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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1346.
Published online 2010 October 2. doi:  10.1107/S1600536810038493
PMCID: PMC3009243

Aqua­dipyridine­bis­(N-p-tolysulfonyl-l-leucinato)nickel(II)

Abstract

In each of the two mol­ecules in the asymmetric unit of the title compound, [Ni(C13H18NO4S)2(C5H5N)2(H2O)], the geometry of the Ni2+ ion is an extremely distorted trans-NiN2O4 octa­hedron, arising from its coordination by one water mol­ecule, two pyridine mol­ecules, and one O-monodentate and one O,O′-bidentate deprotonated N-p-tolysulfonyl-l-leucine ligand. In the crystal, mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds, forming chains along the c axis. An intra­molecular O—H(...)O hydrogen bond occurs in one of the mol­ecules.

Related literature

For background to amino acid derivatives in coordination chemistry, see: Brown et al. (2008 [triangle]). For a related structure, see: Li et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1346-scheme1.jpg

Experimental

Crystal data

  • [Ni(C13H18NO4S)2(C5H5N)2(H2O)]
  • M r = 803.61
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1346-efi1.jpg
  • a = 18.1023 (16) Å
  • b = 19.5538 (19) Å
  • c = 22.956 (2) Å
  • V = 8125.7 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.64 mm−1
  • T = 298 K
  • 0.38 × 0.36 × 0.31 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.794, T max = 0.828
  • 41421 measured reflections
  • 14319 independent reflections
  • 8009 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.242
  • S = 1.05
  • 14319 reflections
  • 949 parameters
  • H-atom parameters constrained
  • Δρmax = 1.08 e Å−3
  • Δρmin = −0.73 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 6501 Friedel pairs
  • Flack parameter: −0.02 (3)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038493/hb5641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038493/hb5641Isup2.hkl

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

Acknowledgments

The author would like to thank the Natural Science Foundation of Shandong (Y2007B60) for a research grant.

supplementary crystallographic information

Comment

Amino acid is an important for a class of physiological active substance, and the metal complexes of its small molecular ligands, not only are of important biological functions, but also are often essential active center that maintain structure and function of macromolecular organism complexes, such as metalloproteins and metal enzymes [Brown, et al., 2008]. In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Scheme I).

It can be seen that the coordination environment of the nickel atom consists of two nitrogen atoms from the two pyridine groups, three oxygen atoms from the two N-p-tolysulfonyl-L-leucine groups and one oxygen atom from the free water molecule, making up a distorted octahedral environment. The coordination oxygen atoms (O(1), O(2), O(5), O(9))and (O(10), O(11), O(14), O(18)) are situated equatorial place, and the nitrogen atoms are situated axial place. In addition, the four atoms (O(1), O(2), N(3), N(4)) are nearly coplanar. And the three atoms including (O(5), Ni(1), O(2)); (N(3), Ni(1), N(4)) and (N(7), Ni(2), N(8)) are nearly collinear. The distances of the Ni—O bonds are 1.993 (5)–2.215 (6)Å and Ni—N bonds are in the range of 2.084 (7)–2.123 (7)Å, respectively. They are similar to the Ni—O and Ni—N bond lengths reported previously [Li, et al., 2009]. The dihedral angles between the benzene rings are 3.6 °, and between the pyridine rings are 3.7 °. In the crystal, the molecules form a one-dimensional chain structure by hydrogen bonds.

Experimental

1 mmol (0.29 g) of nickel nitrate was added to the solution of pyridine (2 mmol, 0.16 g) in 15 ml of CH3OH/H2O (v:v=2:1). The mixture was continuously stirred for 1 h at refluxing temperature, then 2 mmol (0.56 g) of N-p-tolysulfonyl-L-leucine and 2 mmol(0.08 g) of sodium hydroxide were added to the mixture by stirring 6 h at refluxing temperature. The mixture was cooled at room temperature, and was collected by filtration. By evaporation in air at room temperature, light green blocks of (I) were obtained from methanol solution after two weeks. Yield 58%. Anal. Calcd. (%) for C36H48N4NiO9S2: C, 53.80; H, 6.07; N, 7.05. Found (%): C, 53.86; H, 6.10; N, 6.92.

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids.

Crystal data

[Ni(C13H18NO4S)2(C5H5N)2(H2O)]Dx = 1.314 Mg m3
Mr = 803.61Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6010 reflections
a = 18.1023 (16) Åθ = 2.4–23.6°
b = 19.5538 (19) ŵ = 0.64 mm1
c = 22.956 (2) ÅT = 298 K
V = 8125.7 (13) Å3Block, light green
Z = 80.38 × 0.36 × 0.31 mm
F(000) = 3392

Data collection

Bruker SMART CCD diffractometer14319 independent reflections
Radiation source: fine-focus sealed tube8009 reflections with I > 2σ(I)
graphiteRint = 0.056
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −21→21
Tmin = 0.794, Tmax = 0.828k = −12→23
41421 measured reflectionsl = −27→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.242w = 1/[σ2(Fo2) + (0.1133P)2 + 9.1777P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
14319 reflectionsΔρmax = 1.08 e Å3
949 parametersΔρmin = −0.73 e Å3
0 restraintsAbsolute structure: Flack (1983), 6501 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.02 (3)

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
Ni10.76523 (5)0.50099 (6)0.37915 (3)0.0379 (3)
Ni20.77376 (5)0.49881 (6)0.62033 (3)0.0378 (3)
N10.9600 (4)0.4038 (4)0.2580 (3)0.055 (2)
H10.95190.43300.23070.066*
N20.5510 (4)0.5974 (4)0.2472 (3)0.055 (2)
H20.55400.57020.21780.066*
N30.8263 (4)0.5913 (3)0.3807 (3)0.0468 (17)
N40.7028 (4)0.4096 (4)0.3743 (3)0.0523 (19)
N50.9634 (4)0.3977 (3)0.5003 (3)0.0551 (17)
H50.95590.42580.47210.066*
N60.5690 (4)0.5909 (4)0.5067 (3)0.066 (2)
H60.58810.56420.48110.079*
N70.8352 (4)0.5896 (3)0.6156 (3)0.0476 (17)
N80.7105 (4)0.4077 (3)0.6262 (3)0.0504 (18)
O10.8340 (3)0.4698 (3)0.3039 (2)0.0519 (15)
O20.8689 (3)0.4478 (3)0.3936 (2)0.0482 (14)
O30.9887 (4)0.3277 (3)0.1785 (3)0.0734 (19)
O41.0311 (3)0.3015 (4)0.2788 (3)0.074 (2)
O50.6665 (3)0.5502 (3)0.3671 (3)0.0598 (16)
O60.6880 (4)0.5581 (4)0.2726 (3)0.0740 (19)
O70.4767 (3)0.6960 (3)0.2772 (3)0.0629 (17)
O80.5203 (4)0.6836 (3)0.1747 (2)0.0679 (18)
O90.7479 (3)0.5075 (3)0.4669 (2)0.0558 (15)
H9C0.72170.54180.47630.067*
H9D0.78730.50600.48700.067*
O100.8760 (3)0.4474 (3)0.6354 (2)0.0483 (14)
O110.8378 (3)0.4595 (3)0.5458 (2)0.0518 (15)
O120.9871 (4)0.3152 (3)0.4238 (3)0.0724 (19)
O131.0341 (3)0.2958 (3)0.5240 (3)0.0687 (19)
O140.6879 (3)0.5406 (3)0.5735 (2)0.0522 (14)
O150.6206 (4)0.5520 (4)0.6533 (3)0.0693 (19)
O160.5394 (4)0.6662 (4)0.4244 (3)0.075 (2)
O170.4884 (3)0.6901 (3)0.5225 (3)0.0680 (18)
O180.7528 (3)0.5277 (3)0.7019 (2)0.0598 (17)
H18E0.76450.49680.72630.072*
H18F0.70740.53750.70600.072*
S10.97663 (14)0.32680 (13)0.24024 (9)0.0567 (6)
S20.53248 (13)0.67640 (13)0.23657 (9)0.0528 (6)
S30.97783 (13)0.31938 (12)0.48586 (9)0.0574 (6)
S40.54804 (13)0.66715 (12)0.48671 (9)0.0593 (7)
C10.8805 (5)0.4480 (5)0.3397 (4)0.047 (2)
C20.9577 (5)0.4280 (5)0.3194 (4)0.057 (2)
H2A0.97930.39390.34560.068*
C31.0035 (5)0.5003 (6)0.3233 (4)0.076 (3)
H3A0.97900.53340.29830.092*
H3B1.00010.51720.36290.092*
C41.0759 (6)0.4979 (7)0.3081 (5)0.087 (3)
H41.07960.47620.26980.105*
C51.1199 (8)0.4542 (8)0.3521 (6)0.124 (5)
H5A1.13240.48150.38540.187*
H5B1.16430.43790.33390.187*
H5C1.09040.41600.36420.187*
C61.1148 (9)0.5631 (9)0.3057 (8)0.154 (7)
H6A1.10310.58600.26980.231*
H6B1.16710.55520.30770.231*
H6C1.09980.59120.33790.231*
C70.8968 (6)0.2775 (6)0.2514 (4)0.066 (3)
C80.8903 (6)0.2361 (6)0.2997 (5)0.076 (3)
H80.92730.23600.32790.092*
C90.8279 (7)0.1941 (6)0.3065 (5)0.084 (3)
H9A0.82340.16620.33920.101*
C100.7732 (8)0.1944 (6)0.2645 (6)0.083 (3)
C110.7782 (7)0.2371 (6)0.2201 (5)0.083 (3)
H110.73940.23910.19370.099*
C120.8407 (6)0.2802 (6)0.2110 (5)0.075 (3)
H120.84340.30910.17890.090*
C130.7064 (8)0.1472 (7)0.2726 (6)0.112 (5)
H13A0.66630.16300.24880.168*
H13B0.69150.14760.31280.168*
H13C0.71950.10150.26140.168*
C140.6452 (5)0.5585 (5)0.3163 (4)0.052 (2)
C150.5630 (5)0.5703 (5)0.3062 (4)0.053 (2)
H150.54350.60220.33530.063*
C160.5243 (5)0.5001 (6)0.3120 (4)0.065 (2)
H16A0.54430.46970.28250.078*
H16B0.53690.48090.34970.078*
C170.4420 (5)0.5004 (6)0.3064 (4)0.073 (3)
H170.43040.52480.27020.088*
C180.4125 (8)0.4287 (7)0.2995 (6)0.125 (5)
H18A0.43980.39820.32420.188*
H18B0.41750.41450.25970.188*
H18C0.36130.42780.31040.188*
C190.4064 (7)0.5381 (7)0.3538 (6)0.107 (4)
H19A0.41180.51320.38950.160*
H19B0.35490.54380.34520.160*
H19C0.42920.58220.35770.160*
C200.6115 (6)0.7264 (5)0.2529 (4)0.057 (3)
C210.6153 (6)0.7613 (5)0.3054 (4)0.065 (3)
H210.57860.75550.33330.078*
C220.6741 (6)0.8049 (6)0.3160 (5)0.073 (3)
H220.67610.82880.35100.088*
C230.7299 (6)0.8135 (6)0.2754 (5)0.074 (3)
C240.7249 (7)0.7769 (6)0.2252 (5)0.078 (3)
H240.76230.78160.19770.094*
C250.6673 (6)0.7332 (5)0.2131 (4)0.068 (3)
H250.66630.70870.17840.082*
C260.7930 (7)0.8635 (6)0.2853 (6)0.100 (4)
H26A0.78260.90560.26540.150*
H26B0.83800.84430.27050.150*
H26C0.79810.87220.32630.150*
C270.8771 (5)0.6018 (5)0.4220 (4)0.053 (2)
H270.88190.56970.45160.064*
C280.9234 (5)0.6590 (5)0.4227 (4)0.061 (2)
H280.95790.66470.45230.073*
C290.9177 (5)0.7059 (5)0.3800 (4)0.063 (3)
H290.94720.74480.37980.076*
C300.8667 (5)0.6944 (5)0.3366 (4)0.063 (3)
H300.86310.72500.30570.076*
C310.8212 (5)0.6382 (5)0.3385 (4)0.056 (2)
H310.78570.63260.30960.067*
C320.6552 (5)0.3935 (5)0.4169 (4)0.066 (3)
H320.65530.41970.45070.079*
C330.6062 (6)0.3402 (5)0.4127 (5)0.072 (3)
H330.57410.33070.44330.086*
C340.6050 (6)0.3017 (5)0.3642 (5)0.068 (3)
H340.57340.26440.36100.082*
C350.6513 (6)0.3188 (5)0.3197 (5)0.073 (3)
H350.65050.29390.28520.087*
C360.6993 (5)0.3730 (5)0.3258 (4)0.057 (2)
H360.73030.38420.29500.069*
C370.8871 (5)0.4423 (5)0.5815 (4)0.049 (2)
C380.9624 (5)0.4237 (5)0.5604 (4)0.057 (2)
H380.98440.38980.58660.068*
C391.0090 (5)0.4940 (6)0.5636 (4)0.073 (3)
H39A0.98920.52550.53500.088*
H39B1.00170.51420.60180.088*
C401.0858 (6)0.4871 (6)0.5538 (5)0.085 (3)
H401.09280.46100.51780.102*
C411.1208 (8)0.5564 (8)0.5458 (7)0.144 (6)
H41A1.14140.55960.50740.215*
H41B1.15920.56250.57410.215*
H41C1.08410.59130.55080.215*
C421.1211 (8)0.4503 (8)0.6007 (6)0.125 (5)
H42A1.10340.46720.63740.187*
H42B1.17360.45660.59840.187*
H42C1.10970.40250.59740.187*
C430.8980 (5)0.2718 (5)0.5019 (5)0.064 (2)
C440.8944 (6)0.2348 (5)0.5536 (4)0.072 (3)
H440.93250.23740.58070.086*
C450.8325 (6)0.1936 (6)0.5643 (5)0.079 (3)
H450.83000.16780.59820.095*
C460.7745 (7)0.1913 (6)0.5239 (6)0.082 (3)
C470.7809 (7)0.2284 (6)0.4757 (5)0.082 (3)
H470.74280.22580.44860.098*
C480.8397 (6)0.2704 (6)0.4628 (5)0.076 (3)
H480.84030.29690.42920.091*
C490.7092 (7)0.1442 (6)0.5347 (6)0.107 (4)
H49A0.66440.16700.52390.160*
H49B0.70730.13240.57530.160*
H49C0.71480.10340.51190.160*
C500.6281 (5)0.5530 (5)0.5994 (4)0.054 (2)
C510.5579 (5)0.5640 (5)0.5645 (4)0.062 (2)
H510.52730.59680.58590.074*
C520.5157 (6)0.4939 (6)0.5638 (5)0.084 (3)
H52A0.53810.46520.53420.100*
H52B0.52370.47170.60100.100*
C530.4375 (6)0.4962 (7)0.5532 (5)0.095 (3)
H530.42870.51970.51610.114*
C540.4094 (9)0.4213 (8)0.5479 (8)0.158 (7)
H54A0.43920.39200.57190.238*
H54B0.41280.40670.50810.238*
H54C0.35890.41890.56050.238*
C550.3951 (8)0.5313 (8)0.5993 (7)0.134 (6)
H55A0.40010.50660.63520.200*
H55B0.34390.53310.58840.200*
H55C0.41370.57690.60420.200*
C560.6242 (5)0.7204 (5)0.5006 (5)0.069 (3)
C570.6807 (6)0.7248 (6)0.4614 (5)0.080 (3)
H570.68160.69750.42820.096*
C580.7360 (7)0.7708 (6)0.4726 (5)0.089 (4)
H580.77390.77440.44540.106*
C590.7395 (7)0.8112 (6)0.5203 (6)0.087 (3)
C600.6844 (7)0.8042 (6)0.5619 (5)0.087 (3)
H600.68660.82900.59650.105*
C610.6254 (6)0.7596 (6)0.5515 (5)0.077 (3)
H610.58710.75590.57840.093*
C620.8021 (7)0.8594 (6)0.5310 (6)0.111 (4)
H62A0.84350.84660.50730.166*
H62B0.81600.85760.57140.166*
H62C0.78700.90510.52130.166*
C630.8813 (5)0.6052 (5)0.6601 (4)0.055 (2)
H630.88470.57510.69130.065*
C640.9227 (5)0.6632 (5)0.6610 (4)0.062 (3)
H640.95380.67210.69240.074*
C650.9184 (5)0.7078 (5)0.6160 (4)0.062 (3)
H650.94590.74790.61640.074*
C660.8738 (5)0.6932 (5)0.5706 (4)0.066 (3)
H660.87190.72200.53840.079*
C670.8309 (5)0.6345 (5)0.5727 (4)0.056 (2)
H670.79760.62640.54260.067*
C680.6698 (5)0.3942 (5)0.6721 (4)0.061 (2)
H680.67500.42180.70490.073*
C690.6190 (6)0.3405 (5)0.6742 (4)0.065 (3)
H690.59280.33140.70820.078*
C700.6083 (5)0.3013 (5)0.6253 (4)0.065 (3)
H700.57380.26610.62430.078*
C710.6514 (6)0.3169 (5)0.5778 (5)0.068 (3)
H710.64690.29130.54380.082*
C720.7004 (5)0.3692 (5)0.5799 (4)0.057 (2)
H720.72840.37830.54690.068*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0456 (5)0.0384 (6)0.0299 (5)−0.0012 (6)−0.0009 (4)0.0023 (5)
Ni20.0463 (5)0.0375 (5)0.0296 (5)0.0033 (7)−0.0035 (4)0.0000 (5)
N10.060 (5)0.063 (5)0.044 (4)0.014 (4)0.001 (3)0.002 (4)
N20.060 (5)0.057 (5)0.048 (4)0.013 (4)−0.005 (3)−0.005 (4)
N30.053 (4)0.044 (4)0.044 (4)−0.002 (3)−0.004 (4)−0.002 (3)
N40.055 (4)0.049 (5)0.053 (5)−0.006 (4)0.004 (4)0.000 (4)
N50.065 (4)0.057 (4)0.043 (4)0.019 (3)0.006 (4)0.004 (4)
N60.070 (5)0.068 (5)0.061 (5)0.018 (4)−0.011 (4)−0.008 (5)
N70.056 (4)0.045 (4)0.042 (4)0.001 (3)−0.002 (4)0.001 (3)
N80.057 (4)0.049 (5)0.046 (4)0.001 (4)−0.002 (4)0.004 (3)
O10.054 (3)0.052 (4)0.049 (3)0.003 (3)−0.005 (3)0.000 (3)
O20.055 (3)0.050 (4)0.039 (3)0.005 (3)0.005 (3)−0.001 (3)
O30.086 (5)0.074 (5)0.060 (4)0.031 (4)0.019 (4)−0.010 (4)
O40.064 (4)0.086 (5)0.074 (4)0.030 (4)−0.002 (4)0.014 (4)
O50.061 (4)0.055 (4)0.063 (4)0.002 (3)−0.012 (3)0.002 (3)
O60.064 (4)0.085 (5)0.074 (5)0.019 (4)−0.005 (4)−0.012 (4)
O70.055 (4)0.070 (4)0.064 (4)0.017 (3)0.003 (3)−0.015 (3)
O80.092 (5)0.067 (4)0.044 (3)0.019 (4)−0.018 (3)0.001 (3)
O90.052 (3)0.072 (4)0.043 (3)0.013 (3)−0.007 (2)−0.009 (3)
O100.056 (3)0.052 (4)0.036 (3)0.006 (3)0.008 (3)0.001 (3)
O110.054 (3)0.059 (4)0.043 (3)0.009 (3)0.002 (3)0.001 (3)
O120.098 (5)0.075 (5)0.044 (3)0.029 (4)0.014 (3)−0.006 (3)
O130.060 (4)0.074 (4)0.072 (4)0.028 (3)0.002 (3)0.016 (3)
O140.051 (3)0.057 (4)0.049 (3)0.006 (3)0.000 (3)0.005 (3)
O150.071 (4)0.086 (5)0.051 (4)0.028 (4)0.004 (3)0.004 (4)
O160.087 (5)0.091 (5)0.047 (4)0.027 (4)−0.017 (3)0.001 (4)
O170.061 (4)0.080 (5)0.063 (4)0.027 (4)−0.002 (3)−0.010 (3)
O180.063 (4)0.068 (4)0.048 (3)0.001 (3)0.008 (3)−0.003 (3)
S10.0578 (15)0.0663 (17)0.0459 (13)0.0231 (13)0.0074 (11)0.0025 (11)
S20.0584 (14)0.0570 (15)0.0429 (13)0.0214 (12)−0.0021 (10)−0.0054 (10)
S30.0683 (14)0.0610 (15)0.0431 (13)0.0325 (12)0.0091 (11)0.0051 (11)
S40.0666 (14)0.0648 (15)0.0465 (14)0.0265 (12)−0.0127 (11)−0.0076 (11)
C10.052 (5)0.046 (5)0.043 (5)0.002 (4)0.003 (4)0.000 (4)
C20.056 (5)0.069 (6)0.046 (5)0.008 (5)0.001 (4)−0.001 (5)
C30.072 (6)0.086 (7)0.070 (6)0.003 (7)0.006 (5)−0.008 (7)
C40.086 (8)0.091 (8)0.084 (7)−0.003 (8)0.009 (6)−0.002 (8)
C50.116 (11)0.137 (13)0.120 (12)0.008 (10)0.007 (10)0.001 (11)
C60.134 (14)0.149 (16)0.179 (17)−0.041 (13)0.013 (13)−0.001 (14)
C70.070 (7)0.070 (7)0.058 (6)0.017 (6)−0.004 (5)−0.003 (6)
C80.078 (8)0.083 (8)0.068 (7)0.005 (7)−0.002 (6)0.002 (6)
C90.088 (8)0.085 (8)0.079 (8)0.002 (7)−0.001 (7)0.000 (6)
C100.083 (8)0.079 (9)0.088 (9)0.006 (7)−0.001 (8)−0.006 (7)
C110.081 (8)0.086 (9)0.080 (8)0.003 (7)−0.006 (7)−0.008 (7)
C120.078 (7)0.080 (8)0.068 (7)0.011 (6)−0.005 (6)−0.002 (6)
C130.109 (11)0.099 (10)0.129 (12)−0.010 (9)−0.005 (9)−0.003 (9)
C140.057 (6)0.052 (6)0.048 (5)0.001 (5)−0.007 (5)0.001 (5)
C150.049 (5)0.058 (6)0.052 (5)0.006 (4)−0.009 (4)−0.002 (4)
C160.064 (5)0.064 (6)0.066 (5)−0.003 (6)−0.007 (4)−0.001 (6)
C170.067 (6)0.081 (7)0.072 (6)−0.005 (7)−0.006 (5)−0.005 (7)
C180.111 (11)0.131 (13)0.134 (12)−0.045 (10)−0.016 (9)−0.021 (10)
C190.083 (8)0.123 (11)0.114 (10)−0.014 (8)0.002 (8)−0.008 (9)
C200.060 (7)0.057 (6)0.055 (6)0.014 (5)0.001 (4)0.002 (5)
C210.067 (6)0.068 (7)0.060 (6)0.009 (6)0.001 (5)0.002 (5)
C220.076 (7)0.076 (7)0.068 (7)0.010 (6)−0.001 (6)0.001 (6)
C230.071 (7)0.070 (7)0.081 (7)0.004 (6)0.003 (7)0.012 (6)
C240.076 (8)0.083 (8)0.076 (7)0.007 (7)0.013 (7)0.011 (7)
C250.071 (7)0.072 (7)0.062 (6)0.012 (6)0.007 (5)0.001 (5)
C260.092 (9)0.095 (9)0.113 (10)−0.012 (8)−0.003 (8)0.004 (8)
C270.059 (5)0.055 (6)0.046 (5)−0.006 (5)−0.005 (5)0.001 (5)
C280.068 (6)0.060 (6)0.055 (6)−0.015 (5)−0.007 (5)−0.003 (5)
C290.069 (6)0.060 (7)0.061 (6)−0.018 (5)0.000 (5)−0.001 (5)
C300.070 (6)0.060 (7)0.059 (6)−0.013 (5)−0.002 (5)0.010 (5)
C310.061 (6)0.055 (6)0.051 (5)−0.005 (5)−0.006 (4)0.003 (5)
C320.075 (7)0.062 (7)0.060 (6)−0.014 (5)0.011 (5)−0.003 (5)
C330.079 (7)0.068 (7)0.069 (7)−0.021 (6)0.012 (6)0.003 (6)
C340.070 (7)0.060 (7)0.075 (7)−0.022 (5)0.002 (6)−0.001 (6)
C350.079 (7)0.066 (7)0.074 (7)−0.007 (6)0.002 (6)−0.006 (6)
C360.063 (6)0.055 (6)0.055 (6)−0.006 (5)0.003 (5)0.001 (5)
C370.055 (5)0.051 (5)0.042 (5)0.006 (4)0.004 (4)0.004 (4)
C380.060 (6)0.063 (6)0.047 (5)0.013 (5)0.003 (4)0.003 (4)
C390.073 (6)0.075 (7)0.071 (6)0.003 (7)0.008 (5)0.002 (7)
C400.080 (7)0.090 (10)0.084 (8)−0.004 (7)0.007 (6)0.003 (7)
C410.130 (12)0.145 (14)0.156 (14)−0.050 (12)0.007 (12)0.014 (12)
C420.111 (11)0.140 (13)0.122 (12)−0.011 (10)−0.010 (10)0.013 (11)
C430.075 (6)0.062 (6)0.056 (5)0.021 (5)−0.010 (6)−0.006 (6)
C440.080 (7)0.069 (7)0.066 (7)0.010 (6)−0.006 (6)0.000 (6)
C450.085 (8)0.076 (8)0.076 (7)0.006 (6)−0.010 (6)−0.005 (6)
C460.079 (8)0.075 (8)0.092 (9)0.007 (7)−0.010 (7)−0.009 (7)
C470.087 (9)0.081 (8)0.077 (8)0.006 (7)−0.015 (7)−0.014 (7)
C480.082 (8)0.076 (8)0.070 (7)0.016 (7)−0.008 (6)−0.004 (6)
C490.095 (9)0.098 (10)0.128 (11)−0.011 (8)−0.004 (8)−0.008 (8)
C500.060 (6)0.053 (6)0.049 (6)0.006 (5)−0.002 (5)−0.004 (4)
C510.057 (5)0.060 (6)0.067 (6)0.008 (5)−0.013 (5)−0.002 (5)
C520.076 (7)0.076 (8)0.098 (8)0.003 (7)−0.014 (6)−0.011 (7)
C530.090 (8)0.092 (9)0.103 (9)−0.006 (9)−0.007 (7)−0.013 (9)
C540.154 (15)0.141 (15)0.180 (17)−0.048 (13)0.003 (13)−0.032 (13)
C550.119 (12)0.145 (15)0.137 (13)−0.031 (10)0.013 (10)−0.020 (11)
C560.069 (6)0.075 (7)0.062 (6)0.019 (5)−0.007 (6)−0.001 (6)
C570.081 (8)0.088 (8)0.072 (7)0.013 (7)−0.002 (6)−0.003 (6)
C580.087 (9)0.096 (10)0.083 (8)0.007 (8)0.002 (7)0.006 (7)
C590.085 (8)0.083 (9)0.093 (9)0.005 (7)−0.009 (7)0.005 (7)
C600.086 (8)0.086 (9)0.089 (9)0.010 (7)−0.006 (7)−0.008 (7)
C610.077 (7)0.082 (8)0.072 (7)0.012 (6)−0.003 (6)−0.009 (6)
C620.103 (10)0.101 (10)0.128 (12)−0.012 (8)−0.007 (9)−0.002 (8)
C630.064 (6)0.051 (6)0.049 (5)−0.006 (5)−0.005 (5)0.005 (4)
C640.067 (6)0.061 (7)0.057 (6)−0.019 (5)−0.012 (5)−0.001 (5)
C650.068 (6)0.057 (6)0.060 (6)−0.016 (5)−0.003 (5)−0.003 (5)
C660.072 (6)0.063 (7)0.063 (6)−0.008 (5)−0.004 (5)0.008 (5)
C670.063 (6)0.056 (6)0.048 (5)−0.006 (5)−0.006 (5)0.004 (5)
C680.071 (6)0.059 (6)0.052 (6)−0.011 (5)0.000 (5)0.000 (5)
C690.077 (7)0.060 (7)0.059 (6)−0.016 (5)0.003 (5)0.008 (5)
C700.073 (7)0.059 (6)0.064 (7)−0.018 (5)−0.003 (5)0.000 (5)
C710.078 (7)0.061 (7)0.065 (6)−0.013 (6)−0.005 (6)−0.007 (5)
C720.065 (6)0.056 (6)0.049 (5)−0.006 (5)0.000 (5)−0.006 (5)

Geometric parameters (Å, °)

Ni1—O92.042 (5)C22—C231.386 (15)
Ni1—O52.048 (6)C22—H220.9300
Ni1—N32.084 (7)C23—C241.359 (15)
Ni1—N42.117 (7)C23—C261.520 (15)
Ni1—O22.171 (6)C24—C251.376 (15)
Ni1—O12.215 (6)C24—H240.9300
Ni2—O181.993 (5)C25—H250.9300
Ni2—O142.059 (6)C26—H26A0.9600
Ni2—N72.097 (7)C26—H26B0.9600
Ni2—N82.123 (7)C26—H26C0.9600
Ni2—O102.134 (6)C27—C281.398 (12)
Ni2—O112.205 (5)C27—H270.9300
N1—C21.488 (10)C28—C291.345 (12)
N1—S11.588 (8)C28—H280.9300
N1—H10.8600C29—C301.376 (12)
N2—C151.471 (10)C29—H290.9300
N2—S21.600 (7)C30—C311.376 (12)
N2—H20.8600C30—H300.9300
N3—C311.336 (10)C31—H310.9300
N3—C271.338 (10)C32—C331.372 (13)
N4—C361.325 (10)C32—H320.9300
N4—C321.341 (11)C33—C341.345 (13)
N5—C381.471 (11)C33—H330.9300
N5—S31.589 (7)C34—C351.363 (13)
N5—H50.8600C34—H340.9300
N6—C511.441 (12)C35—C361.377 (13)
N6—S41.605 (7)C35—H350.9300
N6—H60.8600C36—H360.9300
N7—C671.323 (10)C37—C381.492 (12)
N7—C631.354 (10)C38—C391.613 (13)
N8—C681.313 (10)C38—H380.9800
N8—C721.316 (10)C39—C401.415 (14)
O1—C11.251 (10)C39—H39A0.9700
O2—C11.254 (9)C39—H39B0.9700
O3—S11.434 (6)C40—C421.443 (16)
O4—S11.413 (6)C40—C411.508 (17)
O5—C141.239 (10)C40—H400.9800
O6—C141.268 (10)C41—H41A0.9600
O7—S21.427 (6)C41—H41B0.9600
O8—S21.444 (6)C41—H41C0.9600
O9—H9C0.8501C42—H42A0.9600
O9—H9D0.8500C42—H42B0.9600
O10—C371.259 (9)C42—H42C0.9600
O11—C371.256 (10)C43—C481.384 (13)
O12—S31.436 (6)C43—C441.392 (13)
O13—S31.420 (6)C44—C451.401 (14)
O14—C501.259 (10)C44—H440.9300
O15—C501.245 (10)C45—C461.401 (15)
O16—S41.439 (6)C45—H450.9300
O17—S41.429 (6)C46—C471.327 (14)
O18—H18E0.8500C46—C491.519 (16)
O18—H18F0.8500C47—C481.377 (15)
S1—C71.757 (12)C47—H470.9300
S2—C201.773 (11)C48—H480.9300
S3—C431.758 (10)C49—H49A0.9600
S4—C561.758 (11)C49—H49B0.9600
C1—C21.525 (12)C49—H49C0.9600
C2—C31.640 (14)C50—C511.518 (12)
C2—H2A0.9800C51—C521.570 (14)
C3—C41.357 (14)C51—H510.9800
C3—H3A0.9700C52—C531.438 (14)
C3—H3B0.9700C52—H52A0.9700
C4—C61.458 (18)C52—H52B0.9700
C4—C51.544 (17)C53—C551.476 (16)
C4—H40.9800C53—C541.555 (18)
C5—H5A0.9600C53—H530.9800
C5—H5B0.9600C54—H54A0.9600
C5—H5C0.9600C54—H54B0.9600
C6—H6A0.9600C54—H54C0.9600
C6—H6B0.9600C55—H55A0.9600
C6—H6C0.9600C55—H55B0.9600
C7—C121.377 (14)C55—H55C0.9600
C7—C81.377 (14)C56—C571.365 (14)
C8—C91.406 (15)C56—C611.397 (14)
C8—H80.9300C57—C581.370 (15)
C9—C101.383 (16)C57—H570.9300
C9—H9A0.9300C58—C591.353 (15)
C10—C111.321 (15)C58—H580.9300
C10—C131.531 (17)C59—C601.388 (16)
C11—C121.426 (15)C59—C621.495 (16)
C11—H110.9300C60—C611.400 (15)
C12—H120.9300C60—H600.9300
C13—H13A0.9600C61—H610.9300
C13—H13B0.9600C62—H62A0.9600
C13—H13C0.9600C62—H62B0.9600
C14—C151.523 (12)C62—H62C0.9600
C15—C161.547 (13)C63—C641.359 (12)
C15—H150.9800C63—H630.9300
C16—C171.494 (12)C64—C651.355 (12)
C16—H16A0.9700C64—H640.9300
C16—H16B0.9700C65—C661.349 (12)
C17—C191.465 (15)C65—H650.9300
C17—C181.508 (16)C66—C671.387 (12)
C17—H170.9800C66—H660.9300
C18—H18A0.9600C67—H670.9300
C18—H18B0.9600C68—C691.397 (13)
C18—H18C0.9600C68—H680.9300
C19—H19A0.9600C69—C701.373 (13)
C19—H19B0.9600C69—H690.9300
C19—H19C0.9600C70—C711.375 (13)
C20—C251.369 (13)C70—H700.9300
C20—C211.386 (13)C71—C721.353 (12)
C21—C221.386 (14)C71—H710.9300
C21—H210.9300C72—H720.9300
O9—Ni1—O588.3 (2)C24—C23—C22117.3 (11)
O9—Ni1—N390.7 (3)C24—C23—C26121.1 (11)
O5—Ni1—N393.8 (3)C22—C23—C26121.6 (11)
O9—Ni1—N491.3 (3)C23—C24—C25123.2 (11)
O5—Ni1—N485.6 (3)C23—C24—H24118.4
N3—Ni1—N4177.9 (3)C25—C24—H24118.4
O9—Ni1—O290.7 (2)C20—C25—C24119.0 (10)
O5—Ni1—O2178.8 (2)C20—C25—H25120.5
N3—Ni1—O286.8 (3)C24—C25—H25120.5
N4—Ni1—O293.8 (3)C23—C26—H26A109.5
O9—Ni1—O1150.8 (2)C23—C26—H26B109.5
O5—Ni1—O1120.9 (2)H26A—C26—H26B109.5
N3—Ni1—O187.1 (2)C23—C26—H26C109.5
N4—Ni1—O191.5 (2)H26A—C26—H26C109.5
O2—Ni1—O160.1 (2)H26B—C26—H26C109.5
O18—Ni2—O14103.6 (2)N3—C27—C28122.9 (9)
O18—Ni2—N784.8 (2)N3—C27—H27118.6
O14—Ni2—N792.1 (2)C28—C27—H27118.6
O18—Ni2—N894.3 (3)C29—C28—C27119.4 (9)
O14—Ni2—N887.7 (2)C29—C28—H28120.3
N7—Ni2—N8179.1 (3)C27—C28—H28120.3
O18—Ni2—O1098.4 (2)C28—C29—C30117.9 (9)
O14—Ni2—O10157.8 (2)C28—C29—H29121.1
N7—Ni2—O1087.0 (2)C30—C29—H29121.1
N8—Ni2—O1093.5 (2)C31—C30—C29120.6 (9)
O18—Ni2—O11158.1 (2)C31—C30—H30119.7
O14—Ni2—O1197.5 (2)C29—C30—H30119.7
N7—Ni2—O1188.6 (2)N3—C31—C30122.0 (8)
N8—Ni2—O1192.3 (2)N3—C31—H31119.0
O10—Ni2—O1160.4 (2)C30—C31—H31119.0
C2—N1—S1123.4 (6)N4—C32—C33122.9 (10)
C2—N1—H1118.3N4—C32—H32118.6
S1—N1—H1118.3C33—C32—H32118.6
C15—N2—S2121.3 (6)C34—C33—C32119.6 (10)
C15—N2—H2119.4C34—C33—H33120.2
S2—N2—H2119.4C32—C33—H33120.2
C31—N3—C27117.1 (7)C33—C34—C35118.2 (9)
C31—N3—Ni1122.1 (6)C33—C34—H34120.9
C27—N3—Ni1120.5 (6)C35—C34—H34120.9
C36—N4—C32117.0 (8)C34—C35—C36120.1 (10)
C36—N4—Ni1121.8 (6)C34—C35—H35120.0
C32—N4—Ni1120.2 (6)C36—C35—H35120.0
C38—N5—S3122.1 (6)N4—C36—C35122.1 (9)
C38—N5—H5118.9N4—C36—H36118.9
S3—N5—H5118.9C35—C36—H36118.9
C51—N6—S4124.7 (7)O11—C37—O10120.4 (8)
C51—N6—H6117.6O11—C37—C38120.2 (8)
S4—N6—H6117.6O10—C37—C38118.9 (8)
C67—N7—C63116.6 (8)N5—C38—C37113.5 (7)
C67—N7—Ni2124.7 (6)N5—C38—C39109.3 (7)
C63—N7—Ni2118.6 (6)C37—C38—C39104.9 (7)
C68—N8—C72117.1 (8)N5—C38—H38109.7
C68—N8—Ni2121.5 (6)C37—C38—H38109.7
C72—N8—Ni2120.3 (6)C39—C38—H38109.7
C1—O1—Ni187.7 (5)C40—C39—C38115.2 (10)
C1—O2—Ni189.6 (5)C40—C39—H39A108.5
C14—O5—Ni1117.5 (6)C38—C39—H39A108.5
Ni1—O9—H9C112.7C40—C39—H39B108.5
Ni1—O9—H9D113.8C38—C39—H39B108.5
H9C—O9—H9D110.9H39A—C39—H39B107.5
C37—O10—Ni290.9 (5)C39—C40—C42111.3 (11)
C37—O11—Ni287.8 (5)C39—C40—C41110.3 (11)
C50—O14—Ni2118.5 (5)C42—C40—C41110.7 (12)
Ni2—O18—H18E111.7C39—C40—H40108.1
Ni2—O18—H18F110.6C42—C40—H40108.1
H18E—O18—H18F109.2C41—C40—H40108.1
O4—S1—O3121.1 (4)C40—C41—H41A109.5
O4—S1—N1107.6 (4)C40—C41—H41B109.5
O3—S1—N1105.7 (4)H41A—C41—H41B109.5
O4—S1—C7106.9 (5)C40—C41—H41C109.5
O3—S1—C7106.0 (5)H41A—C41—H41C109.5
N1—S1—C7109.1 (5)H41B—C41—H41C109.5
O7—S2—O8120.5 (4)C40—C42—H42A109.5
O7—S2—N2107.9 (4)C40—C42—H42B109.5
O8—S2—N2106.0 (4)H42A—C42—H42B109.5
O7—S2—C20106.6 (4)C40—C42—H42C109.5
O8—S2—C20106.1 (4)H42A—C42—H42C109.5
N2—S2—C20109.4 (4)H42B—C42—H42C109.5
O13—S3—O12120.6 (4)C48—C43—C44120.4 (10)
O13—S3—N5107.6 (4)C48—C43—S3120.1 (9)
O12—S3—N5106.3 (4)C44—C43—S3119.5 (8)
O13—S3—C43106.8 (4)C43—C44—C45119.1 (10)
O12—S3—C43105.9 (5)C43—C44—H44120.5
N5—S3—C43109.3 (4)C45—C44—H44120.5
O17—S4—O16119.6 (4)C44—C45—C46120.1 (11)
O17—S4—N6107.8 (4)C44—C45—H45119.9
O16—S4—N6107.4 (4)C46—C45—H45119.9
O17—S4—C56107.6 (5)C47—C46—C45117.9 (12)
O16—S4—C56105.8 (5)C47—C46—C49122.4 (12)
N6—S4—C56108.3 (4)C45—C46—C49119.6 (12)
O1—C1—O2122.5 (8)C46—C47—C48124.9 (12)
O1—C1—C2120.2 (7)C46—C47—H47117.5
O2—C1—C2117.0 (8)C48—C47—H47117.5
N1—C2—C1113.3 (7)C47—C48—C43117.5 (11)
N1—C2—C3108.2 (7)C47—C48—H48121.3
C1—C2—C3103.1 (7)C43—C48—H48121.3
N1—C2—H2A110.7C46—C49—H49A109.5
C1—C2—H2A110.7C46—C49—H49B109.5
C3—C2—H2A110.7H49A—C49—H49B109.5
C4—C3—C2116.4 (11)C46—C49—H49C109.5
C4—C3—H3A108.2H49A—C49—H49C109.5
C2—C3—H3A108.2H49B—C49—H49C109.5
C4—C3—H3B108.2O15—C50—O14124.1 (8)
C2—C3—H3B108.2O15—C50—C51115.8 (9)
H3A—C3—H3B107.3O14—C50—C51119.8 (8)
C3—C4—C6116.5 (13)N6—C51—C50115.0 (8)
C3—C4—C5110.5 (11)N6—C51—C52112.1 (8)
C6—C4—C5105.1 (12)C50—C51—C52106.8 (8)
C3—C4—H4108.2N6—C51—H51107.6
C6—C4—H4108.2C50—C51—H51107.6
C5—C4—H4108.2C52—C51—H51107.6
C4—C5—H5A109.5C53—C52—C51117.0 (10)
C4—C5—H5B109.5C53—C52—H52A108.0
H5A—C5—H5B109.5C51—C52—H52A108.0
C4—C5—H5C109.5C53—C52—H52B108.0
H5A—C5—H5C109.5C51—C52—H52B108.0
H5B—C5—H5C109.5H52A—C52—H52B107.3
C4—C6—H6A109.5C52—C53—C55113.9 (11)
C4—C6—H6B109.5C52—C53—C54107.8 (12)
H6A—C6—H6B109.5C55—C53—C54108.9 (12)
C4—C6—H6C109.5C52—C53—H53108.7
H6A—C6—H6C109.5C55—C53—H53108.7
H6B—C6—H6C109.5C54—C53—H53108.7
C12—C7—C8120.2 (11)C53—C54—H54A109.5
C12—C7—S1119.1 (9)C53—C54—H54B109.5
C8—C7—S1120.7 (9)H54A—C54—H54B109.5
C7—C8—C9120.0 (11)C53—C54—H54C109.5
C7—C8—H8120.0H54A—C54—H54C109.5
C9—C8—H8120.0H54B—C54—H54C109.5
C10—C9—C8119.8 (12)C53—C55—H55A109.5
C10—C9—H9A120.1C53—C55—H55B109.5
C8—C9—H9A120.1H55A—C55—H55B109.5
C11—C10—C9119.4 (13)C53—C55—H55C109.5
C11—C10—C13121.9 (13)H55A—C55—H55C109.5
C9—C10—C13118.6 (12)H55B—C55—H55C109.5
C10—C11—C12122.9 (12)C57—C56—C61120.5 (11)
C10—C11—H11118.6C57—C56—S4120.3 (9)
C12—C11—H11118.6C61—C56—S4119.2 (9)
C7—C12—C11117.5 (11)C56—C57—C58117.7 (11)
C7—C12—H12121.2C56—C57—H57121.1
C11—C12—H12121.2C58—C57—H57121.1
C10—C13—H13A109.5C59—C58—C57124.6 (12)
C10—C13—H13B109.5C59—C58—H58117.7
H13A—C13—H13B109.5C57—C58—H58117.7
C10—C13—H13C109.5C58—C59—C60117.9 (12)
H13A—C13—H13C109.5C58—C59—C62122.5 (13)
H13B—C13—H13C109.5C60—C59—C62119.5 (12)
O5—C14—O6123.5 (9)C59—C60—C61119.5 (12)
O5—C14—C15117.9 (9)C59—C60—H60120.3
O6—C14—C15118.6 (8)C61—C60—H60120.3
N2—C15—C14109.8 (7)C56—C61—C60119.7 (11)
N2—C15—C16109.4 (7)C56—C61—H61120.2
C14—C15—C16107.2 (7)C60—C61—H61120.2
N2—C15—H15110.1C59—C62—H62A109.5
C14—C15—H15110.1C59—C62—H62B109.5
C16—C15—H15110.1H62A—C62—H62B109.5
C17—C16—C15116.2 (9)C59—C62—H62C109.5
C17—C16—H16A108.2H62A—C62—H62C109.5
C15—C16—H16A108.2H62B—C62—H62C109.5
C17—C16—H16B108.2N7—C63—C64122.7 (8)
C15—C16—H16B108.2N7—C63—H63118.6
H16A—C16—H16B107.4C64—C63—H63118.6
C19—C17—C16112.1 (9)C65—C64—C63119.5 (9)
C19—C17—C18112.9 (11)C65—C64—H64120.2
C16—C17—C18111.1 (11)C63—C64—H64120.2
C19—C17—H17106.8C66—C65—C64119.2 (9)
C16—C17—H17106.8C66—C65—H65120.4
C18—C17—H17106.8C64—C65—H65120.4
C17—C18—H18A109.5C65—C66—C67118.9 (9)
C17—C18—H18B109.5C65—C66—H66120.6
H18A—C18—H18B109.5C67—C66—H66120.6
C17—C18—H18C109.5N7—C67—C66122.8 (9)
H18A—C18—H18C109.5N7—C67—H67118.6
H18B—C18—H18C109.5C66—C67—H67118.6
C17—C19—H19A109.5N8—C68—C69123.2 (9)
C17—C19—H19B109.5N8—C68—H68118.4
H19A—C19—H19B109.5C69—C68—H68118.4
C17—C19—H19C109.5C70—C69—C68119.0 (9)
H19A—C19—H19C109.5C70—C69—H69120.5
H19B—C19—H19C109.5C68—C69—H69120.5
C25—C20—C21119.7 (10)C69—C70—C71116.4 (9)
C25—C20—S2120.5 (8)C69—C70—H70121.8
C21—C20—S2119.7 (8)C71—C70—H70121.8
C22—C21—C20119.6 (10)C72—C71—C70120.7 (9)
C22—C21—H21120.2C72—C71—H71119.6
C20—C21—H21120.2C70—C71—H71119.6
C23—C22—C21121.1 (11)N8—C72—C71123.5 (9)
C23—C22—H22119.5N8—C72—H72118.2
C21—C22—H22119.5C71—C72—H72118.2
O9—Ni1—N3—C31−140.7 (7)S2—N2—C15—C16138.4 (7)
O5—Ni1—N3—C31−52.3 (7)O5—C14—C15—N2164.5 (8)
N4—Ni1—N3—C3122 (8)O6—C14—C15—N2−15.0 (12)
O2—Ni1—N3—C31128.7 (7)O5—C14—C15—C16−76.7 (10)
O1—Ni1—N3—C3168.5 (7)O6—C14—C15—C16103.8 (10)
O9—Ni1—N3—C2745.0 (6)N2—C15—C16—C17−63.7 (10)
O5—Ni1—N3—C27133.3 (6)C14—C15—C16—C17177.3 (8)
N4—Ni1—N3—C27−152 (7)C15—C16—C17—C19−65.2 (12)
O2—Ni1—N3—C27−45.7 (6)C15—C16—C17—C18167.5 (9)
O1—Ni1—N3—C27−105.8 (6)O7—S2—C20—C25−162.6 (8)
O9—Ni1—N4—C36−172.3 (7)O8—S2—C20—C25−33.0 (9)
O5—Ni1—N4—C3699.5 (7)N2—S2—C20—C2581.0 (9)
N3—Ni1—N4—C3625 (8)O7—S2—C20—C2114.6 (9)
O2—Ni1—N4—C36−81.6 (7)O8—S2—C20—C21144.2 (8)
O1—Ni1—N4—C36−21.4 (7)N2—S2—C20—C21−101.9 (8)
O9—Ni1—N4—C3219.5 (7)C25—C20—C21—C222.6 (15)
O5—Ni1—N4—C32−68.7 (7)S2—C20—C21—C22−174.6 (8)
N3—Ni1—N4—C32−143 (7)C20—C21—C22—C23−1.0 (16)
O2—Ni1—N4—C32110.3 (7)C21—C22—C23—C24−0.7 (16)
O1—Ni1—N4—C32170.4 (7)C21—C22—C23—C26177.3 (10)
O18—Ni2—N7—C67−132.4 (7)C22—C23—C24—C250.9 (17)
O14—Ni2—N7—C67−28.9 (7)C26—C23—C24—C25−177.1 (10)
N8—Ni2—N7—C67−108 (17)C21—C20—C25—C24−2.5 (15)
O10—Ni2—N7—C67128.9 (7)S2—C20—C25—C24174.7 (8)
O11—Ni2—N7—C6768.5 (7)C23—C24—C25—C200.7 (17)
O18—Ni2—N7—C6345.5 (6)C31—N3—C27—C280.5 (13)
O14—Ni2—N7—C63149.0 (6)Ni1—N3—C27—C28175.1 (7)
N8—Ni2—N7—C6370 (17)N3—C27—C28—C29−0.4 (14)
O10—Ni2—N7—C63−53.2 (6)C27—C28—C29—C30−1.2 (14)
O11—Ni2—N7—C63−113.6 (6)C28—C29—C30—C312.8 (15)
O18—Ni2—N8—C687.0 (7)C27—N3—C31—C301.2 (13)
O14—Ni2—N8—C68−96.5 (7)Ni1—N3—C31—C30−173.4 (7)
N7—Ni2—N8—C68−18 (17)C29—C30—C31—N3−2.8 (15)
O10—Ni2—N8—C68105.7 (7)C36—N4—C32—C332.4 (14)
O11—Ni2—N8—C68166.1 (7)Ni1—N4—C32—C33171.1 (8)
O18—Ni2—N8—C72174.6 (7)N4—C32—C33—C34−0.1 (16)
O14—Ni2—N8—C7271.1 (7)C32—C33—C34—C35−2.1 (16)
N7—Ni2—N8—C72150 (17)C33—C34—C35—C362.0 (16)
O10—Ni2—N8—C72−86.7 (7)C32—N4—C36—C35−2.6 (14)
O11—Ni2—N8—C72−26.3 (7)Ni1—N4—C36—C35−171.1 (7)
O9—Ni1—O1—C1−0.8 (8)C34—C35—C36—N40.4 (15)
O5—Ni1—O1—C1178.0 (5)Ni2—O11—C37—O106.8 (8)
N3—Ni1—O1—C185.3 (5)Ni2—O11—C37—C38−165.5 (8)
N4—Ni1—O1—C1−96.2 (5)Ni2—O10—C37—O11−7.1 (9)
O2—Ni1—O1—C1−2.7 (5)Ni2—O10—C37—C38165.4 (7)
O9—Ni1—O2—C1−176.4 (5)S3—N5—C38—C37−108.0 (8)
O5—Ni1—O2—C1151 (11)S3—N5—C38—C39135.3 (6)
N3—Ni1—O2—C1−85.7 (5)O11—C37—C38—N5−26.3 (12)
N4—Ni1—O2—C192.3 (5)O10—C37—C38—N5161.2 (8)
O1—Ni1—O2—C12.7 (5)O11—C37—C38—C3992.9 (10)
O9—Ni1—O5—C14−176.8 (7)O10—C37—C38—C39−79.5 (10)
N3—Ni1—O5—C1492.6 (7)N5—C38—C39—C40−67.0 (11)
N4—Ni1—O5—C14−85.4 (7)C37—C38—C39—C40171.1 (9)
O2—Ni1—O5—C14−144 (11)C38—C39—C40—C42−68.1 (13)
O1—Ni1—O5—C143.7 (7)C38—C39—C40—C41168.6 (10)
O18—Ni2—O10—C37−170.5 (5)O13—S3—C43—C48−163.5 (8)
O14—Ni2—O10—C372.1 (9)O12—S3—C43—C48−33.8 (9)
N7—Ni2—O10—C37−86.2 (5)N5—S3—C43—C4880.4 (9)
N8—Ni2—O10—C3794.6 (5)O13—S3—C43—C4415.4 (9)
O11—Ni2—O10—C374.0 (5)O12—S3—C43—C44145.1 (8)
O18—Ni2—O11—C3710.9 (9)N5—S3—C43—C44−100.7 (8)
O14—Ni2—O11—C37175.3 (5)C48—C43—C44—C453.0 (15)
N7—Ni2—O11—C3783.3 (5)S3—C43—C44—C45−176.0 (8)
N8—Ni2—O11—C37−96.8 (5)C43—C44—C45—C46−1.5 (16)
O10—Ni2—O11—C37−4.0 (5)C44—C45—C46—C470.8 (17)
O18—Ni2—O14—C50−24.8 (7)C44—C45—C46—C49177.5 (10)
N7—Ni2—O14—C50−110.0 (7)C45—C46—C47—C48−1.5 (18)
N8—Ni2—O14—C5069.1 (7)C49—C46—C47—C48−178.1 (11)
O10—Ni2—O14—C50162.8 (7)C46—C47—C48—C433.0 (17)
O11—Ni2—O14—C50161.1 (6)C44—C43—C48—C47−3.6 (15)
C2—N1—S1—O4−37.8 (8)S3—C43—C48—C47175.3 (8)
C2—N1—S1—O3−168.5 (7)Ni2—O14—C50—O1512.0 (13)
C2—N1—S1—C777.8 (8)Ni2—O14—C50—C51−162.4 (6)
C15—N2—S2—O7−46.4 (8)S4—N6—C51—C50−108.8 (9)
C15—N2—S2—O8−176.8 (7)S4—N6—C51—C52129.0 (8)
C15—N2—S2—C2069.1 (8)O15—C50—C51—N6157.2 (8)
C38—N5—S3—O13−40.1 (8)O14—C50—C51—N6−28.0 (13)
C38—N5—S3—O12−170.6 (7)O15—C50—C51—C52−77.8 (11)
C38—N5—S3—C4375.6 (8)O14—C50—C51—C5297.0 (10)
C51—N6—S4—O17−27.6 (8)N6—C51—C52—C53−75.9 (12)
C51—N6—S4—O16−157.7 (7)C50—C51—C52—C53157.4 (10)
C51—N6—S4—C5688.5 (8)C51—C52—C53—C55−65.0 (16)
Ni1—O1—C1—O24.8 (9)C51—C52—C53—C54174.1 (11)
Ni1—O1—C1—C2−168.0 (8)O17—S4—C56—C57−159.9 (8)
Ni1—O2—C1—O1−4.9 (9)O16—S4—C56—C57−31.0 (9)
Ni1—O2—C1—C2168.1 (7)N6—S4—C56—C5783.8 (9)
S1—N1—C2—C1−111.1 (8)O17—S4—C56—C6118.5 (9)
S1—N1—C2—C3135.2 (7)O16—S4—C56—C61147.4 (8)
O1—C1—C2—N1−28.9 (12)N6—S4—C56—C61−97.8 (8)
O2—C1—C2—N1157.9 (8)C61—C56—C57—C58−2.9 (16)
O1—C1—C2—C387.8 (9)S4—C56—C57—C58175.5 (8)
O2—C1—C2—C3−85.4 (9)C56—C57—C58—C591.4 (18)
N1—C2—C3—C4−60.5 (12)C57—C58—C59—C602.1 (19)
C1—C2—C3—C4179.2 (9)C57—C58—C59—C62178.6 (11)
C2—C3—C4—C6173.9 (11)C58—C59—C60—C61−4.1 (18)
C2—C3—C4—C5−66.3 (13)C62—C59—C60—C61179.3 (11)
O4—S1—C7—C12−165.3 (8)C57—C56—C61—C600.9 (16)
O3—S1—C7—C12−34.8 (10)S4—C56—C61—C60−177.5 (8)
N1—S1—C7—C1278.6 (9)C59—C60—C61—C562.7 (17)
O4—S1—C7—C814.3 (10)C67—N7—C63—C64−1.3 (13)
O3—S1—C7—C8144.7 (9)Ni2—N7—C63—C64−179.4 (7)
N1—S1—C7—C8−101.8 (9)N7—C63—C64—C650.0 (15)
C12—C7—C8—C93.0 (17)C63—C64—C65—C66−1.0 (15)
S1—C7—C8—C9−176.5 (8)C64—C65—C66—C673.1 (15)
C7—C8—C9—C100.1 (17)C63—N7—C67—C663.6 (13)
C8—C9—C10—C11−3.9 (18)Ni2—N7—C67—C66−178.4 (7)
C8—C9—C10—C13179.1 (10)C65—C66—C67—N7−4.6 (15)
C9—C10—C11—C124.6 (18)C72—N8—C68—C692.0 (14)
C13—C10—C11—C12−178.4 (11)Ni2—N8—C68—C69170.0 (7)
C8—C7—C12—C11−2.4 (16)N8—C68—C69—C70−2.9 (15)
S1—C7—C12—C11177.2 (8)C68—C69—C70—C712.3 (15)
C10—C11—C12—C7−1.5 (17)C69—C70—C71—C72−1.1 (15)
Ni1—O5—C14—O6−22.3 (12)C68—N8—C72—C71−0.7 (14)
Ni1—O5—C14—C15158.2 (6)Ni2—N8—C72—C71−168.8 (7)
S2—N2—C15—C14−104.3 (8)C70—C71—C72—N80.3 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O15i0.862.232.942 (10)140
N2—H2···O10i0.862.303.017 (9)140
N5—H5···O20.862.433.144 (9)141
O9—H9C···O140.852.312.754 (7)113
O9—H9D···O110.851.872.610 (7)145
O18—H18E···O6ii0.851.742.569 (9)165
O18—H18F···O150.852.002.683 (9)136
O18—H18F···O1ii0.852.372.820 (7)113

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+3/2, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5641).

References

  • Brown, N. J., Wu, C. W. & Shannon, L. S. (2008). Biochemistry, 47, 1808–1818. [PubMed]
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Li, W., Li, C. H., Yang, Y. C. & Xie, H. P. (2009). Chin. J. Inorg. Chem.25, 934–937.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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