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

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

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

Syntheses and crystal structures of three metal complexes [M(acac)₂(TMEDA)] [M = Mn (1), Fe (2) and Zn (3)] with acetylacetonate and N,N,N′,N′-tetramethylethylenediamine are discussed.

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

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019016372/wm5524sup1.cif Contains datablocks 1, 2, 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016372/wm55241sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016372/wm55242sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016372/wm55243sup4.hkl Contains datablock 3

CCDC references: 1969941; 1969940; 1969939

checkCIF report

Key indicators

Structure: 1

Single-crystal X-ray study
T = 213 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.099
Data-to-parameter ratio = 19.2

Structure: 2

Single-crystal X-ray study
T = 213 K
Mean (C-C) = 0.002 Å
R factor = 0.031
wR factor = 0.086
Data-to-parameter ratio = 24.4

Structure: 3

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R factor = 0.027
wR factor = 0.076
Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         31 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         13 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          2 Check

Alert level G
PLAT794_ALERT_5_G Tentative Bond Valency for Mn        (II)      .       2.07 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         52 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2       ..O1       .       2.62 Ang.
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe       --O2       .        7.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe       --O3       .        5.8 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Fe        (II)      .       2.07 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         63 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report

Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn       --O2       .        6.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn       --O4       .        6.0 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Zn        (II)      .       1.97 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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

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