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Acta Crystallogr Sect E Struct Rep Online. 2012 February 1; 68(Pt 2): m183–m184.
Published online 2012 January 21. doi:  10.1107/S1600536811055383
PMCID: PMC3274909

Bis{N-ethyl-2-[3-(hy­droxy­imino-κN)butan-2-yl­idene]hydrazinecarbothio­amide-κ2 N 2,S}nickel(II) dichloride

Abstract

In the title complex, [Ni(C7H14N4OS)2]Cl2, the NiII ion is six-coordinated in a distorted octa­hedral geometry by four N atoms from the two imine and two oxime groups, and two S atoms from the thione groups. Two chloride ions complete the asymmetric unit. In the crystal, mol­ecules are linked through N—H(...)Cl and O—H(...)Cl hydrogen bonds into an infinite chain propagating along [101].

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For a related structure, see: Choi et al. (2008 [triangle]). For the biological activity, pharmacological properties and analytical applications of thio­semicarbazones and their metal complexes, see: Cowley et al. (2002 [triangle]); Ming (2003 [triangle]); Lobana et al. (2004 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-0m183-scheme1.jpg

Experimental

Crystal data

  • [Ni(C7H14N4OS)2]Cl2
  • M r = 534.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-0m183-efi1.jpg
  • a = 18.4990 (11) Å
  • b = 14.2097 (9) Å
  • c = 9.2422 (6) Å
  • β = 98.542 (1)°
  • V = 2402.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.23 mm−1
  • T = 293 K
  • 0.42 × 0.20 × 0.12 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.625, T max = 0.869
  • 30693 measured reflections
  • 8190 independent reflections
  • 6071 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.089
  • S = 1.03
  • 8190 reflections
  • 292 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055383/is5020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055383/is5020Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the Inter­national University of Africa (Sudan) for providing research leave. HAF and AQA each thank the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

supplementary crystallographic information

Comment

Thiosemicarbazones and their metal complexes have attracted significant attention because of their wide-ranging biological and pharmacological properties, analytical applications, specific structures, and chemical properties (Cowley et al., 2002; Ming, 2003; Lobana et al., 2007; Lobana et al., 2004). In this paper we report the crystal structure of bis{N-ethyl-2-[2-(hydroxyimino-κN)butan-2-ylidene]hydrazinecarbothioamide-κ2N2,S}nickle(II)dichloride.

In the mononuclear title complex (Fig. 1), [Ni(C7H14N4OS)2]Cl2, the nickel(II) ion is six-coordinated in a distorted octahedral geometry by four N atoms from two imine groups and two oxime groups and two S atoms from two thione groups. The Ni—N and Ni—S bond distances (Table 1) and the bond angles around Ni1 are in agreement with the values found for related Ni(II) complex (Choi et al., 2008). Bond lengths and angles observed in the structure are normal (Allen et al., 1987). Ni1 is a meeting-point of four five-membered rings, namely: A (Ni1/S1/N2/N3/C9), B ((Ni1/S2/N6/N7/C12), C ((Ni1/N1/N2/C1/C2) and D ((Ni1/N5/N6/C5/C6).The dihedral angles between these four rings as follows: A/B = 87.11 (5)°, A/C = 4.37 (6)°, A/D = 88.83 (6)°, B/C = 88.55 (6)°, B/D = 4.26 (6)° and C/D = 86.88 (7)°. In the crystal, molecules are linked through intermolecular N4—H1N4···Cl1, O2—H1O2···Cl1, N7—H1N7···Cl2, N3—H1N3···Cl1, O1—H1O1···Cl2 and N8—H1N8···Cl2 hydrogen bonds (Table 2) into infinite chains propagating along [101] (Fig. 2).

Experimental

The ligand was prepared by the mixing of 2,3-butanedione monoxime (1.01 g) dissolved in 20 ml of EtOH with 4-ethyl-3-thiosemicarbazide (1.19 g) dissolved in 20 ml of EtOH and a few drops of acetic acid. The mixture was boiled under reflux with stirring for 3 h. The mixture was filtered and left to cool and evaporate the solvent at room temperature and the resulting white solid formed was collected by suction filtration and washed with cold EtOH (yield 66%, m.p. 475.2 - 477.2 K). To a solution of the ligand (0.2021 g) in EtOH (20 ml) was added a solution of (NiCl2.6H2O) (0.2377 g) in EtOH (20 ml). The mixture was boiled under reflux for 2 h with stirring. The mixture was filtered and left to cool accompanied by slow evaporation of the solvent at room temperature. The brown crystals were grown in DMF-acetone (1:4) mixture by slow evaporation at room temperature for 2 weeks (yield 45%, m.p. 513.9 K).

Refinement

N- and-O bound H atoms were located in a difference Fourier map and were refined freely. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 or 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene groups and 1.5Ueq(C) for methyl groups. The highest residual electron density peak is located 0.83 Å from Cl1 and the deepest hole is located 0.68 Å from Cl1.

Figures

Fig. 1.
The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

[Ni(C7H14N4OS)2]Cl2F(000) = 1112
Mr = 534.17Dx = 1.477 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7955 reflections
a = 18.4990 (11) Åθ = 2.7–31.5°
b = 14.2097 (9) ŵ = 1.23 mm1
c = 9.2422 (6) ÅT = 293 K
β = 98.542 (1)°Block, purple
V = 2402.5 (3) Å30.42 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer8190 independent reflections
Radiation source: fine-focus sealed tube6071 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 31.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −27→24
Tmin = 0.625, Tmax = 0.869k = −21→19
30693 measured reflectionsl = −12→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0413P)2 + 0.4822P] where P = (Fo2 + 2Fc2)/3
8190 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.36 e Å3

Special details

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.
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)

xyzUiso*/Ueq
Ni10.254705 (10)0.544056 (14)0.720936 (19)0.03000 (6)
S10.19095 (2)0.69236 (3)0.69747 (5)0.04214 (10)
S20.33886 (2)0.59247 (4)0.55926 (4)0.04259 (11)
O10.32326 (8)0.33683 (10)0.76904 (16)0.0528 (3)
O20.15128 (7)0.47332 (11)0.94881 (14)0.0493 (3)
N10.27241 (7)0.39758 (10)0.69614 (14)0.0355 (3)
N20.17389 (7)0.50408 (10)0.56264 (13)0.0318 (3)
N30.12478 (8)0.56856 (10)0.50132 (15)0.0376 (3)
N40.07395 (8)0.71317 (11)0.49656 (17)0.0422 (3)
N50.21534 (7)0.51429 (10)0.92075 (14)0.0345 (3)
N60.33784 (7)0.58110 (9)0.87569 (13)0.0322 (3)
N70.40248 (8)0.61137 (11)0.83749 (15)0.0405 (3)
N80.47653 (9)0.63277 (13)0.66593 (19)0.0510 (4)
C10.17121 (8)0.41842 (12)0.51582 (16)0.0351 (3)
C20.22784 (9)0.35631 (12)0.59529 (17)0.0373 (3)
C30.11569 (11)0.38175 (14)0.39472 (19)0.0484 (4)
H3A0.10580.42880.31990.073*
H3B0.07140.36680.43240.073*
H3C0.13430.32610.35420.073*
C40.23136 (14)0.25422 (14)0.5599 (3)0.0642 (6)
H4A0.26500.22330.63400.096*
H4B0.24770.24680.46670.096*
H4C0.18370.22680.55630.096*
C50.32848 (9)0.58058 (12)1.01105 (16)0.0363 (3)
C60.25807 (9)0.53975 (12)1.03697 (16)0.0360 (3)
C70.38261 (11)0.61688 (17)1.13467 (19)0.0564 (5)
H7A0.40710.67081.10260.085*
H7B0.41780.56871.16620.085*
H7C0.35770.63441.21460.085*
C80.24030 (12)0.52761 (18)1.18843 (19)0.0585 (6)
H8A0.19390.49681.18410.088*
H8B0.23820.58821.23370.088*
H8C0.27750.49011.24480.088*
C90.12641 (8)0.65727 (11)0.55863 (16)0.0336 (3)
C100.06787 (12)0.81258 (14)0.5282 (2)0.0518 (5)
H10A0.11300.84440.51640.062*
H10B0.05960.82080.62860.062*
C110.00570 (14)0.85451 (17)0.4263 (3)0.0682 (6)
H11A0.00350.92100.44380.102*
H11B−0.03930.82570.44290.102*
H11C0.01300.84370.32700.102*
C120.41003 (9)0.61232 (12)0.69315 (17)0.0365 (3)
C130.49817 (12)0.64029 (17)0.5214 (2)0.0592 (5)
H13A0.47890.69800.47470.071*
H13B0.47830.58780.46120.071*
C140.58014 (14)0.64005 (19)0.5352 (3)0.0805 (8)
H14A0.59440.64310.43950.121*
H14B0.59900.58330.58310.121*
H14C0.59940.69350.59160.121*
Cl10.03036 (3)0.42615 (5)0.70489 (5)0.06167 (15)
Cl20.43204 (3)0.39179 (4)1.01970 (8)0.07468 (19)
H1N40.0469 (11)0.6925 (15)0.440 (2)0.043 (6)*
H1O20.1237 (14)0.4674 (16)0.869 (3)0.063 (7)*
H1N70.4416 (12)0.6072 (15)0.903 (2)0.050 (6)*
H1N30.0897 (12)0.5517 (14)0.456 (2)0.046 (6)*
H1O10.3480 (13)0.3666 (16)0.829 (3)0.055 (7)*
H1N80.5085 (13)0.6376 (15)0.742 (2)0.055 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.02577 (10)0.03547 (11)0.02620 (9)−0.00196 (8)−0.00457 (6)−0.00166 (7)
S10.0396 (2)0.0390 (2)0.0418 (2)0.00331 (17)−0.01353 (16)−0.00551 (16)
S20.0354 (2)0.0605 (3)0.03009 (18)−0.00913 (19)−0.00085 (14)0.00010 (17)
O10.0535 (8)0.0468 (8)0.0519 (7)0.0120 (6)−0.0134 (6)−0.0010 (6)
O20.0352 (7)0.0699 (9)0.0409 (6)−0.0168 (6)−0.0004 (5)0.0024 (6)
N10.0325 (7)0.0383 (7)0.0339 (6)0.0037 (5)−0.0007 (5)0.0004 (5)
N20.0265 (6)0.0375 (7)0.0294 (5)−0.0032 (5)−0.0027 (4)−0.0015 (5)
N30.0293 (7)0.0418 (8)0.0367 (7)−0.0015 (6)−0.0116 (5)−0.0021 (5)
N40.0345 (8)0.0467 (8)0.0407 (7)0.0033 (6)−0.0094 (6)0.0010 (6)
N50.0284 (6)0.0406 (7)0.0329 (6)−0.0031 (5)−0.0014 (5)−0.0009 (5)
N60.0267 (6)0.0373 (7)0.0301 (6)−0.0021 (5)−0.0042 (4)−0.0001 (5)
N70.0287 (7)0.0552 (9)0.0345 (6)−0.0070 (6)−0.0062 (5)0.0000 (6)
N80.0317 (8)0.0696 (11)0.0509 (9)−0.0086 (7)0.0035 (6)0.0000 (8)
C10.0299 (8)0.0434 (9)0.0310 (7)−0.0063 (6)0.0010 (5)−0.0059 (6)
C20.0375 (8)0.0375 (8)0.0363 (7)−0.0027 (7)0.0037 (6)−0.0039 (6)
C30.0464 (10)0.0529 (11)0.0416 (8)−0.0103 (8)−0.0073 (7)−0.0127 (8)
C40.0733 (15)0.0421 (11)0.0715 (14)0.0015 (10)−0.0082 (11)−0.0138 (10)
C50.0341 (8)0.0420 (9)0.0293 (6)−0.0019 (7)−0.0070 (6)−0.0018 (6)
C60.0366 (8)0.0408 (8)0.0287 (6)−0.0006 (7)−0.0017 (6)0.0004 (6)
C70.0516 (11)0.0787 (14)0.0341 (8)−0.0182 (10)−0.0090 (7)−0.0095 (9)
C80.0573 (12)0.0867 (16)0.0300 (8)−0.0173 (11)0.0020 (7)0.0016 (9)
C90.0272 (7)0.0411 (8)0.0306 (6)−0.0015 (6)−0.0018 (5)0.0019 (6)
C100.0532 (11)0.0482 (11)0.0497 (10)0.0130 (9)−0.0064 (8)0.0007 (8)
C110.0692 (15)0.0600 (13)0.0677 (13)0.0232 (11)−0.0153 (11)0.0093 (11)
C120.0301 (8)0.0401 (8)0.0379 (7)−0.0024 (6)0.0001 (6)0.0004 (6)
C130.0509 (12)0.0671 (13)0.0637 (12)−0.0074 (10)0.0218 (10)0.0040 (10)
C140.0590 (15)0.0699 (16)0.122 (2)−0.0031 (12)0.0435 (15)−0.0051 (15)
Cl10.0405 (3)0.0975 (4)0.0438 (2)−0.0219 (3)−0.00425 (18)−0.0083 (2)
Cl20.0534 (3)0.0625 (3)0.0937 (4)−0.0016 (3)−0.0363 (3)0.0016 (3)

Geometric parameters (Å, °)

Ni1—N12.1247 (14)C1—C31.496 (2)
Ni1—N22.0120 (12)C2—C41.491 (3)
Ni1—N52.1258 (13)C3—H3A0.9600
Ni1—N62.0086 (12)C3—H3B0.9600
Ni1—S12.4089 (5)C3—H3C0.9600
Ni1—S22.4126 (5)C4—H4A0.9600
S1—C91.6927 (15)C4—H4B0.9600
S2—C121.6912 (16)C4—H4C0.9600
O1—N11.3769 (18)C5—C61.478 (2)
O1—H1O10.79 (2)C5—C71.495 (2)
O2—N51.3791 (18)C6—C81.495 (2)
O2—H1O20.83 (2)C7—H7A0.9600
N1—C21.290 (2)C7—H7B0.9600
N2—C11.290 (2)C7—H7C0.9600
N2—N31.3538 (19)C8—H8A0.9600
N3—C91.366 (2)C8—H8B0.9600
N3—H1N30.76 (2)C8—H8C0.9600
N4—C91.318 (2)C10—C111.497 (3)
N4—C101.450 (3)C10—H10A0.9700
N4—H1N40.73 (2)C10—H10B0.9700
N5—C61.2873 (19)C11—H11A0.9600
N6—C51.288 (2)C11—H11B0.9600
N6—N71.3656 (19)C11—H11C0.9600
N7—C121.362 (2)C13—C141.503 (3)
N7—H1N70.87 (2)C13—H13A0.9700
N8—C121.324 (2)C13—H13B0.9700
N8—C131.454 (3)C14—H14A0.9600
N8—H1N80.85 (2)C14—H14B0.9600
C1—C21.479 (2)C14—H14C0.9600
N6—Ni1—N2177.98 (5)C2—C4—H4A109.5
N6—Ni1—N1102.68 (5)C2—C4—H4B109.5
N2—Ni1—N175.81 (5)H4A—C4—H4B109.5
N6—Ni1—N576.02 (5)C2—C4—H4C109.5
N2—Ni1—N5105.19 (5)H4A—C4—H4C109.5
N1—Ni1—N588.68 (5)H4B—C4—H4C109.5
N6—Ni1—S198.49 (4)N6—C5—C6114.12 (13)
N2—Ni1—S183.14 (4)N6—C5—C7124.67 (16)
N1—Ni1—S1158.21 (4)C6—C5—C7121.21 (14)
N5—Ni1—S191.49 (4)N5—C6—C5114.95 (13)
N6—Ni1—S282.53 (4)N5—C6—C8123.77 (16)
N2—Ni1—S296.22 (4)C5—C6—C8121.26 (14)
N1—Ni1—S295.08 (4)C5—C7—H7A109.5
N5—Ni1—S2158.53 (4)C5—C7—H7B109.5
S1—Ni1—S292.701 (19)H7A—C7—H7B109.5
C9—S1—Ni195.24 (6)C5—C7—H7C109.5
C12—S2—Ni195.63 (6)H7A—C7—H7C109.5
N1—O1—H1O1107.0 (17)H7B—C7—H7C109.5
N5—O2—H1O2107.9 (17)C6—C8—H8A109.5
C2—N1—O1112.67 (14)C6—C8—H8B109.5
C2—N1—Ni1115.53 (11)H8A—C8—H8B109.5
O1—N1—Ni1131.80 (10)C6—C8—H8C109.5
C1—N2—N3120.53 (13)H8A—C8—H8C109.5
C1—N2—Ni1119.84 (11)H8B—C8—H8C109.5
N3—N2—Ni1119.56 (10)N4—C9—N3114.52 (14)
N2—N3—C9119.17 (12)N4—C9—S1122.91 (13)
N2—N3—H1N3118.9 (16)N3—C9—S1122.57 (12)
C9—N3—H1N3118.3 (16)N4—C10—C11109.65 (17)
C9—N4—C10125.00 (15)N4—C10—H10A109.7
C9—N4—H1N4116.9 (17)C11—C10—H10A109.7
C10—N4—H1N4118.1 (17)N4—C10—H10B109.7
C6—N5—O2113.58 (13)C11—C10—H10B109.7
C6—N5—Ni1114.95 (11)H10A—C10—H10B108.2
O2—N5—Ni1131.47 (10)C10—C11—H11A109.5
C5—N6—N7120.14 (13)C10—C11—H11B109.5
C5—N6—Ni1119.40 (11)H11A—C11—H11B109.5
N7—N6—Ni1120.38 (9)C10—C11—H11C109.5
C12—N7—N6118.52 (13)H11A—C11—H11C109.5
C12—N7—H1N7118.8 (14)H11B—C11—H11C109.5
N6—N7—H1N7118.0 (14)N8—C12—N7114.94 (15)
C12—N8—C13125.52 (17)N8—C12—S2122.81 (13)
C12—N8—H1N8114.4 (15)N7—C12—S2122.22 (12)
C13—N8—H1N8119.9 (15)N8—C13—C14109.5 (2)
N2—C1—C2114.04 (13)N8—C13—H13A109.8
N2—C1—C3124.57 (15)C14—C13—H13A109.8
C2—C1—C3121.38 (15)N8—C13—H13B109.8
N1—C2—C1114.65 (14)C14—C13—H13B109.8
N1—C2—C4123.84 (17)H13A—C13—H13B108.2
C1—C2—C4121.51 (15)C13—C14—H14A109.5
C1—C3—H3A109.5C13—C14—H14B109.5
C1—C3—H3B109.5H14A—C14—H14B109.5
H3A—C3—H3B109.5C13—C14—H14C109.5
C1—C3—H3C109.5H14A—C14—H14C109.5
H3A—C3—H3C109.5H14B—C14—H14C109.5
H3B—C3—H3C109.5
N6—Ni1—S1—C9176.16 (7)N1—Ni1—N6—N791.00 (12)
N2—Ni1—S1—C9−2.63 (6)N5—Ni1—N6—N7176.39 (13)
N1—Ni1—S1—C9−17.59 (12)S1—Ni1—N6—N7−94.19 (12)
N5—Ni1—S1—C9−107.75 (6)S2—Ni1—N6—N7−2.56 (11)
S2—Ni1—S1—C993.31 (6)C5—N6—N7—C12−179.00 (16)
N6—Ni1—S2—C125.33 (7)Ni1—N6—N7—C12−2.5 (2)
N2—Ni1—S2—C12−173.07 (7)N3—N2—C1—C2−179.18 (14)
N1—Ni1—S2—C12−96.83 (7)Ni1—N2—C1—C24.00 (18)
N5—Ni1—S2—C122.54 (13)N3—N2—C1—C3−0.5 (2)
S1—Ni1—S2—C12103.55 (6)Ni1—N2—C1—C3−177.35 (13)
N6—Ni1—N1—C2−176.40 (12)O1—N1—C2—C1178.83 (13)
N2—Ni1—N1—C22.22 (11)Ni1—N1—C2—C1−0.92 (18)
N5—Ni1—N1—C2108.25 (12)O1—N1—C2—C4−0.7 (3)
S1—Ni1—N1—C217.54 (19)Ni1—N1—C2—C4179.55 (16)
S2—Ni1—N1—C2−92.93 (12)N2—C1—C2—N1−1.9 (2)
N6—Ni1—N1—O13.91 (15)C3—C1—C2—N1179.44 (15)
N2—Ni1—N1—O1−177.48 (15)N2—C1—C2—C4177.68 (18)
N5—Ni1—N1—O1−71.44 (15)C3—C1—C2—C4−1.0 (3)
S1—Ni1—N1—O1−162.15 (10)N7—N6—C5—C6−175.83 (14)
S2—Ni1—N1—O187.38 (14)Ni1—N6—C5—C67.6 (2)
N1—Ni1—N2—C1−3.45 (12)N7—N6—C5—C73.9 (3)
N5—Ni1—N2—C1−88.10 (12)Ni1—N6—C5—C7−172.64 (15)
S1—Ni1—N2—C1−177.77 (12)O2—N5—C6—C5177.75 (14)
S2—Ni1—N2—C190.24 (12)Ni1—N5—C6—C5−3.03 (19)
N1—Ni1—N2—N3179.70 (12)O2—N5—C6—C8−0.7 (2)
N5—Ni1—N2—N395.05 (12)Ni1—N5—C6—C8178.50 (15)
S1—Ni1—N2—N35.37 (11)N6—C5—C6—N5−2.7 (2)
S2—Ni1—N2—N3−86.61 (11)C7—C5—C6—N5177.58 (17)
C1—N2—N3—C9176.31 (14)N6—C5—C6—C8175.84 (17)
Ni1—N2—N3—C9−6.9 (2)C7—C5—C6—C8−3.9 (3)
N6—Ni1—N5—C65.21 (12)C10—N4—C9—N3−173.91 (17)
N2—Ni1—N5—C6−176.46 (12)C10—N4—C9—S15.8 (3)
N1—Ni1—N5—C6108.63 (12)N2—N3—C9—N4−176.40 (14)
S1—Ni1—N5—C6−93.17 (12)N2—N3—C9—S13.9 (2)
S2—Ni1—N5—C68.1 (2)Ni1—S1—C9—N4−179.39 (14)
N6—Ni1—N5—O2−175.74 (15)Ni1—S1—C9—N30.27 (14)
N2—Ni1—N5—O22.59 (15)C9—N4—C10—C11174.47 (19)
N1—Ni1—N5—O2−72.32 (14)C13—N8—C12—N7−178.54 (19)
S1—Ni1—N5—O285.88 (14)C13—N8—C12—S2−0.6 (3)
S2—Ni1—N5—O2−172.89 (10)N6—N7—C12—N8−173.06 (16)
N1—Ni1—N6—C5−92.46 (13)N6—N7—C12—S28.9 (2)
N5—Ni1—N6—C5−7.07 (12)Ni1—S2—C12—N8173.07 (15)
S1—Ni1—N6—C582.35 (13)Ni1—S2—C12—N7−9.10 (15)
S2—Ni1—N6—C5173.99 (13)C12—N8—C13—C14−165.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H1N4···Cl1i0.730 (19)2.47 (2)3.1689 (17)161 (2)
O2—H1O2···Cl10.84 (3)2.20 (3)3.0062 (14)161 (2)
N7—H1N7···Cl2ii0.87 (2)2.34 (2)3.1488 (16)153.9 (17)
N3—H1N3···Cl1i0.76 (2)2.50 (2)3.2015 (16)154 (2)
O1—H1O1···Cl20.79 (3)2.20 (3)2.9396 (16)157 (2)
N8—H1N8···Cl2ii0.85 (2)2.349 (19)3.1567 (19)159 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5020).

References

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