trans-Bis[2,5-bis­(pyridin-2-yl)-1,3,4-thia­diazole-κ2N2,N3]bis­(methanol-κO)iron(II) bis­(perchlorate)

Kaase, D.; Klingele, J.

doi:10.1107/S160053681401277X

metal-organic compounds

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Volume 70| Part 7| July 2014| Pages m252-m253

https://doi.org/10.1107/S160053681401277X

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trans-Bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ²N²,N³]bis(methanol-κO)iron(II) bis(perchlorate)

Dominic Kaase ^a and Julia Klingele ^a ^*

^aInstitut für Anorganische und Analytische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Br., Germany
^*Correspondence e-mail: julia.klingele@ac.uni-freiburg.de

(Received 16 May 2014; accepted 2 June 2014; online 7 June 2014)

The title compound, [Fe(C₁₂H₈N₄S)₂(CH₃OH)₂](ClO₄)₂, crystallized in the solvent-free form from a methanol solution. The Fe^II ion is located on a centre of inversion. The distorted N₄O₂ octahedral coordination geometry is formed by two N,N′-chelating equatorial 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole ligands and axially coordinating methanol coligands, resulting in the mononuclear trans-(N²,N³,O)₂ coordination mode. The methanol co-ligand is involved in a hydrogen bond to the perchlorate counter-ion.

CCDC reference: 1006207

Related literature

For other 3d metal structures of 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole, see: Klingele et al. (2010 , 2012 ); Bentiss, Lagrenee, Mentre et al. (2004 ); Bentiss, Lagrenee, Vezin et al. (2004 ); Zheng et al. (2006 ); Bentiss et al. (2002 ); Wan et al. (2007 ). For related compounds, see: Guionneau et al. (2004 ). For the bridging capability of 4,4′-bispyridine-N,N′-dioxide, see: Jia et al. (2008 ).

Experimental

Crystal data

[Fe(C₁₂H₈N₄S)₂(CH₄O)₂](ClO₄)₂
M_r = 799.40
Triclinic, $[P \overline 1]$
a = 8.8410 (3) Å
b = 9.5579 (4) Å
c = 9.5875 (4) Å
α = 87.169 (2)°
β = 88.945 (2)°
γ = 74.735 (2)°
V = 780.61 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 100 K
0.18 × 0.08 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.861, T_max = 0.975
18025 measured reflections
3128 independent reflections
2789 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.062
S = 1.05
3128 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20⋯O11	0.78 (3)	1.91 (3)	2.690 (2)	178 (3)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: OLEX2.refine (Puschmann et al., 2013 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ) and OLEX2.refine (Puschmann et al., 2013); molecular graphics: DIAMOND (Brandenburg & Putz, 2011 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1006207

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S160053681401277X/lr2128sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681401277X/lr2128Isup2.hkl

checkCIF report

Introduction top

The ligand 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole (L) is well known to have a suitable ligand field for the preparation of iron(II) spin crossover complexes (Klingele. et al., 2010). Known examples are the 2:1-type complexes [Fe(L)₂(NCS)₂], [Fe(L)₂(NCSe)₂] and [Fe(L)₂(NCBH₃)₂] (Klingele et al., 2012). 4,4'-Bispyridine-N,N'-dioxide is able to bridge metal ions to form multidimensional structures (Jia et al., 2008). The title compound [Fe(L)₂(MeOH)₂](ClO₄)₂ was obtained unintendedly in the attempt to isolate one-dimensional chains of 4,4'-bispyridine-N,N'-dioxide-bridged [Fe(L)₂]²⁺ units.

Experimental top

Synthesis and crystallization top

Single crystals suitable for X-ray diffraction of the title compound were obtained unexpectedly by layering a MeOH solution of iron(II) perchlorate with a MeOH solution of 2,5-di(pyridin-2-yl)-1,3,4-thiadiazole and 4,4'-bispyridine-N,N'-dioxide in an argon atmosphere.

Refinement top

Crystal data, data collection and structure refinement details are summarized in the Table below. All hydrogen atoms of the ligand and of the methyl hydrogen atoms of the methanol coligand were positioned geometrically and refined using a riding model. The hydrogen atom of the methanol hydroxyl group was located from the difference maps and refined freely and isotropically.

Results and discussion top

The ligand L was synthesized according to literature procedure (Klingele et al., 2012). A single-crystal of [Fe(L)₂(MeOH)₂](ClO₄)₂ suitable for X-ray diffraction was obtained unexpectedly by layering a MeOH solution of iron(II) perchlorate with a MeOH solution of L and 4,4'-bispyridine-N,N'-dioxide. The mononuclear complex cation is formed by high-spin iron(II) ion coordinated by two bidentate ligands L and two MeOH coligands. The Fe—N [Fe—N_pyr 2.1516 (15), Fe—N_tda 2.2015 (15) Å] and Fe—O [2.0886 (13) Å] distances are in the expected range for high-spin iron(II) (Guionneau et al., 2004).

Related literature top

For other 3d metal structures of 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole, see: Klingele et al. (2010, 2012); Bentiss, Lagrenee, Mentre et al. (2004); Bentiss, Lagrenee, Vezin et al. (2004); Zheng et al. (2006); Bentiss et al. (2002); Wan et al. (2007). For related compounds, see: Guionneau et al. (2004). For the bridging capability of 4,4'-bispyridine-N,N'-dioxide Jia et al. (2008).

Structure description top

For other 3d metal structures of 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole, see: Klingele et al. (2010, 2012); Bentiss, Lagrenee, Mentre et al. (2004); Bentiss, Lagrenee, Vezin et al. (2004); Zheng et al. (2006); Bentiss et al. (2002); Wan et al. (2007). For related compounds, see: Guionneau et al. (2004). For the bridging capability of 4,4'-bispyridine-N,N'-dioxide Jia et al. (2008).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: OLEX2.refine (Puschmann et al., 2013); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and OLEX2.refine (Puschmann et al., 2013); molecular graphics: DIAMOND (Brandenburg et al., 2011); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the complex [Fe(L)₂(MeOH)₂](ClO₄)₂. Displacement ellipsoids are shown at the 50% probability level and H atoms are drawn with arbitrary radii. [Symmetry code: (A) -x, -y+2, -z.]

trans-Bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ²N²,N³]bis(methanol-κO)iron(II) bis(perchlorate) top

Crystal data top

[Fe(C₁₂H₈N₄S)₂(CH₄O)₂](ClO₄)₂	Z = 1
M_r = 799.40	F(000) = 408
Triclinic, P1	D_x = 1.701 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8410 (3) Å	Cell parameters from 9969 reflections
b = 9.5579 (4) Å	θ = 2.2–30.5°
c = 9.5875 (4) Å	µ = 0.86 mm⁻¹
α = 87.169 (2)°	T = 100 K
β = 88.945 (2)°	Plate, red
γ = 74.735 (2)°	0.18 × 0.08 × 0.03 mm
V = 780.61 (5) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3128 independent reflections
Radiation source: microfocus sealed tube	2789 reflections with I > 2σ(I)
Multilayer mirror optics monochromator	R_int = 0.019
φ and ω scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.861, T_max = 0.975	k = −11→11
18025 measured reflections	l = −11→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0172P)² + 0.9493P] where P = (F_o² + 2F_c²)/3
3128 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Fe(C₁₂H₈N₄S)₂(CH₄O)₂](ClO₄)₂	γ = 74.735 (2)°
M_r = 799.40	V = 780.61 (5) Å³
Triclinic, P1	Z = 1
a = 8.8410 (3) Å	Mo Kα radiation
b = 9.5579 (4) Å	µ = 0.86 mm⁻¹
c = 9.5875 (4) Å	T = 100 K
α = 87.169 (2)°	0.18 × 0.08 × 0.03 mm
β = 88.945 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3128 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2789 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.975	R_int = 0.019
18025 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.49 e Å⁻³
3128 reflections	Δρ_min = −0.38 e Å⁻³
227 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Fe1	0.0000	1.0000	0.0000	0.01139 (10)
S1	0.22171 (5)	0.51392 (5)	0.06646 (5)	0.01390 (11)
N1	0.18464 (17)	0.89318 (16)	−0.14602 (15)	0.0128 (3)
N2	0.05730 (17)	0.77550 (16)	0.07183 (16)	0.0131 (3)
N3	−0.00347 (18)	0.70371 (17)	0.17709 (16)	0.0144 (3)
N4	0.14375 (19)	0.33511 (17)	0.30380 (17)	0.0171 (3)
C1	0.2469 (2)	0.9547 (2)	−0.25294 (19)	0.0154 (4)
H1	0.2034	1.0550	−0.2760	0.018*
C2	0.3724 (2)	0.8783 (2)	−0.33180 (19)	0.0162 (4)
H2	0.4130	0.9255	−0.4075	0.019*
C3	0.4371 (2)	0.7330 (2)	−0.2986 (2)	0.0154 (4)
H3	0.5228	0.6786	−0.3510	0.018*
C4	0.3748 (2)	0.6677 (2)	−0.18715 (19)	0.0138 (4)
H4	0.4174	0.5679	−0.1617	0.017*
C5	0.2495 (2)	0.75062 (19)	−0.11400 (18)	0.0115 (4)
C6	0.1740 (2)	0.69113 (19)	0.00391 (18)	0.0118 (4)
C7	0.0705 (2)	0.5668 (2)	0.18660 (19)	0.0131 (4)
C8	0.0312 (2)	0.4599 (2)	0.28666 (19)	0.0131 (4)
C9	−0.1131 (2)	0.4898 (2)	0.35465 (19)	0.0158 (4)
H9	−0.1888	0.5801	0.3387	0.019*
C10	−0.1429 (2)	0.3835 (2)	0.4465 (2)	0.0186 (4)
H10	−0.2402	0.3992	0.4949	0.022*
C11	−0.0285 (2)	0.2540 (2)	0.4665 (2)	0.0200 (4)
H11	−0.0462	0.1794	0.5288	0.024*
C12	0.1125 (2)	0.2350 (2)	0.3942 (2)	0.0201 (4)
H12	0.1908	0.1463	0.4098	0.024*
C20	−0.2991 (2)	0.9010 (2)	−0.0662 (2)	0.0234 (5)
H20A	−0.3466	0.8617	−0.1416	0.035*
H20B	−0.3792	0.9775	−0.0223	0.035*
H20C	−0.2552	0.8232	0.0036	0.035*
O20	−0.17589 (15)	0.96075 (15)	−0.12275 (15)	0.0173 (3)
H20	−0.212 (3)	1.021 (3)	−0.179 (3)	0.026*
Cl10	−0.46099 (5)	1.25579 (5)	−0.29619 (5)	0.01521 (11)
O11	−0.30426 (17)	1.16340 (19)	−0.32171 (16)	0.0353 (4)
O12	−0.47275 (19)	1.39590 (16)	−0.36152 (17)	0.0320 (4)
O13	−0.57261 (18)	1.19384 (18)	−0.35684 (18)	0.0339 (4)
O14	−0.48818 (18)	1.26721 (19)	−0.14843 (15)	0.0327 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01072 (18)	0.00969 (19)	0.01282 (19)	−0.00126 (14)	0.00130 (14)	0.00030 (14)
S1	0.0141 (2)	0.0101 (2)	0.0162 (2)	−0.00128 (17)	0.00275 (17)	0.00076 (18)
N1	0.0137 (8)	0.0124 (8)	0.0118 (8)	−0.0027 (6)	0.0007 (6)	−0.0007 (6)
N2	0.0133 (7)	0.0125 (8)	0.0128 (8)	−0.0024 (6)	0.0018 (6)	0.0005 (6)
N3	0.0159 (8)	0.0134 (8)	0.0136 (8)	−0.0042 (6)	0.0017 (6)	0.0012 (6)
N4	0.0202 (8)	0.0136 (8)	0.0171 (8)	−0.0041 (7)	0.0023 (7)	0.0009 (7)
C1	0.0184 (9)	0.0129 (9)	0.0153 (9)	−0.0048 (8)	0.0005 (7)	−0.0001 (7)
C2	0.0177 (9)	0.0198 (10)	0.0134 (9)	−0.0090 (8)	0.0025 (7)	−0.0020 (8)
C3	0.0124 (9)	0.0184 (10)	0.0163 (9)	−0.0047 (7)	0.0026 (7)	−0.0070 (8)
C4	0.0137 (9)	0.0115 (9)	0.0157 (9)	−0.0021 (7)	−0.0010 (7)	−0.0026 (7)
C5	0.0119 (8)	0.0128 (9)	0.0104 (8)	−0.0041 (7)	−0.0022 (7)	−0.0014 (7)
C6	0.0117 (8)	0.0109 (9)	0.0126 (9)	−0.0026 (7)	−0.0025 (7)	−0.0009 (7)
C7	0.0115 (9)	0.0152 (9)	0.0127 (9)	−0.0036 (7)	−0.0007 (7)	−0.0015 (7)
C8	0.0159 (9)	0.0129 (9)	0.0118 (9)	−0.0060 (7)	−0.0007 (7)	−0.0015 (7)
C9	0.0152 (9)	0.0170 (10)	0.0161 (9)	−0.0057 (8)	−0.0035 (7)	−0.0003 (8)
C10	0.0184 (10)	0.0262 (11)	0.0153 (10)	−0.0130 (8)	0.0002 (8)	−0.0026 (8)
C11	0.0301 (11)	0.0198 (10)	0.0144 (10)	−0.0145 (9)	0.0005 (8)	0.0011 (8)
C12	0.0272 (11)	0.0131 (10)	0.0189 (10)	−0.0037 (8)	−0.0001 (8)	0.0015 (8)
C20	0.0144 (10)	0.0255 (11)	0.0320 (12)	−0.0074 (8)	0.0032 (8)	−0.0068 (9)
O20	0.0145 (7)	0.0178 (7)	0.0192 (7)	−0.0037 (6)	−0.0026 (5)	0.0009 (6)
Cl10	0.0138 (2)	0.0166 (2)	0.0151 (2)	−0.00390 (17)	0.00130 (17)	0.00016 (18)
O11	0.0177 (8)	0.0490 (11)	0.0267 (9)	0.0102 (7)	0.0051 (6)	0.0129 (8)
O12	0.0452 (10)	0.0162 (8)	0.0349 (9)	−0.0095 (7)	0.0194 (7)	−0.0019 (7)
O13	0.0289 (9)	0.0383 (10)	0.0423 (10)	−0.0201 (7)	0.0035 (7)	−0.0160 (8)
O14	0.0312 (9)	0.0527 (11)	0.0135 (7)	−0.0105 (8)	0.0059 (6)	−0.0004 (7)

Geometric parameters (Å, º) top

Fe1—O20	2.0886 (13)	C1—C2	1.391 (3)
Fe1—O20ⁱ	2.0886 (13)	C2—C3	1.379 (3)
Fe1—N2ⁱ	2.1516 (15)	C3—C4	1.389 (3)
Fe1—N2	2.1516 (15)	C4—C5	1.382 (3)
Fe1—N1ⁱ	2.2015 (15)	C5—C6	1.468 (2)
Fe1—N1	2.2015 (15)	C7—C8	1.471 (2)
S1—C6	1.7144 (18)	C8—C9	1.389 (3)
S1—C7	1.7364 (19)	C9—C10	1.386 (3)
N1—C1	1.338 (2)	C10—C11	1.384 (3)
N1—C5	1.354 (2)	C11—C12	1.389 (3)
N2—C6	1.315 (2)	C20—O20	1.443 (2)
N2—N3	1.372 (2)	Cl10—O13	1.4232 (15)
N3—C7	1.299 (2)	Cl10—O12	1.4292 (15)
N4—C12	1.339 (2)	Cl10—O14	1.4372 (15)
N4—C8	1.342 (2)	Cl10—O11	1.4574 (15)

O20—Fe1—O20ⁱ	180.00 (4)	C2—C3—C4	118.88 (17)
O20—Fe1—N2ⁱ	91.48 (6)	C5—C4—C3	118.73 (17)
O20ⁱ—Fe1—N2ⁱ	88.52 (6)	N1—C5—C4	122.90 (16)
O20—Fe1—N2	88.52 (6)	N1—C5—C6	114.25 (16)
O20ⁱ—Fe1—N2	91.48 (6)	C4—C5—C6	122.85 (16)
N2ⁱ—Fe1—N2	180.0	N2—C6—C5	120.39 (16)
O20—Fe1—N1ⁱ	87.99 (5)	N2—C6—S1	113.48 (13)
O20ⁱ—Fe1—N1ⁱ	92.01 (5)	C5—C6—S1	126.13 (14)
N2ⁱ—Fe1—N1ⁱ	76.37 (6)	N3—C7—C8	124.64 (17)
N2—Fe1—N1ⁱ	103.63 (6)	N3—C7—S1	114.73 (13)
O20—Fe1—N1	92.01 (5)	C8—C7—S1	120.61 (14)
O20ⁱ—Fe1—N1	87.99 (5)	N4—C8—C9	124.49 (17)
N2ⁱ—Fe1—N1	103.63 (6)	N4—C8—C7	114.70 (16)
N2—Fe1—N1	76.37 (6)	C9—C8—C7	120.81 (17)
N1ⁱ—Fe1—N1	180.0	C10—C9—C8	117.74 (18)
C6—S1—C7	86.84 (9)	C11—C10—C9	118.93 (18)
C1—N1—C5	117.61 (16)	C10—C11—C12	118.91 (18)
C1—N1—Fe1	127.76 (12)	N4—C12—C11	123.43 (19)
C5—N1—Fe1	114.39 (11)	C20—O20—Fe1	123.03 (12)
C6—N2—N3	113.63 (15)	O13—Cl10—O12	109.10 (10)
C6—N2—Fe1	114.27 (12)	O13—Cl10—O14	110.30 (10)
N3—N2—Fe1	132.09 (12)	O12—Cl10—O14	110.33 (10)
C7—N3—N2	111.33 (15)	O13—Cl10—O11	108.75 (10)
C12—N4—C8	116.48 (17)	O12—Cl10—O11	108.62 (9)
N1—C1—C2	122.82 (17)	O14—Cl10—O11	109.71 (9)
C3—C2—C1	119.05 (17)

O20—Fe1—N1—C1	92.67 (15)	Fe1—N2—C6—C5	−2.5 (2)
O20ⁱ—Fe1—N1—C1	−87.33 (15)	N3—N2—C6—S1	−0.96 (19)
N2ⁱ—Fe1—N1—C1	0.65 (16)	Fe1—N2—C6—S1	178.04 (8)
N2—Fe1—N1—C1	−179.35 (16)	N1—C5—C6—N2	−2.2 (2)
O20—Fe1—N1—C5	−93.28 (12)	C4—C5—C6—N2	178.55 (16)
O20ⁱ—Fe1—N1—C5	86.72 (12)	N1—C5—C6—S1	177.18 (13)
N2ⁱ—Fe1—N1—C5	174.71 (12)	C4—C5—C6—S1	−2.0 (3)
N2—Fe1—N1—C5	−5.29 (12)	C7—S1—C6—N2	0.74 (14)
O20—Fe1—N2—C6	96.46 (13)	C7—S1—C6—C5	−178.71 (16)
O20ⁱ—Fe1—N2—C6	−83.54 (13)	N2—N3—C7—C8	−178.46 (16)
N1ⁱ—Fe1—N2—C6	−175.97 (12)	N2—N3—C7—S1	−0.07 (19)
N1—Fe1—N2—C6	4.03 (12)	C6—S1—C7—N3	−0.37 (15)
O20—Fe1—N2—N3	−84.78 (15)	C6—S1—C7—C8	178.09 (15)
O20ⁱ—Fe1—N2—N3	95.22 (15)	C12—N4—C8—C9	−0.7 (3)
N1ⁱ—Fe1—N2—N3	2.79 (16)	C12—N4—C8—C7	179.92 (17)
N1—Fe1—N2—N3	−177.21 (16)	N3—C7—C8—N4	−163.82 (17)
C6—N2—N3—C7	0.7 (2)	S1—C7—C8—N4	17.9 (2)
Fe1—N2—N3—C7	−178.11 (13)	N3—C7—C8—C9	16.8 (3)
C5—N1—C1—C2	0.7 (3)	S1—C7—C8—C9	−161.50 (14)
Fe1—N1—C1—C2	174.61 (13)	N4—C8—C9—C10	0.0 (3)
N1—C1—C2—C3	−0.5 (3)	C7—C8—C9—C10	179.33 (17)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—C11	0.3 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	0.1 (3)
C1—N1—C5—C4	−0.4 (3)	C8—N4—C12—C11	1.2 (3)
Fe1—N1—C5—C4	−175.14 (13)	C10—C11—C12—N4	−0.9 (3)
C1—N1—C5—C6	−179.67 (15)	N2ⁱ—Fe1—O20—C20	−124.06 (14)
Fe1—N1—C5—C6	5.64 (19)	N2—Fe1—O20—C20	55.94 (14)
C3—C4—C5—N1	−0.1 (3)	N1ⁱ—Fe1—O20—C20	−47.76 (14)
C3—C4—C5—C6	179.08 (16)	N1—Fe1—O20—C20	132.24 (14)
N3—N2—C6—C5	178.53 (15)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···O11	0.78 (3)	1.91 (3)	2.690 (2)	178 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···O11	0.78 (3)	1.91 (3)	2.690 (2)	178 (3)

Acknowledgements

Financial support by the European Social Fund, by the Ministry of Science, Research and the Arts Baden-Württemberg within the Margarete von Wrangell Program, the Baden-Württemberg Stiftung within the Eliteprogramme for Postdocs, the Fonds der Chemischen Industrie (FCI) and the Universität Freiburg is gratefully acknowledged.

References

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Volume 70| Part 7| July 2014| Pages m252-m253

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