Literature DB >> 31921454

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

Jan Henrik Halz1, Christian Heiser1, Christoph Wagner1, Kurt Merzweiler1.   

Abstract

The complexes bis-(acetyl-acetonato-κ2 O,O')(N,N,N',N'-tetra-methyl-ethylenedi-amine-κ2 N,N')manganese(II), [Mn(C5H7O2)2(C6H16N2)], bis-(acetyl-acetonato-κ2 O,O')(N,N,N',N'-tetra-methyl-ethylenedi-amine-κ2 N,N')iron(II), [Fe(C5H7O2)2(C6H16N2)], and bis-(acetyl-acetonato-κ2 O,O')(N,N,N',N'-tetra-methyl-ethylenedi-amine-κ2 N,N')zinc(II), [Zn(C5H7O2)2(C6H16N2)], were synthesized from the reaction of the corresponding metal acetyl-acetonates [M(acac)2(H2O)2] with N,N,N',N'-tetra-methyl-ethylenedi-amine (TMEDA) in toluene. Each of the complexes displays a central metal atom which is nearly octa-hedrally 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. © Halz et al. 2020.

Entities:  

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

Year:  2020        PMID： 31921454      PMCID： PMC6944083          DOI： 10.1107/S2056989019016372

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


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)(TMEDA)] (5.7 B.M.) and [Fe(acac)2(TMEDA)] (5.1 B.M.) indicates a high-spin configuration in both cases.

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 ▸].
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.

Table 1

Selected geometric parameters (Å, °) for 1

Mn—O12.1271 (13)Mn—O42.1365 (12)
Mn—O22.1500 (12)Mn—N12.3643 (15)
Mn—O32.1375 (12)Mn—N22.3560 (15)
    
O1—Mn—O283.61 (5)O2—Mn—N290.36 (5)
O1—Mn—O3107.00 (5)O3—Mn—O483.78 (5)
O1—Mn—O493.25 (5)O3—Mn—N1165.43 (5)
O1—Mn—N186.01 (5)O3—Mn—N290.61 (5)
O1—Mn—N2161.29 (6)O4—Mn—N189.07 (5)
O2—Mn—O389.71 (5)O4—Mn—N294.95 (6)
O2—Mn—O4171.63 (5)N1—Mn—N277.34 (6)
O2—Mn—N198.41 (5)  
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—O12.0876 (10)Fe—O42.0520 (9)
Fe—O22.0497 (10)Fe—N12.3021 (12)
Fe—O32.0970 (10)Fe—N22.3184 (12)
    
O1—Fe—O285.58 (4)O2—Fe—N284.18 (4)
O1—Fe—O393.98 (4)O3—Fe—O486.00 (4)
O1—Fe—O499.11 (4)O3—Fe—N1170.93 (4)
O1—Fe—N192.44 (4)O3—Fe—N295.43 (4)
O1—Fe—N2166.73 (4)O4—Fe—N186.66 (4)
O2—Fe—O395.84 (4)O4—Fe—N290.87 (4)
O2—Fe—O4174.85 (4)N1—Fe—N279.35 (4)
O2—Fe—N191.04 (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—O12.0771 (12)Zn—O42.0607 (10)
Zn—O22.0611 (11)Zn—N12.2722 (13)
Zn—O32.0645 (11)Zn—N22.2533 (13)
    
O1—Zn—O287.50 (4)O2—Zn—N289.57 (5)
O1—Zn—O3101.58 (5)O3—Zn—O487.96 (4)
O1—Zn—O488.49 (4)O3—Zn—N1168.61 (5)
O1—Zn—N189.28 (5)O3—Zn—N289.09 (5)
O1—Zn—N2168.94 (5)O4—Zn—N188.92 (5)
O2—Zn—O390.18 (5)O4—Zn—N294.86 (5)
O2—Zn—O4175.16 (4)N1—Zn—N280.27 (5)
O2—Zn—N193.76 (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 C 2 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)].

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 R 2 2(8) type motifs, forming centrosymmetric dimers (Fig. 5 ▸).
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.

Table 4

Hydrogen-bond geometry (Å, °) for 2

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H2⋯O1i 0.962.623.5269 (18)157

Symmetry code: (i) .

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.

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-CH 2), 2.31 (s, 12H, (CH 3)2N), 1.85 [s, 12H, CH 3C(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.

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. = (wD 2/)0.5 where D = F o 2 - F c 2.
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 369.36370.27379.79
Crystal system, space groupMonoclinic, P21/n Monoclinic, P21/n Monoclinic, P21/n
Temperature (K)213213200
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 444
Radiation typeMo KαMo KαMo Kα
μ (mm−1)0.690.791.28
Crystal size (mm)0.35 × 0.25 × 0.200.26 × 0.25 × 0.230.45 × 0.39 × 0.33
 
Data collection
DiffractometerSTOE IPDS 2STOE IPDS 2STOE IPDS 2T
Absorption correctionNumerical (X-AREA; Stoe & Cie, 2016 ▸)Numerical (X-AREA; Stoe & Cie, 2016 ▸)Numerical (X-AREA; Stoe & Cie, 2016 ▸)
T min, T max 0.798, 0.9120.814, 0.8940.627, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections12607, 4139, 347518586, 5276, 442522385, 4124, 3456
R int 0.0300.0370.047
(sin θ/λ)max (Å−1)0.6340.6880.633
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.034, 0.099, 1.060.031, 0.086, 1.040.027, 0.076, 1.07
No. of reflections413952764124
No. of parameters216216216
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.240.32, −0.220.37, −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 ▸).

Crystal structure: contains datablock(s) 1, 2, 3. DOI: 10.1107/S2056989019016372/wm5524sup1.cif Structure factors: contains datablock(s) 1. DOI: 10.1107/S2056989019016372/wm55241sup2.hkl Structure factors: contains datablock(s) 2. DOI: 10.1107/S2056989019016372/wm55242sup3.hkl Structure factors: contains datablock(s) 3. DOI: 10.1107/S2056989019016372/wm55243sup4.hkl CCDC references: 1969941, 1969940, 1969939 Additional supporting information: crystallographic information; 3D view; checkCIF report
[Mn(C5H7O2)2(C6H16N2)]F(000) = 788
Mr = 369.36Dx = 1.241 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.4234 (4) ÅCell parameters from 13227 reflections
b = 14.3123 (5) Åθ = 1.4–27.2°
c = 13.6047 (5) ŵ = 0.69 mm−1
β = 103.154 (3)°T = 213 K
V = 1976.33 (13) Å3Block, clear yellow
Z = 40.35 × 0.25 × 0.20 mm
STOE IPDS 2 diffractometer4139 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus, Incoatec Iµs3475 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.030
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 2.1°
rotation method scansh = −13→13
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)k = −17→18
Tmin = 0.798, Tmax = 0.912l = −17→16
12607 measured reflections
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.099w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6571P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4139 reflectionsΔρmax = 0.22 e Å−3
216 parametersΔρmin = −0.24 e Å−3
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.
xyzUiso*/Ueq
Mn0.50579 (2)0.74721 (2)0.49407 (2)0.04120 (11)
O10.67069 (13)0.65614 (9)0.53426 (10)0.0602 (3)
O20.64605 (12)0.84003 (9)0.45153 (11)0.0554 (3)
O30.50538 (13)0.83274 (9)0.62280 (10)0.0546 (3)
O40.38216 (14)0.65820 (9)0.55845 (10)0.0565 (3)
N10.44810 (15)0.65991 (11)0.34289 (11)0.0523 (4)
N20.33093 (14)0.83481 (11)0.39666 (12)0.0533 (4)
C10.8801 (3)0.5868 (2)0.5617 (2)0.0943 (9)
H10.84770.54840.60860.141*
H30.96670.60890.59280.141*
H20.88380.55060.50290.141*
C20.7888 (2)0.66910 (16)0.53114 (14)0.0593 (5)
C30.8405 (2)0.75159 (16)0.50286 (17)0.0664 (6)
H40.93080.75320.50700.080*
C40.76938 (18)0.83223 (14)0.46880 (15)0.0568 (5)
C50.8448 (2)0.91826 (18)0.4505 (2)0.0885 (8)
H50.91360.90060.41780.133*
H60.88270.94770.51380.133*
H70.78600.96110.40820.133*
C60.4607 (2)0.89848 (16)0.77048 (18)0.0714 (6)
H80.55210.91440.79360.107*
H100.42630.87820.82670.107*
H90.41250.95220.74000.107*
C70.44674 (17)0.82045 (13)0.69347 (13)0.0498 (4)
C80.3712 (2)0.74328 (13)0.70557 (16)0.0568 (5)
H110.33670.74160.76290.068*
C90.34284 (19)0.66822 (13)0.63927 (15)0.0558 (4)
C100.2576 (3)0.59062 (18)0.6645 (2)0.0920 (9)
H120.21710.61070.71760.138*
H130.31090.53650.68610.138*
H140.19040.57540.60570.138*
C110.3189 (2)0.69516 (18)0.28808 (16)0.0693 (6)
H160.25060.66840.31730.083*
H150.30300.67530.21820.083*
C120.3114 (2)0.79961 (18)0.29216 (16)0.0703 (6)
H170.37810.82630.26120.084*
H180.22600.81990.25350.084*
C130.4397 (3)0.55956 (14)0.36410 (18)0.0728 (6)
H200.37430.54960.40260.109*
H210.52360.53780.40180.109*
H190.41560.52580.30160.109*
C140.5481 (2)0.67378 (17)0.28339 (15)0.0647 (5)
H240.52270.64030.22080.097*
H220.63160.65090.32070.097*
H230.55530.73920.26980.097*
C150.21051 (19)0.82208 (18)0.43395 (18)0.0711 (6)
H250.18890.75680.43310.107*
H270.13930.85570.39140.107*
H260.22460.84540.50170.107*
C160.3638 (2)0.93462 (15)0.4003 (2)0.0784 (7)
H290.29450.96850.35600.118*
H280.44480.94350.37930.118*
H300.37360.95720.46800.118*
U11U22U33U12U13U23
Mn0.03895 (15)0.04541 (18)0.03899 (15)−0.00103 (10)0.00838 (10)0.00066 (10)
O10.0612 (8)0.0613 (8)0.0561 (8)0.0159 (6)0.0090 (6)0.0076 (6)
O20.0433 (6)0.0523 (7)0.0725 (9)−0.0029 (5)0.0168 (6)0.0043 (6)
O30.0591 (7)0.0537 (7)0.0526 (7)−0.0101 (6)0.0160 (6)−0.0103 (6)
O40.0700 (8)0.0495 (7)0.0567 (8)−0.0136 (6)0.0282 (6)−0.0085 (6)
N10.0538 (8)0.0612 (9)0.0426 (8)−0.0076 (7)0.0124 (6)−0.0048 (7)
N20.0431 (7)0.0595 (9)0.0546 (9)0.0040 (7)0.0054 (6)0.0063 (7)
C10.0924 (18)0.108 (2)0.0744 (15)0.0575 (16)0.0027 (13)−0.0049 (14)
C20.0561 (11)0.0758 (14)0.0411 (9)0.0216 (10)0.0009 (8)−0.0109 (9)
C30.0392 (9)0.0933 (17)0.0658 (13)0.0089 (10)0.0100 (9)−0.0196 (11)
C40.0454 (9)0.0699 (12)0.0589 (11)−0.0094 (9)0.0197 (8)−0.0190 (9)
C50.0657 (14)0.0870 (17)0.124 (2)−0.0267 (13)0.0450 (15)−0.0239 (16)
C60.0770 (14)0.0710 (14)0.0676 (13)0.0026 (11)0.0191 (11)−0.0237 (11)
C70.0473 (9)0.0556 (10)0.0450 (9)0.0070 (8)0.0076 (7)−0.0062 (8)
C80.0628 (12)0.0614 (12)0.0525 (10)−0.0014 (9)0.0262 (9)−0.0058 (8)
C90.0581 (10)0.0560 (11)0.0590 (11)−0.0039 (9)0.0253 (9)−0.0014 (9)
C100.110 (2)0.0822 (17)0.104 (2)−0.0364 (15)0.0658 (17)−0.0179 (15)
C110.0544 (11)0.0974 (17)0.0505 (11)−0.0062 (11)0.0004 (9)−0.0157 (11)
C120.0594 (12)0.0975 (17)0.0483 (11)0.0137 (11)0.0000 (9)0.0114 (11)
C130.1012 (17)0.0554 (12)0.0660 (13)−0.0177 (11)0.0276 (12)−0.0174 (10)
C140.0666 (12)0.0849 (15)0.0466 (10)−0.0047 (11)0.0210 (9)−0.0051 (10)
C150.0432 (10)0.0931 (16)0.0760 (14)0.0085 (10)0.0118 (9)0.0033 (12)
C160.0653 (13)0.0614 (13)0.1024 (19)0.0125 (10)0.0063 (12)0.0203 (12)
Mn—O12.1271 (13)C6—H100.9600
Mn—O22.1500 (12)C6—H90.9600
Mn—O32.1375 (12)C6—C71.515 (3)
Mn—O42.1365 (12)C7—C81.388 (3)
Mn—N12.3643 (15)C8—H110.9300
Mn—N22.3560 (15)C8—C91.391 (3)
O1—C21.255 (2)C9—C101.510 (3)
O2—C41.258 (2)C10—H120.9600
O3—C71.263 (2)C10—H130.9600
O4—C91.266 (2)C10—H140.9600
N1—C111.472 (3)C11—H160.9700
N1—C131.472 (3)C11—H150.9700
N1—C141.472 (2)C11—C121.499 (4)
N2—C121.478 (3)C12—H170.9700
N2—C151.468 (2)C12—H180.9700
N2—C161.467 (3)C13—H200.9600
C1—H10.9600C13—H210.9600
C1—H30.9600C13—H190.9600
C1—H20.9600C14—H240.9600
C1—C21.512 (3)C14—H220.9600
C2—C31.388 (3)C14—H230.9600
C3—H40.9300C15—H250.9600
C3—C41.393 (3)C15—H270.9600
C4—C51.512 (3)C15—H260.9600
C5—H50.9600C16—H290.9600
C5—H60.9600C16—H280.9600
C5—H70.9600C16—H300.9600
C6—H80.9600
O1—Mn—O283.61 (5)C7—C6—H8109.5
O1—Mn—O3107.00 (5)C7—C6—H10109.5
O1—Mn—O493.25 (5)C7—C6—H9109.5
O1—Mn—N186.01 (5)O3—C7—C6115.89 (17)
O1—Mn—N2161.29 (6)O3—C7—C8125.92 (17)
O2—Mn—O389.71 (5)C8—C7—C6118.18 (17)
O2—Mn—O4171.63 (5)C7—C8—H11117.2
O2—Mn—N198.41 (5)C7—C8—C9125.50 (18)
O2—Mn—N290.36 (5)C9—C8—H11117.2
O3—Mn—O483.78 (5)O4—C9—C8125.99 (17)
O3—Mn—N1165.43 (5)O4—C9—C10115.94 (18)
O3—Mn—N290.61 (5)C8—C9—C10118.07 (18)
O4—Mn—N189.07 (5)C9—C10—H12109.5
O4—Mn—N294.95 (6)C9—C10—H13109.5
N1—Mn—N277.34 (6)C9—C10—H14109.5
C2—O1—Mn129.95 (14)H12—C10—H13109.5
C4—O2—Mn128.56 (13)H12—C10—H14109.5
C7—O3—Mn129.44 (12)H13—C10—H14109.5
C9—O4—Mn129.29 (12)N1—C11—H16109.2
C11—N1—Mn106.37 (12)N1—C11—H15109.2
C13—N1—Mn111.10 (12)N1—C11—C12111.88 (17)
C13—N1—C11110.20 (18)H16—C11—H15107.9
C13—N1—C14108.71 (17)C12—C11—H16109.2
C14—N1—Mn109.60 (12)C12—C11—H15109.2
C14—N1—C11110.86 (16)N2—C12—C11112.25 (17)
C12—N2—Mn106.22 (12)N2—C12—H17109.2
C15—N2—Mn110.63 (12)N2—C12—H18109.2
C15—N2—C12110.40 (17)C11—C12—H17109.2
C16—N2—Mn110.75 (12)C11—C12—H18109.2
C16—N2—C12110.14 (18)H17—C12—H18107.9
C16—N2—C15108.69 (17)N1—C13—H20109.5
H1—C1—H3109.5N1—C13—H21109.5
H1—C1—H2109.5N1—C13—H19109.5
H3—C1—H2109.5H20—C13—H21109.5
C2—C1—H1109.5H20—C13—H19109.5
C2—C1—H3109.5H21—C13—H19109.5
C2—C1—H2109.5N1—C14—H24109.5
O1—C2—C1115.9 (2)N1—C14—H22109.5
O1—C2—C3125.51 (18)N1—C14—H23109.5
C3—C2—C1118.6 (2)H24—C14—H22109.5
C2—C3—H4117.1H24—C14—H23109.5
C2—C3—C4125.86 (18)H22—C14—H23109.5
C4—C3—H4117.1N2—C15—H25109.5
O2—C4—C3125.44 (19)N2—C15—H27109.5
O2—C4—C5116.4 (2)N2—C15—H26109.5
C3—C4—C5118.17 (19)H25—C15—H27109.5
C4—C5—H5109.5H25—C15—H26109.5
C4—C5—H6109.5H27—C15—H26109.5
C4—C5—H7109.5N2—C16—H29109.5
H5—C5—H6109.5N2—C16—H28109.5
H5—C5—H7109.5N2—C16—H30109.5
H6—C5—H7109.5H29—C16—H28109.5
H8—C6—H10109.5H29—C16—H30109.5
H8—C6—H9109.5H28—C16—H30109.5
H10—C6—H9109.5
Mn—O1—C2—C1−177.50 (14)N1—C11—C12—N2−60.6 (2)
Mn—O1—C2—C32.8 (3)C1—C2—C3—C4177.1 (2)
Mn—O2—C4—C313.4 (3)C2—C3—C4—O2−5.6 (3)
Mn—O2—C4—C5−166.67 (16)C2—C3—C4—C5174.5 (2)
Mn—O3—C7—C6−176.26 (13)C6—C7—C8—C9176.5 (2)
Mn—O3—C7—C83.2 (3)C7—C8—C9—O40.7 (4)
Mn—O4—C9—C81.1 (3)C7—C8—C9—C10−179.4 (2)
Mn—O4—C9—C10−178.82 (17)C13—N1—C11—C12162.74 (17)
Mn—N1—C11—C1242.22 (19)C14—N1—C11—C12−76.9 (2)
Mn—N2—C12—C1142.41 (19)C15—N2—C12—C11−77.6 (2)
O1—C2—C3—C4−3.2 (3)C16—N2—C12—C11162.39 (17)
O3—C7—C8—C9−3.0 (3)
[Fe(C5H7O2)2(C6H16N2)]F(000) = 792
Mr = 370.27Dx = 1.253 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.2021 (3) ÅCell parameters from 16780 reflections
b = 15.4708 (4) Åθ = 1.6–29.6°
c = 12.4881 (4) ŵ = 0.79 mm−1
β = 95.382 (3)°T = 213 K
V = 1962.37 (10) Å3Block, clear reddish brown
Z = 40.26 × 0.25 × 0.23 mm
STOE IPDS 2 diffractometer5276 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus, Incoatec Iµs4425 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.037
Detector resolution: 6.67 pixels mm-1θmax = 29.3°, θmin = 2.1°
rotation method scansh = −13→13
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)k = −21→20
Tmin = 0.814, Tmax = 0.894l = −17→17
18586 measured reflections
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.086w = 1/[σ2(Fo2) + (0.0464P)2 + 0.3681P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
5276 reflectionsΔρmax = 0.32 e Å−3
216 parametersΔρmin = −0.22 e Å−3
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.
xyzUiso*/Ueq
C10.63613 (15)0.53037 (11)0.42322 (12)0.0444 (3)
H20.58470.47970.43380.067*
H30.70610.51600.38000.067*
H10.58100.57390.38740.067*
C20.69359 (13)0.56425 (9)0.53071 (11)0.0352 (3)
C30.81769 (14)0.53357 (9)0.57243 (12)0.0396 (3)
H40.86030.49480.53050.047*
C40.88149 (13)0.55660 (9)0.67116 (12)0.0388 (3)
C51.01582 (16)0.51923 (13)0.70525 (16)0.0584 (4)
H71.03430.47330.65720.088*
H51.01720.49700.77710.088*
H61.08130.56360.70310.088*
C60.39240 (17)0.48770 (10)0.87153 (14)0.0496 (4)
H100.30000.48170.84990.074*
H90.40640.48880.94860.074*
H80.43910.43970.84460.074*
C70.44227 (13)0.57093 (9)0.82668 (11)0.0359 (3)
C80.35444 (13)0.64029 (10)0.81410 (12)0.0379 (3)
H110.27070.63210.83590.046*
C90.38200 (13)0.72026 (9)0.77178 (11)0.0350 (3)
C100.27918 (16)0.79023 (12)0.77050 (16)0.0542 (4)
H140.26940.81710.70090.081*
H130.30590.83280.82410.081*
H120.19670.76540.78570.081*
C110.78186 (19)0.85071 (11)0.76164 (14)0.0537 (4)
H160.70200.87930.77920.064*
H150.84400.89490.74460.064*
C120.83901 (17)0.80004 (13)0.85721 (14)0.0545 (4)
H170.91920.77180.83980.065*
H180.86170.83930.91670.065*
C130.6596 (2)0.83936 (13)0.58754 (16)0.0593 (4)
H190.63810.80220.52690.089*
H210.70000.89120.56410.089*
H200.58070.85390.61980.089*
C140.87086 (16)0.77473 (12)0.61406 (14)0.0519 (4)
H240.90420.82680.58470.078*
H220.84990.73380.55720.078*
H230.93630.75060.66580.078*
C150.64471 (18)0.77489 (13)0.94987 (14)0.0549 (4)
H260.58250.73190.96770.082*
H250.60010.81880.90600.082*
H270.68530.80051.01470.082*
C160.8174 (2)0.67090 (14)0.96194 (14)0.0619 (5)
H290.88340.64280.92440.093*
H280.75660.62860.98400.093*
H300.85870.70001.02420.093*
Fe0.65967 (2)0.67126 (2)0.73081 (2)0.03242 (7)
N10.75139 (12)0.79468 (8)0.66685 (10)0.0407 (3)
N20.74634 (12)0.73421 (9)0.89046 (10)0.0418 (3)
O10.62568 (9)0.61851 (7)0.57684 (8)0.0395 (2)
O20.83743 (9)0.60880 (7)0.73746 (9)0.0426 (2)
O30.55981 (10)0.57212 (6)0.80388 (9)0.0414 (2)
O40.48936 (9)0.74134 (6)0.73429 (8)0.0384 (2)
U11U22U33U12U13U23
C10.0435 (7)0.0512 (8)0.0393 (7)−0.0086 (6)0.0082 (6)−0.0108 (6)
C20.0360 (6)0.0341 (6)0.0368 (7)−0.0081 (5)0.0096 (5)−0.0039 (5)
C30.0380 (7)0.0368 (7)0.0453 (8)0.0022 (5)0.0111 (6)−0.0064 (6)
C40.0301 (6)0.0407 (7)0.0465 (8)0.0000 (5)0.0089 (5)0.0000 (6)
C50.0374 (8)0.0703 (12)0.0670 (11)0.0127 (8)0.0019 (7)−0.0056 (9)
C60.0539 (9)0.0434 (8)0.0515 (9)−0.0121 (7)0.0050 (7)0.0076 (7)
C70.0380 (6)0.0369 (7)0.0328 (6)−0.0079 (5)0.0028 (5)−0.0029 (5)
C80.0303 (6)0.0435 (7)0.0413 (7)−0.0049 (5)0.0102 (5)−0.0045 (6)
C90.0315 (6)0.0393 (7)0.0349 (6)0.0017 (5)0.0056 (5)−0.0047 (5)
C100.0439 (8)0.0539 (9)0.0670 (11)0.0149 (7)0.0163 (7)0.0022 (8)
C110.0674 (11)0.0428 (8)0.0540 (10)−0.0207 (8)0.0222 (8)−0.0125 (7)
C120.0508 (9)0.0685 (11)0.0451 (9)−0.0275 (8)0.0092 (7)−0.0158 (8)
C130.0626 (11)0.0614 (11)0.0559 (10)−0.0011 (8)0.0154 (8)0.0167 (8)
C140.0496 (8)0.0561 (9)0.0537 (9)−0.0149 (7)0.0247 (7)−0.0073 (7)
C150.0550 (9)0.0690 (11)0.0429 (8)−0.0094 (8)0.0167 (7)−0.0164 (8)
C160.0650 (11)0.0792 (13)0.0401 (9)0.0011 (9)−0.0027 (8)−0.0002 (8)
Fe0.02688 (10)0.03490 (11)0.03626 (11)−0.00268 (7)0.00714 (7)−0.00567 (7)
N10.0432 (6)0.0415 (6)0.0395 (6)−0.0086 (5)0.0147 (5)−0.0039 (5)
N20.0395 (6)0.0513 (7)0.0354 (6)−0.0101 (5)0.0077 (5)−0.0055 (5)
O10.0329 (5)0.0440 (5)0.0416 (5)0.0005 (4)0.0028 (4)−0.0112 (4)
O20.0313 (5)0.0535 (6)0.0429 (5)0.0021 (4)0.0031 (4)−0.0100 (5)
O30.0352 (5)0.0352 (5)0.0543 (6)−0.0009 (4)0.0075 (4)0.0014 (4)
O40.0349 (5)0.0348 (5)0.0471 (5)0.0018 (4)0.0124 (4)0.0023 (4)
C1—H20.9600C11—C121.499 (3)
C1—H30.9600C11—N11.477 (2)
C1—H10.9600C12—H170.9700
C1—C21.5076 (19)C12—H180.9700
C2—C31.406 (2)C12—N21.475 (2)
C2—O11.2615 (16)C13—H190.9600
C3—H40.9300C13—H210.9600
C3—C41.386 (2)C13—H200.9600
C4—C51.511 (2)C13—N11.471 (2)
C4—O21.2687 (17)C14—H240.9600
C5—H70.9600C14—H220.9600
C5—H50.9600C14—H230.9600
C5—H60.9600C14—N11.4718 (19)
C6—H100.9600C15—H260.9600
C6—H90.9600C15—H250.9600
C6—H80.9600C15—H270.9600
C6—C71.511 (2)C15—N21.472 (2)
C7—C81.397 (2)C16—H290.9600
C7—O31.2583 (17)C16—H280.9600
C8—H110.9300C16—H300.9600
C8—C91.385 (2)C16—N21.470 (2)
C9—C101.506 (2)Fe—O12.0876 (10)
C9—O41.2734 (16)Fe—O22.0497 (10)
C10—H140.9600Fe—O32.0970 (10)
C10—H130.9600Fe—O42.0520 (9)
C10—H120.9600Fe—N12.3021 (12)
C11—H160.9700Fe—N22.3184 (12)
C11—H150.9700
H2—C1—H3109.5H19—C13—H20109.5
H2—C1—H1109.5H21—C13—H20109.5
H3—C1—H1109.5N1—C13—H19109.5
C2—C1—H2109.5N1—C13—H21109.5
C2—C1—H3109.5N1—C13—H20109.5
C2—C1—H1109.5H24—C14—H22109.5
C3—C2—C1118.30 (12)H24—C14—H23109.5
O1—C2—C1116.98 (13)H22—C14—H23109.5
O1—C2—C3124.72 (13)N1—C14—H24109.5
C2—C3—H4117.5N1—C14—H22109.5
C4—C3—C2125.07 (13)N1—C14—H23109.5
C4—C3—H4117.5H26—C15—H25109.5
C3—C4—C5119.35 (14)H26—C15—H27109.5
O2—C4—C3125.36 (13)H25—C15—H27109.5
O2—C4—C5115.28 (14)N2—C15—H26109.5
C4—C5—H7109.5N2—C15—H25109.5
C4—C5—H5109.5N2—C15—H27109.5
C4—C5—H6109.5H29—C16—H28109.5
H7—C5—H5109.5H29—C16—H30109.5
H7—C5—H6109.5H28—C16—H30109.5
H5—C5—H6109.5N2—C16—H29109.5
H10—C6—H9109.5N2—C16—H28109.5
H10—C6—H8109.5N2—C16—H30109.5
H9—C6—H8109.5O1—Fe—O285.58 (4)
C7—C6—H10109.5O1—Fe—O393.98 (4)
C7—C6—H9109.5O1—Fe—O499.11 (4)
C7—C6—H8109.5O1—Fe—N192.44 (4)
C8—C7—C6117.47 (13)O1—Fe—N2166.73 (4)
O3—C7—C6117.22 (13)O2—Fe—O395.84 (4)
O3—C7—C8125.31 (13)O2—Fe—O4174.85 (4)
C7—C8—H11117.3O2—Fe—N191.04 (5)
C9—C8—C7125.32 (12)O2—Fe—N284.18 (4)
C9—C8—H11117.3O3—Fe—O486.00 (4)
C8—C9—C10118.69 (13)O3—Fe—N1170.93 (4)
O4—C9—C8125.57 (12)O3—Fe—N295.43 (4)
O4—C9—C10115.74 (13)O4—Fe—N186.66 (4)
C9—C10—H14109.5O4—Fe—N290.87 (4)
C9—C10—H13109.5N1—Fe—N279.35 (4)
C9—C10—H12109.5C11—N1—Fe105.70 (9)
H14—C10—H13109.5C13—N1—C11109.69 (14)
H14—C10—H12109.5C13—N1—C14107.39 (13)
H13—C10—H12109.5C13—N1—Fe111.69 (10)
H16—C11—H15108.0C14—N1—C11111.18 (13)
C12—C11—H16109.3C14—N1—Fe111.24 (10)
C12—C11—H15109.3C12—N2—Fe104.52 (9)
N1—C11—H16109.3C15—N2—C12110.31 (14)
N1—C11—H15109.3C15—N2—Fe112.54 (10)
N1—C11—C12111.60 (14)C16—N2—C12109.77 (14)
C11—C12—H17109.2C16—N2—C15108.03 (14)
C11—C12—H18109.2C16—N2—Fe111.65 (10)
H17—C12—H18107.9C2—O1—Fe129.04 (9)
N2—C12—C11111.91 (13)C4—O2—Fe129.79 (9)
N2—C12—H17109.2C7—O3—Fe128.42 (10)
N2—C12—H18109.2C9—O4—Fe129.18 (9)
H19—C13—H21109.5
D—H···AD—HH···AD···AD—H···A
C1—H2···O1i0.962.623.5269 (18)157
[Zn(C5H7O2)2(C6H16N2)]F(000) = 808
Mr = 379.79Dx = 1.293 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.2335 (3) ÅCell parameters from 19126 reflections
b = 14.2134 (6) Åθ = 2.1–27.2°
c = 13.6738 (5) ŵ = 1.28 mm−1
β = 101.208 (3)°T = 200 K
V = 1950.96 (12) Å3Block, clear colourless
Z = 40.45 × 0.39 × 0.33 mm
STOE IPDS 2T diffractometer3456 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.047
rotation method, ω scansθmax = 26.7°, θmin = 2.1°
Absorption correction: numerical (X-AREA; Stoe & Cie, 2016)h = −12→12
Tmin = 0.627, Tmax = 0.779k = −17→16
22385 measured reflectionsl = −17→17
4124 independent reflections
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.076w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4124 reflectionsΔρmax = 0.37 e Å−3
216 parametersΔρmin = −0.26 e Å−3
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.
xyzUiso*/Ueq
Zn0.74026 (2)0.26429 (2)0.54676 (2)0.03991 (8)
O10.73445 (12)0.33774 (8)0.41466 (9)0.0534 (3)
O20.85986 (11)0.16705 (8)0.49492 (8)0.0507 (3)
O30.57869 (11)0.17554 (8)0.50853 (9)0.0529 (3)
O40.61242 (9)0.36299 (8)0.58630 (8)0.0441 (2)
N10.91461 (12)0.35505 (11)0.62041 (10)0.0499 (3)
N20.78674 (12)0.19573 (11)0.69813 (10)0.0459 (3)
C10.76595 (19)0.38103 (13)0.25509 (13)0.0575 (4)
H10.67250.40060.23730.086*
H20.79220.35040.19770.086*
H30.82220.43630.27430.086*
C20.78276 (15)0.31277 (12)0.34146 (11)0.0450 (4)
C30.85137 (17)0.22957 (12)0.33344 (13)0.0492 (4)
H40.87640.21690.27140.059*
C40.88628 (15)0.16331 (12)0.40893 (12)0.0462 (4)
C50.9672 (2)0.07864 (15)0.38836 (14)0.0672 (5)
H51.04930.07520.43890.101*
H60.98960.08490.32220.101*
H70.91490.02120.39070.101*
C60.3632 (2)0.11210 (15)0.48710 (15)0.0691 (5)
H80.37970.06460.54010.104*
H90.37580.08380.42420.104*
H100.27170.13540.47960.104*
C70.45930 (16)0.19273 (13)0.51387 (11)0.0476 (4)
C80.41127 (15)0.27812 (12)0.54200 (12)0.0475 (4)
H110.31800.28260.53910.057*
C90.48712 (14)0.35764 (11)0.57395 (11)0.0412 (3)
C100.41684 (16)0.44556 (13)0.59729 (13)0.0554 (4)
H120.33930.42830.62570.083*
H130.38750.48170.53590.083*
H140.47800.48380.64540.083*
C110.93211 (19)0.33443 (17)0.72727 (14)0.0676 (5)
H150.86440.36920.75560.081*
H161.02120.35630.76150.081*
C120.91917 (19)0.23151 (16)0.74583 (15)0.0651 (5)
H170.98870.19690.71940.078*
H180.93350.22000.81850.078*
C130.88618 (18)0.45547 (14)0.60157 (16)0.0671 (5)
H190.96290.49290.63410.101*
H200.80760.47320.62850.101*
H210.86910.46730.52960.101*
C141.03600 (16)0.33196 (16)0.58256 (16)0.0651 (5)
H221.02120.34490.51080.098*
H231.05730.26520.59440.098*
H241.11020.37040.61720.098*
C150.68709 (18)0.21961 (14)0.75840 (13)0.0560 (4)
H250.68350.28810.76600.084*
H260.71180.19020.82430.084*
H270.59950.19640.72510.084*
C160.7902 (2)0.09286 (14)0.68935 (15)0.0680 (5)
H280.70240.07000.65620.102*
H290.81370.06490.75600.102*
H300.85680.07500.65000.102*
U11U22U33U12U13U23
Zn0.03590 (11)0.04475 (13)0.04087 (12)0.00666 (7)0.01186 (8)−0.00208 (7)
O10.0628 (7)0.0534 (7)0.0470 (6)0.0178 (6)0.0187 (5)0.0051 (5)
O20.0555 (6)0.0545 (7)0.0465 (6)0.0158 (5)0.0204 (5)0.0024 (5)
O30.0488 (6)0.0496 (7)0.0592 (7)−0.0007 (5)0.0078 (5)−0.0096 (5)
O40.0335 (5)0.0470 (6)0.0538 (6)0.0028 (4)0.0136 (4)−0.0040 (5)
N10.0353 (6)0.0602 (9)0.0557 (8)−0.0041 (6)0.0125 (6)−0.0053 (7)
N20.0431 (7)0.0537 (8)0.0422 (7)0.0079 (6)0.0114 (5)0.0024 (6)
C10.0653 (11)0.0582 (11)0.0492 (10)−0.0021 (9)0.0114 (8)0.0046 (8)
C20.0406 (8)0.0525 (10)0.0417 (8)−0.0032 (7)0.0077 (6)−0.0012 (7)
C30.0529 (9)0.0559 (10)0.0417 (9)0.0035 (7)0.0163 (7)−0.0050 (7)
C40.0444 (8)0.0481 (9)0.0485 (9)0.0042 (7)0.0149 (7)−0.0079 (7)
C50.0817 (13)0.0620 (12)0.0632 (11)0.0230 (10)0.0271 (10)−0.0048 (9)
C60.0680 (12)0.0741 (14)0.0632 (12)−0.0250 (10)0.0074 (9)−0.0086 (10)
C70.0474 (8)0.0576 (10)0.0356 (8)−0.0083 (8)0.0028 (6)0.0009 (7)
C80.0323 (7)0.0653 (11)0.0451 (9)−0.0004 (7)0.0081 (6)0.0028 (7)
C90.0368 (7)0.0515 (9)0.0370 (8)0.0066 (6)0.0113 (6)0.0068 (6)
C100.0443 (8)0.0596 (11)0.0674 (11)0.0127 (7)0.0233 (8)0.0043 (8)
C110.0517 (10)0.0963 (16)0.0527 (11)−0.0182 (10)0.0053 (8)−0.0141 (10)
C120.0449 (9)0.0990 (16)0.0484 (10)0.0056 (9)0.0017 (8)0.0119 (10)
C130.0529 (10)0.0562 (11)0.0935 (14)−0.0131 (9)0.0175 (10)−0.0120 (10)
C140.0375 (8)0.0825 (14)0.0785 (13)−0.0044 (8)0.0194 (8)−0.0032 (11)
C150.0540 (10)0.0724 (12)0.0452 (9)0.0086 (8)0.0183 (8)0.0043 (8)
C160.0905 (14)0.0552 (11)0.0627 (11)0.0198 (10)0.0256 (10)0.0137 (9)
Zn—O12.0771 (12)C6—H90.9800
Zn—O22.0611 (11)C6—H100.9800
Zn—O32.0645 (11)C6—C71.508 (2)
Zn—O42.0607 (10)C7—C81.391 (3)
Zn—N12.2722 (13)C8—H110.9500
Zn—N22.2533 (13)C8—C91.393 (2)
O1—C21.2509 (19)C9—C101.507 (2)
O2—C41.2578 (19)C10—H120.9800
O3—C71.2619 (19)C10—H130.9800
O4—C91.2626 (17)C10—H140.9800
N1—C111.467 (2)C11—H150.9900
N1—C131.469 (2)C11—H160.9900
N1—C141.473 (2)C11—C121.495 (3)
N2—C121.476 (2)C12—H170.9900
N2—C151.470 (2)C12—H180.9900
N2—C161.468 (2)C13—H190.9800
C1—H10.9800C13—H200.9800
C1—H20.9800C13—H210.9800
C1—H30.9800C14—H220.9800
C1—C21.512 (2)C14—H230.9800
C2—C31.390 (2)C14—H240.9800
C3—H40.9500C15—H250.9800
C3—C41.392 (2)C15—H260.9800
C4—C51.518 (2)C15—H270.9800
C5—H50.9800C16—H280.9800
C5—H60.9800C16—H290.9800
C5—H70.9800C16—H300.9800
C6—H80.9800
O1—Zn—O287.50 (4)C7—C6—H8109.5
O1—Zn—O3101.58 (5)C7—C6—H9109.5
O1—Zn—O488.49 (4)C7—C6—H10109.5
O1—Zn—N189.28 (5)O3—C7—C6115.59 (16)
O1—Zn—N2168.94 (5)O3—C7—C8125.65 (15)
O2—Zn—O390.18 (5)C8—C7—C6118.76 (16)
O2—Zn—O4175.16 (4)C7—C8—H11116.9
O2—Zn—N193.76 (5)C7—C8—C9126.12 (15)
O2—Zn—N289.57 (5)C9—C8—H11116.9
O3—Zn—O487.96 (4)O4—C9—C8125.48 (15)
O3—Zn—N1168.61 (5)O4—C9—C10115.84 (15)
O3—Zn—N289.09 (5)C8—C9—C10118.67 (13)
O4—Zn—N188.92 (5)C9—C10—H12109.5
O4—Zn—N294.86 (5)C9—C10—H13109.5
N1—Zn—N280.27 (5)C9—C10—H14109.5
C2—O1—Zn127.18 (11)H12—C10—H13109.5
C4—O2—Zn126.86 (11)H12—C10—H14109.5
C7—O3—Zn127.15 (11)H13—C10—H14109.5
C9—O4—Zn127.15 (10)N1—C11—H15109.3
C11—N1—Zn105.16 (10)N1—C11—H16109.3
C11—N1—C13110.51 (16)N1—C11—C12111.53 (16)
C11—N1—C14110.95 (15)H15—C11—H16108.0
C13—N1—Zn111.23 (10)C12—C11—H15109.3
C13—N1—C14107.86 (15)C12—C11—H16109.3
C14—N1—Zn111.17 (11)N2—C12—C11111.49 (15)
C12—N2—Zn105.59 (11)N2—C12—H17109.3
C15—N2—Zn111.69 (10)N2—C12—H18109.3
C15—N2—C12110.50 (15)C11—C12—H17109.3
C16—N2—Zn111.08 (11)C11—C12—H18109.3
C16—N2—C12110.16 (14)H17—C12—H18108.0
C16—N2—C15107.84 (15)N1—C13—H19109.5
H1—C1—H2109.5N1—C13—H20109.5
H1—C1—H3109.5N1—C13—H21109.5
H2—C1—H3109.5H19—C13—H20109.5
C2—C1—H1109.5H19—C13—H21109.5
C2—C1—H2109.5H20—C13—H21109.5
C2—C1—H3109.5N1—C14—H22109.5
O1—C2—C1116.12 (15)N1—C14—H23109.5
O1—C2—C3126.06 (16)N1—C14—H24109.5
C3—C2—C1117.82 (15)H22—C14—H23109.5
C2—C3—H4117.4H22—C14—H24109.5
C2—C3—C4125.30 (15)H23—C14—H24109.5
C4—C3—H4117.4N2—C15—H25109.5
O2—C4—C3126.43 (15)N2—C15—H26109.5
O2—C4—C5115.53 (15)N2—C15—H27109.5
C3—C4—C5118.02 (15)H25—C15—H26109.5
C4—C5—H5109.5H25—C15—H27109.5
C4—C5—H6109.5H26—C15—H27109.5
C4—C5—H7109.5N2—C16—H28109.5
H5—C5—H6109.5N2—C16—H29109.5
H5—C5—H7109.5N2—C16—H30109.5
H6—C5—H7109.5H28—C16—H29109.5
H8—C6—H9109.5H28—C16—H30109.5
H8—C6—H10109.5H29—C16—H30109.5
H9—C6—H10109.5
  9 in total

1.  Adducts of bis(acetylacetonato)zinc(II) with 1,10-phenanthroline and 2,2'-bipyridine.

Authors:  Sanjaya Brahma; H P Sachin; S A Shivashankar; T Narasimhamurthy; R S Rathore
Journal:  Acta Crystallogr C       Date:  2008-02-16       Impact factor: 1.172

2.  From Positive to Negative Zero-Field Splitting in a Series of Strongly Magnetically Anisotropic Mononuclear Metal Complexes.

Authors:  Ghénadie Novitchi; Shangda Jiang; Sergiu Shova; Fatima Rida; Ivo Hlavička; Milan Orlita; Wolfgang Wernsdorfer; Rana Hamze; Cyril Martins; Nicolas Suaud; Nathalie Guihéry; Anne-Laure Barra; Cyrille Train
Journal:  Inorg Chem       Date:  2017-11-28       Impact factor: 5.165

3.  Synthesis and X-ray structure of ruthenium bis(acetylacetonate)(N,N,N',N'-tetramethylethylenediamine).

Authors:  Robert L Halbach; Grégory Nocton; Richard A Andersen
Journal:  Dalton Trans       Date:  2012-06-15       Impact factor: 4.390

4.  β-Fe2O3 nanomaterials from an iron(II) diketonate-diamine complex: a study from molecular precursor to growth process.

Authors:  Davide Barreca; Giorgio Carraro; Anjana Devi; Ettore Fois; Alberto Gasparotto; Roberta Seraglia; Chiara Maccato; Cinzia Sada; Gloria Tabacchi; Eugenio Tondello; Alfonso Venzo; Manuela Winter
Journal:  Dalton Trans       Date:  2011-11-02       Impact factor: 4.390

5.  MOCVD-derived highly transparent, conductive zinc- and tin-doped indium oxide thin films: precursor synthesis, metastable phase film growth and characterization, and application as anodes in polymer light-emitting diodes.

Authors:  Jun Ni; He Yan; Anchuang Wang; Yu Yang; Charlotte L Stern; Andrew W Metz; Shu Jin; Lian Wang; Tobin J Marks; John R Ireland; Carl R Kannewurf
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

6.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

7.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

8.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20

9.  The Cambridge Structural Database.

Authors:  Colin R Groom; Ian J Bruno; Matthew P Lightfoot; Suzanna C Ward
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2016-04-01
  9 in total
  1 in total

1.  Fluorinated β-diketonate complexes M(tfac)2(TMEDA) (M = Fe, Ni, Cu, Zn) as precursors for the MOCVD growth of metal and metal oxide thin films.

Authors:  Christian Stienen; Julian Grahl; Christoph Wölper; Stephan Schulz; Georg Bendt
Journal:  RSC Adv       Date:  2022-08-16       Impact factor: 4.036
  1 in total

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