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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m841–m842.
Published online 2010 June 26. doi:  10.1107/S1600536810022476
PMCID: PMC3006769

Bis(μ-4-methyl­benzoato-κ2 O:O′)bis­[aqua­(4-methyl­benzoato-κ2 O,O′)zinc(II)]–bis­(μ-4-methyl­benzoato-κ2 O:O′)bis­[(4-methyl­benzoato-κO)(nicotinamide-κN)zinc(II)]–water (1/1/2)

Abstract

The crystal structure of the title compound, [Zn2(C8H7O2)4(H2O)2]·[Zn2(C8H7O2)4(C6H6N2O)2]·2H2O, consists of two kinds of dinuclear ZnII complexes (complex A and complex B) and uncoordinated water mol­ecules. In complex A, [Zn2(C8H7O2)4(H2O)2], each Zn cation is chelated by a 4-methyl­benzoate (PMB) anion and coordinated by a water mol­ecule, and is further bridged by two PMB anions in a trigonal-bipyramidal geometry. In complex B, [Zn2(C8H7O2)4(C6H6N2O)2], each ZnII cation is coordinated by a monodentate PMB anion and one nicotinamide (NA) ligand, and is further bridged by two PMB anions in a tetra­hedral geometry. Weak intra-mol­ecular π–π stacking between adjacent benzene rings is observed in complex B, the centroid–centroid distance being 3.710 (2) Å. Extensive O—H(...)O and N—H(...)O hydrogen bonding and weak C—H(...)O hydrogen bonding is present in the crystal structure. The crystal studied was a racemic twin; the minor twin component refined to 38%.

Related literature

For related structures, see: Greenaway et al. (1984 [triangle]); Hökelek & Necefoğlu (1996 [triangle]); Hökelek et al. (2009a [triangle],b [triangle],c [triangle],d [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m841-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C8H7O2)4(H2O)2]·[Zn2(C8H7O2)4(C6H6N2O)2]·2H2O
  • M r = 1658.97
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m841-efi1.jpg
  • a = 19.7038 (3) Å
  • b = 12.2884 (2) Å
  • c = 15.4477 (3) Å
  • β = 98.708 (1)°
  • V = 3697.21 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.36 mm−1
  • T = 100 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.718, T max = 0.863
  • 35979 measured reflections
  • 16444 independent reflections
  • 14033 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.080
  • S = 1.01
  • 16444 reflections
  • 964 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.52 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 7229 Friedel pairs
  • Flack parameter: 0.382 (7)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022476/xu2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022476/xu2762Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

supplementary crystallographic information

Comment

As part of our ongoing study on transition metal complexes of benzoate and nicotinamide, herein we report the synthesis and the structure of the title cocrystal diaquabis(µ-4-methylbenzoato-κ2O:O')- bis(4-methylbenzoato-κ2O:O')dizinc(II), (A), and bis(nicotinamide-κN')- bis(µ-4-methylbenzoato-κ2O:O')bis(4-methylbenzoato-κO)dizinc(II) dihydrate, (B).

The components of the title compound, [Zn2(C8H7O2)4(H2O)2], (A), and [Zn2(C8H7O2)4(C6H6N2O)2].2(H2O), (B), are binuclear complexes. In the complex A, each Zn cation is chelated by a 4-methylbenzoate (PMB) anion and coordinated by a water molecule, and is further bridged by two PMB anions with a trigonal bipyramidal geometry. In the complex B, each ZnII cation is coordinated by a monodentate PMB anion and one nicotinamide (NA) ligand, and is further bridged by two PMB anions with a tetrahedral geometry. The intramolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2) link the two uncoordinated water molecules to the O, N and C atoms of the carboxylate and NA groups, respectively (Fig. 1).

The average Zn—O bond lengths (Table 1) are 2.071 (3) and 1.942 (3) Å for (A) and (B), respectively, and the Zn atoms are displaced out of the least-squares planes of the carboxylate groups: Zn1 atom for (O1/C1/O2), (O3/C9/O4) and (O7/C25/O8) by 0.0892 (4), -0.0858 (4) and -0.2690 (4) Å, respectively, Zn2 atom for (O1/C1/O2), (O3/C9/O4) and (O5/C17/O6) by -0.0702 (4), 0.0213 (4) and -0.2301 (4) Å, respectively, Zn3 atom for (O11/C33/O12), (O13/C41/O14) and (O15/C49/O16) by -0.1442 (4), -0.0176 (4) and 0.0844 (3) Å, respectively, and Zn4 atom for (O11/C33/O12), (O13/C41/O14) and (O17/C57/O18) by 0.0461 (4), 0.1211 (4) and -0.0012 (3) Å, respectively. In (A), the O7—Zn1—O8 and O5—Zn2—O6 angles are 57.37 (10) and 58.03 (10) °, respectively. The corresponding O—M—O (where M is a metal) angles are 52.91 (4)° and 53.96 (4)° in [Cd(C8H5O3)2(C6H6N2O)2(H2O)].H2O (Hökelek et al., 2009a), 60.70 (4)° in [Co(C9H10NO2)2(C6H6N2O)(H2O)2] (Hökelek et al., 2009b), 58.45 (9)° in [Mn(C9H10NO2)2(C6H6N2O)(H2O)2] (Hökelek et al., 2009c), 60.03 (6)° in [Zn(C8H8NO2)2(C6H6N2O)2].H2O (Hökelek et al., 2009d), 58.3 (3)° in [Zn2(DENA)2(C7H5O3)4].2H2O (Hökelek & Necefoğlu, 1996) and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2—C7), B (C10—C15), C (C18—C23), D (C26—C31), G (C34—C39), H (C42—C47), I (C50—C55) and J (C58—C63) are 4.44 (26), 1.40 (21), 5.40 (15), 8.20 (14), 3.33 (26), 10.45 (26), 9.93 (10) and 9.86 (11) °, respectively, while those between rings A, B, C, D, E (Zn1/O7/O8/C25), F (Zn2/O5/O6/C17) and G, H, I, J, K (N1/C65—C69), L (N3/C71—C75) are A/B = 63.10 (12), A/C = 77.01 (12), A/D = 82.24 (13), B/C = 78.45 (12), B/D = 86.45 (14), C/D = 8.23 (13), E/F = 6.17 (9) ° and G/H = 62.85 (10), G/I = 79.23 (12), G/J = 78.86 (12), H/I = 81.13 (12), H/J = 80.21 (11), I/J = 1.32 (10), K/L = 65.25 (10) °.

In the crystal structure, extensive O—H···O, N—H···O hydrogen bonding and weak C—H···O hydrogen bonding (Table 2) are present, in which they may be effective in the stabilization of the structure. The π–π contact between the benzene rings, Cg9—Cg10, where Cg9 and Cg10 are the centroids of the rings I (C50—C55) and J (C58—C33), respectively] may further stabilize the structure, with centroid-centroid distance of 3.710 (2) Å.

Experimental

The title compound was prepared by the reaction of ZnSO4.H2O (0.90 g, 5 mmol) in H2O (200 ml) and NA (1.22 g, 10 mmol) in H2O (10 ml) with sodium 4-methylbenzoate (1.58 g, 10 mmol) in H2O (150 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colorless single crystals.

Refinement

Water H atoms were placed in chemical sensitive positions and refined in a riding mode with Uiso(H) = 1.2Ueq(O). Methyl H atoms were placed in calculated positions with C—H = 0.98 Å, and torsion angles were refined to fit the electron density, Uiso(H) = 1.5Ueq(C). The remaining H atoms were positioned geometrically with N—H = 0.88 Å and C—H = 0.95 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. Hydrogen bonds are shown as dashed lines.

Crystal data

[Zn2(C8H7O2)4(H2O)2]·[Zn2(C8H7O2)4(C6H6N2O)2]·2H2OF(000) = 1712
Mr = 1658.97Dx = 1.490 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 7336 reflections
a = 19.7038 (3) Åθ = 2.5–25.5°
b = 12.2884 (2) ŵ = 1.36 mm1
c = 15.4477 (3) ÅT = 100 K
β = 98.708 (1)°Block, colorless
V = 3697.21 (11) Å30.35 × 0.25 × 0.15 mm
Z = 2

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer16444 independent reflections
Radiation source: fine-focus sealed tube14033 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 28.3°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −26→23
Tmin = 0.718, Tmax = 0.863k = −16→16
35979 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.080w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.004
16444 reflectionsΔρmax = 0.38 e Å3
964 parametersΔρmin = −0.52 e Å3
2 restraintsAbsolute structure: Flack (1983), 7229 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.382 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
Zn10.28355 (2)0.10592 (3)0.15711 (2)0.01471 (9)
Zn20.20670 (2)0.07066 (3)0.32791 (2)0.01696 (10)
Zn30.69302 (2)0.99800 (3)0.33479 (2)0.01354 (10)
Zn40.79811 (2)1.00907 (3)0.16901 (2)0.01335 (10)
N10.63153 (16)1.0446 (2)0.42375 (17)0.0155 (7)
N20.41642 (17)0.9780 (2)0.39318 (18)0.0175 (7)
H2A0.37330.95760.38940.021*
H2B0.43760.97340.34710.021*
N30.85772 (15)1.0568 (2)0.07915 (17)0.0137 (6)
N41.07081 (17)0.9790 (2)0.0974 (2)0.0201 (7)
H4A1.11380.95800.10010.024*
H4B1.04970.97140.14330.024*
O10.34255 (14)0.18920 (19)0.24754 (14)0.0201 (6)
O20.28988 (14)0.1544 (2)0.36336 (15)0.0205 (6)
O30.19960 (13)0.1879 (2)0.12372 (14)0.0200 (6)
O40.14732 (14)0.1571 (2)0.23982 (15)0.0220 (6)
O50.26286 (15)−0.0934 (2)0.39755 (15)0.0205 (6)
O60.17315 (14)−0.0784 (2)0.29432 (16)0.0205 (6)
O70.22349 (14)−0.0618 (2)0.09298 (15)0.0192 (6)
O80.30657 (14)−0.0412 (2)0.20415 (15)0.0215 (6)
O90.32937 (13)0.1279 (2)0.05389 (14)0.0175 (6)
H910.30020.1244−0.00290.021*
H920.36500.07330.05280.021*
O100.16159 (13)0.1037 (2)0.43203 (15)0.0194 (6)
H1010.12720.05020.44170.023*
H1020.19880.09720.48100.023*
O110.64993 (14)1.0712 (2)0.23049 (15)0.0195 (6)
O120.71470 (14)1.09187 (19)0.12404 (15)0.0173 (6)
O130.77572 (14)1.08106 (18)0.38194 (15)0.0162 (6)
O140.84098 (14)1.0780 (2)0.27519 (14)0.0182 (6)
O150.60792 (14)0.8331 (2)0.27054 (15)0.0204 (6)
O160.71267 (14)0.84434 (19)0.34807 (15)0.0170 (6)
O170.77405 (14)0.85598 (18)0.15918 (15)0.0160 (6)
O180.87894 (14)0.8431 (2)0.23425 (16)0.0205 (6)
O190.42153 (14)1.0236 (2)0.53595 (15)0.0186 (6)
O201.06431 (14)1.0350 (2)−0.04234 (16)0.0233 (6)
O210.47309 (16)0.9262 (3)0.23420 (17)0.0376 (9)
H2110.52120.90780.23630.045*
H2120.45460.94190.18180.045*
O221.01450 (19)0.9193 (3)0.2565 (2)0.0570 (12)
H2211.04050.93090.31430.068*
H2220.97370.87820.26480.068*
C10.3372 (2)0.1966 (3)0.3273 (2)0.0161 (8)
C20.39105 (19)0.2606 (3)0.3843 (2)0.0151 (8)
C30.3864 (2)0.2793 (3)0.4718 (2)0.0207 (9)
H30.34850.25160.49630.025*
C40.4373 (2)0.3387 (3)0.5235 (2)0.0264 (9)
H40.43380.35150.58330.032*
C50.4930 (2)0.3792 (3)0.4892 (2)0.0277 (10)
C60.4968 (2)0.3615 (3)0.4017 (2)0.0284 (9)
H60.53450.38970.37710.034*
C70.4462 (2)0.3030 (3)0.3495 (2)0.0242 (9)
H70.44940.29190.28940.029*
C80.5502 (2)0.4410 (4)0.5459 (3)0.0426 (12)
H8A0.57380.48810.50880.064*
H8B0.58300.38910.57690.064*
H8C0.53060.48560.58860.064*
C90.1499 (2)0.1971 (3)0.1652 (2)0.0145 (8)
C100.0896 (2)0.2605 (3)0.1232 (2)0.0159 (8)
C110.03233 (19)0.2751 (3)0.1654 (2)0.0205 (8)
H110.03230.24490.22200.025*
C12−0.0243 (2)0.3327 (3)0.1262 (2)0.0246 (9)
H12−0.06240.34190.15650.029*
C13−0.02635 (19)0.3774 (3)0.0431 (2)0.0206 (8)
C140.0302 (2)0.3623 (3)0.0009 (2)0.0261 (9)
H140.02970.3917−0.05610.031*
C150.08771 (19)0.3052 (3)0.0402 (2)0.0190 (8)
H150.12600.29670.01010.023*
C16−0.0885 (2)0.4377 (3)−0.0005 (3)0.0328 (10)
H16A−0.11350.46810.04420.049*
H16B−0.11850.3876−0.03800.049*
H16C−0.07410.4969−0.03620.049*
C170.2132 (2)−0.1365 (3)0.3483 (2)0.0162 (8)
C180.1993 (2)−0.2550 (3)0.3528 (2)0.0188 (8)
C190.1421 (2)−0.3021 (3)0.3038 (2)0.0252 (9)
H190.1100−0.25750.26780.030*
C200.1312 (2)−0.4126 (3)0.3065 (2)0.0355 (11)
H200.0916−0.44290.27240.043*
C210.1768 (2)−0.4807 (3)0.3578 (2)0.0327 (10)
C220.2338 (2)−0.4338 (3)0.4076 (3)0.0302 (10)
H220.2656−0.47850.44400.036*
C230.2451 (2)−0.3228 (3)0.4050 (2)0.0250 (9)
H230.2847−0.29240.43930.030*
C240.1652 (3)−0.6017 (3)0.3607 (3)0.0542 (14)
H24A0.2076−0.63990.35290.081*
H24B0.1284−0.62250.31370.081*
H24C0.1523−0.62160.41740.081*
C250.2687 (2)−0.1023 (3)0.1512 (2)0.0170 (9)
C260.2772 (2)−0.2220 (3)0.1571 (2)0.0174 (8)
C270.2314 (2)−0.2910 (3)0.1080 (2)0.0236 (9)
H270.1943−0.26130.06860.028*
C280.2385 (2)−0.4027 (3)0.1151 (3)0.0275 (10)
H280.2058−0.44850.08120.033*
C290.2919 (2)−0.4482 (3)0.1703 (3)0.0307 (10)
C300.3389 (2)−0.3788 (3)0.2193 (2)0.0323 (11)
H300.3765−0.40890.25750.039*
C310.3318 (2)−0.2670 (3)0.2132 (2)0.0263 (10)
H310.3642−0.22100.24740.032*
C320.2998 (3)−0.5691 (3)0.1791 (3)0.0514 (13)
H32A0.3443−0.59090.16380.077*
H32B0.2629−0.60500.13960.077*
H32C0.2973−0.59050.23960.077*
C330.66019 (19)1.1070 (3)0.1573 (2)0.0124 (7)
C340.60372 (19)1.1704 (3)0.1063 (2)0.0140 (7)
C350.54184 (19)1.1833 (3)0.1390 (2)0.0162 (8)
H350.53681.15330.19440.019*
C360.4880 (2)1.2394 (3)0.0912 (2)0.0207 (8)
H360.44661.24890.11470.025*
C370.4934 (2)1.2820 (3)0.0092 (2)0.0202 (8)
C380.5552 (2)1.2687 (3)−0.0227 (2)0.0233 (9)
H380.56021.2974−0.07850.028*
C390.6092 (2)1.2145 (3)0.0256 (2)0.0178 (8)
H390.65111.20720.00280.021*
C400.4339 (2)1.3391 (4)−0.0450 (3)0.0319 (10)
H40A0.45121.3983−0.07810.048*
H40B0.40341.3690−0.00640.048*
H40C0.40841.2872−0.08580.048*
C410.82912 (19)1.1045 (3)0.3500 (2)0.0136 (7)
C420.88448 (19)1.1675 (3)0.4058 (2)0.0130 (7)
C430.87193 (19)1.2131 (3)0.4849 (2)0.0161 (8)
H430.82831.20540.50340.019*
C440.9243 (2)1.2698 (3)0.5357 (2)0.0208 (8)
H440.91571.30210.58880.025*
C450.9888 (2)1.2809 (3)0.5114 (2)0.0212 (9)
C461.0001 (2)1.2349 (3)0.4332 (2)0.0215 (8)
H461.04401.24180.41530.026*
C470.94859 (19)1.1793 (3)0.3805 (2)0.0173 (8)
H470.95721.14890.32670.021*
C481.0455 (2)1.3396 (3)0.5700 (2)0.0323 (10)
H48A1.07401.37950.53390.048*
H48B1.07391.28670.60650.048*
H48C1.02541.39100.60750.048*
C490.6605 (2)0.7893 (3)0.3108 (2)0.0151 (8)
C500.6655 (2)0.6689 (3)0.3203 (2)0.0176 (8)
C510.6159 (2)0.6022 (3)0.2732 (2)0.0171 (8)
H510.57880.63370.23490.021*
C520.6203 (2)0.4904 (3)0.2821 (2)0.0229 (9)
H520.58700.44590.24790.027*
C530.6722 (2)0.4418 (3)0.3395 (2)0.0246 (9)
C540.7219 (2)0.5089 (3)0.3868 (2)0.0241 (9)
H540.75820.47760.42640.029*
C550.7185 (2)0.6202 (3)0.3764 (2)0.0202 (8)
H550.75320.66450.40820.024*
C560.6738 (2)0.3198 (3)0.3533 (3)0.0362 (11)
H56A0.72160.29480.36430.054*
H56B0.64980.28370.30090.054*
H56C0.65120.30170.40380.054*
C570.8255 (2)0.8002 (3)0.1982 (2)0.0139 (8)
C580.81646 (19)0.6797 (3)0.1965 (2)0.0146 (8)
C590.76113 (19)0.6313 (3)0.1440 (2)0.0191 (8)
H590.72800.67560.10940.023*
C600.7538 (2)0.5190 (3)0.1416 (3)0.0241 (9)
H600.71580.48700.10520.029*
C610.8017 (2)0.4529 (3)0.1921 (2)0.0245 (9)
C620.8570 (2)0.5018 (3)0.2451 (2)0.0231 (9)
H620.88970.45790.28080.028*
C630.86452 (19)0.6136 (3)0.2460 (2)0.0188 (8)
H630.90320.64560.28100.023*
C640.7929 (3)0.3304 (3)0.1886 (3)0.0432 (12)
H64A0.83120.29600.22660.065*
H64B0.79210.30520.12830.065*
H64C0.74960.31080.20870.065*
C650.5648 (2)1.0193 (3)0.4140 (2)0.0149 (8)
H650.54540.97840.36410.018*
C660.52289 (19)1.0508 (3)0.4743 (2)0.0126 (7)
C670.5516 (2)1.1111 (3)0.5462 (2)0.0160 (8)
H670.52391.13480.58780.019*
C680.6204 (2)1.1368 (3)0.5574 (2)0.0197 (8)
H680.64101.17750.60680.024*
C690.6588 (2)1.1020 (3)0.4948 (2)0.0161 (8)
H690.70641.11910.50230.019*
C700.4496 (2)1.0156 (3)0.4684 (2)0.0148 (8)
C710.9239 (2)1.0286 (3)0.0847 (2)0.0161 (8)
H710.94390.98650.13350.019*
C720.96465 (19)1.0578 (3)0.0227 (2)0.0163 (8)
C730.9348 (2)1.1208 (3)−0.0482 (2)0.0200 (9)
H730.96111.1436−0.09170.024*
C740.8664 (2)1.1497 (3)−0.0544 (2)0.0183 (8)
H740.84501.1917−0.10250.022*
C750.8297 (2)1.1165 (3)0.0103 (2)0.0160 (8)
H750.78281.13680.00580.019*
C761.0381 (2)1.0218 (3)0.0246 (2)0.0177 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0127 (2)0.0163 (2)0.01528 (19)0.00210 (19)0.00272 (16)−0.00207 (17)
Zn20.0139 (2)0.0175 (2)0.0189 (2)−0.00305 (19)0.00077 (16)0.00476 (18)
Zn30.0115 (3)0.01344 (19)0.01577 (19)−0.00085 (17)0.00219 (16)0.00244 (17)
Zn40.0120 (3)0.0133 (2)0.0149 (2)0.00080 (18)0.00251 (16)−0.00128 (16)
N10.0163 (19)0.0153 (15)0.0151 (13)−0.0018 (13)0.0031 (12)0.0040 (12)
N20.012 (2)0.0215 (17)0.0204 (14)−0.0003 (14)0.0068 (13)0.0002 (13)
N30.0102 (18)0.0145 (15)0.0171 (14)−0.0025 (13)0.0047 (11)−0.0034 (12)
N40.0061 (19)0.0269 (18)0.0279 (16)0.0040 (14)0.0042 (13)−0.0005 (14)
O10.0243 (17)0.0180 (13)0.0177 (12)−0.0008 (12)0.0018 (10)−0.0010 (10)
O20.0142 (15)0.0221 (14)0.0253 (13)−0.0050 (12)0.0032 (10)0.0042 (11)
O30.0140 (15)0.0247 (14)0.0213 (12)0.0057 (12)0.0033 (10)0.0001 (10)
O40.0184 (16)0.0249 (15)0.0215 (13)0.0009 (12)−0.0006 (10)0.0059 (11)
O50.0230 (17)0.0218 (14)0.0163 (11)−0.0077 (12)0.0016 (11)0.0003 (10)
O60.0193 (16)0.0210 (14)0.0204 (12)−0.0018 (12)0.0008 (10)0.0007 (11)
O70.0189 (16)0.0178 (13)0.0214 (13)0.0065 (11)0.0051 (11)0.0021 (10)
O80.0264 (17)0.0160 (13)0.0210 (12)0.0024 (12)0.0000 (11)−0.0016 (11)
O90.0156 (16)0.0209 (13)0.0163 (11)0.0037 (11)0.0033 (10)−0.0003 (10)
O100.0137 (16)0.0222 (14)0.0217 (12)−0.0038 (11)0.0004 (10)0.0036 (10)
O110.0159 (16)0.0241 (14)0.0185 (12)0.0018 (12)0.0031 (10)0.0075 (11)
O120.0162 (17)0.0170 (13)0.0191 (12)0.0023 (11)0.0036 (10)0.0002 (10)
O130.0103 (16)0.0146 (13)0.0237 (13)−0.0032 (11)0.0030 (10)0.0002 (10)
O140.0154 (16)0.0228 (14)0.0166 (12)−0.0010 (11)0.0036 (10)−0.0056 (10)
O150.0168 (17)0.0206 (14)0.0230 (13)0.0020 (12)0.0008 (11)0.0020 (11)
O160.0161 (16)0.0147 (12)0.0199 (13)−0.0024 (11)0.0018 (11)0.0014 (10)
O170.0160 (16)0.0123 (12)0.0191 (12)0.0025 (11)0.0009 (10)−0.0006 (10)
O180.0136 (16)0.0205 (14)0.0269 (13)−0.0023 (11)0.0020 (11)−0.0033 (11)
O190.0146 (16)0.0226 (14)0.0202 (12)−0.0015 (12)0.0081 (11)0.0001 (10)
O200.0174 (17)0.0257 (15)0.0286 (14)0.0040 (13)0.0093 (12)−0.0008 (12)
O210.015 (2)0.073 (3)0.0232 (15)0.0114 (16)−0.0023 (13)−0.0068 (14)
O220.025 (2)0.112 (3)0.0313 (17)−0.020 (2)−0.0062 (15)0.0273 (19)
C10.017 (2)0.0107 (17)0.0203 (17)0.0053 (15)0.0001 (15)0.0024 (13)
C20.014 (2)0.0141 (17)0.0171 (16)0.0005 (15)0.0013 (14)0.0037 (13)
C30.021 (2)0.020 (2)0.0217 (17)−0.0030 (17)0.0052 (15)−0.0015 (15)
C40.029 (3)0.029 (2)0.0189 (18)0.0005 (19)−0.0038 (16)−0.0077 (16)
C50.034 (3)0.019 (2)0.0249 (19)−0.0094 (19)−0.0104 (17)−0.0005 (15)
C60.019 (2)0.035 (2)0.031 (2)−0.0128 (19)0.0011 (16)0.0060 (17)
C70.024 (2)0.031 (2)0.0171 (17)−0.0038 (18)0.0023 (15)0.0034 (16)
C80.048 (3)0.028 (2)0.043 (2)−0.017 (2)−0.021 (2)0.001 (2)
C90.017 (2)0.0074 (16)0.0175 (16)0.0003 (14)−0.0015 (14)−0.0015 (13)
C100.016 (2)0.0117 (17)0.0187 (16)0.0014 (15)−0.0005 (14)−0.0005 (13)
C110.018 (2)0.026 (2)0.0171 (16)0.0004 (17)0.0024 (14)−0.0006 (14)
C120.016 (2)0.029 (2)0.0292 (19)0.0064 (17)0.0050 (15)−0.0073 (17)
C130.019 (2)0.0136 (18)0.0269 (18)0.0034 (16)−0.0042 (15)−0.0029 (15)
C140.024 (3)0.029 (2)0.0245 (19)0.0009 (18)−0.0011 (16)0.0057 (16)
C150.015 (2)0.023 (2)0.0194 (17)0.0008 (16)0.0047 (14)0.0004 (15)
C160.026 (2)0.027 (2)0.042 (2)0.0132 (19)−0.0059 (18)0.0008 (19)
C170.020 (2)0.0186 (18)0.0117 (15)0.0003 (17)0.0065 (14)0.0001 (14)
C180.022 (2)0.0156 (18)0.0205 (17)−0.0034 (17)0.0090 (15)−0.0028 (14)
C190.033 (3)0.024 (2)0.0156 (17)−0.0065 (19)−0.0038 (15)0.0035 (15)
C200.051 (3)0.028 (2)0.025 (2)−0.018 (2)−0.0045 (19)−0.0018 (17)
C210.052 (3)0.022 (2)0.0259 (19)−0.011 (2)0.0125 (19)−0.0063 (16)
C220.033 (3)0.017 (2)0.041 (2)0.0033 (19)0.0071 (19)0.0034 (17)
C230.020 (2)0.019 (2)0.035 (2)−0.0002 (17)0.0019 (16)−0.0024 (16)
C240.087 (4)0.018 (2)0.059 (3)−0.015 (3)0.015 (3)−0.004 (2)
C250.021 (2)0.0171 (18)0.0164 (16)0.0038 (16)0.0142 (16)0.0041 (15)
C260.020 (2)0.0185 (18)0.0143 (15)−0.0010 (17)0.0058 (14)0.0014 (15)
C270.014 (2)0.020 (2)0.035 (2)−0.0005 (17)−0.0005 (16)0.0016 (16)
C280.028 (3)0.020 (2)0.033 (2)−0.0034 (18)0.0026 (17)0.0013 (16)
C290.046 (3)0.0159 (19)0.031 (2)0.002 (2)0.0064 (19)0.0046 (17)
C300.043 (3)0.023 (2)0.027 (2)0.007 (2)−0.0082 (19)0.0052 (17)
C310.039 (3)0.021 (2)0.0172 (17)0.0027 (19)−0.0026 (16)−0.0014 (15)
C320.063 (4)0.028 (2)0.057 (3)0.007 (3)−0.008 (3)0.001 (2)
C330.013 (2)0.0059 (15)0.0176 (16)−0.0033 (14)0.0008 (14)−0.0026 (13)
C340.015 (2)0.0092 (16)0.0166 (16)−0.0023 (15)−0.0010 (13)−0.0031 (13)
C350.015 (2)0.0168 (18)0.0176 (16)−0.0006 (15)0.0036 (14)0.0006 (14)
C360.015 (2)0.023 (2)0.0254 (18)−0.0005 (17)0.0054 (15)0.0001 (15)
C370.015 (2)0.0164 (18)0.0268 (19)0.0003 (16)−0.0045 (15)0.0016 (15)
C380.027 (3)0.024 (2)0.0186 (17)0.0037 (18)0.0027 (16)0.0077 (15)
C390.015 (2)0.0213 (19)0.0181 (16)0.0036 (16)0.0066 (14)0.0009 (15)
C400.022 (3)0.035 (2)0.036 (2)0.009 (2)−0.0044 (18)0.0085 (19)
C410.013 (2)0.0072 (15)0.0200 (16)0.0009 (15)0.0019 (14)0.0006 (13)
C420.014 (2)0.0097 (16)0.0146 (15)−0.0008 (14)0.0009 (13)0.0021 (13)
C430.010 (2)0.021 (2)0.0180 (17)−0.0031 (16)0.0058 (14)0.0003 (15)
C440.023 (2)0.022 (2)0.0175 (17)−0.0028 (17)0.0023 (15)−0.0026 (15)
C450.022 (2)0.0175 (19)0.0225 (18)−0.0026 (17)−0.0031 (15)−0.0013 (15)
C460.011 (2)0.024 (2)0.0301 (19)−0.0044 (16)0.0026 (15)−0.0024 (16)
C470.019 (2)0.0198 (19)0.0140 (15)−0.0004 (16)0.0042 (14)−0.0014 (14)
C480.024 (3)0.034 (2)0.036 (2)−0.0047 (19)−0.0053 (18)−0.0100 (18)
C490.015 (2)0.0191 (19)0.0133 (15)−0.0023 (16)0.0075 (14)0.0030 (14)
C500.022 (2)0.0149 (18)0.0174 (16)0.0022 (16)0.0096 (15)0.0029 (14)
C510.018 (2)0.0178 (18)0.0159 (16)−0.0023 (16)0.0045 (14)0.0022 (14)
C520.032 (3)0.021 (2)0.0169 (17)−0.0047 (18)0.0072 (16)−0.0020 (15)
C530.031 (3)0.0122 (19)0.033 (2)0.0025 (17)0.0135 (18)0.0037 (16)
C540.022 (2)0.020 (2)0.030 (2)0.0038 (17)0.0038 (16)0.0064 (16)
C550.013 (2)0.021 (2)0.0259 (18)0.0013 (17)0.0020 (15)0.0020 (15)
C560.046 (3)0.013 (2)0.050 (3)0.002 (2)0.009 (2)0.0016 (18)
C570.017 (2)0.0149 (17)0.0113 (15)0.0013 (16)0.0071 (14)0.0012 (13)
C580.016 (2)0.0145 (18)0.0141 (15)0.0007 (15)0.0041 (13)0.0005 (14)
C590.017 (2)0.0152 (19)0.0254 (18)0.0017 (16)0.0028 (15)−0.0028 (15)
C600.020 (2)0.021 (2)0.032 (2)−0.0043 (17)0.0073 (17)−0.0032 (16)
C610.033 (2)0.0109 (18)0.033 (2)0.0032 (17)0.0156 (18)0.0018 (15)
C620.029 (2)0.0191 (19)0.0217 (18)0.0044 (17)0.0050 (16)0.0018 (15)
C630.017 (2)0.0184 (19)0.0218 (17)0.0012 (16)0.0059 (15)−0.0007 (14)
C640.051 (3)0.017 (2)0.066 (3)0.000 (2)0.021 (3)0.001 (2)
C650.013 (2)0.0140 (18)0.0173 (16)−0.0012 (15)0.0001 (14)0.0014 (14)
C660.010 (2)0.0111 (17)0.0162 (15)0.0028 (14)0.0017 (13)0.0056 (13)
C670.014 (2)0.0174 (18)0.0179 (17)−0.0014 (16)0.0051 (14)0.0015 (14)
C680.025 (3)0.0165 (18)0.0174 (17)−0.0045 (17)0.0032 (15)−0.0013 (14)
C690.015 (2)0.0169 (18)0.0162 (16)−0.0021 (16)0.0003 (14)0.0078 (14)
C700.013 (2)0.0107 (17)0.0221 (18)0.0026 (15)0.0057 (15)0.0019 (14)
C710.014 (2)0.0142 (17)0.0195 (17)0.0022 (16)0.0015 (15)−0.0008 (14)
C720.014 (2)0.0163 (18)0.0188 (17)−0.0014 (16)0.0039 (14)−0.0053 (14)
C730.031 (3)0.0155 (19)0.0145 (17)−0.0009 (17)0.0082 (16)−0.0008 (14)
C740.018 (2)0.0193 (19)0.0164 (16)−0.0002 (16)0.0001 (14)−0.0006 (14)
C750.012 (2)0.0176 (18)0.0180 (16)0.0007 (15)0.0000 (14)−0.0027 (14)
C760.019 (2)0.0115 (18)0.0228 (18)−0.0029 (16)0.0039 (16)−0.0032 (14)

Geometric parameters (Å, °)

Zn1—O11.964 (2)C24—H24A0.9800
Zn1—O31.939 (3)C24—H24B0.9800
Zn1—O72.505 (3)C24—H24C0.9800
Zn1—O81.975 (2)C25—C261.482 (5)
Zn1—O91.966 (2)C26—C271.379 (5)
Zn2—O21.942 (3)C26—C311.390 (5)
Zn2—O41.967 (2)C27—C281.382 (5)
Zn2—O52.467 (3)C27—H270.9500
Zn2—O61.989 (3)C28—C291.370 (6)
Zn2—O101.994 (2)C28—H280.9500
Zn3—O111.926 (2)C29—C301.394 (6)
Zn3—O131.967 (3)C29—C321.498 (5)
Zn3—O161.932 (2)C30—C311.383 (5)
Zn3—N12.047 (3)C30—H300.9500
Zn4—O121.968 (3)C31—H310.9500
Zn4—O141.924 (2)C32—H32A0.9800
Zn4—O171.940 (2)C32—H32B0.9800
Zn4—N32.036 (3)C32—H32C0.9800
N1—C651.336 (5)C33—C341.484 (5)
N1—C691.347 (4)C34—C391.378 (4)
N2—C701.328 (4)C34—C351.398 (5)
N2—H2A0.8800C35—C361.382 (5)
N2—H2B0.8800C35—H350.9500
N3—C711.339 (5)C36—C371.389 (5)
N3—C751.341 (4)C36—H360.9500
N4—C761.318 (5)C37—C381.391 (5)
N4—H4A0.8800C37—C401.507 (5)
N4—H4B0.8800C38—C391.375 (5)
O1—C11.255 (4)C38—H380.9500
O2—C11.267 (4)C39—H390.9500
O3—C91.255 (4)C40—H40A0.9800
O4—C91.261 (4)C40—H40B0.9800
O5—C171.262 (4)C40—H40C0.9800
O6—C171.275 (4)C41—C421.500 (5)
O7—C251.268 (4)C42—C471.385 (5)
O8—C251.267 (5)C42—C431.399 (4)
O9—H910.9738C43—C441.386 (5)
O9—H920.9734C43—H430.9500
O10—H1010.9719C44—C451.385 (5)
O10—H1020.9734C44—H440.9500
O11—C331.258 (4)C45—C461.383 (5)
O12—C331.272 (4)C45—C481.510 (5)
O13—C411.261 (4)C46—C471.382 (5)
O14—C411.256 (4)C46—H460.9500
O15—C491.247 (4)C47—H470.9500
O16—C491.290 (4)C48—H48A0.9800
O17—C571.295 (4)C48—H48B0.9800
O18—C571.233 (4)C48—H48C0.9800
O19—C701.257 (4)C49—C501.489 (5)
O20—C761.235 (4)C50—C551.388 (5)
O21—H2110.9712C50—C511.393 (5)
O21—H2120.8577C51—C521.382 (5)
O22—H2210.9708C51—H510.9500
O22—H2220.9737C52—C531.384 (5)
C1—C21.496 (5)C52—H520.9500
C2—C71.386 (5)C53—C541.399 (5)
C2—C31.387 (4)C53—C561.514 (5)
C3—C41.391 (5)C54—C551.377 (5)
C3—H30.9500C54—H540.9500
C4—C51.381 (5)C55—H550.9500
C4—H40.9500C56—H56A0.9800
C5—C61.383 (5)C56—H56B0.9800
C5—C81.522 (5)C56—H56C0.9800
C6—C71.383 (5)C57—C581.490 (5)
C6—H60.9500C58—C631.387 (5)
C7—H70.9500C58—C591.390 (5)
C8—H8A0.9800C59—C601.388 (5)
C8—H8B0.9800C59—H590.9500
C8—H8C0.9800C60—C611.391 (5)
C9—C101.485 (5)C60—H600.9500
C10—C151.390 (5)C61—C621.396 (6)
C10—C111.398 (5)C61—C641.516 (5)
C11—C121.380 (5)C62—C631.381 (5)
C11—H110.9500C62—H620.9500
C12—C131.391 (5)C63—H630.9500
C12—H120.9500C64—H64A0.9800
C13—C141.386 (5)C64—H64B0.9800
C13—C161.501 (5)C64—H64C0.9800
C14—C151.391 (5)C65—C661.391 (5)
C14—H140.9500C65—H650.9500
C15—H150.9500C66—C671.383 (5)
C16—H16A0.9800C66—C701.496 (5)
C16—H16B0.9800C67—C681.378 (5)
C16—H16C0.9800C67—H670.9500
C17—C181.486 (5)C68—C691.382 (5)
C18—C191.385 (5)C68—H680.9500
C18—C231.392 (5)C69—H690.9500
C19—C201.377 (5)C71—C721.387 (5)
C19—H190.9500C71—H710.9500
C20—C211.384 (6)C72—C731.397 (5)
C20—H200.9500C72—C761.509 (5)
C21—C221.387 (6)C73—C741.382 (5)
C21—C241.507 (5)C73—H730.9500
C22—C231.384 (5)C74—C751.381 (5)
C22—H220.9500C74—H740.9500
C23—H230.9500C75—H750.9500
O3—Zn1—O1107.92 (10)C26—C27—H27119.5
O3—Zn1—O9101.01 (10)C28—C27—H27119.5
O1—Zn1—O9102.14 (10)C29—C28—C27120.9 (4)
O3—Zn1—O8135.45 (11)C29—C28—H28119.5
O1—Zn1—O897.87 (10)C27—C28—H28119.5
O9—Zn1—O8108.41 (10)C28—C29—C30118.2 (4)
O3—Zn1—C25114.78 (12)C28—C29—C32121.4 (4)
O1—Zn1—C25126.49 (11)C30—C29—C32120.4 (4)
O9—Zn1—C2599.84 (10)C31—C30—C29121.2 (4)
O8—Zn1—C2528.64 (11)C31—C30—H30119.4
O2—Zn2—O4107.30 (10)C29—C30—H30119.4
O2—Zn2—O6142.57 (11)C30—C31—C26119.9 (4)
O4—Zn2—O6100.23 (11)C30—C31—H31120.1
O2—Zn2—O1097.18 (10)C26—C31—H31120.1
O4—Zn2—O1099.04 (10)C29—C32—H32A109.5
O6—Zn2—O10103.10 (10)C29—C32—H32B109.5
O2—Zn2—O590.36 (10)H32A—C32—H32B109.5
O4—Zn2—O5157.49 (9)C29—C32—H32C109.5
O6—Zn2—O558.03 (9)H32A—C32—H32C109.5
O10—Zn2—O592.28 (9)H32B—C32—H32C109.5
O2—Zn2—C17117.82 (12)O11—C33—O12124.9 (3)
O4—Zn2—C17129.36 (11)O11—C33—C34116.8 (3)
O6—Zn2—C1729.17 (11)O12—C33—C34118.3 (3)
O10—Zn2—C1797.06 (10)C39—C34—C35118.4 (3)
O5—Zn2—C1728.95 (10)C39—C34—C33122.1 (3)
O11—Zn3—O16126.93 (10)C35—C34—C33119.5 (3)
O11—Zn3—O13107.64 (10)C36—C35—C34120.2 (3)
O16—Zn3—O13109.04 (11)C36—C35—H35119.9
O11—Zn3—N1101.55 (11)C34—C35—H35119.9
O16—Zn3—N1109.37 (11)C35—C36—C37121.2 (4)
O13—Zn3—N198.49 (11)C35—C36—H36119.4
O14—Zn4—O17124.32 (10)C37—C36—H36119.4
O14—Zn4—O12107.99 (10)C36—C37—C38118.0 (3)
O17—Zn4—O12107.01 (11)C36—C37—C40121.5 (4)
O14—Zn4—N3103.33 (11)C38—C37—C40120.5 (3)
O17—Zn4—N3112.65 (11)C39—C38—C37120.8 (3)
O12—Zn4—N398.50 (11)C39—C38—H38119.6
C65—N1—C69118.6 (3)C37—C38—H38119.6
C65—N1—Zn3122.1 (2)C38—C39—C34121.4 (4)
C69—N1—Zn3119.3 (3)C38—C39—H39119.3
C70—N2—H2A120.0C34—C39—H39119.3
C70—N2—H2B120.0C37—C40—H40A109.5
H2A—N2—H2B120.0C37—C40—H40B109.5
C71—N3—C75118.2 (3)H40A—C40—H40B109.5
C71—N3—Zn4122.6 (2)C37—C40—H40C109.5
C75—N3—Zn4119.2 (2)H40A—C40—H40C109.5
C76—N4—H4A120.0H40B—C40—H40C109.5
C76—N4—H4B120.0O14—C41—O13125.7 (3)
H4A—N4—H4B120.0O14—C41—C42116.3 (3)
C1—O1—Zn1127.3 (2)O13—C41—C42118.1 (3)
C1—O2—Zn2137.6 (2)C47—C42—C43119.6 (3)
C9—O3—Zn1127.7 (2)C47—C42—C41120.4 (3)
C9—O4—Zn2137.8 (3)C43—C42—C41120.0 (3)
C17—O5—Zn279.8 (2)C44—C43—C42118.7 (3)
C17—O6—Zn2101.3 (2)C44—C43—H43120.6
C25—O8—Zn1103.0 (2)C42—C43—H43120.6
Zn1—O9—H91116.3C45—C44—C43122.1 (3)
Zn1—O9—H92109.9C45—C44—H44119.0
H91—O9—H92106.5C43—C44—H44119.0
Zn2—O10—H101113.1C46—C45—C44118.2 (3)
Zn2—O10—H102103.6C46—C45—C48121.1 (4)
H101—O10—H102106.5C44—C45—C48120.7 (3)
C33—O11—Zn3143.6 (3)C47—C46—C45121.0 (4)
C33—O12—Zn4130.1 (2)C47—C46—H46119.5
C41—O13—Zn3131.9 (2)C45—C46—H46119.5
C41—O14—Zn4141.2 (3)C46—C47—C42120.4 (3)
C49—O16—Zn3109.4 (2)C46—C47—H47119.8
C57—O17—Zn4108.2 (2)C42—C47—H47119.8
H211—O21—H212110.9C45—C48—H48A109.5
H221—O22—H222106.5C45—C48—H48B109.5
O1—C1—O2125.4 (3)H48A—C48—H48B109.5
O1—C1—C2117.3 (3)C45—C48—H48C109.5
O2—C1—C2117.3 (3)H48A—C48—H48C109.5
C7—C2—C3119.1 (3)H48B—C48—H48C109.5
C7—C2—C1119.8 (3)O15—C49—O16122.8 (3)
C3—C2—C1121.0 (3)O15—C49—C50121.0 (3)
C2—C3—C4119.9 (4)O16—C49—C50116.2 (3)
C2—C3—H3120.0C55—C50—C51118.4 (3)
C4—C3—H3120.0C55—C50—C49121.5 (3)
C5—C4—C3120.9 (3)C51—C50—C49120.2 (3)
C5—C4—H4119.5C52—C51—C50120.3 (4)
C3—C4—H4119.5C52—C51—H51119.9
C4—C5—C6118.8 (3)C50—C51—H51119.9
C4—C5—C8121.4 (3)C51—C52—C53121.5 (4)
C6—C5—C8119.7 (4)C51—C52—H52119.3
C5—C6—C7120.7 (4)C53—C52—H52119.3
C5—C6—H6119.6C52—C53—C54118.1 (3)
C7—C6—H6119.6C52—C53—C56121.0 (4)
C6—C7—C2120.5 (3)C54—C53—C56120.8 (4)
C6—C7—H7119.8C55—C54—C53120.4 (4)
C2—C7—H7119.8C55—C54—H54119.8
C5—C8—H8A109.5C53—C54—H54119.8
C5—C8—H8B109.5C54—C55—C50121.3 (4)
H8A—C8—H8B109.5C54—C55—H55119.3
C5—C8—H8C109.5C50—C55—H55119.3
H8A—C8—H8C109.5C53—C56—H56A109.5
H8B—C8—H8C109.5C53—C56—H56B109.5
O3—C9—O4125.1 (3)H56A—C56—H56B109.5
O3—C9—C10117.3 (3)C53—C56—H56C109.5
O4—C9—C10117.7 (3)H56A—C56—H56C109.5
C15—C10—C11117.9 (3)H56B—C56—H56C109.5
C15—C10—C9121.3 (3)O18—C57—O17122.6 (3)
C11—C10—C9120.8 (3)O18—C57—C58121.6 (3)
C12—C11—C10121.1 (3)O17—C57—C58115.8 (3)
C12—C11—H11119.4C63—C58—C59118.7 (3)
C10—C11—H11119.4C63—C58—C57120.2 (3)
C11—C12—C13121.1 (3)C59—C58—C57121.1 (3)
C11—C12—H12119.5C60—C59—C58120.7 (3)
C13—C12—H12119.5C60—C59—H59119.6
C14—C13—C12117.9 (3)C58—C59—H59119.6
C14—C13—C16120.9 (3)C59—C60—C61120.4 (4)
C12—C13—C16121.2 (3)C59—C60—H60119.8
C13—C14—C15121.4 (3)C61—C60—H60119.8
C13—C14—H14119.3C60—C61—C62118.8 (3)
C15—C14—H14119.3C60—C61—C64119.7 (4)
C10—C15—C14120.6 (3)C62—C61—C64121.6 (4)
C10—C15—H15119.7C63—C62—C61120.4 (4)
C14—C15—H15119.7C63—C62—H62119.8
C13—C16—H16A109.5C61—C62—H62119.8
C13—C16—H16B109.5C62—C63—C58121.0 (4)
H16A—C16—H16B109.5C62—C63—H63119.5
C13—C16—H16C109.5C58—C63—H63119.5
H16A—C16—H16C109.5C61—C64—H64A109.5
H16B—C16—H16C109.5C61—C64—H64B109.5
O5—C17—O6120.4 (3)H64A—C64—H64B109.5
O5—C17—C18120.9 (3)C61—C64—H64C109.5
O6—C17—C18118.6 (3)H64A—C64—H64C109.5
O5—C17—Zn271.2 (2)H64B—C64—H64C109.5
O6—C17—Zn249.49 (17)N1—C65—C66122.2 (3)
C18—C17—Zn2166.5 (3)N1—C65—H65118.9
C19—C18—C23118.0 (3)C66—C65—H65118.9
C19—C18—C17121.6 (4)C67—C66—C65118.4 (3)
C23—C18—C17120.4 (4)C67—C66—C70118.5 (3)
C20—C19—C18120.9 (4)C65—C66—C70123.0 (3)
C20—C19—H19119.6C68—C67—C66119.9 (3)
C18—C19—H19119.6C68—C67—H67120.0
C19—C20—C21121.5 (4)C66—C67—H67120.0
C19—C20—H20119.3C67—C68—C69118.3 (3)
C21—C20—H20119.3C67—C68—H68120.8
C20—C21—C22117.9 (4)C69—C68—H68120.8
C20—C21—C24121.7 (4)N1—C69—C68122.6 (4)
C22—C21—C24120.4 (4)N1—C69—H69118.7
C23—C22—C21120.9 (4)C68—C69—H69118.7
C23—C22—H22119.5O19—C70—N2122.2 (4)
C21—C22—H22119.5O19—C70—C66118.0 (3)
C22—C23—C18120.8 (4)N2—C70—C66119.8 (3)
C22—C23—H23119.6N3—C71—C72123.3 (3)
C18—C23—H23119.6N3—C71—H71118.4
C21—C24—H24A109.5C72—C71—H71118.4
C21—C24—H24B109.5C71—C72—C73117.8 (4)
H24A—C24—H24B109.5C71—C72—C76124.3 (3)
C21—C24—H24C109.5C73—C72—C76117.9 (3)
H24A—C24—H24C109.5C74—C73—C72119.1 (3)
H24B—C24—H24C109.5C74—C73—H73120.4
O8—C25—O7120.5 (3)C72—C73—H73120.4
O8—C25—C26120.0 (3)C75—C74—C73119.1 (3)
O7—C25—C26119.6 (4)C75—C74—H74120.4
O8—C25—Zn148.34 (17)C73—C74—H74120.4
O7—C25—Zn172.5 (2)N3—C75—C74122.5 (3)
C26—C25—Zn1166.7 (3)N3—C75—H75118.7
C27—C26—C31118.7 (3)C74—C75—H75118.7
C27—C26—C25121.2 (4)O20—C76—N4123.7 (4)
C31—C26—C25120.2 (4)O20—C76—C72117.8 (3)
C26—C27—C28121.1 (4)N4—C76—C72118.5 (3)
O11—Zn3—N1—C6561.7 (3)C17—C18—C23—C22−178.0 (3)
O16—Zn3—N1—C65−74.5 (3)Zn1—O8—C25—O7−7.9 (4)
O13—Zn3—N1—C65171.8 (3)Zn1—O8—C25—C26172.1 (3)
O11—Zn3—N1—C69−118.8 (3)O3—Zn1—C25—O8−142.4 (2)
O16—Zn3—N1—C69105.0 (3)O1—Zn1—C25—O8−2.6 (3)
O13—Zn3—N1—C69−8.7 (3)O9—Zn1—C25—O8110.6 (2)
O14—Zn4—N3—C7163.8 (3)O3—Zn1—C25—O730.5 (2)
O17—Zn4—N3—C71−72.9 (3)O1—Zn1—C25—O7170.20 (18)
O12—Zn4—N3—C71174.6 (3)O9—Zn1—C25—O7−76.6 (2)
O14—Zn4—N3—C75−117.9 (3)O8—Zn1—C25—O7172.8 (4)
O17—Zn4—N3—C75105.4 (3)O3—Zn1—C25—C26−173.6 (11)
O12—Zn4—N3—C75−7.1 (3)O1—Zn1—C25—C26−33.8 (11)
O3—Zn1—O1—C177.9 (3)O9—Zn1—C25—C2679.4 (11)
O9—Zn1—O1—C1−176.1 (3)O8—Zn1—C25—C26−31.2 (10)
O8—Zn1—O1—C1−65.3 (3)O8—C25—C26—C27171.7 (4)
C25—Zn1—O1—C1−64.0 (3)O7—C25—C26—C27−8.3 (5)
O4—Zn2—O2—C1−57.6 (4)Zn1—C25—C26—C27−161.8 (9)
O6—Zn2—O2—C177.8 (4)O8—C25—C26—C31−7.8 (5)
O10—Zn2—O2—C1−159.5 (4)O7—C25—C26—C31172.2 (3)
O5—Zn2—O2—C1108.2 (4)Zn1—C25—C26—C3118.7 (13)
C17—Zn2—O2—C198.6 (4)C31—C26—C27—C281.1 (6)
O1—Zn1—O3—C9−76.5 (3)C25—C26—C27—C28−178.4 (4)
O9—Zn1—O3—C9176.7 (3)C26—C27—C28—C29−0.9 (6)
O8—Zn1—O3—C945.7 (3)C27—C28—C29—C300.1 (6)
C25—Zn1—O3—C970.4 (3)C27—C28—C29—C32179.5 (4)
O2—Zn2—O4—C960.2 (4)C28—C29—C30—C310.6 (7)
O6—Zn2—O4—C9−94.1 (3)C32—C29—C30—C31−178.8 (4)
O10—Zn2—O4—C9160.7 (3)C29—C30—C31—C26−0.4 (6)
O5—Zn2—O4—C9−80.0 (5)C27—C26—C31—C30−0.4 (6)
C17—Zn2—O4—C9−92.3 (4)C25—C26—C31—C30179.1 (4)
O2—Zn2—O5—C17−162.3 (2)Zn3—O11—C33—O127.3 (6)
O4—Zn2—O5—C17−20.0 (4)Zn3—O11—C33—C34−173.4 (3)
O6—Zn2—O5—C17−3.6 (2)Zn4—O12—C33—O111.7 (5)
O10—Zn2—O5—C17100.5 (2)Zn4—O12—C33—C34−177.6 (2)
O2—Zn2—O6—C1740.1 (3)O11—C33—C34—C39179.5 (3)
O4—Zn2—O6—C17177.2 (2)O12—C33—C34—C39−1.1 (5)
O10—Zn2—O6—C17−80.9 (2)O11—C33—C34—C35−2.9 (5)
O5—Zn2—O6—C173.5 (2)O12—C33—C34—C35176.5 (3)
O3—Zn1—O8—C2552.2 (3)C39—C34—C35—C36−0.3 (5)
O1—Zn1—O8—C25177.9 (2)C33—C34—C35—C36−178.1 (3)
O9—Zn1—O8—C25−76.5 (2)C34—C35—C36—C371.4 (5)
O16—Zn3—O11—C33−77.5 (4)C35—C36—C37—C38−1.4 (5)
O13—Zn3—O11—C3354.4 (4)C35—C36—C37—C40177.4 (4)
N1—Zn3—O11—C33157.3 (4)C36—C37—C38—C390.3 (6)
O14—Zn4—O12—C33−64.0 (3)C40—C37—C38—C39−178.5 (4)
O17—Zn4—O12—C3372.0 (3)C37—C38—C39—C340.8 (6)
N3—Zn4—O12—C33−171.1 (3)C35—C34—C39—C38−0.8 (5)
O11—Zn3—O13—C41−60.7 (3)C33—C34—C39—C38176.9 (3)
O16—Zn3—O13—C4180.3 (3)Zn4—O14—C41—O135.8 (6)
N1—Zn3—O13—C41−165.7 (3)Zn4—O14—C41—C42−175.5 (3)
O17—Zn4—O14—C41−68.0 (4)Zn3—O13—C41—O140.6 (5)
O12—Zn4—O14—C4158.4 (4)Zn3—O13—C41—C42−178.1 (2)
N3—Zn4—O14—C41162.1 (4)O14—C41—C42—C47−10.0 (5)
O11—Zn3—O16—C49−43.4 (3)O13—C41—C42—C47168.8 (3)
O13—Zn3—O16—C49−174.8 (2)O14—C41—C42—C43171.2 (3)
N1—Zn3—O16—C4978.6 (2)O13—C41—C42—C43−10.0 (5)
O14—Zn4—O17—C57−45.3 (3)C47—C42—C43—C440.4 (5)
O12—Zn4—O17—C57−172.2 (2)C41—C42—C43—C44179.2 (3)
N3—Zn4—O17—C5780.7 (2)C42—C43—C44—C45−1.2 (5)
Zn1—O1—C1—O2−3.3 (5)C43—C44—C45—C461.1 (5)
Zn1—O1—C1—C2176.7 (2)C43—C44—C45—C48−177.7 (4)
Zn2—O2—C1—O1−2.8 (6)C44—C45—C46—C47−0.2 (5)
Zn2—O2—C1—C2177.1 (2)C48—C45—C46—C47178.7 (3)
O1—C1—C2—C7−3.9 (5)C45—C46—C47—C42−0.6 (6)
O2—C1—C2—C7176.1 (3)C43—C42—C47—C460.5 (5)
O1—C1—C2—C3175.4 (3)C41—C42—C47—C46−178.3 (3)
O2—C1—C2—C3−4.5 (5)Zn3—O16—C49—O152.5 (4)
C7—C2—C3—C4−0.9 (5)Zn3—O16—C49—C50−176.1 (2)
C1—C2—C3—C4179.7 (3)O15—C49—C50—C55−169.5 (3)
C2—C3—C4—C5−0.3 (6)O16—C49—C50—C559.1 (5)
C3—C4—C5—C61.1 (6)O15—C49—C50—C519.7 (5)
C3—C4—C5—C8−177.9 (4)O16—C49—C50—C51−171.8 (3)
C4—C5—C6—C7−0.8 (6)C55—C50—C51—C52−0.7 (5)
C8—C5—C6—C7178.3 (4)C49—C50—C51—C52−179.8 (3)
C5—C6—C7—C2−0.5 (6)C50—C51—C52—C532.3 (5)
C3—C2—C7—C61.3 (6)C51—C52—C53—C54−2.2 (5)
C1—C2—C7—C6−179.4 (3)C51—C52—C53—C56175.7 (4)
Zn1—O3—C9—O43.2 (5)C52—C53—C54—C550.5 (6)
Zn1—O3—C9—C10−177.0 (2)C56—C53—C54—C55−177.5 (4)
Zn2—O4—C9—O30.7 (6)C53—C54—C55—C501.2 (6)
Zn2—O4—C9—C10−179.1 (2)C51—C50—C55—C54−1.0 (5)
O3—C9—C10—C151.7 (5)C49—C50—C55—C54178.1 (3)
O4—C9—C10—C15−178.5 (3)Zn4—O17—C57—O180.2 (4)
O3—C9—C10—C11−179.6 (3)Zn4—O17—C57—C58−179.4 (2)
O4—C9—C10—C110.2 (5)O18—C57—C58—C638.9 (5)
C15—C10—C11—C12−0.4 (5)O17—C57—C58—C63−171.5 (3)
C9—C10—C11—C12−179.1 (3)O18—C57—C58—C59−169.4 (3)
C10—C11—C12—C130.5 (6)O17—C57—C58—C5910.2 (5)
C11—C12—C13—C140.0 (6)C63—C58—C59—C600.5 (5)
C11—C12—C13—C16178.5 (3)C57—C58—C59—C60178.8 (3)
C12—C13—C14—C15−0.5 (6)C58—C59—C60—C610.3 (6)
C16—C13—C14—C15−179.0 (4)C59—C60—C61—C620.0 (6)
C11—C10—C15—C14−0.1 (5)C59—C60—C61—C64−180.0 (4)
C9—C10—C15—C14178.6 (3)C60—C61—C62—C63−1.1 (5)
C13—C14—C15—C100.6 (6)C64—C61—C62—C63178.9 (4)
Zn2—O5—C17—O65.5 (3)C61—C62—C63—C581.9 (5)
Zn2—O5—C17—C18−173.5 (3)C59—C58—C63—C62−1.6 (5)
Zn2—O6—C17—O5−6.8 (4)C57—C58—C63—C62−179.9 (3)
Zn2—O6—C17—C18172.2 (3)C69—N1—C65—C660.4 (5)
O2—Zn2—C17—O520.1 (2)Zn3—N1—C65—C66179.9 (2)
O4—Zn2—C17—O5170.26 (17)N1—C65—C66—C670.6 (5)
O6—Zn2—C17—O5173.8 (4)N1—C65—C66—C70−174.9 (3)
O10—Zn2—C17—O5−81.9 (2)C65—C66—C67—C68−1.2 (5)
O2—Zn2—C17—O6−153.7 (2)C70—C66—C67—C68174.5 (3)
O4—Zn2—C17—O6−3.5 (3)C66—C67—C68—C690.8 (5)
O10—Zn2—C17—O6104.3 (2)C65—N1—C69—C68−0.9 (5)
O5—Zn2—C17—O6−173.8 (4)Zn3—N1—C69—C68179.5 (3)
O2—Zn2—C17—C18175.6 (10)C67—C68—C69—N10.3 (5)
O4—Zn2—C17—C18−34.2 (11)C67—C66—C70—O19−13.7 (5)
O6—Zn2—C17—C18−30.7 (9)C65—C66—C70—O19161.8 (3)
O10—Zn2—C17—C1873.6 (10)C67—C66—C70—N2166.0 (3)
O5—Zn2—C17—C18155.5 (11)C65—C66—C70—N2−18.5 (5)
O5—C17—C18—C19175.2 (3)C75—N3—C71—C72−0.2 (5)
O6—C17—C18—C19−3.8 (5)Zn4—N3—C71—C72178.1 (3)
Zn2—C17—C18—C1922.4 (12)N3—C71—C72—C730.8 (5)
O5—C17—C18—C23−6.8 (5)N3—C71—C72—C76−176.3 (3)
O6—C17—C18—C23174.2 (3)C71—C72—C73—C74−1.1 (5)
Zn2—C17—C18—C23−159.5 (8)C76—C72—C73—C74176.3 (3)
C23—C18—C19—C20−0.3 (6)C72—C73—C74—C750.8 (5)
C17—C18—C19—C20177.8 (4)C71—N3—C75—C740.0 (5)
C18—C19—C20—C21−0.2 (6)Zn4—N3—C75—C74−178.4 (3)
C19—C20—C21—C220.7 (6)C73—C74—C75—N3−0.3 (5)
C19—C20—C21—C24−179.8 (4)C71—C72—C76—O20166.0 (3)
C20—C21—C22—C23−0.8 (6)C73—C72—C76—O20−11.1 (5)
C24—C21—C22—C23179.6 (4)C71—C72—C76—N4−14.5 (5)
C21—C22—C23—C180.4 (6)C73—C72—C76—N4168.4 (3)
C19—C18—C23—C220.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O5i0.882.293.161 (4)173
N2—H2B···O210.882.062.918 (4)165
N4—H4A···O7ii0.882.193.061 (4)168
N4—H4B···O220.882.082.939 (5)166
O9—H91···O5iii0.971.652.602 (3)166
O9—H92···O19iv0.971.682.644 (4)172
O10—H101···O20v0.971.672.639 (4)176
O10—H102···O7vi0.971.782.649 (3)147
O21—H211···O150.971.942.869 (4)159
O21—H212···O19vii0.862.293.138 (4)171
O22—H221···O20viii0.972.233.164 (4)160
O22—H222···O180.971.902.802 (5)152
C65—H65···O210.952.373.282 (4)161
C71—H71···O220.952.333.256 (5)165

Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x, −y, z−1/2; (iv) x, −y+1, z−1/2; (v) x−1, −y+1, z+1/2; (vi) x, −y, z+1/2; (vii) x, −y+2, z−1/2; (viii) x, −y+2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2762).

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