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

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ISSN: 2056-9890

Ethyl­enedi­ammonium tetra­kis({2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}nickel(II)) bis­­(perchlorate) di­methyl­formamide monosolvate

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com

(Received 26 April 2010; accepted 11 May 2010; online 15 May 2010)

The title compound, (C2H10N2)[Ni(C16H14N2O2)]4(ClO4)2·C3H7NO, crystallizes with four Ni(salen) mol­ecules {salen is 2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolate}, one ethyl­enediammonium cation (actually two half-cations, each located on a center of inversion), two perchlorate anions and one dimethyl­formamide solvent mol­ecule in the asymmetric unit. Each NiII cation in the Ni(salen) complex is four-coordinated by two imine N atoms and two phenolate O atoms from the tetra­dentate ligand. The Ni(salen) units form parallel slipped stacks with Ni⋯Ni separations of 3.4541 (4) and 3.6442 (6) Å. The crystal packing is stabilized by inter­molecular hydrogen bonds between the ammonium H atoms and the perchlorate and salen O atoms, which generate a three-dimensional structure.

Related literature

For applications of nickel–Schiff base complexes in homogeneous and heterogeneous catalysis, see: Santos et al. (2000[Santos, I. C., Vilas-Boas, M., Piedade, M. F. M., Freire, C., Duarte, M. T. & de Castro, B. (2000). Polyhedron, 19, 655-664.]); Silva et al. (2002[Silva, A. R., Martins, M., Freitas, M. M. A., Valente, A., Freire, C., de Castro, B. & Figueiredo, J. L. (2002). Microporous Mesoporous Mater. 55, 275-284.]); Yoon & Burrows (1988[Yoon, H. & Burrows, C. J. (1988). J. Am. Chem. Soc. 110, 4087-4089.]); Mitra & Chatterjee (1999[Mitra, A. & Chatterjee, D. (1999). J. Mol. Catal. A Chem. 144, 363-367.]). For other properties of Ni(salen) complexes, see: Abe et al. (2006[Abe, Y., Akao, H., Yoshida, Y., Takashima, H., Tanase, T., Mukai, H. & Ohta, K. (2006). Inorg. Chim. Acta, 359, 3147-3155.]); Gaetani Manfredotti & Guastini (1983[Gaetani Manfredotti, A. & Guastini, C. (1983). Acta Cryst. C39, 863-865.]); Pahor et al. (1976[Pahor, N. M., Calligaris, M., Delise, P., Nardin, G., Randaccio, L., Zotti, E., Fachinetti, G. & Floriani, C. (1976). J. Chem. Soc. Dalton Trans. pp. 2310-2316.]); Prabhakar et al. (2006[Prabhakar, M., Zacharias, P. S. & Das, S. K. (2006). Inorg. Chem. Commun. 9, 899-902.]); Santos et al. (2000[Santos, I. C., Vilas-Boas, M., Piedade, M. F. M., Freire, C., Duarte, M. T. & de Castro, B. (2000). Polyhedron, 19, 655-664.]); Silva et al. (2002[Silva, A. R., Martins, M., Freitas, M. M. A., Valente, A., Freire, C., de Castro, B. & Figueiredo, J. L. (2002). Microporous Mesoporous Mater. 55, 275-284.]). For the structures of Ni(salen) co-crystallization complexes, see: Giacomelli et al. (1982[Giacomelli, A., Floriani, C. & Perego, G. (1982). Chem. Commun. pp. 650-652.]); Ryaza­nov et al. (2001[Ryazanov, M. V., Troyanov, S. I., Malkerova, I. P., Alikhanyan, A. S. & Kuz'mina, N. P. (2001). Zh. Neorg. Khim. 46, 256-265.]); Skovsgaard et al. (2005[Skovsgaard, S., Bond, A. D. & McKenzie, C. J. (2005). Acta Cryst. E61, m135-m137.]); Feng et al. (2007[Feng, X., Du, Z.-X., Ye, B.-K. & Cui, F.-N. (2007). Jiegou Huaxue, 26, 1033-1038.]); Sun et al. (1991[Sun, M. Z., Wang, Y. & Yu, B. K. (1991). Chin. Chem. Lett. 2, 781-782.]); Lutz (2003[Lutz, M. (2003). Acta Cryst. E59, m950-m952.]).

[Scheme 1]

Experimental

Crystal data
  • (C2H10N2)[Ni(C16H14N2O2)]4·(ClO4)2·C3H7NO

  • Mr = 1634.12

  • Triclinic, [P \overline 1]

  • a = 15.0209 (11) Å

  • b = 15.0492 (13) Å

  • c = 18.2709 (8) Å

  • α = 85.990 (5)°

  • β = 86.506 (5)°

  • γ = 62.963 (8)°

  • V = 3667.8 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.16 mm−1

  • T = 200 K

  • 0.53 × 0.28 × 0.24 mm

Data collection
  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.832, Tmax = 1.000

  • 31940 measured reflections

  • 13062 independent reflections

  • 9248 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.110

  • S = 0.95

  • 13062 reflections

  • 936 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N11S—H11B⋯O2A 0.91 1.97 2.877 (3) 173
N11S—H11B⋯O1A 0.91 2.45 2.949 (3) 115
N11S—H11D⋯O2D 0.91 2.00 2.876 (3) 162
N11S—H11D⋯O1D 0.91 2.48 3.132 (3) 128
N22S—H22A⋯O1B 0.91 1.97 2.830 (3) 157
N22S—H22A⋯O2B 0.91 2.34 2.884 (3) 118
N22S—H22B⋯O1C 0.91 1.98 2.853 (3) 160
N22S—H22B⋯O2C 0.91 2.45 3.118 (3) 130
N22S—H22C⋯O1SB 0.91 1.91 2.706 (5) 145
N22S—H22C⋯O1SA 0.91 1.90 2.778 (6) 161

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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


Comment top

Schiff base complexes of transition metals are of paramount importance due to their application in homogeneous and heterogeneous catalysis (Santos et al. 2000; Silva et al. 2002). Nickel(II) Schiff bases have been described as being active catalytically in oxidation and reduction reactions both as homogeneous (Yoon & Burrows 1988) and heterogeneous catalysts (Mitra & Chatterjee 1999). [Ethylenebis(salicylideneiminato-κ4N,N',O,O']nickel(II) {Nisalen} complexes with mesomorphic properties, known as metallomesogens, have been synthesized and investigated (Abe et al. 2006). In addition, there have been several instances of Ni(salen) type species co-crystallizing with other salts and molecules (Giacomelli et al., 1982; Ryazanov et al., 2001; Skovsgaard et al., 2005; Feng et al., 2007; Sun et al., 1991; Lutz, 2003).

The work presented here describes the synthesis and structural characterization of NiII salen complex co-crystallizing with ethylenediammonium perchlorate and N,N'-dimethylformamide presented in Fig. 1. The asymmetric unit contains four neutral Ni(salen) molecules, ethylenediammonium perchlorate (actually two half ethylenediammonium cations lying on centers of inversion), and an N,N'-dimethylformamide solvate molecule. All species are linked together by an extensive series of hydrogen bonds between the ethylenediammonium cations and perchlorate anions, neutral Ni(salen) and N,N'-dimethylformamide molecules. This is a good example of molecular recognition. The Ni—O phenolate bond distances range from 1.8353 (15) to 1.8576 (14) Å and the Ni—N distances range from 1.836 (2) to 1.8497 (18) Å and are comparable to those found in literature for similar neutral Ni(salen) complexes reported earlier (Prabhakar et al. 2006). The coordination around NiII ions shows a slightly distorted square planer geometry. The Ni(salen) units form parallel slipped stacks with Ni—Ni separations of 3.4541 (4) and 3.6442 (6) Å.

Related literature top

For applications of nickel–Schiff base complexes in homogeneous and heterogeneous catalysis, see: Santos et al. (2000); Silva et al. (2002); Yoon & Burrows (1988); Mitra & Chatterjee (1999). For other properties of Ni(salen) complexes, see: Abe et al. (2006); Gaetani Manfredotti & Guastini (1983); Pahor et al. (1976); Prabhakar et al. (2006); Santos et al. (2000); Silva et al. (2002). For the structures of Ni(salen) co-crystallization complexes, see: Giacomelli et al. (1982); Ryazanov et al. (2001); Skovsgaard et al. (2005); Feng et al. (2007); Sun et al. (1991); Lutz (2003).

Experimental top

The ligand ethylenebis(salicylideneimine) was synthesized by reacting a solution of (5 g, 83.19 mmol) of ethylenediamine in 10 ml ethanol with a solution of (20.32 g, 166.38 mmol) salicylaldehyde in 40 ml ethanol. The mixture was refluxed for 24 hrs. The mixture was then evaporated under reduced pressure and yellow solids were obtained with a yield of 96.6%.

The complex was synthesized by reacting 1.36 g (3.73 mmol) of Ni(ClO4)2.6H2O in methanol (10 ml) with 1 g (3.73 mmol) of ethylenebis(salicylideneimine) in CH2Cl2 (10 ml) for 24 hours while stirring with magnetic stirrer at room temperature. The mixture was evaporated under reduced pressure and brownish solids were obtained. These solids were dissolved in N,N'-dimethylformamide. The solution obtained was filtered and layered with diethyl ether. Brownish X-ray quality crystals were obtained after slow diffusion of the diethyl ether into the N,N'-dimethylformamide solution of the complex over a period of several days.

Refinement top

One DMF molecule was disordered in a manner that was not possible to model successfully. This was removed using the SQUEEZE routine from Platon. The output files from Platon are appended to the cif file and the fcf file has been modified using the Calc-FCF routine from Platon. H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distance of 0.95 and 0.99 Å Uiso(H) = 1.2Ueq(C) and 0.98 Å for CH3 [Uiso(H) = 1.5Ueq(C)]. The H atoms attached to N were idealized with an N–H distance of 0.91 Å.

Structure description top

Schiff base complexes of transition metals are of paramount importance due to their application in homogeneous and heterogeneous catalysis (Santos et al. 2000; Silva et al. 2002). Nickel(II) Schiff bases have been described as being active catalytically in oxidation and reduction reactions both as homogeneous (Yoon & Burrows 1988) and heterogeneous catalysts (Mitra & Chatterjee 1999). [Ethylenebis(salicylideneiminato-κ4N,N',O,O']nickel(II) {Nisalen} complexes with mesomorphic properties, known as metallomesogens, have been synthesized and investigated (Abe et al. 2006). In addition, there have been several instances of Ni(salen) type species co-crystallizing with other salts and molecules (Giacomelli et al., 1982; Ryazanov et al., 2001; Skovsgaard et al., 2005; Feng et al., 2007; Sun et al., 1991; Lutz, 2003).

The work presented here describes the synthesis and structural characterization of NiII salen complex co-crystallizing with ethylenediammonium perchlorate and N,N'-dimethylformamide presented in Fig. 1. The asymmetric unit contains four neutral Ni(salen) molecules, ethylenediammonium perchlorate (actually two half ethylenediammonium cations lying on centers of inversion), and an N,N'-dimethylformamide solvate molecule. All species are linked together by an extensive series of hydrogen bonds between the ethylenediammonium cations and perchlorate anions, neutral Ni(salen) and N,N'-dimethylformamide molecules. This is a good example of molecular recognition. The Ni—O phenolate bond distances range from 1.8353 (15) to 1.8576 (14) Å and the Ni—N distances range from 1.836 (2) to 1.8497 (18) Å and are comparable to those found in literature for similar neutral Ni(salen) complexes reported earlier (Prabhakar et al. 2006). The coordination around NiII ions shows a slightly distorted square planer geometry. The Ni(salen) units form parallel slipped stacks with Ni—Ni separations of 3.4541 (4) and 3.6442 (6) Å.

For applications of nickel–Schiff base complexes in homogeneous and heterogeneous catalysis, see: Santos et al. (2000); Silva et al. (2002); Yoon & Burrows (1988); Mitra & Chatterjee (1999). For other properties of Ni(salen) complexes, see: Abe et al. (2006); Gaetani Manfredotti & Guastini (1983); Pahor et al. (1976); Prabhakar et al. (2006); Santos et al. (2000); Silva et al. (2002). For the structures of Ni(salen) co-crystallization complexes, see: Giacomelli et al. (1982); Ryazanov et al. (2001); Skovsgaard et al. (2005); Feng et al. (2007); Sun et al. (1991); Lutz (2003).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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. Showing the contents of the asymmetric unit with complete ethylenediammonium cations (generated by symmetry codes 1-x, 1-y, 1-z and 2-x, -y, 2-z). Hydrogen bonding between cations and perchlorate anions, neutral Ni(salen), and N,N'-dimethylformamide solvate molecule is shown by dashed lines. For clarity only the Ni, Cl O and N (from diammonium cations) atoms are labeled.
[Figure 2] Fig. 2. The molecular packing for C69H73Cl2N11Ni4O17 viewed down the a axis showing the intermolecular N—H···O interactions.
Ethylenediammonium tetrakis({2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)) bis(perchlorate) dimethylformamide monosolvate top
Crystal data top
(C2H10N2)[Ni(C16H14N2O2)]4·(ClO4)2·C3H7NOZ = 2
Mr = 1634.12F(000) = 1692
Triclinic, P1Dx = 1.480 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 15.0209 (11) ÅCell parameters from 14342 reflections
b = 15.0492 (13) Åθ = 4.5–34.7°
c = 18.2709 (8) ŵ = 1.16 mm1
α = 85.990 (5)°T = 200 K
β = 86.506 (5)°Thick needle, translucent red-brown
γ = 62.963 (8)°0.53 × 0.28 × 0.24 mm
V = 3667.8 (4) Å3
Data collection top
Oxford Diffraction Gemini R
diffractometer
13062 independent reflections
Radiation source: Enhance (Mo) X-ray Source9248 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.5081 pixels mm-1θmax = 25.2°, θmin = 4.5°
ω scansh = 1818
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1718
Tmin = 0.832, Tmax = 1.000l = 2120
31940 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0701P)2]
where P = (Fo2 + 2Fc2)/3
13062 reflections(Δ/σ)max = 0.002
936 parametersΔρmax = 0.56 e Å3
14 restraintsΔρmin = 0.32 e Å3
Crystal data top
(C2H10N2)[Ni(C16H14N2O2)]4·(ClO4)2·C3H7NOγ = 62.963 (8)°
Mr = 1634.12V = 3667.8 (4) Å3
Triclinic, P1Z = 2
a = 15.0209 (11) ÅMo Kα radiation
b = 15.0492 (13) ŵ = 1.16 mm1
c = 18.2709 (8) ÅT = 200 K
α = 85.990 (5)°0.53 × 0.28 × 0.24 mm
β = 86.506 (5)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
13062 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
9248 reflections with I > 2σ(I)
Tmin = 0.832, Tmax = 1.000Rint = 0.031
31940 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03914 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 0.95Δρmax = 0.56 e Å3
13062 reflectionsΔρmin = 0.32 e Å3
936 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqOcc. (<1)
Ni10.36564 (2)0.67261 (2)0.77292 (2)0.02687 (10)
Ni20.76060 (3)0.25911 (3)0.82558 (2)0.03289 (11)
Ni31.11277 (3)0.12736 (3)0.75047 (2)0.02913 (10)
Ni40.71105 (3)0.29506 (3)0.64077 (2)0.03068 (10)
Cl11.18947 (6)0.10251 (6)0.48440 (5)0.0453 (2)
Cl20.29975 (6)0.41268 (6)1.01193 (5)0.0489 (2)
O111.11501 (19)0.0697 (2)0.49421 (18)0.0781 (9)
O121.2601 (3)0.0623 (3)0.5382 (2)0.1211 (14)
O131.2386 (3)0.0697 (3)0.4153 (2)0.1121 (13)
O141.1438 (3)0.2069 (2)0.4780 (2)0.1056 (12)
O210.3826 (2)0.4327 (2)0.9983 (2)0.0895 (10)
O220.3318 (3)0.3094 (2)1.0094 (2)0.1025 (12)
O230.2627 (3)0.4388 (3)1.0858 (2)0.1168 (13)
O240.2220 (3)0.4681 (3)0.9663 (2)0.1207 (14)
O1A0.44445 (14)0.70365 (14)0.70528 (11)0.0323 (5)
O2A0.32163 (13)0.63858 (13)0.69153 (10)0.0278 (4)
O1B0.78134 (13)0.13008 (14)0.85054 (12)0.0361 (5)
O2B0.88915 (14)0.19722 (13)0.78735 (11)0.0338 (5)
O1C1.16007 (13)0.08894 (14)0.82778 (11)0.0319 (5)
O2C1.03643 (14)0.15448 (14)0.82302 (11)0.0348 (5)
O1D0.58011 (14)0.35649 (13)0.67428 (12)0.0365 (5)
O2D0.69133 (14)0.42452 (14)0.61834 (12)0.0360 (5)
N1A0.41689 (17)0.69773 (17)0.85393 (13)0.0331 (6)
N2A0.27928 (17)0.64977 (17)0.83877 (13)0.0321 (6)
N1B0.63144 (18)0.31786 (19)0.86463 (15)0.0415 (7)
N2B0.74371 (19)0.38617 (17)0.80112 (14)0.0378 (6)
N1C1.19653 (17)0.10758 (16)0.67991 (13)0.0312 (6)
N2C1.05854 (17)0.15817 (16)0.67420 (13)0.0324 (6)
N1D0.73038 (18)0.16699 (17)0.66650 (14)0.0336 (6)
N2D0.84188 (18)0.23644 (17)0.60470 (14)0.0357 (6)
N11S0.48787 (17)0.56377 (17)0.58756 (13)0.0322 (6)
H11B0.43900.58440.62350.048*
H11C0.49610.61700.56810.048*
H11D0.54620.51730.60690.048*
N22S0.97904 (17)0.04318 (17)0.90083 (13)0.0318 (6)
H22A0.92440.06300.87300.048*
H22B1.03150.00970.88050.048*
H22C0.99500.09450.90280.048*
C1A0.50091 (19)0.74663 (19)0.71817 (17)0.0311 (7)
C2A0.5383 (2)0.7840 (2)0.6580 (2)0.0391 (8)
H2AA0.52120.77940.60970.047*
C3A0.5994 (2)0.8273 (2)0.6684 (2)0.0480 (9)
H3AA0.62500.85100.62690.058*
C4A0.6247 (2)0.8372 (2)0.7380 (2)0.0507 (10)
H4AA0.66690.86760.74420.061*
C5A0.5885 (2)0.8029 (2)0.7970 (2)0.0474 (9)
H5AA0.60620.80900.84480.057*
C6A0.5251 (2)0.7581 (2)0.78923 (19)0.0361 (8)
C7A0.4821 (2)0.7316 (2)0.85369 (18)0.0367 (8)
H7AA0.50300.73940.89980.044*
C8A0.3795 (2)0.6719 (2)0.92469 (18)0.0437 (8)
H8AA0.37730.71660.96280.052*
H8AB0.42380.60210.94090.052*
C9A0.2767 (2)0.6846 (2)0.91269 (18)0.0447 (8)
H9AA0.25830.64450.95020.054*
H9AB0.22700.75560.91580.054*
C10A0.2171 (2)0.6167 (2)0.82453 (17)0.0349 (7)
H10A0.17880.60670.86460.042*
C11A0.20118 (19)0.5937 (2)0.75343 (17)0.0308 (7)
C12A0.1293 (2)0.5591 (2)0.74596 (19)0.0390 (8)
H12A0.09560.54820.78870.047*
C13A0.1070 (2)0.5411 (2)0.6799 (2)0.0446 (8)
H13A0.05820.51800.67660.053*
C14A0.1555 (2)0.5565 (2)0.6168 (2)0.0434 (8)
H14A0.14050.54320.57030.052*
C15A0.2259 (2)0.5911 (2)0.62179 (18)0.0343 (7)
H15A0.25730.60330.57820.041*
C16A0.25146 (19)0.60843 (19)0.68946 (16)0.0272 (6)
C1B0.7138 (2)0.1011 (2)0.87479 (17)0.0356 (7)
C2B0.7414 (2)0.0013 (2)0.87984 (19)0.0444 (8)
H2BA0.80790.04720.86640.053*
C3B0.6748 (3)0.0372 (3)0.9038 (2)0.0501 (9)
H3BA0.69590.10720.90700.060*
C4B0.5765 (3)0.0284 (3)0.9234 (2)0.0593 (10)
H4BA0.53000.00370.93870.071*
C5B0.5481 (2)0.1284 (3)0.92040 (19)0.0531 (10)
H5BA0.48180.17290.93570.064*
C6B0.6145 (2)0.1683 (3)0.89507 (18)0.0409 (8)
C7B0.5794 (2)0.2739 (3)0.89050 (18)0.0451 (9)
H7BA0.51300.31450.90770.054*
C8B0.5881 (2)0.4281 (2)0.8668 (2)0.0540 (10)
H8BA0.60000.44690.91480.065*
H8BB0.51510.45920.85990.065*
C9B0.6376 (2)0.4631 (2)0.8065 (2)0.0494 (9)
H9BA0.60440.47110.75960.059*
H9BB0.63370.52830.81760.059*
C10B0.8120 (2)0.4119 (2)0.78000 (17)0.0397 (8)
H10B0.79350.48130.77420.048*
C11B0.9148 (2)0.3429 (2)0.76451 (17)0.0357 (7)
C12B0.9835 (3)0.3799 (2)0.7430 (2)0.0483 (9)
H12B0.96240.44970.74370.058*
C13B1.0798 (3)0.3185 (3)0.7212 (2)0.0573 (10)
H13B1.12510.34500.70660.069*
C14B1.1098 (2)0.2167 (3)0.7208 (2)0.0535 (10)
H14B1.17640.17350.70530.064*
C15B1.0457 (2)0.1767 (2)0.74222 (19)0.0426 (8)
H15B1.06820.10670.74110.051*
C16B0.9465 (2)0.2391 (2)0.76587 (16)0.0327 (7)
C1C1.2291 (2)0.0573 (2)0.82443 (17)0.0309 (7)
C2C1.2578 (2)0.0351 (2)0.89003 (19)0.0405 (8)
H2CA1.22710.04350.93520.049*
C3C1.3286 (2)0.0019 (2)0.8903 (2)0.0454 (9)
H3CA1.34650.01240.93540.054*
C4C1.3751 (2)0.0113 (2)0.8242 (2)0.0458 (9)
H4CA1.42370.03520.82420.055*
C5C1.3495 (2)0.0105 (2)0.7602 (2)0.0411 (8)
H5CA1.38120.00180.71560.049*
C6C1.2775 (2)0.0456 (2)0.75791 (17)0.0325 (7)
C7C1.2592 (2)0.0733 (2)0.68950 (18)0.0354 (8)
H7CA1.29620.06580.64750.042*
C8C1.1948 (2)0.1447 (2)0.60766 (17)0.0388 (8)
H8CA1.24630.21490.60430.047*
H8CB1.20860.10390.56800.047*
C9C1.0926 (2)0.1371 (2)0.60039 (17)0.0398 (8)
H9CA1.04600.06920.58170.048*
H9CB1.09530.18600.56570.048*
C10C0.9931 (2)0.1919 (2)0.67934 (18)0.0363 (8)
H10C0.96910.20110.63500.044*
C11C0.9543 (2)0.2164 (2)0.74688 (18)0.0350 (7)
C12C0.8921 (2)0.2642 (2)0.7440 (2)0.0446 (9)
H12C0.87130.27220.69790.053*
C13C0.8619 (2)0.2986 (3)0.8070 (2)0.0518 (9)
H13C0.82050.33080.80480.062*
C14C0.8919 (2)0.2866 (2)0.8738 (2)0.0468 (9)
H14C0.87170.31190.91740.056*
C15C0.9501 (2)0.2387 (2)0.87894 (19)0.0416 (8)
H15C0.96910.23090.92580.050*
C16C0.9819 (2)0.2011 (2)0.81519 (17)0.0314 (7)
C1D0.5271 (2)0.3129 (2)0.70293 (17)0.0334 (7)
C2D0.4297 (2)0.3737 (2)0.7293 (2)0.0488 (9)
H2DA0.40510.44410.72640.059*
C3D0.3693 (2)0.3333 (2)0.7590 (2)0.0582 (11)
H3DA0.30340.37630.77600.070*
C4D0.4031 (3)0.2306 (3)0.7645 (2)0.0551 (10)
H4DA0.36050.20320.78430.066*
C5D0.4985 (2)0.1698 (2)0.74121 (19)0.0440 (8)
H5DA0.52240.09940.74570.053*
C6D0.5617 (2)0.2087 (2)0.71094 (17)0.0339 (7)
C7D0.6643 (2)0.1403 (2)0.69302 (17)0.0352 (7)
H7DA0.68440.07090.70140.042*
C8D0.8360 (2)0.0903 (2)0.66086 (19)0.0417 (8)
H8DA0.84010.02520.64920.050*
H8DB0.86960.08180.70770.050*
C9D0.8844 (3)0.1272 (2)0.6003 (2)0.0499 (9)
H9DA0.95760.09570.60610.060*
H9DB0.87090.11040.55210.060*
C10D0.8955 (2)0.2802 (2)0.58442 (18)0.0397 (8)
H10D0.96230.23980.56790.048*
C11D0.8623 (2)0.3857 (2)0.58476 (17)0.0356 (7)
C12D0.9321 (2)0.4235 (3)0.56833 (18)0.0440 (8)
H12D0.99920.37880.55520.053*
C13D0.9052 (2)0.5231 (3)0.5709 (2)0.0479 (9)
H13D0.95320.54710.55990.058*
C14D0.8064 (2)0.5895 (3)0.5900 (2)0.0470 (9)
H14D0.78740.65880.59170.056*
C15D0.7365 (2)0.5548 (2)0.6064 (2)0.0437 (8)
H15D0.67000.60050.62010.052*
C16D0.7620 (2)0.4527 (2)0.60309 (17)0.0341 (7)
C1S0.4589 (2)0.5194 (2)0.52937 (16)0.0315 (7)
H1SA0.39650.57040.50720.038*
H1SB0.44620.46390.55100.038*
C2S0.9568 (2)0.0137 (2)0.97578 (16)0.0308 (7)
H2SA0.94240.04410.97390.037*
H2SB0.89670.06960.99660.037*
O1SA1.0125 (5)0.2006 (2)0.9393 (4)0.0541 (12)0.475 (7)
O1SB0.9653 (4)0.2151 (3)0.9490 (4)0.0541 (12)0.525 (7)
C11S0.9732 (4)0.2955 (2)0.9377 (2)0.0765 (13)
H11A0.90660.34740.94010.092*
N1S1.0477 (2)0.3206 (2)0.92681 (17)0.0540 (8)
C12S1.1467 (4)0.2466 (4)0.9204 (3)0.118 (2)
H12E1.17930.23630.96730.176*
H12F1.18260.26760.88200.176*
H12G1.14760.18410.90750.176*
C13S1.0265 (4)0.4245 (3)0.9169 (3)0.0888 (15)
H13E0.95390.46660.91900.133*
H13F1.05390.43570.86900.133*
H13G1.05710.44170.95590.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02955 (18)0.02476 (18)0.0227 (2)0.00915 (14)0.00090 (15)0.00292 (14)
Ni20.02913 (19)0.0295 (2)0.0315 (2)0.00472 (15)0.00538 (16)0.00590 (16)
Ni30.03140 (19)0.02646 (19)0.0248 (2)0.00951 (15)0.00294 (15)0.00093 (15)
Ni40.0333 (2)0.02499 (19)0.0293 (2)0.00892 (15)0.00515 (16)0.00059 (15)
Cl10.0452 (4)0.0433 (4)0.0488 (6)0.0217 (4)0.0073 (4)0.0049 (4)
Cl20.0408 (4)0.0520 (5)0.0502 (6)0.0171 (4)0.0040 (4)0.0049 (4)
O110.0602 (16)0.0778 (19)0.107 (3)0.0428 (14)0.0024 (16)0.0130 (17)
O120.118 (3)0.154 (3)0.116 (3)0.086 (2)0.075 (2)0.070 (3)
O130.102 (2)0.153 (3)0.095 (3)0.070 (2)0.037 (2)0.041 (2)
O140.134 (3)0.0545 (18)0.134 (3)0.0464 (19)0.021 (2)0.0071 (19)
O210.0608 (17)0.103 (2)0.118 (3)0.0481 (16)0.0177 (17)0.027 (2)
O220.105 (2)0.066 (2)0.130 (3)0.0320 (18)0.011 (2)0.014 (2)
O230.118 (3)0.162 (4)0.077 (3)0.068 (3)0.030 (2)0.048 (2)
O240.093 (2)0.139 (3)0.132 (3)0.059 (2)0.061 (2)0.076 (3)
O1A0.0360 (10)0.0373 (11)0.0285 (12)0.0204 (9)0.0020 (9)0.0066 (9)
O2A0.0288 (9)0.0321 (10)0.0238 (11)0.0151 (8)0.0030 (8)0.0031 (8)
O1B0.0269 (10)0.0337 (11)0.0439 (14)0.0103 (9)0.0014 (9)0.0032 (9)
O2B0.0331 (10)0.0254 (10)0.0350 (13)0.0062 (8)0.0036 (9)0.0001 (9)
O1C0.0324 (10)0.0363 (11)0.0294 (12)0.0183 (9)0.0065 (8)0.0035 (9)
O2C0.0400 (11)0.0403 (11)0.0283 (12)0.0221 (9)0.0053 (9)0.0042 (9)
O1D0.0300 (10)0.0235 (10)0.0518 (15)0.0086 (8)0.0063 (9)0.0041 (9)
O2D0.0326 (10)0.0282 (10)0.0455 (14)0.0127 (9)0.0048 (9)0.0051 (9)
N1A0.0379 (13)0.0276 (12)0.0246 (15)0.0060 (11)0.0024 (11)0.0049 (10)
N2A0.0347 (13)0.0295 (13)0.0217 (14)0.0061 (11)0.0021 (10)0.0000 (10)
N1B0.0335 (14)0.0420 (15)0.0373 (17)0.0049 (12)0.0054 (12)0.0121 (12)
N2B0.0392 (14)0.0293 (13)0.0321 (16)0.0029 (11)0.0074 (12)0.0078 (11)
N1C0.0338 (13)0.0237 (12)0.0261 (15)0.0052 (10)0.0032 (10)0.0021 (10)
N2C0.0340 (13)0.0271 (12)0.0272 (15)0.0060 (11)0.0025 (11)0.0006 (10)
N1D0.0379 (13)0.0252 (12)0.0295 (15)0.0057 (11)0.0063 (11)0.0065 (10)
N2D0.0421 (14)0.0286 (13)0.0287 (15)0.0094 (11)0.0019 (11)0.0029 (10)
N11S0.0326 (12)0.0297 (13)0.0267 (15)0.0077 (10)0.0023 (10)0.0027 (10)
N22S0.0355 (13)0.0332 (13)0.0229 (14)0.0124 (10)0.0020 (10)0.0013 (10)
C1A0.0261 (14)0.0214 (14)0.041 (2)0.0056 (11)0.0022 (13)0.0060 (12)
C2A0.0344 (16)0.0355 (17)0.050 (2)0.0178 (13)0.0037 (14)0.0075 (15)
C3A0.0347 (17)0.0365 (18)0.071 (3)0.0149 (14)0.0022 (17)0.0028 (17)
C4A0.0356 (17)0.0396 (19)0.081 (3)0.0187 (15)0.0092 (18)0.0079 (18)
C5A0.0396 (17)0.0381 (18)0.064 (3)0.0144 (15)0.0191 (17)0.0086 (17)
C6A0.0290 (15)0.0259 (15)0.047 (2)0.0062 (12)0.0081 (14)0.0041 (13)
C7A0.0389 (17)0.0272 (15)0.036 (2)0.0063 (13)0.0111 (14)0.0071 (13)
C8A0.0526 (19)0.0417 (18)0.027 (2)0.0127 (15)0.0002 (15)0.0046 (14)
C9A0.054 (2)0.0471 (19)0.0242 (19)0.0162 (16)0.0075 (15)0.0059 (14)
C10A0.0305 (15)0.0321 (16)0.0310 (19)0.0067 (13)0.0085 (13)0.0062 (13)
C11A0.0250 (14)0.0246 (14)0.0352 (19)0.0060 (11)0.0032 (12)0.0057 (12)
C12A0.0314 (15)0.0357 (17)0.047 (2)0.0148 (13)0.0014 (14)0.0102 (14)
C13A0.0422 (18)0.0420 (18)0.056 (3)0.0252 (15)0.0061 (16)0.0049 (16)
C14A0.0361 (16)0.0398 (18)0.057 (2)0.0183 (14)0.0085 (16)0.0038 (16)
C15A0.0279 (14)0.0371 (16)0.038 (2)0.0143 (13)0.0032 (13)0.0059 (13)
C16A0.0216 (13)0.0200 (13)0.0347 (18)0.0051 (11)0.0001 (12)0.0008 (12)
C1B0.0317 (15)0.0520 (19)0.0260 (18)0.0206 (14)0.0047 (13)0.0059 (14)
C2B0.0406 (17)0.051 (2)0.044 (2)0.0222 (15)0.0009 (15)0.0049 (16)
C3B0.051 (2)0.065 (2)0.046 (2)0.0371 (18)0.0023 (17)0.0017 (17)
C4B0.054 (2)0.097 (3)0.045 (2)0.051 (2)0.0020 (18)0.002 (2)
C5B0.0351 (17)0.089 (3)0.034 (2)0.0273 (18)0.0042 (15)0.0066 (19)
C6B0.0299 (16)0.061 (2)0.0275 (19)0.0162 (15)0.0038 (13)0.0067 (15)
C7B0.0284 (16)0.062 (2)0.032 (2)0.0070 (16)0.0002 (14)0.0162 (16)
C8B0.0418 (18)0.0427 (19)0.057 (3)0.0018 (15)0.0020 (17)0.0231 (17)
C9B0.0430 (18)0.0317 (17)0.053 (2)0.0040 (14)0.0117 (17)0.0122 (16)
C10B0.056 (2)0.0290 (16)0.0245 (18)0.0103 (15)0.0087 (15)0.0022 (13)
C11B0.0517 (18)0.0281 (15)0.0231 (18)0.0142 (14)0.0095 (14)0.0043 (12)
C12B0.064 (2)0.0368 (18)0.047 (2)0.0262 (17)0.0061 (17)0.0059 (15)
C13B0.055 (2)0.047 (2)0.072 (3)0.0275 (18)0.0059 (19)0.0167 (18)
C14B0.0376 (18)0.045 (2)0.070 (3)0.0146 (16)0.0005 (17)0.0157 (18)
C15B0.0387 (17)0.0283 (16)0.051 (2)0.0081 (14)0.0042 (15)0.0097 (14)
C16B0.0385 (16)0.0353 (16)0.0223 (17)0.0150 (13)0.0078 (13)0.0052 (12)
C1C0.0254 (14)0.0233 (14)0.0359 (19)0.0044 (12)0.0032 (12)0.0022 (12)
C2C0.0358 (16)0.0450 (18)0.040 (2)0.0185 (14)0.0101 (14)0.0078 (15)
C3C0.0369 (17)0.0448 (19)0.055 (2)0.0176 (15)0.0015 (16)0.0109 (16)
C4C0.0317 (16)0.0359 (17)0.069 (3)0.0158 (14)0.0042 (16)0.0007 (16)
C5C0.0358 (16)0.0335 (17)0.050 (2)0.0139 (14)0.0048 (15)0.0070 (15)
C6C0.0298 (15)0.0253 (15)0.0337 (19)0.0061 (12)0.0053 (13)0.0012 (12)
C7C0.0302 (15)0.0292 (15)0.0332 (19)0.0037 (13)0.0084 (13)0.0061 (13)
C8C0.0447 (18)0.0357 (17)0.0241 (18)0.0092 (14)0.0056 (14)0.0030 (13)
C9C0.0533 (19)0.0350 (17)0.0220 (18)0.0123 (14)0.0014 (14)0.0017 (13)
C10C0.0333 (16)0.0311 (16)0.033 (2)0.0040 (13)0.0077 (13)0.0014 (13)
C11C0.0272 (14)0.0311 (16)0.039 (2)0.0065 (12)0.0022 (13)0.0008 (13)
C12C0.0343 (16)0.0451 (19)0.052 (2)0.0145 (14)0.0083 (15)0.0058 (16)
C13C0.0356 (17)0.052 (2)0.070 (3)0.0225 (15)0.0047 (17)0.0007 (19)
C14C0.0377 (17)0.051 (2)0.052 (2)0.0225 (16)0.0038 (16)0.0060 (17)
C15C0.0421 (17)0.0460 (19)0.037 (2)0.0211 (15)0.0006 (15)0.0024 (15)
C16C0.0269 (14)0.0285 (15)0.0332 (19)0.0081 (12)0.0008 (12)0.0003 (12)
C1D0.0313 (15)0.0290 (15)0.0382 (19)0.0118 (13)0.0102 (13)0.0039 (13)
C2D0.0343 (17)0.0295 (16)0.076 (3)0.0098 (14)0.0055 (17)0.0095 (16)
C3D0.0358 (18)0.0370 (19)0.091 (3)0.0095 (15)0.0011 (19)0.0100 (19)
C4D0.0455 (19)0.046 (2)0.077 (3)0.0253 (16)0.0047 (18)0.0129 (18)
C5D0.0504 (19)0.0275 (16)0.052 (2)0.0163 (15)0.0045 (16)0.0045 (14)
C6D0.0383 (16)0.0272 (15)0.0341 (19)0.0124 (13)0.0088 (13)0.0007 (13)
C7D0.0465 (18)0.0261 (15)0.0324 (19)0.0154 (14)0.0041 (14)0.0035 (13)
C8D0.0435 (18)0.0221 (15)0.046 (2)0.0028 (13)0.0007 (15)0.0055 (14)
C9D0.056 (2)0.0298 (17)0.050 (2)0.0084 (15)0.0124 (17)0.0093 (15)
C10D0.0374 (16)0.0412 (18)0.032 (2)0.0103 (14)0.0022 (14)0.0039 (14)
C11D0.0334 (15)0.0426 (18)0.0268 (18)0.0139 (13)0.0043 (13)0.0023 (13)
C12D0.0378 (17)0.059 (2)0.035 (2)0.0218 (16)0.0031 (14)0.0017 (16)
C13D0.0461 (19)0.060 (2)0.047 (2)0.0328 (17)0.0051 (16)0.0046 (17)
C14D0.054 (2)0.0451 (19)0.051 (2)0.0312 (16)0.0081 (17)0.0043 (16)
C15D0.0365 (17)0.0363 (17)0.054 (2)0.0134 (14)0.0057 (15)0.0028 (15)
C16D0.0375 (16)0.0353 (16)0.0300 (19)0.0169 (13)0.0087 (13)0.0056 (13)
C1S0.0299 (14)0.0375 (16)0.0252 (17)0.0135 (12)0.0040 (12)0.0057 (12)
C2S0.0329 (15)0.0367 (16)0.0245 (17)0.0183 (12)0.0012 (12)0.0039 (12)
O1SA0.079 (3)0.0598 (16)0.053 (2)0.0575 (18)0.008 (2)0.0071 (14)
O1SB0.079 (3)0.0598 (16)0.053 (2)0.0575 (18)0.008 (2)0.0071 (14)
C11S0.120 (4)0.085 (3)0.037 (3)0.058 (3)0.024 (2)0.008 (2)
N1S0.077 (2)0.0476 (17)0.050 (2)0.0389 (16)0.0076 (16)0.0001 (14)
C12S0.104 (4)0.112 (4)0.082 (4)0.002 (3)0.002 (3)0.027 (3)
C13S0.129 (4)0.069 (3)0.081 (4)0.055 (3)0.004 (3)0.012 (2)
Geometric parameters (Å, º) top
Ni1—O1A1.841 (2)C5B—H5BA0.9500
Ni1—N2A1.845 (3)C6B—C7B1.427 (5)
Ni1—N1A1.846 (2)C7B—H7BA0.9500
Ni1—O2A1.8561 (19)C8B—C9B1.489 (5)
Ni1—Ni3i3.6441 (6)C8B—H8BA0.9900
Ni2—N2B1.837 (3)C8B—H8BB0.9900
Ni2—O2B1.8371 (19)C9B—H9BA0.9900
Ni2—N1B1.848 (3)C9B—H9BB0.9900
Ni2—O1B1.849 (2)C10B—C11B1.440 (4)
Ni2—Ni43.4544 (6)C10B—H10B0.9500
Ni3—N2C1.842 (3)C11B—C12B1.404 (5)
Ni3—O2C1.845 (2)C11B—C16B1.409 (4)
Ni3—N1C1.850 (2)C12B—C13B1.369 (5)
Ni3—O1C1.856 (2)C12B—H12B0.9500
Ni4—O1D1.8377 (19)C13B—C14B1.387 (5)
Ni4—N1D1.844 (2)C13B—H13B0.9500
Ni4—N2D1.850 (2)C14B—C15B1.376 (5)
Ni4—O2D1.8519 (19)C14B—H14B0.9500
Cl1—O121.385 (3)C15B—C16B1.412 (4)
Cl1—O141.399 (3)C15B—H15B0.9500
Cl1—O111.411 (3)C1C—C2C1.408 (4)
Cl1—O131.424 (4)C1C—C6C1.420 (4)
Cl2—O241.375 (3)C2C—C3C1.365 (5)
Cl2—O221.406 (3)C2C—H2CA0.9500
Cl2—O211.412 (3)C3C—C4C1.406 (5)
Cl2—O231.438 (4)C3C—H3CA0.9500
O1A—C1A1.318 (3)C4C—C5C1.358 (5)
O2A—C16A1.327 (3)C4C—H4CA0.9500
O1B—C1B1.318 (4)C5C—C6C1.405 (4)
O2B—C16B1.309 (4)C5C—H5CA0.9500
O1C—C1C1.320 (3)C6C—C7C1.425 (4)
O2C—C16C1.317 (4)C7C—H7CA0.9500
O1D—C1D1.309 (4)C8C—C9C1.500 (5)
O2D—C16D1.320 (4)C8C—H8CA0.9900
N1A—C7A1.293 (4)C8C—H8CB0.9900
N1A—C8A1.476 (4)C9C—H9CA0.9900
N2A—C10A1.287 (4)C9C—H9CB0.9900
N2A—C9A1.475 (4)C10C—C11C1.430 (4)
N1B—C7B1.287 (4)C10C—H10C0.9500
N1B—C8B1.484 (4)C11C—C16C1.405 (4)
N2B—C10B1.282 (4)C11C—C12C1.419 (5)
N2B—C9B1.487 (4)C12C—C13C1.367 (5)
N1C—C7C1.287 (4)C12C—H12C0.9500
N1C—C8C1.475 (4)C13C—C14C1.378 (5)
N2C—C10C1.291 (4)C13C—H13C0.9500
N2C—C9C1.478 (4)C14C—C15C1.372 (5)
N1D—C7D1.287 (4)C14C—H14C0.9500
N1D—C8D1.481 (4)C15C—C16C1.412 (4)
N2D—C10D1.278 (4)C15C—H15C0.9500
N2D—C9D1.474 (4)C1D—C2D1.403 (4)
N11S—C1S1.478 (4)C1D—C6D1.410 (4)
N11S—H11B0.9100C2D—C3D1.372 (5)
N11S—H11C0.9100C2D—H2DA0.9500
N11S—H11D0.9100C3D—C4D1.388 (5)
N22S—C2S1.476 (4)C3D—H3DA0.9500
N22S—H22A0.9100C4D—C5D1.365 (5)
N22S—H22B0.9100C4D—H4DA0.9500
N22S—H22C0.9100C5D—C6D1.395 (5)
C1A—C2A1.402 (4)C5D—H5DA0.9500
C1A—C6A1.412 (4)C6D—C7D1.444 (4)
C2A—C3A1.374 (5)C7D—H7DA0.9500
C2A—H2AA0.9500C8D—C9D1.497 (5)
C3A—C4A1.385 (5)C8D—H8DA0.9900
C3A—H3AA0.9500C8D—H8DB0.9900
C4A—C5A1.354 (5)C9D—H9DA0.9900
C4A—H4AA0.9500C9D—H9DB0.9900
C5A—C6A1.412 (5)C10D—C11D1.432 (4)
C5A—H5AA0.9500C10D—H10D0.9500
C6A—C7A1.428 (5)C11D—C12D1.411 (5)
C7A—H7AA0.9500C11D—C16D1.416 (4)
C8A—C9A1.496 (5)C12D—C13D1.367 (5)
C8A—H8AA0.9900C12D—H12D0.9500
C8A—H8AB0.9900C13D—C14D1.399 (5)
C9A—H9AA0.9900C13D—H13D0.9500
C9A—H9AB0.9900C14D—C15D1.381 (5)
C10A—C11A1.428 (4)C14D—H14D0.9500
C10A—H10A0.9500C15D—C16D1.408 (4)
C11A—C16A1.412 (4)C15D—H15D0.9500
C11A—C12A1.413 (4)C1S—C1Sii1.512 (5)
C12A—C13A1.348 (5)C1S—H1SA0.9900
C12A—H12A0.9500C1S—H1SB0.9900
C13A—C14A1.388 (5)C2S—C2Siii1.497 (5)
C13A—H13A0.9500C2S—H2SA0.9900
C14A—C15A1.385 (4)C2S—H2SB0.9900
C14A—H14A0.9500O1SA—C11S1.2720 (10)
C15A—C16A1.392 (4)O1SB—C11S1.2699 (10)
C15A—H15A0.9500C11S—N1S1.335 (5)
C1B—C2B1.400 (4)C11S—H11A0.9500
C1B—C6B1.413 (4)N1S—C12S1.399 (5)
C2B—C3B1.374 (5)N1S—C13S1.447 (5)
C2B—H2BA0.9500C12S—H12E0.9800
C3B—C4B1.394 (5)C12S—H12F0.9800
C3B—H3BA0.9500C12S—H12G0.9800
C4B—C5B1.363 (5)C13S—H13E0.9800
C4B—H4BA0.9500C13S—H13F0.9800
C5B—C6B1.421 (5)C13S—H13G0.9800
O1A—Ni1—N2A176.03 (9)C9B—C8B—H8BB110.2
O1A—Ni1—N1A95.23 (10)H8BA—C8B—H8BB108.5
N2A—Ni1—N1A85.89 (12)N2B—C9B—C8B107.0 (3)
O1A—Ni1—O2A84.32 (8)N2B—C9B—H9BA110.3
N2A—Ni1—O2A94.83 (10)C8B—C9B—H9BA110.3
N1A—Ni1—O2A176.02 (9)N2B—C9B—H9BB110.3
O1A—Ni1—Ni3i105.44 (6)C8B—C9B—H9BB110.3
N2A—Ni1—Ni3i70.59 (7)H9BA—C9B—H9BB108.6
N1A—Ni1—Ni3i107.78 (7)N2B—C10B—C11B124.5 (3)
O2A—Ni1—Ni3i76.13 (5)N2B—C10B—H10B117.8
N2B—Ni2—O2B94.75 (10)C11B—C10B—H10B117.8
N2B—Ni2—N1B86.87 (12)C12B—C11B—C16B119.2 (3)
O2B—Ni2—N1B178.38 (11)C12B—C11B—C10B119.4 (3)
N2B—Ni2—O1B178.41 (10)C16B—C11B—C10B121.3 (3)
O2B—Ni2—O1B83.90 (9)C13B—C12B—C11B122.0 (3)
N1B—Ni2—O1B94.49 (11)C13B—C12B—H12B119.0
N2B—Ni2—Ni475.14 (8)C11B—C12B—H12B119.0
O2B—Ni2—Ni480.61 (6)C12B—C13B—C14B118.5 (3)
N1B—Ni2—Ni499.72 (8)C12B—C13B—H13B120.7
O1B—Ni2—Ni4105.42 (7)C14B—C13B—H13B120.7
N2C—Ni3—O2C95.11 (10)C15B—C14B—C13B121.7 (3)
N2C—Ni3—N1C86.16 (11)C15B—C14B—H14B119.2
O2C—Ni3—N1C176.24 (9)C13B—C14B—H14B119.2
N2C—Ni3—O1C176.42 (9)C14B—C15B—C16B120.3 (3)
O2C—Ni3—O1C83.96 (9)C14B—C15B—H15B119.8
N1C—Ni3—O1C94.99 (10)C16B—C15B—H15B119.8
O1D—Ni4—N1D95.37 (10)O2B—C16B—C11B123.8 (3)
O1D—Ni4—N2D178.16 (10)O2B—C16B—C15B118.0 (3)
N1D—Ni4—N2D86.17 (11)C11B—C16B—C15B118.2 (3)
O1D—Ni4—O2D83.91 (9)O1C—C1C—C2C118.8 (3)
N1D—Ni4—O2D178.02 (10)O1C—C1C—C6C123.4 (3)
N2D—Ni4—O2D94.58 (10)C2C—C1C—C6C117.8 (3)
O1D—Ni4—Ni283.51 (7)C3C—C2C—C1C121.7 (3)
N1D—Ni4—Ni274.24 (8)C3C—C2C—H2CA119.2
N2D—Ni4—Ni297.88 (8)C1C—C2C—H2CA119.2
O2D—Ni4—Ni2103.84 (7)C2C—C3C—C4C120.4 (3)
O12—Cl1—O14113.8 (2)C2C—C3C—H3CA119.8
O12—Cl1—O11112.2 (2)C4C—C3C—H3CA119.8
O14—Cl1—O11109.2 (2)C5C—C4C—C3C119.1 (3)
O12—Cl1—O13108.4 (3)C5C—C4C—H4CA120.4
O14—Cl1—O13105.7 (2)C3C—C4C—H4CA120.4
O11—Cl1—O13107.1 (2)C4C—C5C—C6C122.1 (3)
O24—Cl2—O22112.7 (2)C4C—C5C—H5CA119.0
O24—Cl2—O21113.1 (2)C6C—C5C—H5CA119.0
O22—Cl2—O21109.3 (2)C5C—C6C—C1C119.0 (3)
O24—Cl2—O23107.0 (3)C5C—C6C—C7C119.0 (3)
O22—Cl2—O23106.3 (3)C1C—C6C—C7C121.9 (3)
O21—Cl2—O23108.2 (2)N1C—C7C—C6C125.3 (3)
C1A—O1A—Ni1126.6 (2)N1C—C7C—H7CA117.3
C16A—O2A—Ni1127.90 (18)C6C—C7C—H7CA117.3
C1B—O1B—Ni2127.18 (18)N1C—C8C—C9C107.3 (2)
C16B—O2B—Ni2127.14 (17)N1C—C8C—H8CA110.3
C1C—O1C—Ni3127.25 (19)C9C—C8C—H8CA110.3
C16C—O2C—Ni3126.25 (19)N1C—C8C—H8CB110.3
C1D—O1D—Ni4126.93 (17)C9C—C8C—H8CB110.3
C16D—O2D—Ni4126.05 (17)H8CA—C8C—H8CB108.5
C7A—N1A—C8A119.3 (3)N2C—C9C—C8C107.2 (3)
C7A—N1A—Ni1126.7 (2)N2C—C9C—H9CA110.3
C8A—N1A—Ni1114.0 (2)C8C—C9C—H9CA110.3
C10A—N2A—C9A119.1 (3)N2C—C9C—H9CB110.3
C10A—N2A—Ni1126.9 (2)C8C—C9C—H9CB110.3
C9A—N2A—Ni1113.7 (2)H9CA—C9C—H9CB108.5
C7B—N1B—C8B119.3 (3)N2C—C10C—C11C124.8 (3)
C7B—N1B—Ni2127.4 (2)N2C—C10C—H10C117.6
C8B—N1B—Ni2113.3 (2)C11C—C10C—H10C117.6
C10B—N2B—C9B119.9 (3)C16C—C11C—C12C119.7 (3)
C10B—N2B—Ni2126.9 (2)C16C—C11C—C10C121.7 (3)
C9B—N2B—Ni2113.2 (2)C12C—C11C—C10C118.4 (3)
C7C—N1C—C8C119.0 (3)C13C—C12C—C11C120.5 (3)
C7C—N1C—Ni3126.9 (2)C13C—C12C—H12C119.7
C8C—N1C—Ni3113.9 (2)C11C—C12C—H12C119.7
C10C—N2C—C9C118.7 (3)C12C—C13C—C14C119.7 (3)
C10C—N2C—Ni3126.8 (2)C12C—C13C—H13C120.2
C9C—N2C—Ni3114.4 (2)C14C—C13C—H13C120.2
C7D—N1D—C8D118.6 (3)C15C—C14C—C13C121.5 (3)
C7D—N1D—Ni4127.1 (2)C15C—C14C—H14C119.3
C8D—N1D—Ni4114.1 (2)C13C—C14C—H14C119.3
C10D—N2D—C9D119.6 (3)C14C—C15C—C16C120.5 (3)
C10D—N2D—Ni4127.1 (2)C14C—C15C—H15C119.7
C9D—N2D—Ni4113.3 (2)C16C—C15C—H15C119.7
C1S—N11S—H11B109.5O2C—C16C—C11C123.8 (3)
C1S—N11S—H11C109.5O2C—C16C—C15C118.3 (3)
H11B—N11S—H11C109.5C11C—C16C—C15C118.0 (3)
C1S—N11S—H11D109.5O1D—C1D—C2D118.1 (3)
H11B—N11S—H11D109.5O1D—C1D—C6D124.7 (3)
H11C—N11S—H11D109.5C2D—C1D—C6D117.2 (3)
C2S—N22S—H22A109.5C3D—C2D—C1D121.3 (3)
C2S—N22S—H22B109.5C3D—C2D—H2DA119.3
H22A—N22S—H22B109.5C1D—C2D—H2DA119.3
C2S—N22S—H22C109.5C2D—C3D—C4D120.9 (3)
H22A—N22S—H22C109.5C2D—C3D—H3DA119.6
H22B—N22S—H22C109.5C4D—C3D—H3DA119.6
O1A—C1A—C2A118.2 (3)C5D—C4D—C3D119.0 (3)
O1A—C1A—C6A123.7 (3)C5D—C4D—H4DA120.5
C2A—C1A—C6A118.1 (3)C3D—C4D—H4DA120.5
C3A—C2A—C1A120.4 (3)C4D—C5D—C6D121.4 (3)
C3A—C2A—H2AA119.8C4D—C5D—H5DA119.3
C1A—C2A—H2AA119.8C6D—C5D—H5DA119.3
C2A—C3A—C4A121.7 (4)C5D—C6D—C1D120.1 (3)
C2A—C3A—H3AA119.2C5D—C6D—C7D118.6 (3)
C4A—C3A—H3AA119.2C1D—C6D—C7D121.2 (3)
C5A—C4A—C3A119.0 (3)N1D—C7D—C6D124.5 (3)
C5A—C4A—H4AA120.5N1D—C7D—H7DA117.8
C3A—C4A—H4AA120.5C6D—C7D—H7DA117.8
C4A—C5A—C6A121.5 (4)N1D—C8D—C9D106.2 (2)
C4A—C5A—H5AA119.2N1D—C8D—H8DA110.5
C6A—C5A—H5AA119.2C9D—C8D—H8DA110.5
C1A—C6A—C5A119.3 (3)N1D—C8D—H8DB110.5
C1A—C6A—C7A121.8 (3)C9D—C8D—H8DB110.5
C5A—C6A—C7A118.8 (3)H8DA—C8D—H8DB108.7
N1A—C7A—C6A124.9 (3)N2D—C9D—C8D107.6 (2)
N1A—C7A—H7AA117.6N2D—C9D—H9DA110.2
C6A—C7A—H7AA117.6C8D—C9D—H9DA110.2
N1A—C8A—C9A106.9 (3)N2D—C9D—H9DB110.2
N1A—C8A—H8AA110.3C8D—C9D—H9DB110.2
C9A—C8A—H8AA110.3H9DA—C9D—H9DB108.5
N1A—C8A—H8AB110.3N2D—C10D—C11D124.8 (3)
C9A—C8A—H8AB110.3N2D—C10D—H10D117.6
H8AA—C8A—H8AB108.6C11D—C10D—H10D117.6
N2A—C9A—C8A106.4 (2)C12D—C11D—C16D119.2 (3)
N2A—C9A—H9AA110.4C12D—C11D—C10D119.1 (3)
C8A—C9A—H9AA110.4C16D—C11D—C10D121.7 (3)
N2A—C9A—H9AB110.4C13D—C12D—C11D121.4 (3)
C8A—C9A—H9AB110.4C13D—C12D—H12D119.3
H9AA—C9A—H9AB108.6C11D—C12D—H12D119.3
N2A—C10A—C11A125.4 (3)C12D—C13D—C14D119.7 (3)
N2A—C10A—H10A117.3C12D—C13D—H13D120.1
C11A—C10A—H10A117.3C14D—C13D—H13D120.1
C16A—C11A—C12A118.4 (3)C15D—C14D—C13D120.2 (3)
C16A—C11A—C10A122.5 (3)C15D—C14D—H14D119.9
C12A—C11A—C10A119.1 (3)C13D—C14D—H14D119.9
C13A—C12A—C11A122.0 (3)C14D—C15D—C16D121.2 (3)
C13A—C12A—H12A119.0C14D—C15D—H15D119.4
C11A—C12A—H12A119.0C16D—C15D—H15D119.4
C12A—C13A—C14A119.9 (3)O2D—C16D—C15D118.2 (3)
C12A—C13A—H13A120.1O2D—C16D—C11D123.5 (3)
C14A—C13A—H13A120.1C15D—C16D—C11D118.3 (3)
C15A—C14A—C13A119.9 (3)N11S—C1S—C1Sii110.3 (3)
C15A—C14A—H14A120.0N11S—C1S—H1SA109.6
C13A—C14A—H14A120.0C1Sii—C1S—H1SA109.6
C14A—C15A—C16A121.2 (3)N11S—C1S—H1SB109.6
C14A—C15A—H15A119.4C1Sii—C1S—H1SB109.6
C16A—C15A—H15A119.4H1SA—C1S—H1SB108.1
O2A—C16A—C15A118.9 (3)N22S—C2S—C2Siii110.8 (3)
O2A—C16A—C11A122.4 (3)N22S—C2S—H2SA109.5
C15A—C16A—C11A118.6 (3)C2Siii—C2S—H2SA109.5
O1B—C1B—C2B118.3 (3)N22S—C2S—H2SB109.5
O1B—C1B—C6B123.3 (3)C2Siii—C2S—H2SB109.5
C2B—C1B—C6B118.4 (3)H2SA—C2S—H2SB108.1
C3B—C2B—C1B121.7 (3)O1SB—C11S—O1SA30.0 (3)
C3B—C2B—H2BA119.1O1SB—C11S—N1S136.5 (4)
C1B—C2B—H2BA119.1O1SA—C11S—N1S106.9 (5)
C2B—C3B—C4B120.4 (4)O1SB—C11S—H11A105.0
C2B—C3B—H3BA119.8O1SA—C11S—H11A134.6
C4B—C3B—H3BA119.8N1S—C11S—H11A118.4
C5B—C4B—C3B119.2 (4)C11S—N1S—C12S120.3 (4)
C5B—C4B—H4BA120.4C11S—N1S—C13S120.3 (3)
C3B—C4B—H4BA120.4C12S—N1S—C13S119.3 (4)
C4B—C5B—C6B121.9 (3)N1S—C12S—H12E109.5
C4B—C5B—H5BA119.0N1S—C12S—H12F109.5
C6B—C5B—H5BA119.0H12E—C12S—H12F109.5
C1B—C6B—C5B118.4 (3)N1S—C12S—H12G109.5
C1B—C6B—C7B122.2 (3)H12E—C12S—H12G109.5
C5B—C6B—C7B119.4 (3)H12F—C12S—H12G109.5
N1B—C7B—C6B124.5 (3)N1S—C13S—H13E109.5
N1B—C7B—H7BA117.8N1S—C13S—H13F109.5
C6B—C7B—H7BA117.8H13E—C13S—H13F109.5
N1B—C8B—C9B107.7 (3)N1S—C13S—H13G109.5
N1B—C8B—H8BA110.2H13E—C13S—H13G109.5
C9B—C8B—H8BA110.2H13F—C13S—H13G109.5
N1B—C8B—H8BB110.2
N2B—Ni2—Ni4—O1D83.41 (11)C10A—C11A—C12A—C13A176.5 (3)
O2B—Ni2—Ni4—O1D179.08 (9)C11A—C12A—C13A—C14A0.1 (5)
N1B—Ni2—Ni4—O1D0.68 (11)C12A—C13A—C14A—C15A0.6 (5)
O1B—Ni2—Ni4—O1D98.13 (9)C13A—C14A—C15A—C16A1.9 (4)
N2B—Ni2—Ni4—N1D179.11 (12)Ni1—O2A—C16A—C15A176.85 (17)
O2B—Ni2—Ni4—N1D81.61 (10)Ni1—O2A—C16A—C11A2.8 (3)
N1B—Ni2—Ni4—N1D96.79 (12)C14A—C15A—C16A—O2A177.9 (2)
O1B—Ni2—Ni4—N1D0.66 (10)C14A—C15A—C16A—C11A2.5 (4)
N2B—Ni2—Ni4—N2D95.37 (12)C12A—C11A—C16A—O2A178.5 (2)
O2B—Ni2—Ni4—N2D2.13 (10)C10A—C11A—C16A—O2A4.4 (4)
N1B—Ni2—Ni4—N2D179.47 (12)C12A—C11A—C16A—C15A1.9 (4)
O1B—Ni2—Ni4—N2D83.08 (10)C10A—C11A—C16A—C15A175.3 (2)
N2B—Ni2—Ni4—O2D1.35 (10)Ni2—O1B—C1B—C2B170.2 (2)
O2B—Ni2—Ni4—O2D98.85 (9)Ni2—O1B—C1B—C6B9.0 (4)
N1B—Ni2—Ni4—O2D82.75 (11)O1B—C1B—C2B—C3B179.2 (3)
O1B—Ni2—Ni4—O2D179.80 (8)C6B—C1B—C2B—C3B0.0 (5)
N2A—Ni1—O1A—C1A95.6 (15)C1B—C2B—C3B—C4B0.5 (5)
N1A—Ni1—O1A—C1A10.7 (2)C2B—C3B—C4B—C5B1.7 (5)
O2A—Ni1—O1A—C1A173.3 (2)C3B—C4B—C5B—C6B2.5 (5)
Ni3i—Ni1—O1A—C1A99.4 (2)O1B—C1B—C6B—C5B179.9 (3)
O1A—Ni1—O2A—C16A176.6 (2)C2B—C1B—C6B—C5B0.7 (4)
N2A—Ni1—O2A—C16A0.5 (2)O1B—C1B—C6B—C7B0.3 (5)
N1A—Ni1—O2A—C16A99.8 (15)C2B—C1B—C6B—C7B178.9 (3)
Ni3i—Ni1—O2A—C16A69.09 (18)C4B—C5B—C6B—C1B2.0 (5)
N2B—Ni2—O1B—C1B159 (4)C4B—C5B—C6B—C7B177.6 (3)
O2B—Ni2—O1B—C1B169.1 (2)C8B—N1B—C7B—C6B176.6 (3)
N1B—Ni2—O1B—C1B10.8 (2)Ni2—N1B—C7B—C6B1.5 (5)
Ni4—Ni2—O1B—C1B90.6 (2)C1B—C6B—C7B—N1B3.6 (5)
N2B—Ni2—O2B—C16B11.8 (2)C5B—C6B—C7B—N1B176.0 (3)
N1B—Ni2—O2B—C16B172 (32)C7B—N1B—C8B—C9B154.3 (3)
O1B—Ni2—O2B—C16B167.3 (2)Ni2—N1B—C8B—C9B27.4 (3)
Ni4—Ni2—O2B—C16B85.9 (2)C10B—N2B—C9B—C8B149.2 (3)
N2C—Ni3—O1C—C1C107.1 (16)Ni2—N2B—C9B—C8B31.8 (3)
O2C—Ni3—O1C—C1C177.8 (2)N1B—C8B—C9B—N2B36.3 (4)
N1C—Ni3—O1C—C1C1.5 (2)C9B—N2B—C10B—C11B172.3 (3)
N2C—Ni3—O2C—C16C12.6 (2)Ni2—N2B—C10B—C11B6.6 (5)
N1C—Ni3—O2C—C16C97.0 (16)N2B—C10B—C11B—C12B178.8 (3)
O1C—Ni3—O2C—C16C170.9 (2)N2B—C10B—C11B—C16B5.3 (5)
N1D—Ni4—O1D—C1D2.4 (3)C16B—C11B—C12B—C13B2.0 (5)
N2D—Ni4—O1D—C1D145 (3)C10B—C11B—C12B—C13B173.9 (3)
O2D—Ni4—O1D—C1D179.5 (2)C11B—C12B—C13B—C14B0.3 (6)
Ni2—Ni4—O1D—C1D75.8 (2)C12B—C13B—C14B—C15B0.5 (6)
O1D—Ni4—O2D—C16D164.4 (2)C13B—C14B—C15B—C16B0.4 (6)
N1D—Ni4—O2D—C16D96 (3)Ni2—O2B—C16B—C11B4.3 (4)
N2D—Ni4—O2D—C16D16.7 (2)Ni2—O2B—C16B—C15B176.1 (2)
Ni2—Ni4—O2D—C16D82.6 (2)C12B—C11B—C16B—O2B177.7 (3)
O1A—Ni1—N1A—C7A3.5 (2)C10B—C11B—C16B—O2B6.5 (5)
N2A—Ni1—N1A—C7A172.6 (2)C12B—C11B—C16B—C15B2.8 (4)
O2A—Ni1—N1A—C7A86.8 (15)C10B—C11B—C16B—C15B173.1 (3)
Ni3i—Ni1—N1A—C7A104.5 (2)C14B—C15B—C16B—O2B178.4 (3)
O1A—Ni1—N1A—C8A174.27 (18)C14B—C15B—C16B—C11B2.0 (5)
N2A—Ni1—N1A—C8A9.55 (19)Ni3—O1C—C1C—C2C177.59 (18)
O2A—Ni1—N1A—C8A91.0 (15)Ni3—O1C—C1C—C6C1.6 (4)
Ni3i—Ni1—N1A—C8A77.66 (18)O1C—C1C—C2C—C3C179.8 (3)
O1A—Ni1—N2A—C10A80.2 (15)C6C—C1C—C2C—C3C1.0 (4)
N1A—Ni1—N2A—C10A173.3 (2)C1C—C2C—C3C—C4C0.1 (5)
O2A—Ni1—N2A—C10A2.8 (2)C2C—C3C—C4C—C5C0.8 (5)
Ni3i—Ni1—N2A—C10A76.2 (2)C3C—C4C—C5C—C6C0.3 (4)
O1A—Ni1—N2A—C9A92.8 (15)C4C—C5C—C6C—C1C0.8 (4)
N1A—Ni1—N2A—C9A13.72 (19)C4C—C5C—C6C—C7C175.9 (3)
O2A—Ni1—N2A—C9A170.21 (19)O1C—C1C—C6C—C5C179.4 (2)
Ni3i—Ni1—N2A—C9A96.76 (19)C2C—C1C—C6C—C5C1.4 (4)
N2B—Ni2—N1B—C7B173.8 (3)O1C—C1C—C6C—C7C4.0 (4)
O2B—Ni2—N1B—C7B2 (4)C2C—C1C—C6C—C7C175.2 (2)
O1B—Ni2—N1B—C7B7.1 (3)C8C—N1C—C7C—C6C172.5 (2)
Ni4—Ni2—N1B—C7B99.4 (3)Ni3—N1C—C7C—C6C1.4 (4)
N2B—Ni2—N1B—C8B8.1 (2)C5C—C6C—C7C—N1C179.0 (2)
O2B—Ni2—N1B—C8B176 (100)C1C—C6C—C7C—N1C2.5 (4)
O1B—Ni2—N1B—C8B171.1 (2)C7C—N1C—C8C—C9C155.6 (2)
Ni4—Ni2—N1B—C8B82.4 (2)Ni3—N1C—C8C—C9C29.7 (3)
O2B—Ni2—N2B—C10B12.9 (3)C10C—N2C—C9C—C8C154.9 (2)
N1B—Ni2—N2B—C10B167.2 (3)Ni3—N2C—C9C—C8C27.5 (3)
O1B—Ni2—N2B—C10B19 (4)N1C—C8C—C9C—N2C34.8 (3)
Ni4—Ni2—N2B—C10B91.9 (3)C9C—N2C—C10C—C11C179.4 (2)
O2B—Ni2—N2B—C9B166.0 (2)Ni3—N2C—C10C—C11C3.3 (4)
N1B—Ni2—N2B—C9B13.8 (2)N2C—C10C—C11C—C16C2.9 (4)
O1B—Ni2—N2B—C9B162 (4)N2C—C10C—C11C—C12C172.4 (3)
Ni4—Ni2—N2B—C9B87.1 (2)C16C—C11C—C12C—C13C2.4 (4)
N2C—Ni3—N1C—C7C173.7 (2)C10C—C11C—C12C—C13C173.0 (3)
O2C—Ni3—N1C—C7C76.5 (16)C11C—C12C—C13C—C14C0.2 (5)
O1C—Ni3—N1C—C7C2.9 (2)C12C—C13C—C14C—C15C1.3 (5)
N2C—Ni3—N1C—C8C12.17 (18)C13C—C14C—C15C—C16C0.6 (5)
O2C—Ni3—N1C—C8C97.7 (16)Ni3—O2C—C16C—C11C16.0 (4)
O1C—Ni3—N1C—C8C171.23 (18)Ni3—O2C—C16C—C15C163.4 (2)
O2C—Ni3—N2C—C10C3.1 (2)C12C—C11C—C16C—O2C177.6 (2)
N1C—Ni3—N2C—C10C173.3 (2)C10C—C11C—C16C—O2C7.2 (4)
O1C—Ni3—N2C—C10C77.8 (17)C12C—C11C—C16C—C15C3.0 (4)
O2C—Ni3—N2C—C9C174.25 (18)C10C—C11C—C16C—C15C172.2 (3)
N1C—Ni3—N2C—C9C9.30 (18)C14C—C15C—C16C—O2C179.0 (3)
O1C—Ni3—N2C—C9C99.6 (16)C14C—C15C—C16C—C11C1.6 (4)
O1D—Ni4—N1D—C7D5.0 (3)Ni4—O1D—C1D—C2D176.3 (2)
N2D—Ni4—N1D—C7D174.1 (3)Ni4—O1D—C1D—C6D2.1 (4)
O2D—Ni4—N1D—C7D74 (3)O1D—C1D—C2D—C3D179.0 (3)
Ni2—Ni4—N1D—C7D86.6 (3)C6D—C1D—C2D—C3D2.5 (5)
O1D—Ni4—N1D—C8D169.6 (2)C1D—C2D—C3D—C4D0.6 (6)
N2D—Ni4—N1D—C8D11.4 (2)C2D—C3D—C4D—C5D1.2 (6)
O2D—Ni4—N1D—C8D101 (3)C3D—C4D—C5D—C6D1.1 (6)
Ni2—Ni4—N1D—C8D87.9 (2)C4D—C5D—C6D—C1D0.9 (5)
O1D—Ni4—N2D—C10D44 (4)C4D—C5D—C6D—C7D174.9 (3)
N1D—Ni4—N2D—C10D168.4 (3)O1D—C1D—C6D—C5D179.0 (3)
O2D—Ni4—N2D—C10D9.7 (3)C2D—C1D—C6D—C5D2.6 (5)
Ni2—Ni4—N2D—C10D94.9 (3)O1D—C1D—C6D—C7D5.4 (5)
O1D—Ni4—N2D—C9D136 (3)C2D—C1D—C6D—C7D173.1 (3)
N1D—Ni4—N2D—C9D11.5 (2)C8D—N1D—C7D—C6D171.2 (3)
O2D—Ni4—N2D—C9D170.3 (2)Ni4—N1D—C7D—C6D3.2 (4)
Ni2—Ni4—N2D—C9D85.0 (2)C5D—C6D—C7D—N1D178.3 (3)
Ni1—O1A—C1A—C2A166.28 (19)C1D—C6D—C7D—N1D2.6 (5)
Ni1—O1A—C1A—C6A13.0 (4)C7D—N1D—C8D—C9D154.6 (3)
O1A—C1A—C2A—C3A178.4 (2)Ni4—N1D—C8D—C9D30.4 (3)
C6A—C1A—C2A—C3A2.3 (4)C10D—N2D—C9D—C8D149.1 (3)
C1A—C2A—C3A—C4A1.2 (4)Ni4—N2D—C9D—C8D30.9 (3)
C2A—C3A—C4A—C5A0.3 (5)N1D—C8D—C9D—N2D37.4 (4)
C3A—C4A—C5A—C6A0.5 (5)C9D—N2D—C10D—C11D178.8 (3)
O1A—C1A—C6A—C5A178.2 (2)Ni4—N2D—C10D—C11D1.2 (5)
C2A—C1A—C6A—C5A2.5 (4)N2D—C10D—C11D—C12D173.4 (3)
O1A—C1A—C6A—C7A5.8 (4)N2D—C10D—C11D—C16D4.9 (5)
C2A—C1A—C6A—C7A173.5 (2)C16D—C11D—C12D—C13D1.1 (5)
C4A—C5A—C6A—C1A1.7 (4)C10D—C11D—C12D—C13D177.2 (3)
C4A—C5A—C6A—C7A174.4 (3)C11D—C12D—C13D—C14D0.2 (5)
C8A—N1A—C7A—C6A179.2 (2)C12D—C13D—C14D—C15D0.2 (5)
Ni1—N1A—C7A—C6A1.5 (4)C13D—C14D—C15D—C16D1.1 (5)
C1A—C6A—C7A—N1A1.8 (4)Ni4—O2D—C16D—C15D163.5 (2)
C5A—C6A—C7A—N1A174.2 (3)Ni4—O2D—C16D—C11D15.5 (4)
C7A—N1A—C8A—C9A152.6 (3)C14D—C15D—C16D—O2D179.0 (3)
Ni1—N1A—C8A—C9A29.5 (3)C14D—C15D—C16D—C11D2.0 (5)
C10A—N2A—C9A—C8A153.8 (3)C12D—C11D—C16D—O2D179.1 (3)
Ni1—N2A—C9A—C8A32.6 (3)C10D—C11D—C16D—O2D2.6 (5)
N1A—C8A—C9A—N2A37.8 (3)C12D—C11D—C16D—C15D1.9 (4)
C9A—N2A—C10A—C11A170.7 (2)C10D—C11D—C16D—C15D176.3 (3)
Ni1—N2A—C10A—C11A1.9 (4)O1SB—C11S—N1S—C12S5.2 (8)
N2A—C10A—C11A—C16A2.0 (4)O1SA—C11S—N1S—C12S0.6 (6)
N2A—C10A—C11A—C12A179.2 (3)O1SB—C11S—N1S—C13S178.7 (6)
C16A—C11A—C12A—C13A0.8 (4)O1SA—C11S—N1S—C13S175.4 (5)
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11S—H11B···O2A0.911.972.877 (3)173
N11S—H11B···O1A0.912.452.949 (3)115
N11S—H11D···O2D0.912.002.876 (3)162
N11S—H11D···O1D0.912.483.132 (3)128
N22S—H22A···O1B0.911.972.830 (3)157
N22S—H22A···O2B0.912.342.884 (3)118
N22S—H22B···O1C0.911.982.853 (3)160
N22S—H22B···O2C0.912.453.118 (3)130
N22S—H22C···O1SB0.911.912.706 (5)145
N22S—H22C···O1SA0.911.902.778 (6)161

Experimental details

Crystal data
Chemical formula(C2H10N2)[Ni(C16H14N2O2)]4·(ClO4)2·C3H7NO
Mr1634.12
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)15.0209 (11), 15.0492 (13), 18.2709 (8)
α, β, γ (°)85.990 (5), 86.506 (5), 62.963 (8)
V3)3667.8 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.16
Crystal size (mm)0.53 × 0.28 × 0.24
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.832, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
31940, 13062, 9248
Rint0.031
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.110, 0.95
No. of reflections13062
No. of parameters936
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11S—H11B···O2A0.911.972.877 (3)172.8
N11S—H11B···O1A0.912.452.949 (3)115.0
N11S—H11D···O2D0.912.002.876 (3)161.6
N11S—H11D···O1D0.912.483.132 (3)128.4
N22S—H22A···O1B0.911.972.830 (3)156.8
N22S—H22A···O2B0.912.342.884 (3)117.9
N22S—H22B···O1C0.911.982.853 (3)160.4
N22S—H22B···O2C0.912.453.118 (3)130.2
N22S—H22C···O1SB0.911.912.706 (5)145.3
N22S—H22C···O1SA0.911.902.778 (6)161.1
 

Acknowledgements

RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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