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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m882.
Published online 2009 July 8. doi:  10.1107/S1600536809025355
PMCID: PMC2977391

Perchloratobis[1-(1,10-phenanthrolin-2-yl)-2-pyridone]zinc(II) perchlorate

Abstract

In the title mononuclear complex, [Zn(ClO4)(C17H11N3O)2]ClO4, the ZnII ion is coordinated in a distorted octa­hedral geometry. The dihedral angles between the pyridine rings and the mean planes of the 1,10-phenanthroline ring system in each of the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligands is 24.51 (10)° for the tridendate PP ligand and 73.55 (6)° for the bidentate PP ligand. Within the mol­ecule there is a weak π–π inter­action between the pyridine ring of the bidentate ligand and the 1,10-phenanthroline ring system of the tridendate ligand with a centroid–centroid distance of 3.6383 (19) Å.

Related literature

For a related crystal structure and background information, see: Liu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m882-scheme1.jpg

Experimental

Crystal data

  • [Zn(ClO4)(C17H11N3O)2]ClO4
  • M r = 810.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m882-efi1.jpg
  • a = 12.998 (2) Å
  • b = 16.741 (3) Å
  • c = 14.680 (3) Å
  • β = 100.068 (2)°
  • V = 3145.2 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.03 mm−1
  • T = 298 K
  • 0.45 × 0.38 × 0.26 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.655, T max = 0.776
  • 16722 measured reflections
  • 6163 independent reflections
  • 5005 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.130
  • S = 1.08
  • 6163 reflections
  • 480 parameters
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025355/lh2853sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025355/lh2853Isup2.hkl

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

Acknowledgments

The authors thank the Research Project of ‘SUST Spring Bud’ for support (No. 2008BWZ056).

supplementary crystallographic information

Comment

Metal complexes containing derivatives of 1,10-phenanthroline as ligands play a pivotal role in the area of modern coordination chemistry. One of the first metal complexes containing the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligand was published recently (Liu et al., 2008 and references cited within). Our interest in this area motivated us to synthesize the title complex, and here we report its crystal structure.

The asymmetric unit of the title compound (I) is shown in Fig. 1. The data of coordination bond lengths and associated angles (Table 1) indicate that the ZnII ion is in a distorted octahedral geometry. The dihedral angles between pyridine rings and the mean planes of the 1,10-phenanthroline ring system in each of the 1-(1,10-phenanthrolin-2-yl)-2-pyridone (PP) ligands is 24.51 (10)° for the tridendate PP ligand and 73.55 (6)° for the bidentate PP ligand. There is a weak π–π interaction with Cg1···Cg2 = 3.6376 (19)Å and Cg1···Cg2perp = 3.569 Å; α is 15.63° [Cg1 and Cg2 are the centroids of C23C24C27-C29/N4 ring and C13—C17/N5 ring, respectively; Cg1···Cg2iperp is the perpendicular distance from ring Cg1 to ring Cg2; α is the dihedral angle between the Cg1 ring plane and the Cg2 ring plane].

Experimental

Hydrated zinc perchlorate (0.2418 g, 0.65 mmol) and 1-(1,10-phenanthrolin-2-yl)-2-pyridone (0.1774 g, 0.65 mmol) were dissolved in 10 ml methanol, and the solution was stirred for a few minutes. Yellow single crystals were obtained after the filtrate had been allowed to stand at room temperature for one week.

Refinement

All H atoms were placed in calculated positions, and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2eq(C).

Figures

Fig. 1.
The asymmetric unit of (I) showing the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level.

Crystal data

[Zn(ClO4)(C17H11N3O)2]ClO4F(000) = 1648
Mr = 810.85Dx = 1.712 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6273 reflections
a = 12.998 (2) Åθ = 2.3–27.0°
b = 16.741 (3) ŵ = 1.02 mm1
c = 14.680 (3) ÅT = 298 K
β = 100.068 (2)°Block, yellow
V = 3145.2 (10) Å30.45 × 0.38 × 0.26 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer6163 independent reflections
Radiation source: fine-focus sealed tube5005 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→16
Tmin = 0.655, Tmax = 0.776k = −20→19
16722 measured reflectionsl = −17→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0839P)2 + 0.2024P] where P = (Fo2 + 2Fc2)/3
6163 reflections(Δ/σ)max = 0.001
480 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = −0.62 e Å3

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
C10.1039 (2)0.10171 (18)0.5679 (2)0.0474 (7)
H10.06810.06300.59550.057*
C20.1066 (3)0.09526 (19)0.4745 (2)0.0535 (8)
H20.07420.05240.44080.064*
C30.1568 (2)0.1520 (2)0.4320 (2)0.0505 (8)
H30.15730.14900.36880.061*
C40.2076 (2)0.21493 (17)0.48458 (19)0.0395 (6)
C50.20322 (19)0.21620 (15)0.57950 (18)0.0331 (6)
C60.25810 (19)0.27716 (15)0.63721 (18)0.0313 (5)
C70.3130 (2)0.33617 (16)0.5965 (2)0.0370 (6)
C80.2632 (2)0.27598 (19)0.4458 (2)0.0450 (7)
H80.26450.27590.38270.054*
C90.3140 (2)0.33375 (18)0.4999 (2)0.0439 (7)
H90.35050.37280.47350.053*
C100.3663 (2)0.39396 (16)0.6561 (2)0.0440 (7)
H100.40150.43510.63200.053*
C110.3670 (2)0.39036 (18)0.7479 (2)0.0481 (8)
H110.40240.42860.78730.058*
C120.3138 (2)0.32829 (16)0.7828 (2)0.0382 (6)
C130.2868 (3)0.3608 (2)1.0268 (2)0.0610 (9)
H130.25370.39431.06320.073*
C140.3496 (3)0.3029 (2)1.0683 (2)0.0624 (9)
H140.35890.29691.13220.075*
C150.4010 (3)0.25162 (19)1.0158 (2)0.0590 (9)
H150.44480.21171.04460.071*
C160.3864 (2)0.26046 (18)0.9239 (2)0.0498 (7)
H160.42050.22640.88880.060*
C170.2688 (3)0.37307 (19)0.9287 (2)0.0507 (8)
C180.3225 (2)0.04946 (19)0.7636 (2)0.0497 (8)
H180.32010.06050.70110.060*
C190.3877 (2)−0.0110 (2)0.8049 (3)0.0617 (9)
H190.4280−0.04010.77020.074*
C200.3924 (3)−0.02735 (19)0.8950 (3)0.0579 (9)
H200.4367−0.06750.92250.069*
C210.3313 (2)0.01527 (16)0.9483 (2)0.0447 (7)
C220.2667 (2)0.07564 (15)0.90174 (19)0.0349 (6)
C230.2012 (2)0.12133 (15)0.95101 (18)0.0330 (6)
C240.1966 (2)0.10129 (16)1.04237 (19)0.0381 (6)
C250.2612 (2)0.03954 (18)1.0871 (2)0.0484 (7)
H250.25780.02661.14810.058*
C260.3269 (2)−0.00048 (18)1.0429 (2)0.0525 (8)
H260.3704−0.03921.07450.063*
C270.0828 (2)0.22394 (15)0.94907 (18)0.0334 (6)
C280.0674 (2)0.20372 (18)1.0379 (2)0.0433 (7)
H280.01770.23061.06480.052*
C290.1256 (2)0.14452 (17)1.0849 (2)0.0437 (7)
H290.11830.13271.14540.052*
C30−0.0805 (3)0.35800 (18)0.7785 (2)0.0520 (8)
H6−0.11050.36000.71620.062*
C31−0.0005 (3)0.35034 (18)0.9622 (2)0.0501 (8)
H310.02850.34941.02480.060*
C32−0.0680 (3)0.40880 (19)0.9300 (3)0.0584 (9)
H32−0.08580.44730.97010.070*
C33−0.1111 (3)0.41155 (19)0.8361 (3)0.0588 (9)
H33−0.16070.45010.81370.071*
C34−0.0037 (2)0.29806 (15)0.8084 (2)0.0378 (6)
Cl10.05475 (7)0.33552 (5)0.23847 (6)0.0555 (2)
Cl2−0.06238 (5)0.05947 (4)0.78950 (5)0.03671 (17)
N10.25867 (16)0.27400 (12)0.72957 (15)0.0331 (5)
N20.15024 (18)0.16100 (13)0.62039 (15)0.0359 (5)
N30.26358 (17)0.09182 (13)0.81097 (16)0.0371 (5)
N40.14672 (16)0.18319 (11)0.90497 (15)0.0306 (5)
N50.32214 (18)0.31891 (13)0.88079 (16)0.0398 (5)
N60.02718 (18)0.29118 (13)0.90430 (16)0.0378 (5)
O10.2131 (2)0.42378 (16)0.88607 (18)0.0763 (8)
O20.03168 (15)0.25565 (11)0.75179 (13)0.0405 (4)
O30.03026 (16)0.07488 (12)0.75009 (15)0.0481 (5)
O4−0.03149 (17)0.03559 (13)0.88350 (15)0.0530 (5)
O5−0.12309 (19)0.12974 (14)0.78672 (19)0.0675 (7)
O6−0.1177 (2)−0.00388 (17)0.73801 (17)0.0728 (7)
O70.0442 (3)0.3557 (2)0.3300 (2)0.1018 (10)
O8−0.0400 (3)0.3197 (3)0.1845 (3)0.147 (2)
O90.0971 (5)0.3960 (3)0.1999 (4)0.204 (3)
O100.1218 (5)0.2717 (3)0.2398 (3)0.208 (3)
Zn10.15585 (2)0.180720 (18)0.76169 (2)0.03378 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0607 (19)0.0447 (17)0.0382 (17)−0.0144 (14)0.0122 (14)−0.0046 (13)
C20.069 (2)0.0489 (18)0.0416 (18)−0.0119 (15)0.0075 (15)−0.0141 (14)
C30.0567 (19)0.064 (2)0.0315 (16)−0.0010 (16)0.0106 (14)−0.0058 (14)
C40.0419 (15)0.0451 (15)0.0323 (15)0.0039 (12)0.0089 (12)0.0034 (12)
C50.0349 (14)0.0356 (14)0.0302 (14)0.0023 (11)0.0093 (11)0.0015 (11)
C60.0317 (13)0.0307 (13)0.0333 (14)0.0025 (10)0.0102 (10)0.0032 (10)
C70.0364 (14)0.0340 (13)0.0433 (16)0.0027 (11)0.0140 (12)0.0085 (12)
C80.0476 (16)0.0552 (18)0.0350 (16)0.0061 (14)0.0150 (13)0.0072 (13)
C90.0440 (16)0.0451 (16)0.0465 (18)0.0024 (13)0.0188 (13)0.0144 (13)
C100.0473 (17)0.0347 (14)0.0526 (19)−0.0091 (12)0.0162 (14)0.0057 (13)
C110.0525 (18)0.0362 (15)0.057 (2)−0.0146 (13)0.0129 (15)−0.0034 (13)
C120.0393 (15)0.0383 (15)0.0369 (15)−0.0046 (11)0.0069 (12)−0.0014 (11)
C130.081 (2)0.063 (2)0.0414 (19)−0.0055 (19)0.0151 (17)−0.0133 (16)
C140.081 (3)0.066 (2)0.0362 (18)−0.0190 (19)−0.0007 (17)0.0011 (16)
C150.065 (2)0.054 (2)0.051 (2)−0.0065 (17)−0.0107 (16)0.0078 (16)
C160.0538 (18)0.0426 (16)0.051 (2)−0.0052 (14)0.0020 (15)−0.0002 (14)
C170.061 (2)0.0456 (17)0.0462 (19)−0.0025 (15)0.0113 (15)−0.0036 (14)
C180.0421 (16)0.0528 (18)0.055 (2)0.0031 (14)0.0107 (14)−0.0121 (15)
C190.0441 (18)0.058 (2)0.084 (3)0.0136 (15)0.0133 (17)−0.0142 (19)
C200.0464 (18)0.0453 (18)0.077 (3)0.0107 (14)−0.0031 (16)−0.0034 (17)
C210.0391 (15)0.0338 (15)0.057 (2)−0.0004 (12)−0.0026 (13)0.0009 (13)
C220.0316 (13)0.0317 (13)0.0396 (16)−0.0043 (11)0.0006 (11)0.0016 (11)
C230.0340 (13)0.0300 (13)0.0330 (14)−0.0089 (10)0.0007 (11)0.0028 (11)
C240.0436 (16)0.0362 (14)0.0327 (15)−0.0108 (12)0.0022 (12)0.0042 (11)
C250.0531 (18)0.0465 (17)0.0410 (17)−0.0109 (14)−0.0047 (14)0.0134 (13)
C260.0464 (18)0.0407 (16)0.063 (2)−0.0018 (14)−0.0124 (15)0.0181 (15)
C270.0384 (14)0.0308 (13)0.0309 (14)−0.0059 (11)0.0053 (11)−0.0012 (11)
C280.0512 (17)0.0440 (16)0.0374 (16)−0.0071 (13)0.0153 (13)−0.0065 (13)
C290.0548 (18)0.0459 (17)0.0314 (15)−0.0124 (14)0.0096 (13)0.0029 (12)
C300.0535 (19)0.0446 (17)0.057 (2)0.0101 (14)0.0080 (15)0.0073 (15)
C310.062 (2)0.0409 (16)0.0491 (19)0.0017 (14)0.0137 (15)−0.0110 (14)
C320.068 (2)0.0382 (17)0.073 (3)0.0093 (15)0.0222 (18)−0.0109 (16)
C330.062 (2)0.0423 (17)0.075 (3)0.0170 (15)0.0190 (18)0.0094 (16)
C340.0427 (15)0.0299 (13)0.0417 (16)−0.0015 (11)0.0101 (12)0.0042 (12)
Cl10.0624 (5)0.0548 (5)0.0495 (5)−0.0031 (4)0.0100 (4)−0.0099 (4)
Cl20.0390 (4)0.0355 (3)0.0378 (4)−0.0005 (3)0.0129 (3)0.0017 (3)
N10.0370 (12)0.0304 (11)0.0330 (12)−0.0025 (9)0.0092 (9)0.0011 (9)
N20.0419 (13)0.0348 (11)0.0317 (12)−0.0072 (10)0.0082 (10)−0.0019 (9)
N30.0361 (12)0.0350 (12)0.0403 (14)−0.0001 (10)0.0070 (10)−0.0024 (10)
N40.0330 (11)0.0280 (11)0.0309 (12)−0.0038 (8)0.0054 (9)−0.0003 (8)
N50.0455 (14)0.0369 (12)0.0362 (13)−0.0077 (10)0.0046 (10)−0.0012 (10)
N60.0424 (13)0.0329 (12)0.0394 (14)0.0003 (10)0.0105 (10)−0.0020 (10)
O10.098 (2)0.0762 (17)0.0574 (16)0.0310 (16)0.0201 (14)0.0083 (14)
O20.0461 (11)0.0398 (11)0.0353 (11)0.0070 (8)0.0063 (9)0.0018 (8)
O30.0490 (12)0.0427 (11)0.0591 (14)−0.0064 (9)0.0277 (10)−0.0052 (10)
O40.0644 (14)0.0554 (13)0.0409 (12)0.0072 (11)0.0135 (10)0.0092 (10)
O50.0689 (15)0.0610 (15)0.0807 (18)0.0316 (12)0.0357 (13)0.0232 (13)
O60.0808 (17)0.0791 (17)0.0607 (16)−0.0412 (15)0.0188 (13)−0.0191 (13)
O70.119 (3)0.123 (3)0.063 (2)−0.016 (2)0.0161 (17)−0.0431 (18)
O80.067 (2)0.260 (5)0.115 (3)−0.034 (3)0.021 (2)−0.117 (3)
O90.217 (5)0.220 (5)0.181 (5)−0.126 (5)0.050 (4)0.049 (4)
O100.331 (7)0.161 (4)0.094 (3)0.145 (5)−0.069 (4)−0.068 (3)
Zn10.0430 (2)0.03160 (19)0.02842 (19)−0.00084 (12)0.01094 (14)0.00178 (12)

Geometric parameters (Å, °)

C1—N21.334 (4)C21—C221.412 (4)
C1—C21.382 (4)C21—C261.424 (5)
C1—H10.9300C22—N31.354 (3)
C2—C31.365 (4)C22—C231.431 (4)
C2—H20.9300C23—N41.365 (3)
C3—C41.401 (4)C23—C241.394 (4)
C3—H30.9300C24—C291.402 (4)
C4—C51.405 (4)C24—C251.418 (4)
C4—C81.427 (4)C25—C261.339 (5)
C5—N21.354 (3)C25—H250.9300
C5—C61.434 (4)C26—H260.9300
C6—N11.356 (3)C27—N41.328 (3)
C6—C71.411 (3)C27—C281.396 (4)
C7—C101.403 (4)C27—N61.434 (3)
C7—C91.421 (4)C28—C291.359 (4)
C8—C91.349 (4)C28—H280.9300
C8—H80.9300C29—H290.9300
C9—H90.9300C30—C331.340 (5)
C10—C111.348 (4)C30—C341.429 (4)
C10—H100.9300C30—H60.9300
C11—C121.395 (4)C31—C321.344 (5)
C11—H110.9300C31—N61.393 (4)
C12—N11.324 (3)C31—H310.9300
C12—N51.432 (4)C32—C331.395 (5)
C13—C141.342 (5)C32—H320.9300
C13—C171.433 (5)C33—H330.9300
C13—H130.9300C34—O21.241 (3)
C14—C151.398 (5)C34—N61.400 (4)
C14—H140.9300Cl1—O91.326 (4)
C15—C161.338 (4)Cl1—O81.369 (3)
C15—H150.9300Cl1—O101.377 (4)
C16—N51.368 (4)Cl1—O71.416 (3)
C16—H160.9300Cl2—O51.413 (2)
C17—O11.216 (4)Cl2—O61.423 (2)
C17—N51.403 (4)Cl2—O41.425 (2)
C18—N31.327 (4)Cl2—O31.4473 (19)
C18—C191.389 (5)N1—Zn12.160 (2)
C18—H180.9300N2—Zn12.089 (2)
C19—C201.341 (5)N3—Zn12.084 (2)
C19—H190.9300N4—Zn12.128 (2)
C20—C211.403 (4)O2—Zn12.0291 (19)
C20—H200.9300O3—Zn12.395 (2)
N2—C1—C2122.9 (3)C25—C26—C21121.2 (3)
N2—C1—H1118.5C25—C26—H26119.4
C2—C1—H1118.5C21—C26—H26119.4
C3—C2—C1119.8 (3)N4—C27—C28122.4 (2)
C3—C2—H2120.1N4—C27—N6119.2 (2)
C1—C2—H2120.1C28—C27—N6118.4 (2)
C2—C3—C4119.2 (3)C29—C28—C27119.5 (3)
C2—C3—H3120.4C29—C28—H28120.2
C4—C3—H3120.4C27—C28—H28120.2
C3—C4—C5117.5 (3)C28—C29—C24120.1 (3)
C3—C4—C8122.8 (3)C28—C29—H29120.0
C5—C4—C8119.7 (3)C24—C29—H29120.0
N2—C5—C4122.8 (2)C33—C30—C34123.0 (3)
N2—C5—C6117.6 (2)C33—C30—H6118.5
C4—C5—C6119.6 (2)C34—C30—H6118.5
N1—C6—C7122.4 (2)C32—C31—N6121.7 (3)
N1—C6—C5118.6 (2)C32—C31—H31119.2
C7—C6—C5119.0 (2)N6—C31—H31119.2
C10—C7—C6116.7 (3)C31—C32—C33119.8 (3)
C10—C7—C9123.5 (2)C31—C32—H32120.1
C6—C7—C9119.8 (3)C33—C32—H32120.1
C9—C8—C4120.6 (3)C30—C33—C32119.3 (3)
C9—C8—H8119.7C30—C33—H33120.4
C4—C8—H8119.7C32—C33—H33120.4
C8—C9—C7121.3 (3)O2—C34—N6123.5 (2)
C8—C9—H9119.4O2—C34—C30121.2 (3)
C7—C9—H9119.4N6—C34—C30115.4 (3)
C11—C10—C7120.6 (3)O9—Cl1—O8107.5 (4)
C11—C10—H10119.7O9—Cl1—O10106.8 (4)
C7—C10—H10119.7O8—Cl1—O10111.2 (3)
C10—C11—C12119.0 (3)O9—Cl1—O7109.8 (3)
C10—C11—H11120.5O8—Cl1—O7111.6 (2)
C12—C11—H11120.5O10—Cl1—O7109.8 (2)
N1—C12—C11123.1 (3)O5—Cl2—O6112.17 (18)
N1—C12—N5117.1 (2)O5—Cl2—O4108.84 (14)
C11—C12—N5119.7 (3)O6—Cl2—O4109.63 (15)
C14—C13—C17122.6 (3)O5—Cl2—O3109.85 (13)
C14—C13—H13118.7O6—Cl2—O3107.41 (14)
C17—C13—H13118.7O4—Cl2—O3108.88 (13)
C13—C14—C15120.3 (3)C12—N1—C6118.1 (2)
C13—C14—H14119.8C12—N1—Zn1131.17 (18)
C15—C14—H14119.8C6—N1—Zn1110.56 (16)
C16—C15—C14119.4 (3)C1—N2—C5117.8 (2)
C16—C15—H15120.3C1—N2—Zn1128.65 (19)
C14—C15—H15120.3C5—N2—Zn1113.59 (17)
C15—C16—N5120.8 (3)C18—N3—C22119.3 (3)
C15—C16—H16119.6C18—N3—Zn1127.9 (2)
N5—C16—H16119.6C22—N3—Zn1112.77 (17)
O1—C17—N5119.7 (3)C27—N4—C23117.6 (2)
O1—C17—C13126.6 (3)C27—N4—Zn1129.78 (18)
N5—C17—C13113.8 (3)C23—N4—Zn1111.17 (16)
N3—C18—C19121.6 (3)C16—N5—C17123.1 (3)
N3—C18—H18119.2C16—N5—C12118.4 (2)
C19—C18—H18119.2C17—N5—C12118.4 (2)
C20—C19—C18119.9 (3)C31—N6—C34119.7 (2)
C20—C19—H19120.0C31—N6—C27116.2 (2)
C18—C19—H19120.0C34—N6—C27124.0 (2)
C19—C20—C21120.9 (3)C34—O2—Zn1133.58 (19)
C19—C20—H20119.6Cl2—O3—Zn1135.05 (12)
C21—C20—H20119.6O2—Zn1—N3160.72 (8)
C20—C21—C22116.2 (3)O2—Zn1—N297.89 (8)
C20—C21—C26124.9 (3)N3—Zn1—N297.84 (9)
C22—C21—C26118.9 (3)O2—Zn1—N482.97 (8)
N3—C22—C21122.2 (3)N3—Zn1—N479.69 (8)
N3—C22—C23118.2 (2)N2—Zn1—N4170.52 (8)
C21—C22—C23119.6 (3)O2—Zn1—N192.99 (8)
N4—C23—C24123.6 (2)N3—Zn1—N1100.85 (8)
N4—C23—C22117.3 (2)N2—Zn1—N179.22 (8)
C24—C23—C22119.1 (2)N4—Zn1—N1110.20 (8)
C23—C24—C29116.5 (3)O2—Zn1—O385.91 (8)
C23—C24—C25120.0 (3)N3—Zn1—O384.52 (8)
C29—C24—C25123.5 (3)N2—Zn1—O384.69 (8)
C26—C25—C24121.1 (3)N4—Zn1—O385.96 (7)
C26—C25—H25119.4N1—Zn1—O3163.57 (8)
C24—C25—H25119.4
N2—C1—C2—C3−1.2 (5)N6—C27—N4—C23177.7 (2)
C1—C2—C3—C41.9 (5)C28—C27—N4—Zn1162.4 (2)
C2—C3—C4—C5−0.4 (4)N6—C27—N4—Zn1−17.5 (3)
C2—C3—C4—C8179.0 (3)C24—C23—N4—C27−2.9 (4)
C3—C4—C5—N2−1.8 (4)C22—C23—N4—C27177.5 (2)
C8—C4—C5—N2178.8 (3)C24—C23—N4—Zn1−170.4 (2)
C3—C4—C5—C6177.1 (3)C22—C23—N4—Zn110.1 (3)
C8—C4—C5—C6−2.4 (4)C15—C16—N5—C170.6 (4)
N2—C5—C6—N13.4 (4)C15—C16—N5—C12176.8 (3)
C4—C5—C6—N1−175.5 (2)O1—C17—N5—C16179.7 (3)
N2—C5—C6—C7−179.2 (2)C13—C17—N5—C16−0.8 (4)
C4—C5—C6—C71.9 (4)O1—C17—N5—C123.6 (4)
N1—C6—C7—C10−2.1 (4)C13—C17—N5—C12−177.0 (3)
C5—C6—C7—C10−179.3 (2)N1—C12—N5—C1674.3 (3)
N1—C6—C7—C9176.6 (2)C11—C12—N5—C16−102.5 (3)
C5—C6—C7—C9−0.7 (4)N1—C12—N5—C17−109.3 (3)
C3—C4—C8—C9−177.6 (3)C11—C12—N5—C1773.9 (4)
C5—C4—C8—C91.8 (4)C32—C31—N6—C349.1 (4)
C4—C8—C9—C7−0.6 (4)C32—C31—N6—C27−168.1 (3)
C10—C7—C9—C8178.6 (3)O2—C34—N6—C31167.6 (3)
C6—C7—C9—C80.1 (4)C30—C34—N6—C31−12.5 (4)
C6—C7—C10—C112.3 (4)O2—C34—N6—C27−15.4 (4)
C9—C7—C10—C11−176.3 (3)C30—C34—N6—C27164.4 (2)
C7—C10—C11—C12−0.1 (5)N4—C27—N6—C31−153.0 (2)
C10—C11—C12—N1−2.7 (5)C28—C27—N6—C3127.1 (4)
C10—C11—C12—N5173.8 (3)N4—C27—N6—C3430.0 (4)
C17—C13—C14—C150.2 (5)C28—C27—N6—C34−150.0 (3)
C13—C14—C15—C16−0.5 (5)N6—C34—O2—Zn1−13.4 (4)
C14—C15—C16—N50.0 (5)C30—C34—O2—Zn1166.7 (2)
C14—C13—C17—O1179.8 (4)O5—Cl2—O3—Zn143.3 (2)
C14—C13—C17—N50.4 (5)O6—Cl2—O3—Zn1165.51 (19)
N3—C18—C19—C20−0.3 (5)O4—Cl2—O3—Zn1−75.8 (2)
C18—C19—C20—C210.7 (5)C34—O2—Zn1—N345.0 (4)
C19—C20—C21—C22−0.5 (5)C34—O2—Zn1—N2−170.5 (2)
C19—C20—C21—C26176.6 (3)C34—O2—Zn1—N419.0 (2)
C20—C21—C22—N3−0.1 (4)C34—O2—Zn1—N1−91.0 (2)
C26—C21—C22—N3−177.4 (2)C34—O2—Zn1—O3105.4 (2)
C20—C21—C22—C23179.4 (2)C18—N3—Zn1—O2156.0 (3)
C26—C21—C22—C232.1 (4)C22—N3—Zn1—O2−20.7 (4)
N3—C22—C23—N4−5.7 (3)C18—N3—Zn1—N211.6 (2)
C21—C22—C23—N4174.8 (2)C22—N3—Zn1—N2−165.17 (17)
N3—C22—C23—C24174.7 (2)C18—N3—Zn1—N4−177.7 (2)
C21—C22—C23—C24−4.8 (4)C22—N3—Zn1—N45.57 (17)
N4—C23—C24—C294.8 (4)C18—N3—Zn1—N1−68.9 (2)
C22—C23—C24—C29−175.7 (2)C22—N3—Zn1—N1114.38 (18)
N4—C23—C24—C25−175.7 (2)C18—N3—Zn1—O395.4 (2)
C22—C23—C24—C253.9 (4)C22—N3—Zn1—O3−81.31 (18)
C23—C24—C25—C26−0.2 (4)C1—N2—Zn1—O2−94.4 (3)
C29—C24—C25—C26179.3 (3)C5—N2—Zn1—O286.92 (19)
C24—C25—C26—C21−2.6 (5)C1—N2—Zn1—N374.4 (3)
C20—C21—C26—C25−175.4 (3)C5—N2—Zn1—N3−104.27 (19)
C22—C21—C26—C251.6 (4)C1—N2—Zn1—N40.2 (7)
N4—C27—C28—C295.6 (4)C5—N2—Zn1—N4−178.5 (4)
N6—C27—C28—C29−174.5 (3)C1—N2—Zn1—N1174.0 (3)
C27—C28—C29—C24−3.4 (4)C5—N2—Zn1—N1−4.64 (18)
C23—C24—C29—C28−1.5 (4)C1—N2—Zn1—O3−9.3 (3)
C25—C24—C29—C28179.0 (3)C5—N2—Zn1—O3172.02 (19)
N6—C31—C32—C33−0.7 (5)C27—N4—Zn1—O2−2.4 (2)
C34—C30—C33—C32−0.9 (5)C23—N4—Zn1—O2163.13 (17)
C31—C32—C33—C30−3.4 (5)C27—N4—Zn1—N3−173.9 (2)
C33—C30—C34—O2−171.4 (3)C23—N4—Zn1—N3−8.39 (16)
C33—C30—C34—N68.8 (4)C27—N4—Zn1—N2−98.2 (5)
C11—C12—N1—C63.0 (4)C23—N4—Zn1—N267.3 (6)
N5—C12—N1—C6−173.7 (2)C27—N4—Zn1—N188.2 (2)
C11—C12—N1—Zn1−172.3 (2)C23—N4—Zn1—N1−106.26 (16)
N5—C12—N1—Zn111.1 (4)C27—N4—Zn1—O3−88.7 (2)
C7—C6—N1—C12−0.5 (4)C23—N4—Zn1—O376.77 (16)
C5—C6—N1—C12176.8 (2)C12—N1—Zn1—O284.3 (2)
C7—C6—N1—Zn1175.66 (19)C6—N1—Zn1—O2−91.27 (17)
C5—C6—N1—Zn1−7.0 (3)C12—N1—Zn1—N3−82.2 (2)
C2—C1—N2—C5−0.9 (4)C6—N1—Zn1—N3102.23 (17)
C2—C1—N2—Zn1−179.6 (2)C12—N1—Zn1—N2−178.3 (3)
C4—C5—N2—C12.5 (4)C6—N1—Zn1—N26.21 (16)
C6—C5—N2—C1−176.4 (2)C12—N1—Zn1—N40.6 (3)
C4—C5—N2—Zn1−178.7 (2)C6—N1—Zn1—N4−174.87 (16)
C6—C5—N2—Zn12.4 (3)C12—N1—Zn1—O3169.9 (2)
C19—C18—N3—C22−0.2 (4)C6—N1—Zn1—O3−5.6 (4)
C19—C18—N3—Zn1−176.8 (2)Cl2—O3—Zn1—O2−42.73 (19)
C21—C22—N3—C180.5 (4)Cl2—O3—Zn1—N3120.5 (2)
C23—C22—N3—C18−179.0 (2)Cl2—O3—Zn1—N2−141.1 (2)
C21—C22—N3—Zn1177.5 (2)Cl2—O3—Zn1—N440.50 (19)
C23—C22—N3—Zn1−2.0 (3)Cl2—O3—Zn1—N1−129.4 (2)
C28—C27—N4—C23−2.4 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2853).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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