Fe1—N1	2.1022 (12)	O6—C45	1.4222 (19)
Fe1—N3	2.1097 (12)	C29—C30	1.503 (3)
Fe1—N2	2.1106 (12)	C29—H29A	0.9900
Fe1—N4	2.1276 (12)	C29—H29B	0.9900
N1—C102	1.3711 (18)	C30—H30A	0.9900
N1—C101	1.3754 (18)	C30—H30B	0.9900
N2—C103	1.3715 (18)	C31—C32	1.492 (3)
N2—C104	1.3742 (18)	C31—H31A	0.9900
N3—C106	1.3715 (18)	C31—H31B	0.9900
N3—C105	1.3756 (18)	C32—H32A	0.9900
N4—C108	1.3719 (18)	C32—H32B	0.9900
N4—C107	1.3727 (18)	C33—C34	1.508 (3)
C101—C301	1.4044 (19)	C33—H33A	0.9900
C101—C201	1.446 (2)	C33—H33B	0.9900
C102—C302	1.3998 (19)	C34—H34A	0.9900
C102—C202	1.442 (2)	C34—H34B	0.9900
C103—C302	1.405 (2)	C35—C36	1.506 (2)
C103—C203	1.4441 (19)	C35—H35A	0.9900
C104—C303	1.4060 (19)	C35—H35B	0.9900
C104—C204	1.446 (2)	C36—H36A	0.9900
C105—C303	1.4064 (19)	C36—H36B	0.9900
C105—C205	1.4436 (19)	C37—C38	1.492 (2)
C106—C304	1.405 (2)	C37—H37A	0.9900
C106—C206	1.444 (2)	C37—H37B	0.9900
C107—C304	1.401 (2)	C38—H38A	0.9900
C107—C207	1.4440 (19)	C38—H38B	0.9900
C108—C301	1.407 (2)	C39—C40	1.500 (2)
C108—C208	1.4474 (19)	C39—H39A	0.9900
C201—C202	1.349 (2)	C39—H39B	0.9900
C201—H20A	0.9500	C40—H40A	0.9900
C202—H20B	0.9500	C40—H40B	0.9900
C203—C204	1.352 (2)	C41—C42	1.502 (2)
C203—H20C	0.9500	C41—H41A	0.9900
C204—H20D	0.9500	C41—H41B	0.9900
C205—C206	1.351 (2)	C42—H42A	0.9900
C205—H20E	0.9500	C42—H42B	0.9900
C206—H20F	0.9500	C43—C44	1.492 (2)
C207—C208	1.348 (2)	C43—H43A	0.9900
C207—H20G	0.9500	C43—H43B	0.9900
C208—H20H	0.9500	C44—H44A	0.9900
C301—C1	1.4922 (19)	C44—H44B	0.9900
C302—C7	1.4963 (19)	C45—C46	1.504 (2)
C303—C13	1.4951 (19)	C45—H45A	0.9900
C304—C19	1.5008 (19)	C45—H45B	0.9900
C1—C2	1.394 (2)	C46—H46A	0.9900
C1—C6	1.398 (2)	C46—H46B	0.9900
C2—C3	1.388 (2)	N9A—C49A	1.320 (6)
C2—H2A	0.9500	N9A—C47A	1.390 (6)
C3—C4	1.385 (2)	N10A—C49A	1.336 (6)
C3—H3A	0.9500	N10A—C48A	1.372 (4)
C4—C5	1.387 (2)	N10A—H10B	0.8800
C4—H4A	0.9500	C47A—C48A	1.357 (5)
C5—C6	1.390 (2)	C47A—H47A	0.9500
C5—H5A	0.9500	C48A—H48A	0.9500
C6—H6A	0.9500	C49A—C50A	1.509 (8)
C7—C8	1.390 (2)	C50A—H50A	0.9800
C7—C12	1.393 (2)	C50A—H50B	0.9800
C8—C9	1.391 (2)	C50A—H50C	0.9800
C8—H8A	0.9500	N9B—C49B	1.316 (11)
C9—C10	1.385 (2)	N9B—C47B	1.378 (7)
C9—H9A	0.9500	N10B—C48B	1.358 (13)
C10—C11	1.381 (2)	N10B—C49B	1.364 (9)
C10—H10A	0.9500	N10B—H10C	0.8800
C11—C12	1.389 (2)	C47B—C48B	1.365 (9)
C11—H11A	0.9500	C47B—H47B	0.9500
C12—H12A	0.9500	C48B—H48B	0.9500
C13—C18	1.394 (2)	C49B—C50B	1.494 (10)
C13—C14	1.395 (2)	C50B—H50D	0.9800
C14—C15	1.391 (2)	C50B—H50E	0.9800
C14—H14A	0.9500	C50B—H50F	0.9800
C15—C16	1.386 (2)	O7A—C51A	1.416 (10)
C15—H15A	0.9500	O7A—C54A	1.427 (9)
C16—C17	1.384 (2)	C51A—C52A	1.516 (10)
C16—H16A	0.9500	C51A—H51A	0.9900
C17—C18	1.392 (2)	C51A—H51B	0.9900
C17—H17A	0.9500	C52A—C53A	1.523 (7)
C18—H18A	0.9500	C52A—H52A	0.9900
C19—C20	1.376 (2)	C52A—H52B	0.9900
C19—C24	1.383 (2)	C53A—C54A	1.517 (9)
C20—C21	1.390 (2)	C53A—H53A	0.9900
C20—H20I	0.9500	C53A—H53B	0.9900
C21—C22	1.367 (3)	C54A—H54A	0.9900
C21—H21A	0.9500	C54A—H54B	0.9900
C22—C23	1.366 (3)	O7B—C54B	1.421 (9)
C22—H22A	0.9500	O7B—C51B	1.426 (10)
C23—C24	1.392 (2)	C51B—C52B	1.522 (10)
C23—H23A	0.9500	C51B—H51C	0.9900
C24—H24A	0.9500	C51B—H51D	0.9900
N5—C27	1.346 (2)	C52B—C53B	1.515 (6)
N5—C25	1.3782 (19)	C52B—H52C	0.9900
N6—C27	1.339 (2)	C52B—H52D	0.9900
N6—C26	1.370 (2)	C53B—C54B	1.507 (9)
C25—C26	1.361 (2)	C53B—H53C	0.9900
C25—H25A	0.9500	C53B—H53D	0.9900
C26—H26A	0.9500	C54B—H54C	0.9900
C27—C28	1.493 (2)	C54B—H54D	0.9900
C28—H28A	0.9800	O8A—C55A	1.434 (6)
C28—H28B	0.9800	O8A—C58A	1.440 (8)
C28—H28C	0.9800	C55A—C56A	1.512 (7)
K1—O5	2.7874 (11)	C55A—H55A	0.9900
K1—O2	2.8040 (12)	C55A—H55B	0.9900
K1—O1	2.8223 (12)	C56A—C57A	1.474 (8)
K1—O3	2.8269 (12)	C56A—H56A	0.9900
K1—O4	2.8364 (12)	C56A—H56B	0.9900
K1—O6	2.8377 (11)	C57A—C58A	1.522 (8)
K1—N7	3.0423 (14)	C57A—H57A	0.9900
K1—N8	3.0555 (14)	C57A—H57B	0.9900
N7—C40	1.469 (2)	C58A—H58A	0.9900
N7—C46	1.471 (2)	C58A—H58B	0.9900
N7—C34	1.477 (2)	O8B—C55B	1.407 (7)
N8—C29	1.465 (2)	O8B—C58B	1.427 (9)
N8—C35	1.469 (2)	C55B—C56B	1.499 (8)
N8—C41	1.471 (2)	C55B—H55C	0.9900
O1—C31	1.413 (2)	C55B—H55D	0.9900
O1—C30	1.428 (2)	C56B—C57B	1.503 (8)
O2—C33	1.418 (2)	C56B—H56C	0.9900
O2—C32	1.432 (2)	C56B—H56D	0.9900
O3—C37	1.427 (2)	C57B—C58B	1.518 (9)
O3—C36	1.433 (2)	C57B—H57C	0.9900
O4—C38	1.4245 (19)	C57B—H57D	0.9900
O4—C39	1.4268 (19)	C58B—H58C	0.9900
O5—C43	1.4184 (19)	C58B—H58D	0.9900
O5—C42	1.4297 (19)
N5—Fe1—N1	108.84 (5)	C29—C30—H30A	110.1
N5—Fe1—N3	100.09 (5)	O1—C30—H30B	110.1
N1—Fe1—N3	151.06 (5)	C29—C30—H30B	110.1
N5—Fe1—N2	102.93 (5)	H30A—C30—H30B	108.4
N1—Fe1—N2	86.98 (4)	O1—C31—C32	109.16 (15)
N3—Fe1—N2	85.89 (4)	O1—C31—H31A	109.8
N5—Fe1—N4	108.44 (5)	C32—C31—H31A	109.8
N1—Fe1—N4	85.40 (4)	O1—C31—H31B	109.8
N3—Fe1—N4	86.19 (4)	C32—C31—H31B	109.8
N2—Fe1—N4	148.53 (5)	H31A—C31—H31B	108.3
C102—N1—C101	106.30 (11)	O2—C32—C31	108.92 (14)
C102—N1—Fe1	125.55 (9)	O2—C32—H32A	109.9
C101—N1—Fe1	127.21 (9)	C31—C32—H32A	109.9
C103—N2—C104	106.13 (11)	O2—C32—H32B	109.9
C103—N2—Fe1	126.47 (9)	C31—C32—H32B	109.9
C104—N2—Fe1	126.34 (9)	H32A—C32—H32B	108.3
C106—N3—C105	106.35 (11)	O2—C33—C34	110.01 (13)
C106—N3—Fe1	125.26 (9)	O2—C33—H33A	109.7
C105—N3—Fe1	124.94 (9)	C34—C33—H33A	109.7
C108—N4—C107	106.14 (11)	O2—C33—H33B	109.7
C108—N4—Fe1	126.37 (9)	C34—C33—H33B	109.7
C107—N4—Fe1	125.54 (9)	H33A—C33—H33B	108.2
N1—C101—C301	125.42 (13)	N7—C34—C33	113.33 (13)
N1—C101—C201	109.56 (12)	N7—C34—H34A	108.9
C301—C101—C201	124.95 (13)	C33—C34—H34A	108.9
N1—C102—C302	125.91 (13)	N7—C34—H34B	108.9
N1—C102—C202	109.97 (12)	C33—C34—H34B	108.9
C302—C102—C202	123.97 (13)	H34A—C34—H34B	107.7
N2—C103—C302	125.01 (13)	N8—C35—C36	113.65 (14)
N2—C103—C203	109.99 (12)	N8—C35—H35A	108.8
C302—C103—C203	124.99 (13)	C36—C35—H35A	108.8
N2—C104—C303	125.36 (13)	N8—C35—H35B	108.8
N2—C104—C204	109.98 (12)	C36—C35—H35B	108.8
C303—C104—C204	124.65 (13)	H35A—C35—H35B	107.7
N3—C105—C303	125.55 (12)	O3—C36—C35	108.54 (14)
N3—C105—C205	109.68 (12)	O3—C36—H36A	110.0
C303—C105—C205	124.77 (13)	C35—C36—H36A	110.0
N3—C106—C304	125.23 (13)	O3—C36—H36B	110.0
N3—C106—C206	109.80 (12)	C35—C36—H36B	110.0
C304—C106—C206	124.96 (13)	H36A—C36—H36B	108.4
N4—C107—C304	125.58 (13)	O3—C37—C38	108.86 (14)
N4—C107—C207	109.93 (12)	O3—C37—H37A	109.9
C304—C107—C207	124.47 (13)	C38—C37—H37A	109.9
N4—C108—C301	125.31 (12)	O3—C37—H37B	109.9
N4—C108—C208	109.91 (12)	C38—C37—H37B	109.9
C301—C108—C208	124.78 (13)	H37A—C37—H37B	108.3
C202—C201—C101	107.17 (13)	O4—C38—C37	109.55 (14)
C202—C201—H20A	126.4	O4—C38—H38A	109.8
C101—C201—H20A	126.4	C37—C38—H38A	109.8
C201—C202—C102	107.00 (13)	O4—C38—H38B	109.8
C201—C202—H20B	126.5	C37—C38—H38B	109.8
C102—C202—H20B	126.5	H38A—C38—H38B	108.2
C204—C203—C103	107.07 (13)	O4—C39—C40	109.30 (13)
C204—C203—H20C	126.5	O4—C39—H39A	109.8
C103—C203—H20C	126.5	C40—C39—H39A	109.8
C203—C204—C104	106.82 (13)	O4—C39—H39B	109.8
C203—C204—H20D	126.6	C40—C39—H39B	109.8
C104—C204—H20D	126.6	H39A—C39—H39B	108.3
C206—C205—C105	107.09 (12)	N7—C40—C39	114.45 (14)
C206—C205—H20E	126.5	N7—C40—H40A	108.6
C105—C205—H20E	126.5	C39—C40—H40A	108.6
C205—C206—C106	107.05 (12)	N7—C40—H40B	108.6
C205—C206—H20F	126.5	C39—C40—H40B	108.6
C106—C206—H20F	126.5	H40A—C40—H40B	107.6
C208—C207—C107	107.11 (12)	N8—C41—C42	112.68 (13)
C208—C207—H20G	126.4	N8—C41—H41A	109.1
C107—C207—H20G	126.4	C42—C41—H41A	109.1
C207—C208—C108	106.90 (12)	N8—C41—H41B	109.1
C207—C208—H20H	126.5	C42—C41—H41B	109.1
C108—C208—H20H	126.5	H41A—C41—H41B	107.8
C101—C301—C108	124.89 (13)	O5—C42—C41	108.78 (13)
C101—C301—C1	116.49 (12)	O5—C42—H42A	109.9
C108—C301—C1	118.53 (12)	C41—C42—H42A	109.9
C102—C302—C103	125.78 (13)	O5—C42—H42B	109.9
C102—C302—C7	116.78 (12)	C41—C42—H42B	109.9
C103—C302—C7	117.43 (12)	H42A—C42—H42B	108.3
C104—C303—C105	124.85 (13)	O5—C43—C44	109.00 (13)
C104—C303—C13	117.83 (12)	O5—C43—H43A	109.9
C105—C303—C13	117.31 (12)	C44—C43—H43A	109.9
C107—C304—C106	125.77 (13)	O5—C43—H43B	109.9
C107—C304—C19	116.90 (12)	C44—C43—H43B	109.9
C106—C304—C19	117.32 (12)	H43A—C43—H43B	108.3
C2—C1—C6	118.42 (13)	O6—C44—C43	108.82 (13)
C2—C1—C301	120.49 (13)	O6—C44—H44A	109.9
C6—C1—C301	121.02 (13)	C43—C44—H44A	109.9
C3—C2—C1	121.20 (14)	O6—C44—H44B	109.9
C3—C2—H2A	119.4	C43—C44—H44B	109.9
C1—C2—H2A	119.4	H44A—C44—H44B	108.3
C4—C3—C2	119.74 (14)	O6—C45—C46	109.17 (13)
C4—C3—H3A	120.1	O6—C45—H45A	109.8
C2—C3—H3A	120.1	C46—C45—H45A	109.8
C3—C4—C5	119.90 (14)	O6—C45—H45B	109.8
C3—C4—H4A	120.0	C46—C45—H45B	109.8
C5—C4—H4A	120.0	H45A—C45—H45B	108.3
C4—C5—C6	120.30 (15)	N7—C46—C45	112.26 (13)
C4—C5—H5A	119.9	N7—C46—H46A	109.2
C6—C5—H5A	119.9	C45—C46—H46A	109.2
C5—C6—C1	120.41 (14)	N7—C46—H46B	109.2
C5—C6—H6A	119.8	C45—C46—H46B	109.2
C1—C6—H6A	119.8	H46A—C46—H46B	107.9
C8—C7—C12	118.66 (13)	C49A—N9A—C47A	104.1 (4)
C8—C7—C302	121.97 (13)	C49A—N10A—C48A	106.7 (3)
C12—C7—C302	119.37 (13)	C49A—N10A—H10B	126.7
C7—C8—C9	120.56 (14)	C48A—N10A—H10B	126.7
C7—C8—H8A	119.7	C48A—C47A—N9A	109.9 (4)
C9—C8—H8A	119.7	C48A—C47A—H47A	125.1
C10—C9—C8	120.15 (15)	N9A—C47A—H47A	125.1
C10—C9—H9A	119.9	C47A—C48A—N10A	106.3 (4)
C8—C9—H9A	119.9	C47A—C48A—H48A	126.8
C11—C10—C9	119.81 (14)	N10A—C48A—H48A	126.8
C11—C10—H10A	120.1	N9A—C49A—N10A	113.0 (5)
C9—C10—H10A	120.1	N9A—C49A—C50A	125.0 (5)
C10—C11—C12	120.03 (15)	N10A—C49A—C50A	122.0 (5)
C10—C11—H11A	120.0	C49A—C50A—H50A	109.5
C12—C11—H11A	120.0	C49A—C50A—H50B	109.5
C11—C12—C7	120.76 (15)	H50A—C50A—H50B	109.5
C11—C12—H12A	119.6	C49A—C50A—H50C	109.5
C7—C12—H12A	119.6	H50A—C50A—H50C	109.5
C18—C13—C14	118.74 (13)	H50B—C50A—H50C	109.5
C18—C13—C303	120.66 (13)	C49B—N9B—C47B	104.3 (5)
C14—C13—C303	120.58 (13)	C48B—N10B—C49B	106.9 (6)
C15—C14—C13	120.54 (14)	C48B—N10B—H10C	126.5
C15—C14—H14A	119.7	C49B—N10B—H10C	126.5
C13—C14—H14A	119.7	C48B—C47B—N9B	110.7 (6)
C16—C15—C14	120.10 (15)	C48B—C47B—H47B	124.6
C16—C15—H15A	120.0	N9B—C47B—H47B	124.6
C14—C15—H15A	120.0	N10B—C48B—C47B	105.9 (8)
C17—C16—C15	119.96 (14)	N10B—C48B—H48B	127.1
C17—C16—H16A	120.0	C47B—C48B—H48B	127.1
C15—C16—H16A	120.0	N9B—C49B—N10B	112.2 (7)
C16—C17—C18	120.02 (15)	N9B—C49B—C50B	126.1 (8)
C16—C17—H17A	120.0	N10B—C49B—C50B	121.7 (8)
C18—C17—H17A	120.0	C49B—C50B—H50D	109.5
C17—C18—C13	120.64 (14)	C49B—C50B—H50E	109.5
C17—C18—H18A	119.7	H50D—C50B—H50E	109.5
C13—C18—H18A	119.7	C49B—C50B—H50F	109.5
C20—C19—C24	118.09 (14)	H50D—C50B—H50F	109.5
C20—C19—C304	120.82 (14)	H50E—C50B—H50F	109.5
C24—C19—C304	121.08 (14)	C51A—O7A—C54A	108.5 (9)
C19—C20—C21	121.10 (17)	O7A—C51A—C52A	108.3 (8)
C19—C20—H20I	119.4	O7A—C51A—H51A	110.0
C21—C20—H20I	119.4	C52A—C51A—H51A	110.0
C22—C21—C20	120.29 (18)	O7A—C51A—H51B	110.0
C22—C21—H21A	119.9	C52A—C51A—H51B	110.0
C20—C21—H21A	119.9	H51A—C51A—H51B	108.4
C23—C22—C21	119.34 (16)	C51A—C52A—C53A	103.0 (6)
C23—C22—H22A	120.3	C51A—C52A—H52A	111.2
C21—C22—H22A	120.3	C53A—C52A—H52A	111.2
C22—C23—C24	120.62 (17)	C51A—C52A—H52B	111.2
C22—C23—H23A	119.7	C53A—C52A—H52B	111.2
C24—C23—H23A	119.7	H52A—C52A—H52B	109.1
C19—C24—C23	120.54 (17)	C54A—C53A—C52A	101.1 (6)
C19—C24—H24A	119.7	C54A—C53A—H53A	111.5
C23—C24—H24A	119.7	C52A—C53A—H53A	111.5
C27—N5—C25	103.93 (13)	C54A—C53A—H53B	111.5
C27—N5—Fe1	132.48 (10)	C52A—C53A—H53B	111.5
C25—N5—Fe1	123.58 (10)	H53A—C53A—H53B	109.4
C27—N6—C26	104.11 (13)	O7A—C54A—C53A	105.7 (8)
C26—C25—N5	108.62 (14)	O7A—C54A—H54A	110.6
C26—C25—H25A	125.7	C53A—C54A—H54A	110.6
N5—C25—H25A	125.7	O7A—C54A—H54B	110.6
C25—C26—N6	109.27 (14)	C53A—C54A—H54B	110.6
C25—C26—H26A	125.4	H54A—C54A—H54B	108.7
N6—C26—H26A	125.4	C54B—O7B—C51B	109.2 (8)
N6—C27—N5	114.06 (14)	O7B—C51B—C52B	104.8 (8)
N6—C27—C28	122.53 (14)	O7B—C51B—H51C	110.8
N5—C27—C28	123.41 (14)	C52B—C51B—H51C	110.8
C27—C28—H28A	109.5	O7B—C51B—H51D	110.8
C27—C28—H28B	109.5	C52B—C51B—H51D	110.8
H28A—C28—H28B	109.5	H51C—C51B—H51D	108.9
C27—C28—H28C	109.5	C53B—C52B—C51B	100.1 (7)
H28A—C28—H28C	109.5	C53B—C52B—H52C	111.8
H28B—C28—H28C	109.5	C51B—C52B—H52C	111.8
O5—K1—O2	128.19 (4)	C53B—C52B—H52D	111.8
O5—K1—O1	92.88 (4)	C51B—C52B—H52D	111.8
O2—K1—O1	60.51 (4)	H52C—C52B—H52D	109.5
O5—K1—O3	98.36 (4)	C54B—C53B—C52B	103.5 (5)
O2—K1—O3	127.75 (4)	C54B—C53B—H53C	111.1
O1—K1—O3	99.98 (4)	C52B—C53B—H53C	111.1
O5—K1—O4	124.64 (4)	C54B—C53B—H53D	111.1
O2—K1—O4	100.85 (3)	C52B—C53B—H53D	111.1
O1—K1—O4	137.78 (4)	H53C—C53B—H53D	109.0
O3—K1—O4	59.77 (3)	O7B—C54B—C53B	106.7 (8)
O5—K1—O6	60.26 (3)	O7B—C54B—H54C	110.4
O2—K1—O6	93.15 (4)	C53B—C54B—H54C	110.4
O1—K1—O6	119.28 (3)	O7B—C54B—H54D	110.4
O3—K1—O6	134.55 (4)	C53B—C54B—H54D	110.4
O4—K1—O6	97.83 (3)	H54C—C54B—H54D	108.6
O5—K1—N7	119.73 (4)	C55A—O8A—C58A	107.4 (4)
O2—K1—N7	60.54 (4)	O8A—C55A—C56A	104.4 (5)
O1—K1—N7	120.81 (4)	O8A—C55A—H55A	110.9
O3—K1—N7	119.60 (4)	C56A—C55A—H55A	110.9
O4—K1—N7	60.08 (3)	O8A—C55A—H55B	110.9
O6—K1—N7	59.73 (3)	C56A—C55A—H55B	110.9
O5—K1—N8	60.57 (3)	H55A—C55A—H55B	108.9
O2—K1—N8	119.45 (4)	C57A—C56A—C55A	107.8 (5)
O1—K1—N8	59.21 (4)	C57A—C56A—H56A	110.1
O3—K1—N8	60.12 (4)	C55A—C56A—H56A	110.1
O4—K1—N8	119.65 (4)	C57A—C56A—H56B	110.1
O6—K1—N8	120.58 (4)	C55A—C56A—H56B	110.1
N7—K1—N8	179.66 (4)	H56A—C56A—H56B	108.5
C40—N7—C46	109.30 (13)	C56A—C57A—C58A	104.2 (5)
C40—N7—C34	110.36 (13)	C56A—C57A—H57A	110.9
C46—N7—C34	109.74 (13)	C58A—C57A—H57A	110.9
C40—N7—K1	109.39 (9)	C56A—C57A—H57B	110.9
C46—N7—K1	110.11 (9)	C58A—C57A—H57B	110.9
C34—N7—K1	107.93 (9)	H57A—C57A—H57B	108.9
C29—N8—C35	109.86 (13)	O8A—C58A—C57A	107.2 (6)
C29—N8—C41	109.58 (13)	O8A—C58A—H58A	110.3
C35—N8—C41	110.36 (13)	C57A—C58A—H58A	110.3
C29—N8—K1	110.52 (10)	O8A—C58A—H58B	110.3
C35—N8—K1	108.87 (10)	C57A—C58A—H58B	110.3
C41—N8—K1	107.63 (9)	H58A—C58A—H58B	108.5
C31—O1—C30	111.47 (13)	C55B—O8B—C58B	106.1 (6)
C31—O1—K1	115.10 (10)	O8B—C55B—C56B	109.3 (5)
C30—O1—K1	114.56 (9)	O8B—C55B—H55C	109.8
C33—O2—C32	112.38 (13)	C56B—C55B—H55C	109.8
C33—O2—K1	118.12 (9)	O8B—C55B—H55D	109.8
C32—O2—K1	112.43 (9)	C56B—C55B—H55D	109.8
C37—O3—C36	110.54 (12)	H55C—C55B—H55D	108.3
C37—O3—K1	115.26 (9)	C55B—C56B—C57B	100.3 (5)
C36—O3—K1	115.30 (9)	C55B—C56B—H56C	111.7
C38—O4—C39	112.03 (12)	C57B—C56B—H56C	111.7
C38—O4—K1	114.89 (9)	C55B—C56B—H56D	111.7
C39—O4—K1	116.38 (9)	C57B—C56B—H56D	111.7
C43—O5—C42	111.67 (12)	H56C—C56B—H56D	109.5
C43—O5—K1	115.26 (9)	C56B—C57B—C58B	99.7 (5)
C42—O5—K1	115.32 (9)	C56B—C57B—H57C	111.8
C44—O6—C45	111.54 (12)	C58B—C57B—H57C	111.8
C44—O6—K1	113.19 (9)	C56B—C57B—H57D	111.8
C45—O6—K1	114.82 (8)	C58B—C57B—H57D	111.8
N8—C29—C30	112.96 (14)	H57C—C57B—H57D	109.6
N8—C29—H29A	109.0	O8B—C58B—C57B	107.1 (6)
C30—C29—H29A	109.0	O8B—C58B—H58C	110.3
N8—C29—H29B	109.0	C57B—C58B—H58C	110.3
C30—C29—H29B	109.0	O8B—C58B—H58D	110.3
H29A—C29—H29B	107.8	C57B—C58B—H58D	110.3
O1—C30—C29	108.13 (13)	H58C—C58B—H58D	108.6
O1—C30—H30A	110.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10A—H10B···N6	0.88	1.92	2.774 (3)	163
N10B—H10C···N6	0.88	1.95	2.798 (5)	160
C36—H36B···N6^i	0.99	2.66	3.548 (2)	150
C45—H45B···N10B^ii	0.99	2.60	3.374 (4)	135
C48B—H48B···O4^iii	0.95	2.59	3.366 (12)	139

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2.