Bis[tris­(pyridin-2-yl)amine]­iron(II) tris­(di­cyano­methyl­idene)methane­diide

Setifi, Z.; Setifi, F.; Dege, N.; Al-Douh, M.H.; Glidewell, C.

doi:10.1107/S241431462001278X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 9| September 2020| x201278

https://doi.org/10.1107/S241431462001278X

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Bis[tris(pyridin-2-yl)amine]iron(II) tris(dicyanomethylidene)methanediide

Zouaoui Setifi,^a,^b Fatima Setifi,^b ^* Necmi Dege,^c Mohammed Hadi Al-Douh ^d and Christopher Glidewell ^e

^aDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^bLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Atakum-Samsun, Turkey, ^dChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen, and ^eSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
^*Correspondence e-mail: fat_setifi@yahoo.fr

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 10 September 2020; accepted 20 September 2020; online 25 September 2020)

In the title compound, [Fe{(C₅H₄N)₃N}₂][C{C(CN)₂}₃], both ions lie across centres of inversion, with the anion being statistically disordered over two sets of atomic sites having equal occupancy. The cation and anion have approximate $[\overline{3}]$ and 32 symmetry, respectively, and the Fe—N bond lengths indicate low-spin Fe^II. A combination of two-centre C—H⋯N and three-centre C—H⋯(N)₂ hydrogen bonds link the ions into complex sheets. Several low-occupancy water molecules are present, whose H atoms could not be located: accordingly, the reflection data were subjected to the SQUEEZE procedure [Spek (2015 ). Acta Cryst. C71, 9–18].

Keywords: synthesis; crystal structure; molecular structure; disorder.

CCDC reference: 2032866

Structure description

As a consequence of their ability to link metal ions in a variety of different ways, polynitrile anions, either functioning alone or in combination with neutral co-ligands, provide opportunities for the generation of molecular architectures with varying dimensions and topologies (Miyazaki et al., 2003 ; Benmansour et al., 2007 , 2008 , 2012 ; Atmani et al., 2008 ; Yuste et al., 2009 ). The presence of other potential donor groups such as those derived from –OH, –SH or –NH₂, together with their rigidity and electronic delocalization, mean that polynitrile anions can also lead to new bistable materials (Benmansour et al., 2010 ; Setifi et al., 2009 , 2014 ; Pittala et al., 2017 ). As a part of our continuing study of the structural and magnetic properties of iron(II) complexes containing both polynitrile and polypyridyl units (Setifi et al., 2013 , 2017 , 2018a ,b ), we report here the molecular and supramolecular structure of a new compound based on tri(2-pyridyl)amine (tpa) as ligand and the tris(dicyanomethylene)methanediide dianion (tcpd²⁻) as the counter-ion.

The structure consists of a [Fe((C₅H₄N)₃N)₂]²⁺ cation containing six-coordinate Fe in an octahedral coordination environment and a [C(C(CN)₂)₃]²⁻ anion (Fig. 1). In addition, there are also partial-occupancy water molecules present, but these could not be structurally characterized in a satisfactory manner. The cation lies across a centre of inversion (½, ½, ½) with the unique ligand coordinated in a tripodal fashion, such that the point symmetry of the cation approximates very closely to S₆ ( $[\overline{3}]$ ). The Fe—N distances lie in the range 1.981 (3)–1.997 (3) Å. This is typical for six-coordinate low-spin Fe^II complexes, whereas Fe—N distances in analogous high-spin Fe^II complexes are typically observed at around 2.15 Å (Orpen et al., 1989 ). The trigonal anion is disordered across another centre of inversion (½, 1, 0). The geometry at the central atom C4 is exactly planar, but the three independent C(CN)₂ groups are twisted out of this plane, making dihedral angles with it of 26.2 (9), 27.7 (13) and 29.3 (9)°, so that the point symmetry of the anion approximates very closely to D₃ (32). The anion is chiral, but the inversion symmetry confirms that equal numbers of the two enantiomeric conformations are present.

Figure 1
The structure of the two ionic components, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The anion is disordered across a centre of inversion and the atoms marked `a′ or `b′ are at the symmetry positions (1 − x, 1 − y, 1 − z) and (1 − x, 2 − y, −z), respectively.

Within the selected asymmetric unit, the cation is linked to both orientations of the disordered anion by one two-centre C—H⋯N hydrogen bond and one three-centre C—H⋯(N)₂ hydrogen bond (Table 1), forming an ion pair. An additional further three-centre system links these ion pairs into complex sheets lying parallel to (100) (Fig. 2): within this sheet, each anion site is occupied by one of the two possible orientations of the anion, and these orientations are distributed at random throughout the structure such that equal numbers of the two exist in the crystal as a whole.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯N412	0.93	2.52	3.404 (16)	159
C26—H26⋯N421	0.93	2.31	3.23 (3)	170
C26—H26⋯N432ⁱ	0.93	2.54	3.47 (3)	173
C36—H36⋯N412ⁱⁱ	0.93	2.48	3.352 (17)	157
C36—H36⋯N431ⁱⁱⁱ	0.93	2.50	3.39 (2)	160
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z.

Figure 2
Part of the crystal structure showing the formation of a hydrogen-bonded sheet lying parallel to (100). Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted. Each anion site is occupied by one of the two possible orientations of the anion, distributed at random.

Synthesis and crystallization

The title compound was synthesized solvothermally under autogenous pressure using a mixture of iron(II) sulfate heptahydrate (28 mg, 0.1 mmol), tri(2-pyridyl)amine (31 mg, 0.1 mmol) and dipotassium tris(dicycanomethylene)methanediide (28 mg, 0.1 mmol) in water-ethanol (3:1 v/v, 20 ml). The mixture was sealed in a Teflon-lined autoclave and held at 423 K for 3 d, and then cooled to ambient temperature at a rate of 10 K per hour (yield 45%). Red needles of the title complex suitable for single-crystal X-ray diffraction were selected directly from the synthesized product.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Because of the extensive overlapping of the atomic sites in the disordered anion, it was found necessary to restrain the bonded C—C and C—N distances in the anion to values of 1.42 (2) and 1.16 (2) Å, respectively, while the 1,3 non-bonded C⋯N distances were restrained to 2.58 (4) Å. Conventional refinement then indicated the presence of several low-occupancy water molecules, whose H atoms could not be located: accordingly, the reflection data were subjected to the SQUEEZE procedure (Spek, 2015), which indicated a void volume of 149 Å³ centred at the origin, and a total of 11 electrons per unit cell in addition to those of the ionic components.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₁₅H₁₂N₄)₂](C₁₀N₆)
M_r	756.58
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	9.8291 (8), 10.0499 (8), 11.0308 (9)
α, β, γ (°)	98.825 (7), 90.900 (7), 117.747 (6)
V (Å³)	948.18 (14)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.45
Crystal size (mm)	0.39 × 0.12 × 0.11

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.899, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	9558, 3955, 2609
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.164, 0.96
No. of reflections	3955
No. of parameters	319
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.25
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXS86 (Sheldrick, 2015 ), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2020 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2032866

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431462001278X/im4010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462001278X/im4010Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2020).

Bis[tris(pyridin-2-yl)amine]iron(II) tris(dicyanomethylidene)methanediide top

Crystal data top

[Fe(C₁₅H₁₂N₄)₂](C₁₀N₆)	Z = 1
M_r = 756.58	F(000) = 388
Triclinic, P1	D_x = 1.325 Mg m⁻³
a = 9.8291 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0499 (8) Å	Cell parameters from 4139 reflections
c = 11.0308 (9) Å	θ = 1.9–27.1°
α = 98.825 (7)°	µ = 0.45 mm⁻¹
β = 90.900 (7)°	T = 296 K
γ = 117.747 (6)°	Needle, red
V = 948.18 (14) Å³	0.39 × 0.12 × 0.11 mm

Data collection top

STOE IPDS 2 diffractometer	3955 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2609 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
rotation method scans	θ_max = 26.6°, θ_min = 1.9°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −12→12
T_min = 0.899, T_max = 0.952	k = −12→12
9558 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0793P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
3955 reflections	Δρ_max = 1.01 e Å⁻³
319 parameters	Δρ_min = −0.25 e Å⁻³
21 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.5000	0.5000	0.5000	0.0477 (2)
N1	0.6353 (4)	0.6637 (3)	0.7523 (3)	0.0559 (7)
N11	0.3931 (4)	0.4694 (4)	0.6537 (3)	0.0543 (7)
C12	0.4770 (5)	0.5581 (4)	0.7590 (3)	0.0547 (9)
C13	0.4143 (6)	0.5505 (5)	0.8704 (4)	0.0666 (11)
H13	0.4751	0.6135	0.9422	0.080*
C14	0.2641 (6)	0.4510 (6)	0.8747 (4)	0.0801 (13)
H14	0.2197	0.4468	0.9487	0.096*
C15	0.1770 (5)	0.3547 (6)	0.7664 (4)	0.0752 (12)
H15	0.0743	0.2826	0.7671	0.090*
C16	0.2460 (5)	0.3686 (5)	0.6582 (4)	0.0648 (10)
H16	0.1878	0.3053	0.5855	0.078*
N21	0.5931 (3)	0.7238 (3)	0.5604 (3)	0.0541 (7)
C22	0.6498 (4)	0.7761 (4)	0.6797 (3)	0.0542 (8)
C23	0.7155 (5)	0.9278 (4)	0.7338 (4)	0.0641 (10)
H23	0.7532	0.9593	0.8167	0.077*
C24	0.7241 (5)	1.0313 (5)	0.6631 (4)	0.0716 (11)
H24	0.7671	1.1347	0.6972	0.086*
C25	0.6677 (5)	0.9800 (5)	0.5398 (4)	0.0686 (11)
H25	0.6731	1.0489	0.4902	0.082*
C26	0.6037 (5)	0.8267 (5)	0.4910 (4)	0.0608 (9)
H26	0.5669	0.7934	0.4079	0.073*
N31	0.6765 (3)	0.5035 (3)	0.5924 (3)	0.0513 (7)
C32	0.7226 (4)	0.5871 (4)	0.7074 (3)	0.0512 (8)
C33	0.8442 (5)	0.6016 (5)	0.7805 (4)	0.0635 (10)
H33	0.8723	0.6618	0.8588	0.076*
C34	0.9249 (5)	0.5253 (5)	0.7360 (4)	0.0685 (11)
H34	1.0080	0.5323	0.7832	0.082*
C35	0.8768 (5)	0.4382 (5)	0.6184 (4)	0.0644 (10)
H35	0.9279	0.3850	0.5858	0.077*
C36	0.7564 (4)	0.4297 (4)	0.5503 (4)	0.0578 (9)
H36	0.7274	0.3708	0.4715	0.069*
C4	0.5000	1.0000	0.0000	0.0528 (12)
C41	0.6447 (8)	1.1099 (8)	0.0634 (6)	0.0546 (17)	0.5
C42	0.4036 (9)	0.8718 (8)	0.0533 (6)	0.0577 (19)	0.5
C43	0.4494 (9)	1.0165 (9)	−0.1150 (6)	0.0536 (17)	0.5
C411	0.768 (3)	1.194 (3)	−0.001 (3)	0.081 (9)	0.5
N411	0.867 (2)	1.287 (2)	−0.042 (2)	0.093 (6)	0.5
C412	0.673 (2)	1.129 (2)	0.1959 (11)	0.053 (4)	0.5
N412	0.704 (3)	1.168 (2)	0.3007 (12)	0.078 (4)	0.5
C421	0.462 (4)	0.816 (3)	0.142 (3)	0.057 (5)	0.5
N421	0.508 (3)	0.755 (2)	0.198 (3)	0.088 (7)	0.5
C422	0.2396 (13)	0.790 (3)	0.024 (2)	0.054 (5)	0.5
N422	0.1088 (13)	0.7435 (18)	0.0259 (19)	0.073 (3)	0.5
C431	0.353 (3)	0.888 (3)	−0.204 (2)	0.100 (10)	0.5
N431	0.267 (4)	0.791 (3)	−0.2778 (18)	0.095 (6)	0.5
C432	0.499 (4)	1.164 (3)	−0.145 (3)	0.074 (10)	0.5
N432	0.545 (3)	1.275 (3)	−0.184 (3)	0.086 (6)	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0555 (5)	0.0561 (5)	0.0382 (4)	0.0336 (4)	0.0043 (3)	0.0028 (3)
N1	0.070 (2)	0.0617 (18)	0.0440 (16)	0.0404 (17)	0.0011 (14)	0.0008 (14)
N11	0.0626 (19)	0.0666 (19)	0.0452 (16)	0.0405 (17)	0.0106 (14)	0.0082 (14)
C12	0.071 (2)	0.062 (2)	0.0450 (19)	0.043 (2)	0.0107 (16)	0.0086 (17)
C13	0.089 (3)	0.081 (3)	0.048 (2)	0.054 (3)	0.016 (2)	0.0118 (19)
C14	0.103 (4)	0.100 (3)	0.066 (3)	0.066 (3)	0.038 (3)	0.033 (3)
C15	0.072 (3)	0.091 (3)	0.079 (3)	0.047 (3)	0.027 (2)	0.030 (3)
C16	0.065 (3)	0.077 (3)	0.060 (2)	0.039 (2)	0.0115 (19)	0.014 (2)
N21	0.0614 (19)	0.0607 (18)	0.0473 (16)	0.0364 (16)	0.0050 (13)	0.0050 (14)
C22	0.061 (2)	0.061 (2)	0.0462 (19)	0.0361 (18)	0.0027 (16)	0.0019 (17)
C23	0.073 (3)	0.061 (2)	0.059 (2)	0.037 (2)	−0.0034 (19)	−0.0055 (19)
C24	0.079 (3)	0.061 (2)	0.075 (3)	0.038 (2)	0.005 (2)	−0.001 (2)
C25	0.080 (3)	0.064 (2)	0.070 (3)	0.040 (2)	0.009 (2)	0.016 (2)
C26	0.066 (2)	0.067 (2)	0.057 (2)	0.037 (2)	0.0058 (18)	0.0144 (19)
N31	0.0567 (17)	0.0574 (17)	0.0448 (15)	0.0334 (15)	0.0038 (12)	0.0022 (13)
C32	0.056 (2)	0.057 (2)	0.0467 (19)	0.0323 (17)	0.0010 (15)	0.0046 (16)
C33	0.070 (3)	0.069 (2)	0.053 (2)	0.036 (2)	−0.0039 (18)	0.0051 (19)
C34	0.060 (2)	0.078 (3)	0.072 (3)	0.037 (2)	−0.0026 (19)	0.015 (2)
C35	0.063 (2)	0.076 (3)	0.069 (3)	0.045 (2)	0.0118 (19)	0.013 (2)
C36	0.065 (2)	0.065 (2)	0.053 (2)	0.040 (2)	0.0092 (17)	0.0065 (18)
C4	0.062 (3)	0.060 (3)	0.043 (3)	0.036 (3)	0.006 (2)	0.001 (2)
C41	0.056 (4)	0.060 (4)	0.047 (4)	0.028 (4)	0.003 (4)	0.005 (4)
C42	0.080 (6)	0.064 (5)	0.038 (4)	0.043 (4)	0.002 (3)	0.001 (3)
C43	0.059 (4)	0.060 (5)	0.042 (4)	0.030 (4)	−0.001 (3)	0.004 (4)
C411	0.119 (19)	0.065 (13)	0.058 (10)	0.046 (11)	−0.005 (8)	−0.001 (8)
N411	0.124 (15)	0.088 (9)	0.099 (9)	0.073 (10)	0.023 (8)	0.029 (6)
C412	0.054 (7)	0.057 (7)	0.033 (6)	0.023 (5)	−0.006 (5)	−0.022 (5)
N412	0.094 (12)	0.084 (11)	0.034 (5)	0.026 (8)	−0.007 (7)	0.000 (6)
C421	0.071 (13)	0.069 (11)	0.050 (8)	0.045 (9)	0.013 (7)	0.022 (7)
N421	0.15 (2)	0.071 (8)	0.059 (7)	0.065 (12)	−0.008 (11)	0.010 (8)
C422	0.044 (7)	0.042 (6)	0.064 (10)	0.007 (6)	0.025 (7)	0.020 (6)
N422	0.052 (6)	0.066 (8)	0.092 (8)	0.022 (6)	0.018 (5)	0.013 (6)
C431	0.078 (13)	0.117 (18)	0.12 (2)	0.052 (12)	0.016 (11)	0.050 (15)
N431	0.099 (11)	0.085 (12)	0.072 (12)	0.022 (9)	0.006 (9)	0.010 (8)
C432	0.078 (16)	0.085 (12)	0.053 (9)	0.033 (9)	0.019 (9)	0.009 (9)
N432	0.097 (12)	0.094 (12)	0.061 (10)	0.038 (9)	0.007 (8)	0.019 (9)

Geometric parameters (Å, º) top

Fe1—N31ⁱ	1.981 (3)	N31—C32	1.349 (4)
Fe1—N31	1.981 (3)	N31—C36	1.353 (4)
Fe1—N21ⁱ	1.986 (3)	C32—C33	1.368 (5)
Fe1—N21	1.986 (3)	C33—C34	1.386 (6)
Fe1—N11ⁱ	1.997 (3)	C33—H33	0.9300
Fe1—N11	1.997 (3)	C34—C35	1.386 (6)
N1—C12	1.430 (5)	C34—H34	0.9300
N1—C22	1.438 (5)	C35—C36	1.353 (5)
N1—C32	1.444 (4)	C35—H35	0.9300
N11—C16	1.331 (5)	C36—H36	0.9300
N11—C12	1.339 (5)	C4—C41ⁱⁱ	1.414 (7)
C12—C13	1.380 (5)	C4—C41	1.414 (7)
C13—C14	1.350 (7)	C4—C43	1.416 (7)
C13—H13	0.9300	C4—C43ⁱⁱ	1.416 (7)
C14—C15	1.392 (7)	C4—C42	1.420 (7)
C14—H14	0.9300	C4—C42ⁱⁱ	1.420 (7)
C15—C16	1.376 (6)	C41—C411	1.395 (15)
C15—H15	0.9300	C41—C412	1.450 (14)
C16—H16	0.9300	C42—C422	1.431 (14)
N21—C26	1.346 (5)	C42—C421	1.435 (16)
N21—C22	1.346 (4)	C43—C431	1.402 (16)
C22—C23	1.374 (5)	C43—C432	1.426 (16)
C23—C24	1.367 (6)	C411—N411	1.147 (17)
C23—H23	0.9300	C412—N412	1.150 (15)
C24—C25	1.385 (6)	C421—N421	1.149 (16)
C24—H24	0.9300	C422—N422	1.147 (14)
C25—C26	1.375 (6)	C431—N431	1.138 (17)
C25—H25	0.9300	C432—N432	1.147 (17)
C26—H26	0.9300

N31ⁱ—Fe1—N31	180.00 (17)	C431ⁱⁱ—C41—C422ⁱⁱ	135.0 (14)
N31ⁱ—Fe1—N21ⁱ	88.18 (12)	C4—C42—C43ⁱⁱ	59.7 (4)
N31—Fe1—N21ⁱ	91.82 (11)	C4—C42—C422	122.3 (11)
N31ⁱ—Fe1—N21	91.82 (12)	C43ⁱⁱ—C42—C422	159.3 (13)
N31—Fe1—N21	88.18 (12)	C4—C42—C41ⁱⁱ	59.5 (4)
N21ⁱ—Fe1—N21	180.00 (10)	C43ⁱⁱ—C42—C41ⁱⁱ	119.1 (7)
N31ⁱ—Fe1—N11ⁱ	87.54 (12)	C422—C42—C41ⁱⁱ	67.0 (10)
N31—Fe1—N11ⁱ	92.46 (12)	C4—C42—C421	122.9 (14)
N21ⁱ—Fe1—N11ⁱ	87.97 (12)	C43ⁱⁱ—C42—C421	66.9 (12)
N21—Fe1—N11ⁱ	92.03 (12)	C422—C42—C421	114.8 (17)
N31ⁱ—Fe1—N11	92.46 (12)	C41ⁱⁱ—C42—C421	159.9 (16)
N31—Fe1—N11	87.55 (12)	C4—C42—C411ⁱⁱ	110.2 (10)
N21ⁱ—Fe1—N11	92.03 (12)	C43ⁱⁱ—C42—C411ⁱⁱ	157.1 (15)
N21—Fe1—N11	87.97 (12)	C41ⁱⁱ—C42—C411ⁱⁱ	55.5 (9)
N11ⁱ—Fe1—N11	180.00 (18)	C421—C42—C411ⁱⁱ	126.9 (16)
C12—N1—C22	111.5 (3)	C4—C42—C432ⁱⁱ	111.2 (11)
C12—N1—C32	112.0 (3)	C43ⁱⁱ—C42—C432ⁱⁱ	56.5 (9)
C22—N1—C32	111.1 (3)	C422—C42—C432ⁱⁱ	126.6 (15)
C16—N11—C12	118.5 (3)	C41ⁱⁱ—C42—C432ⁱⁱ	155.9 (16)
C16—N11—Fe1	124.8 (3)	C411ⁱⁱ—C42—C432ⁱⁱ	138.6 (14)
C12—N11—Fe1	116.8 (3)	C41ⁱⁱ—C43—C431	67.3 (15)
N11—C12—C13	121.9 (4)	C41ⁱⁱ—C43—C4	60.5 (4)
N11—C12—N1	117.5 (3)	C431—C43—C4	121.2 (14)
C13—C12—N1	120.6 (4)	C41ⁱⁱ—C43—C432	155.1 (18)
C14—C13—C12	119.7 (4)	C431—C43—C432	118 (2)
C14—C13—H13	120.2	C4—C43—C432	120.7 (15)
C12—C13—H13	120.2	C41ⁱⁱ—C43—C42ⁱⁱ	120.4 (6)
C13—C14—C15	118.9 (4)	C431—C43—C42ⁱⁱ	153.4 (14)
C13—C14—H14	120.5	C4—C43—C42ⁱⁱ	59.9 (4)
C15—C14—H14	120.5	C432—C43—C42ⁱⁱ	66.9 (13)
C16—C15—C14	118.6 (4)	C41ⁱⁱ—C43—C412ⁱⁱ	59.6 (8)
C16—C15—H15	120.7	C4—C43—C412ⁱⁱ	116.2 (9)
C14—C15—H15	120.7	C432—C43—C412ⁱⁱ	122.8 (16)
N11—C16—C15	122.4 (4)	C42ⁱⁱ—C43—C412ⁱⁱ	159.8 (10)
N11—C16—H16	118.8	C41ⁱⁱ—C43—C421ⁱⁱ	162.5 (15)
C15—C16—H16	118.8	C431—C43—C421ⁱⁱ	124.0 (17)
C26—N21—C22	117.7 (3)	C4—C43—C421ⁱⁱ	113.7 (11)
C26—N21—Fe1	124.9 (3)	C42ⁱⁱ—C43—C421ⁱⁱ	56.8 (10)
C22—N21—Fe1	117.4 (2)	C412ⁱⁱ—C43—C421ⁱⁱ	130.0 (13)
N21—C22—C23	123.4 (3)	C422ⁱⁱ—C411—N422ⁱⁱ	83 (4)
N21—C22—N1	116.6 (3)	C422ⁱⁱ—C411—N411	59 (4)
C23—C22—N1	119.9 (3)	C422ⁱⁱ—C411—C41	117 (6)
C24—C23—C22	118.5 (4)	N422ⁱⁱ—C411—C41	159 (3)
C24—C23—H23	120.7	N411—C411—C41	167 (4)
C22—C23—H23	120.7	C422ⁱⁱ—C411—C42ⁱⁱ	62 (5)
C23—C24—C25	118.9 (4)	N422ⁱⁱ—C411—C42ⁱⁱ	142 (3)
C23—C24—H24	120.5	N411—C411—C42ⁱⁱ	121 (3)
C25—C24—H24	120.5	C41—C411—C42ⁱⁱ	57.7 (9)
C26—C25—C24	119.8 (4)	N422ⁱⁱ—N411—C422ⁱⁱ	91 (3)
C26—C25—H25	120.1	N422ⁱⁱ—N411—C411	76 (3)
C24—C25—H25	120.1	C431ⁱⁱ—C412—N431ⁱⁱ	101 (6)
N21—C26—C25	121.6 (4)	C431ⁱⁱ—C412—N412	79 (7)
N21—C26—H26	119.2	C431ⁱⁱ—C412—C41	108 (7)
C25—C26—H26	119.2	N431ⁱⁱ—C412—C41	145 (2)
C32—N31—C36	116.5 (3)	N412—C412—C41	169 (2)
C32—N31—Fe1	117.7 (2)	C431ⁱⁱ—C412—C43ⁱⁱ	59 (5)
C36—N31—Fe1	125.8 (2)	N431ⁱⁱ—C412—C43ⁱⁱ	158 (2)
N31—C32—C33	123.8 (3)	N412—C412—C43ⁱⁱ	134 (2)
N31—C32—N1	116.2 (3)	C41—C412—C43ⁱⁱ	55.9 (5)
C33—C32—N1	120.0 (3)	N431ⁱⁱ—N412—C431ⁱⁱ	79 (4)
C32—C33—C34	119.0 (4)	N431ⁱⁱ—N412—C412	67 (3)
C32—C33—H33	120.5	C432ⁱⁱ—C421—N432ⁱⁱ	96 (5)
C34—C33—H33	120.5	C432ⁱⁱ—C421—N421	73 (5)
C35—C34—C33	117.3 (4)	C432ⁱⁱ—C421—C42	108 (6)
C35—C34—H34	121.3	N432ⁱⁱ—C421—C42	151 (3)
C33—C34—H34	121.3	N421—C421—C42	169 (4)
C36—C35—C34	120.8 (3)	C432ⁱⁱ—C421—C43ⁱⁱ	58 (5)
C36—C35—H35	119.6	N432ⁱⁱ—C421—C43ⁱⁱ	152 (3)
C34—C35—H35	119.6	N421—C421—C43ⁱⁱ	128 (3)
C35—C36—N31	122.6 (4)	C42—C421—C43ⁱⁱ	56.3 (7)
C35—C36—H36	118.7	N432ⁱⁱ—N421—C432ⁱⁱ	84 (4)
N31—C36—H36	118.7	N432ⁱⁱ—N421—C421	67 (4)
C41ⁱⁱ—C4—C41	180.0 (5)	C411ⁱⁱ—C422—N411ⁱⁱ	104 (6)
C41ⁱⁱ—C4—C43	58.9 (5)	C411ⁱⁱ—C422—N422	80 (5)
C41—C4—C43	121.1 (5)	C411ⁱⁱ—C422—C42	106 (5)
C41ⁱⁱ—C4—C43ⁱⁱ	121.1 (5)	N411ⁱⁱ—C422—C42	150 (3)
C41—C4—C43ⁱⁱ	58.9 (5)	N422—C422—C42	164 (3)
C43—C4—C43ⁱⁱ	180.0 (7)	C411ⁱⁱ—C422—C41ⁱⁱ	52 (4)
C41ⁱⁱ—C4—C42	60.7 (4)	N411ⁱⁱ—C422—C41ⁱⁱ	153 (3)
C41—C4—C42	119.3 (4)	N422—C422—C41ⁱⁱ	131 (2)
C43—C4—C42	119.6 (4)	C42—C422—C41ⁱⁱ	56.5 (5)
C43ⁱⁱ—C4—C42	60.4 (4)	N411ⁱⁱ—N422—C411ⁱⁱ	78 (3)
C41ⁱⁱ—C4—C42ⁱⁱ	119.3 (4)	N411ⁱⁱ—N422—C422	62 (3)
C41—C4—C42ⁱⁱ	60.7 (4)	C412ⁱⁱ—C431—N412ⁱⁱ	88 (6)
C43—C4—C42ⁱⁱ	60.4 (4)	C412ⁱⁱ—C431—N431	67 (5)
C43ⁱⁱ—C4—C42ⁱⁱ	119.6 (4)	C412ⁱⁱ—C431—C43	112 (6)
C42—C4—C42ⁱⁱ	180.0	N412ⁱⁱ—C431—C43	152 (3)
C43ⁱⁱ—C41—C411	154.6 (16)	N431—C431—C43	174 (4)
C43ⁱⁱ—C41—C4	60.6 (4)	C412ⁱⁱ—C431—C41ⁱⁱ	63 (7)
C411—C41—C4	120.8 (14)	N412ⁱⁱ—C431—C41ⁱⁱ	150 (3)
C43ⁱⁱ—C41—C42ⁱⁱ	120.5 (7)	N431—C431—C41ⁱⁱ	126 (3)
C411—C41—C42ⁱⁱ	66.8 (14)	C43—C431—C41ⁱⁱ	56.1 (9)
C4—C41—C42ⁱⁱ	59.9 (4)	N412ⁱⁱ—N431—C412ⁱⁱ	87 (4)
C43ⁱⁱ—C41—C412	64.6 (9)	N412ⁱⁱ—N431—C431	76 (4)
C411—C41—C412	118.0 (16)	C421ⁱⁱ—C432—N421ⁱⁱ	90 (5)
C4—C41—C412	120.9 (10)	C421ⁱⁱ—C432—N432	67 (5)
C42ⁱⁱ—C41—C412	159.6 (10)	C421ⁱⁱ—C432—C43	111 (6)
C43ⁱⁱ—C41—C431ⁱⁱ	56.7 (10)	N421ⁱⁱ—C432—C43	154 (3)
C411—C41—C431ⁱⁱ	127.1 (17)	N432—C432—C43	170 (4)
C4—C41—C431ⁱⁱ	111.9 (11)	C421ⁱⁱ—C432—C42ⁱⁱ	60 (6)
C42ⁱⁱ—C41—C431ⁱⁱ	156.5 (12)	N421ⁱⁱ—C432—C42ⁱⁱ	149 (3)
C43ⁱⁱ—C41—C422ⁱⁱ	160.3 (12)	N432—C432—C42ⁱⁱ	125 (3)
C4—C41—C422ⁱⁱ	112.9 (9)	C43—C432—C42ⁱⁱ	56.6 (8)
C42ⁱⁱ—C41—C422ⁱⁱ	56.5 (8)	N421ⁱⁱ—N432—C421ⁱⁱ	88 (4)
C412—C41—C422ⁱⁱ	126.1 (13)	N421ⁱⁱ—N432—C432	72 (4)

C16—N11—C12—C13	−1.7 (5)	C412—C41—C411—C42ⁱⁱ	−158.0 (11)
Fe1—N11—C12—C13	178.1 (3)	C431ⁱⁱ—C41—C411—C42ⁱⁱ	−158.0 (16)
C16—N11—C12—N1	178.9 (3)	C422ⁱⁱ—C41—C411—C42ⁱⁱ	−19 (12)
Fe1—N11—C12—N1	−1.3 (4)	C422ⁱⁱ—C411—N411—N422ⁱⁱ	−154 (12)
C22—N1—C12—N11	63.6 (4)	C41—C411—N411—N422ⁱⁱ	128 (13)
C32—N1—C12—N11	−61.7 (4)	C42ⁱⁱ—C411—N411—N422ⁱⁱ	−150 (5)
C22—N1—C12—C13	−115.8 (4)	N422ⁱⁱ—C411—N411—C422ⁱⁱ	154 (12)
C32—N1—C12—C13	118.9 (3)	C41—C411—N411—C422ⁱⁱ	−78 (17)
N11—C12—C13—C14	0.1 (6)	C42ⁱⁱ—C411—N411—C422ⁱⁱ	4 (9)
N1—C12—C13—C14	179.4 (3)	C43ⁱⁱ—C41—C412—C431ⁱⁱ	−28 (11)
C12—C13—C14—C15	2.0 (6)	C411—C41—C412—C431ⁱⁱ	−180 (11)
C13—C14—C15—C16	−2.3 (6)	C4—C41—C412—C431ⁱⁱ	−5 (11)
C12—N11—C16—C15	1.3 (5)	C42ⁱⁱ—C41—C412—C431ⁱⁱ	81 (11)
Fe1—N11—C16—C15	−178.4 (3)	C422ⁱⁱ—C41—C412—C431ⁱⁱ	171 (10)
C14—C15—C16—N11	0.7 (6)	C43ⁱⁱ—C41—C412—N431ⁱⁱ	−171 (5)
C26—N21—C22—C23	0.9 (5)	C411—C41—C412—N431ⁱⁱ	38 (5)
Fe1—N21—C22—C23	−179.2 (3)	C4—C41—C412—N431ⁱⁱ	−147 (4)
C26—N21—C22—N1	179.3 (3)	C42ⁱⁱ—C41—C412—N431ⁱⁱ	−61 (6)
Fe1—N21—C22—N1	−0.8 (4)	C431ⁱⁱ—C41—C412—N431ⁱⁱ	−142 (13)
C12—N1—C22—N21	−62.2 (4)	C422ⁱⁱ—C41—C412—N431ⁱⁱ	29 (5)
C32—N1—C22—N21	63.6 (4)	C43ⁱⁱ—C41—C412—N412	−156 (15)
C12—N1—C22—C23	116.3 (4)	C411—C41—C412—N412	52 (15)
C32—N1—C22—C23	−118.0 (4)	C4—C41—C412—N412	−133 (14)
N21—C22—C23—C24	−0.1 (6)	C42ⁱⁱ—C41—C412—N412	−47 (16)
N1—C22—C23—C24	−178.4 (4)	C431ⁱⁱ—C41—C412—N412	−128 (23)
C22—C23—C24—C25	−0.5 (6)	C422ⁱⁱ—C41—C412—N412	43 (15)
C23—C24—C25—C26	0.3 (7)	C411—C41—C412—C43ⁱⁱ	−151.7 (19)
C22—N21—C26—C25	−1.1 (5)	C4—C41—C412—C43ⁱⁱ	23.3 (9)
Fe1—N21—C26—C25	179.0 (3)	C42ⁱⁱ—C41—C412—C43ⁱⁱ	109 (3)
C24—C25—C26—N21	0.5 (6)	C431ⁱⁱ—C41—C412—C43ⁱⁱ	28 (11)
C36—N31—C32—C33	0.8 (5)	C422ⁱⁱ—C41—C412—C43ⁱⁱ	−160.6 (15)
Fe1—N31—C32—C33	−178.8 (3)	C431ⁱⁱ—C412—N412—N431ⁱⁱ	−150 (13)
C36—N31—C32—N1	−179.1 (3)	C41—C412—N412—N431ⁱⁱ	−20 (21)
Fe1—N31—C32—N1	1.2 (4)	C43ⁱⁱ—C412—N412—N431ⁱⁱ	−172 (7)
C12—N1—C32—N31	61.7 (4)	N431ⁱⁱ—C412—N412—C431ⁱⁱ	150 (13)
C22—N1—C32—N31	−63.8 (4)	C41—C412—N412—C431ⁱⁱ	130 (22)
C12—N1—C32—C33	−118.3 (4)	C43ⁱⁱ—C412—N412—C431ⁱⁱ	−22 (9)
C22—N1—C32—C33	116.2 (4)	C4—C42—C421—C432ⁱⁱ	−6 (15)
N31—C32—C33—C34	−0.9 (6)	C43ⁱⁱ—C42—C421—C432ⁱⁱ	−27 (13)
N1—C32—C33—C34	179.1 (4)	C422—C42—C421—C432ⁱⁱ	176 (13)
C32—C33—C34—C35	0.2 (6)	C41ⁱⁱ—C42—C421—C432ⁱⁱ	85 (13)
C33—C34—C35—C36	0.4 (6)	C411ⁱⁱ—C42—C421—C432ⁱⁱ	174 (13)
C34—C35—C36—N31	−0.4 (6)	C4—C42—C421—N432ⁱⁱ	−150 (7)
C32—N31—C36—C35	−0.2 (5)	C43ⁱⁱ—C42—C421—N432ⁱⁱ	−171 (9)
Fe1—N31—C36—C35	179.5 (3)	C422—C42—C421—N432ⁱⁱ	31 (9)
C43—C4—C41—C43ⁱⁱ	179.999 (2)	C41ⁱⁱ—C42—C421—N432ⁱⁱ	−59 (11)
C42—C4—C41—C43ⁱⁱ	0.5 (6)	C411ⁱⁱ—C42—C421—N432ⁱⁱ	30 (9)
C42ⁱⁱ—C4—C41—C43ⁱⁱ	−179.5 (6)	C432ⁱⁱ—C42—C421—N432ⁱⁱ	−144 (21)
C43—C4—C41—C411	−29.3 (19)	C4—C42—C421—N421	−96 (17)
C43ⁱⁱ—C4—C41—C411	150.7 (19)	C43ⁱⁱ—C42—C421—N421	−118 (18)
C42—C4—C41—C411	151.1 (18)	C432ⁱⁱ—C42—C421—N421	−91 (26)
C42ⁱⁱ—C4—C41—C411	−28.9 (18)	C4—C42—C421—C43ⁱⁱ	21.5 (16)
C43—C4—C41—C42ⁱⁱ	−0.5 (6)	C422—C42—C421—C43ⁱⁱ	−157.4 (14)
C43ⁱⁱ—C4—C41—C42ⁱⁱ	179.5 (6)	C41ⁱⁱ—C42—C421—C43ⁱⁱ	112 (4)
C42—C4—C41—C42ⁱⁱ	179.999 (2)	C411ⁱⁱ—C42—C421—C43ⁱⁱ	−158.7 (18)
C43—C4—C41—C412	155.8 (10)	C432ⁱⁱ—C42—C421—C43ⁱⁱ	27 (13)
C43ⁱⁱ—C4—C41—C412	−24.2 (10)	C432ⁱⁱ—C421—N421—N432ⁱⁱ	−166 (16)
C42—C4—C41—C412	−23.7 (11)	C42—C421—N421—N432ⁱⁱ	−72 (21)
C42ⁱⁱ—C4—C41—C412	156.3 (11)	C43ⁱⁱ—C421—N421—N432ⁱⁱ	177 (8)
C43—C4—C41—C431ⁱⁱ	154.9 (12)	N432ⁱⁱ—C421—N421—C432ⁱⁱ	166 (16)
C43ⁱⁱ—C4—C41—C431ⁱⁱ	−25.1 (12)	C43ⁱⁱ—C421—N421—C432ⁱⁱ	−17 (10)
C42—C4—C41—C431ⁱⁱ	−24.6 (13)	C4—C42—C422—C411ⁱⁱ	6 (12)
C42ⁱⁱ—C4—C41—C431ⁱⁱ	155.4 (13)	C43ⁱⁱ—C42—C422—C411ⁱⁱ	95 (11)
C43—C4—C41—C422ⁱⁱ	−20.8 (13)	C41ⁱⁱ—C42—C422—C411ⁱⁱ	−17 (11)
C43ⁱⁱ—C4—C41—C422ⁱⁱ	159.2 (13)	C421—C42—C422—C411ⁱⁱ	−175 (11)
C42—C4—C41—C422ⁱⁱ	159.7 (12)	C432ⁱⁱ—C42—C422—C411ⁱⁱ	−174 (11)
C42ⁱⁱ—C4—C41—C422ⁱⁱ	−20.3 (12)	C4—C42—C422—N411ⁱⁱ	−167 (5)
C41ⁱⁱ—C4—C42—C43ⁱⁱ	179.5 (6)	C43ⁱⁱ—C42—C422—N411ⁱⁱ	−78 (7)
C41—C4—C42—C43ⁱⁱ	−0.5 (6)	C41ⁱⁱ—C42—C422—N411ⁱⁱ	170 (6)
C43—C4—C42—C43ⁱⁱ	180.001 (2)	C421—C42—C422—N411ⁱⁱ	12 (6)
C41ⁱⁱ—C4—C42—C422	−24.7 (14)	C411ⁱⁱ—C42—C422—N411ⁱⁱ	−173 (16)
C41—C4—C42—C422	155.3 (14)	C432ⁱⁱ—C42—C422—N411ⁱⁱ	13 (7)
C43—C4—C42—C422	−24.2 (15)	C4—C42—C422—N422	−102 (9)
C43ⁱⁱ—C4—C42—C422	155.8 (15)	C43ⁱⁱ—C42—C422—N422	−14 (12)
C41—C4—C42—C41ⁱⁱ	179.999 (2)	C41ⁱⁱ—C42—C422—N422	−125 (9)
C43—C4—C42—C41ⁱⁱ	0.5 (6)	C421—C42—C422—N422	77 (9)
C43ⁱⁱ—C4—C42—C41ⁱⁱ	−179.5 (6)	C411ⁱⁱ—C42—C422—N422	−109 (17)
C41ⁱⁱ—C4—C42—C421	156.5 (19)	C432ⁱⁱ—C42—C422—N422	78 (9)
C41—C4—C42—C421	−23.5 (19)	C4—C42—C422—C41ⁱⁱ	23.0 (13)
C43—C4—C42—C421	157.0 (18)	C43ⁱⁱ—C42—C422—C41ⁱⁱ	112 (3)
C43ⁱⁱ—C4—C42—C421	−23.0 (18)	C421—C42—C422—C41ⁱⁱ	−158.1 (17)
C41ⁱⁱ—C4—C42—C411ⁱⁱ	−23.3 (14)	C411ⁱⁱ—C42—C422—C41ⁱⁱ	17 (11)
C41—C4—C42—C411ⁱⁱ	156.7 (14)	C432ⁱⁱ—C42—C422—C41ⁱⁱ	−157 (2)
C43—C4—C42—C411ⁱⁱ	−22.8 (15)	C411ⁱⁱ—C422—N422—N411ⁱⁱ	155 (12)
C43ⁱⁱ—C4—C42—C411ⁱⁱ	157.2 (15)	C42—C422—N422—N411ⁱⁱ	−93 (10)
C41ⁱⁱ—C4—C42—C432ⁱⁱ	155.3 (17)	C41ⁱⁱ—C422—N422—N411ⁱⁱ	152 (5)
C41—C4—C42—C432ⁱⁱ	−24.7 (17)	N411ⁱⁱ—C422—N422—C411ⁱⁱ	−155 (12)
C43—C4—C42—C432ⁱⁱ	155.8 (16)	C42—C422—N422—C411ⁱⁱ	112 (16)
C43ⁱⁱ—C4—C42—C432ⁱⁱ	−24.2 (16)	C41ⁱⁱ—C422—N422—C411ⁱⁱ	−3 (8)
C41—C4—C43—C41ⁱⁱ	180.001 (3)	C41ⁱⁱ—C43—C431—C412ⁱⁱ	30 (12)
C42—C4—C43—C41ⁱⁱ	−0.5 (6)	C4—C43—C431—C412ⁱⁱ	58 (13)
C42ⁱⁱ—C4—C43—C41ⁱⁱ	179.5 (6)	C432—C43—C431—C412ⁱⁱ	−123 (12)
C41ⁱⁱ—C4—C43—C431	−30.5 (16)	C42ⁱⁱ—C43—C431—C412ⁱⁱ	142 (11)
C41—C4—C43—C431	149.5 (16)	C421ⁱⁱ—C43—C431—C412ⁱⁱ	−135 (12)
C42—C4—C43—C431	−30.9 (16)	C41ⁱⁱ—C43—C431—N412ⁱⁱ	166 (7)
C42ⁱⁱ—C4—C43—C431	149.1 (16)	C4—C43—C431—N412ⁱⁱ	−166 (6)
C41ⁱⁱ—C4—C43—C432	151 (2)	C432—C43—C431—N412ⁱⁱ	13 (7)
C41—C4—C43—C432	−29 (2)	C42ⁱⁱ—C43—C431—N412ⁱⁱ	−81 (7)
C42—C4—C43—C432	150.6 (19)	C412ⁱⁱ—C43—C431—N412ⁱⁱ	136 (16)
C42ⁱⁱ—C4—C43—C432	−29.4 (19)	C421ⁱⁱ—C43—C431—N412ⁱⁱ	1 (7)
C41ⁱⁱ—C4—C43—C42ⁱⁱ	−179.5 (6)	C4—C43—C431—C41ⁱⁱ	28.6 (13)
C41—C4—C43—C42ⁱⁱ	0.5 (6)	C432—C43—C431—C41ⁱⁱ	−153 (2)
C42—C4—C43—C42ⁱⁱ	180.001 (3)	C42ⁱⁱ—C43—C431—C41ⁱⁱ	113 (3)
C41ⁱⁱ—C4—C43—C412ⁱⁱ	−22.0 (9)	C412ⁱⁱ—C43—C431—C41ⁱⁱ	−30 (12)
C41—C4—C43—C412ⁱⁱ	158.0 (9)	C421ⁱⁱ—C43—C431—C41ⁱⁱ	−164.6 (18)
C42—C4—C43—C412ⁱⁱ	−22.5 (11)	C412ⁱⁱ—C431—N431—N412ⁱⁱ	149 (13)
C42ⁱⁱ—C4—C43—C412ⁱⁱ	157.5 (11)	C41ⁱⁱ—C431—N431—N412ⁱⁱ	172 (7)
C41ⁱⁱ—C4—C43—C421ⁱⁱ	161.5 (16)	N412ⁱⁱ—C431—N431—C412ⁱⁱ	−149 (13)
C41—C4—C43—C421ⁱⁱ	−18.5 (16)	C41ⁱⁱ—C431—N431—C412ⁱⁱ	23 (9)
C42—C4—C43—C421ⁱⁱ	161.0 (15)	C41ⁱⁱ—C43—C432—C421ⁱⁱ	141 (12)
C42ⁱⁱ—C4—C43—C421ⁱⁱ	−19.0 (15)	C431—C43—C432—C421ⁱⁱ	−123 (14)
C43ⁱⁱ—C41—C411—C422ⁱⁱ	131 (11)	C4—C43—C432—C421ⁱⁱ	55 (15)
C4—C41—C411—C422ⁱⁱ	46 (13)	C42ⁱⁱ—C43—C432—C421ⁱⁱ	28 (14)
C42ⁱⁱ—C41—C411—C422ⁱⁱ	19 (12)	C412ⁱⁱ—C43—C432—C421ⁱⁱ	−132 (14)
C412—C41—C411—C422ⁱⁱ	−139 (12)	C41ⁱⁱ—C43—C432—N421ⁱⁱ	−77 (11)
C431ⁱⁱ—C41—C411—C422ⁱⁱ	−139 (12)	C431—C43—C432—N421ⁱⁱ	19 (10)
C43ⁱⁱ—C41—C411—N422ⁱⁱ	−57 (11)	C4—C43—C432—N421ⁱⁱ	−162 (8)
C4—C41—C411—N422ⁱⁱ	−142 (9)	C42ⁱⁱ—C43—C432—N421ⁱⁱ	170 (10)
C42ⁱⁱ—C41—C411—N422ⁱⁱ	−169 (10)	C412ⁱⁱ—C43—C432—N421ⁱⁱ	10 (10)
C412—C41—C411—N422ⁱⁱ	33 (10)	C421ⁱⁱ—C43—C432—N421ⁱⁱ	142 (22)
C431ⁱⁱ—C41—C411—N422ⁱⁱ	33 (11)	C41ⁱⁱ—C43—C432—C42ⁱⁱ	113 (3)
C422ⁱⁱ—C41—C411—N422ⁱⁱ	172 (22)	C431—C43—C432—C42ⁱⁱ	−151.0 (16)
C43ⁱⁱ—C41—C411—N411	−157 (12)	C4—C43—C432—C42ⁱⁱ	27.5 (17)
C4—C41—C411—N411	117 (13)	C412ⁱⁱ—C43—C432—C42ⁱⁱ	−159.9 (12)
C42ⁱⁱ—C41—C411—N411	90 (14)	C421ⁱⁱ—C43—C432—C42ⁱⁱ	−28 (14)
C412—C41—C411—N411	−68 (14)	C421ⁱⁱ—C432—N432—N421ⁱⁱ	166 (16)
C431ⁱⁱ—C41—C411—N411	−68 (14)	C42ⁱⁱ—C432—N432—N421ⁱⁱ	−176 (7)
C422ⁱⁱ—C41—C411—N411	71 (17)	N421ⁱⁱ—C432—N432—C421ⁱⁱ	−166 (16)
C43ⁱⁱ—C41—C411—C42ⁱⁱ	113 (3)	C42ⁱⁱ—C432—N432—C421ⁱⁱ	18 (10)
C4—C41—C411—C42ⁱⁱ	27.0 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···N412	0.93	2.52	3.404 (16)	159
C26—H26···N421	0.93	2.31	3.23 (3)	170
C26—H26···N432ⁱⁱ	0.93	2.54	3.47 (3)	173
C36—H36···N412ⁱⁱⁱ	0.93	2.48	3.352 (17)	157
C36—H36···N431^iv	0.93	2.50	3.39 (2)	160

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

Funding information

FS gratefully acknowledges the Algerian MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique), the DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique), as well as the Université Ferhat Abbas Sétif 1 for financial support.

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