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The title compound, (2,6-diacetyl­pyridine bis­{[2-(hydroxy­imino)­propanoyl]­hydrazone}(2-))nickel(II) dimethyl sulfox­ide solvate monohydrate, [Ni(C15H17N7O4)]·C2H6OS·H2O, represents the first example of square-planar N4 coordination via N atoms with four different functions, namely amide, azomethine, hydroxyimino and pyridine. The coordination poly­hedron of the central Ni atom has a slightly distorted square-planar geometry. The 2,6-diacetyl­pyridine bis­{[2-(hy­droxy­imino)­propanoyl]­hydrazone} ligand forms one six- and two five-membered chelate rings, and a pseudo-chelate ring through an intra­molecular hydrogen bond with an amide group as donor and a deprotonated hydroxyimino group as acceptor, resulting in a pseudomacrocyclic arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108003065/fa3126sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108003065/fa3126Isup2.hkl
Contains datablock I

CCDC reference: 682800

Comment top

2,6-Diacetylpyridine acylhydrazones and bis(acylhydrazones) are an interesting class of compounds due to their ability to form stable metal complexes, their versatility as chelating agents and their flexibility in assuming different conformations (Wester & Palenik, 1974; Carcelli et al., 1999; Kasuga et al., 2003). Complexes of this type of ligand with 3 d metals reveal biological activity and can be used in bioinorganic modelling of active sites of redox and hydrolytic enzymes. To date, more than 65 complexes based on 2,6-diacetylpyridine derivatives of different compositions have been characterized by X-ray crystallographic analysis. In almost all cases the ligands are five-coordinated via pyridine, two azomethine N atoms and two O or S atoms (Pelizzi et al., 1986). The title compound, [Ni(C15H17N7O4]·DMSO·H2O, (I) (DMSO is dimethyl sulfoxide), is a complex of NiII with a novel polynucleative derivative of 2,6-diacetylpyridine, namely 2,6-diacetylpyridine bis(2-(hydroxymino)propanehydrazide), L. The presence of three powerful chelate centres in the ligand may be used for obtaining polynuclear metal complexes (see the second scheme).

The structure of (I) consists of the neutral asymmetric complex and solvent DMSO and water molecules (Fig. 1). Thus ligand L is doubly deprotonated at the amide (N3) and oximic (O2) groups, which was confirmed by 1H NMR data. Compound (I) represents the first example of square-planar N4 coordination via N atoms of different functions, namely amide (N3), azomethine (N5), oximic (N4) and pyridine (N1). A structure reported by Simonov et al. (1993) contains the NiN4 chromophore with four chemically different N atoms but the groups are the same: oximic and hydrazone.

The Ni—N coordination bond lengths (Table 1) fall in the range 1.828 (3)–1.888 (3) Å and are typical for square-planar NiII complexes with deprotonated amide ligands (Leininger et al., 2000; Leovac et al., 2000; Hlavica & Lewis, 2001; Moroz et al., 2006). The azomethine double-bond distances N2C6 and N5C11 [1.295 (5) and 1.301 (4) Å, respectively] are about the same. On the other hand, the N2—N3 [1.355 (4) Å] and N4—O2 [1.320 (4) Å] bonds are shorter than the N5—N6 [1.394 (4) Å] and N7—O4 [1.392 (4) Å] bonds. The differences can be explained by the deprotonation of atoms N3 and O2. As a result of the formation of five- and six-membered chelate rings, the bite angles around Ni1 deviate from ideal square-planar values (Table 1). The chelate rings are essentially planar. A pseudochelate ring is formed via the presence of an intramolecular hydrogen bond with amide atom N6 as donor and the deprotonated oximic group (O2) as acceptor (Table 2), resulting in a pseudomacrocyclic arrangement. The non-coordinated part of L is not planar, because of the tendency to reduce repulsion between CO and CH3 groups and also because of the presence of an intermolecular hydrogen bond with oximic group O4 as donor and DMSO as acceptor. The C11—N5—N6—C13 torsion angle is 60.5 (4)°.

The elements of the structure are connected through a system of hydrogen bonds and ππ stacking interactions. The solvent water molecules and protonated oximic groups (O4) act as donors, and amide (O3) and DMSO O atoms act as acceptors (Table 2). An extensive three-dimensional system of hydrogen bonds is formed (Fig. 2). The ππ stacking (3.45 Å) is realised between neighbouring molecules of the complex along the crystallographic a direction. Slabs of (I) form columns, with DMSO and water molecules between them.

Related literature top

For related literature, see: Carcelli et al. (1999); Fritsky et al. (1998); Hlavica & Lewis (2001); Kasuga et al. (2003); Leininger et al. (2000); Leovac et al. (2000); Moroz et al. (2006); Pelizzi et al. (1986); Simonov et al. (1993); Wester & Palenik (1974).

Experimental top

The synthesis of the ligand was carried out as follows. To 2-(hydroxymino)propanehydrazide (5 g, 0.043 mol) (Fritsky et al., 1998) dissolved in EtOH (20 ml), 2,6-diacetylpyridine (3.4 g, 0.021 mol) was added. The resulting mixture was heated for 1 h. After cooling, a white precipitate was formed. The precipitate was separated by filtration and recrystallized from dimethylformamide (yield 6.95 g, 91%). Spectroscopic analysis: 1H NMR (Solvent? Frequency?, δ, p.p.m.): 1.986 (6H, s, CH3), 2.432 (6H, s, CH3), 7.929 (1H, t, pyH), 8.086 (2H, d, pyH), 10.27 (2H, s, NH), 12.148 (2H, s, OH).

To prepare crystals of (I), NiCl2 6H2O (0,0291 g, 0,1 mmol) and L (0.0361 g, 0.1 mmol) were dissolved in DMSO (20 ml) and aqueous NaOH (1 ml, 0.1 mmol) was added. The mixture was heated for 40 min, filtered and left in a desiccator for crystallization. After one week, red crystals of (I) suitable for X-ray analysis were obtained (yield 0.0544 g, 45%). Spectroscopic analysis: 1H NMR (Solvent? Frequency?, δ, p.p.m.): 1.792 (3H, s, CH3), 1.979 (3H, s, CH3), 2.28 (3H, s, CH3), 2.518 (3H, s, CH3), 8.1 (1H, d, pyH), 8.171 (1H, d, pyH), 8.375 (1H, t, pyH), 12.332 (1H, s, NH), 15.485 (1H, s, OH).

Refinement top

OH and NH H atoms were located in a difference Fourier map but constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(parent atom). Other H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95–0.98 Å, and Uiso(H) = 1.2–1.5Ueq(parent atom). The highest peak is located 1.10 Å from atom H16B and the deepest hole is located 0.61 Å from atom S1.

Computing details top

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Compound (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are indicated by dashed lines.
[Figure 2] Fig. 2. A packing diagram for complex (I), projected along the a direction. Hydrogen bonds are indicated by dashed lines. H atoms have been omitted for clarity.
(2,6-Diacetylpyridine bis{[2-(hydroxyimino)propanoyl]hydrazone}(2-)]nickel(II) dimethyl sulfoxide solvate monohydrate top
Crystal data top
[Ni(C15H17N7O4)]·C2H6OS·H2OZ = 2
Mr = 514.21F(000) = 536
Triclinic, P1Dx = 1.614 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3076 (2) ÅCell parameters from 13132 reflections
b = 11.1899 (5) Åθ = 1.0–26.0°
c = 13.9875 (6) ŵ = 1.07 mm1
α = 74.652 (2)°T = 120 K
β = 84.472 (2)°Needle, red
γ = 73.641 (2)°0.19 × 0.05 × 0.03 mm
V = 1058.04 (7) Å3
Data collection top
Nonius KappaCCD
diffractometer
4128 independent reflections
Radiation source: fine-focus sealed tube3008 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.092
Detector resolution: 9 pixels mm-1θmax = 26.1°, θmin = 3.8°
ϕ scans and ω scans with κ offseth = 89
Absorption correction: multi-scan
[SADABS (Version 2.10; Sheldrick, 2003)]
k = 1213
Tmin = 0.822, Tmax = 0.965l = 1717
18361 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0292P)2 + 1.8037P]
where P = (Fo2 + 2Fc2)/3
4128 reflections(Δ/σ)max = 0.005
296 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
[Ni(C15H17N7O4)]·C2H6OS·H2Oγ = 73.641 (2)°
Mr = 514.21V = 1058.04 (7) Å3
Triclinic, P1Z = 2
a = 7.3076 (2) ÅMo Kα radiation
b = 11.1899 (5) ŵ = 1.07 mm1
c = 13.9875 (6) ÅT = 120 K
α = 74.652 (2)°0.19 × 0.05 × 0.03 mm
β = 84.472 (2)°
Data collection top
Nonius KappaCCD
diffractometer
4128 independent reflections
Absorption correction: multi-scan
[SADABS (Version 2.10; Sheldrick, 2003)]
3008 reflections with I > 2σ(I)
Tmin = 0.822, Tmax = 0.965Rint = 0.092
18361 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.06Δρmax = 0.49 e Å3
4128 reflectionsΔρmin = 0.43 e Å3
296 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.

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) top
xyzUiso*/Ueq
Ni10.19844 (7)0.05511 (5)0.41026 (3)0.01806 (15)
O10.2455 (4)0.3306 (3)0.52378 (19)0.0284 (6)
O20.0736 (4)0.2587 (2)0.23917 (18)0.0259 (6)
O30.3419 (4)0.1075 (2)0.15473 (19)0.0235 (6)
O40.0134 (4)0.2508 (3)0.05788 (18)0.0275 (6)
H4O0.08380.33530.05560.041*
O50.2621 (4)0.4760 (3)0.0573 (2)0.0293 (6)
O60.6060 (4)0.3151 (3)0.2933 (2)0.0366 (7)
H6O0.53180.24050.25760.055*
H6P0.64760.29020.34260.055*
N10.2541 (4)0.1106 (3)0.4948 (2)0.0185 (7)
N20.3044 (4)0.0765 (3)0.5981 (2)0.0214 (7)
N30.2456 (4)0.1297 (3)0.5035 (2)0.0199 (7)
N40.1358 (4)0.2244 (3)0.3306 (2)0.0196 (7)
N50.1554 (4)0.0295 (3)0.3178 (2)0.0176 (6)
N60.1019 (4)0.0331 (3)0.2204 (2)0.0190 (7)
H6N0.07360.11630.21780.029*
N70.0255 (4)0.1808 (3)0.0396 (2)0.0226 (7)
C10.2302 (5)0.2016 (3)0.4529 (3)0.0197 (8)
C20.2695 (5)0.3313 (4)0.5038 (3)0.0230 (8)
H20.25310.39380.47310.028*
C30.3327 (5)0.3665 (4)0.5998 (3)0.0274 (9)
H30.36190.45410.63580.033*
C40.3533 (5)0.2741 (4)0.6433 (3)0.0248 (9)
H40.39480.29810.70970.030*
C50.3130 (5)0.1437 (4)0.5895 (3)0.0199 (8)
C60.3345 (5)0.0458 (4)0.6367 (3)0.0222 (8)
C70.3969 (6)0.0885 (4)0.7429 (3)0.0272 (9)
H7A0.41460.01510.76310.041*
H7B0.51750.15600.74890.041*
H7C0.29910.12200.78580.041*
C80.2201 (5)0.2617 (3)0.4733 (3)0.0204 (8)
C90.1593 (5)0.3121 (3)0.3700 (3)0.0211 (8)
C100.1250 (6)0.4510 (4)0.3181 (3)0.0301 (9)
H10A0.16230.45940.24790.045*
H10B0.20090.49010.34840.045*
H10C0.01060.49460.32380.045*
C110.1635 (5)0.1510 (3)0.3504 (3)0.0174 (7)
C120.1019 (5)0.2308 (4)0.2976 (3)0.0233 (8)
H12A0.02220.17490.24200.035*
H12B0.02840.28360.34340.035*
H12C0.21430.28670.27260.035*
C130.2103 (5)0.0090 (3)0.1444 (3)0.0194 (8)
C140.1550 (5)0.0747 (3)0.0426 (3)0.0193 (8)
C150.2522 (6)0.0303 (4)0.0450 (3)0.0255 (9)
H15A0.15960.05200.09730.038*
H15B0.30690.06310.02580.038*
H15C0.35410.07260.06960.038*
S10.22590 (14)0.56401 (9)0.00002 (7)0.0261 (2)
C160.4258 (6)0.7008 (4)0.0204 (3)0.0320 (10)
H16A0.42130.75180.08890.048*
H16B0.42300.75340.02520.048*
H16C0.54350.67300.00870.048*
C170.2786 (7)0.4974 (4)0.1268 (3)0.0354 (10)
H17A0.40660.48420.13280.053*
H17B0.27330.55660.16640.053*
H17C0.18480.41480.15090.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0214 (3)0.0156 (3)0.0164 (2)0.00344 (18)0.00120 (18)0.00391 (18)
O10.0375 (16)0.0242 (15)0.0271 (15)0.0083 (12)0.0018 (12)0.0120 (12)
O20.0396 (16)0.0165 (14)0.0199 (14)0.0031 (12)0.0102 (12)0.0033 (11)
O30.0235 (14)0.0202 (14)0.0241 (14)0.0020 (11)0.0001 (11)0.0055 (11)
O40.0368 (16)0.0221 (14)0.0184 (14)0.0002 (12)0.0050 (11)0.0028 (11)
O60.0450 (18)0.0263 (16)0.0358 (17)0.0020 (13)0.0152 (14)0.0106 (13)
N10.0191 (16)0.0194 (16)0.0169 (16)0.0052 (13)0.0016 (12)0.0051 (13)
N20.0208 (16)0.0296 (19)0.0139 (16)0.0057 (14)0.0014 (12)0.0062 (14)
N30.0217 (16)0.0181 (16)0.0204 (16)0.0061 (13)0.0005 (13)0.0049 (13)
N40.0226 (16)0.0189 (16)0.0176 (16)0.0051 (13)0.0015 (13)0.0062 (13)
N50.0153 (15)0.0170 (16)0.0184 (16)0.0020 (12)0.0008 (12)0.0033 (13)
N60.0234 (16)0.0135 (15)0.0174 (16)0.0010 (12)0.0024 (13)0.0025 (12)
N70.0268 (17)0.0224 (17)0.0179 (16)0.0074 (14)0.0030 (13)0.0018 (13)
C10.0161 (18)0.0163 (19)0.026 (2)0.0036 (15)0.0046 (15)0.0068 (16)
C20.025 (2)0.020 (2)0.024 (2)0.0075 (16)0.0052 (16)0.0045 (16)
C30.027 (2)0.019 (2)0.028 (2)0.0030 (16)0.0001 (17)0.0044 (17)
C40.024 (2)0.025 (2)0.020 (2)0.0053 (16)0.0012 (16)0.0007 (16)
C50.0164 (18)0.022 (2)0.0176 (19)0.0027 (15)0.0035 (14)0.0027 (15)
C60.0198 (19)0.025 (2)0.0204 (19)0.0032 (16)0.0019 (15)0.0061 (16)
C70.023 (2)0.035 (2)0.020 (2)0.0023 (17)0.0010 (16)0.0071 (17)
C80.0178 (19)0.019 (2)0.027 (2)0.0061 (15)0.0040 (15)0.0107 (16)
C90.026 (2)0.0152 (19)0.024 (2)0.0067 (15)0.0001 (16)0.0072 (16)
C100.046 (3)0.0140 (19)0.030 (2)0.0060 (18)0.0071 (19)0.0045 (17)
C110.0191 (18)0.0148 (18)0.0189 (18)0.0049 (14)0.0022 (14)0.0056 (15)
C120.030 (2)0.020 (2)0.023 (2)0.0097 (16)0.0022 (16)0.0065 (16)
C130.0204 (19)0.0177 (19)0.0218 (19)0.0076 (16)0.0006 (15)0.0054 (15)
C140.0199 (19)0.0187 (19)0.0195 (19)0.0051 (15)0.0013 (15)0.0049 (15)
C150.030 (2)0.027 (2)0.020 (2)0.0051 (17)0.0023 (16)0.0079 (16)
S10.0251 (5)0.0215 (5)0.0305 (5)0.0040 (4)0.0029 (4)0.0060 (4)
O50.0319 (15)0.0226 (15)0.0329 (16)0.0026 (12)0.0057 (12)0.0094 (12)
C160.032 (2)0.023 (2)0.038 (2)0.0045 (18)0.0077 (19)0.0040 (18)
C170.046 (3)0.027 (2)0.029 (2)0.0038 (19)0.009 (2)0.0048 (18)
Geometric parameters (Å, º) top
Ni1—N31.828 (3)C4—H40.9500
Ni1—N11.873 (3)C5—C61.469 (5)
Ni1—N41.879 (3)C6—C71.508 (5)
Ni1—N51.888 (3)C7—H7A0.9800
O1—C81.234 (4)C7—H7B0.9800
O2—N41.320 (4)C7—H7C0.9800
O3—C131.227 (4)C8—C91.468 (5)
O4—N71.392 (4)C9—C101.491 (5)
O4—H4O0.9475C10—H10A0.9800
O6—H6O0.9039C10—H10B0.9800
O6—H6P0.9148C10—H10C0.9800
N1—C51.356 (5)C11—C121.477 (5)
N1—C11.358 (5)C12—H12A0.9800
N2—C61.295 (5)C12—H12B0.9800
N2—N31.355 (4)C12—H12C0.9800
N3—C81.387 (5)C13—C141.504 (5)
N4—C91.302 (5)C14—C151.485 (5)
N5—C111.301 (4)C15—H15A0.9800
N5—N61.394 (4)C15—H15B0.9800
N6—C131.368 (5)C15—H15C0.9800
N6—H6N0.8861S1—O51.512 (3)
N7—C141.287 (5)S1—C161.774 (4)
C1—C21.398 (5)S1—C171.783 (4)
C1—C111.471 (5)C16—H16A0.9800
C2—C31.382 (5)C16—H16B0.9800
C2—H20.9500C16—H16C0.9800
C3—C41.378 (6)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C51.415 (5)C17—H17C0.9800
N3—Ni1—N194.01 (13)O1—C8—N3126.3 (3)
N3—Ni1—N483.99 (13)O1—C8—C9122.8 (3)
N1—Ni1—N4177.21 (14)N3—C8—C9110.9 (3)
N3—Ni1—N5177.34 (13)N4—C9—C8113.3 (3)
N1—Ni1—N583.41 (13)N4—C9—C10124.5 (3)
N4—Ni1—N598.61 (13)C8—C9—C10122.2 (3)
N7—O4—H4O107.0C9—C10—H10A109.5
H6O—O6—H6P102.7C9—C10—H10B109.5
C5—N1—C1120.1 (3)H10A—C10—H10B109.5
C5—N1—Ni1126.1 (3)C9—C10—H10C109.5
C1—N1—Ni1113.8 (2)H10A—C10—H10C109.5
C6—N2—N3121.2 (3)H10B—C10—H10C109.5
N2—N3—C8114.1 (3)N5—C11—C1111.5 (3)
N2—N3—Ni1130.3 (2)N5—C11—C12126.4 (3)
C8—N3—Ni1115.6 (2)C1—C11—C12121.9 (3)
C9—N4—O2119.0 (3)C11—C12—H12A109.5
C9—N4—Ni1116.1 (2)C11—C12—H12B109.5
O2—N4—Ni1124.9 (2)H12A—C12—H12B109.5
C11—N5—N6119.3 (3)C11—C12—H12C109.5
C11—N5—Ni1117.0 (2)H12A—C12—H12C109.5
N6—N5—Ni1123.6 (2)H12B—C12—H12C109.5
C13—N6—N5119.0 (3)O3—C13—N6124.9 (3)
C13—N6—H6N117.9O3—C13—C14120.4 (3)
N5—N6—H6N105.3N6—C13—C14114.7 (3)
C14—N7—O4110.9 (3)N7—C14—C15125.6 (3)
N1—C1—C2122.0 (3)N7—C14—C13115.8 (3)
N1—C1—C11114.0 (3)C15—C14—C13118.6 (3)
C2—C1—C11124.0 (3)C14—C15—H15A109.5
C3—C2—C1118.3 (4)C14—C15—H15B109.5
C3—C2—H2120.8H15A—C15—H15B109.5
C1—C2—H2120.8C14—C15—H15C109.5
C4—C3—C2119.9 (3)H15A—C15—H15C109.5
C4—C3—H3120.1H15B—C15—H15C109.5
C2—C3—H3120.1O5—S1—C16105.84 (18)
C3—C4—C5120.3 (4)O5—S1—C17106.01 (19)
C3—C4—H4119.9C16—S1—C1797.4 (2)
C5—C4—H4119.9S1—C16—H16A109.5
N1—C5—C4119.3 (3)S1—C16—H16B109.5
N1—C5—C6120.8 (3)H16A—C16—H16B109.5
C4—C5—C6119.9 (3)S1—C16—H16C109.5
N2—C6—C5127.6 (3)H16A—C16—H16C109.5
N2—C6—C7114.2 (3)H16B—C16—H16C109.5
C5—C6—C7118.2 (3)S1—C17—H17A109.5
C6—C7—H7A109.5S1—C17—H17B109.5
C6—C7—H7B109.5H17A—C17—H17B109.5
H7A—C7—H7B109.5S1—C17—H17C109.5
C6—C7—H7C109.5H17A—C17—H17C109.5
H7A—C7—H7C109.5H17B—C17—H17C109.5
H7B—C7—H7C109.5
N3—Ni1—N1—C51.8 (3)N3—N2—C6—C50.1 (6)
N5—Ni1—N1—C5177.6 (3)N3—N2—C6—C7179.3 (3)
N3—Ni1—N1—C1178.2 (2)N1—C5—C6—N20.6 (6)
N5—Ni1—N1—C12.5 (2)C4—C5—C6—N2179.7 (3)
C6—N2—N3—C8179.9 (3)N1—C5—C6—C7178.8 (3)
C6—N2—N3—Ni10.8 (5)C4—C5—C6—C70.9 (5)
N1—Ni1—N3—N21.4 (3)N2—N3—C8—O10.1 (5)
N4—Ni1—N3—N2179.4 (3)Ni1—N3—C8—O1179.3 (3)
N1—Ni1—N3—C8179.5 (2)N2—N3—C8—C9179.2 (3)
N4—Ni1—N3—C81.4 (2)Ni1—N3—C8—C90.0 (4)
N3—Ni1—N4—C92.9 (3)O2—N4—C9—C8177.2 (3)
N5—Ni1—N4—C9176.5 (3)Ni1—N4—C9—C83.6 (4)
N3—Ni1—N4—O2178.0 (3)O2—N4—C9—C101.5 (6)
N5—Ni1—N4—O22.6 (3)Ni1—N4—C9—C10177.6 (3)
N1—Ni1—N5—C115.8 (3)O1—C8—C9—N4178.3 (3)
N4—Ni1—N5—C11172.3 (3)N3—C8—C9—N42.3 (4)
N1—Ni1—N5—N6179.4 (3)O1—C8—C9—C100.5 (6)
N4—Ni1—N5—N62.6 (3)N3—C8—C9—C10178.8 (3)
C11—N5—N6—C1360.5 (4)N6—N5—C11—C1177.6 (3)
Ni1—N5—N6—C13124.7 (3)Ni1—N5—C11—C17.3 (4)
C5—N1—C1—C21.7 (5)N6—N5—C11—C126.8 (5)
Ni1—N1—C1—C2178.3 (3)Ni1—N5—C11—C12168.3 (3)
C5—N1—C1—C11179.3 (3)N1—C1—C11—N55.1 (4)
Ni1—N1—C1—C110.6 (4)C2—C1—C11—N5173.9 (3)
N1—C1—C2—C30.6 (5)N1—C1—C11—C12170.7 (3)
C11—C1—C2—C3179.5 (3)C2—C1—C11—C1210.3 (5)
C1—C2—C3—C40.8 (5)N5—N6—C13—O38.2 (5)
C2—C3—C4—C51.0 (6)N5—N6—C13—C14172.7 (3)
C1—N1—C5—C41.4 (5)O4—N7—C14—C150.1 (5)
Ni1—N1—C5—C4178.7 (3)O4—N7—C14—C13179.6 (3)
C1—N1—C5—C6178.3 (3)O3—C13—C14—N7174.8 (3)
Ni1—N1—C5—C61.6 (5)N6—C13—C14—N76.1 (5)
C3—C4—C5—N10.1 (5)O3—C13—C14—C154.9 (5)
C3—C4—C5—C6179.7 (3)N6—C13—C14—C15174.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6O···O30.902.072.948 (4)162
N6—H6N···O20.891.702.555 (4)162
O4—H4O···O50.951.732.661 (4)165
O6—H6P···O1i0.911.992.819 (4)151
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C15H17N7O4)]·C2H6OS·H2O
Mr514.21
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)7.3076 (2), 11.1899 (5), 13.9875 (6)
α, β, γ (°)74.652 (2), 84.472 (2), 73.641 (2)
V3)1058.04 (7)
Z2
Radiation typeMo Kα
µ (mm1)1.07
Crystal size (mm)0.19 × 0.05 × 0.03
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
[SADABS (Version 2.10; Sheldrick, 2003)]
Tmin, Tmax0.822, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
18361, 4128, 3008
Rint0.092
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.109, 1.06
No. of reflections4128
No. of parameters296
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.43

Computer programs: COLLECT (Bruker, 2004), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top
Ni1—N31.828 (3)Ni1—N41.879 (3)
Ni1—N11.873 (3)Ni1—N51.888 (3)
N3—Ni1—N194.01 (13)N1—Ni1—N583.41 (13)
N3—Ni1—N483.99 (13)N4—Ni1—N598.61 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6O···O30.902.072.948 (4)162.4
N6—H6N···O20.891.702.555 (4)162.2
O4—H4O···O50.951.732.661 (4)165.0
O6—H6P···O1i0.911.992.819 (4)150.8
Symmetry code: (i) x+1, y, z+1.
 

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