Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024944/cf2107sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024944/cf2107Isup2.hkl |
CCDC reference: 290725
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.130
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.87 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.91 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.62 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C66 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N10 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N11 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N12
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.06 PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn2 (2) 2.02 PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn3 (2) 2.05 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
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).
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.
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].
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.
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).
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.
Fig. 1. Molecular structure of the title complex, showing labelling of the non-H atoms and 20% probability ellipsoids. |
[Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NO | F(000) = 3024 |
Mr = 975.61 | Dx = 1.439 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 8439 reflections |
a = 24.5015 (16) Å | θ = 2.2–24.1° |
b = 10.3868 (7) Å | µ = 1.13 mm−1 |
c = 28.8550 (18) Å | T = 292 K |
β = 113.127 (1)° | Block, yellow |
V = 6753.2 (8) Å3 | 0.20 × 0.16 × 0.10 mm |
Z = 6 |
Bruker SMART CCD area-detector diffractometer | 15421 independent reflections |
Radiation source: fine-focus sealed tube | 9826 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 27.5°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −31→31 |
Tmin = 0.805, Tmax = 0.895 | k = −13→13 |
45215 measured reflections | l = −37→33 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H 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 parameters | Δρmax = 0.46 e Å−3 |
8 restraints | Δρmin = −0.37 e Å−3 |
[Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NO | V = 6753.2 (8) Å3 |
Mr = 975.61 | Z = 6 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.5015 (16) Å | µ = 1.13 mm−1 |
b = 10.3868 (7) Å | T = 292 K |
c = 28.8550 (18) Å | 0.20 × 0.16 × 0.10 mm |
β = 113.127 (1)° |
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 = 0.895 | Rint = 0.042 |
45215 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 8 restraints |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.46 e Å−3 |
15421 reflections | Δρmin = −0.37 e Å−3 |
889 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C39 | −0.13981 (15) | 1.1389 (3) | 0.83565 (12) | 0.0698 (10) | |
H39 | −0.1424 | 1.1270 | 0.8029 | 0.084* | |
C40 | −0.18049 (15) | 1.2164 (3) | 0.84285 (12) | 0.0716 (10) | |
H40 | −0.2098 | 1.2571 | 0.8157 | 0.086* | |
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 | −0.1293 | 1.1915 | 0.9642 | 0.060* | |
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 | −0.0621 | 0.9880 | 0.8279 | 0.067* | |
C46 | 0.05520 (12) | 0.7705 (3) | 0.90646 (11) | 0.0465 (7) | |
C47 | 0.09223 (13) | 0.6838 (3) | 0.89027 (12) | 0.0538 (8) | |
C48 | 0.08175 (17) | 0.6626 (4) | 0.83995 (15) | 0.0757 (11) | |
C49 | 0.1161 (2) | 0.5736 (4) | 0.82740 (17) | 0.0942 (13) | |
H49 | 0.1081 | 0.5570 | 0.7937 | 0.113* | |
C50 | 0.16137 (19) | 0.5107 (4) | 0.86387 (19) | 0.0927 (14) | |
H50 | 0.1841 | 0.4519 | 0.8549 | 0.111* | |
C51 | 0.17375 (17) | 0.5333 (4) | 0.91381 (17) | 0.0871 (12) | |
H51 | 0.2052 | 0.4916 | 0.9388 | 0.105* | |
C52 | 0.13887 (15) | 0.6184 (3) | 0.92632 (14) | 0.0710 (10) | |
H52 | 0.1469 | 0.6326 | 0.9602 | 0.085* | |
C53 | −0.10147 (16) | 0.7683 (4) | 0.97847 (14) | 0.0773 (11) | |
H53 | −0.1066 | 0.8520 | 0.9874 | 0.093* | |
C54 | −0.14351 (18) | 0.6781 (5) | 0.97527 (17) | 0.0975 (14) | |
H54 | −0.1765 | 0.7007 | 0.9819 | 0.117* | |
C55 | −0.13668 (19) | 0.5562 (4) | 0.96245 (16) | 0.0903 (13) | |
H55 | −0.1640 | 0.4928 | 0.9612 | 0.108* | |
C56 | −0.08934 (19) | 0.5283 (4) | 0.95149 (15) | 0.0885 (12) | |
H56 | −0.0844 | 0.4458 | 0.9413 | 0.106* | |
C57 | −0.04889 (15) | 0.6221 (3) | 0.95547 (14) | 0.0680 (10) | |
H57 | −0.0163 | 0.6012 | 0.9481 | 0.082* | |
N7 | −0.01495 (10) | 0.9209 (2) | 0.89227 (9) | 0.0465 (6) | |
N8 | 0.01622 (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) | |
O11 | 0.06377 (8) | 0.77032 (19) | 0.95335 (7) | 0.0522 (5) | |
C1 | 0.53682 (14) | 1.1453 (3) | 0.50955 (12) | 0.0604 (9) | |
H1A | 0.5347 | 1.1337 | 0.4769 | 0.072* | |
C2 | 0.49826 (13) | 1.2285 (3) | 0.51657 (11) | 0.0568 (8) | |
H2 | 0.4711 | 1.2738 | 0.4895 | 0.068* | |
C3 | 0.50004 (12) | 1.2449 (3) | 0.56487 (11) | 0.0458 (7) | |
C4 | 0.54248 (11) | 1.1813 (3) | 0.60507 (10) | 0.0419 (6) | |
H4A | 0.5441 | 1.1954 | 0.6374 | 0.050* | |
C5 | 0.58279 (11) | 1.0970 (2) | 0.59834 (10) | 0.0377 (6) | |
C6 | 0.57988 (12) | 1.0755 (3) | 0.54859 (10) | 0.0429 (7) | |
C7 | 0.61585 (13) | 0.9864 (3) | 0.53544 (11) | 0.0490 (7) | |
H7 | 0.6098 | 0.9824 | 0.5016 | 0.059* | |
C8 | 0.72613 (12) | 0.7633 (3) | 0.57867 (12) | 0.0445 (7) | |
C9 | 0.76086 (13) | 0.6715 (3) | 0.56169 (12) | 0.0514 (8) | |
C10 | 0.74549 (16) | 0.6407 (3) | 0.51100 (14) | 0.0641 (9) | |
C11 | 0.77854 (19) | 0.5498 (4) | 0.49796 (16) | 0.0834 (12) | |
H11 | 0.7677 | 0.5275 | 0.4643 | 0.100* | |
C12 | 0.82691 (19) | 0.4927 (4) | 0.53409 (19) | 0.0898 (13) | |
H12A | 0.8487 | 0.4322 | 0.5248 | 0.108* | |
C13 | 0.84336 (16) | 0.5242 (4) | 0.58397 (17) | 0.0851 (12) | |
H13 | 0.8766 | 0.4863 | 0.6084 | 0.102* | |
C14 | 0.81059 (14) | 0.6118 (3) | 0.59757 (14) | 0.0668 (10) | |
H14 | 0.8217 | 0.6319 | 0.6315 | 0.080* | |
C15 | 0.79873 (16) | 0.8112 (4) | 0.83424 (13) | 0.0778 (11) | |
H15A | 0.7970 | 0.8095 | 0.8659 | 0.093* | |
C16 | 0.84181 (16) | 0.7417 (4) | 0.82722 (14) | 0.0776 (11) | |
H16 | 0.8681 | 0.6919 | 0.8532 | 0.093* | |
C17 | 0.84613 (13) | 0.7458 (3) | 0.78087 (13) | 0.0593 (9) | |
C18 | 0.80483 (12) | 0.8150 (3) | 0.74174 (11) | 0.0506 (7) | |
H18 | 0.8072 | 0.8146 | 0.7104 | 0.061* | |
C19 | 0.76020 (12) | 0.8844 (3) | 0.74804 (11) | 0.0431 (7) | |
C20 | 0.75654 (13) | 0.8857 (3) | 0.79604 (11) | 0.0538 (8) | |
C21 | 0.71601 (14) | 0.9616 (3) | 0.80886 (11) | 0.0609 (9) | |
H21 | 0.7176 | 0.9529 | 0.8415 | 0.073* | |
C22 | 0.60709 (12) | 1.1883 (3) | 0.76932 (11) | 0.0453 (7) | |
C23 | 0.56973 (13) | 1.2669 (3) | 0.78813 (12) | 0.0547 (8) | |
C24 | 0.57610 (17) | 1.2643 (4) | 0.83837 (15) | 0.0786 (11) | |
C25 | 0.5423 (2) | 1.3450 (5) | 0.85447 (17) | 0.1076 (16) | |
H25 | 0.5474 | 1.3445 | 0.8881 | 0.129* | |
C26 | 0.5015 (2) | 1.4254 (5) | 0.8213 (2) | 0.1072 (17) | |
H26 | 0.4789 | 1.4791 | 0.8326 | 0.129* | |
C27 | 0.49319 (19) | 1.4278 (4) | 0.7711 (2) | 0.0972 (15) | |
H27 | 0.4651 | 1.4821 | 0.7484 | 0.117* | |
C28 | 0.52743 (15) | 1.3481 (3) | 0.75535 (15) | 0.0718 (10) | |
H28 | 0.5219 | 1.3488 | 0.7216 | 0.086* | |
C29 | 0.60496 (14) | 0.6467 (3) | 0.61160 (12) | 0.0590 (8) | |
H29 | 0.6175 | 0.6513 | 0.5851 | 0.071* | |
C30 | 0.56612 (17) | 0.5516 (4) | 0.61068 (14) | 0.0794 (11) | |
H30 | 0.5524 | 0.4937 | 0.5840 | 0.095* | |
C31 | 0.54776 (17) | 0.5426 (4) | 0.64922 (15) | 0.0826 (12) | |
H31 | 0.5208 | 0.4796 | 0.6492 | 0.099* | |
C32 | 0.56997 (17) | 0.6286 (4) | 0.68808 (14) | 0.0822 (12) | |
H32 | 0.5590 | 0.6233 | 0.7154 | 0.099* | |
C33 | 0.60830 (14) | 0.7221 (3) | 0.68643 (12) | 0.0630 (9) | |
H33 | 0.6228 | 0.7805 | 0.7129 | 0.076* | |
C34 | 0.76581 (14) | 1.2361 (3) | 0.69807 (12) | 0.0622 (9) | |
H34 | 0.7751 | 1.1533 | 0.6913 | 0.075* | |
C35 | 0.80319 (17) | 1.3359 (4) | 0.69887 (15) | 0.0842 (12) | |
H35 | 0.8371 | 1.3202 | 0.6928 | 0.101* | |
C36 | 0.79015 (19) | 1.4575 (4) | 0.70864 (15) | 0.0866 (12) | |
H36 | 0.8147 | 1.5262 | 0.7091 | 0.104* | |
C37 | 0.74053 (19) | 1.4763 (4) | 0.71765 (15) | 0.0882 (12) | |
H37 | 0.7307 | 1.5584 | 0.7246 | 0.106* | |
C38 | 0.70497 (15) | 1.3735 (3) | 0.71641 (13) | 0.0666 (9) | |
H38 | 0.6710 | 1.3879 | 0.7227 | 0.080* | |
C58 | 0.69475 (18) | 0.2615 (4) | 0.49964 (16) | 0.0981 (14) | |
H58A | 0.7361 | 0.2826 | 0.5113 | 0.147* | |
H58B | 0.6775 | 0.2619 | 0.4635 | 0.147* | |
H58C | 0.6904 | 0.1776 | 0.5117 | 0.147* | |
C59 | 0.68097 (18) | 0.3602 (4) | 0.57223 (14) | 0.0984 (14) | |
H59A | 0.6457 | 0.3637 | 0.5791 | 0.148* | |
H59B | 0.7048 | 0.4352 | 0.5860 | 0.148* | |
H59C | 0.7032 | 0.2844 | 0.5873 | 0.148* | |
C60 | 0.62674 (15) | 0.4399 (4) | 0.48899 (13) | 0.0661 (9) | |
H60 | 0.6189 | 0.4349 | 0.4548 | 0.079* | |
C61 | 0.6792 (2) | 0.5286 (5) | 0.90595 (19) | 0.1362 (19) | |
H61A | 0.7166 | 0.5631 | 0.9285 | 0.204* | |
H61B | 0.6834 | 0.4381 | 0.9014 | 0.204* | |
H61C | 0.6500 | 0.5417 | 0.9200 | 0.204* | |
C62 | 0.6224 (2) | 0.7033 (5) | 0.8490 (2) | 0.146 (2) | |
H62A | 0.6108 | 0.7308 | 0.8147 | 0.219* | |
H62B | 0.6432 | 0.7719 | 0.8713 | 0.219* | |
H62C | 0.5878 | 0.6808 | 0.8550 | 0.219* | |
C63 | 0.6769 (2) | 0.5424 (6) | 0.82513 (19) | 0.1182 (18) | |
H63 | 0.6635 | 0.5845 | 0.7942 | 0.142* | |
C64 | 0.0345 (2) | 0.2513 (5) | 0.82233 (19) | 0.1297 (19) | |
H64A | 0.0745 | 0.2781 | 0.8294 | 0.195* | |
H64B | 0.0126 | 0.2478 | 0.7865 | 0.195* | |
H64C | 0.0349 | 0.1676 | 0.8366 | 0.195* | |
C65 | 0.0269 (2) | 0.3277 (5) | 0.89926 (18) | 0.145 (2) | |
H65A | 0.0108 | 0.3965 | 0.9123 | 0.217* | |
H65B | 0.0694 | 0.3307 | 0.9146 | 0.217* | |
H65C | 0.0133 | 0.2467 | 0.9068 | 0.217* | |
C66 | −0.0273 (2) | 0.4296 (5) | 0.8205 (2) | 0.124 (2) | |
H66 | −0.0382 | 0.4350 | 0.7859 | 0.149* | |
N1 | 0.65551 (10) | 0.9115 (2) | 0.56540 (9) | 0.0430 (5) | |
N2 | 0.68481 (10) | 0.8309 (2) | 0.54383 (9) | 0.0501 (6) | |
N3 | 0.67750 (10) | 1.0409 (2) | 0.77984 (8) | 0.0461 (6) | |
N4 | 0.64395 (11) | 1.1071 (2) | 0.80141 (9) | 0.0539 (7) | |
N5 | 0.62581 (9) | 0.7330 (2) | 0.64829 (9) | 0.0439 (6) | |
N6 | 0.71668 (10) | 1.2541 (2) | 0.70666 (8) | 0.0449 (6) | |
N10 | 0.66478 (12) | 0.3565 (3) | 0.51865 (11) | 0.0645 (7) | |
N11 | 0.66080 (16) | 0.5928 (4) | 0.85816 (14) | 0.0903 (10) | |
N12 | 0.00686 (15) | 0.3419 (4) | 0.84401 (14) | 0.0911 (10) | |
O1 | 0.46196 (9) | 1.3230 (2) | 0.57503 (8) | 0.0603 (6) | |
H1 | 0.4395 (14) | 1.354 (4) | 0.5493 (11) | 0.090* | |
O2 | 0.62409 (7) | 1.03809 (17) | 0.63830 (6) | 0.0414 (4) | |
O3 | 0.73819 (8) | 0.77002 (19) | 0.62614 (7) | 0.0532 (5) | |
O4 | 0.69857 (14) | 0.6951 (3) | 0.47371 (10) | 0.0908 (9) | |
H4 | 0.6820 (19) | 0.742 (4) | 0.4860 (16) | 0.136* | |
O5 | 0.88845 (10) | 0.6825 (3) | 0.77117 (10) | 0.0828 (8) | |
H5 | 0.9114 (16) | 0.639 (4) | 0.7946 (13) | 0.124* | |
O6 | 0.72031 (8) | 0.94960 (17) | 0.70896 (7) | 0.0433 (4) | |
O7 | 0.60160 (8) | 1.20387 (19) | 0.72382 (7) | 0.0511 (5) | |
O8 | 0.61562 (15) | 1.1868 (4) | 0.87241 (10) | 0.1209 (12) | |
H8 | 0.631 (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* | |
O12 | 0.03810 (15) | 0.7243 (4) | 0.80240 (11) | 0.1214 (13) | |
H12 | 0.024 (2) | 0.788 (4) | 0.810 (2) | 0.182* | |
O13 | 0.60078 (11) | 0.5232 (2) | 0.50210 (9) | 0.0738 (7) | |
O14 | 0.70709 (14) | 0.4477 (3) | 0.82828 (11) | 0.1173 (11) | |
O15 | −0.04849 (13) | 0.5139 (3) | 0.84213 (12) | 0.1122 (11) | |
Zn1 | 0.677430 (13) | 0.88007 (3) | 0.640099 (12) | 0.03916 (10) | |
Zn2 | 0.664039 (13) | 1.10261 (3) | 0.708892 (12) | 0.04011 (10) | |
Zn3 | 0.003714 (13) | 0.88356 (3) | 0.966433 (11) | 0.04081 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C39 | 0.078 (2) | 0.078 (3) | 0.0405 (19) | 0.025 (2) | 0.0094 (17) | 0.0031 (17) |
C40 | 0.069 (2) | 0.074 (3) | 0.046 (2) | 0.0267 (19) | −0.0050 (17) | 0.0024 (18) |
C41 | 0.0477 (18) | 0.053 (2) | 0.056 (2) | 0.0091 (15) | 0.0060 (15) | −0.0066 (16) |
C42 | 0.0517 (17) | 0.0462 (18) | 0.0450 (18) | 0.0069 (14) | 0.0118 (14) | 0.0010 (14) |
C43 | 0.0438 (16) | 0.0358 (16) | 0.0390 (16) | −0.0019 (12) | 0.0065 (13) | 0.0002 (12) |
C44 | 0.0525 (18) | 0.0536 (19) | 0.0381 (17) | 0.0060 (15) | 0.0081 (14) | 0.0013 (14) |
C45 | 0.059 (2) | 0.064 (2) | 0.0388 (18) | 0.0065 (16) | 0.0145 (15) | 0.0012 (15) |
C46 | 0.0431 (16) | 0.0508 (19) | 0.0489 (19) | −0.0057 (14) | 0.0217 (14) | −0.0049 (15) |
C47 | 0.0515 (18) | 0.056 (2) | 0.061 (2) | −0.0023 (15) | 0.0298 (16) | −0.0071 (16) |
C48 | 0.078 (3) | 0.092 (3) | 0.069 (3) | 0.011 (2) | 0.041 (2) | −0.009 (2) |
C49 | 0.106 (3) | 0.113 (4) | 0.084 (3) | 0.016 (3) | 0.060 (3) | −0.018 (3) |
C50 | 0.094 (3) | 0.085 (3) | 0.123 (4) | 0.019 (2) | 0.068 (3) | −0.014 (3) |
C51 | 0.082 (3) | 0.077 (3) | 0.107 (4) | 0.028 (2) | 0.043 (3) | −0.001 (2) |
C52 | 0.069 (2) | 0.075 (3) | 0.073 (3) | 0.0154 (19) | 0.034 (2) | −0.0070 (19) |
C53 | 0.084 (3) | 0.064 (2) | 0.106 (3) | −0.008 (2) | 0.061 (2) | −0.004 (2) |
C54 | 0.087 (3) | 0.094 (3) | 0.138 (4) | −0.017 (3) | 0.073 (3) | 0.002 (3) |
C55 | 0.089 (3) | 0.077 (3) | 0.103 (3) | −0.030 (2) | 0.036 (3) | 0.014 (3) |
C56 | 0.100 (3) | 0.053 (2) | 0.115 (4) | −0.018 (2) | 0.045 (3) | −0.003 (2) |
C57 | 0.069 (2) | 0.047 (2) | 0.090 (3) | −0.0024 (17) | 0.033 (2) | −0.0021 (18) |
N7 | 0.0459 (14) | 0.0533 (16) | 0.0402 (14) | 0.0043 (12) | 0.0170 (11) | 0.0018 (11) |
N8 | 0.0542 (15) | 0.0627 (17) | 0.0439 (15) | 0.0068 (13) | 0.0231 (12) | −0.0006 (13) |
N9 | 0.0519 (15) | 0.0430 (15) | 0.0475 (15) | 0.0005 (11) | 0.0194 (12) | 0.0043 (11) |
O10 | 0.0495 (11) | 0.0439 (12) | 0.0356 (11) | 0.0111 (9) | 0.0061 (9) | −0.0006 (9) |
O11 | 0.0513 (12) | 0.0610 (14) | 0.0449 (12) | 0.0116 (10) | 0.0194 (10) | −0.0014 (10) |
C1 | 0.072 (2) | 0.065 (2) | 0.0403 (19) | 0.0176 (18) | 0.0169 (16) | 0.0099 (15) |
C2 | 0.060 (2) | 0.054 (2) | 0.0438 (19) | 0.0164 (16) | 0.0065 (15) | 0.0118 (15) |
C3 | 0.0413 (16) | 0.0352 (16) | 0.053 (2) | 0.0025 (13) | 0.0103 (14) | 0.0017 (13) |
C4 | 0.0441 (16) | 0.0389 (16) | 0.0393 (16) | 0.0009 (13) | 0.0127 (13) | 0.0016 (12) |
C5 | 0.0372 (14) | 0.0325 (15) | 0.0386 (16) | −0.0024 (12) | 0.0098 (12) | 0.0035 (12) |
C6 | 0.0458 (16) | 0.0429 (17) | 0.0382 (16) | 0.0038 (13) | 0.0144 (13) | 0.0019 (13) |
C7 | 0.0606 (19) | 0.0505 (19) | 0.0377 (17) | 0.0024 (15) | 0.0212 (14) | 0.0018 (14) |
C8 | 0.0426 (16) | 0.0444 (17) | 0.0528 (19) | −0.0047 (13) | 0.0253 (15) | −0.0027 (14) |
C9 | 0.0582 (19) | 0.0411 (17) | 0.068 (2) | −0.0009 (14) | 0.0394 (17) | −0.0036 (15) |
C10 | 0.083 (2) | 0.057 (2) | 0.069 (3) | 0.0070 (18) | 0.048 (2) | 0.0037 (18) |
C11 | 0.112 (3) | 0.073 (3) | 0.094 (3) | 0.013 (2) | 0.071 (3) | −0.007 (2) |
C12 | 0.100 (3) | 0.070 (3) | 0.131 (4) | 0.022 (2) | 0.080 (3) | −0.002 (3) |
C13 | 0.071 (2) | 0.073 (3) | 0.119 (4) | 0.026 (2) | 0.046 (2) | −0.004 (2) |
C14 | 0.0539 (19) | 0.065 (2) | 0.085 (3) | 0.0096 (17) | 0.0322 (19) | −0.0060 (19) |
C15 | 0.088 (3) | 0.088 (3) | 0.047 (2) | 0.038 (2) | 0.0156 (19) | 0.0174 (19) |
C16 | 0.075 (2) | 0.076 (3) | 0.060 (2) | 0.033 (2) | 0.0018 (19) | 0.0125 (19) |
C17 | 0.0439 (18) | 0.053 (2) | 0.062 (2) | 0.0103 (15) | 0.0012 (16) | −0.0030 (16) |
C18 | 0.0464 (17) | 0.0456 (18) | 0.0511 (19) | 0.0068 (14) | 0.0098 (14) | −0.0001 (14) |
C19 | 0.0404 (15) | 0.0342 (16) | 0.0433 (17) | −0.0003 (12) | 0.0043 (13) | −0.0012 (13) |
C20 | 0.0540 (18) | 0.056 (2) | 0.0410 (18) | 0.0122 (15) | 0.0072 (14) | 0.0077 (15) |
C21 | 0.070 (2) | 0.073 (2) | 0.0372 (18) | 0.0171 (18) | 0.0182 (16) | 0.0092 (16) |
C22 | 0.0432 (16) | 0.0481 (18) | 0.0450 (18) | −0.0017 (13) | 0.0178 (14) | −0.0061 (14) |
C23 | 0.0546 (19) | 0.056 (2) | 0.060 (2) | −0.0039 (15) | 0.0286 (16) | −0.0128 (16) |
C24 | 0.072 (2) | 0.104 (3) | 0.064 (3) | 0.007 (2) | 0.031 (2) | −0.023 (2) |
C25 | 0.095 (3) | 0.155 (5) | 0.086 (3) | 0.008 (3) | 0.049 (3) | −0.051 (3) |
C26 | 0.092 (3) | 0.098 (4) | 0.158 (5) | −0.001 (3) | 0.077 (4) | −0.050 (3) |
C27 | 0.095 (3) | 0.072 (3) | 0.150 (5) | 0.025 (2) | 0.075 (3) | 0.005 (3) |
C28 | 0.071 (2) | 0.061 (2) | 0.097 (3) | 0.0165 (19) | 0.048 (2) | 0.010 (2) |
C29 | 0.075 (2) | 0.054 (2) | 0.048 (2) | −0.0143 (17) | 0.0242 (17) | −0.0028 (16) |
C30 | 0.102 (3) | 0.068 (3) | 0.065 (3) | −0.037 (2) | 0.030 (2) | −0.0117 (19) |
C31 | 0.093 (3) | 0.075 (3) | 0.083 (3) | −0.039 (2) | 0.037 (2) | 0.000 (2) |
C32 | 0.097 (3) | 0.093 (3) | 0.073 (3) | −0.026 (2) | 0.052 (2) | 0.001 (2) |
C33 | 0.070 (2) | 0.067 (2) | 0.059 (2) | −0.0104 (18) | 0.0332 (18) | −0.0059 (17) |
C34 | 0.066 (2) | 0.056 (2) | 0.071 (2) | −0.0017 (17) | 0.0347 (19) | 0.0000 (17) |
C35 | 0.074 (3) | 0.085 (3) | 0.106 (3) | −0.016 (2) | 0.049 (2) | 0.000 (2) |
C36 | 0.097 (3) | 0.064 (3) | 0.100 (3) | −0.032 (2) | 0.040 (3) | −0.004 (2) |
C37 | 0.101 (3) | 0.051 (2) | 0.112 (4) | −0.012 (2) | 0.041 (3) | −0.007 (2) |
C38 | 0.071 (2) | 0.048 (2) | 0.079 (3) | −0.0020 (17) | 0.0283 (19) | −0.0031 (17) |
C58 | 0.094 (3) | 0.076 (3) | 0.118 (4) | 0.025 (2) | 0.035 (3) | 0.010 (3) |
C59 | 0.112 (3) | 0.093 (3) | 0.058 (3) | −0.005 (3) | −0.001 (2) | 0.019 (2) |
C60 | 0.076 (2) | 0.068 (2) | 0.046 (2) | 0.010 (2) | 0.0149 (18) | 0.0052 (18) |
C61 | 0.171 (5) | 0.119 (5) | 0.125 (5) | 0.002 (4) | 0.066 (4) | −0.005 (4) |
C62 | 0.142 (5) | 0.111 (4) | 0.144 (5) | 0.058 (4) | 0.011 (4) | −0.018 (4) |
C63 | 0.115 (4) | 0.139 (5) | 0.077 (4) | 0.042 (4) | 0.012 (3) | 0.024 (3) |
C64 | 0.133 (4) | 0.123 (4) | 0.119 (4) | 0.038 (4) | 0.034 (3) | −0.009 (3) |
C65 | 0.166 (5) | 0.143 (5) | 0.091 (4) | −0.009 (4) | 0.013 (4) | 0.008 (3) |
C66 | 0.089 (3) | 0.101 (4) | 0.145 (5) | 0.031 (3) | 0.006 (3) | 0.042 (4) |
N1 | 0.0468 (13) | 0.0421 (14) | 0.0449 (14) | 0.0029 (11) | 0.0232 (11) | 0.0018 (11) |
N2 | 0.0594 (15) | 0.0505 (16) | 0.0481 (16) | 0.0091 (12) | 0.0295 (13) | 0.0003 (12) |
N3 | 0.0466 (14) | 0.0521 (15) | 0.0382 (14) | 0.0085 (12) | 0.0150 (11) | 0.0024 (11) |
N4 | 0.0570 (15) | 0.0653 (18) | 0.0401 (15) | 0.0127 (13) | 0.0200 (12) | −0.0004 (13) |
N5 | 0.0471 (14) | 0.0404 (14) | 0.0437 (15) | −0.0006 (11) | 0.0170 (11) | 0.0027 (11) |
N6 | 0.0482 (14) | 0.0399 (14) | 0.0420 (14) | −0.0011 (11) | 0.0128 (11) | 0.0012 (11) |
N10 | 0.0677 (18) | 0.0538 (18) | 0.0618 (19) | 0.0052 (14) | 0.0144 (15) | 0.0086 (14) |
N11 | 0.098 (3) | 0.095 (3) | 0.066 (2) | 0.011 (2) | 0.021 (2) | −0.008 (2) |
N12 | 0.086 (2) | 0.096 (3) | 0.077 (3) | 0.005 (2) | 0.016 (2) | −0.011 (2) |
O1 | 0.0512 (13) | 0.0585 (15) | 0.0624 (16) | 0.0203 (11) | 0.0130 (11) | 0.0047 (12) |
O2 | 0.0432 (10) | 0.0404 (11) | 0.0338 (11) | 0.0093 (8) | 0.0079 (8) | −0.0003 (8) |
O3 | 0.0485 (12) | 0.0605 (14) | 0.0508 (13) | 0.0150 (10) | 0.0198 (10) | −0.0031 (10) |
O4 | 0.122 (2) | 0.100 (2) | 0.0624 (18) | 0.0381 (18) | 0.0494 (16) | 0.0043 (15) |
O5 | 0.0574 (15) | 0.087 (2) | 0.087 (2) | 0.0349 (13) | 0.0100 (14) | 0.0024 (15) |
O6 | 0.0454 (11) | 0.0380 (11) | 0.0386 (11) | 0.0100 (9) | 0.0081 (9) | 0.0008 (8) |
O7 | 0.0523 (12) | 0.0583 (13) | 0.0440 (13) | 0.0140 (10) | 0.0205 (10) | 0.0033 (10) |
O8 | 0.126 (3) | 0.192 (4) | 0.0504 (18) | 0.060 (2) | 0.0415 (17) | 0.005 (2) |
O9 | 0.0729 (18) | 0.090 (2) | 0.0721 (19) | 0.0392 (15) | 0.0107 (14) | −0.0042 (15) |
O12 | 0.126 (3) | 0.185 (4) | 0.0566 (18) | 0.073 (2) | 0.0401 (17) | 0.004 (2) |
O13 | 0.0861 (17) | 0.0692 (17) | 0.0656 (16) | 0.0234 (14) | 0.0293 (13) | 0.0055 (13) |
O14 | 0.115 (2) | 0.134 (3) | 0.090 (2) | 0.061 (2) | 0.0260 (18) | 0.020 (2) |
O15 | 0.095 (2) | 0.101 (3) | 0.137 (3) | 0.0457 (19) | 0.042 (2) | 0.028 (2) |
Zn1 | 0.04099 (18) | 0.03685 (19) | 0.0397 (2) | 0.00210 (14) | 0.01589 (14) | −0.00053 (14) |
Zn2 | 0.04315 (18) | 0.03859 (19) | 0.03748 (19) | 0.00409 (14) | 0.01463 (14) | 0.00014 (14) |
Zn3 | 0.04396 (19) | 0.0392 (2) | 0.03812 (19) | 0.00194 (14) | 0.01485 (14) | −0.00090 (14) |
C39—C40 | 1.359 (4) | C22—N4 | 1.315 (4) |
C39—C44 | 1.401 (4) | C22—C23 | 1.480 (4) |
C39—H39 | 0.930 | C23—C28 | 1.382 (4) |
C40—C41 | 1.384 (4) | C23—C24 | 1.396 (4) |
C40—H40 | 0.930 | C24—O8 | 1.343 (5) |
C41—O9 | 1.354 (4) | C24—C25 | 1.380 (5) |
C41—C42 | 1.389 (4) | C25—C26 | 1.364 (6) |
C42—C43 | 1.376 (4) | C25—H25 | 0.930 |
C42—H42 | 0.930 | C26—C27 | 1.383 (6) |
C43—O10 | 1.339 (3) | C26—H26 | 0.930 |
C43—C44 | 1.422 (4) | C27—C28 | 1.376 (5) |
C44—C45 | 1.436 (4) | C27—H27 | 0.930 |
C45—N7 | 1.280 (3) | C28—H28 | 0.930 |
C45—H45 | 0.930 | C29—N5 | 1.327 (4) |
C46—O11 | 1.285 (3) | C29—C30 | 1.364 (4) |
C46—N8 | 1.319 (4) | C29—H29 | 0.930 |
C46—C47 | 1.478 (4) | C30—C31 | 1.357 (5) |
C47—C52 | 1.384 (4) | C30—H30 | 0.930 |
C47—C48 | 1.389 (4) | C31—C32 | 1.368 (5) |
C48—O12 | 1.348 (5) | C31—H31 | 0.930 |
C48—C49 | 1.391 (5) | C32—C33 | 1.365 (4) |
C49—C50 | 1.359 (6) | C32—H32 | 0.930 |
C49—H49 | 0.930 | C33—N5 | 1.334 (3) |
C50—C51 | 1.371 (5) | C33—H33 | 0.930 |
C50—H50 | 0.930 | C34—N6 | 1.334 (3) |
C51—C52 | 1.373 (4) | C34—C35 | 1.378 (4) |
C51—H51 | 0.930 | C34—H34 | 0.930 |
C52—H52 | 0.930 | C35—C36 | 1.359 (5) |
C53—N9 | 1.326 (4) | C35—H35 | 0.930 |
C53—C54 | 1.368 (5) | C36—C37 | 1.354 (5) |
C53—H53 | 0.930 | C36—H36 | 0.930 |
C54—C55 | 1.348 (6) | C37—C38 | 1.370 (5) |
C54—H54 | 0.930 | C37—H37 | 0.930 |
C55—C56 | 1.348 (5) | C38—N6 | 1.328 (4) |
C55—H55 | 0.930 | C38—H38 | 0.930 |
C56—C57 | 1.362 (5) | C58—N10 | 1.459 (4) |
C56—H56 | 0.930 | C58—H58A | 0.960 |
C57—N9 | 1.322 (4) | C58—H58B | 0.960 |
C57—H57 | 0.930 | C58—H58C | 0.960 |
N7—N8 | 1.398 (3) | C59—N10 | 1.438 (4) |
N7—Zn3 | 2.042 (2) | C59—H59A | 0.960 |
N9—Zn3 | 2.064 (2) | C59—H59B | 0.960 |
O10—Zn3i | 1.9900 (18) | C59—H59C | 0.960 |
O10—Zn3 | 2.0798 (18) | C60—O13 | 1.219 (4) |
O11—Zn3 | 2.0316 (18) | C60—N10 | 1.313 (4) |
C1—C2 | 1.353 (4) | C60—H60 | 0.930 |
C1—C6 | 1.405 (4) | C61—N11 | 1.435 (5) |
C1—H1A | 0.930 | C61—H61A | 0.960 |
C2—C3 | 1.388 (4) | C61—H61B | 0.960 |
C2—H2 | 0.930 | C61—H61C | 0.960 |
C3—O1 | 1.353 (3) | C62—N11 | 1.441 (5) |
C3—C4 | 1.384 (4) | C62—H62A | 0.960 |
C4—C5 | 1.390 (3) | C62—H62B | 0.960 |
C4—H4A | 0.930 | C62—H62C | 0.960 |
C5—O2 | 1.346 (3) | C63—O14 | 1.213 (5) |
C5—C6 | 1.427 (4) | C63—N11 | 1.278 (5) |
C6—C7 | 1.428 (4) | C63—H63 | 0.930 |
C7—N1 | 1.279 (3) | C64—N12 | 1.439 (5) |
C7—H7 | 0.930 | C64—H64A | 0.960 |
C8—O3 | 1.285 (3) | C64—H64B | 0.960 |
C8—N2 | 1.315 (4) | C64—H64C | 0.960 |
C8—C9 | 1.483 (4) | C65—N12 | 1.480 (5) |
C9—C10 | 1.397 (4) | C65—H65A | 0.960 |
C9—C14 | 1.397 (4) | C65—H65B | 0.960 |
C10—O4 | 1.351 (4) | C65—H65C | 0.960 |
C10—C11 | 1.389 (4) | C66—N12 | 1.243 (5) |
C11—C12 | 1.368 (5) | C66—O15 | 1.296 (6) |
C11—H11 | 0.930 | C66—H66 | 0.930 |
C12—C13 | 1.373 (5) | N1—N2 | 1.398 (3) |
C12—H12A | 0.930 | N1—Zn1 | 2.033 (2) |
C13—C14 | 1.369 (4) | N3—N4 | 1.392 (3) |
C13—H13 | 0.930 | N3—Zn2 | 2.045 (2) |
C14—H14 | 0.930 | N5—Zn1 | 2.056 (2) |
C15—C16 | 1.358 (4) | N6—Zn2 | 2.051 (2) |
C15—C20 | 1.410 (4) | O1—H1 | 0.80 (2) |
C15—H15A | 0.930 | O2—Zn2 | 1.9976 (17) |
C16—C17 | 1.383 (5) | O2—Zn1 | 2.0859 (17) |
C16—H16 | 0.930 | O3—Zn1 | 2.0388 (18) |
C17—O5 | 1.346 (4) | O4—H4 | 0.80 (5) |
C17—C18 | 1.385 (4) | O5—H5 | 0.82 (5) |
C18—C19 | 1.380 (4) | O6—Zn1 | 1.9834 (18) |
C18—H18 | 0.930 | O6—Zn2 | 2.1035 (17) |
C19—O6 | 1.349 (3) | O7—Zn2 | 2.0372 (18) |
C19—C20 | 1.423 (4) | O8—H8 | 0.87 (3) |
C20—C21 | 1.426 (4) | O9—H9 | 0.73 (3) |
C21—N3 | 1.284 (4) | O12—H12 | 0.82 (3) |
C21—H21 | 0.930 | Zn3—O10i | 1.9900 (18) |
C22—O7 | 1.276 (3) | Zn3—Zn3i | 3.1486 (6) |
C40—C39—C44 | 123.5 (3) | C27—C28—H28 | 118.9 |
C40—C39—H39 | 118.2 | C23—C28—H28 | 118.9 |
C44—C39—H39 | 118.2 | N5—C29—C30 | 123.5 (3) |
C39—C40—C41 | 118.6 (3) | N5—C29—H29 | 118.3 |
C39—C40—H40 | 120.7 | C30—C29—H29 | 118.3 |
C41—C40—H40 | 120.7 | C31—C30—C29 | 119.1 (3) |
O9—C41—C40 | 123.3 (3) | C31—C30—H30 | 120.4 |
O9—C41—C42 | 116.8 (3) | C29—C30—H30 | 120.4 |
C40—C41—C42 | 119.9 (3) | C30—C31—C32 | 118.3 (3) |
C43—C42—C41 | 121.8 (3) | C30—C31—H31 | 120.9 |
C43—C42—H42 | 119.1 | C32—C31—H31 | 120.9 |
C41—C42—H42 | 119.1 | C33—C32—C31 | 119.6 (3) |
O10—C43—C42 | 120.0 (3) | C33—C32—H32 | 120.2 |
O10—C43—C44 | 121.2 (3) | C31—C32—H32 | 120.2 |
C42—C43—C44 | 118.9 (3) | N5—C33—C32 | 122.5 (3) |
C39—C44—C43 | 117.2 (3) | N5—C33—H33 | 118.7 |
C39—C44—C45 | 117.7 (3) | C32—C33—H33 | 118.7 |
C43—C44—C45 | 125.1 (3) | N6—C34—C35 | 122.3 (3) |
N7—C45—C44 | 125.9 (3) | N6—C34—H34 | 118.9 |
N7—C45—H45 | 117.0 | C35—C34—H34 | 118.9 |
C44—C45—H45 | 117.0 | C36—C35—C34 | 119.6 (4) |
O11—C46—N8 | 125.1 (3) | C36—C35—H35 | 120.2 |
O11—C46—C47 | 117.7 (3) | C34—C35—H35 | 120.2 |
N8—C46—C47 | 117.2 (3) | C37—C36—C35 | 118.4 (4) |
C52—C47—C48 | 117.8 (3) | C37—C36—H36 | 120.8 |
C52—C47—C46 | 119.3 (3) | C35—C36—H36 | 120.8 |
C48—C47—C46 | 122.9 (3) | C36—C37—C38 | 119.5 (4) |
O12—C48—C47 | 121.8 (3) | C36—C37—H37 | 120.3 |
O12—C48—C49 | 118.5 (4) | C38—C37—H37 | 120.3 |
C47—C48—C49 | 119.7 (4) | N6—C38—C37 | 123.1 (3) |
C50—C49—C48 | 120.7 (4) | N6—C38—H38 | 118.5 |
C50—C49—H49 | 119.6 | C37—C38—H38 | 118.5 |
C48—C49—H49 | 119.6 | N10—C58—H58A | 109.5 |
C49—C50—C51 | 120.6 (4) | N10—C58—H58B | 109.5 |
C49—C50—H50 | 119.7 | H58A—C58—H58B | 109.5 |
C51—C50—H50 | 119.7 | N10—C58—H58C | 109.5 |
C50—C51—C52 | 118.9 (4) | H58A—C58—H58C | 109.5 |
C50—C51—H51 | 120.6 | H58B—C58—H58C | 109.5 |
C52—C51—H51 | 120.6 | N10—C59—H59A | 109.5 |
C51—C52—C47 | 122.3 (4) | N10—C59—H59B | 109.5 |
C51—C52—H52 | 118.9 | H59A—C59—H59B | 109.5 |
C47—C52—H52 | 118.9 | N10—C59—H59C | 109.5 |
N9—C53—C54 | 122.8 (4) | H59A—C59—H59C | 109.5 |
N9—C53—H53 | 118.6 | H59B—C59—H59C | 109.5 |
C54—C53—H53 | 118.6 | O13—C60—N10 | 126.1 (3) |
C55—C54—C53 | 119.4 (4) | O13—C60—H60 | 116.9 |
C55—C54—H54 | 120.3 | N10—C60—H60 | 116.9 |
C53—C54—H54 | 120.3 | N11—C61—H61A | 109.5 |
C54—C55—C56 | 118.5 (4) | N11—C61—H61B | 109.5 |
C54—C55—H55 | 120.7 | H61A—C61—H61B | 109.5 |
C56—C55—H55 | 120.7 | N11—C61—H61C | 109.5 |
C55—C56—C57 | 119.4 (4) | H61A—C61—H61C | 109.5 |
C55—C56—H56 | 120.3 | H61B—C61—H61C | 109.5 |
C57—C56—H56 | 120.3 | N11—C62—H62A | 109.5 |
N9—C57—C56 | 123.2 (3) | N11—C62—H62B | 109.5 |
N9—C57—H57 | 118.4 | H62A—C62—H62B | 109.5 |
C56—C57—H57 | 118.4 | N11—C62—H62C | 109.5 |
C45—N7—N8 | 117.0 (2) | H62A—C62—H62C | 109.5 |
C45—N7—Zn3 | 128.5 (2) | H62B—C62—H62C | 109.5 |
N8—N7—Zn3 | 113.79 (17) | O14—C63—N11 | 129.3 (5) |
C46—N8—N7 | 110.9 (2) | O14—C63—H63 | 115.3 |
C57—N9—C53 | 116.6 (3) | N11—C63—H63 | 115.3 |
C57—N9—Zn3 | 121.0 (2) | N12—C64—H64A | 109.5 |
C53—N9—Zn3 | 121.8 (2) | N12—C64—H64B | 109.5 |
C43—O10—Zn3i | 129.77 (17) | H64A—C64—H64B | 109.5 |
C43—O10—Zn3 | 128.08 (17) | N12—C64—H64C | 109.5 |
Zn3i—O10—Zn3 | 101.34 (7) | H64A—C64—H64C | 109.5 |
C46—O11—Zn3 | 111.35 (17) | H64B—C64—H64C | 109.5 |
C2—C1—C6 | 123.9 (3) | N12—C65—H65A | 109.5 |
C2—C1—H1A | 118.0 | N12—C65—H65B | 109.5 |
C6—C1—H1A | 118.0 | H65A—C65—H65B | 109.5 |
C1—C2—C3 | 118.7 (3) | N12—C65—H65C | 109.5 |
C1—C2—H2 | 120.6 | H65A—C65—H65C | 109.5 |
C3—C2—H2 | 120.6 | H65B—C65—H65C | 109.5 |
O1—C3—C4 | 117.4 (3) | N12—C66—O15 | 122.9 (5) |
O1—C3—C2 | 122.6 (3) | N12—C66—H66 | 118.5 |
C4—C3—C2 | 120.0 (3) | O15—C66—H66 | 118.5 |
C3—C4—C5 | 121.7 (3) | C7—N1—N2 | 116.7 (2) |
C3—C4—H4A | 119.2 | C7—N1—Zn1 | 128.9 (2) |
C5—C4—H4A | 119.2 | N2—N1—Zn1 | 114.07 (17) |
O2—C5—C4 | 120.2 (2) | C8—N2—N1 | 110.8 (2) |
O2—C5—C6 | 121.0 (2) | C21—N3—N4 | 115.9 (2) |
C4—C5—C6 | 118.8 (2) | C21—N3—Zn2 | 130.0 (2) |
C1—C6—C5 | 116.8 (3) | N4—N3—Zn2 | 113.66 (17) |
C1—C6—C7 | 118.0 (3) | C22—N4—N3 | 111.4 (2) |
C5—C6—C7 | 125.2 (3) | C29—N5—C33 | 117.0 (3) |
N1—C7—C6 | 126.8 (3) | C29—N5—Zn1 | 118.2 (2) |
N1—C7—H7 | 116.6 | C33—N5—Zn1 | 124.7 (2) |
C6—C7—H7 | 116.6 | C38—N6—C34 | 117.1 (3) |
O3—C8—N2 | 124.9 (3) | C38—N6—Zn2 | 121.2 (2) |
O3—C8—C9 | 117.7 (3) | C34—N6—Zn2 | 121.5 (2) |
N2—C8—C9 | 117.4 (3) | C60—N10—C59 | 120.5 (3) |
C10—C9—C14 | 118.2 (3) | C60—N10—C58 | 122.3 (3) |
C10—C9—C8 | 122.6 (3) | C59—N10—C58 | 117.1 (3) |
C14—C9—C8 | 119.2 (3) | C63—N11—C61 | 117.0 (4) |
O4—C10—C11 | 118.2 (3) | C63—N11—C62 | 124.1 (4) |
O4—C10—C9 | 122.2 (3) | C61—N11—C62 | 118.8 (4) |
C11—C10—C9 | 119.6 (4) | C66—N12—C64 | 125.0 (5) |
C12—C11—C10 | 120.7 (4) | C66—N12—C65 | 121.9 (5) |
C12—C11—H11 | 119.6 | C64—N12—C65 | 112.9 (4) |
C10—C11—H11 | 119.6 | C3—O1—H1 | 109 (3) |
C11—C12—C13 | 120.3 (4) | C5—O2—Zn2 | 128.58 (16) |
C11—C12—H12A | 119.8 | C5—O2—Zn1 | 129.18 (16) |
C13—C12—H12A | 119.8 | Zn2—O2—Zn1 | 100.80 (7) |
C14—C13—C12 | 119.7 (4) | C8—O3—Zn1 | 111.17 (17) |
C14—C13—H13 | 120.2 | C10—O4—H4 | 109 (3) |
C12—C13—H13 | 120.2 | C17—O5—H5 | 115 (3) |
C13—C14—C9 | 121.5 (4) | C19—O6—Zn1 | 125.41 (17) |
C13—C14—H14 | 119.3 | C19—O6—Zn2 | 129.76 (17) |
C9—C14—H14 | 119.3 | Zn1—O6—Zn2 | 100.66 (7) |
C16—C15—C20 | 123.3 (3) | C22—O7—Zn2 | 111.57 (17) |
C16—C15—H15A | 118.3 | C24—O8—H8 | 109 (4) |
C20—C15—H15A | 118.3 | C41—O9—H9 | 110 (4) |
C15—C16—C17 | 119.2 (3) | C48—O12—H12 | 117 (4) |
C15—C16—H16 | 120.4 | O6—Zn1—N1 | 145.01 (9) |
C17—C16—H16 | 120.4 | O6—Zn1—O3 | 105.16 (8) |
O5—C17—C16 | 122.9 (3) | N1—Zn1—O3 | 77.87 (8) |
O5—C17—C18 | 117.4 (3) | O6—Zn1—N5 | 105.26 (8) |
C16—C17—C18 | 119.7 (3) | N1—Zn1—N5 | 108.85 (9) |
C19—C18—C17 | 121.8 (3) | O3—Zn1—N5 | 97.82 (9) |
C19—C18—H18 | 119.1 | O6—Zn1—O2 | 79.55 (7) |
C17—C18—H18 | 119.1 | N1—Zn1—O2 | 86.86 (8) |
O6—C19—C18 | 120.2 (3) | O3—Zn1—O2 | 159.26 (8) |
O6—C19—C20 | 120.5 (2) | N5—Zn1—O2 | 100.37 (8) |
C18—C19—C20 | 119.3 (3) | O2—Zn2—O7 | 106.32 (7) |
C15—C20—C19 | 116.7 (3) | O2—Zn2—N3 | 137.52 (9) |
C15—C20—C21 | 118.2 (3) | O7—Zn2—N3 | 77.84 (8) |
C19—C20—C21 | 125.0 (3) | O2—Zn2—N6 | 106.71 (8) |
N3—C21—C20 | 126.4 (3) | O7—Zn2—N6 | 98.30 (9) |
N3—C21—H21 | 116.8 | N3—Zn2—N6 | 114.57 (9) |
C20—C21—H21 | 116.8 | O2—Zn2—O6 | 78.81 (7) |
O7—C22—N4 | 124.9 (3) | O7—Zn2—O6 | 159.44 (8) |
O7—C22—C23 | 118.5 (3) | N3—Zn2—O6 | 85.08 (8) |
N4—C22—C23 | 116.6 (3) | N6—Zn2—O6 | 99.18 (8) |
C28—C23—C24 | 118.1 (3) | O10i—Zn3—O11 | 105.13 (8) |
C28—C23—C22 | 119.4 (3) | O10i—Zn3—N7 | 142.28 (9) |
C24—C23—C22 | 122.5 (3) | O11—Zn3—N7 | 78.21 (8) |
O8—C24—C25 | 118.2 (4) | O10i—Zn3—N9 | 108.91 (9) |
O8—C24—C23 | 121.7 (3) | O11—Zn3—N9 | 98.54 (9) |
C25—C24—C23 | 120.0 (4) | N7—Zn3—N9 | 107.63 (9) |
C26—C25—C24 | 120.5 (4) | O10i—Zn3—O10 | 78.66 (7) |
C26—C25—H25 | 119.8 | O11—Zn3—O10 | 158.66 (8) |
C24—C25—H25 | 119.8 | N7—Zn3—O10 | 86.15 (8) |
C25—C26—C27 | 120.8 (4) | N9—Zn3—O10 | 99.99 (9) |
C25—C26—H26 | 119.6 | O10i—Zn3—Zn3i | 40.37 (5) |
C27—C26—H26 | 119.6 | O11—Zn3—Zn3i | 141.28 (6) |
C28—C27—C26 | 118.5 (4) | N7—Zn3—Zn3i | 117.10 (7) |
C28—C27—H27 | 120.8 | N9—Zn3—Zn3i | 108.63 (7) |
C26—C27—H27 | 120.8 | O10—Zn3—Zn3i | 38.29 (5) |
C27—C28—C23 | 122.1 (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—C42 | 2.8 (5) | C32—C33—N5—Zn1 | 174.4 (3) |
O9—C41—C42—C43 | 178.1 (3) | C37—C38—N6—C34 | 0.3 (5) |
C40—C41—C42—C43 | −2.5 (5) | C37—C38—N6—Zn2 | 176.8 (3) |
C41—C42—C43—O10 | 179.6 (3) | C35—C34—N6—C38 | −0.3 (5) |
C41—C42—C43—C44 | 0.1 (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—C45 | 176.8 (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—C39 | 1.9 (4) | O14—C63—N11—C62 | −177.2 (5) |
O10—C43—C44—C45 | 4.2 (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—N7 | 2.9 (5) | C6—C5—O2—Zn2 | 148.0 (2) |
O11—C46—C47—C52 | −7.7 (4) | C4—C5—O2—Zn1 | 165.08 (18) |
N8—C46—C47—C52 | 171.6 (3) | C6—C5—O2—Zn1 | −15.6 (3) |
O11—C46—C47—C48 | 171.0 (3) | N2—C8—O3—Zn1 | 8.1 (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—Zn1 | 47.2 (3) |
C46—C47—C48—O12 | 2.6 (6) | C20—C19—O6—Zn1 | −132.4 (2) |
C52—C47—C48—C49 | 2.8 (5) | C18—C19—O6—Zn2 | −160.4 (2) |
C46—C47—C48—C49 | −176.0 (3) | C20—C19—O6—Zn2 | 20.1 (4) |
O12—C48—C49—C50 | 178.8 (4) | N4—C22—O7—Zn2 | −6.8 (4) |
C47—C48—C49—C50 | −2.5 (7) | C23—C22—O7—Zn2 | 173.0 (2) |
C48—C49—C50—C51 | 0.4 (7) | C19—O6—Zn1—N1 | −129.2 (2) |
C49—C50—C51—C52 | 1.4 (7) | Zn2—O6—Zn1—N1 | 72.01 (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—O3 | 162.43 (8) |
C46—C47—C52—C51 | 177.8 (3) | C19—O6—Zn1—N5 | 63.9 (2) |
N9—C53—C54—C55 | 0.2 (7) | Zn2—O6—Zn1—N5 | −94.86 (9) |
C53—C54—C55—C56 | −2.2 (7) | C19—O6—Zn1—O2 | 162.0 (2) |
C54—C55—C56—C57 | 2.4 (7) | Zn2—O6—Zn1—O2 | 3.15 (7) |
C55—C56—C57—N9 | −0.5 (6) | C7—N1—Zn1—O6 | −77.5 (3) |
C44—C45—N7—N8 | 178.6 (3) | N2—N1—Zn1—O6 | 108.6 (2) |
C44—C45—N7—Zn3 | 9.3 (5) | C7—N1—Zn1—O3 | −176.7 (3) |
O11—C46—N8—N7 | 0.1 (4) | N2—N1—Zn1—O3 | 9.48 (17) |
C47—C46—N8—N7 | −179.2 (2) | C7—N1—Zn1—N5 | 89.1 (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—O2 | 175.36 (18) |
C56—C57—N9—Zn3 | −172.7 (3) | C8—O3—Zn1—O6 | −153.15 (18) |
C54—C53—N9—C57 | 1.7 (5) | C8—O3—Zn1—N1 | −9.06 (18) |
C54—C53—N9—Zn3 | 172.8 (3) | C8—O3—Zn1—N5 | 98.64 (19) |
C42—C43—O10—Zn3i | −34.3 (4) | C8—O3—Zn1—O2 | −52.5 (3) |
C44—C43—O10—Zn3i | 145.2 (2) | C29—N5—Zn1—O6 | −161.7 (2) |
C42—C43—O10—Zn3 | 158.0 (2) | C33—N5—Zn1—O6 | 22.9 (3) |
C44—C43—O10—Zn3 | −22.6 (4) | C29—N5—Zn1—N1 | 26.2 (2) |
N8—C46—O11—Zn3 | 5.7 (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—O3 | 131.0 (2) |
C1—C2—C3—O1 | −177.9 (3) | C29—N5—Zn1—O2 | 116.4 (2) |
C1—C2—C3—C4 | 2.9 (5) | C33—N5—Zn1—O2 | −59.0 (2) |
O1—C3—C4—C5 | 178.7 (2) | C5—O2—Zn1—O6 | 163.7 (2) |
C2—C3—C4—C5 | −2.2 (4) | Zn2—O2—Zn1—O6 | −3.32 (7) |
C3—C4—C5—O2 | 179.0 (2) | C5—O2—Zn1—N1 | 16.1 (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—O3 | 58.4 (3) |
C2—C1—C6—C7 | 177.1 (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—C1 | 1.9 (4) | Zn2—O2—Zn1—N5 | 100.47 (9) |
O2—C5—C6—C7 | 4.5 (4) | C5—O2—Zn2—O7 | 36.5 (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—N3 | 126.2 (2) |
C5—C6—C7—N1 | 0.8 (5) | Zn1—O2—Zn2—N3 | −66.64 (13) |
O3—C8—C9—C10 | 169.4 (3) | C5—O2—Zn2—N6 | −67.7 (2) |
N2—C8—C9—C10 | −10.0 (4) | Zn1—O2—Zn2—N6 | 99.47 (9) |
O3—C8—C9—C14 | −9.9 (4) | C5—O2—Zn2—O6 | −164.0 (2) |
N2—C8—C9—C14 | 170.8 (3) | Zn1—O2—Zn2—O6 | 3.14 (7) |
C14—C9—C10—O4 | −179.1 (3) | C22—O7—Zn2—O2 | 143.21 (19) |
C8—C9—C10—O4 | 1.6 (5) | C22—O7—Zn2—N3 | 6.90 (19) |
C14—C9—C10—C11 | 2.0 (5) | C22—O7—Zn2—N6 | −106.58 (19) |
C8—C9—C10—C11 | −177.3 (3) | C22—O7—Zn2—O6 | 41.4 (3) |
O4—C10—C11—C12 | 179.3 (4) | C21—N3—Zn2—O2 | 80.7 (3) |
C9—C10—C11—C12 | −1.8 (6) | N4—N3—Zn2—O2 | −107.6 (2) |
C10—C11—C12—C13 | 0.3 (6) | C21—N3—Zn2—O7 | −178.3 (3) |
C11—C12—C13—C14 | 1.0 (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—N6 | 87.1 (2) |
C8—C9—C14—C13 | 178.5 (3) | C21—N3—Zn2—O6 | 13.2 (3) |
C20—C15—C16—C17 | 1.8 (6) | N4—N3—Zn2—O6 | −175.09 (19) |
C15—C16—C17—O5 | 178.2 (3) | C38—N6—Zn2—O2 | 113.0 (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—O7 | 3.1 (2) |
C16—C17—C18—C19 | 2.3 (5) | C34—N6—Zn2—O7 | 179.4 (2) |
C17—C18—C19—O6 | −179.3 (3) | C38—N6—Zn2—N3 | −77.3 (3) |
C17—C18—C19—C20 | 0.3 (4) | C34—N6—Zn2—N3 | 99.1 (2) |
C16—C15—C20—C19 | 0.8 (6) | C38—N6—Zn2—O6 | −166.0 (2) |
C16—C15—C20—C21 | −175.7 (4) | C34—N6—Zn2—O6 | 10.3 (2) |
O6—C19—C20—C15 | 177.8 (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—C21 | 174.4 (3) | Zn1—O6—Zn2—O7 | 103.4 (2) |
C15—C20—C21—N3 | 175.3 (3) | C19—O6—Zn2—N3 | −20.3 (2) |
C19—C20—C21—N3 | −0.9 (6) | Zn1—O6—Zn2—N3 | 137.20 (10) |
O7—C22—C23—C28 | 4.3 (4) | C19—O6—Zn2—N6 | 93.9 (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—C24 | 5.3 (5) | C46—O11—Zn3—N7 | −6.48 (19) |
C28—C23—C24—O8 | 179.1 (4) | C46—O11—Zn3—N9 | 99.87 (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—C25 | 176.4 (4) | C45—N7—Zn3—O10i | −84.1 (3) |
O8—C24—C25—C26 | −179.9 (4) | N8—N7—Zn3—O10i | 106.4 (2) |
C23—C24—C25—C26 | 1.6 (7) | C45—N7—Zn3—O11 | 176.4 (3) |
C24—C25—C26—C27 | −0.1 (8) | N8—N7—Zn3—O11 | 6.82 (18) |
C25—C26—C27—C28 | −0.5 (7) | C45—N7—Zn3—N9 | 81.0 (3) |
C26—C27—C28—C23 | −0.4 (6) | N8—N7—Zn3—N9 | −88.50 (19) |
C24—C23—C28—C27 | 1.9 (5) | C45—N7—Zn3—O10 | −18.2 (3) |
C22—C23—C28—C27 | −177.0 (3) | N8—N7—Zn3—O10 | 172.22 (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—Zn3i | 148.87 (16) |
C30—C31—C32—C33 | 1.7 (6) | C57—N9—Zn3—O10i | −120.0 (2) |
C31—C32—C33—N5 | −0.7 (6) | C53—N9—Zn3—O10i | 69.3 (3) |
N6—C34—C35—C36 | −0.1 (6) | C57—N9—Zn3—O11 | −10.7 (3) |
C34—C35—C36—C37 | 0.4 (6) | C53—N9—Zn3—O11 | 178.6 (3) |
C35—C36—C37—C38 | −0.4 (6) | C57—N9—Zn3—N7 | 69.5 (3) |
C36—C37—C38—N6 | 0.0 (6) | C53—N9—Zn3—N7 | −101.2 (3) |
C6—C7—N1—N2 | 179.2 (3) | C57—N9—Zn3—O10 | 158.7 (2) |
C6—C7—N1—Zn1 | 5.5 (5) | C53—N9—Zn3—O10 | −12.0 (3) |
O3—C8—N2—N1 | 0.0 (4) | C57—N9—Zn3—Zn3i | −162.7 (2) |
C9—C8—N2—N1 | 179.2 (2) | C53—N9—Zn3—Zn3i | 26.5 (3) |
C7—N1—N2—C8 | 177.1 (2) | C43—O10—Zn3—O10i | 170.4 (3) |
Zn1—N1—N2—C8 | −8.2 (3) | Zn3i—O10—Zn3—O10i | 0.0 |
C20—C21—N3—N4 | −178.2 (3) | C43—O10—Zn3—O11 | 67.8 (3) |
C20—C21—N3—Zn2 | −6.6 (5) | Zn3i—O10—Zn3—O11 | −102.6 (2) |
O7—C22—N4—N3 | 1.1 (4) | C43—O10—Zn3—N7 | 25.1 (2) |
C23—C22—N4—N3 | −178.7 (2) | Zn3i—O10—Zn3—N7 | −145.29 (10) |
C21—N3—N4—C22 | 178.2 (3) | C43—O10—Zn3—N9 | −82.1 (2) |
Zn2—N3—N4—C22 | 5.2 (3) | Zn3i—O10—Zn3—N9 | 107.47 (9) |
C30—C29—N5—C33 | 1.7 (5) | C43—O10—Zn3—Zn3i | 170.4 (3) |
Symmetry code: (i) −x, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···N2 | 0.80 (5) | 1.89 (3) | 2.595 (3) | 147 (5) |
O12—H12···N8 | 0.82 (3) | 1.94 (4) | 2.575 (3) | 134 (5) |
O8—H8···N4 | 0.87 (3) | 1.77 (4) | 2.546 (3) | 147 (5) |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C14H10N2O4)2(C5H5N)2]·2C3H7NO |
Mr | 975.61 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 24.5015 (16), 10.3868 (7), 28.8550 (18) |
β (°) | 113.127 (1) |
V (Å3) | 6753.2 (8) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 1.13 |
Crystal size (mm) | 0.20 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.805, 0.895 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45215, 15421, 9826 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.130, 1.01 |
No. of reflections | 15421 |
No. of parameters | 889 |
No. of restraints | 8 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.37 |
Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
N7—Zn3 | 2.042 (2) | N6—Zn2 | 2.051 (2) |
N9—Zn3 | 2.064 (2) | O2—Zn2 | 1.9976 (17) |
O10—Zn3 | 2.0798 (18) | O2—Zn1 | 2.0859 (17) |
O11—Zn3 | 2.0316 (18) | O3—Zn1 | 2.0388 (18) |
N1—Zn1 | 2.033 (2) | O6—Zn1 | 1.9834 (18) |
N3—Zn2 | 2.045 (2) | O6—Zn2 | 2.1035 (17) |
N5—Zn1 | 2.056 (2) | O7—Zn2 | 2.0372 (18) |
O6—Zn1—N1 | 145.01 (9) | O2—Zn2—N3 | 137.52 (9) |
O6—Zn1—O3 | 105.16 (8) | O7—Zn2—N3 | 77.84 (8) |
N1—Zn1—O3 | 77.87 (8) | O10i—Zn3—O11 | 105.13 (8) |
O6—Zn1—O2 | 79.55 (7) | O10i—Zn3—N7 | 142.28 (9) |
N1—Zn1—O2 | 86.86 (8) | O10i—Zn3—O10 | 78.66 (7) |
O3—Zn1—O2 | 159.26 (8) | O10i—Zn3—Zn3i | 40.37 (5) |
O2—Zn2—O7 | 106.32 (7) | O11—Zn3—Zn3i | 141.28 (6) |
Symmetry code: (i) −x, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···N2 | 0.80 (5) | 1.89 (3) | 2.595 (3) | 147 (5) |
O12—H12···N8 | 0.82 (3) | 1.94 (4) | 2.575 (3) | 134 (5) |
O8—H8···N4 | 0.87 (3) | 1.77 (4) | 2.546 (3) | 147 (5) |
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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.