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Acta Cryst. (2007). E63, m2904    [ doi:10.1107/S160053680705430X ]

Bis[1-(3-cyanobenzyl)triphenylphosphonium] bis(1,2-dicyanoethene-1,2-dithiolato-[kappa]2S,S')nickelate(II)

C. Ni, J. Zhou and Y. Hou

Abstract top

The title complex, (C26H21NP)2[Ni(C4N2S2)2], is a salt of the mCNBzTPP+cation and the [Ni(mnt)2]2- anion [mCNBzTPP+ is the 1-(3-cyanobenzyltriphenylphosphonium) cation and mnt2- is the maleonitriledithiolate anion] and was prepared by the direct reaction of NiCl2, Na2mnt and (mCNBzTPP)+·Br- in ethanol. The asymmetric unit consists of two unique mCNBzTPP+cations and half each of two [Ni(mnt)2]2- anions with each Ni atom lying on an inversion centre. The NiII ions adopt a square-planar coordination geometry, binding to the S atoms of two mnt2- ligands. Both [mCNBzTPP]+ cations adopt conformations in which their four aromatic rings are twisted with respect to the planes that include the P atoms and the two C atoms linking them to the 3-cyanobenzyl rings. Three weak C-H...N hydrogen bonds play an important role in stabilizing the crystal structure.

Comment top

Much effort has been devoted to the study of square planar M(dithiolene)2 complexes (Robertson & Cronin, 2002; Ni et al., 2004; Nishijo et al., 2003; Canadell, 1999). Recently, we have carried out a systematic investigation on the coordination chemistry of salts containing Ni(mnt)2 anion and substituted benzyltriphenylphosphonium cations and obtained some Ni(mnt)22−-based molecular solids (Ni et al., 2005; Yang & Ni, 2006; Liu & Ni, 2006; Zhou et al., 2007). In this paper, we report the structure of the title compound, Fig. 1. There are two halves of non-equivalent Ni(mnt)22− anions and two (mCNBzTPP)+ cations in the asymmetric unit. For the two Ni(mnt)22− anions. The Ni1 and Ni2 atoms are each coordinated to four sulfur atoms and exhibit square planar coordination geometry with the Ni atoms lying on inversion centres. The N atoms of the four unique CN groups deviate from the C1/C2/Ni1/S1/S2 or C5/C6/Ni2/S3/S4 planes by 0.029 (3) Å for N1, −0.077 (3) Å for N2, −0.216 (2) Å for N3 and −0.242 (2) Å for N4 respectively.

The two (mCNBzTPP)+ cations adopt a conformation where four phenyl rings are twisted with respect to the plane including the P atom and the two C atoms linking it to the 3-cyanobenzyl ring. For the cation containing P1, the dihedral angles are 88.7 (3) for the C9/C10/C11/C12/C13/C14 ring, 84.0 (2) ° for the C17/C18/C19/C20/C21/C22 ring, 24.4 (2) ° for the C23/C24/C25/C26/C27/C28 ring, and 87.7 (2) ° for the C29/C30/C31/C32/C33/C34 ring. For the cation containing P2, the dihedral angles are 90.6 (3) for the C35/C36/C37/C38/C39/C40 ring, 93.2 (2) ° for the C43/C44/C45/C46/C47/C48 ring, 23.0 (2) ° for the C49/C50/C51/C52/C53/C54 ring, and 82.1 (2) ° for the C55/C56/C57/C58/C59/C60 ring. The deviations of the N5 and N6 atoms from the C9/C10/C11/C12/C13/C14 and C35/C36/C37/C38/C39/C40 phenyl ring planes are −0.052 (2)Å and 0.130 (2) Å respectively.

The crystal structure is stabilized by C10—H10···N4, C33—H33···N2 and C36—H36···N hydrogen bonds, Fig 2, Table 1.

Related literature top

For details of other square planar M(dithiolene)2 complexes, see: Robertson & Cronin (2002); Ni et al. (2004); Nishijo et al. (2003); Canadell (1999). For the structures of related Ni(mnt)22− complexes with square-planar geometry and a substituted triphenylphosphonium counter-ion, see: Ni et al. (2005); Yang & Ni (2006); Liu & Ni, 2006; Zhou et al. (2007).

Experimental top

The title compound was prepared by the direct reaction of NiCl2·6H2O, Na2mnt and (mCNBzTPP)+Br− in methanol. Red block-shaped single crystals were obtained by slow evaporation of a CH3CN solution at room temperature over two weeks.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic and 0.97 Å, Uiso = 1.2Ueq (C) for CH2 atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Labelled atoms are related to unlabelled atoms by the symmetry operations −x + 1, −y, −z + 2 and −x + 2, −y, −z + 2.
[Figure 2] Fig. 2. Crystal packing of (I) showing the C—H···N hydrogen bonds between the anions and cations drawn as dashed lines.
Bis[1-(3-cyanobenzyl)triphenylphosphonium] bis(1,2-dicyanoethene-1,2- dithiolato-κ2S,S')nickelate(II) top
Crystal data top
(C26H21NP)2[Ni(C4N2S2)2]F000 = 2264
Mr = 1095.89Dx = 1.369 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 957 reflections
a = 19.158 (4) Åθ = 2.6–22.9º
b = 14.956 (3) ŵ = 0.63 mm−1
c = 19.598 (4) ÅT = 298 (2) K
β = 108.785 (4)ºBlock, red
V = 5316.3 (19) Å30.34 × 0.22 × 0.15 mm
Z = 4
Data collection top
Bruker Smart Apex CCD
diffractometer		9356 independent reflections
Radiation source: fine-focus sealed tube6235 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.076
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −22→22
Tmin = 0.834, Tmax = 0.912k = −17→8
25624 measured reflectionsl = −23→23
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)] = 0.061H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0541P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.015
9356 reflectionsΔρmax = 0.83 e Å−3
661 parametersΔρmin = −0.73 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C26H21NP)2[Ni(C4N2S2)2]V = 5316.3 (19) Å3
Mr = 1095.89Z = 4
Monoclinic, P21/nMo Kα
a = 19.158 (4) ŵ = 0.63 mm−1
b = 14.956 (3) ÅT = 298 (2) K
c = 19.598 (4) Å0.34 × 0.22 × 0.15 mm
β = 108.785 (4)º
Data collection top
Bruker Smart Apex CCD
diffractometer		9356 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		6235 reflections with I > 2σ(I)
Tmin = 0.834, Tmax = 0.912Rint = 0.076
25624 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061661 parameters
wR(F2) = 0.139H-atom parameters constrained
S = 1.09Δρmax = 0.83 e Å−3
9356 reflectionsΔρmin = −0.73 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.00001.00000.05280 (19)
Ni21.00000.00001.00000.05428 (19)
C10.42984 (18)0.1858 (2)0.98368 (18)0.0558 (9)
C20.45351 (18)0.1800 (2)0.92638 (19)0.0589 (9)
C30.4419 (2)0.2543 (3)0.8777 (2)0.0668 (10)
C40.3917 (2)0.2625 (3)0.9953 (2)0.0682 (11)
C50.9070 (2)0.1704 (2)0.97231 (18)0.0587 (9)
C60.96210 (19)0.1926 (2)0.94730 (18)0.0568 (9)
C70.9619 (2)0.2757 (3)0.9121 (2)0.0655 (10)
C80.8462 (2)0.2295 (3)0.9644 (2)0.0664 (10)
C90.6312 (2)0.2789 (3)0.07367 (19)0.0657 (10)
C100.6713 (3)0.3359 (4)0.0437 (2)0.0982 (16)
H100.70840.31270.02790.118*
C110.6563 (3)0.4260 (4)0.0376 (3)0.122 (2)
H110.68350.46300.01740.146*
C120.6027 (3)0.4618 (3)0.0604 (3)0.1008 (16)
H120.59340.52290.05660.121*
C130.5623 (3)0.4066 (3)0.0892 (2)0.0733 (11)
C140.5765 (2)0.3156 (3)0.09584 (18)0.0617 (10)
H140.54860.27900.11550.074*
C150.6486 (2)0.1806 (3)0.08122 (17)0.0658 (10)
H15A0.66520.16170.04160.079*
H15B0.60400.14770.07780.079*
C160.5037 (3)0.4444 (3)0.1115 (2)0.0886 (14)
C170.78815 (18)0.2373 (2)0.18514 (17)0.0524 (9)
C180.8438 (2)0.2316 (3)0.1540 (2)0.0670 (10)
H180.84750.18140.12740.080*
C190.8927 (2)0.2998 (3)0.1626 (2)0.0858 (13)
H190.92980.29580.14170.103*
C200.8882 (3)0.3739 (3)0.2014 (3)0.0920 (14)
H200.92230.41990.20700.110*
C210.8336 (3)0.3806 (3)0.2323 (2)0.0834 (13)
H210.83070.43110.25900.100*
C220.7827 (2)0.3126 (3)0.22363 (19)0.0653 (10)
H220.74500.31760.24370.078*
C230.76030 (19)0.0478 (2)0.15672 (18)0.0527 (9)
C240.7239 (2)−0.0135 (3)0.1050 (2)0.0703 (11)
H240.6769−0.00110.07380.084*
C250.7578 (3)−0.0931 (3)0.1001 (2)0.0819 (13)
H250.7337−0.13410.06470.098*
C260.8260 (3)−0.1129 (3)0.1461 (3)0.0789 (12)
H260.8481−0.16720.14220.095*
C270.8621 (2)−0.0529 (3)0.1983 (2)0.0777 (12)
H270.9088−0.06630.22980.093*
C280.8297 (2)0.0267 (3)0.2043 (2)0.0661 (10)
H280.85400.06700.24030.079*
C290.68050 (19)0.1447 (2)0.23794 (18)0.0498 (8)
C300.60572 (19)0.1288 (2)0.2250 (2)0.0593 (9)
H300.57340.12630.17810.071*
C310.5804 (2)0.1170 (3)0.2823 (2)0.0721 (11)
H310.53020.10830.27360.087*
C320.6266 (3)0.1177 (3)0.3513 (2)0.0750 (12)
H320.60840.10890.38940.090*
C330.7008 (2)0.1317 (3)0.3643 (2)0.0729 (11)
H330.73300.13130.41140.088*
C340.7278 (2)0.1462 (2)0.30799 (19)0.0638 (10)
H340.77780.15700.31720.077*
C350.1902 (2)0.3078 (3)0.07543 (17)0.0595 (9)
C360.2387 (2)0.3790 (3)0.0796 (2)0.0723 (11)
H360.28710.36750.08180.087*
C370.2153 (3)0.4658 (3)0.0803 (2)0.0841 (13)
H370.24820.51230.08290.101*
C380.1447 (3)0.4850 (3)0.0772 (2)0.0800 (13)
H380.12940.54390.07790.096*
C390.0969 (2)0.4154 (3)0.0731 (2)0.0683 (11)
C400.1188 (2)0.3278 (3)0.07163 (17)0.0623 (10)
H400.08510.28180.06800.075*
C410.2163 (2)0.2123 (2)0.07693 (17)0.0617 (10)
H41A0.25410.20900.05390.074*
H41B0.17540.17490.04980.074*
C420.0227 (3)0.4321 (3)0.0721 (2)0.0849 (13)
C430.32015 (19)0.2503 (2)0.21637 (18)0.0550 (9)
C440.3895 (2)0.2469 (3)0.20863 (19)0.0642 (10)
H440.40220.19930.18450.077*
C450.4392 (2)0.3137 (3)0.2365 (2)0.0781 (12)
H450.48580.31140.23150.094*
C460.4205 (3)0.3839 (3)0.2717 (2)0.0821 (13)
H460.45450.42910.29050.099*
C470.3521 (3)0.3884 (3)0.2798 (2)0.0799 (12)
H470.33990.43610.30420.096*
C480.3014 (2)0.3214 (3)0.25145 (19)0.0669 (10)
H480.25460.32440.25610.080*
C490.2971 (2)0.0648 (2)0.1677 (2)0.0581 (9)
C500.2752 (2)0.0107 (3)0.1084 (2)0.0779 (12)
H500.23860.02970.06690.094*
C510.3071 (3)−0.0713 (3)0.1102 (3)0.0985 (16)
H510.2919−0.10780.06970.118*
C520.3601 (3)−0.1002 (3)0.1694 (4)0.0963 (16)
H520.3815−0.15610.16970.116*
C530.3825 (3)−0.0470 (3)0.2295 (3)0.0910 (14)
H530.4193−0.06670.27050.109*
C540.3509 (2)0.0355 (3)0.2293 (2)0.0768 (11)
H540.36560.07130.27020.092*
C550.18144 (19)0.1573 (2)0.20786 (18)0.0534 (9)
C560.1109 (2)0.1369 (2)0.1647 (2)0.0597 (9)
H560.10030.13130.11510.072*
C570.0561 (2)0.1250 (3)0.1953 (2)0.0723 (11)
H570.00840.11180.16620.087*
C580.0715 (3)0.1324 (3)0.2675 (3)0.0786 (12)
H580.03380.12570.28750.094*
C590.1418 (3)0.1498 (3)0.3114 (2)0.0778 (12)
H590.15210.15290.36110.093*
C600.1974 (2)0.1626 (2)0.2818 (2)0.0658 (10)
H600.24510.17470.31130.079*
N10.4317 (2)0.3151 (3)0.84045 (19)0.0875 (11)
N20.3606 (2)0.3238 (3)1.0040 (2)0.1000 (13)
N30.9608 (2)0.3414 (2)0.8829 (2)0.0867 (11)
N40.7969 (2)0.2761 (3)0.9571 (2)0.0936 (12)
N50.4584 (3)0.4751 (3)0.1290 (3)0.1336 (19)
N6−0.0351 (2)0.4436 (3)0.0736 (2)0.1084 (14)
P10.71916 (5)0.15259 (6)0.16601 (5)0.0517 (2)
P20.25325 (5)0.17021 (6)0.16846 (5)0.0535 (3)
S10.44310 (5)0.09780 (7)1.04475 (5)0.0612 (3)
S20.49732 (6)0.08587 (7)0.91018 (5)0.0721 (3)
S30.90439 (5)0.06748 (7)1.01219 (6)0.0694 (3)
S41.03274 (5)0.11747 (7)0.95286 (5)0.0627 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0455 (4)0.0584 (4)0.0527 (4)0.0018 (3)0.0133 (3)0.0064 (3)
Ni20.0468 (4)0.0560 (4)0.0551 (4)0.0025 (3)0.0096 (3)0.0013 (3)
C10.0410 (19)0.061 (2)0.063 (2)0.0029 (18)0.0134 (17)0.0062 (19)
C20.051 (2)0.062 (2)0.063 (2)0.0034 (19)0.0166 (18)0.009 (2)
C30.063 (3)0.069 (3)0.073 (3)0.007 (2)0.028 (2)0.007 (2)
C40.066 (3)0.069 (3)0.073 (3)0.004 (2)0.027 (2)0.003 (2)
C50.055 (2)0.057 (2)0.056 (2)0.012 (2)0.0077 (18)0.0009 (18)
C60.054 (2)0.058 (2)0.056 (2)0.0011 (19)0.0143 (18)0.0000 (19)
C70.070 (3)0.065 (3)0.063 (2)0.006 (2)0.025 (2)0.001 (2)
C80.070 (3)0.066 (3)0.061 (2)0.004 (2)0.018 (2)0.002 (2)
C90.059 (2)0.078 (3)0.054 (2)0.012 (2)0.0104 (19)0.010 (2)
C100.085 (3)0.122 (5)0.097 (3)0.024 (3)0.043 (3)0.045 (3)
C110.123 (5)0.116 (5)0.142 (5)0.015 (4)0.064 (4)0.070 (4)
C120.127 (5)0.075 (3)0.102 (4)0.008 (3)0.039 (3)0.035 (3)
C130.096 (3)0.061 (3)0.058 (2)0.007 (3)0.019 (2)0.012 (2)
C140.069 (3)0.058 (3)0.057 (2)0.001 (2)0.0195 (19)0.0055 (19)
C150.058 (2)0.080 (3)0.058 (2)0.005 (2)0.0168 (19)−0.009 (2)
C160.134 (5)0.057 (3)0.080 (3)0.015 (3)0.042 (3)0.007 (2)
C170.050 (2)0.053 (2)0.055 (2)0.0036 (17)0.0169 (17)0.0043 (18)
C180.079 (3)0.056 (2)0.076 (3)−0.004 (2)0.039 (2)0.000 (2)
C190.092 (3)0.068 (3)0.121 (4)−0.011 (3)0.066 (3)−0.001 (3)
C200.097 (4)0.062 (3)0.131 (4)−0.026 (3)0.056 (3)−0.008 (3)
C210.102 (4)0.048 (3)0.108 (3)−0.011 (3)0.046 (3)−0.016 (2)
C220.072 (3)0.057 (2)0.074 (2)0.005 (2)0.035 (2)−0.004 (2)
C230.054 (2)0.046 (2)0.059 (2)−0.0021 (18)0.0206 (19)−0.0077 (18)
C240.058 (2)0.072 (3)0.080 (3)−0.002 (2)0.021 (2)−0.024 (2)
C250.087 (3)0.068 (3)0.099 (3)−0.012 (3)0.042 (3)−0.031 (3)
C260.089 (3)0.049 (3)0.118 (4)0.006 (2)0.059 (3)−0.006 (3)
C270.072 (3)0.059 (3)0.100 (3)0.016 (2)0.025 (2)−0.003 (2)
C280.066 (3)0.055 (2)0.073 (2)0.000 (2)0.015 (2)−0.008 (2)
C290.051 (2)0.040 (2)0.060 (2)0.0013 (16)0.0196 (18)−0.0042 (17)
C300.047 (2)0.056 (2)0.071 (2)0.0061 (18)0.0144 (19)0.0035 (19)
C310.058 (2)0.065 (3)0.106 (3)0.006 (2)0.043 (3)0.011 (3)
C320.086 (3)0.071 (3)0.085 (3)−0.001 (2)0.051 (3)0.003 (2)
C330.076 (3)0.075 (3)0.068 (2)−0.002 (2)0.024 (2)−0.002 (2)
C340.060 (2)0.069 (3)0.064 (2)−0.006 (2)0.024 (2)−0.005 (2)
C350.064 (2)0.065 (3)0.050 (2)0.003 (2)0.0187 (18)0.0066 (19)
C360.070 (3)0.078 (3)0.081 (3)−0.004 (2)0.040 (2)0.006 (2)
C370.099 (4)0.065 (3)0.098 (3)−0.012 (3)0.046 (3)0.010 (3)
C380.093 (3)0.061 (3)0.098 (3)0.006 (3)0.048 (3)0.019 (2)
C390.075 (3)0.063 (3)0.075 (3)0.012 (2)0.034 (2)0.015 (2)
C400.059 (2)0.067 (3)0.060 (2)−0.004 (2)0.0176 (19)0.007 (2)
C410.056 (2)0.072 (3)0.058 (2)−0.001 (2)0.0185 (18)−0.0052 (19)
C420.095 (4)0.068 (3)0.101 (3)0.019 (3)0.045 (3)0.031 (2)
C430.055 (2)0.051 (2)0.056 (2)−0.0016 (18)0.0136 (18)−0.0009 (18)
C440.062 (2)0.056 (2)0.077 (3)−0.005 (2)0.026 (2)−0.001 (2)
C450.065 (3)0.064 (3)0.106 (3)−0.013 (2)0.028 (2)0.002 (3)
C460.083 (3)0.063 (3)0.090 (3)−0.022 (3)0.013 (3)0.005 (2)
C470.108 (4)0.052 (3)0.075 (3)−0.005 (3)0.021 (3)−0.009 (2)
C480.077 (3)0.056 (2)0.070 (2)0.001 (2)0.027 (2)−0.007 (2)
C490.057 (2)0.049 (2)0.073 (2)−0.0080 (19)0.029 (2)−0.010 (2)
C500.076 (3)0.070 (3)0.091 (3)−0.002 (2)0.031 (2)−0.025 (2)
C510.112 (4)0.070 (3)0.132 (5)−0.007 (3)0.067 (4)−0.032 (3)
C520.112 (4)0.050 (3)0.159 (5)0.006 (3)0.088 (4)−0.001 (3)
C530.085 (3)0.068 (3)0.125 (4)0.017 (3)0.040 (3)0.012 (3)
C540.083 (3)0.059 (3)0.089 (3)0.006 (2)0.028 (3)−0.003 (2)
C550.053 (2)0.047 (2)0.061 (2)0.0034 (18)0.0197 (19)−0.0019 (18)
C560.061 (2)0.052 (2)0.065 (2)0.0040 (19)0.017 (2)0.0067 (19)
C570.062 (3)0.065 (3)0.093 (3)0.002 (2)0.031 (2)0.010 (2)
C580.078 (3)0.059 (3)0.118 (4)0.006 (2)0.060 (3)0.012 (3)
C590.104 (4)0.069 (3)0.075 (3)0.006 (3)0.050 (3)0.004 (2)
C600.074 (3)0.060 (3)0.065 (2)0.000 (2)0.024 (2)−0.001 (2)
N10.095 (3)0.079 (3)0.090 (3)0.008 (2)0.032 (2)0.023 (2)
N20.107 (3)0.089 (3)0.117 (3)0.029 (3)0.056 (3)0.002 (2)
N30.104 (3)0.066 (2)0.099 (3)0.012 (2)0.045 (2)0.013 (2)
N40.082 (3)0.097 (3)0.102 (3)0.032 (2)0.031 (2)0.006 (2)
N50.211 (6)0.083 (3)0.142 (4)0.051 (3)0.106 (4)0.015 (3)
N60.104 (3)0.093 (3)0.147 (4)0.027 (3)0.068 (3)0.046 (3)
P10.0482 (5)0.0511 (6)0.0556 (5)0.0023 (4)0.0166 (4)−0.0061 (5)
P20.0509 (6)0.0529 (6)0.0574 (5)−0.0007 (5)0.0182 (4)−0.0080 (5)
S10.0583 (6)0.0668 (6)0.0607 (6)0.0045 (5)0.0221 (5)0.0076 (5)
S20.0835 (7)0.0727 (7)0.0708 (6)0.0205 (6)0.0397 (6)0.0171 (5)
S30.0596 (6)0.0699 (7)0.0816 (7)0.0097 (5)0.0268 (5)0.0137 (6)
S40.0561 (6)0.0621 (6)0.0705 (6)0.0069 (5)0.0215 (5)0.0061 (5)
Geometric parameters (Å, °) top
Ni1—S2i2.1661 (10)C29—C301.392 (4)
Ni1—S22.1661 (10)C29—P11.795 (3)
Ni1—S12.1709 (10)C30—C311.370 (5)
Ni1—S1i2.1709 (10)C30—H300.9300
Ni2—S4ii2.1695 (10)C31—C321.357 (5)
Ni2—S42.1695 (10)C31—H310.9300
Ni2—S32.1709 (10)C32—C331.377 (5)
Ni2—S3ii2.1709 (10)C32—H320.9300
C1—C21.342 (4)C33—C341.378 (5)
C1—C41.416 (5)C33—H330.9300
C1—S11.742 (4)C34—H340.9300
C2—C31.434 (5)C35—C401.379 (5)
C2—S21.720 (4)C35—C361.398 (5)
C3—N11.143 (5)C35—C411.510 (5)
C4—N21.137 (5)C36—C371.375 (5)
C5—C61.341 (5)C36—H360.9300
C5—C81.430 (5)C37—C381.365 (6)
C5—S31.735 (4)C37—H370.9300
C6—C71.421 (5)C38—C391.371 (5)
C6—S41.735 (4)C38—H380.9300
C7—N31.135 (4)C39—C401.379 (5)
C8—N41.145 (5)C39—C421.437 (6)
C9—C141.372 (5)C40—H400.9300
C9—C101.397 (6)C41—P21.816 (3)
C9—C151.505 (5)C41—H41A0.9700
C10—C111.375 (7)C41—H41B0.9700
C10—H100.9300C42—N61.130 (5)
C11—C121.357 (7)C43—C481.376 (5)
C11—H110.9300C43—C441.386 (5)
C12—C131.370 (6)C43—P21.784 (4)
C12—H120.9300C44—C451.367 (5)
C13—C141.387 (5)C44—H440.9300
C13—C161.445 (6)C45—C461.365 (5)
C14—H140.9300C45—H450.9300
C15—P11.821 (3)C46—C471.371 (6)
C15—H15A0.9700C46—H460.9300
C15—H15B0.9700C47—C481.381 (5)
C16—N51.128 (6)C47—H470.9300
C17—C221.378 (5)C48—H480.9300
C17—C181.392 (5)C49—C501.366 (5)
C17—P11.781 (3)C49—C541.383 (5)
C18—C191.357 (5)C49—P21.788 (4)
C18—H180.9300C50—C511.367 (6)
C19—C201.363 (6)C50—H500.9300
C19—H190.9300C51—C521.344 (7)
C20—C211.371 (5)C51—H510.9300
C20—H200.9300C52—C531.370 (6)
C21—C221.381 (5)C52—H520.9300
C21—H210.9300C53—C541.374 (6)
C22—H220.9300C53—H530.9300
C23—C241.377 (5)C54—H540.9300
C23—C281.392 (5)C55—C601.383 (5)
C23—P11.790 (3)C55—C561.378 (5)
C24—C251.375 (5)C55—P21.792 (3)
C24—H240.9300C56—C571.377 (5)
C25—C261.361 (6)C56—H560.9300
C25—H250.9300C57—C581.355 (5)
C26—C271.370 (6)C57—H570.9300
C26—H260.9300C58—C591.369 (6)
C27—C281.365 (5)C58—H580.9300
C27—H270.9300C59—C601.381 (5)
C28—H280.9300C59—H590.9300
C29—C341.380 (4)C60—H600.9300
S2i—Ni1—S2180.0C32—C33—C34120.4 (4)
S2i—Ni1—S187.41 (4)C32—C33—H33119.8
S2—Ni1—S192.59 (4)C34—C33—H33119.8
S2i—Ni1—S1i92.59 (4)C29—C34—C33119.9 (4)
S2—Ni1—S1i87.41 (4)C29—C34—H34120.1
S1—Ni1—S1i180.000 (1)C33—C34—H34120.1
S4ii—Ni2—S4180.0C40—C35—C36117.9 (4)
S4ii—Ni2—S387.69 (4)C40—C35—C41121.5 (4)
S4—Ni2—S392.31 (4)C36—C35—C41120.6 (4)
S4ii—Ni2—S3ii92.31 (4)C37—C36—C35120.4 (4)
S4—Ni2—S3ii87.69 (4)C37—C36—H36119.8
S3—Ni2—S3ii180.00 (5)C35—C36—H36119.8
C2—C1—C4121.2 (3)C38—C37—C36121.4 (4)
C2—C1—S1120.8 (3)C38—C37—H37119.3
C4—C1—S1118.0 (3)C36—C37—H37119.3
C1—C2—C3118.9 (3)C37—C38—C39118.4 (4)
C1—C2—S2121.6 (3)C37—C38—H38120.8
C3—C2—S2119.4 (3)C39—C38—H38120.8
N1—C3—C2177.7 (4)C40—C39—C38121.4 (4)
N2—C4—C1179.4 (5)C40—C39—C42118.1 (4)
C6—C5—C8121.1 (3)C38—C39—C42120.5 (4)
C6—C5—S3121.6 (3)C39—C40—C35120.5 (4)
C8—C5—S3117.2 (3)C39—C40—H40119.7
C5—C6—C7120.9 (3)C35—C40—H40119.7
C5—C6—S4120.4 (3)C35—C41—P2111.6 (2)
C7—C6—S4118.5 (3)C35—C41—H41A109.3
N3—C7—C6178.7 (5)P2—C41—H41A109.3
N4—C8—C5179.0 (5)C35—C41—H41B109.3
C14—C9—C10118.0 (4)P2—C41—H41B109.3
C14—C9—C15121.8 (4)H41A—C41—H41B108.0
C10—C9—C15120.2 (4)N6—C42—C39177.6 (5)
C11—C10—C9120.5 (5)C48—C43—C44119.8 (3)
C11—C10—H10119.7C48—C43—P2121.5 (3)
C9—C10—H10119.7C44—C43—P2118.0 (3)
C12—C11—C10121.1 (5)C45—C44—C43119.9 (4)
C12—C11—H11119.5C45—C44—H44120.1
C10—C11—H11119.5C43—C44—H44120.0
C11—C12—C13119.1 (5)C44—C45—C46120.1 (4)
C11—C12—H12120.5C44—C45—H45120.0
C13—C12—H12120.5C46—C45—H45120.0
C14—C13—C12120.7 (4)C47—C46—C45120.8 (4)
C14—C13—C16120.2 (4)C47—C46—H46119.6
C12—C13—C16119.0 (4)C45—C46—H46119.6
C9—C14—C13120.6 (4)C46—C47—C48119.5 (4)
C9—C14—H14119.7C46—C47—H47120.2
C13—C14—H14119.7C48—C47—H47120.2
C9—C15—P1113.0 (2)C43—C48—C47119.9 (4)
C9—C15—H15A109.0C43—C48—H48120.1
P1—C15—H15A109.0C47—C48—H48120.1
C9—C15—H15B109.0C50—C49—C54119.6 (4)
P1—C15—H15B109.0C50—C49—P2120.9 (3)
H15A—C15—H15B107.8C54—C49—P2119.5 (3)
N5—C16—C13179.0 (6)C51—C50—C49119.8 (5)
C22—C17—C18119.6 (3)C51—C50—H50120.1
C22—C17—P1121.0 (3)C49—C50—H50120.1
C18—C17—P1119.1 (3)C52—C51—C50121.2 (5)
C19—C18—C17119.7 (4)C52—C51—H51119.4
C19—C18—H18120.1C50—C51—H51119.4
C17—C18—H18120.1C51—C52—C53119.7 (5)
C18—C19—C20121.0 (4)C51—C52—H52120.1
C18—C19—H19119.5C53—C52—H52120.1
C20—C19—H19119.5C54—C53—C52120.2 (5)
C19—C20—C21120.0 (4)C54—C53—H53119.9
C19—C20—H20120.0C52—C53—H53119.9
C21—C20—H20120.0C53—C54—C49119.4 (4)
C20—C21—C22120.1 (4)C53—C54—H54120.3
C20—C21—H21120.0C49—C54—H54120.3
C22—C21—H21120.0C60—C55—C56119.8 (3)
C17—C22—C21119.6 (4)C60—C55—P2120.3 (3)
C17—C22—H22120.2C56—C55—P2119.8 (3)
C21—C22—H22120.2C55—C56—C57119.7 (4)
C24—C23—C28119.4 (3)C55—C56—H56120.2
C24—C23—P1121.5 (3)C57—C56—H56120.2
C28—C23—P1119.1 (3)C58—C57—C56120.3 (4)
C25—C24—C23119.3 (4)C58—C57—H57119.8
C25—C24—H24120.3C56—C57—H57119.8
C23—C24—H24120.3C57—C58—C59120.7 (4)
C26—C25—C24121.1 (4)C57—C58—H58119.7
C26—C25—H25119.4C59—C58—H58119.7
C24—C25—H25119.4C58—C59—C60119.9 (4)
C25—C26—C27119.9 (4)C58—C59—H59120.1
C25—C26—H26120.1C60—C59—H59120.1
C27—C26—H26120.1C55—C60—C59119.5 (4)
C28—C27—C26120.1 (4)C55—C60—H60120.2
C28—C27—H27119.9C59—C60—H60120.2
C26—C27—H27119.9C17—P1—C23108.84 (16)
C27—C28—C23120.1 (4)C17—P1—C29110.34 (16)
C27—C28—H28119.9C23—P1—C29109.18 (15)
C23—C28—H28119.9C17—P1—C15108.13 (17)
C34—C29—C30119.4 (3)C23—P1—C15109.27 (16)
C34—C29—P1118.4 (3)C29—P1—C15111.05 (17)
C30—C29—P1121.9 (3)C43—P2—C49109.69 (17)
C31—C30—C29119.2 (3)C43—P2—C55111.52 (17)
C31—C30—H30120.4C49—P2—C55109.65 (16)
C29—C30—H30120.4C43—P2—C41105.81 (17)
C32—C31—C30121.7 (4)C49—P2—C41109.37 (17)
C32—C31—H31119.2C55—P2—C41110.73 (16)
C30—C31—H31119.2C1—S1—Ni1102.29 (13)
C31—C32—C33119.3 (4)C2—S2—Ni1102.74 (12)
C31—C32—H32120.3C5—S3—Ni2102.43 (13)
C33—C32—H32120.3C6—S4—Ni2102.97 (13)
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+2, −y, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10···N4iii0.932.573.479 (7)165
C33—H33···N2iv0.932.623.452 (6)149
C36—H36···N2iii0.932.473.250 (6)141
Symmetry codes: (iii) x, y, z−1; (iv) x+1/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10···N4i0.932.573.479 (7)165
C33—H33···N2ii0.932.623.452 (6)149
C36—H36···N2i0.932.473.250 (6)141
Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+1/2, z−1/2.
Acknowledgements top

The authors thank the Science and Technology Project (No. 2007 K092) from Guangdong Science and Technology Department and the President's Science Foundation of South China Agricultural University (No. 2005 K092) for financial support.

references
References top

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