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The title compound, [di­acetyl­pyridine bis(S-methyl­iso­thio­semicarbazonato)]­iodo­nickel(II), [Ni(C13H18N7S2)I], is the first example of a complex involving the 2N coordination of the iso­thio­semicarbazide moiety. 2,6-Di­acetyl­pyridine bis(S-methyl­iso­thio­semicarbazone), as a potentially pentadentate ligand (N5), is coordinated as a tetradentate species, whereby one (deprotonated) iso­thio­semicarbazide moiety is coordinated in the usual way (1N4N), but the other (neutral) is bonded via the 2N atom only, the fourth ligator being the pyridine nitro­gen. The difference in coordination mode of the iso­thio­semicarbazide moiety is reflected in the 1N-2N bond lengths of 1.359 (4) and 1.379 (3) Å in the deprotonated and undeprotonated moieties, respectively. The structure contains three fused chelate rings in a 5:5:6 arrangement. The six-membered ring has a non-planar conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007228/na1472sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007228/na1472Isup2.hkl
Contains datablock I

CCDC reference: 150313

Comment top

Up to now, more than 60 metal complexes with isothiosemicarbazides and isothiosemicarbazones of different dentacity have been characterized by X-ray analysis (Malinovskii et al., 1985; Obadović et al., 1997; Bogdanović et al., 1999). At that, it has been found that the isothiosemicarbazone moiety is coordinated via the terminal nitrogen atoms 1N and 4N. To our knowledge, the only exceptions are the NiII complex with diacethylmonoxime S-methylisothiosemicarbazone (Biyuskin et al., 1986) and the PdII complex with salicylaldehyde S-methylisothiosemicarbazide (Revenko et al., 1996), in which the isothiosemicarbazide moiety is coordinated only via 1N and 1N plus the alkylated sulfur atom, respectively.

The common 1N4N coordination mode of both isothiosemicarbazide moieties has also been found in the pentagonal-bipyramidal MnII complex with 2,6-diacetylpyridine bis(S-methylisothiosemicarbazone) (L) as a pentadentate ligand (N5), of the formula [Mn(NCS)L(MeOH)]NCS (Leovac et al., 1997).

The solved crystal structure of the NiII complex with the monoanion of this ligand (L—H), (I), described in the present work, represents the first example of a new mode of coordination of this class of ligands. Namely, one isothiosemicarbazide moiety is coordinated only through the nitrogen atom 2N which, together with common 1N4N coordination of the other (deprotonated) isothiosemicarbazide moiety and the pyridine nitrogen, gives rise to a tetradentate character of this ligand (Fig. 1). \sch

The consequence of such an asymmetric coordination is most clearly seen as the difference in the N1—N2 and N1'-N2' bond lengths, which are 1.379 (3) and 1.359 (3) Å, as well as the location of the hydrogen atom in the neutrally coordinated isothiosemicarbazide fragment. Namely, if the isothiosemicarbazide moiety is coordinated in its neutral form in the usual way, one of the hydrogen atoms is always bound to 2N: 1N—2NH— 3C(—SR) 4NH (imido form), so that this fragment has an E configuration. Such an instance has also been found in the structure of the previously mentioned MnII complex with L, in which a bidentate coordination (1N4N) in the imido-form has been observed for the both isothiosemicarbazide fragments. In contrast to this, the neutral free ligands (Argay et al., 1983; Bourosh et al., 1987; Bourosh et al., 1989; Simonov et al., 1990) are characterized by a Z configuration with both H atoms located on the 4N atom: 1N—2N 3C(—SR)—4NH2 (amido form). Because of the absence of the coordinated N3 atom in the titled Ni II complex, undeprotonated isothiosemicarbazide fragment from this complex retains a Z configuration and amido form as in the case with the non-coordinated ligands (contrary to the coordinated ligands).

The Ni atom is located in a pseudo-square-pyramidal surroundings (with the tetradentate ligand around the central ion in the basal plane and the I atom in the apical position). The bond Ni—I of 3.485 (2) Å is very elongated, and it can be considered as an electrostatic interaction between the two atoms. However, considering that the iodine is situated in the regular apical position, with angles to the corresponding coordinated atoms from the basal plane of less than 100.4°, it can be supposed that the Ni atom is in a pseudo-square-pyramidal surroundings. The basal coordination plane is slightly puckered showing a tetrahedral distortion with a maximum displacement of 0.097 (3) Å, while the Ni atom is displaced by 0.0495 (13) Å from this plane towards the apical iodine.

The basal coordination plane is characterized by the very deformed angles between the coordinated atoms and metal atom. The largest deviation shows the angle N2—Ni—N3', which is a consequence of the steric hindrance between the N3'H and N3H2 groups with the closest distance of 2.31 (5) Å between the hydrogen atoms. The N1', N2', C1', N3' fragment is nearly planar with a torsion angle of 3.4 (4)°, which is commonly observed with the isothiosemicarbazide ligands. However, in contrast to it, the corresponding N1, N2, C1, N3 fragment is not planar, the torsion angle being 167.5 (3)°. This difference is also a consequence of the ligand tendency to diminish the repulsion of the N3'H and N3H2 groups. The Ni—N1' distance is significantly shorter than the distances to the other nitrogen atoms, which could be related to the distribution of the negative charge on the deprotonated isothiosemicarbazide fragment to which N1' belongs.

The five-membered rings are almost planar. Their total puckering amplitudes are 0.074 (3) and 0.052 (2) Å for Ni,N1',N2',C1'N3' and Ni,N1',C3',C9,N4 showing half-chair and envelop conformation, respectively. The six-membered chelate ring is puckered and it assumes the conformation between half-chair and envelope, which can be explained in terms of the 6S7 form (Boeyens, 1978) (the Ni atom was taken as the first atom in the ring). The puckering parameters (Cremer & Pople, 1975) for Ni,N4,C5,C3,N1,N2 sequence are q2 = 0.210 (3) Å, q3 = −0.079 (3) Å, Q = 0.224 (3) Å, θ = 110.7 (9)° and ϕ = 139.4 (8)°. The maximum deviation from the best plane is 0.292 (3) Å for the N2 atom.

The crystal-packing arrangement in (I) consists of parallel layers with a shortest distance C1'···C8i of 3.455 (5) Å [symmetry code: (i) −x + 1, −y + 1, −z + 1). Inside the layers the shortest contact is between the sulfur atoms: S2···S2ii = 3.364 (2) Å [symmetry code: (ii) −x + 1, −y + 1, −z].

Experimental top

The dark-brown diamagnetic monocrystals of the title complex result from a template synthesis, i.e. the reaction of equimolar amounts of warm MeOH solutions (reflux, 40 min) of NiL'2I2 (L' = 3-methylisothiosemicarbazide) (Leovac et al., 1980) and 2,6-diacetylpyridine.

Refinement top

The structure was solved by Patterson and difference Fourier methods and refined by full-matrix least-squares methods. All H atoms were found in difference Fourier maps, but those connected to C atoms were placed at calculated positions using a riding model [isotropic displacement parameters equal to 1.2 (or 1.5 for methyl H atoms) times the equivalent isotropic displacement parameter of the parent atom]. The intensities were corrected for absorption with the program ABSORB (DeTitta, 1985).

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); data reduction: a local modification of MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I) showing the atom labels. Displacement ellipsoids are shown at the 50% probability level.
[2,6-diacetylpyridine bis(S-methylisothiosemicarbazone)]iodonickel(II) top
Crystal data top
[Ni(C13H18N7S2)I]Z = 2
Mr = 522.07F(000) = 516
Triclinic, P1Dx = 1.878 Mg m3
a = 7.713 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.653 (3) ÅCell parameters from 23 reflections
c = 12.535 (3) Åθ = 12.1–16.6°
α = 108.08 (5)°µ = 2.96 mm1
β = 101.01 (4)°T = 293 K
γ = 101.51 (6)°Prismatic, dark-brown
V = 923.4 (4) Å30.34 × 0.29 × 0.28 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2926 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.3°, θmin = 3.6°
ο/2θ scansh = 99
Absorption correction: integration
(ABSORB; De Titta, 1985)
k = 1212
Tmin = 0.363, Tmax = 0.437l = 1415
4230 measured reflections2 standard reflections every 120 min
3325 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 1.36Calculated w = 1/[σ2(Fo2) + (0.0337P)2 + 0.0788P]
where P = (Fo2 + 2Fc2)/3
3325 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.71 e Å3
Crystal data top
[Ni(C13H18N7S2)I]γ = 101.51 (6)°
Mr = 522.07V = 923.4 (4) Å3
Triclinic, P1Z = 2
a = 7.713 (2) ÅMo Kα radiation
b = 10.653 (3) ŵ = 2.96 mm1
c = 12.535 (3) ÅT = 293 K
α = 108.08 (5)°0.34 × 0.29 × 0.28 mm
β = 101.01 (4)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2926 reflections with I > 2σ(I)
Absorption correction: integration
(ABSORB; De Titta, 1985)
Rint = 0.020
Tmin = 0.363, Tmax = 0.4372 standard reflections every 120 min
4230 measured reflections intensity decay: none
3325 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 1.36Δρmax = 0.79 e Å3
3325 reflectionsΔρmin = 0.71 e Å3
229 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I0.18566 (3)0.16205 (2)0.170131 (19)0.05443 (10)
Ni0.26735 (5)0.24242 (4)0.33439 (3)0.03389 (11)
S20.41127 (14)0.40533 (10)0.07212 (8)0.0532 (2)
N1'0.2894 (3)0.4240 (2)0.3531 (2)0.0365 (6)
N2'0.3214 (4)0.4686 (3)0.2663 (2)0.0436 (6)
N3'0.3390 (4)0.2432 (3)0.1986 (2)0.0414 (6)
C2'0.3933 (6)0.2423 (4)0.0329 (3)0.0567 (9)
H2'10.42370.25470.10040.085*
H2'20.26980.18460.05510.085*
H2'30.47660.19980.00030.085*
C1'0.3520 (4)0.3633 (3)0.1876 (3)0.0402 (7)
C3'0.2651 (4)0.5032 (3)0.4482 (3)0.0370 (6)
C4'0.2767 (5)0.6521 (3)0.4761 (3)0.0466 (8)
H4'10.29820.67770.41170.070*
H4'20.37610.70610.54460.070*
H4'30.16340.66810.48980.070*
S10.22480 (13)0.20741 (8)0.22971 (8)0.0475 (2)
N10.2571 (4)0.0114 (3)0.4129 (2)0.0412 (6)
N20.2342 (4)0.0565 (2)0.3206 (2)0.0366 (5)
N30.1398 (5)0.0394 (3)0.1206 (3)0.0484 (7)
C10.1994 (4)0.0510 (3)0.2211 (3)0.0374 (7)
C20.1374 (6)0.3225 (4)0.0806 (4)0.0586 (10)
H2A0.14530.41280.07560.088*
H2B0.20870.29070.03450.088*
H2C0.01130.32550.05210.088*
C30.2496 (4)0.0831 (3)0.5147 (3)0.0397 (7)
C40.2694 (6)0.0132 (4)0.6019 (3)0.0556 (9)
H4A0.28430.07620.56550.083*
H4B0.16150.00390.62950.083*
H4C0.37520.06720.66630.083*
N40.2373 (3)0.2970 (2)0.4858 (2)0.0340 (5)
C50.2243 (4)0.2217 (3)0.5537 (3)0.0362 (6)
C60.1910 (5)0.2764 (4)0.6621 (3)0.0448 (8)
H60.17690.22300.70780.054*
C70.1792 (5)0.4094 (4)0.7011 (3)0.0505 (8)
H70.15460.44530.77250.061*
C80.2038 (5)0.4890 (3)0.6346 (3)0.0466 (8)
H80.20040.58000.66130.056*
C90.2336 (4)0.4308 (3)0.5268 (3)0.0355 (6)
H100.380 (5)0.191 (4)0.154 (3)0.051 (11)*
H110.105 (6)0.028 (5)0.114 (4)0.067 (13)*
H120.135 (5)0.102 (4)0.056 (4)0.059 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.07527 (18)0.05148 (16)0.04053 (14)0.03428 (13)0.01922 (11)0.00955 (11)
Ni0.0480 (2)0.0260 (2)0.0320 (2)0.01316 (16)0.01684 (17)0.01086 (16)
S20.0749 (6)0.0474 (5)0.0471 (5)0.0148 (4)0.0263 (4)0.0259 (4)
N1'0.0443 (14)0.0279 (13)0.0389 (14)0.0095 (11)0.0147 (11)0.0127 (11)
N2'0.0560 (16)0.0350 (14)0.0483 (16)0.0146 (12)0.0210 (13)0.0210 (12)
N3'0.0597 (17)0.0349 (14)0.0407 (15)0.0196 (13)0.0254 (13)0.0178 (12)
C2'0.067 (2)0.061 (2)0.0426 (19)0.0158 (19)0.0204 (17)0.0176 (18)
C1'0.0448 (17)0.0398 (17)0.0405 (17)0.0121 (14)0.0145 (14)0.0188 (14)
C3'0.0386 (15)0.0274 (15)0.0405 (16)0.0092 (12)0.0085 (13)0.0075 (13)
C4'0.055 (2)0.0274 (16)0.055 (2)0.0134 (14)0.0130 (16)0.0121 (15)
S10.0674 (5)0.0288 (4)0.0474 (5)0.0164 (4)0.0161 (4)0.0130 (4)
N10.0588 (16)0.0312 (13)0.0364 (14)0.0140 (12)0.0132 (12)0.0150 (11)
N20.0520 (15)0.0286 (13)0.0308 (12)0.0129 (11)0.0132 (11)0.0108 (11)
N30.077 (2)0.0333 (15)0.0349 (15)0.0267 (15)0.0126 (14)0.0062 (13)
C10.0471 (17)0.0324 (15)0.0380 (16)0.0157 (13)0.0185 (13)0.0129 (13)
C20.071 (2)0.0321 (18)0.062 (2)0.0161 (17)0.0146 (19)0.0027 (17)
C30.0469 (17)0.0370 (17)0.0342 (16)0.0070 (13)0.0108 (13)0.0145 (14)
C40.084 (3)0.048 (2)0.0428 (19)0.0193 (19)0.0193 (18)0.0253 (17)
N40.0398 (13)0.0293 (13)0.0311 (12)0.0094 (10)0.0111 (10)0.0077 (10)
C50.0395 (15)0.0347 (16)0.0311 (15)0.0061 (13)0.0093 (12)0.0100 (13)
C60.0537 (19)0.0466 (19)0.0321 (16)0.0087 (15)0.0147 (14)0.0129 (14)
C70.058 (2)0.053 (2)0.0343 (17)0.0144 (17)0.0195 (15)0.0045 (15)
C80.0512 (19)0.0351 (17)0.0439 (18)0.0109 (14)0.0168 (15)0.0004 (15)
C90.0374 (15)0.0286 (15)0.0350 (15)0.0089 (12)0.0100 (12)0.0043 (12)
Geometric parameters (Å, º) top
Ni—N1'1.844 (2)S1—C21.793 (4)
Ni—N41.879 (2)N1—C31.286 (4)
Ni—N3'1.890 (3)N1—N21.379 (3)
Ni—N21.893 (3)N2—C11.343 (4)
S2—C1'1.754 (3)N3—C11.308 (4)
S2—C2'1.785 (4)C3—C51.471 (4)
N1'—C3'1.300 (4)C3—C41.503 (4)
N1'—N2'1.359 (4)N4—C51.342 (4)
N2'—C1'1.339 (4)N4—C91.365 (4)
N3'—C1'1.315 (4)C5—C61.397 (4)
C3'—C91.454 (4)C6—C71.375 (5)
C3'—C4'1.494 (4)C7—C81.373 (5)
S1—C11.750 (3)C8—C91.385 (4)
N1'—Ni—N483.92 (12)C1—N2—Ni125.9 (2)
N1'—Ni—N3'80.91 (12)N1—N2—Ni125.0 (2)
N4—Ni—N3'162.78 (12)N3—C1—N2120.1 (3)
N1'—Ni—N2176.51 (11)N3—C1—S1121.3 (2)
N4—Ni—N293.21 (12)N2—C1—S1118.5 (2)
N3'—Ni—N2102.21 (12)N1—C3—C5127.9 (3)
C1'—S2—C2'103.2 (2)N1—C3—C4114.3 (3)
C3'—N1'—N2'122.6 (3)C5—C3—C4117.8 (3)
C3'—N1'—Ni117.7 (2)C5—N4—C9119.9 (3)
N2'—N1'—Ni119.6 (2)C5—N4—Ni127.6 (2)
C1'—N2'—N1'105.8 (2)C9—N4—Ni112.5 (2)
C1'—N3'—Ni110.8 (2)N4—C5—C6120.0 (3)
N3'—C1'—N2'122.4 (3)N4—C5—C3119.7 (3)
N3'—C1'—S2125.1 (3)C6—C5—C3120.3 (3)
N2'—C1'—S2112.5 (2)C7—C6—C5119.9 (3)
N1'—C3'—C9111.7 (3)C8—C7—C6120.0 (3)
N1'—C3'—C4'124.3 (3)C7—C8—C9118.6 (3)
C9—C3'—C4'123.9 (3)N4—C9—C8121.5 (3)
C1—S1—C2102.7 (2)N4—C9—C3'113.9 (3)
C3—N1—N2122.5 (3)C8—C9—C3'124.6 (3)
C1—N2—N1108.9 (2)
N4—Ni—N1'—C3'4.2 (2)C2—S1—C1—N33.9 (3)
N3'—Ni—N1'—C3'176.1 (3)C2—S1—C1—N2173.0 (3)
N2—Ni—N1'—C3'30 (2)N2—N1—C3—C52.6 (5)
N4—Ni—N1'—N2'178.7 (2)N2—N1—C3—C4177.3 (3)
N3'—Ni—N1'—N2'6.9 (2)N1'—Ni—N4—C5174.2 (3)
N2—Ni—N1'—N2'147 (2)N3'—Ni—N4—C5145.9 (4)
C3'—N1'—N2'—C1'175.8 (3)N2—Ni—N4—C57.8 (3)
Ni—N1'—N2'—C1'7.4 (3)N1'—Ni—N4—C94.2 (2)
N1'—Ni—N3'—C1'4.3 (2)N3'—Ni—N4—C932.6 (5)
N4—Ni—N3'—C1'32.9 (5)N2—Ni—N4—C9173.8 (2)
N2—Ni—N3'—C1'174.1 (2)C9—N4—C5—C65.5 (4)
Ni—N3'—C1'—N2'1.5 (4)Ni—N4—C5—C6176.1 (2)
Ni—N3'—C1'—S2178.9 (2)C9—N4—C5—C3173.0 (3)
N1'—N2'—C1'—N3'3.5 (4)Ni—N4—C5—C35.3 (4)
N1'—N2'—C1'—S2176.1 (2)N1—C3—C5—N411.3 (5)
C2'—S2—C1'—N3'12.9 (3)C4—C3—C5—N4168.7 (3)
C2'—S2—C1'—N2'167.5 (3)N1—C3—C5—C6170.1 (3)
N2'—N1'—C3'—C9179.9 (2)C4—C3—C5—C69.8 (5)
Ni—N1'—C3'—C93.2 (3)N4—C5—C6—C72.7 (5)
N2'—N1'—C3'—C4'2.6 (5)C3—C5—C6—C7175.9 (3)
Ni—N1'—C3'—C4'179.5 (2)C5—C6—C7—C81.3 (5)
C3—N1—N2—C1163.4 (3)C6—C7—C8—C92.3 (5)
C3—N1—N2—Ni21.4 (4)C5—N4—C9—C84.6 (4)
N1'—Ni—N2—C1130 (2)Ni—N4—C9—C8176.9 (2)
N4—Ni—N2—C1164.7 (3)C5—N4—C9—C3'174.9 (3)
N3'—Ni—N2—C123.0 (3)Ni—N4—C9—C3'3.7 (3)
N1'—Ni—N2—N156 (2)C7—C8—C9—N40.6 (5)
N4—Ni—N2—N121.0 (3)C7—C8—C9—C3'178.8 (3)
N3'—Ni—N2—N1151.3 (2)N1'—C3'—C9—N40.5 (4)
N1—N2—C1—N3167.5 (3)C4'—C3'—C9—N4176.9 (3)
Ni—N2—C1—N317.4 (4)N1'—C3'—C9—C8179.9 (3)
N1—N2—C1—S19.4 (3)C4'—C3'—C9—C82.6 (5)
Ni—N2—C1—S1165.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H11···I0.84 (6)2.97 (5)3.635 (4)138 (4)
N3—H12···Ii0.86 (4)2.83 (5)3.583 (4)147 (4)
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formula[Ni(C13H18N7S2)I]
Mr522.07
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.713 (2), 10.653 (3), 12.535 (3)
α, β, γ (°)108.08 (5), 101.01 (4), 101.51 (6)
V3)923.4 (4)
Z2
Radiation typeMo Kα
µ (mm1)2.96
Crystal size (mm)0.34 × 0.29 × 0.28
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionIntegration
(ABSORB; De Titta, 1985)
Tmin, Tmax0.363, 0.437
No. of measured, independent and
observed [I > 2σ(I)] reflections
4230, 3325, 2926
Rint0.020
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.070, 1.36
No. of reflections3325
No. of parameters229
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.79, 0.71

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), a local modification of MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
Ni—N1'1.844 (2)N2'—C1'1.339 (4)
Ni—N41.879 (2)N3'—C1'1.315 (4)
Ni—N3'1.890 (3)N1—C31.286 (4)
Ni—N21.893 (3)N1—N21.379 (3)
N1'—C3'1.300 (4)N2—C11.343 (4)
N1'—N2'1.359 (4)N3—C11.308 (4)
N1'—Ni—N483.92 (12)N1'—Ni—N2176.51 (11)
N1'—Ni—N3'80.91 (12)N4—Ni—N293.21 (12)
N4—Ni—N3'162.78 (12)N3'—Ni—N2102.21 (12)
C3—N1—N2—Ni21.4 (4)N2—Ni—N4—C57.8 (3)
N4—Ni—N2—N121.0 (3)Ni—N4—C5—C35.3 (4)
N2—N1—C3—C52.6 (5)N1—C3—C5—N411.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H11···I0.84 (6)2.97 (5)3.635 (4)138 (4)
N3—H12···Ii0.86 (4)2.83 (5)3.583 (4)147 (4)
Symmetry code: (i) x, y, z.
 

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