1,1,1-Tris(2-hydroxybenzyl­idene­amino)­methyl­propane iron(III) chloro­form solvate

The X-ray crystal structure of the hexadentate Schiff base complex, [Fe(C₂₇H₂₆N₃O₃)]·CHCl₃, is presented. This species contains an iron atom coordinated within an octahedral N₃O₃ environment.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.087
• Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

As a consequence of our recent studies on the coordination chemistry of tetradentate Schiff bases with 1,3-propanediamine (Reglinski et al., 2002a,b), we wished to extend our catalogue of complexes to include hexadentate species with similar steric influences around the imine regions. To this end we prepared 1,1,1-tris(2-hydroxy- benzylideneamino)methylpropane from the relevant triamine (Fleischer et al., 1971; Hellmann et al., 1995) and salicylaldehyde. To ensure that the ligand behaved in the expected manner we prepared a sample of the iron(III) complex, (I), from ferrous acetate.

S2. Experimental

On recrystallization of the title complex from chloroform/diethyl ether uisng vapour diffusion methods, we obtained deep-red crystals of (I) suitable for X-ray analysis (Found C, 54.46; H, 4.15; N, 6.75: Expected for C₂₇H₂₆N₃O₃Fe·CHCl₃ C, 54.62; H, 4.42; N, 6.82).

S3. Refinement

All hydrogen atoms were found in the difference Fourier synthesis and refined isotropically. The C—H bond lengths are 0.90 (2)–1.00 (2) Å.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988); cell refinement: DENZO & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ORTEPII view of (I), with non-H atoms drawn as 50% probability ellipsoids.

1,1,1-tris(2-hydroxybenzylideneaminomethyl)propane iron(III)

Crystal data

[Fe(C27H26N3O3)]·CHCl3	Dx = 1.475 Mg m^−3
Mr = 615.75	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6345 reflections
a = 13.6479 (2) Å	θ = 3.2–27.5°
b = 18.8071 (2) Å	µ = 0.87 mm^−1
c = 21.6016 (3) Å	T = 123 K
V = 5544.64 (13) Å^3	Prism, red
Z = 8	0.27 × 0.15 × 0.12 mm
F(000) = 2536

Data collection

Nonius KappaCCD diffractometer	4670 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ϕ and ω scans	h = −17→17
11957 measured reflections	k = −24→24
6345 independent reflections	l = −27→28

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	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 2.1937P] where P = (Fo^2 + 2Fc^2)/3
6345 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.47 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
Fe1	0.783074 (19)	0.083565 (14)	0.463759 (12)	0.02065 (8)
Cl1	0.37349 (5)	0.02971 (3)	0.69775 (3)	0.04991 (17)
Cl2	0.16895 (5)	0.02218 (3)	0.73316 (3)	0.04969 (17)
Cl3	0.30161 (6)	−0.09020 (4)	0.76628 (4)	0.0743 (3)
O1	0.67500 (9)	0.11776 (7)	0.41314 (6)	0.0242 (3)
O2	0.76646 (10)	−0.01369 (7)	0.43688 (6)	0.0263 (3)
O3	0.87752 (10)	0.10143 (7)	0.39785 (6)	0.0251 (3)
N1	0.67808 (12)	0.08975 (8)	0.53894 (7)	0.0224 (3)
N2	0.87175 (12)	0.04095 (8)	0.53727 (7)	0.0236 (4)
N3	0.82652 (11)	0.18425 (8)	0.49912 (7)	0.0219 (3)
C1	0.57934 (14)	0.11015 (10)	0.41811 (9)	0.0236 (4)
C2	0.52012 (16)	0.12292 (11)	0.36602 (10)	0.0306 (5)
C3	0.42009 (16)	0.11500 (12)	0.36854 (10)	0.0341 (5)
C4	0.37370 (17)	0.09523 (11)	0.42331 (11)	0.0337 (5)
C5	0.42946 (15)	0.08420 (10)	0.47548 (10)	0.0273 (4)
C6	0.53216 (14)	0.09137 (10)	0.47439 (9)	0.0234 (4)
C7	0.58493 (15)	0.08627 (10)	0.53204 (9)	0.0239 (4)
C8	0.71506 (15)	0.09327 (12)	0.60323 (9)	0.0261 (4)
C9	0.81008 (14)	0.13698 (10)	0.60654 (8)	0.0246 (4)
C10	0.89765 (16)	0.08967 (11)	0.58811 (9)	0.0276 (5)
C11	0.89594 (14)	−0.02469 (11)	0.54382 (9)	0.0255 (4)
C12	0.87342 (14)	−0.08191 (10)	0.50183 (9)	0.0245 (4)
C13	0.91180 (16)	−0.14959 (11)	0.51541 (11)	0.0324 (5)
C14	0.89727 (16)	−0.20674 (12)	0.47690 (11)	0.0354 (5)
C15	0.84289 (16)	−0.19729 (11)	0.42335 (11)	0.0335 (5)
C16	0.80137 (15)	−0.13240 (11)	0.40943 (10)	0.0301 (5)
C17	0.81314 (14)	−0.07345 (10)	0.44906 (9)	0.0241 (4)
C18	0.80388 (16)	0.20216 (11)	0.56405 (9)	0.0260 (4)
C19	0.86208 (14)	0.23443 (11)	0.46574 (9)	0.0241 (4)
C20	0.89542 (14)	0.22835 (10)	0.40235 (8)	0.0230 (4)
C21	0.92824 (15)	0.29034 (11)	0.37274 (9)	0.0277 (4)
C22	0.96975 (16)	0.28834 (12)	0.31479 (10)	0.0328 (5)
C23	0.98025 (16)	0.22292 (12)	0.28552 (10)	0.0339 (5)
C24	0.94883 (15)	0.16141 (12)	0.31289 (9)	0.0299 (5)
C25	0.90448 (13)	0.16192 (10)	0.37200 (9)	0.0231 (4)
C26	0.82788 (18)	0.16237 (12)	0.67366 (9)	0.0318 (5)
C27	0.7570 (2)	0.21740 (15)	0.69879 (12)	0.0419 (6)
C28	0.27264 (18)	−0.02655 (12)	0.70988 (11)	0.0376 (5)
H2	0.5532 (15)	0.1381 (11)	0.3285 (10)	0.029 (5)*
H3	0.3820 (17)	0.1234 (12)	0.3313 (10)	0.038 (6)*
H4	0.3036 (18)	0.0901 (12)	0.4241 (10)	0.039 (6)*
H5	0.3997 (15)	0.0691 (11)	0.5133 (10)	0.024 (5)*
H7	0.5431 (15)	0.0826 (10)	0.5672 (9)	0.022 (5)*
H8A	0.6672 (16)	0.1133 (11)	0.6304 (10)	0.032 (6)*
H8B	0.7267 (14)	0.0452 (11)	0.6186 (9)	0.025 (5)*
H10A	0.9201 (15)	0.0609 (11)	0.6242 (9)	0.024 (5)*
H10B	0.9514 (16)	0.1195 (11)	0.5750 (9)	0.031 (6)*
H11	0.9316 (14)	−0.0393 (10)	0.5820 (9)	0.022 (5)*
H13	0.9474 (16)	−0.1538 (11)	0.5527 (10)	0.030 (6)*
H14	0.9262 (16)	−0.2485 (13)	0.4856 (10)	0.033 (6)*
H15	0.8300 (16)	−0.2367 (12)	0.3960 (10)	0.038 (6)*
H16	0.7650 (16)	−0.1258 (11)	0.3736 (10)	0.032 (6)*
H18A	0.7391 (15)	0.2240 (10)	0.5652 (8)	0.019 (5)*
H18B	0.8514 (15)	0.2380 (11)	0.5774 (9)	0.025 (5)*
H19	0.8719 (14)	0.2805 (10)	0.4825 (8)	0.016 (5)*
H21	0.9201 (15)	0.3346 (12)	0.3932 (9)	0.030 (6)*
H22	0.9920 (15)	0.3325 (12)	0.2950 (10)	0.032 (6)*
H23	1.0104 (18)	0.2222 (12)	0.2470 (11)	0.040 (6)*
H24	0.9564 (16)	0.1175 (12)	0.2938 (10)	0.034 (6)*
H26A	0.8265 (16)	0.1208 (12)	0.6995 (10)	0.031 (6)*
H26B	0.8932 (17)	0.1823 (12)	0.6737 (9)	0.034 (6)*
H27A	0.690 (2)	0.2005 (14)	0.6965 (12)	0.054 (8)*
H27B	0.756 (2)	0.2580 (16)	0.6744 (13)	0.057 (8)*
H27C	0.7763 (19)	0.2311 (14)	0.7416 (14)	0.060 (8)*
H28	0.2575 (17)	−0.0473 (12)	0.6728 (11)	0.036 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02141 (15)	0.01807 (14)	0.02246 (14)	0.00025 (11)	−0.00183 (11)	−0.00028 (11)
Cl1	0.0528 (4)	0.0423 (4)	0.0546 (4)	−0.0121 (3)	0.0101 (3)	−0.0106 (3)
Cl2	0.0460 (4)	0.0501 (4)	0.0530 (4)	0.0035 (3)	0.0008 (3)	−0.0072 (3)
Cl3	0.0652 (5)	0.0787 (5)	0.0790 (5)	0.0220 (4)	0.0313 (4)	0.0437 (4)
O1	0.0222 (7)	0.0258 (7)	0.0245 (7)	0.0018 (6)	−0.0012 (6)	0.0026 (6)
O2	0.0301 (8)	0.0182 (7)	0.0304 (7)	0.0004 (6)	−0.0058 (6)	−0.0004 (6)
O3	0.0257 (7)	0.0215 (7)	0.0281 (7)	−0.0007 (6)	0.0026 (6)	−0.0017 (6)
N1	0.0252 (8)	0.0191 (8)	0.0228 (8)	0.0001 (7)	−0.0019 (7)	0.0000 (6)
N2	0.0230 (8)	0.0227 (9)	0.0251 (8)	−0.0006 (7)	−0.0030 (7)	−0.0014 (7)
N3	0.0226 (8)	0.0206 (8)	0.0224 (8)	0.0022 (7)	−0.0014 (7)	−0.0022 (7)
C1	0.0238 (10)	0.0166 (9)	0.0302 (10)	0.0020 (8)	−0.0029 (8)	−0.0047 (8)
C2	0.0294 (11)	0.0319 (12)	0.0305 (11)	0.0033 (9)	−0.0038 (9)	0.0004 (9)
C3	0.0320 (12)	0.0343 (12)	0.0362 (12)	0.0055 (10)	−0.0109 (10)	−0.0043 (10)
C4	0.0226 (11)	0.0289 (12)	0.0497 (13)	0.0007 (9)	−0.0059 (10)	−0.0084 (10)
C5	0.0264 (11)	0.0211 (10)	0.0345 (11)	−0.0019 (8)	0.0014 (9)	−0.0042 (9)
C6	0.0246 (10)	0.0160 (9)	0.0297 (10)	−0.0006 (7)	−0.0012 (8)	−0.0025 (8)
C7	0.0253 (10)	0.0190 (10)	0.0274 (10)	−0.0014 (8)	0.0036 (9)	−0.0021 (8)
C8	0.0290 (11)	0.0301 (12)	0.0192 (9)	−0.0023 (9)	0.0002 (9)	0.0002 (9)
C9	0.0289 (10)	0.0234 (10)	0.0216 (9)	−0.0019 (8)	−0.0022 (8)	−0.0003 (8)
C10	0.0286 (11)	0.0273 (11)	0.0267 (10)	−0.0024 (9)	−0.0079 (9)	0.0000 (9)
C11	0.0206 (10)	0.0271 (11)	0.0288 (10)	0.0024 (8)	−0.0042 (8)	0.0039 (9)
C12	0.0188 (10)	0.0217 (10)	0.0329 (11)	−0.0007 (8)	0.0005 (8)	0.0011 (8)
C13	0.0256 (11)	0.0283 (12)	0.0432 (13)	0.0022 (9)	−0.0050 (10)	0.0033 (10)
C14	0.0285 (12)	0.0199 (11)	0.0577 (15)	0.0040 (9)	−0.0009 (11)	0.0009 (10)
C15	0.0303 (12)	0.0223 (11)	0.0479 (13)	−0.0037 (9)	0.0023 (10)	−0.0074 (10)
C16	0.0292 (11)	0.0255 (11)	0.0355 (12)	−0.0041 (9)	−0.0025 (10)	−0.0011 (9)
C17	0.0206 (9)	0.0193 (10)	0.0325 (10)	−0.0033 (8)	0.0031 (8)	0.0021 (8)
C18	0.0312 (12)	0.0222 (10)	0.0246 (10)	−0.0009 (9)	0.0009 (9)	−0.0060 (8)
C19	0.0229 (10)	0.0207 (10)	0.0288 (10)	0.0022 (8)	−0.0034 (8)	−0.0029 (9)
C20	0.0199 (10)	0.0233 (10)	0.0257 (9)	0.0019 (8)	−0.0029 (8)	0.0013 (8)
C21	0.0290 (11)	0.0241 (11)	0.0301 (11)	0.0010 (9)	−0.0010 (9)	0.0005 (9)
C22	0.0345 (12)	0.0305 (12)	0.0335 (11)	−0.0028 (9)	0.0037 (10)	0.0080 (9)
C23	0.0349 (12)	0.0384 (13)	0.0284 (11)	−0.0005 (10)	0.0062 (10)	0.0004 (10)
C24	0.0310 (11)	0.0285 (12)	0.0302 (10)	0.0000 (9)	0.0022 (9)	−0.0056 (9)
C25	0.0168 (9)	0.0262 (10)	0.0262 (10)	0.0008 (8)	−0.0019 (8)	0.0004 (8)
C26	0.0382 (13)	0.0333 (13)	0.0237 (11)	−0.0046 (10)	−0.0022 (9)	−0.0021 (9)
C27	0.0466 (16)	0.0469 (16)	0.0321 (13)	−0.0014 (12)	0.0003 (11)	−0.0117 (12)
C28	0.0483 (14)	0.0327 (12)	0.0318 (12)	−0.0050 (11)	0.0040 (11)	−0.0039 (10)

Geometric parameters (Å, º)

Fe1—N1	2.1690 (16)	N1—C7	1.282 (3)
Fe1—N2	2.1514 (15)	N1—C8	1.479 (2)
Fe1—N3	2.1262 (15)	O1—C1	1.318 (2)
Fe1—O1	1.9454 (13)	N2—C11	1.286 (2)
Fe1—O2	1.9323 (13)	N2—C10	1.473 (2)
Fe1—O3	1.9498 (13)	C7—C6	1.442 (3)
O3—C25	1.320 (2)	C7—H7	0.95 (2)
N3—C19	1.283 (2)	C12—C13	1.407 (3)
N3—C18	1.475 (2)	C12—C17	1.415 (3)
C19—C20	1.447 (3)	C12—C11	1.441 (3)
C19—H19	0.949 (19)	C8—C9	1.537 (3)
C18—C9	1.534 (3)	C8—H8B	0.98 (2)
C18—H18A	0.98 (2)	C8—H8A	0.95 (2)
C18—H18B	0.98 (2)	C10—C9	1.542 (3)
C27—C26	1.517 (3)	C10—H10A	1.00 (2)
C27—H27A	0.97 (3)	C10—H10B	0.97 (2)
C27—H27C	0.99 (3)	C11—H11	0.995 (19)
C27—H27B	0.93 (3)	C16—C15	1.379 (3)
C26—C9	1.546 (3)	C16—C17	1.410 (3)
C26—H26A	0.96 (2)	C16—H16	0.93 (2)
C26—H26B	0.97 (2)	C13—C14	1.373 (3)
C20—C21	1.403 (3)	C13—H13	0.94 (2)
C20—C25	1.416 (3)	C5—C4	1.376 (3)
C25—C24	1.413 (3)	C5—C6	1.408 (3)
C28—Cl3	1.753 (2)	C5—H5	0.95 (2)
C28—Cl1	1.756 (2)	C2—C3	1.374 (3)
C28—Cl2	1.759 (2)	C2—C1	1.406 (3)
C28—H28	0.91 (2)	C2—H2	0.97 (2)
C21—C22	1.375 (3)	C6—C1	1.420 (3)
C21—H21	0.95 (2)	C14—C15	1.386 (3)
C23—C24	1.368 (3)	C14—H14	0.90 (2)
C23—C22	1.391 (3)	C3—C4	1.392 (3)
C23—H23	0.93 (2)	C3—H3	0.97 (2)
C24—H24	0.93 (2)	C4—H4	0.96 (2)
C22—H22	0.98 (2)	C15—H15	0.96 (2)
O2—C17	1.318 (2)
C25—O3—Fe1	129.93 (12)	C7—N1—Fe1	124.44 (13)
C19—N3—C18	116.46 (16)	C8—N1—Fe1	118.69 (13)
C19—N3—Fe1	123.96 (13)	C1—O1—Fe1	132.03 (12)
C18—N3—Fe1	119.12 (12)	C11—N2—C10	116.97 (16)
N3—C19—C20	126.33 (18)	C11—N2—Fe1	125.69 (13)
N3—C19—H19	120.7 (11)	C10—N2—Fe1	116.96 (12)
C20—C19—H19	112.9 (11)	N1—C7—C6	126.34 (18)
N3—C18—C9	112.02 (15)	N1—C7—H7	120.3 (12)
N3—C18—H18A	108.0 (11)	C6—C7—H7	113.3 (12)
C9—C18—H18A	111.9 (11)	C13—C12—C17	119.08 (18)
N3—C18—H18B	107.4 (12)	C13—C12—C11	117.71 (18)
C9—C18—H18B	109.7 (12)	C17—C12—C11	123.19 (17)
H18A—C18—H18B	107.6 (16)	N1—C8—C9	110.82 (16)
C26—C27—H27A	111.1 (16)	N1—C8—H8B	109.5 (11)
C26—C27—H27C	109.9 (15)	C9—C8—H8B	110.0 (12)
H27A—C27—H27C	112 (2)	N1—C8—H8A	111.2 (13)
C26—C27—H27B	111.6 (17)	C9—C8—H8A	109.7 (13)
H27A—C27—H27B	103 (2)	H8B—C8—H8A	105.5 (17)
H27C—C27—H27B	109 (2)	N2—C10—C9	111.43 (16)
C27—C26—C9	116.50 (19)	N2—C10—H10A	108.6 (11)
C27—C26—H26A	109.6 (13)	C9—C10—H10A	110.5 (11)
C9—C26—H26A	106.8 (13)	N2—C10—H10B	109.0 (12)
C27—C26—H26B	108.9 (13)	C9—C10—H10B	109.2 (13)
C9—C26—H26B	105.3 (12)	H10A—C10—H10B	108.1 (17)
H26A—C26—H26B	109.4 (19)	N2—C11—C12	126.39 (18)
C21—C20—C25	119.61 (17)	N2—C11—H11	118.8 (11)
C21—C20—C19	117.77 (17)	C12—C11—H11	114.8 (11)
C25—C20—C19	122.35 (17)	C15—C16—C17	121.1 (2)
O3—C25—C24	119.73 (17)	C15—C16—H16	121.3 (13)
O3—C25—C20	122.71 (16)	C17—C16—H16	117.6 (13)
C24—C25—C20	117.49 (18)	C14—C13—C12	121.9 (2)
Cl3—C28—Cl1	109.78 (14)	C14—C13—H13	121.7 (13)
Cl3—C28—Cl2	109.78 (12)	C12—C13—H13	116.4 (13)
Cl1—C28—Cl2	111.05 (13)	C4—C5—C6	121.5 (2)
Cl3—C28—H28	111.6 (14)	C4—C5—H5	120.7 (12)
Cl1—C28—H28	107.7 (14)	C6—C5—H5	117.8 (12)
Cl2—C28—H28	106.9 (15)	O2—C17—C16	119.62 (18)
C22—C21—C20	121.59 (19)	O2—C17—C12	122.51 (17)
C22—C21—H21	119.8 (12)	C16—C17—C12	117.85 (18)
C20—C21—H21	118.6 (12)	C3—C2—C1	121.4 (2)
C24—C23—C22	121.3 (2)	C3—C2—H2	121.9 (12)
C24—C23—H23	120.9 (14)	C1—C2—H2	116.8 (12)
C22—C23—H23	117.8 (14)	C18—C9—C8	110.68 (16)
C23—C24—C25	121.3 (2)	C18—C9—C10	110.45 (16)
C23—C24—H24	121.7 (13)	C8—C9—C10	109.46 (16)
C25—C24—H24	117.0 (13)	C18—C9—C26	108.85 (16)
C21—C22—C23	118.7 (2)	C8—C9—C26	109.96 (16)
C21—C22—H22	120.1 (12)	C10—C9—C26	107.37 (16)
C23—C22—H22	121.2 (12)	C5—C6—C1	119.30 (18)
O2—Fe1—O1	93.16 (6)	C5—C6—C7	118.45 (18)
O2—Fe1—O3	91.22 (6)	C1—C6—C7	121.96 (18)
O1—Fe1—O3	91.94 (5)	C13—C14—C15	118.8 (2)
O2—Fe1—N3	169.63 (6)	C13—C14—H14	119.6 (14)
O1—Fe1—N3	96.83 (6)	C15—C14—H14	121.5 (14)
O3—Fe1—N3	85.67 (6)	O1—C1—C2	119.06 (18)
O2—Fe1—N2	86.28 (6)	O1—C1—C6	123.09 (17)
O1—Fe1—N2	164.68 (6)	C2—C1—C6	117.83 (18)
O3—Fe1—N2	103.37 (6)	C2—C3—C4	120.9 (2)
N3—Fe1—N2	84.82 (6)	C2—C3—H3	118.8 (13)
O2—Fe1—N1	101.43 (6)	C4—C3—H3	120.2 (13)
O1—Fe1—N1	84.39 (6)	C5—C4—C3	119.0 (2)
O3—Fe1—N1	166.98 (6)	C5—C4—H4	121.3 (14)
N3—Fe1—N1	82.38 (6)	C3—C4—H4	119.7 (14)
N2—Fe1—N1	80.73 (6)	C16—C15—C14	121.0 (2)
C17—O2—Fe1	133.65 (12)	C16—C15—H15	118.2 (13)
C7—N1—C8	116.74 (17)	C14—C15—H15	120.7 (13)
C18—N3—C19—C20	175.88 (18)	N3—Fe1—N2—C11	−170.02 (17)
Fe1—N3—C19—C20	−12.0 (3)	N1—Fe1—N2—C11	106.88 (17)
C19—N3—C18—C9	−152.53 (17)	O2—Fe1—N2—C10	−168.07 (14)
Fe1—N3—C18—C9	34.9 (2)	O1—Fe1—N2—C10	−79.7 (3)
N3—C19—C20—C21	177.33 (19)	O3—Fe1—N2—C10	101.56 (14)
N3—C19—C20—C25	−8.8 (3)	N3—Fe1—N2—C10	17.26 (14)
Fe1—O3—C25—C24	−159.46 (14)	N1—Fe1—N2—C10	−65.84 (14)
Fe1—O3—C25—C20	23.8 (3)	C8—N1—C7—C6	171.69 (18)
C21—C20—C25—O3	178.16 (17)	Fe1—N1—C7—C6	−12.7 (3)
C19—C20—C25—O3	4.3 (3)	C7—N1—C8—C9	−148.22 (17)
C21—C20—C25—C24	1.3 (3)	Fe1—N1—C8—C9	35.9 (2)
C19—C20—C25—C24	−172.50 (18)	C11—N2—C10—C9	−132.35 (19)
C25—C20—C21—C22	−0.4 (3)	Fe1—N2—C10—C9	41.0 (2)
C19—C20—C21—C22	173.73 (19)	C10—N2—C11—C12	176.40 (19)
C22—C23—C24—C25	0.0 (3)	Fe1—N2—C11—C12	3.7 (3)
O3—C25—C24—C23	−178.08 (19)	C13—C12—C11—N2	176.1 (2)
C20—C25—C24—C23	−1.1 (3)	C17—C12—C11—N2	−5.5 (3)
C20—C21—C22—C23	−0.8 (3)	C17—C12—C13—C14	4.0 (3)
C24—C23—C22—C21	1.0 (3)	C11—C12—C13—C14	−177.6 (2)
C25—O3—Fe1—O2	157.44 (15)	Fe1—O2—C17—C16	−162.23 (14)
C25—O3—Fe1—O1	64.24 (15)	Fe1—O2—C17—C12	19.5 (3)
C25—O3—Fe1—N3	−32.47 (15)	C15—C16—C17—O2	−174.88 (19)
C25—O3—Fe1—N2	−116.09 (15)	C15—C16—C17—C12	3.4 (3)
C25—O3—Fe1—N1	−9.0 (3)	C13—C12—C17—O2	172.84 (18)
C19—N3—Fe1—O2	98.6 (3)	C11—C12—C17—O2	−5.5 (3)
C18—N3—Fe1—O2	−89.5 (3)	C13—C12—C17—C16	−5.4 (3)
C19—N3—Fe1—O1	−65.72 (16)	C11—C12—C17—C16	176.21 (18)
C18—N3—Fe1—O1	106.21 (13)	N3—C18—C9—C8	−81.9 (2)
C19—N3—Fe1—O3	25.72 (15)	N3—C18—C9—C10	39.5 (2)
C18—N3—Fe1—O3	−162.35 (14)	N3—C18—C9—C26	157.13 (17)
C19—N3—Fe1—N2	129.59 (16)	N1—C8—C9—C18	39.9 (2)
C18—N3—Fe1—N2	−58.47 (14)	N1—C8—C9—C10	−82.0 (2)
C19—N3—Fe1—N1	−149.09 (16)	N1—C8—C9—C26	160.24 (17)
C18—N3—Fe1—N1	22.84 (13)	N2—C10—C9—C18	−84.1 (2)
O1—Fe1—O2—C17	178.72 (17)	N2—C10—C9—C8	38.0 (2)
O3—Fe1—O2—C17	86.71 (17)	N2—C10—C9—C26	157.36 (17)
N3—Fe1—O2—C17	14.3 (4)	C27—C26—C9—C18	52.9 (3)
N2—Fe1—O2—C17	−16.62 (17)	C27—C26—C9—C8	−68.5 (3)
N1—Fe1—O2—C17	−96.38 (17)	C27—C26—C9—C10	172.5 (2)
O2—Fe1—N1—C7	−67.32 (16)	C4—C5—C6—C1	−0.2 (3)
O1—Fe1—N1—C7	24.78 (15)	C4—C5—C6—C7	173.67 (18)
O3—Fe1—N1—C7	98.9 (3)	N1—C7—C6—C5	178.11 (19)
N3—Fe1—N1—C7	122.47 (16)	N1—C7—C6—C1	−8.1 (3)
N2—Fe1—N1—C7	−151.58 (16)	C12—C13—C14—C15	−0.3 (3)
O2—Fe1—N1—C8	108.26 (13)	Fe1—O1—C1—C2	−161.81 (14)
O1—Fe1—N1—C8	−159.65 (14)	Fe1—O1—C1—C6	20.0 (3)
O3—Fe1—N1—C8	−85.6 (3)	C3—C2—C1—O1	179.29 (19)
N3—Fe1—N1—C8	−61.96 (14)	C3—C2—C1—C6	−2.4 (3)
N2—Fe1—N1—C8	24.00 (13)	C5—C6—C1—O1	−179.85 (17)
O2—Fe1—O1—C1	71.81 (16)	C7—C6—C1—O1	6.5 (3)
O3—Fe1—O1—C1	163.14 (16)	C5—C6—C1—C2	1.9 (3)
N3—Fe1—O1—C1	−110.99 (16)	C7—C6—C1—C2	−171.79 (17)
N2—Fe1—O1—C1	−15.6 (3)	C1—C2—C3—C4	1.2 (3)
N1—Fe1—O1—C1	−29.38 (16)	C6—C5—C4—C3	−1.0 (3)
O2—Fe1—N2—C11	4.64 (16)	C2—C3—C4—C5	0.6 (3)
O1—Fe1—N2—C11	93.0 (3)	C17—C16—C15—C14	0.3 (3)
O3—Fe1—N2—C11	−85.73 (17)	C13—C14—C15—C16	−1.9 (3)