N,N'-Butane­dioylbis(5-ferrocen­yl-3-meth­yl-1H-pyrazole)

The title compound, [Fe₂(C₅H₅)₂(C₂₂H₂₀N₄O₂)], has been synthesized by the reaction of ferrocenoylacetone and butane­dioic acid dihydrazide in ethanol. The dihedral angles between one pyrazole ring and the attached cyclopentadienyl ring and carbonyl plane are 33.5 (4) and 4.4 (8)°, respectively; for the other pyrazole ring, the corresponding angles are 29.5 (4) and 11.2 (8)°, respecively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.061
• wR factor = 0.207
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 115
              The title compound, [Fe~2~(C~5~H~5~)~2~(C~22~H~20~N~4~O~2~)]~, has been
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-Butanedioylbis(5-ferrocenyl-3-methyl-1H-pyrazole)

Crystal data

[Fe2(C5H5)2(C22H20N4O2)]	F(000) = 636
Mr = 614.30	Dx = 1.517 Mg m^−3
Triclinic, P1	Melting point: 407 K
a = 9.0105 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.633 (3) Å	Cell parameters from 25 reflections
c = 13.717 (3) Å	θ = 10–13°
α = 64.45 (3)°	µ = 1.12 mm^−1
β = 73.85 (3)°	T = 293 K
γ = 88.61 (3)°	Prism, orange
V = 1344.8 (6) Å^3	0.4 × 0.3 × 0.2 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	4140 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω/2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = −15→15
Tmin = 0.656, Tmax = 0.796	l = −16→16
5623 measured reflections	3 standard reflections every 200 reflections
5268 independent reflections	intensity decay: 0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.207	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 8.9P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
5268 reflections	Δρmax = 0.76 e Å^−3
362 parameters	Δρmin = −0.61 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

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	0.71152 (9)	0.33386 (6)	0.45748 (6)	0.0318 (3)
Fe2	1.29939 (9)	−0.33022 (6)	0.04043 (6)	0.0326 (3)
O1	0.9595 (6)	0.2047 (4)	0.1892 (4)	0.0578 (13)
O2	1.2865 (7)	−0.0890 (5)	0.1210 (4)	0.0682 (16)
N1	0.9049 (5)	−0.0570 (4)	0.4374 (4)	0.0351 (10)
N2	0.8901 (5)	0.0588 (4)	0.3685 (4)	0.0321 (9)
N3	1.2196 (5)	0.1180 (4)	−0.1264 (4)	0.0375 (10)
N4	1.2663 (5)	0.0142 (4)	−0.0566 (4)	0.0349 (10)
C1	0.7658 (10)	0.4557 (6)	0.5061 (7)	0.060 (2)
H1	0.7709	0.5416	0.4637	0.072*
C2	0.6348 (9)	0.3799 (7)	0.5874 (6)	0.0548 (17)
H2	0.5318	0.4037	0.6112	0.066*
C4	0.8335 (7)	0.2677 (6)	0.5725 (5)	0.0451 (14)
H4	0.8926	0.1993	0.5849	0.054*
C5	0.8912 (8)	0.3858 (6)	0.4962 (6)	0.0536 (16)
H5	0.9978	0.4149	0.4463	0.064*
C3	0.6745 (8)	0.2652 (6)	0.6281 (5)	0.0514 (16)
H3	0.6045	0.1945	0.6856	0.062*
C6	0.5522 (8)	0.3640 (6)	0.3699 (6)	0.0495 (16)
H6	0.4573	0.4020	0.3826	0.059*
C7	0.5654 (6)	0.2409 (5)	0.4252 (5)	0.0383 (12)
H7	0.4812	0.1796	0.4818	0.046*
C8	0.7240 (6)	0.2226 (5)	0.3831 (5)	0.0328 (11)
C9	0.8053 (7)	0.3349 (5)	0.3036 (5)	0.0435 (13)
H9	0.9162	0.3504	0.2617	0.052*
C10	0.6989 (9)	0.4222 (6)	0.2951 (5)	0.0492 (15)
H10	0.7240	0.5073	0.2467	0.059*
C11	0.7770 (6)	0.1042 (5)	0.4276 (4)	0.0302 (11)
C12	0.7220 (6)	0.0143 (5)	0.5341 (5)	0.0349 (11)
H12	0.6446	0.0166	0.5941	0.042*
C13	0.8039 (6)	−0.0823 (5)	0.5363 (5)	0.0345 (11)
C14	0.7881 (7)	−0.2015 (5)	0.6321 (5)	0.0451 (14)
H14A	0.8603	−0.2487	0.6079	0.068*
H14B	0.6841	−0.2386	0.6566	0.068*
H14C	0.8098	−0.1940	0.6937	0.068*
C15	0.9751 (6)	0.1067 (5)	0.2535 (5)	0.0376 (12)
C16	1.0863 (7)	0.0292 (5)	0.2193 (5)	0.0415 (13)
H16A	1.0387	−0.0519	0.2586	0.050*
H16B	1.1797	0.0323	0.2404	0.050*
C17	1.1280 (7)	0.0708 (5)	0.0927 (5)	0.0366 (12)
H17A	1.0340	0.0711	0.0712	0.044*
H17B	1.1795	0.1508	0.0536	0.044*
C18	1.2338 (7)	−0.0096 (5)	0.0584 (5)	0.0392 (13)
C19	1.2317 (8)	0.2216 (6)	−0.3245 (5)	0.0488 (15)
H19A	1.1819	0.2774	−0.2996	0.073*
H19B	1.1661	0.1952	−0.3559	0.073*
H19C	1.3293	0.2586	−0.3811	0.073*
C20	1.2591 (6)	0.1186 (5)	−0.2265 (4)	0.0366 (12)
C21	1.3287 (6)	0.0166 (5)	−0.2233 (4)	0.0372 (12)
H21	1.3646	−0.0022	−0.2837	0.045*
C22	1.3340 (6)	−0.0502 (5)	−0.1147 (4)	0.0323 (11)
C23	1.5358 (7)	−0.3192 (6)	0.0047 (6)	0.0487 (15)
H23	1.5940	−0.3728	0.0528	0.058*
C24	1.4909 (7)	−0.3336 (6)	−0.0796 (5)	0.0492 (16)
H24	1.5128	−0.3987	−0.1004	0.059*
C25	1.4064 (7)	−0.2376 (5)	−0.1290 (5)	0.0422 (13)
H25	1.3606	−0.2253	−0.1895	0.051*
C26	1.3983 (6)	−0.1638 (5)	−0.0735 (5)	0.0349 (12)
C27	1.4789 (7)	−0.2144 (5)	0.0101 (5)	0.0431 (13)
H27	1.4925	−0.1830	0.0615	0.052*
C28	1.1522 (8)	−0.3703 (7)	0.1978 (5)	0.0559 (17)
H28	1.1643	−0.3382	0.2491	0.067*
C29	1.2108 (8)	−0.4721 (6)	0.1927 (6)	0.0577 (18)
H29	1.2719	−0.5232	0.2400	0.069*
C30	1.1688 (8)	−0.4887 (5)	0.1083 (6)	0.0552 (17)
H30	1.1942	−0.5533	0.0872	0.066*
C31	1.0825 (7)	−0.3961 (6)	0.0607 (6)	0.0542 (17)
H31	1.0382	−0.3845	−0.0004	0.065*
C32	1.0713 (7)	−0.3224 (6)	0.1155 (6)	0.0504 (16)
H32	1.0178	−0.2511	0.0994	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0337 (4)	0.0305 (4)	0.0365 (4)	0.0066 (3)	−0.0152 (3)	−0.0168 (3)
Fe2	0.0305 (4)	0.0307 (4)	0.0331 (4)	0.0057 (3)	−0.0062 (3)	−0.0129 (3)
O1	0.076 (3)	0.051 (3)	0.036 (2)	0.027 (2)	−0.008 (2)	−0.016 (2)
O2	0.107 (4)	0.066 (3)	0.039 (2)	0.049 (3)	−0.031 (3)	−0.026 (2)
N1	0.035 (2)	0.035 (2)	0.035 (2)	0.0077 (19)	−0.0111 (19)	−0.016 (2)
N2	0.034 (2)	0.032 (2)	0.031 (2)	0.0087 (18)	−0.0116 (18)	−0.0150 (19)
N3	0.041 (3)	0.034 (2)	0.034 (2)	0.006 (2)	−0.007 (2)	−0.015 (2)
N4	0.041 (3)	0.033 (2)	0.029 (2)	0.0077 (19)	−0.0079 (19)	−0.0144 (19)
C1	0.097 (6)	0.032 (3)	0.073 (5)	0.012 (3)	−0.048 (4)	−0.029 (3)
C2	0.057 (4)	0.070 (5)	0.065 (4)	0.023 (4)	−0.029 (3)	−0.049 (4)
C4	0.051 (4)	0.048 (4)	0.051 (4)	0.017 (3)	−0.033 (3)	−0.026 (3)
C5	0.045 (4)	0.064 (4)	0.061 (4)	−0.005 (3)	−0.021 (3)	−0.032 (4)
C3	0.064 (4)	0.059 (4)	0.035 (3)	0.000 (3)	−0.020 (3)	−0.020 (3)
C6	0.057 (4)	0.050 (4)	0.069 (4)	0.032 (3)	−0.043 (4)	−0.036 (3)
C7	0.028 (3)	0.049 (3)	0.053 (3)	0.010 (2)	−0.017 (2)	−0.033 (3)
C8	0.032 (3)	0.038 (3)	0.036 (3)	0.007 (2)	−0.014 (2)	−0.022 (2)
C9	0.047 (3)	0.042 (3)	0.040 (3)	0.001 (3)	−0.008 (3)	−0.019 (3)
C10	0.074 (5)	0.040 (3)	0.038 (3)	0.017 (3)	−0.029 (3)	−0.016 (3)
C11	0.026 (2)	0.034 (3)	0.036 (3)	0.006 (2)	−0.010 (2)	−0.020 (2)
C12	0.032 (3)	0.037 (3)	0.034 (3)	0.004 (2)	−0.004 (2)	−0.017 (2)
C13	0.033 (3)	0.037 (3)	0.039 (3)	0.004 (2)	−0.014 (2)	−0.019 (2)
C14	0.045 (3)	0.037 (3)	0.046 (3)	0.002 (3)	−0.015 (3)	−0.011 (3)
C15	0.036 (3)	0.048 (3)	0.035 (3)	0.015 (2)	−0.014 (2)	−0.021 (3)
C16	0.043 (3)	0.048 (3)	0.038 (3)	0.019 (3)	−0.012 (2)	−0.023 (3)
C17	0.038 (3)	0.040 (3)	0.034 (3)	0.009 (2)	−0.009 (2)	−0.019 (2)
C18	0.046 (3)	0.038 (3)	0.033 (3)	0.008 (3)	−0.010 (2)	−0.018 (2)
C19	0.054 (4)	0.047 (4)	0.039 (3)	0.011 (3)	−0.012 (3)	−0.016 (3)
C20	0.035 (3)	0.037 (3)	0.032 (3)	−0.001 (2)	−0.005 (2)	−0.012 (2)
C21	0.040 (3)	0.042 (3)	0.029 (3)	0.005 (2)	−0.005 (2)	−0.019 (2)
C22	0.027 (2)	0.035 (3)	0.032 (3)	0.002 (2)	−0.003 (2)	−0.016 (2)
C23	0.033 (3)	0.046 (3)	0.060 (4)	0.010 (3)	−0.012 (3)	−0.018 (3)
C24	0.045 (3)	0.042 (3)	0.051 (4)	0.011 (3)	0.004 (3)	−0.022 (3)
C25	0.046 (3)	0.039 (3)	0.035 (3)	0.005 (3)	0.001 (2)	−0.019 (3)
C26	0.028 (3)	0.033 (3)	0.038 (3)	0.003 (2)	−0.001 (2)	−0.015 (2)
C27	0.035 (3)	0.041 (3)	0.052 (4)	0.006 (2)	−0.011 (3)	−0.020 (3)
C28	0.051 (4)	0.068 (5)	0.035 (3)	−0.002 (3)	0.004 (3)	−0.020 (3)
C29	0.051 (4)	0.049 (4)	0.045 (4)	0.008 (3)	−0.009 (3)	0.001 (3)
C30	0.049 (4)	0.031 (3)	0.072 (5)	−0.001 (3)	−0.004 (3)	−0.019 (3)
C31	0.038 (3)	0.059 (4)	0.052 (4)	−0.008 (3)	−0.008 (3)	−0.015 (3)
C32	0.030 (3)	0.045 (3)	0.055 (4)	0.007 (3)	0.003 (3)	−0.012 (3)

Geometric parameters (Å, º)

O1—C15	1.203 (7)	C19—H19B	0.9600
N1—C13	1.313 (7)	C19—H19C	0.9600
N1—N2	1.385 (6)	C20—C21	1.409 (8)
N2—C11	1.392 (6)	C21—C22	1.373 (8)
N2—C15	1.403 (7)	C21—H21	0.9300
C1—C2	1.398 (11)	C22—C26	1.468 (7)
C1—C5	1.430 (10)	C23—C24	1.407 (10)
C1—H1	0.9800	C23—C27	1.432 (9)
C2—C3	1.388 (10)	C23—H23	0.9800
C2—H2	0.9800	C24—C25	1.429 (9)
C4—C5	1.407 (9)	C24—H24	0.9800
C4—C3	1.417 (9)	C25—C26	1.425 (8)
C3—H3	0.9800	C25—H25	0.9800
C4—H4	0.9800	C26—C27	1.436 (8)
C5—H5	0.9800	C27—H27	0.9800
C6—C10	1.408 (10)	C28—C29	1.400 (10)
C6—C7	1.425 (9)	C28—C32	1.422 (10)
C6—H6	0.9800	C28—H28	0.9800
C7—C8	1.439 (7)	C29—C30	1.409 (11)
C7—H7	0.9800	C29—H29	0.9800
C8—C9	1.418 (8)	C30—C31	1.406 (10)
C8—C11	1.476 (7)	C30—H30	0.9800
C9—C10	1.431 (9)	C31—C32	1.413 (10)
C9—H9	0.9800	C31—H31	0.9800
C10—H10	0.9800	C32—H32	0.9800
C11—C12	1.365 (7)	Fe1—C9	2.037 (6)
C12—C13	1.404 (8)	Fe1—C1	2.038 (6)
C12—H12	0.9300	Fe1—C7	2.039 (5)
C13—C14	1.488 (8)	Fe1—C5	2.041 (6)
C14—H14A	0.9600	Fe1—C3	2.042 (6)
C14—H14B	0.9600	Fe1—C4	2.044 (6)
C14—H14C	0.9600	Fe1—C2	2.045 (6)
C15—C16	1.507 (7)	Fe1—C6	2.046 (6)
C16—C17	1.515 (7)	Fe1—C8	2.048 (5)
C16—H16A	0.9700	Fe1—C10	2.051 (6)
C16—H16B	0.9700	Fe2—C29	2.031 (6)
C17—C18	1.509 (7)	Fe2—C26	2.035 (5)
C17—H17A	0.9700	Fe2—C27	2.036 (6)
C17—H17B	0.9700	Fe2—C30	2.039 (6)
O2—C18	1.195 (7)	Fe2—C25	2.040 (6)
N3—C20	1.315 (7)	Fe2—C31	2.041 (6)
N3—N4	1.389 (6)	Fe2—C24	2.041 (6)
N4—C18	1.415 (7)	Fe2—C23	2.042 (6)
N4—C22	1.391 (7)	Fe2—C28	2.043 (6)
C19—C20	1.491 (8)	Fe2—C32	2.048 (6)
C19—H19A	0.9600
C9—Fe1—C1	126.5 (3)	Fe1—C6—H6	125.7
C9—Fe1—C7	68.6 (2)	C6—C7—C8	108.0 (5)
C1—Fe1—C7	154.3 (3)	C6—C7—Fe1	69.9 (3)
C9—Fe1—C5	106.0 (3)	C8—C7—Fe1	69.7 (3)
C1—Fe1—C5	41.1 (3)	C6—C7—H7	126.0
C7—Fe1—C5	163.7 (3)	C8—C7—H7	126.0
C9—Fe1—C3	152.8 (3)	Fe1—C7—H7	126.0
C1—Fe1—C3	67.4 (3)	C9—C8—C7	107.0 (5)
C7—Fe1—C3	109.4 (3)	C9—C8—C11	131.7 (5)
C5—Fe1—C3	68.0 (3)	C7—C8—C11	121.2 (5)
C9—Fe1—C4	117.7 (3)	C9—C8—Fe1	69.3 (3)
C1—Fe1—C4	68.0 (3)	C7—C8—Fe1	69.0 (3)
C7—Fe1—C4	127.2 (3)	C11—C8—Fe1	123.9 (4)
C5—Fe1—C4	40.3 (3)	C8—C9—C10	108.8 (5)
C3—Fe1—C4	40.6 (3)	C8—C9—Fe1	70.1 (3)
C9—Fe1—C2	164.7 (3)	C10—C9—Fe1	70.0 (3)
C1—Fe1—C2	40.0 (3)	C8—C9—H9	125.6
C7—Fe1—C2	120.9 (3)	C10—C9—H9	125.6
C5—Fe1—C2	68.1 (3)	Fe1—C9—H9	125.6
C3—Fe1—C2	39.7 (3)	C6—C10—C9	107.8 (5)
C4—Fe1—C2	67.6 (3)	C6—C10—Fe1	69.7 (3)
C9—Fe1—C6	68.3 (3)	C9—C10—Fe1	69.0 (3)
C1—Fe1—C6	119.9 (3)	C6—C10—H10	126.1
C7—Fe1—C6	40.8 (2)	C9—C10—H10	126.1
C5—Fe1—C6	153.1 (3)	Fe1—C10—H10	126.1
C3—Fe1—C6	128.9 (3)	C12—C11—N2	105.2 (4)
C4—Fe1—C6	165.9 (3)	C12—C11—C8	127.5 (5)
C2—Fe1—C6	110.2 (3)	N2—C11—C8	127.3 (5)
C9—Fe1—C8	40.6 (2)	C11—C12—C13	107.3 (5)
C1—Fe1—C8	163.4 (3)	C11—C12—H12	126.4
C7—Fe1—C8	41.2 (2)	C13—C12—H12	126.4
C5—Fe1—C8	124.8 (3)	N1—C13—C12	111.2 (5)
C3—Fe1—C8	119.6 (3)	N1—C13—C14	120.1 (5)
C4—Fe1—C8	106.7 (2)	C12—C13—C14	128.7 (5)
C2—Fe1—C8	154.3 (3)	C13—C14—H14A	109.5
C6—Fe1—C8	68.9 (2)	C13—C14—H14B	109.5
C9—Fe1—C10	41.0 (3)	H14A—C14—H14B	109.5
C1—Fe1—C10	108.0 (3)	C13—C14—H14C	109.5
C7—Fe1—C10	68.4 (3)	H14A—C14—H14C	109.5
C5—Fe1—C10	118.3 (3)	H14B—C14—H14C	109.5
C3—Fe1—C10	165.6 (3)	O1—C15—N2	120.5 (5)
C4—Fe1—C10	152.1 (3)	O1—C15—C16	123.9 (5)
C2—Fe1—C10	128.1 (3)	N2—C15—C16	115.6 (5)
C6—Fe1—C10	40.2 (3)	C15—C16—C17	109.8 (5)
C8—Fe1—C10	68.8 (2)	C15—C16—H16A	109.7
C29—Fe2—C26	158.9 (3)	C17—C16—H16A	109.7
C29—Fe2—C27	122.3 (3)	C15—C16—H16B	109.7
C26—Fe2—C27	41.3 (2)	C17—C16—H16B	109.7
C29—Fe2—C30	40.5 (3)	H16A—C16—H16B	108.2
C26—Fe2—C30	159.3 (3)	C18—C17—C16	110.2 (5)
C27—Fe2—C30	157.6 (3)	C18—C17—H17A	109.6
C29—Fe2—C25	158.7 (3)	C16—C17—H17A	109.6
C26—Fe2—C25	40.9 (2)	C18—C17—H17B	109.6
C27—Fe2—C25	69.1 (3)	C16—C17—H17B	109.6
C30—Fe2—C25	122.5 (3)	H17A—C17—H17B	108.1
C29—Fe2—C31	67.7 (3)	O2—C18—N4	120.7 (5)
C26—Fe2—C31	123.8 (3)	O2—C18—C17	124.7 (5)
C27—Fe2—C31	160.6 (3)	N4—C18—C17	114.6 (5)
C30—Fe2—C31	40.3 (3)	C20—C19—H19A	109.5
C25—Fe2—C31	107.7 (3)	C20—C19—H19B	109.5
C29—Fe2—C24	122.3 (3)	H19A—C19—H19B	109.5
C26—Fe2—C24	69.0 (2)	C20—C19—H19C	109.5
C27—Fe2—C24	68.8 (3)	H19A—C19—H19C	109.5
C30—Fe2—C24	106.3 (3)	H19B—C19—H19C	109.5
C25—Fe2—C24	41.0 (2)	N3—C20—C21	111.2 (5)
C31—Fe2—C24	122.1 (3)	N3—C20—C19	119.5 (5)
C29—Fe2—C23	107.1 (3)	C21—C20—C19	129.3 (5)
C26—Fe2—C23	69.1 (2)	C22—C21—C20	107.6 (5)
C27—Fe2—C23	41.1 (2)	C22—C21—H21	126.2
C30—Fe2—C23	121.2 (3)	C20—C21—H21	126.2
C25—Fe2—C23	68.5 (3)	C21—C22—N4	104.4 (5)
C31—Fe2—C23	157.1 (3)	C21—C22—C26	126.0 (5)
C24—Fe2—C23	40.3 (3)	N4—C22—C26	129.5 (5)
C29—Fe2—C28	40.2 (3)	C24—C23—C27	108.5 (6)
C26—Fe2—C28	123.4 (3)	C24—C23—Fe2	69.8 (4)
C27—Fe2—C28	107.8 (3)	C27—C23—Fe2	69.2 (3)
C30—Fe2—C28	68.2 (3)	C24—C23—H23	125.7
C25—Fe2—C28	159.5 (3)	C27—C23—H23	125.7
C31—Fe2—C28	68.1 (3)	Fe2—C23—H23	125.7
C24—Fe2—C28	158.4 (3)	C23—C24—C25	108.3 (5)
C23—Fe2—C28	123.3 (3)	C23—C24—Fe2	69.9 (3)
C29—Fe2—C32	67.8 (3)	C25—C24—Fe2	69.4 (3)
C26—Fe2—C32	108.5 (2)	C23—C24—H24	125.9
C27—Fe2—C32	124.2 (3)	C25—C24—H24	125.9
C30—Fe2—C32	68.1 (3)	Fe2—C24—H24	125.9
C25—Fe2—C32	123.2 (3)	C26—C25—C24	108.1 (6)
C31—Fe2—C32	40.4 (3)	C26—C25—Fe2	69.3 (3)
C24—Fe2—C32	158.6 (3)	C24—C25—Fe2	69.6 (3)
C23—Fe2—C32	160.4 (3)	C26—C25—H25	126.0
C28—Fe2—C32	40.7 (3)	C24—C25—H25	126.0
C13—N1—N2	105.4 (4)	Fe2—C25—H25	126.0
N1—N2—C11	110.9 (4)	C25—C26—C27	107.7 (5)
N1—N2—C15	118.1 (4)	C25—C26—C22	120.7 (5)
C11—N2—C15	130.7 (4)	C27—C26—C22	131.1 (5)
N3—N4—C22	111.8 (4)	C25—C26—Fe2	69.7 (3)
N3—N4—C18	116.5 (4)	C27—C26—Fe2	69.4 (3)
C22—N4—C18	131.7 (5)	C22—C26—Fe2	132.5 (4)
C20—N3—N4	105.0 (4)	C23—C27—C26	107.4 (5)
C2—C1—C5	107.9 (6)	C23—C27—Fe2	69.7 (3)
C2—C1—Fe1	70.3 (4)	C26—C27—Fe2	69.3 (3)
C5—C1—Fe1	69.6 (3)	C23—C27—H27	126.3
C2—C1—H1	126.0	C26—C27—H27	126.3
C5—C1—H1	126.0	Fe2—C27—H27	126.3
Fe1—C1—H1	126.0	C29—C28—C32	107.5 (6)
C3—C2—C1	108.6 (6)	C29—C28—Fe2	69.5 (4)
C3—C2—Fe1	70.0 (4)	C32—C28—Fe2	69.9 (3)
C1—C2—Fe1	69.7 (4)	C29—C28—H28	126.3
C3—C2—H2	125.7	C32—C28—H28	126.3
C1—C2—H2	125.7	Fe2—C28—H28	126.3
Fe1—C2—H2	125.7	C28—C29—C30	109.1 (6)
C5—C4—C3	107.8 (6)	C28—C29—Fe2	70.4 (4)
C5—C4—Fe1	69.7 (3)	C30—C29—Fe2	70.0 (4)
C3—C4—Fe1	69.6 (3)	C28—C29—H29	125.5
C5—C4—H4	126.1	C30—C29—H29	125.5
C3—C4—H4	126.1	Fe2—C29—H29	125.5
Fe1—C4—H4	126.1	C31—C30—C29	107.4 (6)
C4—C5—C1	107.2 (6)	C31—C30—Fe2	69.9 (4)
C4—C5—Fe1	70.0 (3)	C29—C30—Fe2	69.4 (4)
C1—C5—Fe1	69.4 (4)	C31—C30—H30	126.3
C4—C5—H5	126.4	C29—C30—H30	126.3
C1—C5—H5	126.4	Fe2—C30—H30	126.3
Fe1—C5—H5	126.4	C30—C31—C32	108.5 (6)
C2—C3—C4	108.4 (6)	C30—C31—Fe2	69.7 (4)
C2—C3—Fe1	70.3 (4)	C32—C31—Fe2	70.0 (4)
C4—C3—Fe1	69.8 (3)	C30—C31—H31	125.8
C2—C3—H3	125.8	C32—C31—H31	125.8
C4—C3—H3	125.8	Fe2—C31—H31	125.8
Fe1—C3—H3	125.8	C31—C32—C28	107.6 (6)
C10—C6—C7	108.5 (5)	C31—C32—Fe2	69.5 (4)
C10—C6—Fe1	70.1 (3)	C28—C32—Fe2	69.5 (3)
C7—C6—Fe1	69.3 (3)	C31—C32—H32	126.2
C10—C6—H6	125.7	C28—C32—H32	126.2
C7—C6—H6	125.7	Fe2—C32—H32	126.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1^i	0.98	2.58	3.534 (9)	164
C19—H19B···N1^ii	0.96	2.62	3.493 (9)	152

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