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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m786.
Published online 2009 June 17. doi:  10.1107/S1600536809022296
PMCID: PMC2969297

Bis[1,3-bis­(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane]zinc(II) dipicrate dimethyl­formamide disolvate

Abstract

In the title compound, [Zn(C30H26N4O)2](C6H2N3O7)2·2C3H7NO, the ZnII ion is coordinated in a distorted octa­hedral environment involving four equatorial N atoms and two O atoms in axial sites. The dihedral angles between the benzimidazole ring system and the phenyl rings in each of the benzyl­benzimidazole units are 78.56 (12), 81.68 (11), 75.76 (10) and 85.78 (9)°. In the crystal structure, there are weak but significant inter­molecular π–π stacking inter­actions with centroid–centroid distances of 3.685 (1) and 3.978 (1) Å.

Related literature

For the nickel(II) ethanol 0.25-solvate analog of the title compound, see: Wu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m786-scheme1.jpg

Experimental

Crystal data

  • [Zn(C30H26N4O)2](C6H2N3O7)2·2C3H7NO
  • M r = 1584.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m786-efi1.jpg
  • a = 13.3235 (2) Å
  • b = 18.1630 (3) Å
  • c = 30.0144 (5) Å
  • β = 97.267 (1)°
  • V = 7205.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.43 mm−1
  • T = 153 K
  • 0.33 × 0.25 × 0.14 mm

Data collection

  • Rigaku R-AXIS SPIDER diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.872, T max = 0.943
  • 65605 measured reflections
  • 16426 independent reflections
  • 11777 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.129
  • S = 1.15
  • 16426 reflections
  • 1019 parameters
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.86 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL .

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022296/lh2840sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022296/lh2840Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2008–041) of Lanzhou Jiaotong University. A grant from ‘Long Yuan Qing Nian’ of Gansu Province is also is acknowledged.

supplementary crystallographic information

Comment

For background information see Wu et al. (2009). The asymmetric unit of the title compound consists of a discrete di[1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxapropane] zinc(II) cation (Fig.1), two picrate anions and two molecules of dimethylformamide. The ZnII ion is six-coordinated with a N4O2 ligand set. The bobb (1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxapropane) ligand acts as a tridentate donor. The coordination geometry of the ZnII ion is distorted octahedral. This geometry is assumed by the ZnII ion presumably to relieve steric crowding. In the crystal structure there are weak but significant intermolecular π–π stacking interactions with centroid to centroid distances of 3.685 (1) and 3.978 (1)Å (Fig. 2).

Experimental

To a stirred solution of 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxapropane (0.183 g, 0.4 mmol) in hot MeOH (15 ml) was added Zn(C6H2N3O7)2 (0.104 g, 0.2 mmol) in MeOH (5 ml). A yellow crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF resulting in a yellow solution. Yellow crystals suitable for X-ray diffraction studies were obtained by ether diffusion into a DMF solution of the title compound after three days at room temperature. Yield, 0.191 g (70%). (found: C, 59.20; H, 4.41; N,14.18. Calcd. for C78 H70 N16 Zn O18: C, 59.11; H, 4.45; N, 14.14)

Refinement

All H atoms were found in difference Fourier maps and were subsequently refined in a riding-model approximation with fixed C—H distances ranging from 0.95 to 0.99Å and Uiso(H) = 1.2 Ueq or Uiso(H) = 1.5Ueq of the carrier atom, respectively.

Figures

Fig. 1.
Molecular structure and atom numbering for the cation. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
Fig. 2.
Part of the crystal structure. H atoms are not shown.

Crystal data

[Zn(C30H26N4O)2](C6H2N3O7)2·2C3H7NOF(000) = 3296
Mr = 1584.87Dx = 1.461 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7749 reflections
a = 13.3235 (2) Åθ = 3.2–27.5°
b = 18.1630 (3) ŵ = 0.43 mm1
c = 30.0144 (5) ÅT = 153 K
β = 97.267 (1)°Block, yellow
V = 7205.0 (2) Å30.33 × 0.25 × 0.14 mm
Z = 4

Data collection

Rigaku R-AXIS SPIDER diffractometer16426 independent reflections
Radiation source: fine-focus sealed tube11777 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −17→17
Tmin = 0.872, Tmax = 0.943k = −23→22
65605 measured reflectionsl = −38→38

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.129w = 1/[σ2(Fo2) + (0.067P)2 + 0.9168P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.018
16426 reflectionsΔρmax = 0.54 e Å3
1019 parametersΔρmin = −0.86 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00109 (16)

Special details

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)

xyzUiso*/Ueq
Zn0.638400 (17)0.988839 (12)0.247281 (7)0.02001 (8)
O10.71979 (11)0.96447 (9)0.32014 (5)0.0313 (4)
O20.53999 (13)1.02713 (8)0.18066 (5)0.0314 (4)
O30.69357 (13)0.88365 (10)−0.14192 (5)0.0419 (4)
O40.7828 (2)1.01940 (12)−0.14526 (6)0.0719 (7)
O50.78149 (16)1.06606 (11)−0.07982 (7)0.0570 (5)
O60.98063 (13)0.92170 (10)0.03757 (5)0.0416 (4)
O71.00246 (14)0.80582 (10)0.02480 (6)0.0469 (5)
O80.69600 (15)0.70231 (10)−0.07005 (6)0.0505 (5)
O90.71053 (13)0.73280 (10)−0.13856 (5)0.0432 (4)
O101.11818 (14)0.57178 (10)0.11553 (5)0.0456 (5)
O111.27610 (15)0.62688 (15)0.07752 (8)0.0723 (7)
O121.22390 (15)0.72272 (12)0.04024 (7)0.0569 (5)
O130.95381 (16)0.66027 (10)−0.08094 (6)0.0515 (5)
O140.83893 (15)0.58166 (12)−0.06673 (6)0.0540 (5)
O150.85306 (15)0.46392 (11)0.07245 (6)0.0515 (5)
O160.94946 (15)0.50220 (11)0.13070 (6)0.0506 (5)
O170.68321 (13)0.07282 (10)0.09630 (6)0.0417 (4)
O180.82449 (17)0.73430 (15)0.05674 (7)0.0777 (7)
N10.53073 (13)0.97799 (9)0.29215 (5)0.0223 (4)
N20.47479 (13)0.96348 (9)0.35851 (5)0.0235 (4)
N30.78731 (13)0.95312 (9)0.24456 (5)0.0225 (4)
N40.93027 (13)0.89371 (9)0.26902 (6)0.0249 (4)
N50.58236 (13)0.89780 (9)0.20769 (5)0.0222 (4)
N60.49619 (13)0.83874 (9)0.14987 (6)0.0243 (4)
N70.64458 (12)1.10460 (9)0.24216 (5)0.0217 (4)
N80.59794 (13)1.21333 (9)0.21164 (6)0.0232 (4)
N90.78936 (16)1.01361 (12)−0.10466 (7)0.0394 (5)
N100.96116 (14)0.86512 (11)0.01545 (6)0.0327 (4)
N110.72462 (14)0.74446 (11)−0.09777 (6)0.0346 (4)
N121.21010 (16)0.66128 (14)0.05444 (7)0.0426 (5)
N130.91676 (17)0.61739 (12)−0.05536 (6)0.0393 (5)
N140.92265 (15)0.50290 (10)0.09008 (7)0.0340 (5)
N150.83209 (15)0.12038 (11)0.07982 (6)0.0330 (4)
N160.86059 (16)0.69339 (12)0.12819 (7)0.0429 (5)
C10.42520 (15)0.98170 (10)0.28564 (7)0.0212 (4)
C20.35658 (15)0.99316 (10)0.24695 (7)0.0230 (4)
H2A0.37920.99770.21830.028*
C30.25569 (17)0.99758 (11)0.25170 (7)0.0289 (5)
H3A0.20791.00530.22580.035*
C40.22116 (17)0.99103 (12)0.29380 (8)0.0308 (5)
H4A0.15080.99530.29580.037*
C50.28706 (17)0.97857 (12)0.33252 (7)0.0295 (5)
H5A0.26390.97360.36100.035*
C60.38890 (16)0.97376 (11)0.32733 (7)0.0236 (4)
C70.55559 (15)0.96714 (10)0.33578 (6)0.0211 (4)
C80.66268 (16)0.95911 (12)0.35676 (7)0.0270 (5)
H8A0.68130.99880.37890.032*
H8B0.67350.91090.37200.032*
C90.81783 (16)0.93253 (12)0.32635 (7)0.0261 (5)
H9A0.81660.88350.34070.031*
H9B0.86630.96450.34510.031*
C100.84499 (15)0.92633 (11)0.27992 (7)0.0233 (4)
C110.92802 (16)0.90006 (11)0.22272 (7)0.0268 (5)
C120.99580 (19)0.87888 (14)0.19389 (8)0.0380 (6)
H12A1.05730.85450.20450.046*
C130.9696 (2)0.89491 (15)0.14870 (8)0.0448 (6)
H13A1.01440.88180.12780.054*
C140.8783 (2)0.93001 (15)0.13348 (8)0.0446 (6)
H14A0.86190.93920.10230.054*
C150.81116 (19)0.95166 (13)0.16244 (7)0.0341 (5)
H15A0.74950.97580.15180.041*
C160.83743 (16)0.93669 (11)0.20773 (7)0.0263 (5)
C170.47390 (18)0.94909 (12)0.40680 (7)0.0281 (5)
H17A0.54100.93000.41960.034*
H17B0.42320.91040.41040.034*
C180.44972 (16)1.01602 (12)0.43293 (7)0.0253 (4)
C190.4996 (2)1.08176 (13)0.42855 (8)0.0364 (5)
H19A0.54721.08540.40760.044*
C200.4813 (2)1.14228 (14)0.45412 (8)0.0457 (7)
H20A0.51741.18680.45120.055*
C210.4112 (2)1.13830 (15)0.48382 (8)0.0457 (7)
H21A0.39741.18030.50090.055*
C220.36073 (19)1.07298 (17)0.48872 (8)0.0433 (6)
H22A0.31231.06990.50930.052*
C230.38073 (18)1.01153 (14)0.46346 (8)0.0353 (5)
H23A0.34680.96640.46730.042*
C241.00640 (16)0.85285 (12)0.29916 (7)0.0283 (5)
H24A0.99890.86570.33060.034*
H24B1.07470.86870.29340.034*
C250.99832 (15)0.77029 (12)0.29365 (7)0.0252 (4)
C260.91468 (17)0.73262 (13)0.30530 (8)0.0314 (5)
H26A0.86080.75930.31560.038*
C270.90888 (18)0.65670 (13)0.30215 (8)0.0355 (5)
H27A0.85110.63170.31010.043*
C280.98740 (19)0.61710 (13)0.28745 (8)0.0370 (6)
H28A0.98390.56490.28560.044*
C291.07080 (19)0.65395 (13)0.27557 (8)0.0366 (5)
H29A1.12480.62710.26550.044*
C301.07551 (17)0.72998 (12)0.27840 (7)0.0302 (5)
H30A1.13260.75500.26970.036*
C310.58910 (15)0.82256 (11)0.21604 (7)0.0222 (4)
C320.63884 (16)0.78461 (12)0.25259 (7)0.0277 (5)
H32A0.67570.80990.27710.033*
C330.63265 (18)0.70887 (12)0.25184 (8)0.0331 (5)
H33A0.66610.68140.27620.040*
C340.57790 (18)0.67173 (12)0.21575 (8)0.0347 (5)
H34A0.57480.61950.21640.042*
C350.52805 (18)0.70878 (12)0.17908 (8)0.0309 (5)
H35A0.49070.68350.15470.037*
C360.53579 (16)0.78486 (11)0.17999 (7)0.0248 (4)
C370.52721 (15)0.90414 (11)0.16806 (7)0.0216 (4)
C380.50469 (17)0.97679 (11)0.14638 (7)0.0266 (5)
H38A0.54110.98300.11980.032*
H38B0.43120.98290.13700.032*
C390.53686 (17)1.10210 (10)0.16844 (7)0.0250 (4)
H39A0.46621.12010.16300.030*
H39B0.56971.11020.14100.030*
C400.59380 (15)1.13949 (11)0.20783 (7)0.0219 (4)
C410.65688 (15)1.22920 (11)0.25217 (7)0.0233 (4)
C420.68580 (17)1.29543 (12)0.27277 (8)0.0296 (5)
H42A0.66631.34140.25920.035*
C430.74447 (17)1.29117 (12)0.31400 (8)0.0329 (5)
H43A0.76541.33520.32950.039*
C440.77373 (17)1.22329 (13)0.33333 (8)0.0331 (5)
H44A0.81441.22250.36170.040*
C450.74529 (16)1.15698 (12)0.31241 (7)0.0283 (5)
H45A0.76571.11110.32580.034*
C460.68584 (15)1.16080 (11)0.27114 (7)0.0229 (4)
C470.43576 (17)0.82781 (12)0.10608 (7)0.0290 (5)
H47A0.37240.85660.10500.035*
H47B0.41710.77520.10260.035*
C480.49104 (17)0.85072 (11)0.06750 (7)0.0282 (5)
C490.5921 (2)0.83515 (15)0.06703 (9)0.0444 (6)
H49A0.62870.81020.09180.053*
C500.6408 (2)0.85553 (18)0.03091 (10)0.0568 (8)
H50A0.71060.84460.03110.068*
C510.5896 (2)0.89111 (16)−0.00503 (9)0.0519 (7)
H51A0.62340.9051−0.02970.062*
C520.4890 (2)0.90652 (18)−0.00514 (9)0.0539 (8)
H52A0.45280.9310−0.03020.065*
C530.4395 (2)0.88672 (15)0.03101 (8)0.0415 (6)
H53A0.36980.89800.03070.050*
C540.54907 (17)1.26622 (11)0.17870 (7)0.0274 (5)
H54A0.54621.31500.19320.033*
H54B0.47871.25010.16890.033*
C550.60443 (17)1.27339 (11)0.13814 (7)0.0271 (5)
C560.70172 (18)1.30224 (12)0.14248 (8)0.0347 (5)
H56A0.73401.31630.17130.042*
C570.7517 (2)1.31053 (14)0.10528 (10)0.0474 (7)
H57A0.81791.33100.10840.057*
C580.7055 (2)1.28898 (15)0.06341 (9)0.0495 (7)
H58A0.74021.29450.03780.059*
C590.6098 (2)1.25962 (14)0.05872 (8)0.0435 (6)
H59A0.57851.24470.02990.052*
C600.55879 (19)1.25165 (12)0.09604 (7)0.0329 (5)
H60A0.49261.23130.09270.039*
C610.75450 (16)0.87863 (13)−0.10704 (7)0.0311 (5)
C620.80654 (17)0.94103 (12)−0.08451 (7)0.0294 (5)
C630.86873 (16)0.93764 (13)−0.04457 (7)0.0290 (5)
H63A0.89820.9811−0.03110.035*
C640.88791 (16)0.86988 (12)−0.02421 (7)0.0271 (5)
C650.84019 (16)0.80636 (13)−0.04190 (7)0.0290 (5)
H65A0.85070.7605−0.02680.035*
C660.77756 (16)0.81147 (13)−0.08177 (7)0.0300 (5)
C671.07224 (18)0.58171 (12)0.07767 (7)0.0305 (5)
C681.11109 (17)0.62750 (13)0.04350 (7)0.0313 (5)
C691.06011 (18)0.64184 (13)0.00217 (7)0.0324 (5)
H69A1.08770.6745−0.01780.039*
C700.96760 (18)0.60822 (12)−0.01038 (7)0.0296 (5)
C710.92477 (17)0.56267 (12)0.01889 (7)0.0300 (5)
H71A0.86160.53960.00970.036*
C720.97367 (17)0.55091 (12)0.06127 (7)0.0281 (5)
C730.75874 (19)0.11133 (13)0.10514 (8)0.0349 (5)
H73A0.76510.13720.13290.042*
C740.8282 (2)0.08428 (17)0.03657 (8)0.0492 (7)
H74A0.76540.05590.03060.074*
H74B0.88630.05110.03680.074*
H74C0.83040.12140.01300.074*
C750.9203 (2)0.16543 (16)0.09386 (9)0.0465 (6)
H75A0.91430.18710.12330.070*
H75B0.92490.20480.07190.070*
H75C0.98130.13480.09590.070*
C760.8832 (2)0.72248 (16)0.09019 (9)0.0515 (7)
H76A0.95200.73530.08910.062*
C770.7586 (3)0.6747 (3)0.13267 (16)0.1046 (17)
H77A0.71580.68420.10420.157*
H77B0.73510.70460.15650.157*
H77C0.75470.62240.14040.157*
C780.9360 (2)0.68289 (18)0.16708 (9)0.0561 (8)
H78A1.00260.69720.15950.084*
H78B0.93730.63100.17600.084*
H78C0.91870.71340.19200.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn0.02450 (13)0.01631 (12)0.01856 (12)0.00111 (9)0.00018 (9)0.00033 (9)
O10.0264 (8)0.0458 (9)0.0218 (7)0.0124 (7)0.0040 (6)0.0057 (7)
O20.0528 (10)0.0166 (7)0.0226 (7)−0.0046 (7)−0.0045 (7)0.0016 (6)
O30.0338 (9)0.0574 (11)0.0316 (9)0.0018 (8)−0.0076 (7)0.0001 (8)
O40.129 (2)0.0533 (13)0.0301 (10)−0.0022 (13)−0.0038 (12)0.0101 (9)
O50.0720 (14)0.0432 (11)0.0544 (12)0.0265 (10)0.0031 (10)−0.0019 (10)
O60.0460 (10)0.0505 (11)0.0266 (8)−0.0021 (8)−0.0022 (7)−0.0066 (8)
O70.0463 (11)0.0431 (10)0.0472 (10)0.0030 (8)−0.0096 (9)0.0121 (8)
O80.0605 (12)0.0477 (11)0.0450 (10)−0.0182 (9)0.0139 (9)−0.0015 (9)
O90.0435 (10)0.0541 (11)0.0316 (9)−0.0091 (8)0.0029 (8)−0.0122 (8)
O100.0508 (11)0.0529 (11)0.0287 (8)−0.0126 (9)−0.0122 (8)0.0100 (8)
O110.0347 (11)0.1035 (18)0.0757 (15)−0.0012 (11)−0.0049 (11)0.0239 (14)
O120.0586 (13)0.0581 (13)0.0550 (12)−0.0234 (10)0.0108 (10)−0.0014 (10)
O130.0759 (14)0.0499 (11)0.0269 (9)0.0046 (10)0.0000 (9)0.0096 (8)
O140.0495 (12)0.0763 (14)0.0318 (9)−0.0010 (10)−0.0124 (9)−0.0029 (9)
O150.0534 (12)0.0500 (11)0.0509 (11)−0.0184 (9)0.0057 (9)0.0031 (9)
O160.0498 (12)0.0695 (13)0.0323 (9)−0.0053 (9)0.0045 (9)0.0165 (9)
O170.0411 (10)0.0422 (10)0.0422 (10)0.0029 (8)0.0071 (8)0.0070 (8)
O180.0608 (14)0.111 (2)0.0582 (13)0.0030 (13)−0.0056 (11)0.0370 (14)
N10.0321 (10)0.0154 (8)0.0183 (8)0.0019 (7)−0.0016 (7)0.0000 (6)
N20.0305 (10)0.0218 (8)0.0184 (8)0.0022 (7)0.0037 (7)0.0006 (7)
N30.0231 (9)0.0211 (8)0.0228 (8)0.0032 (7)0.0010 (7)0.0002 (7)
N40.0243 (9)0.0256 (9)0.0243 (9)0.0049 (7)0.0006 (7)−0.0002 (7)
N50.0284 (9)0.0189 (8)0.0189 (8)−0.0010 (7)0.0012 (7)−0.0001 (7)
N60.0291 (9)0.0218 (9)0.0219 (8)−0.0018 (7)0.0020 (7)−0.0020 (7)
N70.0246 (9)0.0182 (8)0.0221 (8)0.0013 (7)0.0023 (7)0.0004 (7)
N80.0291 (9)0.0160 (8)0.0245 (9)0.0018 (7)0.0034 (7)0.0029 (7)
N90.0386 (12)0.0416 (12)0.0361 (11)0.0058 (9)−0.0029 (9)0.0026 (10)
N100.0325 (10)0.0410 (12)0.0245 (9)−0.0010 (9)0.0028 (8)0.0022 (9)
N110.0290 (10)0.0437 (12)0.0322 (10)−0.0030 (9)0.0077 (8)−0.0056 (9)
N120.0373 (12)0.0607 (15)0.0307 (11)−0.0063 (11)0.0076 (9)−0.0013 (10)
N130.0498 (13)0.0414 (12)0.0249 (10)0.0131 (10)−0.0025 (9)−0.0001 (9)
N140.0331 (11)0.0343 (11)0.0348 (11)0.0046 (8)0.0048 (9)0.0047 (9)
N150.0362 (11)0.0362 (11)0.0273 (10)0.0048 (9)0.0063 (8)−0.0021 (8)
N160.0416 (12)0.0477 (13)0.0398 (12)0.0076 (10)0.0070 (10)0.0092 (10)
C10.0240 (10)0.0137 (9)0.0256 (10)−0.0007 (8)0.0012 (8)−0.0011 (8)
C20.0259 (11)0.0192 (9)0.0238 (10)−0.0012 (8)0.0024 (9)0.0003 (8)
C30.0328 (12)0.0227 (11)0.0291 (11)0.0003 (9)−0.0046 (9)−0.0008 (9)
C40.0259 (11)0.0297 (11)0.0367 (12)0.0000 (9)0.0032 (10)0.0002 (10)
C50.0351 (12)0.0269 (11)0.0279 (11)0.0006 (9)0.0097 (9)0.0008 (9)
C60.0295 (11)0.0176 (10)0.0235 (10)0.0009 (8)0.0030 (9)0.0002 (8)
C70.0268 (11)0.0161 (9)0.0208 (9)0.0015 (8)0.0044 (8)0.0006 (8)
C80.0320 (12)0.0299 (11)0.0188 (10)0.0052 (9)0.0014 (9)−0.0029 (9)
C90.0252 (11)0.0289 (11)0.0230 (10)0.0079 (9)−0.0019 (9)−0.0017 (9)
C100.0245 (10)0.0185 (10)0.0257 (10)0.0003 (8)−0.0019 (8)−0.0023 (8)
C110.0293 (11)0.0254 (11)0.0261 (10)0.0037 (9)0.0054 (9)0.0025 (9)
C120.0380 (14)0.0401 (13)0.0368 (13)0.0115 (11)0.0080 (11)0.0048 (11)
C130.0491 (16)0.0534 (16)0.0345 (13)0.0137 (13)0.0160 (12)0.0061 (12)
C140.0513 (16)0.0555 (16)0.0287 (12)0.0134 (13)0.0114 (11)0.0105 (12)
C150.0392 (13)0.0359 (13)0.0270 (11)0.0082 (10)0.0039 (10)0.0075 (10)
C160.0321 (12)0.0222 (10)0.0252 (10)0.0034 (9)0.0052 (9)0.0017 (8)
C170.0397 (13)0.0260 (11)0.0188 (10)0.0013 (9)0.0040 (9)0.0033 (8)
C180.0285 (11)0.0300 (11)0.0169 (9)−0.0001 (9)0.0009 (8)0.0014 (8)
C190.0520 (15)0.0314 (12)0.0269 (11)−0.0031 (11)0.0096 (11)0.0001 (10)
C200.0719 (19)0.0318 (13)0.0346 (13)−0.0030 (13)0.0120 (13)−0.0065 (11)
C210.0598 (18)0.0421 (15)0.0346 (13)0.0105 (13)0.0034 (13)−0.0143 (11)
C220.0340 (14)0.0697 (19)0.0272 (12)0.0026 (13)0.0070 (10)−0.0159 (12)
C230.0315 (12)0.0485 (14)0.0261 (11)−0.0100 (11)0.0041 (10)−0.0056 (10)
C240.0236 (11)0.0284 (11)0.0309 (11)0.0037 (9)−0.0044 (9)0.0000 (9)
C250.0224 (10)0.0282 (11)0.0243 (10)0.0045 (8)−0.0002 (8)0.0026 (9)
C260.0263 (11)0.0334 (12)0.0350 (12)0.0042 (9)0.0054 (10)−0.0006 (10)
C270.0324 (13)0.0344 (13)0.0409 (13)−0.0019 (10)0.0093 (11)0.0037 (10)
C280.0417 (14)0.0275 (12)0.0420 (13)0.0015 (10)0.0052 (11)−0.0013 (10)
C290.0349 (13)0.0338 (13)0.0425 (13)0.0080 (10)0.0100 (11)−0.0029 (11)
C300.0277 (11)0.0335 (12)0.0299 (11)0.0023 (9)0.0056 (9)0.0016 (10)
C310.0256 (11)0.0194 (10)0.0224 (10)−0.0001 (8)0.0067 (8)−0.0004 (8)
C320.0297 (12)0.0260 (11)0.0274 (11)0.0005 (9)0.0041 (9)0.0013 (9)
C330.0375 (13)0.0268 (11)0.0357 (12)0.0062 (10)0.0078 (10)0.0098 (10)
C340.0434 (14)0.0190 (10)0.0435 (13)0.0002 (10)0.0121 (11)0.0025 (10)
C350.0388 (13)0.0224 (11)0.0330 (12)−0.0036 (9)0.0100 (10)−0.0056 (9)
C360.0278 (11)0.0226 (10)0.0252 (10)−0.0002 (8)0.0080 (9)−0.0013 (8)
C370.0215 (10)0.0210 (10)0.0225 (10)−0.0032 (8)0.0033 (8)−0.0027 (8)
C380.0372 (12)0.0203 (10)0.0202 (10)−0.0023 (9)−0.0043 (9)−0.0021 (8)
C390.0315 (11)0.0175 (10)0.0253 (10)0.0005 (8)0.0008 (9)0.0041 (8)
C400.0238 (10)0.0192 (10)0.0235 (10)0.0006 (8)0.0057 (8)0.0035 (8)
C410.0248 (10)0.0211 (10)0.0257 (10)−0.0001 (8)0.0096 (8)0.0004 (8)
C420.0331 (12)0.0208 (10)0.0362 (12)−0.0025 (9)0.0098 (10)−0.0010 (9)
C430.0351 (13)0.0288 (12)0.0363 (12)−0.0074 (10)0.0105 (10)−0.0114 (10)
C440.0308 (12)0.0370 (13)0.0308 (12)−0.0049 (10)0.0006 (10)−0.0050 (10)
C450.0295 (11)0.0270 (11)0.0280 (11)−0.0005 (9)0.0020 (9)0.0022 (9)
C460.0246 (10)0.0195 (10)0.0252 (10)−0.0002 (8)0.0056 (8)−0.0005 (8)
C470.0340 (12)0.0303 (11)0.0218 (10)−0.0061 (9)0.0000 (9)−0.0059 (9)
C480.0363 (12)0.0246 (11)0.0238 (10)−0.0039 (9)0.0040 (9)−0.0070 (9)
C490.0436 (15)0.0520 (16)0.0393 (14)0.0124 (12)0.0116 (12)0.0091 (12)
C500.0453 (17)0.073 (2)0.0565 (18)0.0096 (15)0.0234 (14)0.0086 (16)
C510.064 (2)0.0597 (18)0.0362 (14)−0.0078 (15)0.0234 (14)0.0009 (13)
C520.066 (2)0.0651 (19)0.0297 (13)−0.0015 (15)0.0030 (13)0.0097 (13)
C530.0413 (14)0.0546 (16)0.0268 (12)−0.0019 (12)−0.0026 (11)0.0018 (11)
C540.0345 (12)0.0189 (10)0.0289 (11)0.0074 (9)0.0046 (9)0.0073 (9)
C550.0332 (12)0.0181 (10)0.0312 (11)0.0051 (9)0.0080 (9)0.0080 (9)
C560.0385 (13)0.0260 (11)0.0392 (13)0.0010 (10)0.0034 (11)0.0089 (10)
C570.0444 (15)0.0387 (14)0.0626 (18)0.0024 (12)0.0197 (14)0.0162 (13)
C580.0636 (19)0.0460 (16)0.0440 (15)0.0157 (14)0.0269 (14)0.0154 (13)
C590.0640 (18)0.0351 (13)0.0316 (13)0.0142 (13)0.0069 (12)0.0051 (11)
C600.0411 (13)0.0259 (11)0.0311 (11)0.0059 (10)0.0025 (10)0.0054 (9)
C610.0240 (11)0.0455 (13)0.0242 (11)0.0030 (10)0.0048 (9)−0.0030 (10)
C620.0290 (11)0.0347 (12)0.0251 (11)0.0046 (9)0.0054 (9)0.0014 (9)
C630.0290 (11)0.0333 (12)0.0258 (10)0.0030 (9)0.0073 (9)−0.0041 (9)
C640.0262 (11)0.0360 (12)0.0195 (10)0.0020 (9)0.0039 (9)−0.0021 (9)
C650.0268 (11)0.0350 (12)0.0267 (11)0.0012 (9)0.0087 (9)0.0003 (9)
C660.0260 (11)0.0365 (12)0.0279 (11)−0.0029 (9)0.0049 (9)−0.0039 (10)
C670.0378 (13)0.0286 (11)0.0244 (10)0.0019 (10)0.0011 (10)0.0007 (9)
C680.0307 (12)0.0352 (12)0.0273 (11)0.0018 (10)0.0012 (9)−0.0011 (10)
C690.0406 (13)0.0304 (12)0.0267 (11)0.0026 (10)0.0058 (10)0.0009 (9)
C700.0377 (13)0.0305 (12)0.0195 (10)0.0078 (10)−0.0005 (9)−0.0004 (9)
C710.0314 (12)0.0287 (11)0.0288 (11)0.0060 (9)−0.0003 (9)−0.0052 (9)
C720.0315 (12)0.0261 (11)0.0269 (11)0.0018 (9)0.0044 (9)0.0028 (9)
C730.0388 (14)0.0360 (13)0.0310 (12)0.0110 (11)0.0089 (11)0.0037 (10)
C740.0451 (16)0.0676 (19)0.0355 (13)0.0022 (14)0.0079 (12)−0.0147 (13)
C750.0414 (15)0.0531 (16)0.0456 (15)0.0001 (12)0.0083 (12)−0.0095 (13)
C760.0499 (17)0.0576 (18)0.0472 (16)0.0064 (14)0.0072 (14)0.0097 (14)
C770.052 (2)0.143 (4)0.117 (3)−0.011 (2)0.004 (2)0.079 (3)
C780.0624 (19)0.0607 (19)0.0432 (15)0.0029 (15)−0.0012 (14)0.0041 (14)

Geometric parameters (Å, °)

Zn—N12.0974 (18)C24—C251.511 (3)
Zn—N32.0988 (17)C24—H24A0.9900
Zn—N72.1106 (16)C24—H24B0.9900
Zn—N52.1164 (16)C25—C301.387 (3)
Zn—O22.3533 (14)C25—C261.389 (3)
Zn—O12.3567 (14)C26—C271.384 (3)
O1—C91.420 (2)C26—H26A0.9500
O1—C81.417 (3)C27—C281.387 (3)
O2—C391.409 (2)C27—H27A0.9500
O2—C381.412 (2)C28—C291.382 (4)
O3—C611.244 (3)C28—H28A0.9500
O4—N91.215 (3)C29—C301.384 (3)
O5—N91.222 (3)C29—H29A0.9500
O6—N101.233 (2)C30—H30A0.9500
O7—N101.226 (3)C31—C321.391 (3)
O8—N111.227 (3)C31—C361.396 (3)
O9—N111.233 (2)C32—C331.378 (3)
O10—C671.234 (2)C32—H32A0.9500
O11—N121.220 (3)C33—C341.400 (3)
O12—N121.217 (3)C33—H33A0.9500
O13—N131.239 (3)C34—C351.386 (3)
O14—N131.234 (3)C34—H34A0.9500
O15—N141.232 (3)C35—C361.386 (3)
O16—N141.226 (3)C35—H35A0.9500
O17—C731.227 (3)C37—C381.485 (3)
O18—C761.211 (3)C38—H38A0.9900
N1—C71.324 (2)C38—H38B0.9900
N1—C11.396 (3)C39—C401.486 (3)
N2—C71.347 (3)C39—H39A0.9900
N2—C61.396 (3)C39—H39B0.9900
N2—C171.474 (2)C41—C421.385 (3)
N3—C101.322 (2)C41—C461.400 (3)
N3—C161.394 (3)C42—C431.380 (3)
N4—C101.358 (3)C42—H42A0.9500
N4—C111.391 (3)C43—C441.397 (3)
N4—C241.472 (3)C43—H43A0.9500
N5—C371.322 (2)C44—C451.389 (3)
N5—C311.390 (2)C44—H44A0.9500
N6—C371.350 (2)C45—C461.385 (3)
N6—C361.390 (3)C45—H45A0.9500
N6—C471.465 (2)C47—C481.507 (3)
N7—C401.321 (2)C47—H47A0.9900
N7—C461.407 (3)C47—H47B0.9900
N8—C401.347 (2)C48—C491.378 (3)
N8—C411.392 (3)C48—C531.381 (3)
N8—C541.470 (2)C49—C501.382 (4)
N9—C621.456 (3)C49—H49A0.9500
N10—C641.443 (3)C50—C511.364 (4)
N11—C661.457 (3)C50—H50A0.9500
N12—C681.454 (3)C51—C521.369 (4)
N13—C701.441 (3)C51—H51A0.9500
N14—C721.456 (3)C52—C531.386 (4)
N15—C731.322 (3)C52—H52A0.9500
N15—C751.450 (3)C53—H53A0.9500
N15—C741.449 (3)C54—C551.507 (3)
N16—C761.326 (3)C54—H54A0.9900
N16—C771.423 (4)C54—H54B0.9900
N16—C781.453 (3)C55—C561.389 (3)
C1—C21.400 (3)C55—C601.389 (3)
C1—C61.405 (3)C56—C571.379 (4)
C2—C31.372 (3)C56—H56A0.9500
C2—H2A0.9500C57—C581.384 (4)
C3—C41.403 (3)C57—H57A0.9500
C3—H3A0.9500C58—C591.373 (4)
C4—C51.384 (3)C58—H58A0.9500
C4—H4A0.9500C59—C601.389 (4)
C5—C61.388 (3)C59—H59A0.9500
C5—H5A0.9500C60—H60A0.9500
C7—C81.492 (3)C61—C661.449 (3)
C8—H8A0.9900C61—C621.450 (3)
C8—H8B0.9900C62—C631.370 (3)
C9—C101.488 (3)C63—C641.384 (3)
C9—H9A0.9900C63—H63A0.9500
C9—H9B0.9900C64—C651.390 (3)
C11—C121.382 (3)C65—C661.373 (3)
C11—C161.402 (3)C65—H65A0.9500
C12—C131.388 (3)C67—C721.455 (3)
C12—H12A0.9500C67—C681.465 (3)
C13—C141.398 (4)C68—C691.362 (3)
C13—H13A0.9500C69—C701.384 (3)
C14—C151.381 (3)C69—H69A0.9500
C14—H14A0.9500C70—C711.382 (3)
C15—C161.387 (3)C71—C721.371 (3)
C15—H15A0.9500C71—H71A0.9500
C17—C181.504 (3)C73—H73A0.9500
C17—H17A0.9900C74—H74A0.9800
C17—H17B0.9900C74—H74B0.9800
C18—C191.381 (3)C74—H74C0.9800
C18—C231.380 (3)C75—H75A0.9800
C19—C201.380 (3)C75—H75B0.9800
C19—H19A0.9500C75—H75C0.9800
C20—C211.373 (4)C76—H76A0.9500
C20—H20A0.9500C77—H77A0.9800
C21—C221.381 (4)C77—H77B0.9800
C21—H21A0.9500C77—H77C0.9800
C22—C231.394 (4)C78—H78A0.9800
C22—H22A0.9500C78—H78B0.9800
C23—H23A0.9500C78—H78C0.9800
N1—Zn—N3136.28 (6)C29—C30—H30A119.4
N1—Zn—N7100.17 (6)N5—C31—C32130.01 (18)
N3—Zn—N7105.03 (7)N5—C31—C36109.11 (17)
N1—Zn—N593.77 (6)C32—C31—C36120.88 (19)
N3—Zn—N590.27 (7)C33—C32—C31117.4 (2)
N7—Zn—N5138.74 (6)C33—C32—H32A121.3
N1—Zn—O2102.74 (6)C31—C32—H32A121.3
N3—Zn—O2119.08 (6)C32—C33—C34121.2 (2)
N7—Zn—O270.51 (5)C32—C33—H33A119.4
N5—Zn—O268.58 (5)C34—C33—H33A119.4
N1—Zn—O170.02 (6)C35—C34—C33122.1 (2)
N3—Zn—O169.62 (6)C35—C34—H34A119.0
N7—Zn—O1103.72 (6)C33—C34—H34A119.0
N5—Zn—O1117.55 (6)C34—C35—C36116.2 (2)
O2—Zn—O1170.22 (5)C34—C35—H35A121.9
C9—O1—C8116.46 (15)C36—C35—H35A121.9
C9—O1—Zn120.42 (12)C35—C36—N6131.91 (19)
C8—O1—Zn120.22 (11)C35—C36—C31122.2 (2)
C39—O2—C38116.10 (15)N6—C36—C31105.83 (17)
C39—O2—Zn120.11 (11)N5—C37—N6113.21 (17)
C38—O2—Zn121.75 (12)N5—C37—C38122.02 (17)
C7—N1—C1105.49 (17)N6—C37—C38124.75 (17)
C7—N1—Zn122.89 (14)O2—C38—C37103.06 (15)
C1—N1—Zn131.60 (13)O2—C38—H38A111.2
C7—N2—C6107.08 (16)C37—C38—H38A111.2
C7—N2—C17127.81 (17)O2—C38—H38B111.2
C6—N2—C17125.09 (18)C37—C38—H38B111.2
C10—N3—C16105.64 (17)H38A—C38—H38B109.1
C10—N3—Zn122.61 (14)O2—C39—C40103.83 (15)
C16—N3—Zn130.32 (13)O2—C39—H39A111.0
C10—N4—C11106.96 (16)C40—C39—H39A111.0
C10—N4—C24127.20 (18)O2—C39—H39B111.0
C11—N4—C24125.60 (18)C40—C39—H39B111.0
C37—N5—C31105.30 (16)H39A—C39—H39B109.0
C37—N5—Zn123.62 (13)N7—C40—N8113.58 (17)
C31—N5—Zn131.04 (13)N7—C40—C39124.14 (17)
C37—N6—C36106.55 (16)N8—C40—C39122.28 (17)
C37—N6—C47125.96 (17)C42—C41—N8131.64 (19)
C36—N6—C47127.46 (17)C42—C41—C46122.83 (19)
C40—N7—C46104.82 (16)N8—C41—C46105.53 (17)
C40—N7—Zn120.92 (13)C43—C42—C41116.5 (2)
C46—N7—Zn133.90 (13)C43—C42—H42A121.8
C40—N8—C41107.03 (16)C41—C42—H42A121.8
C40—N8—C54125.72 (17)C42—C43—C44121.2 (2)
C41—N8—C54127.25 (17)C42—C43—H43A119.4
O4—N9—O5122.9 (2)C44—C43—H43A119.4
O4—N9—C62118.8 (2)C45—C44—C43122.1 (2)
O5—N9—C62118.2 (2)C45—C44—H44A118.9
O7—N10—O6123.45 (18)C43—C44—H44A118.9
O7—N10—C64118.59 (19)C46—C45—C44116.97 (19)
O6—N10—C64117.94 (19)C46—C45—H45A121.5
O8—N11—O9123.0 (2)C44—C45—H45A121.5
O8—N11—C66118.47 (19)C45—C46—C41120.34 (19)
O9—N11—C66118.5 (2)C45—C46—N7130.63 (18)
O12—N12—O11122.6 (2)C41—C46—N7109.03 (17)
O12—N12—C68118.7 (2)N6—C47—C48112.66 (18)
O11—N12—C68118.7 (2)N6—C47—H47A109.1
O14—N13—O13123.07 (19)C48—C47—H47A109.1
O14—N13—C70118.5 (2)N6—C47—H47B109.1
O13—N13—C70118.4 (2)C48—C47—H47B109.1
O16—N14—O15122.0 (2)H47A—C47—H47B107.8
O16—N14—C72119.84 (19)C49—C48—C53118.5 (2)
O15—N14—C72118.16 (19)C49—C48—C47121.6 (2)
C73—N15—C75122.3 (2)C53—C48—C47119.9 (2)
C73—N15—C74120.9 (2)C48—C49—C50120.6 (2)
C75—N15—C74116.8 (2)C48—C49—H49A119.7
C76—N16—C77120.0 (3)C50—C49—H49A119.7
C76—N16—C78122.3 (3)C51—C50—C49120.6 (3)
C77—N16—C78117.6 (3)C51—C50—H50A119.7
N1—C1—C2131.6 (2)C49—C50—H50A119.7
N1—C1—C6108.92 (17)C50—C51—C52119.4 (3)
C2—C1—C6119.47 (19)C50—C51—H51A120.3
C3—C2—C1117.9 (2)C52—C51—H51A120.3
C3—C2—H2A121.0C51—C52—C53120.5 (3)
C1—C2—H2A121.0C51—C52—H52A119.8
C2—C3—C4121.7 (2)C53—C52—H52A119.8
C2—C3—H3A119.1C48—C53—C52120.4 (3)
C4—C3—H3A119.1C48—C53—H53A119.8
C5—C4—C3121.6 (2)C52—C53—H53A119.8
C5—C4—H4A119.2N8—C54—C55112.29 (17)
C3—C4—H4A119.2N8—C54—H54A109.1
C4—C5—C6116.2 (2)C55—C54—H54A109.1
C4—C5—H5A121.9N8—C54—H54B109.1
C6—C5—H5A121.9C55—C54—H54B109.1
C5—C6—N2131.5 (2)H54A—C54—H54B107.9
C5—C6—C1123.02 (19)C56—C55—C60119.3 (2)
N2—C6—C1105.40 (18)C56—C55—C54120.2 (2)
N1—C7—N2113.09 (17)C60—C55—C54120.5 (2)
N1—C7—C8122.55 (19)C57—C56—C55120.4 (2)
N2—C7—C8124.35 (17)C57—C56—H56A119.8
O1—C8—C7104.16 (15)C55—C56—H56A119.8
O1—C8—H8A110.9C56—C57—C58120.0 (3)
C7—C8—H8A110.9C56—C57—H57A120.0
O1—C8—H8B110.9C58—C57—H57A120.0
C7—C8—H8B110.9C59—C58—C57120.2 (3)
H8A—C8—H8B108.9C59—C58—H58A119.9
O1—C9—C10103.69 (15)C57—C58—H58A119.9
O1—C9—H9A111.0C58—C59—C60120.0 (2)
C10—C9—H9A111.0C58—C59—H59A120.0
O1—C9—H9B111.0C60—C59—H59A120.0
C10—C9—H9B111.0C59—C60—C55120.1 (2)
H9A—C9—H9B109.0C59—C60—H60A120.0
N3—C10—N4112.73 (18)C55—C60—H60A120.0
N3—C10—C9122.59 (18)O3—C61—C66125.1 (2)
N4—C10—C9124.67 (17)O3—C61—C62123.9 (2)
C12—C11—N4132.0 (2)C66—C61—C62110.90 (18)
C12—C11—C16122.4 (2)C63—C62—C61125.0 (2)
N4—C11—C16105.60 (18)C63—C62—N9116.7 (2)
C11—C12—C13116.7 (2)C61—C62—N9118.23 (19)
C11—C12—H12A121.6C62—C63—C64119.0 (2)
C13—C12—H12A121.6C62—C63—H63A120.5
C12—C13—C14121.1 (2)C64—C63—H63A120.5
C12—C13—H13A119.5C63—C64—C65121.30 (19)
C14—C13—H13A119.5C63—C64—N10119.04 (19)
C15—C14—C13122.0 (2)C65—C64—N10119.6 (2)
C15—C14—H14A119.0C66—C65—C64118.4 (2)
C13—C14—H14A119.0C66—C65—H65A120.8
C14—C15—C16117.2 (2)C64—C65—H65A120.8
C14—C15—H15A121.4C65—C66—C61125.4 (2)
C16—C15—H15A121.4C65—C66—N11116.5 (2)
C15—C16—N3130.4 (2)C61—C66—N11117.96 (18)
C15—C16—C11120.5 (2)O10—C67—C72125.2 (2)
N3—C16—C11109.05 (17)O10—C67—C68123.3 (2)
N2—C17—C18113.49 (17)C72—C67—C68111.43 (18)
N2—C17—H17A108.9C69—C68—N12117.3 (2)
C18—C17—H17A108.9C69—C68—C67124.5 (2)
N2—C17—H17B108.9N12—C68—C67118.18 (19)
C18—C17—H17B108.9C68—C69—C70119.2 (2)
H17A—C17—H17B107.7C68—C69—H69A120.4
C19—C18—C23118.9 (2)C70—C69—H69A120.4
C19—C18—C17120.8 (2)C71—C70—C69121.07 (19)
C23—C18—C17120.2 (2)C71—C70—N13118.8 (2)
C20—C19—C18121.0 (2)C69—C70—N13120.0 (2)
C20—C19—H19A119.5C72—C71—C70119.8 (2)
C18—C19—H19A119.5C72—C71—H71A120.1
C21—C20—C19120.1 (2)C70—C71—H71A120.1
C21—C20—H20A119.9C71—C72—N14116.2 (2)
C19—C20—H20A119.9C71—C72—C67123.8 (2)
C20—C21—C22119.7 (2)N14—C72—C67119.92 (18)
C20—C21—H21A120.2O17—C73—N15126.3 (2)
C22—C21—H21A120.2O17—C73—H73A116.8
C21—C22—C23120.1 (2)N15—C73—H73A116.8
C21—C22—H22A120.0N15—C74—H74A109.5
C23—C22—H22A120.0N15—C74—H74B109.5
C18—C23—C22120.2 (2)H74A—C74—H74B109.5
C18—C23—H23A119.9N15—C74—H74C109.5
C22—C23—H23A119.9H74A—C74—H74C109.5
N4—C24—C25113.52 (16)H74B—C74—H74C109.5
N4—C24—H24A108.9N15—C75—H75A109.5
C25—C24—H24A108.9N15—C75—H75B109.5
N4—C24—H24B108.9H75A—C75—H75B109.5
C25—C24—H24B108.9N15—C75—H75C109.5
H24A—C24—H24B107.7H75A—C75—H75C109.5
C30—C25—C26118.4 (2)H75B—C75—H75C109.5
C30—C25—C24121.0 (2)O18—C76—N16126.2 (3)
C26—C25—C24120.6 (2)O18—C76—H76A116.9
C27—C26—C25120.9 (2)N16—C76—H76A116.9
C27—C26—H26A119.6N16—C77—H77A109.5
C25—C26—H26A119.6N16—C77—H77B109.5
C28—C27—C26120.0 (2)H77A—C77—H77B109.5
C28—C27—H27A120.0N16—C77—H77C109.5
C26—C27—H27A120.0H77A—C77—H77C109.5
C29—C28—C27119.6 (2)H77B—C77—H77C109.5
C29—C28—H28A120.2N16—C78—H78A109.5
C27—C28—H28A120.2N16—C78—H78B109.5
C28—C29—C30119.9 (2)H78A—C78—H78B109.5
C28—C29—H29A120.0N16—C78—H78C109.5
C30—C29—H29A120.0H78A—C78—H78C109.5
C25—C30—C29121.1 (2)H78B—C78—H78C109.5
C25—C30—H30A119.4
N1—Zn—O1—C9156.43 (16)C37—N5—C31—C36−0.1 (2)
N3—Zn—O1—C9−6.37 (15)Zn—N5—C31—C36177.52 (15)
N7—Zn—O1—C9−107.57 (15)N5—C31—C32—C33−179.9 (2)
N5—Zn—O1—C972.79 (16)C36—C31—C32—C33−0.5 (3)
N1—Zn—O1—C8−3.60 (14)C31—C32—C33—C34−0.3 (3)
N3—Zn—O1—C8−166.40 (16)C32—C33—C34—C350.4 (4)
N7—Zn—O1—C892.41 (15)C33—C34—C35—C360.3 (4)
N5—Zn—O1—C8−87.24 (15)C34—C35—C36—N6−179.6 (2)
N1—Zn—O2—C39100.04 (16)C34—C35—C36—C31−1.1 (3)
N3—Zn—O2—C39−93.16 (16)C37—N6—C36—C35179.4 (2)
N7—Zn—O2—C393.61 (15)C47—N6—C36—C35−2.7 (4)
N5—Zn—O2—C39−170.90 (17)C37—N6—C36—C310.8 (2)
N1—Zn—O2—C38−96.86 (16)C47—N6—C36—C31178.6 (2)
N3—Zn—O2—C3869.94 (17)N5—C31—C36—C35−179.2 (2)
N7—Zn—O2—C38166.71 (18)C32—C31—C36—C351.2 (3)
N5—Zn—O2—C38−7.80 (16)N5—C31—C36—N6−0.4 (2)
N3—Zn—N1—C726.50 (19)C32—C31—C36—N6−179.94 (19)
N7—Zn—N1—C7−98.16 (15)C31—N5—C37—N60.7 (2)
N5—Zn—N1—C7120.85 (15)Zn—N5—C37—N6−177.22 (14)
O2—Zn—N1—C7−170.28 (14)C31—N5—C37—C38−178.33 (19)
O1—Zn—N1—C72.86 (14)Zn—N5—C37—C383.8 (3)
N3—Zn—N1—C1−155.33 (15)C36—N6—C37—N5−0.9 (2)
N7—Zn—N1—C180.02 (17)C47—N6—C37—N5−178.84 (19)
N5—Zn—N1—C1−60.98 (17)C36—N6—C37—C38178.0 (2)
O2—Zn—N1—C17.89 (17)C47—N6—C37—C380.1 (3)
O1—Zn—N1—C1−178.97 (18)C39—O2—C38—C37174.49 (18)
N1—Zn—N3—C10−14.3 (2)Zn—O2—C38—C3710.8 (2)
N7—Zn—N3—C10108.75 (16)N5—C37—C38—O2−9.2 (3)
N5—Zn—N3—C10−110.03 (16)N6—C37—C38—O2171.9 (2)
O2—Zn—N3—C10−175.49 (14)C38—O2—C39—C40−170.54 (18)
O1—Zn—N3—C109.42 (15)Zn—O2—C39—C40−6.5 (2)
N1—Zn—N3—C16150.02 (16)C46—N7—C40—N80.0 (2)
N7—Zn—N3—C16−86.95 (18)Zn—N7—C40—N8174.07 (13)
N5—Zn—N3—C1654.28 (18)C46—N7—C40—C39−179.9 (2)
O2—Zn—N3—C16−11.2 (2)Zn—N7—C40—C39−5.8 (3)
O1—Zn—N3—C16173.72 (19)C41—N8—C40—N70.0 (2)
N1—Zn—N5—C37104.08 (17)C54—N8—C40—N7179.88 (19)
N3—Zn—N5—C37−119.49 (17)C41—N8—C40—C39179.96 (19)
N7—Zn—N5—C37−6.0 (2)C54—N8—C40—C39−0.2 (3)
O2—Zn—N5—C371.86 (16)O2—C39—C40—N77.9 (3)
O1—Zn—N5—C37173.48 (15)O2—C39—C40—N8−171.98 (19)
N1—Zn—N5—C31−73.21 (18)C40—N8—C41—C42180.0 (2)
N3—Zn—N5—C3163.22 (18)C54—N8—C41—C420.1 (4)
N7—Zn—N5—C31176.72 (16)C40—N8—C41—C460.0 (2)
O2—Zn—N5—C31−175.4 (2)C54—N8—C41—C46−179.88 (19)
O1—Zn—N5—C31−3.8 (2)N8—C41—C42—C43179.1 (2)
N1—Zn—N7—C40−98.91 (16)C46—C41—C42—C43−0.9 (3)
N3—Zn—N7—C40117.15 (16)C41—C42—C43—C440.8 (3)
N5—Zn—N7—C408.9 (2)C42—C43—C44—C45−0.3 (4)
O2—Zn—N7—C401.12 (15)C43—C44—C45—C46−0.1 (3)
O1—Zn—N7—C40−170.64 (15)C44—C45—C46—C410.0 (3)
N1—Zn—N7—C4673.14 (19)C44—C45—C46—N7−179.4 (2)
N3—Zn—N7—C46−70.8 (2)C42—C41—C46—C450.5 (3)
N5—Zn—N7—C46−179.06 (17)N8—C41—C46—C45−179.47 (19)
O2—Zn—N7—C46173.2 (2)C42—C41—C46—N7−180.0 (2)
O1—Zn—N7—C461.4 (2)N8—C41—C46—N70.0 (2)
C7—N1—C1—C2179.1 (2)C40—N7—C46—C45179.4 (2)
Zn—N1—C1—C20.7 (3)Zn—N7—C46—C456.5 (4)
C7—N1—C1—C60.9 (2)C40—N7—C46—C410.0 (2)
Zn—N1—C1—C6−177.48 (13)Zn—N7—C46—C41−172.97 (15)
N1—C1—C2—C3−176.82 (19)C37—N6—C47—C4865.2 (3)
C6—C1—C2—C31.2 (3)C36—N6—C47—C48−112.3 (2)
C1—C2—C3—C40.1 (3)N6—C47—C48—C4941.1 (3)
C2—C3—C4—C5−1.1 (3)N6—C47—C48—C53−140.4 (2)
C3—C4—C5—C60.7 (3)C53—C48—C49—C500.3 (4)
C4—C5—C6—N2178.4 (2)C47—C48—C49—C50178.8 (2)
C4—C5—C6—C10.7 (3)C48—C49—C50—C51−0.3 (5)
C7—N2—C6—C5−176.6 (2)C49—C50—C51—C52−0.1 (5)
C17—N2—C6—C55.1 (3)C50—C51—C52—C530.5 (5)
C7—N2—C6—C11.3 (2)C49—C48—C53—C520.0 (4)
C17—N2—C6—C1−176.92 (17)C47—C48—C53—C52−178.5 (2)
N1—C1—C6—C5176.77 (18)C51—C52—C53—C48−0.4 (4)
C2—C1—C6—C5−1.7 (3)C40—N8—C54—C55−75.7 (3)
N1—C1—C6—N2−1.4 (2)C41—N8—C54—C55104.1 (2)
C2—C1—C6—N2−179.86 (17)N8—C54—C55—C56−65.1 (2)
C1—N1—C7—N2−0.1 (2)N8—C54—C55—C60115.2 (2)
Zn—N1—C7—N2178.52 (12)C60—C55—C56—C571.2 (3)
C1—N1—C7—C8179.30 (18)C54—C55—C56—C57−178.4 (2)
Zn—N1—C7—C8−2.1 (3)C55—C56—C57—C58−1.0 (4)
C6—N2—C7—N1−0.8 (2)C56—C57—C58—C590.3 (4)
C17—N2—C7—N1177.36 (18)C57—C58—C59—C600.2 (4)
C6—N2—C7—C8179.82 (18)C58—C59—C60—C550.0 (3)
C17—N2—C7—C8−2.0 (3)C56—C55—C60—C59−0.8 (3)
C9—O1—C8—C7−157.35 (17)C54—C55—C60—C59178.93 (19)
Zn—O1—C8—C73.4 (2)O3—C61—C62—C63175.5 (2)
N1—C7—C8—O1−1.1 (3)C66—C61—C62—C63−0.4 (3)
N2—C7—C8—O1178.20 (18)O3—C61—C62—N9−2.2 (3)
C8—O1—C9—C10163.49 (17)C66—C61—C62—N9−178.1 (2)
Zn—O1—C9—C102.7 (2)O4—N9—C62—C63142.8 (3)
C16—N3—C10—N40.4 (2)O5—N9—C62—C63−37.7 (3)
Zn—N3—C10—N4168.07 (13)O4—N9—C62—C61−39.2 (3)
C16—N3—C10—C9−179.99 (19)O5—N9—C62—C61140.2 (2)
Zn—N3—C10—C9−12.4 (3)C61—C62—C63—C642.6 (4)
C11—N4—C10—N30.2 (2)N9—C62—C63—C64−179.6 (2)
C24—N4—C10—N3−174.32 (18)C62—C63—C64—C65−4.3 (3)
C11—N4—C10—C9−179.35 (19)C62—C63—C64—N10173.9 (2)
C24—N4—C10—C96.1 (3)O7—N10—C64—C63−156.3 (2)
O1—C9—C10—N35.4 (3)O6—N10—C64—C6322.0 (3)
O1—C9—C10—N4−175.12 (19)O7—N10—C64—C6521.9 (3)
C10—N4—C11—C12177.9 (2)O6—N10—C64—C65−159.8 (2)
C24—N4—C11—C12−7.4 (4)C63—C64—C65—C663.8 (3)
C10—N4—C11—C16−0.8 (2)N10—C64—C65—C66−174.4 (2)
C24—N4—C11—C16173.88 (19)C64—C65—C66—C61−1.5 (3)
N4—C11—C12—C13−179.2 (2)C64—C65—C66—N11−176.59 (19)
C16—C11—C12—C13−0.7 (4)O3—C61—C66—C65−176.0 (2)
C11—C12—C13—C14−0.7 (4)C62—C61—C66—C65−0.2 (3)
C12—C13—C14—C151.3 (4)O3—C61—C66—N11−1.0 (3)
C13—C14—C15—C16−0.5 (4)C62—C61—C66—N11174.88 (19)
C14—C15—C16—N3178.3 (2)O8—N11—C66—C6535.6 (3)
C14—C15—C16—C11−0.9 (3)O9—N11—C66—C65−144.5 (2)
C10—N3—C16—C15179.8 (2)O8—N11—C66—C61−139.9 (2)
Zn—N3—C16—C1513.5 (3)O9—N11—C66—C6140.0 (3)
C10—N3—C16—C11−0.9 (2)O12—N12—C68—C6935.4 (3)
Zn—N3—C16—C11−167.23 (14)O11—N12—C68—C69−144.6 (2)
C12—C11—C16—C151.5 (3)O12—N12—C68—C67−143.5 (2)
N4—C11—C16—C15−179.6 (2)O11—N12—C68—C6736.5 (3)
C12—C11—C16—N3−177.8 (2)O10—C67—C68—C69−177.1 (2)
N4—C11—C16—N31.1 (2)C72—C67—C68—C692.3 (3)
C7—N2—C17—C18107.5 (2)O10—C67—C68—N121.7 (4)
C6—N2—C17—C18−74.6 (3)C72—C67—C68—N12−178.9 (2)
N2—C17—C18—C19−49.2 (3)N12—C68—C69—C70177.2 (2)
N2—C17—C18—C23134.1 (2)C67—C68—C69—C70−4.0 (4)
C23—C18—C19—C200.0 (3)C68—C69—C70—C712.4 (3)
C17—C18—C19—C20−176.7 (2)C68—C69—C70—N13−174.4 (2)
C18—C19—C20—C21−1.4 (4)O14—N13—C70—C71−3.1 (3)
C19—C20—C21—C221.5 (4)O13—N13—C70—C71177.6 (2)
C20—C21—C22—C23−0.3 (4)O14—N13—C70—C69173.8 (2)
C19—C18—C23—C221.2 (3)O13—N13—C70—C69−5.6 (3)
C17—C18—C23—C22178.0 (2)C69—C70—C71—C720.7 (3)
C21—C22—C23—C18−1.1 (4)N13—C70—C71—C72177.5 (2)
C10—N4—C24—C25103.3 (2)C70—C71—C72—N14179.3 (2)
C11—N4—C24—C25−70.3 (3)C70—C71—C72—C67−2.4 (3)
N4—C24—C25—C30115.6 (2)O16—N14—C72—C71−164.2 (2)
N4—C24—C25—C26−66.7 (3)O15—N14—C72—C7115.7 (3)
C30—C25—C26—C270.6 (3)O16—N14—C72—C6717.4 (3)
C24—C25—C26—C27−177.2 (2)O15—N14—C72—C67−162.6 (2)
C25—C26—C27—C280.3 (3)O10—C67—C72—C71−179.6 (2)
C26—C27—C28—C29−0.6 (4)C68—C67—C72—C711.0 (3)
C27—C28—C29—C300.0 (4)O10—C67—C72—N14−1.4 (4)
C26—C25—C30—C29−1.2 (3)C68—C67—C72—N14179.22 (19)
C24—C25—C30—C29176.5 (2)C75—N15—C73—O17−178.0 (2)
C28—C29—C30—C250.9 (4)C74—N15—C73—O171.1 (4)
C37—N5—C31—C32179.4 (2)C77—N16—C76—O18−1.7 (5)
Zn—N5—C31—C32−3.0 (3)C78—N16—C76—O18−178.5 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2840).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, H., Yun, R., Li, K., Wang, K. & Huang, X. (2009). Acta Cryst. E65, m751–m752. [PMC free article] [PubMed]

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