Two transition metal coordination polymers of the 7,7,8,8-tetra­cyano­quinodimethane dianion (TCNQ^2-)

Each of the two novel title transition metal coordination polymers, namely catena-poly[[bis­{[tris­(2-pyridyl­methyl)amine]cobalt(II)}-[mu]₄-7,7,8,8-tetra­cyano­quinodimethanide(2-)] bis­[7,7,8,8-tetra­cyano­quino­dimethanide(1-)] methanol disolvate], {[Co₂(C₁₂H₄N₄)(C₁₈H₁₈N₄)₂](C₁₂H₄N₄)₂·2CH₃OH}_n, (I), and catena-poly[[[[tris­(2-pyridyl­methyl)amine]iron(II)]-[mu]₂-7,7,8,8-tetra­cyano­quino­dimethanide(2-)] methanol sol­vate], {[Fe(C₁₂H₄N₄)(C₁₈H₁₈N₄)]·CH₃OH}_n, (II), contains [eta]⁴-TPA and cis-bridging TCNQ^2- ligands [TPA is tris­(2-pyridyl­methyl)amine and TCNQ is 7,7,8,8-tetra­cyano­quino­di­methane], but the two compounds adopt entirely different structural motifs. Compound (I) consists of a ribbon coordination polymer featuring [mu]₄-TCNQ^2- radical anion ligands bridging four different octa­hedral Co^II centers. Each formula unit of the polymer is flanked by two uncoordinated TCNQ^- anions and two methanol solvent mol­ecules. All three TCNQ anions have crystallographic inversion symmetry. In (II), the 2₁ symmetry operator generates a one-dimensional zigzag chain of octa­hedral Fe^II centers with [mu]₂-TCNQ^2- bridges. A methanol solvent mol­ecule forms hydrogen bonds to one of the terminal N atoms of the bridging TCNQ^2- dianion. To the best of our knowledge, these are the first examples of one-dimensional coordination polymers forming from cis coordination of two TCNQ ligands to octa­hedral metal centers.

S1. Comment

The ability of 7,7,8,8-tetracyanoquinodimethane anions (TCNQ^n-, n = 1 or 2) to coordinate to transition metal fragments and to act as bridging σ-donor ligands (µ₂, µ₃, or µ₄) can be exploited to construct extended molecular assemblies. Interest in this area has been spurred, in part, by several observations of long-range magnetic order in TCNQ^- bridged structures involving V, Mn, Fe, Co, and Ni ions (Vickers et al., 2004, 2005; Clérac et al., 2003). A review of this area includes descriptions of the various modes of coordination, as well as compilations of IR, X-ray, and electrochemical data (Kaim & Moscherosch, 1994).

For the case when exactly two TCNQ ligands coordinate to an octahedral metal center, a search of the Cambridge Structural Database (Version?; Allen, 2002) using CONQUEST (Macrae et al., 2006) indicates a preference for trans-TCNQ coordination to the metal center (Kunkeler et al., 1996; Cornelissen et al., 1992; Ballester et al., 1994; Oshio et al., 1995; Azcondo et al., 1996; Sugiura et al., 1999; Choi & Suh, 2003; Ballester, Gil et al., 1997; Ballester, Gutiérrez et al., 1997; Ballester et al., 2002, 2004). In this context, trans and cis refer to the relative geometry of two ligands about a single metal center, and syn, anti and gem describe the three possible µ₂-bridging geometries of the TCNQ ligand. Additionally, there are examples of four TCNQ ligands or TCNQ–TCNQ σ-dimers coordinated equatorially to an octahedral metal center to form M(L₂)(TCNQ)₄ or ML₂(TCNQ)₂(TCNQ–TCNQ)₂ (Zhao et al., 1999; Shimomura et al., 2006). These complexes form coordination polymers, three via µ₂-TCNQ bridging (two gem and one syn) and one via µ₄-TCNQ bridging. To the best of our knowledge, there is only one example of cis-geometry when only two TCNQ ligands are coordinated to an octahedral metal center (Ballester, Gutiérrez et al., 1997) and no examples that give rise to pseudo-one-dimensional coordination polymers, as occur in the title compounds, (I) and (II).

The µ₄-bridging mode is also relatively rare, though not unprecedented. The discrete complex [(µ₄-TCNQ){fac-Re(CO)₃(bpy)}₄]⁴⁺ has been formulated to contain neutral TCNQ (Hartmann et al., 2001). The compounds [{M₂(O₂CCF₃)₄}₂(µ₄-TCNQ).3(solvate)]_∞ (M = Rh, Ru or Mo) are reported to contain a partially reduced, but formally neutral, bridging TCNQ (Miyasaka et al., 2000, 2006; Campana et al., 1996). The ends of each {M₂(O₂CCF₃)₄}₂ `barrel' are coordinated by two TCNQ ligands to give either a one-dimensional chain (Mo) or two-dimensional sheets (Rh, Ru). In contrast, [Ag(µ₄-TCNQ)]_∞ (Shields, 1985) and a Cu analog (Heintz et al., 1999) possess the ligand in the radical anionic state and form three-dimensional structures comprised of two interpenetrating networks. Shimomura et al. (2006) have reported a porous framework consisting of Zn^II ions bridged by µ₄-TCNQ^2- to form corrugated sheets that are connected by 4,4'-bipyridine pillars. Most relevant to the present work, [Mn^III(salen)(µ₄-TCNQ)_0.5][Mn^III(salen)(µ₂-TCNQ)_0.5(CH₃OH)] contains two crystallographically independent TCNQs, one anti-µ₂-TCNQ^2- and one µ₄-bridging (Oshio et al., 1995).

Our original goal was to exploit the bridging propensity and radical property of TCNQ^- to prepare discrete magnetic molecular squares with octahedral transition metal complexes as the corners and radical anions as the edges. One reason for this line of research was to prepare nanoscale fragments of the above-mentioned magnetically ordered phases. To achieve this, we chose the tripodal tetradentate ligand tris(2-pyridylmethyl)amine (TPA) to cap four of the available coordination sites, leaving two cis sites on each metal center open for the TCNQ^- binding necessary to close the square. Oshio et al. (1993) have previously reported an Mn(TPA)(TCNQ)(CH₃OH) complex in which the N_TCNQ—Mn—O angle is 90.5°, seemingly ideal for our goal of coordinating two cis-TCNQ anions to form a corner building block.

Unfortunately, our first efforts in this area have not yielded the desired squares. Instead, we have discovered that LiTCNQ reacts with Fe^IITPA and Co^IITPA complexes to give magnetically unremarkable but structurally interesting coordination polymers. In each case, a known reaction occurs involving disproportionation of two TCNQ radical anions to yield the diamagnetic TCNQ^2- (Grossel et al., 2000). Although the goal of synthesizing molecular squares was not met, it is gratifying to see two TCNQ^2- dianions coordinated cis to each metal center, as would be required for square construction.

The asymmetric unit of (I) comprises one Co(TPA)(TCNQ)_0.5 formula unit, two uncoordinated 0.5TCNQ^- located on inversion centers, and one methanol solvate molecule (Fig. 1). The Co^II ion adopts a distorted octahedral geometry, with the TPA ligand occupying four coordination sites and two cis-coordinated TCNQ^2- ligands occupying the remaining two sites. The Co—N bond lengths are all within expected ranges (Table 1) (Allen, 2002; Macrae et al., 2006). The coordinated TCNQ^2- ligand adopts a µ₄-bridging mode to four different Co atoms, forming an infinite ribbon (Fig. 2). The two non-bonded TCNQ^- anions and the methanol solvate molecule flank the ribbon on all sides. One of these non-bonded TCNQ^- anions is nearly coplanar with the µ₄-TCNQ^2- ligand (dihedral angle 2.0°; Fig. 3, TCNQ^- A [Looks more like B?]) and the other TCNQ^- anion is nearly coplanar with the pyridyl group of the TPA ligand (dihedral angle 7.3°; Fig. 3, TCNQ^- B [Looks more like A?]). The hydroxide group of the methanol is hydrogen-bonded to an N atom of a non-bonded TCNQ^- (Table 2). For charge balance, the three TCNQ entities in the formula unit must have a total charge of -4. The formal charges of -2 for the µ₄-TCNQ and -1 for the two uncoordinated TCNQs are assigned based on the C—C bond lengths observed in the crystal structure (see below). [See query below regarding anion designators]

The asymmetric unit of (II) comprises one Fe(TPA)(TCNQ) unit and one methanol solvate molecule (Fig. 4). The Fe^II ion adopts a distorted octahedral geometry, with a tetradentate TPA ligand and two cis-coordinated TCNQ^- [Should this be TCNQ^2-?] coordinated to the metal. The Fe—N bond lengths (Table 3) are typical of other Fe^II low-spin TPA complexes (Allen, 2002; Macrae et al., 2006). Each µ₂-TCNQ^2- ligand adopts an anti bridging mode to form a zigzag chain propagating along the crystallographic b axis (Fig. 5). The infinite chain is generated by a 2₁ screw axis at (1/2, y, 1/4) (origin at 1) and neighboring chains are related by inversion symmetry. The hydroxy group of the methanol solvate molecule is hydrogen-bonded to a free N atom of the TCNQ^- [Should this be TCNQ^2-?] (Fig. 5; Table 4).

X-ray crystallography can be used to confirm the oxidation states of the TCNQ species in these materials. Successive reduction of TCNQ leads to a progressive and characteristic increase in benzoid character in the six-membered ring and a lengthening of the exocyclic C—C bonds (Fig. 6) (Zhao et al., 1996; Miyasaka et al., 2000). Table 5 lists selected intramolecular bond distances for the TCNQ anions in complexes (I) and (II), as well as typical values for TCNQ, TCNQ^- and TCNQ^2-. In (I), there are three unique TCNQ anions, A, B and C. The bond lengths in TCNQ A, which is coordinated to Co^II in a µ₄-bridging mode, are consistent with TCNQ^2-. The bond lengths in the uncoordinated anions B and C are consistent with TCNQ^-. These oxidation state assignments give a total charge of -4 to balance the +2 charge of the two Co^II ions and give an empirical formula of [Co^II₂(TPA)₂(µ₄-TCNQ^2-)][TCNQ^-]₂.CH₃OH. In (II), the bond lengths in the one crystallographically independent TCNQ anion indicate a charge of -2, which balances the +2 charge of the Fe^II cation and gives an empirical formula of [Fe^II(TPA)(µ₂-TCNQ^2-)].CH₃OH. [NB The anion designators A, B, C in this paragraph and in Table 5 (A = TCNQ^2-) do not match those given two paragraphs above, or those in Fig. 3. Please clarify and render consistent]

S2. Experimental

Hazard warning: Perchlorate salts are potentially explosive and should be used in small amounts and handled with care. Preparations of air-sensitive compounds were carried out in a nitrogen-filled Vacuum Atmospheres glove box using standard Schlenk techniques. Reagents were used as received except as noted below. Solvents were distilled from the appropriate drying agent under nitrogen: dichloromethane and acetonitrile were distilled from P₂O₅; diethyl ether was distilled from Na/benzophenone; methanol was distilled from Na. All solvents were degassed with glove-box N₂ prior to use. Tris(2-pyridylmethyl)amine and [Fe(TPA)(CH₃CN)₂](ClO₄)₂ were prepared according to literature procedures (Karlin et al., 1982; Zang et al., 1993, 1997). LiTCNQ was prepared by adding a boiling solution of LiI (400 mg, 3 mmol) in acetonitrile (20 ml) to a boiling solution of TCNQ (210 mg, 1.0 mmol) in acetonitrile (200 ml). A dark-purple precipitate was collected by suction (Bozio et al., 1975). IR spectra were measured using a MIDAC M-series FT–IR spectrometer equipped with an ATR attachment. Elemental analyses were performed by Desert Analytics, Tucson, Arizona.

The preparation of [Co₂(TPA)₂(µ₄-TCNQ^2-)][TCNQ^-]₂.CH₃OH, (I), was carried out as follows. To a mixture of Co(NO₃)₂.6H₂O (29.1 mg, 0.100 mmol) and TPA (29.0 mg, 0.100 mmol) in methanol (4 ml) was added LiTCNQ (42.2 mg, 0.200 mmol) in methanol (3 ml). The mixture was stirred for 3 h at room temperature, and the blue–black precipitate that formed was filtered off washed with methanol and ether, and dried in vacuo. Dark-green plates of (I) were crystallized from methanol–diethyl ether (Solvent ratio?) by vapor diffusion at room temperature (yield 7.0 mg, 10%). Analysis, calculated for C₃₇H₂₈CoN₁₀O: C 64.63, H 4.10, N 20.34%; found: C 64.77, H 3.89, N 20.44%. Spectroscopic analysis: IR (Medium?, ν, cm^-1): 2188, 2176, 2140, 2059, 824.

The preparation of [Fe(TPA)(µ₂-TCNQ)].CH₃OH, (II), was carried out as follows. The red solid [Fe(TPA)(CH₃CN)₂](ClO₄)₂ (62.7 mg, 0.100 mmol) was dissolved in CH₂Cl₂ (6 ml) to yield a yellow solution. A green solution of LiTCNQ (42.2 mg, 0.200 mmol) in CH₃OH (6 ml) was added, leading to a deep-green solution. The solution was stirred for 3 h at room temperature and a dark-blue solid was filtered off, washed with methanol and ether, and dried in vacuo. Dark-orange bricks of (II) were crystallized from methanol–diethyl ether (Solvent ratio?) by vapor diffusion at room temperature (yield 6.2 mg, 11%). Analysis, calculated for C₃₁H₂₆FeN₈O: C 63.93, H 4.50, N 19.24%; found: C 64.01, H 3.50, N 20.50%. Spectroscopic analysis: IR (Medium?, ν, cm^-1): 2187, 2180, 2155, 2106, 822.

S3. Refinement

H atoms were treated using a riding model, with C—H_aromatic = 0.95 Å and U_iso(H) = 1.2U_eq(C), and C—H_alkyl = 0.98–0.99 Å and U_iso(H) = 1.5U_eq(C).

Computing details

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007). Program(s) used to solve structure: SHELXS86 (Sheldrick, 2008) and WinGX (Farrugia, 1999) for (I); SHELXS97 (Sheldrick, 2008) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL NT (Sheldrick, 2008); software used to prepare material for publication: SHELXTL NT (Sheldrick, 2008).

Figures

	Fig. 1. A view of the asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. [Symmetry codes: (i) -x, -y + 1, -z; (ii) -x + 1, -y + 1, -z + 1; (iii) -x, -y + 3, -z + 1; (iv) -x, -y + 2, -z + 1.]
	Fig. 2. A view of the structure of (I) down the a* direction, showing the one-dimensional ribbon architecture. The methanol solvate molecules and uncoordinated TCNQ^- anions have been omitted for clarity.
	Fig. 3. A view of (I) down the b axis, illustrating the hydrogen bonding (dotted lines) with the methanol molecules and the packing of the uncoordinated TCNQ^- anions. [Please see query in text regarding anion designators]
	Fig. 4. A view of the asymmetric unit of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probabilitylevel and H atoms have been omitted for clarity. [Symmetry codes: (i) -x + 1, y - 1/2, -z + 1/2; (ii) -x + 1, y + 1/2, -z + 1/2.]
	Fig. 5. A view of (II) down the c axis, showing the one-dimensional zigzag chain architecture and the hydrogen bonding (dotted lines) with the methanol molecules.
	Fig. 6. The bond labeling used in Table 5.

(I) catena-poly[[bis{[tris(2-pyridylmethyl)amine]cobalt(II)}- µ₄-7,7',8,8'-tetracyanoquinodimethanide(2-)] bis[7,7',8,8'-tetracyanoquinodimethanide(1-)] methanol disolvate]

Crystal data

[Co2(C12H4N4)(C18H18N4)2](C12H4N4)2·2CH4O	Z = 1
Mr = 1375.24	F(000) = 710
Triclinic, P1	Dx = 1.420 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.954 (2) Å	Cell parameters from 1930 reflections
b = 11.371 (3) Å	θ = 2.0–18.9°
c = 17.066 (4) Å	µ = 0.58 mm^−1
α = 73.45 (2)°	T = 100 K
β = 85.55 (2)°	Plate, dark green
γ = 74.93 (2)°	0.14 × 0.11 × 0.03 mm
V = 1608.3 (7) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer	3386 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.3°, θmin = 3.8°
Detector resolution: 16.0355 pixels mm^-1	h = −10→9
ϕ and ω scans	k = −13→11
11614 measured reflections	l = −20→20
5716 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0505P)^2] where P = (Fo^2 + 2Fc^2)/3
5716 reflections	(Δ/σ)max = 0.001
444 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

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. The chosen crystals of (I) and (II) were centered on the goniometer of an Oxford Diffraction Xcalibur S diffractometer. The data collection routine, unit cell refinement, and data processing were carried out with the program CrysAlisPro (Oxford Diffraction, 2007)

The Laue symmetry of (I) was consistent with the triclinic space group P1. The structure was solved by direct methods using SHELXS86 (Sheldrick, 2008) via the WinGX graphical interface (Farrugia, 1999) and refined using SHELXTL NT (Sheldrick, 2008). The asymmetric unit of the structure comprises one Co atom, one TPA molecule, three half-TCNQ molecules, and one methanol solvate. The final refinement model involved anisotropic displacement parameters for all non-H atoms and a riding model for the H atoms.

For compound (II), the Laue symmetry and systematic absences were consistent with the monoclinic space group P2₁/c. The structure was solved by direct methods and refined using SHELXTL NT. The asymmetric unit of the structure comprises one crystallographically independent Fe(TPA)(TCNQ) formula unit and one methanol solvate. The final refinement model involved anisotropic displacement parameters for all non-H atoms and a riding model for the H atoms.

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
Co1	0.20784 (5)	0.87358 (4)	0.68868 (3)	0.02379 (15)
N1	0.2500 (3)	0.9471 (2)	0.78647 (16)	0.0255 (7)
N2	0.4177 (3)	0.9272 (3)	0.65006 (17)	0.0306 (7)
N3	0.3405 (3)	0.7030 (2)	0.76702 (16)	0.0239 (6)
N4	0.0174 (3)	0.8473 (2)	0.76802 (16)	0.0247 (6)
N5	0.0826 (3)	1.0534 (2)	0.61974 (17)	0.0257 (7)
N6	−0.1746 (3)	1.2062 (2)	0.39804 (17)	0.0271 (7)
N7	0.2256 (4)	0.7811 (3)	0.2649 (2)	0.0602 (10)
N8	0.2310 (4)	0.3843 (3)	0.3167 (2)	0.0540 (9)
N9	0.1751 (4)	0.8205 (3)	0.05181 (19)	0.0429 (8)
N10	−0.1577 (4)	0.6569 (3)	0.2295 (2)	0.0447 (8)
C1	0.3325 (4)	1.0465 (3)	0.7486 (2)	0.0365 (9)
H1A	0.3806	1.0673	0.7916	0.044*
H1B	0.2587	1.1243	0.7179	0.044*
C2	0.4555 (4)	0.9991 (3)	0.6916 (2)	0.0339 (9)
C3	0.5972 (5)	1.0314 (4)	0.6789 (3)	0.0530 (12)
H3	0.6232	1.0813	0.7094	0.064*
C4	0.6986 (5)	0.9902 (5)	0.6221 (3)	0.0648 (15)
H4	0.7949	1.0124	0.6121	0.078*
C5	0.6594 (5)	0.9164 (5)	0.5798 (3)	0.0619 (14)
H5	0.7280	0.8868	0.5403	0.074*
C6	0.5186 (4)	0.8861 (4)	0.5957 (2)	0.0439 (10)
H6	0.4922	0.8340	0.5669	0.053*
C7	0.3458 (4)	0.8432 (3)	0.8514 (2)	0.0304 (8)
H7A	0.2869	0.8351	0.9034	0.036*
H7B	0.4404	0.8682	0.8591	0.036*
C8	0.3932 (3)	0.7154 (3)	0.8348 (2)	0.0239 (8)
C9	0.4869 (4)	0.6146 (3)	0.8900 (2)	0.0332 (9)
H9	0.5249	0.6262	0.9370	0.040*
C10	0.5241 (4)	0.4972 (3)	0.8758 (2)	0.0375 (10)
H10	0.5871	0.4263	0.9132	0.045*
C11	0.4690 (4)	0.4835 (3)	0.8068 (2)	0.0358 (9)
H11	0.4928	0.4032	0.7961	0.043*
C12	0.3788 (4)	0.5884 (3)	0.7534 (2)	0.0296 (8)
H12	0.3424	0.5792	0.7052	0.036*
C13	0.0963 (4)	0.9988 (3)	0.8189 (2)	0.0325 (9)
H13A	0.0479	1.0827	0.7819	0.039*
H13B	0.1082	1.0100	0.8733	0.039*
C14	−0.0057 (4)	0.9101 (3)	0.8259 (2)	0.0278 (8)
C15	−0.1190 (4)	0.8950 (3)	0.8857 (2)	0.0355 (9)
H15	−0.1330	0.9394	0.9262	0.043*
C16	−0.2100 (4)	0.8156 (4)	0.8855 (2)	0.0398 (10)
H16	−0.2881	0.8042	0.9259	0.048*
C17	−0.1873 (4)	0.7523 (4)	0.8263 (2)	0.0384 (10)
H17	−0.2502	0.6973	0.8250	0.046*
C18	−0.0717 (4)	0.7697 (3)	0.7686 (2)	0.0305 (8)
H18	−0.0554	0.7249	0.7282	0.037*
C19	0.0781 (4)	1.5150 (3)	0.56135 (19)	0.0254 (8)
H19	0.1324	1.5245	0.6039	0.030*
C20	0.0595 (4)	1.3975 (3)	0.56439 (19)	0.0228 (8)
H20	0.1009	1.3273	0.6093	0.027*
C21	−0.0179 (4)	1.3789 (3)	0.50363 (19)	0.0223 (7)
C22	−0.0370 (4)	1.2525 (3)	0.50693 (19)	0.0242 (8)
C23	0.0284 (4)	1.1444 (3)	0.5697 (2)	0.0218 (7)
C24	−0.1122 (4)	1.2293 (3)	0.4470 (2)	0.0246 (8)
C25	0.4473 (4)	0.4053 (3)	0.4844 (2)	0.0375 (9)
H25	0.4106	0.3399	0.4741	0.045*
C26	0.4047 (4)	0.5287 (3)	0.4305 (2)	0.0344 (9)
C27	0.4613 (4)	0.6228 (3)	0.4496 (2)	0.0376 (9)
H27	0.4346	0.7073	0.4155	0.045*
C28	0.3111 (4)	0.5569 (3)	0.3610 (2)	0.0364 (9)
C29	0.2624 (4)	0.6803 (4)	0.3085 (3)	0.0417 (10)
C30	0.2652 (4)	0.4610 (4)	0.3379 (2)	0.0397 (10)
C31	0.1037 (4)	0.5759 (3)	−0.0188 (2)	0.0300 (8)
H31	0.1748	0.6279	−0.0320	0.036*
C32	0.0048 (4)	0.5800 (3)	0.0500 (2)	0.0273 (8)
C33	−0.0986 (4)	0.5012 (3)	0.0663 (2)	0.0308 (8)
H33	−0.1668	0.5018	0.1117	0.037*
C34	0.0084 (4)	0.6611 (3)	0.0991 (2)	0.0277 (8)
C35	0.0995 (4)	0.7496 (3)	0.0755 (2)	0.0328 (9)
C36	−0.0819 (4)	0.6593 (3)	0.1715 (2)	0.0331 (9)
O1	0.4918 (4)	0.8168 (4)	0.0244 (2)	0.0828 (10)
H1	0.3959	0.8258	0.0308	0.124*
C37	0.5486 (6)	0.8571 (4)	0.0831 (3)	0.0683 (14)
H37A	0.6197	0.9096	0.0572	0.102*
H37B	0.6038	0.7833	0.1251	0.102*
H37C	0.4624	0.9068	0.1083	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0212 (3)	0.0230 (3)	0.0266 (3)	−0.00421 (19)	−0.00074 (19)	−0.0070 (2)
N1	0.0255 (16)	0.0242 (15)	0.0270 (16)	−0.0099 (13)	−0.0008 (12)	−0.0039 (13)
N2	0.0233 (16)	0.0316 (17)	0.0321 (18)	−0.0043 (13)	0.0014 (13)	−0.0037 (14)
N3	0.0205 (15)	0.0227 (16)	0.0283 (17)	−0.0060 (12)	0.0045 (12)	−0.0074 (13)
N4	0.0247 (16)	0.0218 (15)	0.0263 (17)	−0.0053 (13)	−0.0025 (12)	−0.0047 (13)
N5	0.0248 (16)	0.0210 (16)	0.0296 (17)	−0.0049 (13)	−0.0028 (13)	−0.0040 (14)
N6	0.0312 (17)	0.0210 (15)	0.0277 (17)	−0.0042 (13)	−0.0044 (13)	−0.0052 (13)
N7	0.062 (3)	0.049 (2)	0.066 (3)	0.005 (2)	−0.026 (2)	−0.023 (2)
N8	0.049 (2)	0.058 (2)	0.064 (3)	−0.0145 (19)	−0.0063 (18)	−0.028 (2)
N9	0.044 (2)	0.044 (2)	0.049 (2)	−0.0149 (17)	0.0094 (16)	−0.0257 (17)
N10	0.047 (2)	0.048 (2)	0.038 (2)	−0.0056 (16)	0.0043 (17)	−0.0167 (17)
C1	0.043 (2)	0.030 (2)	0.038 (2)	−0.0155 (18)	−0.0078 (18)	−0.0044 (18)
C2	0.030 (2)	0.034 (2)	0.034 (2)	−0.0137 (17)	−0.0106 (17)	0.0049 (18)
C3	0.047 (3)	0.055 (3)	0.050 (3)	−0.032 (2)	−0.018 (2)	0.019 (2)
C4	0.026 (2)	0.083 (4)	0.059 (3)	−0.022 (2)	−0.005 (2)	0.030 (3)
C5	0.026 (2)	0.078 (3)	0.057 (3)	−0.006 (2)	0.012 (2)	0.011 (3)
C6	0.033 (2)	0.045 (2)	0.040 (2)	−0.0030 (19)	0.0066 (19)	0.000 (2)
C7	0.030 (2)	0.036 (2)	0.025 (2)	−0.0092 (17)	−0.0055 (15)	−0.0055 (16)
C8	0.0150 (17)	0.0278 (19)	0.027 (2)	−0.0072 (15)	0.0026 (15)	−0.0029 (16)
C9	0.0224 (19)	0.043 (2)	0.030 (2)	−0.0089 (17)	−0.0002 (16)	−0.0018 (18)
C10	0.026 (2)	0.034 (2)	0.036 (2)	0.0007 (17)	0.0046 (17)	0.0077 (18)
C11	0.032 (2)	0.0205 (19)	0.045 (2)	0.0017 (16)	0.0121 (18)	−0.0032 (17)
C12	0.029 (2)	0.029 (2)	0.032 (2)	−0.0067 (16)	0.0089 (16)	−0.0122 (17)
C13	0.036 (2)	0.028 (2)	0.030 (2)	−0.0004 (17)	0.0003 (16)	−0.0096 (16)
C14	0.027 (2)	0.0261 (19)	0.026 (2)	−0.0006 (16)	−0.0036 (16)	−0.0054 (16)
C15	0.031 (2)	0.039 (2)	0.031 (2)	−0.0005 (18)	0.0048 (17)	−0.0099 (18)
C16	0.023 (2)	0.052 (3)	0.037 (2)	−0.0048 (19)	0.0062 (17)	−0.006 (2)
C17	0.025 (2)	0.049 (2)	0.038 (2)	−0.0157 (18)	0.0016 (17)	−0.001 (2)
C18	0.027 (2)	0.031 (2)	0.032 (2)	−0.0074 (17)	−0.0032 (16)	−0.0064 (17)
C19	0.0243 (18)	0.029 (2)	0.0231 (19)	−0.0046 (15)	−0.0006 (15)	−0.0091 (16)
C20	0.0251 (19)	0.0195 (18)	0.0217 (19)	−0.0023 (15)	−0.0023 (15)	−0.0046 (15)
C21	0.0215 (18)	0.0237 (18)	0.0195 (18)	−0.0029 (14)	0.0045 (14)	−0.0062 (15)
C22	0.0259 (19)	0.0226 (19)	0.0230 (19)	−0.0045 (15)	0.0017 (15)	−0.0062 (15)
C23	0.0214 (18)	0.025 (2)	0.023 (2)	−0.0098 (16)	0.0032 (15)	−0.0114 (16)
C24	0.0241 (19)	0.0147 (18)	0.028 (2)	−0.0003 (14)	0.0035 (16)	0.0000 (15)
C25	0.035 (2)	0.037 (2)	0.047 (3)	−0.0100 (18)	0.0011 (19)	−0.020 (2)
C26	0.028 (2)	0.034 (2)	0.040 (2)	−0.0010 (17)	0.0055 (17)	−0.0166 (19)
C27	0.039 (2)	0.031 (2)	0.042 (2)	−0.0049 (18)	−0.0024 (19)	−0.0133 (18)
C28	0.028 (2)	0.036 (2)	0.047 (3)	−0.0021 (17)	−0.0003 (18)	−0.0195 (19)
C29	0.035 (2)	0.042 (3)	0.050 (3)	−0.003 (2)	−0.002 (2)	−0.022 (2)
C30	0.028 (2)	0.046 (3)	0.044 (3)	−0.0048 (19)	0.0012 (18)	−0.016 (2)
C31	0.026 (2)	0.032 (2)	0.032 (2)	−0.0064 (16)	0.0042 (16)	−0.0102 (17)
C32	0.0222 (19)	0.0262 (19)	0.027 (2)	0.0022 (16)	−0.0016 (15)	−0.0045 (16)
C33	0.0260 (19)	0.034 (2)	0.028 (2)	−0.0038 (16)	0.0080 (15)	−0.0067 (17)
C34	0.026 (2)	0.027 (2)	0.031 (2)	−0.0068 (16)	0.0041 (16)	−0.0096 (16)
C35	0.035 (2)	0.033 (2)	0.028 (2)	0.0024 (19)	0.0004 (17)	−0.0136 (18)
C36	0.036 (2)	0.030 (2)	0.033 (2)	−0.0048 (17)	−0.0018 (19)	−0.0123 (18)
O1	0.063 (2)	0.106 (3)	0.084 (3)	−0.024 (2)	0.006 (2)	−0.030 (2)
C37	0.085 (4)	0.070 (3)	0.057 (3)	−0.029 (3)	−0.038 (3)	−0.010 (3)

Geometric parameters (Å, º)

Co1—N6^i	2.019 (3)	C13—C14	1.503 (4)
Co1—N5	2.113 (3)	C13—H13A	0.99
Co1—N4	2.122 (3)	C13—H13B	0.99
Co1—N2	2.124 (3)	C14—C15	1.389 (5)
Co1—N3	2.129 (3)	C15—C16	1.365 (5)
Co1—N1	2.164 (3)	C15—H15	0.95
N1—C1	1.478 (4)	C16—C17	1.373 (5)
N1—C13	1.481 (4)	C16—H16	0.95
N1—C7	1.494 (4)	C17—C18	1.385 (5)
N2—C6	1.339 (4)	C17—H17	0.95
N2—C2	1.340 (4)	C18—H18	0.95
N3—C8	1.339 (4)	C19—C20	1.375 (4)
N3—C12	1.340 (4)	C19—C21^ii	1.403 (4)
N4—C18	1.332 (4)	C19—H19	0.95
N4—C14	1.349 (4)	C20—C21	1.383 (4)
N5—C23	1.156 (4)	C20—H20	0.95
N6—C24	1.164 (4)	C21—C19^ii	1.403 (4)
N6—Co1^i	2.019 (3)	C21—C22	1.476 (4)
N7—C29	1.154 (5)	C22—C24	1.386 (5)
N8—C30	1.149 (4)	C22—C23	1.405 (4)
N9—C35	1.152 (4)	C25—C27^iii	1.357 (5)
N10—C36	1.153 (4)	C25—C26	1.414 (5)
C1—C2	1.509 (5)	C25—H25	0.95
C1—H1A	0.99	C26—C28	1.417 (5)
C1—H1B	0.99	C26—C27	1.420 (5)
C2—C3	1.394 (5)	C27—C25^iii	1.357 (5)
C3—C4	1.374 (6)	C27—H27	0.95
C3—H3	0.95	C28—C29	1.410 (5)
C4—C5	1.372 (6)	C28—C30	1.420 (5)
C4—H4	0.95	C31—C33^iv	1.363 (5)
C5—C6	1.379 (5)	C31—C32	1.418 (4)
C5—H5	0.95	C31—H31	0.95
C6—H6	0.95	C32—C33	1.410 (4)
C7—C8	1.506 (4)	C32—C34	1.419 (4)
C7—H7A	0.99	C33—C31^iv	1.363 (5)
C7—H7B	0.99	C33—H33	0.95
C8—C9	1.384 (4)	C34—C35	1.409 (5)
C9—C10	1.376 (5)	C34—C36	1.422 (5)
C9—H9	0.95	O1—C37	1.390 (5)
C10—C11	1.373 (5)	O1—H1	0.84
C10—H10	0.95	C37—H37A	0.98
C11—C12	1.378 (5)	C37—H37B	0.98
C11—H11	0.95	C37—H37C	0.98
C12—H12	0.95
N6^i—Co1—N5	91.03 (11)	N4—C14—C13	115.1 (3)
N6^i—Co1—N4	101.59 (11)	C15—C14—C13	123.3 (3)
N5—Co1—N4	92.35 (10)	C16—C15—C14	119.3 (3)
N6^i—Co1—N2	102.31 (12)	C16—C15—H15	120.4
N5—Co1—N2	89.58 (10)	C14—C15—H15	120.4
N4—Co1—N2	155.98 (11)	C15—C16—C17	119.3 (3)
N6^i—Co1—N3	95.29 (11)	C15—C16—C31^v	84.7 (2)
N5—Co1—N3	173.62 (11)	C17—C16—C31^v	84.4 (2)
N4—Co1—N3	87.24 (10)	C15—C16—H16	120.4
N2—Co1—N3	88.23 (10)	C17—C16—H16	120.4
N6^i—Co1—N1	176.35 (11)	C31^v—C16—H16	100.8
N5—Co1—N1	92.60 (10)	C16—C17—C18	119.2 (3)
N4—Co1—N1	77.85 (10)	C16—C17—C33^vi	94.7 (2)
N2—Co1—N1	78.15 (11)	C18—C17—C33^vi	84.1 (2)
N3—Co1—N1	81.09 (10)	C16—C17—H17	120.4
C1—N1—C13	112.3 (3)	C18—C17—H17	120.4
C1—N1—C7	111.1 (3)	C33^vi—C17—H17	91.1
C13—N1—C7	111.0 (2)	N4—C18—C17	122.1 (3)
C1—N1—Co1	105.9 (2)	N4—C18—H18	119.0
C13—N1—Co1	106.39 (19)	C17—C18—H18	119.0
C7—N1—Co1	109.89 (19)	C20—C19—C21^ii	121.0 (3)
C6—N2—C2	119.0 (3)	C20—C19—C30^i	82.6 (2)
C6—N2—Co1	126.3 (3)	C21^ii—C19—C30^i	92.7 (2)
C2—N2—Co1	114.4 (2)	C20—C19—H19	119.5
C8—N3—C12	118.5 (3)	C21^ii—C19—H19	119.5
C8—N3—Co1	115.1 (2)	C30^i—C19—H19	94.8
C12—N3—Co1	126.4 (2)	C19—C20—C21	121.6 (3)
C18—N4—C14	118.6 (3)	C19—C20—C28^i	96.7 (2)
C18—N4—Co1	126.1 (2)	C21—C20—C28^i	78.67 (19)
C14—N4—Co1	115.1 (2)	C19—C20—C30^i	74.44 (19)
C23—N5—Co1	167.1 (3)	C21—C20—C30^i	97.3 (2)
C24—N6—Co1^i	159.7 (3)	C19—C20—H20	119.2
N1—C1—C2	109.1 (3)	C21—C20—H20	119.2
N1—C1—H1A	109.9	C28^i—C20—H20	94.7
C2—C1—H1A	109.9	C30^i—C20—H20	98.3
N1—C1—H1B	109.9	C20—C21—C19^ii	117.4 (3)
C2—C1—H1B	109.9	C20—C21—C22	121.4 (3)
H1A—C1—H1B	108.3	C19^ii—C21—C22	121.2 (3)
N2—C2—C3	121.2 (4)	C20—C21—C28^i	78.05 (19)
N2—C2—C1	115.5 (3)	C19^ii—C21—C28^i	96.0 (2)
C3—C2—C1	123.2 (4)	C22—C21—C28^i	95.67 (19)
C4—C3—C2	119.3 (4)	C24—C22—C23	114.8 (3)
C4—C3—H3	120.3	C24—C22—C21	123.3 (3)
C2—C3—H3	120.3	C23—C22—C21	121.8 (3)
C5—C4—C3	119.3 (4)	N5—C23—C22	177.9 (3)
C5—C4—H4	120.4	N6—C24—C22	178.0 (3)
C3—C4—H4	120.4	C27^iii—C25—C26	122.2 (3)
C4—C5—C6	118.8 (4)	C27^iii—C25—H25	118.9
C4—C5—H5	120.6	C26—C25—H25	118.9
C6—C5—H5	120.6	C25—C26—C28	121.9 (3)
N2—C6—C5	122.4 (4)	C25—C26—C27	116.3 (3)
N2—C6—H6	118.8	C28—C26—C27	121.7 (3)
C5—C6—H6	118.8	C25^iii—C27—C26	121.4 (3)
N1—C7—C8	115.5 (3)	C25^iii—C27—H27	119.3
N1—C7—H7A	108.4	C26—C27—H27	119.3
C8—C7—H7A	108.4	C29—C28—C26	122.7 (3)
N1—C7—H7B	108.4	C29—C28—C30	115.5 (3)
C8—C7—H7B	108.4	C26—C28—C30	121.8 (3)
H7A—C7—H7B	107.5	N7—C29—C28	178.6 (4)
N3—C8—C9	122.1 (3)	N8—C30—C28	177.6 (4)
N3—C8—C7	118.3 (3)	C33^iv—C31—C32	121.2 (3)
C9—C8—C7	119.6 (3)	C33^iv—C31—H31	119.4
C10—C9—C8	118.9 (3)	C32—C31—H31	119.4
C10—C9—H9	120.6	C33—C32—C31	116.8 (3)
C8—C9—H9	120.6	C33—C32—C34	121.8 (3)
C11—C10—C9	119.3 (3)	C31—C32—C34	121.5 (3)
C11—C10—H10	120.4	C31^iv—C33—C32	122.0 (3)
C9—C10—H10	120.4	C31^iv—C33—H33	119.0
C10—C11—C12	118.9 (3)	C32—C33—H33	119.0
C10—C11—H11	120.5	C35—C34—C32	120.3 (3)
C12—C11—H11	120.5	C35—C34—C36	117.7 (3)
N3—C12—C11	122.3 (3)	C32—C34—C36	122.0 (3)
N3—C12—H12	118.8	N9—C35—C34	175.9 (4)
C11—C12—H12	118.8	N10—C36—C34	178.4 (4)
N1—C13—C14	109.9 (3)	C37—O1—H1	109.5
N1—C13—H13A	109.7	O1—C37—H37A	109.5
C14—C13—H13A	109.7	O1—C37—H37B	109.5
N1—C13—H13B	109.7	H37A—C37—H37B	109.5
C14—C13—H13B	109.7	O1—C37—H37C	109.5
H13A—C13—H13B	108.2	H37A—C37—H37C	109.5
N4—C14—C15	121.6 (3)	H37B—C37—H37C	109.5
N5—Co1—N1—C1	−58.3 (2)	Co1—N3—C8—C7	4.1 (3)
N4—Co1—N1—C1	−150.1 (2)	N1—C7—C8—N3	−3.5 (4)
N2—Co1—N1—C1	30.8 (2)	N1—C7—C8—C9	177.6 (3)
N3—Co1—N1—C1	120.8 (2)	N3—C8—C9—C10	−1.5 (5)
N5—Co1—N1—C13	61.4 (2)	C7—C8—C9—C10	177.3 (3)
N4—Co1—N1—C13	−30.43 (19)	C8—C9—C10—C11	0.8 (5)
N2—Co1—N1—C13	150.4 (2)	C9—C10—C11—C12	0.5 (5)
N3—Co1—N1—C13	−119.5 (2)	C8—N3—C12—C11	0.5 (5)
N5—Co1—N1—C7	−178.4 (2)	Co1—N3—C12—C11	178.2 (2)
N4—Co1—N1—C7	89.8 (2)	C10—C11—C12—N3	−1.2 (5)
N2—Co1—N1—C7	−89.4 (2)	C1—N1—C13—C14	157.9 (3)
N3—Co1—N1—C7	0.7 (2)	C7—N1—C13—C14	−77.1 (3)
N6^i—Co1—N2—C6	−15.8 (3)	Co1—N1—C13—C14	42.4 (3)
N5—Co1—N2—C6	−106.8 (3)	C18—N4—C14—C15	0.3 (5)
N4—Co1—N2—C6	158.4 (3)	Co1—N4—C14—C15	−175.4 (2)
N3—Co1—N2—C6	79.2 (3)	C18—N4—C14—C13	−178.0 (3)
N1—Co1—N2—C6	160.5 (3)	Co1—N4—C14—C13	6.3 (3)
N6^i—Co1—N2—C2	171.2 (2)	N1—C13—C14—N4	−33.6 (4)
N5—Co1—N2—C2	80.2 (2)	N1—C13—C14—C15	148.1 (3)
N4—Co1—N2—C2	−14.6 (4)	N4—C14—C15—C16	−0.5 (5)
N3—Co1—N2—C2	−93.8 (2)	C13—C14—C15—C16	177.6 (3)
N1—Co1—N2—C2	−12.5 (2)	C14—C15—C16—C17	0.1 (5)
N6^i—Co1—N3—C8	177.9 (2)	C14—C15—C16—C31^v	80.7 (3)
N4—Co1—N3—C8	−80.7 (2)	C15—C16—C17—C18	0.6 (5)
N2—Co1—N3—C8	75.7 (2)	C31^v—C16—C17—C18	−80.2 (3)
N1—Co1—N3—C8	−2.6 (2)	C15—C16—C17—C33^vi	86.4 (3)
N6^i—Co1—N3—C12	0.2 (3)	C31^v—C16—C17—C33^vi	5.67 (11)
N4—Co1—N3—C12	101.5 (3)	C14—N4—C18—C17	0.4 (5)
N2—Co1—N3—C12	−102.0 (3)	Co1—N4—C18—C17	175.6 (2)
N1—Co1—N3—C12	179.7 (3)	C16—C17—C18—N4	−0.8 (5)
N6^i—Co1—N4—C18	15.0 (3)	C33^vi—C17—C18—N4	−93.0 (3)
N5—Co1—N4—C18	106.5 (3)	C21^ii—C19—C20—C21	0.4 (5)
N2—Co1—N4—C18	−159.2 (3)	C30^i—C19—C20—C21	89.1 (3)
N3—Co1—N4—C18	−79.8 (3)	C21^ii—C19—C20—C28^i	−80.4 (3)
N1—Co1—N4—C18	−161.3 (3)	C30^i—C19—C20—C28^i	8.30 (12)
N6^i—Co1—N4—C14	−169.7 (2)	C21^ii—C19—C20—C30^i	−88.7 (3)
N5—Co1—N4—C14	−78.1 (2)	C19—C20—C21—C19^ii	−0.3 (5)
N2—Co1—N4—C14	16.1 (4)	C28^i—C20—C21—C19^ii	90.6 (3)
N3—Co1—N4—C14	95.5 (2)	C30^i—C20—C21—C19^ii	75.8 (3)
N1—Co1—N4—C14	14.0 (2)	C19—C20—C21—C22	179.7 (3)
N6^i—Co1—N5—C23	−39.4 (11)	C28^i—C20—C21—C22	−89.4 (3)
N4—Co1—N5—C23	−141.1 (11)	C30^i—C20—C21—C22	−104.1 (3)
N2—Co1—N5—C23	62.9 (11)	C19—C20—C21—C28^i	−90.9 (3)
N1—Co1—N5—C23	141.0 (11)	C30^i—C20—C21—C28^i	−14.71 (10)
C13—N1—C1—C2	−159.6 (3)	C20—C21—C22—C24	−179.3 (3)
C7—N1—C1—C2	75.5 (3)	C19^ii—C21—C22—C24	0.8 (5)
Co1—N1—C1—C2	−43.8 (3)	C28^i—C21—C22—C24	101.3 (3)
C6—N2—C2—C3	0.0 (5)	C20—C21—C22—C23	−2.9 (5)
Co1—N2—C2—C3	173.6 (3)	C19^ii—C21—C22—C23	177.2 (3)
C6—N2—C2—C1	177.2 (3)	C28^i—C21—C22—C23	−82.4 (3)
Co1—N2—C2—C1	−9.2 (4)	C27^iii—C25—C26—C28	179.0 (4)
N1—C1—C2—N2	36.8 (4)	C27^iii—C25—C26—C27	−0.8 (6)
N1—C1—C2—C3	−146.1 (3)	C25—C26—C27—C25^iii	0.8 (6)
N2—C2—C3—C4	1.0 (5)	C28—C26—C27—C25^iii	−179.0 (4)
C1—C2—C3—C4	−176.0 (3)	C25—C26—C28—C29	177.4 (3)
C2—C3—C4—C5	−1.0 (6)	C27—C26—C28—C29	−2.8 (5)
C3—C4—C5—C6	0.1 (6)	C25—C26—C28—C30	−5.2 (5)
C2—N2—C6—C5	−0.9 (5)	C27—C26—C28—C30	174.6 (3)
Co1—N2—C6—C5	−173.7 (3)	C33^iv—C31—C32—C33	−0.2 (5)
C4—C5—C6—N2	0.9 (6)	C33^iv—C31—C32—C34	−179.3 (3)
C1—N1—C7—C8	−115.8 (3)	C31—C32—C33—C31^iv	0.2 (5)
C13—N1—C7—C8	118.5 (3)	C34—C32—C33—C31^iv	179.3 (3)
Co1—N1—C7—C8	1.1 (3)	C33—C32—C34—C35	−172.3 (3)
C12—N3—C8—C9	0.8 (4)	C31—C32—C34—C35	6.7 (5)
Co1—N3—C8—C9	−177.1 (2)	C33—C32—C34—C36	5.7 (5)
C12—N3—C8—C7	−178.0 (3)	C31—C32—C34—C36	−175.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N9	0.84	1.99	2.829 (5)	172

(II) catena-poly[[[[tris(2-pyridylmethyl)amine]iron(II)]-µ₂- 7,7',8,8'-tetracyanoquinodimethanide(2-)] methanol solvate]

Crystal data

[Fe(C12H4N4)(C18H18N4)]·CH4O	F(000) = 1208
Mr = 582.45	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2713 reflections
a = 9.4197 (10) Å	θ = 2.2–22.3°
b = 18.2526 (18) Å	µ = 0.58 mm^−1
c = 17.0040 (18) Å	T = 100 K
β = 105.275 (9)°	Brick, orange
V = 2820.3 (5) Å^3	0.14 × 0.12 × 0.10 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer	3180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.6°, θmin = 3.6°
Detector resolution: 16.0355 pixels mm^-1	h = −11→11
ϕ and ω scans	k = −19→22
15228 measured reflections	l = −20→18
5257 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0464P)^2] where P = (Fo^2 + 2Fc^2)/3
5257 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.9601 (0.0020) x + 11.8396 (0.0052) y + 6.3030 (0.0059) z = 4.7795 (0.0026)

* 0.0287 (0.0020) C19 * 0.1633 (0.0020) C20 * 0.1278 (0.0020) C21 * -0.0292 (0.0020) C22 * -0.1783 (0.0020) C23 * -0.1488 (0.0020) C24 * 0.0550 (0.0022) C25 * -0.0799 (0.0021) C26 * 0.1159 (0.0022) C27 * -0.0032 (0.0021) C28 * -0.0270 (0.0020) C29 * 0.0298 (0.0021) C30 * -0.2320 (0.0018) N5 * 0.1576 (0.0020) N6 * -0.0610 (0.0017) N7 * 0.0812 (0.0019) N8

Rms deviation of fitted atoms = 0.1151

6.9601 (0.0020) x + 11.8396 (0.0052) y - 6.3030 (0.0059) z = 2.6683 (0.0014)

Angle to previous plane (with approximate e.s.d.) = 80.88 (0.02)

* 0.0287 (0.0020) C19_$2 * 0.1633 (0.0020) C20_$2 * 0.1278 (0.0020) C21_$2 * -0.0292 (0.0020) C22_$2 * -0.1783 (0.0020) C23_$2 * -0.1488 (0.0020) C24_$2 * 0.0550 (0.0022) C25_$2 * -0.0799 (0.0021) C26_$2 * 0.1159 (0.0022) C27_$2 * -0.0032 (0.0021) C28_$2 * -0.0270 (0.0020) C29_$2 * 0.0298 (0.0021) C30_$2 * -0.2320 (0.0018) N5_$2 * 0.1576 (0.0020) N6_$2 * -0.0610 (0.0017) N7_$2 * 0.0812 (0.0019) N8_$2

Rms deviation of fitted atoms = 0.1151 EQIV $2 - x + 1, y - 1/2, -z + 1/2

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	0.00217 (3)	0.253651 (19)	0.171808 (19)	0.02819 (11)
N1	−0.09659 (19)	0.15504 (10)	0.19265 (11)	0.0261 (4)
N2	−0.1354 (2)	0.23753 (10)	0.05576 (11)	0.0297 (5)
N3	−0.1861 (2)	0.29797 (10)	0.19239 (11)	0.0295 (5)
N4	0.1079 (2)	0.23360 (10)	0.29336 (12)	0.0320 (5)
N5	0.0851 (2)	0.35138 (14)	0.15547 (12)	0.0412 (6)
N6	0.1705 (3)	0.52489 (13)	−0.01435 (15)	0.0556 (6)
N7	0.8354 (2)	0.69905 (11)	0.35803 (11)	0.0354 (5)
N8	0.7224 (2)	0.55072 (13)	0.53443 (14)	0.0490 (6)
C1	−0.1477 (3)	0.11718 (13)	0.11326 (14)	0.0314 (6)
H1A	−0.2260	0.0817	0.1156	0.038*
H1B	−0.0650	0.0898	0.1014	0.038*
C2	−0.2063 (2)	0.17207 (13)	0.04681 (14)	0.0299 (5)
C3	−0.3215 (3)	0.15624 (15)	−0.02047 (15)	0.0436 (7)
H3	−0.3702	0.1102	−0.0251	0.052*
C4	−0.3643 (3)	0.20840 (18)	−0.08062 (16)	0.0560 (8)
H4	−0.4426	0.1987	−0.1276	0.067*
C5	−0.2924 (3)	0.27449 (17)	−0.07183 (17)	0.0507 (8)
H5	−0.3202	0.3110	−0.1129	0.061*
C6	−0.1793 (3)	0.28764 (15)	−0.00280 (16)	0.0391 (6)
H6	−0.1311	0.3338	0.0031	0.047*
C7	−0.2218 (3)	0.17299 (13)	0.22791 (15)	0.0347 (6)
H7A	−0.1877	0.1703	0.2881	0.042*
H7B	−0.3006	0.1361	0.2094	0.042*
C8	−0.2837 (2)	0.24770 (13)	0.20363 (12)	0.0270 (5)
C9	−0.4290 (3)	0.26470 (14)	0.19687 (14)	0.0361 (6)
H9	−0.4960	0.2281	0.2043	0.043*
C10	−0.4751 (3)	0.33591 (17)	0.17917 (16)	0.0481 (7)
H10	−0.5746	0.3492	0.1742	0.058*
C11	−0.3747 (3)	0.38766 (15)	0.16883 (18)	0.0515 (8)
H11	−0.4040	0.4372	0.1573	0.062*
C12	−0.2318 (3)	0.36670 (14)	0.17546 (15)	0.0396 (6)
H12	−0.1634	0.4024	0.1677	0.047*
C13	0.0134 (2)	0.11170 (12)	0.25282 (14)	0.0302 (5)
H13A	0.0805	0.0864	0.2256	0.036*
H13B	−0.0365	0.0742	0.2781	0.036*
C14	0.0995 (3)	0.16307 (14)	0.31705 (14)	0.0334 (6)
C15	0.1664 (3)	0.13989 (17)	0.39537 (16)	0.0506 (7)
H15	0.1582	0.0904	0.4109	0.061*
C16	0.2455 (4)	0.1899 (2)	0.45074 (18)	0.0710 (10)
H16	0.2930	0.1751	0.5048	0.085*
C17	0.2547 (3)	0.26070 (19)	0.42703 (18)	0.0606 (9)
H17	0.3093	0.2957	0.4643	0.073*
C18	0.1841 (3)	0.28099 (15)	0.34842 (17)	0.0456 (7)
H18	0.1897	0.3306	0.3327	0.055*
C19	0.3341 (2)	0.49939 (13)	0.19369 (14)	0.0314 (6)
C20	0.3541 (2)	0.47925 (13)	0.27501 (14)	0.0292 (5)
H20	0.2897	0.4442	0.2885	0.035*
C21	0.4658 (2)	0.50907 (12)	0.33665 (14)	0.0287 (5)
H21	0.4766	0.4936	0.3912	0.034*
C22	0.5626 (2)	0.56119 (12)	0.32071 (14)	0.0274 (5)
C23	0.5441 (2)	0.58124 (13)	0.23905 (14)	0.0297 (5)
H23	0.6089	0.6161	0.2256	0.036*
C24	0.4329 (3)	0.55101 (13)	0.17767 (14)	0.0324 (6)
H24	0.4232	0.5657	0.1229	0.039*
C25	0.2167 (3)	0.46749 (14)	0.12813 (15)	0.0363 (6)
C26	0.1409 (3)	0.40453 (16)	0.14133 (14)	0.0360 (6)
C27	0.1874 (3)	0.49767 (15)	0.04878 (17)	0.0422 (7)
C28	0.6762 (2)	0.59476 (13)	0.38727 (14)	0.0293 (5)
C29	0.7643 (3)	0.65216 (13)	0.37295 (13)	0.0290 (5)
C30	0.7023 (3)	0.57012 (14)	0.46761 (16)	0.0352 (6)
O1	0.9961 (2)	0.54698 (11)	0.66068 (11)	0.0511 (5)
H1	0.9099	0.5459	0.6304	0.077*
C31	1.0910 (3)	0.57864 (16)	0.61782 (18)	0.0542 (8)
H31A	1.0770	0.5541	0.5650	0.081*
H31B	1.1934	0.5728	0.6497	0.081*
H31C	1.0683	0.6309	0.6090	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02775 (17)	0.0286 (2)	0.02662 (18)	0.00636 (16)	0.00429 (13)	−0.00020 (16)
N1	0.0259 (10)	0.0226 (11)	0.0293 (11)	0.0002 (8)	0.0065 (9)	0.0004 (8)
N2	0.0291 (10)	0.0282 (13)	0.0332 (11)	0.0049 (9)	0.0108 (9)	0.0045 (9)
N3	0.0351 (11)	0.0220 (12)	0.0302 (11)	−0.0019 (9)	0.0065 (9)	−0.0002 (9)
N4	0.0385 (11)	0.0259 (13)	0.0350 (12)	−0.0004 (9)	0.0154 (9)	−0.0051 (9)
N5	0.0257 (12)	0.0638 (17)	0.0314 (13)	−0.0020 (11)	0.0027 (10)	−0.0058 (11)
N6	0.0706 (17)	0.0380 (15)	0.0443 (15)	−0.0026 (12)	−0.0094 (12)	−0.0021 (12)
N7	0.0422 (12)	0.0296 (13)	0.0288 (12)	−0.0095 (10)	−0.0006 (10)	0.0021 (9)
N8	0.0500 (14)	0.0514 (16)	0.0387 (14)	−0.0196 (11)	−0.0005 (11)	0.0109 (11)
C1	0.0314 (13)	0.0243 (14)	0.0355 (14)	−0.0042 (10)	0.0035 (11)	−0.0025 (10)
C2	0.0292 (13)	0.0295 (15)	0.0302 (14)	0.0029 (11)	0.0063 (11)	−0.0027 (11)
C3	0.0458 (16)	0.0387 (17)	0.0404 (16)	0.0038 (13)	0.0010 (13)	−0.0074 (13)
C4	0.062 (2)	0.063 (2)	0.0329 (17)	0.0181 (17)	−0.0058 (14)	−0.0039 (15)
C5	0.066 (2)	0.055 (2)	0.0335 (16)	0.0260 (16)	0.0177 (15)	0.0152 (14)
C6	0.0450 (15)	0.0321 (16)	0.0461 (17)	0.0088 (13)	0.0226 (14)	0.0128 (13)
C7	0.0320 (14)	0.0311 (15)	0.0429 (15)	−0.0029 (11)	0.0130 (12)	0.0020 (12)
C8	0.0283 (11)	0.0270 (13)	0.0264 (12)	0.0002 (11)	0.0086 (9)	0.0000 (11)
C9	0.0291 (13)	0.0440 (18)	0.0365 (14)	0.0002 (12)	0.0110 (11)	−0.0014 (12)
C10	0.0385 (16)	0.057 (2)	0.0513 (18)	0.0177 (14)	0.0153 (14)	0.0016 (15)
C11	0.064 (2)	0.0319 (17)	0.066 (2)	0.0197 (15)	0.0296 (16)	0.0041 (14)
C12	0.0512 (17)	0.0252 (15)	0.0452 (16)	−0.0001 (12)	0.0179 (13)	−0.0015 (12)
C13	0.0336 (13)	0.0239 (14)	0.0325 (14)	0.0030 (11)	0.0076 (11)	0.0047 (10)
C14	0.0370 (14)	0.0313 (15)	0.0312 (14)	0.0018 (11)	0.0082 (11)	−0.0019 (11)
C15	0.072 (2)	0.0422 (18)	0.0320 (16)	0.0041 (15)	0.0042 (14)	0.0052 (13)
C16	0.092 (3)	0.075 (3)	0.0323 (17)	−0.004 (2)	−0.0071 (16)	−0.0004 (17)
C17	0.073 (2)	0.061 (2)	0.0444 (18)	−0.0187 (18)	0.0103 (16)	−0.0239 (16)
C18	0.0552 (17)	0.0396 (17)	0.0451 (18)	−0.0147 (14)	0.0185 (15)	−0.0158 (13)
C19	0.0293 (13)	0.0288 (14)	0.0347 (15)	0.0080 (11)	0.0060 (11)	−0.0029 (11)
C20	0.0258 (12)	0.0244 (14)	0.0361 (15)	0.0024 (10)	0.0061 (11)	−0.0017 (11)
C21	0.0305 (13)	0.0245 (14)	0.0307 (13)	0.0054 (10)	0.0070 (11)	0.0028 (10)
C22	0.0247 (12)	0.0248 (14)	0.0324 (14)	0.0072 (10)	0.0070 (10)	0.0003 (10)
C23	0.0294 (13)	0.0261 (14)	0.0342 (14)	0.0056 (10)	0.0095 (11)	0.0016 (11)
C24	0.0366 (14)	0.0300 (15)	0.0299 (14)	0.0082 (11)	0.0077 (11)	−0.0002 (11)
C25	0.0317 (14)	0.0393 (17)	0.0328 (15)	0.0078 (12)	−0.0007 (11)	−0.0062 (12)
C26	0.0208 (13)	0.054 (2)	0.0293 (14)	0.0065 (13)	−0.0005 (11)	−0.0102 (13)
C27	0.0432 (16)	0.0325 (16)	0.0424 (18)	0.0022 (12)	−0.0037 (13)	−0.0078 (13)
C28	0.0278 (13)	0.0283 (14)	0.0301 (14)	−0.0002 (10)	0.0045 (11)	0.0034 (10)
C29	0.0310 (13)	0.0280 (15)	0.0241 (13)	0.0045 (11)	0.0004 (11)	0.0020 (10)
C30	0.0274 (13)	0.0338 (16)	0.0400 (16)	−0.0078 (11)	0.0013 (12)	0.0042 (12)
O1	0.0543 (12)	0.0468 (12)	0.0484 (12)	−0.0086 (10)	0.0070 (10)	0.0074 (9)
C31	0.0546 (18)	0.0502 (19)	0.0593 (19)	−0.0045 (15)	0.0175 (15)	0.0030 (15)

Geometric parameters (Å, º)

Fe1—N5	1.996 (3)	C10—C11	1.380 (4)
Fe1—N7^i	2.000 (2)	C10—H10	0.95
Fe1—N3	2.0611 (19)	C11—C12	1.375 (3)
Fe1—N2	2.0767 (19)	C11—H11	0.95
Fe1—N4	2.077 (2)	C12—H12	0.95
Fe1—N1	2.0987 (18)	C13—C14	1.504 (3)
N1—C13	1.479 (3)	C13—H13A	0.99
N1—C1	1.480 (3)	C13—H13B	0.99
N1—C7	1.494 (3)	C14—C15	1.381 (3)
N2—C6	1.335 (3)	C15—C16	1.380 (4)
N2—C2	1.357 (3)	C15—H15	0.95
N3—C12	1.333 (3)	C16—C17	1.364 (4)
N3—C8	1.348 (3)	C16—H16	0.95
N4—C18	1.336 (3)	C17—C18	1.378 (4)
N4—C14	1.358 (3)	C17—H17	0.95
N5—C26	1.158 (3)	C18—H18	0.95
N6—C27	1.155 (3)	C19—C20	1.395 (3)
N7—C29	1.156 (3)	C19—C24	1.401 (3)
N7—Fe1^ii	2.000 (2)	C19—C25	1.468 (3)
N8—C30	1.157 (3)	C20—C21	1.386 (3)
C1—C2	1.502 (3)	C20—H20	0.95
C1—H1A	0.99	C21—C22	1.393 (3)
C1—H1B	0.99	C21—H21	0.95
C2—C3	1.384 (3)	C22—C23	1.402 (3)
C3—C4	1.378 (4)	C22—C28	1.471 (3)
C3—H3	0.95	C23—C24	1.384 (3)
C4—C5	1.372 (4)	C23—H23	0.95
C4—H4	0.95	C24—H24	0.95
C5—C6	1.383 (4)	C25—C26	1.402 (4)
C5—H5	0.95	C25—C27	1.416 (4)
C6—H6	0.95	C28—C30	1.397 (3)
C7—C8	1.497 (3)	C28—C29	1.397 (3)
C7—H7A	0.99	O1—C31	1.417 (3)
C7—H7B	0.99	O1—H1	0.84
C8—C9	1.379 (3)	C31—H31A	0.98
C9—C10	1.378 (4)	C31—H31B	0.98
C9—H9	0.95	C31—H31C	0.98
N5—Fe1—N7^i	93.23 (8)	C9—C10—C11	119.1 (2)
N5—Fe1—N3	93.37 (8)	C9—C10—H10	120.5
N7^i—Fe1—N3	171.28 (8)	C11—C10—H10	120.5
N5—Fe1—N2	99.42 (8)	C12—C11—C10	119.2 (3)
N7^i—Fe1—N2	90.92 (7)	C12—C11—H11	120.4
N3—Fe1—N2	82.38 (7)	C10—C11—H11	120.4
N5—Fe1—N4	101.14 (8)	N3—C12—C11	122.2 (2)
N7^i—Fe1—N4	88.06 (7)	N3—C12—H12	118.9
N3—Fe1—N4	96.24 (7)	C11—C12—H12	118.9
N2—Fe1—N4	159.44 (7)	N1—C13—C14	108.30 (19)
N5—Fe1—N1	175.69 (7)	N1—C13—H13A	110.0
N7^i—Fe1—N1	91.04 (8)	C14—C13—H13A	110.0
N3—Fe1—N1	82.44 (7)	N1—C13—H13B	110.0
N2—Fe1—N1	81.11 (7)	C14—C13—H13B	110.0
N4—Fe1—N1	78.38 (7)	H13A—C13—H13B	108.4
C13—N1—C1	112.43 (18)	N4—C14—C15	121.9 (2)
C13—N1—C7	108.86 (17)	N4—C14—C13	116.0 (2)
C1—N1—C7	111.53 (18)	C15—C14—C13	122.1 (2)
C13—N1—Fe1	108.33 (13)	C16—C15—C14	118.9 (3)
C1—N1—Fe1	107.38 (13)	C16—C15—H15	120.6
C7—N1—Fe1	108.17 (13)	C14—C15—H15	120.6
C6—N2—C2	118.2 (2)	C17—C16—C15	119.4 (3)
C6—N2—Fe1	127.20 (18)	C17—C16—H16	120.3
C2—N2—Fe1	113.37 (15)	C15—C16—H16	120.3
C12—N3—C8	118.5 (2)	C16—C17—C18	119.3 (3)
C12—N3—Fe1	125.19 (16)	C16—C17—H17	120.4
C8—N3—Fe1	113.98 (15)	C18—C17—H17	120.4
C18—N4—C14	118.0 (2)	N4—C18—C17	122.6 (3)
C18—N4—Fe1	127.69 (18)	N4—C18—H18	118.7
C14—N4—Fe1	114.34 (15)	C17—C18—H18	118.7
C26—N5—Fe1	173.2 (2)	C20—C19—C24	116.5 (2)
C29—N7—Fe1^ii	162.0 (2)	C20—C19—C25	121.8 (2)
N1—C1—C2	109.97 (19)	C24—C19—C25	121.7 (2)
N1—C1—H1A	109.7	C21—C20—C19	121.6 (2)
C2—C1—H1A	109.7	C21—C20—H20	119.2
N1—C1—H1B	109.7	C19—C20—H20	119.2
C2—C1—H1B	109.7	C20—C21—C22	121.8 (2)
H1A—C1—H1B	108.2	C20—C21—H21	119.1
N2—C2—C3	122.1 (2)	C22—C21—H21	119.1
N2—C2—C1	115.5 (2)	C21—C22—C23	117.0 (2)
C3—C2—C1	122.3 (2)	C21—C22—C28	121.0 (2)
C4—C3—C2	118.8 (3)	C23—C22—C28	121.9 (2)
C4—C3—H3	120.6	C24—C23—C22	121.0 (2)
C2—C3—H3	120.6	C24—C23—H23	119.5
C5—C4—C3	119.2 (3)	C22—C23—H23	119.5
C5—C4—H4	120.4	C23—C24—C19	122.1 (2)
C3—C4—H4	120.4	C23—C24—H24	118.9
C4—C5—C6	119.5 (3)	C19—C24—H24	118.9
C4—C5—H5	120.2	C26—C25—C27	119.5 (2)
C6—C5—H5	120.2	C26—C25—C19	121.1 (2)
N2—C6—C5	122.1 (3)	C27—C25—C19	119.2 (2)
N2—C6—H6	118.9	N5—C26—C25	176.3 (3)
C5—C6—H6	118.9	N6—C27—C25	176.0 (3)
N1—C7—C8	112.33 (18)	C30—C28—C29	116.9 (2)
N1—C7—H7A	109.1	C30—C28—C22	121.6 (2)
C8—C7—H7A	109.1	C29—C28—C22	121.6 (2)
N1—C7—H7B	109.1	N7—C29—C28	177.4 (2)
C8—C7—H7B	109.1	N8—C30—C28	178.8 (3)
H7A—C7—H7B	107.9	C31—O1—H1	109.5
N3—C8—C9	122.3 (2)	O1—C31—H31A	109.5
N3—C8—C7	115.40 (19)	O1—C31—H31B	109.5
C9—C8—C7	122.2 (2)	H31A—C31—H31B	109.5
C10—C9—C8	118.6 (2)	O1—C31—H31C	109.5
C10—C9—H9	120.7	H31A—C31—H31C	109.5
C8—C9—H9	120.7	H31B—C31—H31C	109.5
N7^i—Fe1—N1—C13	55.31 (14)	C2—N2—C6—C5	−0.7 (3)
N3—Fe1—N1—C13	−130.51 (14)	Fe1—N2—C6—C5	−167.34 (17)
N2—Fe1—N1—C13	146.07 (14)	C4—C5—C6—N2	1.0 (4)
N4—Fe1—N1—C13	−32.50 (14)	C13—N1—C7—C8	143.7 (2)
N7^i—Fe1—N1—C1	−66.35 (14)	C1—N1—C7—C8	−91.7 (2)
N3—Fe1—N1—C1	107.83 (14)	Fe1—N1—C7—C8	26.2 (2)
N2—Fe1—N1—C1	24.42 (13)	C12—N3—C8—C9	1.1 (3)
N4—Fe1—N1—C1	−154.16 (14)	Fe1—N3—C8—C9	−162.57 (17)
N7^i—Fe1—N1—C7	173.16 (14)	C12—N3—C8—C7	−176.1 (2)
N3—Fe1—N1—C7	−12.66 (14)	Fe1—N3—C8—C7	20.3 (2)
N2—Fe1—N1—C7	−96.07 (14)	N1—C7—C8—N3	−31.7 (3)
N4—Fe1—N1—C7	85.35 (14)	N1—C7—C8—C9	151.1 (2)
N5—Fe1—N2—C6	−14.83 (19)	N3—C8—C9—C10	−1.0 (3)
N7^i—Fe1—N2—C6	−108.25 (19)	C7—C8—C9—C10	176.0 (2)
N3—Fe1—N2—C6	77.35 (18)	C8—C9—C10—C11	0.0 (4)
N4—Fe1—N2—C6	164.81 (19)	C9—C10—C11—C12	0.8 (4)
N1—Fe1—N2—C6	160.84 (19)	C8—N3—C12—C11	−0.3 (3)
N5—Fe1—N2—C2	177.97 (15)	Fe1—N3—C12—C11	161.41 (19)
N7^i—Fe1—N2—C2	84.55 (15)	C10—C11—C12—N3	−0.7 (4)
N3—Fe1—N2—C2	−89.85 (15)	C1—N1—C13—C14	158.66 (17)
N4—Fe1—N2—C2	−2.4 (3)	C7—N1—C13—C14	−77.2 (2)
N1—Fe1—N2—C2	−6.36 (14)	Fe1—N1—C13—C14	40.2 (2)
N5—Fe1—N3—C12	14.8 (2)	C18—N4—C14—C15	0.1 (3)
N2—Fe1—N3—C12	−84.3 (2)	Fe1—N4—C14—C15	178.56 (19)
N4—Fe1—N3—C12	116.39 (19)	C18—N4—C14—C13	−179.6 (2)
N1—Fe1—N3—C12	−166.3 (2)	Fe1—N4—C14—C13	−1.2 (2)
N5—Fe1—N3—C8	177.20 (15)	N1—C13—C14—N4	−26.3 (3)
N2—Fe1—N3—C8	78.14 (15)	N1—C13—C14—C15	153.9 (2)
N4—Fe1—N3—C8	−81.19 (15)	N4—C14—C15—C16	−0.7 (4)
N1—Fe1—N3—C8	−3.84 (14)	C13—C14—C15—C16	179.0 (3)
N5—Fe1—N4—C18	12.9 (2)	C14—C15—C16—C17	0.4 (5)
N7^i—Fe1—N4—C18	105.8 (2)	C15—C16—C17—C18	0.4 (5)
N3—Fe1—N4—C18	−81.8 (2)	C14—N4—C18—C17	0.8 (4)
N2—Fe1—N4—C18	−166.7 (2)	Fe1—N4—C18—C17	−177.42 (19)
N1—Fe1—N4—C18	−162.7 (2)	C16—C17—C18—N4	−1.1 (4)
N5—Fe1—N4—C14	−165.35 (16)	C24—C19—C20—C21	0.2 (3)
N7^i—Fe1—N4—C14	−72.45 (16)	C25—C19—C20—C21	179.5 (2)
N3—Fe1—N4—C14	99.95 (16)	C19—C20—C21—C22	0.7 (3)
N2—Fe1—N4—C14	15.0 (3)	C20—C21—C22—C23	−1.3 (3)
N1—Fe1—N4—C14	19.02 (15)	C20—C21—C22—C28	177.2 (2)
C13—N1—C1—C2	−156.75 (18)	C21—C22—C23—C24	0.9 (3)
C7—N1—C1—C2	80.6 (2)	C28—C22—C23—C24	−177.5 (2)
Fe1—N1—C1—C2	−37.7 (2)	C22—C23—C24—C19	0.0 (3)
C6—N2—C2—C3	−0.2 (3)	C20—C19—C24—C23	−0.6 (3)
Fe1—N2—C2—C3	168.25 (18)	C25—C19—C24—C23	−179.8 (2)
C6—N2—C2—C1	177.73 (19)	C20—C19—C25—C26	−14.2 (3)
Fe1—N2—C2—C1	−13.8 (2)	C24—C19—C25—C26	165.0 (2)
N1—C1—C2—N2	35.3 (3)	C20—C19—C25—C27	170.6 (2)
N1—C1—C2—C3	−146.8 (2)	C24—C19—C25—C27	−10.2 (3)
N2—C2—C3—C4	0.8 (4)	C21—C22—C28—C30	7.2 (3)
C1—C2—C3—C4	−177.0 (2)	C23—C22—C28—C30	−174.4 (2)
C2—C3—C4—C5	−0.5 (4)	C21—C22—C28—C29	−173.6 (2)
C3—C4—C5—C6	−0.3 (4)	C23—C22—C28—C29	4.8 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N8	0.84	2.07	2.889 (3)	166