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The title compound, [5,10,15,20-meso-tetrakis(4-hydroxy­phenyl)­porphyrinato-κ4N]­zinc(II) tris(dibenzo-24-crown-8) methanol tetrasolvate, [Zn(C44H28N4O4)]·3C24H32O8·4CH4O, was synthesized and its molecular structure precisely charac­terized by low-temperature single-crystal analysis. All the components are involved in hydrogen bonding with each other, thus forming an extensively hydrogen-bonded supramolecular lattice. The functionalized porphyrin moiety coordinates both equatorially and axially to the neighboring species.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010200776X/gd1198sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010200776X/gd1198Isup2.hkl
Contains datablock I

CCDC reference: 188600

Comment top

The zinc–tetrakis(4-hydroxyphenyl)porphyrin molecule, (I), has been used previously as a potential building block for the supramolecular synthesis of multiporphyrin arrays (Goldberg et al., 1995; Goldberg, 2000). The peripheral OH functional groups provide self-complementary binding sites for a simultaneous lateral association of every building block to several neighboring species by multiple hydrogen bonding. The ZnII ion in the porphyrin center may allow additional coordination in the axial direction to other ligands. A relevant example of such axial coordination of zinc– and manganese–tetraphenylporphyrin to 18-crown-6, via a water ligand bound to the metal ion, has been reported previously (Diskin-Posner et al., 1999). This report describes the extensive hydrogen bonding between the porphyrin moiety and the surrounding dibenzo-24-crown-8 species, (II), either directly or through methanol bridges, in directions parallel to the porphyrin plane, as well as perpendicular to it. The resulting structure represents a fascinating supramolecular lattice composed of three different species and held together by a co-operative array of hydrogen bonds.

The central core of the porphyrin moiety is nearly planar with only a slight puckering, the deviations of the individual atoms from the mean plane of the 24-atom macrocycle being between -0.091 (6) and 0.077 (5) Å. The ZnII ion is five-coordinate, deviating by 0.335 (3) Å from the plane of the four pyrrole N atoms towards the axial methanol ligand coordinated to it, and assuming a square-pyramidal coordination environment (shown in Fig. 3). The hydroxyphenyl rings are oriented in an almost perpendicular manner with respect to the porphyrin macrocycle, the corresponding dihedral angles being 76.2 (2), 73.4 (1), 75.6 (2) and 72.6 (2)°. The coordination bond lengths to the ZnII ion are given in Table 1. The three dibenzo-24-crown-8 species assume a roughly flat conformation (Fig. 1), with some of the methylene groups turned inward to fill the space within the macrocyclic rings. Correspondingly, while a fully open crown structure is characterized by a gauche conformation about the C—C bonds and a trans conformation about the C—O bonds, in this compound, some of the latter are also gauche. All O—C—C—O fragments preserved, however, their gauche arrangement. The molecular geometries of the constituent species are, otherwise, characterized by common features.

The supramolecular structure consists of layers of species interconnected by a network of hydrogen bonds, as shown in Fig. 2. Within a given layer, every porphyrin unit is hydrogen bonded in lateral directions to four different crown-ether moieties, either directly or through bridging methanol molecules. The direct porphyrin–crown ether interaction involves OH31···O82, OH31···O85, OH45···O114, and possibly also OH45···O117 hydrogen bonds on opposite sides of the porphyrin framework (Table 2). In the other directions, one side the porphyrin hydrogen bonds to a third crown-ether species through one methanol molecule (OH38···O152 and OH152···O98), while at the other end, it links through two methanol moieties (OH52···O154, OH154···O156 and OH156···O146; Table 2). The layers formed consist of two different rows (extending in the a-2 b direction) arranged side-by-side in an alternating manner. One row consists of crown-ether molecules only, while the other row contains paired porphyrin–crown-ether assemblies (Fig. 2). These layers are stacked along the a axis of the crystal in an offset manner, which also facilitates additional hydrogen bonding between the layers. The offset is along a-2 b by a half vector translation in order to position the crown-ether ring of one layer above the porphyrin-coordinated axial methanol ligand of another layer, and optimize the interlayer hydrogen bond, OH54···O149 (Table 2). Figs. 3 and 4 illustrate the stacking arrangement along the a axis of the crystal. The resulting structure thus contains columns of alternating porphyrin and crown-ether species, as well as separate stacks of the other crown-ether moieties (Fig. 4), all of which are interconnected to each other by the methanol bridges. The efficient intermolecular hydrogen bonding yielded a relatively well packed chiral (though the analyzed crystal represents a racemic twin) and polar structure of previously unknown supramolecular features. These results are particularly significant in the context of the crystal engineering of new supramolecular materials.

Experimental top

All chemicals used were obtained commercially. Zinc–tetrakis(4-carboxyphenyl)porphyrin (7.5 mg, 0.01 mmol) was reacted with dibenzo-24-crown-8 (5 mg, 0.01 mmol) in warm methanol (4 ml). Toluene (10 drops) was added to this solution to control solubility. Single crystals of the title compound were then obtained by slow evaporation in open air.

Refinement top

The title compound is a racemic twin. The methyl group of the zinc-bound methanol molecule is orientationally disordered. These features, along with the somewhat high mosaicity of the analyzed crystal and the large number of available data, affected, to some extent, the precision of the crystallographic determination and resulted in somewhat high R factors. Atom H31 (bonded to O31) was located directly from a difference map, with an O—H distance of 0.78 Å; the remaining H atoms were placed in calculated postions, with C—H distances in the range 0.95–0.99 Å and O—H distances in the range 0.93–0.96 Å.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski, 1985); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of the porphyrin, crown ether and methanol components of the title compound, showing the atom-labeling scheme. The ellipsoids represent displacement parameters at the 50% probability level at ca 110 K. The methanol species labeled O54 and C55 is coordinated to zinc through atom O54. Bond lengths involving the ZnII ion in the porphyrin core are listed in Table 1.
[Figure 2] Fig. 2. Perspective view of the layered molecular arrangement in the title structure, roughly down the a axis of the crystal (all the heteroatoms are represented by crossed circles, while C atoms are represented by open circles). All the intralayer hydrogen bonds which interconnect between the different species are indicated by thin lines. The translation vectors, which relate between equivalent molecules, are also marked.
[Figure 3] Fig. 3. A slice of the structure parallel to the ab plane, emphasizing the additional porphyrin–crown-ether hydrogen bonding through an axial methanol ligand in a direction perpendicular to the porphyrin plane. Also illustrated is the stacked organization of the layers shown in Fig. 2. This slice of the structure is sandwiched from above and below between sections consisting of stacked crown-ether moieties only (see Fig. 4), accounting for the 1:3 ratio between the porphyrin and crown-ether components. Note the slight deviation of the ZnII ion from the porphyrin core towards the axial ligand.
[Figure 4] Fig. 4. Stereoview of the intermolecular stacking down the a axis (c is roughly vertical). Two layers are shown. Note the separate columns of the overlapping crown ethers, and of the axially hydrogen-bonded porphyrin and crown-ether species. The columns are interlinked to each other laterally by methanol bridges.
(I) top
Crystal data top
[Zn(C44H28N4O4)]·3C24H32O8·4CH4OZ = 1
Mr = 2215.73F(000) = 1174
Triclinic, P1Dx = 1.339 Mg m3
a = 10.2643 (3) ÅMo Kα radiation, λ = 0.71070 Å
b = 13.4878 (4) ÅCell parameters from 18559 reflections
c = 21.1227 (8) Åθ = 1.9–27.8°
α = 86.2858 (10)°µ = 0.31 mm1
β = 77.9955 (13)°T = 110 K
γ = 73.932 (3)°Prism, red
V = 2748.51 (15) Å30.35 × 0.30 × 0.25 mm
Data collection top
Nonius KappaCCD
diffractometer
13092 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
Detector resolution: 56 microns pixels mm-1h = 1112
0.8° ϕ and ω scansk = 1416
15453 measured reflectionsl = 2425
15453 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0644P)2 + 4.9932P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.136
15453 reflectionsΔρmax = 0.96 e Å3
1420 parametersΔρmin = 0.55 e Å3
4 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.477 (13)
Crystal data top
[Zn(C44H28N4O4)]·3C24H32O8·4CH4Oγ = 73.932 (3)°
Mr = 2215.73V = 2748.51 (15) Å3
Triclinic, P1Z = 1
a = 10.2643 (3) ÅMo Kα radiation
b = 13.4878 (4) ŵ = 0.31 mm1
c = 21.1227 (8) ÅT = 110 K
α = 86.2858 (10)°0.35 × 0.30 × 0.25 mm
β = 77.9955 (13)°
Data collection top
Nonius KappaCCD
diffractometer
13092 reflections with I > 2σ(I)
15453 measured reflectionsRint = 0.000
15453 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.167(Δ/σ)max = 0.136
S = 1.05Δρmax = 0.96 e Å3
15453 reflectionsΔρmin = 0.55 e Å3
1420 parametersAbsolute structure: Flack (1983)
4 restraintsAbsolute structure parameter: 0.477 (13)
Special details top

Experimental. 'Intensity data were measured up to theta=27.84 °. with completeness factor of 0.90, while to theta=25.0 °. the completeness was 94%. Due to the large size of the problem, the emphasis placed on the analysis of intermolecular organization rather than on fine details of the molecular structure, and very weak high-angle intensities, the smaller but more complete shell was used in the least-squares refinement calculations.'

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.

The compound is a racemic twin. The methyl group of the zinc-bound methanol is orientationally disordered. These features, along with somewhat high mosaicity of the analyzed crystal and the large number of available data, affected to some extent the precision of the crystallographic determination and resulted in somewhat high R-factors.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7625 (5)0.0493 (4)0.7037 (2)0.0208 (11)
N20.6142 (5)0.1550 (4)0.8216 (2)0.0202 (12)
N30.6011 (5)0.0399 (3)0.8838 (2)0.0171 (11)
N40.7547 (5)0.1478 (4)0.7662 (2)0.0174 (11)
C50.8239 (6)0.1825 (4)0.7056 (3)0.0191 (13)
C60.8670 (6)0.1230 (5)0.6530 (3)0.0223 (14)
C70.8403 (6)0.0149 (5)0.6516 (3)0.0220 (14)
C80.8768 (7)0.0476 (5)0.5967 (3)0.0259 (15)
H80.92740.02340.55500.031*
C90.8262 (7)0.1468 (5)0.6150 (3)0.0263 (15)
H90.83600.20520.58870.032*
C100.7544 (7)0.1492 (5)0.6818 (3)0.0217 (13)
C110.6891 (6)0.2375 (4)0.7180 (3)0.0201 (13)
C120.6243 (6)0.2392 (4)0.7840 (3)0.0181 (12)
C130.5584 (6)0.3327 (5)0.8217 (3)0.0224 (14)
H130.55300.40140.80690.027*
C140.5063 (7)0.3031 (4)0.8815 (3)0.0217 (13)
H140.45720.34710.91710.026*
C150.5397 (6)0.1919 (4)0.8813 (3)0.0191 (13)
C160.4979 (6)0.1310 (4)0.9344 (3)0.0170 (13)
C170.5248 (6)0.0235 (5)0.9349 (3)0.0181 (13)
C180.4766 (6)0.0369 (5)0.9881 (3)0.0200 (13)
H180.42190.01131.02880.024*
C190.5231 (7)0.1371 (5)0.9700 (3)0.0232 (14)
H190.50840.19500.99560.028*
C200.5996 (6)0.1388 (4)0.9040 (3)0.0176 (12)
C210.6602 (6)0.2290 (4)0.8662 (3)0.0202 (13)
C220.7307 (7)0.2315 (4)0.8024 (3)0.0206 (13)
C230.7864 (7)0.3234 (5)0.7634 (3)0.0254 (14)
H230.78290.39140.77660.030*
C240.8450 (7)0.2934 (5)0.7039 (3)0.0233 (14)
H240.89120.33710.66790.028*
C250.9457 (6)0.1787 (5)0.5921 (3)0.0179 (13)
C261.0899 (7)0.1963 (5)0.5728 (3)0.0248 (14)
H261.13830.16830.59770.030*
C271.1617 (7)0.2530 (5)0.5191 (3)0.0283 (15)
H271.25930.26510.50730.034*
C281.0913 (7)0.2930 (5)0.4818 (3)0.0224 (14)
C290.9498 (6)0.2752 (5)0.4988 (3)0.0220 (14)
H290.90170.30140.47290.026*
C300.8778 (7)0.2191 (5)0.5538 (3)0.0211 (13)
H300.78030.20800.56560.025*
O311.1691 (5)0.3493 (4)0.4285 (2)0.0337 (12)
H311.10880.37020.42280.021 (18)*
C320.6900 (6)0.3386 (4)0.6850 (3)0.0184 (13)
C330.5673 (6)0.4025 (5)0.6679 (3)0.0206 (13)
H330.48380.38220.67910.025*
C340.5687 (7)0.4939 (5)0.6352 (3)0.0235 (14)
H340.48620.53600.62350.028*
C350.6881 (7)0.5251 (5)0.6192 (3)0.0234 (14)
C360.8076 (7)0.4646 (5)0.6367 (3)0.0276 (15)
H360.89010.48630.62590.033*
C370.8085 (7)0.3728 (5)0.6698 (3)0.0249 (14)
H370.89120.33270.68220.030*
O380.6968 (5)0.6139 (3)0.5846 (2)0.0337 (11)
H380.62680.63810.55870.09 (4)*
C390.4118 (7)0.1851 (4)0.9950 (3)0.0181 (13)
C400.4715 (6)0.2258 (5)1.0357 (3)0.0200 (13)
H400.56750.22131.02440.024*
C410.3938 (7)0.2741 (5)1.0938 (3)0.0240 (14)
H410.43700.30021.12210.029*
C420.2538 (7)0.2828 (5)1.1090 (3)0.0252 (15)
C430.1903 (7)0.2437 (5)1.0671 (3)0.0267 (14)
H430.09370.25011.07710.032*
C440.2722 (7)0.1952 (5)1.0104 (3)0.0229 (14)
H440.23030.16850.98180.027*
O450.1715 (5)0.3315 (4)1.1630 (2)0.0388 (12)
H450.22770.32881.19390.047*
C460.6494 (6)0.3289 (4)0.9001 (3)0.0191 (13)
C470.7643 (7)0.3938 (5)0.9192 (3)0.0216 (13)
H470.85050.37760.90770.026*
C480.7554 (7)0.4840 (5)0.9555 (3)0.0235 (14)
H480.83480.52890.96840.028*
C490.6280 (7)0.5057 (5)0.9720 (3)0.0234 (14)
C500.5124 (7)0.4439 (5)0.9517 (3)0.0253 (14)
H500.42710.46170.96180.030*
C510.5232 (6)0.3545 (5)0.9160 (3)0.0229 (13)
H510.44410.31070.90240.028*
O520.6124 (5)0.5914 (3)1.0093 (2)0.0300 (10)
H520.69760.63311.01870.036*
Zn530.71368 (6)0.00275 (5)0.79772 (3)0.01856 (17)
O540.9125 (4)0.0027 (3)0.8144 (2)0.0297 (10)
H540.93810.00610.85510.036*
C551.0233 (16)0.0404 (12)0.7588 (7)0.132 (6)*
H55A1.04770.00180.71980.198*
H55B1.10690.03630.77550.198*
H55C0.98080.11230.74810.198*
O561.0016 (5)0.2932 (3)0.4393 (2)0.0285 (10)
C571.0558 (7)0.1880 (5)0.4347 (3)0.0254 (14)
C581.1421 (7)0.1298 (6)0.4729 (3)0.0335 (16)
H581.16960.16230.50450.040*
C591.1890 (8)0.0243 (6)0.4655 (4)0.0387 (18)
H591.24730.01600.49260.046*
C601.1509 (8)0.0234 (6)0.4181 (4)0.046 (2)
H601.18510.09600.41260.055*
C611.0652 (8)0.0333 (6)0.3799 (4)0.0386 (18)
H611.04010.00010.34790.046*
C621.0138 (7)0.1403 (5)0.3874 (3)0.0325 (16)
O630.9258 (5)0.2037 (3)0.3525 (2)0.0303 (11)
C640.8660 (8)0.1562 (6)0.3108 (3)0.0378 (18)
H64A0.82920.10090.33460.045*
H64B0.93770.12490.27310.045*
C650.7494 (9)0.2384 (7)0.2877 (3)0.044 (2)
H65A0.68250.20340.27830.053*
H65B0.70060.28570.32430.053*
O660.7841 (7)0.3004 (5)0.2320 (3)0.0549 (16)
C670.8443 (9)0.3796 (8)0.2462 (4)0.051 (2)
H67A0.78340.42140.28330.061*
H67B0.93540.34740.25780.061*
C680.8599 (10)0.4428 (7)0.1909 (5)0.061 (3)
H68A0.92920.48010.19330.074*
H68B0.89360.39940.15170.074*
O690.7327 (5)0.5141 (4)0.1868 (3)0.0435 (13)
C700.7406 (8)0.5539 (6)0.1211 (4)0.0401 (18)
H70A0.68370.52520.09870.048*
H70B0.83760.53260.09710.048*
C710.6896 (8)0.6694 (5)0.1218 (3)0.0315 (16)
H71A0.68630.69590.07720.038*
H71B0.59490.69090.14820.038*
O720.7804 (5)0.7114 (3)0.1484 (2)0.0271 (10)
C730.7436 (6)0.8167 (5)0.1545 (3)0.0214 (13)
C740.6422 (7)0.8835 (5)0.1255 (3)0.0257 (14)
H740.59490.85700.09930.031*
C750.6107 (7)0.9894 (5)0.1351 (3)0.0313 (16)
H750.54121.03480.11560.038*
C760.6786 (7)1.0289 (5)0.1724 (3)0.0301 (15)
H760.65651.10130.17850.036*
C770.7813 (7)0.9616 (5)0.2014 (3)0.0292 (15)
H770.82860.98880.22720.035*
C780.8137 (6)0.8567 (5)0.1929 (3)0.0229 (14)
O790.9096 (4)0.7850 (3)0.2208 (2)0.0258 (10)
C800.9684 (8)0.8243 (6)0.2658 (4)0.0350 (17)
H80A0.89470.86240.30070.042*
H80B1.02210.87170.24380.042*
C811.0634 (8)0.7307 (6)0.2940 (4)0.0399 (18)
H81A1.12180.68460.25840.048*
H81B1.12540.75460.31600.048*
O820.9873 (5)0.6751 (4)0.3384 (2)0.0322 (11)
C830.9696 (7)0.5840 (5)0.3143 (3)0.0277 (15)
H83A1.05730.54480.28710.033*
H83B0.89750.60260.28770.033*
C840.9274 (7)0.5204 (5)0.3714 (3)0.0276 (15)
H84A0.83860.55880.39800.033*
H84B0.91580.45560.35680.033*
O851.0341 (5)0.4981 (3)0.4081 (2)0.0287 (10)
C860.9961 (8)0.4590 (5)0.4720 (3)0.0320 (16)
H86A0.89410.47370.48380.038*
H86B1.02640.49540.50320.038*
C871.0589 (7)0.3452 (5)0.4776 (3)0.0285 (15)
H87A1.16040.32870.46250.034*
H87B1.03950.32280.52330.034*
O880.3322 (5)0.7063 (3)0.1582 (2)0.0282 (10)
C890.2854 (7)0.8117 (5)0.1630 (3)0.0248 (14)
C900.2027 (7)0.8742 (5)0.1245 (3)0.0324 (16)
H900.17530.84510.09130.039*
C910.1591 (8)0.9813 (6)0.1346 (4)0.0385 (18)
H910.09921.02450.10920.046*
C920.2031 (8)1.0241 (5)0.1814 (3)0.0366 (17)
H920.17761.09680.18660.044*
C930.2836 (7)0.9610 (5)0.2203 (3)0.0324 (16)
H930.30840.99010.25430.039*
C940.3293 (6)0.8554 (5)0.2105 (3)0.0250 (14)
O950.4142 (5)0.7880 (3)0.2460 (2)0.0274 (10)
C960.4787 (7)0.8319 (5)0.2877 (3)0.0303 (15)
H96A0.40860.86580.32520.036*
H96B0.52100.88440.26360.036*
C970.5882 (8)0.7463 (6)0.3108 (3)0.0371 (18)
H97A0.63840.69960.27420.045*
H97B0.65560.77670.32420.045*
O980.5361 (5)0.6860 (4)0.3641 (2)0.0421 (13)
C990.4943 (8)0.5982 (6)0.3442 (4)0.0365 (17)
H99A0.40670.62380.32820.044*
H99B0.56630.56020.30870.044*
C1000.4761 (8)0.5304 (6)0.3993 (3)0.0377 (17)
H10A0.41350.57020.43680.045*
H10B0.43470.47680.38890.045*
O1010.6068 (5)0.4840 (4)0.4144 (3)0.0385 (12)
C1020.5971 (8)0.4367 (6)0.4777 (4)0.0396 (18)
H10C0.49950.45800.50090.047*
H10D0.65280.46280.50230.047*
C1030.6437 (7)0.3250 (5)0.4767 (3)0.0287 (15)
H10E0.64450.29800.52130.034*
H10F0.73910.30250.45100.034*
O1040.5511 (5)0.2840 (3)0.4480 (2)0.0283 (10)
C1050.5931 (7)0.1796 (5)0.4390 (3)0.0229 (14)
C1060.6928 (7)0.1110 (5)0.4671 (3)0.0308 (16)
H1060.73660.13590.49570.037*
C1070.7299 (8)0.0060 (5)0.4540 (3)0.0339 (17)
H1070.79910.04040.47320.041*
C1080.6655 (8)0.0300 (5)0.4131 (3)0.0351 (17)
H1080.69090.10170.40410.042*
C1090.5656 (7)0.0355 (5)0.3851 (3)0.0294 (15)
H1090.52260.00860.35710.035*
C1100.5254 (7)0.1418 (5)0.3970 (3)0.0233 (14)
O1110.4294 (5)0.2127 (3)0.3715 (2)0.0264 (10)
C1120.3652 (7)0.1762 (6)0.3261 (3)0.0309 (16)
H11A0.31570.12600.34780.037*
H11B0.43700.14110.28950.037*
C1130.2660 (7)0.2660 (6)0.3015 (3)0.0381 (18)
H11C0.19990.24100.28310.046*
H11D0.21260.31220.33810.046*
O1140.3359 (5)0.3233 (3)0.2529 (2)0.0325 (11)
C1150.3700 (7)0.4076 (5)0.2751 (3)0.0296 (15)
H11E0.44660.38280.29900.035*
H11F0.28910.45110.30430.035*
C1160.4134 (8)0.4680 (6)0.2157 (4)0.0362 (17)
H11G0.43910.52840.22830.043*
H11H0.49470.42410.18680.043*
O1170.2995 (4)0.5014 (3)0.1830 (2)0.0255 (10)
C1180.3356 (7)0.5418 (5)0.1198 (3)0.0299 (15)
H11I0.30360.50740.08840.036*
H11J0.43750.52750.10720.036*
C1190.2702 (8)0.6575 (5)0.1179 (3)0.0309 (16)
H11K0.28680.68370.07290.037*
H11L0.16910.67310.13420.037*
O1200.0446 (5)0.2269 (4)0.0175 (2)0.0349 (11)
C1210.0781 (7)0.3313 (5)0.0301 (4)0.0303 (16)
C1220.0627 (7)0.3985 (6)0.0194 (3)0.0331 (16)
H1220.02680.37280.06210.040*
C1230.0976 (7)0.5031 (5)0.0094 (4)0.0354 (16)
H1230.08530.54860.04510.042*
C1240.1501 (8)0.5420 (6)0.0518 (4)0.0414 (18)
H1240.17300.61420.05890.050*
C1250.1696 (7)0.4740 (6)0.1038 (4)0.0386 (17)
H1250.20800.50050.14630.046*
C1260.1338 (7)0.3697 (6)0.0940 (3)0.0329 (16)
O1270.1450 (5)0.2942 (4)0.1406 (2)0.0435 (13)
C1280.1711 (9)0.3312 (6)0.2062 (4)0.0459 (19)
H12A0.10500.37040.21050.055*
H12B0.26630.37670.21810.055*
C1290.1530 (8)0.2378 (7)0.2484 (4)0.048 (2)
H12C0.14950.25820.29210.058*
H12D0.06280.18890.23090.058*
O1300.2599 (6)0.1851 (4)0.2545 (2)0.0465 (13)
C1310.3809 (9)0.2340 (6)0.2961 (4)0.050 (2)
H13A0.35980.24990.33740.060*
H13B0.42680.29960.27650.060*
C1320.4757 (8)0.1631 (6)0.3087 (4)0.0460 (19)
H13C0.48910.14180.26700.055*
H13D0.56720.20000.33380.055*
O1330.4148 (5)0.0727 (4)0.3445 (2)0.0374 (12)
C1340.5083 (8)0.0111 (6)0.3632 (4)0.0446 (19)
H13E0.58820.04790.39600.053*
H13F0.54340.00210.32520.053*
C1350.4373 (9)0.0874 (7)0.3904 (4)0.049 (2)
H13G0.50540.12570.41020.059*
H13H0.39110.07420.42450.059*
O1360.3370 (6)0.1474 (4)0.3400 (2)0.0467 (14)
C1370.2849 (8)0.2518 (6)0.3493 (3)0.0359 (17)
C1380.3075 (9)0.3061 (6)0.4066 (4)0.044 (2)
H1380.36330.26990.44410.053*
C1390.2521 (8)0.4099 (6)0.4107 (4)0.0423 (19)
H1390.26900.44500.45080.051*
C1400.1698 (8)0.4650 (7)0.3556 (4)0.049 (2)
H1400.13330.53770.35760.059*
C1410.1424 (7)0.4101 (6)0.2971 (4)0.0405 (18)
H1410.08350.44600.26010.049*
C1420.2001 (7)0.3048 (5)0.2931 (3)0.0317 (16)
O1430.1702 (5)0.2530 (4)0.2372 (2)0.0346 (11)
C1440.2874 (7)0.2100 (6)0.2057 (3)0.0367 (17)
H14A0.27360.24850.16540.044*
H14B0.37280.21890.23450.044*
C1450.3049 (7)0.0976 (5)0.1897 (3)0.0310 (15)
H14C0.29910.06100.22780.037*
H14D0.39710.06680.17890.037*
O1460.1991 (5)0.0857 (3)0.1359 (2)0.0302 (10)
C1470.2221 (7)0.0213 (5)0.1162 (3)0.0306 (15)
H14E0.31810.04940.10940.037*
H14F0.20830.06230.15030.037*
C1480.1209 (8)0.0283 (6)0.0541 (4)0.0430 (19)
H14G0.14970.09720.03390.052*
H14H0.12020.02430.02330.052*
O1490.0146 (5)0.0117 (4)0.0673 (2)0.0360 (12)
C1500.1051 (7)0.0587 (6)0.0196 (3)0.0320 (16)
H15A0.20260.02090.01970.038*
H15B0.08710.05220.02400.038*
C1510.0843 (7)0.1692 (5)0.0330 (3)0.0315 (15)
H15C0.16070.19410.00650.038*
H15D0.08360.17830.07920.038*
O1520.5288 (6)0.6896 (4)0.5006 (2)0.0449 (13)
H1520.53800.68810.45540.054*
C1530.5041 (9)0.7971 (5)0.5042 (4)0.0408 (18)
H15E0.44310.82180.54550.061*
H15F0.46010.83040.46850.061*
H15G0.59210.81420.50100.061*
O1540.8529 (5)0.2933 (4)0.0358 (2)0.0377 (12)
H1540.89710.27710.00710.045*
C1550.8330 (9)0.2058 (6)0.0733 (5)0.056 (3)
H15H0.91200.17710.09440.085*
H15I0.82520.15370.04510.085*
H15J0.74810.22620.10620.085*
O1560.9785 (5)0.2477 (4)0.0858 (2)0.0425 (13)
H1561.05450.19190.10330.051*
C1570.8756 (8)0.2643 (7)0.1250 (4)0.049 (2)
H15K0.82180.33680.12250.074*
H15L0.81390.22020.10920.074*
H15M0.92100.24700.17000.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.030 (3)0.012 (3)0.021 (3)0.003 (2)0.009 (2)0.002 (2)
N20.034 (3)0.012 (3)0.016 (3)0.005 (2)0.007 (2)0.005 (2)
N30.027 (3)0.006 (2)0.018 (3)0.001 (2)0.007 (2)0.001 (2)
N40.023 (3)0.013 (3)0.014 (3)0.002 (2)0.002 (2)0.003 (2)
C50.028 (4)0.017 (3)0.011 (3)0.003 (2)0.005 (2)0.002 (2)
C60.018 (3)0.022 (3)0.027 (3)0.002 (2)0.006 (3)0.006 (3)
C70.025 (4)0.021 (3)0.019 (3)0.003 (3)0.003 (2)0.009 (2)
C80.044 (4)0.021 (4)0.011 (3)0.007 (3)0.004 (3)0.001 (2)
C90.039 (4)0.019 (3)0.016 (3)0.006 (3)0.001 (3)0.000 (3)
C100.026 (4)0.018 (3)0.023 (3)0.009 (3)0.007 (3)0.007 (3)
C110.027 (4)0.017 (3)0.017 (3)0.004 (3)0.009 (3)0.000 (2)
C120.021 (3)0.015 (3)0.020 (3)0.006 (2)0.002 (2)0.007 (2)
C130.026 (4)0.014 (3)0.027 (3)0.003 (3)0.006 (3)0.007 (3)
C140.034 (4)0.012 (3)0.017 (3)0.002 (3)0.006 (3)0.003 (2)
C150.021 (3)0.015 (3)0.021 (3)0.005 (2)0.006 (2)0.001 (2)
C160.023 (3)0.015 (3)0.012 (3)0.003 (2)0.001 (2)0.008 (2)
C170.024 (3)0.020 (3)0.011 (3)0.006 (2)0.007 (2)0.001 (2)
C180.023 (3)0.022 (3)0.015 (3)0.004 (3)0.004 (2)0.010 (2)
C190.026 (4)0.019 (3)0.024 (3)0.005 (3)0.007 (3)0.005 (3)
C200.020 (3)0.012 (3)0.021 (3)0.003 (2)0.006 (2)0.001 (2)
C210.027 (4)0.010 (3)0.024 (3)0.004 (2)0.008 (3)0.001 (2)
C220.029 (4)0.012 (3)0.025 (3)0.010 (2)0.007 (3)0.000 (2)
C230.028 (4)0.014 (3)0.037 (4)0.005 (3)0.011 (3)0.002 (3)
C240.026 (4)0.023 (3)0.019 (3)0.006 (3)0.001 (3)0.005 (3)
C250.023 (4)0.016 (3)0.013 (3)0.004 (2)0.000 (2)0.003 (2)
C260.033 (4)0.026 (4)0.019 (3)0.011 (3)0.008 (3)0.003 (3)
C270.021 (4)0.040 (4)0.022 (3)0.007 (3)0.001 (3)0.005 (3)
C280.023 (4)0.023 (4)0.019 (3)0.007 (3)0.001 (3)0.001 (3)
C290.023 (4)0.026 (4)0.019 (3)0.006 (3)0.007 (3)0.008 (3)
C300.023 (4)0.021 (3)0.020 (3)0.006 (3)0.005 (3)0.002 (2)
O310.017 (3)0.057 (3)0.027 (2)0.010 (2)0.0050 (18)0.027 (2)
C320.034 (4)0.011 (3)0.011 (3)0.006 (3)0.006 (2)0.001 (2)
C330.025 (4)0.018 (3)0.021 (3)0.010 (3)0.004 (2)0.002 (2)
C340.030 (4)0.023 (3)0.017 (3)0.005 (3)0.003 (3)0.004 (2)
C350.033 (4)0.012 (3)0.026 (3)0.006 (3)0.008 (3)0.003 (2)
C360.033 (4)0.027 (4)0.026 (3)0.016 (3)0.004 (3)0.001 (3)
C370.029 (4)0.021 (4)0.027 (3)0.011 (3)0.005 (3)0.003 (3)
O380.048 (3)0.020 (2)0.036 (3)0.015 (2)0.008 (2)0.009 (2)
C390.027 (4)0.013 (3)0.015 (3)0.007 (2)0.005 (3)0.000 (2)
C400.020 (3)0.018 (3)0.020 (3)0.004 (2)0.002 (2)0.007 (2)
C410.030 (4)0.026 (4)0.020 (3)0.012 (3)0.007 (3)0.004 (3)
C420.034 (4)0.024 (4)0.013 (3)0.006 (3)0.004 (3)0.007 (3)
C430.015 (3)0.035 (4)0.032 (4)0.009 (3)0.005 (3)0.003 (3)
C440.031 (4)0.020 (3)0.018 (3)0.006 (3)0.006 (3)0.009 (2)
O450.028 (3)0.069 (4)0.022 (2)0.019 (2)0.003 (2)0.020 (2)
C460.028 (4)0.012 (3)0.020 (3)0.007 (2)0.009 (3)0.000 (2)
C470.022 (3)0.020 (3)0.025 (3)0.009 (3)0.004 (3)0.004 (3)
C480.029 (4)0.014 (3)0.027 (3)0.006 (3)0.006 (3)0.001 (3)
C490.035 (4)0.013 (3)0.022 (3)0.008 (3)0.002 (3)0.005 (2)
C500.020 (4)0.022 (3)0.035 (4)0.007 (3)0.005 (3)0.002 (3)
C510.024 (4)0.020 (3)0.029 (3)0.008 (3)0.011 (3)0.001 (3)
O520.034 (3)0.021 (2)0.031 (2)0.010 (2)0.0020 (19)0.0055 (19)
Zn530.0215 (4)0.0152 (3)0.0188 (3)0.0046 (3)0.0034 (3)0.0024 (3)
O540.030 (3)0.034 (3)0.030 (2)0.011 (2)0.014 (2)0.0002 (19)
O560.036 (3)0.020 (2)0.030 (3)0.004 (2)0.011 (2)0.0011 (19)
C570.031 (4)0.016 (3)0.027 (3)0.006 (3)0.000 (3)0.000 (3)
C580.029 (4)0.034 (4)0.034 (4)0.008 (3)0.001 (3)0.009 (3)
C590.029 (4)0.031 (4)0.046 (5)0.004 (3)0.007 (3)0.009 (3)
C600.038 (5)0.021 (4)0.066 (6)0.006 (3)0.017 (4)0.001 (4)
C610.034 (4)0.028 (4)0.050 (5)0.013 (3)0.010 (3)0.007 (3)
C620.031 (4)0.024 (4)0.040 (4)0.013 (3)0.006 (3)0.001 (3)
O630.031 (3)0.030 (3)0.034 (3)0.011 (2)0.008 (2)0.009 (2)
C640.040 (5)0.053 (5)0.027 (4)0.028 (4)0.007 (3)0.020 (3)
C650.064 (6)0.059 (5)0.027 (4)0.046 (5)0.015 (4)0.011 (4)
O660.080 (5)0.057 (4)0.039 (3)0.034 (3)0.014 (3)0.003 (3)
C670.041 (5)0.078 (7)0.039 (4)0.027 (4)0.002 (4)0.018 (4)
C680.055 (6)0.039 (5)0.095 (7)0.008 (4)0.033 (5)0.002 (5)
O690.035 (3)0.022 (3)0.069 (4)0.001 (2)0.014 (3)0.013 (2)
C700.048 (5)0.030 (4)0.038 (4)0.017 (3)0.010 (3)0.006 (3)
C710.047 (5)0.034 (4)0.020 (3)0.027 (3)0.001 (3)0.003 (3)
O720.030 (3)0.020 (2)0.030 (2)0.0079 (19)0.0033 (19)0.0009 (19)
C730.024 (4)0.022 (4)0.016 (3)0.009 (3)0.005 (2)0.000 (2)
C740.037 (4)0.026 (4)0.019 (3)0.016 (3)0.006 (3)0.005 (3)
C750.032 (4)0.037 (4)0.022 (3)0.006 (3)0.006 (3)0.007 (3)
C760.035 (4)0.023 (4)0.033 (4)0.011 (3)0.006 (3)0.004 (3)
C770.037 (4)0.029 (4)0.026 (4)0.013 (3)0.010 (3)0.002 (3)
C780.021 (4)0.027 (4)0.017 (3)0.005 (3)0.000 (2)0.003 (3)
O790.022 (2)0.031 (3)0.025 (2)0.0050 (19)0.0082 (18)0.0005 (19)
C800.039 (4)0.035 (4)0.038 (4)0.016 (3)0.017 (3)0.010 (3)
C810.044 (5)0.040 (5)0.044 (4)0.017 (4)0.022 (4)0.014 (3)
O820.051 (3)0.031 (3)0.020 (2)0.020 (2)0.010 (2)0.0061 (19)
C830.039 (4)0.026 (4)0.022 (3)0.007 (3)0.014 (3)0.006 (3)
C840.029 (4)0.032 (4)0.030 (4)0.015 (3)0.016 (3)0.002 (3)
O850.034 (3)0.028 (3)0.026 (2)0.010 (2)0.012 (2)0.0001 (19)
C860.043 (4)0.021 (4)0.030 (4)0.005 (3)0.009 (3)0.001 (3)
C870.033 (4)0.030 (4)0.027 (4)0.012 (3)0.014 (3)0.004 (3)
O880.029 (3)0.026 (3)0.032 (3)0.008 (2)0.011 (2)0.003 (2)
C890.023 (4)0.028 (4)0.024 (3)0.008 (3)0.004 (3)0.003 (3)
C900.042 (4)0.022 (4)0.032 (4)0.005 (3)0.009 (3)0.000 (3)
C910.035 (4)0.031 (4)0.042 (4)0.003 (3)0.005 (3)0.016 (3)
C920.050 (5)0.020 (4)0.037 (4)0.013 (3)0.002 (3)0.004 (3)
C930.031 (4)0.033 (4)0.035 (4)0.013 (3)0.003 (3)0.005 (3)
C940.022 (4)0.022 (4)0.027 (3)0.001 (3)0.002 (3)0.005 (3)
O950.032 (3)0.029 (3)0.024 (2)0.010 (2)0.0070 (19)0.0029 (19)
C960.035 (4)0.034 (4)0.024 (3)0.015 (3)0.001 (3)0.011 (3)
C970.048 (5)0.052 (5)0.020 (3)0.028 (4)0.010 (3)0.011 (3)
O980.046 (3)0.048 (3)0.033 (3)0.014 (3)0.007 (2)0.009 (2)
C990.038 (4)0.035 (4)0.043 (4)0.015 (3)0.010 (3)0.018 (3)
C1000.044 (5)0.042 (4)0.032 (4)0.017 (3)0.014 (3)0.003 (3)
O1010.025 (3)0.029 (3)0.059 (3)0.004 (2)0.009 (2)0.007 (2)
C1020.048 (5)0.038 (4)0.037 (4)0.021 (4)0.004 (3)0.004 (3)
C1030.030 (4)0.037 (4)0.021 (3)0.009 (3)0.006 (3)0.007 (3)
O1040.036 (3)0.024 (3)0.025 (2)0.009 (2)0.005 (2)0.0060 (19)
C1050.030 (4)0.019 (3)0.017 (3)0.006 (3)0.001 (3)0.002 (2)
C1060.040 (4)0.036 (4)0.019 (3)0.016 (3)0.006 (3)0.007 (3)
C1070.044 (5)0.020 (4)0.036 (4)0.006 (3)0.012 (3)0.015 (3)
C1080.049 (5)0.018 (4)0.038 (4)0.009 (3)0.008 (3)0.003 (3)
C1090.033 (4)0.031 (4)0.030 (4)0.018 (3)0.004 (3)0.006 (3)
C1100.027 (4)0.027 (4)0.016 (3)0.012 (3)0.001 (3)0.001 (3)
O1110.029 (3)0.023 (3)0.028 (2)0.0056 (19)0.0077 (19)0.0049 (19)
C1120.030 (4)0.039 (4)0.032 (4)0.023 (3)0.008 (3)0.004 (3)
C1130.034 (4)0.060 (5)0.032 (4)0.027 (4)0.016 (3)0.015 (3)
O1140.054 (3)0.028 (3)0.021 (2)0.019 (2)0.009 (2)0.0017 (19)
C1150.032 (4)0.036 (4)0.026 (3)0.012 (3)0.014 (3)0.000 (3)
C1160.033 (4)0.033 (4)0.048 (4)0.012 (3)0.015 (3)0.001 (3)
O1170.026 (3)0.028 (3)0.025 (2)0.0080 (19)0.0091 (18)0.0037 (18)
C1180.041 (4)0.028 (4)0.022 (3)0.012 (3)0.006 (3)0.002 (3)
C1190.047 (5)0.037 (4)0.014 (3)0.015 (3)0.013 (3)0.002 (3)
O1200.033 (3)0.028 (3)0.046 (3)0.006 (2)0.016 (2)0.000 (2)
C1210.024 (4)0.019 (4)0.052 (4)0.007 (3)0.017 (3)0.003 (3)
C1220.019 (4)0.046 (5)0.037 (4)0.016 (3)0.006 (3)0.009 (3)
C1230.022 (4)0.034 (4)0.045 (4)0.004 (3)0.003 (3)0.005 (3)
C1240.033 (4)0.032 (4)0.056 (5)0.008 (3)0.004 (3)0.004 (4)
C1250.030 (4)0.035 (4)0.048 (4)0.004 (3)0.009 (3)0.000 (3)
C1260.030 (4)0.040 (4)0.035 (4)0.017 (3)0.013 (3)0.010 (3)
O1270.046 (3)0.041 (3)0.044 (3)0.011 (2)0.008 (2)0.006 (2)
C1280.057 (6)0.044 (5)0.037 (4)0.019 (4)0.004 (4)0.003 (3)
C1290.039 (5)0.065 (6)0.045 (4)0.014 (4)0.017 (4)0.000 (4)
O1300.053 (4)0.041 (3)0.045 (3)0.015 (3)0.004 (3)0.003 (2)
C1310.059 (6)0.032 (4)0.044 (5)0.002 (4)0.004 (4)0.001 (4)
C1320.032 (5)0.043 (5)0.060 (5)0.005 (3)0.010 (4)0.003 (4)
O1330.030 (3)0.038 (3)0.044 (3)0.006 (2)0.009 (2)0.002 (2)
C1340.038 (5)0.041 (5)0.055 (5)0.014 (4)0.001 (4)0.013 (4)
C1350.047 (5)0.056 (6)0.034 (4)0.007 (4)0.010 (3)0.013 (4)
O1360.060 (4)0.031 (3)0.037 (3)0.002 (2)0.007 (2)0.000 (2)
C1370.035 (4)0.042 (4)0.029 (4)0.010 (3)0.005 (3)0.003 (3)
C1380.052 (5)0.048 (5)0.044 (5)0.025 (4)0.018 (4)0.007 (4)
C1390.041 (5)0.048 (5)0.046 (5)0.024 (4)0.017 (4)0.022 (4)
C1400.029 (5)0.045 (5)0.076 (6)0.006 (4)0.023 (4)0.012 (4)
C1410.025 (4)0.049 (5)0.046 (4)0.011 (3)0.004 (3)0.006 (4)
C1420.027 (4)0.033 (4)0.038 (4)0.009 (3)0.010 (3)0.003 (3)
O1430.029 (3)0.041 (3)0.032 (3)0.011 (2)0.001 (2)0.004 (2)
C1440.030 (4)0.050 (5)0.037 (4)0.024 (3)0.008 (3)0.009 (3)
C1450.028 (4)0.040 (4)0.024 (3)0.009 (3)0.008 (3)0.006 (3)
O1460.033 (3)0.030 (3)0.031 (2)0.015 (2)0.005 (2)0.0041 (19)
C1470.035 (4)0.022 (4)0.037 (4)0.007 (3)0.016 (3)0.006 (3)
C1480.057 (5)0.048 (5)0.042 (4)0.033 (4)0.029 (4)0.017 (4)
O1490.038 (3)0.041 (3)0.038 (3)0.018 (2)0.019 (2)0.013 (2)
C1500.026 (4)0.037 (4)0.030 (4)0.010 (3)0.001 (3)0.005 (3)
C1510.030 (4)0.031 (4)0.033 (4)0.006 (3)0.008 (3)0.002 (3)
O1520.060 (4)0.034 (3)0.040 (3)0.011 (2)0.012 (3)0.006 (2)
C1530.056 (5)0.028 (4)0.044 (4)0.016 (4)0.018 (4)0.001 (3)
O1540.040 (3)0.035 (3)0.038 (3)0.012 (2)0.008 (2)0.010 (2)
C1550.052 (6)0.045 (5)0.085 (7)0.023 (4)0.042 (5)0.040 (5)
O1560.035 (3)0.042 (3)0.047 (3)0.004 (2)0.005 (2)0.010 (2)
C1570.037 (5)0.054 (5)0.060 (5)0.009 (4)0.014 (4)0.019 (4)
Geometric parameters (Å, º) top
N1—C101.381 (8)C84—H84A0.9900
N1—C71.406 (8)C84—H84B0.9900
N1—Zn532.047 (5)O85—C861.434 (8)
N2—C121.358 (8)C86—C871.499 (9)
N2—C151.376 (8)C86—H86A0.9900
N2—Zn532.068 (5)C86—H86B0.9899
N3—C201.377 (7)C87—H87A0.9900
N3—C171.380 (7)C87—H87B0.9900
N3—Zn532.081 (5)O88—C891.372 (8)
N4—C51.370 (7)O88—C1191.447 (8)
N4—C221.373 (7)C89—C901.376 (9)
N4—Zn532.081 (5)C89—C941.403 (9)
C5—C61.396 (9)C90—C911.405 (10)
C5—C241.454 (8)C90—H900.9500
C6—C71.405 (8)C91—C921.386 (11)
C6—C251.494 (8)C91—H910.9500
C7—C81.437 (9)C92—C931.372 (10)
C8—C91.345 (9)C92—H920.9500
C8—H80.9500C93—C941.386 (9)
C9—C101.447 (9)C93—H930.9500
C9—H90.9500C94—O951.377 (8)
C10—C111.384 (8)O95—C961.446 (8)
C11—C121.414 (8)C96—C971.507 (10)
C11—C321.492 (8)C96—H96A0.9900
C12—C131.454 (8)C96—H96B0.9900
C13—C141.347 (9)C97—O981.444 (8)
C13—H130.9500C97—H97A0.9901
C14—C151.444 (8)C97—H97B0.9899
C14—H140.9500O98—C991.478 (8)
C15—C161.411 (8)C99—C1001.448 (11)
C16—C171.399 (8)C99—H99A0.9901
C16—C391.499 (8)C99—H99B0.9900
C17—C181.430 (9)C100—O1011.407 (8)
C18—C191.354 (9)C100—H10A0.9899
C18—H180.9500C100—H10B0.9900
C19—C201.450 (9)O101—C1021.440 (9)
C19—H190.9500C102—C1031.449 (10)
C20—C211.416 (8)C102—H10C0.9900
C21—C221.388 (9)C102—H10D0.9900
C21—C461.506 (8)C103—O1041.466 (8)
C22—C231.444 (9)C103—H10E0.9900
C23—C241.363 (9)C103—H10F0.9899
C23—H230.9500O104—C1051.368 (7)
C24—H240.9500C105—C1061.383 (9)
C25—C301.393 (8)C105—C1101.428 (9)
C25—C261.407 (9)C106—C1071.390 (10)
C26—C271.366 (9)C106—H1060.9500
C26—H260.9500C107—C1081.375 (10)
C27—C281.394 (9)C107—H1070.9500
C27—H270.9500C108—C1091.365 (10)
C28—O311.373 (7)C108—H1080.9500
C28—C291.378 (9)C109—C1101.401 (9)
C29—C301.383 (8)C109—H1090.9500
C29—H290.9500C110—O1111.346 (8)
C30—H300.9500O111—C1121.450 (8)
O31—H310.7805C112—C1131.494 (10)
C32—C371.388 (9)C112—H11A0.9900
C32—C331.417 (8)C112—H11B0.9899
C33—C341.377 (9)C113—O1141.437 (8)
C33—H330.9500C113—H11C0.9900
C34—C351.374 (9)C113—H11D0.9899
C34—H340.9500O114—C1151.411 (8)
C35—O381.377 (7)C115—C1161.507 (10)
C35—C361.380 (9)C115—H11E0.9900
C36—C371.380 (9)C115—H11F0.9900
C36—H360.9500C116—O1171.432 (8)
C37—H370.9500C116—H11G0.9900
O38—H380.9649C116—H11H0.9900
C39—C441.371 (9)O117—C1181.425 (8)
C39—C401.372 (8)C118—C1191.520 (10)
C40—C411.405 (9)C118—H11I0.9900
C40—H400.9500C118—H11J0.9900
C41—C421.379 (9)C119—H11K0.9900
C41—H410.9500C119—H11L0.9900
C42—O451.354 (7)O120—C1211.385 (8)
C42—C431.407 (9)O120—C1511.428 (8)
C43—C441.394 (9)C121—C1221.351 (9)
C43—H430.9500C121—C1261.421 (10)
C44—H440.9500C122—C1231.375 (10)
O45—H450.9505C122—H1220.9500
C46—C471.378 (9)C123—C1241.370 (10)
C46—C511.400 (9)C123—H1230.9500
C47—C481.409 (9)C124—C1251.404 (10)
C47—H470.9500C124—H1240.9500
C48—C491.388 (9)C125—C1261.370 (10)
C48—H480.9500C125—H1250.9500
C49—C501.379 (9)C126—O1271.381 (8)
C49—O521.383 (7)O127—C1281.449 (9)
C50—C511.398 (9)C128—C1291.486 (11)
C50—H500.9500C128—H12A0.9900
C51—H510.9500C128—H12B0.9900
O52—H520.9518C129—O1301.446 (10)
Zn53—O542.123 (4)C129—H12C0.9901
O54—C551.654 (13)C129—H12D0.9899
O54—H540.9440O130—C1311.385 (10)
C55—H55A0.9800C131—C1321.519 (12)
C55—H55B0.9800C131—H13A0.9900
C55—H55C0.9800C131—H13B0.9900
O56—C571.375 (8)C132—O1331.451 (9)
O56—C871.411 (8)C132—H13C0.9899
C57—C581.372 (10)C132—H13D0.9900
C57—C621.419 (10)O133—C1341.418 (9)
C58—C591.378 (10)C134—C1351.472 (12)
C58—H580.9500C134—H13E0.9900
C59—C601.398 (12)C134—H13F0.9900
C59—H590.9500C135—O1361.429 (9)
C60—C611.362 (12)C135—H13G0.9899
C60—H600.9500C135—H13H0.9900
C61—C621.400 (10)O136—C1371.378 (9)
C61—H610.9500C137—C1381.384 (10)
C62—O631.363 (8)C137—C1421.419 (10)
O63—C641.442 (8)C138—C1391.361 (11)
C64—C651.529 (12)C138—H1380.9500
C64—H64A0.9900C139—C1401.406 (12)
C64—H64B0.9901C139—H1390.9500
C65—O661.440 (9)C140—C1411.417 (11)
C65—H65A0.9900C140—H1400.9500
C65—H65B0.9900C141—C1421.383 (10)
O66—C671.448 (10)C141—H1410.9500
C67—C681.409 (13)C142—O1431.355 (8)
C67—H67A0.9901O143—C1441.458 (8)
C67—H67B0.9898C144—C1451.502 (10)
C68—O691.407 (10)C144—H14A0.9900
C68—H68A0.9902C144—H14B0.9900
C68—H68B0.9905C145—O1461.434 (8)
O69—C701.451 (9)C145—H14C0.9900
C70—C711.499 (10)C145—H14D0.9900
C70—H70A0.9900O146—C1471.444 (8)
C70—H70B0.9900C147—C1481.511 (10)
C71—O721.435 (8)C147—H14E0.9900
C71—H71A0.9900C147—H14F0.9900
C71—H71B0.9901C148—O1491.430 (9)
O72—C731.372 (7)C148—H14G0.9900
C73—C741.395 (9)C148—H14H0.9900
C73—C781.407 (9)O149—C1501.460 (8)
C74—C751.392 (9)C150—C1511.483 (10)
C74—H740.9500C150—H15A0.9900
C75—C761.370 (10)C150—H15B0.9900
C75—H750.9500C151—H15C0.9900
C76—C771.407 (10)C151—H15D0.9900
C76—H760.9500O152—C1531.406 (8)
C77—C781.375 (9)O152—H1520.9410
C77—H770.9500C153—H15E0.9800
C78—O791.376 (7)C153—H15F0.9800
O79—C801.425 (8)C153—H15G0.9800
C80—C811.537 (10)O154—C1551.415 (9)
C80—H80A0.9900O154—H1540.9344
C80—H80B0.9900C155—H15H0.9800
C81—O821.406 (8)C155—H15I0.9800
C81—H81A0.9900C155—H15J0.9800
C81—H81B0.9900O156—C1571.435 (9)
O82—C831.430 (8)O156—H1560.9497
C83—C841.494 (9)C157—H15K0.9800
C83—H83A0.9900C157—H15L0.9800
C83—H83B0.9900C157—H15M0.9800
C84—O851.426 (7)
C10—N1—C7106.0 (5)C83—C84—H84B110.3
C10—N1—Zn53126.7 (4)H84A—C84—H84B108.5
C7—N1—Zn53125.8 (4)C84—O85—C86114.4 (5)
C12—N2—C15106.2 (5)O85—C86—C87112.4 (6)
C12—N2—Zn53126.6 (4)O85—C86—H86A109.1
C15—N2—Zn53126.7 (4)C87—C86—H86A109.1
C20—N3—C17106.0 (5)O85—C86—H86B109.1
C20—N3—Zn53126.6 (4)C87—C86—H86B109.1
C17—N3—Zn53127.1 (4)H86A—C86—H86B107.9
C5—N4—C22107.5 (5)O56—C87—C86108.8 (5)
C5—N4—Zn53124.8 (4)O56—C87—H87A109.9
C22—N4—Zn53127.5 (4)C86—C87—H87A109.9
N4—C5—C6126.8 (5)O56—C87—H87B109.9
N4—C5—C24108.7 (5)C86—C87—H87B109.9
C6—C5—C24124.5 (5)H87A—C87—H87B108.3
C5—C6—C7126.0 (6)C89—O88—C119116.6 (5)
C5—C6—C25117.2 (5)O88—C89—C90124.6 (6)
C7—C6—C25116.8 (5)O88—C89—C94115.4 (5)
C6—C7—N1124.0 (6)C90—C89—C94120.0 (6)
C6—C7—C8126.5 (5)C89—C90—C91119.6 (6)
N1—C7—C8109.3 (5)C89—C90—H90120.2
C9—C8—C7107.4 (5)C91—C90—H90120.2
C9—C8—H8126.3C92—C91—C90120.2 (7)
C7—C8—H8126.3C92—C91—H91119.9
C8—C9—C10108.1 (6)C90—C91—H91119.9
C8—C9—H9125.9C93—C92—C91119.7 (7)
C10—C9—H9125.9C93—C92—H92120.1
N1—C10—C11125.6 (6)C91—C92—H92120.1
N1—C10—C9109.2 (5)C92—C93—C94120.8 (6)
C11—C10—C9125.3 (5)C92—C93—H93119.6
C10—C11—C12125.0 (5)C94—C93—H93119.6
C10—C11—C32117.4 (5)O95—C94—C93123.9 (6)
C12—C11—C32117.5 (5)O95—C94—C89116.5 (5)
N2—C12—C11125.7 (5)C93—C94—C89119.6 (6)
N2—C12—C13110.0 (5)C94—O95—C96117.4 (5)
C11—C12—C13124.4 (6)O95—C96—C97108.4 (5)
C14—C13—C12106.9 (5)O95—C96—H96A110.0
C14—C13—H13126.5C97—C96—H96A110.0
C12—C13—H13126.5O95—C96—H96B110.0
C13—C14—C15106.8 (5)C97—C96—H96B110.0
C13—C14—H14126.6H96A—C96—H96B108.4
C15—C14—H14126.6O98—C97—C96114.5 (6)
N2—C15—C16125.5 (5)O98—C97—H97A108.6
N2—C15—C14110.0 (5)C96—C97—H97A108.6
C16—C15—C14124.5 (5)O98—C97—H97B108.6
C17—C16—C15125.6 (5)C96—C97—H97B108.6
C17—C16—C39116.3 (5)H97A—C97—H97B107.6
C15—C16—C39118.0 (5)C97—O98—C99114.1 (5)
N3—C17—C16125.0 (5)C100—C99—O98108.8 (6)
N3—C17—C18110.0 (5)C100—C99—H99A109.9
C16—C17—C18125.0 (5)O98—C99—H99A109.9
C19—C18—C17107.5 (5)C100—C99—H99B109.9
C19—C18—H18126.2O98—C99—H99B109.9
C17—C18—H18126.2H99A—C99—H99B108.3
C18—C19—C20106.7 (5)O101—C100—C99108.0 (6)
C18—C19—H19126.6O101—C100—H10A110.1
C20—C19—H19126.6C99—C100—H10A110.1
N3—C20—C21125.9 (5)O101—C100—H10B110.1
N3—C20—C19109.7 (5)C99—C100—H10B110.1
C21—C20—C19124.5 (5)H10A—C100—H10B108.4
C22—C21—C20125.1 (5)C100—O101—C102112.3 (6)
C22—C21—C46119.0 (5)O101—C102—C103113.9 (6)
C20—C21—C46115.8 (5)O101—C102—H10C108.8
N4—C22—C21125.7 (5)C103—C102—H10C108.8
N4—C22—C23109.7 (5)O101—C102—H10D108.8
C21—C22—C23124.6 (5)C103—C102—H10D108.8
C24—C23—C22106.6 (5)H10C—C102—H10D107.7
C24—C23—H23126.7C102—C103—O104109.8 (5)
C22—C23—H23126.7C102—C103—H10E109.7
C23—C24—C5107.5 (5)O104—C103—H10E109.7
C23—C24—H24126.3C102—C103—H10F109.7
C5—C24—H24126.3O104—C103—H10F109.7
C30—C25—C26117.8 (6)H10E—C103—H10F108.2
C30—C25—C6120.2 (6)C105—O104—C103114.6 (5)
C26—C25—C6121.9 (5)O104—C105—C106125.3 (6)
C27—C26—C25121.3 (6)O104—C105—C110115.2 (5)
C27—C26—H26119.4C106—C105—C110119.5 (6)
C25—C26—H26119.4C105—C106—C107120.9 (6)
C26—C27—C28119.8 (6)C105—C106—H106119.5
C26—C27—H27120.1C107—C106—H106119.5
C28—C27—H27120.1C108—C107—C106119.4 (6)
O31—C28—C29122.8 (5)C108—C107—H107120.3
O31—C28—C27117.1 (6)C106—C107—H107120.3
C29—C28—C27120.2 (6)C109—C108—C107121.1 (7)
C28—C29—C30119.9 (6)C109—C108—H108119.4
C28—C29—H29120.1C107—C108—H108119.4
C30—C29—H29120.1C108—C109—C110121.2 (6)
C29—C30—C25121.1 (6)C108—C109—H109119.4
C29—C30—H30119.5C110—C109—H109119.4
C25—C30—H30119.5O111—C110—C109125.8 (6)
C28—O31—H3194.0O111—C110—C105116.3 (5)
C37—C32—C33118.1 (6)C109—C110—C105117.8 (6)
C37—C32—C11122.1 (6)C110—O111—C112116.9 (5)
C33—C32—C11119.9 (5)O111—C112—C113109.0 (6)
C34—C33—C32120.1 (6)O111—C112—H11A109.9
C34—C33—H33119.9C113—C112—H11A109.9
C32—C33—H33119.9O111—C112—H11B109.9
C35—C34—C33120.8 (6)C113—C112—H11B109.9
C35—C34—H34119.6H11A—C112—H11B108.3
C33—C34—H34119.6O114—C113—C112111.7 (6)
C34—C35—O38123.3 (6)O114—C113—H11C109.3
C34—C35—C36119.6 (6)C112—C113—H11C109.3
O38—C35—C36117.1 (6)O114—C113—H11D109.3
C35—C36—C37120.6 (6)C112—C113—H11D109.3
C35—C36—H36119.7H11C—C113—H11D107.9
C37—C36—H36119.7C115—O114—C113116.0 (5)
C36—C37—C32120.7 (6)O114—C115—C116106.3 (5)
C36—C37—H37119.6O114—C115—H11E110.5
C32—C37—H37119.6C116—C115—H11E110.5
C35—O38—H38113.8O114—C115—H11F110.5
C44—C39—C40119.1 (6)C116—C115—H11F110.5
C44—C39—C16120.6 (5)H11E—C115—H11F108.7
C40—C39—C16120.4 (6)O117—C116—C115108.1 (6)
C39—C40—C41121.5 (6)O117—C116—H11G110.1
C39—C40—H40119.3C115—C116—H11G110.1
C41—C40—H40119.3O117—C116—H11H110.1
C42—C41—C40118.9 (6)C115—C116—H11H110.1
C42—C41—H41120.6H11G—C116—H11H108.4
C40—C41—H41120.6C118—O117—C116113.5 (5)
O45—C42—C41122.2 (6)O117—C118—C119110.6 (5)
O45—C42—C43117.4 (6)O117—C118—H11I109.5
C41—C42—C43120.4 (6)C119—C118—H11I109.5
C44—C43—C42118.6 (6)O117—C118—H11J109.5
C44—C43—H43120.7C119—C118—H11J109.5
C42—C43—H43120.7H11I—C118—H11J108.1
C39—C44—C43121.6 (6)O88—C119—C118107.9 (5)
C39—C44—H44119.2O88—C119—H11K110.1
C43—C44—H44119.2C118—C119—H11K110.1
C42—O45—H45107.8O88—C119—H11L110.1
C47—C46—C51119.2 (6)C118—C119—H11L110.1
C47—C46—C21119.3 (6)H11K—C119—H11L108.4
C51—C46—C21121.4 (5)C121—O120—C151114.1 (5)
C46—C47—C48120.8 (6)C122—C121—O120119.6 (7)
C46—C47—H47119.6C122—C121—C126119.3 (6)
C48—C47—H47119.6O120—C121—C126121.1 (6)
C49—C48—C47118.5 (6)C121—C122—C123121.7 (7)
C49—C48—H48120.8C121—C122—H122119.2
C47—C48—H48120.8C123—C122—H122119.2
C50—C49—O52117.3 (6)C124—C123—C122120.2 (7)
C50—C49—C48121.9 (6)C124—C123—H123119.9
O52—C49—C48120.9 (6)C122—C123—H123119.9
C49—C50—C51118.7 (6)C123—C124—C125119.2 (7)
C49—C50—H50120.6C123—C124—H124120.4
C51—C50—H50120.6C125—C124—H124120.4
C50—C51—C46120.8 (6)C126—C125—C124120.5 (7)
C50—C51—H51119.6C126—C125—H125119.7
C46—C51—H51119.6C124—C125—H125119.7
C49—O52—H52112.6C125—C126—O127126.7 (7)
N1—Zn53—N288.46 (19)C125—C126—C121119.1 (6)
N1—Zn53—N489.46 (18)O127—C126—C121114.3 (6)
N2—Zn53—N4162.08 (19)C126—O127—C128113.6 (6)
N1—Zn53—N3160.60 (19)O127—C128—C129106.1 (6)
N2—Zn53—N388.18 (19)O127—C128—H12A110.5
N4—Zn53—N387.90 (18)C129—C128—H12A110.5
N1—Zn53—O5492.14 (19)O127—C128—H12B110.5
N2—Zn53—O5499.05 (19)C129—C128—H12B110.5
N4—Zn53—O5498.82 (18)H12A—C128—H12B108.7
N3—Zn53—O54107.26 (18)O130—C129—C128114.8 (6)
C55—O54—Zn53120.3 (6)O130—C129—H12C108.6
C55—O54—H54110.1C128—C129—H12C108.5
Zn53—O54—H54126.4O130—C129—H12D108.6
O54—C55—H55A109.5C128—C129—H12D108.6
O54—C55—H55B109.5H12C—C129—H12D107.5
H55A—C55—H55B109.5C131—O130—C129113.0 (6)
O54—C55—H55C109.5O130—C131—C132108.6 (6)
H55A—C55—H55C109.5O130—C131—H13A110.0
H55B—C55—H55C109.5C132—C131—H13A110.0
C57—O56—C87116.6 (5)O130—C131—H13B110.0
C58—C57—O56124.3 (6)C132—C131—H13B110.0
C58—C57—C62120.5 (6)H13A—C131—H13B108.3
O56—C57—C62115.2 (6)O133—C132—C131109.5 (6)
C57—C58—C59120.1 (7)O133—C132—H13C109.8
C57—C58—H58119.9C131—C132—H13C109.8
C59—C58—H58119.9O133—C132—H13D109.8
C58—C59—C60120.0 (7)C131—C132—H13D109.8
C58—C59—H59120.0H13C—C132—H13D108.2
C60—C59—H59120.0C134—O133—C132110.5 (6)
C61—C60—C59120.6 (7)O133—C134—C135109.5 (7)
C61—C60—H60119.7O133—C134—H13E109.8
C59—C60—H60119.7C135—C134—H13E109.8
C60—C61—C62120.5 (8)O133—C134—H13F109.8
C60—C61—H61119.8C135—C134—H13F109.8
C62—C61—H61119.8H13E—C134—H13F108.2
O63—C62—C61125.1 (7)O136—C135—C134109.3 (6)
O63—C62—C57116.5 (6)O136—C135—H13G109.8
C61—C62—C57118.3 (7)C134—C135—H13G109.8
C62—O63—C64117.7 (6)O136—C135—H13H109.8
O63—C64—C65108.9 (6)C134—C135—H13H109.8
O63—C64—H64A109.9H13G—C135—H13H108.3
C65—C64—H64A109.9C137—O136—C135119.5 (6)
O63—C64—H64B109.9O136—C137—C138126.4 (7)
C65—C64—H64B109.9O136—C137—C142114.1 (6)
H64A—C64—H64B108.3C138—C137—C142119.6 (7)
O66—C65—C64118.6 (7)C139—C138—C137122.0 (8)
O66—C65—H65A107.7C139—C138—H138119.0
C64—C65—H65A107.7C137—C138—H138119.0
O66—C65—H65B107.7C138—C139—C140119.9 (7)
C64—C65—H65B107.7C138—C139—H139120.1
H65A—C65—H65B107.1C140—C139—H139120.1
C65—O66—C67113.0 (6)C139—C140—C141118.8 (7)
C68—C67—O66108.5 (7)C139—C140—H140120.6
C68—C67—H67A110.0C141—C140—H140120.6
O66—C67—H67A110.0C142—C141—C140120.9 (7)
C68—C67—H67B110.0C142—C141—H141119.5
O66—C67—H67B110.0C140—C141—H141119.5
H67A—C67—H67B108.4O143—C142—C141120.2 (6)
O69—C68—C67110.2 (9)O143—C142—C137120.9 (6)
O69—C68—H68A109.6C141—C142—C137118.8 (7)
C67—C68—H68A109.7C142—O143—C144114.4 (5)
O69—C68—H68B109.6O143—C144—C145111.9 (5)
C67—C68—H68B109.6O143—C144—H14A109.2
H68A—C68—H68B108.1C145—C144—H14A109.2
C68—O69—C70108.4 (7)O143—C144—H14B109.2
O69—C70—C71109.9 (5)C145—C144—H14B109.2
O69—C70—H70A109.7H14A—C144—H14B107.9
C71—C70—H70A109.7O146—C145—C144109.8 (6)
O69—C70—H70B109.7O146—C145—H14C109.7
C71—C70—H70B109.7C144—C145—H14C109.7
H70A—C70—H70B108.2O146—C145—H14D109.7
O72—C71—C70109.6 (6)C144—C145—H14D109.7
O72—C71—H71A109.8H14C—C145—H14D108.2
C70—C71—H71A109.8C145—O146—C147110.4 (5)
O72—C71—H71B109.8O146—C147—C148108.5 (6)
C70—C71—H71B109.8O146—C147—H14E110.0
H71A—C71—H71B108.2C148—C147—H14E110.0
C73—O72—C71116.2 (5)O146—C147—H14F110.0
O72—C73—C74123.8 (5)C148—C147—H14F110.0
O72—C73—C78116.4 (5)H14E—C147—H14F108.4
C74—C73—C78119.8 (6)O149—C148—C147109.8 (5)
C75—C74—C73119.6 (6)O149—C148—H14G109.7
C75—C74—H74120.2C147—C148—H14G109.7
C73—C74—H74120.2O149—C148—H14H109.7
C76—C75—C74120.9 (6)C147—C148—H14H109.7
C76—C75—H75119.5H14G—C148—H14H108.2
C74—C75—H75119.5C148—O149—C150113.9 (5)
C75—C76—C77119.5 (6)O149—C150—C151112.3 (6)
C75—C76—H76120.2O149—C150—H15A109.1
C77—C76—H76120.2C151—C150—H15A109.1
C78—C77—C76120.6 (6)O149—C150—H15B109.1
C78—C77—H77119.7C151—C150—H15B109.1
C76—C77—H77119.7H15A—C150—H15B107.9
C77—C78—O79124.6 (6)O120—C151—C150108.7 (5)
C77—C78—C73119.5 (6)O120—C151—H15C110.0
O79—C78—C73115.8 (5)C150—C151—H15C110.0
C78—O79—C80115.9 (5)O120—C151—H15D110.0
O79—C80—C81106.7 (6)C150—C151—H15D110.0
O79—C80—H80A110.4H15C—C151—H15D108.3
C81—C80—H80A110.4C153—O152—H15295.4
O79—C80—H80B110.4O152—C153—H15E109.5
C81—C80—H80B110.4O152—C153—H15F109.5
H80A—C80—H80B108.6H15E—C153—H15F109.5
O82—C81—C80111.7 (6)O152—C153—H15G109.5
O82—C81—H81A109.3H15E—C153—H15G109.5
C80—C81—H81A109.3H15F—C153—H15G109.5
O82—C81—H81B109.3C155—O154—H154113.0
C80—C81—H81B109.3O154—C155—H15H109.5
H81A—C81—H81B107.9O154—C155—H15I109.5
C81—O82—C83116.2 (5)H15H—C155—H15I109.5
O82—C83—C84107.6 (5)O154—C155—H15J109.5
O82—C83—H83A110.2H15H—C155—H15J109.5
C84—C83—H83A110.2H15I—C155—H15J109.5
O82—C83—H83B110.2C157—O156—H156108.7
C84—C83—H83B110.2O156—C157—H15K109.5
H83A—C83—H83B108.5O156—C157—H15L109.5
O85—C84—C83107.3 (5)H15K—C157—H15L109.5
O85—C84—H84A110.3O156—C157—H15M109.5
C83—C84—H84A110.3H15K—C157—H15M109.5
O85—C84—H84B110.3H15L—C157—H15M109.5
C22—N4—C5—C6179.0 (6)C5—N4—Zn53—N3175.3 (5)
Zn53—N4—C5—C66.5 (9)C22—N4—Zn53—N311.2 (5)
C22—N4—C5—C240.4 (7)C5—N4—Zn53—O5477.5 (5)
Zn53—N4—C5—C24174.1 (4)C22—N4—Zn53—O5495.9 (5)
N4—C5—C6—C73.9 (10)C20—N3—Zn53—N194.2 (7)
C24—C5—C6—C7175.4 (6)C17—N3—Zn53—N193.1 (7)
N4—C5—C6—C25177.8 (6)C20—N3—Zn53—N2174.3 (5)
C24—C5—C6—C252.9 (9)C17—N3—Zn53—N213.0 (5)
C5—C6—C7—N11.2 (10)C20—N3—Zn53—N411.8 (5)
C25—C6—C7—N1177.1 (6)C17—N3—Zn53—N4175.5 (5)
C5—C6—C7—C8175.9 (7)C20—N3—Zn53—O5486.7 (5)
C25—C6—C7—C82.3 (9)C17—N3—Zn53—O5486.0 (5)
C10—N1—C7—C6177.0 (6)N1—Zn53—O54—C557.2 (7)
Zn53—N1—C7—C616.4 (8)N2—Zn53—O54—C5581.6 (7)
C10—N1—C7—C81.5 (7)N4—Zn53—O54—C5596.9 (7)
Zn53—N1—C7—C8168.1 (4)N3—Zn53—O54—C55172.5 (7)
C6—C7—C8—C9176.9 (6)C87—O56—C57—C5811.9 (9)
N1—C7—C8—C91.5 (7)C87—O56—C57—C62169.4 (6)
C7—C8—C9—C101.0 (8)O56—C57—C58—C59178.7 (6)
C7—N1—C10—C11178.6 (6)C62—C57—C58—C590.1 (10)
Zn53—N1—C10—C1112.1 (9)C57—C58—C59—C601.3 (11)
C7—N1—C10—C90.9 (7)C58—C59—C60—C611.4 (11)
Zn53—N1—C10—C9167.4 (4)C59—C60—C61—C620.0 (11)
C8—C9—C10—N10.1 (8)C60—C61—C62—O63178.8 (7)
C8—C9—C10—C11179.6 (6)C60—C61—C62—C571.4 (10)
N1—C10—C11—C122.3 (10)C58—C57—C62—O63178.8 (6)
C9—C10—C11—C12177.1 (6)O56—C57—C62—O630.0 (9)
N1—C10—C11—C32179.1 (5)C58—C57—C62—C611.4 (10)
C9—C10—C11—C321.5 (9)O56—C57—C62—C61179.8 (6)
C15—N2—C12—C11177.9 (6)C61—C62—O63—C648.8 (9)
Zn53—N2—C12—C119.7 (9)C57—C62—O63—C64171.4 (6)
C15—N2—C12—C132.1 (7)C62—O63—C64—C65168.2 (6)
Zn53—N2—C12—C13170.3 (4)O63—C64—C65—O6684.7 (7)
C10—C11—C12—N21.1 (10)C64—C65—O66—C6776.1 (9)
C32—C11—C12—N2179.7 (5)C65—O66—C67—C68173.5 (8)
C10—C11—C12—C13178.8 (6)O66—C67—C68—O6979.5 (9)
C32—C11—C12—C130.2 (9)C67—C68—O69—C70161.9 (7)
N2—C12—C13—C141.4 (7)C68—O69—C70—C71131.6 (7)
C11—C12—C13—C14178.7 (6)O69—C70—C71—O7265.0 (7)
C12—C13—C14—C150.1 (7)C70—C71—O72—C73177.6 (5)
C12—N2—C15—C16176.3 (6)C71—O72—C73—C7412.9 (8)
Zn53—N2—C15—C1611.4 (9)C71—O72—C73—C78166.7 (5)
C12—N2—C15—C142.1 (7)O72—C73—C74—C75179.2 (5)
Zn53—N2—C15—C14170.3 (4)C78—C73—C74—C750.4 (9)
C13—C14—C15—N21.3 (7)C73—C74—C75—C760.4 (10)
C13—C14—C15—C16177.1 (6)C74—C75—C76—C770.2 (10)
N2—C15—C16—C170.4 (10)C75—C76—C77—C780.1 (11)
C14—C15—C16—C17177.8 (6)C76—C77—C78—O79178.1 (6)
N2—C15—C16—C39177.4 (5)C76—C77—C78—C730.2 (10)
C14—C15—C16—C390.7 (9)O72—C73—C78—C77179.5 (5)
C20—N3—C17—C16178.8 (6)C74—C73—C78—C770.1 (9)
Zn53—N3—C17—C167.3 (8)O72—C73—C78—O791.1 (8)
C20—N3—C17—C180.9 (6)C74—C73—C78—O79178.5 (5)
Zn53—N3—C17—C18173.0 (4)C77—C78—O79—C805.7 (9)
C15—C16—C17—N32.5 (9)C73—C78—O79—C80172.6 (6)
C39—C16—C17—N3179.6 (5)C78—O79—C80—C81176.1 (5)
C15—C16—C17—C18177.1 (6)O79—C80—C81—O8274.4 (7)
C39—C16—C17—C180.0 (9)C80—C81—O82—C8399.8 (7)
N3—C17—C18—C190.1 (7)C81—O82—C83—C84162.6 (5)
C16—C17—C18—C19179.7 (6)O82—C83—C84—O8558.8 (7)
C17—C18—C19—C200.9 (7)C83—C84—O85—C86165.8 (5)
C17—N3—C20—C21177.2 (6)C84—O85—C86—C87104.6 (6)
Zn53—N3—C20—C218.8 (8)C57—O56—C87—C86175.1 (5)
C17—N3—C20—C191.4 (6)O85—C86—C87—O5666.3 (7)
Zn53—N3—C20—C19172.5 (4)C119—O88—C89—C9011.3 (9)
C18—C19—C20—N31.5 (7)C119—O88—C89—C94169.6 (6)
C18—C19—C20—C21177.2 (6)O88—C89—C90—C91178.9 (6)
N3—C20—C21—C220.3 (10)C94—C89—C90—C912.1 (10)
C19—C20—C21—C22178.2 (6)C89—C90—C91—C922.3 (11)
N3—C20—C21—C46177.7 (5)C90—C91—C92—C933.4 (11)
C19—C20—C21—C463.8 (9)C91—C92—C93—C944.3 (11)
C5—N4—C22—C21178.4 (6)C92—C93—C94—O95177.6 (6)
Zn53—N4—C22—C217.2 (9)C92—C93—C94—C894.1 (10)
C5—N4—C22—C230.1 (7)O88—C89—C94—O950.5 (8)
Zn53—N4—C22—C23174.4 (4)C90—C89—C94—O95178.6 (6)
C20—C21—C22—N41.1 (10)O88—C89—C94—C93177.9 (6)
C46—C21—C22—N4176.8 (5)C90—C89—C94—C933.0 (10)
C20—C21—C22—C23176.9 (6)C93—C94—O95—C9611.5 (9)
C46—C21—C22—C235.2 (9)C89—C94—O95—C96170.2 (6)
N4—C22—C23—C240.6 (7)C94—O95—C96—C97168.4 (5)
C21—C22—C23—C24179.0 (6)O95—C96—C97—O9880.3 (7)
C22—C23—C24—C50.9 (7)C96—C97—O98—C9987.6 (7)
N4—C5—C24—C230.8 (7)C97—O98—C99—C100166.4 (6)
C6—C5—C24—C23178.6 (6)O98—C99—C100—O10168.2 (7)
C5—C6—C25—C3073.2 (8)C99—C100—O101—C102164.9 (6)
C7—C6—C25—C30105.3 (7)C100—O101—C102—C103111.0 (7)
C5—C6—C25—C26104.0 (7)O101—C102—C103—O10465.9 (7)
C7—C6—C25—C2677.6 (8)C102—C103—O104—C105174.1 (5)
C30—C25—C26—C271.4 (9)C103—O104—C105—C10615.3 (9)
C6—C25—C26—C27175.8 (6)C103—O104—C105—C110164.9 (5)
C25—C26—C27—C281.1 (10)O104—C105—C106—C107178.9 (6)
C26—C27—C28—O31179.9 (6)C110—C105—C106—C1071.2 (10)
C26—C27—C28—C290.2 (10)C105—C106—C107—C1080.6 (10)
O31—C28—C29—C30179.0 (6)C106—C107—C108—C1090.1 (11)
C27—C28—C29—C301.2 (10)C107—C108—C109—C1100.1 (11)
C28—C29—C30—C250.9 (10)C108—C109—C110—O111179.3 (7)
C26—C25—C30—C290.4 (9)C108—C109—C110—C1050.5 (10)
C6—C25—C30—C29176.9 (6)O104—C105—C110—O1110.0 (8)
C10—C11—C32—C3772.7 (7)C106—C105—C110—O111179.9 (6)
C12—C11—C32—C37106.0 (7)O104—C105—C110—C109179.0 (5)
C10—C11—C32—C33106.7 (7)C106—C105—C110—C1091.1 (9)
C12—C11—C32—C3374.6 (7)C109—C110—O111—C1122.1 (9)
C37—C32—C33—C342.1 (8)C105—C110—O111—C112176.8 (5)
C11—C32—C33—C34177.3 (5)C110—O111—C112—C113178.1 (5)
C32—C33—C34—C350.6 (9)O111—C112—C113—O11478.2 (7)
C33—C34—C35—O38177.7 (6)C112—C113—O114—C11593.0 (7)
C33—C34—C35—C360.7 (9)C113—O114—C115—C116168.3 (6)
C34—C35—C36—C370.4 (10)O114—C115—C116—O11759.9 (7)
O38—C35—C36—C37178.1 (6)C115—C116—O117—C118168.4 (5)
C35—C36—C37—C321.2 (9)C116—O117—C118—C119110.6 (6)
C33—C32—C37—C362.4 (9)C89—O88—C119—C118179.6 (5)
C11—C32—C37—C36177.0 (6)O117—C118—C119—O8866.2 (7)
C17—C16—C39—C4473.8 (7)C151—O120—C121—C122103.4 (7)
C15—C16—C39—C44103.5 (7)C151—O120—C121—C12679.1 (8)
C17—C16—C39—C40106.6 (7)O120—C121—C122—C123178.5 (6)
C15—C16—C39—C4076.1 (7)C126—C121—C122—C1231.0 (10)
C44—C39—C40—C412.4 (9)C121—C122—C123—C1240.3 (10)
C16—C39—C40—C41178.0 (6)C122—C123—C124—C1250.9 (11)
C39—C40—C41—C421.8 (9)C123—C124—C125—C1261.5 (11)
C40—C41—C42—O45177.6 (6)C124—C125—C126—O127178.8 (7)
C40—C41—C42—C430.2 (10)C124—C125—C126—C1210.8 (10)
O45—C42—C43—C44178.6 (6)C122—C121—C126—C1250.4 (10)
C41—C42—C43—C440.6 (10)O120—C121—C126—C125177.9 (6)
C40—C39—C44—C431.5 (9)C122—C121—C126—O127179.9 (6)
C16—C39—C44—C43178.9 (6)O120—C121—C126—O1272.5 (9)
C42—C43—C44—C390.0 (10)C125—C126—O127—C12813.1 (10)
C22—C21—C46—C4773.6 (8)C121—C126—O127—C128166.6 (6)
C20—C21—C46—C47104.5 (7)C126—O127—C128—C129169.3 (6)
C22—C21—C46—C51110.2 (7)O127—C128—C129—O13070.6 (8)
C20—C21—C46—C5171.8 (7)C128—C129—O130—C13177.2 (8)
C51—C46—C47—C481.3 (9)C129—O130—C131—C132169.7 (6)
C21—C46—C47—C48175.0 (5)O130—C131—C132—O13366.5 (8)
C46—C47—C48—C490.4 (9)C131—C132—O133—C134173.3 (6)
C47—C48—C49—C502.6 (9)C132—O133—C134—C135171.3 (6)
C47—C48—C49—O52177.9 (5)O133—C134—C135—O13668.8 (8)
O52—C49—C50—C51177.6 (5)C134—C135—O136—C137162.3 (7)
C48—C49—C50—C512.9 (9)C135—O136—C137—C1388.0 (11)
C49—C50—C51—C461.1 (9)C135—O136—C137—C142172.3 (7)
C47—C46—C51—C501.0 (9)O136—C137—C138—C139179.4 (7)
C21—C46—C51—C50175.3 (6)C142—C137—C138—C1390.9 (11)
C10—N1—Zn53—N214.6 (5)C137—C138—C139—C1400.3 (12)
C7—N1—Zn53—N2178.5 (5)C138—C139—C140—C1412.2 (11)
C10—N1—Zn53—N4176.8 (5)C139—C140—C141—C1422.8 (11)
C7—N1—Zn53—N419.3 (5)C140—C141—C142—O143178.4 (7)
C10—N1—Zn53—N394.6 (7)C140—C141—C142—C1371.6 (11)
C7—N1—Zn53—N3101.4 (7)O136—C137—C142—O1433.1 (10)
C10—N1—Zn53—O5484.4 (5)C138—C137—C142—O143176.5 (7)
C7—N1—Zn53—O5479.5 (5)O136—C137—C142—C141180.0 (6)
C12—N2—Zn53—N113.5 (5)C138—C137—C142—C1410.3 (11)
C15—N2—Zn53—N1175.7 (5)C141—C142—O143—C144113.9 (7)
C12—N2—Zn53—N496.9 (8)C137—C142—O143—C14469.3 (8)
C15—N2—Zn53—N492.2 (8)C142—O143—C144—C145128.7 (6)
C12—N2—Zn53—N3174.3 (5)O143—C144—C145—O14673.6 (7)
C15—N2—Zn53—N314.8 (5)C144—C145—O146—C147174.7 (5)
C12—N2—Zn53—O5478.5 (5)C145—O146—C147—C148172.1 (5)
C15—N2—Zn53—O5492.4 (5)O146—C147—C148—O14973.6 (7)
C5—N4—Zn53—N114.6 (5)C147—C148—O149—C150154.9 (6)
C22—N4—Zn53—N1172.0 (5)C148—O149—C150—C15183.7 (7)
C5—N4—Zn53—N297.9 (8)C121—O120—C151—C150177.9 (6)
C22—N4—Zn53—N288.7 (8)O149—C150—C151—O12072.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O85i0.782.182.878 (7)149
O31—H31···O82i0.782.342.875 (6)127
O38—H38···O1520.961.742.688 (7)168
O45—H45···O114ii0.951.822.769 (6)180
O45—H45···O117ii0.952.613.030 (7)107
O52—H52···O154iii0.951.732.677 (7)179
O54—H54···O149iv0.941.802.740 (6)179
O152—H152···O980.941.932.872 (7)174
O154—H154···O1560.931.722.651 (7)180
O156—H156···O146v0.951.812.755 (7)180
Symmetry codes: (i) x, y1, z; (ii) x, y, z+1; (iii) x, y1, z+1; (iv) x+1, y, z+1; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Zn(C44H28N4O4)]·3C24H32O8·4CH4O
Mr2215.73
Crystal system, space groupTriclinic, P1
Temperature (K)110
a, b, c (Å)10.2643 (3), 13.4878 (4), 21.1227 (8)
α, β, γ (°)86.2858 (10), 77.9955 (13), 73.932 (3)
V3)2748.51 (15)
Z1
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15453, 15453, 13092
Rint0.000
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.167, 1.05
No. of reflections15453
No. of parameters1420
No. of restraints4
H-atom treatmentH-atom parameters constrained
(Δ/σ)max0.136
Δρmax, Δρmin (e Å3)0.96, 0.55
Absolute structureFlack (1983)
Absolute structure parameter0.477 (13)

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski, 1985), DENZO, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

Selected bond lengths (Å) top
N1—Zn532.047 (5)N4—Zn532.081 (5)
N2—Zn532.068 (5)Zn53—O542.123 (4)
N3—Zn532.081 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O85i0.782.182.878 (7)149
O31—H31···O82i0.782.342.875 (6)127
O38—H38···O1520.961.742.688 (7)168
O45—H45···O114ii0.951.822.769 (6)180
O45—H45···O117ii0.952.613.030 (7)107
O52—H52···O154iii0.951.732.677 (7)179
O54—H54···O149iv0.941.802.740 (6)179
O152—H152···O980.941.932.872 (7)174
O154—H154···O1560.931.722.651 (7)180
O156—H156···O146v0.951.812.755 (7)180
Symmetry codes: (i) x, y1, z; (ii) x, y, z+1; (iii) x, y1, z+1; (iv) x+1, y, z+1; (v) x+1, y, z.
 

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