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In the title compound, [Zn(C14H12N4)4](ClO4)2, the Zn atom is coordinated tetra­hedrally by four monodentate 3,5-diphenyl-4-amino-4H-1,2,4-triazole ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020714/hb6215sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020714/hb6215Isup2.hkl
Contains datablock I

CCDC reference: 282357

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.055
  • wR factor = 0.149
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.76 Ratio PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C23 -C28 1.37 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C37 -C42 1.37 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N9 - H9B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Tetrakis(3,5-diphenyl-4-amino-4H-1,2,4-triazole-κN1)zinc(II) bis(perchlorate) top
Crystal data top
[Zn(C14H12N4)4](ClO4)2F(000) = 2496
Mr = 1209.37Dx = 1.434 Mg m3
Dm = 1.434 Mg m3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1922 reflections
a = 20.566 (5) Åθ = 2.3–17.4°
b = 20.174 (5) ŵ = 0.61 mm1
c = 14.243 (3) ÅT = 293 K
β = 108.614 (3)°Block, colourless
V = 5600 (2) Å30.26 × 0.22 × 0.14 mm
Z = 4
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
9901 independent reflections
Radiation source: fine-focus sealed tube5141 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.859, Tmax = 0.920k = 2412
29708 measured reflectionsl = 1616
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0302P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9901 reflectionsΔρmax = 0.49 e Å3
748 parametersΔρmin = 0.28 e Å3
12 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.257 (15)
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*/Ueq
Zn10.27073 (2)0.55166 (2)0.74627 (4)0.04285 (17)
N10.47288 (19)0.6744 (2)1.0440 (3)0.0776 (13)
H1A0.44710.67401.08460.093*
H1B0.47440.71661.02430.093*
N20.43503 (19)0.63567 (18)0.9628 (3)0.0561 (10)
N30.35271 (17)0.58122 (18)0.8580 (3)0.0522 (9)
N40.41433 (19)0.55372 (19)0.8555 (3)0.0549 (10)
N50.38252 (18)0.49740 (18)0.4515 (3)0.0579 (10)
H5A0.42100.47550.48610.070*
H5B0.39530.53940.44350.070*
N60.34267 (18)0.49684 (17)0.5159 (3)0.0476 (9)
N70.25391 (17)0.47935 (17)0.5655 (3)0.0507 (9)
N80.29696 (18)0.52507 (16)0.6276 (3)0.0488 (9)
N90.1746 (2)0.31801 (17)0.8509 (3)0.0744 (13)
H9A0.13670.30720.80080.089*
H9B0.21080.29930.83860.089*
N100.18367 (19)0.38583 (18)0.8316 (3)0.0559 (10)
N110.22822 (18)0.47624 (18)0.7974 (3)0.0531 (9)
N120.18740 (18)0.49312 (18)0.8545 (3)0.0525 (9)
N130.05960 (19)0.73126 (19)0.6610 (3)0.0716 (12)
H13A0.03170.71770.60190.086*
H13B0.04140.71810.70780.086*
N140.12449 (19)0.70022 (19)0.6887 (3)0.0524 (9)
N150.20527 (18)0.62884 (17)0.7059 (3)0.0494 (9)
N160.23558 (18)0.69081 (18)0.7197 (3)0.0509 (9)
C10.5861 (3)0.6234 (3)0.9659 (4)0.0890 (18)
H10.57510.66430.98700.107*
C20.6525 (3)0.6101 (5)0.9666 (5)0.116 (3)
H20.68630.64260.98630.140*
C30.6678 (4)0.5488 (6)0.9379 (6)0.127 (3)
H30.71270.53940.94090.152*
C40.6187 (4)0.5011 (4)0.9052 (5)0.114 (3)
H40.62970.46030.88380.137*
C50.5531 (3)0.5140 (3)0.9042 (4)0.0840 (17)
H50.51970.48130.88380.101*
C60.5364 (2)0.5747 (3)0.9331 (3)0.0650 (14)
C70.4632 (2)0.5869 (2)0.9195 (3)0.0548 (12)
C80.3655 (2)0.6299 (2)0.9230 (3)0.0502 (11)
C90.3140 (2)0.6697 (2)0.9463 (3)0.0501 (11)
C100.3194 (3)0.7378 (2)0.9552 (3)0.0639 (13)
H100.35900.75900.95300.077*
C110.2662 (3)0.7743 (3)0.9673 (4)0.0778 (16)
H110.27010.82010.97430.093*
C120.2072 (3)0.7428 (3)0.9689 (4)0.0747 (16)
H120.17070.76780.97490.090*
C130.2016 (3)0.6754 (3)0.9619 (3)0.0696 (14)
H130.16200.65450.96450.084*
C140.2553 (2)0.6388 (2)0.9509 (3)0.0571 (12)
H140.25180.59290.94660.068*
C150.3884 (3)0.6461 (2)0.6636 (3)0.0585 (12)
H150.34290.65670.65500.070*
C160.4386 (4)0.6914 (3)0.7015 (4)0.0830 (17)
H160.42720.73330.71880.100*
C170.5053 (4)0.6765 (3)0.7144 (4)0.092 (2)
H170.53910.70830.73970.111*
C180.5228 (3)0.6153 (3)0.6907 (4)0.0804 (17)
H180.56870.60520.70050.096*
C190.4726 (2)0.5677 (3)0.6518 (3)0.0636 (13)
H190.48420.52570.63550.076*
C200.4055 (2)0.5840 (2)0.6378 (3)0.0482 (11)
C210.3505 (2)0.5358 (2)0.5968 (3)0.0464 (11)
C220.2825 (2)0.4628 (2)0.4993 (3)0.0478 (11)
C230.2529 (2)0.4155 (2)0.4182 (3)0.0536 (12)
C240.2927 (3)0.3789 (2)0.3765 (4)0.0772 (16)
H240.34030.38180.40070.093*
C250.2609 (4)0.3375 (3)0.2977 (5)0.097 (2)
H250.28750.31250.26890.116*
C260.1910 (4)0.3328 (3)0.2616 (5)0.095 (2)
H260.17010.30700.20610.114*
C270.1525 (3)0.3659 (3)0.3069 (5)0.0897 (18)
H270.10520.36020.28580.108*
C280.1828 (3)0.4076 (2)0.3838 (4)0.0723 (14)
H280.15560.43110.41340.087*
C290.3328 (3)0.3807 (3)0.7562 (4)0.0761 (15)
H290.35630.40970.80640.091*
C300.3674 (3)0.3446 (4)0.7037 (5)0.0937 (19)
H300.41470.34920.71960.112*
C310.3337 (4)0.3031 (3)0.6305 (6)0.099 (2)
H310.35800.27990.59610.118*
C320.2638 (4)0.2942 (3)0.6054 (4)0.0876 (18)
H320.24110.26500.55500.105*
C330.2277 (3)0.3294 (2)0.6565 (4)0.0652 (14)
H330.18050.32410.64010.078*
C340.2618 (2)0.3724 (2)0.7316 (4)0.0554 (12)
C350.2255 (2)0.4116 (2)0.7842 (3)0.0502 (11)
C360.1610 (2)0.4379 (2)0.8751 (3)0.0524 (12)
C370.1167 (2)0.4325 (2)0.9365 (3)0.0544 (12)
C380.0605 (3)0.3906 (2)0.9120 (4)0.0721 (15)
H380.05090.36450.85540.086*
C390.0188 (3)0.3870 (3)0.9702 (4)0.0792 (16)
H390.01940.35920.95250.095*
C400.0335 (3)0.4240 (3)1.0536 (4)0.0902 (18)
H400.00650.42031.09470.108*
C410.0874 (3)0.4666 (3)1.0776 (4)0.0911 (18)
H410.09640.49271.13420.109*
C420.1288 (2)0.4713 (3)1.0184 (4)0.0714 (15)
H420.16510.50111.03450.086*
C430.1540 (3)0.8463 (3)0.7546 (4)0.0720 (15)
H430.11380.82920.76170.086*
C440.1701 (3)0.9118 (3)0.7760 (4)0.0869 (17)
H440.14140.93890.79800.104*
C450.2295 (4)0.9369 (3)0.7643 (4)0.0879 (18)
H450.24030.98140.77720.106*
C460.2724 (3)0.8971 (3)0.7340 (4)0.0835 (17)
H460.31260.91440.72730.100*
C470.2562 (3)0.8313 (3)0.7134 (4)0.0666 (14)
H470.28580.80430.69300.080*
C480.1968 (3)0.8050 (2)0.7225 (3)0.0561 (12)
C490.1858 (2)0.7340 (2)0.7095 (3)0.0486 (11)
C500.1383 (2)0.6351 (2)0.6859 (3)0.0482 (11)
C510.0906 (2)0.5798 (2)0.6700 (3)0.0513 (11)
C520.0989 (2)0.5264 (2)0.6135 (3)0.0610 (13)
H520.13190.52810.58150.073*
C530.0584 (3)0.4712 (3)0.6046 (4)0.0709 (15)
H530.06430.43510.56760.085*
C540.0088 (3)0.4695 (3)0.6510 (4)0.0763 (16)
H540.01890.43220.64490.092*
C550.0002 (3)0.5218 (3)0.7050 (4)0.0749 (15)
H550.03390.52040.73480.090*
C560.0411 (2)0.5773 (2)0.7167 (4)0.0619 (13)
H560.03540.61250.75550.074*
Cl10.47435 (7)0.64819 (7)0.38329 (12)0.0753 (4)
O10.5042 (3)0.7094 (2)0.4167 (4)0.1449 (19)
O20.5178 (2)0.5956 (2)0.4225 (4)0.1436 (19)
O30.4558 (2)0.6466 (2)0.2775 (3)0.1111 (14)
O40.4154 (2)0.6413 (2)0.4137 (3)0.1140 (15)
Cl20.00401 (8)0.27316 (7)0.61845 (11)0.0766 (4)
O50.0317 (4)0.3044 (3)0.7075 (4)0.196 (3)
O60.0559 (2)0.2639 (3)0.5749 (4)0.154 (2)
O70.0228 (3)0.2126 (2)0.6338 (4)0.1340 (18)
O80.0453 (2)0.3138 (2)0.5551 (4)0.1329 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0451 (3)0.0369 (3)0.0511 (3)0.0035 (2)0.0217 (2)0.0042 (2)
N10.069 (3)0.083 (3)0.075 (3)0.016 (2)0.015 (2)0.018 (3)
N20.055 (3)0.054 (3)0.060 (3)0.005 (2)0.021 (2)0.003 (2)
N30.052 (2)0.045 (2)0.063 (3)0.0015 (19)0.022 (2)0.002 (2)
N40.054 (2)0.061 (3)0.052 (2)0.009 (2)0.020 (2)0.005 (2)
N50.062 (2)0.056 (2)0.067 (3)0.008 (2)0.034 (2)0.002 (2)
N60.054 (2)0.040 (2)0.055 (2)0.0011 (18)0.026 (2)0.0016 (19)
N70.051 (2)0.046 (2)0.058 (2)0.0054 (19)0.021 (2)0.0061 (19)
N80.052 (2)0.040 (2)0.057 (2)0.0053 (18)0.0219 (19)0.0077 (18)
N90.092 (3)0.039 (2)0.109 (4)0.002 (2)0.055 (3)0.005 (2)
N100.063 (3)0.042 (2)0.065 (3)0.007 (2)0.024 (2)0.001 (2)
N110.054 (2)0.046 (2)0.063 (3)0.0001 (19)0.023 (2)0.0029 (19)
N120.053 (2)0.048 (2)0.059 (2)0.0040 (19)0.022 (2)0.0027 (19)
N130.057 (3)0.070 (3)0.079 (3)0.020 (2)0.009 (2)0.003 (2)
N140.056 (2)0.049 (2)0.051 (2)0.010 (2)0.0149 (19)0.0007 (18)
N150.050 (2)0.047 (2)0.055 (2)0.0019 (19)0.0223 (19)0.0033 (18)
N160.056 (2)0.042 (2)0.058 (2)0.001 (2)0.0212 (19)0.0040 (18)
C10.049 (3)0.131 (6)0.078 (4)0.002 (4)0.009 (3)0.007 (4)
C20.059 (4)0.176 (8)0.110 (6)0.009 (5)0.022 (4)0.030 (6)
C30.059 (4)0.215 (11)0.106 (6)0.050 (6)0.026 (4)0.055 (7)
C40.095 (5)0.147 (7)0.112 (6)0.057 (5)0.051 (5)0.043 (5)
C50.086 (4)0.089 (5)0.090 (4)0.030 (4)0.046 (3)0.026 (3)
C60.050 (3)0.090 (4)0.053 (3)0.011 (3)0.014 (3)0.020 (3)
C70.054 (3)0.059 (3)0.053 (3)0.010 (3)0.020 (3)0.013 (3)
C80.050 (3)0.047 (3)0.055 (3)0.008 (2)0.019 (2)0.003 (2)
C90.052 (3)0.049 (3)0.051 (3)0.005 (2)0.018 (2)0.001 (2)
C100.071 (3)0.054 (3)0.063 (3)0.003 (3)0.015 (3)0.010 (3)
C110.094 (4)0.065 (4)0.063 (4)0.017 (4)0.008 (3)0.016 (3)
C120.067 (4)0.092 (5)0.059 (3)0.021 (3)0.012 (3)0.012 (3)
C130.059 (3)0.092 (5)0.061 (3)0.002 (3)0.023 (3)0.007 (3)
C140.061 (3)0.059 (3)0.054 (3)0.004 (3)0.023 (3)0.011 (2)
C150.073 (3)0.044 (3)0.057 (3)0.005 (3)0.019 (3)0.000 (2)
C160.116 (5)0.057 (4)0.065 (4)0.024 (4)0.013 (4)0.001 (3)
C170.109 (5)0.081 (5)0.077 (4)0.053 (4)0.016 (4)0.004 (3)
C180.064 (4)0.113 (5)0.064 (4)0.025 (4)0.020 (3)0.003 (4)
C190.062 (3)0.073 (4)0.057 (3)0.014 (3)0.022 (3)0.008 (3)
C200.053 (3)0.045 (3)0.050 (3)0.004 (2)0.021 (2)0.002 (2)
C210.054 (3)0.034 (3)0.053 (3)0.000 (2)0.021 (2)0.001 (2)
C220.047 (3)0.045 (3)0.053 (3)0.001 (2)0.017 (2)0.001 (2)
C230.065 (3)0.040 (3)0.053 (3)0.004 (2)0.015 (3)0.002 (2)
C240.087 (4)0.060 (3)0.096 (4)0.017 (3)0.046 (3)0.028 (3)
C250.124 (6)0.072 (4)0.106 (5)0.015 (4)0.054 (5)0.042 (4)
C260.127 (6)0.067 (4)0.077 (4)0.023 (4)0.011 (4)0.018 (3)
C270.079 (4)0.071 (4)0.102 (5)0.008 (3)0.004 (4)0.026 (4)
C280.064 (4)0.061 (3)0.085 (4)0.003 (3)0.014 (3)0.012 (3)
C290.069 (4)0.078 (4)0.091 (4)0.014 (3)0.038 (3)0.015 (3)
C300.081 (4)0.117 (6)0.097 (5)0.026 (4)0.046 (4)0.018 (4)
C310.129 (6)0.083 (5)0.106 (6)0.040 (5)0.069 (5)0.015 (4)
C320.131 (6)0.055 (4)0.090 (5)0.016 (4)0.055 (4)0.003 (3)
C330.083 (4)0.042 (3)0.076 (4)0.001 (3)0.031 (3)0.003 (3)
C340.064 (3)0.041 (3)0.066 (3)0.008 (2)0.027 (3)0.012 (3)
C350.054 (3)0.045 (3)0.055 (3)0.003 (2)0.023 (2)0.002 (2)
C360.051 (3)0.050 (3)0.056 (3)0.008 (2)0.016 (2)0.003 (2)
C370.057 (3)0.054 (3)0.055 (3)0.007 (2)0.022 (2)0.006 (2)
C380.084 (4)0.068 (4)0.070 (4)0.033 (3)0.033 (3)0.018 (3)
C390.090 (4)0.084 (4)0.079 (4)0.030 (3)0.049 (3)0.008 (3)
C400.100 (5)0.114 (5)0.072 (4)0.023 (4)0.049 (4)0.004 (4)
C410.095 (4)0.108 (5)0.081 (4)0.031 (4)0.043 (4)0.033 (4)
C420.062 (3)0.079 (4)0.078 (4)0.011 (3)0.029 (3)0.009 (3)
C430.076 (3)0.054 (3)0.079 (4)0.007 (3)0.014 (3)0.006 (3)
C440.098 (5)0.048 (4)0.106 (5)0.013 (3)0.019 (4)0.016 (3)
C450.116 (5)0.045 (3)0.090 (4)0.003 (4)0.015 (4)0.006 (3)
C460.105 (4)0.059 (4)0.088 (4)0.018 (4)0.031 (4)0.004 (3)
C470.077 (4)0.056 (3)0.067 (3)0.004 (3)0.024 (3)0.003 (3)
C480.069 (3)0.044 (3)0.052 (3)0.008 (3)0.014 (3)0.003 (2)
C490.061 (3)0.042 (3)0.046 (3)0.001 (3)0.022 (2)0.001 (2)
C500.049 (3)0.049 (3)0.047 (3)0.007 (2)0.016 (2)0.004 (2)
C510.049 (3)0.047 (3)0.055 (3)0.000 (2)0.013 (2)0.005 (2)
C520.055 (3)0.067 (3)0.060 (3)0.000 (3)0.018 (2)0.015 (3)
C530.070 (3)0.055 (3)0.083 (4)0.004 (3)0.018 (3)0.023 (3)
C540.065 (3)0.062 (4)0.099 (4)0.014 (3)0.021 (3)0.010 (3)
C550.065 (3)0.066 (4)0.103 (4)0.008 (3)0.039 (3)0.009 (3)
C560.059 (3)0.054 (3)0.077 (4)0.002 (3)0.027 (3)0.011 (3)
Cl10.0802 (10)0.0538 (9)0.1019 (12)0.0096 (8)0.0430 (9)0.0156 (8)
O10.185 (5)0.087 (3)0.171 (5)0.058 (3)0.069 (4)0.025 (3)
O20.167 (4)0.120 (4)0.156 (4)0.096 (3)0.069 (4)0.058 (3)
O30.143 (4)0.108 (3)0.091 (3)0.000 (3)0.050 (3)0.011 (3)
O40.098 (3)0.121 (4)0.151 (4)0.008 (3)0.079 (3)0.017 (3)
Cl20.0906 (10)0.0666 (9)0.0704 (10)0.0077 (8)0.0224 (8)0.0088 (8)
O50.326 (8)0.138 (5)0.083 (4)0.020 (5)0.007 (4)0.050 (3)
O60.114 (4)0.167 (5)0.213 (6)0.028 (3)0.096 (4)0.004 (4)
O70.175 (4)0.063 (3)0.205 (5)0.020 (3)0.119 (4)0.001 (3)
O80.115 (3)0.110 (4)0.146 (4)0.001 (3)0.002 (3)0.028 (3)
Geometric parameters (Å, º) top
Zn1—N112.004 (4)C19—H190.9300
Zn1—N82.004 (3)C20—C211.464 (6)
Zn1—N32.005 (4)C22—C231.471 (6)
Zn1—N152.018 (3)C23—C241.372 (6)
N1—N21.407 (5)C23—C281.376 (6)
N1—H1A0.9010C24—C251.383 (7)
N1—H1B0.9006C24—H240.9300
N2—C81.365 (5)C25—C261.368 (8)
N2—C71.382 (5)C25—H250.9300
N3—C81.316 (5)C26—C271.346 (7)
N3—N41.395 (4)C26—H260.9300
N4—C71.306 (5)C27—C281.364 (7)
N5—N61.412 (4)C27—H270.9300
N5—H5A0.9026C28—H280.9300
N5—H5B0.9050C29—C301.391 (7)
N6—C211.362 (5)C29—C341.400 (6)
N6—C221.368 (5)C29—H290.9300
N7—C221.305 (5)C30—C311.345 (8)
N7—N81.385 (4)C30—H300.9300
N8—C211.327 (5)C31—C321.377 (8)
N9—N101.419 (5)C31—H310.9300
N9—H9A0.8990C32—C331.390 (7)
N9—H9B0.9011C32—H320.9300
N10—C351.356 (5)C33—C341.381 (6)
N10—C361.373 (5)C33—H330.9300
N11—C351.315 (5)C34—C351.450 (6)
N11—N121.385 (4)C36—C371.456 (6)
N12—C361.313 (5)C37—C421.359 (6)
N13—N141.412 (4)C37—C381.384 (6)
N13—H13A0.8966C38—C391.372 (6)
N13—H13B0.9026C38—H380.9300
N14—C501.347 (5)C39—C401.353 (7)
N14—C491.379 (5)C39—H390.9300
N15—C501.321 (5)C40—C411.356 (7)
N15—N161.383 (4)C40—H400.9300
N16—C491.317 (5)C41—C421.380 (6)
C1—C61.387 (7)C41—H410.9300
C1—C21.389 (8)C42—H420.9300
C1—H10.9300C43—C441.373 (7)
C2—C31.371 (10)C43—C481.390 (6)
C2—H20.9300C43—H430.9300
C3—C41.365 (10)C44—C451.380 (7)
C3—H30.9300C44—H440.9300
C4—C51.370 (8)C45—C461.360 (7)
C4—H40.9300C45—H450.9300
C5—C61.371 (7)C46—C471.378 (7)
C5—H50.9300C46—H460.9300
C6—C71.476 (6)C47—C481.376 (6)
C8—C91.451 (6)C47—H470.9300
C9—C141.380 (6)C48—C491.452 (6)
C9—C101.381 (6)C50—C511.455 (6)
C10—C111.373 (6)C51—C561.385 (6)
C10—H100.9300C51—C521.387 (6)
C11—C121.376 (7)C52—C531.373 (6)
C11—H110.9300C52—H520.9300
C12—C131.366 (7)C53—C541.382 (6)
C12—H120.9300C53—H530.9300
C13—C141.377 (6)C54—C551.351 (7)
C13—H130.9300C54—H540.9300
C14—H140.9300C55—C561.376 (6)
C15—C161.356 (6)C55—H550.9300
C15—C201.381 (6)C56—H560.9300
C15—H150.9300Cl1—O21.385 (4)
C16—C171.359 (8)Cl1—O11.392 (4)
C16—H160.9300Cl1—O41.418 (4)
C17—C181.359 (8)Cl1—O31.431 (4)
C17—H170.9300Cl2—O51.367 (5)
C18—C191.390 (7)Cl2—O71.386 (4)
C18—H180.9300Cl2—O81.390 (4)
C19—C201.370 (6)Cl2—O61.408 (4)
N11—Zn1—N8111.65 (15)C24—C23—C22122.3 (4)
N11—Zn1—N3106.94 (14)C28—C23—C22118.6 (4)
N8—Zn1—N3111.39 (14)C23—C24—C25118.9 (5)
N11—Zn1—N15111.13 (15)C23—C24—H24120.6
N8—Zn1—N15107.51 (14)C25—C24—H24120.6
N3—Zn1—N15108.19 (15)C26—C25—C24121.0 (6)
N2—N1—H1A103.8C26—C25—H25119.5
N2—N1—H1B109.5C24—C25—H25119.5
H1A—N1—H1B107.1C27—C26—C25119.6 (6)
C8—N2—C7106.6 (4)C27—C26—H26120.2
C8—N2—N1128.4 (4)C25—C26—H26120.2
C7—N2—N1124.1 (4)C26—C27—C28120.2 (6)
C8—N3—N4109.6 (4)C26—C27—H27119.9
C8—N3—Zn1135.1 (3)C28—C27—H27119.9
N4—N3—Zn1113.7 (3)C27—C28—C23121.0 (5)
C7—N4—N3106.3 (4)C27—C28—H28119.5
N6—N5—H5A103.3C23—C28—H28119.5
N6—N5—H5B110.0C30—C29—C34118.3 (6)
H5A—N5—H5B106.6C30—C29—H29120.9
C21—N6—C22107.0 (3)C34—C29—H29120.9
C21—N6—N5127.5 (3)C31—C30—C29121.2 (6)
C22—N6—N5124.9 (4)C31—C30—H30119.4
C22—N7—N8106.8 (3)C29—C30—H30119.4
C21—N8—N7109.1 (3)C30—C31—C32121.2 (6)
C21—N8—Zn1135.3 (3)C30—C31—H31119.4
N7—N8—Zn1115.3 (3)C32—C31—H31119.4
N10—N9—H9A102.4C31—C32—C33119.0 (6)
N10—N9—H9B101.4C31—C32—H32120.5
H9A—N9—H9B107.7C33—C32—H32120.5
C35—N10—C36106.9 (4)C34—C33—C32120.1 (5)
C35—N10—N9127.6 (4)C34—C33—H33119.9
C36—N10—N9124.4 (4)C32—C33—H33119.9
C35—N11—N12108.7 (3)C33—C34—C29120.1 (5)
C35—N11—Zn1134.8 (3)C33—C34—C35121.7 (4)
N12—N11—Zn1116.3 (3)C29—C34—C35118.2 (5)
C36—N12—N11107.1 (4)N11—C35—N10108.3 (4)
N14—N13—H13A113.1N11—C35—C34127.5 (4)
N14—N13—H13B104.0N10—C35—C34124.1 (4)
H13A—N13—H13B108.2N12—C36—N10109.0 (4)
C50—N14—C49107.6 (4)N12—C36—C37125.4 (4)
C50—N14—N13127.9 (4)N10—C36—C37125.6 (4)
C49—N14—N13123.9 (4)C42—C37—C38118.6 (4)
C50—N15—N16109.6 (3)C42—C37—C36119.6 (4)
C50—N15—Zn1133.7 (3)C38—C37—C36121.8 (4)
N16—N15—Zn1115.3 (3)C39—C38—C37120.8 (5)
C49—N16—N15106.4 (3)C39—C38—H38119.6
C6—C1—C2118.9 (7)C37—C38—H38119.6
C6—C1—H1120.6C40—C39—C38119.5 (5)
C2—C1—H1120.6C40—C39—H39120.2
C3—C2—C1119.4 (8)C38—C39—H39120.2
C3—C2—H2120.3C39—C40—C41120.5 (5)
C1—C2—H2120.3C39—C40—H40119.8
C4—C3—C2121.5 (7)C41—C40—H40119.8
C4—C3—H3119.2C40—C41—C42120.2 (5)
C2—C3—H3119.2C40—C41—H41119.9
C3—C4—C5119.2 (8)C42—C41—H41119.9
C3—C4—H4120.4C37—C42—C41120.3 (5)
C5—C4—H4120.4C37—C42—H42119.9
C4—C5—C6120.5 (7)C41—C42—H42119.9
C4—C5—H5119.7C44—C43—C48121.1 (5)
C6—C5—H5119.7C44—C43—H43119.4
C5—C6—C1120.4 (5)C48—C43—H43119.4
C5—C6—C7116.9 (5)C43—C44—C45119.1 (5)
C1—C6—C7122.5 (5)C43—C44—H44120.5
N4—C7—N2109.7 (4)C45—C44—H44120.5
N4—C7—C6122.1 (5)C46—C45—C44120.7 (5)
N2—C7—C6128.0 (5)C46—C45—H45119.6
N3—C8—N2107.7 (4)C44—C45—H45119.6
N3—C8—C9125.3 (4)C45—C46—C47119.9 (6)
N2—C8—C9127.0 (4)C45—C46—H46120.0
C14—C9—C10119.4 (4)C47—C46—H46120.0
C14—C9—C8118.3 (4)C48—C47—C46120.9 (5)
C10—C9—C8122.0 (4)C48—C47—H47119.6
C11—C10—C9120.1 (5)C46—C47—H47119.6
C11—C10—H10120.0C47—C48—C43118.3 (5)
C9—C10—H10120.0C47—C48—C49118.4 (4)
C10—C11—C12119.8 (5)C43—C48—C49122.9 (5)
C10—C11—H11120.1N16—C49—N14108.8 (4)
C12—C11—H11120.1N16—C49—C48123.6 (4)
C13—C12—C11120.8 (5)N14—C49—C48127.6 (4)
C13—C12—H12119.6N15—C50—N14107.6 (4)
C11—C12—H12119.6N15—C50—C51124.4 (4)
C12—C13—C14119.4 (5)N14—C50—C51127.9 (4)
C12—C13—H13120.3C56—C51—C52119.7 (4)
C14—C13—H13120.3C56—C51—C50121.1 (4)
C13—C14—C9120.5 (5)C52—C51—C50119.0 (4)
C13—C14—H14119.7C53—C52—C51120.0 (4)
C9—C14—H14119.7C53—C52—H52120.0
C16—C15—C20119.5 (5)C51—C52—H52120.0
C16—C15—H15120.3C52—C53—C54119.7 (5)
C20—C15—H15120.3C52—C53—H53120.2
C15—C16—C17120.8 (6)C54—C53—H53120.2
C15—C16—H16119.6C55—C54—C53120.2 (5)
C17—C16—H16119.6C55—C54—H54119.9
C16—C17—C18120.3 (6)C53—C54—H54119.9
C16—C17—H17119.9C54—C55—C56121.3 (5)
C18—C17—H17119.9C54—C55—H55119.3
C17—C18—C19120.3 (5)C56—C55—H55119.3
C17—C18—H18119.8C55—C56—C51119.1 (5)
C19—C18—H18119.8C55—C56—H56120.5
C20—C19—C18118.6 (5)C51—C56—H56120.5
C20—C19—H19120.7O2—Cl1—O1112.6 (4)
C18—C19—H19120.7O2—Cl1—O4107.8 (3)
C19—C20—C15120.6 (4)O1—Cl1—O4108.0 (3)
C19—C20—C21120.8 (4)O2—Cl1—O3109.1 (3)
C15—C20—C21118.6 (4)O1—Cl1—O3108.7 (3)
N8—C21—N6107.4 (4)O4—Cl1—O3110.7 (3)
N8—C21—C20126.4 (4)O5—Cl2—O7109.2 (4)
N6—C21—C20126.0 (4)O5—Cl2—O8109.4 (4)
N7—C22—N6109.7 (4)O7—Cl2—O8112.2 (3)
N7—C22—C23124.3 (4)O5—Cl2—O6108.7 (4)
N6—C22—C23125.9 (4)O7—Cl2—O6110.3 (3)
C24—C23—C28119.1 (5)O8—Cl2—O6106.9 (3)
N11—Zn1—N3—C8100.0 (4)C21—N6—C22—N70.1 (5)
N8—Zn1—N3—C8137.8 (4)N5—N6—C22—N7171.7 (4)
N15—Zn1—N3—C819.8 (4)C21—N6—C22—C23179.0 (4)
N11—Zn1—N3—N496.3 (3)N5—N6—C22—C237.2 (6)
N8—Zn1—N3—N426.0 (3)N7—C22—C23—C24152.6 (5)
N15—Zn1—N3—N4143.9 (3)N6—C22—C23—C2428.7 (7)
C8—N3—N4—C70.1 (5)N7—C22—C23—C2827.1 (7)
Zn1—N3—N4—C7167.8 (3)N6—C22—C23—C28151.6 (4)
C22—N7—N8—C210.8 (4)C28—C23—C24—C253.1 (8)
C22—N7—N8—Zn1173.4 (3)C22—C23—C24—C25177.2 (5)
N11—Zn1—N8—C21138.1 (4)C23—C24—C25—C260.0 (9)
N3—Zn1—N8—C2118.6 (4)C24—C25—C26—C274.0 (10)
N15—Zn1—N8—C2199.8 (4)C25—C26—C27—C284.9 (10)
N11—Zn1—N8—N734.1 (3)C26—C27—C28—C231.8 (9)
N3—Zn1—N8—N7153.6 (3)C24—C23—C28—C272.2 (8)
N15—Zn1—N8—N788.1 (3)C22—C23—C28—C27178.1 (5)
N8—Zn1—N11—C3515.9 (5)C34—C29—C30—C310.6 (9)
N3—Zn1—N11—C35106.2 (4)C29—C30—C31—C320.8 (10)
N15—Zn1—N11—C35135.9 (4)C30—C31—C32—C330.6 (9)
N8—Zn1—N11—N12158.3 (3)C31—C32—C33—C340.3 (8)
N3—Zn1—N11—N1279.6 (3)C32—C33—C34—C290.2 (7)
N15—Zn1—N11—N1238.3 (3)C32—C33—C34—C35177.9 (4)
C35—N11—N12—C360.3 (5)C30—C29—C34—C330.3 (7)
Zn1—N11—N12—C36176.0 (3)C30—C29—C34—C35178.1 (5)
N11—Zn1—N15—C5017.4 (4)N12—N11—C35—N100.0 (5)
N8—Zn1—N15—C50105.0 (4)Zn1—N11—C35—N10174.5 (3)
N3—Zn1—N15—C50134.6 (4)N12—N11—C35—C34178.1 (4)
N11—Zn1—N15—N16147.3 (3)Zn1—N11—C35—C347.4 (7)
N8—Zn1—N15—N1690.2 (3)C36—N10—C35—N110.3 (5)
N3—Zn1—N15—N1630.2 (3)N9—N10—C35—N11168.8 (4)
C50—N15—N16—C491.2 (5)C36—N10—C35—C34177.9 (4)
Zn1—N15—N16—C49167.2 (3)N9—N10—C35—C349.3 (7)
C6—C1—C2—C32.0 (9)C33—C34—C35—N11126.4 (5)
C1—C2—C3—C42.4 (11)C29—C34—C35—N1151.3 (7)
C2—C3—C4—C52.3 (11)C33—C34—C35—N1055.8 (6)
C3—C4—C5—C61.8 (9)C29—C34—C35—N10126.5 (5)
C4—C5—C6—C11.4 (8)N11—N12—C36—N100.5 (5)
C4—C5—C6—C7173.5 (5)N11—N12—C36—C37177.8 (4)
C2—C1—C6—C51.5 (8)C35—N10—C36—N120.5 (5)
C2—C1—C6—C7173.1 (5)N9—N10—C36—N12169.5 (4)
N3—N4—C7—N20.6 (5)C35—N10—C36—C37177.8 (4)
N3—N4—C7—C6176.1 (4)N9—N10—C36—C378.8 (7)
C8—N2—C7—N41.1 (5)N12—C36—C37—C4237.8 (7)
N1—N2—C7—N4171.2 (4)N10—C36—C37—C42140.2 (5)
C8—N2—C7—C6176.2 (4)N12—C36—C37—C38139.7 (5)
N1—N2—C7—C613.7 (7)N10—C36—C37—C3842.2 (7)
C5—C6—C7—N422.4 (7)C42—C37—C38—C391.5 (8)
C1—C6—C7—N4152.4 (5)C36—C37—C38—C39179.1 (5)
C5—C6—C7—N2163.0 (4)C37—C38—C39—C401.2 (9)
C1—C6—C7—N222.1 (7)C38—C39—C40—C412.7 (9)
N4—N3—C8—N20.8 (5)C39—C40—C41—C421.6 (10)
Zn1—N3—C8—N2163.4 (3)C38—C37—C42—C412.7 (8)
N4—N3—C8—C9179.5 (4)C36—C37—C42—C41179.7 (5)
Zn1—N3—C8—C916.2 (7)C40—C41—C42—C371.2 (9)
C7—N2—C8—N31.2 (5)C48—C43—C44—C450.7 (8)
N1—N2—C8—N3170.7 (4)C43—C44—C45—C461.4 (9)
C7—N2—C8—C9179.2 (4)C44—C45—C46—C470.9 (9)
N1—N2—C8—C99.6 (7)C45—C46—C47—C480.3 (8)
N3—C8—C9—C1438.9 (6)C46—C47—C48—C431.0 (7)
N2—C8—C9—C14141.6 (5)C46—C47—C48—C49173.9 (5)
N3—C8—C9—C10135.3 (5)C44—C43—C48—C470.5 (7)
N2—C8—C9—C1044.3 (7)C44—C43—C48—C49173.1 (5)
C14—C9—C10—C110.8 (7)N15—N16—C49—N140.5 (4)
C8—C9—C10—C11173.3 (4)N15—N16—C49—C48177.4 (4)
C9—C10—C11—C121.0 (7)C50—N14—C49—N160.4 (5)
C10—C11—C12—C132.1 (8)N13—N14—C49—N16171.7 (4)
C11—C12—C13—C141.4 (8)C50—N14—C49—C48178.1 (4)
C12—C13—C14—C90.5 (7)N13—N14—C49—C4810.5 (7)
C10—C9—C14—C131.6 (7)C47—C48—C49—N1621.7 (6)
C8—C9—C14—C13172.8 (4)C43—C48—C49—N16150.9 (5)
C20—C15—C16—C170.1 (8)C47—C48—C49—N14160.8 (4)
C15—C16—C17—C180.9 (9)C43—C48—C49—N1426.6 (7)
C16—C17—C18—C190.8 (9)N16—N15—C50—N141.4 (5)
C17—C18—C19—C200.2 (8)Zn1—N15—C50—N14164.0 (3)
C18—C19—C20—C151.2 (7)N16—N15—C50—C51178.1 (4)
C18—C19—C20—C21179.8 (4)Zn1—N15—C50—C5112.7 (7)
C16—C15—C20—C191.1 (7)C49—N14—C50—N151.1 (5)
C16—C15—C20—C21179.9 (4)N13—N14—C50—N15172.0 (4)
N7—N8—C21—N60.7 (4)C49—N14—C50—C51177.7 (4)
Zn1—N8—C21—N6171.8 (3)N13—N14—C50—C5111.4 (7)
N7—N8—C21—C20175.6 (4)N15—C50—C51—C56132.6 (5)
Zn1—N8—C21—C2011.9 (7)N14—C50—C51—C5643.5 (7)
C22—N6—C21—N80.4 (4)N15—C50—C51—C5242.2 (6)
N5—N6—C21—N8171.9 (4)N14—C50—C51—C52141.8 (5)
C22—N6—C21—C20175.9 (4)C56—C51—C52—C530.5 (7)
N5—N6—C21—C204.4 (7)C50—C51—C52—C53174.3 (4)
C19—C20—C21—N8137.8 (5)C51—C52—C53—C541.0 (7)
C15—C20—C21—N841.3 (6)C52—C53—C54—C550.2 (8)
C19—C20—C21—N646.7 (6)C53—C54—C55—C561.1 (8)
C15—C20—C21—N6134.3 (4)C54—C55—C56—C511.6 (8)
N8—N7—C22—N60.5 (4)C52—C51—C56—C550.8 (7)
N8—N7—C22—C23179.4 (4)C50—C51—C56—C55175.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.902.363.153 (6)148
N5—H5A···O2ii0.902.072.932 (6)159
N5—H5B···O40.912.173.067 (6)174
N9—H9A···O50.902.143.009 (8)161
N13—H13A···O8iii0.902.433.132 (7)136
N13—H13B···O7iv0.902.413.266 (7)159
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x, y+1, z+1; (iv) x, y+1/2, z+3/2.
 

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