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The title compound, [Ni(C20H17N3OP)(N3)], is the first complex with a semicarbazide-based ligand having a P atom as one of the donors. The influence of the P atom on the deformation of the coordination geometry of the NiII ion is evident but less expressed than in the cases of complexes with analogous seleno- and thio­semicarbazide ligands. The torsion angles involving the two bonds formed by the P atom within the six-membered chelate ring have the largest values [C—P—Ni—N = 24.3 (2)° and C—C—P—Ni = −24.2 (4)°], suggesting that the P atom considerably influences the conformation of the ring. Two types of N—H...N hydrogen bond connect the complex units into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109021970/gz3164sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109021970/gz3164IIsup2.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270109021970/gz3164sup3.pdf
Supplementary material

CCDC reference: 742231

Comment top

Semicarbazones, thiosemicarbazones and selenosemicarbazones and their metal complexes have been the subject of extensive investigations because of their potential pharmacological properties (Beraldo & Gambino, 2004; Gómez-Quiroga & Navarro Ranninger, 2004). Besides their relevance for biological studies, the structural diversity of these ligands, their good complexation abilities and their different numbers of coordination modes have prompted the development of a very rich structural chemistry related to these compounds (Campbell, 1975; Padhyé & Kauffman, 1985; West et al., 1991, 1993; Fanning, 1991; Dittes et al., 1997; Casas et al., 2000). The similarity in composition and structure which can be attained by the analogous semi-, thiosemi- and selenosemicarbazone ligands offers an opportunity for an investigation of the changes in metal–ligand bonding when the donor set is partly modified by a donor of different radius (O, S and Se, respectively). It also allows a comparison of the extent of the deformation of the metal coordination environment caused by different donor sets, as well as the effect on the manner of intermolecular association. According to a survey of the Cambridge Structural Database (CSD, Version?; Allen, 2002), among the 201 crystal structures containing the fragment (I) there are only six which have a P atom as the X2 donor coordinated to a metal atom (Brčeski et al., 2004; Castineiras & Pedrido, 2008; Abram et al., 2000; Argay et al., 2000; Leovac et al., 1996; You et al. 1997). The title complex, [NiL(N3)] [HL = 2-(diphenylphosphino)benzaldehyde semicarbazone], (II), represents the first complex with a semicarbazone-based ligand (X1 = O) which, besides the standard N and O donors, involves a P atom as the third donor in the coordination environment of the metal.

In the crystal structure of (II), the Ni atom is in a rather deformed square-planar environment formed by atoms P1, N1 and O1 of the deprotonated semicarbazone ligand and azide atom N4 (Fig. 1). While in the cases of complexes with equivalent Se and S ligands, [NiL'(NCS)] [HL' = 2-(diphenylphosphino)benzaldehyde selenosemicarbazone], (III) (Brčeski et al., 2004), and [NiL''(py)]NO3 [HL'' = 2-(diphenylphosphino)benzaldehyde thiosemicarbazone] (Leovac et al., 1996), considerable deviation of the P atom from the mean planes defined by Ni and the rest of the coordinated atoms has been reported [0.494 (3) and 0.683 (3) Å, respectively], in the present case the deviation of P is less expressed and equal to 0.079 (4) Å.

Selected geometric parameters for (II) are given in Table 1. It is worth noting that three metal–ligand bonds (one Ni—O and two Ni—N) have almost identical lengths, while Ni—P is longer, as expected. Comparison of this geometry with related Ni complexes with Se and S ligands points to substantial shortening of the Ni—P bond by 0.048 and 0.041 Å, respectively. Similarly, the Ni—N1 bond in (II) is on average 0.024 Å shorter than those in the previously characterized complexes. This finding suggests that the presence of the O atom as a donor instead of S or Se induces stronger binding of the ligand in general.

Coordination of the tridentate ligand to the metal atom in (II) results in the formation of the two fused chelate rings, one five-membered (semicarbazide) and the other six-membered [(2-diphenylphosphino)benzaldehyde]. The five-membered ring is nearly planar, with an r.m.s. deviation of the constituent atoms of 0.057 Å. The six-membered ring, on the other hand, exhibits considerable deviation of its atoms from the mean plane (0.136 Å). The ring-puckering parameters defined for the atom sequence P1—C4—C3—C2—N1—Ni are θ = 62.0 (8)°, ϕ = -20.1 (8)° and Q = 0.337 (3) Å (Cremer & Pople, 1975). A similar deformation of the six-membered chelate ring containing the P atom was observed and explained in more detail in a previously reported paper (Brčeski et al., 2004), and it was also described in other structural reports (Drašković et al., 2006; Bogdanović et al., 1998). The P atom is the only one in the chelate ligand which has four bonds and it shows a tendency towards a tetrahedral arrangement. The Ni—P1—C4 angle is therefore 111.95 (13)°, which is in contrast with the planar form of the ring, which requires a wider angle of about 125°. Considering also that atoms N1, C2, C3 and C4 are sp2-hybridized and prefer a planar geometry, the most pronounced deformation of the corresponding chelate ring is evident in the torsion angles involving the two bonds formed by P, C—P—Ni—N = 24.3 (2) and C—C—P—Ni = 24.2 (4)°. The other torsion angles within this chelate ring are below 12°. The torsion angles involving P in (II) are, however, smaller than in (III) [29.6 (1) and 27.1 (1)°, respectively] and [NiL''(py)]NO3 [31.5 (2) and 25.1 (2)°, respectively].

The crystal structure arrangement of (II) is dominated by two relatively strong N—H···N hydrogen bonds (Table 2). Both of these interactions connect centrosymmetrically related molecules into two types of dimers and further into chain of dimers (Fig. 2). The stronger N3—H3B···N2 hydrogen bond engages the semicarbazide parts of a neighbouring complex molecule, forming a cyclic centrosymmetric R22(8) motif (Etter, 1990) centred at (0, 0, 1/2). In the second dimer, the same atom N3 acts as a hydrogen-bond donor via atom H3A to terminal azide atom N6. This pair of interactions therefore results in a centrosymmetric macrocyclic R22(14) motif, centred at (1/2, 1/2, 1/2). In the further arrangement of (II), neighbouring chains of dimers mutually orient their diphenylphosphine moieties (Fig. 2), probably giving rise to C—H···π interactions, as some of the perpendicular distances from H atoms to phenyl ring planes do not exceed 2.8 Å (Desiraju & Steiner, 1999). It should be also mentioned that in the crystal packing of the complex units, the chelate rings which represent widely delocalized systems have a parallel arrangement, resulting in very weak π-stacking interactions. The mean planes of these rings are at a distance of 3.7 Å from each other and the shortest distance of 3.42 Å was observed between atoms C3 and O1 (see Fig. S1 in the Supplementary Material [Please provide this figure]).

Probably the most interesting result concerning the crystal structures of (II) and complexes with analogous ligands is obtained by comparison of the intermolecular interactions in (II) and (III). Although the coordination environments of the corresponding Ni atoms in (II) and (III) differ in half the atoms (P, N, O and azide N, and P, N, Se and thiocianate N, respectively), and in (III) the voluminous Se takes the place of the much smaller O donor, these two complexes arrange in very similar ways (see Fig. S2 in the Supplementary Material [Please provide this figure]). Complex (III) also displays two main structural motifs, R22(8), which here involves the N donors and acceptors from the analogous selenosemicarbazide fragment, and the larger R22(14) motif, where the role of the acceptor is delegated to the S atom of the linear thiocyanate ligand. Finally, as in the case of (II), the bulky diphenylphosphine moieties tend to accumulate in separate regions.

Experimental top

A mixture of 2-(diphenylphosphino)benzaldehyde semicarbazone (100 mg) and Ni(NO3)2.6H2O (100 mg) was dissolved in MeOH (6 ml) with heating. To this solution a warm solution of NaN3 (35 mg) in MeOH (4 ml) was added. A white snow-like precipitate was readily formed which, after 24 h, transformed into red single crystals of complex (II). The crystals were filtered off and washed with MeOH (yield 140 mg).

Refinement top

All H atoms were found in a difference Fourier map, but they were placed in geometrically calculated positions and refined using a riding model, with N—H = 0.86 Å and C—H = 0.93 Å, with Uiso(H) = 1.2Ueq(parent).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: Please provide details; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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), PLATON (Spek, 2009) and PARST (Nardelli, 1983, 1995).

Figures top
[Figure 1] Fig. 1. Molecular drawing of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A segment of the crystal packing of (II), viewed approximately along the c axis, displaying two chains of molecules generated by N—H···N hydrogen bonds separated by regions of accumulated phenyl rings. See Table 2 for symmetry codes.
azido[2-(diphenylphosphino)benzaldehyde semicarbazonato-κ2P,N1,O]nickel(II) top
Crystal data top
[Ni(C20H17N6OP)]Z = 2
Mr = 447.08F(000) = 460
Triclinic, P1Dx = 1.539 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8700 (15) ÅCell parameters from 24 reflections
b = 10.004 (3) Åθ = 11.3–16.1°
c = 12.870 (2) ŵ = 1.11 mm1
α = 69.993 (19)°T = 293 K
β = 70.598 (14)°Prismatic, red
γ = 67.556 (19)°0.30 × 0.28 × 0.25 mm
V = 964.7 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.7°
Graphite monochromatorh = 011
ω/2θ scansk = 1112
4745 measured reflectionsl = 1516
4206 independent reflections3 standard reflections every 60 min
2877 reflections with I > 2σ(I) intensity decay: none
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1138P)2]
where P = (Fo2 + 2Fc2)/3
4206 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.95 e Å3
Crystal data top
[Ni(C20H17N6OP)]γ = 67.556 (19)°
Mr = 447.08V = 964.7 (4) Å3
Triclinic, P1Z = 2
a = 8.8700 (15) ÅMo Kα radiation
b = 10.004 (3) ŵ = 1.11 mm1
c = 12.870 (2) ÅT = 293 K
α = 69.993 (19)°0.30 × 0.28 × 0.25 mm
β = 70.598 (14)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.025
4745 measured reflections3 standard reflections every 60 min
4206 independent reflections intensity decay: none
2877 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.01Δρmax = 0.92 e Å3
4206 reflectionsΔρmin = 0.95 e Å3
262 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
Ni10.57057 (7)0.18910 (5)0.33705 (4)0.0341 (2)
P10.52524 (13)0.12099 (10)0.21331 (9)0.0306 (2)
N10.7209 (4)0.0042 (4)0.3884 (3)0.0360 (8)
N20.8146 (5)0.0123 (4)0.4535 (3)0.0464 (9)
N30.8234 (5)0.1741 (5)0.5389 (3)0.0529 (11)
H3A0.78580.25980.55430.063*
H3B0.90680.10660.56440.063*
N40.4346 (5)0.3818 (4)0.2844 (4)0.0475 (10)
N50.3206 (6)0.4496 (4)0.3454 (4)0.0525 (10)
N60.2078 (8)0.5271 (7)0.3972 (5)0.0911 (19)
O10.6267 (4)0.2498 (3)0.4380 (3)0.0413 (7)
C10.7522 (6)0.1460 (5)0.4753 (4)0.0406 (10)
C20.7549 (6)0.1272 (4)0.3761 (4)0.0388 (10)
H20.84080.20130.40790.047*
C30.6749 (5)0.1733 (4)0.3184 (3)0.0325 (8)
C40.5653 (5)0.0778 (4)0.2485 (3)0.0320 (8)
C50.4895 (6)0.1392 (5)0.2053 (4)0.0405 (10)
H50.41600.07590.15910.049*
C60.5200 (6)0.2905 (5)0.2292 (4)0.0429 (10)
H60.46640.32910.20060.051*
C70.6310 (6)0.3845 (5)0.2960 (4)0.0469 (11)
H70.65410.48730.31150.056*
C80.7081 (6)0.3273 (5)0.3399 (4)0.0434 (10)
H80.78340.39190.38460.052*
C90.6661 (5)0.1669 (4)0.0753 (3)0.0330 (8)
C100.7635 (6)0.0623 (5)0.0127 (4)0.0451 (10)
H100.76210.03620.04210.054*
C110.8627 (6)0.1041 (6)0.0930 (4)0.0529 (12)
H110.92700.03390.13540.063*
C120.8671 (6)0.2497 (6)0.1365 (4)0.0535 (12)
H120.93440.27740.20790.064*
C130.7715 (7)0.3539 (6)0.0739 (4)0.0546 (13)
H130.77440.45200.10300.065*
C140.6720 (6)0.3127 (5)0.0314 (4)0.0447 (11)
H140.60800.38320.07360.054*
C150.3180 (5)0.2038 (4)0.1846 (4)0.0344 (9)
C160.2959 (6)0.2417 (5)0.0754 (4)0.0441 (10)
H160.38870.22580.01510.053*
C170.1348 (7)0.3035 (6)0.0556 (5)0.0557 (13)
H170.11980.32770.01750.067*
C180.0007 (7)0.3279 (6)0.1436 (6)0.0625 (15)
H180.10680.36930.13050.075*
C190.0214 (6)0.2921 (7)0.2524 (5)0.0654 (16)
H190.07180.31060.31200.078*
C200.1807 (6)0.2286 (5)0.2731 (4)0.0502 (12)
H200.19440.20280.34680.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0426 (3)0.0232 (3)0.0406 (3)0.0109 (2)0.0194 (2)0.0021 (2)
P10.0364 (6)0.0213 (5)0.0383 (6)0.0100 (4)0.0201 (4)0.0000 (4)
N10.044 (2)0.0308 (17)0.0390 (18)0.0123 (15)0.0209 (16)0.0032 (14)
N20.062 (2)0.039 (2)0.050 (2)0.0118 (18)0.0335 (19)0.0083 (17)
N30.064 (3)0.050 (2)0.056 (2)0.009 (2)0.031 (2)0.020 (2)
N40.060 (3)0.0259 (19)0.059 (2)0.0036 (18)0.031 (2)0.0069 (18)
N50.068 (3)0.032 (2)0.056 (3)0.010 (2)0.030 (2)0.001 (2)
N60.098 (4)0.062 (3)0.073 (4)0.004 (3)0.016 (3)0.004 (3)
O10.0486 (18)0.0341 (15)0.0479 (18)0.0100 (13)0.0197 (14)0.0126 (13)
C10.054 (3)0.035 (2)0.036 (2)0.017 (2)0.016 (2)0.0049 (18)
C20.050 (3)0.0217 (19)0.046 (2)0.0025 (17)0.027 (2)0.0047 (17)
C30.041 (2)0.0218 (18)0.037 (2)0.0104 (16)0.0164 (17)0.0019 (15)
C40.035 (2)0.0242 (18)0.036 (2)0.0099 (16)0.0121 (17)0.0028 (16)
C50.048 (3)0.027 (2)0.052 (3)0.0140 (18)0.026 (2)0.0006 (18)
C60.051 (3)0.030 (2)0.059 (3)0.0206 (19)0.017 (2)0.009 (2)
C70.062 (3)0.025 (2)0.057 (3)0.017 (2)0.021 (2)0.0038 (19)
C80.051 (3)0.024 (2)0.056 (3)0.0061 (18)0.026 (2)0.0032 (19)
C90.036 (2)0.030 (2)0.038 (2)0.0148 (17)0.0182 (17)0.0006 (16)
C100.044 (3)0.041 (2)0.054 (3)0.014 (2)0.018 (2)0.008 (2)
C110.043 (3)0.057 (3)0.054 (3)0.009 (2)0.012 (2)0.015 (2)
C120.044 (3)0.065 (3)0.048 (3)0.024 (2)0.014 (2)0.000 (2)
C130.063 (3)0.051 (3)0.053 (3)0.033 (3)0.021 (2)0.010 (2)
C140.057 (3)0.034 (2)0.050 (3)0.020 (2)0.023 (2)0.0013 (19)
C150.036 (2)0.0195 (17)0.049 (2)0.0093 (15)0.0231 (19)0.0028 (16)
C160.045 (2)0.038 (2)0.054 (3)0.007 (2)0.026 (2)0.008 (2)
C170.061 (3)0.043 (3)0.073 (4)0.007 (2)0.043 (3)0.009 (2)
C180.047 (3)0.047 (3)0.098 (5)0.017 (2)0.038 (3)0.000 (3)
C190.032 (3)0.065 (4)0.079 (4)0.016 (2)0.012 (2)0.006 (3)
C200.046 (3)0.049 (3)0.049 (3)0.021 (2)0.016 (2)0.008 (2)
Geometric parameters (Å, º) top
Ni1—N11.871 (3)C7—C81.376 (6)
Ni1—N41.872 (4)C7—H70.9300
Ni1—O11.872 (3)C8—H80.9300
Ni1—P12.1306 (11)C9—C101.384 (6)
P1—C41.799 (4)C9—C141.387 (6)
P1—C151.811 (4)C10—C111.377 (7)
P1—C91.826 (4)C10—H100.9300
N1—C21.285 (5)C11—C121.381 (8)
N1—N21.401 (5)C11—H110.9300
N2—C11.327 (6)C12—C131.379 (8)
N3—C11.335 (6)C12—H120.9300
N3—H3A0.8600C13—C141.374 (7)
N3—H3B0.8600C13—H130.9300
N4—N51.189 (6)C14—H140.9300
N5—N61.168 (7)C15—C201.373 (7)
O1—C11.297 (5)C15—C161.385 (6)
C2—C31.451 (6)C16—C171.396 (7)
C2—H20.9300C16—H160.9300
C3—C41.396 (5)C17—C181.353 (8)
C3—C81.397 (5)C17—H170.9300
C4—C51.391 (6)C18—C191.378 (8)
C5—C61.373 (6)C18—H180.9300
C5—H50.9300C19—C201.386 (7)
C6—C71.376 (7)C19—H190.9300
C6—H60.9300C20—H200.9300
N1—Ni1—O184.20 (14)C8—C7—H7119.8
N4—Ni1—O192.28 (15)C6—C7—H7119.8
N1—Ni1—P194.74 (11)C7—C8—C3120.9 (4)
N4—Ni1—P188.49 (13)C7—C8—H8119.6
O1—Ni1—P1175.49 (11)C3—C8—H8119.6
N1—Ni1—N4174.91 (17)C10—C9—C14119.4 (4)
C4—P1—Ni1111.95 (13)C10—C9—P1122.2 (3)
C15—P1—Ni1117.29 (15)C14—C9—P1118.4 (3)
C9—P1—Ni1110.42 (13)C11—C10—C9119.9 (5)
C4—P1—C15106.06 (18)C11—C10—H10120.0
C4—P1—C9105.94 (19)C9—C10—H10120.0
C15—P1—C9104.32 (19)C10—C11—C12120.4 (5)
C2—N1—N2114.1 (3)C10—C11—H11119.8
C2—N1—Ni1133.3 (3)C12—C11—H11119.8
N2—N1—Ni1112.6 (3)C13—C12—C11119.9 (5)
C1—N2—N1109.0 (4)C13—C12—H12120.1
C1—N3—H3A120.0C11—C12—H12120.1
C1—N3—H3B120.0C14—C13—C12119.9 (5)
H3A—N3—H3B120.0C14—C13—H13120.0
N5—N4—Ni1123.0 (3)C12—C13—H13120.0
N6—N5—N4174.1 (5)C13—C14—C9120.5 (5)
C1—O1—Ni1109.4 (3)C13—C14—H14119.7
O1—C1—N2123.4 (4)C9—C14—H14119.7
O1—C1—N3118.7 (4)C20—C15—C16119.6 (4)
N2—C1—N3117.9 (4)C20—C15—P1119.2 (3)
N1—C2—C3127.4 (4)C16—C15—P1121.2 (3)
N1—C2—H2116.3C15—C16—C17120.2 (5)
C3—C2—H2116.3C15—C16—H16119.9
C4—C3—C8118.9 (4)C17—C16—H16119.9
C4—C3—C2125.7 (3)C18—C17—C16119.5 (5)
C8—C3—C2115.4 (4)C18—C17—H17120.2
C5—C4—C3118.8 (4)C16—C17—H17120.2
C5—C4—P1120.6 (3)C17—C18—C19120.7 (5)
C3—C4—P1120.6 (3)C17—C18—H18119.6
C6—C5—C4121.8 (4)C19—C18—H18119.6
C6—C5—H5119.1C18—C19—C20120.2 (5)
C4—C5—H5119.1C18—C19—H19119.9
C5—C6—C7119.2 (4)C20—C19—H19119.9
C5—C6—H6120.4C15—C20—C19119.8 (5)
C7—C6—H6120.4C15—C20—H20120.1
C8—C7—C6120.4 (4)C19—C20—H20120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N2i0.862.273.051 (7)152
N3—H3A···N6ii0.862.443.254 (8)158
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C20H17N6OP)]
Mr447.08
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.8700 (15), 10.004 (3), 12.870 (2)
α, β, γ (°)69.993 (19), 70.598 (14), 67.556 (19)
V3)964.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.11
Crystal size (mm)0.30 × 0.28 × 0.25
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4745, 4206, 2877
Rint0.025
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.169, 1.01
No. of reflections4206
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.92, 0.95

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), Please provide details, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1983, 1995).

Selected geometric parameters (Å, º) top
Ni1—N11.871 (3)P1—C91.826 (4)
Ni1—N41.872 (4)N1—C21.285 (5)
Ni1—O11.872 (3)N1—N21.401 (5)
Ni1—P12.1306 (11)N2—C11.327 (6)
P1—C41.799 (4)N3—C11.335 (6)
P1—C151.811 (4)O1—C11.297 (5)
N1—Ni1—O184.20 (14)C4—P1—Ni1111.95 (13)
N4—Ni1—O192.28 (15)C15—P1—Ni1117.29 (15)
N1—Ni1—P194.74 (11)C9—P1—Ni1110.42 (13)
N4—Ni1—P188.49 (13)C4—P1—C15106.06 (18)
O1—Ni1—P1175.49 (11)C4—P1—C9105.94 (19)
N1—Ni1—N4174.91 (17)C15—P1—C9104.32 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N2i0.862.273.051 (7)152
N3—H3A···N6ii0.862.443.254 (8)158
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y+1, z+1.
 

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