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Acta Cryst. (2007). E63, m2170-m2171    [ doi:10.1107/S1600536807024944 ]

Bis[[mu]-2-hydroxy-N'-(4-hydroxy-2-oxidobenzylidene)benzohydrazide]bis[pyridinezinc(II)] dimethylformamide disolvate

J.-S. Huang and M.-T. Li

Abstract top

Reaction of 2,4-dihydroxybenzaldehye salicylhydrazide (L) with Zn(OAc)2·2H2O in a mixed solvent of pyridine and N,N-dimethylformamide (DMF) resulted in the formation of the title complex, [Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NO. The asymmetric unit contains one complete neutral zinc complex and one-half of a second complex with crystallographic inversion symmetry, together with three DMF solvent molecules. The Zn atoms, all having the same coordination geometry, are coordinated by three O atoms and two N atoms in a distorted tetragonal-pyramidal geometry, with phenolate O atoms acting as bridges between the Zn atoms.

Comment top

Studies of Schiff bases and their metal compounds are of current interest owing to their wide range of applications as biocides and homogeneous catalysts in the industry, antitumor activities and structural elucidation (Schurig et al., 1980; Siddall et al., 1983, Ando et al., 2004; Maurya et al., 2005). We report here the crystal structure of such a Zn(II) Schiff base compound, (I) [Zn2(L)2(py)2].2DMF, (L is 2,4-dihydroxybenzaldehyde salicylhydrazide, py is pyridine and DMF is N,N-dimethylformamide).

The molecular structure of (I) is shown in Fig.1. The crystal structure of the title complex consists of neutral binuclear Zn(II) dimers and solvent DMF molecules. Selected bond lengths and angles are given in Table 1. There are crystallographically independent zinc(II) centers with identical coordination geometry within the asymmetric unit of the title complex. All Zn(II) atoms are coordinated by three O atoms and two N atoms, in a distorted tetragonal-pyramidal geometry, due to the different distances of Zn—O and Zn—N. Three O atoms and one N atom from L ligands are located in the basal plane of the distorted square pyramid, and the apical position is occupied by an N atom belonging to a pyridine molecule. The Zn atoms are displaced by 0.4519 (3), 0.045 (3) and 0.4810 (3) Å, respectively, for Zn1, Zn2 and Zn3 out of the basal planes. Pairs of zinc atoms are bridged by two phenolate O atoms, to give a neutral dimer containing a planar Zn2O2 ring. It is interesting that the plane constructed by Zn1, Zn2, O2 and O6 is asymmetric because of the slight differences in coordination bonds and angles; however, the other dinuclear complex containing Zn3 has exact inversion symmetry. The distances of Zn—N and Zn—O (Table 1) are in agreement with the complex [Zn2(dhaash)2(py)4] (H2dhaash is 2,4-dihydroxy-5-acetylacetophenone-N-salicylhydrazone; Zn—N, 2.0818 (19), 2.255 (2) and 2.234 (2) Å; Zn—O, 2.234 (2), 2.0511 (17) and 2.085 (17) Å) (Hu et al., 2006). The Zn···Zn distances are 3.147 (2) and 3.149 (2) Å for Zn1···Zn2 and Zn3···-Zn3a (a: -x, -y, -z), respectively, which are comparable with those of the complex [Zn2(dhaash)2(py)4].

The ligand L, acting in a tridentate mode through the imide N, phenolate O and carbonyl O, forms two five/six-membered chelate rings. The dihedral angle of the pyridine molecules coordinated to Zn1 and Zn2 is 48.88 (18)°, whereas it is exactly zero by symmetry in the Zn3 complex.

Although DMF molecules are uncoordinated to metal atoms, they play an important role in stabilizing the crystal structure of the title complex. O—H···N hydrogen bonds are formed by the phenolic hydroxyl groups and N atoms belonging to DMF molecules.

Related literature top

For chemically related materials arising from metal–Schiff base compounds which contain Zn coordinated by N and O atoms, see: Hu et al. (2005, 2006). For details of the preparation of the Schiff base, see: Liu et al. (2001). For related literature, see: Ando et al. (2004); Maurya et al. (2005); Schurig et al. (1980); Siddall et al. (1983).

Experimental top

2,4-Dihydroxybenzaldehyde salicylhydrazide was prepared by a standard method reported in the literature (Liu et al., 2001). To a solution of 2,4-dihydroxybenzaldehyde salicylhydrazide (0.136 g, 0.5 mmol) in DMF (10 ml) was added Zn(OAc)2.2H2O (0.110 g, 1 mmol) dissolved in pyridine (5 ml). The mixture was stirred for 5 h at 323 K. After filtering, the yellow solution was allowed to stand at room temperature. Well shaped yellow block-like crystals were obtained by slow evaporation of the solvent at room temperature after seven days.

Refinement top

All H atoms were initially located in a difference Fourier map. The hydroxyl H atoms were then refined with the distance restraint O—H = 0.83 (3) Å and with Uiso(H) = 1.5Ueq(O). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) [Uiso(H) = 1.5Ueq(C) for methyl groups].

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex, showing labelling of the non-H atoms and 20% probability ellipsoids.
Bis[µ-2-hydroxy-N'-(4-hydroxy-2- oxidobenzylidene)benzohydrazide]bis[pyridinezinc(II)] dimethylformamide disolvate top
Crystal data top
[Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NOF(000) = 3024
Mr = 975.61Dx = 1.439 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 8439 reflections
a = 24.5015 (16) Åθ = 2.2–24.1°
b = 10.3868 (7) ŵ = 1.13 mm−1
c = 28.8550 (18) ÅT = 292 K
β = 113.127 (1)°Block, yellow
V = 6753.2 (8) Å30.20 × 0.16 × 0.10 mm
Z = 6
Data collection top
Bruker SMART CCD area-detector
diffractometer		15421 independent reflections
Radiation source: fine-focus sealed tube9826 reflections with I > 2σ(I)
graphiteRint = 0.042
φ and ω scansθmax = 27.5°, θmin = 0.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −31→31
Tmin = 0.805, Tmax = 0.895k = −13→13
45215 measured reflectionsl = −37→33
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.3991P]
where P = (Fo2 + 2Fc2)/3
15421 reflections(Δ/σ)max = 0.019
889 parametersΔρmax = 0.46 e Å−3
8 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NOV = 6753.2 (8) Å3
Mr = 975.61Z = 6
Monoclinic, P21/cMo Kα radiation
a = 24.5015 (16) ŵ = 1.13 mm−1
b = 10.3868 (7) ÅT = 292 K
c = 28.8550 (18) Å0.20 × 0.16 × 0.10 mm
β = 113.127 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		15421 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		9826 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 0.895Rint = 0.042
45215 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130Δρmax = 0.46 e Å−3
S = 1.01Δρmin = −0.37 e Å−3
15421 reflectionsAbsolute structure: ?
889 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C39−0.13981 (15)1.1389 (3)0.83565 (12)0.0698 (10)
H39−0.14241.12700.80290.084*
C40−0.18049 (15)1.2164 (3)0.84285 (12)0.0716 (10)
H40−0.20981.25710.81570.086*
C41−0.17738 (13)1.2335 (3)0.89139 (12)0.0570 (8)
C42−0.13180 (12)1.1765 (3)0.93168 (11)0.0498 (7)
H42−0.12931.19150.96420.060*
C43−0.09024 (12)1.0985 (3)0.92473 (10)0.0425 (6)
C44−0.09424 (13)1.0761 (3)0.87489 (11)0.0511 (7)
C45−0.05620 (13)0.9916 (3)0.86169 (11)0.0555 (8)
H45−0.06210.98800.82790.067*
C460.05520 (12)0.7705 (3)0.90646 (11)0.0465 (7)
C470.09223 (13)0.6838 (3)0.89027 (12)0.0538 (8)
C480.08175 (17)0.6626 (4)0.83995 (15)0.0757 (11)
C490.1161 (2)0.5736 (4)0.82740 (17)0.0942 (13)
H490.10810.55700.79370.113*
C500.16137 (19)0.5107 (4)0.86387 (19)0.0927 (14)
H500.18410.45190.85490.111*
C510.17375 (17)0.5333 (4)0.91381 (17)0.0871 (12)
H510.20520.49160.93880.105*
C520.13887 (15)0.6184 (3)0.92632 (14)0.0710 (10)
H520.14690.63260.96020.085*
C53−0.10147 (16)0.7683 (4)0.97847 (14)0.0773 (11)
H53−0.10660.85200.98740.093*
C54−0.14351 (18)0.6781 (5)0.97527 (17)0.0975 (14)
H54−0.17650.70070.98190.117*
C55−0.13668 (19)0.5562 (4)0.96245 (16)0.0903 (13)
H55−0.16400.49280.96120.108*
C56−0.08934 (19)0.5283 (4)0.95149 (15)0.0885 (12)
H56−0.08440.44580.94130.106*
C57−0.04889 (15)0.6221 (3)0.95547 (14)0.0680 (10)
H57−0.01630.60120.94810.082*
N7−0.01495 (10)0.9209 (2)0.89227 (9)0.0465 (6)
N80.01622 (11)0.8430 (3)0.87155 (9)0.0524 (6)
N9−0.05371 (10)0.7414 (2)0.96935 (9)0.0475 (6)
O10−0.04673 (8)1.04600 (18)0.96459 (7)0.0463 (5)
O110.06377 (8)0.77032 (19)0.95335 (7)0.0522 (5)
C10.53682 (14)1.1453 (3)0.50955 (12)0.0604 (9)
H1A0.53471.13370.47690.072*
C20.49826 (13)1.2285 (3)0.51657 (11)0.0568 (8)
H20.47111.27380.48950.068*
C30.50004 (12)1.2449 (3)0.56487 (11)0.0458 (7)
C40.54248 (11)1.1813 (3)0.60507 (10)0.0419 (6)
H4A0.54411.19540.63740.050*
C50.58279 (11)1.0970 (2)0.59834 (10)0.0377 (6)
C60.57988 (12)1.0755 (3)0.54859 (10)0.0429 (7)
C70.61585 (13)0.9864 (3)0.53544 (11)0.0490 (7)
H70.60980.98240.50160.059*
C80.72613 (12)0.7633 (3)0.57867 (12)0.0445 (7)
C90.76086 (13)0.6715 (3)0.56169 (12)0.0514 (8)
C100.74549 (16)0.6407 (3)0.51100 (14)0.0641 (9)
C110.77854 (19)0.5498 (4)0.49796 (16)0.0834 (12)
H110.76770.52750.46430.100*
C120.82691 (19)0.4927 (4)0.53409 (19)0.0898 (13)
H12A0.84870.43220.52480.108*
C130.84336 (16)0.5242 (4)0.58397 (17)0.0851 (12)
H130.87660.48630.60840.102*
C140.81059 (14)0.6118 (3)0.59757 (14)0.0668 (10)
H140.82170.63190.63150.080*
C150.79873 (16)0.8112 (4)0.83424 (13)0.0778 (11)
H15A0.79700.80950.86590.093*
C160.84181 (16)0.7417 (4)0.82722 (14)0.0776 (11)
H160.86810.69190.85320.093*
C170.84613 (13)0.7458 (3)0.78087 (13)0.0593 (9)
C180.80483 (12)0.8150 (3)0.74174 (11)0.0506 (7)
H180.80720.81460.71040.061*
C190.76020 (12)0.8844 (3)0.74804 (11)0.0431 (7)
C200.75654 (13)0.8857 (3)0.79604 (11)0.0538 (8)
C210.71601 (14)0.9616 (3)0.80886 (11)0.0609 (9)
H210.71760.95290.84150.073*
C220.60709 (12)1.1883 (3)0.76932 (11)0.0453 (7)
C230.56973 (13)1.2669 (3)0.78813 (12)0.0547 (8)
C240.57610 (17)1.2643 (4)0.83837 (15)0.0786 (11)
C250.5423 (2)1.3450 (5)0.85447 (17)0.1076 (16)
H250.54741.34450.88810.129*
C260.5015 (2)1.4254 (5)0.8213 (2)0.1072 (17)
H260.47891.47910.83260.129*
C270.49319 (19)1.4278 (4)0.7711 (2)0.0972 (15)
H270.46511.48210.74840.117*
C280.52743 (15)1.3481 (3)0.75535 (15)0.0718 (10)
H280.52191.34880.72160.086*
C290.60496 (14)0.6467 (3)0.61160 (12)0.0590 (8)
H290.61750.65130.58510.071*
C300.56612 (17)0.5516 (4)0.61068 (14)0.0794 (11)
H300.55240.49370.58400.095*
C310.54776 (17)0.5426 (4)0.64922 (15)0.0826 (12)
H310.52080.47960.64920.099*
C320.56997 (17)0.6286 (4)0.68808 (14)0.0822 (12)
H320.55900.62330.71540.099*
C330.60830 (14)0.7221 (3)0.68643 (12)0.0630 (9)
H330.62280.78050.71290.076*
C340.76581 (14)1.2361 (3)0.69807 (12)0.0622 (9)
H340.77511.15330.69130.075*
C350.80319 (17)1.3359 (4)0.69887 (15)0.0842 (12)
H350.83711.32020.69280.101*
C360.79015 (19)1.4575 (4)0.70864 (15)0.0866 (12)
H360.81471.52620.70910.104*
C370.74053 (19)1.4763 (4)0.71765 (15)0.0882 (12)
H370.73071.55840.72460.106*
C380.70497 (15)1.3735 (3)0.71641 (13)0.0666 (9)
H380.67101.38790.72270.080*
C580.69475 (18)0.2615 (4)0.49964 (16)0.0981 (14)
H58A0.73610.28260.51130.147*
H58B0.67750.26190.46350.147*
H58C0.69040.17760.51170.147*
C590.68097 (18)0.3602 (4)0.57223 (14)0.0984 (14)
H59A0.64570.36370.57910.148*
H59B0.70480.43520.58600.148*
H59C0.70320.28440.58730.148*
C600.62674 (15)0.4399 (4)0.48899 (13)0.0661 (9)
H600.61890.43490.45480.079*
C610.6792 (2)0.5286 (5)0.90595 (19)0.1362 (19)
H61A0.71660.56310.92850.204*
H61B0.68340.43810.90140.204*
H61C0.65000.54170.92000.204*
C620.6224 (2)0.7033 (5)0.8490 (2)0.146 (2)
H62A0.61080.73080.81470.219*
H62B0.64320.77190.87130.219*
H62C0.58780.68080.85500.219*
C630.6769 (2)0.5424 (6)0.82513 (19)0.1182 (18)
H630.66350.58450.79420.142*
C640.0345 (2)0.2513 (5)0.82233 (19)0.1297 (19)
H64A0.07450.27810.82940.195*
H64B0.01260.24780.78650.195*
H64C0.03490.16760.83660.195*
C650.0269 (2)0.3277 (5)0.89926 (18)0.145 (2)
H65A0.01080.39650.91230.217*
H65B0.06940.33070.91460.217*
H65C0.01330.24670.90680.217*
C66−0.0273 (2)0.4296 (5)0.8205 (2)0.124 (2)
H66−0.03820.43500.78590.149*
N10.65551 (10)0.9115 (2)0.56540 (9)0.0430 (5)
N20.68481 (10)0.8309 (2)0.54383 (9)0.0501 (6)
N30.67750 (10)1.0409 (2)0.77984 (8)0.0461 (6)
N40.64395 (11)1.1071 (2)0.80141 (9)0.0539 (7)
N50.62581 (9)0.7330 (2)0.64829 (9)0.0439 (6)
N60.71668 (10)1.2541 (2)0.70666 (8)0.0449 (6)
N100.66478 (12)0.3565 (3)0.51865 (11)0.0645 (7)
N110.66080 (16)0.5928 (4)0.85816 (14)0.0903 (10)
N120.00686 (15)0.3419 (4)0.84401 (14)0.0911 (10)
O10.46196 (9)1.3230 (2)0.57503 (8)0.0603 (6)
H10.4395 (14)1.354 (4)0.5493 (11)0.090*
O20.62409 (7)1.03809 (17)0.63830 (6)0.0414 (4)
O30.73819 (8)0.77002 (19)0.62614 (7)0.0532 (5)
O40.69857 (14)0.6951 (3)0.47371 (10)0.0908 (9)
H40.6820 (19)0.742 (4)0.4860 (16)0.136*
O50.88845 (10)0.6825 (3)0.77117 (10)0.0828 (8)
H50.9114 (16)0.639 (4)0.7946 (13)0.124*
O60.72031 (8)0.94960 (17)0.70896 (7)0.0433 (4)
O70.60160 (8)1.20387 (19)0.72382 (7)0.0511 (5)
O80.61562 (15)1.1868 (4)0.87241 (10)0.1209 (12)
H80.631 (2)1.137 (4)0.8569 (19)0.181*
O9−0.21681 (11)1.3052 (3)0.90247 (10)0.0839 (8)
H9−0.2375 (18)1.337 (5)0.8795 (13)0.126*
O120.03810 (15)0.7243 (4)0.80240 (11)0.1214 (13)
H120.024 (2)0.788 (4)0.810 (2)0.182*
O130.60078 (11)0.5232 (2)0.50210 (9)0.0738 (7)
O140.70709 (14)0.4477 (3)0.82828 (11)0.1173 (11)
O15−0.04849 (13)0.5139 (3)0.84213 (12)0.1122 (11)
Zn10.677430 (13)0.88007 (3)0.640099 (12)0.03916 (10)
Zn20.664039 (13)1.10261 (3)0.708892 (12)0.04011 (10)
Zn30.003714 (13)0.88356 (3)0.966433 (11)0.04081 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C390.078 (2)0.078 (3)0.0405 (19)0.025 (2)0.0094 (17)0.0031 (17)
C400.069 (2)0.074 (3)0.046 (2)0.0267 (19)−0.0050 (17)0.0024 (18)
C410.0477 (18)0.053 (2)0.056 (2)0.0091 (15)0.0060 (15)−0.0066 (16)
C420.0517 (17)0.0462 (18)0.0450 (18)0.0069 (14)0.0118 (14)0.0010 (14)
C430.0438 (16)0.0358 (16)0.0390 (16)−0.0019 (12)0.0065 (13)0.0002 (12)
C440.0525 (18)0.0536 (19)0.0381 (17)0.0060 (15)0.0081 (14)0.0013 (14)
C450.059 (2)0.064 (2)0.0388 (18)0.0065 (16)0.0145 (15)0.0012 (15)
C460.0431 (16)0.0508 (19)0.0489 (19)−0.0057 (14)0.0217 (14)−0.0049 (15)
C470.0515 (18)0.056 (2)0.061 (2)−0.0023 (15)0.0298 (16)−0.0071 (16)
C480.078 (3)0.092 (3)0.069 (3)0.011 (2)0.041 (2)−0.009 (2)
C490.106 (3)0.113 (4)0.084 (3)0.016 (3)0.060 (3)−0.018 (3)
C500.094 (3)0.085 (3)0.123 (4)0.019 (2)0.068 (3)−0.014 (3)
C510.082 (3)0.077 (3)0.107 (4)0.028 (2)0.043 (3)−0.001 (2)
C520.069 (2)0.075 (3)0.073 (3)0.0154 (19)0.034 (2)−0.0070 (19)
C530.084 (3)0.064 (2)0.106 (3)−0.008 (2)0.061 (2)−0.004 (2)
C540.087 (3)0.094 (3)0.138 (4)−0.017 (3)0.073 (3)0.002 (3)
C550.089 (3)0.077 (3)0.103 (3)−0.030 (2)0.036 (3)0.014 (3)
C560.100 (3)0.053 (2)0.115 (4)−0.018 (2)0.045 (3)−0.003 (2)
C570.069 (2)0.047 (2)0.090 (3)−0.0024 (17)0.033 (2)−0.0021 (18)
N70.0459 (14)0.0533 (16)0.0402 (14)0.0043 (12)0.0170 (11)0.0018 (11)
N80.0542 (15)0.0627 (17)0.0439 (15)0.0068 (13)0.0231 (12)−0.0006 (13)
N90.0519 (15)0.0430 (15)0.0475 (15)0.0005 (11)0.0194 (12)0.0043 (11)
O100.0495 (11)0.0439 (12)0.0356 (11)0.0111 (9)0.0061 (9)−0.0006 (9)
O110.0513 (12)0.0610 (14)0.0449 (12)0.0116 (10)0.0194 (10)−0.0014 (10)
C10.072 (2)0.065 (2)0.0403 (19)0.0176 (18)0.0169 (16)0.0099 (15)
C20.060 (2)0.054 (2)0.0438 (19)0.0164 (16)0.0065 (15)0.0118 (15)
C30.0413 (16)0.0352 (16)0.053 (2)0.0025 (13)0.0103 (14)0.0017 (13)
C40.0441 (16)0.0389 (16)0.0393 (16)0.0009 (13)0.0127 (13)0.0016 (12)
C50.0372 (14)0.0325 (15)0.0386 (16)−0.0024 (12)0.0098 (12)0.0035 (12)
C60.0458 (16)0.0429 (17)0.0382 (16)0.0038 (13)0.0144 (13)0.0019 (13)
C70.0606 (19)0.0505 (19)0.0377 (17)0.0024 (15)0.0212 (14)0.0018 (14)
C80.0426 (16)0.0444 (17)0.0528 (19)−0.0047 (13)0.0253 (15)−0.0027 (14)
C90.0582 (19)0.0411 (17)0.068 (2)−0.0009 (14)0.0394 (17)−0.0036 (15)
C100.083 (2)0.057 (2)0.069 (3)0.0070 (18)0.048 (2)0.0037 (18)
C110.112 (3)0.073 (3)0.094 (3)0.013 (2)0.071 (3)−0.007 (2)
C120.100 (3)0.070 (3)0.131 (4)0.022 (2)0.080 (3)−0.002 (3)
C130.071 (2)0.073 (3)0.119 (4)0.026 (2)0.046 (2)−0.004 (2)
C140.0539 (19)0.065 (2)0.085 (3)0.0096 (17)0.0322 (19)−0.0060 (19)
C150.088 (3)0.088 (3)0.047 (2)0.038 (2)0.0156 (19)0.0174 (19)
C160.075 (2)0.076 (3)0.060 (2)0.033 (2)0.0018 (19)0.0125 (19)
C170.0439 (18)0.053 (2)0.062 (2)0.0103 (15)0.0012 (16)−0.0030 (16)
C180.0464 (17)0.0456 (18)0.0511 (19)0.0068 (14)0.0098 (14)−0.0001 (14)
C190.0404 (15)0.0342 (16)0.0433 (17)−0.0003 (12)0.0043 (13)−0.0012 (13)
C200.0540 (18)0.056 (2)0.0410 (18)0.0122 (15)0.0072 (14)0.0077 (15)
C210.070 (2)0.073 (2)0.0372 (18)0.0171 (18)0.0182 (16)0.0092 (16)
C220.0432 (16)0.0481 (18)0.0450 (18)−0.0017 (13)0.0178 (14)−0.0061 (14)
C230.0546 (19)0.056 (2)0.060 (2)−0.0039 (15)0.0286 (16)−0.0128 (16)
C240.072 (2)0.104 (3)0.064 (3)0.007 (2)0.031 (2)−0.023 (2)
C250.095 (3)0.155 (5)0.086 (3)0.008 (3)0.049 (3)−0.051 (3)
C260.092 (3)0.098 (4)0.158 (5)−0.001 (3)0.077 (4)−0.050 (3)
C270.095 (3)0.072 (3)0.150 (5)0.025 (2)0.075 (3)0.005 (3)
C280.071 (2)0.061 (2)0.097 (3)0.0165 (19)0.048 (2)0.010 (2)
C290.075 (2)0.054 (2)0.048 (2)−0.0143 (17)0.0242 (17)−0.0028 (16)
C300.102 (3)0.068 (3)0.065 (3)−0.037 (2)0.030 (2)−0.0117 (19)
C310.093 (3)0.075 (3)0.083 (3)−0.039 (2)0.037 (2)0.000 (2)
C320.097 (3)0.093 (3)0.073 (3)−0.026 (2)0.052 (2)0.001 (2)
C330.070 (2)0.067 (2)0.059 (2)−0.0104 (18)0.0332 (18)−0.0059 (17)
C340.066 (2)0.056 (2)0.071 (2)−0.0017 (17)0.0347 (19)0.0000 (17)
C350.074 (3)0.085 (3)0.106 (3)−0.016 (2)0.049 (2)0.000 (2)
C360.097 (3)0.064 (3)0.100 (3)−0.032 (2)0.040 (3)−0.004 (2)
C370.101 (3)0.051 (2)0.112 (4)−0.012 (2)0.041 (3)−0.007 (2)
C380.071 (2)0.048 (2)0.079 (3)−0.0020 (17)0.0283 (19)−0.0031 (17)
C580.094 (3)0.076 (3)0.118 (4)0.025 (2)0.035 (3)0.010 (3)
C590.112 (3)0.093 (3)0.058 (3)−0.005 (3)−0.001 (2)0.019 (2)
C600.076 (2)0.068 (2)0.046 (2)0.010 (2)0.0149 (18)0.0052 (18)
C610.171 (5)0.119 (5)0.125 (5)0.002 (4)0.066 (4)−0.005 (4)
C620.142 (5)0.111 (4)0.144 (5)0.058 (4)0.011 (4)−0.018 (4)
C630.115 (4)0.139 (5)0.077 (4)0.042 (4)0.012 (3)0.024 (3)
C640.133 (4)0.123 (4)0.119 (4)0.038 (4)0.034 (3)−0.009 (3)
C650.166 (5)0.143 (5)0.091 (4)−0.009 (4)0.013 (4)0.008 (3)
C660.089 (3)0.101 (4)0.145 (5)0.031 (3)0.006 (3)0.042 (4)
N10.0468 (13)0.0421 (14)0.0449 (14)0.0029 (11)0.0232 (11)0.0018 (11)
N20.0594 (15)0.0505 (16)0.0481 (16)0.0091 (12)0.0295 (13)0.0003 (12)
N30.0466 (14)0.0521 (15)0.0382 (14)0.0085 (12)0.0150 (11)0.0024 (11)
N40.0570 (15)0.0653 (18)0.0401 (15)0.0127 (13)0.0200 (12)−0.0004 (13)
N50.0471 (14)0.0404 (14)0.0437 (15)−0.0006 (11)0.0170 (11)0.0027 (11)
N60.0482 (14)0.0399 (14)0.0420 (14)−0.0011 (11)0.0128 (11)0.0012 (11)
N100.0677 (18)0.0538 (18)0.0618 (19)0.0052 (14)0.0144 (15)0.0086 (14)
N110.098 (3)0.095 (3)0.066 (2)0.011 (2)0.021 (2)−0.008 (2)
N120.086 (2)0.096 (3)0.077 (3)0.005 (2)0.016 (2)−0.011 (2)
O10.0512 (13)0.0585 (15)0.0624 (16)0.0203 (11)0.0130 (11)0.0047 (12)
O20.0432 (10)0.0404 (11)0.0338 (11)0.0093 (8)0.0079 (8)−0.0003 (8)
O30.0485 (12)0.0605 (14)0.0508 (13)0.0150 (10)0.0198 (10)−0.0031 (10)
O40.122 (2)0.100 (2)0.0624 (18)0.0381 (18)0.0494 (16)0.0043 (15)
O50.0574 (15)0.087 (2)0.087 (2)0.0349 (13)0.0100 (14)0.0024 (15)
O60.0454 (11)0.0380 (11)0.0386 (11)0.0100 (9)0.0081 (9)0.0008 (8)
O70.0523 (12)0.0583 (13)0.0440 (13)0.0140 (10)0.0205 (10)0.0033 (10)
O80.126 (3)0.192 (4)0.0504 (18)0.060 (2)0.0415 (17)0.005 (2)
O90.0729 (18)0.090 (2)0.0721 (19)0.0392 (15)0.0107 (14)−0.0042 (15)
O120.126 (3)0.185 (4)0.0566 (18)0.073 (2)0.0401 (17)0.004 (2)
O130.0861 (17)0.0692 (17)0.0656 (16)0.0234 (14)0.0293 (13)0.0055 (13)
O140.115 (2)0.134 (3)0.090 (2)0.061 (2)0.0260 (18)0.020 (2)
O150.095 (2)0.101 (3)0.137 (3)0.0457 (19)0.042 (2)0.028 (2)
Zn10.04099 (18)0.03685 (19)0.0397 (2)0.00210 (14)0.01589 (14)−0.00053 (14)
Zn20.04315 (18)0.03859 (19)0.03748 (19)0.00409 (14)0.01463 (14)0.00014 (14)
Zn30.04396 (19)0.0392 (2)0.03812 (19)0.00194 (14)0.01485 (14)−0.00090 (14)
Geometric parameters (Å, °) top
C39—C401.359 (4)C22—N41.315 (4)
C39—C441.401 (4)C22—C231.480 (4)
C39—H390.930C23—C281.382 (4)
C40—C411.384 (4)C23—C241.396 (4)
C40—H400.930C24—O81.343 (5)
C41—O91.354 (4)C24—C251.380 (5)
C41—C421.389 (4)C25—C261.364 (6)
C42—C431.376 (4)C25—H250.930
C42—H420.930C26—C271.383 (6)
C43—O101.339 (3)C26—H260.930
C43—C441.422 (4)C27—C281.376 (5)
C44—C451.436 (4)C27—H270.930
C45—N71.280 (3)C28—H280.930
C45—H450.930C29—N51.327 (4)
C46—O111.285 (3)C29—C301.364 (4)
C46—N81.319 (4)C29—H290.930
C46—C471.478 (4)C30—C311.357 (5)
C47—C521.384 (4)C30—H300.930
C47—C481.389 (4)C31—C321.368 (5)
C48—O121.348 (5)C31—H310.930
C48—C491.391 (5)C32—C331.365 (4)
C49—C501.359 (6)C32—H320.930
C49—H490.930C33—N51.334 (3)
C50—C511.371 (5)C33—H330.930
C50—H500.930C34—N61.334 (3)
C51—C521.373 (4)C34—C351.378 (4)
C51—H510.930C34—H340.930
C52—H520.930C35—C361.359 (5)
C53—N91.326 (4)C35—H350.930
C53—C541.368 (5)C36—C371.354 (5)
C53—H530.930C36—H360.930
C54—C551.348 (6)C37—C381.370 (5)
C54—H540.930C37—H370.930
C55—C561.348 (5)C38—N61.328 (4)
C55—H550.930C38—H380.930
C56—C571.362 (5)C58—N101.459 (4)
C56—H560.930C58—H58A0.960
C57—N91.322 (4)C58—H58B0.960
C57—H570.930C58—H58C0.960
N7—N81.398 (3)C59—N101.438 (4)
N7—Zn32.042 (2)C59—H59A0.960
N9—Zn32.064 (2)C59—H59B0.960
O10—Zn3i1.9900 (18)C59—H59C0.960
O10—Zn32.0798 (18)C60—O131.219 (4)
O11—Zn32.0316 (18)C60—N101.313 (4)
C1—C21.353 (4)C60—H600.930
C1—C61.405 (4)C61—N111.435 (5)
C1—H1A0.930C61—H61A0.960
C2—C31.388 (4)C61—H61B0.960
C2—H20.930C61—H61C0.960
C3—O11.353 (3)C62—N111.441 (5)
C3—C41.384 (4)C62—H62A0.960
C4—C51.390 (3)C62—H62B0.960
C4—H4A0.930C62—H62C0.960
C5—O21.346 (3)C63—O141.213 (5)
C5—C61.427 (4)C63—N111.278 (5)
C6—C71.428 (4)C63—H630.930
C7—N11.279 (3)C64—N121.439 (5)
C7—H70.930C64—H64A0.960
C8—O31.285 (3)C64—H64B0.960
C8—N21.315 (4)C64—H64C0.960
C8—C91.483 (4)C65—N121.480 (5)
C9—C101.397 (4)C65—H65A0.960
C9—C141.397 (4)C65—H65B0.960
C10—O41.351 (4)C65—H65C0.960
C10—C111.389 (4)C66—N121.243 (5)
C11—C121.368 (5)C66—O151.296 (6)
C11—H110.930C66—H660.930
C12—C131.373 (5)N1—N21.398 (3)
C12—H12A0.930N1—Zn12.033 (2)
C13—C141.369 (4)N3—N41.392 (3)
C13—H130.930N3—Zn22.045 (2)
C14—H140.930N5—Zn12.056 (2)
C15—C161.358 (4)N6—Zn22.051 (2)
C15—C201.410 (4)O1—H10.80 (2)
C15—H15A0.930O2—Zn21.9976 (17)
C16—C171.383 (5)O2—Zn12.0859 (17)
C16—H160.930O3—Zn12.0388 (18)
C17—O51.346 (4)O4—H40.80 (5)
C17—C181.385 (4)O5—H50.82 (5)
C18—C191.380 (4)O6—Zn11.9834 (18)
C18—H180.930O6—Zn22.1035 (17)
C19—O61.349 (3)O7—Zn22.0372 (18)
C19—C201.423 (4)O8—H80.87 (3)
C20—C211.426 (4)O9—H90.73 (3)
C21—N31.284 (4)O12—H120.82 (3)
C21—H210.930Zn3—O10i1.9900 (18)
C22—O71.276 (3)Zn3—Zn3i3.1486 (6)
C40—C39—C44123.5 (3)C27—C28—H28118.9
C40—C39—H39118.2C23—C28—H28118.9
C44—C39—H39118.2N5—C29—C30123.5 (3)
C39—C40—C41118.6 (3)N5—C29—H29118.3
C39—C40—H40120.7C30—C29—H29118.3
C41—C40—H40120.7C31—C30—C29119.1 (3)
O9—C41—C40123.3 (3)C31—C30—H30120.4
O9—C41—C42116.8 (3)C29—C30—H30120.4
C40—C41—C42119.9 (3)C30—C31—C32118.3 (3)
C43—C42—C41121.8 (3)C30—C31—H31120.9
C43—C42—H42119.1C32—C31—H31120.9
C41—C42—H42119.1C33—C32—C31119.6 (3)
O10—C43—C42120.0 (3)C33—C32—H32120.2
O10—C43—C44121.2 (3)C31—C32—H32120.2
C42—C43—C44118.9 (3)N5—C33—C32122.5 (3)
C39—C44—C43117.2 (3)N5—C33—H33118.7
C39—C44—C45117.7 (3)C32—C33—H33118.7
C43—C44—C45125.1 (3)N6—C34—C35122.3 (3)
N7—C45—C44125.9 (3)N6—C34—H34118.9
N7—C45—H45117.0C35—C34—H34118.9
C44—C45—H45117.0C36—C35—C34119.6 (4)
O11—C46—N8125.1 (3)C36—C35—H35120.2
O11—C46—C47117.7 (3)C34—C35—H35120.2
N8—C46—C47117.2 (3)C37—C36—C35118.4 (4)
C52—C47—C48117.8 (3)C37—C36—H36120.8
C52—C47—C46119.3 (3)C35—C36—H36120.8
C48—C47—C46122.9 (3)C36—C37—C38119.5 (4)
O12—C48—C47121.8 (3)C36—C37—H37120.3
O12—C48—C49118.5 (4)C38—C37—H37120.3
C47—C48—C49119.7 (4)N6—C38—C37123.1 (3)
C50—C49—C48120.7 (4)N6—C38—H38118.5
C50—C49—H49119.6C37—C38—H38118.5
C48—C49—H49119.6N10—C58—H58A109.5
C49—C50—C51120.6 (4)N10—C58—H58B109.5
C49—C50—H50119.7H58A—C58—H58B109.5
C51—C50—H50119.7N10—C58—H58C109.5
C50—C51—C52118.9 (4)H58A—C58—H58C109.5
C50—C51—H51120.6H58B—C58—H58C109.5
C52—C51—H51120.6N10—C59—H59A109.5
C51—C52—C47122.3 (4)N10—C59—H59B109.5
C51—C52—H52118.9H59A—C59—H59B109.5
C47—C52—H52118.9N10—C59—H59C109.5
N9—C53—C54122.8 (4)H59A—C59—H59C109.5
N9—C53—H53118.6H59B—C59—H59C109.5
C54—C53—H53118.6O13—C60—N10126.1 (3)
C55—C54—C53119.4 (4)O13—C60—H60116.9
C55—C54—H54120.3N10—C60—H60116.9
C53—C54—H54120.3N11—C61—H61A109.5
C54—C55—C56118.5 (4)N11—C61—H61B109.5
C54—C55—H55120.7H61A—C61—H61B109.5
C56—C55—H55120.7N11—C61—H61C109.5
C55—C56—C57119.4 (4)H61A—C61—H61C109.5
C55—C56—H56120.3H61B—C61—H61C109.5
C57—C56—H56120.3N11—C62—H62A109.5
N9—C57—C56123.2 (3)N11—C62—H62B109.5
N9—C57—H57118.4H62A—C62—H62B109.5
C56—C57—H57118.4N11—C62—H62C109.5
C45—N7—N8117.0 (2)H62A—C62—H62C109.5
C45—N7—Zn3128.5 (2)H62B—C62—H62C109.5
N8—N7—Zn3113.79 (17)O14—C63—N11129.3 (5)
C46—N8—N7110.9 (2)O14—C63—H63115.3
C57—N9—C53116.6 (3)N11—C63—H63115.3
C57—N9—Zn3121.0 (2)N12—C64—H64A109.5
C53—N9—Zn3121.8 (2)N12—C64—H64B109.5
C43—O10—Zn3i129.77 (17)H64A—C64—H64B109.5
C43—O10—Zn3128.08 (17)N12—C64—H64C109.5
Zn3i—O10—Zn3101.34 (7)H64A—C64—H64C109.5
C46—O11—Zn3111.35 (17)H64B—C64—H64C109.5
C2—C1—C6123.9 (3)N12—C65—H65A109.5
C2—C1—H1A118.0N12—C65—H65B109.5
C6—C1—H1A118.0H65A—C65—H65B109.5
C1—C2—C3118.7 (3)N12—C65—H65C109.5
C1—C2—H2120.6H65A—C65—H65C109.5
C3—C2—H2120.6H65B—C65—H65C109.5
O1—C3—C4117.4 (3)N12—C66—O15122.9 (5)
O1—C3—C2122.6 (3)N12—C66—H66118.5
C4—C3—C2120.0 (3)O15—C66—H66118.5
C3—C4—C5121.7 (3)C7—N1—N2116.7 (2)
C3—C4—H4A119.2C7—N1—Zn1128.9 (2)
C5—C4—H4A119.2N2—N1—Zn1114.07 (17)
O2—C5—C4120.2 (2)C8—N2—N1110.8 (2)
O2—C5—C6121.0 (2)C21—N3—N4115.9 (2)
C4—C5—C6118.8 (2)C21—N3—Zn2130.0 (2)
C1—C6—C5116.8 (3)N4—N3—Zn2113.66 (17)
C1—C6—C7118.0 (3)C22—N4—N3111.4 (2)
C5—C6—C7125.2 (3)C29—N5—C33117.0 (3)
N1—C7—C6126.8 (3)C29—N5—Zn1118.2 (2)
N1—C7—H7116.6C33—N5—Zn1124.7 (2)
C6—C7—H7116.6C38—N6—C34117.1 (3)
O3—C8—N2124.9 (3)C38—N6—Zn2121.2 (2)
O3—C8—C9117.7 (3)C34—N6—Zn2121.5 (2)
N2—C8—C9117.4 (3)C60—N10—C59120.5 (3)
C10—C9—C14118.2 (3)C60—N10—C58122.3 (3)
C10—C9—C8122.6 (3)C59—N10—C58117.1 (3)
C14—C9—C8119.2 (3)C63—N11—C61117.0 (4)
O4—C10—C11118.2 (3)C63—N11—C62124.1 (4)
O4—C10—C9122.2 (3)C61—N11—C62118.8 (4)
C11—C10—C9119.6 (4)C66—N12—C64125.0 (5)
C12—C11—C10120.7 (4)C66—N12—C65121.9 (5)
C12—C11—H11119.6C64—N12—C65112.9 (4)
C10—C11—H11119.6C3—O1—H1109 (3)
C11—C12—C13120.3 (4)C5—O2—Zn2128.58 (16)
C11—C12—H12A119.8C5—O2—Zn1129.18 (16)
C13—C12—H12A119.8Zn2—O2—Zn1100.80 (7)
C14—C13—C12119.7 (4)C8—O3—Zn1111.17 (17)
C14—C13—H13120.2C10—O4—H4109 (3)
C12—C13—H13120.2C17—O5—H5115 (3)
C13—C14—C9121.5 (4)C19—O6—Zn1125.41 (17)
C13—C14—H14119.3C19—O6—Zn2129.76 (17)
C9—C14—H14119.3Zn1—O6—Zn2100.66 (7)
C16—C15—C20123.3 (3)C22—O7—Zn2111.57 (17)
C16—C15—H15A118.3C24—O8—H8109 (4)
C20—C15—H15A118.3C41—O9—H9110 (4)
C15—C16—C17119.2 (3)C48—O12—H12117 (4)
C15—C16—H16120.4O6—Zn1—N1145.01 (9)
C17—C16—H16120.4O6—Zn1—O3105.16 (8)
O5—C17—C16122.9 (3)N1—Zn1—O377.87 (8)
O5—C17—C18117.4 (3)O6—Zn1—N5105.26 (8)
C16—C17—C18119.7 (3)N1—Zn1—N5108.85 (9)
C19—C18—C17121.8 (3)O3—Zn1—N597.82 (9)
C19—C18—H18119.1O6—Zn1—O279.55 (7)
C17—C18—H18119.1N1—Zn1—O286.86 (8)
O6—C19—C18120.2 (3)O3—Zn1—O2159.26 (8)
O6—C19—C20120.5 (2)N5—Zn1—O2100.37 (8)
C18—C19—C20119.3 (3)O2—Zn2—O7106.32 (7)
C15—C20—C19116.7 (3)O2—Zn2—N3137.52 (9)
C15—C20—C21118.2 (3)O7—Zn2—N377.84 (8)
C19—C20—C21125.0 (3)O2—Zn2—N6106.71 (8)
N3—C21—C20126.4 (3)O7—Zn2—N698.30 (9)
N3—C21—H21116.8N3—Zn2—N6114.57 (9)
C20—C21—H21116.8O2—Zn2—O678.81 (7)
O7—C22—N4124.9 (3)O7—Zn2—O6159.44 (8)
O7—C22—C23118.5 (3)N3—Zn2—O685.08 (8)
N4—C22—C23116.6 (3)N6—Zn2—O699.18 (8)
C28—C23—C24118.1 (3)O10i—Zn3—O11105.13 (8)
C28—C23—C22119.4 (3)O10i—Zn3—N7142.28 (9)
C24—C23—C22122.5 (3)O11—Zn3—N778.21 (8)
O8—C24—C25118.2 (4)O10i—Zn3—N9108.91 (9)
O8—C24—C23121.7 (3)O11—Zn3—N998.54 (9)
C25—C24—C23120.0 (4)N7—Zn3—N9107.63 (9)
C26—C25—C24120.5 (4)O10i—Zn3—O1078.66 (7)
C26—C25—H25119.8O11—Zn3—O10158.66 (8)
C24—C25—H25119.8N7—Zn3—O1086.15 (8)
C25—C26—C27120.8 (4)N9—Zn3—O1099.99 (9)
C25—C26—H26119.6O10i—Zn3—Zn3i40.37 (5)
C27—C26—H26119.6O11—Zn3—Zn3i141.28 (6)
C28—C27—C26118.5 (4)N7—Zn3—Zn3i117.10 (7)
C28—C27—H27120.8N9—Zn3—Zn3i108.63 (7)
C26—C27—H27120.8O10—Zn3—Zn3i38.29 (5)
C27—C28—C23122.1 (4)
C44—C39—C40—C41−0.7 (6)C30—C29—N5—Zn1−174.0 (3)
C39—C40—C41—O9−177.8 (4)C32—C33—N5—C29−1.0 (5)
C39—C40—C41—C422.8 (5)C32—C33—N5—Zn1174.4 (3)
O9—C41—C42—C43178.1 (3)C37—C38—N6—C340.3 (5)
C40—C41—C42—C43−2.5 (5)C37—C38—N6—Zn2176.8 (3)
C41—C42—C43—O10179.6 (3)C35—C34—N6—C38−0.3 (5)
C41—C42—C43—C440.1 (4)C35—C34—N6—Zn2−176.8 (3)
C40—C39—C44—C43−1.6 (5)O13—C60—N10—C59−2.1 (6)
C40—C39—C44—C45176.8 (3)O13—C60—N10—C58−178.7 (4)
O10—C43—C44—C39−177.5 (3)O14—C63—N11—C61−1.6 (9)
C42—C43—C44—C391.9 (4)O14—C63—N11—C62−177.2 (5)
O10—C43—C44—C454.2 (5)O15—C66—N12—C64−175.8 (5)
C42—C43—C44—C45−176.4 (3)O15—C66—N12—C65−0.8 (8)
C39—C44—C45—N7−175.4 (3)C4—C5—O2—Zn2−31.3 (3)
C43—C44—C45—N72.9 (5)C6—C5—O2—Zn2148.0 (2)
O11—C46—C47—C52−7.7 (4)C4—C5—O2—Zn1165.08 (18)
N8—C46—C47—C52171.6 (3)C6—C5—O2—Zn1−15.6 (3)
O11—C46—C47—C48171.0 (3)N2—C8—O3—Zn18.1 (3)
N8—C46—C47—C48−9.6 (5)C9—C8—O3—Zn1−171.20 (19)
C52—C47—C48—O12−178.6 (4)C18—C19—O6—Zn147.2 (3)
C46—C47—C48—O122.6 (6)C20—C19—O6—Zn1−132.4 (2)
C52—C47—C48—C492.8 (5)C18—C19—O6—Zn2−160.4 (2)
C46—C47—C48—C49−176.0 (3)C20—C19—O6—Zn220.1 (4)
O12—C48—C49—C50178.8 (4)N4—C22—O7—Zn2−6.8 (4)
C47—C48—C49—C50−2.5 (7)C23—C22—O7—Zn2173.0 (2)
C48—C49—C50—C510.4 (7)C19—O6—Zn1—N1−129.2 (2)
C49—C50—C51—C521.4 (7)Zn2—O6—Zn1—N172.01 (15)
C50—C51—C52—C47−1.1 (6)C19—O6—Zn1—O3−38.8 (2)
C48—C47—C52—C51−1.0 (5)Zn2—O6—Zn1—O3162.43 (8)
C46—C47—C52—C51177.8 (3)C19—O6—Zn1—N563.9 (2)
N9—C53—C54—C550.2 (7)Zn2—O6—Zn1—N5−94.86 (9)
C53—C54—C55—C56−2.2 (7)C19—O6—Zn1—O2162.0 (2)
C54—C55—C56—C572.4 (7)Zn2—O6—Zn1—O23.15 (7)
C55—C56—C57—N9−0.5 (6)C7—N1—Zn1—O6−77.5 (3)
C44—C45—N7—N8178.6 (3)N2—N1—Zn1—O6108.6 (2)
C44—C45—N7—Zn39.3 (5)C7—N1—Zn1—O3−176.7 (3)
O11—C46—N8—N70.1 (4)N2—N1—Zn1—O39.48 (17)
C47—C46—N8—N7−179.2 (2)C7—N1—Zn1—N589.1 (3)
C45—N7—N8—C46−176.8 (3)N2—N1—Zn1—N5−84.75 (18)
Zn3—N7—N8—C46−5.9 (3)C7—N1—Zn1—O2−10.8 (3)
C56—C57—N9—C53−1.5 (5)N2—N1—Zn1—O2175.36 (18)
C56—C57—N9—Zn3−172.7 (3)C8—O3—Zn1—O6−153.15 (18)
C54—C53—N9—C571.7 (5)C8—O3—Zn1—N1−9.06 (18)
C54—C53—N9—Zn3172.8 (3)C8—O3—Zn1—N598.64 (19)
C42—C43—O10—Zn3i−34.3 (4)C8—O3—Zn1—O2−52.5 (3)
C44—C43—O10—Zn3i145.2 (2)C29—N5—Zn1—O6−161.7 (2)
C42—C43—O10—Zn3158.0 (2)C33—N5—Zn1—O622.9 (3)
C44—C43—O10—Zn3−22.6 (4)C29—N5—Zn1—N126.2 (2)
N8—C46—O11—Zn35.7 (4)C33—N5—Zn1—N1−149.2 (2)
C47—C46—O11—Zn3−174.9 (2)C29—N5—Zn1—O3−53.6 (2)
C6—C1—C2—C3−1.3 (5)C33—N5—Zn1—O3131.0 (2)
C1—C2—C3—O1−177.9 (3)C29—N5—Zn1—O2116.4 (2)
C1—C2—C3—C42.9 (5)C33—N5—Zn1—O2−59.0 (2)
O1—C3—C4—C5178.7 (2)C5—O2—Zn1—O6163.7 (2)
C2—C3—C4—C5−2.2 (4)Zn2—O2—Zn1—O6−3.32 (7)
C3—C4—C5—O2179.0 (2)C5—O2—Zn1—N116.1 (2)
C3—C4—C5—C6−0.3 (4)Zn2—O2—Zn1—N1−150.93 (9)
C2—C1—C6—C5−1.1 (5)C5—O2—Zn1—O358.4 (3)
C2—C1—C6—C7177.1 (3)Zn2—O2—Zn1—O3−108.6 (2)
O2—C5—C6—C1−177.5 (3)C5—O2—Zn1—N5−92.5 (2)
C4—C5—C6—C11.9 (4)Zn2—O2—Zn1—N5100.47 (9)
O2—C5—C6—C74.5 (4)C5—O2—Zn2—O736.5 (2)
C4—C5—C6—C7−176.2 (3)Zn1—O2—Zn2—O7−156.34 (8)
C1—C6—C7—N1−177.2 (3)C5—O2—Zn2—N3126.2 (2)
C5—C6—C7—N10.8 (5)Zn1—O2—Zn2—N3−66.64 (13)
O3—C8—C9—C10169.4 (3)C5—O2—Zn2—N6−67.7 (2)
N2—C8—C9—C10−10.0 (4)Zn1—O2—Zn2—N699.47 (9)
O3—C8—C9—C14−9.9 (4)C5—O2—Zn2—O6−164.0 (2)
N2—C8—C9—C14170.8 (3)Zn1—O2—Zn2—O63.14 (7)
C14—C9—C10—O4−179.1 (3)C22—O7—Zn2—O2143.21 (19)
C8—C9—C10—O41.6 (5)C22—O7—Zn2—N36.90 (19)
C14—C9—C10—C112.0 (5)C22—O7—Zn2—N6−106.58 (19)
C8—C9—C10—C11−177.3 (3)C22—O7—Zn2—O641.4 (3)
O4—C10—C11—C12179.3 (4)C21—N3—Zn2—O280.7 (3)
C9—C10—C11—C12−1.8 (6)N4—N3—Zn2—O2−107.6 (2)
C10—C11—C12—C130.3 (6)C21—N3—Zn2—O7−178.3 (3)
C11—C12—C13—C141.0 (6)N4—N3—Zn2—O7−6.61 (18)
C12—C13—C14—C9−0.8 (6)C21—N3—Zn2—N6−84.6 (3)
C10—C9—C14—C13−0.7 (5)N4—N3—Zn2—N687.1 (2)
C8—C9—C14—C13178.5 (3)C21—N3—Zn2—O613.2 (3)
C20—C15—C16—C171.8 (6)N4—N3—Zn2—O6−175.09 (19)
C15—C16—C17—O5178.2 (3)C38—N6—Zn2—O2113.0 (2)
C15—C16—C17—C18−3.3 (5)C34—N6—Zn2—O2−70.7 (2)
O5—C17—C18—C19−179.1 (3)C38—N6—Zn2—O73.1 (2)
C16—C17—C18—C192.3 (5)C34—N6—Zn2—O7179.4 (2)
C17—C18—C19—O6−179.3 (3)C38—N6—Zn2—N3−77.3 (3)
C17—C18—C19—C200.3 (4)C34—N6—Zn2—N399.1 (2)
C16—C15—C20—C190.8 (6)C38—N6—Zn2—O6−166.0 (2)
C16—C15—C20—C21−175.7 (4)C34—N6—Zn2—O610.3 (2)
O6—C19—C20—C15177.8 (3)C19—O6—Zn2—O2−160.8 (2)
C18—C19—C20—C15−1.8 (4)Zn1—O6—Zn2—O2−3.30 (7)
O6—C19—C20—C21−6.0 (5)C19—O6—Zn2—O7−54.0 (3)
C18—C19—C20—C21174.4 (3)Zn1—O6—Zn2—O7103.4 (2)
C15—C20—C21—N3175.3 (3)C19—O6—Zn2—N3−20.3 (2)
C19—C20—C21—N3−0.9 (6)Zn1—O6—Zn2—N3137.20 (10)
O7—C22—C23—C284.3 (4)C19—O6—Zn2—N693.9 (2)
N4—C22—C23—C28−175.9 (3)Zn1—O6—Zn2—N6−108.66 (9)
O7—C22—C23—C24−174.5 (3)C46—O11—Zn3—O10i−147.80 (18)
N4—C22—C23—C245.3 (5)C46—O11—Zn3—N7−6.48 (19)
C28—C23—C24—O8179.1 (4)C46—O11—Zn3—N999.87 (19)
C22—C23—C24—O8−2.1 (6)C46—O11—Zn3—O10−50.2 (3)
C28—C23—C24—C25−2.4 (6)C46—O11—Zn3—Zn3i−125.41 (17)
C22—C23—C24—C25176.4 (4)C45—N7—Zn3—O10i−84.1 (3)
O8—C24—C25—C26−179.9 (4)N8—N7—Zn3—O10i106.4 (2)
C23—C24—C25—C261.6 (7)C45—N7—Zn3—O11176.4 (3)
C24—C25—C26—C27−0.1 (8)N8—N7—Zn3—O116.82 (18)
C25—C26—C27—C28−0.5 (7)C45—N7—Zn3—N981.0 (3)
C26—C27—C28—C23−0.4 (6)N8—N7—Zn3—N9−88.50 (19)
C24—C23—C28—C271.9 (5)C45—N7—Zn3—O10−18.2 (3)
C22—C23—C28—C27−177.0 (3)N8—N7—Zn3—O10172.22 (19)
N5—C29—C30—C31−0.6 (6)C45—N7—Zn3—Zn3i−41.6 (3)
C29—C30—C31—C32−1.1 (6)N8—N7—Zn3—Zn3i148.87 (16)
C30—C31—C32—C331.7 (6)C57—N9—Zn3—O10i−120.0 (2)
C31—C32—C33—N5−0.7 (6)C53—N9—Zn3—O10i69.3 (3)
N6—C34—C35—C36−0.1 (6)C57—N9—Zn3—O11−10.7 (3)
C34—C35—C36—C370.4 (6)C53—N9—Zn3—O11178.6 (3)
C35—C36—C37—C38−0.4 (6)C57—N9—Zn3—N769.5 (3)
C36—C37—C38—N60.0 (6)C53—N9—Zn3—N7−101.2 (3)
C6—C7—N1—N2179.2 (3)C57—N9—Zn3—O10158.7 (2)
C6—C7—N1—Zn15.5 (5)C53—N9—Zn3—O10−12.0 (3)
O3—C8—N2—N10.0 (4)C57—N9—Zn3—Zn3i−162.7 (2)
C9—C8—N2—N1179.2 (2)C53—N9—Zn3—Zn3i26.5 (3)
C7—N1—N2—C8177.1 (2)C43—O10—Zn3—O10i170.4 (3)
Zn1—N1—N2—C8−8.2 (3)Zn3i—O10—Zn3—O10i0.0
C20—C21—N3—N4−178.2 (3)C43—O10—Zn3—O1167.8 (3)
C20—C21—N3—Zn2−6.6 (5)Zn3i—O10—Zn3—O11−102.6 (2)
O7—C22—N4—N31.1 (4)C43—O10—Zn3—N725.1 (2)
C23—C22—N4—N3−178.7 (2)Zn3i—O10—Zn3—N7−145.29 (10)
C21—N3—N4—C22178.2 (3)C43—O10—Zn3—N9−82.1 (2)
Zn2—N3—N4—C225.2 (3)Zn3i—O10—Zn3—N9107.47 (9)
C30—C29—N5—C331.7 (5)C43—O10—Zn3—Zn3i170.4 (3)
Symmetry codes: (i) −x, −y+2, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N20.80 (5)1.89 (3)2.595 (3)147 (5)
O12—H12···N80.82 (3)1.94 (4)2.575 (3)134 (5)
O8—H8···N40.87 (3)1.77 (4)2.546 (3)147 (5)
Table 1
Selected geometric parameters (Å, °) top
N7—Zn32.042 (2)N6—Zn22.051 (2)
N9—Zn32.064 (2)O2—Zn21.9976 (17)
O10—Zn32.0798 (18)O2—Zn12.0859 (17)
O11—Zn32.0316 (18)O3—Zn12.0388 (18)
N1—Zn12.033 (2)O6—Zn11.9834 (18)
N3—Zn22.045 (2)O6—Zn22.1035 (17)
N5—Zn12.056 (2)O7—Zn22.0372 (18)
O6—Zn1—N1145.01 (9)O2—Zn2—N3137.52 (9)
O6—Zn1—O3105.16 (8)O7—Zn2—N377.84 (8)
N1—Zn1—O377.87 (8)O10i—Zn3—O11105.13 (8)
O6—Zn1—O279.55 (7)O10i—Zn3—N7142.28 (9)
N1—Zn1—O286.86 (8)O10i—Zn3—O1078.66 (7)
O3—Zn1—O2159.26 (8)O10i—Zn3—Zn3i40.37 (5)
O2—Zn2—O7106.32 (7)O11—Zn3—Zn3i141.28 (6)
Symmetry codes: (i) −x, −y+2, −z+2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N20.80 (5)1.89 (3)2.595 (3)147 (5)
O12—H12···N80.82 (3)1.94 (4)2.575 (3)134 (5)
O8—H8···N40.87 (3)1.77 (4)2.546 (3)147 (5)
references
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