Crystal structure of poly[tetra-μ-cyanido-ethanol-bis(2-iodo-pyrazine)-digold(I)iron(II)].

In the title polymeric complex, [Au2Fe(CN)4(C4H3IN2)2(C2H6O)] n , the FeII cation is coordinated by two iodo-pyrazine mol-ecules, one ethanol mol-ecule and three di-cyano-aurate anions in a distorted N5O octa-hedral geometry. In the crystal, the di-cyano-aurate anions bridge the FeII cations to form polymeric chains propagating along the b-axis direction. Stabilization of the crystal structure is provided by O-H⋯N hydrogen bonds and π-π stacking between parallel iodo-pyrazine rings of neighbouring chains, the centroid-centroid distances being 3.654 (10) and 3.658 (9) Å.

Chemical context

Among all coordination compounds, cyanide-based complexes attract considerable attention. The cyanide group can be coordinated in either a monodentate or bridging way, connecting different metal ions, leading to the formation of one-, two- or three-dimensional frameworks. The variety of possible structures of cyanide-based complexes results in a variety of functional properties for these coordination materials, such as the ability to include small guest mol­ecules (Klausmeyer et al., 1998 ▸), act as room-temperature magnets (Garde et al., 2002 ▸), display photomagnetic and magneto-optical properties (Mizuno et al., 2000 ▸; Mercurol et al., 2010 ▸), etc. The most representative examples of cyanide-bridged complexes are Prussian blue analogues, which form three-dimensional frameworks with general formula A I M A II[M B III(CN)6] (A = alkali ion, M A and M B = transition metal ions; Keggin & Miles, 1936 ▸). Prussian blue analogues are very attractive because of their facile synthesis and the possibility to manipulate the magnetic ordering of the material by selecting appropriate spin sources (Ohkoshi et al., 1997 ▸).

Cyano­metallate complexes are typically characterized by a low-spin state of the metal ions; however, the introduction of a complementary ligand with weak ligand field strength can lead to the formation of spin-crossover compounds. This type of compound is mostly represented by Hofmann clathrate analogues with general formula [M(L){M′(CN)4}] where M = Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+ and Mn2+, M′ = Ni2+, Pd2+, Pt2+ and L is either a unidentate or bridging ligand. The first compound of this type reported by Hofmann & Höchtlen (1903 ▸) was the [Ni(NH3)2{Ni(CN)4}] clathrate, which is able to incorporate benzene or other aromatic mol­ecules. In this structure, the bridging tetra­cyano­nikelate anions contribute to the formation of infinite layers that propagate in the ab plane (Powell & Rayner, 1949 ▸). However, the first Hofmann-clathrate analogue displaying spin-crossover behavior was [Fe(py)2{Ni(CN)4}] (Kitazawa et al., 1996 ▸). Later, different examples have been obtained for the modification of the original Hofmann clathrates, notably with di- or octa­cyano­metallates (Gural’skiy et al., 2016b ▸; Wei et al., 2016 ▸). Another modification method is the use of different organic ligands; for example, the inclusion of a bidentate ligand such as pyrazine leads to the formation of a three-dimensional network (Niel et al., 2001 ▸). Here we report a new cyanide-based compound with general formula [Fe(Ipz)2(EtOH){Au(CN)2}2] in which the FeII ions are stabilized in the high-spin state.

Structural commentary

The crystal structure of the title compound was determined at 296 K. It crystallizes in the triclinic P space group with two formula units per cell. The FeII site has a distorted octa­hedral [FeN5O] coordination environment formed by two iodo­pyrazine N atoms, three di­cyano­aurate N atoms and one ethanol O atom (Fig. 1 ▸). Two iodo­pyrazine mol­ecules are coordinated in the cis configuration with the Fe—N distances of 2.216 (7) and 2.272 (7) Å (Table 1 ▸) indicating the high-spin state of the FeII cation. One of the di­cyano­aurate fragments is N-coordinated to the FeII site in the form of an anion [Fe1—N2 = 2.096 (7) Å], while the other two are coordinated in a trans configuration, further connecting the framework into a chain [Fe1—N1 = 2.105 (8) and Fe1—N5 = 2.096 (8) Å]. The CN− anions bridge the FeII and AuI cations in a quasi-linear mode with C1—Au1—C2 = 178.8 (3) and C3—Au2—C4 = 178.9 (3)°. In addition, one of the coordination sites of the FeII ion is occupied by an O-coordinated ethanol molecule nwith Fe1—O1 = 2.106 (6) Å, which is a typical value for Fe—Oalcohol bonds. There is a deviation from an ideal octa­hedral geometry, Σ|90 - Θ| = 33.1°, where Θ is the cis-N—Fe—N or cis-O—Fe—N angle in the coordination environment of FeII. This value indicates a significant polyhedral distortion that can be explained by the Jahn–Teller effect and the presence of four different types of ligands.

Figure 1

A fragment of the mol­ecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry codes: (i) x, 1 + y, z; (ii) x, −1 + y, z].

Table 1

Selected bond lengths (Å)

Au1—C1	1.948 (9)	Fe1—N1	2.105 (8)
Au1—C2	1.952 (8)	Fe1—N2	2.096 (7)
Au2—C3	1.970 (8)	Fe1—N3	2.272 (7)
Au2—C4	1.981 (9)	Fe1—N4	2.216 (7)
Fe1—O1	2.106 (6)	Fe1—N5i	2.096 (8)

Symmetry code: (i) .

Supra­molecular features

The coordination framework is connected by bridging di­cyano­aurate moieties into chains that propagate along the b-axis direction. In addition, the crystal packing is supported by N⋯H—O hydrogen bonds (Fig. 2 ▸ a, Table 2 ▸) in which H atoms from the ethanol hydroxyl group participate in weak inter­actions with the N atoms of the di­cyano­aurate anions. The structure includes parallel-displaced π–π inter­actions with a distance of 3.381 (5) Å between the planes of the aromatic rings (Fig. 2 ▸ b). Short Au ⋯ Au distances of 3.163 (5) Å indicate inter­molecular aurophilic inter­actions between the Au atoms of the monodentate and bridging di­cyano­aurate moieties (Fig. 2 ▸ c). The same type of aurophilic inter­action was observed for a very similar Au–Fe–pyrazine complex, which displays high-temperature spin-transition behavior [Au⋯Au (LS, 340 K) = 3.3886 (3) Å, Au⋯Au (HS, 360 K) = 3.5870 (5) Å; Gural’skiy et al., 2016a ▸]. The Au⋯Au distances in the above-mentioned structure are longer because they are defined by a three-dimensional framework of the complex; however, in the case of the title compound, the di­cyano­aurate anions are non-bridging and therefore are more flexible, which leads to the creation of aurophilic contacts that are closer to the optimum distance of 3 Å (Schmidbaur, 2000 ▸).

Figure 2

The crystal structure of the title compound. (a) View in the ac plane showing N⋯H—O hydrogen bonds (dashed lines). H atoms, except those involved in hydrogen bonding, are omitted for clarity. (b) Structure of the title compound showing π–π contacts (dashed lines). (c) View in the bc plane showing aurophilic inter­actions (dashed lines). Colour key: Fe dark red; Ag cyan; N blue; O red; C grey; I purple.

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N6ii	0.86 (5)	1.98 (5)	2.765 (13)	151 (6)

Symmetry code: (ii) .

Database survey

A survey of the Cambridge structural Database (Version 5.38; Groom et al., 2016 ▸) confirmed that the title compound has never been published before. It also revealed numerous examples of CN-bridged Au–Fe bimetallic frameworks supported by substituted azines (Li et al., 2015 ▸; Agustí et al., 2008 ▸; Kosone et al., 2009 ▸) and non-substituted azines (Niel et al., 2003 ▸; Gural’skiy et al., 2016a ▸; Kosone et al., 2008 ▸).

Synthesis and crystallization

Crystals of the title compound were obtained by the slow-diffusion method with three layers in a 5 ml tube. The first layer was a solution of K[Au(CN)2] (29 mg, 0.1 mmol) in water (1 ml), the second layer was a water/ethanol mixture (1:1, 2.5 ml) and the third layer was a solution of Fe(OTs)2·6H2O (OTs = toluene­sulfonate) (50.6 mg, 0.1 mmol) and iodo­pyrazine (41.2 mg, 0.2 mmol) in ethanol (1 ml). After two weeks, yellow crystals grew in the middle layer; these were collected and kept under the mother solution prior to measurement.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. All hydrogen atoms were placed geometrically at their expected calculated positions with C—H = 0.96 (CH3), 0.97 (CH2), 0.93 Å (Carom), O—H = 0.859 (10) Å, and with U iso(H) = 1.2U eq(C) with the exception of methyl hydrogen atoms, which were refined with U iso(H) = 1.5U eq(C). The idealized CH3 group was fixed using an AFIX 137 command that allowed the H atoms to ride on the C atom and rotate around th C—C bond.

Table 3

Experimental details

Crystal data
Chemical formula	[Au2Fe(CN)4(C4H3IN2)2(C2H6O)]
M r	1011.90
Crystal system, space group	Triclinic, P
Temperature (K)	296
a, b, c (Å)	9.40 (2), 10.30 (2), 12.81 (3)
α, β, γ (°)	92.05 (6), 99.67 (7), 114.30 (6)
V (Å3)	1106 (4)
Z	2
Radiation type	Mo Kα
μ (mm−1)	16.70
Crystal size (mm)	0.20 × 0.05 × 0.03
Data collection
Diffractometer	Bruker SMART
Absorption correction	Part of the refinement model (ΔF) (Walker & Stuart, 1983 ▸)
T min, T max	0.298, 0.456
No. of measured, independent and observed [I > 2σ(I)] reflections	5556, 5556, 4453
R int	0.097
(sin θ/λ)max (Å−1)	0.680
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.038, 0.077, 0.92
No. of reflections	5556
No. of parameters	257
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	2.26, −2.28

Computer programs: SMART and SAINT (Bruker, 2013 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL (Sheldrick, 2015b ▸), DIAMOND (Brandenburg et al., 1999 ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989017014785/xu5907sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017014785/xu5907Isup2.hkl

CCDC reference: 1579611

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Au2Fe(CN)4(C4H3IN2)2(C2H6O)]	Z = 2
Mr = 1011.90	F(000) = 900
Triclinic, P1	Dx = 3.039 Mg m−3
a = 9.40 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.30 (2) Å	Cell parameters from 5517 reflections
c = 12.81 (3) Å	θ = 2.4–28.1°
α = 92.05 (6)°	µ = 16.70 mm−1
β = 99.67 (7)°	T = 296 K
γ = 114.30 (6)°	Needle, yellow
V = 1106 (4) Å3	0.20 × 0.05 × 0.03 mm

Bruker SMART diffractometer	4453 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.097
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	θmax = 28.9°, θmin = 1.6°
Tmin = 0.298, Tmax = 0.456	h = −10→12
5556 measured reflections	k = −13→8
5556 independent reflections	l = −16→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0259P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
5556 reflections	Δρmax = 2.26 e Å−3
257 parameters	Δρmin = −2.28 e Å−3
3 restraints

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.

	x	y	z	Uiso*/Ueq
Au1	0.59034 (4)	0.85190 (3)	0.70913 (2)	0.01892 (7)
Au2	0.11598 (3)	0.01716 (3)	0.40500 (2)	0.02116 (8)
I1	0.85042 (7)	0.17524 (6)	0.33540 (4)	0.03085 (13)
I2	1.09742 (8)	0.86712 (6)	0.99527 (4)	0.03868 (15)
Fe1	0.58906 (12)	0.35008 (10)	0.69926 (7)	0.0154 (2)
O1	0.4739 (6)	0.3148 (6)	0.8300 (4)	0.0229 (11)
H1	0.379 (4)	0.310 (7)	0.825 (3)	0.034*
N4	0.8280 (7)	0.4651 (6)	0.8031 (4)	0.0197 (13)
N6	−0.1459 (9)	−0.2072 (8)	0.2275 (5)	0.0306 (16)
N2	0.3802 (7)	0.2347 (7)	0.5851 (4)	0.0206 (13)
N3	0.7137 (7)	0.3977 (6)	0.5585 (4)	0.0184 (12)
N7	0.8521 (8)	0.4547 (7)	0.3799 (5)	0.0252 (14)
C4	−0.0500 (9)	−0.1237 (9)	0.2898 (5)	0.0242 (16)
N8	1.1356 (8)	0.6149 (7)	0.9205 (5)	0.0270 (14)
N1	0.5698 (7)	0.5466 (6)	0.6996 (4)	0.0200 (12)
C3	0.2821 (9)	0.1544 (8)	0.5205 (5)	0.0186 (14)
N5	0.6142 (8)	1.1576 (7)	0.7088 (4)	0.0215 (13)
C6	0.8096 (9)	0.3307 (8)	0.4158 (5)	0.0196 (14)
C5	0.7384 (9)	0.2989 (8)	0.5038 (5)	0.0215 (15)
H5	0.707513	0.207434	0.525019	0.026*
C9	0.8752 (10)	0.5910 (8)	0.8594 (5)	0.0245 (16)
H9	0.802733	0.630763	0.860960	0.029*
C2	0.6042 (9)	1.0464 (8)	0.7107 (5)	0.0195 (14)
C8	0.7562 (9)	0.5225 (8)	0.5231 (5)	0.0223 (15)
H8	0.740253	0.594317	0.558402	0.027*
C1	0.5725 (9)	0.6564 (8)	0.7050 (5)	0.0211 (15)
C10	1.0299 (10)	0.6648 (8)	0.9160 (5)	0.0270 (18)
C7	0.8257 (10)	0.5510 (9)	0.4327 (6)	0.0289 (18)
H7	0.853931	0.641261	0.409642	0.035*
C12	0.9357 (9)	0.4135 (8)	0.8064 (5)	0.0227 (15)
H12	0.908739	0.325149	0.768484	0.027*
C11	1.0847 (10)	0.4878 (9)	0.8641 (6)	0.0271 (17)
H11	1.156693	0.447104	0.864451	0.033*
C13	0.4932 (10)	0.2326 (9)	0.9133 (5)	0.0290 (18)
H13A	0.603756	0.247389	0.930592	0.035*
H13B	0.428430	0.131598	0.889179	0.035*
C14	0.4467 (14)	0.2727 (13)	1.0106 (6)	0.055 (3)
H14A	0.340589	0.266687	0.992360	0.082*
H14B	0.519379	0.369119	1.039883	0.082*
H14C	0.449934	0.208333	1.062348	0.082*

	U11	U22	U33	U12	U13	U23
Au1	0.02856 (16)	0.01474 (13)	0.02017 (13)	0.01414 (12)	0.00870 (11)	0.00444 (10)
Au2	0.02192 (16)	0.02330 (14)	0.01917 (13)	0.00997 (12)	0.00570 (11)	0.00122 (11)
I1	0.0417 (3)	0.0313 (3)	0.0298 (2)	0.0205 (3)	0.0201 (2)	0.0053 (2)
I2	0.0482 (4)	0.0259 (3)	0.0367 (3)	0.0140 (3)	0.0020 (3)	−0.0082 (2)
Fe1	0.0220 (5)	0.0131 (4)	0.0152 (4)	0.0100 (4)	0.0070 (4)	0.0039 (4)
O1	0.026 (3)	0.032 (3)	0.018 (2)	0.018 (3)	0.008 (2)	0.007 (2)
N4	0.026 (3)	0.019 (3)	0.017 (3)	0.011 (3)	0.005 (2)	0.007 (2)
N6	0.033 (4)	0.044 (4)	0.025 (3)	0.024 (4)	0.010 (3)	0.003 (3)
N2	0.025 (4)	0.024 (3)	0.022 (3)	0.017 (3)	0.010 (3)	0.010 (3)
N3	0.021 (3)	0.022 (3)	0.017 (3)	0.012 (3)	0.010 (2)	0.008 (2)
N7	0.034 (4)	0.025 (3)	0.025 (3)	0.018 (3)	0.013 (3)	0.013 (3)
C4	0.027 (4)	0.036 (4)	0.023 (3)	0.025 (4)	0.010 (3)	0.001 (3)
N8	0.024 (4)	0.028 (3)	0.029 (3)	0.011 (3)	0.004 (3)	0.002 (3)
N1	0.023 (3)	0.017 (3)	0.022 (3)	0.010 (3)	0.004 (2)	0.004 (2)
C3	0.019 (4)	0.019 (3)	0.022 (3)	0.011 (3)	0.003 (3)	0.003 (3)
N5	0.025 (3)	0.020 (3)	0.023 (3)	0.011 (3)	0.011 (3)	0.004 (2)
C6	0.019 (4)	0.021 (3)	0.019 (3)	0.007 (3)	0.009 (3)	0.006 (3)
C5	0.025 (4)	0.022 (4)	0.018 (3)	0.009 (3)	0.008 (3)	0.004 (3)
C9	0.031 (4)	0.027 (4)	0.022 (3)	0.017 (4)	0.007 (3)	0.003 (3)
C2	0.023 (4)	0.020 (3)	0.023 (3)	0.014 (3)	0.010 (3)	0.002 (3)
C8	0.029 (4)	0.022 (4)	0.024 (3)	0.016 (3)	0.012 (3)	0.009 (3)
C1	0.024 (4)	0.021 (4)	0.023 (3)	0.013 (3)	0.008 (3)	0.002 (3)
C10	0.041 (5)	0.024 (4)	0.014 (3)	0.010 (4)	0.011 (3)	0.002 (3)
C7	0.040 (5)	0.026 (4)	0.032 (4)	0.018 (4)	0.024 (4)	0.019 (3)
C12	0.026 (4)	0.018 (3)	0.024 (3)	0.009 (3)	0.005 (3)	0.001 (3)
C11	0.030 (4)	0.033 (4)	0.026 (4)	0.021 (4)	0.005 (3)	0.004 (3)
C13	0.030 (5)	0.035 (4)	0.025 (4)	0.015 (4)	0.009 (3)	0.010 (3)
C14	0.060 (7)	0.086 (8)	0.024 (4)	0.032 (7)	0.017 (4)	0.011 (5)

Au1—Au2i	3.163 (5)	N7—C7	1.309 (10)
Au1—C1	1.948 (9)	N8—C10	1.287 (11)
Au1—C2	1.952 (8)	N8—C11	1.329 (10)
Au2—C3	1.970 (8)	N1—C1	1.119 (10)
Au2—C4	1.981 (9)	N5—C2	1.111 (10)
I1—C6	2.071 (8)	C6—C5	1.387 (9)
I2—C10	2.078 (9)	C5—H5	0.9300
Fe1—O1	2.106 (6)	C9—H9	0.9300
Fe1—N1	2.105 (8)	C9—C10	1.384 (11)
Fe1—N2	2.096 (7)	C8—H8	0.9300
Fe1—N3	2.272 (7)	C8—C7	1.404 (10)
Fe1—N4	2.216 (7)	C7—H7	0.9300
Fe1—N5ii	2.096 (8)	C12—H12	0.9300
O1—H1	0.859 (10)	C12—C11	1.350 (11)
O1—C13	1.419 (9)	C11—H11	0.9300
N4—C9	1.323 (10)	C13—H13A	0.9700
N4—C12	1.318 (10)	C13—H13B	0.9700
N6—C4	1.122 (10)	C13—C14	1.486 (11)
N2—C3	1.134 (9)	C14—H14A	0.9600
N3—C5	1.333 (9)	C14—H14B	0.9600
N3—C8	1.302 (9)	C14—H14C	0.9600
N7—C6	1.298 (9)
C2—Au1—Au2i	82.5 (2)	N7—C6—C5	123.1 (7)
C1—Au1—Au2i	97.8 (2)	C5—C6—I1	119.6 (5)
C1—Au1—C2	178.8 (3)	N3—C5—C6	120.9 (7)
C4—Au2—Au1i	101.9 (3)	N3—C5—H5	119.5
C3—Au2—Au1i	78.1 (3)	C6—C5—H5	119.5
C3—Au2—C4	178.9 (3)	N4—C9—H9	119.3
O1—Fe1—N4	92.6 (3)	N4—C9—C10	121.4 (8)
O1—Fe1—N3	177.6 (2)	C10—C9—H9	119.3
N4—Fe1—N3	87.1 (3)	N5—C2—Au1	177.8 (7)
N2—Fe1—O1	94.9 (3)	N3—C8—H8	119.3
N2—Fe1—N4	171.7 (2)	N3—C8—C7	121.5 (7)
N2—Fe1—N3	85.6 (3)	C7—C8—H8	119.3
N2—Fe1—N1	95.8 (3)	N1—C1—Au1	175.8 (7)
N1—Fe1—O1	86.5 (2)	N8—C10—I2	118.1 (6)
N1—Fe1—N4	88.1 (3)	N8—C10—C9	123.0 (7)
N1—Fe1—N3	91.1 (2)	C9—C10—I2	118.9 (6)
N5ii—Fe1—O1	91.3 (2)	N7—C7—C8	122.2 (7)
N5ii—Fe1—N4	89.4 (3)	N7—C7—H7	118.9
N5ii—Fe1—N2	87.0 (3)	C8—C7—H7	118.9
N5ii—Fe1—N3	91.1 (2)	N4—C12—H12	119.7
N5ii—Fe1—N1	176.6 (2)	N4—C12—C11	120.6 (7)
Fe1—O1—H1	122.0 (18)	C11—C12—H12	119.7
C13—O1—Fe1	126.0 (5)	N8—C11—C12	124.5 (8)
C13—O1—H1	105.7 (18)	N8—C11—H11	117.8
C9—N4—Fe1	123.4 (5)	C12—C11—H11	117.8
C12—N4—Fe1	120.4 (5)	O1—C13—H13A	109.3
C12—N4—C9	116.1 (7)	O1—C13—H13B	109.3
C3—N2—Fe1	165.9 (6)	O1—C13—C14	111.7 (8)
C5—N3—Fe1	122.6 (5)	H13A—C13—H13B	107.9
C8—N3—Fe1	120.9 (5)	C14—C13—H13A	109.3
C8—N3—C5	116.4 (6)	C14—C13—H13B	109.3
C6—N7—C7	116.0 (6)	C13—C14—H14A	109.5
N6—C4—Au2	177.2 (7)	C13—C14—H14B	109.5
C10—N8—C11	114.3 (7)	C13—C14—H14C	109.5
C1—N1—Fe1	174.0 (6)	H14A—C14—H14B	109.5
N2—C3—Au2	178.2 (6)	H14A—C14—H14C	109.5
C2—N5—Fe1iii	169.9 (7)	H14B—C14—H14C	109.5
N7—C6—I1	117.3 (5)
I1—C6—C5—N3	178.6 (5)	C6—N7—C7—C8	0.3 (12)
Fe1—O1—C13—C14	158.4 (6)	C5—N3—C8—C7	−0.6 (11)
Fe1—N4—C9—C10	−174.4 (5)	C9—N4—C12—C11	−0.3 (10)
Fe1—N4—C12—C11	175.7 (5)	C8—N3—C5—C6	1.6 (10)
Fe1—N3—C5—C6	177.5 (5)	C10—N8—C11—C12	−0.3 (11)
Fe1—N3—C8—C7	−176.6 (6)	C7—N7—C6—I1	−179.6 (6)
N4—C9—C10—I2	176.5 (5)	C7—N7—C6—C5	0.8 (11)
N4—C9—C10—N8	−2.2 (11)	C12—N4—C9—C10	1.5 (10)
N4—C12—C11—N8	−0.3 (12)	C11—N8—C10—I2	−177.3 (5)
N3—C8—C7—N7	−0.4 (13)	C11—N8—C10—C9	1.5 (10)
N7—C6—C5—N3	−1.8 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N6iv	0.86 (5)	1.98 (5)	2.765 (13)	151 (6)