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Acta Cryst. (2007). E63, m2980    [ doi:10.1107/S1600536807055821 ]

Bis[2-(4-bromobenzyl)isoquinolinium] bis(1,2-dicyanoethene-1,2-dithiolato-[kappa]2S,S')nickel(II)

A.-Q. Zhou, J.-R. Zhou and C.-L. Ni

Abstract top

The new title nickel(II) complex, (C16H13BrN)2[Ni(C4N2S2)2], is a salt obtained by the direct reaction of NiCl2, disodium maleonitriledithiolate (Na2mnt) and 1-(4-bromobenzyl)isoquinolinium bromide, (BrBzIQl)+Br-, in methanol. The structure contains two (BrBzIQl)+ cations and an Ni(mnt)22- anion in the asymmetric unit. In the two (BrBzIQl)+ cations, the dihedral angles between the benzene ring and the isoquinoline plane are 71.0 (4) and 82.1 (4)°. The [Ni(mnt)2]2- anion exhibits a slightly distorted square-planar coordination geometry. The crystal structure is stabilized by three weak C-H...N hydrogen bonds and a [pi]-[pi] stacking interaction involving the benzene ring and isoquinoline plane [centroid-centroid separation 3.774 (2) Å]

Comment top

1,2-Dithiolene metal complexes are important molecular materials with interesting physical properties such as electical conductivity, superconductivity, photoelectric and magnetic properties (Robertson & Cronin, 2002; Ni et al., 2004; Xie et al., 2002; Ren et al., 2002; Nishijo et al., 2003; Canadell, 1999). Recently, some substituted isoquinolinium cations have been introduced into the Ni(mnt)2 system to obtain Ni(mnt)22−-based molecular solids showing unusual magnetic properties (Ni et al., 2005; Ni et al., 2006; Ni et al., 2007). To gain more insight into how the substituted groups affects the stacking mode of Ni(mnt)22− anion, we herein present a new Ni(mnt)22− salt containing the 1-(4-bromobenzyl)isoquinolinium cation as shown in Fig.1. The salt consists of two (BrBzIQl)+ cations and a Ni(mnt)22− anion in the asymmetric unit. In the cations, the dihedral angles between the benzene rings and the isoquinoline groups are 71.0 (4) ° for the cation containing N5, and 82.1 (4) ° for the cation containing N6. The Ni(II) ion of the [Ni(mnt)2](2-) anion and exhibits a slightly distorted square-planar coordination geometry. The four CN groups of [Ni(mnt)2]2− are slightly tipped out of the S1/S2/Ni1/S3/S4 plane and the deviations from the plane are −0.294 (3) Å for N1, −0.324 (3) Å for N2, −0.237 (3) Å for N3 and 0.195 (3)Å for N4, respectively.

The crystal structure is stabilized by C17—H17···N1, C31—H31A···N2 and C36—H36···N2 hydrogen bonds, Table 1, and a π···π stacking interaction between the N5/C16···C24 group and the C25i···C30i ring [Symmetry Code:(i)1 − x,1 − y,1 − z] with a distance of 3.774 (2) Å between the centroids of the two systems, Fig 2.

Related literature top

For details of other square planar 1,2-dithiolene metal complexes, see: Robertson & Cronin (2002); Ni et al. (2004) Please check – reference not in list; Xie et al. (2002); Ren et al. (2002); Nishijo et al. (2003); Canadell (1999). For the structures of related Ni(mnt)2− complexes with square-planar geometry and a substituted isoquinolinium counter-ion, see: Ni, Dang et al. (2005) Ni, Yang & Meng (2005), Ni et al. 2006, 2007).

Experimental top

The title compound was prepared by the direct reaction of NiCl2·6H2O, Na2mnt and (BrBzIQl)+Br− in in methanol. The brown block-like single crystals were obtained by slow evaporation of a mixed solution of CH3CN and i-PrOH (1:1) at room temperature for about 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.
[Figure 2] Fig. 2. The π···π interaction in the structure of (I) [Symmetry Code:(A)1 − x,1 − y,1 − z].
Bis[2-(4-bromobenzyl)isoquinolinium] bis(1,2-dicyanoethene-1,2-dithiolato-κ2S,S')nickel(II) top
Crystal data top
(C16H13BrN)2[Ni(C4N2S2)2]Z = 2
Mr = 937.44F000 = 940
Triclinic, P1Dx = 1.562 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 11.320 (4) ÅCell parameters from 698 reflections
b = 13.354 (5) Åθ = 2.8–20.4º
c = 14.754 (5) ŵ = 2.74 mm−1
α = 110.776 (7)ºT = 291 (2) K
β = 101.261 (6)ºBlock, brown
γ = 97.880 (7)º0.30 × 0.30 × 0.10 mm
V = 1992.8 (12) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		6871 independent reflections
Radiation source: fine-focus sealed tube3408 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.085
T = 291(2) Kθmax = 25.0º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −13→13
Tmin = 0.461, Tmax = 0.762k = −15→9
9888 measured reflectionsl = −14→17
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6871 reflectionsΔρmax = 0.96 e Å−3
466 parametersΔρmin = −0.68 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C16H13BrN)2[Ni(C4N2S2)2]γ = 97.880 (7)º
Mr = 937.44V = 1992.8 (12) Å3
Triclinic, P1Z = 2
a = 11.320 (4) ÅMo Kα
b = 13.354 (5) ŵ = 2.74 mm−1
c = 14.754 (5) ÅT = 291 (2) K
α = 110.776 (7)º0.30 × 0.30 × 0.10 mm
β = 101.261 (6)º
Data collection top
Bruker SMART APEX CCD
diffractometer		6871 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		3408 reflections with I > 2σ(I)
Tmin = 0.461, Tmax = 0.762Rint = 0.085
9888 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066466 parameters
wR(F2) = 0.147H-atom parameters constrained
S = 1.04Δρmax = 0.96 e Å−3
6871 reflectionsΔρmin = −0.68 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.32855 (7)0.37256 (6)0.16612 (5)0.0583 (2)
Br11.19531 (9)0.73115 (8)0.60159 (10)0.1871 (6)
Br20.17434 (9)0.03355 (11)0.37778 (7)0.1603 (5)
C10.4413 (5)0.2335 (4)0.2708 (4)0.0585 (16)
C20.4826 (5)0.2076 (4)0.1883 (4)0.0562 (15)
C30.5536 (6)0.1275 (5)0.1648 (4)0.0650 (17)
C40.4693 (6)0.1786 (6)0.3371 (5)0.0705 (18)
C50.1738 (5)0.5346 (5)0.1360 (5)0.0657 (17)
C60.2167 (5)0.5077 (4)0.0552 (5)0.0617 (17)
C70.1943 (7)0.5541 (5)−0.0193 (5)0.0727 (19)
C80.0952 (6)0.6130 (5)0.1550 (5)0.0761 (19)
C91.0375 (8)0.6558 (6)0.5121 (8)0.107
C100.9467 (8)0.6324 (6)0.5551 (5)0.099 (3)
H100.96250.65130.62410.119*
C110.8294 (7)0.5790 (6)0.4910 (6)0.096 (2)
H110.76540.56170.51770.115*
C120.8059 (7)0.5513 (5)0.3897 (6)0.0724 (19)
C130.9011 (8)0.5752 (6)0.3523 (5)0.089 (2)
H130.88800.55550.28340.106*
C141.0172 (7)0.6285 (6)0.4156 (7)0.102 (2)
H141.08180.64510.38900.122*
C150.6783 (6)0.4941 (5)0.3214 (5)0.097 (2)
H15A0.68500.44670.25630.117*
H15B0.63650.44830.34930.117*
C160.5567 (9)0.6257 (8)0.3865 (7)0.119 (3)
H160.57160.60730.44220.143*
C170.4902 (8)0.7017 (8)0.3868 (6)0.124 (3)
H170.46040.73620.44160.148*
C180.4681 (7)0.7266 (6)0.3041 (7)0.092 (2)
C190.3982 (8)0.8111 (7)0.3006 (7)0.118 (3)
H190.36820.84940.35400.141*
C200.3801 (8)0.8300 (6)0.2136 (8)0.107 (3)
H200.33580.88200.20750.129*
C210.4259 (7)0.7737 (7)0.1355 (6)0.094 (2)
H210.41250.79010.07870.113*
C220.4893 (6)0.6959 (6)0.1375 (6)0.084 (2)
H220.51740.65780.08280.101*
C230.5108 (6)0.6752 (5)0.2229 (6)0.0746 (19)
C240.5810 (6)0.5931 (5)0.2271 (6)0.079 (2)
H240.60960.55480.17270.095*
C250.1943 (7)0.0626 (7)0.5152 (5)0.095
C260.1321 (7)0.1321 (6)0.5688 (6)0.100 (2)
H260.08130.16610.53760.120*
C270.1436 (6)0.1519 (5)0.6671 (6)0.084 (2)
H270.09710.19610.70190.100*
C280.2237 (5)0.1071 (4)0.7157 (5)0.0587 (15)
C290.2878 (6)0.0399 (5)0.6612 (5)0.0728 (18)
H290.34080.00770.69260.087*
C300.2760 (6)0.0186 (5)0.5605 (5)0.087 (2)
H300.3227−0.02470.52500.104*
C310.2412 (6)0.1313 (5)0.8254 (4)0.0690 (17)
H31A0.30780.10000.84780.083*
H31B0.26490.21030.86310.083*
C320.0844 (6)−0.0256 (5)0.8057 (4)0.0639 (17)
H320.1244−0.07150.76490.077*
C33−0.0166 (6)−0.0677 (5)0.8254 (4)0.0648 (17)
H33−0.0463−0.14350.79650.078*
C34−0.0797 (5)−0.0037 (5)0.8871 (4)0.0528 (15)
C35−0.1846 (6)−0.0443 (5)0.9091 (4)0.0673 (18)
H35−0.2181−0.11960.88170.081*
C36−0.2396 (6)0.0265 (6)0.9718 (5)0.0749 (19)
H36−0.3104−0.00110.98620.090*
C37−0.1891 (6)0.1402 (6)1.0139 (5)0.0757 (19)
H37−0.22580.18731.05700.091*
C38−0.0882 (6)0.1812 (5)0.9925 (4)0.0687 (17)
H38−0.05640.25681.02010.082*
C39−0.0302 (6)0.1117 (5)0.9290 (4)0.0549 (15)
C400.0727 (6)0.1510 (5)0.9056 (4)0.0563 (15)
H400.10460.22650.93270.068*
N10.4949 (6)0.1342 (5)0.3877 (4)0.095 (2)
N20.6105 (6)0.0614 (5)0.1465 (4)0.097 (2)
N30.1829 (6)0.5868 (5)−0.0815 (5)0.093 (2)
N40.0365 (6)0.6768 (5)0.1724 (5)0.098 (2)
N50.6030 (5)0.5746 (5)0.3085 (6)0.0826 (17)
N60.1288 (4)0.0869 (4)0.8465 (3)0.0573 (12)
S10.35194 (16)0.32994 (13)0.29755 (11)0.0708 (5)
S20.44630 (15)0.26760 (12)0.10251 (11)0.0654 (5)
S30.31046 (15)0.41468 (12)0.03658 (11)0.0676 (5)
S40.20597 (17)0.47605 (14)0.22340 (13)0.0810 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0551 (5)0.0450 (5)0.0682 (5)0.0130 (3)0.0170 (4)0.0135 (3)
Br10.1028 (7)0.0784 (7)0.2734 (14)0.0060 (5)−0.0676 (8)0.0123 (7)
Br20.1135 (8)0.2950 (15)0.0978 (7)0.0386 (9)0.0250 (6)0.1107 (8)
C10.052 (4)0.055 (4)0.059 (4)0.012 (3)0.010 (3)0.014 (3)
C20.048 (4)0.051 (4)0.061 (4)0.009 (3)0.010 (3)0.014 (3)
C30.066 (4)0.078 (5)0.066 (4)0.031 (4)0.029 (3)0.034 (3)
C40.067 (5)0.078 (5)0.064 (5)0.022 (4)0.014 (4)0.025 (4)
C50.055 (4)0.055 (4)0.082 (5)0.015 (3)0.016 (3)0.021 (3)
C60.064 (4)0.036 (3)0.069 (4)0.007 (3)0.008 (3)0.009 (3)
C70.087 (5)0.049 (4)0.072 (5)0.020 (4)0.013 (4)0.014 (4)
C80.079 (5)0.064 (5)0.097 (5)0.028 (4)0.035 (4)0.035 (4)
C90.0760.0850.1210.014−0.0110.015
C100.111 (7)0.079 (5)0.078 (5)0.035 (5)0.001 (5)0.004 (4)
C110.089 (6)0.107 (6)0.089 (6)0.022 (5)0.023 (5)0.035 (5)
C120.074 (5)0.046 (4)0.083 (5)0.009 (3)0.009 (4)0.016 (3)
C130.087 (6)0.092 (6)0.085 (5)0.026 (5)0.022 (5)0.031 (4)
C140.074 (6)0.093 (6)0.143 (7)0.019 (5)0.031 (5)0.051 (5)
C150.088 (5)0.054 (4)0.119 (6)0.001 (4)−0.005 (5)0.020 (4)
C160.126 (8)0.132 (8)0.105 (7)0.049 (7)0.036 (6)0.043 (6)
C170.126 (8)0.160 (9)0.080 (6)0.068 (7)0.032 (6)0.027 (6)
C180.083 (5)0.087 (6)0.080 (6)0.017 (4)0.013 (5)0.009 (5)
C190.119 (7)0.105 (7)0.099 (7)0.045 (6)0.019 (6)0.003 (5)
C200.094 (6)0.084 (6)0.118 (7)0.029 (5)0.008 (6)0.016 (6)
C210.079 (5)0.081 (6)0.110 (6)0.010 (5)0.014 (5)0.032 (5)
C220.065 (5)0.084 (6)0.093 (6)0.008 (4)0.020 (4)0.026 (4)
C230.064 (4)0.054 (4)0.079 (5)−0.003 (4)0.009 (4)0.007 (4)
C240.062 (5)0.056 (5)0.092 (6)−0.003 (4)0.006 (4)0.011 (4)
C250.0880.1180.0870.0220.0190.054
C260.099 (6)0.128 (7)0.121 (7)0.052 (5)0.033 (5)0.090 (6)
C270.082 (5)0.082 (5)0.106 (6)0.041 (4)0.028 (5)0.051 (4)
C280.053 (4)0.050 (4)0.076 (4)0.012 (3)0.016 (3)0.028 (3)
C290.079 (5)0.070 (5)0.072 (5)0.033 (4)0.017 (4)0.026 (3)
C300.083 (5)0.108 (6)0.073 (5)0.036 (4)0.022 (4)0.034 (4)
C310.061 (4)0.062 (4)0.075 (5)0.008 (3)0.017 (3)0.019 (3)
C320.066 (4)0.048 (4)0.072 (4)0.015 (3)0.013 (3)0.018 (3)
C330.073 (5)0.044 (4)0.063 (4)0.001 (3)0.005 (4)0.015 (3)
C340.057 (4)0.053 (4)0.044 (3)0.006 (3)−0.003 (3)0.024 (3)
C350.062 (4)0.069 (5)0.059 (4)−0.005 (4)−0.002 (3)0.027 (3)
C360.068 (5)0.094 (6)0.065 (4)0.006 (4)0.013 (4)0.040 (4)
C370.080 (5)0.084 (6)0.077 (5)0.026 (4)0.031 (4)0.039 (4)
C380.082 (5)0.059 (4)0.080 (5)0.025 (4)0.032 (4)0.035 (3)
C390.063 (4)0.049 (4)0.059 (4)0.016 (3)0.015 (3)0.029 (3)
C400.063 (4)0.045 (4)0.062 (4)0.014 (3)0.013 (3)0.024 (3)
N10.115 (5)0.106 (5)0.081 (4)0.054 (4)0.029 (4)0.044 (4)
N20.113 (5)0.116 (5)0.099 (4)0.073 (4)0.051 (4)0.054 (4)
N30.124 (5)0.072 (4)0.083 (5)0.035 (4)0.015 (4)0.030 (3)
N40.099 (5)0.084 (4)0.136 (5)0.050 (4)0.049 (4)0.052 (4)
N50.064 (4)0.065 (4)0.097 (5)0.004 (3)0.009 (4)0.017 (4)
N60.057 (3)0.048 (3)0.065 (3)0.012 (3)0.011 (3)0.022 (3)
S10.0789 (12)0.0677 (11)0.0693 (11)0.0304 (9)0.0312 (9)0.0198 (8)
S20.0724 (11)0.0620 (10)0.0691 (10)0.0270 (9)0.0271 (9)0.0255 (8)
S30.0786 (11)0.0489 (10)0.0704 (10)0.0211 (8)0.0216 (9)0.0143 (8)
S40.0877 (13)0.0815 (13)0.0977 (13)0.0462 (11)0.0460 (11)0.0414 (10)
Geometric parameters (Å, °) top
Ni1—S32.1571 (19)C19—H190.9300
Ni1—S22.1657 (17)C20—C211.373 (10)
Ni1—S42.1691 (18)C20—H200.9300
Ni1—S12.186 (2)C21—C221.346 (9)
Br1—C91.895 (8)C21—H210.9300
Br2—C251.884 (7)C22—C231.367 (9)
C1—C21.338 (7)C22—H220.9300
C1—C41.430 (9)C23—C241.450 (9)
C1—S11.729 (6)C24—N51.296 (8)
C2—C31.411 (8)C24—H240.9300
C2—S21.737 (6)C25—C301.355 (9)
C3—N21.149 (7)C25—C261.363 (10)
C4—N11.127 (7)C26—C271.354 (8)
C5—C61.325 (8)C26—H260.9300
C5—C81.453 (9)C27—C281.377 (8)
C5—S41.737 (7)C27—H270.9300
C6—C71.440 (9)C28—C291.368 (7)
C6—S31.726 (6)C28—C311.500 (7)
C7—N31.142 (7)C29—C301.385 (8)
C8—N41.140 (7)C29—H290.9300
C9—C141.302 (10)C30—H300.9300
C9—C101.366 (11)C31—N61.465 (7)
C10—C111.393 (9)C31—H31A0.9700
C10—H100.9300C31—H31B0.9700
C11—C121.365 (9)C32—C331.332 (8)
C11—H110.9300C32—N61.380 (6)
C12—C131.354 (9)C32—H320.9300
C12—C151.506 (9)C33—C341.393 (8)
C13—C141.379 (9)C33—H330.9300
C13—H130.9300C34—C351.382 (8)
C14—H140.9300C34—C391.422 (7)
C15—N51.500 (8)C35—C361.380 (8)
C15—H15A0.9700C35—H350.9300
C15—H15B0.9700C36—C371.404 (8)
C16—C171.343 (11)C36—H360.9300
C16—N51.357 (9)C37—C381.340 (8)
C16—H160.9300C37—H370.9300
C17—C181.362 (10)C38—C391.401 (8)
C17—H170.9300C38—H380.9300
C18—C231.369 (9)C39—C401.368 (7)
C18—C191.474 (10)C40—N61.315 (6)
C19—C201.377 (10)C40—H400.9300
S3—Ni1—S286.47 (7)C22—C23—C18123.5 (8)
S3—Ni1—S491.51 (7)C22—C23—C24118.3 (8)
S2—Ni1—S4177.56 (8)C18—C23—C24118.2 (8)
S3—Ni1—S1178.51 (7)N5—C24—C23118.3 (7)
S2—Ni1—S192.37 (7)N5—C24—H24120.8
S4—Ni1—S189.67 (7)C23—C24—H24120.8
C2—C1—C4119.3 (6)C30—C25—C26120.9 (7)
C2—C1—S1121.3 (5)C30—C25—Br2119.1 (6)
C4—C1—S1119.4 (5)C26—C25—Br2119.9 (6)
C1—C2—C3121.7 (5)C27—C26—C25120.6 (7)
C1—C2—S2121.4 (5)C27—C26—H26119.7
C3—C2—S2116.9 (4)C25—C26—H26119.7
N2—C3—C2178.9 (7)C26—C27—C28120.4 (6)
N1—C4—C1177.4 (8)C26—C27—H27119.8
C6—C5—C8121.7 (6)C28—C27—H27119.8
C6—C5—S4121.8 (5)C29—C28—C27118.1 (6)
C8—C5—S4116.5 (5)C29—C28—C31120.7 (6)
C5—C6—C7124.4 (6)C27—C28—C31121.2 (6)
C5—C6—S3119.8 (5)C28—C29—C30121.9 (6)
C7—C6—S3115.7 (5)C28—C29—H29119.0
N3—C7—C6174.8 (8)C30—C29—H29119.0
N4—C8—C5177.9 (8)C25—C30—C29117.9 (6)
C14—C9—C10122.2 (7)C25—C30—H30121.0
C14—C9—Br1121.9 (8)C29—C30—H30121.0
C10—C9—Br1115.9 (8)N6—C31—C28112.1 (5)
C9—C10—C11116.9 (7)N6—C31—H31A109.2
C9—C10—H10121.6C28—C31—H31A109.2
C11—C10—H10121.6N6—C31—H31B109.2
C12—C11—C10121.7 (7)C28—C31—H31B109.2
C12—C11—H11119.1H31A—C31—H31B107.9
C10—C11—H11119.1C33—C32—N6119.3 (6)
C13—C12—C11118.0 (7)C33—C32—H32120.4
C13—C12—C15120.9 (7)N6—C32—H32120.4
C11—C12—C15121.1 (8)C32—C33—C34123.2 (6)
C12—C13—C14120.4 (7)C32—C33—H33118.4
C12—C13—H13119.8C34—C33—H33118.4
C14—C13—H13119.8C35—C34—C33124.9 (6)
C9—C14—C13120.7 (8)C35—C34—C39119.2 (6)
C9—C14—H14119.7C33—C34—C39116.0 (6)
C13—C14—H14119.7C36—C35—C34120.1 (6)
N5—C15—C12111.7 (5)C36—C35—H35119.9
N5—C15—H15A109.3C34—C35—H35119.9
C12—C15—H15A109.3C35—C36—C37120.2 (6)
N5—C15—H15B109.3C35—C36—H36119.9
C12—C15—H15B109.3C37—C36—H36119.9
H15A—C15—H15B107.9C38—C37—C36120.5 (6)
C17—C16—N5122.9 (9)C38—C37—H37119.8
C17—C16—H16118.5C36—C37—H37119.8
N5—C16—H16118.5C37—C38—C39120.8 (6)
C16—C17—C18117.6 (8)C37—C38—H38119.6
C16—C17—H17121.2C39—C38—H38119.6
C18—C17—H17121.2C40—C39—C38122.2 (6)
C17—C18—C23121.3 (8)C40—C39—C34118.6 (5)
C17—C18—C19120.4 (9)C38—C39—C34119.2 (6)
C23—C18—C19118.3 (8)N6—C40—C39123.0 (6)
C20—C19—C18116.0 (8)N6—C40—H40118.5
C20—C19—H19122.0C39—C40—H40118.5
C18—C19—H19122.0C24—N5—C16121.5 (7)
C21—C20—C19121.5 (9)C24—N5—C15122.3 (7)
C21—C20—H20119.2C16—N5—C15116.2 (8)
C19—C20—H20119.2C40—N6—C32119.9 (5)
C22—C21—C20123.1 (8)C40—N6—C31121.7 (5)
C22—C21—H21118.5C32—N6—C31118.4 (5)
C20—C21—H21118.5C1—S1—Ni1102.3 (2)
C21—C22—C23117.5 (7)C2—S2—Ni1102.5 (2)
C21—C22—H22121.2C6—S3—Ni1104.1 (2)
C23—C22—H22121.2C5—S4—Ni1102.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N1i0.932.403.226 (10)148
C31—H31A···N2ii0.972.483.359 (10)151
C36—H36···N2iii0.932.593.288 (9)132
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N1i0.932.403.226 (10)148
C31—H31A···N2ii0.972.483.359 (10)151
C36—H36···N2iii0.932.593.288 (9)132
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z+1.
Acknowledgements top

The authors thank the Science and Technology Project (No. 2007B011000008) of Guangdong Science and Technology Department and the President's Science Foundation of South China Agricultural University (No.2005 K092) for financial support.

references
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