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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1346
https://doi.org/10.1107/S1600536810038493

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

Xi-Shi Taia*

aDepartment of Chemistry, Weifangl University, Weifang 261061, People's Republic of China
*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 18 September 2010; accepted 26 September 2010; online 2 October 2010)

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[Brown, N. J., Wu, C. W. & Shannon, L. S. (2008). Biochemistry, 47, 1808-1818.]). For a related structure, see: Li et al. (2009[Li, W., Li, C. H., Yang, Y. C. & Xie, H. P. (2009). Chin. J. Inorg. Chem. 25, 934-937.]).

[Scheme 1]

Experimental

Crystal data

  • [Ni(C13H18NO4S)2(C5H5N)2(H2O)]

  • Mr = 803.61

  • Orthorhombic, P 21 21 21

  • 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.794, Tmax = 0.828

  • 41421 measured reflections

  • 14319 independent reflections

  • 8009 reflections with I > 2σ(I)

  • Rint = 0.056
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6501 Friedel pairs

  • Flack parameter: −0.02 (3)

Table 1
Selected bond lengths (Å)

Ni1—O9 2.042 (5)
Ni1—O5 2.048 (6)
Ni1—N3 2.084 (7)
Ni1—N4 2.117 (7)
Ni1—O2 2.171 (6)
Ni1—O1 2.215 (6)
Ni2—O18 1.993 (5)
Ni2—O14 2.059 (6)
Ni2—N7 2.097 (7)
Ni2—N8 2.123 (7)
Ni2—O10 2.134 (6)
Ni2—O11 2.205 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O15i 0.86 2.23 2.942 (10) 140
N2—H2⋯O10i 0.86 2.30 3.017 (9) 140
N5—H5⋯O2 0.86 2.43 3.144 (9) 141
O9—H9C⋯O14 0.85 2.31 2.754 (7) 113
O9—H9D⋯O11 0.85 1.87 2.610 (7) 145
O18—H18E⋯O6ii 0.85 1.74 2.569 (9) 165
O18—H18F⋯O15 0.85 2.00 2.683 (9) 136
O18—H18F⋯O1ii 0.85 2.37 2.820 (7) 113
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038493/hb5641Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

For background to amino acid derivatives in coordination chemistry, see: Brown et al. (2008). For a related structure, see: Li et al. (2009). AUTHOR: give full details of treatment of hydrogen atoms for inclusion in _publ_section_exptl_refinement section

Experimental top

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.

Structure description top

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.

For background to amino acid derivatives in coordination chemistry, see: Brown et al. (2008). For a related structure, see: Li et al. (2009). AUTHOR: give full details of treatment of hydrogen atoms for inclusion in _publ_section_exptl_refinement section

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.
Aquadipyridinebis(N-p-tolysulfonyl-L-leucinato)nickel(II) top
Crystal data top
[Ni(C13H18NO4S)2(C5H5N)2(H2O)]Dx = 1.314 Mg m−3
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 mm−1
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 top
Bruker SMART CCD
diffractometer		14319 independent reflections
Radiation source: fine-focus sealed tube8009 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.242 w = 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 Å−3
949 parametersΔρmin = −0.73 e Å−3
0 restraintsAbsolute structure: Flack (1983), 6501 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.02 (3)
Crystal data top
[Ni(C13H18NO4S)2(C5H5N)2(H2O)]V = 8125.7 (13) Å3
Mr = 803.61Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 18.1023 (16) ŵ = 0.64 mm−1
b = 19.5538 (19) ÅT = 298 K
c = 22.956 (2) Å0.38 × 0.36 × 0.31 mm
Data collection top
Bruker SMART CCD
diffractometer		14319 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		8009 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.828Rint = 0.056
41421 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.242Δρmax = 1.08 e Å−3
S = 1.05Δρmin = −0.73 e Å−3
14319 reflectionsAbsolute structure: Flack (1983), 6501 Friedel pairs
949 parametersAbsolute structure parameter: −0.02 (3)
0 restraints
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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formula[Ni(C13H18NO4S)2(C5H5N)2(H2O)]
Mr803.61
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)18.1023 (16), 19.5538 (19), 22.956 (2)
V (Å3)8125.7 (13)
Z8
Radiation typeMo Kα
µ (mm−1)0.64
Crystal size (mm)0.38 × 0.36 × 0.31
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.794, 0.828
No. of measured, independent and
observed [I > 2σ(I)] reflections		41421, 14319, 8009
Rint0.056
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.242, 1.05
No. of reflections14319
No. of parameters949
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.08, −0.73
Absolute structureFlack (1983), 6501 Friedel pairs
Absolute structure parameter−0.02 (3)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—O92.042 (5)Ni2—O181.993 (5)
Ni1—O52.048 (6)Ni2—O142.059 (6)
Ni1—N32.084 (7)Ni2—N72.097 (7)
Ni1—N42.117 (7)Ni2—N82.123 (7)
Ni1—O22.171 (6)Ni2—O102.134 (6)
Ni1—O12.215 (6)Ni2—O112.205 (5)
Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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

References

First citationBrown, N. J., Wu, C. W. & Shannon, L. S. (2008). Biochemistry, 47, 1808–1818.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationLi, W., Li, C. H., Yang, Y. C. & Xie, H. P. (2009). Chin. J. Inorg. Chem. 25, 934–937.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1346
https://doi.org/10.1107/S1600536810038493
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