{Bis(3,5-Di-tert-butyl-2-oxidobenzyl)[2-(N,N-dimethyl­amino)ethyl]amine-κ4N,N′,O,O′}zinc(II) and {bis­(3-tert-butyl-5-methyl-2-oxidobenzyl)[2-(N,N-dimethyl­amino)ethyl]amine-κ4N,N′,O,O′}(tetra­hdyrofuran)zinc(II)

Howard, R.H.; Bochmann, M.; Wright, J.A.

doi:10.1107/S0108270106018695

metal-organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages m293-m296

doi:10.1107/S0108270106018695

{Bis(3,5-Di-tert-butyl-2-oxidobenzyl)[2-(N,N-dimethylamino)ethyl]amine-κ⁴N,N′,O,O′}zinc(II) and {bis(3-tert-butyl-5-methyl-2-oxidobenzyl)[2-(N,N-dimethylamino)ethyl]amine-κ⁴N,N′,O,O′}(tetrahdyrofuran)zinc(II)

Ruth H. Howard,^a Manfred Bochmann ^a and Joseph A. Wright ^a ^*

^aSchool of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, England
^*Correspondence e-mail: joseph.wright@uea.ac.uk

(Received 3 May 2006; accepted 19 May 2006; online 23 June 2006)

The title zinc(II) complexes, [Zn(C₃₄H₅₄N₂O₂)], (II), and [Zn(C₂₈H₄₂N₂O₂)(C₄H₈O)], (III), were obtained as monomeric 1:1 complexes, in contrast with the calcium complexes supported by the same ligand class. Complex (II) crystallizes with two independent molecules in the asymmetric unit, which have similar geometric parameters. The donor atoms in (II) form a distorted trigonal–pyramidal arrangement around the zinc centre. Complex (III) contains a coordinated tetrahydrofuran molecule, resulting in a five-coordinate trigonal–bipyramidal arrangement around the Zn atom. The electron density provided by the coordination of this tetrahydrofuran molecule elongates the Zn—O and Zn—N bonds by approximately 0.07 and 0.10 Å, respectively, in comparison with (II). Neither (II) nor (III) is active as an ∊-caprolactone polymerization catalyst. The data presented here demonstrate that Zn may bind both an ONNO ligand and an additional oxygen-based ligand. The lack of activity is thus not due to steric hinderance at the metal atom.

Comment

The use of biodegradable polymers is of increasing interest, with environmental factors being a key driving force (Drumright et al., 2000 ). A principle route to these materials is the ring-opening polymerization of ∊-caprolactone (CL) (systematic name: oxepan-2-one) or lactide (LA) (systematic name: 3,6-dimethyl-1,4-dioxane-2,5-dione) to give polyesters. Both of these monomers are readily available from corn, and so are themselves renewable (O'Keefe et al., 2001 ; Dechy-Cabaret et al., 2004 ). In order to control the physical properties and tacticity of these polyesters, a variety of main-group and transition metal complexes have attracted attention.

The syntheses of a number of catalysts for CL and LA polymerization based on substituted aminobis(2-hydroxyarylmethyl) (ONNO) ligand systems have recently been

reported (Sarazin et al., 2006

). The first complexes of this class of ligands were those of group IV metals; in particular, the titanium, hafnium and zirconium benzyl complexes were structurally characterised and observed to be highly active in the polymerization of α-olefins (Tshuva et al., 2001a

, 2002

; Groysman et al., 2003

). Although Sarazin et al. (2006

) reported solution data on the magnesium, calcium, titanium and zinc complexes of the ONNO ligand (Ia)

(R = ^tBu), only the calcium [compound (IV)] and titanium [compound (V)] systems were structurally characterized. The calcium system was found to form a dimeric complex, both in the solid state and in solution. The solid-state structure showed one Ca⋯H agostic bond at each metal centre (Ca⋯H distances of 2.31 and 2.41 Å), resulting in distorted octahedral geometry at both Ca atoms. On the other hand, the titanium system was found to be monomeric and six-coordinate, with two coordination sites occupied by ⁱPrO⁻ groups. Equally, solution NMR data for the zinc system, (II)

, suggested a similar monomeric 1:1 structure. This is in line with the ionic radii of the metal ions, with calcium significantly larger than either titanium or zinc (Ca²⁺ = 1.14 Å, Zn²⁺ = 0.88 Å and Ti⁴⁺ = 0.75 Å; Atkins et al., 2006

). The monomeric nature of the zinc–ONNO complex, (II)

, has now been established by X-ray analysis. The related complex, (III)

, bearing a less bulky ONNO ligand, has also been synthesized and characterized for the first time.

Complex (II) crystallizes in the triclinic space group P $[\overline{1}]$ , with two independent molecules in the asymmetric unit (Fig. 1). Table 1 highlights the bond lengths and angles around the metal centre. It can be seen that the two independent molecules exhibit similar geometric values. The metal–donor distances in (II) (Table 1) are similar to those in the previously reported monomeric titanium complex, (V). The M—O distances in (II) fall close to those in (V) [1.9034 (15) and 1.9009 (15) Å], consistent with the similar ionic radii of the central atoms. However, the M—N distances are much longer in the titanium complex [2.400 (2) and 2.335 (2) Å] than in (II). In contrast, the dimeric calcium complex, (IV), exhibits significantly longer (non-bridging) M—O distances [2.1842 (16) and 2.1817 (16) Å] than (II). The M—N distances are again significantly shorter in (II) than in (IV) [2.4981 (19)–2.552 (2) Å]. The donor atoms form a distorted trigonal–pyramidal arrangement around the Zn atom, which lies 0.205 (1) Å from mean plane of the O and N atoms which form the base of the pyramid. The N_axial—Zn—donor angles demonstrate the distortion of the molecule from ideal geometry, with the two O atoms bent away from the Zn—N_axial bond.

Complex (III) is trigonal–bipyramidal, with the fifth coordination site occupied by a tetrahydrofuran (THF) molecule (Fig. 2). The change of R group from tert-butyl to methyl is remote from the metal centre, and so it is reasonable to compare the geometry of (III) with that seen in (II). As expected, the additional electron density donated by the THF molecule results in the elongation of the metal–donor bond lengths in (III) compared with (II) (Tables 1 and 2). The Zn—O bonds are lengthened by approximately 0.07 Å, whilst the Zn—N bonds are extended by approximately 0.1 Å. The geometry of the ONNO ligand at the metal centre is similar to that in (II), although the metal atom is displaced by only 0.0185 (16) Å from the mean plane of the equatorial donors.

Neither complex (II) nor (III) is active in the polymerization of LA or CL, in contrast with (IV). The structures presented in this report demonstrate the ability of the metal centre to bind both the ONNO ligand and an additional oxygen-based ligand. The lack of polymerization activity cannot, therefore, be due to steric protection of the Lewis acidic site.

Figure 1
The two independent molecules of (II)

in the asymmetric unit, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. Both molecules are shown in an arbitary orientation to allow comparison.

Figure 2
A representation of (III)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.

Experimental

The ligands (Ia) (Tshuva et al., 2001a) and (Ib) (Sarazin et al., 2006) were produced according to literature methods, as was complex (II) (Sarazin et al., 2006). Crystals of (II) suitable for X-ray diffraction were grown from a light petroleum–diethyl ether (1:3 v/v) solution at 268 K. Complex (III) was prepared by a method analogous to that used to produce (II). Reaction of Zn[N(SiMe₃)₂]₂ (0.97 g, 2.5 mmol) and (Ib) (1.1 g, 2.5 mmol) in light petroleum (30 ml) gave a white solid. ¹H NMR (300 MHz, C₆D₆): δ 7.31 (d, 2H, Ar), 6.60 (d, 2H, Ar), 3.76 (s, 1H, Ar–CH₂), 3.72 (s, 1H, Ar–CH₂), 3.07 (d, 1H, Ar–CH₂), 3.03 (s, 1H, Ar–CH₂), 2.34 (s, 6H, 2 × MeAr), 2.04 (t, 1H, N–CH₂–CH₂–N), 1.76 (s, 18H, ^tBu), 1.59 (t, 1H, N–CH₂–CH₂–N), 1.49 (s, 6H, NMe₂); ¹³C NMR (75MHz, C₆D₆): δ 164.9 (C–O), 138.7 (C_Ar), 130.5 (C_Ar), 128.9(C_Ar), 123.0 (C_Ar), 122.9 (C_Ar), 60.1 (Ar–CH₂), 59.4 (N–CH₂), 46.5 (N–CH₂), 41.8 [N(CH₃)₂], 35.8 [C(CH₃)₃], 30.2 [C(CH₃)₃], 22.9 (Ar–CH₃). Crystals of (III) suitable for X-ray diffraction were grown from a tetrahydrofuran–light petroleum–diethyl ether solution (1:1:3 v/v/v) at 268 K.

Compound (II)

Crystal data

[Zn(C₃₄H₅₄N₂O₂)]
M_r = 588.16
Triclinic, $[P \overline 1]$
a = 12.9275 (12) Å
b = 14.0002 (13) Å
c = 19.6729 (14) Å
α = 100.747 (7)°
β = 102.467 (7)°
γ = 96.879 (8)°
V = 3367.8 (5) Å³
Z = 4
D_x = 1.160 Mg m⁻³
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 140 (1) K
Plate, colourless
0.20 × 0.08 × 0.02 mm

Data collection

Oxford Xcalibur-3 CCD area-detector diffractometer
Thin-slice φ and ω scans
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003 $[Oxford Diffraction (2003). ABSPACK, CrysAlis CCD and CrysAlis RED. Versions 1.171. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.925, T_max = 0.983
42426 measured reflections
15272 independent reflections
8001 reflections with I > 2σ(I)
R_int = 0.076
θ_max = 27.6°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.071
S = 0.79
15272 reflections
744 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0243P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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

Zn1—O101	1.8918 (15)
Zn1—O102	1.8960 (17)
Zn1—N101	2.065 (2)
Zn1—N102	2.0864 (19)
Zn2—O201	1.8821 (16)
Zn2—O202	1.8899 (17)
Zn2—N201	2.0643 (18)
Zn2—N202	2.0727 (19)

O101—Zn1—O102	125.35 (7)
O101—Zn1—N101	99.58 (7)
O102—Zn1—N101	99.77 (7)
O101—Zn1—N102	112.76 (7)
O102—Zn1—N102	118.59 (8)
N101—Zn1—N102	87.81 (8)
O201—Zn2—O202	121.39 (7)
O201—Zn2—N201	99.95 (7)
O202—Zn2—N201	99.80 (7)
O201—Zn2—N202	113.08 (8)
O202—Zn2—N202	122.20 (8)
N201—Zn2—N202	88.07 (7)

Compound (III)

Crystal data

[Zn(C₂₈H₄₂N₂O₂)(C₄H₈O)]
M_r = 576.11
Monoclinic, P 2₁ /c
a = 13.669 (3) Å
b = 17.476 (4) Å
c = 12.989 (4) Å
β = 93.14 (2)°
V = 3098.1 (14) Å³
Z = 4
D_x = 1.235 Mg m⁻³
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 140 (1) K
Block, light yellow
0.06 × 0.06 × 0.02 mm

Data collection

Oxford X-calibur-3 CCD area-detector diffractometer
Thin-slice φ and ω scans
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003 $[Oxford Diffraction (2003). ABSPACK, CrysAlis CCD and CrysAlis RED. Versions 1.171. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.801, T_max = 0.984
33137 measured reflections
7121 independent reflections
2308 reflections with I > 2σ(I)
R_int = 0.195
θ_max = 27.8°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.073
S = 0.68
7121 reflections
353 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0123P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.49 e Å⁻³

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

Zn1—O102	1.958 (2)
Zn1—O101	1.961 (2)
Zn1—N101	2.163 (3)
Zn1—N102	2.166 (3)
Zn1—O103	2.246 (3)

O102—Zn1—O101	127.59 (10)
O102—Zn1—N101	93.35 (11)
O101—Zn1—N101	94.41 (10)
O102—Zn1—N102	112.67 (11)
O101—Zn1—N102	119.71 (11)
N101—Zn1—N102	82.88 (12)
O102—Zn1—O103	91.02 (10)
O101—Zn1—O103	87.46 (9)
N101—Zn1—O103	172.77 (11)
N102—Zn1—O103	90.13 (11)

All H atoms were refined using a riding model, with C—H = 0.98–0.99 Å and U_iso(H) = 1.5 or 1.2 times U_eq(C). Methyl H atoms were positioned using residual electron density (HFIX 137). One tert-butyl group of (II) (central atom C112, and methyl atoms C113, C114 and C115) was found to be disordered and was freely refined over two positions. This gave a final occupancy of 0.853 (3) for the major position (shown in Fig. 2). The central atom-to-methyl bonds were restrained to a distance of 1.55 Å for all of the disordered C atoms (DFIX 1.55 0.02). A second tert-butyl group (central atom C127, and methyl atoms C128, C129 and C130) showed evidence of disorder, particularly in the displacement parameters for atom C129. However, this could not be successfully modelled.

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). ABSPACK, CrysAlis CCD and CrysAlis RED. Versions 1.171. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ), WinGX (Farrugia, 1999 ) and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks global, II, III. DOI: 10.1107/S0108270106018695/fg3023sup1.cif

Structure factors: contains datablock II. DOI: 10.1107/S0108270106018695/fg3023IIsup2.hkl

Structure factors: contains datablock III. DOI: 10.1107/S0108270106018695/fg3023IIIsup3.hkl

Comment top

The use of biodegradable polymers is of increasing interest, with environmental factors being a key driving force (Drumright et al., 2000). A principle route to these materials is the ring-opening polymerization of ε-caprolactone (CL) (systematic name: oxepan-2-one) or lactide (LA) (systematic name: 3,6-dimethyl-[1,4]dioxane-2,5-dione) (Fig. 1) to give polyesters. Both of these monomers are readily available from corn, and so are themselves renewable (O'Keefe et al., 2001; Dechy-Cabaret et al., 2004). In order to control the physical properties and tacticity of these polyesters, a variety of main-group and transition metal complexes have attracted attention.

The synthesis of a number of catalysts for CL and LA polymerization based on substituted amino-bis(2-hydroxyarylmethyl) (ONNO) ligand systems has recently been reported (Sarazin et al., 2006). The first complexes of this class of ligands were those of group IV metals; in particular, the titanium, hafnium and zirconium benzyl complexes were structurally characterized and observed to be highly active in the polymerization of α-olefins (Tshuva et al., 2001a,b; Tshuva et al., 2002; Groysman et al., 2003). Although Sarazin et al. (2006) reported solution data on the magnesium, calcium, titanium and zinc complexes of the ONNO ligand (Ia) (R = ^tBu), only the calcium [(IV)] and titanium [(V)] systems were structurally characterized. The calcium system was found to form a dimeric complex, both in the solid state and in solution. The solid-state structure showed one Ca···H agostic bond at each metal centre (Ca···H distances of 2.31 and 2.41 Å), resulting in distorted octahedral geometry at both Ca atoms. On the other hand, the titanium system was found to be monomeric and six coordinate, with two coordination sites occupied by ⁱPrO⁻ groups. Equally, solution NMR data for the zinc system, (II), suggested a similar monomeric 1:1 structure. This is in line with the ionic radii of the metal ions, with calcium significantly larger than either titanium or zinc (Ca²⁺ 1.14 Å, Zn²⁺ 0.88 Å, Ti⁴⁺ 0.75 Å; Atkins et al., 2006). The monomeric nature of the zinc–ONNO complex, (II), has now been established by X-ray analysis. The related complex, (III), bearing a less bulky ONNO ligand, has also been synthesized and characterized for the first time.

Complex (II) crystallizes in the triclinic spacegroup P1, with two independent molecules in the asymmetric unit (Fig. 2). Table 1 highlights the bond lengths and angles around the metal centre. It can be seen that the two independent molecules exhibit similar geometric values. The metal–donor distances in (II) (Table 1) are similar to those in the previously reported monomeric titanium complex, (V). The M—O distances in (II) fall close to those in (V) [1.9034 (15) and 1.9009 (15) Å], consistent with the similar ionic radii of the central atoms. However, the M—N distances are much longer in the titanium complex [2.400 (2) and 2.335 (2) Å] than in (II). In contrast, the dimeric calcium complex, (IV), exhibits significantly longer (non-bridging) M—O [2.1842 (16) and 2.1817 (16) Å] distances than (II). The M—N distances are again significantly shorter in (II) than in (IV) [2.4981 (19)–2.552 (2) Å]. The donor atoms form a distorted trigonal–pyramidal arrangement around the Zn. The Zn atom is 0.205 (1) Å from mean plane of the O and N atoms which form the base of the pyramid. The N_axial—Zn—donor angles demonstrate the distortion of the molecule from ideal geometry, with the two O atoms bent away from the Zn—N_axial bond.

Complex (III) is trigonal–bipyramidal, with the fifth coordination site occupied by a tetrahydrofuran (THF) molecule (Fig. 3). The change of R group from ^tBu to methyl is remote from the metal centre, and so it is reasonable to compare the geometry of (III) with that seen in (II). As would be expected, the additional electron density donated by the THF molecule results in the elongation of the metal—donor bond lengths in (III) compared with complex (II) (Table 1 and Table 2). The Zn—O bonds are lengthened by approximately 0.07 Å, whilst the Zn—N bonds are extended by approximately 0.1 Å. The geometry of the ONNO ligand at the metal centre is similar to that in (II), although the metal is displaced by only 0.0185 (16) Å from the mean plane of the equatorial donors.

Neither complex (II) nor complex (III) is active in the polymerization of LA or CL, in contrast with (IV). The structures presented in this report demonstrate the ability of the metal centre to bind both the ONNO ligand and an additional oxygen-based ligand. The lack of polymerization activity cannot, therefore, be due to steric protection of the Lewis acidic site.

Experimental top

The ligands (Ia) (Tshuva et al., 2001a) and (Ib) (Sarazin et al., 2006) were produced by the literature methods, as was complex (II) (Sarazin et al., 2006). Crystals of (II) suitable for X-ray diffraction were grown from a 1:3 light petroleum—diethyl ether solution at 268 K. Complex (III) was prepared by a method analogous to that used to produce (II). Reaction of Zn[N(SiMe₃)₂]₂ (0.97 g, 2.5 mmol) and (Ib) (1.1 g, 2.5 mmol) in light petroleum (30 ml) gave a white solid. Spectroscopic analysis: ¹H NMR (300 MHz, C₆D₆, δ, p.p.m.): 7.31 (d, 2H, Ar), 6.60 (d, 2H, Ar), 3.76 (s, 1H, Ar—CH₂), 3.72 (s, 1H, Ar—CH₂), 3.07 (d, 1H, Ar—CH₂), 3.03 (s, 1H, Ar—CH₂), 2.34 (s, 6H, 2 × MeAr), 2.04 (t, 1H, N—CH₂—CH₂—N), 1.76 (s, 18H, ^tBu), 1.59 (t, 1H, N—CH₂—CH₂—N), 1.49 (s, 6H, NMe₂); ¹³C NMR (75 MHz, C₆D₆, δ, p.p.m.): 164.9 (C—O), 138.7 (C_Ar), 130.5 (C_Ar), 128.9(C_Ar), 123.0 (C_Ar), 122.9 (C_Ar), 60.1 (Ar—CH₂), 59.4 (N—CH₂), 46.5 (N—CH₂), 41.8 [N(CH₃)₂], 35.8 [C(CH₃)₃], 30.2 [C(CH₃)₃], 22.9 (Ar—CH₃). Crystals of (III) suitable for X-ray diffraction were grown from a 1:1:3 tetrahydrofuran–light petroleum–diethyl ether solution at 268 K.

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

Figures top

Fig. 1. ε-Caprolactone and lactide

Fig. 2. The two independent molecules of (II) in the asymmetric unit, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. Both molecules are shown in an arbitary orientation to allow comparison.

Fig. 3. A representation of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.

(II) {Bis(3,5-Di-tert-butyl-2-oxidobenzyl)[2-(N,N-dimethylamino)ethyl]amine- κ⁴N,N',O,O'}zinc(II) top

Crystal data top

[Zn(C₃₄H₅₄N₂O₂)]	Z = 4
M_r = 588.16	F(000) = 1272
Triclinic, P1	D_x = 1.160 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.9275 (12) Å	Cell parameters from 15277 reflections
b = 14.0002 (13) Å	θ = 3.7–27.6°
c = 19.6729 (14) Å	µ = 0.76 mm⁻¹
α = 100.747 (7)°	T = 140 K
β = 102.467 (7)°	Plate, colourless
γ = 96.879 (8)°	0.20 × 0.08 × 0.02 mm
V = 3367.8 (5) Å³

Data collection top

Oxford Xcalibur3 CCD area-detector diffractometer	15272 independent reflections
Radiation source: Enhance (Mo) X-ray Source	8001 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
Detector resolution: 16.0050 pixels mm^-1	θ_max = 27.6°, θ_min = 3.7°
Thin slice ϕ and ω scans	h = −16→16
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003)	k = −18→18
T_min = 0.925, T_max = 0.983	l = −25→25
42426 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 0.79	w = 1/[σ²(F_o²) + (0.0243P)²] where P = (F_o² + 2F_c²)/3
15272 reflections	(Δ/σ)_max = 0.001
744 parameters	Δρ_max = 0.45 e Å⁻³
12 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Zn(C₃₄H₅₄N₂O₂)]	γ = 96.879 (8)°
M_r = 588.16	V = 3367.8 (5) Å³
Triclinic, P1	Z = 4
a = 12.9275 (12) Å	Mo Kα radiation
b = 14.0002 (13) Å	µ = 0.76 mm⁻¹
c = 19.6729 (14) Å	T = 140 K
α = 100.747 (7)°	0.20 × 0.08 × 0.02 mm
β = 102.467 (7)°

Data collection top

Oxford Xcalibur3 CCD area-detector diffractometer	15272 independent reflections
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003)	8001 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.983	R_int = 0.076
42426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	12 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 0.79	Δρ_max = 0.45 e Å⁻³
15272 reflections	Δρ_min = −0.43 e Å⁻³
744 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.21611 (2)	0.06073 (2)	0.826370 (15)	0.02147 (8)
Zn2	0.83543 (2)	0.48447 (2)	0.314827 (15)	0.02080 (8)
C101	0.32137 (19)	0.01416 (17)	0.71210 (13)	0.0256 (6)
H10A	0.3196	−0.0032	0.6607	0.031*
H10B	0.3589	−0.0332	0.7354	0.031*
C102	0.38484 (19)	0.11712 (16)	0.74353 (12)	0.0207 (6)
C103	0.40703 (19)	0.15618 (17)	0.81766 (12)	0.0197 (6)
C104	0.47591 (19)	0.24934 (17)	0.84629 (12)	0.0206 (6)
C105	0.51285 (19)	0.29836 (17)	0.79840 (12)	0.0226 (6)
H105	0.5580	0.3606	0.8174	0.027*
C106	0.48846 (19)	0.26283 (17)	0.72477 (12)	0.0217 (6)
C107	0.42495 (19)	0.17083 (18)	0.69919 (13)	0.0236 (6)
H107	0.4080	0.1431	0.6494	0.028*
C108	0.50685 (19)	0.29201 (17)	0.92665 (12)	0.0234 (6)
C109	0.5824 (2)	0.39143 (19)	0.94640 (13)	0.0383 (8)
H10C	0.6475	0.3832	0.9296	0.057*
H10D	0.6018	0.4153	0.9983	0.057*
H10E	0.5461	0.4392	0.9239	0.057*
C110	0.5659 (2)	0.22020 (18)	0.96521 (13)	0.0289 (6)
H11A	0.5181	0.1569	0.9557	0.043*
H11B	0.5871	0.2481	1.0167	0.043*
H11C	0.6302	0.2101	0.9477	0.043*
C111	0.4072 (2)	0.30963 (18)	0.95451 (13)	0.0292 (6)
H11D	0.3715	0.3569	0.9310	0.044*
H11E	0.4289	0.3360	1.0062	0.044*
H11F	0.3575	0.2472	0.9441	0.044*
C112	0.5324 (2)	0.32285 (19)	0.67592 (13)	0.0280 (6)
C113	0.6569 (2)	0.3308 (2)	0.69166 (18)	0.0364 (9)	0.853 (3)
H11G	0.6848	0.3703	0.6613	0.055*	0.853 (3)
H11H	0.6755	0.2646	0.6817	0.055*	0.853 (3)
H11I	0.6887	0.3625	0.7419	0.055*	0.853 (3)
C114	0.4844 (3)	0.2784 (2)	0.59823 (15)	0.0395 (10)	0.853 (3)
H11J	0.5099	0.3221	0.5695	0.059*	0.853 (3)
H11K	0.4059	0.2702	0.5887	0.059*	0.853 (3)
H11L	0.5062	0.2140	0.5857	0.059*	0.853 (3)
C115	0.5075 (3)	0.4286 (2)	0.69173 (16)	0.0291 (8)	0.853 (3)
H11M	0.5390	0.4594	0.7422	0.044*	0.853 (3)
H11N	0.4295	0.4264	0.6811	0.044*	0.853 (3)
H11O	0.5382	0.4672	0.6619	0.044*	0.853 (3)
C313	0.5950 (15)	0.2543 (12)	0.6328 (10)	0.0364 (9)	0.147 (3)
H33A	0.6275	0.2905	0.6024	0.055*	0.147 (3)
H33B	0.5450	0.1960	0.6030	0.055*	0.147 (3)
H33C	0.6515	0.2338	0.6661	0.055*	0.147 (3)
C314	0.4328 (14)	0.3315 (15)	0.6112 (9)	0.0395 (10)	0.147 (3)
H34A	0.3956	0.3847	0.6282	0.059*	0.147 (3)
H34B	0.3824	0.2691	0.5955	0.059*	0.147 (3)
H34C	0.4609	0.3460	0.5711	0.059*	0.147 (3)
C315	0.5887 (15)	0.4250 (10)	0.7067 (9)	0.0291 (8)	0.147 (3)
H35A	0.6010	0.4570	0.6683	0.044*	0.147 (3)
H35B	0.6578	0.4242	0.7389	0.044*	0.147 (3)
H35C	0.5446	0.4615	0.7334	0.044*	0.147 (3)
C116	0.1446 (2)	0.06182 (18)	0.67715 (13)	0.0265 (6)
H11P	0.1351	0.0317	0.6260	0.032*
H11Q	0.1854	0.1293	0.6865	0.032*
C117	0.0354 (2)	0.06885 (17)	0.69117 (13)	0.0244 (6)
C118	0.02346 (19)	0.11206 (16)	0.75938 (13)	0.0220 (6)
C119	−0.0807 (2)	0.12601 (17)	0.76780 (14)	0.0252 (6)
C120	−0.1674 (2)	0.09147 (18)	0.70836 (14)	0.0303 (7)
H120	−0.2371	0.0997	0.7141	0.036*
C121	−0.1581 (2)	0.04578 (18)	0.64143 (15)	0.0343 (7)
C122	−0.0556 (2)	0.03642 (17)	0.63422 (14)	0.0320 (7)
H122	−0.0465	0.0068	0.5888	0.038*
C123	−0.0975 (2)	0.17830 (18)	0.83949 (14)	0.0287 (6)
C124	−0.0317 (2)	0.28366 (17)	0.86243 (13)	0.0291 (6)
H12A	−0.0569	0.3217	0.8269	0.044*
H12B	0.0445	0.2802	0.8660	0.044*
H12C	−0.0411	0.3159	0.9089	0.044*
C125	−0.0624 (2)	0.11926 (18)	0.89690 (13)	0.0350 (7)
H12D	−0.0791	0.1498	0.9414	0.053*
H12E	0.0151	0.1192	0.9052	0.053*
H12F	−0.1009	0.0513	0.8806	0.053*
C126	−0.2150 (2)	0.1888 (2)	0.83663 (16)	0.0469 (8)
H12G	−0.2391	0.2288	0.8022	0.070*
H12H	−0.2211	0.2211	0.8840	0.070*
H12I	−0.2598	0.1234	0.8219	0.070*
C127	−0.2555 (2)	0.0094 (2)	0.57674 (16)	0.0462 (9)
C128	−0.2519 (3)	0.0781 (3)	0.52605 (17)	0.0745 (12)
H12J	−0.1844	0.0790	0.5110	0.112*
H12K	−0.2564	0.1448	0.5502	0.112*
H12L	−0.3126	0.0550	0.4841	0.112*
C129	−0.2536 (3)	−0.0951 (2)	0.5405 (2)	0.124 (2)
H12M	−0.3182	−0.1190	0.5014	0.186*
H12N	−0.2518	−0.1373	0.5751	0.186*
H12O	−0.1897	−0.0970	0.5214	0.186*
C130	−0.3631 (3)	0.0113 (3)	0.59868 (19)	0.0814 (13)
H13D	−0.4228	−0.0151	0.5566	0.122*
H13E	−0.3684	0.0794	0.6193	0.122*
H13F	−0.3663	−0.0290	0.6341	0.122*
C131	0.1584 (2)	−0.10094 (16)	0.70662 (13)	0.0268 (6)
H13G	0.1793	−0.1393	0.6655	0.032*
H13H	0.0793	−0.1060	0.6943	0.032*
C132	0.1933 (2)	−0.14385 (17)	0.77191 (13)	0.0283 (6)
H13I	0.1544	−0.2121	0.7629	0.034*
H13J	0.2712	−0.1464	0.7806	0.034*
C133	0.2350 (2)	−0.10487 (19)	0.90182 (14)	0.0432 (8)
H13K	0.2154	−0.1746	0.9020	0.065*
H13L	0.2206	−0.0638	0.9438	0.065*
H13M	0.3116	−0.0905	0.9031	0.065*
C134	0.0546 (2)	−0.10599 (18)	0.83519 (15)	0.0370 (7)
H13N	0.0347	−0.1768	0.8320	0.056*
H13O	0.0113	−0.0874	0.7938	0.056*
H13P	0.0416	−0.0688	0.8790	0.056*
C201	0.65527 (17)	0.45778 (17)	0.19360 (12)	0.0197 (6)
H20A	0.6241	0.4415	0.1414	0.024*
H20B	0.6323	0.5197	0.2136	0.024*
C202	0.61032 (17)	0.37572 (16)	0.22537 (12)	0.0174 (5)
C203	0.63793 (18)	0.38410 (17)	0.29998 (13)	0.0196 (6)
C204	0.59083 (19)	0.30878 (17)	0.32866 (12)	0.0204 (6)
C205	0.51772 (18)	0.23105 (17)	0.28150 (12)	0.0211 (6)
H205	0.4863	0.1807	0.3007	0.025*
C206	0.48736 (18)	0.22222 (17)	0.20753 (12)	0.0202 (6)
C207	0.53645 (18)	0.29562 (16)	0.18092 (12)	0.0183 (6)
H207	0.5193	0.2913	0.1309	0.022*
C208	0.6194 (2)	0.31407 (18)	0.40947 (12)	0.0242 (6)
C209	0.5605 (2)	0.22461 (18)	0.42853 (13)	0.0348 (7)
H20C	0.5832	0.2291	0.4800	0.052*
H20D	0.5778	0.1639	0.4030	0.052*
H20E	0.4828	0.2237	0.4147	0.052*
C210	0.5884 (2)	0.40755 (17)	0.44889 (13)	0.0266 (6)
H21A	0.5103	0.4042	0.4346	0.040*
H21B	0.6241	0.4656	0.4368	0.040*
H21C	0.6108	0.4126	0.5005	0.040*
C211	0.7409 (2)	0.31509 (19)	0.43651 (13)	0.0328 (7)
H21D	0.7814	0.3722	0.4262	0.049*
H21E	0.7602	0.2544	0.4124	0.049*
H21F	0.7583	0.3193	0.4881	0.049*
C212	0.40207 (19)	0.13512 (17)	0.16153 (13)	0.0235 (6)
C213	0.29744 (19)	0.13683 (18)	0.18712 (14)	0.0298 (7)
H21G	0.2733	0.2002	0.1849	0.045*
H21H	0.3107	0.1282	0.2364	0.045*
H21I	0.2418	0.0832	0.1563	0.045*
C214	0.3769 (2)	0.13907 (18)	0.08281 (12)	0.0313 (7)
H21J	0.3544	0.2022	0.0773	0.047*
H21K	0.3190	0.0849	0.0558	0.047*
H21L	0.4413	0.1327	0.0647	0.047*
C215	0.4407 (2)	0.03678 (17)	0.16800 (14)	0.0324 (7)
H21M	0.3852	−0.0180	0.1386	0.049*
H21N	0.4546	0.0311	0.2179	0.049*
H21O	0.5070	0.0345	0.1516	0.049*
C216	0.81327 (18)	0.39133 (17)	0.16733 (13)	0.0206 (6)
H21P	0.7934	0.3919	0.1159	0.025*
H21Q	0.7753	0.3290	0.1735	0.025*
C217	0.93294 (18)	0.39221 (16)	0.18959 (12)	0.0184 (6)
C218	0.98275 (18)	0.38766 (16)	0.26066 (12)	0.0191 (5)
C219	1.09358 (19)	0.38057 (16)	0.27772 (12)	0.0204 (6)
C220	1.14985 (19)	0.38320 (16)	0.22483 (13)	0.0226 (6)
H220	1.2243	0.3796	0.2367	0.027*
C221	1.10328 (19)	0.39089 (16)	0.15538 (13)	0.0204 (6)
C222	0.99400 (18)	0.39491 (16)	0.13988 (13)	0.0208 (6)
H222	0.9596	0.3997	0.0931	0.025*
C223	1.14889 (19)	0.36973 (18)	0.35306 (13)	0.0239 (6)
C224	1.0919 (2)	0.27716 (18)	0.37025 (13)	0.0309 (7)
H22A	1.1264	0.2719	0.4186	0.046*
H22B	1.0969	0.2184	0.3359	0.046*
H22C	1.0161	0.2823	0.3671	0.046*
C225	1.1460 (2)	0.46093 (18)	0.40904 (13)	0.0332 (7)
H22D	1.1842	0.4545	0.4563	0.050*
H22E	1.0712	0.4666	0.4091	0.050*
H22F	1.1807	0.5200	0.3976	0.050*
C226	1.2677 (2)	0.3587 (2)	0.35992 (14)	0.0369 (7)
H22G	1.3070	0.4176	0.3511	0.055*
H22H	1.2724	0.3006	0.3249	0.055*
H22I	1.2993	0.3507	0.4081	0.055*
C227	1.16632 (19)	0.38907 (18)	0.09749 (13)	0.0244 (6)
C228	1.1392 (2)	0.4676 (2)	0.05450 (14)	0.0376 (7)
H22J	1.1578	0.5330	0.0866	0.056*
H22K	1.0622	0.4546	0.0315	0.056*
H22L	1.1803	0.4655	0.0180	0.056*
C229	1.1350 (2)	0.28661 (18)	0.04725 (14)	0.0334 (7)
H22M	1.1747	0.2838	0.0100	0.050*
H22N	1.0577	0.2743	0.0252	0.050*
H22O	1.1526	0.2363	0.0745	0.050*
C230	1.28785 (19)	0.40901 (18)	0.12852 (13)	0.0292 (6)
H23A	1.3085	0.4733	0.1620	0.044*
H23B	1.3245	0.4091	0.0898	0.044*
H23C	1.3085	0.3574	0.1537	0.044*
C231	0.81672 (19)	0.57145 (16)	0.19410 (12)	0.0212 (6)
H23D	0.7678	0.5844	0.1519	0.025*
H23E	0.8883	0.5696	0.1840	0.025*
C232	0.8256 (2)	0.65388 (17)	0.25868 (13)	0.0260 (6)
H23F	0.8586	0.7169	0.2504	0.031*
H23G	0.7529	0.6609	0.2653	0.031*
C233	0.8727 (2)	0.69441 (19)	0.38847 (14)	0.0426 (8)
H23H	0.9161	0.6795	0.4314	0.064*
H23I	0.7964	0.6806	0.3881	0.064*
H23J	0.8926	0.7642	0.3884	0.064*
C234	1.0084 (2)	0.65339 (19)	0.32612 (15)	0.0352 (7)
H23K	1.0274	0.7217	0.3223	0.053*
H23L	1.0234	0.6086	0.2861	0.053*
H23M	1.0511	0.6436	0.3711	0.053*
N101	0.20907 (16)	0.00364 (13)	0.72052 (10)	0.0218 (5)
N102	0.17089 (17)	−0.08316 (14)	0.83635 (11)	0.0284 (5)
N201	0.77509 (15)	0.47478 (13)	0.20724 (10)	0.0187 (5)
N202	0.89223 (16)	0.63242 (14)	0.32436 (11)	0.0253 (5)
O101	0.36577 (12)	0.10567 (11)	0.86029 (8)	0.0227 (4)
O102	0.10972 (13)	0.14260 (11)	0.81524 (8)	0.0224 (4)
O201	0.70621 (12)	0.46305 (11)	0.34334 (8)	0.0216 (4)
O202	0.92543 (12)	0.38776 (11)	0.31033 (8)	0.0213 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02403 (18)	0.01658 (17)	0.02199 (18)	0.00116 (13)	0.00418 (14)	0.00286 (13)
Zn2	0.01902 (17)	0.01911 (17)	0.02331 (18)	0.00040 (13)	0.00428 (14)	0.00509 (14)
C101	0.0316 (16)	0.0234 (14)	0.0220 (15)	0.0048 (12)	0.0091 (12)	0.0020 (12)
C102	0.0234 (14)	0.0159 (13)	0.0202 (14)	0.0009 (10)	0.0052 (11)	−0.0010 (11)
C103	0.0212 (14)	0.0181 (13)	0.0221 (14)	0.0055 (11)	0.0072 (11)	0.0063 (11)
C104	0.0223 (14)	0.0194 (13)	0.0205 (14)	0.0031 (11)	0.0077 (11)	0.0026 (11)
C105	0.0228 (14)	0.0216 (14)	0.0214 (14)	−0.0011 (11)	0.0073 (11)	0.0006 (11)
C106	0.0222 (14)	0.0230 (14)	0.0207 (14)	0.0020 (11)	0.0088 (11)	0.0038 (11)
C107	0.0283 (15)	0.0251 (15)	0.0180 (14)	0.0054 (12)	0.0080 (12)	0.0031 (12)
C108	0.0242 (15)	0.0241 (14)	0.0200 (14)	−0.0011 (11)	0.0072 (11)	0.0016 (11)
C109	0.0476 (19)	0.0385 (17)	0.0196 (15)	−0.0116 (14)	0.0086 (14)	−0.0047 (13)
C110	0.0255 (15)	0.0381 (16)	0.0216 (15)	0.0052 (12)	0.0061 (12)	0.0030 (12)
C111	0.0354 (16)	0.0302 (15)	0.0233 (15)	0.0106 (12)	0.0102 (13)	0.0027 (12)
C112	0.0324 (17)	0.0293 (16)	0.0256 (16)	0.0021 (13)	0.0163 (13)	0.0057 (13)
C113	0.036 (2)	0.036 (2)	0.047 (2)	0.0081 (16)	0.0238 (17)	0.0160 (17)
C114	0.058 (3)	0.038 (2)	0.0239 (18)	−0.0050 (17)	0.0205 (17)	0.0051 (16)
C115	0.033 (2)	0.0315 (18)	0.0257 (18)	0.0038 (16)	0.0101 (16)	0.0115 (15)
C313	0.036 (2)	0.036 (2)	0.047 (2)	0.0081 (16)	0.0238 (17)	0.0160 (17)
C314	0.058 (3)	0.038 (2)	0.0239 (18)	−0.0050 (17)	0.0205 (17)	0.0051 (16)
C315	0.033 (2)	0.0315 (18)	0.0257 (18)	0.0038 (16)	0.0101 (16)	0.0115 (15)
C116	0.0376 (17)	0.0189 (14)	0.0199 (15)	0.0036 (12)	0.0029 (12)	0.0025 (11)
C117	0.0277 (15)	0.0182 (14)	0.0245 (15)	0.0002 (11)	0.0005 (12)	0.0066 (12)
C118	0.0239 (15)	0.0126 (13)	0.0245 (15)	−0.0016 (11)	−0.0020 (12)	0.0035 (11)
C119	0.0248 (15)	0.0158 (14)	0.0320 (16)	−0.0018 (11)	0.0019 (13)	0.0073 (12)
C120	0.0234 (15)	0.0258 (15)	0.0381 (18)	0.0021 (12)	−0.0021 (13)	0.0107 (13)
C121	0.0341 (18)	0.0194 (15)	0.0397 (18)	−0.0009 (12)	−0.0121 (14)	0.0101 (13)
C122	0.0471 (19)	0.0180 (14)	0.0219 (15)	0.0033 (13)	−0.0068 (14)	0.0016 (12)
C123	0.0230 (15)	0.0281 (15)	0.0356 (17)	0.0009 (12)	0.0078 (13)	0.0095 (13)
C124	0.0297 (16)	0.0254 (15)	0.0334 (16)	0.0054 (12)	0.0111 (13)	0.0046 (12)
C125	0.0386 (18)	0.0273 (15)	0.0356 (17)	−0.0075 (13)	0.0090 (14)	0.0065 (13)
C126	0.0276 (17)	0.061 (2)	0.053 (2)	0.0051 (15)	0.0159 (15)	0.0110 (17)
C127	0.044 (2)	0.0327 (18)	0.044 (2)	0.0073 (14)	−0.0230 (16)	0.0030 (15)
C128	0.072 (3)	0.092 (3)	0.047 (2)	0.013 (2)	−0.0203 (19)	0.022 (2)
C129	0.106 (4)	0.047 (2)	0.137 (4)	0.028 (2)	−0.097 (3)	−0.044 (2)
C130	0.040 (2)	0.096 (3)	0.081 (3)	−0.012 (2)	−0.028 (2)	0.017 (2)
C131	0.0363 (16)	0.0140 (13)	0.0268 (15)	−0.0003 (11)	0.0080 (13)	−0.0011 (11)
C132	0.0294 (16)	0.0169 (14)	0.0357 (17)	0.0005 (12)	0.0047 (13)	0.0043 (12)
C133	0.063 (2)	0.0321 (17)	0.0344 (18)	0.0113 (15)	0.0057 (16)	0.0128 (14)
C134	0.0449 (19)	0.0196 (15)	0.0480 (19)	−0.0029 (13)	0.0193 (15)	0.0067 (13)
C201	0.0160 (13)	0.0223 (14)	0.0203 (14)	0.0023 (10)	0.0040 (11)	0.0049 (11)
C202	0.0133 (13)	0.0180 (13)	0.0216 (14)	0.0017 (10)	0.0054 (10)	0.0052 (11)
C203	0.0162 (13)	0.0191 (13)	0.0232 (14)	0.0041 (10)	0.0049 (11)	0.0029 (11)
C204	0.0212 (14)	0.0189 (13)	0.0226 (14)	0.0047 (11)	0.0074 (11)	0.0047 (11)
C205	0.0205 (14)	0.0189 (13)	0.0269 (15)	0.0007 (11)	0.0105 (11)	0.0086 (11)
C206	0.0177 (14)	0.0190 (14)	0.0223 (14)	0.0008 (11)	0.0045 (11)	0.0024 (11)
C207	0.0172 (13)	0.0214 (14)	0.0168 (13)	0.0041 (11)	0.0057 (11)	0.0030 (11)
C208	0.0287 (15)	0.0243 (14)	0.0193 (14)	0.0035 (12)	0.0063 (12)	0.0040 (11)
C209	0.0546 (19)	0.0272 (15)	0.0233 (15)	0.0024 (14)	0.0131 (14)	0.0062 (12)
C210	0.0256 (15)	0.0306 (15)	0.0254 (15)	0.0034 (12)	0.0097 (12)	0.0074 (12)
C211	0.0394 (17)	0.0366 (16)	0.0222 (15)	0.0130 (13)	0.0048 (13)	0.0051 (13)
C212	0.0216 (14)	0.0208 (14)	0.0247 (15)	−0.0018 (11)	0.0050 (12)	0.0009 (12)
C213	0.0226 (15)	0.0290 (15)	0.0349 (17)	−0.0020 (12)	0.0069 (13)	0.0038 (13)
C214	0.0250 (15)	0.0331 (16)	0.0276 (16)	−0.0082 (12)	0.0025 (12)	−0.0007 (13)
C215	0.0275 (16)	0.0222 (15)	0.0405 (18)	−0.0020 (12)	0.0043 (14)	−0.0018 (13)
C216	0.0201 (14)	0.0173 (13)	0.0239 (15)	0.0021 (11)	0.0043 (11)	0.0051 (11)
C217	0.0145 (13)	0.0156 (13)	0.0242 (14)	0.0023 (10)	0.0033 (11)	0.0040 (11)
C218	0.0186 (13)	0.0126 (12)	0.0247 (14)	−0.0019 (10)	0.0046 (11)	0.0047 (11)
C219	0.0186 (14)	0.0162 (13)	0.0236 (14)	0.0007 (10)	0.0008 (11)	0.0038 (11)
C220	0.0134 (13)	0.0209 (14)	0.0315 (16)	0.0013 (11)	0.0031 (11)	0.0043 (12)
C221	0.0181 (14)	0.0173 (13)	0.0244 (15)	0.0024 (10)	0.0040 (11)	0.0026 (11)
C222	0.0207 (14)	0.0183 (13)	0.0211 (14)	0.0020 (10)	0.0019 (11)	0.0031 (11)
C223	0.0206 (14)	0.0264 (15)	0.0224 (15)	0.0032 (11)	0.0006 (11)	0.0053 (12)
C224	0.0271 (15)	0.0319 (16)	0.0344 (17)	0.0054 (12)	0.0021 (13)	0.0148 (13)
C225	0.0321 (17)	0.0360 (17)	0.0249 (16)	0.0051 (13)	−0.0041 (13)	0.0038 (13)
C226	0.0241 (16)	0.0526 (19)	0.0328 (17)	0.0080 (13)	−0.0027 (13)	0.0164 (15)
C227	0.0198 (14)	0.0288 (15)	0.0256 (15)	0.0065 (11)	0.0074 (12)	0.0044 (12)
C228	0.0306 (17)	0.0501 (19)	0.0449 (18)	0.0155 (14)	0.0183 (14)	0.0260 (15)
C229	0.0264 (16)	0.0391 (17)	0.0303 (16)	0.0045 (13)	0.0053 (13)	−0.0009 (13)
C230	0.0255 (15)	0.0310 (15)	0.0318 (16)	0.0046 (12)	0.0112 (12)	0.0039 (12)
C231	0.0198 (14)	0.0170 (13)	0.0278 (15)	0.0001 (10)	0.0067 (11)	0.0085 (11)
C232	0.0228 (15)	0.0170 (14)	0.0383 (17)	0.0009 (11)	0.0066 (12)	0.0088 (12)
C233	0.058 (2)	0.0310 (17)	0.0339 (18)	0.0070 (15)	0.0071 (16)	0.0011 (14)
C234	0.0300 (17)	0.0260 (16)	0.0448 (19)	−0.0059 (13)	0.0010 (14)	0.0122 (14)
N101	0.0259 (12)	0.0134 (11)	0.0244 (12)	0.0010 (9)	0.0053 (10)	0.0023 (9)
N102	0.0332 (14)	0.0221 (12)	0.0272 (13)	0.0009 (10)	0.0025 (11)	0.0069 (10)
N201	0.0161 (11)	0.0133 (10)	0.0259 (12)	0.0006 (8)	0.0039 (9)	0.0050 (9)
N202	0.0265 (13)	0.0183 (12)	0.0282 (13)	−0.0003 (9)	0.0048 (10)	0.0024 (10)
O101	0.0233 (10)	0.0241 (9)	0.0192 (9)	0.0002 (7)	0.0032 (8)	0.0056 (8)
O102	0.0216 (10)	0.0204 (9)	0.0214 (10)	0.0027 (7)	0.0005 (8)	0.0009 (8)
O201	0.0201 (9)	0.0190 (9)	0.0221 (10)	−0.0033 (7)	0.0052 (8)	0.0000 (7)
O202	0.0211 (10)	0.0227 (9)	0.0236 (10)	0.0038 (7)	0.0072 (8)	0.0112 (8)

Geometric parameters (Å, º) top

Zn1—O101	1.8918 (15)	C132—H13I	0.9900
Zn1—O102	1.8960 (17)	C132—H13J	0.9900
Zn1—N101	2.065 (2)	C133—N102	1.478 (3)
Zn1—N102	2.0864 (19)	C133—H13K	0.9800
Zn2—O201	1.8821 (16)	C133—H13L	0.9800
Zn2—O202	1.8899 (17)	C133—H13M	0.9800
Zn2—N201	2.0643 (18)	C134—N102	1.493 (3)
Zn2—N202	2.0727 (19)	C134—H13N	0.9800
C101—N101	1.490 (3)	C134—H13O	0.9800
C101—C102	1.516 (3)	C134—H13P	0.9800
C101—H10A	0.9900	C201—N201	1.495 (3)
C101—H10B	0.9900	C201—C202	1.521 (3)
C102—C107	1.394 (3)	C201—H20A	0.9900
C102—C103	1.412 (3)	C201—H20B	0.9900
C103—O101	1.346 (2)	C202—C207	1.397 (3)
C103—C104	1.429 (3)	C202—C203	1.412 (3)
C104—C105	1.394 (3)	C203—O201	1.348 (3)
C104—C108	1.528 (3)	C203—C204	1.420 (3)
C105—C106	1.393 (3)	C204—C205	1.392 (3)
C105—H105	0.9500	C204—C208	1.538 (3)
C106—C107	1.383 (3)	C205—C206	1.401 (3)
C106—C112	1.541 (3)	C205—H205	0.9500
C107—H107	0.9500	C206—C207	1.386 (3)
C108—C111	1.534 (3)	C206—C212	1.535 (3)
C108—C109	1.533 (3)	C207—H207	0.9500
C108—C110	1.545 (3)	C208—C210	1.535 (3)
C109—H10C	0.9800	C208—C209	1.536 (3)
C109—H10D	0.9800	C208—C211	1.543 (3)
C109—H10E	0.9800	C209—H20C	0.9800
C110—H11A	0.9800	C209—H20D	0.9800
C110—H11B	0.9800	C209—H20E	0.9800
C110—H11C	0.9800	C210—H21A	0.9800
C111—H11D	0.9800	C210—H21B	0.9800
C111—H11E	0.9800	C210—H21C	0.9800
C111—H11F	0.9800	C211—H21D	0.9800
C112—C315	1.476 (13)	C211—H21E	0.9800
C112—C114	1.500 (4)	C211—H21F	0.9800
C112—C115	1.542 (4)	C212—C214	1.525 (3)
C112—C113	1.558 (4)	C212—C215	1.537 (3)
C112—C313	1.573 (14)	C212—C213	1.543 (3)
C112—C314	1.638 (14)	C213—H21G	0.9800
C113—H11G	0.9800	C213—H21H	0.9800
C113—H11H	0.9800	C213—H21I	0.9800
C113—H11I	0.9800	C214—H21J	0.9800
C114—H11J	0.9800	C214—H21K	0.9800
C114—H11K	0.9800	C214—H21L	0.9800
C114—H11L	0.9800	C215—H21M	0.9800
C115—H11M	0.9800	C215—H21N	0.9800
C115—H11N	0.9800	C215—H21O	0.9800
C115—H11O	0.9800	C216—N201	1.479 (3)
C313—H33A	0.9800	C216—C217	1.512 (3)
C313—H33B	0.9800	C216—H21P	0.9900
C313—H33C	0.9800	C216—H21Q	0.9900
C314—H34A	0.9800	C217—C222	1.386 (3)
C314—H34B	0.9800	C217—C218	1.424 (3)
C314—H34C	0.9800	C218—O202	1.348 (3)
C315—H35A	0.9800	C218—C219	1.419 (3)
C315—H35B	0.9800	C219—C220	1.396 (3)
C315—H35C	0.9800	C219—C223	1.544 (3)
C116—N101	1.484 (3)	C220—C221	1.399 (3)
C116—C117	1.506 (4)	C220—H220	0.9500
C116—H11P	0.9900	C221—C222	1.390 (3)
C116—H11Q	0.9900	C221—C227	1.535 (3)
C117—C122	1.400 (3)	C222—H222	0.9500
C117—C118	1.414 (3)	C223—C225	1.533 (3)
C118—O102	1.347 (3)	C223—C226	1.542 (3)
C118—C119	1.424 (3)	C223—C224	1.543 (3)
C119—C120	1.397 (3)	C224—H22A	0.9800
C119—C123	1.535 (4)	C224—H22B	0.9800
C120—C121	1.389 (4)	C224—H22C	0.9800
C120—H120	0.9500	C225—H22D	0.9800
C121—C122	1.382 (4)	C225—H22E	0.9800
C121—C127	1.542 (3)	C225—H22F	0.9800
C122—H122	0.9500	C226—H22G	0.9800
C123—C126	1.533 (4)	C226—H22H	0.9800
C123—C125	1.543 (3)	C226—H22I	0.9800
C123—C124	1.545 (3)	C227—C230	1.529 (3)
C124—H12A	0.9800	C227—C228	1.536 (3)
C124—H12B	0.9800	C227—C229	1.536 (3)
C124—H12C	0.9800	C228—H22J	0.9800
C125—H12D	0.9800	C228—H22K	0.9800
C125—H12E	0.9800	C228—H22L	0.9800
C125—H12F	0.9800	C229—H22M	0.9800
C126—H12G	0.9800	C229—H22N	0.9800
C126—H12H	0.9800	C229—H22O	0.9800
C126—H12I	0.9800	C230—H23A	0.9800
C127—C129	1.509 (4)	C230—H23B	0.9800
C127—C128	1.513 (4)	C230—H23C	0.9800
C127—C130	1.545 (5)	C231—N201	1.485 (2)
C128—H12J	0.9800	C231—C232	1.522 (3)
C128—H12K	0.9800	C231—H23D	0.9900
C128—H12L	0.9800	C231—H23E	0.9900
C129—H12M	0.9800	C232—N202	1.493 (3)
C129—H12N	0.9800	C232—H23F	0.9900
C129—H12O	0.9800	C232—H23G	0.9900
C130—H13D	0.9800	C233—N202	1.480 (3)
C130—H13E	0.9800	C233—H23H	0.9800
C130—H13F	0.9800	C233—H23I	0.9800
C131—N101	1.480 (3)	C233—H23J	0.9800
C131—C132	1.522 (3)	C234—N202	1.487 (3)
C131—H13G	0.9900	C234—H23K	0.9800
C131—H13H	0.9900	C234—H23L	0.9800
C132—N102	1.493 (3)	C234—H23M	0.9800

O101—Zn1—O102	125.35 (7)	N201—C201—H20A	108.8
O101—Zn1—N101	99.58 (7)	C202—C201—H20A	108.8
O102—Zn1—N101	99.77 (7)	N201—C201—H20B	108.8
O101—Zn1—N102	112.76 (7)	C202—C201—H20B	108.8
O102—Zn1—N102	118.59 (8)	H20A—C201—H20B	107.7
N101—Zn1—N102	87.81 (8)	C207—C202—C203	120.41 (19)
O201—Zn2—O202	121.39 (7)	C207—C202—C201	119.6 (2)
O201—Zn2—N201	99.95 (7)	C203—C202—C201	119.85 (19)
O202—Zn2—N201	99.80 (7)	O201—C203—C202	120.64 (19)
O201—Zn2—N202	113.08 (8)	O201—C203—C204	120.6 (2)
O202—Zn2—N202	122.20 (8)	C202—C203—C204	118.8 (2)
N201—Zn2—N202	88.07 (7)	C205—C204—C203	117.9 (2)
N101—C101—C102	113.5 (2)	C205—C204—C208	121.4 (2)
N101—C101—H10A	108.9	C203—C204—C208	120.7 (2)
C102—C101—H10A	108.9	C204—C205—C206	124.3 (2)
N101—C101—H10B	108.9	C204—C205—H205	117.9
C102—C101—H10B	108.9	C206—C205—H205	117.9
H10A—C101—H10B	107.7	C207—C206—C205	116.5 (2)
C107—C102—C103	120.4 (2)	C207—C206—C212	124.2 (2)
C107—C102—C101	119.5 (2)	C205—C206—C212	119.29 (19)
C103—C102—C101	120.0 (2)	C206—C207—C202	122.1 (2)
O101—C103—C102	120.5 (2)	C206—C207—H207	119.0
O101—C103—C104	121.1 (2)	C202—C207—H207	119.0
C102—C103—C104	118.4 (2)	C210—C208—C209	108.1 (2)
C105—C104—C103	117.6 (2)	C210—C208—C204	109.91 (19)
C105—C104—C108	122.2 (2)	C209—C208—C204	111.91 (19)
C103—C104—C108	120.25 (19)	C210—C208—C211	109.6 (2)
C106—C105—C104	124.9 (2)	C209—C208—C211	107.1 (2)
C106—C105—H105	117.6	C204—C208—C211	110.2 (2)
C104—C105—H105	117.6	C208—C209—H20C	109.5
C107—C106—C105	116.0 (2)	C208—C209—H20D	109.5
C107—C106—C112	122.8 (2)	H20C—C209—H20D	109.5
C105—C106—C112	121.1 (2)	C208—C209—H20E	109.5
C106—C107—C102	122.6 (2)	H20C—C209—H20E	109.5
C106—C107—H107	118.7	H20D—C209—H20E	109.5
C102—C107—H107	118.7	C208—C210—H21A	109.5
C104—C108—C111	110.94 (19)	C208—C210—H21B	109.5
C104—C108—C109	112.04 (19)	H21A—C210—H21B	109.5
C111—C108—C109	106.9 (2)	C208—C210—H21C	109.5
C104—C108—C110	109.4 (2)	H21A—C210—H21C	109.5
C111—C108—C110	109.88 (19)	H21B—C210—H21C	109.5
C109—C108—C110	107.6 (2)	C208—C211—H21D	109.5
C108—C109—H10C	109.5	C208—C211—H21E	109.5
C108—C109—H10D	109.5	H21D—C211—H21E	109.5
H10C—C109—H10D	109.5	C208—C211—H21F	109.5
C108—C109—H10E	109.5	H21D—C211—H21F	109.5
H10C—C109—H10E	109.5	H21E—C211—H21F	109.5
H10D—C109—H10E	109.5	C214—C212—C206	112.00 (18)
C108—C110—H11A	109.5	C214—C212—C215	107.8 (2)
C108—C110—H11B	109.5	C206—C212—C215	110.6 (2)
H11A—C110—H11B	109.5	C214—C212—C213	108.4 (2)
C108—C110—H11C	109.5	C206—C212—C213	109.4 (2)
H11A—C110—H11C	109.5	C215—C212—C213	108.62 (19)
H11B—C110—H11C	109.5	C212—C213—H21G	109.5
C108—C111—H11D	109.5	C212—C213—H21H	109.5
C108—C111—H11E	109.5	H21G—C213—H21H	109.5
H11D—C111—H11E	109.5	C212—C213—H21I	109.5
C108—C111—H11F	109.5	H21G—C213—H21I	109.5
H11D—C111—H11F	109.5	H21H—C213—H21I	109.5
H11E—C111—H11F	109.5	C212—C214—H21J	109.5
C114—C112—C115	108.0 (2)	C212—C214—H21K	109.5
C315—C112—C106	118.9 (7)	H21J—C214—H21K	109.5
C114—C112—C106	112.5 (2)	C212—C214—H21L	109.5
C115—C112—C106	109.8 (2)	H21J—C214—H21L	109.5
C114—C112—C113	109.3 (3)	H21K—C214—H21L	109.5
C115—C112—C113	107.4 (2)	C212—C215—H21M	109.5
C106—C112—C113	109.7 (2)	C212—C215—H21N	109.5
C315—C112—C313	115.3 (10)	H21M—C215—H21N	109.5
C106—C112—C313	106.4 (6)	C212—C215—H21O	109.5
C315—C112—C314	105.1 (10)	H21M—C215—H21O	109.5
C106—C112—C314	109.1 (7)	H21N—C215—H21O	109.5
C313—C112—C314	100.3 (11)	N201—C216—C217	114.68 (19)
C112—C113—H11G	109.5	N201—C216—H21P	108.6
C112—C113—H11H	109.5	C217—C216—H21P	108.6
C112—C113—H11I	109.5	N201—C216—H21Q	108.6
C112—C114—H11J	109.5	C217—C216—H21Q	108.6
C112—C114—H11K	109.5	H21P—C216—H21Q	107.6
C112—C114—H11L	109.5	C222—C217—C218	119.8 (2)
C112—C115—H11M	109.5	C222—C217—C216	119.6 (2)
C112—C115—H11N	109.5	C218—C217—C216	120.5 (2)
C112—C115—H11O	109.5	O202—C218—C219	120.6 (2)
C112—C313—H33A	109.5	O202—C218—C217	120.8 (2)
C112—C313—H33B	109.5	C219—C218—C217	118.6 (2)
H33A—C313—H33B	109.5	C220—C219—C218	118.3 (2)
C112—C313—H33C	109.5	C220—C219—C223	121.6 (2)
H33A—C313—H33C	109.5	C218—C219—C223	120.1 (2)
H33B—C313—H33C	109.5	C219—C220—C221	124.0 (2)
C112—C314—H34A	109.5	C219—C220—H220	118.0
C112—C314—H34B	109.5	C221—C220—H220	118.0
H34A—C314—H34B	109.5	C222—C221—C220	116.2 (2)
C112—C314—H34C	109.5	C222—C221—C227	121.0 (2)
H34A—C314—H34C	109.5	C220—C221—C227	122.7 (2)
H34B—C314—H34C	109.5	C217—C222—C221	123.0 (2)
C112—C315—H35A	109.5	C217—C222—H222	118.5
C112—C315—H35B	109.5	C221—C222—H222	118.5
H35A—C315—H35B	109.5	C225—C223—C226	107.4 (2)
C112—C315—H35C	109.5	C225—C223—C224	109.4 (2)
H35A—C315—H35C	109.5	C226—C223—C224	107.3 (2)
H35B—C315—H35C	109.5	C225—C223—C219	110.3 (2)
N101—C116—C117	114.7 (2)	C226—C223—C219	112.2 (2)
N101—C116—H11P	108.6	C224—C223—C219	110.14 (18)
C117—C116—H11P	108.6	C223—C224—H22A	109.5
N101—C116—H11Q	108.6	C223—C224—H22B	109.5
C117—C116—H11Q	108.6	H22A—C224—H22B	109.5
H11P—C116—H11Q	107.6	C223—C224—H22C	109.5
C122—C117—C118	119.5 (3)	H22A—C224—H22C	109.5
C122—C117—C116	118.8 (2)	H22B—C224—H22C	109.5
C118—C117—C116	121.5 (2)	C223—C225—H22D	109.5
O102—C118—C117	120.6 (2)	C223—C225—H22E	109.5
O102—C118—C119	120.3 (2)	H22D—C225—H22E	109.5
C117—C118—C119	119.1 (2)	C223—C225—H22F	109.5
C120—C119—C118	117.8 (2)	H22D—C225—H22F	109.5
C120—C119—C123	120.9 (2)	H22E—C225—H22F	109.5
C118—C119—C123	121.3 (2)	C223—C226—H22G	109.5
C121—C120—C119	124.2 (3)	C223—C226—H22H	109.5
C121—C120—H120	117.9	H22G—C226—H22H	109.5
C119—C120—H120	117.9	C223—C226—H22I	109.5
C122—C121—C120	116.7 (2)	H22G—C226—H22I	109.5
C122—C121—C127	120.4 (3)	H22H—C226—H22I	109.5
C120—C121—C127	122.8 (3)	C230—C227—C228	107.4 (2)
C121—C122—C117	122.6 (3)	C230—C227—C229	108.7 (2)
C121—C122—H122	118.7	C228—C227—C229	109.3 (2)
C117—C122—H122	118.7	C230—C227—C221	112.47 (19)
C126—C123—C119	113.1 (2)	C228—C227—C221	110.7 (2)
C126—C123—C125	107.1 (2)	C229—C227—C221	108.19 (19)
C119—C123—C125	109.9 (2)	C227—C228—H22J	109.5
C126—C123—C124	106.8 (2)	C227—C228—H22K	109.5
C119—C123—C124	109.94 (19)	H22J—C228—H22K	109.5
C125—C123—C124	109.9 (2)	C227—C228—H22L	109.5
C123—C124—H12A	109.5	H22J—C228—H22L	109.5
C123—C124—H12B	109.5	H22K—C228—H22L	109.5
H12A—C124—H12B	109.5	C227—C229—H22M	109.5
C123—C124—H12C	109.5	C227—C229—H22N	109.5
H12A—C124—H12C	109.5	H22M—C229—H22N	109.5
H12B—C124—H12C	109.5	C227—C229—H22O	109.5
C123—C125—H12D	109.5	H22M—C229—H22O	109.5
C123—C125—H12E	109.5	H22N—C229—H22O	109.5
H12D—C125—H12E	109.5	C227—C230—H23A	109.5
C123—C125—H12F	109.5	C227—C230—H23B	109.5
H12D—C125—H12F	109.5	H23A—C230—H23B	109.5
H12E—C125—H12F	109.5	C227—C230—H23C	109.5
C123—C126—H12G	109.5	H23A—C230—H23C	109.5
C123—C126—H12H	109.5	H23B—C230—H23C	109.5
H12G—C126—H12H	109.5	N201—C231—C232	110.62 (18)
C123—C126—H12I	109.5	N201—C231—H23D	109.5
H12G—C126—H12I	109.5	C232—C231—H23D	109.5
H12H—C126—H12I	109.5	N201—C231—H23E	109.5
C129—C127—C128	111.1 (3)	C232—C231—H23E	109.5
C129—C127—C121	110.1 (2)	H23D—C231—H23E	108.1
C128—C127—C121	108.6 (2)	N202—C232—C231	110.71 (19)
C129—C127—C130	108.0 (3)	N202—C232—H23F	109.5
C128—C127—C130	107.1 (3)	C231—C232—H23F	109.5
C121—C127—C130	111.9 (3)	N202—C232—H23G	109.5
C127—C128—H12J	109.5	C231—C232—H23G	109.5
C127—C128—H12K	109.5	H23F—C232—H23G	108.1
H12J—C128—H12K	109.5	N202—C233—H23H	109.5
C127—C128—H12L	109.5	N202—C233—H23I	109.5
H12J—C128—H12L	109.5	H23H—C233—H23I	109.5
H12K—C128—H12L	109.5	N202—C233—H23J	109.5
C127—C129—H12M	109.5	H23H—C233—H23J	109.5
C127—C129—H12N	109.5	H23I—C233—H23J	109.5
H12M—C129—H12N	109.5	N202—C234—H23K	109.5
C127—C129—H12O	109.5	N202—C234—H23L	109.5
H12M—C129—H12O	109.5	H23K—C234—H23L	109.5
H12N—C129—H12O	109.5	N202—C234—H23M	109.5
C127—C130—H13D	109.5	H23K—C234—H23M	109.5
C127—C130—H13E	109.5	H23L—C234—H23M	109.5
H13D—C130—H13E	109.5	C131—N101—C116	112.97 (18)
C127—C130—H13F	109.5	C131—N101—C101	112.12 (19)
H13D—C130—H13F	109.5	C116—N101—C101	110.95 (18)
H13E—C130—H13F	109.5	C131—N101—Zn1	105.41 (13)
N101—C131—C132	110.62 (19)	C116—N101—Zn1	107.63 (15)
N101—C131—H13G	109.5	C101—N101—Zn1	107.36 (14)
C132—C131—H13G	109.5	C133—N102—C134	108.6 (2)
N101—C131—H13H	109.5	C133—N102—C132	110.2 (2)
C132—C131—H13H	109.5	C134—N102—C132	110.09 (19)
H13G—C131—H13H	108.1	C133—N102—Zn1	112.54 (15)
N102—C132—C131	111.0 (2)	C134—N102—Zn1	112.60 (16)
N102—C132—H13I	109.4	C132—N102—Zn1	102.73 (14)
C131—C132—H13I	109.4	C216—N201—C231	112.96 (18)
N102—C132—H13J	109.4	C216—N201—C201	111.35 (17)
C131—C132—H13J	109.4	C231—N201—C201	111.65 (17)
H13I—C132—H13J	108.0	C216—N201—Zn2	108.05 (14)
N102—C133—H13K	109.5	C231—N201—Zn2	105.30 (13)
N102—C133—H13L	109.5	C201—N201—Zn2	107.10 (14)
H13K—C133—H13L	109.5	C233—N202—C234	108.8 (2)
N102—C133—H13M	109.5	C233—N202—C232	109.8 (2)
H13K—C133—H13M	109.5	C234—N202—C232	110.57 (19)
H13L—C133—H13M	109.5	C233—N202—Zn2	111.58 (15)
N102—C134—H13N	109.5	C234—N202—Zn2	113.50 (16)
N102—C134—H13O	109.5	C232—N202—Zn2	102.38 (13)
H13N—C134—H13O	109.5	C103—O101—Zn1	113.05 (13)
N102—C134—H13P	109.5	C118—O102—Zn1	118.15 (15)
H13N—C134—H13P	109.5	C203—O201—Zn2	111.79 (14)
H13O—C134—H13P	109.5	C218—O202—Zn2	115.18 (13)
N201—C201—C202	113.91 (18)

N101—C101—C102—C107	−118.9 (2)	C217—C218—C219—C220	3.1 (3)
N101—C101—C102—C103	63.9 (3)	O202—C218—C219—C223	1.8 (3)
C107—C102—C103—O101	178.1 (2)	C217—C218—C219—C223	−176.6 (2)
C101—C102—C103—O101	−4.8 (3)	C218—C219—C220—C221	−1.0 (3)
C107—C102—C103—C104	−3.2 (3)	C223—C219—C220—C221	178.7 (2)
C101—C102—C103—C104	173.9 (2)	C219—C220—C221—C222	−0.7 (3)
O101—C103—C104—C105	−178.2 (2)	C219—C220—C221—C227	−177.3 (2)
C102—C103—C104—C105	3.1 (3)	C218—C217—C222—C221	1.7 (3)
O101—C103—C104—C108	1.9 (3)	C216—C217—C222—C221	−176.7 (2)
C102—C103—C104—C108	−176.8 (2)	C220—C221—C222—C217	0.4 (3)
C103—C104—C105—C106	−0.7 (4)	C227—C221—C222—C217	177.0 (2)
C108—C104—C105—C106	179.3 (2)	C220—C219—C223—C225	117.5 (3)
C104—C105—C106—C107	−1.7 (4)	C218—C219—C223—C225	−62.8 (3)
C104—C105—C106—C112	179.5 (2)	C220—C219—C223—C226	−2.2 (3)
C105—C106—C107—C102	1.6 (4)	C218—C219—C223—C226	177.5 (2)
C112—C106—C107—C102	−179.6 (2)	C220—C219—C223—C224	−121.7 (2)
C103—C102—C107—C106	0.8 (4)	C218—C219—C223—C224	58.0 (3)
C101—C102—C107—C106	−176.3 (2)	C222—C221—C227—C230	166.5 (2)
C105—C104—C108—C111	118.6 (2)	C220—C221—C227—C230	−17.1 (3)
C103—C104—C108—C111	−61.5 (3)	C222—C221—C227—C228	46.3 (3)
C105—C104—C108—C109	−0.8 (3)	C220—C221—C227—C228	−137.3 (2)
C103—C104—C108—C109	179.1 (2)	C222—C221—C227—C229	−73.4 (3)
C105—C104—C108—C110	−120.0 (2)	C220—C221—C227—C229	103.0 (2)
C103—C104—C108—C110	59.9 (3)	N201—C231—C232—N202	54.9 (2)
C107—C106—C112—C315	172.9 (9)	C132—C131—N101—C116	−152.8 (2)
C105—C106—C112—C315	−8.4 (10)	C132—C131—N101—C101	80.9 (3)
C107—C106—C112—C114	9.4 (4)	C132—C131—N101—Zn1	−35.6 (2)
C105—C106—C112—C114	−171.9 (3)	C117—C116—N101—C131	62.4 (3)
C107—C106—C112—C115	129.7 (3)	C117—C116—N101—C101	−170.7 (2)
C105—C106—C112—C115	−51.5 (3)	C117—C116—N101—Zn1	−53.5 (2)
C107—C106—C112—C113	−112.5 (3)	C102—C101—N101—C131	−165.37 (18)
C105—C106—C112—C113	66.2 (3)	C102—C101—N101—C116	67.3 (2)
C107—C106—C112—C313	−55.0 (8)	C102—C101—N101—Zn1	−50.1 (2)
C105—C106—C112—C313	123.8 (8)	O101—Zn1—N101—C131	122.62 (14)
C107—C106—C112—C314	52.4 (9)	O102—Zn1—N101—C131	−108.74 (15)
C105—C106—C112—C314	−128.8 (9)	N102—Zn1—N101—C131	9.91 (15)
N101—C116—C117—C122	−122.9 (2)	O101—Zn1—N101—C116	−116.56 (14)
N101—C116—C117—C118	60.5 (3)	O102—Zn1—N101—C116	12.08 (15)
C122—C117—C118—O102	179.09 (19)	N102—Zn1—N101—C116	130.73 (15)
C116—C117—C118—O102	−4.4 (3)	O101—Zn1—N101—C101	2.93 (15)
C122—C117—C118—C119	−3.0 (3)	O102—Zn1—N101—C101	131.57 (14)
C116—C117—C118—C119	173.5 (2)	N102—Zn1—N101—C101	−109.78 (15)
O102—C118—C119—C120	−178.99 (19)	C131—C132—N102—C133	−161.6 (2)
C117—C118—C119—C120	3.1 (3)	C131—C132—N102—C134	78.6 (2)
O102—C118—C119—C123	1.7 (3)	C131—C132—N102—Zn1	−41.5 (2)
C117—C118—C119—C123	−176.2 (2)	O101—Zn1—N102—C133	36.1 (2)
C118—C119—C120—C121	−1.0 (3)	O102—Zn1—N102—C133	−124.49 (19)
C123—C119—C120—C121	178.3 (2)	N101—Zn1—N102—C133	135.6 (2)
C119—C120—C121—C122	−1.2 (4)	O101—Zn1—N102—C134	159.25 (15)
C119—C120—C121—C127	−179.4 (2)	O102—Zn1—N102—C134	−1.34 (19)
C120—C121—C122—C117	1.4 (4)	N101—Zn1—N102—C134	−101.28 (17)
C127—C121—C122—C117	179.6 (2)	O101—Zn1—N102—C132	−82.36 (15)
C118—C117—C122—C121	0.7 (3)	O102—Zn1—N102—C132	117.05 (15)
C116—C117—C122—C121	−175.9 (2)	N101—Zn1—N102—C132	17.11 (15)
C120—C119—C123—C126	−1.2 (3)	C217—C216—N201—C231	65.6 (2)
C118—C119—C123—C126	178.1 (2)	C217—C216—N201—C201	−167.82 (18)
C120—C119—C123—C125	118.4 (2)	C217—C216—N201—Zn2	−50.5 (2)
C118—C119—C123—C125	−62.3 (3)	C232—C231—N201—C216	−151.28 (19)
C120—C119—C123—C124	−120.5 (2)	C232—C231—N201—C201	82.3 (2)
C118—C119—C123—C124	58.8 (3)	C232—C231—N201—Zn2	−33.6 (2)
C122—C121—C127—C129	50.7 (4)	C202—C201—N201—C216	69.0 (2)
C120—C121—C127—C129	−131.2 (3)	C202—C201—N201—C231	−163.70 (19)
C122—C121—C127—C128	−71.2 (3)	C202—C201—N201—Zn2	−48.9 (2)
C120—C121—C127—C128	106.9 (3)	O201—Zn2—N201—C216	−118.55 (13)
C122—C121—C127—C130	170.8 (3)	O202—Zn2—N201—C216	5.99 (14)
C120—C121—C127—C130	−11.1 (4)	N202—Zn2—N201—C216	128.35 (14)
N101—C131—C132—N102	54.8 (3)	O201—Zn2—N201—C231	120.49 (14)
N201—C201—C202—C207	−122.2 (2)	O202—Zn2—N201—C231	−114.98 (14)
N201—C201—C202—C203	62.0 (3)	N202—Zn2—N201—C231	7.39 (15)
C207—C202—C203—O201	−177.6 (2)	O201—Zn2—N201—C201	1.52 (15)
C201—C202—C203—O201	−1.8 (3)	O202—Zn2—N201—C201	126.05 (14)
C207—C202—C203—C204	1.2 (3)	N202—Zn2—N201—C201	−111.59 (15)
C201—C202—C203—C204	177.0 (2)	C231—C232—N202—C233	−162.33 (19)
O201—C203—C204—C205	177.5 (2)	C231—C232—N202—C234	77.5 (2)
C202—C203—C204—C205	−1.3 (3)	C231—C232—N202—Zn2	−43.7 (2)
O201—C203—C204—C208	−1.9 (3)	O201—Zn2—N202—C233	37.09 (18)
C202—C203—C204—C208	179.3 (2)	O202—Zn2—N202—C233	−122.54 (17)
C203—C204—C205—C206	−0.1 (4)	N201—Zn2—N202—C233	137.09 (17)
C208—C204—C205—C206	179.4 (2)	O201—Zn2—N202—C234	160.49 (15)
C204—C205—C206—C207	1.5 (4)	O202—Zn2—N202—C234	0.86 (19)
C204—C205—C206—C212	−177.3 (2)	N201—Zn2—N202—C234	−99.52 (17)
C205—C206—C207—C202	−1.6 (4)	O201—Zn2—N202—C232	−80.33 (16)
C212—C206—C207—C202	177.2 (2)	O202—Zn2—N202—C232	120.04 (15)
C203—C202—C207—C206	0.3 (4)	N201—Zn2—N202—C232	19.67 (15)
C201—C202—C207—C206	−175.5 (2)	C102—C103—O101—Zn1	−49.8 (3)
C205—C204—C208—C210	−118.9 (2)	C104—C103—O101—Zn1	131.49 (19)
C203—C204—C208—C210	60.6 (3)	O102—Zn1—O101—C103	−63.10 (18)
C205—C204—C208—C209	1.3 (3)	N101—Zn1—O101—C103	46.21 (16)
C203—C204—C208—C209	−179.3 (2)	N102—Zn1—O101—C103	137.86 (16)
C205—C204—C208—C211	120.3 (2)	C117—C118—O102—Zn1	−42.2 (2)
C203—C204—C208—C211	−60.3 (3)	C119—C118—O102—Zn1	139.94 (18)
C207—C206—C212—C214	−0.4 (3)	O101—Zn1—O102—C118	143.80 (15)
C205—C206—C212—C214	178.4 (2)	N101—Zn1—O102—C118	34.58 (16)
C207—C206—C212—C215	119.8 (3)	N102—Zn1—O102—C118	−58.27 (17)
C205—C206—C212—C215	−61.4 (3)	C202—C203—O201—Zn2	−52.7 (3)
C207—C206—C212—C213	−120.6 (3)	C204—C203—O201—Zn2	128.5 (2)
C205—C206—C212—C213	58.1 (3)	O202—Zn2—O201—C203	−59.93 (16)
N201—C216—C217—C222	−120.8 (2)	N201—Zn2—O201—C203	48.10 (15)
N201—C216—C217—C218	60.9 (3)	N202—Zn2—O201—C203	140.25 (14)
C222—C217—C218—O202	178.1 (2)	C219—C218—O202—Zn2	134.45 (18)
C216—C217—C218—O202	−3.5 (3)	C217—C218—O202—Zn2	−47.1 (2)
C222—C217—C218—C219	−3.4 (3)	O201—Zn2—O202—C218	149.80 (14)
C216—C217—C218—C219	174.9 (2)	N201—Zn2—O202—C218	41.69 (15)
O202—C218—C219—C220	−178.5 (2)	N202—Zn2—O202—C218	−52.23 (17)

(III) {bis(3-tert-butyl-5-methyl-2-oxidobenzyl)[2-(N,N- dimethylamino)ethyl]amine-κ⁴N,N',O,O'}(tetrahdyrofuran)zinc(II) top

Crystal data top

[Zn(C₂₈H₄₂N₂O₂)(C₄H₈O)]	F(000) = 1240
M_r = 576.11	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33137 reflections
a = 13.669 (3) Å	θ = 3.5–27.8°
b = 17.476 (4) Å	µ = 0.83 mm⁻¹
c = 12.989 (4) Å	T = 140 K
β = 93.14 (2)°	Block, light yellow
V = 3098.1 (14) Å³	0.06 × 0.06 × 0.02 mm
Z = 4

Data collection top

Oxford Xcalibur3 CCD area-detector diffractometer	7121 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2308 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.195
Detector resolution: 16.0050 pixels mm^-1	θ_max = 27.8°, θ_min = 3.5°
Thin slice ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003)	k = −22→22
T_min = 0.801, T_max = 0.984	l = −17→17
33137 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 0.68	w = 1/[σ²(F_o²) + (0.0123P)²] where P = (F_o² + 2F_c²)/3
7121 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Zn(C₂₈H₄₂N₂O₂)(C₄H₈O)]	V = 3098.1 (14) Å³
M_r = 576.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.669 (3) Å	µ = 0.83 mm⁻¹
b = 17.476 (4) Å	T = 140 K
c = 12.989 (4) Å	0.06 × 0.06 × 0.02 mm
β = 93.14 (2)°

Data collection top

Oxford Xcalibur3 CCD area-detector diffractometer	7121 independent reflections
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2003)	2308 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.984	R_int = 0.195
33137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 0.68	Δρ_max = 0.37 e Å⁻³
7121 reflections	Δρ_min = −0.49 e Å⁻³
353 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
Zn1	0.22744 (3)	0.61170 (3)	0.54949 (4)	0.02396 (13)
C101	0.1033 (2)	0.4792 (2)	0.6099 (3)	0.0253 (11)
H10A	0.0811	0.4750	0.5363	0.030*
H10B	0.0946	0.4284	0.6420	0.030*
C102	0.0392 (3)	0.5365 (2)	0.6613 (3)	0.0214 (10)
C103	0.0319 (2)	0.6109 (3)	0.6210 (3)	0.0207 (9)
C104	−0.0403 (3)	0.6613 (2)	0.6631 (3)	0.0223 (10)
C105	−0.0899 (2)	0.6363 (2)	0.7476 (3)	0.0265 (11)
H105	−0.1354	0.6701	0.7764	0.032*
C106	−0.0765 (3)	0.5643 (2)	0.7922 (3)	0.0256 (11)
C107	−0.0114 (3)	0.5146 (2)	0.7466 (3)	0.0295 (11)
H107	−0.0016	0.4647	0.7744	0.035*
C108	−0.0585 (3)	0.7421 (2)	0.6183 (3)	0.0247 (11)
C109	−0.1424 (3)	0.7858 (2)	0.6676 (3)	0.0430 (13)
H10C	−0.2035	0.7567	0.6573	0.064*
H10D	−0.1504	0.8362	0.6352	0.064*
H10E	−0.1266	0.7921	0.7416	0.064*
C110	−0.0869 (2)	0.7375 (2)	0.5015 (3)	0.0332 (12)
H11A	−0.0364	0.7091	0.4667	0.050*
H11B	−0.0923	0.7893	0.4729	0.050*
H11C	−0.1499	0.7111	0.4909	0.050*
C111	0.0355 (3)	0.7915 (2)	0.6355 (3)	0.0358 (12)
H11D	0.0488	0.8001	0.7095	0.054*
H11E	0.0259	0.8408	0.6004	0.054*
H11F	0.0912	0.7648	0.6073	0.054*
C112	−0.1278 (3)	0.5405 (2)	0.8888 (3)	0.0404 (13)
H11G	−0.0856	0.5524	0.9502	0.061*
H11H	−0.1410	0.4854	0.8864	0.061*
H11I	−0.1897	0.5685	0.8919	0.061*
C116	0.2477 (2)	0.5003 (2)	0.7264 (3)	0.0238 (10)
H11J	0.2407	0.4482	0.7551	0.029*
H11K	0.2055	0.5350	0.7649	0.029*
C117	0.3533 (3)	0.5255 (2)	0.7448 (3)	0.0203 (10)
C118	0.3853 (2)	0.5982 (2)	0.7136 (3)	0.0239 (11)
C119	0.4821 (2)	0.6238 (2)	0.7508 (3)	0.0223 (10)
C120	0.5386 (3)	0.5738 (2)	0.8123 (3)	0.0251 (11)
H120	0.6016	0.5908	0.8370	0.030*
C121	0.5098 (3)	0.5005 (2)	0.8406 (3)	0.0240 (10)
C122	0.4153 (3)	0.4777 (2)	0.8068 (3)	0.0261 (11)
H122	0.3923	0.4288	0.8262	0.031*
C123	0.5177 (3)	0.7050 (2)	0.7271 (3)	0.0252 (11)
C124	0.4451 (2)	0.7647 (2)	0.7650 (3)	0.0316 (12)
H12A	0.3808	0.7570	0.7294	0.047*
H12B	0.4689	0.8162	0.7503	0.047*
H12C	0.4393	0.7589	0.8395	0.047*
C125	0.5299 (2)	0.7143 (2)	0.6099 (3)	0.0310 (12)
H12D	0.5813	0.6796	0.5883	0.047*
H12E	0.5482	0.7672	0.5951	0.047*
H12F	0.4680	0.7019	0.5720	0.047*
C126	0.6184 (2)	0.7233 (2)	0.7830 (3)	0.0375 (13)
H12G	0.6130	0.7190	0.8577	0.056*
H12H	0.6382	0.7755	0.7658	0.056*
H12I	0.6676	0.6870	0.7607	0.056*
C127	0.5753 (2)	0.4501 (2)	0.9102 (3)	0.0338 (12)
H12J	0.6120	0.4150	0.8679	0.051*
H12K	0.5349	0.4206	0.9560	0.051*
H12L	0.6212	0.4822	0.9515	0.051*
C131	0.2679 (2)	0.4449 (2)	0.5555 (3)	0.0280 (11)
H13I	0.2420	0.3926	0.5642	0.034*
H13J	0.3376	0.4452	0.5807	0.034*
C132	0.2601 (3)	0.4663 (2)	0.4442 (3)	0.0281 (11)
H13K	0.3028	0.4322	0.4057	0.034*
H13L	0.1918	0.4583	0.4170	0.034*
C133	0.2600 (2)	0.5684 (2)	0.3200 (3)	0.0364 (12)
H13P	0.2875	0.5316	0.2725	0.055*
H13Q	0.2850	0.6197	0.3060	0.055*
H13R	0.1884	0.5683	0.3102	0.055*
C134	0.3991 (2)	0.5550 (2)	0.4403 (3)	0.0352 (12)
H13M	0.4304	0.5226	0.3900	0.053*
H13N	0.4208	0.5391	0.5102	0.053*
H13O	0.4175	0.6085	0.4298	0.053*
C135	0.1758 (3)	0.7394 (2)	0.3759 (3)	0.0362 (12)
H13A	0.1162	0.7076	0.3796	0.043*
H13B	0.2045	0.7303	0.3086	0.043*
C136	0.1512 (3)	0.8229 (2)	0.3880 (3)	0.0380 (13)
H13C	0.0942	0.8295	0.4311	0.046*
H13D	0.1365	0.8473	0.3201	0.046*
C137	0.2433 (2)	0.8563 (2)	0.4406 (3)	0.0340 (12)
H13E	0.2908	0.8717	0.3896	0.041*
H13F	0.2280	0.9010	0.4836	0.041*
C138	0.2821 (3)	0.7908 (2)	0.5060 (3)	0.0315 (12)
H13G	0.3546	0.7913	0.5098	0.038*
H13H	0.2596	0.7957	0.5769	0.038*
N101	0.21178 (19)	0.49954 (17)	0.6170 (2)	0.0202 (8)
N102	0.2883 (2)	0.54682 (17)	0.4261 (2)	0.0231 (9)
O101	0.08671 (15)	0.63419 (13)	0.54433 (19)	0.0262 (7)
O102	0.32714 (16)	0.64392 (13)	0.65463 (19)	0.0268 (7)
O103	0.24679 (16)	0.72042 (15)	0.4607 (2)	0.0295 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0181 (2)	0.0245 (3)	0.0287 (3)	−0.0006 (3)	−0.00329 (19)	−0.0010 (3)
C101	0.022 (2)	0.018 (3)	0.036 (3)	−0.005 (2)	−0.007 (2)	0.002 (2)
C102	0.018 (2)	0.019 (3)	0.027 (3)	−0.003 (2)	−0.003 (2)	−0.005 (2)
C103	0.020 (2)	0.020 (2)	0.022 (3)	−0.004 (2)	−0.0040 (18)	−0.003 (3)
C104	0.018 (2)	0.023 (3)	0.026 (3)	0.001 (2)	−0.003 (2)	−0.001 (2)
C105	0.019 (2)	0.031 (3)	0.030 (3)	0.000 (2)	0.002 (2)	−0.006 (2)
C106	0.023 (2)	0.026 (3)	0.027 (3)	−0.011 (2)	−0.002 (2)	0.003 (2)
C107	0.024 (2)	0.026 (3)	0.039 (3)	−0.005 (2)	−0.001 (2)	0.006 (2)
C108	0.018 (2)	0.027 (3)	0.029 (3)	0.006 (2)	0.008 (2)	0.002 (2)
C109	0.042 (3)	0.033 (3)	0.055 (4)	0.009 (2)	0.010 (2)	0.004 (3)
C110	0.026 (2)	0.030 (3)	0.043 (3)	−0.005 (2)	−0.007 (2)	0.002 (2)
C111	0.035 (3)	0.029 (3)	0.042 (3)	−0.002 (2)	−0.006 (2)	−0.006 (2)
C112	0.030 (3)	0.052 (3)	0.038 (3)	−0.006 (2)	−0.001 (2)	0.001 (3)
C116	0.021 (2)	0.020 (3)	0.030 (3)	−0.0033 (19)	−0.002 (2)	0.000 (2)
C117	0.014 (2)	0.024 (3)	0.022 (3)	0.000 (2)	−0.0004 (19)	0.000 (2)
C118	0.020 (2)	0.028 (3)	0.023 (3)	0.004 (2)	−0.0033 (19)	0.001 (2)
C119	0.019 (2)	0.028 (3)	0.020 (2)	0.004 (2)	0.0011 (18)	0.003 (2)
C120	0.019 (2)	0.026 (3)	0.029 (3)	0.002 (2)	−0.006 (2)	−0.004 (2)
C121	0.021 (2)	0.030 (3)	0.021 (3)	0.005 (2)	−0.001 (2)	0.003 (2)
C122	0.029 (3)	0.020 (3)	0.030 (3)	−0.005 (2)	0.004 (2)	0.003 (2)
C123	0.019 (2)	0.028 (3)	0.028 (3)	−0.002 (2)	−0.006 (2)	0.001 (2)
C124	0.029 (2)	0.030 (3)	0.035 (3)	−0.006 (2)	−0.006 (2)	−0.006 (2)
C125	0.021 (2)	0.030 (3)	0.042 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C126	0.016 (2)	0.047 (3)	0.049 (3)	−0.008 (2)	−0.007 (2)	0.010 (3)
C127	0.026 (2)	0.032 (3)	0.042 (3)	0.006 (2)	−0.005 (2)	0.006 (2)
C131	0.017 (2)	0.023 (3)	0.044 (3)	−0.004 (2)	−0.005 (2)	−0.004 (2)
C132	0.023 (2)	0.031 (3)	0.030 (3)	0.005 (2)	−0.003 (2)	0.002 (3)
C133	0.030 (2)	0.035 (3)	0.044 (3)	−0.009 (2)	0.000 (2)	−0.006 (2)
C134	0.025 (2)	0.039 (3)	0.042 (3)	0.005 (2)	0.000 (2)	−0.008 (2)
C135	0.033 (3)	0.048 (3)	0.027 (3)	−0.004 (2)	−0.009 (2)	0.003 (3)
C136	0.031 (3)	0.041 (3)	0.041 (3)	−0.001 (2)	−0.008 (2)	0.013 (3)
C137	0.030 (3)	0.029 (3)	0.043 (3)	−0.004 (2)	−0.007 (2)	0.004 (2)
C138	0.028 (3)	0.032 (3)	0.034 (3)	0.002 (2)	−0.004 (2)	0.003 (3)
N101	0.0116 (17)	0.025 (2)	0.024 (2)	−0.0014 (16)	−0.0028 (15)	−0.0080 (18)
N102	0.024 (2)	0.017 (2)	0.027 (3)	−0.0112 (16)	−0.0055 (17)	−0.0003 (17)
O101	0.0175 (14)	0.035 (2)	0.0258 (18)	0.0036 (13)	0.0026 (12)	0.0045 (14)
O102	0.0221 (15)	0.0262 (18)	0.0309 (19)	−0.0008 (13)	−0.0102 (13)	0.0015 (14)
O103	0.0271 (17)	0.0294 (19)	0.030 (2)	−0.0073 (14)	−0.0117 (14)	0.0005 (17)

Geometric parameters (Å, º) top

Zn1—O102	1.958 (2)	C121—C122	1.399 (4)
Zn1—O101	1.961 (2)	C121—C127	1.518 (4)
Zn1—N101	2.163 (3)	C122—H122	0.9500
Zn1—N102	2.166 (3)	C123—C124	1.540 (5)
Zn1—O103	2.246 (3)	C123—C125	1.550 (5)
C101—C102	1.510 (5)	C123—C126	1.554 (4)
C101—N101	1.523 (4)	C124—H12A	0.9800
C101—H10A	0.9900	C124—H12B	0.9800
C101—H10B	0.9900	C124—H12C	0.9800
C102—C107	1.392 (5)	C125—H12D	0.9800
C102—C103	1.404 (5)	C125—H12E	0.9800
C103—O101	1.342 (4)	C125—H12F	0.9800
C103—C104	1.451 (5)	C126—H12G	0.9800
C104—C105	1.393 (5)	C126—H12H	0.9800
C104—C108	1.542 (5)	C126—H12I	0.9800
C105—C106	1.393 (5)	C127—H12J	0.9800
C105—H105	0.9500	C127—H12K	0.9800
C106—C107	1.398 (5)	C127—H12L	0.9800
C106—C112	1.529 (5)	C131—N101	1.484 (4)
C107—H107	0.9500	C131—C132	1.492 (5)
C108—C109	1.546 (4)	C131—H13I	0.9900
C108—C110	1.547 (5)	C131—H13J	0.9900
C108—C111	1.555 (4)	C132—N102	1.481 (4)
C109—H10C	0.9800	C132—H13K	0.9900
C109—H10D	0.9800	C132—H13L	0.9900
C109—H10E	0.9800	C133—N102	1.461 (4)
C110—H11A	0.9800	C133—H13P	0.9800
C110—H11B	0.9800	C133—H13Q	0.9800
C110—H11C	0.9800	C133—H13R	0.9800
C111—H11D	0.9800	C134—N102	1.522 (4)
C111—H11E	0.9800	C134—H13M	0.9800
C111—H11F	0.9800	C134—H13N	0.9800
C112—H11G	0.9800	C134—H13O	0.9800
C112—H11H	0.9800	C135—O103	1.466 (4)
C112—H11I	0.9800	C135—C136	1.508 (5)
C116—N101	1.478 (4)	C135—H13A	0.9900
C116—C117	1.515 (4)	C135—H13B	0.9900
C116—H11J	0.9900	C136—C137	1.516 (4)
C116—H11K	0.9900	C136—H13C	0.9900
C117—C118	1.411 (5)	C136—H13D	0.9900
C117—C122	1.411 (5)	C137—C138	1.504 (4)
C118—O102	1.337 (4)	C137—H13E	0.9900
C118—C119	1.454 (4)	C137—H13F	0.9900
C119—C120	1.389 (5)	C138—O103	1.436 (4)
C119—C123	1.538 (5)	C138—H13G	0.9900
C120—C121	1.395 (5)	C138—H13H	0.9900
C120—H120	0.9500

O102—Zn1—O101	127.59 (10)	C124—C123—C126	106.4 (3)
O102—Zn1—N101	93.35 (11)	C125—C123—C126	107.3 (3)
O101—Zn1—N101	94.41 (10)	C123—C124—H12A	109.5
O102—Zn1—N102	112.67 (11)	C123—C124—H12B	109.5
O101—Zn1—N102	119.71 (11)	H12A—C124—H12B	109.5
N101—Zn1—N102	82.88 (12)	C123—C124—H12C	109.5
O102—Zn1—O103	91.02 (10)	H12A—C124—H12C	109.5
O101—Zn1—O103	87.46 (9)	H12B—C124—H12C	109.5
N101—Zn1—O103	172.77 (11)	C123—C125—H12D	109.5
N102—Zn1—O103	90.13 (11)	C123—C125—H12E	109.5
C102—C101—N101	113.9 (3)	H12D—C125—H12E	109.5
C102—C101—H10A	108.8	C123—C125—H12F	109.5
N101—C101—H10A	108.8	H12D—C125—H12F	109.5
C102—C101—H10B	108.8	H12E—C125—H12F	109.5
N101—C101—H10B	108.8	C123—C126—H12G	109.5
H10A—C101—H10B	107.7	C123—C126—H12H	109.5
C107—C102—C103	121.6 (4)	H12G—C126—H12H	109.5
C107—C102—C101	119.7 (4)	C123—C126—H12I	109.5
C103—C102—C101	118.7 (4)	H12G—C126—H12I	109.5
O101—C103—C102	121.7 (4)	H12H—C126—H12I	109.5
O101—C103—C104	121.0 (4)	C121—C127—H12J	109.5
C102—C103—C104	117.3 (4)	C121—C127—H12K	109.5
C105—C104—C103	118.5 (4)	H12J—C127—H12K	109.5
C105—C104—C108	120.6 (4)	C121—C127—H12L	109.5
C103—C104—C108	120.9 (4)	H12J—C127—H12L	109.5
C104—C105—C106	123.6 (4)	H12K—C127—H12L	109.5
C104—C105—H105	118.2	N101—C131—C132	110.4 (3)
C106—C105—H105	118.2	N101—C131—H13I	109.6
C105—C106—C107	117.2 (4)	C132—C131—H13I	109.6
C105—C106—C112	122.1 (4)	N101—C131—H13J	109.6
C107—C106—C112	120.7 (4)	C132—C131—H13J	109.6
C102—C107—C106	121.5 (4)	H13I—C131—H13J	108.1
C102—C107—H107	119.3	N102—C132—C131	112.7 (3)
C106—C107—H107	119.3	N102—C132—H13K	109.0
C104—C108—C109	113.8 (3)	C131—C132—H13K	109.0
C104—C108—C110	110.4 (3)	N102—C132—H13L	109.0
C109—C108—C110	106.3 (3)	C131—C132—H13L	109.0
C104—C108—C111	109.8 (3)	H13K—C132—H13L	107.8
C109—C108—C111	107.0 (3)	N102—C133—H13P	109.5
C110—C108—C111	109.3 (3)	N102—C133—H13Q	109.5
C108—C109—H10C	109.5	H13P—C133—H13Q	109.5
C108—C109—H10D	109.5	N102—C133—H13R	109.5
H10C—C109—H10D	109.5	H13P—C133—H13R	109.5
C108—C109—H10E	109.5	H13Q—C133—H13R	109.5
H10C—C109—H10E	109.5	N102—C134—H13M	109.5
H10D—C109—H10E	109.5	N102—C134—H13N	109.5
C108—C110—H11A	109.5	H13M—C134—H13N	109.5
C108—C110—H11B	109.5	N102—C134—H13O	109.5
H11A—C110—H11B	109.5	H13M—C134—H13O	109.5
C108—C110—H11C	109.5	H13N—C134—H13O	109.5
H11A—C110—H11C	109.5	O103—C135—C136	106.5 (3)
H11B—C110—H11C	109.5	O103—C135—H13A	110.4
C108—C111—H11D	109.5	C136—C135—H13A	110.4
C108—C111—H11E	109.5	O103—C135—H13B	110.4
H11D—C111—H11E	109.5	C136—C135—H13B	110.4
C108—C111—H11F	109.5	H13A—C135—H13B	108.6
H11D—C111—H11F	109.5	C135—C136—C137	103.5 (3)
H11E—C111—H11F	109.5	C135—C136—H13C	111.1
C106—C112—H11G	109.5	C137—C136—H13C	111.1
C106—C112—H11H	109.5	C135—C136—H13D	111.1
H11G—C112—H11H	109.5	C137—C136—H13D	111.1
C106—C112—H11I	109.5	H13C—C136—H13D	109.0
H11G—C112—H11I	109.5	C138—C137—C136	102.8 (3)
H11H—C112—H11I	109.5	C138—C137—H13E	111.2
N101—C116—C117	114.7 (3)	C136—C137—H13E	111.2
N101—C116—H11J	108.6	C138—C137—H13F	111.2
C117—C116—H11J	108.6	C136—C137—H13F	111.2
N101—C116—H11K	108.6	H13E—C137—H13F	109.1
C117—C116—H11K	108.6	O103—C138—C137	108.6 (3)
H11J—C116—H11K	107.6	O103—C138—H13G	110.0
C118—C117—C122	120.7 (3)	C137—C138—H13G	110.0
C118—C117—C116	121.6 (3)	O103—C138—H13H	110.0
C122—C117—C116	117.1 (3)	C137—C138—H13H	110.0
O102—C118—C117	121.2 (3)	H13G—C138—H13H	108.3
O102—C118—C119	120.6 (4)	C116—N101—C131	111.7 (3)
C117—C118—C119	118.1 (4)	C116—N101—C101	109.3 (3)
C120—C119—C118	117.7 (4)	C131—N101—C101	110.3 (3)
C120—C119—C123	121.6 (3)	C116—N101—Zn1	110.3 (2)
C118—C119—C123	120.6 (3)	C131—N101—Zn1	107.4 (2)
C119—C120—C121	125.0 (3)	C101—N101—Zn1	107.7 (2)
C119—C120—H120	117.5	C133—N102—C132	109.7 (3)
C121—C120—H120	117.5	C133—N102—C134	107.5 (3)
C120—C121—C122	116.5 (4)	C132—N102—C134	109.6 (3)
C120—C121—C127	121.6 (3)	C133—N102—Zn1	118.0 (2)
C122—C121—C127	121.7 (4)	C132—N102—Zn1	105.4 (2)
C121—C122—C117	121.8 (4)	C134—N102—Zn1	106.4 (2)
C121—C122—H122	119.1	C103—O101—Zn1	120.1 (2)
C117—C122—H122	119.1	C118—O102—Zn1	126.6 (2)
C119—C123—C124	110.2 (3)	C138—O103—C135	107.9 (3)
C119—C123—C125	110.2 (3)	C138—O103—Zn1	124.1 (2)
C124—C123—C125	110.4 (3)	C135—O103—Zn1	119.1 (2)
C119—C123—C126	112.3 (3)

N101—C101—C102—C107	−115.4 (4)	C117—C116—N101—Zn1	−57.5 (3)
N101—C101—C102—C103	65.0 (4)	C132—C131—N101—C116	−157.3 (3)
C107—C102—C103—O101	174.4 (3)	C132—C131—N101—C101	80.9 (4)
C101—C102—C103—O101	−6.1 (5)	C132—C131—N101—Zn1	−36.3 (3)
C107—C102—C103—C104	−7.8 (5)	C102—C101—N101—C116	62.7 (4)
C101—C102—C103—C104	171.8 (3)	C102—C101—N101—C131	−174.1 (3)
O101—C103—C104—C105	−175.3 (3)	C102—C101—N101—Zn1	−57.1 (3)
C102—C103—C104—C105	6.8 (5)	O102—Zn1—N101—C116	20.8 (2)
O101—C103—C104—C108	2.2 (5)	O101—Zn1—N101—C116	−107.3 (2)
C102—C103—C104—C108	−175.7 (3)	N102—Zn1—N101—C116	133.3 (2)
C103—C104—C105—C106	−2.1 (6)	O102—Zn1—N101—C131	−101.0 (2)
C108—C104—C105—C106	−179.6 (3)	O101—Zn1—N101—C131	130.8 (2)
C104—C105—C106—C107	−2.0 (6)	N102—Zn1—N101—C131	11.4 (2)
C104—C105—C106—C112	176.3 (3)	O102—Zn1—N101—C101	140.1 (2)
C103—C102—C107—C106	3.8 (6)	O101—Zn1—N101—C101	12.0 (2)
C101—C102—C107—C106	−175.7 (3)	N102—Zn1—N101—C101	−107.4 (2)
C105—C106—C107—C102	1.2 (6)	C131—C132—N102—C133	−168.3 (3)
C112—C106—C107—C102	−177.1 (3)	C131—C132—N102—C134	73.9 (4)
C105—C104—C108—C109	−6.4 (5)	C131—C132—N102—Zn1	−40.2 (3)
C103—C104—C108—C109	176.2 (3)	O102—Zn1—N102—C133	−131.6 (2)
C105—C104—C108—C110	−125.8 (4)	O101—Zn1—N102—C133	46.7 (3)
C103—C104—C108—C110	56.8 (4)	N101—Zn1—N102—C133	137.7 (2)
C105—C104—C108—C111	113.6 (4)	O103—Zn1—N102—C133	−40.5 (2)
C103—C104—C108—C111	−63.8 (4)	O102—Zn1—N102—C132	105.5 (2)
N101—C116—C117—C118	59.3 (5)	O101—Zn1—N102—C132	−76.2 (3)
N101—C116—C117—C122	−129.2 (4)	N101—Zn1—N102—C132	14.8 (2)
C122—C117—C118—O102	179.9 (3)	O103—Zn1—N102—C132	−163.4 (2)
C116—C117—C118—O102	−8.9 (6)	O102—Zn1—N102—C134	−10.9 (3)
C122—C117—C118—C119	−2.7 (5)	O101—Zn1—N102—C134	167.4 (2)
C116—C117—C118—C119	168.5 (3)	N101—Zn1—N102—C134	−101.5 (2)
O102—C118—C119—C120	179.5 (3)	O103—Zn1—N102—C134	80.3 (2)
C117—C118—C119—C120	2.1 (5)	C102—C103—O101—Zn1	−45.9 (4)
O102—C118—C119—C123	2.6 (5)	C104—C103—O101—Zn1	136.3 (3)
C117—C118—C119—C123	−174.8 (3)	O102—Zn1—O101—C103	−60.3 (3)
C118—C119—C120—C121	0.4 (6)	N101—Zn1—O101—C103	37.4 (3)
C123—C119—C120—C121	177.3 (4)	N102—Zn1—O101—C103	121.7 (3)
C119—C120—C121—C122	−2.4 (6)	O103—Zn1—O101—C103	−149.6 (3)
C119—C120—C121—C127	−178.6 (4)	C117—C118—O102—Zn1	−31.9 (5)
C120—C121—C122—C117	1.8 (6)	C119—C118—O102—Zn1	150.7 (3)
C127—C121—C122—C117	178.0 (4)	O101—Zn1—O102—C118	120.9 (3)
C118—C117—C122—C121	0.7 (6)	N101—Zn1—O102—C118	22.7 (3)
C116—C117—C122—C121	−170.9 (3)	N102—Zn1—O102—C118	−61.0 (3)
C120—C119—C123—C124	−120.8 (4)	O103—Zn1—O102—C118	−151.5 (3)
C118—C119—C123—C124	56.0 (5)	C137—C138—O103—C135	−7.5 (4)
C120—C119—C123—C125	117.1 (4)	C137—C138—O103—Zn1	−154.2 (2)
C118—C119—C123—C125	−66.1 (4)	C136—C135—O103—C138	−13.5 (4)
C120—C119—C123—C126	−2.5 (5)	C136—C135—O103—Zn1	135.2 (2)
C118—C119—C123—C126	174.3 (3)	O102—Zn1—O103—C138	−25.4 (3)
N101—C131—C132—N102	53.6 (4)	O101—Zn1—O103—C138	102.2 (3)
O103—C135—C136—C137	28.7 (4)	N102—Zn1—O103—C138	−138.1 (3)
C135—C136—C137—C138	−32.1 (4)	O102—Zn1—O103—C135	−168.8 (3)
C136—C137—C138—O103	25.1 (4)	O101—Zn1—O103—C135	−41.2 (3)
C117—C116—N101—C131	61.9 (4)	N102—Zn1—O103—C135	78.6 (3)
C117—C116—N101—C101	−175.8 (3)

Experimental details

	(II)	(III)
Crystal data
Chemical formula	[Zn(C₃₄H₅₄N₂O₂)]	[Zn(C₂₈H₄₂N₂O₂)(C₄H₈O)]
M_r	588.16	576.11
Crystal system, space group	Triclinic, P1	Monoclinic, P2₁/c
Temperature (K)	140	140
a, b, c (Å)	12.9275 (12), 14.0002 (13), 19.6729 (14)	13.669 (3), 17.476 (4), 12.989 (4)
α, β, γ (°)	100.747 (7), 102.467 (7), 96.879 (8)	90, 93.14 (2), 90
V (Å³)	3367.8 (5)	3098.1 (14)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.76	0.83
Crystal size (mm)	0.20 × 0.08 × 0.02	0.06 × 0.06 × 0.02

Data collection
Diffractometer	Oxford Xcalibur3 CCD area-detector diffractometer	Oxford Xcalibur3 CCD area-detector diffractometer
Absorption correction	Multi-scan (ABSPACK; Oxford Diffraction, 2003)	Multi-scan (ABSPACK; Oxford Diffraction, 2003)
T_min, T_max	0.925, 0.983	0.801, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	42426, 15272, 8001	33137, 7121, 2308
R_int	0.076	0.195
(sin θ/λ)_max (Å⁻¹)	0.652	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.071, 0.79	0.049, 0.073, 0.68
No. of reflections	15272	7121
No. of parameters	744	353
No. of restraints	12	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43	0.37, −0.49

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97, PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

Selected geometric parameters (Å, º) for (II) top

Zn1—O101	1.8918 (15)	Zn2—O201	1.8821 (16)
Zn1—O102	1.8960 (17)	Zn2—O202	1.8899 (17)
Zn1—N101	2.065 (2)	Zn2—N201	2.0643 (18)
Zn1—N102	2.0864 (19)	Zn2—N202	2.0727 (19)

O101—Zn1—O102	125.35 (7)	O201—Zn2—O202	121.39 (7)
O101—Zn1—N101	99.58 (7)	O201—Zn2—N201	99.95 (7)
O102—Zn1—N101	99.77 (7)	O202—Zn2—N201	99.80 (7)
O101—Zn1—N102	112.76 (7)	O201—Zn2—N202	113.08 (8)
O102—Zn1—N102	118.59 (8)	O202—Zn2—N202	122.20 (8)
N101—Zn1—N102	87.81 (8)	N201—Zn2—N202	88.07 (7)

Selected geometric parameters (Å, º) for (III) top

Zn1—O102	1.958 (2)	Zn1—N102	2.166 (3)
Zn1—O101	1.961 (2)	Zn1—O103	2.246 (3)
Zn1—N101	2.163 (3)

O102—Zn1—O101	127.59 (10)	N101—Zn1—N102	82.88 (12)
O102—Zn1—N101	93.35 (11)	O102—Zn1—O103	91.02 (10)
O101—Zn1—N101	94.41 (10)	O101—Zn1—O103	87.46 (9)
O102—Zn1—N102	112.67 (11)	N101—Zn1—O103	172.77 (11)
O101—Zn1—N102	119.71 (11)	N102—Zn1—O103	90.13 (11)

Acknowledgements

RHH and JAW thank the EPSRC for funding.

References

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ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages m293-m296

doi:10.1107/S0108270106018695

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