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The [2+2] cyclo­condensation reaction between sodium 2,6-di­formyl-4-chloro­phenolate and benzyl­diethyl­enetri­amine, using the sodium template method, followed by transmetal­lation with Zn(CH3COO)2·2H2O, gave an unexpected 18-membered macrocyclic product in which ring contractions have occurred to produce two imidazolidine rings. In the macrocyclic complex, [μ-3,17-di­benzyl-13,27-di­chloro-3,6,9,17,20,23-hexa­aza­penta­cyclo­[23.3.1.111,15.02,6.016,20]­triaconta-1(29),9,11(30),12,14,23,25,27-octaene-29,30-diolato]­bis­[(acetato-κO)­zinc(II)] ethanol 1.75-solvate 0.25-hydrate, [Zn2(C38H38Cl2N6O2)(CH3COO)2]·1.75C2H6O·0.25H2O, each of the two ZnII ions has a distorted trigonal bipyramidal environment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201036X/ci6131sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201036X/ci6131Isup2.hkl
Contains datablock I

CCDC reference: 189869

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.056
  • wR factor = 0.154
  • Data-to-parameter ratio = 19.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 36.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

(I) top
Crystal data top
[Zn2(C38H38Cl2N6O2)(C2H3O2)2]·1.75C2H6O·0.25H2OF(000) = 2112
Mr = 1015.60Dx = 1.407 Mg m3
Monoclinic, P21/cMelting point = 488–497 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 26.0725 (4) ÅCell parameters from 8192 reflections
b = 9.5836 (1) Åθ = 2.4–28.3°
c = 19.7483 (1) ŵ = 1.17 mm1
β = 103.658 (1)°T = 293 K
V = 4794.94 (9) Å3Slab, pale yellow
Z = 40.54 × 0.44 × 0.26 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
11428 independent reflections
Radiation source: fine-focus sealed tube7553 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.093
Detector resolution: 8.33 pixels mm-1θmax = 28.2°, θmin = 2.4°
ω scansh = 3034
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.571, Tmax = 0.751l = 2326
28105 measured 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)] = 0.056H-atom parameters constrained
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0609P)2P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
11428 reflectionsΔρmax = 0.81 e Å3
584 parametersΔρmin = 1.04 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0035 (4)
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.269754 (15)0.64198 (4)0.63759 (2)0.02491 (12)
Zn20.220378 (15)0.49683 (4)0.74888 (2)0.02565 (12)
Cl10.43154 (5)0.95767 (14)0.94726 (5)0.0577 (3)
Cl20.00810 (4)0.97639 (10)0.61455 (6)0.0442 (3)
O10.28967 (9)0.5965 (3)0.74306 (11)0.0266 (5)
O20.19385 (8)0.6056 (2)0.65590 (12)0.0256 (5)
O30.25569 (16)0.2921 (3)0.83281 (15)0.0719 (11)
O40.23253 (10)0.3046 (3)0.71954 (12)0.0315 (6)
O50.27729 (11)0.4591 (3)0.59440 (12)0.0358 (6)
O60.26397 (10)0.6081 (3)0.50650 (13)0.0393 (7)
N10.43859 (11)0.7024 (4)0.71021 (15)0.0346 (7)
N20.34949 (11)0.7331 (3)0.64832 (14)0.0310 (7)
N30.24682 (11)0.8416 (3)0.61205 (15)0.0266 (6)
N40.05061 (11)0.4419 (3)0.68676 (16)0.0293 (7)
N50.13676 (11)0.4641 (3)0.75359 (15)0.0281 (7)
N60.22313 (11)0.5982 (3)0.84016 (14)0.0253 (6)
C10.32072 (13)0.6771 (3)0.79093 (16)0.0237 (7)
C20.30674 (13)0.7210 (4)0.85286 (16)0.0248 (7)
C30.34118 (14)0.8112 (4)0.89969 (18)0.0298 (8)
H30.33170.84340.93950.036*
C40.38821 (15)0.8507 (4)0.88656 (18)0.0327 (8)
C50.40291 (14)0.8101 (4)0.82616 (17)0.0306 (8)
H50.43440.84120.81720.037*
C60.36944 (13)0.7217 (4)0.77924 (17)0.0290 (8)
C70.38400 (13)0.6708 (4)0.71311 (18)0.0302 (8)
H70.37940.56930.71060.036*
C80.43851 (15)0.7155 (6)0.6355 (2)0.0587 (14)
H8A0.46060.64430.62190.070*
H8B0.45140.80650.62580.070*
C90.38060 (14)0.6963 (5)0.59631 (19)0.0379 (9)
H9A0.37170.75770.55620.046*
H9B0.37390.60070.58070.046*
C100.34117 (13)0.8876 (4)0.65021 (19)0.0321 (8)
H10A0.37080.93620.63930.039*
H10B0.33850.91570.69640.039*
C110.29031 (13)0.9249 (4)0.59675 (19)0.0318 (8)
H11A0.28281.02360.59950.038*
H11B0.29410.90460.55010.038*
C120.20139 (13)0.8983 (4)0.60717 (18)0.0276 (8)
H120.19780.99110.59300.033*
C130.15476 (13)0.8310 (3)0.62173 (17)0.0242 (7)
C140.10942 (13)0.9175 (4)0.61197 (19)0.0298 (8)
H140.11061.00830.59580.036*
C150.06350 (13)0.8667 (4)0.62659 (19)0.0305 (8)
C160.06105 (13)0.7313 (4)0.65114 (18)0.0298 (8)
H160.03010.69890.66150.036*
C170.10467 (13)0.6449 (4)0.66015 (18)0.0259 (7)
C180.15265 (12)0.6912 (3)0.64623 (17)0.0228 (7)
C190.10319 (13)0.4926 (4)0.68297 (18)0.0276 (8)
H190.11580.43410.64950.033*
C200.05957 (15)0.3213 (4)0.7349 (2)0.0380 (9)
H20A0.04830.23520.70990.046*
H20B0.04050.33260.77110.046*
C210.11922 (14)0.3207 (4)0.7658 (2)0.0333 (8)
H21A0.12710.29970.81520.040*
H21B0.13650.25210.74260.040*
C220.12853 (14)0.5616 (4)0.80982 (19)0.0321 (8)
H22A0.09830.53180.82680.039*
H22B0.12190.65540.79130.039*
C230.17813 (14)0.5603 (4)0.86940 (18)0.0313 (8)
H23A0.17460.62670.90510.038*
H23B0.18340.46820.89030.038*
C240.25936 (13)0.6796 (3)0.87459 (17)0.0244 (7)
H240.25490.71480.91670.029*
C250.47594 (15)0.5982 (5)0.7488 (2)0.0433 (10)
H25A0.47550.51640.71970.052*
H25B0.46460.56980.79000.052*
C260.53133 (14)0.6539 (4)0.7701 (2)0.0363 (9)
C270.55077 (17)0.7032 (5)0.8372 (2)0.0542 (12)
H270.53020.69900.86980.065*
C280.6026 (2)0.7603 (6)0.8557 (3)0.0718 (17)
H280.61550.79490.90050.086*
C290.63340 (18)0.7652 (5)0.8092 (3)0.0667 (15)
H290.66700.80390.82180.080*
C300.61471 (17)0.7131 (6)0.7438 (3)0.0620 (14)
H300.63590.71440.71200.074*
C310.56461 (16)0.6585 (5)0.7248 (2)0.0484 (11)
H310.55260.62340.67990.058*
C320.01579 (14)0.4119 (4)0.61823 (19)0.0348 (9)
H32A0.02510.32170.60230.042*
H32B0.02150.48160.58520.042*
C330.04195 (14)0.4110 (4)0.61919 (19)0.0308 (8)
C340.06017 (15)0.4573 (4)0.6760 (2)0.0336 (8)
H340.03600.48630.71600.040*
C350.11364 (16)0.4611 (4)0.6742 (2)0.0413 (10)
H350.12500.49080.71310.050*
C360.15037 (16)0.4204 (4)0.6142 (2)0.0427 (10)
H360.18630.42550.61240.051*
C370.13310 (16)0.3722 (4)0.5571 (2)0.0442 (10)
H370.15750.34500.51690.053*
C380.07955 (16)0.3649 (4)0.5602 (2)0.0394 (9)
H380.06830.32860.52250.047*
C390.24767 (15)0.2326 (4)0.77573 (19)0.0331 (8)
C400.27346 (13)0.4890 (4)0.53037 (18)0.0309 (8)
C410.2818 (2)0.3710 (5)0.4837 (2)0.0560 (13)
H41A0.25590.37620.44030.084*
H41B0.27850.28350.50600.084*
H41C0.31650.37800.47510.084*
C420.25493 (19)0.0796 (4)0.7699 (2)0.0486 (11)
H42A0.27250.04280.81460.073*
H42B0.27590.06150.73690.073*
H42C0.22110.03560.75450.073*
O70.16291 (14)0.2267 (3)0.59201 (17)0.0675 (10)
H7A0.18410.26850.62250.101*
C430.1521 (2)0.3067 (6)0.5301 (2)0.0693 (16)
H43A0.18320.31030.51120.083*
H43B0.14310.40140.54020.083*
C440.1076 (2)0.2431 (7)0.4782 (2)0.0749 (17)
H44A0.10040.29750.43620.112*
H44B0.07680.24090.49690.112*
H44C0.11680.14970.46810.112*
O80.3354 (2)0.0652 (5)0.4492 (3)0.0775 (15)0.75
H80.30780.09370.42410.116*0.75
C450.3726 (5)0.1048 (9)0.4263 (6)0.101 (3)0.75
H45A0.37850.20350.43590.121*0.75
H45B0.36430.09200.37620.121*0.75
C460.4174 (6)0.0323 (19)0.4558 (11)0.240 (11)0.75
H46A0.44600.06510.43710.360*0.75
H46B0.41170.06520.44570.360*0.75
H46C0.42590.04620.50530.360*0.75
O1W0.4633 (8)0.187 (2)0.4667 (9)0.109 (6)*0.25
H1W0.45100.27290.45280.164*0.25
H2W0.49790.17470.48560.164*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0222 (2)0.0288 (2)0.0230 (2)0.00032 (16)0.00388 (15)0.00475 (17)
Zn20.0262 (2)0.0259 (2)0.0241 (2)0.00037 (16)0.00447 (16)0.00391 (16)
Cl10.0590 (7)0.0791 (9)0.0325 (6)0.0376 (6)0.0060 (5)0.0206 (5)
Cl20.0279 (5)0.0369 (6)0.0684 (7)0.0092 (4)0.0125 (5)0.0064 (5)
O10.0274 (13)0.0342 (14)0.0181 (11)0.0042 (10)0.0051 (9)0.0067 (10)
O20.0208 (12)0.0237 (13)0.0311 (13)0.0037 (9)0.0040 (10)0.0029 (10)
O30.134 (3)0.042 (2)0.0328 (17)0.026 (2)0.0062 (19)0.0013 (15)
O40.0369 (14)0.0250 (13)0.0317 (14)0.0013 (11)0.0061 (11)0.0007 (11)
O50.0510 (17)0.0322 (15)0.0244 (13)0.0036 (12)0.0093 (12)0.0029 (11)
O60.0423 (16)0.0459 (18)0.0288 (14)0.0033 (13)0.0067 (12)0.0076 (12)
N10.0203 (15)0.050 (2)0.0322 (17)0.0002 (14)0.0037 (13)0.0041 (15)
N20.0206 (15)0.052 (2)0.0193 (14)0.0002 (13)0.0034 (11)0.0074 (14)
N30.0255 (15)0.0259 (16)0.0280 (15)0.0036 (12)0.0058 (12)0.0012 (12)
N40.0245 (15)0.0254 (16)0.0367 (17)0.0059 (12)0.0049 (13)0.0032 (13)
N50.0284 (15)0.0215 (15)0.0332 (17)0.0046 (12)0.0050 (13)0.0022 (12)
N60.0277 (15)0.0273 (16)0.0214 (14)0.0017 (12)0.0069 (12)0.0006 (12)
C10.0257 (17)0.0244 (18)0.0185 (16)0.0024 (13)0.0002 (13)0.0027 (13)
C20.0261 (17)0.0305 (19)0.0158 (16)0.0002 (14)0.0011 (13)0.0004 (14)
C30.039 (2)0.0275 (19)0.0205 (17)0.0038 (15)0.0034 (15)0.0036 (14)
C40.037 (2)0.036 (2)0.0216 (17)0.0080 (16)0.0003 (15)0.0054 (15)
C50.0246 (18)0.038 (2)0.0252 (18)0.0052 (15)0.0023 (14)0.0003 (16)
C60.0235 (17)0.040 (2)0.0214 (17)0.0009 (15)0.0005 (14)0.0022 (15)
C70.0232 (17)0.037 (2)0.0287 (19)0.0015 (15)0.0033 (14)0.0030 (16)
C80.025 (2)0.118 (5)0.032 (2)0.001 (2)0.0055 (17)0.006 (3)
C90.0233 (18)0.060 (3)0.032 (2)0.0015 (17)0.0104 (16)0.0092 (19)
C100.0255 (18)0.042 (2)0.0294 (19)0.0073 (15)0.0068 (15)0.0026 (16)
C110.0276 (19)0.035 (2)0.033 (2)0.0062 (15)0.0088 (15)0.0057 (16)
C120.0288 (18)0.0210 (18)0.0310 (19)0.0035 (14)0.0035 (15)0.0029 (14)
C130.0214 (16)0.0225 (18)0.0285 (18)0.0008 (13)0.0055 (14)0.0051 (14)
C140.0297 (19)0.0200 (18)0.038 (2)0.0013 (14)0.0052 (16)0.0043 (15)
C150.0229 (17)0.030 (2)0.039 (2)0.0037 (14)0.0070 (15)0.0008 (16)
C160.0216 (17)0.037 (2)0.0298 (19)0.0028 (14)0.0047 (14)0.0001 (16)
C170.0240 (17)0.0249 (18)0.0278 (18)0.0038 (13)0.0040 (14)0.0013 (14)
C180.0229 (16)0.0193 (17)0.0248 (17)0.0002 (12)0.0025 (13)0.0007 (13)
C190.0216 (17)0.0295 (19)0.0314 (19)0.0042 (14)0.0057 (14)0.0019 (15)
C200.035 (2)0.027 (2)0.052 (2)0.0072 (16)0.0113 (18)0.0070 (18)
C210.034 (2)0.0198 (18)0.046 (2)0.0052 (14)0.0095 (17)0.0051 (16)
C220.0292 (19)0.031 (2)0.038 (2)0.0003 (15)0.0129 (16)0.0008 (17)
C230.036 (2)0.033 (2)0.0272 (19)0.0024 (16)0.0124 (16)0.0003 (16)
C240.0328 (19)0.0226 (18)0.0179 (16)0.0025 (14)0.0063 (14)0.0004 (13)
C250.032 (2)0.042 (2)0.053 (3)0.0011 (17)0.0053 (19)0.005 (2)
C260.0258 (19)0.033 (2)0.046 (2)0.0033 (15)0.0008 (17)0.0019 (18)
C270.040 (3)0.064 (3)0.052 (3)0.010 (2)0.000 (2)0.010 (2)
C280.048 (3)0.074 (4)0.072 (4)0.010 (3)0.028 (3)0.029 (3)
C290.030 (2)0.050 (3)0.112 (5)0.004 (2)0.000 (3)0.003 (3)
C300.029 (2)0.075 (4)0.081 (4)0.004 (2)0.011 (2)0.022 (3)
C310.031 (2)0.059 (3)0.053 (3)0.0118 (19)0.0065 (19)0.004 (2)
C320.034 (2)0.034 (2)0.035 (2)0.0081 (16)0.0067 (16)0.0080 (17)
C330.033 (2)0.0239 (19)0.034 (2)0.0069 (15)0.0048 (16)0.0042 (16)
C340.031 (2)0.032 (2)0.035 (2)0.0039 (15)0.0011 (16)0.0024 (16)
C350.039 (2)0.037 (2)0.050 (3)0.0023 (17)0.013 (2)0.0035 (19)
C360.030 (2)0.034 (2)0.062 (3)0.0030 (17)0.0051 (19)0.011 (2)
C370.036 (2)0.044 (3)0.044 (2)0.0074 (18)0.0057 (19)0.010 (2)
C380.041 (2)0.043 (2)0.031 (2)0.0075 (18)0.0038 (17)0.0023 (18)
C390.035 (2)0.033 (2)0.031 (2)0.0065 (16)0.0076 (16)0.0019 (16)
C400.0219 (18)0.046 (2)0.0231 (18)0.0013 (15)0.0007 (14)0.0005 (16)
C410.075 (3)0.062 (3)0.033 (2)0.009 (3)0.016 (2)0.012 (2)
C420.064 (3)0.028 (2)0.055 (3)0.010 (2)0.016 (2)0.001 (2)
O70.086 (3)0.0416 (19)0.056 (2)0.0086 (17)0.0204 (18)0.0025 (16)
C430.095 (4)0.060 (3)0.048 (3)0.032 (3)0.009 (3)0.001 (3)
C440.087 (4)0.089 (4)0.040 (3)0.014 (3)0.003 (3)0.000 (3)
O80.112 (5)0.040 (3)0.084 (4)0.011 (3)0.031 (3)0.012 (3)
C450.147 (10)0.056 (5)0.119 (8)0.049 (6)0.070 (8)0.017 (5)
C460.129 (13)0.225 (19)0.36 (3)0.078 (12)0.037 (15)0.195 (18)
Geometric parameters (Å, º) top
Zn1—O51.979 (3)C17—C191.531 (5)
Zn1—N32.032 (3)C19—H190.98
Zn1—O12.071 (2)C20—C211.531 (5)
Zn1—O22.123 (2)C20—H20A0.97
Zn1—N22.219 (3)C20—H20B0.97
Zn1—C402.596 (4)C21—H21A0.97
Zn1—Zn23.1238 (6)C21—H21B0.97
Zn2—O41.979 (2)C22—C231.529 (5)
Zn2—N62.034 (3)C22—H22A0.97
Zn2—O12.070 (2)C22—H22B0.97
Zn2—O22.083 (2)C23—H23A0.97
Zn2—N52.226 (3)C23—H23B0.97
Cl1—C41.768 (4)C24—H240.93
Cl2—C151.756 (4)C25—C261.504 (5)
O1—C11.336 (4)C25—H25A0.97
O2—C181.329 (4)C25—H25B0.97
O3—C391.236 (4)C26—C271.386 (6)
O4—C391.287 (4)C26—C311.387 (6)
O5—C401.277 (4)C27—C281.423 (7)
O6—C401.237 (4)C27—H270.93
N1—C71.469 (4)C28—C291.356 (8)
N1—C251.475 (5)C28—H280.93
N1—C81.481 (5)C29—C301.364 (7)
N2—C91.493 (4)C29—H290.93
N2—C101.498 (5)C30—C311.374 (6)
N2—C71.503 (4)C30—H300.93
N3—C121.286 (4)C31—H310.93
N3—C111.475 (4)C32—C331.510 (5)
N4—C321.469 (4)C32—H32A0.97
N4—C191.473 (4)C32—H32B0.97
N4—C201.480 (5)C33—C341.390 (5)
N5—C211.486 (4)C33—C381.405 (5)
N5—C191.486 (4)C34—C351.387 (5)
N5—C221.505 (5)C34—H340.93
N6—C241.288 (4)C35—C361.392 (6)
N6—C231.471 (4)C35—H350.93
C1—C61.410 (5)C36—C371.388 (6)
C1—C21.420 (4)C36—H360.93
C2—C31.420 (5)C37—C381.385 (6)
C2—C241.455 (5)C37—H370.93
C3—C41.366 (5)C38—H380.93
C3—H30.93C39—C421.486 (5)
C4—C51.392 (5)C40—C411.507 (5)
C5—C61.399 (5)C41—H41A0.96
C5—H50.93C41—H41B0.96
C6—C71.524 (5)C41—H41C0.96
C7—H70.98C42—H42A0.96
C8—C91.536 (5)C42—H42B0.96
C8—H8A0.97C42—H42C0.96
C8—H8B0.97O7—C431.414 (5)
C9—H9A0.97O7—H7A0.82
C9—H9B0.97C43—C441.485 (6)
C10—C111.530 (5)C43—H43A0.97
C10—H10A0.97C43—H43B0.97
C10—H10B0.97C44—H44A0.96
C11—H11A0.97C44—H44B0.96
C11—H11B0.97C44—H44C0.96
C12—C131.464 (4)O8—C451.222 (10)
C12—H120.93O8—H80.82
C13—C141.419 (5)C45—C461.365 (19)
C13—C181.430 (5)C45—H45A0.97
C14—C151.385 (5)C45—H45B0.97
C14—H140.93C46—H46A0.96
C15—C161.393 (5)C46—H46B0.96
C16—C171.384 (5)C46—H46C0.96
C16—H160.93O1W—H1W0.90
C17—C181.414 (4)O1W—H2W0.90
O5—Zn1—N3141.26 (11)C18—C17—C19116.2 (3)
O5—Zn1—O1102.72 (10)O2—C18—C17120.0 (3)
N3—Zn1—O1115.93 (10)O2—C18—C13122.2 (3)
O5—Zn1—O296.87 (10)C17—C18—C13117.8 (3)
N3—Zn1—O288.01 (10)N4—C19—N5103.9 (3)
O1—Zn1—O279.43 (9)N4—C19—C17114.7 (3)
O5—Zn1—N2101.75 (11)N5—C19—C17113.6 (3)
N3—Zn1—N282.36 (12)N4—C19—H19108.1
O1—Zn1—N288.87 (9)N5—C19—H19108.1
O2—Zn1—N2159.82 (10)C17—C19—H19108.1
O5—Zn1—C4028.57 (11)N4—C20—C21104.5 (3)
N3—Zn1—C40113.23 (12)N4—C20—H20A110.8
O1—Zn1—C40130.76 (11)C21—C20—H20A110.8
O2—Zn1—C40105.20 (10)N4—C20—H20B110.8
N2—Zn1—C4094.91 (11)C21—C20—H20B110.8
O5—Zn1—Zn290.47 (8)H20A—C20—H20B108.9
N3—Zn1—Zn2116.61 (8)N5—C21—C20104.8 (3)
O1—Zn1—Zn241.03 (6)N5—C21—H21A110.8
O2—Zn1—Zn241.54 (6)C20—C21—H21A110.8
N2—Zn1—Zn2129.85 (7)N5—C21—H21B110.8
C40—Zn1—Zn2115.05 (9)C20—C21—H21B110.8
O4—Zn2—N6136.85 (11)H21A—C21—H21B108.9
O4—Zn2—O1102.18 (10)N5—C22—C23108.7 (3)
N6—Zn2—O188.87 (10)N5—C22—H22A110.0
O4—Zn2—O2104.52 (10)C23—C22—H22A110.0
N6—Zn2—O2118.48 (11)N5—C22—H22B110.0
O1—Zn2—O280.36 (9)C23—C22—H22B110.0
O4—Zn2—N596.15 (10)H22A—C22—H22B108.3
N6—Zn2—N581.96 (11)N6—C23—C22107.7 (3)
O1—Zn2—N5160.60 (10)N6—C23—H23A110.2
O2—Zn2—N589.01 (10)C22—C23—H23A110.2
O4—Zn2—Zn195.02 (7)N6—C23—H23B110.2
N6—Zn2—Zn1118.46 (8)C22—C23—H23B110.2
O1—Zn2—Zn141.03 (6)H23A—C23—H23B108.5
O2—Zn2—Zn142.52 (6)N6—C24—C2125.2 (3)
N5—Zn2—Zn1131.49 (8)N6—C24—H24117.4
C1—O1—Zn2128.2 (2)C2—C24—H24117.4
C1—O1—Zn1123.8 (2)N1—C25—C26112.2 (3)
Zn2—O1—Zn197.94 (9)N1—C25—H25A109.2
C18—O2—Zn2121.6 (2)C26—C25—H25A109.2
C18—O2—Zn1129.0 (2)N1—C25—H25B109.2
Zn2—O2—Zn195.94 (9)C26—C25—H25B109.2
C39—O4—Zn2106.5 (2)H25A—C25—H25B107.9
C40—O5—Zn1103.6 (2)C27—C26—C31117.6 (4)
C7—N1—C25111.6 (3)C27—C26—C25120.0 (4)
C7—N1—C8106.4 (3)C31—C26—C25122.4 (4)
C25—N1—C8114.7 (3)C26—C27—C28119.2 (5)
C9—N2—C10110.8 (3)C26—C27—H27120.4
C9—N2—C7100.3 (3)C28—C27—H27120.4
C10—N2—C7115.6 (3)C29—C28—C27121.2 (5)
C9—N2—Zn1119.4 (2)C29—C28—H28119.4
C10—N2—Zn1104.7 (2)C27—C28—H28119.4
C7—N2—Zn1106.5 (2)C28—C29—C30119.5 (4)
C12—N3—C11119.7 (3)C28—C29—H29120.3
C12—N3—Zn1128.9 (2)C30—C29—H29120.3
C11—N3—Zn1111.4 (2)C29—C30—C31120.2 (5)
C32—N4—C19113.4 (3)C29—C30—H30119.9
C32—N4—C20114.1 (3)C31—C30—H30119.9
C19—N4—C20106.4 (3)C30—C31—C26122.3 (5)
C21—N5—C19100.7 (3)C30—C31—H31118.8
C21—N5—C22110.6 (3)C26—C31—H31118.8
C19—N5—C22115.0 (3)N4—C32—C33113.0 (3)
C21—N5—Zn2118.6 (2)N4—C32—H32A109.0
C19—N5—Zn2107.5 (2)C33—C32—H32A109.0
C22—N5—Zn2104.8 (2)N4—C32—H32B109.0
C24—N6—C23119.7 (3)C33—C32—H32B109.0
C24—N6—Zn2128.7 (2)H32A—C32—H32B107.8
C23—N6—Zn2111.4 (2)C34—C33—C38117.7 (3)
O1—C1—C6118.6 (3)C34—C33—C32122.7 (3)
O1—C1—C2123.0 (3)C38—C33—C32119.6 (3)
C6—C1—C2118.4 (3)C35—C34—C33121.4 (4)
C1—C2—C3119.3 (3)C35—C34—H34119.3
C1—C2—C24125.6 (3)C33—C34—H34119.3
C3—C2—C24115.1 (3)C34—C35—C36119.9 (4)
C4—C3—C2120.2 (3)C34—C35—H35120.0
C4—C3—H3119.9C36—C35—H35120.0
C2—C3—H3119.9C37—C36—C35119.7 (4)
C3—C4—C5121.8 (3)C37—C36—H36120.2
C3—C4—Cl1119.4 (3)C35—C36—H36120.2
C5—C4—Cl1118.8 (3)C38—C37—C36119.9 (4)
C4—C5—C6118.8 (3)C38—C37—H37120.1
C4—C5—H5120.6C36—C37—H37120.1
C6—C5—H5120.6C37—C38—C33121.3 (4)
C5—C6—C1121.4 (3)C37—C38—H38119.3
C5—C6—C7121.3 (3)C33—C38—H38119.3
C1—C6—C7117.4 (3)O3—C39—O4119.3 (3)
N1—C7—N2106.0 (3)O3—C39—C42121.9 (4)
N1—C7—C6114.0 (3)O4—C39—C42118.8 (3)
N2—C7—C6112.5 (3)O6—C40—O5123.1 (4)
N1—C7—H7108.0O6—C40—C41120.3 (3)
N2—C7—H7108.0O5—C40—C41116.6 (4)
C6—C7—H7108.0O6—C40—Zn175.4 (2)
N1—C8—C9105.2 (3)C41—C40—Zn1164.0 (3)
N1—C8—H8A110.7C40—C41—H41A109.5
C9—C8—H8A110.7C40—C41—H41B109.5
N1—C8—H8B110.7H41A—C41—H41B109.5
C9—C8—H8B110.7C40—C41—H41C109.5
H8A—C8—H8B108.8H41A—C41—H41C109.5
N2—C9—C8104.7 (3)H41B—C41—H41C109.5
N2—C9—H9A110.8C39—C42—H42A109.5
C8—C9—H9A110.8C39—C42—H42B109.5
N2—C9—H9B110.8H42A—C42—H42B109.5
C8—C9—H9B110.8C39—C42—H42C109.5
H9A—C9—H9B108.9H42A—C42—H42C109.5
N2—C10—C11108.7 (3)H42B—C42—H42C109.5
N2—C10—H10A109.9C43—O7—H7A109.5
C11—C10—H10A109.9O7—C43—C44109.7 (4)
N2—C10—H10B109.9O7—C43—H43A109.7
C11—C10—H10B109.9C44—C43—H43A109.7
H10A—C10—H10B108.3O7—C43—H43B109.7
N3—C11—C10108.4 (3)C44—C43—H43B109.7
N3—C11—H11A110.0H43A—C43—H43B108.2
C10—C11—H11A110.0C43—C44—H44A109.5
N3—C11—H11B110.0C43—C44—H44B109.5
C10—C11—H11B110.0H44A—C44—H44B109.5
H11A—C11—H11B108.4C43—C44—H44C109.5
N3—C12—C13126.3 (3)H44A—C44—H44C109.5
N3—C12—H12116.8H44B—C44—H44C109.5
C13—C12—H12116.8C45—O8—H8109.5
C14—C13—C18119.7 (3)O8—C45—C46110.9 (11)
C14—C13—C12114.8 (3)O8—C45—H45A109.5
C18—C13—C12125.4 (3)C46—C45—H45A109.5
C15—C14—C13120.0 (3)O8—C45—H45B109.5
C15—C14—H14120.0C46—C45—H45B109.5
C13—C14—H14120.0H45A—C45—H45B108.0
C14—C15—C16120.9 (3)C45—C46—H46A109.5
C14—C15—Cl2119.0 (3)C45—C46—H46B109.5
C16—C15—Cl2120.1 (3)H46A—C46—H46B109.5
C17—C16—C15119.9 (3)C45—C46—H46C109.5
C17—C16—H16120.0H46A—C46—H46C109.5
C15—C16—H16120.0H46B—C46—H46C109.5
C16—C17—C18121.7 (3)H1W—O1W—H2W120.0
C16—C17—C19122.1 (3)
O5—Zn1—Zn2—O46.22 (10)O1—C1—C2—C243.5 (5)
N3—Zn1—Zn2—O4157.45 (11)C6—C1—C2—C24177.0 (3)
O1—Zn1—Zn2—O4102.81 (12)C1—C2—C3—C42.5 (5)
O2—Zn1—Zn2—O4106.06 (12)C24—C2—C3—C4176.5 (3)
N2—Zn1—Zn2—O499.57 (13)C2—C3—C4—C53.0 (6)
C40—Zn1—Zn2—O421.30 (11)C2—C3—C4—Cl1177.6 (3)
O5—Zn1—Zn2—N6157.94 (12)C3—C4—C5—C62.7 (6)
N3—Zn1—Zn2—N650.83 (13)Cl1—C4—C5—C6177.9 (3)
O1—Zn1—Zn2—N648.92 (14)C4—C5—C6—C12.1 (5)
O2—Zn1—Zn2—N6102.21 (13)C4—C5—C6—C7178.5 (3)
N2—Zn1—Zn2—N652.15 (14)O1—C1—C6—C5177.8 (3)
C40—Zn1—Zn2—N6173.02 (12)C2—C1—C6—C51.7 (5)
O5—Zn1—Zn2—O1109.02 (13)O1—C1—C6—C71.7 (5)
N3—Zn1—Zn2—O199.74 (13)C2—C1—C6—C7178.8 (3)
O2—Zn1—Zn2—O1151.13 (14)C25—N1—C7—N2153.0 (3)
N2—Zn1—Zn2—O13.23 (15)C8—N1—C7—N227.2 (4)
C40—Zn1—Zn2—O1124.10 (13)C25—N1—C7—C682.7 (4)
O5—Zn1—Zn2—O299.85 (12)C8—N1—C7—C6151.5 (4)
N3—Zn1—Zn2—O251.39 (13)C9—N2—C7—N140.8 (4)
O1—Zn1—Zn2—O2151.13 (14)C10—N2—C7—N178.4 (3)
N2—Zn1—Zn2—O2154.36 (14)Zn1—N2—C7—N1165.8 (2)
C40—Zn1—Zn2—O284.77 (13)C9—N2—C7—C6166.1 (3)
O5—Zn1—Zn2—N596.57 (13)C10—N2—C7—C646.8 (4)
N3—Zn1—Zn2—N554.66 (14)Zn1—N2—C7—C669.0 (3)
O1—Zn1—Zn2—N5154.41 (14)C5—C6—C7—N110.0 (5)
O2—Zn1—Zn2—N53.28 (13)C1—C6—C7—N1170.5 (3)
N2—Zn1—Zn2—N5157.64 (15)C5—C6—C7—N2110.7 (4)
C40—Zn1—Zn2—N581.49 (13)C1—C6—C7—N268.8 (4)
O4—Zn2—O1—C1130.9 (3)C7—N1—C8—C92.5 (5)
N6—Zn2—O1—C17.0 (3)C25—N1—C8—C9126.4 (4)
O2—Zn2—O1—C1126.2 (3)C10—N2—C9—C884.3 (4)
N5—Zn2—O1—C168.5 (4)C7—N2—C9—C838.4 (4)
Zn1—Zn2—O1—C1145.5 (3)Zn1—N2—C9—C8154.0 (3)
O4—Zn2—O1—Zn183.59 (11)N1—C8—C9—N223.1 (5)
N6—Zn2—O1—Zn1138.49 (11)C9—N2—C10—C1189.3 (3)
O2—Zn2—O1—Zn119.33 (9)C7—N2—C10—C11157.4 (3)
N5—Zn2—O1—Zn177.0 (3)Zn1—N2—C10—C1140.6 (3)
O5—Zn1—O1—C1136.6 (2)C12—N3—C11—C10139.6 (3)
N3—Zn1—O1—C146.1 (3)Zn1—N3—C11—C1041.4 (3)
O2—Zn1—O1—C1128.6 (3)N2—C10—C11—N355.6 (4)
N2—Zn1—O1—C134.9 (3)C11—N3—C12—C13178.8 (3)
C40—Zn1—O1—C1130.4 (2)Zn1—N3—C12—C132.3 (5)
Zn2—Zn1—O1—C1147.6 (3)N3—C12—C13—C14179.8 (3)
O5—Zn1—O1—Zn275.73 (12)N3—C12—C13—C182.3 (6)
N3—Zn1—O1—Zn2101.54 (12)C18—C13—C14—C150.4 (5)
O2—Zn1—O1—Zn219.01 (9)C12—C13—C14—C15177.6 (3)
N2—Zn1—O1—Zn2177.52 (11)C13—C14—C15—C160.2 (6)
C40—Zn1—O1—Zn282.01 (14)C13—C14—C15—Cl2179.6 (3)
O4—Zn2—O2—C18134.8 (2)C14—C15—C16—C171.0 (5)
N6—Zn2—O2—C1841.6 (3)Cl2—C15—C16—C17179.6 (3)
O1—Zn2—O2—C18125.0 (2)C15—C16—C17—C181.2 (5)
N5—Zn2—O2—C1838.7 (2)C15—C16—C17—C19176.4 (3)
Zn1—Zn2—O2—C18143.8 (3)Zn2—O2—C18—C1750.8 (4)
O4—Zn2—O2—Zn181.44 (10)Zn1—O2—C18—C17178.4 (2)
N6—Zn2—O2—Zn1102.15 (11)Zn2—O2—C18—C13129.3 (3)
O1—Zn2—O2—Zn118.75 (9)Zn1—O2—C18—C131.5 (4)
N5—Zn2—O2—Zn1177.55 (10)C16—C17—C18—O2179.6 (3)
O5—Zn1—O2—C18137.4 (3)C19—C17—C18—O22.7 (5)
N3—Zn1—O2—C184.0 (3)C16—C17—C18—C130.5 (5)
O1—Zn1—O2—C18120.9 (3)C19—C17—C18—C13177.2 (3)
N2—Zn1—O2—C1865.3 (4)C14—C13—C18—O2179.6 (3)
C40—Zn1—O2—C18109.5 (3)C12—C13—C18—O22.5 (5)
Zn2—Zn1—O2—C18139.7 (3)C14—C13—C18—C170.3 (5)
O5—Zn1—O2—Zn282.91 (10)C12—C13—C18—C17177.6 (3)
N3—Zn1—O2—Zn2135.65 (11)C32—N4—C19—N5159.0 (3)
O1—Zn1—O2—Zn218.81 (9)C20—N4—C19—N532.8 (4)
N2—Zn1—O2—Zn274.3 (3)C32—N4—C19—C1776.3 (4)
C40—Zn1—O2—Zn2110.80 (11)C20—N4—C19—C17157.5 (3)
N6—Zn2—O4—C392.9 (3)C21—N5—C19—N444.2 (3)
O1—Zn2—O4—C3998.7 (2)C22—N5—C19—N474.7 (3)
O2—Zn2—O4—C39178.3 (2)Zn2—N5—C19—N4169.0 (2)
N5—Zn2—O4—C3987.7 (2)C21—N5—C19—C17169.5 (3)
Zn1—Zn2—O4—C39139.6 (2)C22—N5—C19—C1750.6 (4)
N3—Zn1—O5—C4013.9 (3)Zn2—N5—C19—C1765.7 (3)
O1—Zn1—O5—C40170.0 (2)C16—C17—C19—N46.5 (5)
O2—Zn1—O5—C40109.3 (2)C18—C17—C19—N4171.2 (3)
N2—Zn1—O5—C4078.5 (2)C16—C17—C19—N5112.9 (4)
Zn2—Zn1—O5—C40150.5 (2)C18—C17—C19—N569.4 (4)
O5—Zn1—N2—C931.1 (3)C32—N4—C20—C21133.9 (3)
N3—Zn1—N2—C9109.8 (3)C19—N4—C20—C218.1 (4)
O1—Zn1—N2—C9133.9 (3)C19—N5—C21—C2038.8 (4)
O2—Zn1—N2—C9172.0 (3)C22—N5—C21—C2083.3 (4)
C40—Zn1—N2—C93.0 (3)Zn2—N5—C21—C20155.7 (2)
Zn2—Zn1—N2—C9131.7 (2)N4—C20—C21—N519.4 (4)
O5—Zn1—N2—C10155.8 (2)C21—N5—C22—C2389.5 (3)
N3—Zn1—N2—C1014.9 (2)C19—N5—C22—C23157.3 (3)
O1—Zn1—N2—C10101.4 (2)Zn2—N5—C22—C2339.5 (3)
O2—Zn1—N2—C1047.3 (4)C24—N6—C23—C22139.8 (3)
C40—Zn1—N2—C10127.8 (2)Zn2—N6—C23—C2244.2 (3)
Zn2—Zn1—N2—C10103.5 (2)N5—C22—C23—N656.4 (4)
O5—Zn1—N2—C781.2 (2)C23—N6—C24—C2177.6 (3)
N3—Zn1—N2—C7137.9 (2)Zn2—N6—C24—C22.4 (5)
O1—Zn1—N2—C721.5 (2)C1—C2—C24—N60.7 (6)
O2—Zn1—N2—C775.7 (4)C3—C2—C24—N6179.7 (3)
C40—Zn1—N2—C7109.3 (2)C7—N1—C25—C26158.0 (3)
Zn2—Zn1—N2—C719.4 (3)C8—N1—C25—C2680.9 (4)
O5—Zn1—N3—C1294.2 (3)N1—C25—C26—C2798.8 (5)
O1—Zn1—N3—C1281.6 (3)N1—C25—C26—C3181.2 (5)
O2—Zn1—N3—C124.3 (3)C31—C26—C27—C282.3 (6)
N2—Zn1—N3—C12166.6 (3)C25—C26—C27—C28177.7 (4)
C40—Zn1—N3—C12101.4 (3)C26—C27—C28—C291.0 (8)
Zn2—Zn1—N3—C1235.6 (3)C27—C28—C29—C300.8 (8)
O5—Zn1—N3—C1184.8 (3)C28—C29—C30—C311.3 (8)
O1—Zn1—N3—C1199.5 (2)C29—C30—C31—C260.0 (7)
O2—Zn1—N3—C11176.7 (2)C27—C26—C31—C301.8 (6)
N2—Zn1—N3—C1114.5 (2)C25—C26—C31—C30178.1 (4)
C40—Zn1—N3—C1177.6 (2)C19—N4—C32—C33159.3 (3)
Zn2—Zn1—N3—C11145.50 (19)C20—N4—C32—C3378.7 (4)
O4—Zn2—N5—C2125.4 (3)N4—C32—C33—C3410.4 (5)
N6—Zn2—N5—C21111.1 (3)N4—C32—C33—C38171.1 (3)
O1—Zn2—N5—C21173.6 (3)C38—C33—C34—C351.5 (6)
O2—Zn2—N5—C21129.9 (3)C32—C33—C34—C35177.1 (4)
Zn1—Zn2—N5—C21127.7 (2)C33—C34—C35—C361.2 (6)
O4—Zn2—N5—C1987.8 (2)C34—C35—C36—C371.9 (6)
N6—Zn2—N5—C19135.7 (2)C35—C36—C37—C380.1 (6)
O1—Zn2—N5—C1973.1 (4)C36—C37—C38—C332.8 (6)
O2—Zn2—N5—C1916.7 (2)C34—C33—C38—C373.5 (6)
Zn1—Zn2—N5—C1914.5 (2)C32—C33—C38—C37175.1 (4)
O4—Zn2—N5—C22149.4 (2)Zn2—O4—C39—O35.7 (4)
N6—Zn2—N5—C2212.8 (2)Zn2—O4—C39—C42174.2 (3)
O1—Zn2—N5—C2249.7 (4)Zn1—O5—C40—O63.8 (4)
O2—Zn2—N5—C22106.1 (2)Zn1—O5—C40—C41175.5 (3)
Zn1—Zn2—N5—C22108.3 (2)O5—Zn1—C40—O6176.7 (4)
O4—Zn2—N6—C24102.3 (3)N3—Zn1—C40—O66.2 (2)
O1—Zn2—N6—C244.4 (3)O1—Zn1—C40—O6170.37 (18)
O2—Zn2—N6—C2482.8 (3)O2—Zn1—C40—O6100.6 (2)
N5—Zn2—N6—C24167.2 (3)N2—Zn1—C40—O677.6 (2)
Zn1—Zn2—N6—C2434.0 (3)Zn2—Zn1—C40—O6143.78 (18)
O4—Zn2—N6—C2373.2 (3)N3—Zn1—C40—O5170.6 (2)
O1—Zn2—N6—C23179.9 (2)O1—Zn1—C40—O512.9 (3)
O2—Zn2—N6—C23101.7 (2)O2—Zn1—C40—O576.1 (2)
N5—Zn2—N6—C2317.3 (2)N2—Zn1—C40—O5105.6 (2)
Zn1—Zn2—N6—C23150.4 (2)Zn2—Zn1—C40—O533.0 (2)
Zn2—O1—C1—C6172.8 (2)O5—Zn1—C40—C4114.8 (10)
Zn1—O1—C1—C649.6 (4)N3—Zn1—C40—C41174.6 (10)
Zn2—O1—C1—C27.7 (5)O1—Zn1—C40—C411.9 (11)
Zn1—O1—C1—C2129.9 (3)O2—Zn1—C40—C4190.9 (11)
O1—C1—C2—C3177.6 (3)N2—Zn1—C40—C4190.8 (11)
C6—C1—C2—C31.9 (5)Zn2—Zn1—C40—C4147.8 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O40.822.072.835 (4)158
C3—H3···O6i0.932.493.332 (4)151
C12—H12···O7ii0.932.433.295 (5)154
C14—H14···O7ii0.932.513.338 (5)149
C24—H24···O6i0.932.433.285 (4)154
C29—H29···O5iii0.932.433.226 (6)143
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+1/2, z+3/2.
 

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