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Acta Cryst. (2009). E65, m242    [ doi:10.1107/S160053680900302X ]

cis-Bis[N-(2-furoyl)-N',N'-diphenylthioureato-[kappa]2O,S]nickel(II)

H. Pérez, R. S. Corrêa, A. M. Plutín, O. Calderón and J. Duque

Abstract top

In the title compound, [Ni(C18H13N2O2S)2], the NiII atom is coordinated by the S and O atoms of two N-furoyl-N',N'-diphenylthioureate ligands in a slightly distorted square-planar coordination geometry. The two O and two S atoms are cis to each other.

Comment top

N-Acyl-N',N'-disubstituted thioureas are well known as chelating agents. Over recent years, many transition metal complexes with N-benzoyl- and N-furoyl-N',N'-disubstituted thioureas have been reported (Jia et al., 2007). During the complex formation, the ligand is deprotonated, which results in a neutral complex with a six-membered ring chelating metal ion. In this paper, we report the crystal structure of the title compound.

In the structure of complex, the two furoylthiourea ligands have cis arrangement when bonded to the central NiII ion as shown in Fig. 1. The complex coordination geometry is a slightly distorted square-planar as reflected by the angles O3—Ni1—S1 [176.26 (8)°] and O1—Ni1—S2 [176.87 (8)°].

Selected geometric parameters are listed in Table 1. The Ni—S and Ni—O bond lengths lie within the range of those found in the related structures (Pérez et al., 2008). The lengths of C—O, C—S and C—N bonds in the chelate ring are between characteristic single and double bond lengths (Arslan et al., 2006), which are shorter than single and longer than double bonds. Fig. 2 shows the arrangement of the complex molecules in the unit cell.

Related literature top

For general background, see: Arslan et al. (2006). For related structures, see: Jia et al. (2007); Pérez et al. (2008). For the synthesis of the ligand, see: Hernández et al. (2003).

Experimental top

N-Furoyl-N',N'-diphenylthiourea ligand was synthesized according to a procedure described by Hernández et al. (2003), by converting furoyl chloride into furoyl isothiocyanate and then condensing with an appropriate amine. To an ethanol solution (30 ml) containing the ligand (0.64 g, 2 mmol) was added an ethanol solution of Ni(CH3COO)2.4H2O (0.25 g, 1 mmol). The solution was stirred at room temperature for 2 h, and at once a solution of NaOH (1 N) was added to adjust pH to the neutral value. The mixture was filtered and the filtrate was evaporated under reduced pressure to give a red solid, which was washed with acetone. Single crystals were obtained by slow evaporation of a chloroform/N,N-diphenylformamide solution (1:1, v/v) of the complex.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Enraf–Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the unit cell of the title complex.
cis-Bis[N-(2-furoyl)-N',N'-diphenylthioureato- κ2O,S]nickel(II) top
Crystal data top
[Ni(C18H13N2O2S)2]Z = 2
Mr = 701.46F(000) = 724
Triclinic, P1Dx = 1.434 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0458 (2) ÅCell parameters from 83255 reflections
b = 11.0030 (3) Åθ = 2.9–27.1°
c = 15.9718 (3) ŵ = 0.77 mm−1
α = 72.755 (2)°T = 294 K
β = 88.792 (2)°Prism, red
γ = 74.874 (1)°0.14 × 0.09 × 0.06 mm
V = 1624.61 (7) Å3
Data collection top
Nonius KappaCCD
diffractometer		5083 reflections with I > 2σ(I)
φ and ω scansRint = 0.053
Absorption correction: gaussian
(Coppens et al., 1965)		θmax = 27.1°, θmin = 3.1°
Tmin = 0.955, Tmax = 0.980h = −12→12
12907 measured reflectionsk = −13→14
7027 independent reflectionsl = −17→20
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.064 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2693P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145(Δ/σ)max < 0.001
S = 1.22Δρmax = 0.33 e Å−3
7027 reflectionsΔρmin = −0.45 e Å−3
424 parameters
Crystal data top
[Ni(C18H13N2O2S)2]γ = 74.874 (1)°
Mr = 701.46V = 1624.61 (7) Å3
Triclinic, P1Z = 2
a = 10.0458 (2) ÅMo Kα radiation
b = 11.0030 (3) ŵ = 0.77 mm−1
c = 15.9718 (3) ÅT = 294 K
α = 72.755 (2)°0.14 × 0.09 × 0.06 mm
β = 88.792 (2)°
Data collection top
Nonius KappaCCD
diffractometer		7027 independent reflections
Absorption correction: gaussian
(Coppens et al., 1965)		5083 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.980Rint = 0.053
12907 measured reflectionsθmax = 27.1°
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.145Δρmax = 0.33 e Å−3
S = 1.22Δρmin = −0.45 e Å−3
7027 reflectionsAbsolute structure: ?
424 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.10992 (4)0.16148 (4)0.22008 (2)0.04396 (16)
S20.17245 (9)0.12133 (9)0.09958 (6)0.0542 (3)
S10.27714 (9)−0.00834 (9)0.27898 (6)0.0562 (3)
C250.1818 (3)0.1120 (3)−0.0847 (2)0.0468 (8)
C30.0498 (3)0.2104 (3)0.4681 (2)0.0461 (8)
O2−0.0374 (2)0.3346 (2)0.43990 (16)0.0594 (6)
C5−0.0320 (4)0.2626 (5)0.5856 (3)0.0802 (13)
H5−0.05040.25820.64360.096*
O10.0615 (2)0.2029 (2)0.32411 (14)0.0539 (6)
C160.4337 (4)−0.2623 (4)0.7121 (2)0.0608 (10)
H160.4447−0.29310.77310.073*
C90.5753 (5)−0.4263 (4)0.3721 (3)0.0758 (12)
H90.568−0.51090.37780.091*
O3−0.0437 (2)0.3025 (2)0.16983 (14)0.0551 (6)
N40.0672 (3)0.2042 (3)−0.06320 (16)0.0485 (7)
O4−0.2840 (2)0.4849 (2)0.14960 (16)0.0649 (7)
C150.5424 (4)−0.2347 (4)0.6641 (2)0.0592 (9)
H150.6265−0.24590.69260.071*
N20.3911 (3)−0.1353 (3)0.43740 (16)0.0433 (6)
N10.2152 (3)0.0424 (3)0.43601 (16)0.0427 (6)
C31−0.0362 (3)0.2842 (3)−0.1339 (2)0.0459 (8)
C170.3089 (4)−0.2447 (4)0.6709 (2)0.0593 (10)
H170.2351−0.26280.70390.071*
C22−0.3081 (4)0.5271 (4)0.0059 (3)0.0696 (11)
H22−0.29110.5258−0.05130.084*
C21−0.2258 (3)0.4548 (3)0.0779 (2)0.0467 (8)
C130.4024 (3)−0.1739 (3)0.5320 (2)0.0420 (7)
C70.4894 (3)−0.2189 (3)0.3976 (2)0.0456 (8)
C120.5971 (4)−0.1767 (4)0.3554 (2)0.0641 (10)
H120.6045−0.09210.34950.077*
C180.2929 (3)−0.2002 (3)0.5805 (2)0.0491 (8)
H180.2082−0.1880.55240.059*
N3−0.0573 (3)0.3195 (3)0.02013 (16)0.0476 (7)
C10.1123 (3)0.1489 (3)0.4017 (2)0.0424 (7)
C260.3131 (4)0.1250 (4)−0.0810 (2)0.0650 (10)
H260.32930.1915−0.06110.078*
C36−0.1497 (4)0.2426 (4)−0.1455 (2)0.0574 (9)
H36−0.16170.1644−0.10750.069*
C140.5278 (3)−0.1902 (3)0.5730 (2)0.0521 (9)
H140.6016−0.17160.54020.063*
C200.0522 (3)0.2238 (3)0.0169 (2)0.0439 (8)
C40.0562 (4)0.1639 (4)0.5560 (2)0.0667 (11)
H40.10890.0820.59070.08*
C19−0.0975 (3)0.3501 (3)0.0924 (2)0.0463 (8)
C32−0.0178 (4)0.3994 (4)−0.1894 (2)0.0598 (10)
H320.05950.4273−0.18160.072*
C270.4219 (4)0.0402 (5)−0.1067 (3)0.0723 (12)
H270.51060.0504−0.10440.087*
C35−0.2467 (4)0.3177 (4)−0.2142 (3)0.0692 (11)
H35−0.32350.2895−0.22290.083*
C23−0.4244 (4)0.6049 (4)0.0329 (3)0.0777 (13)
H23−0.49940.6652−0.00280.093*
C80.4766 (4)−0.3430 (4)0.4059 (2)0.0582 (9)
H80.4028−0.37070.43380.07*
C110.6944 (4)−0.2612 (5)0.3217 (3)0.0796 (13)
H110.7676−0.23350.29290.095*
C300.1591 (4)0.0128 (4)−0.1135 (3)0.0716 (12)
H300.07050.0024−0.1160.086*
C100.6831 (5)−0.3862 (5)0.3306 (3)0.0824 (15)
H100.749−0.44330.30830.099*
C20.2900 (3)−0.0298 (3)0.3898 (2)0.0406 (7)
C33−0.1163 (5)0.4739 (4)−0.2575 (2)0.0729 (12)
H33−0.10510.5524−0.29570.087*
C6−0.0839 (4)0.3632 (4)0.5149 (3)0.0714 (12)
H6−0.14410.44280.5160.086*
C280.4000 (5)−0.0574 (4)−0.1351 (3)0.0759 (12)
H280.4735−0.1146−0.1520.091*
C24−0.4066 (4)0.5758 (4)0.1190 (3)0.0731 (12)
H24−0.46960.61270.15410.088*
C34−0.2292 (5)0.4322 (4)−0.2686 (3)0.0727 (12)
H34−0.29510.4831−0.31410.087*
C290.2695 (5)−0.0716 (4)−0.1389 (3)0.0892 (15)
H290.2545−0.1387−0.15870.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0427 (3)0.0473 (3)0.0365 (3)−0.00044 (19)0.00223 (18)−0.01466 (19)
S20.0514 (5)0.0615 (6)0.0397 (5)0.0050 (4)0.0030 (4)−0.0179 (4)
S10.0577 (6)0.0587 (6)0.0390 (5)0.0128 (4)−0.0016 (4)−0.0198 (4)
C250.0448 (19)0.054 (2)0.0376 (17)−0.0041 (16)0.0069 (14)−0.0156 (15)
C30.0386 (18)0.050 (2)0.050 (2)0.0001 (16)0.0030 (15)−0.0261 (16)
O20.0571 (15)0.0555 (15)0.0630 (16)0.0006 (12)0.0088 (12)−0.0282 (12)
C50.074 (3)0.107 (4)0.062 (3)0.003 (3)0.009 (2)−0.053 (3)
O10.0560 (14)0.0540 (14)0.0398 (13)0.0092 (11)−0.0010 (11)−0.0170 (11)
C160.085 (3)0.051 (2)0.0396 (19)−0.005 (2)−0.001 (2)−0.0148 (16)
C90.092 (3)0.055 (3)0.072 (3)0.012 (2)−0.007 (2)−0.033 (2)
O30.0536 (14)0.0612 (15)0.0385 (13)0.0073 (12)−0.0005 (11)−0.0164 (11)
N40.0485 (16)0.0541 (17)0.0400 (15)−0.0026 (14)0.0014 (12)−0.0197 (13)
O40.0590 (16)0.0630 (17)0.0567 (15)0.0087 (13)0.0086 (12)−0.0164 (13)
C150.063 (2)0.059 (2)0.054 (2)−0.0102 (19)−0.0128 (19)−0.0181 (18)
N20.0391 (14)0.0483 (16)0.0365 (14)0.0020 (12)0.0014 (11)−0.0161 (12)
N10.0402 (15)0.0449 (16)0.0402 (15)−0.0032 (13)0.0032 (12)−0.0157 (12)
C310.0480 (19)0.048 (2)0.0372 (17)−0.0029 (16)0.0041 (15)−0.0148 (15)
C170.063 (2)0.058 (2)0.048 (2)−0.0072 (19)0.0146 (18)−0.0113 (17)
C220.068 (3)0.064 (3)0.065 (3)0.009 (2)−0.016 (2)−0.025 (2)
C210.0481 (19)0.0432 (19)0.0446 (19)−0.0021 (16)0.0011 (15)−0.0156 (15)
C130.0431 (18)0.0412 (18)0.0402 (17)−0.0040 (15)0.0019 (14)−0.0164 (14)
C70.0408 (18)0.050 (2)0.0373 (17)0.0059 (15)0.0032 (14)−0.0159 (15)
C120.052 (2)0.076 (3)0.060 (2)−0.005 (2)0.0154 (18)−0.026 (2)
C180.0429 (19)0.056 (2)0.0444 (19)−0.0071 (16)0.0036 (15)−0.0140 (16)
N30.0529 (17)0.0500 (17)0.0378 (15)−0.0060 (14)0.0036 (13)−0.0170 (13)
C10.0399 (18)0.0474 (19)0.0410 (18)−0.0105 (16)0.0067 (14)−0.0161 (15)
C260.059 (2)0.086 (3)0.060 (2)−0.020 (2)0.0100 (19)−0.036 (2)
C360.057 (2)0.056 (2)0.056 (2)−0.0100 (19)−0.0011 (18)−0.0170 (18)
C140.049 (2)0.056 (2)0.050 (2)−0.0113 (17)−0.0010 (16)−0.0159 (17)
C200.0463 (19)0.048 (2)0.0381 (17)−0.0114 (16)0.0077 (14)−0.0151 (15)
C40.062 (2)0.085 (3)0.046 (2)0.007 (2)−0.0003 (18)−0.030 (2)
C190.0476 (19)0.0430 (19)0.0439 (19)−0.0068 (16)0.0017 (15)−0.0110 (15)
C320.066 (2)0.056 (2)0.057 (2)−0.015 (2)0.0057 (19)−0.0177 (19)
C270.049 (2)0.104 (4)0.067 (3)−0.013 (2)0.0125 (19)−0.037 (3)
C350.055 (2)0.075 (3)0.078 (3)−0.003 (2)−0.010 (2)−0.034 (2)
C230.061 (3)0.059 (3)0.097 (4)0.016 (2)−0.026 (2)−0.025 (2)
C80.065 (2)0.054 (2)0.053 (2)−0.0037 (19)0.0029 (18)−0.0217 (18)
C110.054 (2)0.107 (4)0.068 (3)0.000 (3)0.017 (2)−0.031 (3)
C300.063 (3)0.069 (3)0.100 (3)−0.022 (2)0.023 (2)−0.047 (2)
C100.064 (3)0.108 (4)0.054 (3)0.024 (3)0.004 (2)−0.035 (3)
C20.0364 (17)0.0440 (19)0.0410 (17)−0.0074 (15)0.0015 (14)−0.0149 (15)
C330.095 (3)0.053 (2)0.052 (2)−0.003 (2)0.004 (2)−0.0043 (19)
C60.061 (2)0.077 (3)0.083 (3)0.000 (2)0.012 (2)−0.052 (3)
C280.070 (3)0.073 (3)0.076 (3)0.000 (2)0.022 (2)−0.027 (2)
C240.057 (3)0.059 (3)0.090 (3)0.010 (2)0.007 (2)−0.025 (2)
C340.074 (3)0.070 (3)0.060 (3)0.012 (2)−0.016 (2)−0.026 (2)
C290.084 (3)0.068 (3)0.135 (4)−0.021 (3)0.037 (3)−0.061 (3)
Geometric parameters (Å, °) top
Ni1—O31.870 (2)C22—C231.400 (5)
Ni1—O11.872 (2)C22—H220.93
Ni1—S12.1412 (9)C21—C191.456 (4)
Ni1—S22.1452 (9)C13—C181.376 (4)
S2—C201.717 (3)C13—C141.376 (4)
S1—C21.718 (3)C7—C81.372 (5)
C25—C261.368 (5)C7—C121.374 (5)
C25—C301.373 (5)C12—C111.383 (5)
C25—N41.433 (4)C12—H120.93
C3—C41.341 (5)C18—H180.93
C3—O21.366 (4)N3—C201.322 (4)
C3—C11.468 (4)N3—C191.323 (4)
O2—C61.370 (4)C26—C271.381 (5)
C5—C61.325 (6)C26—H260.93
C5—C41.405 (5)C36—C351.388 (5)
C5—H50.93C36—H360.93
O1—C11.257 (4)C14—H140.93
C16—C151.368 (5)C4—H40.93
C16—C171.369 (5)C32—C331.388 (5)
C16—H160.93C32—H320.93
C9—C101.361 (6)C27—C281.350 (6)
C9—C81.381 (5)C27—H270.93
C9—H90.93C35—C341.354 (6)
O3—C191.261 (4)C35—H350.93
N4—C201.357 (4)C23—C241.321 (6)
N4—C311.452 (4)C23—H230.93
O4—C241.360 (4)C8—H80.93
O4—C211.364 (4)C11—C101.374 (6)
C15—C141.387 (5)C11—H110.93
C15—H150.93C30—C291.387 (5)
N2—C21.360 (4)C30—H300.93
N2—C71.440 (4)C10—H100.93
N2—C131.441 (4)C33—C341.363 (6)
N1—C21.323 (4)C33—H330.93
N1—C11.324 (4)C6—H60.93
C31—C361.369 (5)C28—C291.365 (6)
C31—C321.370 (5)C28—H280.93
C17—C181.379 (4)C24—H240.93
C17—H170.93C34—H340.93
C22—C211.339 (5)C29—H290.93
O3—Ni1—O184.21 (9)N1—C1—C3112.0 (3)
O3—Ni1—S1176.26 (8)C25—C26—C27120.5 (4)
O1—Ni1—S195.90 (7)C25—C26—H26119.7
O3—Ni1—S295.82 (7)C27—C26—H26119.7
O1—Ni1—S2176.87 (8)C31—C36—C35119.7 (4)
S1—Ni1—S284.28 (3)C31—C36—H36120.2
C20—S2—Ni1108.55 (11)C35—C36—H36120.2
C2—S1—Ni1108.64 (11)C13—C14—C15119.0 (3)
C26—C25—C30119.3 (3)C13—C14—H14120.5
C26—C25—N4120.9 (3)C15—C14—H14120.5
C30—C25—N4119.7 (3)N3—C20—N4114.0 (3)
C4—C3—O2110.4 (3)N3—C20—S2128.9 (2)
C4—C3—C1131.4 (3)N4—C20—S2117.1 (2)
O2—C3—C1118.1 (3)C3—C4—C5106.7 (4)
C3—O2—C6105.1 (3)C3—C4—H4126.6
C6—C5—C4106.7 (4)C5—C4—H4126.6
C6—C5—H5126.7O3—C19—N3130.4 (3)
C4—C5—H5126.7O3—C19—C21116.7 (3)
C1—O1—Ni1131.4 (2)N3—C19—C21112.8 (3)
C15—C16—C17120.4 (3)C31—C32—C33119.1 (4)
C15—C16—H16119.8C31—C32—H32120.4
C17—C16—H16119.8C33—C32—H32120.4
C10—C9—C8120.9 (4)C28—C27—C26120.3 (4)
C10—C9—H9119.6C28—C27—H27119.8
C8—C9—H9119.6C26—C27—H27119.8
C19—O3—Ni1131.6 (2)C34—C35—C36119.7 (4)
C20—N4—C25124.4 (3)C34—C35—H35120.1
C20—N4—C31118.9 (3)C36—C35—H35120.1
C25—N4—C31116.6 (2)C24—C23—C22106.4 (4)
C24—O4—C21105.7 (3)C24—C23—H23126.8
C16—C15—C14120.3 (3)C22—C23—H23126.8
C16—C15—H15119.8C7—C8—C9118.9 (4)
C14—C15—H15119.8C7—C8—H8120.5
C2—N2—C7122.7 (2)C9—C8—H8120.5
C2—N2—C13121.6 (2)C10—C11—C12120.1 (4)
C7—N2—C13115.6 (2)C10—C11—H11120
C2—N1—C1123.9 (3)C12—C11—H11120
C36—C31—C32120.5 (3)C25—C30—C29119.4 (4)
C36—C31—N4119.8 (3)C25—C30—H30120.3
C32—C31—N4119.7 (3)C29—C30—H30120.3
C16—C17—C18119.9 (3)C9—C10—C11119.9 (4)
C16—C17—H17120.1C9—C10—H10120
C18—C17—H17120.1C11—C10—H10120
C21—C22—C23107.3 (4)N1—C2—N2114.9 (3)
C21—C22—H22126.4N1—C2—S1129.1 (2)
C23—C22—H22126.4N2—C2—S1116.0 (2)
C22—C21—O4109.6 (3)C34—C33—C32120.1 (4)
C22—C21—C19132.7 (3)C34—C33—H33120
O4—C21—C19117.7 (3)C32—C33—H33120
C18—C13—C14120.5 (3)C5—C6—O2111.1 (3)
C18—C13—N2121.0 (3)C5—C6—H6124.5
C14—C13—N2118.4 (3)O2—C6—H6124.5
C8—C7—C12120.9 (3)C27—C28—C29119.7 (4)
C8—C7—N2118.7 (3)C27—C28—H28120.1
C12—C7—N2120.3 (3)C29—C28—H28120.1
C7—C12—C11119.3 (4)C23—C24—O4111.1 (4)
C7—C12—H12120.3C23—C24—H24124.5
C11—C12—H12120.3O4—C24—H24124.5
C13—C18—C17119.9 (3)C35—C34—C33120.9 (4)
C13—C18—H18120.1C35—C34—H34119.6
C17—C18—H18120.1C33—C34—H34119.6
C20—N3—C19124.5 (3)C28—C29—C30120.7 (4)
O1—C1—N1131.0 (3)C28—C29—H29119.7
O1—C1—C3117.0 (3)C30—C29—H29119.7
C4—C3—O2—C60.5 (4)C25—N4—C20—S2−5.4 (4)
C1—C3—O2—C6177.2 (3)C31—N4—C20—S2176.9 (2)
C26—C25—N4—C20−62.4 (5)Ni1—S2—C20—N34.5 (3)
C30—C25—N4—C20120.9 (4)Ni1—S2—C20—N4−173.9 (2)
C26—C25—N4—C31115.4 (4)O2—C3—C4—C50.4 (5)
C30—C25—N4—C31−61.4 (4)C1—C3—C4—C5−175.7 (3)
C17—C16—C15—C14−0.8 (6)C6—C5—C4—C3−1.3 (5)
C20—N4—C31—C36−89.2 (4)Ni1—O3—C19—N3−4.2 (6)
C25—N4—C31—C3693.0 (4)Ni1—O3—C19—C21174.8 (2)
C20—N4—C31—C3292.1 (4)C20—N3—C19—O32.3 (6)
C25—N4—C31—C32−85.8 (4)C20—N3—C19—C21−176.7 (3)
C15—C16—C17—C180.6 (6)C22—C21—C19—O3179.0 (4)
C23—C22—C21—O4−0.9 (5)O4—C21—C19—O3−5.6 (5)
C23—C22—C21—C19174.7 (4)C22—C21—C19—N3−1.8 (6)
C24—O4—C21—C221.5 (4)O4—C21—C19—N3173.5 (3)
C24—O4—C21—C19−174.8 (3)C36—C31—C32—C330.3 (5)
C2—N2—C13—C1855.4 (4)N4—C31—C32—C33179.0 (3)
C7—N2—C13—C18−122.0 (3)C25—C26—C27—C28−0.5 (6)
C2—N2—C13—C14−127.7 (3)C31—C36—C35—C34−0.8 (6)
C7—N2—C13—C1455.0 (4)C21—C22—C23—C240.0 (5)
C2—N2—C7—C8−106.7 (4)C12—C7—C8—C90.9 (5)
C13—N2—C7—C870.7 (4)N2—C7—C8—C9−176.3 (3)
C2—N2—C7—C1276.1 (4)C10—C9—C8—C7−0.5 (6)
C13—N2—C7—C12−106.6 (4)C7—C12—C11—C10−0.1 (6)
C8—C7—C12—C11−0.6 (5)C26—C25—C30—C29−0.4 (6)
N2—C7—C12—C11176.6 (3)N4—C25—C30—C29176.4 (4)
C14—C13—C18—C17−0.8 (5)C8—C9—C10—C11−0.2 (6)
N2—C13—C18—C17176.1 (3)C12—C11—C10—C90.5 (7)
C16—C17—C18—C130.2 (5)C1—N1—C2—N2180.0 (3)
C2—N1—C1—O11.4 (6)C1—N1—C2—S10.3 (5)
C2—N1—C1—C3−178.9 (3)C7—N2—C2—N1−175.0 (3)
C4—C3—C1—O1162.4 (4)C13—N2—C2—N17.8 (4)
O2—C3—C1—O1−13.5 (4)C7—N2—C2—S14.8 (4)
C4—C3—C1—N1−17.3 (5)C13—N2—C2—S1−172.4 (2)
O2—C3—C1—N1166.8 (3)Ni1—S1—C2—N1−1.0 (3)
C30—C25—C26—C270.5 (6)Ni1—S1—C2—N2179.3 (2)
N4—C25—C26—C27−176.3 (3)C31—C32—C33—C34−0.1 (6)
C32—C31—C36—C350.2 (5)C4—C5—C6—O21.6 (5)
N4—C31—C36—C35−178.6 (3)C3—O2—C6—C5−1.4 (4)
C18—C13—C14—C150.6 (5)C26—C27—C28—C290.4 (7)
N2—C13—C14—C15−176.3 (3)C22—C23—C24—O41.0 (5)
C16—C15—C14—C130.2 (5)C21—O4—C24—C23−1.6 (5)
C19—N3—C20—N4175.3 (3)C36—C35—C34—C331.0 (6)
C19—N3—C20—S2−3.1 (5)C32—C33—C34—C35−0.6 (6)
C25—N4—C20—N3176.0 (3)C27—C28—C29—C30−0.2 (7)
C31—N4—C20—N3−1.7 (4)C25—C30—C29—C280.3 (7)
Table 1
Selected geometric parameters (Å, °) top
Ni1—O31.870 (2)Ni1—S12.1412 (9)
Ni1—O11.872 (2)Ni1—S22.1452 (9)
O3—Ni1—O184.21 (9)O3—Ni1—S295.82 (7)
O3—Ni1—S1176.26 (8)O1—Ni1—S2176.87 (8)
O1—Ni1—S195.90 (7)S1—Ni1—S284.28 (3)
Acknowledgements top

The authors thank the Crystallography Group, São Carlos Physics Institute, USP, Brazil, for allowing the X-ray data collection. The authors acknowledge financial support from Brazilian agencies CAPES (Project No. 018/05) and CNPq (Project No. 134576/2007-1).

references
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