cis-Bis[N-(2-furoyl)-N′,N′-diphenyl­thio­ureato-κ2O,S]nickel(II)

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

doi:10.1107/S160053680900302X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m242

doi:10.1107/S160053680900302X

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cis-Bis[N-(2-furoyl)-N′,N′-diphenylthioureato-κ²O,S]nickel(II)

Hiram Pérez,^a Rodrigo S. Corrêa,^b Ana María Plutín,^c Osmar Calderón ^c and Julio Duque ^d ^*

^aDepartamento de Química Inorgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, ^bGrupo de Cristalografía, Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil, ^cLaboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, and ^dInstituto de Ciencia y Tecnología de Materiales, Universidad de la Habana, Habana 10400, Cuba
^*Correspondence e-mail: hperez@fq.uh.cu

(Received 21 January 2009; accepted 23 January 2009; online 31 January 2009)

In the title compound, [Ni(C₁₈H₁₃N₂O₂S)₂], the Ni^II 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.

Related literature

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

Crystal data

[Ni(C₁₈H₁₃N₂O₂S)₂]
M_r = 701.46
Triclinic, $[P \overline 1]$
a = 10.0458 (2) Å
b = 11.0030 (3) Å
c = 15.9718 (3) Å
α = 72.755 (2)°
β = 88.792 (2)°
γ = 74.874 (1)°
V = 1624.61 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 294 K
0.15 × 0.09 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: Gaussian (Coppens et al., 1965 ) T_min = 0.955, T_max = 0.980
12907 measured reflections
7027 independent reflections
5083 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.145
S = 1.22
7027 reflections
424 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O3	1.870 (2)
Ni1—O1	1.872 (2)
Ni1—S1	2.1412 (9)
Ni1—S2	2.1452 (9)

O3—Ni1—O1	84.21 (9)
O3—Ni1—S1	176.26 (8)
O1—Ni1—S1	95.90 (7)
O3—Ni1—S2	95.82 (7)
O1—Ni1—S2	176.87 (8)
S1—Ni1—S2	84.28 (3)

Data collection: COLLECT (Enraf–Nonius, 2000 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900302X/gk2187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900302X/gk2187Isup2.hkl

checkCIF report

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 Ni^II 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.

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

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	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
M_r = 701.46	F(000) = 724
Triclinic, P1	D_x = 1.434 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0458 (2) Å	Cell parameters from 83255 reflections
b = 11.0030 (3) Å	θ = 2.9–27.1°
c = 15.9718 (3) Å	µ = 0.77 mm⁻¹
α = 72.755 (2)°	T = 294 K
β = 88.792 (2)°	Prism, red
γ = 74.874 (1)°	0.15 × 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 scans	R_int = 0.053
Absorption correction: gaussian (Coppens et al., 1965)	θ_max = 27.1°, θ_min = 3.1°
T_min = 0.955, T_max = 0.980	h = −12→12
12907 measured reflections	k = −13→14
7027 independent reflections	l = −17→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.064	w = 1/[σ²(F_o²) + (0.0511P)² + 0.2693P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.22	Δρ_max = 0.33 e Å⁻³
7027 reflections	Δρ_min = −0.46 e Å⁻³
424 parameters

Crystal data top

[Ni(C₁₈H₁₃N₂O₂S)₂]	γ = 74.874 (1)°
M_r = 701.46	V = 1624.61 (7) Å³
Triclinic, P1	Z = 2
a = 10.0458 (2) Å	Mo Kα radiation
b = 11.0030 (3) Å	µ = 0.77 mm⁻¹
c = 15.9718 (3) Å	T = 294 K
α = 72.755 (2)°	0.15 × 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)
T_min = 0.955, T_max = 0.980	R_int = 0.053
12907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.22	Δρ_max = 0.33 e Å⁻³
7027 reflections	Δρ_min = −0.46 e Å⁻³
424 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.10992 (4)	0.16148 (4)	0.22008 (2)	0.04396 (16)
S2	0.17245 (9)	0.12133 (9)	0.09958 (6)	0.0542 (3)
S1	0.27714 (9)	−0.00834 (9)	0.27898 (6)	0.0562 (3)
C25	0.1818 (3)	0.1120 (3)	−0.0847 (2)	0.0468 (8)
C3	0.0498 (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	−0.0504	0.2582	0.6436	0.096*
O1	0.0615 (2)	0.2029 (2)	0.32411 (14)	0.0539 (6)
C16	0.4337 (4)	−0.2623 (4)	0.7121 (2)	0.0608 (10)
H16	0.4447	−0.2931	0.7731	0.073*
C9	0.5753 (5)	−0.4263 (4)	0.3721 (3)	0.0758 (12)
H9	0.568	−0.5109	0.3778	0.091*
O3	−0.0437 (2)	0.3025 (2)	0.16983 (14)	0.0551 (6)
N4	0.0672 (3)	0.2042 (3)	−0.06320 (16)	0.0485 (7)
O4	−0.2840 (2)	0.4849 (2)	0.14960 (16)	0.0649 (7)
C15	0.5424 (4)	−0.2347 (4)	0.6641 (2)	0.0592 (9)
H15	0.6265	−0.2459	0.6926	0.071*
N2	0.3911 (3)	−0.1353 (3)	0.43740 (16)	0.0433 (6)
N1	0.2152 (3)	0.0424 (3)	0.43601 (16)	0.0427 (6)
C31	−0.0362 (3)	0.2842 (3)	−0.1339 (2)	0.0459 (8)
C17	0.3089 (4)	−0.2447 (4)	0.6709 (2)	0.0593 (10)
H17	0.2351	−0.2628	0.7039	0.071*
C22	−0.3081 (4)	0.5271 (4)	0.0059 (3)	0.0696 (11)
H22	−0.2911	0.5258	−0.0513	0.084*
C21	−0.2258 (3)	0.4548 (3)	0.0779 (2)	0.0467 (8)
C13	0.4024 (3)	−0.1739 (3)	0.5320 (2)	0.0420 (7)
C7	0.4894 (3)	−0.2189 (3)	0.3976 (2)	0.0456 (8)
C12	0.5971 (4)	−0.1767 (4)	0.3554 (2)	0.0641 (10)
H12	0.6045	−0.0921	0.3495	0.077*
C18	0.2929 (3)	−0.2002 (3)	0.5805 (2)	0.0491 (8)
H18	0.2082	−0.188	0.5524	0.059*
N3	−0.0573 (3)	0.3195 (3)	0.02013 (16)	0.0476 (7)
C1	0.1123 (3)	0.1489 (3)	0.4017 (2)	0.0424 (7)
C26	0.3131 (4)	0.1250 (4)	−0.0810 (2)	0.0650 (10)
H26	0.3293	0.1915	−0.0611	0.078*
C36	−0.1497 (4)	0.2426 (4)	−0.1455 (2)	0.0574 (9)
H36	−0.1617	0.1644	−0.1075	0.069*
C14	0.5278 (3)	−0.1902 (3)	0.5730 (2)	0.0521 (9)
H14	0.6016	−0.1716	0.5402	0.063*
C20	0.0522 (3)	0.2238 (3)	0.0169 (2)	0.0439 (8)
C4	0.0562 (4)	0.1639 (4)	0.5560 (2)	0.0667 (11)
H4	0.1089	0.082	0.5907	0.08*
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)
H32	0.0595	0.4273	−0.1816	0.072*
C27	0.4219 (4)	0.0402 (5)	−0.1067 (3)	0.0723 (12)
H27	0.5106	0.0504	−0.1044	0.087*
C35	−0.2467 (4)	0.3177 (4)	−0.2142 (3)	0.0692 (11)
H35	−0.3235	0.2895	−0.2229	0.083*
C23	−0.4244 (4)	0.6049 (4)	0.0329 (3)	0.0777 (13)
H23	−0.4994	0.6652	−0.0028	0.093*
C8	0.4766 (4)	−0.3430 (4)	0.4059 (2)	0.0582 (9)
H8	0.4028	−0.3707	0.4338	0.07*
C11	0.6944 (4)	−0.2612 (5)	0.3217 (3)	0.0796 (13)
H11	0.7676	−0.2335	0.2929	0.095*
C30	0.1591 (4)	0.0128 (4)	−0.1135 (3)	0.0716 (12)
H30	0.0705	0.0024	−0.116	0.086*
C10	0.6831 (5)	−0.3862 (5)	0.3306 (3)	0.0824 (15)
H10	0.749	−0.4433	0.3083	0.099*
C2	0.2900 (3)	−0.0298 (3)	0.3898 (2)	0.0406 (7)
C33	−0.1163 (5)	0.4739 (4)	−0.2575 (2)	0.0729 (12)
H33	−0.1051	0.5524	−0.2957	0.087*
C6	−0.0839 (4)	0.3632 (4)	0.5149 (3)	0.0714 (12)
H6	−0.1441	0.4428	0.516	0.086*
C28	0.4000 (5)	−0.0574 (4)	−0.1351 (3)	0.0759 (12)
H28	0.4735	−0.1146	−0.152	0.091*
C24	−0.4066 (4)	0.5758 (4)	0.1190 (3)	0.0731 (12)
H24	−0.4696	0.6127	0.1541	0.088*
C34	−0.2292 (5)	0.4322 (4)	−0.2686 (3)	0.0727 (12)
H34	−0.2951	0.4831	−0.3141	0.087*
C29	0.2695 (5)	−0.0716 (4)	−0.1389 (3)	0.0892 (15)
H29	0.2545	−0.1387	−0.1587	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0427 (3)	0.0473 (3)	0.0365 (3)	−0.00044 (19)	0.00223 (18)	−0.01466 (19)
S2	0.0514 (5)	0.0615 (6)	0.0397 (5)	0.0050 (4)	0.0030 (4)	−0.0179 (4)
S1	0.0577 (6)	0.0587 (6)	0.0390 (5)	0.0128 (4)	−0.0016 (4)	−0.0198 (4)
C25	0.0448 (19)	0.054 (2)	0.0376 (17)	−0.0041 (16)	0.0069 (14)	−0.0156 (15)
C3	0.0386 (18)	0.050 (2)	0.050 (2)	0.0001 (16)	0.0030 (15)	−0.0261 (16)
O2	0.0571 (15)	0.0555 (15)	0.0630 (16)	0.0006 (12)	0.0088 (12)	−0.0282 (12)
C5	0.074 (3)	0.107 (4)	0.062 (3)	0.003 (3)	0.009 (2)	−0.053 (3)
O1	0.0560 (14)	0.0540 (14)	0.0398 (13)	0.0092 (11)	−0.0010 (11)	−0.0170 (11)
C16	0.085 (3)	0.051 (2)	0.0396 (19)	−0.005 (2)	−0.001 (2)	−0.0148 (16)
C9	0.092 (3)	0.055 (3)	0.072 (3)	0.012 (2)	−0.007 (2)	−0.033 (2)
O3	0.0536 (14)	0.0612 (15)	0.0385 (13)	0.0073 (12)	−0.0005 (11)	−0.0164 (11)
N4	0.0485 (16)	0.0541 (17)	0.0400 (15)	−0.0026 (14)	0.0014 (12)	−0.0197 (13)
O4	0.0590 (16)	0.0630 (17)	0.0567 (15)	0.0087 (13)	0.0086 (12)	−0.0164 (13)
C15	0.063 (2)	0.059 (2)	0.054 (2)	−0.0102 (19)	−0.0128 (19)	−0.0181 (18)
N2	0.0391 (14)	0.0483 (16)	0.0365 (14)	0.0020 (12)	0.0014 (11)	−0.0161 (12)
N1	0.0402 (15)	0.0449 (16)	0.0402 (15)	−0.0032 (13)	0.0032 (12)	−0.0157 (12)
C31	0.0480 (19)	0.048 (2)	0.0372 (17)	−0.0029 (16)	0.0041 (15)	−0.0148 (15)
C17	0.063 (2)	0.058 (2)	0.048 (2)	−0.0072 (19)	0.0146 (18)	−0.0113 (17)
C22	0.068 (3)	0.064 (3)	0.065 (3)	0.009 (2)	−0.016 (2)	−0.025 (2)
C21	0.0481 (19)	0.0432 (19)	0.0446 (19)	−0.0021 (16)	0.0011 (15)	−0.0156 (15)
C13	0.0431 (18)	0.0412 (18)	0.0402 (17)	−0.0040 (15)	0.0019 (14)	−0.0164 (14)
C7	0.0408 (18)	0.050 (2)	0.0373 (17)	0.0059 (15)	0.0032 (14)	−0.0159 (15)
C12	0.052 (2)	0.076 (3)	0.060 (2)	−0.005 (2)	0.0154 (18)	−0.026 (2)
C18	0.0429 (19)	0.056 (2)	0.0444 (19)	−0.0071 (16)	0.0036 (15)	−0.0140 (16)
N3	0.0529 (17)	0.0500 (17)	0.0378 (15)	−0.0060 (14)	0.0036 (13)	−0.0170 (13)
C1	0.0399 (18)	0.0474 (19)	0.0410 (18)	−0.0105 (16)	0.0067 (14)	−0.0161 (15)
C26	0.059 (2)	0.086 (3)	0.060 (2)	−0.020 (2)	0.0100 (19)	−0.036 (2)
C36	0.057 (2)	0.056 (2)	0.056 (2)	−0.0100 (19)	−0.0011 (18)	−0.0170 (18)
C14	0.049 (2)	0.056 (2)	0.050 (2)	−0.0113 (17)	−0.0010 (16)	−0.0159 (17)
C20	0.0463 (19)	0.048 (2)	0.0381 (17)	−0.0114 (16)	0.0077 (14)	−0.0151 (15)
C4	0.062 (2)	0.085 (3)	0.046 (2)	0.007 (2)	−0.0003 (18)	−0.030 (2)
C19	0.0476 (19)	0.0430 (19)	0.0439 (19)	−0.0068 (16)	0.0017 (15)	−0.0110 (15)
C32	0.066 (2)	0.056 (2)	0.057 (2)	−0.015 (2)	0.0057 (19)	−0.0177 (19)
C27	0.049 (2)	0.104 (4)	0.067 (3)	−0.013 (2)	0.0125 (19)	−0.037 (3)
C35	0.055 (2)	0.075 (3)	0.078 (3)	−0.003 (2)	−0.010 (2)	−0.034 (2)
C23	0.061 (3)	0.059 (3)	0.097 (4)	0.016 (2)	−0.026 (2)	−0.025 (2)
C8	0.065 (2)	0.054 (2)	0.053 (2)	−0.0037 (19)	0.0029 (18)	−0.0217 (18)
C11	0.054 (2)	0.107 (4)	0.068 (3)	0.000 (3)	0.017 (2)	−0.031 (3)
C30	0.063 (3)	0.069 (3)	0.100 (3)	−0.022 (2)	0.023 (2)	−0.047 (2)
C10	0.064 (3)	0.108 (4)	0.054 (3)	0.024 (3)	0.004 (2)	−0.035 (3)
C2	0.0364 (17)	0.0440 (19)	0.0410 (17)	−0.0074 (15)	0.0015 (14)	−0.0149 (15)
C33	0.095 (3)	0.053 (2)	0.052 (2)	−0.003 (2)	0.004 (2)	−0.0043 (19)
C6	0.061 (2)	0.077 (3)	0.083 (3)	0.000 (2)	0.012 (2)	−0.052 (3)
C28	0.070 (3)	0.073 (3)	0.076 (3)	0.000 (2)	0.022 (2)	−0.027 (2)
C24	0.057 (3)	0.059 (3)	0.090 (3)	0.010 (2)	0.007 (2)	−0.025 (2)
C34	0.074 (3)	0.070 (3)	0.060 (3)	0.012 (2)	−0.016 (2)	−0.026 (2)
C29	0.084 (3)	0.068 (3)	0.135 (4)	−0.021 (3)	0.037 (3)	−0.061 (3)

Geometric parameters (Å, º) top

Ni1—O3	1.870 (2)	C22—C23	1.400 (5)
Ni1—O1	1.872 (2)	C22—H22	0.93
Ni1—S1	2.1412 (9)	C21—C19	1.456 (4)
Ni1—S2	2.1452 (9)	C13—C18	1.376 (4)
S2—C20	1.717 (3)	C13—C14	1.376 (4)
S1—C2	1.718 (3)	C7—C8	1.372 (5)
C25—C26	1.368 (5)	C7—C12	1.374 (5)
C25—C30	1.373 (5)	C12—C11	1.383 (5)
C25—N4	1.433 (4)	C12—H12	0.93
C3—C4	1.341 (5)	C18—H18	0.93
C3—O2	1.366 (4)	N3—C20	1.322 (4)
C3—C1	1.468 (4)	N3—C19	1.323 (4)
O2—C6	1.370 (4)	C26—C27	1.381 (5)
C5—C6	1.325 (6)	C26—H26	0.93
C5—C4	1.405 (5)	C36—C35	1.388 (5)
C5—H5	0.93	C36—H36	0.93
O1—C1	1.257 (4)	C14—H14	0.93
C16—C15	1.368 (5)	C4—H4	0.93
C16—C17	1.369 (5)	C32—C33	1.388 (5)
C16—H16	0.93	C32—H32	0.93
C9—C10	1.361 (6)	C27—C28	1.350 (6)
C9—C8	1.381 (5)	C27—H27	0.93
C9—H9	0.93	C35—C34	1.354 (6)
O3—C19	1.261 (4)	C35—H35	0.93
N4—C20	1.357 (4)	C23—C24	1.321 (6)
N4—C31	1.452 (4)	C23—H23	0.93
O4—C24	1.360 (4)	C8—H8	0.93
O4—C21	1.364 (4)	C11—C10	1.374 (6)
C15—C14	1.387 (5)	C11—H11	0.93
C15—H15	0.93	C30—C29	1.387 (5)
N2—C2	1.360 (4)	C30—H30	0.93
N2—C7	1.440 (4)	C10—H10	0.93
N2—C13	1.441 (4)	C33—C34	1.363 (6)
N1—C2	1.323 (4)	C33—H33	0.93
N1—C1	1.324 (4)	C6—H6	0.93
C31—C36	1.369 (5)	C28—C29	1.365 (6)
C31—C32	1.370 (5)	C28—H28	0.93
C17—C18	1.379 (4)	C24—H24	0.93
C17—H17	0.93	C34—H34	0.93
C22—C21	1.339 (5)	C29—H29	0.93

O3—Ni1—O1	84.21 (9)	N1—C1—C3	112.0 (3)
O3—Ni1—S1	176.26 (8)	C25—C26—C27	120.5 (4)
O1—Ni1—S1	95.90 (7)	C25—C26—H26	119.7
O3—Ni1—S2	95.82 (7)	C27—C26—H26	119.7
O1—Ni1—S2	176.87 (8)	C31—C36—C35	119.7 (4)
S1—Ni1—S2	84.28 (3)	C31—C36—H36	120.2
C20—S2—Ni1	108.55 (11)	C35—C36—H36	120.2
C2—S1—Ni1	108.64 (11)	C13—C14—C15	119.0 (3)
C26—C25—C30	119.3 (3)	C13—C14—H14	120.5
C26—C25—N4	120.9 (3)	C15—C14—H14	120.5
C30—C25—N4	119.7 (3)	N3—C20—N4	114.0 (3)
C4—C3—O2	110.4 (3)	N3—C20—S2	128.9 (2)
C4—C3—C1	131.4 (3)	N4—C20—S2	117.1 (2)
O2—C3—C1	118.1 (3)	C3—C4—C5	106.7 (4)
C3—O2—C6	105.1 (3)	C3—C4—H4	126.6
C6—C5—C4	106.7 (4)	C5—C4—H4	126.6
C6—C5—H5	126.7	O3—C19—N3	130.4 (3)
C4—C5—H5	126.7	O3—C19—C21	116.7 (3)
C1—O1—Ni1	131.4 (2)	N3—C19—C21	112.8 (3)
C15—C16—C17	120.4 (3)	C31—C32—C33	119.1 (4)
C15—C16—H16	119.8	C31—C32—H32	120.4
C17—C16—H16	119.8	C33—C32—H32	120.4
C10—C9—C8	120.9 (4)	C28—C27—C26	120.3 (4)
C10—C9—H9	119.6	C28—C27—H27	119.8
C8—C9—H9	119.6	C26—C27—H27	119.8
C19—O3—Ni1	131.6 (2)	C34—C35—C36	119.7 (4)
C20—N4—C25	124.4 (3)	C34—C35—H35	120.1
C20—N4—C31	118.9 (3)	C36—C35—H35	120.1
C25—N4—C31	116.6 (2)	C24—C23—C22	106.4 (4)
C24—O4—C21	105.7 (3)	C24—C23—H23	126.8
C16—C15—C14	120.3 (3)	C22—C23—H23	126.8
C16—C15—H15	119.8	C7—C8—C9	118.9 (4)
C14—C15—H15	119.8	C7—C8—H8	120.5
C2—N2—C7	122.7 (2)	C9—C8—H8	120.5
C2—N2—C13	121.6 (2)	C10—C11—C12	120.1 (4)
C7—N2—C13	115.6 (2)	C10—C11—H11	120
C2—N1—C1	123.9 (3)	C12—C11—H11	120
C36—C31—C32	120.5 (3)	C25—C30—C29	119.4 (4)
C36—C31—N4	119.8 (3)	C25—C30—H30	120.3
C32—C31—N4	119.7 (3)	C29—C30—H30	120.3
C16—C17—C18	119.9 (3)	C9—C10—C11	119.9 (4)
C16—C17—H17	120.1	C9—C10—H10	120
C18—C17—H17	120.1	C11—C10—H10	120
C21—C22—C23	107.3 (4)	N1—C2—N2	114.9 (3)
C21—C22—H22	126.4	N1—C2—S1	129.1 (2)
C23—C22—H22	126.4	N2—C2—S1	116.0 (2)
C22—C21—O4	109.6 (3)	C34—C33—C32	120.1 (4)
C22—C21—C19	132.7 (3)	C34—C33—H33	120
O4—C21—C19	117.7 (3)	C32—C33—H33	120
C18—C13—C14	120.5 (3)	C5—C6—O2	111.1 (3)
C18—C13—N2	121.0 (3)	C5—C6—H6	124.5
C14—C13—N2	118.4 (3)	O2—C6—H6	124.5
C8—C7—C12	120.9 (3)	C27—C28—C29	119.7 (4)
C8—C7—N2	118.7 (3)	C27—C28—H28	120.1
C12—C7—N2	120.3 (3)	C29—C28—H28	120.1
C7—C12—C11	119.3 (4)	C23—C24—O4	111.1 (4)
C7—C12—H12	120.3	C23—C24—H24	124.5
C11—C12—H12	120.3	O4—C24—H24	124.5
C13—C18—C17	119.9 (3)	C35—C34—C33	120.9 (4)
C13—C18—H18	120.1	C35—C34—H34	119.6
C17—C18—H18	120.1	C33—C34—H34	119.6
C20—N3—C19	124.5 (3)	C28—C29—C30	120.7 (4)
O1—C1—N1	131.0 (3)	C28—C29—H29	119.7
O1—C1—C3	117.0 (3)	C30—C29—H29	119.7

C4—C3—O2—C6	0.5 (4)	C25—N4—C20—S2	−5.4 (4)
C1—C3—O2—C6	177.2 (3)	C31—N4—C20—S2	176.9 (2)
C26—C25—N4—C20	−62.4 (5)	Ni1—S2—C20—N3	4.5 (3)
C30—C25—N4—C20	120.9 (4)	Ni1—S2—C20—N4	−173.9 (2)
C26—C25—N4—C31	115.4 (4)	O2—C3—C4—C5	0.4 (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—C36	93.0 (4)	Ni1—O3—C19—C21	174.8 (2)
C20—N4—C31—C32	92.1 (4)	C20—N3—C19—O3	2.3 (6)
C25—N4—C31—C32	−85.8 (4)	C20—N3—C19—C21	−176.7 (3)
C15—C16—C17—C18	0.6 (6)	C22—C21—C19—O3	179.0 (4)
C23—C22—C21—O4	−0.9 (5)	O4—C21—C19—O3	−5.6 (5)
C23—C22—C21—C19	174.7 (4)	C22—C21—C19—N3	−1.8 (6)
C24—O4—C21—C22	1.5 (4)	O4—C21—C19—N3	173.5 (3)
C24—O4—C21—C19	−174.8 (3)	C36—C31—C32—C33	0.3 (5)
C2—N2—C13—C18	55.4 (4)	N4—C31—C32—C33	179.0 (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—C14	55.0 (4)	C21—C22—C23—C24	0.0 (5)
C2—N2—C7—C8	−106.7 (4)	C12—C7—C8—C9	0.9 (5)
C13—N2—C7—C8	70.7 (4)	N2—C7—C8—C9	−176.3 (3)
C2—N2—C7—C12	76.1 (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—C11	176.6 (3)	N4—C25—C30—C29	176.4 (4)
C14—C13—C18—C17	−0.8 (5)	C8—C9—C10—C11	−0.2 (6)
N2—C13—C18—C17	176.1 (3)	C12—C11—C10—C9	0.5 (7)
C16—C17—C18—C13	0.2 (5)	C1—N1—C2—N2	180.0 (3)
C2—N1—C1—O1	1.4 (6)	C1—N1—C2—S1	0.3 (5)
C2—N1—C1—C3	−178.9 (3)	C7—N2—C2—N1	−175.0 (3)
C4—C3—C1—O1	162.4 (4)	C13—N2—C2—N1	7.8 (4)
O2—C3—C1—O1	−13.5 (4)	C7—N2—C2—S1	4.8 (4)
C4—C3—C1—N1	−17.3 (5)	C13—N2—C2—S1	−172.4 (2)
O2—C3—C1—N1	166.8 (3)	Ni1—S1—C2—N1	−1.0 (3)
C30—C25—C26—C27	0.5 (6)	Ni1—S1—C2—N2	179.3 (2)
N4—C25—C26—C27	−176.3 (3)	C31—C32—C33—C34	−0.1 (6)
C32—C31—C36—C35	0.2 (5)	C4—C5—C6—O2	1.6 (5)
N4—C31—C36—C35	−178.6 (3)	C3—O2—C6—C5	−1.4 (4)
C18—C13—C14—C15	0.6 (5)	C26—C27—C28—C29	0.4 (7)
N2—C13—C14—C15	−176.3 (3)	C22—C23—C24—O4	1.0 (5)
C16—C15—C14—C13	0.2 (5)	C21—O4—C24—C23	−1.6 (5)
C19—N3—C20—N4	175.3 (3)	C36—C35—C34—C33	1.0 (6)
C19—N3—C20—S2	−3.1 (5)	C32—C33—C34—C35	−0.6 (6)
C25—N4—C20—N3	176.0 (3)	C27—C28—C29—C30	−0.2 (7)
C31—N4—C20—N3	−1.7 (4)	C25—C30—C29—C28	0.3 (7)

Experimental details

Crystal data
Chemical formula	[Ni(C₁₈H₁₃N₂O₂S)₂]
M_r	701.46
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	10.0458 (2), 11.0030 (3), 15.9718 (3)
α, β, γ (°)	72.755 (2), 88.792 (2), 74.874 (1)
V (Å³)	1624.61 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.15 × 0.09 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Gaussian (Coppens et al., 1965)
T_min, T_max	0.955, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	12907, 7027, 5083
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.145, 1.22
No. of reflections	7027
No. of parameters	424
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.46

Computer programs: COLLECT (Enraf–Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Ni1—O3	1.870 (2)	Ni1—S1	2.1412 (9)
Ni1—O1	1.872 (2)	Ni1—S2	2.1452 (9)

O3—Ni1—O1	84.21 (9)	O3—Ni1—S2	95.82 (7)
O3—Ni1—S1	176.26 (8)	O1—Ni1—S2	176.87 (8)
O1—Ni1—S1	95.90 (7)	S1—Ni1—S2	84.28 (3)

Acknowledgements

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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