Tetraethyl­ammonium di­chloro­[4,5-di­chloro-1,2-bis(2-pyridine-2-carbox­amido)­benzene]­ferrate(III), [Et₄N][(bpc)FeCl₂]

In the title compound, [Et₄N][(bpc)FeCl₂] or (C₈H₂₀N)[FeCl₂(C₁₈H₁₀N₄O₂)], the metal ion is located in the bpc mean plane and two chloro ligands complete the coordination. The Cl-Fe-Cl angle is 144.26 (8)°. The 4,5-di­chloro­benzene ring of the bpc ligand is slightly tilted from the N1/N2/N3/N4 plane by 1.97 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.044
• wR factor = 0.102
• Data-to-parameter ratio = 8.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.96
         From the CIF: _reflns_number_total               2905
         Count of symmetry unique reflns         2905
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

---

Computing details

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CAD-4-PC Software; data reduction: XCAD4 (Harms, 1997); 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: SHELXL97.

(I)

Crystal data

(C8H20N)[FeCl2(C18H10N4O2)]	F(000) = 662
Mr = 642.20	Dx = 1.516 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.752 (2) Å	θ = 7.7–13.9°
b = 10.473 (2) Å	µ = 0.95 mm^−1
c = 15.685 (3) Å	T = 298 K
β = 101.94 (2)°	Block, dark green
V = 1406.6 (5) Å^3	0.20 × 0.15 × 0.10 mm
Z = 2

Data collection

Enraf-Nonius MACH-3 diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.4°
Graphite monochromator	h = 0→10
ω–2θ scans	k = 0→12
3094 measured reflections	l = −19→18
2905 independent reflections	3 standard reflections every 60 min
1907 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0446P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2905 reflections	Δρmax = 0.35 e Å^−3
348 parameters	Δρmin = −0.48 e Å^−3
1 restraint	Absolute structure: Flack (1983), 0000 Friedel reflections
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (8)

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 data were collected in the 2/m point group, whereas the refinement proved the structure to be non-centrosymetric with the space group P2₁. Although the data does not contain large fraction of Friedel-related reflections, the absolute structure could be evaluated using the TWIN instruction, leading to a BASF value of 0.09 (8). Inverting the structure led to a BASF value of 0.91 (8).

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

	x	y	z	Uiso*/Ueq
Fe1	0.28155 (11)	0.34573 (17)	0.17844 (6)	0.0308 (3)
Cl1	0.7793 (3)	0.6528 (2)	0.51669 (13)	0.0598 (7)
Cl2	0.4828 (3)	0.5993 (2)	0.59449 (12)	0.0569 (6)
Cl3	0.3477 (2)	0.13053 (18)	0.18581 (12)	0.0412 (5)
Cl4	0.1423 (3)	0.5038 (2)	0.09003 (13)	0.0564 (6)
O1	0.0523 (6)	0.4075 (6)	0.3811 (3)	0.0495 (15)
O2	0.6774 (7)	0.5680 (6)	0.2042 (3)	0.0546 (16)
N1	0.4245 (7)	0.3496 (7)	0.0782 (3)	0.0360 (13)
N2	0.4802 (6)	0.4413 (6)	0.2345 (4)	0.0315 (14)
N3	0.2407 (7)	0.3909 (6)	0.2984 (3)	0.0317 (15)
N4	0.0462 (7)	0.2705 (6)	0.1772 (4)	0.0370 (16)
C1	0.3978 (10)	0.2858 (8)	0.0028 (5)	0.048 (2)
H1	0.3141	0.2293	−0.0095	0.058*
C2	0.4908 (12)	0.3017 (9)	−0.0568 (5)	0.058 (3)
H2	0.4704	0.2571	−0.1092	0.070*
C3	0.6151 (11)	0.3849 (9)	−0.0375 (5)	0.057 (3)
H3	0.6784	0.3997	−0.0774	0.068*
C4	0.6427 (11)	0.4439 (9)	0.0394 (5)	0.058 (2)
H4	0.7283	0.4981	0.0540	0.069*
C5	0.5470 (9)	0.4260 (7)	0.0976 (4)	0.0344 (18)
C6	0.5755 (9)	0.4857 (7)	0.1848 (5)	0.0344 (17)
C7	0.4921 (8)	0.4784 (7)	0.3213 (4)	0.0310 (17)
C8	0.6206 (9)	0.5377 (8)	0.3725 (5)	0.0393 (19)
H8	0.7087	0.5530	0.3496	0.047*
C9	0.6197 (9)	0.5741 (7)	0.4562 (4)	0.0367 (18)
C10	0.4899 (10)	0.5507 (7)	0.4912 (5)	0.0395 (19)
C11	0.3619 (9)	0.4872 (7)	0.4417 (4)	0.0345 (17)
H11	0.2763	0.4680	0.4660	0.041*
C12	0.3618 (8)	0.4526 (7)	0.3567 (4)	0.0288 (16)
C13	0.0988 (8)	0.3725 (7)	0.3169 (4)	0.0328 (18)
C14	−0.0062 (8)	0.2983 (7)	0.2484 (5)	0.0309 (17)
C15	−0.1544 (9)	0.2597 (7)	0.2569 (5)	0.043 (2)
H15	−0.1924	0.2823	0.3059	0.052*
C16	−0.2423 (9)	0.1894 (8)	0.1934 (6)	0.048 (2)
H16	−0.3404	0.1611	0.1993	0.057*
C17	−0.1876 (9)	0.1594 (8)	0.1200 (6)	0.052 (2)
H17	−0.2485	0.1127	0.0750	0.062*
C18	−0.0397 (9)	0.2003 (8)	0.1147 (5)	0.047 (2)
H18	0.0005	0.1781	0.0663	0.056*
N5	0.0617 (7)	0.8177 (5)	0.3045 (4)	0.0368 (16)
C51	0.2130 (10)	0.8837 (9)	0.3039 (6)	0.060 (3)
H51A	0.2440	0.9312	0.3579	0.072*
H51B	0.1969	0.9447	0.2564	0.072*
C52	0.3472 (10)	0.7928 (10)	0.2941 (7)	0.075 (3)
H52A	0.3809	0.7458	0.3472	0.112*
H52B	0.4330	0.8417	0.2820	0.112*
H52C	0.3111	0.7344	0.2471	0.112*
C53	0.0086 (11)	0.7405 (11)	0.2224 (5)	0.067 (3)
H53A	−0.0894	0.6991	0.2249	0.081*
H53B	0.0851	0.6743	0.2200	0.081*
C54	−0.0137 (13)	0.8208 (13)	0.1381 (6)	0.099 (4)
H54A	−0.0921	0.8847	0.1389	0.149*
H54B	−0.0460	0.7663	0.0885	0.149*
H54C	0.0831	0.8615	0.1346	0.149*
C55	−0.0546 (9)	0.9213 (9)	0.3122 (6)	0.058 (2)
H55A	−0.0609	0.9802	0.2639	0.069*
H55B	−0.0174	0.9686	0.3656	0.069*
C56	−0.2180 (9)	0.8700 (12)	0.3125 (6)	0.079 (3)
H56A	−0.2486	0.8114	0.2650	0.119*
H56B	−0.2908	0.9396	0.3061	0.119*
H56C	−0.2173	0.8267	0.3665	0.119*
C57	0.0787 (11)	0.7254 (10)	0.3793 (6)	0.064 (3)
H57A	0.1484	0.6573	0.3698	0.077*
H57B	−0.0226	0.6875	0.3789	0.077*
C58	0.1398 (13)	0.7817 (12)	0.4681 (6)	0.091 (4)
H58A	0.2431	0.8147	0.4708	0.136*
H58B	0.1432	0.7167	0.5116	0.136*
H58C	0.0723	0.8496	0.4785	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0277 (6)	0.0339 (6)	0.0312 (5)	−0.0032 (6)	0.0070 (4)	0.0001 (5)
Cl1	0.0555 (15)	0.0695 (16)	0.0486 (12)	−0.0256 (13)	−0.0025 (10)	−0.0087 (11)
Cl2	0.0628 (15)	0.0718 (16)	0.0342 (10)	−0.0035 (13)	0.0053 (10)	−0.0083 (11)
Cl3	0.0389 (11)	0.0353 (11)	0.0510 (11)	−0.0020 (9)	0.0132 (9)	0.0039 (9)
Cl4	0.0618 (15)	0.0574 (14)	0.0504 (12)	0.0192 (12)	0.0123 (11)	0.0166 (11)
O1	0.036 (3)	0.071 (4)	0.047 (3)	0.000 (3)	0.021 (3)	−0.006 (3)
O2	0.054 (4)	0.059 (4)	0.056 (3)	−0.026 (3)	0.021 (3)	−0.006 (3)
N1	0.042 (4)	0.031 (3)	0.036 (3)	0.001 (4)	0.010 (3)	0.002 (3)
N2	0.027 (3)	0.030 (3)	0.040 (3)	−0.007 (3)	0.011 (3)	−0.004 (3)
N3	0.027 (3)	0.037 (4)	0.032 (3)	−0.004 (3)	0.008 (3)	0.000 (3)
N4	0.027 (4)	0.044 (4)	0.040 (3)	0.001 (3)	0.006 (3)	0.004 (3)
C1	0.063 (6)	0.046 (5)	0.038 (4)	−0.009 (5)	0.015 (4)	−0.002 (4)
C2	0.092 (8)	0.056 (6)	0.031 (4)	0.006 (6)	0.023 (5)	−0.003 (4)
C3	0.077 (7)	0.054 (6)	0.050 (5)	0.007 (5)	0.037 (5)	0.005 (4)
C4	0.069 (6)	0.054 (6)	0.062 (6)	−0.014 (5)	0.039 (5)	0.002 (5)
C5	0.043 (5)	0.027 (4)	0.037 (4)	−0.002 (4)	0.016 (4)	0.008 (3)
C6	0.031 (4)	0.022 (4)	0.051 (5)	−0.004 (4)	0.010 (4)	0.003 (4)
C7	0.031 (4)	0.026 (4)	0.034 (4)	0.000 (3)	0.005 (3)	0.002 (3)
C8	0.032 (5)	0.046 (5)	0.040 (4)	−0.008 (4)	0.010 (4)	0.000 (4)
C9	0.032 (4)	0.037 (4)	0.036 (4)	−0.012 (4)	−0.005 (3)	0.003 (4)
C10	0.044 (5)	0.037 (4)	0.034 (4)	0.005 (4)	0.003 (4)	0.000 (4)
C11	0.032 (4)	0.039 (4)	0.032 (4)	−0.006 (4)	0.005 (3)	0.005 (3)
C12	0.029 (4)	0.025 (4)	0.034 (4)	−0.002 (3)	0.010 (3)	0.001 (3)
C13	0.032 (4)	0.028 (5)	0.042 (4)	−0.002 (3)	0.015 (3)	0.004 (3)
C14	0.025 (4)	0.029 (4)	0.038 (4)	0.006 (3)	0.006 (3)	0.005 (3)
C15	0.035 (5)	0.037 (5)	0.058 (5)	0.002 (4)	0.013 (4)	0.005 (4)
C16	0.018 (5)	0.047 (5)	0.076 (6)	0.000 (4)	0.003 (4)	0.013 (5)
C17	0.034 (5)	0.046 (5)	0.067 (6)	0.003 (4)	−0.011 (4)	0.004 (5)
C18	0.033 (5)	0.056 (6)	0.048 (5)	−0.001 (4)	0.002 (4)	−0.005 (4)
N5	0.025 (3)	0.030 (4)	0.056 (4)	−0.006 (3)	0.011 (3)	−0.002 (3)
C51	0.046 (5)	0.063 (7)	0.073 (6)	−0.008 (5)	0.015 (5)	0.010 (5)
C52	0.036 (5)	0.069 (6)	0.126 (9)	0.005 (5)	0.033 (6)	0.015 (6)
C53	0.048 (7)	0.079 (7)	0.073 (6)	0.004 (5)	0.009 (5)	−0.016 (6)
C54	0.091 (8)	0.147 (13)	0.058 (6)	0.030 (9)	0.011 (5)	0.013 (8)
C55	0.048 (6)	0.050 (6)	0.078 (6)	0.013 (5)	0.020 (5)	−0.004 (5)
C56	0.036 (5)	0.101 (9)	0.107 (7)	0.011 (6)	0.031 (5)	0.007 (7)
C57	0.057 (7)	0.054 (6)	0.087 (7)	0.011 (5)	0.030 (6)	0.016 (6)
C58	0.080 (8)	0.133 (11)	0.057 (6)	0.038 (8)	0.009 (5)	0.011 (6)

Geometric parameters (Å, º)

Fe1—N2	2.041 (6)	C4—C5	1.373 (10)
Fe1—N3	2.042 (5)	C5—C6	1.477 (10)
Fe1—N4	2.202 (6)	C7—C8	1.386 (10)
Fe1—N1	2.202 (5)	C7—C12	1.394 (9)
Fe1—Cl3	2.324 (3)	C8—C9	1.369 (10)
Fe1—Cl4	2.334 (3)	C9—C10	1.382 (11)
Cl1—C9	1.727 (7)	C10—C11	1.393 (11)
Cl2—C10	1.712 (8)	C11—C12	1.382 (9)
O1—C13	1.219 (8)	C13—C14	1.481 (10)
O2—C6	1.232 (8)	C14—C15	1.390 (10)
N1—C5	1.322 (9)	C15—C16	1.344 (11)
N1—C1	1.336 (9)	C16—C17	1.372 (11)
N2—C6	1.338 (8)	C17—C18	1.382 (11)
N2—C7	1.399 (8)	N5—C51	1.495 (9)
N3—C13	1.346 (9)	N5—C57	1.503 (10)
N3—C12	1.406 (9)	N5—C53	1.510 (10)
N4—C14	1.326 (8)	N5—C55	1.510 (9)
N4—C18	1.327 (9)	C51—C52	1.544 (12)
C1—C2	1.371 (11)	C53—C54	1.544 (13)
C2—C3	1.378 (12)	C55—C56	1.528 (11)
C3—C4	1.333 (11)	C57—C58	1.505 (13)
N2—Fe1—N3	77.6 (2)	N2—C6—C5	112.7 (6)
N2—Fe1—N4	153.1 (2)	C8—C7—C12	119.2 (6)
N3—Fe1—N4	75.5 (2)	C8—C7—N2	125.2 (6)
N2—Fe1—N1	74.9 (2)	C12—C7—N2	115.5 (6)
N3—Fe1—N1	152.5 (2)	C9—C8—C7	121.1 (7)
N4—Fe1—N1	132.0 (2)	C8—C9—C10	119.9 (7)
N2—Fe1—Cl3	105.86 (19)	C8—C9—Cl1	119.7 (6)
N3—Fe1—Cl3	105.56 (19)	C10—C9—Cl1	120.3 (6)
N4—Fe1—Cl3	82.89 (19)	C9—C10—C11	119.8 (7)
N1—Fe1—Cl3	83.2 (2)	C9—C10—Cl2	121.1 (6)
N2—Fe1—Cl4	101.6 (2)	C11—C10—Cl2	119.1 (6)
N3—Fe1—Cl4	102.33 (19)	C12—C11—C10	120.2 (7)
N4—Fe1—Cl4	82.86 (17)	C11—C12—C7	119.8 (6)
N1—Fe1—Cl4	82.35 (18)	C11—C12—N3	126.7 (6)
Cl3—Fe1—Cl4	144.22 (9)	C7—C12—N3	113.5 (6)
C5—N1—C1	119.4 (6)	O1—C13—N3	128.0 (7)
C5—N1—Fe1	113.6 (5)	O1—C13—C14	119.6 (6)
C1—N1—Fe1	127.0 (5)	N3—C13—C14	112.4 (6)
C6—N2—C7	122.7 (6)	N4—C14—C15	120.6 (7)
C6—N2—Fe1	119.9 (5)	N4—C14—C13	117.1 (6)
C7—N2—Fe1	116.2 (4)	C15—C14—C13	122.3 (7)
C13—N3—C12	122.1 (6)	C16—C15—C14	119.4 (8)
C13—N3—Fe1	120.7 (5)	C15—C16—C17	120.1 (8)
C12—N3—Fe1	117.0 (4)	C16—C17—C18	118.2 (8)
C14—N4—C18	120.1 (7)	N4—C18—C17	121.5 (8)
C14—N4—Fe1	113.6 (5)	C51—N5—C57	110.9 (6)
C18—N4—Fe1	126.3 (5)	C51—N5—C53	111.1 (6)
N1—C1—C2	121.6 (8)	C57—N5—C53	106.6 (7)
C1—C2—C3	118.7 (8)	C51—N5—C55	106.3 (6)
C4—C3—C2	118.6 (8)	C57—N5—C55	111.0 (6)
C3—C4—C5	121.2 (9)	C53—N5—C55	111.1 (6)
N1—C5—C4	120.5 (7)	N5—C51—C52	114.1 (7)
N1—C5—C6	116.3 (6)	N5—C53—C54	113.6 (9)
C4—C5—C6	123.2 (8)	N5—C55—C56	113.2 (7)
O2—C6—N2	127.3 (7)	N5—C57—C58	115.4 (9)
O2—C6—C5	120.0 (7)
N2—Fe1—N1—C5	−10.5 (5)	N1—C5—C6—N2	6.8 (9)
N3—Fe1—N1—C5	−8.2 (9)	C4—C5—C6—N2	−171.4 (7)
N4—Fe1—N1—C5	167.0 (5)	C6—N2—C7—C8	−16.5 (10)
Cl3—Fe1—N1—C5	−119.0 (5)	Fe1—N2—C7—C8	176.2 (6)
Cl4—Fe1—N1—C5	93.8 (5)	C6—N2—C7—C12	163.2 (6)
N2—Fe1—N1—C1	170.4 (7)	Fe1—N2—C7—C12	−4.1 (8)
N3—Fe1—N1—C1	172.7 (6)	C12—C7—C8—C9	−1.7 (11)
N4—Fe1—N1—C1	−12.1 (8)	N2—C7—C8—C9	178.0 (7)
Cl3—Fe1—N1—C1	61.9 (6)	C7—C8—C9—C10	0.6 (11)
Cl4—Fe1—N1—C1	−85.3 (6)	C7—C8—C9—Cl1	−177.7 (6)
N3—Fe1—N2—C6	−163.6 (5)	C8—C9—C10—C11	1.7 (12)
N4—Fe1—N2—C6	−160.5 (6)	Cl1—C9—C10—C11	180.0 (6)
N1—Fe1—N2—C6	15.3 (5)	C8—C9—C10—Cl2	−178.0 (6)
Cl3—Fe1—N2—C6	93.5 (5)	Cl1—C9—C10—Cl2	0.3 (10)
Cl4—Fe1—N2—C6	−63.3 (5)	C9—C10—C11—C12	−2.9 (11)
N3—Fe1—N2—C7	4.0 (5)	Cl2—C10—C11—C12	176.8 (6)
N4—Fe1—N2—C7	7.1 (9)	C10—C11—C12—C7	1.8 (10)
N1—Fe1—N2—C7	−177.0 (5)	C10—C11—C12—N3	−178.5 (7)
Cl3—Fe1—N2—C7	−98.8 (5)	C8—C7—C12—C11	0.5 (10)
Cl4—Fe1—N2—C7	104.3 (5)	N2—C7—C12—C11	−179.2 (6)
N2—Fe1—N3—C13	170.6 (6)	C8—C7—C12—N3	−179.2 (6)
N4—Fe1—N3—C13	−8.0 (5)	N2—C7—C12—N3	1.0 (9)
N1—Fe1—N3—C13	168.3 (6)	C13—N3—C12—C11	8.7 (10)
Cl3—Fe1—N3—C13	−86.2 (5)	Fe1—N3—C12—C11	−177.3 (6)
Cl4—Fe1—N3—C13	71.2 (5)	C13—N3—C12—C7	−171.6 (6)
N2—Fe1—N3—C12	−3.5 (5)	Fe1—N3—C12—C7	2.4 (7)
N4—Fe1—N3—C12	177.9 (5)	C12—N3—C13—O1	2.7 (11)
N1—Fe1—N3—C12	−5.8 (9)	Fe1—N3—C13—O1	−171.1 (6)
Cl3—Fe1—N3—C12	99.7 (4)	C12—N3—C13—C14	−176.3 (6)
Cl4—Fe1—N3—C12	−102.9 (4)	Fe1—N3—C13—C14	10.0 (8)
N2—Fe1—N4—C14	1.1 (9)	C18—N4—C14—C15	−3.2 (10)
N3—Fe1—N4—C14	4.2 (5)	Fe1—N4—C14—C15	178.7 (5)
N1—Fe1—N4—C14	−173.5 (5)	C18—N4—C14—C13	177.5 (6)
Cl3—Fe1—N4—C14	112.4 (5)	Fe1—N4—C14—C13	−0.6 (8)
Cl4—Fe1—N4—C14	−100.5 (5)	O1—C13—C14—N4	175.3 (7)
N2—Fe1—N4—C18	−176.9 (6)	N3—C13—C14—N4	−5.6 (9)
N3—Fe1—N4—C18	−173.8 (6)	O1—C13—C14—C15	−4.0 (10)
N1—Fe1—N4—C18	8.5 (8)	N3—C13—C14—C15	175.1 (6)
Cl3—Fe1—N4—C18	−65.6 (6)	N4—C14—C15—C16	2.6 (11)
Cl4—Fe1—N4—C18	81.5 (6)	C13—C14—C15—C16	−178.1 (7)
C5—N1—C1—C2	−2.8 (12)	C14—C15—C16—C17	−1.9 (11)
Fe1—N1—C1—C2	176.2 (6)	C15—C16—C17—C18	1.7 (12)
N1—C1—C2—C3	0.5 (13)	C14—N4—C18—C17	3.0 (11)
C1—C2—C3—C4	2.0 (13)	Fe1—N4—C18—C17	−179.1 (6)
C2—C3—C4—C5	−2.2 (13)	C16—C17—C18—N4	−2.3 (12)
C1—N1—C5—C4	2.6 (11)	C57—N5—C51—C52	60.6 (9)
Fe1—N1—C5—C4	−176.5 (6)	C53—N5—C51—C52	−57.7 (10)
C1—N1—C5—C6	−175.6 (7)	C55—N5—C51—C52	−178.6 (7)
Fe1—N1—C5—C6	5.3 (8)	C51—N5—C53—C54	−58.6 (10)
C3—C4—C5—N1	−0.1 (13)	C57—N5—C53—C54	−179.5 (8)
C3—C4—C5—C6	177.9 (8)	C55—N5—C53—C54	59.4 (10)
C7—N2—C6—O2	−4.7 (11)	C51—N5—C55—C56	179.2 (7)
Fe1—N2—C6—O2	162.1 (6)	C57—N5—C55—C56	−60.1 (9)
C7—N2—C6—C5	176.0 (6)	C53—N5—C55—C56	58.3 (9)
Fe1—N2—C6—C5	−17.2 (8)	C51—N5—C57—C58	55.7 (10)
N1—C5—C6—O2	−172.5 (7)	C53—N5—C57—C58	176.7 (8)
C4—C5—C6—O2	9.3 (12)	C55—N5—C57—C58	−62.2 (10)