Bis(ferrocenecarbaldehyde) (1,2-diphenyl­ethane-1,2-diyl­idene)dihydrazone

In the title compound, [Fe₂(C₅H₅)₂(C₂₆H₂₀N₄)], two ferrocene units are bridged by a Schiff base linker with an intra­molecular Fe...Fe separation of 7.42 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.044
• wR factor = 0.109
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Bis(ferrocenecarbaldehyde) (1,2-diphenylethane-1,2-diylidene)dihydrazone

Crystal data

[Fe2(C5H5)2(C26H20N4)]	F(000) = 1304
Mr = 630.34	Dx = 1.393 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 380 reflections
a = 12.066 (3) Å	θ = 2.0–28.3°
b = 11.187 (3) Å	µ = 1.00 mm^−1
c = 22.402 (6) Å	T = 293 K
β = 96.284 (5)°	Rod, red
V = 3005.6 (13) Å^3	0.26 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	3782 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −14→14
14449 measured reflections	k = −13→13
5285 independent reflections	l = −14→26

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) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0524P)^2] where P = (Fo^2 + 2Fc^2)/3
5285 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.57 e Å^−3
18 restraints	Δρmin = −0.34 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	0.44035 (3)	0.82439 (3)	0.083294 (19)	0.04335 (14)
Fe2	−0.13375 (3)	0.69682 (4)	−0.05636 (2)	0.05436 (16)
C1	0.5148 (2)	0.7259 (3)	0.02334 (13)	0.0446 (7)
C2	0.5430 (2)	0.8488 (3)	0.01846 (14)	0.0490 (7)
H2B	0.5277	0.8988	−0.0174	0.059*
C3	0.5969 (2)	0.8857 (3)	0.07428 (14)	0.0548 (8)
H3B	0.6243	0.9666	0.0841	0.066*
C4	0.6027 (2)	0.7884 (3)	0.11403 (15)	0.0550 (8)
H4B	0.6350	0.7897	0.1561	0.066*
C5	0.5519 (2)	0.6884 (3)	0.08314 (14)	0.0512 (8)
H5A	0.5439	0.6083	0.0998	0.061*
C6	0.2736 (3)	0.7977 (3)	0.06649 (17)	0.0663 (10)
H6A	0.2367	0.7433	0.0363	0.080*
C7	0.2997 (3)	0.9176 (4)	0.05717 (17)	0.0699 (10)
H7A	0.2838	0.9623	0.0196	0.084*
C8	0.3521 (3)	0.9630 (3)	0.11209 (19)	0.0724 (10)
H8A	0.3796	1.0448	0.1191	0.087*
C9	0.3577 (3)	0.8714 (3)	0.15464 (16)	0.0672 (9)
H9A	0.3902	0.8774	0.1966	0.081*
C10	0.3095 (3)	0.7687 (3)	0.12639 (16)	0.0635 (9)
H10A	0.3024	0.6904	0.1453	0.076*
C11	0.4491 (2)	0.6544 (2)	−0.02111 (13)	0.0446 (7)
H11A	0.4259	0.5787	−0.0107	0.054*
C12	0.2865 (2)	0.6628 (2)	−0.14923 (13)	0.0415 (7)
C13	0.2080 (2)	0.5897 (3)	−0.18919 (13)	0.0472 (7)
C14	0.1923 (3)	0.4695 (3)	−0.17684 (17)	0.0728 (10)
H14A	0.2330	0.4343	−0.1438	0.087*
C15	0.1170 (4)	0.4019 (4)	−0.2132 (2)	0.1002 (14)
H15A	0.1066	0.3219	−0.2042	0.120*
C16	0.0573 (4)	0.4516 (4)	−0.2626 (2)	0.0946 (14)
H16A	0.0068	0.4054	−0.2871	0.114*
C17	0.0722 (3)	0.5680 (4)	−0.27547 (18)	0.0857 (12)
H17A	0.0321	0.6017	−0.3091	0.103*
C18	0.1470 (3)	0.6381 (3)	−0.23874 (16)	0.0684 (10)
H18A	0.1557	0.7184	−0.2479	0.082*
C19	0.2800 (2)	0.7972 (2)	−0.15642 (13)	0.0428 (7)
C20	0.3498 (2)	0.8558 (2)	−0.19766 (12)	0.0448 (7)
C21	0.4513 (3)	0.8071 (3)	−0.20809 (14)	0.0540 (8)
H21A	0.4752	0.7359	−0.1894	0.065*
C22	0.5174 (3)	0.8636 (3)	−0.24611 (15)	0.0652 (9)
H22A	0.5863	0.8313	−0.2522	0.078*
C23	0.4819 (3)	0.9672 (3)	−0.27498 (15)	0.0696 (10)
H23A	0.5258	1.0041	−0.3012	0.084*
C24	0.3808 (3)	1.0163 (3)	−0.26499 (15)	0.0691 (10)
H24A	0.3567	1.0868	−0.2842	0.083*
C25	0.3159 (3)	0.9614 (3)	−0.22684 (14)	0.0577 (8)
H25A	0.2479	0.9952	−0.2203	0.069*
C26	0.0737 (2)	0.8480 (3)	−0.07148 (13)	0.0492 (8)
H26A	0.0592	0.9258	−0.0847	0.059*
C27	0.0044 (2)	0.7947 (3)	−0.02987 (14)	0.0523 (8)
C28	0.0136 (3)	0.6786 (3)	−0.00416 (15)	0.0607 (9)
H28A	0.0716	0.6199	−0.0102	0.073*
C29	−0.0744 (3)	0.6617 (4)	0.03121 (16)	0.0770 (11)
H29A	−0.0888	0.5894	0.0538	0.092*
C30	−0.1393 (3)	0.7673 (4)	0.02782 (17)	0.0799 (11)
H30A	−0.2069	0.7805	0.0475	0.096*
C31	−0.0912 (3)	0.8499 (3)	−0.00967 (16)	0.0644 (9)
H31A	−0.1188	0.9305	−0.0200	0.077*
C32	−0.1571 (3)	0.5534 (4)	−0.11272 (18)	0.0795 (7)
H32A	−0.1136	0.4792	−0.1104	0.095*
C33	−0.1355 (3)	0.6562 (4)	−0.14493 (16)	0.0738 (11)
H33A	−0.0730	0.6668	−0.1689	0.089*
C34	−0.2186 (3)	0.7428 (4)	−0.13711 (17)	0.0737 (7)
H34A	−0.2248	0.8229	−0.1549	0.088*
C35	−0.2901 (3)	0.6914 (3)	−0.10068 (18)	0.0751 (6)
H35A	−0.3556	0.7306	−0.0873	0.090*
C36	−0.2540 (3)	0.5765 (3)	−0.08464 (18)	0.0783 (6)
H36A	−0.2904	0.5209	−0.0591	0.094*
N1	0.42210 (19)	0.69301 (19)	−0.07463 (11)	0.0457 (6)
N2	0.35405 (19)	0.6108 (2)	−0.10960 (11)	0.0440 (6)
N3	0.21207 (19)	0.8603 (2)	−0.12900 (11)	0.0483 (6)
N4	0.1543 (2)	0.7907 (2)	−0.09042 (12)	0.0520 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0453 (3)	0.0418 (2)	0.0426 (3)	0.00514 (18)	0.00358 (19)	−0.00038 (19)
Fe2	0.0384 (3)	0.0671 (3)	0.0584 (3)	0.0021 (2)	0.0089 (2)	−0.0044 (2)
C1	0.0466 (17)	0.0443 (16)	0.0432 (17)	0.0095 (13)	0.0067 (14)	0.0021 (14)
C2	0.0529 (18)	0.0457 (17)	0.0499 (18)	0.0020 (14)	0.0129 (15)	0.0051 (14)
C3	0.0458 (17)	0.0576 (19)	0.060 (2)	−0.0041 (15)	0.0017 (16)	−0.0038 (17)
C4	0.0476 (18)	0.067 (2)	0.0487 (19)	0.0108 (15)	−0.0046 (15)	−0.0013 (16)
C5	0.0527 (18)	0.0490 (18)	0.0516 (19)	0.0143 (14)	0.0043 (16)	0.0061 (15)
C6	0.0445 (19)	0.086 (3)	0.068 (2)	0.0001 (17)	0.0015 (18)	−0.011 (2)
C7	0.053 (2)	0.084 (3)	0.073 (3)	0.0270 (19)	0.0096 (19)	0.018 (2)
C8	0.074 (2)	0.053 (2)	0.095 (3)	0.0132 (18)	0.033 (2)	−0.012 (2)
C9	0.065 (2)	0.085 (3)	0.055 (2)	0.005 (2)	0.0169 (18)	−0.015 (2)
C10	0.056 (2)	0.068 (2)	0.069 (2)	0.0003 (17)	0.0186 (18)	0.0082 (19)
C11	0.0513 (17)	0.0357 (15)	0.0476 (18)	0.0089 (13)	0.0093 (15)	0.0003 (13)
C12	0.0403 (16)	0.0441 (16)	0.0420 (17)	0.0006 (13)	0.0137 (14)	−0.0035 (13)
C13	0.0460 (16)	0.0504 (18)	0.0464 (18)	0.0003 (14)	0.0106 (15)	−0.0067 (14)
C14	0.076 (2)	0.060 (2)	0.079 (3)	−0.0114 (18)	−0.005 (2)	−0.002 (2)
C15	0.110 (3)	0.067 (3)	0.120 (4)	−0.031 (3)	−0.005 (3)	−0.015 (3)
C16	0.086 (3)	0.097 (3)	0.096 (3)	−0.023 (3)	−0.013 (3)	−0.035 (3)
C17	0.080 (3)	0.103 (3)	0.068 (3)	−0.007 (2)	−0.017 (2)	−0.016 (2)
C18	0.071 (2)	0.067 (2)	0.065 (2)	−0.0029 (18)	−0.006 (2)	−0.0086 (18)
C19	0.0425 (16)	0.0388 (16)	0.0459 (17)	−0.0011 (13)	0.0002 (14)	−0.0016 (13)
C20	0.0529 (18)	0.0426 (16)	0.0383 (16)	−0.0032 (13)	0.0022 (14)	−0.0015 (13)
C21	0.062 (2)	0.0484 (18)	0.0540 (19)	−0.0023 (15)	0.0157 (17)	−0.0016 (15)
C22	0.068 (2)	0.070 (2)	0.061 (2)	−0.0102 (18)	0.0268 (19)	−0.0077 (19)
C23	0.094 (3)	0.069 (2)	0.048 (2)	−0.029 (2)	0.018 (2)	−0.0014 (18)
C24	0.091 (3)	0.056 (2)	0.058 (2)	−0.015 (2)	−0.002 (2)	0.0156 (17)
C25	0.0590 (19)	0.0547 (19)	0.059 (2)	−0.0029 (16)	0.0039 (17)	0.0045 (17)
C26	0.0427 (17)	0.0481 (17)	0.0559 (19)	0.0023 (14)	0.0012 (15)	−0.0099 (15)
C27	0.0374 (16)	0.062 (2)	0.058 (2)	0.0079 (14)	0.0039 (15)	−0.0137 (16)
C28	0.0463 (18)	0.077 (2)	0.058 (2)	0.0085 (16)	0.0020 (16)	0.0011 (18)
C29	0.066 (2)	0.107 (3)	0.058 (2)	−0.006 (2)	0.0079 (19)	0.011 (2)
C30	0.056 (2)	0.122 (3)	0.065 (2)	−0.002 (2)	0.021 (2)	−0.020 (2)
C31	0.0502 (19)	0.074 (2)	0.070 (2)	0.0107 (17)	0.0103 (18)	−0.0219 (19)
C32	0.0699 (15)	0.0824 (16)	0.0829 (16)	−0.0039 (14)	−0.0062 (13)	−0.0084 (14)
C33	0.052 (2)	0.112 (3)	0.058 (2)	−0.009 (2)	0.0092 (18)	−0.024 (2)
C34	0.0625 (15)	0.0810 (16)	0.0755 (16)	−0.0043 (13)	−0.0022 (13)	−0.0053 (14)
C35	0.0618 (13)	0.0831 (15)	0.0783 (15)	−0.0053 (12)	−0.0018 (12)	−0.0069 (13)
C36	0.0672 (13)	0.0841 (14)	0.0811 (15)	−0.0094 (12)	−0.0034 (12)	−0.0056 (13)
N1	0.0474 (14)	0.0451 (14)	0.0442 (15)	0.0019 (11)	0.0041 (12)	−0.0008 (12)
N2	0.0435 (13)	0.0435 (13)	0.0455 (14)	0.0006 (11)	0.0068 (12)	−0.0040 (12)
N3	0.0470 (14)	0.0443 (13)	0.0549 (16)	0.0028 (11)	0.0106 (13)	−0.0022 (12)
N4	0.0467 (14)	0.0518 (15)	0.0599 (16)	0.0075 (12)	0.0166 (13)	−0.0020 (13)

Geometric parameters (Å, º)

Fe1—C1	2.022 (3)	C11—H11A	0.9300
Fe1—C2	2.028 (3)	C12—C13	1.477 (4)
Fe1—C3	2.040 (3)	C13—C18	1.374 (4)
Fe1—C4	2.044 (3)	C13—C14	1.390 (4)
Fe1—C5	2.031 (3)	C14—C15	1.378 (5)
Fe1—C6	2.028 (3)	C14—H14A	0.9300
Fe1—C7	2.023 (3)	C15—C16	1.370 (6)
Fe1—C8	2.026 (3)	C15—H15A	0.9300
Fe1—C9	2.043 (3)	C16—C17	1.350 (6)
Fe1—C10	2.036 (3)	C16—H16A	0.9300
Fe2—C27	2.028 (3)	C17—C18	1.395 (5)
Fe2—C28	2.028 (3)	C17—H17A	0.9300
Fe2—C29	2.051 (4)	C18—H18A	0.9300
Fe2—C30	2.052 (4)	C19—C20	1.471 (4)
Fe2—C31	2.043 (3)	C20—C21	1.383 (4)
Fe2—C32	2.042 (4)	C20—C25	1.390 (4)
Fe2—C33	2.033 (4)	C21—C22	1.382 (4)
Fe2—C34	2.044 (4)	C21—H21A	0.9300
Fe2—C35	2.034 (4)	C22—C23	1.373 (5)
Fe2—C36	2.029 (4)	C22—H22A	0.9300
C11—N1	1.282 (3)	C23—C24	1.379 (4)
C19—N3	1.287 (3)	C23—H23A	0.9300
N1—N2	1.411 (3)	C24—C25	1.366 (4)
C12—C19	1.514 (4)	C24—H24A	0.9300
C12—N2	1.277 (3)	C25—H25A	0.9300
C26—N4	1.275 (3)	C26—C27	1.447 (4)
N3—N4	1.404 (3)	C26—H26A	0.9300
C1—C2	1.423 (4)	C27—C28	1.420 (4)
C1—C5	1.428 (4)	C27—C31	1.425 (4)
C1—C11	1.445 (4)	C28—C29	1.405 (5)
C2—C3	1.406 (4)	C28—H28A	0.9800
C2—H2B	0.9800	C29—C30	1.415 (5)
C3—C4	1.403 (4)	C29—H29A	0.9800
C3—H3B	0.9800	C30—C31	1.416 (5)
C4—C5	1.419 (4)	C30—H30A	0.9800
C4—H4B	0.9800	C31—H31A	0.9800
C5—H5A	0.9800	C32—C33	1.397 (5)
C6—C7	1.398 (5)	C32—C36	1.411 (5)
C6—C10	1.403 (5)	C32—H32A	0.9800
C6—H6A	0.9800	C33—C34	1.418 (5)
C7—C8	1.415 (5)	C33—H33A	0.9800
C7—H7A	0.9800	C34—C35	1.376 (5)
C8—C9	1.396 (5)	C34—H34A	0.9800
C8—H8A	0.9800	C35—C36	1.392 (5)
C9—C10	1.407 (5)	C35—H35A	0.9800
C9—H9A	0.9800	C36—H36A	0.9800
C10—H10A	0.9800
C1—Fe1—C7	120.56 (14)	Fe1—C7—H7A	126.2
C1—Fe1—C8	156.30 (14)	C9—C8—C7	108.3 (3)
C7—Fe1—C8	40.90 (14)	C9—C8—Fe1	70.60 (19)
C1—Fe1—C6	107.50 (13)	C7—C8—Fe1	69.42 (19)
C7—Fe1—C6	40.39 (13)	C9—C8—H8A	125.9
C8—Fe1—C6	68.06 (15)	C7—C8—H8A	125.9
C1—Fe1—C2	41.14 (11)	Fe1—C8—H8A	125.9
C7—Fe1—C2	106.39 (14)	C8—C9—C10	107.8 (3)
C8—Fe1—C2	120.56 (14)	C8—C9—Fe1	69.28 (19)
C6—Fe1—C2	123.93 (14)	C10—C9—Fe1	69.56 (18)
C1—Fe1—C5	41.25 (11)	C8—C9—H9A	126.1
C7—Fe1—C5	157.01 (15)	C10—C9—H9A	126.1
C8—Fe1—C5	160.92 (15)	Fe1—C9—H9A	126.1
C6—Fe1—C5	122.26 (14)	C6—C10—C9	108.1 (3)
C2—Fe1—C5	69.06 (12)	C6—C10—Fe1	69.50 (19)
C1—Fe1—C10	124.89 (13)	C9—C10—Fe1	70.08 (18)
C7—Fe1—C10	68.02 (14)	C6—C10—H10A	126.0
C8—Fe1—C10	67.78 (14)	C9—C10—H10A	126.0
C6—Fe1—C10	40.37 (13)	Fe1—C10—H10A	126.0
C2—Fe1—C10	161.23 (14)	N1—C11—C1	121.5 (3)
C5—Fe1—C10	108.65 (14)	N1—C11—H11A	119.3
C1—Fe1—C3	68.51 (12)	C1—C11—H11A	119.3
C7—Fe1—C3	123.67 (14)	N2—C12—C13	119.2 (3)
C8—Fe1—C3	107.38 (14)	N2—C12—C19	123.2 (2)
C6—Fe1—C3	160.30 (14)	C13—C12—C19	117.6 (2)
C2—Fe1—C3	40.46 (11)	C18—C13—C14	118.0 (3)
C5—Fe1—C3	68.32 (12)	C18—C13—C12	121.5 (3)
C10—Fe1—C3	157.53 (14)	C14—C13—C12	120.5 (3)
C1—Fe1—C9	161.86 (14)	C15—C14—C13	120.5 (4)
C7—Fe1—C9	68.15 (15)	C15—C14—H14A	119.7
C8—Fe1—C9	40.12 (13)	C13—C14—H14A	119.7
C6—Fe1—C9	67.91 (14)	C16—C15—C14	120.7 (4)
C2—Fe1—C9	156.10 (14)	C16—C15—H15A	119.7
C5—Fe1—C9	125.06 (14)	C14—C15—H15A	119.7
C10—Fe1—C9	40.36 (13)	C17—C16—C15	119.5 (4)
C3—Fe1—C9	121.82 (14)	C17—C16—H16A	120.2
C1—Fe1—C4	68.73 (12)	C15—C16—H16A	120.2
C7—Fe1—C4	160.32 (15)	C16—C17—C18	120.6 (4)
C8—Fe1—C4	124.13 (15)	C16—C17—H17A	119.7
C6—Fe1—C4	158.17 (14)	C18—C17—H17A	119.7
C2—Fe1—C4	68.27 (13)	C13—C18—C17	120.6 (4)
C5—Fe1—C4	40.74 (12)	C13—C18—H18A	119.7
C10—Fe1—C4	122.96 (14)	C17—C18—H18A	119.7
C3—Fe1—C4	40.19 (12)	N3—C19—C20	119.6 (2)
C9—Fe1—C4	108.60 (14)	N3—C19—C12	121.5 (3)
C28—Fe2—C27	41.00 (12)	C20—C19—C12	118.8 (2)
C28—Fe2—C36	131.68 (15)	C21—C20—C25	118.4 (3)
C27—Fe2—C36	170.50 (14)	C21—C20—C19	120.6 (3)
C28—Fe2—C35	170.35 (14)	C25—C20—C19	121.0 (3)
C27—Fe2—C35	147.92 (14)	C22—C21—C20	120.4 (3)
C36—Fe2—C35	40.06 (13)	C22—C21—H21A	119.8
C28—Fe2—C33	117.07 (14)	C20—C21—H21A	119.8
C27—Fe2—C33	109.08 (14)	C23—C22—C21	120.3 (3)
C36—Fe2—C33	67.43 (15)	C23—C22—H22A	119.8
C35—Fe2—C33	66.84 (15)	C21—C22—H22A	119.8
C28—Fe2—C32	109.28 (14)	C22—C23—C24	119.8 (3)
C27—Fe2—C32	131.18 (13)	C22—C23—H23A	120.1
C36—Fe2—C32	40.56 (14)	C24—C23—H23A	120.1
C35—Fe2—C32	67.48 (15)	C25—C24—C23	120.0 (3)
C33—Fe2—C32	40.09 (14)	C25—C24—H24A	120.0
C28—Fe2—C31	68.52 (13)	C23—C24—H24A	120.0
C27—Fe2—C31	40.97 (11)	C24—C25—C20	121.2 (3)
C36—Fe2—C31	147.90 (14)	C24—C25—H25A	119.4
C35—Fe2—C31	116.27 (14)	C20—C25—H25A	119.4
C33—Fe2—C31	131.46 (16)	N4—C26—C27	121.5 (3)
C32—Fe2—C31	170.12 (15)	N4—C26—H26A	119.2
C28—Fe2—C34	149.07 (14)	C27—C26—H26A	119.2
C27—Fe2—C34	116.04 (15)	C28—C27—C31	107.3 (3)
C36—Fe2—C34	67.59 (16)	C28—C27—C26	127.8 (3)
C35—Fe2—C34	39.44 (14)	C31—C27—C26	124.8 (3)
C33—Fe2—C34	40.70 (14)	C28—C27—Fe2	69.52 (18)
C32—Fe2—C34	68.19 (16)	C31—C27—Fe2	70.09 (18)
C31—Fe2—C34	108.40 (16)	C26—C27—Fe2	123.3 (2)
C28—Fe2—C29	40.30 (13)	C29—C28—C27	108.7 (3)
C27—Fe2—C29	68.53 (14)	C29—C28—Fe2	70.72 (19)
C36—Fe2—C29	109.54 (16)	C27—C28—Fe2	69.48 (18)
C35—Fe2—C29	132.00 (16)	C29—C28—H28A	125.6
C33—Fe2—C29	148.84 (17)	C27—C28—H28A	125.6
C32—Fe2—C29	116.81 (16)	Fe2—C28—H28A	125.6
C31—Fe2—C29	68.23 (16)	C28—C29—C30	107.8 (3)
C34—Fe2—C29	169.40 (15)	C28—C29—Fe2	68.97 (19)
C28—Fe2—C30	67.90 (15)	C30—C29—Fe2	69.9 (2)
C27—Fe2—C30	68.42 (14)	C28—C29—H29A	126.1
C36—Fe2—C30	116.59 (16)	C30—C29—H29A	126.1
C35—Fe2—C30	109.77 (16)	Fe2—C29—H29A	126.1
C33—Fe2—C30	170.00 (18)	C29—C30—C31	108.4 (3)
C32—Fe2—C30	148.66 (18)	C29—C30—Fe2	69.8 (2)
C31—Fe2—C30	40.45 (15)	C31—C30—Fe2	69.4 (2)
C34—Fe2—C30	130.77 (17)	C29—C30—H30A	125.8
C29—Fe2—C30	40.34 (15)	C31—C30—H30A	125.8
C2—C1—C5	107.6 (3)	Fe2—C30—H30A	125.8
C2—C1—C11	126.8 (3)	C30—C31—C27	107.7 (3)
C5—C1—C11	125.2 (3)	C30—C31—Fe2	70.1 (2)
C2—C1—Fe1	69.63 (16)	C27—C31—Fe2	68.94 (18)
C5—C1—Fe1	69.72 (16)	C30—C31—H31A	126.2
C11—C1—Fe1	120.59 (19)	C27—C31—H31A	126.2
C3—C2—C1	107.8 (3)	Fe2—C31—H31A	126.2
C3—C2—Fe1	70.23 (17)	C33—C32—C36	106.8 (4)
C1—C2—Fe1	69.23 (16)	C33—C32—Fe2	69.6 (2)
C3—C2—H2B	126.1	C36—C32—Fe2	69.2 (2)
C1—C2—H2B	126.1	C33—C32—H32A	126.6
Fe1—C2—H2B	126.1	C36—C32—H32A	126.6
C4—C3—C2	108.8 (3)	Fe2—C32—H32A	126.6
C4—C3—Fe1	70.08 (17)	C32—C33—C34	108.9 (3)
C2—C3—Fe1	69.31 (16)	C32—C33—Fe2	70.3 (2)
C4—C3—H3B	125.6	C34—C33—Fe2	70.1 (2)
C2—C3—H3B	125.6	C32—C33—H33A	125.5
Fe1—C3—H3B	125.6	C34—C33—H33A	125.5
C3—C4—C5	108.2 (3)	Fe2—C33—H33A	125.5
C3—C4—Fe1	69.74 (17)	C35—C34—C33	106.6 (4)
C5—C4—Fe1	69.15 (17)	C35—C34—Fe2	69.9 (2)
C3—C4—H4B	125.9	C33—C34—Fe2	69.2 (2)
C5—C4—H4B	125.9	C35—C34—H34A	126.7
Fe1—C4—H4B	125.9	C33—C34—H34A	126.7
C4—C5—C1	107.5 (3)	Fe2—C34—H34A	126.7
C4—C5—Fe1	70.11 (16)	C34—C35—C36	109.9 (4)
C1—C5—Fe1	69.03 (15)	C34—C35—Fe2	70.7 (2)
C4—C5—H5A	126.3	C36—C35—Fe2	69.8 (2)
C1—C5—H5A	126.3	C34—C35—H35A	125.0
Fe1—C5—H5A	126.3	C36—C35—H35A	125.0
C7—C6—C10	108.3 (3)	Fe2—C35—H35A	125.0
C7—C6—Fe1	69.59 (18)	C35—C36—C32	107.7 (4)
C10—C6—Fe1	70.13 (19)	C35—C36—Fe2	70.1 (2)
C7—C6—H6A	125.8	C32—C36—Fe2	70.2 (2)
C10—C6—H6A	125.8	C35—C36—H36A	126.1
Fe1—C6—H6A	125.8	C32—C36—H36A	126.1
C6—C7—C8	107.5 (3)	Fe2—C36—H36A	126.1
C6—C7—Fe1	70.02 (19)	C11—N1—N2	111.9 (2)
C8—C7—Fe1	69.68 (18)	C12—N2—N1	112.2 (2)
C6—C7—H7A	126.2	C19—N3—N4	112.0 (2)
C8—C7—H7A	126.2	C26—N4—N3	112.0 (2)