Crystal structure of catena-poly[[gold(I)-μ-cyanido-[di­aqua­bis­(2-phenyl­pyrazine)­iron(II)]-μ-cyanido] dicyanidogold(I)]

Kucheriv, O.I.; Barakhtii, D.D.; Malinkin, S.O.; Shova, S.; Gural'skiy, I.A.

doi:10.1107/S2056989019009678

research communications

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ISSN: 2056-9890

Volume 75| Part 8| August 2019| Pages 1149-1152

https://doi.org/10.1107/S2056989019009678

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Crystal structure of catena-poly[[gold(I)-μ-cyanido-[diaquabis(2-phenylpyrazine)iron(II)]-μ-cyanido] dicyanidogold(I)]

Olesia I. Kucheriv,^a,^b ^* Diana D. Barakhtii,^a Sergey O. Malinkin,^a Sergiu Shova ^c and Il'ya A. Gural'skiy ^a,^b

^aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska St. 64, Kyiv 01601, Ukraine, ^bUkrOrgSyntez Ltd, Chervonotkatska St., 67, Kyiv 02094, Ukraine, and ^cDepartment of Inorganic Polymers, "Petru Poni" Institute of Macromolecular Chemistry, Romanian Academy of Science, Aleea Grigore Ghica Voda 41-A, Iasi 700487, Romania
^*Correspondence e-mail: lesya.kucheriv@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 4 July 2019; accepted 7 July 2019; online 12 July 2019)

In the title polymeric complex, {[Fe(CN)₂(C₁₀H₈N₂)₂(H₂O)₂][Au(CN)₂]}_n, the Fe^II ion, which is located on a twofold rotation axis, has a slightly distorted FeN₄O₂ octahedral geometry. It is coordinated by two phenylpyrazine molecules, two water molecules and two dicyanoaurate anions, the Au atom also being located on a second twofold rotation axis. In the crystal, the coordinated dicyanoaurate anions bridge the Fe^II ions to form polymeric chains propagating along the b-axis direction. In the crystal, the chains are linked by O_water—H⋯N_{dicyanoaurate anions} hydrogen bonds and aurophillic interactions [Au⋯Au = 3.5661 (3) Å], forming layers parallel to the bc plane. The layers are linked by offset π–π stacking interactions [intercentroid distance = 3.643 (3) Å], forming a supramolecular metal–organic framework.

Keywords: crystal structure; polymeric complex; iron(II) complex; 2-phenylpyrazine; dicyanoaurate; aurophillic interactions; offset π–π interactions; supramolecular metal–organic framework.

CCDC reference: 1938914

1. Chemical context

The design of functional materials based on coordination compounds is an important area of current scientific research. For example, metal–organic frameworks (MOFs), which consist of metal ions and organic ligand linkers, are studied intensively. Fe-based coordination polymers with N-donor bridging ligands are well known as compounds with switchable spin states (Niel et al., 2003 ; Gural'skiy et al., 2016 ; Kucheriv et al., 2016 ). This phenomenon is called spin crossover and can be observed in complexes of 3d⁴–3d⁷ metal ions. Applying external stimuli, such as temperature, pressure, magnetic field, light irradiation or adding a guest can affect this kind of the compound and change their properties significantly (Gütlich & Goodwin, 2004 ). The synthesis and crystallographic characterization of these complexes are of current interest because of the bistability of their magnetic, electrical, mechanical and optical properties (Senthil Kumar & Ruben, 2017 ). The parameters of these transitions could be controlled through a wide variety of available organic ligands and co-ligands. Complexes with metallocyanate bridges as co-ligands to N-bridging ligands form one of the largest family of spin-crossover compounds (Muñoz & Real, 2011 ). Here we report on a new one-dimensional polymeric compound that is similar in its structure to switchable cyanometallates. It employs 2-phenylpyrazine as a ligand and Au(CN)²⁻ as co-ligands, while coordinated H₂O molecules stabilize the Fe^II ions in the high-spin state.

2. Structural commentary

The structure of the title compound features a one-dimensional chain motif that runs parallel to the crystallographic b axis (Figs. 1 and 2). The compound crystallizes in the monoclinic space group C2/c. Selected bond distances and bond angles are given in Table 1. The coordination sphere of the Fe^II cation, atom Fe1, which is located on a twofold rotation axis, has a distorted octahedral environment [FeN₄O₂]. It includes two 2-phenylpyrazine N atoms [Fe1—N3 = 2.223 (5) Å] in axial positions, and two N atoms of cyano bridges and two water O atoms of water molecules [Fe1—O1 = 2.122 (4) Å] in equatorial positions. The two CN⁻ anions bridge the Fe^II and Au^I cations [Fe1⋯Au1 = 5.244 (3) Å] to form a one-dimensional polymeric structure with bond lengths Fe1—N1 = 2.107 (5) Å and Fe1—–N2 = 2.117 (6) Å (Fig. 1 and Table 1). The Fe^II octahedral distortion parameter (the sum of the moduli of the deviations from 90° for all cis-bond angles) is Σ|90 - Θ| = 8.53°, where Θ are the cis-N—Fe—O and cis-N—Fe—N angles in the coordination environment of the Fe^II atom.

Table 1
Selected geometric parameters (Å, °)

Au1—C1	1.975 (7)	Fe1—N2	2.117 (6)
Au1—C2ⁱ	1.988 (7)	Fe1—O1	2.122 (4)
Au2—C13	1.988 (6)	Fe1—N3	2.223 (5)
Fe1—N1	2.107 (5)

C1—Au1—C2ⁱ	180	N2—Fe1—N3	89.60 (10)
C13ⁱⁱ—Au2—C13	180	O1—Fe1—N3	90.09 (16)
N1—Fe1—N2	180	C1—N1—Fe1	180
O1—Fe1—O1ⁱⁱⁱ	176.73 (19)	C2—N2—Fe1	180
N3—Fe1—N3ⁱⁱⁱ	179.19 (19)	N1—C1—Au1	180
N1—Fe1—O1	91.63 (9)	N2—C2—Au1^iv	180
N2—Fe1—O1	88.37 (9)	N5—C13—Au2	175.8 (7)
N1—Fe1—N3	90.40 (10)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z.

Figure 1
A fragment of the molecular structure of the title compound, with the atom labelling Displacement ellipsoids are drawn at the 50% probability level. The Au1⋯Au2 interaction [3.5661 (3) Å] is shown as a dashed line. [Symmetry codes: (i) x, y − 1, z; (ii) x − 1, y − 1, z − 1; (iii) −x − 1, y, −z + $[{3\over 2}]$ ; (iv) x, y + 1, z].

Figure 2
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds (Table 2

) and aurophillic interactions as shown as dashed lines. For clarity, the C-bound H atoms have been omitted.

3. Supramolecular features

The crystal packing features different types of weak interactions (see Table 2 and Figs. 2 and 3). The free dicyanoaurate anions are linked to the polymeric chains by O_water—H⋯N hydrogen bonds [O1—H1A⋯N5^v = 2.02 Å and O1—H1B⋯N5^vi = 2.18 Å; Table 2], and by aurophillic interactions [Au1⋯Au2 = 3.566 (2) Å], forming layers parallel to the bc plane. The layers are then linked via offset π–π interactions involving a pyrazine ring as an acceptor and a phenyl ring as a donor of electron density, forming a supramolecular metal–organic framework [Cg1⋯Cg2 = 3.643 (3) Å, where Cg1 and Cg2 are the centroids of the N3/N4/C3–C6 and C7–C12 rings, respectively; α = 3.8 (3)°, interplanar distances = 3.466 (2) and 3.510 (2) Å, offset = 0.976 Å, symmetry code (i): −x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , −z + 1].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N5^v	0.86	2.02	2.851 (6)	165
O1—H1B⋯N5^vi	0.85	2.18	3.023 (6)	178
Symmetry codes: (v) $[x, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y+1, -z+{\script{3\over 2}}]$ .

Figure 3
A view along the b axis of the crystal packing of the title compound. The O—H⋯N hydrogen bonds and Au⋯Au interactions are shown as dashed lines. For clarity, the C-bound H atoms have been omitted.

4. Database survey

A survey of the Cambridge Structural Database (Version 5.38; Groom et al., 2016 ) confirmed that the structure of the title complex has not been reported previously and revealed 41 Fe–Au CN-bridged frameworks supported axially by different co-ligands. There are 37 compounds with an octahedral FeN₆ environment. The coordination spheres of such compounds are formed by pyridine-azine ligands, substituted pyridines, saturated and substituted pyrazines, and pyrimidine (Clements et al., 2016 ; Arcís-Castillo et al., 2013 ; Agustí et al., 2008 ; Clements et al., 2014 , Kosone & Kitazawa, 2016 ; Niel et al., 2003). Nine such compounds have a stable low- or high-spin state and another 28 are complexes with a switchable spin state. There are also four compounds with an environment formed by the N atoms of organic ligands and water O atoms. The only compound with an FeN₅O environment contains a pyridine-based N-donor ligand (Xu et al., 2014 ), while three compounds have an FeN₄O₂ octahedral geometry. The bidentate bridging organoselenium triazole ligand and two different pyridine-based ligands were used to obtain these latter complexes (Seredyuk et al., 2007 ; Xu et al., 2014).

5. Synthesis and crystallization

Crystals of the title compound were prepared by the slow diffusion method between three layers in a 10 ml tube. The first layer was a solution of K[Au(CN)₂] (0.0058 g, 0.02 mmol) in water (2.5 ml), the second was a mixture of water/acetonitrile (1:2, 5 ml) and the third layer was a solution of 2-phenylpyrazine (0.0078 g, 0.05 mmol) and [Fe(OTs)₂]·6H₂O (0.0101 g, 0.02 mmol) (OTs = p-toluenesulfonate) in acetonitrile (2.5 ml) with 0.3 ml of water. After two weeks, yellow crystals grew in the second layer; these were collected and maintained under the mother solution until measured.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen atoms were placed in their expected calculated positions (C—H = 0.93 Å) and refined as riding with U_iso(H) = 1.2U_iso(C). The idealized OH₂ group was fixed using an AFIX 7 command that allowed the H atoms to ride on the O atom and rotate around the bond.

Table 3
Experimental details

Crystal data
Chemical formula	[AuFe(CN)₂(C₁₀H₈N₂)₂(H₂O)₂][Au(CN)₂]
M_r	902.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.5306 (13), 10.4541 (3), 14.2522 (9)
β (°)	107.509 (7)
V (Å³)	2633.0 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	11.70
Crystal size (mm)	0.3 × 0.3 × 0.1

Data collection
Diffractometer	Rigaku Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.292, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7203, 3265, 2410
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.084, 1.04
No. of reflections	3265
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.37, −1.45
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELX2018 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1938914

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989019009678/su5503sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019009678/su5503Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELX2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

catena-Poly[[gold(I)-µ-cyanido-[diaquabis(2-phenylpyrazine)iron(II)]-µ-cyanido] dicyanidogold(I)] top

Crystal data top

[AuFe(CN)₂(C₁₀H₈N₂)₂(H₂O)₂][Au(CN)₂]	F(000) = 1680
M_r = 902.26	D_x = 2.276 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.5306 (13) Å	Cell parameters from 2258 reflections
b = 10.4541 (3) Å	θ = 2.3–30.8°
c = 14.2522 (9) Å	µ = 11.70 mm⁻¹
β = 107.509 (7)°	T = 293 K
V = 2633.0 (3) Å³	Plate, clear light yellow
Z = 4	0.3 × 0.3 × 0.1 mm

Data collection top

Rigaku Xcalibur Eos diffractometer	3265 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2410 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.0797 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
ω scans	h = −17→24
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −7→13
T_min = 0.292, T_max = 1.000	l = −18→16
7203 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: mixed
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0308P)² + 0.2566P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 1.37 e Å⁻³
0 restraints	Δρ_min = −1.45 e Å⁻³

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
Au1	0.500000	0.51420 (2)	0.750000	0.03916 (11)
Au2	0.500000	0.500000	0.500000	0.04886 (13)
Fe1	0.500000	1.01389 (8)	0.750000	0.0304 (3)
O1	0.4511 (3)	1.0197 (3)	0.8669 (2)	0.0440 (10)
H1A	0.461953	0.949471	0.898996	0.066*
H1B	0.474896	1.072647	0.910236	0.066*
C12	0.2099 (3)	0.8548 (6)	0.3359 (4)	0.0498 (16)
H12	0.177175	0.921680	0.337514	0.060*
N3	0.3852 (3)	1.0154 (3)	0.6414 (3)	0.0372 (11)
N1	0.500000	0.8124 (5)	0.750000	0.0381 (16)
C1	0.500000	0.7031 (6)	0.750000	0.0347 (18)
N4	0.2472 (3)	1.0277 (4)	0.4918 (3)	0.0487 (13)
C3	0.3652 (3)	0.9310 (4)	0.5669 (4)	0.0366 (13)
H3	0.398880	0.865572	0.565374	0.044*
C9	0.3032 (4)	0.6538 (5)	0.3300 (4)	0.0556 (17)
H9	0.335120	0.585689	0.328588	0.067*
C13	0.4723 (4)	0.3157 (6)	0.4880 (4)	0.0519 (17)
C7	0.2772 (3)	0.8418 (5)	0.4104 (4)	0.0355 (12)
C6	0.3334 (3)	1.1041 (5)	0.6411 (4)	0.0453 (15)
H6	0.343207	1.163949	0.691614	0.054*
N5	0.4606 (3)	0.2077 (5)	0.4804 (3)	0.0572 (15)
N2	0.500000	1.2164 (5)	0.750000	0.0465 (19)
C10	0.2365 (4)	0.6684 (6)	0.2558 (4)	0.0558 (18)
H10	0.222790	0.609994	0.204193	0.067*
C8	0.3230 (3)	0.7399 (5)	0.4067 (4)	0.0448 (15)
H8	0.368242	0.728887	0.456743	0.054*
C5	0.2662 (4)	1.1083 (5)	0.5674 (4)	0.0518 (16)
H5	0.231568	1.171427	0.570352	0.062*
C11	0.1910 (4)	0.7682 (6)	0.2584 (4)	0.0553 (17)
H11	0.146242	0.779119	0.207499	0.066*
C4	0.2977 (3)	0.9364 (4)	0.4927 (4)	0.0336 (12)
C2	0.500000	1.3240 (7)	0.750000	0.045 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.0509 (2)	0.01133 (13)	0.0543 (2)	0.000	0.01452 (16)	0.000
Au2	0.0638 (3)	0.02992 (17)	0.0467 (2)	0.00972 (13)	0.00732 (17)	−0.00062 (12)
Fe1	0.0484 (7)	0.0125 (4)	0.0289 (5)	0.000	0.0094 (5)	0.000
O1	0.069 (3)	0.0265 (17)	0.035 (2)	0.0036 (17)	0.0132 (19)	−0.0003 (15)
C12	0.041 (4)	0.062 (4)	0.045 (4)	−0.003 (3)	0.011 (3)	−0.002 (3)
N3	0.045 (3)	0.025 (2)	0.041 (3)	0.0041 (18)	0.011 (2)	0.0012 (18)
N1	0.055 (5)	0.010 (2)	0.045 (4)	0.000	0.010 (3)	0.000
C1	0.038 (5)	0.026 (4)	0.041 (4)	0.000	0.013 (3)	0.000
N4	0.052 (3)	0.044 (2)	0.047 (3)	0.012 (2)	0.011 (2)	0.001 (2)
C3	0.043 (4)	0.023 (2)	0.042 (3)	−0.001 (2)	0.010 (3)	−0.003 (2)
C9	0.070 (5)	0.045 (3)	0.051 (4)	−0.004 (3)	0.018 (3)	−0.010 (3)
C13	0.071 (5)	0.041 (3)	0.040 (3)	0.012 (3)	0.011 (3)	−0.001 (3)
C7	0.036 (3)	0.034 (3)	0.037 (3)	−0.002 (2)	0.013 (2)	0.003 (2)
C6	0.058 (4)	0.034 (3)	0.044 (3)	0.011 (3)	0.015 (3)	−0.003 (2)
N5	0.083 (4)	0.040 (3)	0.047 (3)	0.006 (3)	0.017 (3)	−0.002 (2)
N2	0.075 (6)	0.018 (3)	0.041 (4)	0.000	0.010 (4)	0.000
C10	0.065 (5)	0.055 (4)	0.047 (4)	−0.023 (3)	0.016 (3)	−0.015 (3)
C8	0.045 (4)	0.043 (3)	0.041 (3)	−0.004 (2)	0.005 (3)	−0.008 (2)
C5	0.060 (4)	0.037 (3)	0.060 (4)	0.019 (3)	0.021 (3)	0.004 (3)
C11	0.042 (4)	0.079 (5)	0.037 (4)	−0.016 (3)	0.001 (3)	−0.006 (3)
C4	0.037 (3)	0.029 (2)	0.036 (3)	0.000 (2)	0.012 (2)	0.008 (2)
C2	0.067 (6)	0.019 (3)	0.046 (5)	0.000	0.014 (4)	0.000

Geometric parameters (Å, º) top

Au1—C1	1.975 (7)	N4—C5	1.329 (7)
Au1—C2ⁱ	1.988 (7)	N4—C4	1.333 (7)
Au2—C13ⁱⁱ	1.988 (6)	C3—C4	1.376 (7)
Au2—C13	1.988 (6)	C3—H3	0.9300
Fe1—N1	2.107 (5)	C9—C10	1.373 (7)
Fe1—N2	2.117 (6)	C9—C8	1.377 (7)
Fe1—O1	2.122 (4)	C9—H9	0.9300
Fe1—O1ⁱⁱⁱ	2.122 (4)	C13—N5	1.149 (7)
Fe1—N3	2.223 (5)	C7—C8	1.374 (7)
Fe1—N3ⁱⁱⁱ	2.223 (5)	C7—C4	1.492 (7)
O1—H1A	0.8564	C6—C5	1.368 (7)
O1—H1B	0.8479	C6—H6	0.9300
C12—C7	1.380 (6)	N2—C2	1.125 (8)
C12—C11	1.390 (7)	C10—C11	1.349 (8)
C12—H12	0.9300	C10—H10	0.9300
N3—C6	1.333 (6)	C8—H8	0.9300
N3—C3	1.344 (6)	C5—H5	0.9300
N1—C1	1.143 (8)	C11—H11	0.9300

C1—Au1—C2ⁱ	180	N3—C3—C4	123.4 (5)
C13ⁱⁱ—Au2—C13	180	N3—C3—H3	118.3
N1—Fe1—N2	180	C4—C3—H3	118.3
O1—Fe1—O1ⁱⁱⁱ	176.73 (19)	C10—C9—C8	120.2 (6)
N3—Fe1—N3ⁱⁱⁱ	179.19 (19)	C10—C9—H9	119.9
N1—Fe1—O1	91.63 (9)	C8—C9—H9	119.9
N2—Fe1—O1	88.37 (9)	N2—C2—Au1^iv	180
N1—Fe1—O1ⁱⁱⁱ	91.63 (9)	N5—C13—Au2	175.8 (7)
N2—Fe1—O1ⁱⁱⁱ	88.37 (9)	C8—C7—C12	118.2 (5)
N1—Fe1—N3	90.40 (10)	C8—C7—C4	122.0 (5)
N2—Fe1—N3	89.60 (10)	C12—C7—C4	119.8 (5)
O1—Fe1—N3	90.09 (16)	N3—C6—C5	120.9 (5)
O1ⁱⁱⁱ—Fe1—N3	89.89 (16)	N3—C6—H6	119.6
N1—Fe1—N3ⁱⁱⁱ	90.40 (10)	C5—C6—H6	119.6
N2—Fe1—N3ⁱⁱⁱ	89.60 (10)	C11—C10—C9	119.3 (6)
O1—Fe1—N3ⁱⁱⁱ	89.89 (16)	C11—C10—H10	120.3
O1ⁱⁱⁱ—Fe1—N3ⁱⁱⁱ	90.09 (16)	C9—C10—H10	120.3
Fe1—O1—H1A	108.0	C7—C8—C9	121.2 (5)
Fe1—O1—H1B	109.9	C7—C8—H8	119.4
H1A—O1—H1B	100.6	C9—C8—H8	119.4
C7—C12—C11	120.1 (6)	N4—C5—C6	124.0 (5)
C7—C12—H12	120.0	N4—C5—H5	118.0
C11—C12—H12	120.0	C6—C5—H5	118.0
C6—N3—C3	115.3 (5)	C10—C11—C12	121.1 (6)
C6—N3—Fe1	123.0 (4)	C10—C11—H11	119.5
C3—N3—Fe1	121.6 (4)	C12—C11—H11	119.5
C1—N1—Fe1	180	N4—C4—C3	120.7 (5)
C2—N2—Fe1	180	N4—C4—C7	117.1 (5)
N1—C1—Au1	180	C3—C4—C7	122.3 (5)
C5—N4—C4	115.6 (5)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y, −z+3/2; (iv) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N5^v	0.86	2.02	2.851 (6)	165
O1—H1B···N5^vi	0.85	2.18	3.023 (6)	178

Symmetry codes: (v) x, −y+1, z+1/2; (vi) −x+1, y+1, −z+3/2.

Funding information

Funding for this research was provided by: Ministry of Education and Science of Ukraine (grant Nos. 19BF037-01M, DZ/55-2018); H2020-MSCA-RISE-2016 (grant No. 73422).

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