Syntheses and crystal structures of three [M(acac)2(TMEDA)] complexes (M = Mn, Fe and Zn)

Halz, J.H.; Heiser, C.; Wagner, C.; Merzweiler, K.

doi:10.1107/S2056989019016372

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Volume 76| Part 1| January 2020| Pages 66-71

https://doi.org/10.1107/S2056989019016372

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Syntheses and crystal structures of three [M(acac)₂(TMEDA)] complexes (M = Mn, Fe and Zn)

Jan Henrik Halz,^a Christian Heiser,^a Christoph Wagner ^a and Kurt Merzweiler ^a ^*

^aMartin-Luther-Universität Halle-Wittenberg, Naturwissenschaftliche Fakultät II, Institut für Chemie, D-06099 Halle, Germany
^*Correspondence e-mail: kurt.merzweiler@chemie.uni-halle.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 September 2019; accepted 4 December 2019; online 1 January 2020)

The complexes bis(acetylacetonato-κ²O,O′)(N,N,N′,N′-tetramethylethylenediamine-κ²N,N′)manganese(II), [Mn(C₅H₇O₂)₂(C₆H₁₆N₂)], bis(acetylacetonato-κ²O,O′)(N,N,N′,N′-tetramethylethylenediamine-κ²N,N′)iron(II), [Fe(C₅H₇O₂)₂(C₆H₁₆N₂)], and bis(acetylacetonato-κ²O,O′)(N,N,N′,N′-tetramethylethylenediamine-κ²N,N′)zinc(II), [Zn(C₅H₇O₂)₂(C₆H₁₆N₂)], were synthesized from the reaction of the corresponding metal acetylacetonates [M(acac)₂(H₂O)₂] with N,N,N′,N′-tetramethylethylenediamine (TMEDA) in toluene. Each of the complexes displays a central metal atom which is nearly octahedrally surrounded by two chelating acac and one chelating TMEDA ligand, resulting in an N₂O₄ coordination set. Despite the chemical similarity of the complex units, the packing patterns for compounds 1–3 are different and thus the crystal structures are not isotypic.

Keywords: crystal structure; acetylacetonate; tetramethylethylenediamine; transition metal complex.

CCDC references: 1969941; 1969940; 1969939

1. Chemical context

Pentane-2,4-dionate (acac) and ethylenediamine derivatives are amongst the most widely used chelate ligands in transition metal chemistry. The crystal structures of mixed complexes [M(acac)₂(TMEDA)] (TMEDA = N,N,N′,N′-tetramethylethylenediamine) containing both types of ligands have been reported for several divalent metals, e.g. M = V (Ma et al., 1999 ), Co (Pasko et al., 2004 ), Ni (Trimmel et al., 2002 ; Zeller et al., 2004 ) and Ru (Halbach et al., 2012 ). The synthesis of [Zn(acac)₂(TMEDA)] was reported recently in conjunction with the Ru derivative but without crystal structure determination (Halbach et al., 2012). Typically, [M(acac)₂(TMEDA)] complexes are used as valuable starting materials for the preparation of organometallic and coordination compounds (Kaschube et al. 1988 ; Nelkenbaum et al., 2005 ; Albrecht et al., 2019 ). Moreover, there is an increasing interest in [M(acac)₂(TMEDA)] and related [M(hfa)₂(TMEDA)] (hfa = 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) complexes as precursor materials for CVD deposition of Co₃O₄ (Pasko et al., 2004), Fe₂O₃ (Barreca et al., 2012 ) and MnF₂ (Malandrino et al., 2012 ).

Typically, [M(acac)₂(TMEDA)] complexes are synthesized from the reaction of the metal acetylacetonates with TMEDA. Following this procedure, we obtained the complexes [Mn(acac)₂(TMEDA)] (1), [Fe(acac)₂(TMEDA)] (2) and [Zn(acac)₂(TMEDA)] (3) from the corresponding dihydrates [M(acac)₂(H₂O)₂] and TMEDA in toluene as solvent. Recrystallization from n-hexane at 248 K afforded [Mn(acac)₂(TMEDA)] (1) as yellow, [Fe(acac)₂(TMEDA)] (2) as red–brown and [Zn(acac)₂(TMEDA)] (3) as colorless products. Determination of the magnetic moments for [Mn(acac)₂(TMEDA)] (5.7 B.M.) and [Fe(acac)₂(TMEDA)] (5.1 B.M.) indicates a high-spin configuration in both cases.

2. Structural commentary

Compounds 1–3 crystallize in the monoclinic system, space group P2₁/n with Z = 4. However, despite the similarity of the lattice parameters and the analogous molecular structures, complexes 1–3 are not isotypic. The crystal structures consist of discrete complex molecules [M(acac)₂TMEDA] in which the central metal atoms are coordinated nearly octahedrally by four oxygen atoms of two acac ligands and two nitrogen atoms of the TMEDA ligand (Figs. 1–3 ). Mn complex 1 exhibits Mn—O and Mn—N distances of 2.127 (1)–2.150 (1) Å and 2.356 (2)–2.364 (2) Å, respectively (Table 1). Similar geometric parameters have been reported for [Mn(acac)₂(H₂O)₂] [Mn—O: 2.123 (8)–2.142 (8) Å; Montgomery & Lingafelter, 1968 ], [Mn(acac)₂(1,10-phenanthroline)] [Mn—O: 2.116 (5)–2.152 (5) Å, Mn—N: 2.307 (5) Å; Stephens, 1977 ], [Mn(acac)₂(2,2′-bipyridine)] [Mn—O: 2.148 (2)–2.158 (2) Å, Mn—N: 2.283 (2)–2.288 (3) Å; van Gorkum et al., 2005 ] or [Mn(hfa)₂(TMEDA)] [Mn—O: 2.139 (4)–2.178 (4) Å, Mn—N: 2.299 (5)—2.307 (5) Å; Malandrino et al., 2012].

Table 1
Selected geometric parameters (Å, °) for 1

Mn—O1	2.1271 (13)	Mn—O4	2.1365 (12)
Mn—O2	2.1500 (12)	Mn—N1	2.3643 (15)
Mn—O3	2.1375 (12)	Mn—N2	2.3560 (15)

O1—Mn—O2	83.61 (5)	O2—Mn—N2	90.36 (5)
O1—Mn—O3	107.00 (5)	O3—Mn—O4	83.78 (5)
O1—Mn—O4	93.25 (5)	O3—Mn—N1	165.43 (5)
O1—Mn—N1	86.01 (5)	O3—Mn—N2	90.61 (5)
O1—Mn—N2	161.29 (6)	O4—Mn—N1	89.07 (5)
O2—Mn—O3	89.71 (5)	O4—Mn—N2	94.95 (6)
O2—Mn—O4	171.63 (5)	N1—Mn—N2	77.34 (6)
O2—Mn—N1	98.41 (5)

Figure 1
Molecular structure of complex 1 showing the labeling scheme. Displacement ellipsoids drawn at 50% probability level, H atoms are omitted.

Figure 2
Molecular structure of complex 2 showing the labeling scheme. Displacement ellipsoids drawn at 50% probability level, H atoms are omitted.

Figure 3
Molecular structure of complex 3 showing the labeling scheme. Displacement ellipsoids drawn at 50% probability level, H atoms are omitted.

The Fe—O and Fe—N distances in compound 2 [2.050 (1)–2.097 (1) Å and 2.302 (1)–2.318 (1) Å, respectively; Table 2] are on average shorter than the corresponding Mn—O and Mn—N distances in complex 1. The Fe—O and Fe—N distances compare well with the data that have been observed in the compounds [Fe(acac)₂(H₂O)₂] [Fe—O: 2.034–2.041 Å; Tsodikov et al., 1995 ], [Fe(hfa)₂(picoline)₂] [Fe—O: 2.057 (1) Å, Fe—N: 2.190 (3)–2.224 (3) Å; Novitchi et al., 2017 ] or [Fe(hfa)₂(TMEDA)] [Fe—O: 2.064 (1)–2.094 (1), Fe—N: 2.229 (2) Å; Dickman et al., 1998 ].

Table 2
Selected geometric parameters (Å, °) for 2

Fe—O1	2.0876 (10)	Fe—O4	2.0520 (9)
Fe—O2	2.0497 (10)	Fe—N1	2.3021 (12)
Fe—O3	2.0970 (10)	Fe—N2	2.3184 (12)

O1—Fe—O2	85.58 (4)	O2—Fe—N2	84.18 (4)
O1—Fe—O3	93.98 (4)	O3—Fe—O4	86.00 (4)
O1—Fe—O4	99.11 (4)	O3—Fe—N1	170.93 (4)
O1—Fe—N1	92.44 (4)	O3—Fe—N2	95.43 (4)
O1—Fe—N2	166.73 (4)	O4—Fe—N1	86.66 (4)
O2—Fe—O3	95.84 (4)	O4—Fe—N2	90.87 (4)
O2—Fe—O4	174.85 (4)	N1—Fe—N2	79.35 (4)
O2—Fe—N1	91.04 (5)

[Zn(acac)₂(TMEDA)] (3) displays Zn—O and Zn—N distances of 2.061 (1)–2.077 (1) and 2.253 (1)–2.272 (1) Å, respectively (Table 3). In comparison with the iron complex 2, the average metal–oxygen distances and metal–nitrogen distances are slightly shortened. On the whole, the Zn—O and Zn—N distances in compound 3 are similar to those observed in the related compounds [Zn(acac)₂(H₂O)₂] [Zn—O: 2.032 (1)–2.049 (1) Å; Harbach et al., 2003 ], [Zn(acac)₂(1,10-phenanthroline)] [Zn—O: 2.044 (1)–2.085 (1) Å, Zn—N: 2.196 (1) Å; Brahma et al., 2008 ], [Zn(acac)₂(2,2′-bipyridine)] [Zn—O: 2.051 (1)–2.089 (1) Å, Zn—N: 2.197 (2)–2.208 (2) Å; Brahma et al., 2008] or [Zn(hfa)₂(TMEDA)] [Zn—O: 2.103 (1)–2.126 (1) Å, Zn—N: 2.145 (1)–2.151 (1) Å; Ni et al., 2005 ].

Table 3
Selected geometric parameters (Å, °) for 3

Zn—O1	2.0771 (12)	Zn—O4	2.0607 (10)
Zn—O2	2.0611 (11)	Zn—N1	2.2722 (13)
Zn—O3	2.0645 (11)	Zn—N2	2.2533 (13)

O1—Zn—O2	87.50 (4)	O2—Zn—N2	89.57 (5)
O1—Zn—O3	101.58 (5)	O3—Zn—O4	87.96 (4)
O1—Zn—O4	88.49 (4)	O3—Zn—N1	168.61 (5)
O1—Zn—N1	89.28 (5)	O3—Zn—N2	89.09 (5)
O1—Zn—N2	168.94 (5)	O4—Zn—N1	88.92 (5)
O2—Zn—O3	90.18 (5)	O4—Zn—N2	94.86 (5)
O2—Zn—O4	175.16 (4)	N1—Zn—N2	80.27 (5)
O2—Zn—N1	93.76 (5)

In general, the above-mentioned [M(hfa)₂(TMEDA)] (M = Mn, Fe, Zn) complexes exhibit shorter M—N distances than the corresponding [M(acac)₂(TMEDA)] complexes. This effect is probably due to the electron-withdrawing effect of the CF₃ groups of the hfa ligands.

The iron complex 2 displays a subtle elongation (0.041 Å) of the Fe—O bonds trans to the N atoms with respect to the Fe—O bonds trans to oxygen. A similar effect was observed for [Co(acac)₂(TMEDA)] (Pasko et al., 2004). In the case of the Mn and Zn complexes 1 and 3, the trans influence is negligible as reported for [Ni(acac)₂(TMEDA)] (Trimmel et al., 2002) and [Ru(acac)₂(TMEDA)] (Halbach et al., 2012). A reverse effect with a shortening of the Zn—O bonds trans to nitrogen was detected for [Zn(acac)₂(2,2′-bipyridine)] and [Zn(acac)₂(1,10-phenanthroline)] (Brahma et al., 2008).

Each of the complexes 1–3 exhibits nearly planar six-membered acac-M chelate rings. The maximum deviation from planarity, as indicated by the dihedral angle between the M/O1/O2 (M/O3/O4) plane of the chelate ring and the best plane through O1/C2/C3/C4/O2 (O3/C7/C8/C9/O4), is 6.2 (1)° in the case of the zinc complex 3. PLATON (Spek, 2009 ) was used to calculate the dihedral angles. The five-membered M-TMEDA ring adopts a twist conformation with approximate C₂ symmetry. As a result of the centrosymmetric crystal structure, both types of the enantiomeric chelate rings with λ and δ conformations are present.

The MO₄N₂ coordination polyhedra in compounds 1–3 deviate moderately from a regular octahedron. The O—M—O angles are in the range 171.7 (1)° (complex 1) to 175.2 (1)° (complex 3) and the N—M–-O angles vary from 161.3 (1)° (complex 1) to 170.9 (1)° (complex 2). The smallest acac bite angle is observed in compound 1 [83.6 (1)°], the largest is found in compound 3 [88.0 (1)°]. In the case of the TMEDA ligands, the bite angles are marginally smaller with a range between 77.3 (1)° (compound 1) and 80.3 (1)° (compound 3). Overall, the distortion of the MO₄N₂ octahedra in compounds 1–3 is very similar to that observed in the analogous V, Ni and Co complexes [M(acac)₂(TMEDA)].

3. Supramolecular features

The packing of the [M(acac)₂(TMEDA)] units is dominated by van der Waals interactions. The mutual arrangement of the complex units 1–3 is similar but not identical (Figs. 4–6 ). In the case of the iron compound 2 there is also a contribution from weak C—H⋯O hydrogen bridges (Table 4). As a result, the complexes are associated by R₂²(8) type motifs, forming centrosymmetric dimers (Fig. 5).

Table 4
Hydrogen-bond geometry (Å, °) for 2

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H2⋯O1ⁱ	0.96	2.62	3.5269 (18)	157
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 4
Crystal structure of compound 1, viewed along the b axis.

Figure 5
Crystal structure of compound 2, viewed along the b axis. The intermolecular C—H⋯O hydrogen bonds are shown as dashed lines.

Figure 6
Crystal structure of compound 3, viewed along the b axis.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.40, February 2019 update; Groom et al., 2016 ) for complexes with a composition [M(acac)₂(TMEDA)] analogous to 1–3 revealed the crystal structures for the M = V, Ni, Co and Ru derivatives (Ma et al., 1999; Pasko et al., 2004; Trimmel et al., 2002; Zeller et al., 2004; Halbach et al., 2012). However, none of these complexes is isotypic with the three title compounds. In the case of the related hfa derivatives, complexes of the type [M(hfa)₂(TMEDA)] (hfa = 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) with M = Mg, Mn, Fe, Co, Cu and Zn have been reported.

5. Synthesis and crystallization

TMEDA (7.5 ml, 5.8 g, 50 mmol) was added to a suspension of [M(acac)₂(H₂O)₂] (25 mmol, M = Mn: 9.71 g, Fe: 9.73 g, Zn: 9.97 g) in toluene (30 ml). The suspension was stirred at 323 K for 2 h. After removal of the solvent under reduced pressure, n-hexane (25 ml) was added and insoluble parts were filtered off. The filtrates were kept at 248 K to obtain the products as yellow (1), red–brown (2) and colourless (3) crystalline solids in yields around 90%.

Characterization

[Mn(acac)₂TMEDA] (1)

C₁₆H₃₀MnN₂O₄ calculated C 52.03, H 8.19, N 7.59%, found: C 51.71, H 8.13, N 7.14%; IR (ATR): ν = 3067 w, 2993 w, 2970 w, 2917 w, 2986 w, 2860 w, 2828 w, 2788 w, 2772 w, 1595 m, 1512 s, 1468 m, 1449 m, 1412 s, 1391 m, 1353 m, 1288 m, 1251 m, 1190 w, 1159 w, 1124 w, 1095 w, 1063 w, 1045 m, 1026 w, 1011 m, 950 m, 934 w, 913 m, 794 m, 771 w, 751 m, 650 w, 583 w, 526 m, 468 w, 448 w, 436 w, 400 s, 325 m, 212 s cm⁻¹.

M.p.: 362 K.

[Fe(acac)₂TMEDA] (2)

C₁₆H₃₀FeN₂O₄ calculated C 51.90, H 8.17, N 7.57%, found: C 51.75, H 8.08, N 7.23%; IR (ATR): ν = 3074 w, 3001 w, 2967 w, 2911 w, 2869 w, 2836 w, 2790 w, 1583 m, 1510 s, 1455 m, 1411 s, 1382 m, 1357 w, 1289 m, 1274 w, 1256 m, 1188 w, 1165 w, 1127 w, 1101 w, 1030 w 1012 m, 952 m, 917 m, 793 m, 762 s, 651 w, 583 w, 543 m, 475 w, 436 w, 404 w, 382 s, 296 w, 265 m, 227 s cm⁻¹.

M.p.: 361 K.

[Zn(acac)₂TMEDA] (3)

C₁₆H₃₀N₂O₄Zn calculated C 50.60, H 7.96, N 7.38%, found: C 50.33, H 8.13, N 7.23%; ¹H-NMR (CDCl₃, 399.962 MHz) δ = 5.15 [s, 2H, C(O)CHC(O)], 2.49 (s, 4H, Me₂N-CH₂), 2.31 (s, 12H, (CH₃)₂N), 1.85 [s, 12H, CH₃C(O)]; ¹³C-NMR (CDCl₃,100.581 MHz) δ = 190.9 [C(O)], 98.4 [C(O)CHC(O)], 56.5 (NCH₂), 46.6 [(CH₃)₂N], 28.3 (C(O)CH₃) ppm; IR (ATR): ν = 3071 w, 3001 w, 2975 w, 2881 w, 2835 w, 2792 w, 1615 m, 1593 m, 1515 s, 1469 m, 1455 m, 1411 m, 1390 s, 1354 m, 1290 m, 1252 m, 1190 w, 1166 w, 1128 w, 1101 w, 1061 w, 1032 m, 1013 s, 953 m, 936 w, 918 m, 798 m, 770 m, 754 m, 649 w, 584 w, 543 m, 474 w, 440 m, 405 s, 382 w, 208 s cm⁻¹.

M.p.: 362 K.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. All hydrogen atoms were positioned geometrically and refined using a riding model with U_iso(H) = 1.2(CH and CH₂) or 1.5(CH₃) times U_eq(C). Reflections with error/e.s.d. > 8 were omitted. Error/e.s.d. = (wD²/<wD²>)^0.5 where D = F_o² - F_c².

Table 5
Experimental details

	1	2	3
Crystal data
Chemical formula	[Mn(C₅H₇O₂)₂(C₆H₁₆N₂)]	[Fe(C₅H₇O₂)₂(C₆H₁₆N₂)]	[Zn(C₅H₇O₂)₂(C₆H₁₆N₂)]
M_r	369.36	370.27	379.79
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n	Monoclinic, P2₁/n
Temperature (K)	213	213	200
a, b, c (Å)	10.4234 (4), 14.3123 (5), 13.6047 (5)	10.2021 (3), 15.4708 (4), 12.4881 (4)	10.2335 (3), 14.2134 (6), 13.6738 (5)
β (°)	103.154 (3)	95.382 (3)	101.208 (3)
V (Å³)	1976.33 (13)	1962.37 (10)	1950.96 (12)
Z	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.69	0.79	1.28
Crystal size (mm)	0.35 × 0.25 × 0.20	0.26 × 0.25 × 0.23	0.45 × 0.39 × 0.33

Data collection
Diffractometer	STOE IPDS 2	STOE IPDS 2	STOE IPDS 2T
Absorption correction	Numerical (X-AREA; Stoe & Cie, 2016 )	Numerical (X-AREA; Stoe & Cie, 2016)	Numerical (X-AREA; Stoe & Cie, 2016)
T_min, T_max	0.798, 0.912	0.814, 0.894	0.627, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections	12607, 4139, 3475	18586, 5276, 4425	22385, 4124, 3456
R_int	0.030	0.037	0.047
(sin θ/λ)_max (Å⁻¹)	0.634	0.688	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.06	0.031, 0.086, 1.04	0.027, 0.076, 1.07
No. of reflections	4139	5276	4124
No. of parameters	216	216	216
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24	0.32, −0.22	0.37, −0.26
Computer programs: X-AREA (Stoe & Cie, 2016), SHELXT2014/7 (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg, 2019 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 1969941; 1969940; 1969939

Crystal structure: contains datablocks 1, 2, 3. DOI: https://doi.org/10.1107/S2056989019016372/wm5524sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989019016372/wm55241sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989019016372/wm55242sup3.hkl

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989019016372/wm55243sup4.hkl

checkCIF report

Computing details top

For all structures, data collection: X-AREA (Stoe & Cie, 2016); cell refinement: X-AREA (Stoe & Cie, 2016); data reduction: X-AREA (Stoe & Cie, 2016); program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2019); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(acetylacetonato-κ²O,O')(N,N,N',N'-tetramethylethylenediamine-κ²N,N')manganese(II) (1) top

Crystal data top

[Mn(C₅H₇O₂)₂(C₆H₁₆N₂)]	F(000) = 788
M_r = 369.36	D_x = 1.241 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4234 (4) Å	Cell parameters from 13227 reflections
b = 14.3123 (5) Å	θ = 1.4–27.2°
c = 13.6047 (5) Å	µ = 0.69 mm⁻¹
β = 103.154 (3)°	T = 213 K
V = 1976.33 (13) Å³	Block, clear yellow
Z = 4	0.35 × 0.25 × 0.20 mm

Data collection top

STOE IPDS 2 diffractometer	4139 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus, Incoatec Iµs	3475 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.030
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 2.1°
rotation method scans	h = −13→13
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)	k = −17→18
T_min = 0.798, T_max = 0.912	l = −17→16
12607 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0447P)² + 0.6571P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4139 reflections	Δρ_max = 0.22 e Å⁻³
216 parameters	Δρ_min = −0.24 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
Mn	0.50579 (2)	0.74721 (2)	0.49407 (2)	0.04120 (11)
O1	0.67069 (13)	0.65614 (9)	0.53426 (10)	0.0602 (3)
O2	0.64605 (12)	0.84003 (9)	0.45153 (11)	0.0554 (3)
O3	0.50538 (13)	0.83274 (9)	0.62280 (10)	0.0546 (3)
O4	0.38216 (14)	0.65820 (9)	0.55845 (10)	0.0565 (3)
N1	0.44810 (15)	0.65991 (11)	0.34289 (11)	0.0523 (4)
N2	0.33093 (14)	0.83481 (11)	0.39666 (12)	0.0533 (4)
C1	0.8801 (3)	0.5868 (2)	0.5617 (2)	0.0943 (9)
H1	0.8477	0.5484	0.6086	0.141*
H3	0.9667	0.6089	0.5928	0.141*
H2	0.8838	0.5506	0.5029	0.141*
C2	0.7888 (2)	0.66910 (16)	0.53114 (14)	0.0593 (5)
C3	0.8405 (2)	0.75159 (16)	0.50286 (17)	0.0664 (6)
H4	0.9308	0.7532	0.5070	0.080*
C4	0.76938 (18)	0.83223 (14)	0.46880 (15)	0.0568 (5)
C5	0.8448 (2)	0.91826 (18)	0.4505 (2)	0.0885 (8)
H5	0.9136	0.9006	0.4178	0.133*
H6	0.8827	0.9477	0.5138	0.133*
H7	0.7860	0.9611	0.4082	0.133*
C6	0.4607 (2)	0.89848 (16)	0.77048 (18)	0.0714 (6)
H8	0.5521	0.9144	0.7936	0.107*
H10	0.4263	0.8782	0.8267	0.107*
H9	0.4125	0.9522	0.7400	0.107*
C7	0.44674 (17)	0.82045 (13)	0.69347 (13)	0.0498 (4)
C8	0.3712 (2)	0.74328 (13)	0.70557 (16)	0.0568 (5)
H11	0.3367	0.7416	0.7629	0.068*
C9	0.34284 (19)	0.66822 (13)	0.63927 (15)	0.0558 (4)
C10	0.2576 (3)	0.59062 (18)	0.6645 (2)	0.0920 (9)
H12	0.2171	0.6107	0.7176	0.138*
H13	0.3109	0.5365	0.6861	0.138*
H14	0.1904	0.5754	0.6057	0.138*
C11	0.3189 (2)	0.69516 (18)	0.28808 (16)	0.0693 (6)
H16	0.2506	0.6684	0.3173	0.083*
H15	0.3030	0.6753	0.2182	0.083*
C12	0.3114 (2)	0.79961 (18)	0.29216 (16)	0.0703 (6)
H17	0.3781	0.8263	0.2612	0.084*
H18	0.2260	0.8199	0.2535	0.084*
C13	0.4397 (3)	0.55956 (14)	0.36410 (18)	0.0728 (6)
H20	0.3743	0.5496	0.4026	0.109*
H21	0.5236	0.5378	0.4018	0.109*
H19	0.4156	0.5258	0.3016	0.109*
C14	0.5481 (2)	0.67378 (17)	0.28339 (15)	0.0647 (5)
H24	0.5227	0.6403	0.2208	0.097*
H22	0.6316	0.6509	0.3207	0.097*
H23	0.5553	0.7392	0.2698	0.097*
C15	0.21051 (19)	0.82208 (18)	0.43395 (18)	0.0711 (6)
H25	0.1889	0.7568	0.4331	0.107*
H27	0.1393	0.8557	0.3914	0.107*
H26	0.2246	0.8454	0.5017	0.107*
C16	0.3638 (2)	0.93462 (15)	0.4003 (2)	0.0784 (7)
H29	0.2945	0.9685	0.3560	0.118*
H28	0.4448	0.9435	0.3793	0.118*
H30	0.3736	0.9572	0.4680	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn	0.03895 (15)	0.04541 (18)	0.03899 (15)	−0.00103 (10)	0.00838 (10)	0.00066 (10)
O1	0.0612 (8)	0.0613 (8)	0.0561 (8)	0.0159 (6)	0.0090 (6)	0.0076 (6)
O2	0.0433 (6)	0.0523 (7)	0.0725 (9)	−0.0029 (5)	0.0168 (6)	0.0043 (6)
O3	0.0591 (7)	0.0537 (7)	0.0526 (7)	−0.0101 (6)	0.0160 (6)	−0.0103 (6)
O4	0.0700 (8)	0.0495 (7)	0.0567 (8)	−0.0136 (6)	0.0282 (6)	−0.0085 (6)
N1	0.0538 (8)	0.0612 (9)	0.0426 (8)	−0.0076 (7)	0.0124 (6)	−0.0048 (7)
N2	0.0431 (7)	0.0595 (9)	0.0546 (9)	0.0040 (7)	0.0054 (6)	0.0063 (7)
C1	0.0924 (18)	0.108 (2)	0.0744 (15)	0.0575 (16)	0.0027 (13)	−0.0049 (14)
C2	0.0561 (11)	0.0758 (14)	0.0411 (9)	0.0216 (10)	0.0009 (8)	−0.0109 (9)
C3	0.0392 (9)	0.0933 (17)	0.0658 (13)	0.0089 (10)	0.0100 (9)	−0.0196 (11)
C4	0.0454 (9)	0.0699 (12)	0.0589 (11)	−0.0094 (9)	0.0197 (8)	−0.0190 (9)
C5	0.0657 (14)	0.0870 (17)	0.124 (2)	−0.0267 (13)	0.0450 (15)	−0.0239 (16)
C6	0.0770 (14)	0.0710 (14)	0.0676 (13)	0.0026 (11)	0.0191 (11)	−0.0237 (11)
C7	0.0473 (9)	0.0556 (10)	0.0450 (9)	0.0070 (8)	0.0076 (7)	−0.0062 (8)
C8	0.0628 (12)	0.0614 (12)	0.0525 (10)	−0.0014 (9)	0.0262 (9)	−0.0058 (8)
C9	0.0581 (10)	0.0560 (11)	0.0590 (11)	−0.0039 (9)	0.0253 (9)	−0.0014 (9)
C10	0.110 (2)	0.0822 (17)	0.104 (2)	−0.0364 (15)	0.0658 (17)	−0.0179 (15)
C11	0.0544 (11)	0.0974 (17)	0.0505 (11)	−0.0062 (11)	0.0004 (9)	−0.0157 (11)
C12	0.0594 (12)	0.0975 (17)	0.0483 (11)	0.0137 (11)	0.0000 (9)	0.0114 (11)
C13	0.1012 (17)	0.0554 (12)	0.0660 (13)	−0.0177 (11)	0.0276 (12)	−0.0174 (10)
C14	0.0666 (12)	0.0849 (15)	0.0466 (10)	−0.0047 (11)	0.0210 (9)	−0.0051 (10)
C15	0.0432 (10)	0.0931 (16)	0.0760 (14)	0.0085 (10)	0.0118 (9)	0.0033 (12)
C16	0.0653 (13)	0.0614 (13)	0.1024 (19)	0.0125 (10)	0.0063 (12)	0.0203 (12)

Geometric parameters (Å, º) top

Mn—O1	2.1271 (13)	C6—H10	0.9600
Mn—O2	2.1500 (12)	C6—H9	0.9600
Mn—O3	2.1375 (12)	C6—C7	1.515 (3)
Mn—O4	2.1365 (12)	C7—C8	1.388 (3)
Mn—N1	2.3643 (15)	C8—H11	0.9300
Mn—N2	2.3560 (15)	C8—C9	1.391 (3)
O1—C2	1.255 (2)	C9—C10	1.510 (3)
O2—C4	1.258 (2)	C10—H12	0.9600
O3—C7	1.263 (2)	C10—H13	0.9600
O4—C9	1.266 (2)	C10—H14	0.9600
N1—C11	1.472 (3)	C11—H16	0.9700
N1—C13	1.472 (3)	C11—H15	0.9700
N1—C14	1.472 (2)	C11—C12	1.499 (4)
N2—C12	1.478 (3)	C12—H17	0.9700
N2—C15	1.468 (2)	C12—H18	0.9700
N2—C16	1.467 (3)	C13—H20	0.9600
C1—H1	0.9600	C13—H21	0.9600
C1—H3	0.9600	C13—H19	0.9600
C1—H2	0.9600	C14—H24	0.9600
C1—C2	1.512 (3)	C14—H22	0.9600
C2—C3	1.388 (3)	C14—H23	0.9600
C3—H4	0.9300	C15—H25	0.9600
C3—C4	1.393 (3)	C15—H27	0.9600
C4—C5	1.512 (3)	C15—H26	0.9600
C5—H5	0.9600	C16—H29	0.9600
C5—H6	0.9600	C16—H28	0.9600
C5—H7	0.9600	C16—H30	0.9600
C6—H8	0.9600

O1—Mn—O2	83.61 (5)	C7—C6—H8	109.5
O1—Mn—O3	107.00 (5)	C7—C6—H10	109.5
O1—Mn—O4	93.25 (5)	C7—C6—H9	109.5
O1—Mn—N1	86.01 (5)	O3—C7—C6	115.89 (17)
O1—Mn—N2	161.29 (6)	O3—C7—C8	125.92 (17)
O2—Mn—O3	89.71 (5)	C8—C7—C6	118.18 (17)
O2—Mn—O4	171.63 (5)	C7—C8—H11	117.2
O2—Mn—N1	98.41 (5)	C7—C8—C9	125.50 (18)
O2—Mn—N2	90.36 (5)	C9—C8—H11	117.2
O3—Mn—O4	83.78 (5)	O4—C9—C8	125.99 (17)
O3—Mn—N1	165.43 (5)	O4—C9—C10	115.94 (18)
O3—Mn—N2	90.61 (5)	C8—C9—C10	118.07 (18)
O4—Mn—N1	89.07 (5)	C9—C10—H12	109.5
O4—Mn—N2	94.95 (6)	C9—C10—H13	109.5
N1—Mn—N2	77.34 (6)	C9—C10—H14	109.5
C2—O1—Mn	129.95 (14)	H12—C10—H13	109.5
C4—O2—Mn	128.56 (13)	H12—C10—H14	109.5
C7—O3—Mn	129.44 (12)	H13—C10—H14	109.5
C9—O4—Mn	129.29 (12)	N1—C11—H16	109.2
C11—N1—Mn	106.37 (12)	N1—C11—H15	109.2
C13—N1—Mn	111.10 (12)	N1—C11—C12	111.88 (17)
C13—N1—C11	110.20 (18)	H16—C11—H15	107.9
C13—N1—C14	108.71 (17)	C12—C11—H16	109.2
C14—N1—Mn	109.60 (12)	C12—C11—H15	109.2
C14—N1—C11	110.86 (16)	N2—C12—C11	112.25 (17)
C12—N2—Mn	106.22 (12)	N2—C12—H17	109.2
C15—N2—Mn	110.63 (12)	N2—C12—H18	109.2
C15—N2—C12	110.40 (17)	C11—C12—H17	109.2
C16—N2—Mn	110.75 (12)	C11—C12—H18	109.2
C16—N2—C12	110.14 (18)	H17—C12—H18	107.9
C16—N2—C15	108.69 (17)	N1—C13—H20	109.5
H1—C1—H3	109.5	N1—C13—H21	109.5
H1—C1—H2	109.5	N1—C13—H19	109.5
H3—C1—H2	109.5	H20—C13—H21	109.5
C2—C1—H1	109.5	H20—C13—H19	109.5
C2—C1—H3	109.5	H21—C13—H19	109.5
C2—C1—H2	109.5	N1—C14—H24	109.5
O1—C2—C1	115.9 (2)	N1—C14—H22	109.5
O1—C2—C3	125.51 (18)	N1—C14—H23	109.5
C3—C2—C1	118.6 (2)	H24—C14—H22	109.5
C2—C3—H4	117.1	H24—C14—H23	109.5
C2—C3—C4	125.86 (18)	H22—C14—H23	109.5
C4—C3—H4	117.1	N2—C15—H25	109.5
O2—C4—C3	125.44 (19)	N2—C15—H27	109.5
O2—C4—C5	116.4 (2)	N2—C15—H26	109.5
C3—C4—C5	118.17 (19)	H25—C15—H27	109.5
C4—C5—H5	109.5	H25—C15—H26	109.5
C4—C5—H6	109.5	H27—C15—H26	109.5
C4—C5—H7	109.5	N2—C16—H29	109.5
H5—C5—H6	109.5	N2—C16—H28	109.5
H5—C5—H7	109.5	N2—C16—H30	109.5
H6—C5—H7	109.5	H29—C16—H28	109.5
H8—C6—H10	109.5	H29—C16—H30	109.5
H8—C6—H9	109.5	H28—C16—H30	109.5
H10—C6—H9	109.5

Mn—O1—C2—C1	−177.50 (14)	N1—C11—C12—N2	−60.6 (2)
Mn—O1—C2—C3	2.8 (3)	C1—C2—C3—C4	177.1 (2)
Mn—O2—C4—C3	13.4 (3)	C2—C3—C4—O2	−5.6 (3)
Mn—O2—C4—C5	−166.67 (16)	C2—C3—C4—C5	174.5 (2)
Mn—O3—C7—C6	−176.26 (13)	C6—C7—C8—C9	176.5 (2)
Mn—O3—C7—C8	3.2 (3)	C7—C8—C9—O4	0.7 (4)
Mn—O4—C9—C8	1.1 (3)	C7—C8—C9—C10	−179.4 (2)
Mn—O4—C9—C10	−178.82 (17)	C13—N1—C11—C12	162.74 (17)
Mn—N1—C11—C12	42.22 (19)	C14—N1—C11—C12	−76.9 (2)
Mn—N2—C12—C11	42.41 (19)	C15—N2—C12—C11	−77.6 (2)
O1—C2—C3—C4	−3.2 (3)	C16—N2—C12—C11	162.39 (17)
O3—C7—C8—C9	−3.0 (3)

Bis(acetylacetonato-κ²O,O')(N,N,N',N'-tetramethylethylenediamine-κ²N,N')iron(II) (2) top

Crystal data top

[Fe(C₅H₇O₂)₂(C₆H₁₆N₂)]	F(000) = 792
M_r = 370.27	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2021 (3) Å	Cell parameters from 16780 reflections
b = 15.4708 (4) Å	θ = 1.6–29.6°
c = 12.4881 (4) Å	µ = 0.79 mm⁻¹
β = 95.382 (3)°	T = 213 K
V = 1962.37 (10) Å³	Block, clear reddish brown
Z = 4	0.26 × 0.25 × 0.23 mm

Data collection top

STOE IPDS 2 diffractometer	5276 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus, Incoatec Iµs	4425 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.037
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.3°, θ_min = 2.1°
rotation method scans	h = −13→13
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)	k = −21→20
T_min = 0.814, T_max = 0.894	l = −17→17
18586 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0464P)² + 0.3681P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
5276 reflections	Δρ_max = 0.32 e Å⁻³
216 parameters	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.63613 (15)	0.53037 (11)	0.42322 (12)	0.0444 (3)
H2	0.5847	0.4797	0.4338	0.067*
H3	0.7061	0.5160	0.3800	0.067*
H1	0.5810	0.5739	0.3874	0.067*
C2	0.69359 (13)	0.56425 (9)	0.53071 (11)	0.0352 (3)
C3	0.81769 (14)	0.53357 (9)	0.57243 (12)	0.0396 (3)
H4	0.8603	0.4948	0.5305	0.047*
C4	0.88149 (13)	0.55660 (9)	0.67116 (12)	0.0388 (3)
C5	1.01582 (16)	0.51923 (13)	0.70525 (16)	0.0584 (4)
H7	1.0343	0.4733	0.6572	0.088*
H5	1.0172	0.4970	0.7771	0.088*
H6	1.0813	0.5636	0.7031	0.088*
C6	0.39240 (17)	0.48770 (10)	0.87153 (14)	0.0496 (4)
H10	0.3000	0.4817	0.8499	0.074*
H9	0.4064	0.4888	0.9486	0.074*
H8	0.4391	0.4397	0.8446	0.074*
C7	0.44227 (13)	0.57093 (9)	0.82668 (11)	0.0359 (3)
C8	0.35444 (13)	0.64029 (10)	0.81410 (12)	0.0379 (3)
H11	0.2707	0.6321	0.8359	0.046*
C9	0.38200 (13)	0.72026 (9)	0.77178 (11)	0.0350 (3)
C10	0.27918 (16)	0.79023 (12)	0.77050 (16)	0.0542 (4)
H14	0.2694	0.8171	0.7009	0.081*
H13	0.3059	0.8328	0.8241	0.081*
H12	0.1967	0.7654	0.7857	0.081*
C11	0.78186 (19)	0.85071 (11)	0.76164 (14)	0.0537 (4)
H16	0.7020	0.8793	0.7792	0.064*
H15	0.8440	0.8949	0.7446	0.064*
C12	0.83901 (17)	0.80004 (13)	0.85721 (14)	0.0545 (4)
H17	0.9192	0.7718	0.8398	0.065*
H18	0.8617	0.8393	0.9167	0.065*
C13	0.6596 (2)	0.83936 (13)	0.58754 (16)	0.0593 (4)
H19	0.6381	0.8022	0.5269	0.089*
H21	0.7000	0.8912	0.5641	0.089*
H20	0.5807	0.8539	0.6198	0.089*
C14	0.87086 (16)	0.77473 (12)	0.61406 (14)	0.0519 (4)
H24	0.9042	0.8268	0.5847	0.078*
H22	0.8499	0.7338	0.5572	0.078*
H23	0.9363	0.7506	0.6658	0.078*
C15	0.64471 (18)	0.77489 (13)	0.94987 (14)	0.0549 (4)
H26	0.5825	0.7319	0.9677	0.082*
H25	0.6001	0.8188	0.9060	0.082*
H27	0.6853	0.8005	1.0147	0.082*
C16	0.8174 (2)	0.67090 (14)	0.96194 (14)	0.0619 (5)
H29	0.8834	0.6428	0.9244	0.093*
H28	0.7566	0.6286	0.9840	0.093*
H30	0.8587	0.7000	1.0242	0.093*
Fe	0.65967 (2)	0.67126 (2)	0.73081 (2)	0.03242 (7)
N1	0.75139 (12)	0.79468 (8)	0.66685 (10)	0.0407 (3)
N2	0.74634 (12)	0.73421 (9)	0.89046 (10)	0.0418 (3)
O1	0.62568 (9)	0.61851 (7)	0.57684 (8)	0.0395 (2)
O2	0.83743 (9)	0.60880 (7)	0.73746 (9)	0.0426 (2)
O3	0.55981 (10)	0.57212 (6)	0.80388 (9)	0.0414 (2)
O4	0.48936 (9)	0.74134 (6)	0.73429 (8)	0.0384 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0435 (7)	0.0512 (8)	0.0393 (7)	−0.0086 (6)	0.0082 (6)	−0.0108 (6)
C2	0.0360 (6)	0.0341 (6)	0.0368 (7)	−0.0081 (5)	0.0096 (5)	−0.0039 (5)
C3	0.0380 (7)	0.0368 (7)	0.0453 (8)	0.0022 (5)	0.0111 (6)	−0.0064 (6)
C4	0.0301 (6)	0.0407 (7)	0.0465 (8)	0.0000 (5)	0.0089 (5)	0.0000 (6)
C5	0.0374 (8)	0.0703 (12)	0.0670 (11)	0.0127 (8)	0.0019 (7)	−0.0056 (9)
C6	0.0539 (9)	0.0434 (8)	0.0515 (9)	−0.0121 (7)	0.0050 (7)	0.0076 (7)
C7	0.0380 (6)	0.0369 (7)	0.0328 (6)	−0.0079 (5)	0.0028 (5)	−0.0029 (5)
C8	0.0303 (6)	0.0435 (7)	0.0413 (7)	−0.0049 (5)	0.0102 (5)	−0.0045 (6)
C9	0.0315 (6)	0.0393 (7)	0.0349 (6)	0.0017 (5)	0.0056 (5)	−0.0047 (5)
C10	0.0439 (8)	0.0539 (9)	0.0670 (11)	0.0149 (7)	0.0163 (7)	0.0022 (8)
C11	0.0674 (11)	0.0428 (8)	0.0540 (10)	−0.0207 (8)	0.0222 (8)	−0.0125 (7)
C12	0.0508 (9)	0.0685 (11)	0.0451 (9)	−0.0275 (8)	0.0092 (7)	−0.0158 (8)
C13	0.0626 (11)	0.0614 (11)	0.0559 (10)	−0.0011 (8)	0.0154 (8)	0.0167 (8)
C14	0.0496 (8)	0.0561 (9)	0.0537 (9)	−0.0149 (7)	0.0247 (7)	−0.0073 (7)
C15	0.0550 (9)	0.0690 (11)	0.0429 (8)	−0.0094 (8)	0.0167 (7)	−0.0164 (8)
C16	0.0650 (11)	0.0792 (13)	0.0401 (9)	0.0011 (9)	−0.0027 (8)	−0.0002 (8)
Fe	0.02688 (10)	0.03490 (11)	0.03626 (11)	−0.00268 (7)	0.00714 (7)	−0.00567 (7)
N1	0.0432 (6)	0.0415 (6)	0.0395 (6)	−0.0086 (5)	0.0147 (5)	−0.0039 (5)
N2	0.0395 (6)	0.0513 (7)	0.0354 (6)	−0.0101 (5)	0.0077 (5)	−0.0055 (5)
O1	0.0329 (5)	0.0440 (5)	0.0416 (5)	0.0005 (4)	0.0028 (4)	−0.0112 (4)
O2	0.0313 (5)	0.0535 (6)	0.0429 (5)	0.0021 (4)	0.0031 (4)	−0.0100 (5)
O3	0.0352 (5)	0.0352 (5)	0.0543 (6)	−0.0009 (4)	0.0075 (4)	0.0014 (4)
O4	0.0349 (5)	0.0348 (5)	0.0471 (5)	0.0018 (4)	0.0124 (4)	0.0023 (4)

Geometric parameters (Å, º) top

C1—H2	0.9600	C11—C12	1.499 (3)
C1—H3	0.9600	C11—N1	1.477 (2)
C1—H1	0.9600	C12—H17	0.9700
C1—C2	1.5076 (19)	C12—H18	0.9700
C2—C3	1.406 (2)	C12—N2	1.475 (2)
C2—O1	1.2615 (16)	C13—H19	0.9600
C3—H4	0.9300	C13—H21	0.9600
C3—C4	1.386 (2)	C13—H20	0.9600
C4—C5	1.511 (2)	C13—N1	1.471 (2)
C4—O2	1.2687 (17)	C14—H24	0.9600
C5—H7	0.9600	C14—H22	0.9600
C5—H5	0.9600	C14—H23	0.9600
C5—H6	0.9600	C14—N1	1.4718 (19)
C6—H10	0.9600	C15—H26	0.9600
C6—H9	0.9600	C15—H25	0.9600
C6—H8	0.9600	C15—H27	0.9600
C6—C7	1.511 (2)	C15—N2	1.472 (2)
C7—C8	1.397 (2)	C16—H29	0.9600
C7—O3	1.2583 (17)	C16—H28	0.9600
C8—H11	0.9300	C16—H30	0.9600
C8—C9	1.385 (2)	C16—N2	1.470 (2)
C9—C10	1.506 (2)	Fe—O1	2.0876 (10)
C9—O4	1.2734 (16)	Fe—O2	2.0497 (10)
C10—H14	0.9600	Fe—O3	2.0970 (10)
C10—H13	0.9600	Fe—O4	2.0520 (9)
C10—H12	0.9600	Fe—N1	2.3021 (12)
C11—H16	0.9700	Fe—N2	2.3184 (12)
C11—H15	0.9700

H2—C1—H3	109.5	H19—C13—H20	109.5
H2—C1—H1	109.5	H21—C13—H20	109.5
H3—C1—H1	109.5	N1—C13—H19	109.5
C2—C1—H2	109.5	N1—C13—H21	109.5
C2—C1—H3	109.5	N1—C13—H20	109.5
C2—C1—H1	109.5	H24—C14—H22	109.5
C3—C2—C1	118.30 (12)	H24—C14—H23	109.5
O1—C2—C1	116.98 (13)	H22—C14—H23	109.5
O1—C2—C3	124.72 (13)	N1—C14—H24	109.5
C2—C3—H4	117.5	N1—C14—H22	109.5
C4—C3—C2	125.07 (13)	N1—C14—H23	109.5
C4—C3—H4	117.5	H26—C15—H25	109.5
C3—C4—C5	119.35 (14)	H26—C15—H27	109.5
O2—C4—C3	125.36 (13)	H25—C15—H27	109.5
O2—C4—C5	115.28 (14)	N2—C15—H26	109.5
C4—C5—H7	109.5	N2—C15—H25	109.5
C4—C5—H5	109.5	N2—C15—H27	109.5
C4—C5—H6	109.5	H29—C16—H28	109.5
H7—C5—H5	109.5	H29—C16—H30	109.5
H7—C5—H6	109.5	H28—C16—H30	109.5
H5—C5—H6	109.5	N2—C16—H29	109.5
H10—C6—H9	109.5	N2—C16—H28	109.5
H10—C6—H8	109.5	N2—C16—H30	109.5
H9—C6—H8	109.5	O1—Fe—O2	85.58 (4)
C7—C6—H10	109.5	O1—Fe—O3	93.98 (4)
C7—C6—H9	109.5	O1—Fe—O4	99.11 (4)
C7—C6—H8	109.5	O1—Fe—N1	92.44 (4)
C8—C7—C6	117.47 (13)	O1—Fe—N2	166.73 (4)
O3—C7—C6	117.22 (13)	O2—Fe—O3	95.84 (4)
O3—C7—C8	125.31 (13)	O2—Fe—O4	174.85 (4)
C7—C8—H11	117.3	O2—Fe—N1	91.04 (5)
C9—C8—C7	125.32 (12)	O2—Fe—N2	84.18 (4)
C9—C8—H11	117.3	O3—Fe—O4	86.00 (4)
C8—C9—C10	118.69 (13)	O3—Fe—N1	170.93 (4)
O4—C9—C8	125.57 (12)	O3—Fe—N2	95.43 (4)
O4—C9—C10	115.74 (13)	O4—Fe—N1	86.66 (4)
C9—C10—H14	109.5	O4—Fe—N2	90.87 (4)
C9—C10—H13	109.5	N1—Fe—N2	79.35 (4)
C9—C10—H12	109.5	C11—N1—Fe	105.70 (9)
H14—C10—H13	109.5	C13—N1—C11	109.69 (14)
H14—C10—H12	109.5	C13—N1—C14	107.39 (13)
H13—C10—H12	109.5	C13—N1—Fe	111.69 (10)
H16—C11—H15	108.0	C14—N1—C11	111.18 (13)
C12—C11—H16	109.3	C14—N1—Fe	111.24 (10)
C12—C11—H15	109.3	C12—N2—Fe	104.52 (9)
N1—C11—H16	109.3	C15—N2—C12	110.31 (14)
N1—C11—H15	109.3	C15—N2—Fe	112.54 (10)
N1—C11—C12	111.60 (14)	C16—N2—C12	109.77 (14)
C11—C12—H17	109.2	C16—N2—C15	108.03 (14)
C11—C12—H18	109.2	C16—N2—Fe	111.65 (10)
H17—C12—H18	107.9	C2—O1—Fe	129.04 (9)
N2—C12—C11	111.91 (13)	C4—O2—Fe	129.79 (9)
N2—C12—H17	109.2	C7—O3—Fe	128.42 (10)
N2—C12—H18	109.2	C9—O4—Fe	129.18 (9)
H19—C13—H21	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H2···O1ⁱ	0.96	2.62	3.5269 (18)	157

Symmetry code: (i) −x+1, −y+1, −z+1.

Bis(acetylacetonato-κ²O,O')(N,N,N',N'-tetramethylethylenediamine-κ²N,N')zinc(II) (3) top

Crystal data top

[Zn(C₅H₇O₂)₂(C₆H₁₆N₂)]	F(000) = 808
M_r = 379.79	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2335 (3) Å	Cell parameters from 19126 reflections
b = 14.2134 (6) Å	θ = 2.1–27.2°
c = 13.6738 (5) Å	µ = 1.28 mm⁻¹
β = 101.208 (3)°	T = 200 K
V = 1950.96 (12) Å³	Block, clear colourless
Z = 4	0.45 × 0.39 × 0.33 mm

Data collection top

STOE IPDS 2T diffractometer	3456 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.047
rotation method, ω scans	θ_max = 26.7°, θ_min = 2.1°
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)	h = −12→12
T_min = 0.627, T_max = 0.779	k = −17→16
22385 measured reflections	l = −17→17
4124 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4124 reflections	Δρ_max = 0.37 e Å⁻³
216 parameters	Δρ_min = −0.26 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Zn	0.74026 (2)	0.26429 (2)	0.54676 (2)	0.03991 (8)
O1	0.73445 (12)	0.33774 (8)	0.41466 (9)	0.0534 (3)
O2	0.85986 (11)	0.16705 (8)	0.49492 (8)	0.0507 (3)
O3	0.57869 (11)	0.17554 (8)	0.50853 (9)	0.0529 (3)
O4	0.61242 (9)	0.36299 (8)	0.58630 (8)	0.0441 (2)
N1	0.91461 (12)	0.35505 (11)	0.62041 (10)	0.0499 (3)
N2	0.78674 (12)	0.19573 (11)	0.69813 (10)	0.0459 (3)
C1	0.76595 (19)	0.38103 (13)	0.25509 (13)	0.0575 (4)
H1	0.6725	0.4006	0.2373	0.086*
H2	0.7922	0.3504	0.1977	0.086*
H3	0.8222	0.4363	0.2743	0.086*
C2	0.78276 (15)	0.31277 (12)	0.34146 (11)	0.0450 (4)
C3	0.85137 (17)	0.22957 (12)	0.33344 (13)	0.0492 (4)
H4	0.8764	0.2169	0.2714	0.059*
C4	0.88628 (15)	0.16331 (12)	0.40893 (12)	0.0462 (4)
C5	0.9672 (2)	0.07864 (15)	0.38836 (14)	0.0672 (5)
H5	1.0493	0.0752	0.4389	0.101*
H6	0.9896	0.0849	0.3222	0.101*
H7	0.9149	0.0212	0.3907	0.101*
C6	0.3632 (2)	0.11210 (15)	0.48710 (15)	0.0691 (5)
H8	0.3797	0.0646	0.5401	0.104*
H9	0.3758	0.0838	0.4242	0.104*
H10	0.2717	0.1354	0.4796	0.104*
C7	0.45930 (16)	0.19273 (13)	0.51387 (11)	0.0476 (4)
C8	0.41127 (15)	0.27812 (12)	0.54200 (12)	0.0475 (4)
H11	0.3180	0.2826	0.5391	0.057*
C9	0.48712 (14)	0.35764 (11)	0.57395 (11)	0.0412 (3)
C10	0.41684 (16)	0.44556 (13)	0.59729 (13)	0.0554 (4)
H12	0.3393	0.4283	0.6257	0.083*
H13	0.3875	0.4817	0.5359	0.083*
H14	0.4780	0.4838	0.6454	0.083*
C11	0.93211 (19)	0.33443 (17)	0.72727 (14)	0.0676 (5)
H15	0.8644	0.3692	0.7556	0.081*
H16	1.0212	0.3563	0.7615	0.081*
C12	0.91917 (19)	0.23151 (16)	0.74583 (15)	0.0651 (5)
H17	0.9887	0.1969	0.7194	0.078*
H18	0.9335	0.2200	0.8185	0.078*
C13	0.88618 (18)	0.45547 (14)	0.60157 (16)	0.0671 (5)
H19	0.9629	0.4929	0.6341	0.101*
H20	0.8076	0.4732	0.6285	0.101*
H21	0.8691	0.4673	0.5296	0.101*
C14	1.03600 (16)	0.33196 (16)	0.58256 (16)	0.0651 (5)
H22	1.0212	0.3449	0.5108	0.098*
H23	1.0573	0.2652	0.5944	0.098*
H24	1.1102	0.3704	0.6172	0.098*
C15	0.68709 (18)	0.21961 (14)	0.75840 (13)	0.0560 (4)
H25	0.6835	0.2881	0.7660	0.084*
H26	0.7118	0.1902	0.8243	0.084*
H27	0.5995	0.1964	0.7251	0.084*
C16	0.7902 (2)	0.09286 (14)	0.68935 (15)	0.0680 (5)
H28	0.7024	0.0700	0.6562	0.102*
H29	0.8137	0.0649	0.7560	0.102*
H30	0.8568	0.0750	0.6500	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.03590 (11)	0.04475 (13)	0.04087 (12)	0.00666 (7)	0.01186 (8)	−0.00208 (7)
O1	0.0628 (7)	0.0534 (7)	0.0470 (6)	0.0178 (6)	0.0187 (5)	0.0051 (5)
O2	0.0555 (6)	0.0545 (7)	0.0465 (6)	0.0158 (5)	0.0204 (5)	0.0024 (5)
O3	0.0488 (6)	0.0496 (7)	0.0592 (7)	−0.0007 (5)	0.0078 (5)	−0.0096 (5)
O4	0.0335 (5)	0.0470 (6)	0.0538 (6)	0.0028 (4)	0.0136 (4)	−0.0040 (5)
N1	0.0353 (6)	0.0602 (9)	0.0557 (8)	−0.0041 (6)	0.0125 (6)	−0.0053 (7)
N2	0.0431 (7)	0.0537 (8)	0.0422 (7)	0.0079 (6)	0.0114 (5)	0.0024 (6)
C1	0.0653 (11)	0.0582 (11)	0.0492 (10)	−0.0021 (9)	0.0114 (8)	0.0046 (8)
C2	0.0406 (8)	0.0525 (10)	0.0417 (8)	−0.0032 (7)	0.0077 (6)	−0.0012 (7)
C3	0.0529 (9)	0.0559 (10)	0.0417 (9)	0.0035 (7)	0.0163 (7)	−0.0050 (7)
C4	0.0444 (8)	0.0481 (9)	0.0485 (9)	0.0042 (7)	0.0149 (7)	−0.0079 (7)
C5	0.0817 (13)	0.0620 (12)	0.0632 (11)	0.0230 (10)	0.0271 (10)	−0.0048 (9)
C6	0.0680 (12)	0.0741 (14)	0.0632 (12)	−0.0250 (10)	0.0074 (9)	−0.0086 (10)
C7	0.0474 (8)	0.0576 (10)	0.0356 (8)	−0.0083 (8)	0.0028 (6)	0.0009 (7)
C8	0.0323 (7)	0.0653 (11)	0.0451 (9)	−0.0004 (7)	0.0081 (6)	0.0028 (7)
C9	0.0368 (7)	0.0515 (9)	0.0370 (8)	0.0066 (6)	0.0113 (6)	0.0068 (6)
C10	0.0443 (8)	0.0596 (11)	0.0674 (11)	0.0127 (7)	0.0233 (8)	0.0043 (8)
C11	0.0517 (10)	0.0963 (16)	0.0527 (11)	−0.0182 (10)	0.0053 (8)	−0.0141 (10)
C12	0.0449 (9)	0.0990 (16)	0.0484 (10)	0.0056 (9)	0.0017 (8)	0.0119 (10)
C13	0.0529 (10)	0.0562 (11)	0.0935 (14)	−0.0131 (9)	0.0175 (10)	−0.0120 (10)
C14	0.0375 (8)	0.0825 (14)	0.0785 (13)	−0.0044 (8)	0.0194 (8)	−0.0032 (11)
C15	0.0540 (10)	0.0724 (12)	0.0452 (9)	0.0086 (8)	0.0183 (8)	0.0043 (8)
C16	0.0905 (14)	0.0552 (11)	0.0627 (11)	0.0198 (10)	0.0256 (10)	0.0137 (9)

Geometric parameters (Å, º) top

Zn—O1	2.0771 (12)	C6—H9	0.9800
Zn—O2	2.0611 (11)	C6—H10	0.9800
Zn—O3	2.0645 (11)	C6—C7	1.508 (2)
Zn—O4	2.0607 (10)	C7—C8	1.391 (3)
Zn—N1	2.2722 (13)	C8—H11	0.9500
Zn—N2	2.2533 (13)	C8—C9	1.393 (2)
O1—C2	1.2509 (19)	C9—C10	1.507 (2)
O2—C4	1.2578 (19)	C10—H12	0.9800
O3—C7	1.2619 (19)	C10—H13	0.9800
O4—C9	1.2626 (17)	C10—H14	0.9800
N1—C11	1.467 (2)	C11—H15	0.9900
N1—C13	1.469 (2)	C11—H16	0.9900
N1—C14	1.473 (2)	C11—C12	1.495 (3)
N2—C12	1.476 (2)	C12—H17	0.9900
N2—C15	1.470 (2)	C12—H18	0.9900
N2—C16	1.468 (2)	C13—H19	0.9800
C1—H1	0.9800	C13—H20	0.9800
C1—H2	0.9800	C13—H21	0.9800
C1—H3	0.9800	C14—H22	0.9800
C1—C2	1.512 (2)	C14—H23	0.9800
C2—C3	1.390 (2)	C14—H24	0.9800
C3—H4	0.9500	C15—H25	0.9800
C3—C4	1.392 (2)	C15—H26	0.9800
C4—C5	1.518 (2)	C15—H27	0.9800
C5—H5	0.9800	C16—H28	0.9800
C5—H6	0.9800	C16—H29	0.9800
C5—H7	0.9800	C16—H30	0.9800
C6—H8	0.9800

O1—Zn—O2	87.50 (4)	C7—C6—H8	109.5
O1—Zn—O3	101.58 (5)	C7—C6—H9	109.5
O1—Zn—O4	88.49 (4)	C7—C6—H10	109.5
O1—Zn—N1	89.28 (5)	O3—C7—C6	115.59 (16)
O1—Zn—N2	168.94 (5)	O3—C7—C8	125.65 (15)
O2—Zn—O3	90.18 (5)	C8—C7—C6	118.76 (16)
O2—Zn—O4	175.16 (4)	C7—C8—H11	116.9
O2—Zn—N1	93.76 (5)	C7—C8—C9	126.12 (15)
O2—Zn—N2	89.57 (5)	C9—C8—H11	116.9
O3—Zn—O4	87.96 (4)	O4—C9—C8	125.48 (15)
O3—Zn—N1	168.61 (5)	O4—C9—C10	115.84 (15)
O3—Zn—N2	89.09 (5)	C8—C9—C10	118.67 (13)
O4—Zn—N1	88.92 (5)	C9—C10—H12	109.5
O4—Zn—N2	94.86 (5)	C9—C10—H13	109.5
N1—Zn—N2	80.27 (5)	C9—C10—H14	109.5
C2—O1—Zn	127.18 (11)	H12—C10—H13	109.5
C4—O2—Zn	126.86 (11)	H12—C10—H14	109.5
C7—O3—Zn	127.15 (11)	H13—C10—H14	109.5
C9—O4—Zn	127.15 (10)	N1—C11—H15	109.3
C11—N1—Zn	105.16 (10)	N1—C11—H16	109.3
C11—N1—C13	110.51 (16)	N1—C11—C12	111.53 (16)
C11—N1—C14	110.95 (15)	H15—C11—H16	108.0
C13—N1—Zn	111.23 (10)	C12—C11—H15	109.3
C13—N1—C14	107.86 (15)	C12—C11—H16	109.3
C14—N1—Zn	111.17 (11)	N2—C12—C11	111.49 (15)
C12—N2—Zn	105.59 (11)	N2—C12—H17	109.3
C15—N2—Zn	111.69 (10)	N2—C12—H18	109.3
C15—N2—C12	110.50 (15)	C11—C12—H17	109.3
C16—N2—Zn	111.08 (11)	C11—C12—H18	109.3
C16—N2—C12	110.16 (14)	H17—C12—H18	108.0
C16—N2—C15	107.84 (15)	N1—C13—H19	109.5
H1—C1—H2	109.5	N1—C13—H20	109.5
H1—C1—H3	109.5	N1—C13—H21	109.5
H2—C1—H3	109.5	H19—C13—H20	109.5
C2—C1—H1	109.5	H19—C13—H21	109.5
C2—C1—H2	109.5	H20—C13—H21	109.5
C2—C1—H3	109.5	N1—C14—H22	109.5
O1—C2—C1	116.12 (15)	N1—C14—H23	109.5
O1—C2—C3	126.06 (16)	N1—C14—H24	109.5
C3—C2—C1	117.82 (15)	H22—C14—H23	109.5
C2—C3—H4	117.4	H22—C14—H24	109.5
C2—C3—C4	125.30 (15)	H23—C14—H24	109.5
C4—C3—H4	117.4	N2—C15—H25	109.5
O2—C4—C3	126.43 (15)	N2—C15—H26	109.5
O2—C4—C5	115.53 (15)	N2—C15—H27	109.5
C3—C4—C5	118.02 (15)	H25—C15—H26	109.5
C4—C5—H5	109.5	H25—C15—H27	109.5
C4—C5—H6	109.5	H26—C15—H27	109.5
C4—C5—H7	109.5	N2—C16—H28	109.5
H5—C5—H6	109.5	N2—C16—H29	109.5
H5—C5—H7	109.5	N2—C16—H30	109.5
H6—C5—H7	109.5	H28—C16—H29	109.5
H8—C6—H9	109.5	H28—C16—H30	109.5
H8—C6—H10	109.5	H29—C16—H30	109.5
H9—C6—H10	109.5

Acknowledgements

We thank A. Kiowski for technical support.

Funding information

We acknowledge the financial support within the funding programme Open Access Publishing by the German Research Foundation (DFG).

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Volume 76| Part 1| January 2020| Pages 66-71

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