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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1279.
Published online 2009 October 3. doi:  10.1107/S160053680903877X
PMCID: PMC2971005

Bis[2-(1H-1,2,4-triazol-1-yl-κN 2)-1,10-phenanthroline-κ2 N,N′]zinc(II) bis­(perchlorate)

Abstract

In the title complex, [Zn(C14H9N5)2](ClO4)2, 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline functions as a tridentate ligand and the ZnII ion assumes a distorted octa­hedral ZnN6 coordination geometry. There is a weak π–π stacking inter­action between symmetry-related triazolyl rings with a centroid–centroid distance of 3.802 (4) Å and a perpendicular distance of 3.413 Å between the rings.

Related literature

For related structures, see: Li (2008 [triangle]); Liu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1279-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H9N5)2](ClO4)2
  • M r = 758.79
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1279-efi1.jpg
  • a = 16.382 (2) Å
  • b = 26.278 (4) Å
  • c = 15.701 (2) Å
  • β = 117.399 (2)°
  • V = 6000.8 (14) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.07 mm−1
  • T = 298 K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.815, T max = 0.901
  • 17294 measured reflections
  • 6514 independent reflections
  • 3811 reflections with I > 2σ(I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.078
  • wR(F 2) = 0.198
  • S = 1.02
  • 6514 reflections
  • 442 parameters
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL and local programs.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903877X/bt5062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903877X/bt5062Isup2.hkl

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

Acknowledgments

This project was supported by the National Natural Science Foundation of China (No. 20971080).

supplementary crystallographic information

Comment

Metal complexes containing derivatives of 1,10-phenanthroline as ligands pay an important role in modern coordination chemistry (Li, 2008 and Liu et al. 2008), whereas complexes dealing with 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline as ligand have not been published to our knowledge. Interest in this area resulted in us to synthesize a series of this kind of complexes, and herein the crystal structure of the title complex is reported.

Fig. 1 shows the title complex and the data of Table 1 reveal that ZnII ion is located in a distorted octahedral coordination environment. For each 2-(1H-1,2,4-triazol-1-yl-κN2)-1,10-phenanthroline-k2N,N' ligand, both 1,2,4-triazolyl ring and 1,10-phenanthroline ring are basically located in a plane within 0.0476 Å (for ligand dealing with atom N1) and 0.0485 Å (for ligand dealing with atom N6) with a maximun deviations of 0.1310 (51) Å and 0.1118 (59) Å for atom C4 and atom C16, respectively, and the dihedral angle between the two planes is 88.07 (5)°, and it means that two planes are nearly perpendicular each other. There is a weak π···π stacking interaction involving symmetry-related 1,2,4-triazolyl rings, with the relevant distances being Cg1···Cg1i = 3.802 (4) Å and Cg1···Cg1iperp = 3.413 Å [symmetry code: (i) -x, y, 1/2 - z; Cg1 is the centroids of C1C2N3-N5 ring].

Experimental

5 ml Zn(ClO4).6H2O (0.0473 g, 0.127 mmol) H2O solution was added into 10 ml e thanol solution of 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline (0.0436 g, 0.176 mmol) and the mixed soluton was stirred for a few minutes. The yellow single crystals were obtained after the filtrate had been allowed to stand at room temperature for two weeks.

Refinement

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

Figures

Fig. 1.
Structure of title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[Zn(C14H9N5)2](ClO4)2F(000) = 3072
Mr = 758.79Dx = 1.680 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1862 reflections
a = 16.382 (2) Åθ = 2.6–21.0°
b = 26.278 (4) ŵ = 1.07 mm1
c = 15.701 (2) ÅT = 298 K
β = 117.399 (2)°Block, yellow
V = 6000.8 (14) Å30.20 × 0.15 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer6514 independent reflections
Radiation source: fine-focus sealed tube3811 reflections with I > 2σ(I)
graphiteRint = 0.068
[var phi] and ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −20→11
Tmin = 0.815, Tmax = 0.901k = −33→30
17294 measured reflectionsl = −19→19

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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0973P)2] where P = (Fo2 + 2Fc2)/3
6514 reflections(Δ/σ)max < 0.001
442 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = −0.34 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
C10.0631 (4)0.1459 (2)0.1825 (4)0.0624 (17)
H10.05740.18110.18410.075*
C20.0273 (4)0.0696 (2)0.1503 (4)0.0549 (15)
H2−0.00470.03940.12670.066*
C30.1886 (3)0.03571 (18)0.2340 (3)0.0368 (12)
C40.1711 (4)−0.0158 (2)0.2174 (4)0.0501 (14)
H40.1114−0.02850.18640.060*
C50.2452 (4)−0.0471 (2)0.2484 (4)0.0569 (16)
H50.2363−0.08200.23890.068*
C60.3349 (4)−0.02772 (19)0.2944 (4)0.0478 (14)
C70.3436 (3)0.02411 (18)0.3104 (3)0.0374 (12)
C80.4324 (3)0.04752 (19)0.3634 (4)0.0435 (13)
C90.4165 (5)−0.0573 (2)0.3268 (5)0.0703 (19)
H90.4119−0.09220.31560.084*
C100.4992 (4)−0.0360 (2)0.3727 (5)0.0675 (18)
H100.5510−0.05640.39110.081*
C110.5112 (4)0.0167 (2)0.3945 (4)0.0541 (15)
C120.5163 (4)0.1190 (2)0.4324 (5)0.0604 (16)
H120.51920.15360.44600.072*
C130.5980 (4)0.0915 (2)0.4680 (5)0.0706 (19)
H130.65380.10770.50520.085*
C140.5962 (4)0.0415 (3)0.4483 (5)0.0690 (19)
H140.65090.02340.47010.083*
C150.2538 (4)0.0882 (2)0.5021 (5)0.0575 (16)
H150.22600.05690.47800.069*
C160.3113 (5)0.1493 (3)0.5964 (5)0.0727 (19)
H160.33260.17090.64920.087*
C170.3369 (3)0.2034 (2)0.4786 (4)0.0453 (14)
C180.3637 (4)0.2490 (2)0.5325 (4)0.0580 (17)
H180.36590.25170.59250.070*
C190.3842 (3)0.2848 (2)0.4018 (5)0.0556 (16)
C200.3554 (3)0.23732 (18)0.3545 (4)0.0448 (14)
C210.3478 (3)0.22907 (19)0.2619 (4)0.0465 (14)
C220.4075 (4)0.3237 (2)0.3554 (6)0.075 (2)
H220.42670.35510.38550.090*
C230.4027 (4)0.3165 (2)0.2694 (6)0.076 (2)
H230.42010.34280.24150.091*
C240.3714 (4)0.2690 (2)0.2177 (5)0.0617 (18)
C250.3633 (5)0.2585 (3)0.1270 (6)0.078 (2)
H250.37950.28300.09490.094*
C260.3317 (5)0.2124 (3)0.0855 (5)0.0717 (19)
H260.32650.20540.02510.086*
C270.3073 (4)0.1755 (2)0.1339 (4)0.0592 (16)
H270.28330.14470.10360.071*
C320.3858 (4)0.2883 (2)0.4923 (5)0.067 (2)
H320.40290.31900.52550.081*
Cl10.12715 (11)0.06126 (6)0.95141 (13)0.0646 (5)
Cl20.61091 (10)0.20923 (5)0.65565 (12)0.0611 (4)
N10.2708 (3)0.05547 (14)0.2790 (3)0.0372 (10)
N20.4342 (3)0.09805 (15)0.3799 (3)0.0449 (11)
N30.1183 (3)0.07318 (15)0.2035 (3)0.0423 (10)
N40.1426 (3)0.12261 (15)0.2249 (3)0.0486 (12)
N5−0.0102 (3)0.1146 (2)0.1362 (4)0.0689 (15)
N60.2747 (3)0.12010 (17)0.4512 (3)0.0482 (11)
N70.3125 (3)0.16001 (17)0.5128 (3)0.0480 (11)
N80.2756 (4)0.1038 (2)0.5924 (4)0.0813 (17)
N90.3323 (3)0.19850 (14)0.3942 (3)0.0419 (11)
N100.3171 (3)0.18306 (16)0.2205 (3)0.0482 (11)
O10.5926 (4)0.2410 (2)0.5782 (4)0.1038 (18)
O20.5324 (3)0.18132 (17)0.6394 (4)0.0981 (18)
O30.6377 (4)0.23970 (19)0.7393 (4)0.110 (2)
O40.6827 (3)0.17485 (18)0.6715 (5)0.111 (2)
O50.1527 (6)0.1035 (3)0.9202 (6)0.179 (3)
O60.1939 (5)0.0568 (3)1.0476 (5)0.164 (3)
O70.1428 (6)0.0195 (3)0.9078 (6)0.171 (3)
O80.0439 (5)0.0590 (3)0.9451 (8)0.212 (5)
Zn10.29332 (4)0.13209 (2)0.31319 (4)0.0419 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.042 (4)0.046 (3)0.075 (4)0.008 (3)0.007 (3)0.007 (3)
C20.036 (3)0.052 (4)0.056 (4)−0.010 (3)0.004 (3)0.002 (3)
C30.032 (3)0.038 (3)0.036 (3)−0.003 (2)0.012 (2)−0.007 (2)
C40.051 (4)0.039 (3)0.056 (4)−0.009 (3)0.021 (3)−0.007 (3)
C50.072 (4)0.032 (3)0.064 (4)−0.008 (3)0.029 (3)−0.014 (3)
C60.058 (4)0.031 (3)0.053 (3)0.003 (2)0.025 (3)−0.002 (2)
C70.043 (3)0.033 (3)0.033 (3)0.005 (2)0.016 (2)−0.002 (2)
C80.044 (3)0.036 (3)0.049 (3)0.006 (2)0.021 (3)0.002 (2)
C90.079 (5)0.041 (4)0.089 (5)0.016 (3)0.036 (4)−0.005 (3)
C100.061 (4)0.049 (4)0.094 (5)0.021 (3)0.037 (4)0.011 (4)
C110.041 (3)0.050 (3)0.071 (4)0.012 (3)0.026 (3)0.007 (3)
C120.046 (4)0.046 (3)0.080 (4)−0.006 (3)0.021 (3)−0.003 (3)
C130.034 (3)0.065 (4)0.098 (5)−0.006 (3)0.017 (3)0.005 (4)
C140.031 (3)0.075 (5)0.093 (5)0.012 (3)0.023 (3)0.016 (4)
C150.045 (4)0.058 (4)0.063 (4)0.009 (3)0.020 (3)0.013 (3)
C160.086 (5)0.078 (5)0.051 (4)0.014 (4)0.029 (4)−0.001 (4)
C170.030 (3)0.041 (3)0.051 (4)0.009 (2)0.007 (2)−0.006 (3)
C180.047 (4)0.043 (3)0.061 (4)0.011 (3)0.004 (3)−0.009 (3)
C190.029 (3)0.034 (3)0.079 (5)0.000 (2)0.003 (3)0.002 (3)
C200.026 (3)0.033 (3)0.064 (4)0.000 (2)0.011 (2)0.003 (3)
C210.031 (3)0.032 (3)0.065 (4)0.004 (2)0.013 (3)0.013 (3)
C220.055 (4)0.038 (4)0.103 (6)−0.005 (3)0.012 (4)−0.001 (4)
C230.046 (4)0.044 (4)0.117 (7)−0.004 (3)0.021 (4)0.019 (4)
C240.039 (3)0.054 (4)0.083 (5)0.004 (3)0.020 (3)0.024 (3)
C250.063 (5)0.090 (6)0.086 (6)0.015 (4)0.037 (4)0.038 (5)
C260.072 (5)0.078 (5)0.070 (5)0.011 (4)0.037 (4)0.025 (4)
C270.059 (4)0.056 (4)0.054 (4)−0.002 (3)0.019 (3)0.004 (3)
C320.042 (4)0.048 (4)0.078 (5)0.007 (3)−0.002 (3)−0.020 (3)
Cl10.0555 (10)0.0612 (10)0.0722 (11)−0.0084 (7)0.0251 (8)−0.0016 (8)
Cl20.0475 (9)0.0434 (8)0.0758 (11)0.0065 (6)0.0140 (7)0.0022 (8)
N10.035 (2)0.031 (2)0.040 (2)−0.0009 (17)0.0125 (18)−0.0021 (18)
N20.035 (2)0.036 (2)0.055 (3)−0.0022 (18)0.013 (2)−0.001 (2)
N30.039 (3)0.033 (2)0.044 (3)−0.0050 (18)0.010 (2)−0.0052 (19)
N40.037 (3)0.035 (2)0.058 (3)−0.0018 (18)0.008 (2)0.005 (2)
N50.035 (3)0.059 (3)0.086 (4)−0.002 (2)0.005 (3)0.008 (3)
N60.044 (3)0.049 (3)0.046 (3)−0.002 (2)0.015 (2)−0.003 (2)
N70.041 (3)0.051 (3)0.046 (3)0.008 (2)0.015 (2)0.000 (2)
N80.097 (5)0.081 (5)0.074 (4)0.010 (3)0.046 (4)0.014 (4)
N90.031 (2)0.030 (2)0.053 (3)0.0021 (17)0.009 (2)−0.003 (2)
N100.044 (3)0.045 (3)0.051 (3)0.002 (2)0.018 (2)0.007 (2)
O10.129 (5)0.108 (4)0.094 (4)0.031 (3)0.069 (4)0.030 (3)
O20.046 (3)0.064 (3)0.155 (5)−0.001 (2)0.022 (3)0.009 (3)
O30.164 (6)0.064 (3)0.081 (4)0.001 (3)0.037 (4)−0.009 (3)
O40.050 (3)0.066 (3)0.194 (6)0.021 (2)0.036 (3)0.013 (3)
O50.220 (9)0.107 (6)0.183 (7)−0.039 (5)0.071 (6)0.051 (5)
O60.137 (6)0.225 (9)0.109 (5)−0.035 (6)0.038 (5)0.010 (5)
O70.259 (10)0.101 (5)0.202 (8)0.009 (6)0.147 (7)−0.021 (5)
O80.074 (5)0.219 (9)0.332 (12)−0.024 (5)0.084 (6)−0.080 (8)
Zn10.0370 (4)0.0292 (3)0.0523 (4)−0.0038 (2)0.0143 (3)−0.0033 (3)

Geometric parameters (Å, °)

C1—N41.310 (7)C17—C181.417 (7)
C1—N51.359 (7)C18—C321.342 (9)
C1—H10.9300C18—H180.9300
C2—N51.302 (7)C19—C221.405 (9)
C2—N31.335 (6)C19—C321.413 (9)
C2—H20.9300C19—C201.418 (7)
C3—N11.306 (6)C20—N91.337 (6)
C3—C41.384 (7)C20—C211.416 (8)
C3—N31.420 (6)C21—N101.355 (6)
C4—C51.357 (7)C21—C241.408 (7)
C4—H40.9300C22—C231.330 (10)
C5—C61.401 (7)C22—H220.9300
C5—H50.9300C23—C241.448 (9)
C6—C71.381 (7)C23—H230.9300
C6—C91.423 (8)C24—C251.395 (10)
C7—N11.343 (6)C25—C261.360 (9)
C7—C81.440 (7)C25—H250.9300
C8—N21.351 (6)C26—C271.399 (8)
C8—C111.407 (7)C26—H260.9300
C9—C101.331 (8)C27—N101.309 (7)
C9—H90.9300C27—H270.9300
C10—C111.417 (8)C32—H320.9300
C10—H100.9300Cl1—O81.323 (7)
C11—C141.413 (8)Cl1—O51.356 (6)
C12—N21.331 (7)Cl1—O71.379 (7)
C12—C131.391 (8)Cl1—O61.403 (7)
C12—H120.9300Cl2—O11.390 (5)
C13—C141.347 (8)Cl2—O21.398 (5)
C13—H130.9300Cl2—O41.411 (4)
C14—H140.9300Cl2—O31.424 (5)
C15—N61.308 (7)N1—Zn12.072 (4)
C15—N81.357 (8)N2—Zn12.235 (4)
C15—H150.9300N3—N41.355 (5)
C16—N81.321 (9)N4—Zn12.220 (4)
C16—N71.350 (7)N6—N71.367 (6)
C16—H160.9300N6—Zn12.344 (5)
C17—N91.299 (7)N9—Zn12.079 (4)
C17—N71.395 (7)N10—Zn12.141 (5)
N4—C1—N5114.6 (5)C25—C24—C21115.9 (6)
N4—C1—H1122.7C25—C24—C23125.8 (7)
N5—C1—H1122.7C21—C24—C23118.2 (7)
N5—C2—N3110.3 (5)C26—C25—C24120.1 (7)
N5—C2—H2124.8C26—C25—H25119.9
N3—C2—H2124.8C24—C25—H25119.9
N1—C3—C4124.3 (5)C25—C26—C27119.8 (7)
N1—C3—N3112.4 (4)C25—C26—H26120.1
C4—C3—N3123.4 (4)C27—C26—H26120.1
C5—C4—C3116.8 (5)N10—C27—C26122.0 (6)
C5—C4—H4121.6N10—C27—H27119.0
C3—C4—H4121.6C26—C27—H27119.0
C4—C5—C6121.2 (5)C18—C32—C19122.6 (6)
C4—C5—H5119.4C18—C32—H32118.7
C6—C5—H5119.4C19—C32—H32118.7
C7—C6—C5116.6 (5)O8—Cl1—O5119.2 (6)
C7—C6—C9118.2 (5)O8—Cl1—O7110.4 (5)
C5—C6—C9125.2 (5)O5—Cl1—O7108.3 (5)
N1—C7—C6122.6 (5)O8—Cl1—O6110.0 (6)
N1—C7—C8116.2 (4)O5—Cl1—O6103.9 (5)
C6—C7—C8121.3 (5)O7—Cl1—O6103.7 (5)
N2—C8—C11124.3 (5)O1—Cl2—O2110.2 (3)
N2—C8—C7117.2 (4)O1—Cl2—O4111.5 (4)
C11—C8—C7118.4 (5)O2—Cl2—O4108.6 (3)
C10—C9—C6121.2 (6)O1—Cl2—O3108.6 (3)
C10—C9—H9119.4O2—Cl2—O3109.3 (4)
C6—C9—H9119.4O4—Cl2—O3108.6 (4)
C9—C10—C11122.4 (6)C3—N1—C7118.4 (4)
C9—C10—H10118.8C3—N1—Zn1122.9 (3)
C11—C10—H10118.8C7—N1—Zn1118.6 (3)
C8—C11—C14115.8 (5)C12—N2—C8116.8 (5)
C8—C11—C10118.4 (5)C12—N2—Zn1131.0 (4)
C14—C11—C10125.8 (5)C8—N2—Zn1112.2 (3)
N2—C12—C13123.1 (6)C2—N3—N4109.8 (4)
N2—C12—H12118.4C2—N3—C3131.4 (4)
C13—C12—H12118.4N4—N3—C3118.7 (4)
C14—C13—C12119.9 (6)C1—N4—N3102.2 (4)
C14—C13—H13120.1C1—N4—Zn1145.6 (4)
C12—C13—H13120.1N3—N4—Zn1112.2 (3)
C13—C14—C11120.0 (5)C2—N5—C1103.1 (5)
C13—C14—H14120.0C15—N6—N7102.7 (5)
C11—C14—H14120.0C15—N6—Zn1146.4 (4)
N6—C15—N8115.3 (6)N7—N6—Zn1110.1 (3)
N6—C15—H15122.3C16—N7—N6109.0 (5)
N8—C15—H15122.3C16—N7—C17132.8 (5)
N8—C16—N7110.2 (6)N6—N7—C17118.0 (4)
N8—C16—H16124.9C16—N8—C15102.8 (6)
N7—C16—H16124.9C17—N9—C20120.3 (5)
N9—C17—N7114.9 (5)C17—N9—Zn1124.3 (4)
N9—C17—C18123.3 (6)C20—N9—Zn1115.4 (4)
N7—C17—C18121.8 (6)C27—N10—C21118.4 (5)
C32—C18—C17116.5 (6)C27—N10—Zn1129.6 (4)
C32—C18—H18121.7C21—N10—Zn1112.0 (4)
C17—C18—H18121.7N1—Zn1—N9160.34 (17)
C22—C19—C32126.3 (6)N1—Zn1—N10119.88 (17)
C22—C19—C20118.2 (6)N9—Zn1—N1077.86 (18)
C32—C19—C20115.6 (6)N1—Zn1—N473.44 (15)
N9—C20—C21116.8 (5)N9—Zn1—N4114.63 (15)
N9—C20—C19121.6 (6)N10—Zn1—N498.22 (16)
C21—C20—C19121.6 (5)N1—Zn1—N275.83 (15)
N10—C21—C24123.6 (6)N9—Zn1—N295.08 (15)
N10—C21—C20117.9 (5)N10—Zn1—N295.62 (16)
C24—C21—C20118.5 (5)N4—Zn1—N2149.23 (15)
C23—C22—C19121.3 (6)N1—Zn1—N691.45 (16)
C23—C22—H22119.3N9—Zn1—N671.43 (17)
C19—C22—H22119.3N10—Zn1—N6148.63 (17)
C22—C23—C24122.1 (7)N4—Zn1—N688.99 (16)
C22—C23—H23118.9N2—Zn1—N693.32 (16)
C24—C23—H23118.9
N1—C3—C4—C5−1.6 (8)C15—N6—N7—C16−0.2 (6)
N3—C3—C4—C5178.2 (5)Zn1—N6—N7—C16−172.4 (4)
C3—C4—C5—C6−0.4 (8)C15—N6—N7—C17−175.4 (4)
C4—C5—C6—C72.9 (8)Zn1—N6—N7—C1712.4 (5)
C4—C5—C6—C9−178.1 (6)N9—C17—N7—C16177.3 (5)
C5—C6—C7—N1−3.8 (8)C18—C17—N7—C16−3.2 (9)
C9—C6—C7—N1177.1 (5)N9—C17—N7—N6−8.8 (6)
C5—C6—C7—C8175.4 (5)C18—C17—N7—N6170.6 (4)
C9—C6—C7—C8−3.7 (8)N7—C16—N8—C15−1.1 (7)
N1—C7—C8—N22.7 (7)N6—C15—N8—C161.0 (7)
C6—C7—C8—N2−176.6 (5)N7—C17—N9—C20−179.1 (4)
N1—C7—C8—C11−177.4 (5)C18—C17—N9—C201.5 (7)
C6—C7—C8—C113.3 (8)N7—C17—N9—Zn1−0.6 (6)
C7—C6—C9—C101.1 (9)C18—C17—N9—Zn1−180.0 (4)
C5—C6—C9—C10−177.9 (6)C21—C20—N9—C17−179.5 (4)
C6—C9—C10—C111.8 (11)C19—C20—N9—C17−0.8 (7)
N2—C8—C11—C141.5 (9)C21—C20—N9—Zn11.9 (6)
C7—C8—C11—C14−178.3 (5)C19—C20—N9—Zn1−179.5 (4)
N2—C8—C11—C10179.5 (6)C26—C27—N10—C213.2 (8)
C7—C8—C11—C10−0.3 (8)C26—C27—N10—Zn1−175.8 (4)
C9—C10—C11—C8−2.2 (10)C24—C21—N10—C27−1.2 (7)
C9—C10—C11—C14175.6 (6)C20—C21—N10—C27178.1 (5)
N2—C12—C13—C141.0 (11)C24—C21—N10—Zn1178.0 (4)
C12—C13—C14—C11−2.2 (11)C20—C21—N10—Zn1−2.7 (5)
C8—C11—C14—C131.0 (9)C3—N1—Zn1—N9111.5 (5)
C10—C11—C14—C13−176.8 (7)C7—N1—Zn1—N9−63.6 (6)
N9—C17—C18—C32−0.6 (7)C3—N1—Zn1—N10−95.9 (4)
N7—C17—C18—C32180.0 (5)C7—N1—Zn1—N1089.0 (4)
C22—C19—C20—N9179.8 (5)C3—N1—Zn1—N4−5.9 (4)
C32—C19—C20—N9−0.6 (7)C7—N1—Zn1—N4179.0 (4)
C22—C19—C20—C21−1.6 (7)C3—N1—Zn1—N2175.7 (4)
C32—C19—C20—C21178.0 (5)C7—N1—Zn1—N20.6 (4)
N9—C20—C21—N100.7 (7)C3—N1—Zn1—N682.7 (4)
C19—C20—C21—N10−178.0 (4)C7—N1—Zn1—N6−92.4 (4)
N9—C20—C21—C24180.0 (5)C17—N9—Zn1—N1−25.2 (7)
C19—C20—C21—C241.3 (7)C20—N9—Zn1—N1153.4 (4)
C32—C19—C22—C23−179.4 (6)C17—N9—Zn1—N10178.9 (4)
C20—C19—C22—C230.2 (9)C20—N9—Zn1—N10−2.5 (3)
C19—C22—C23—C241.4 (10)C17—N9—Zn1—N485.3 (4)
N10—C21—C24—C25−1.3 (8)C20—N9—Zn1—N4−96.1 (4)
C20—C21—C24—C25179.4 (5)C17—N9—Zn1—N2−86.4 (4)
N10—C21—C24—C23179.6 (5)C20—N9—Zn1—N292.2 (3)
C20—C21—C24—C230.3 (8)C17—N9—Zn1—N65.4 (4)
C22—C23—C24—C25179.3 (6)C20—N9—Zn1—N6−176.0 (4)
C22—C23—C24—C21−1.7 (9)C27—N10—Zn1—N110.9 (5)
C21—C24—C25—C261.8 (9)C21—N10—Zn1—N1−168.1 (3)
C23—C24—C25—C26−179.2 (6)C27—N10—Zn1—N9−178.2 (5)
C24—C25—C26—C270.1 (10)C21—N10—Zn1—N92.7 (3)
C25—C26—C27—N10−2.7 (10)C27—N10—Zn1—N4−64.6 (5)
C17—C18—C32—C19−0.9 (8)C21—N10—Zn1—N4116.3 (3)
C22—C19—C32—C18−179.0 (6)C27—N10—Zn1—N287.8 (5)
C20—C19—C32—C181.4 (8)C21—N10—Zn1—N2−91.3 (3)
C4—C3—N1—C70.9 (8)C27—N10—Zn1—N6−166.3 (4)
N3—C3—N1—C7−179.0 (4)C21—N10—Zn1—N614.6 (5)
C4—C3—N1—Zn1−174.2 (4)C1—N4—Zn1—N1−175.7 (8)
N3—C3—N1—Zn15.9 (6)N3—N4—Zn1—N14.4 (3)
C6—C7—N1—C32.0 (7)C1—N4—Zn1—N923.5 (8)
C8—C7—N1—C3−177.3 (4)N3—N4—Zn1—N9−156.4 (3)
C6—C7—N1—Zn1177.3 (4)C1—N4—Zn1—N10−56.9 (8)
C8—C7—N1—Zn1−1.9 (6)N3—N4—Zn1—N10123.2 (4)
C13—C12—N2—C81.4 (9)C1—N4—Zn1—N2−172.7 (7)
C13—C12—N2—Zn1−179.5 (5)N3—N4—Zn1—N27.4 (6)
C11—C8—N2—C12−2.6 (8)C1—N4—Zn1—N692.5 (8)
C7—C8—N2—C12177.2 (5)N3—N4—Zn1—N6−87.4 (4)
C11—C8—N2—Zn1178.1 (4)C12—N2—Zn1—N1−178.3 (6)
C7—C8—N2—Zn1−2.1 (6)C8—N2—Zn1—N10.8 (4)
N5—C2—N3—N4−0.7 (7)C12—N2—Zn1—N9−16.0 (5)
N5—C2—N3—C3−176.8 (5)C8—N2—Zn1—N9163.1 (4)
N1—C3—N3—C2174.5 (5)C12—N2—Zn1—N1062.2 (5)
C4—C3—N3—C2−5.3 (9)C8—N2—Zn1—N10−118.6 (4)
N1—C3—N3—N4−1.2 (6)C12—N2—Zn1—N4178.7 (5)
C4—C3—N3—N4178.9 (5)C8—N2—Zn1—N4−2.1 (6)
N5—C1—N4—N30.4 (7)C12—N2—Zn1—N6−87.7 (5)
N5—C1—N4—Zn1−179.5 (5)C8—N2—Zn1—N691.5 (4)
C2—N3—N4—C10.2 (6)C15—N6—Zn1—N1−5.0 (7)
C3—N3—N4—C1176.9 (5)N7—N6—Zn1—N1161.1 (3)
C2—N3—N4—Zn1−179.9 (4)C15—N6—Zn1—N9−175.1 (7)
C3—N3—N4—Zn1−3.2 (6)N7—N6—Zn1—N9−9.0 (3)
N3—C2—N5—C10.9 (7)C15—N6—Zn1—N10172.6 (6)
N4—C1—N5—C2−0.8 (8)N7—N6—Zn1—N10−21.2 (5)
N8—C15—N6—N7−0.5 (6)C15—N6—Zn1—N468.4 (7)
N8—C15—N6—Zn1166.1 (5)N7—N6—Zn1—N4−125.5 (3)
N8—C16—N7—N60.9 (7)C15—N6—Zn1—N2−80.9 (7)
N8—C16—N7—C17175.1 (5)N7—N6—Zn1—N285.2 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5062).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, J. M. (2008). Acta Cryst. E64, m982. [PMC free article] [PubMed]
  • 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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